CN115703803A - Polycyclic aromatic compounds, materials for organic devices, organic electroluminescent elements, display devices, and lighting devices - Google Patents

Abstract

The invention provides a polycyclic aromatic compound, a material for an organic device, an organic electroluminescent element, a display device, and a lighting device. The polycyclic aromatic compound has one or more structures including a structural unit represented by formula (1): formula (1);

[ Ring A, ring B are a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring, ring C is a ring represented by the formula (C), Y ¹ B, etc., X ¹ And X ² Is > N-R, etc. (R is aryl, etc.), X ¹ Or X ² At least one of (a) is > N-G, G is a group represented by the formula (G), two Z's optionally adjacent to each other ^C Is with Y ¹ And X ² Directly bound carbon, other Z ^C And Z ^g Is C-H, etc., X ^c At least one of the aryl or heteroaryl rings in formula (1) may be condensed with at least one cycloalkane]。

Description

Polycyclic aromatic compounds, materials for organic devices, organic electroluminescent elements, display display and lighting

technical field

The present invention relates to a polycyclic aromatic compound. In particular, the present invention relates to a polycyclic aromatic compound comprising nitrogen and boron. The present invention further relates to a material for an organic device, an organic electroluminescence element, a display device, and an illumination device comprising the polycyclic aromatic compound.

Background technique

Conventionally, display devices using light-emitting elements that perform electroluminescence have been researched in various ways because they can save power or reduce thickness. Furthermore, organic electroluminescent elements made of organic materials have been actively studied because they are easy to reduce in weight or increase in size. . In particular, regarding the development of organic materials having light-emitting properties such as blue, which is one of the three primary colors of light, and regarding the development of organic materials with charge transport capabilities including holes, electrons, etc. (with the possibility of becoming semiconductors or superconductors) Development, so far, both high-molecular-weight compounds and low-molecular-weight compounds have been actively studied.

An organic electroluminescent element has a structure including: a pair of electrodes including an anode and a cathode, and one or more layers that are arranged between the pair of electrodes and include an organic compound. Among layers containing organic compounds, there are light emitting layers, or charge transport/injection layers that transport or inject charges of holes, electrons, etc., and various organic materials suitable for these layers have been developed.

Among them, Patent Document 1 discloses that boron-containing polycyclic aromatic compounds are effective as materials for organic electroluminescent elements and the like. It is reported that an organic electroluminescent element containing the polycyclic aromatic compound has good external quantum efficiency.

[Prior art literature]

[Patent Document]

[Patent Document 1] International Publication No. 2015/102118

[Patent Document 2] International Publication No. 2020/111830

[Patent Document 3] International Publication No. 2020/251049

Contents of the invention

[Problem to be Solved by the Invention]

As described above, various materials have been developed as materials for organic electroluminescence (EL) elements, but in order to increase the options of materials for organic EL elements, it is desired to develop materials containing compounds different from conventional ones.

An object of the present invention is to provide a novel compound that can be effectively used as a material for organic devices such as organic EL elements.

[Technical means to solve the problem]

The inventors of the present invention have conducted intensive research to solve the above problems, and succeeded in producing a novel polycyclic aromatic compound having superior light-emitting characteristics among polycyclic aromatic compounds having a structure similar to that of the compound described in Patent Document 1. . In addition, they have found that an excellent organic EL device can be obtained by disposing a layer containing the polycyclic aromatic compound between a pair of electrodes to form an organic EL device, and completed the present invention. That is, the present invention provides the following polycyclic aromatic compound, a material for an organic device including the following polycyclic aromatic compound, and the like.

Specifically, the present invention has the following structures.

<1> A polycyclic aromatic compound having one or more structures comprising structural units represented by the following formula (1);

[chemical 1]

In formula (1),

Ring A and ring B are independently substituted or unsubstituted aryl rings or substituted or unsubstituted heteroaryl rings;

C ring is a ring represented by formula (C),

In formula (C),

X ^c is >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, the >NR, the >C(-R) ₂ and the > R of Si(-R) ₂ are independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted In a substituted cycloalkyl group, the >C(-R) ₂ and the >Si(-R) ₂ Rs can be bonded to each other to form a ring,

Any adjacent two ^ZCs are carbons directly bonded to either ^Y1 or ^X2 , respectively,

Other Z ^C are independently N or ^CRC , R ^C are independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted di Arylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted Alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or An unsubstituted arylthio group or a substituted silyl group, the two aryl groups of the diarylamino group can be bonded to each other via a linking group, and the two heteroaryl groups of the diheteroarylamino group can be bonded to each other via a linking group The aryl group of the arylheteroarylamino group and the heteroaryl group can be bonded to each other through a linking group, and the two aryl groups of the diarylboryl group can be bonded to each other through a single bond or a linking group. bond,

Two adjacent R ^C can be bonded to each other to form an aryl ring or a heteroaryl ring, the formed aryl ring and heteroaryl ring are respectively unsubstituted or substituted by at least one R ^C2 , R ^C2 and R ^C For the same meaning, wherein, R ^C2 is not hydrogen, and two adjacent R ^C2 will not be bonded to each other to form an aryl ring or a heteroaryl ring;

^Y1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, and the R of the Si-R and the Ge-R is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;

X ¹ and X ² are independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, and R in the >NR is hydrogen, substituted or Unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, said >C(-R) ₂ , and the R of >Si(-R) ₂ are independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or For a substituted or unsubstituted cycloalkyl group, the two Rs of the >C(-R) ₂ and the >Si(-R) ₂ can be bonded to each other to form a ring. In addition, the R of the >NR And/or said >C(-R) ₂ R can be bonded to A ring and/or B ring, or A ring and/or C ring through a linking group or a single bond,

Wherein, at least one of X ¹ or X ² is >NG, and G is a group represented by formula (G),

In formula (G),

Z ^g is independently N or CR ^g , and R ^g is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diaryl Amino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkane substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted A substituted arylthio group or a substituted silyl group, the two aryl groups of the diarylamino group can be bonded to each other via a linking group, and the two heteroaryl groups of the diheteroarylamino group can be bonded to each other via a linking group Bonding, the aryl and heteroaryl groups of the arylheteroarylamino group can be bonded to each other via a linking group, and the two aryl groups of the diarylboryl group can be bonded to each other via a single bond or a linking group ,

Two adjacent R ^g can be bonded to each other to form an aryl ring or a heteroaryl ring, and the formed aryl ring and heteroaryl ring are respectively unsubstituted or substituted by at least one R ^g2 , R ^g2 and R ^g For the same meaning, wherein, R ^g2 is not hydrogen, and two adjacent R ^g2 will not be bonded to each other to form an aryl ring or a heteroaryl ring,

* indicates the bonding position with N;

At least one of the aryl ring or heteroaryl ring in the structure may be condensed by at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one _-CH2- in the cycloalkane may be represented by - O-substitution;

At least one hydrogen in the structure may be replaced by cyano, halogen, or deuterium.

<2> The polycyclic aromatic compound according to <1>, wherein the structural unit represented by formula (1) is a structural unit represented by formula (2);

[Chem 2]

In formula (2),

In ring a and ring b, Z is independently N or CR ¹¹ , or Z=Z is independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S , or >Se, the R of the >NR, the >C(-R) ₂ and the >Si(-R) ₂ are independently hydrogen, substituted or unsubstituted aryl, substituted or Unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, the >C(-R) ₂ and the >Si(-R) ₂ Two R can be bonded to each other to form a ring,

R ¹¹ of said CR ¹¹ are independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted Substituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted Substituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl groups,

The two aryl groups of the diarylamino group can be bonded to each other via a linking group, the two heteroaryl groups of the diheteroarylamino group can be bonded to each other via a linking group, and the arylheteroarylamino group can be bonded to each other via a linking group. The aryl group and the heteroaryl group can be bonded to each other via a linking group, and the two aryl groups of the diaryl boron group can be bonded to each other via a single bond or a linking group,

Two adjacent R ¹¹ can be bonded to each other and form an aryl ring or a heteroaryl ring together with the a ring or the b ring, and the formed aryl ring and heteroaryl ring are respectively unsubstituted, or are composed of at least one R ^11b Substitution, R ^11b and R ¹¹ have the same meaning, wherein, R ^11b is not hydrogen, and two adjacent R ^11b will not be bonded to each other to form an aryl ring or a heteroaryl ring,

C ring is the ring represented by formula (C);

^Y1 is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, and the R of the Si-R and the Ge-R is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;

X ¹ and X ² are independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, and R in the >NR is hydrogen, substituted or Unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, said >C(-R) ₂ , and the R of >Si(-R) ₂ are independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or For a substituted or unsubstituted cycloalkyl group, the two Rs of the >C(-R) ₂ and the >Si(-R) ₂ can be bonded to each other to form a ring. In addition, the R of the >NR And/or the R of >C(-R) ₂ can be bonded to a ring and/or b ring, or a ring and/or C ring through a linking group or a single bond, wherein X ¹ or X ² At least one is >NG, and the G of >NG is a group represented by formula (G);

At least one of the aryl ring or heteroaryl ring in the structure may be condensed by at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one _-CH2- in the cycloalkane may be represented by - O-substitution;

At least one hydrogen in the structure may be replaced by cyano, halogen, or deuterium.

<3> The polycyclic aromatic compound according to <2>, wherein the structural unit represented by formula (2) is a structural unit represented by formula (2a-1);

[Chem 3]

In formula (2a-1), Y ¹ , X ¹ , X ² , X ^C have the same meanings as Y ¹ , X ¹ , X ² , and X ^C in formula (2), and R ^11b , R ^C2 have the same meanings as formula ( 2) R ^11b and R ^C2 have the same meaning respectively,

n1 is an integer from 0 to 4, n2 is an integer from 0 to 4, n3 is an integer from 0 to 3,

at least one of the aryl or heteroaryl rings in the structure may be condensed with at least one cycloalkane,

At least one hydrogen in the structure may be replaced by cyano, halogen, or deuterium.

<4> The polycyclic aromatic compound according to <3>, represented by any one of the following formulae.

[chemical 4]

[chemical 5]

[chemical 6]

[chemical 7]

In the formula, Me is methyl, tBu is tert-butyl, and D is deuterium.

<5> The polycyclic aromatic compound according to <2>, wherein the structural unit represented by formula (2) is a structural unit represented by formula (2a-2);

[chemical 8]

In formula (2a-2), Y ¹ , X ¹ , X ² , X ^C have the same meanings as Y ¹ , X ¹ , X ² , and X ^C in formula (2), and R ^11b , R ^C2 have the same meanings as formula ( 2) R ^11b and R ^C2 have the same meaning respectively,

X ³ and X ⁴ are independently a single bond, >O, >NR, >C(-R) ₂ , or >S, wherein X ³ and X ⁴ are not single bonds at the same time,

n1 is an integer of 0 to 4, n2 is an integer of 0 to 4, n3 is an integer of 0 to 3, n4 is an integer of 0 to 2,

at least one of the aryl or heteroaryl rings in the structure may be condensed with at least one cycloalkane,

At least one hydrogen in the structure may be replaced by cyano, halogen, or deuterium.

<6> The polycyclic aromatic compound according to <5>, represented by any one of the following formulae.

[chemical 9]

In the formula, Me is methyl, tBu is tert-butyl, and D is deuterium.

<7> The polycyclic aromatic compound according to <2>, represented by the following formula.

[chemical 10]

<8> A material for an organic device containing the polycyclic aromatic compound according to any one of <1> to <7>.

<9> An organic electroluminescence element, comprising: a pair of electrodes, including an anode and a cathode; A polycyclic aromatic compound according to one item.

<10> The organic electroluminescence element according to <9>, wherein the light emitting layer contains a host, and the polycyclic aromatic compound as a dopant.

化合物。<11> The organic electroluminescent device according to <10>, wherein the host is an anthracene compound, a fluorene compound, or a dibenzo

compound.

<12> A display device or a lighting device including the organic electroluminescent element according to any one of <9> to <11>.

[Effect of the invention]

According to the present invention, it is possible to provide a novel polycyclic aromatic compound which can be effectively used as a material for organic devices such as organic electroluminescent elements. The polycyclic aromatic compound of the present invention can be used to manufacture organic devices such as organic electroluminescent elements.

Description of drawings

FIG. 1 is a schematic cross-sectional view showing an example of an organic electroluminescence element.

FIG. 2 is an energy level diagram showing the energy relationship of a host, an auxiliary dopant, and an emitting dopant in a TAF device using a general fluorescent dopant.

3 is an energy level diagram showing an example of the energy relationship of a host, an auxiliary dopant, and an emitting dopant in an organic electroluminescent device according to an embodiment of the present invention.

[explanation of the symbol]

100: Organic electroluminescence element

101: Substrate

102: anode

103: Hole injection layer

104: hole transport layer

105: Luminous layer

106: Electron transport layer

107: Electron injection layer

108: Cathode

E(1,G): The energy level of the ground state of the host

E(1,S,Sh): The lowest excited singlet energy level of the host

E(1, T, Sh): The lowest excited triplet energy level of the host

E(2,G): the energy level of the ground state of the auxiliary dopant

E(2,S,Sh): the lowest excited singlet energy level of the auxiliary dopant

E(2,T,Sh): the lowest excited triplet energy level of the auxiliary dopant

E(3,G): the energy level of the ground state of the emissive dopant

E(3,S,Sh): the lowest excited singlet energy level of the emissive dopant

E(3,T,Sh): the lowest excited triplet energy level of the emissive dopant

h ⁺ : hole

e ^- : electron

FRET: Fluorescence Resonance Energy Transfer

Detailed ways

Hereinafter, the present invention will be described in detail. The description of the constituent requirements described below may be based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. In addition, the numerical range represented using "-" in this specification means the range which includes the numerical value described before and after "-" as a lower limit and an upper limit. In addition, "hydrogen" in description of a structural formula in this specification means a "hydrogen atom (H)", and "carbon" means a "carbon atom (C)". In this specification, an organic electroluminescent element may be referred to as an organic EL element.

In this specification, a chemical structure or a substituent may be represented by a carbon number, but when a substituent is substituted in the chemical structure, or when a substituent is further substituted on the substituent, the carbon number refers to the carbon number of each of the chemical structure or the substituent. The number does not refer to the total carbon number of the chemical structure and the substituent, or the total carbon number of the substituent and the substituent. For example, the so-called "substituent B with carbon number Y substituted by substituent A with carbon number X" means that "substituent A with carbon number X" is substituted on "substituent B with carbon number Y", and the carbon number Y is not the total carbon number of substituent A and substituent B. In addition, for example, the so-called "substituent B with carbon number Y substituted by substituent A" means that "substituent A (not limited to carbon number)" is substituted on "substituent B with carbon number Y", and the carbon number Y is not the total carbon number of substituent A and substituent B.

The chemical structural formulas described in this specification (including general formulas drawn by Markush structural formulas such as formula (1) described later) are planar structural formulas, so there may actually be enantiomers (enantiomers), Various isomeric structures such as diastereomers or rotamers. In this specification, unless otherwise specified, the compound described may be any isomer structure conceivable from its planar structural formula, and may be a mixture of possible isomers in any ratio.

A plurality of structural formulas of aromatic compounds are described in this specification. Aromatic compounds are described as a combination of double bonds and single bonds, but in fact, π electrons resonate, so even a single substance has an equivalent resonance structure in which multiple double bonds and single bonds are alternately replaced. In this specification, only one resonance structural formula is described for one substance, but unless otherwise specified, other resonance structural formulas equivalent in organic chemistry are also included. For this, reference can be made to the description of "Z=Z" and the like described later. That is, for example, about "Z=Z" in the formula (2) mentioned later, if an example is shown, it will be as follows. However, it is not limited thereto, and it is of course applicable to not only the one resonance structural formula described, but also other conceivable equivalent resonance structural formulas.

[chemical 11]

In addition, the expression "may~" may be used in this specification, and it has the same meaning as "not~, or through~".

In the present specification, "adjacent" is used for two atoms directly bonded by a covalent bond in the structural formula, or two groups to which two atoms directly bonded by a covalent bond are respectively bonded.

In this specification, a substituent may be substituted with a further substituent. For example, regarding a specific substituent, it may be described as "substituted or unsubstituted". This means that at least one hydrogen of the specific substituent is substituted with a further substituent, or is unsubstituted. In this specification, the specific substituent at this time may be referred to as a "first substituent", and the further substituent may be referred to as a "second substituent".

<1. Polycyclic aromatic compounds>

The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure including one or two or more structural units represented by formula (1). It has been known that a compound having a basic skeleton represented by formula (1) can provide a device with a narrow half-value width of light emission and excellent color purity, but the inventors of the present invention found that by making it also has formula (C) and The compound with the partial structure represented by (G) can produce an organic electroluminescent device with lower voltage and higher luminous efficiency.

[chemical 12]

In formula (1), "A", "B", and "C" inside a circle are symbols representing the ring structure represented by each circle. The structural unit represented by the formula (1) has a structure in which at least three aromatic rings among the A ring, B ring, and C ring are linked by heteroelements such as boron, oxygen, nitrogen, and sulfur to form a ring structure. The formed ring structure is a condensed ring structure composed of at least five rings.

In formula (1), ring C is a ring structure represented by formula (C). In formula (C), any adjacent two Z ^C are carbons bonded to ^{either Y1} or ^X2 . Specifically, one of any two adjacent ^ZCs is bonded to ^Y1 , and the other is bonded to ^X2 . As shown in the following specific examples, any adjacent two Z ^Cs on the c1 ring can be carbons bonded to Y ¹ and X ² , and in addition, the two adjacent Z ^Cs on the c2 ring can be carbons bonded to Y ¹ and X 2 X ² bonded carbon.

In formula (C), X ^c is >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, said >NR, said >C(-R ) ₂ and the R of >Si(-R) ₂ are independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl , a substituted or unsubstituted cycloalkyl group, the two Rs of >C(-R) ₂ and >Si(-R) ₂ may be bonded to each other to form a ring. These groups are described as "substituted or unsubstituted", and as a substituent, an aryl group, a heteroaryl group, a diarylamino group, an alkyl group, a cycloalkyl group, or a substituted silyl group are preferred. In addition, two aryl groups of the diarylamino group may be bonded to each other. For details and preferred ranges of the first substituent and the second substituent, refer to the description of preferred substituents described later.

In formula (C), Z ^C other than Z ^C which is a carbon bonded to either Y ¹ or X ² are each independently N or ^CRC , and R ^C are each independently hydrogen, substituted or Unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted Arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl , a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, or a substituted silyl group. In addition, the two aryl groups of the diarylamino group can be bonded to each other, the two heteroaryl groups of the diheteroarylamino group can be bonded to each other, and the aryl group and the heteroaryl group of the arylheteroarylamino group can be bonded to each other. The radicals can be bonded to each other, and the two aryl groups of the diarylboryl group can be bonded to each other. Alternatively, they are linked via a single bond or a linking group.

These groups are described as "substituted or unsubstituted", and as a substituent, an aryl group, a heteroaryl group, a diarylamino group, an alkyl group, a cycloalkyl group, or a substituted silyl group are preferred. In addition, two aryl groups of the diarylamino group may be bonded to each other via a linking group. For details and preferred ranges of the first substituent and the second substituent, refer to the description of preferred substituents described later.

When Z ^C other than Z ^C which is a carbon bonded to any of ^Y1 or ^X2 is ^CRC , it is particularly preferable that any one of R ^C is a substituent, and the rest are hydrogen. As a substituent, tR (especially tert-butyl group) mentioned later is preferable. The substitution position is preferably the para-position of X ^c .

In formula (C), two adjacent R ^C may be bonded to each other (and together with the two carbons to which these R ^C are bonded) to form an aryl ring or a heteroaryl ring. At least one hydrogen of the formed aryl ring and heteroaryl ring is independently substituted with R ^C or unsubstituted. In addition, the description in the specification can be referred to for the terms used here and their preferred ranges.

In formula (C), X ^c is preferably >O, >NR, or >S, more preferably >S. Regarding the preferable range of Z ^C in the formula (C), reference can be made to the description of the following specific examples.

In formula (1), ring A and ring B are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring. The A ring forms a trivalent group having bonding bonds on three consecutive carbons on the ring of the aryl ring or heteroaryl ring in its structure. They are respectively bonded to X ¹ , X ² , and Y ¹ through the three bonding bonds. The ring having the carbons having the three bonding bonds in the A ring as a ring constituting element is preferably a 5-membered ring or a 6-membered ring, more preferably a 6-membered ring. The rings can be further condensed with other rings. Each of the B rings forms a divalent group having bonding bonds on two carbons adjacent to each other on the ring of an aryl ring or a heteroaryl ring in its structure. The B ring is bonded to ^X1 and ^Y1 through the two bonding bonds. The ring having the carbons having the two bonding bonds in ring B as a ring constituting element is preferably a 5-membered ring or a 6-membered ring, more preferably a 6-membered ring. The rings can be further condensed with other rings.

As a substituent, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino , substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted Substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl, the two The two aryl groups of the arylamino group can be bonded to each other via a single bond or a linking group, and the two heteroaryl groups of the diheteroarylamino group can be bonded to each other via a single bond or a linking group. The aryl group and the heteroaryl group of the arylamino group may be bonded to each other via a single bond or a linking group, and the two aryl groups of the diarylboryl group may be bonded to each other via a single bond or a linking group. These groups are described as "substituted or unsubstituted", and where at least one hydrogen is substituted, are preferably aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl . For details and preferred ranges of the first substituent and the second substituent, refer to the description of preferred substituents described later.

X ¹ and X ² in formula (1) are each independently >O, >NR, >Si(-R) ₂ , >C(-R) ₂ , >S, or >Se. Wherein, at least one of ^X1 or ^X2 is>NG. X ¹ and X ² are preferably one of which is >NG, and the other is >NR (including >NG), >C(-R) ₂ , or >O, more preferably one of them is >NG, and the other is >NR (>except for NG).

In formula (1), R as >NR of X ¹ or X ² is hydrogen, aryl that may be substituted (wherein, as a substituent, amino group is excluded), heteroaryl that may be substituted, substituted Alkyl or optionally substituted cycloalkyl. R of > Si(-R) ₂ of ^X1 and ^X2 are independently hydrogen, aryl which may be substituted, heteroaryl which may be substituted, alkyl which may be substituted or cycloalkane which may be substituted base.

In formula (1), as X ¹ or X ² >Si(-R) ₂ and >C(-R) ₂ R are independently hydrogen, aryl that may be substituted, heteroaryl that may be substituted A group, an alkyl group that may be substituted, or a cycloalkyl group that may be substituted, two Rs are preferably the same, and two Rs may be bonded to form a ring.

In formula (1), regarding the aryl, heteroaryl, alkyl, cycloalkane in R of >NR, >Si(-R) ₂ , or >C(-R) ₂ as X ¹ or X ² For groups, refer to the descriptions of these groups in the following groups.

In formula (1), R as >NR of ^X1 or ^X2 is preferably an aryl group which may be substituted, a heteroaryl group which may be substituted or a cycloalkyl group which may be substituted, more preferably a substituted Aryl or optionally substituted heteroaryl. Examples of the cycloalkyl group include those described below. Here, the aryl group is preferably phenyl, biphenyl (especially 2-biphenyl), and terphenyl (especially terphenyl-2'-yl), and the heteroaryl is preferably phenyl Thienyl (2-benzothienyl, 6-benzothienyl, etc.), benzofuryl (2-benzofuryl, 3-benzofuryl, 5-benzofuryl, etc.), diphenyl Dibenzofuryl (2-dibenzofuryl, 3-dibenzofuryl, 4-dibenzofuryl, 5-dibenzofuryl, etc.) and the like. The substituent is preferably a tertiary alkyl group (especially tert-butyl group) or a cycloalkyl group (especially adamantyl group) represented by the following formula (tR). The number of substituents in the aryl group and the heteroaryl group is preferably 0 to 2, more preferably 1 or 2, and still more preferably 1. It is also preferable that the aryl ring in the aryl group is condensed with a cycloalkane which may be substituted as described later. As specific cycloalkane, reference can be made to cycloalkane described later.

In the formula (1), particularly preferable examples of R as >NR of ^X1 or ^X2 include, in addition to >NG described later, other 2-biphenyl groups which may be substituted, which may be substituted by Substituted terphenyl-2'-yl, and aryl (may be substituted) condensed from cycloalkane. As the 2-biphenyl group which may be substituted, a 2-biphenyl group substituted with 1 to 3 t-butyl groups is particularly preferable. As terphenyl-2'-yl which may be substituted, unsubstituted [1,1':3',1"-terphenyl]-2'-yl is particularly preferred. As aryl condensed from cycloalkane The group is particularly preferably as described below.

[chemical 13]

(Me means methyl group, tBu means tert-butyl group, * means bonding position)

In formula (1), R as >NR of X ¹ or X ² is also preferably an aryl group (which may be substituted) condensed from a cycloalkane.

In formula (1), R in at least one of >NR, >Si(-R) ₂ and >C(-R) ₂ as X ¹ or X ² can be connected to ring A and ring A through a linking group or a single bond. Either one of the B rings, or any one of the A rings and C rings is bonded. That is, R in at least one of >NR, >Si(-R) ₂ , and >C(-R) ₂ as ^X1 may be bonded to any one of the A ring and the B ring through a linking group or a single bond. , R in at least one of >NR, >Si(-R) ₂ and >C(-R) ₂ as X ² may be bonded to any one of the A ring and the C ring through a linking group or a single bond. The linking group is preferably -O-, -S-, or -C(-R ¹³ ) ₂ -. R ¹³ of the "-C(-R ¹³ ) ₂ -" is hydrogen, an alkyl group or a cycloalkyl group, and examples of the alkyl group or cycloalkyl group include those described above as the first substituent, respectively. base. Particularly preferred is an alkyl group having 1 to 5 carbon atoms (for example, methyl group, ethyl group, etc.) or a cycloalkyl group having 5 to 10 carbon atoms (preferably cyclohexyl group or adamantyl group).

In addition, the stipulation can also be expressed by a compound represented by the following formula (1-3-2) and having a ring structure in which X ¹ as >NR is introduced into the condensed ring A'. That is, for example, it is a compound having an A' ring formed by condensing another ring with the A ring which is a benzene ring so that any of ^X1 and ^X2 is introduced. The formed condensed ring A' is, for example, a carbazole ring, a phenoxazine ring, or a phenothiazine ring.

[chemical 14]

As an example, it is also preferable that R in the above-mentioned >N-R is an optionally substituted cycloalkyl group and is bonded to the A ring, the B ring, or the C ring via a single bond. The cycloalkyl group is preferably an optionally substituted cyclopentyl group or an optionally substituted cyclohexyl group.

A particularly preferable example of the condensed ring formed as described above includes a structure represented by formula (A11). In formula (A11), * R in "at least one of >NR, >Si(-R) ₂ and >C(-R) ₂ as X ¹ or X ² can be bonded to A through a linking group or a single bond. Any one of the ring and B ring, or any one of the A ring and the C ring is bonded in the aforementioned definition, which corresponds to the form of bonding by a single bond. As mentioned above, in this case, the two carbons substituted with the methyl group are asymmetric carbons, and as the compound represented by formula (1), diastereoisomers and enantiomers can exist, as the formula ( The compound represented by 1) may be any one of these isomers, and may also be a form in which possible isomers are mixed in any ratio.

[chemical 15]

In formula (A11), Me is a methyl group, which is bonded to one of the two rings to which X ¹ or X ² is bonded at the positions of * and **, and to the other ring at the position of *** bond.

Similarly, the following examples in which R in the above-mentioned >N-R is a phenyl group and is bonded to the A ring, B ring, or C ring via a single bond can be mentioned.

[chemical 16]

In the formula (A12), one of the two rings to which X ¹ or X ² is bonded is bonded at the positions of * and **, and bonded to the other ring at the position of ***.

By using the compound of the present invention having R in the preferred range >NR as ^X1 or ^X2 as a light-emitting material in the manufacture of an element, the luminous efficiency or the lifetime of the element can be further improved.

R that is > Si(-R) ₂ of X ¹ or X ² of formula (1) is hydrogen, aryl that may be substituted, heteroaryl that may be substituted, alkyl that may be substituted, or substituted Cycloalkyl. Here, as a substituent when it is substituted, the 2nd substituent mentioned above is mentioned. Examples of the aryl group, heteroaryl group, alkyl group, or cycloalkyl group include those described above as the first substituent. Particularly preferred are aryl groups with 6 to 10 carbons (such as phenyl, naphthyl, etc.), heteroaryl groups with 2 to 15 carbons (such as carbazolyl, etc.), alkyl groups with 1 to 5 carbons (such as methyl , ethyl, etc.) or a cycloalkyl group having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl).

As ^X1 or ^X2 of formula (1)>C(-R) _2R is hydrogen, aryl that may be substituted, heteroaryl that may be substituted, alkyl that may be substituted, or substituted Cycloalkyl. Here, as a substituent when it is substituted, the 2nd substituent mentioned above is mentioned. Examples of the aryl group, heteroaryl group, alkyl group, or cycloalkyl group include those described above as the first substituent. Particularly preferred are aryl groups with 6 to 10 carbons (such as phenyl, naphthyl, etc.), heteroaryl groups with 2 to 15 carbons (such as carbazolyl, etc.), alkyl groups with 1 to 5 carbons (such as methyl , ethyl, etc.) or a cycloalkyl group having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl).

Next, in formula (1), at least one of X ¹ or X ² is >NG. G is a monovalent group represented by the following formula (G).

[chemical 17]

In formula (G), Z ^g is independently N or CR ^g , and R ^g of said CR ^g is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diaryl Boryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted A substituted aryloxy group, a substituted or unsubstituted arylthio group, or a substituted silyl group, the two aryl groups of the diarylamino group can be bonded to each other via a linking group, and the diheteroarylamino group The two heteroaryl groups of the arylheteroarylamino group can be bonded to each other through a linking group, the aryl group and the heteroaryl group of the arylheteroarylamino group can be bonded to each other through a linking group, and the two aryl groups of the diaryl boron group can be bonded to each other through a linking group. The groups may be bonded to each other via a single bond or a linking group. These groups are described as "substituted or unsubstituted", and as a substituent, an aryl group, a heteroaryl group, a diarylamino group, an alkyl group, a cycloalkyl group, or a substituted silyl group are preferred. In addition, two aryl groups of the diarylamino group may be bonded to each other. For details and preferred examples of each substituent, refer to the description of the substituent described later. R ^g is preferably hydrogen, an aryl group, a heteroaryl group or an alkyl group (especially tR described below), most preferably hydrogen or an alkyl group (especially tR described below).

In formula (G), two adjacent R ^g can be bonded to each other (and together with the two carbons to which these R ^g are bonded) to form an aryl ring or a heteroaryl ring, the formed aryl ring and The heteroaryl rings are each unsubstituted, or substituted with at least one ^Rg2 . R ^g2 and R ^g have the same meaning, wherein, R ^g2 is not hydrogen, and two adjacent R ^g2 will not bond with each other to form an aryl ring or a heteroaryl ring.

In formula (G), * represents a bonding position with N in ^X1 or ^X2 .

Specific examples of the monovalent group represented by the formula (G) include the following. However, the specific form of the monovalent group represented by the formula (G) is not limited to these examples. In addition, in the following formulae, Me represents a methyl group, tBu represents a tert-butyl group, and * represents a bonding position with N.

[chemical 18]

[chemical 19]

[chemical 20]

[chem 21]

[chem 22]

As a preferable aspect of the structural unit represented by formula (1), the structural unit represented by following formula (2) is mentioned.

[chem 23]

Ring a and ring b in formula (2) correspond to ring A and ring B in formula (1), respectively. That is, formula (2) corresponds to a structure in which specific rings are selected as the A ring and the B ring of (1). In this sense, the rings in the various formulas are represented by lowercase "a" and "b".

In formula (2), in ring a and ring b, Z are independently N or CR ¹¹ , or Z=Z are independently >O, >NR, >C(-R) ₂ , >Si(- R) ₂ , >S, or >Se, the R of the >NR, the >C(-R) ₂ and the >Si(-R) ₂ are independently hydrogen, substituted or unsubstituted Aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, said>C(-R) ₂ and said>Si( -R) Two Rs of ₂ may be bonded to each other to form a ring. Here, the aryl group, heteroaryl group, alkyl group, and cycloalkyl group are referred to as the first substituent. These groups are described as "substituted or unsubstituted" and, where at least one hydrogen is substituted, are preferably aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silane base. The aryl group, heteroaryl group, diarylamino group, alkyl group, cycloalkyl group, and substituted silyl group are referred to as the second substituent. In addition, two aryl groups of the diarylamino group may be bonded to each other via a linking group.

In formula (2), R ¹¹ of CR ¹¹ are independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, Substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, Substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted An arylthio group or a substituted silyl group, the two aryl groups of the diarylamino group can be bonded to each other via a linking group, and the two heteroaryl groups of the diheteroarylamino group can be bonded to each other via a linking group , the aryl and heteroaryl groups of the arylheteroarylamino group may be bonded to each other via a linking group, and the two aryl groups of the diarylboryl group may be bonded to each other via a single bond or a linking group. These groups are described as "substituted or unsubstituted", and as a substituent, an aryl group, a heteroaryl group, a diarylamino group, an alkyl group, a cycloalkyl group, or a substituted silyl group are preferred.

R ¹¹ is preferably hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted alkyl , a substituted or unsubstituted cycloalkyl group, or a substituted silyl group. Regarding groups other than hydrogen as R ¹¹ , reference may also be made to the description about preferred substituents described later. In addition, two aryl groups of the diarylamino group may be bonded to each other via a linking group. These groups are described as "substituted or unsubstituted", and as a substituent, an aryl group, a heteroaryl group, a diarylamino group, an alkyl group, a cycloalkyl group, or a substituted silyl group are preferred.

In ring a, Z is preferably all CR ¹¹ . In this case, it is preferable that R ¹¹ at the para-position of Y ¹ is hydrogen or a substituent, and the other R ¹¹ is hydrogen. The substituent is preferably an alkyl group such as a methyl group or a tert-butyl group. In ring b, as R ¹¹ when Z is CR ¹¹ , hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diaryl Amino, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, more preferably hydrogen, substituted or unsubstituted diarylamino, or substituted or unsubstituted alkyl , and more preferably hydrogen, a substituted or unsubstituted diarylamino group, or an unsubstituted alkyl group (especially tR described later). When the diarylamino group has a substituent, the substituent is preferably an unsubstituted alkyl group (particularly tR described later) or a phenyl group.

Next, the statement that "Z=Z are each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se" will be described. For example, in ring b in formula (2), the position as "Z=Z" is substituted with >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or The ring obtained by >Se includes a cyclopentadiene ring, a pyrrole ring, a furan ring, a thiophene ring, and the like. The following shows an example where one Z=Z is >NR, >O, >S, >C(-R) ₂ and the remaining Z is CH in the b ring, and one Z=Z is >NR, >O, > An example in which S, >C(-R) ₂ , and the remaining Z is CR ¹¹ , and adjacent R ¹¹ forms a benzene ring as described later. However, the forms that the b ring and the like can take are not limited to the following examples.

[chem 24]

As described above, there are resonance structural formulas that are completely equivalent in organic chemistry in aromatic compounds, so any possible resonance structural formula can be used as a basis. In addition, the R of the >NR, the >C(-R) ₂ and the >Si(-R) ₂ as Z=Z are each independently hydrogen, substituted or unsubstituted aryl, substituted Substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, said >C(-R) ₂ and said >Si(-R) ₂ Two R's of may be bonded to each other to form a ring. These groups are described as "substituted or unsubstituted" and, where at least one hydrogen is substituted, are preferably aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silane base. In addition, two aryl groups of the diarylamino group may be bonded to each other. Regarding the first substituent and the second substituent, as well as the terms used here and their preferred ranges, reference may be made to the description in the specification.

In addition, in formula (2), Z is preferably all independently CR ¹¹ .

Two adjacent R ¹¹ may be bonded to each other and form an aryl ring or a heteroaryl ring together with the a ring or the b ring. The resulting aryl and heteroaryl rings are each unsubstituted or substituted with at least one R ^11b . R ^11b and R ¹¹ have the same meaning, wherein R ^11b is not hydrogen, and two adjacent R ^11b will not bond with each other to form an aryl ring or a heteroaryl ring. R ^11b is preferably substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted alkyl, or Substituted or unsubstituted cycloalkyl, more preferably substituted or unsubstituted diarylamino or substituted or unsubstituted alkyl, further preferably substituted or unsubstituted diarylamino or an unsubstituted alkyl group (particularly tR described later).

As the aryl ring formed together with ring a or ring b, naphthalene ring, anthracene ring, fluorene ring, indene ring, 9,10-dihydroanthracene ring (especially 9,9,10,10-tetramethyl -9,10-dihydroanthracene ring), dihydroacridine ring, or xanthene ring, as the formed heteroaryl ring, preferably benzothiophene ring, indole ring, benzofuran ring, dibenzo Thiophene ring, dibenzofuran ring, or carbazole ring.

An example in which two adjacent R ¹¹ are bonded to each other to form an aryl ring or a heteroaryl ring together with ring b is shown below. In addition, the benzene ring in the structure below may further have at least one R ^11b as a substituent.

[chem 25]

As a more preferable form of formula (2), the following formula (2a), formula (2b), formula (2c), formula (2d), formula (2e), formula (2f), formula (2g) and Formula (2h).

[chem 26]

Preferably, in formula (2a), formula (2b), formula (2c), formula (2d), formula (2e), formula (2f), formula (2g) and formula (2h), Z ^c are independently All are in the form of CR ¹¹ , and in formula (2a), formula (2b), formula (2c), formula (2d), formula (2e), formula (2f), formula (2g) and formula (2h), Z ^c of the c2 ring are all independently CR ^c , and adjacent R ^c form bonds with each other as described later to form an aryl ring (preferably a benzene ring) is also preferable. In addition, among formula (2a), formula (2b), formula (2c), formula (2d), formula (2e), formula (2f), formula (2g) and formula (2h), formula (2a) is preferable , formula (2b), most preferably formula (2a). In addition, the description of this specification mentioned later can be referred to about description of each symbol and a phrase.

In formula (2c), formula (2d), formula (2e), formula (2f), formula (2g) and formula (2h), it is preferred that the Z ^C of the c2 ring are all ^CRC , and the adjacent two R and ^C are bonded to each other to form an aryl ring or a heteroaryl ring (more preferably an aryl ring, still more preferably a benzene ring). This preferred form is shown below. Definitions of symbols in formula (2c-2), formula (2d-2), formula (2e-2), formula (2f-2), formula (2g-2) and formula (2h-2), and their For the preferred range, refer to the description of formula (2).

[chem 27]

Furthermore, the structural unit represented by formula (2a) is preferably a structural unit represented by the following formula (2a-1) or formula (2a-2).

[chem 28]

In formula (2a-1) or formula (2a-2), Y ¹ , X ¹ , X ² , and X ^C have the same meanings as Y ¹ , X ¹ , X ² , and X ^C in formula (1), respectively, and R ^11b and R ^C2 have the same meanings as R ^11b and R ^C2 in formula (2), respectively. X ³ and X ⁴ are each independently a single bond, >O, >NR, >C(-R) ₂ , or >S, wherein X ³ and X ⁴ are not single bonds at the same time. n1 is an integer of 0-4, n2 is an integer of 0-4, n3 is an integer of 0-3, and n4 is an integer of 0-2. At least one of an aryl ring or a heteroaryl ring in one or more structures including structural units represented by formula (2a-1) or formula (2a-2) may be condensed with at least one cycloalkane.

In formula (2a-1) and formula (2a-2), the preferred ranges of Y ¹ , X ¹ , X ² , and X ^C are the same as those of Y ¹ , X ¹ , X ² , and X ^C in formula (1). The preferred range is the same. In formula (2a-2), it is preferred that one of X ³ and X ⁴ is >C(-R) ₂ and the other is >O, >NR, or >C(-R) ₂ , or one of them is a single bond and the other is >O or >NR. In addition, in formula (2a-1) and formula (2a-2), the preferred ranges of R ^11b and R ^C2 are the same as the preferred ranges of the corresponding ring substituents in formula (1) or formula (2). n1 is preferably 0-2, more preferably 0 or 1. n2 is preferably 0-2, more preferably 0 or 1. n3 is preferably 0 or 1. n4 is preferably 0. Regarding the preferred substitution positions of R ^11b and R ^C2 , reference may also be made to the explanations in formula (1) or formula (2). When there is condensation using cycloalkane as described above, it is preferably an aryl ring in a structure containing one or more structural units represented by formula (2a-1) or formula (2a-2) Or one to four of the heteroaryl rings are each condensed with one cycloalkane.

In formula (1), and formula (2) etc. as its preferred form, Y ¹ are each independently B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge -R, preferably B, P=O or P=S, most preferably B. R in the Si-R and Ge-R is an aryl group with 6-12 carbons, an alkyl group with 1-6 carbons, or a cycloalkyl group with 3-14 carbons. R in Si-R and Ge-R in Y1 of formula ( ¹ ) is an aryl group, an alkyl group or a cycloalkyl group, and as the aryl group, an alkyl group or a cycloalkyl group, the above-mentioned base. Particularly preferred is an aryl group with 6 to 10 carbons (such as phenyl, naphthyl, etc.), an alkyl group with 1 to 5 carbons (such as methyl, ethyl, etc.) or a cycloalkyl group with 5 to 10 carbons (preferred is cyclohexyl or adamantyl).

<Polycyclic aromatic compound having a structure including one or two or more structural units>

The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure including one or two or more structural units represented by formula (1) or formula (2), which is a preferred form thereof. Examples of the polycyclic aromatic compound having a structure including one of the above structural units include a polycyclic aromatic compound having a structure represented by formula (1) (or formula (2), which is a preferred embodiment thereof, and the like). As a polycyclic aromatic compound having two or more structures including a structural unit represented by formula (1), polycyclic aromatic compounds represented by the above-described formula corresponding to the structural unit represented by formula (1) can be cited. A compound that is a multimer of aromatic compounds. The multimer is preferably a dimer to a hexamer, more preferably a dimer to a trimer, and particularly preferably a dimer. As long as the multimer has a plurality of such unit structures in one compound, any ring (A ring (a ring), B ring) contained in the structural unit may be shared among the plurality of unit structures. ring (b ring) or C ring (c1 ring, c2 ring, c3 ring)), and any ring included in the unit structure (A ring (a ring) , B rings (b rings) or C rings (c1 rings, c2 rings, c3 rings)) are condensed and bonded to each other. In addition, a plurality of the unit structures may be bonded via a single bond, a linking group such as an alkylene group having 1 to 3 carbon atoms, a phenylene group, or a naphthylene group. Among these, a form in which a bond is shared by sharing a ring is preferable.

<Cycloalkane Condensation>

A polycyclic aromatic compound having one or more structures comprising structural units represented by formula (1), and at least one selected from the group consisting of aryl rings and heteroaryl rings in preferred forms thereof One can be condensed by at least one cycloalkane.

As the cycloalkane, any cycloalkane having 3 to 24 carbon atoms may be used. At this time, at least one hydrogen in the cycloalkane can be substituted by an aryl group with 6 to 30 carbons, a heteroaryl group with 2 to 30 carbons, an alkyl group with 1 to 24 carbons or a cycloalkyl group with 3 to 24 carbons, At least one -CH ₂ - in the cycloalkane may be substituted by -O-, but a cycloalkane in which all are -CH ₂ - is preferred.

In the case where one or more structures comprising the structural unit represented by formula (1) are condensed by at least one cycloalkane, at least one cycloalkane is a cycloalkane with 3 to 20 carbons, preferably among the cycloalkane Cycloalkane which may be substituted with at least one hydrogen in C 6-16 aryl, 2-22 carbon heteroaryl, 1-12 alkyl or 3-16 carbon cycloalkyl.

Examples of "cycloalkane" include: cycloalkane with 3 to 24 carbons, cycloalkane with 3 to 20 carbons, cycloalkane with 3 to 16 carbons, cycloalkane with 3 to 14 carbons, cycloalkane with 5 to 10 carbons cycloalkanes, cycloalkanes with 5 to 8 carbons, cycloalkanes with 5 to 6 carbons, cycloalkanes with 6 carbons, etc.

Specific cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo[1.1.0] Butane, bicyclo[1.1.1]pentane, bicyclo[2.1.0]pentane, bicyclo[2.1.1]hexane, bicyclo[3.1.0]hexane, bicyclo[2.2.1]heptane, bicyclo[ 2.2.2] Octane, adamantane, diamantane (diamantane), decahydronaphthalene and decahydroazulene, and their alkyl (especially methyl) substituents with 1 to 5 carbons, halogen (especially fluorine ) substitutes and deuterium substitutes, etc.

Of these, carbons at the alpha position of cycloalkanes (carbons adjacent to the carbons at the condensation sites in cycloalkyl groups condensed in aryl rings or heteroaryl rings) are preferred, for example, as shown in the following structural formula. , corresponding to a structure in which at least one hydrogen on the benzyl position) is substituted, more preferably a structure in which two hydrogens on the carbon at the α position are substituted, and more preferably a total of four hydrogens on the carbons at the two α positions are substituted by replaced structure. This is to protect the chemically active sites to increase the durability of the compound. Examples of the substituent include C1-5 alkyl (especially methyl) substituents, halogen (especially fluorine) substituents, deuterium substituents, and the like. Particularly preferred is a structure in which a partial structure represented by the following formula (Z-11) is bonded to adjacent carbons in the aryl ring or heteroaryl ring.

[chem 29]

In formula (Z-11), Me represents a methyl group, and * represents a bonding position.

The number of cycloalkanes condensed in one aryl ring or heteroaryl ring is preferably 1 to 4, more preferably 1 to 3, still more preferably 1 or 2. For example, an example in which one or more cycloalkanes are condensed in one benzene ring (phenyl) is shown below. * indicates a bonding position, and the position may be any one of carbons that constitute a benzene ring and do not constitute a cycloalkane. The cycloalkanes condensed like Formula (Cy-1-4) and Formula (Cy-2-4) may also be condensed. Whether the condensed ring (base) is other aryl ring or heteroaryl ring other than benzene ring (phenyl), or the condensed cycloalkane is other cycloalkane other than cyclopentane or cyclohexane The situation is the same.

[chem 30]

At least one -CH ₂ - in cycloalkane may be substituted by -O-. For example, an example in which one or more -CH ₂ - in a cycloalkane condensed in one benzene ring (phenyl) is replaced by -O- is shown below. Regardless of whether the condensed ring (base) is other aromatic rings or heteroaromatic rings other than benzene ring (phenyl), or the condensed cycloalkane is other cycloalkane other than cyclopentane or cyclohexane The situation is the same.

[chem 31]

At least one hydrogen in the cycloalkane may be substituted, and examples of the substituent include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl , an alkyl group, a cycloalkyl group, an alkoxy group, an aryloxy group, a substituted silyl group, a deuterium group, a cyano group, or a halogen. For details of these, reference may be made to the description of the first substituent in this specification. Wherein, the two aryl groups of the diarylamino group can be bonded to each other via a linking group, the two heteroaryl groups of the diheteroarylamino group can be bonded to each other via a linking group, and the aryl heteroaryl The aryl and heteroaryl groups of the ylamino group may be bonded to each other via a linking group, and the two aryl groups of the diarylboryl group may be bonded to each other via a single bond or a linking group. Among these substituents, alkyl groups (eg, alkyl groups having 1 to 6 carbon atoms), cycloalkyl groups (eg, cycloalkyl groups having 3 to 14 carbon atoms), halogens (eg, fluorine), and deuterium are preferred. Moreover, when a cycloalkyl group is substituted, it may be a substitution form which forms a spiro ring structure, and this example is shown below.

[chem 32]

As a form of cycloalkane condensation, first, aryl groups in ring A, ring B, and ring C in polycyclic aromatic compounds having one or more structures including structural units represented by formula (1) can be cited. A form in which a ring or a heteroaryl ring is condensed with a cycloalkane. In particular, a form in which ring a, ring b, ring c1, ring c2 (or ring c3) of a polycyclic aromatic compound having a structure of one or more structural units represented by formula (2) is condensed with cycloalkane .

As other forms of cycloalkane condensation, polycyclic aromatic compounds having one or more structures comprising structural units represented by formula (1), and one of ^X1 and ^X2 among preferred forms thereof >The aryl ring or heteroaryl ring in G of NG is condensed with cycloalkane, and has a diarylamino group condensed with cycloalkane (two aryl groups can be bonded to each other; condensed to its aryl part), Carbazolyl condensed from naphthenes (condensed to its benzene ring portion) or benzocarbazolyl condensed from naphthenes (condensed to its benzene ring portion), aryl condensed from naphthenes, or condensed from naphthenes Examples of heteroaryls. Regarding the diarylamino group (two aryl groups of the diarylamino group may be bonded to each other), the following groups are mentioned as the "first substituent".

In polycyclic aromatic compounds having one or more structures comprising structural units represented by formula (1), the cycloalkane condensation is preferably such that there is condensation in the A ring, the B ring, or the C ring. form (particularly the form condensed in a ring, b ring, c1 ring, c2 ring (or c3 ring) in the formula (2), more preferably a form in which there is condensation in the B ring or C ring (especially the condensed in the form of b ring or c1 ring in formula (2). In addition, it is also preferable to have a form in which both the B ring and the C ring are condensed (in particular, the form in which the b ring and the c1 ring in the formula (2) are condensed, respectively).

In addition, by introducing a cycloalkane structure into the polycyclic aromatic compound of the present invention, it is expected that the melting point or the sublimation temperature will be lowered. This fact means that in sublimation purification, which is almost indispensable as a purification method for materials for organic devices such as organic EL elements requiring high purity, since purification can be performed at relatively low temperature, thermal decomposition of the material and the like can be avoided. In addition, the same is true for the vacuum evaporation process, which is a powerful means for producing organic devices such as organic EL elements. The process can be performed at a relatively low temperature, so thermal decomposition of the material can be avoided, and high performance can be obtained as a result. of organic devices. In addition, since the solubility in an organic solvent is improved by introducing a cycloalkane structure, it can also be applied to element production by a coating process. However, the present invention is not particularly limited to these principles. Therefore, in the polycyclic aromatic compound having one, or two or more structures including the structural unit represented by formula (1), and a preferred embodiment thereof, it is preferable that the aforementioned cycloalkane condensation is introduced.

All or part of the hydrogens in one or more structures including the structural unit represented by formula (1) and its preferred forms may be substituted with deuterium, cyano, or halogen.

For example, in one or more structures comprising the structural unit represented by formula (1) and its preferred forms, A ring (a ring), B ring (b ring), C ring (c1 ring, c2 ring (, c3 ring)), substituents on rings A to C, R (=alkyl, cycloalkyl, aryl) when Y ¹ is Si-R or Ge-R, and among X ¹ and X ² One of > NR of R, or one of ^X1 and ^X2 of > NG in G can be substituted by deuterium, cyano or halogen, and all or all of aryl or heteroaryl can be listed in these A form in which a part of hydrogen is substituted with deuterium, cyano, or halogen. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine or chlorine, still more preferably fluorine. In particular, a form in which hydrogen is substituted with deuterium is preferred because it increases the stability of the compound. When hydrogen is substituted with deuterium, only one hydrogen is substituted with deuterium, but preferably a plurality of hydrogens are substituted with deuterium, more preferably all the hydrogens in the aromatic part are substituted with deuterium, further preferably all hydrogens are substituted with deuterium .

<Description of ring and substituent>

Details of the rings and substituents used in the present specification will be described below.

The "aryl ring" in this specification includes, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 16 carbon atoms, more preferably an aryl ring having 6 to 12 carbon atoms, especially It is preferably an aryl ring having 6 to 10 carbon atoms.

环，作为缩合五环系的苝环、并五苯环等。另外，芴环、苯并芴环、茚环中也分别包括螺键结有芴环、苯并芴环、环戊烷环等的结构。此外，作为芴环、苯并芴环及茚环，也包括亚甲基的两个氢分别被取代为后述的作为第一取代基的甲基等烷基而形成为二甲基芴环、二甲基苯并芴环及二甲基茚环等的环。另外，作为9，10-二氢蒽环，也包括两个亚甲基的四个氢分别被取代为后述的作为第一取代基的甲基等烷基而形成为9，9，10，10-四甲基-9，10-二氢蒽环等的环。Specific "aryl rings" include a benzene ring as a monocyclic system, a biphenyl ring as a bicyclic system, a naphthalene ring and an indene ring as a condensed bicyclic system, and a terphenyl ring as a tricyclic system ( m-terphenyl, o-terphenyl, p-terphenyl), acenaphthylene ring, fluorene ring, phenalenering, phenanthrene ring, anthracycline as condensed tricyclic system , 9,10-dihydroanthracycline, triphenylene ring, pyrene ring, tetracene ring,

ring, a perylene ring, a pentacene ring, etc. as a condensed pentacyclic system. In addition, the fluorene ring, benzofluorene ring, and indene ring also include structures in which a fluorene ring, a benzofluorene ring, a cyclopentane ring, and the like are spiro-bonded, respectively. In addition, as the fluorene ring, the benzofluorene ring and the indene ring, two hydrogens of a methylene group are respectively substituted with an alkyl group such as a methyl group as a first substituent described later to form a dimethylfluorene ring, a benzofluorene ring, and an indene ring. Rings such as a dimethylbenzofluorene ring and a dimethylindene ring. In addition, as a 9,10-dihydroanthracycline, four hydrogens including two methylene groups are respectively substituted with an alkyl group such as a methyl group as a first substituent described later to form 9, 9, 10, Rings such as 10-tetramethyl-9,10-dihydroanthracycline.

The "heteroaryl ring" includes, for example, a heteroaryl ring having 2 to 30 carbon atoms, preferably a heteroaryl ring having 2 to 25 carbon atoms, more preferably a heteroaryl ring having 2 to 20 carbon atoms, and further A heteroaryl ring having 2 to 15 carbon atoms is preferred, and a heteroaryl ring having 2 to 10 carbon atoms is particularly preferred. In addition, examples of the "heteroaryl ring" include heterocyclic rings containing, as ring constituent atoms, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon.

Specific "heteroaryl rings" include, for example, pyrrole rings, oxazole rings, isoxazole rings, thiazole rings, isothiazole rings, imidazole rings, oxadiazole rings (furazan rings, etc.), thiadiazole rings, etc. ring, triazole ring, tetrazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, carboline (carboline) ring, acridine ring, phenothiazine ring, phenoxazine ring, phenothiazine ring, phenazine ring, phenazasiline ring , indazine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, thianthrene ring, indolocarbazole ring, Benzindolocarbazole ring, dibenzoindolocarbazole ring, naphthobenzofuran ring, dioxin ring, dihydroacridine ring, xanthene ring, thioxanthene ring, dibenzodioxin British (dibenzodioxin) ring and so on. In addition, in the dihydroacridine ring, xanthene ring, and thioxanthene ring, it is also preferable that two of the two hydrogens of the methylene group are respectively substituted with an alkyl group such as a methyl group as a first substituent described later. It is a ring such as a dimethyldihydroacridine ring, a dimethylxanthene ring, a dimethylthioxanthene ring, or the like. In addition, a bipyridine ring, a phenylpyridine ring, a pyridylphenyl ring as a bicyclic system, a terpyridyl ring as a tricyclic system, a bipyridylphenyl ring, and a pyridylbiphenyl ring can also be used as "Heteroaryl ring" is listed. In addition, the "heteroaryl ring" also includes a pyran ring.

In addition, the following formula (BO) is also included in the heteroaryl ring.

[chem 33]

At least one hydrogen in the "aryl ring" or "heteroaryl ring" may be replaced by a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl" as the first substituent , substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted Substituted "diarylboryl", substituted or unsubstituted "alkyl", substituted or unsubstituted "alkenyl", substituted or unsubstituted "cycloalkyl", substituted Or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy", substituted or unsubstituted "arylthio", or "substituted silyl". In addition, the two aryl groups of the diarylamino group may be bonded to each other via a linking group, the two heteroaryl groups of the diheteroarylamino group may be bonded to each other via a linking group, and the arylheteroaryl The aryl group and the heteroaryl group of the ylamino group may be bonded to each other via a linking group, and the two aryl groups of the diarylboryl group may be bonded to each other via a single bond or a linking group.

Specifically, the "aryl group" is a monovalent group obtained by removing one hydrogen from the "aryl ring", for example, an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 24 carbon atoms The group is more preferably an aryl group having 6 to 20 carbons, still more preferably an aryl group having 6 to 16 carbons, particularly preferably an aryl group having 6 to 12 carbons, and most preferably an aryl group having 6 to 10 carbons.

In addition, the "heteroaryl group" is a monovalent group obtained by removing one hydrogen from the "heteroaryl ring", for example, a heteroaryl group having 2 to 30 carbon atoms, preferably a heteroaryl group having 2 to 25 carbon atoms The heteroaryl group is more preferably a heteroaryl group having 2 to 20 carbon atoms, still more preferably a heteroaryl group having 2 to 15 carbon atoms, particularly preferably a heteroaryl group having 2 to 10 carbon atoms. Moreover, as a heteroaryl group, the heterocyclic ring etc. which contain 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as a ring constituting atom in addition to carbon are mentioned, for example.

"Substituted or unsubstituted diarylamino", "substituted or unsubstituted diheteroarylamino", "substituted or unsubstituted arylheteroarylamino" as the first substituent Wherein the two aryl groups of the diarylamino group can be bonded to each other via a linking group, the two heteroaryl groups of the diheteroarylamino group can be bonded to each other via a linking group, and the arylheteroaryl group The aryl group and the heteroaryl group of the amino group may be bonded to each other via a linking group, and the two aryl groups of the diarylboryl group may be bonded to each other via a single bond or a linking group. As each aryl group or heteroaryl group, groups described above as "aryl group" or "heteroaryl group" together with their preferred ranges can be cited.

Diarylamino as the first substituent, wherein two aryl groups of the diarylamino can be bonded to each other via a linking group, diheteroarylamino as the first substituent, wherein the diheteroaryl The two heteroaryl groups of the base amino group can be bonded to each other via a linking group, and the aryl heteroaryl amino group as the first substituent, wherein the aryl group and the heteroaryl group of the aryl heteroaryl amino group can be mutually bonded via The description of "bonding via a linking group" in the description of a linking group indicates that, for example, two phenyl groups of a diphenylamino group form a bond through a linking group as shown below. In addition, this explanation is also applicable to the diheteroarylamino group and arylheteroarylamino group formed from an aryl group or a heteroaryl group.

[chem 34]

(*表示键结位置)

(* indicates the bonding position)

As the linking group, specifically, >O, >NR ^x , >C(-R ^x ) ₂ , -(CR ^x )=(CR ^x )-, >Si(-R ^x ) ₂ , >S, >CO, >CS, >SO, > _SO2 , and >Se. R ^X are each independently an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group, and these may be substituted by an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group. In addition, two R ^X in each of >C(-R ^X ) ₂ , -(CR ^X )=(CR ^X )-, and >Si(-R ^X ) ₂ may be bonded to each other via a single bond or a linking group X ^Y Knot to form a ring. Examples of X ^Y include >O, >NR ^Y , >C( ^-RY ) ₂ , >Si(-RY ⁾ ₂ , >S, >CO, >CS, >SO, >SO ₂ , and >Se , R ^Y are each independently an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group, and these may be substituted by an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group. Wherein, when X ^Y is >C(-RY ⁾ ₂ and >Si( ^-RY ) ₂ , two ^RY will not bond to form a ring. Furthermore, an alkenylene group is also mentioned as a linking group. Any hydrogen of the alkenylene group can be independently replaced by R ^2X , R ^2X are independently alkyl, cycloalkyl, substituted silyl, aryl and heteroaryl, these can be represented by alkyl, cycloalkyl , Substituted silyl, aryl substituted. Two R ^X in -(CR ^X )=(CR ^X )- may be bonded to each other and form an aryl ring (benzene ring, etc.) or a heteroaryl ring together with these bonded C═C. That is, -(CR ^x )=(CR ^x )- can be an arylene group (1,2-phenylene, etc.) or a heteroarylene group.

In addition, when only "diarylamino", "diheteroarylamino" or "arylheteroarylamino" is described in this specification, unless otherwise specified, it is deemed that "diaryl The two aryl groups of the diheteroarylamino group can be bonded to each other through a linking group", "the two heteroaryl groups of the diheteroarylamino group can be bonded to each other through a linking group" and "the arylheteroarylamino group The aryl group and the heteroaryl group can be bonded to each other via a linking group".

In addition, the "alkyl group" as the first substituent may be either a straight chain or a branched chain, and examples thereof include a straight chain alkyl group having 1 to 24 carbon atoms or a branched chain alkyl group having 3 to 24 carbon atoms. It is preferably an alkyl group with 1 to 18 carbons (branched chain alkyl with 3 to 18 carbons), more preferably an alkyl group with 1 to 12 carbons (branched alkyl with 3 to 12 carbons), and even more preferably An alkyl group with 1 to 8 carbons (branched chain alkyl with 3 to 8 carbons), particularly preferably an alkyl group with 1 to 6 carbons (branched alkyl with 3 to 6 carbons), most preferably a carbon number Alkyl group of 1 to 5 (branched alkyl group having 3 to 5 carbon atoms).

Specific examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl , t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl Base, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl (1,1,3,3-tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl, 2- Propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl Base, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, Positive twenty bases and so on. In addition, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl , 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-di Methylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2- Tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl Base, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1- Methylbutyl, 1,1-dimethylhexyl, etc.

As the substituent including "alkyl", the tertiary alkyl group represented by the following formula (tR) is particularly suitable as a substituent for the aryl ring or heteroaryl ring in the A ring, B ring, and C ring. One of the preferred substituents. The reason is that the intermolecular distance increases through such a bulky substituent, so the luminescence quantum yield (photoluminescence quantum yield, PLQY) increases. In addition, a substituent in which a tertiary alkyl group represented by the formula (tR) is substituted as a second substituent to another substituent is also preferable. Specifically, a diarylamino group substituted by a tertiary alkyl group represented by (tR), a carbazolyl group (preferably N-carbazolyl) substituted by a tertiary alkyl group represented by (tR), or a carbazolyl group represented by ( tertiary alkyl-substituted benzocarbazolyl (preferably N-benzocarbazolyl) represented by tR). Regarding the "diarylamino group", the groups described below as the "first substituent" are exemplified. As the substitution form of the group of formula (tR) for diarylamino, carbazolyl and benzocarbazolyl, some or all of the hydrogens of the aryl ring or benzene ring in these groups can be changed from the formula (tR) Examples of substituents.

[chem 35]

In formula (tR), R ^a , R ^b and R ^c are each independently an alkyl group with 1 to 24 carbons, any -CH ₂ - in the alkyl group can be substituted by -O-, the formula (tR) The indicated group is substituted at * with at least one hydrogen in the structure including the structural unit represented by formula (1).

The "alkyl group having 1 to 24 carbons" in R ^a , R ^b and R ^c may be either straight chain or branched chain, for example, a straight chain alkyl group having 1 to 24 carbons or a straight chain alkyl group having 3 to 24 carbons. 24 branched chain alkyl, C1-18 alkyl (C3-18 branched alkyl), C1-12 alkyl (C3-12 branched alkyl), carbon An alkyl group having 1 to 6 carbon atoms (branched chain alkyl group having 3 to 6 carbon atoms), and an alkyl group having 1 to 4 carbon atoms (branched chain alkyl group having 3 to 4 carbon atoms).

The sum of the carbon numbers of R ^a , R ^b , and R ^c in the formula (tR) of the formula (1) is preferably 3-20 carbon atoms, particularly preferably 3-10 carbon atoms.

Specific alkyl groups for R ^a , R ^b and R ^c include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl Base, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl , n-heptyl, 1-methylhexyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-decyl Triyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc.

Examples of the group represented by the formula (tR) include t-butyl, t-amyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethyl 1-butyl, 1-ethyl-1-methylbutyl, 1,1,3,3-tetramethylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethyl propyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl- 1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1 -Diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpentyl Methylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl and the like. Among these, tert-butyl and tert-amyl are preferred.

In addition, "cycloalkyl" as the first substituent includes cycloalkyl having 3 to 24 carbons, cycloalkyl having 3 to 20 carbons, cycloalkyl having 3 to 16 carbons, cycloalkyl having 3 to 14 carbons, cycloalkyl, cycloalkyl having 5 to 10 carbons, cycloalkyl having 5 to 8 carbons, cycloalkyl having 5 to 6 carbons, cycloalkyl having 5 carbons, etc. The cycloalkyl group in the present specification includes not only a monocyclic cycloalkyl group, but also a polycyclic cycloalkyl group such as an adamantyl group, as listed below.

Specific cycloalkyl groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornenyl, bicyclo[1.1. 0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[ 2.2.2] Octyl, adamantyl, bisadamantyl, decahydronaphthyl, decahydroazulene, and these alkyl (especially methyl) substituents having 1 to 5 carbons, etc.

The "alkenyl group" as the first substituent includes straight chain alkenyl groups having 2 to 24 carbon atoms or branched chain alkenyl groups having 4 to 24 carbon atoms. It is preferably an alkenyl group having 2 to 18 carbons, more preferably an alkenyl group having 2 to 12 carbons, still more preferably an alkenyl group having 2 to 6 carbons, particularly preferably an alkenyl group having 2 to 4 carbons.

As a specific "alkenyl group", a vinyl group, an allyl group, a butadienyl group, etc. are mentioned.

In addition, the "alkoxy" as the first substituent includes, for example, a straight chain alkoxy group having 1 to 24 carbon atoms or a branched chain alkoxy group having 3 to 24 carbon atoms. Preferably it is an alkoxy group with 1 to 18 carbons (branched alkoxy group with 3 to 18 carbons), more preferably an alkoxy group with 1 to 12 carbons (branched alkoxy group with 3 to 12 carbons) , more preferably an alkoxy group with 1 to 6 carbons (branched alkoxy group with 3 to 6 carbons), particularly preferably an alkoxy group with 1 to 5 carbons (branched alkoxy group with 3 to 5 carbons) base).

Specific alkoxy groups include: methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, tert-amyloxy , pentyloxy, hexyloxy, heptyloxy, octyloxy, etc.

The "aryloxy group" as the first substituent is a group in which the hydrogen of the -OH group is replaced by an aryl group, and the groups described above can be cited for the aryl group and its preferred range.

The "arylthio group" as the first substituent is a group in which the hydrogen of the -SH group is replaced by an aryl group, and the above-mentioned groups may be cited for the aryl group and its preferred range.

In addition, examples of the "substituted silyl group" as the first substituent include a silyl group substituted with three substituents selected from the group consisting of an alkyl group, a cycloalkyl group, and an aryl group. Examples include trialkylsilyl groups, tricycloalkylsilyl groups, dialkylcycloalkylsilyl groups, alkylbicycloalkylsilyl groups, triarylsilyl groups, dialkylarylsilyl groups, and alkyl Diarylsilyl groups.

As the "trialkylsilyl group", three hydrogens in the silyl group are independently substituted by an alkyl group, and the alkyl group and its preferred range can be cited as the "alkyl group" in the first substituent. "And the basis of the description. Preferred alkyl groups for substitution are alkyl groups having 1 to 5 carbon atoms, specifically, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, tert- Pentyl etc.

Specific trialkylsilyl groups include trimethylsilyl groups, triethylsilyl groups, tripropylsilyl groups, triisopropylsilyl groups, tributylsilyl groups, tri-sec-butylsilyl groups, Tri-tert-butylsilyl, tri-tert-amylsilyl, ethyldimethylsilyl, propyldimethylsilyl, isopropyldimethylsilyl, butyldimethylsilyl, sec-butyl Dimethylsilyl, tert-butyldimethylsilyl, tert-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyl Diethylsilyl group, sec-butyldiethylsilyl group, tert-butyldiethylsilyl group, tert-amyldiethylsilyl group, methyldipropylsilyl group, ethyldipropylsilyl group, Butyldipropylsilyl, sec-butyldipropylsilyl, tert-butyldipropylsilyl, tert-amyldipropylsilyl, methyldiisopropylsilyl, ethyldiisopropyl Silyl group, butyldiisopropylsilyl group, sec-butyldiisopropylsilyl group, tert-butyldiisopropylsilyl group, tert-amyldiisopropylsilyl group and the like.

As the "tricycloalkylsilyl group", three hydrogens in the silyl group are independently substituted by a cycloalkyl group, and the cycloalkyl group and its preferred range can be cited as the first substituent. The group specified by "cycloalkyl". A preferred cycloalkyl group for substitution is a cycloalkyl group having 5 to 10 carbon atoms, specifically, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, Bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl base, adamantyl, decalinyl, decalinyl, etc.

As a specific tricycloalkylsilyl group, a tricyclopentylsilyl group, a tricyclohexylsilyl group, etc. are mentioned.

As specific examples of a dialkylcycloalkylsilyl group substituted with two alkyl groups and one cycloalkyl group, and an alkyldicycloalkylsilyl group substituted with one alkyl group and two cycloalkyl groups, substituted There is a silyl group selected from the specific alkyl group and cycloalkyl group.

As a dialkylarylsilyl group substituted with two alkyl groups and one aryl group, an alkyldiarylsilyl group substituted with one alkyl group and two aryl groups, and a triarylsilyl group substituted with three aryl groups Specific examples include silyl groups substituted with groups selected from the specific alkyl groups and aryl groups described above. Specific examples of the triarylsilyl group include a triphenylsilyl group.

In addition, the "aryl" in the "diarylboryl group (two aryl groups can be bonded to each other via a single bond or a linking group)" as the first substituent and its preferred range can refer to the description of the aryl group . In addition, the two aryl groups may be linked via a single bond or a linking group (eg >C(-R) ₂ , >O, >S or >NR). Here, R of >C(-R) ₂ and >NR is an aryl group, a heteroaryl group, a diarylamino group (two aryl groups may be bonded to each other via a linking group), an alkyl group, a cycloalkyl group, an alkane group Oxygen or aryloxy group (the above is the first substituent), in which the first substituent may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl (the above is the second substituent), as Specific examples of these groups include the above-mentioned aryl group, heteroaryl group, diarylamino group (two aryl groups may be bonded to each other via a linking group), alkyl group, cycloalkyl group, alkoxy group, etc. as the first substituent. A description of the radical, or aryloxy group.

As the first substituent, substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted Substituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "diarylboryl", substituted or unsubstituted " Alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkenyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted " As for "aryloxy", substituted or unsubstituted "arylthio", or substituted "silyl", as stated to be substituted or unsubstituted, at least one hydrogen in these may be replaced by a second substituent. As the second substituent, unless otherwise specified, it is preferable to include: aryl group, heteroaryl group, diarylamino group, alkyl group, cycloalkyl group, or substituted silyl group (wherein the two Two aryl groups of the arylamino group can be bonded to each other via a linking group), and specific examples of these can refer to "aryl", "heteroaryl", and "diarylamino" as the first substituent (wherein Two aryl groups of the diarylamino group may be bonded to each other via a linking group), description of "alkyl", "cycloalkyl" or "substituted silyl". In addition, in the aryl group or heteroaryl group as the second substituent, at least one of these hydrogen groups is represented by an aryl group such as a phenyl group (specific examples are the above-mentioned groups), an alkyl group such as a methyl group or a tert-butyl group ( A structure substituted with a cycloalkyl group such as a specific example) or a cyclohexyl group (a specific example is a group described above) is also included in the aryl or heteroaryl group as the second substituent. As an example, when the second substituent is a carbazolyl group, a carbazolyl group in which at least one hydrogen on the 9-position is substituted by an aryl group such as phenyl, an alkyl group such as methyl, or a cycloalkyl group such as cyclohexyl also includes In the heteroaryl as the second substituent. The above description is also applicable to the description of other first substituents and second substituents in this specification.

The emission wavelength can be adjusted by the steric hindrance, electron donating property, and electron withdrawing property of the structure of the first substituent. It is preferably a group represented by the following structural formula, more preferably methyl, tert-butyl, tert-amyl, tert-octyl, neopentyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4- Xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-trimethylphenyl, diphenylamino, di-p-tolylamino, bis(p-(tert-butyl ) phenyl) amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-tert-butylcarbazolyl and phenoxy, more preferably methyl, tert-butyl, tert-amyl Base, tert-octyl, neopentyl, adamantyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolyl Amino, bis(p-(tert-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl and 3,6-di-tert-butylcarbazolyl. From the viewpoint of ease of synthesis, groups with large steric hindrance are preferred for selective synthesis, specifically, tert-butyl, tert-amyl, tert-octyl, adamantyl, o-tolyl, and p-toluene are preferred. Base, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, two-p-tolylamino, bis(p-(tert-butyl yl)phenyl)amino, 3,6-dimethylcarbazolyl and 3,6-di-tert-butylcarbazolyl.

In the following structural formulas, "Me" represents a methyl group, "tBu" represents a t-butyl group, "tAm" represents a t-amyl group, "tOct" represents a t-octyl group, and * represents a bonding position.

[chem 36]

[chem 37]

[chem 38]

[chem 39]

[chemical 40]

[chem 41]

[chem 42]

[chem 43]

[chem 44]

[chem 45]

[chem 46]

[chem 47]

[chem 48]

As a substituent when two or three hydrogens bonded to continuous (adjacent) carbon atoms are substituted, any one of the following groups may be used.

[chem 49]

In each formula, Me is a methyl group. In each formula, only two or three atoms that are continuous (adjacent) on the ring of any aryl ring or heteroaryl ring in the A ring, B ring, and C ring are bonded at *.

The polycyclic aromatic compound having one or two or more structures comprising a structural unit represented by formula (1) and its preferred forms preferably contains at least one tertiary alkyl group represented by the formula (tR) (tert-butyl group, t-pentyl group, etc.), neopentyl group or adamantyl group, more preferably a structure containing a tert-alkyl group represented by formula (tR) (t-butyl group, t-pentyl group, etc.). The reason for this is that the intermolecular distance increases due to such a bulky substituent, so that the luminescence quantum yield (PLQY) increases. In addition, the substituent is also preferably a diarylamino group (two aryl groups may be bonded to each other via a linking group). Furthermore, it is also preferably a diarylamino group substituted by a group of formula (tR) (two aryl groups can be bonded to each other via a linking group), a carbazolyl group substituted by a group of formula (tR) (preferably N- carbazolyl) or benzocarbazolyl (preferably N-benzocarbazolyl) substituted by a group of formula (tR). As the group of formula (tR), the substitution form of diarylamino group (wherein, the two aryl groups of the diarylamino group can be bonded to each other through a linking group), carbazolyl and benzocarbazolyl can be Examples in which some or all of the hydrogens of the aryl ring or benzene ring in these groups are substituted by the group of the formula (tR) are given.

<Specific examples of the polycyclic aromatic compound of the present invention>

Further specific examples of the polycyclic aromatic compound represented by the formula (1) of the present invention include the following compounds. In the following structural formulas, "Me" represents a methyl group, "tBu" represents a tert-butyl group, and "D" represents deuterium. In addition, the following structure is an example.

[chemical 50]

[Chemical 51]

[Chemical 52]

[Chemical 53]

[Chemical 54]

[Chemical 55]

[Chemical 56]

[Chemical 57]

[Chemical 58]

The polycyclic aromatic compound of the present invention can be produced according to the following procedure.

<Production method of polycyclic aromatic compound>

A polycyclic aromatic compound having one or two or more structures comprising structural units represented by formula ( ¹ ) or formula ( ² ) is basically firstly made A The ring (a ring) is bonded to the B ring (b ring) and C ring (condensed ring including c1 ring and c2 ring), thereby producing an intermediate (first reaction), and then, using the bonding group (including ^Y1 group) to bond A ring (a ring), B ring (b ring) and C ring (c ring) to produce the final product (second reaction). In the first reaction, for example, if it is an etherification reaction, common reactions such as nucleophilic substitution reaction and Ullmann reaction (Ullmann Reaction) can be used, and if it is an amination reaction, Buchwald-Hartwig can be used. Common reactions such as Buchwald-Hartwig Reaction. In addition, in the second reaction, a tandem Hetero-Friedel-Crafts Reaction (sequential aromatic electrophilic substitution reaction, hereinafter the same) can be utilized. By using a raw material having a desired condensed ring somewhere in the reaction step or by adding a step of condensing the ring, at least one ring selected from the group consisting of the A ring, the B ring, and the C ring can be selected from A compound is produced from a condensed ring composed of two or more rings in the group consisting of a monocyclic aryl ring, a monocyclic heteroaryl ring, and a cyclopentadiene ring.

<Manufacturing method via intermediate 1>

The polycyclic aromatic compound of the present invention can be produced by a production method including the following steps. For the following steps, the description in International Publication No. 2015/102118 can be referred to.

The following expressions include the reaction of the following reaction procedure: using an organic base compound to metallate the halogen atom (Hal) between ^X1 and ^X2 in the following intermediate 1; using a halide selected from ^Y1 , ^Y1 Reagents from the group consisting of amidohalides of Y ¹ , alkoxylates of Y 1 and aryloxylates of Y ¹ exchange the metal for Y ¹ ; The Y ¹ is used to bond the B ring to the C ring using the Y 1 family of electrophilic substitution reactions.

[Chemical 59]

Examples of the metallating reagent used in the halogen-metal exchange reaction in the schemes described so far include methyllithium, n-butyllithium, sec-butyllithium, tert-butyllithium and other alkyllithiums, and isopropylmagnesium chloride. , isopropylmagnesium bromide, phenylmagnesium chloride, phenylmagnesium bromide, lithium chloride complex of isopropylmagnesium chloride known as Turbo Grignard reagent, and the like.

In addition, examples of metallating reagents used in the ortho metal exchange reaction in the schemes described so far include lithium diisopropylamide, lithium tetramethylpiperidide, hexamethylbis Organic base compounds such as lithium silamide, potassium hexamethyldisilazide, lithium chloride tetramethylpiperidinylmagnesium-lithium chloride complex, and lithium tri-n-butylmagnesate.

Furthermore, as an additive to accelerate the reaction when using an alkyllithium as a metallating agent, N,N,N',N'-tetramethylethylenediamine, 1,4-diazabicyclo[2.2.2] Octane, N, N-dimethylpropylene urea, etc.

In addition, examples of the Lewis acid used in the flow described so far include AlCl ₃ , AlBr ₃ , AlF ₃ , BF ₃ ·OEt ₂ , BCl ₃ , BBr 3 , GaCl ₃ , GaBr ₃ , InCl _{3 ,} InBr ₃ , In( OTf) ₃ , SnCl ₄ , SnBr ₄ , AgOTf, ScCl ₃ , Sc(OTf) ₃ , ZnCl ₂ , ZnBr ₂ , Zn(OTf) ₂ , MgCl ₂ , MgBr ₂ , Mg(OTf) ₂ , LiOTf, NaOTf, KOTf , Me ₃ SiOTf, Cu(OTf) ₂ , CuCl ₂ , YCl ₃ , Y(OTf) ₃ , TiCl ₄ , TiBr ₄ , ZrCl ₄ , ZrBr ₄ , FeCl 3 , FeBr ₃ , CoCl ₃ , CoBr _{3 ,} etc. In addition, those in which these Lewis acids are supported on a solid can also be used in the same manner.

In addition, examples of Brenest's acid used in the processes described so far include p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, fluorosulfonic acid, carboxylic acid, trifluoroacetic acid, (trifluoromethanesulfonyl) imide, tris(trifluoromethanesulfonyl)methane, hydrogen chloride, hydrogen bromide, hydrogen fluoride and the like. In addition, examples of solid Brenest acid include Amberlist (trade name: Dow Chemical), Nation (trade name: Dupont), zeolite ), Taycacure (trade name: Tayca Co., Ltd.), etc.

In addition, examples of amines that can be added in the flow described so far include diisopropylethylamine, triethylamine, tributylamine, 1,4-diazabicyclo[2.2.2]octane, N , N-dimethyl-p-toluidine, N,N-dimethylaniline, pyridine, 2,6-lutidine, 2,6-di-tert-butylamine, etc.

In addition, examples of solvents used in the processes described so far include o-dichlorobenzene, chlorobenzene, toluene, benzene, methylene chloride, chloroform, dichloroethylene, benzotrifluoride, decalin, and cyclohexane. , hexane, heptane, 1,2,4-trimethylbenzene, xylene, diphenyl ether, anisole, cyclopentyl methyl ether, tetrahydrofuran, dioxane, methyl-tert-butyl ether wait.

Here, an example in which Y ¹ is B is described, but a compound in which Y ¹ is P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R can also be synthesized by appropriately changing the raw material.

In the scheme, in order to facilitate the tandem ZF-Ridell-Kuft reaction, Brenest bases or Lewis acids can also be used. Among them, in the case of using ^Y1 halides ^such as Y1 trifluoride, ^Y1 trichloride, ^Y1 tribromide, ^Y1 triiodide, etc., with the progress of the aromatic electrophilic substitution reaction progress, and generate acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide, so it is effective to use Brenstein's base that captures acids. On the other hand, in the case of using the amino halide of ^Y1 and the alkoxylate of ^Y1 , amines and alcohols are generated as the aromatic electrophilic substitution reaction proceeds, so in many cases, it is not necessary to use Brenstein's base, but since the ability to detach an amino group or an alkoxy group is low, it is effective to use a Lewis acid that promotes the detachment.

In addition, the polycyclic aromatic compounds of the present invention also include compounds in which at least a part of hydrogen atoms are substituted by deuterium or cyano groups, or compounds in which halogens such as fluorine or chlorine are substituted. Synthesize in the same manner as described above using chlorinated, cyanided, fluorinated or chlorinated raw materials.

<2. Organic devices>

The polycyclic aromatic compound of the present invention can be used as a material for organic devices. As an organic device, an organic electroluminescent element, an organic field effect transistor, an organic thin film solar cell etc. are mentioned, for example.

The polycyclic aromatic compound of the present invention can be used as a material for organic devices. Examples of organic devices include organic electroluminescence elements, organic field effect transistors, organic thin-film solar cells, and the like, but organic electroluminescence elements are preferred. The polycyclic aromatic compound of the present invention is preferably a material for an organic electroluminescent element, more preferably a material for a light emitting layer (light emitting material), and most preferably a dopant material for a light emitting layer.

<2-1. Organic electroluminescence element>

<2-1-1. Structure of organic electroluminescence element>

FIG. 1 is a schematic cross-sectional view showing an example of an organic EL element.

The organic EL element 100 shown in FIG. 1 comprises: a substrate 101, an anode 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode 102, a hole transport layer 104 disposed on the hole injection layer 103, The light emitting layer 105 disposed on the hole transport layer 104, the electron transport layer 106 disposed on the light emitting layer 105, the electron injection layer 107 disposed on the electron transport layer 106, and the cathode 108 disposed on the electron injection layer 107.

In addition, the organic EL element 100 can also reverse the production order to form, for example, the following structure, which includes: a substrate 101, a cathode 108 disposed on the substrate 101, an electron injection layer 107 disposed on the cathode 108, an electron injection layer 107 disposed on the electron The electron transport layer 106 on the injection layer 107, the light emitting layer 105 disposed on the electron transport layer 106, the hole transport layer 104 disposed on the light emitting layer 105, the hole injection layer 103 disposed on the hole transport layer 104, And the anode 102 disposed on the hole injection layer 103 .

Not all of the above layers are indispensable layers, and the minimum structural unit is set as a structure including an anode 102, a light emitting layer 105, and a cathode 108, a hole injection layer 103, a hole transport layer 104, an electron transport layer 106, an electron The injection layer 107 is an arbitrarily arbitrable layer. In addition, each of the above-mentioned layers may include a single layer or a plurality of layers.

As the form of the layer constituting the organic EL element, in addition to the structural form of the above-mentioned "substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode", it may be " Substrate/anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole injection layer/light emitting layer/electron transport layer/electron injection layer/cathode", "substrate/ Anode / hole injection layer / hole transport layer / light emitting layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode”, “substrate / Anode/Emitting Layer/Electron Transport Layer/Electron Injection Layer/Cathode", "Substrate/Anode/Hole Transport Layer/Emitting Layer/Electron Injection Layer/Cathode", "Substrate/Anode/Hole Transport Layer/Emitting Layer/Electron transport layer/cathode", "substrate/anode/hole injection layer/light emitting layer/electron injection layer/cathode", "substrate/anode/hole injection layer/light emitting layer/electron transport layer/cathode", "substrate/anode /Emitting layer/Electron transport layer/Cathode” and “Substrate/Anode/Emitting layer/Electron injection layer/Cathode” structure.

<2-1-2. Light-emitting layer in organic electroluminescent device>

The polycyclic aromatic compound of the present invention is preferably used as a material for forming one or more organic layers in an organic electroluminescence device, more preferably used as a material for forming a light emitting layer. The light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. As the material forming the light emitting layer 105, as long as it is a compound (luminescent compound) that is excited to emit light by the recombination of holes and electrons, it is preferable that it can form a stable thin film shape and exhibit a strong The luminescence (fluorescence) efficiency of the compound. The polycyclic aromatic compound of the present invention can be used as a material for the light-emitting layer, can also be used as a dopant material, and can also be used as a host material, but it is preferably used as a material for the light-emitting layer, and more preferably used as a dopant material. miscellaneous materials.

In addition, as a dopant, there is an example of using an auxiliary dopant and an emission dopant in combination, but in this specification, when simply described as a "dopant", it refers to an emission dopant used alone. agent.

The light-emitting layer may be a single layer or may include multiple layers, any of which may be used, and each is formed of materials for the light-emitting layer (host material, dopant material). The host material and the dopant material may each be one type, or a combination of multiple types, or any of them may be used. The dopant material may be included in the entire host material, or may be included in a part of the host material, or either. As a doping method, it may be formed by co-evaporation with the host material, or it may be mixed with the host material in advance and then vapor-deposited simultaneously. Specific examples of dopants to be combined with the compound of the present invention in the case of combining multiple dopants are shown below. In the following structural formulas, "Me" represents a methyl group, "tBu" represents a tert-butyl group, and "D" represents deuterium.

[Chemical 60]

[Chemical 61]

[chem 62]

[chem 63]

The amount of the host material used varies depending on the type of the host material, and may be determined in accordance with the properties of the host material. The usage-amount of the host material is preferably 50-99.999 mass%, more preferably 80-99.95 mass%, and still more preferably 90-99.9 mass%, of the entire light-emitting layer material.

The amount of the dopant material used varies depending on the type of the dopant material, and may be determined in accordance with the characteristics of the dopant material. The amount of dopant used is preferably 0.001% by mass to 50% by mass, more preferably 0.05% by mass to 20% by mass, and still more preferably 0.1% by mass to 10% by mass of the entire light emitting layer material. If it is the said range, it is preferable at the point which can prevent a concentration quenching phenomenon, for example.

<Main material>

或芴等的稠环衍生物、双苯乙烯基蒽衍生物或二苯乙烯基苯衍生物等的双苯乙烯基衍生物、四苯基丁二烯衍生物、环戊二烯衍生物、芴衍生物、苯并芴衍生物等。As the host material, anthracene, pyrene, dibenzo

or fused ring derivatives such as fluorene, bistyryl derivatives such as bistyryl anthracene derivatives or distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzofluorene derivatives, etc.

Moreover, as a host material, the compound represented by any one of following formula (H1), formula (H2), and formula (H3), for example can be used.

[chem 64]

In formula (H1), formula (H2) and formula (H3), ^L1 is an arylene group with 6 to 24 carbons, a heteroarylene group with 2 to 24 carbons, or a heteroarylene group with 6 to 24 carbons Arylene and arylene heteroarylene with 6 to 24 carbons, preferably arylene with 6 to 16 carbons, more preferably arylene with 6 to 12 carbons, especially preferably carbon Specific examples of the arylene group having a number of 6 to 10 include divalent groups such as a benzene ring, a biphenyl ring, a terphenyl ring, and a fluorene ring. The heteroarylene group is preferably a heteroarylene group having 2 to 24 carbon atoms, more preferably a heteroarylene group having 2 to 20 carbon atoms, still more preferably a heteroarylene group having 2 to 15 carbon atoms, particularly preferably A heteroarylene group having 2 to 10 carbon atoms, specifically, pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring (furazan ring, etc.) , Thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring , benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenothiazine ring, phenoxazine ring, phenothiazine ring, phenazine ring, indazine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, and divalent groups such as thianthracycline. At least one hydrogen in the compounds represented by the above formulas may be substituted with an alkyl group having 1 to 6 carbons, a cyano group, a halogen or deuterium.

Preferred specific examples include compounds represented by any of the structural formulas listed below. In addition, in the structural formulas listed below, at least one hydrogen may be substituted by halogen, cyano, alkyl having 1 to 4 carbons (such as methyl or tert-butyl), phenyl or naphthyl, and the like.

[chem 65]

[chem 66]

[chem 67]

[chem 68]

<Anthracene compound>

Examples of the main anthracene compound include compounds represented by formula (3-H) and compounds represented by formula (3-H2).

[chem 69]

In formula (3-H),

X and ^Ar are independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, optionally substituted diheteroaryl substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted alkyl, optionally substituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted Substituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio or substituted silyl, all X and Ar ⁴ will not become hydrogen at the same time, the diarylamino The two aryl groups of the said diheteroarylamino group can be bonded to each other through a linking group, the two heteroaryl groups of the diheteroarylamino group can be bonded to each other through a linking group, and the aryl group and the heteroaryl group of the arylheteroarylamino group can be bonded to each other through a linking group. The groups may be bonded to each other via a linking group.

At least one hydrogen in the compound represented by formula (3-H) is substituted by halogen, cyano, deuterium or heteroaryl which may be substituted, or is unsubstituted.

In addition, a multimer (preferably a dimer) may be formed by using the structure represented by the formula (3-H) as a unit structure. In this case, for example, a form in which the unit structures represented by the formula (3-H) are bonded via X, and examples of X include a single bond, an arylene group (phenylene, biphenylene, and naphthylene, etc.) and heteroarylene (pyridine ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, benzocarbazole ring and phenyl substituted carbazole ring, etc.) base) etc.

The details of each group in the compound represented by the formula (3-H) can be referred to the description of the above formula (1), and further described in the column of the following preferred embodiments.

Preferred forms of the anthracene compound will be described below. The definitions of symbols in the following structures are the same as those described above.

[chem 70]

In formula (3-H), X is independently represented by formula (3-X1), formula (3-X2) or formula (3-X3), and formula (3-X1), formula (3-X2 ) or the group represented by the formula (3-X3) is bonded to the anthracycline of the formula (3-H) at *. It is preferable that two Xs do not become groups represented by the formula (3-X3) at the same time. More preferably, two Xs do not become groups represented by the formula (3-X2) at the same time.

In addition, a multimer (preferably a dimer) may be formed by using the structure represented by the formula (3-H) as a unit structure. In this case, for example, a form in which the unit structures represented by the formula (3-H) are bonded via X, and examples of X include a single bond, an arylene group (phenylene, biphenylene, and naphthylene, etc.) and heteroarylene (pyridine ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, benzocarbazole ring and phenyl substituted carbazole ring, etc.) base) etc.

The naphthylene moiety in formula (3-X1) and formula (3-X2) can be condensed by a benzene ring. The structures condensed in this manner are shown below.

[chem 71]

基、三亚苯基、芘基、或式(A)所表示的基(也包含咔唑基、苯并咔唑基及苯基取代咔唑基)。此外，在Ar¹或Ar²为式(A)所表示的基的情况下，式(A)所表示的基在所述*处与式(3-X1)或式(3-X2)中的萘环键结。Ar ¹ and Ar ² are independently hydrogen, phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthrenyl, fluorenyl, benzofluorenyl,

group, triphenylene group, pyrenyl group, or a group represented by formula (A) (also including carbazolyl, benzocarbazolyl and phenyl-substituted carbazolyl). In addition, when Ar ¹ or Ar ² is a group represented by formula (A), the group represented by formula (A) is the same as that in formula (3-X1) or formula (3-X2) at said * Naphthalene ring bonded.

基、三亚苯基、芘基、或式(A)所表示的基(也包含咔唑基、苯并咔唑基及苯基取代咔唑基)。此外，在Ar³为式(A)所表示的基的情况下，式(A)所表示的基在所述*处与式(3-X3)中的直线所表示的单键键结。即，式(3-H)的蒽环与式(A)所表示的基直接键结。Ar ³ is phenyl, biphenyl, terphenyl, quaternyl, naphthyl, phenanthrenyl, fluorenyl, benzofluorenyl,

group, triphenylene group, pyrenyl group, or a group represented by formula (A) (also including carbazolyl, benzocarbazolyl and phenyl-substituted carbazolyl). In addition, when Ar ³ is a group represented by the formula (A), the group represented by the formula (A) is bonded to the single bond represented by the straight line in the formula (3-X3) at the *. That is, the anthracycline of the formula (3-H) is directly bonded to the group represented by the formula (A).

基、三亚苯基、芘基、或式(A)所表示的基(也包含咔唑基及苯基取代咔唑基)取代。此外，在Ar³所具有的取代基为式(A)所表示的基的情况下，式(A)所表示的基在所述*处与式(3-X3)中的Ar³键结。In addition, Ar ³ may have a substituent, and at least one hydrogen in Ar ³ may be an alkyl group having 1 to 4 carbons, a cycloalkyl group having 5 to 10 carbons, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, etc. , phenanthrenyl, fluorenyl,

group, triphenylene group, pyrenyl group, or a group represented by formula (A) (also including carbazolyl and phenyl-substituted carbazolyl). In addition, when the substituent of Ar ³ is a group represented by formula (A), the group represented by formula (A) is bonded to Ar ³ in formula (3-X3) at the above-mentioned *.

Ar4 are independently hydrogen, phenyl, biphenyl, terphenyl, naphthyl, or alkyl (methyl, ethyl, tert-butyl, etc.) with 1 to 4 carbons and/or 5 to 4 carbons 10 Cycloalkyl-substituted silyl groups.

Alkyl groups with 1 to 4 carbon atoms substituted in silyl groups include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, cyclobutyl, etc. Three hydrogens are independently substituted by these alkyl groups.

Specific "silyl groups substituted with alkyl groups having 1 to 4 carbon atoms" include trimethylsilyl groups, triethylsilyl groups, tripropylsilyl groups, triisopropylsilyl groups, and tributylsilyl groups. Silyl group, tri-sec-butylsilyl group, tri-tert-butylsilyl group, ethyldimethylsilyl group, propyldimethylsilyl group, isopropyldimethylsilyl group, butyldimethylsilyl group, sec-butyldimethylsilyl, tert-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyldiethylsilyl , sec-butyldiethylsilyl, tert-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilane base, tert-butyldipropylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, butyldiisopropylsilyl, sec-butyldiisopropylsilyl, tert-butyl Diisopropylsilyl, etc.

Cycloalkyl groups with 5 to 10 carbon atoms substituted in silyl groups include: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl , bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl (norbornyl), bicyclo[2.2.2]octyl, adamantine An alkyl group, a decahydronaphthyl group, a decahydroazulene group, etc., and three hydrogens in a silyl group are independently substituted by these cycloalkyl groups.

Specific examples of the "silyl group substituted with a cycloalkyl group having 5 to 10 carbon atoms" include a tricyclopentylsilyl group and a tricyclohexylsilyl group.

As substituted silyl groups, there are also dialkylcycloalkylsilyl groups substituted with two alkyl groups and one cycloalkyl group, and alkyldicycloalkylsilyl groups substituted with one alkyl group and two cycloalkyl groups , Specific examples of the substituted alkyl group and cycloalkyl group include those mentioned above.

In addition, hydrogen in the chemical structure of the anthracene compound represented by formula (3-H) may be substituted by a group represented by formula (A). When substituting with a group represented by formula (A), the group represented by formula (A) is substituted with at least one hydrogen in the compound represented by formula (3-H) at the above-mentioned *.

The group represented by formula (A) is one of the substituents that the anthracene compound represented by formula (3-H) may have.

[chem 72]

In formula (A), Y is -O-, -S- or >NR ²⁹ , R ²¹ to R ²⁸ are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted Aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dioxane Cycloalkylsilyl group, alkylbicycloalkylsilyl group, amino group that may be substituted, halogen, hydroxyl group or cyano group, the adjacent groups in R ²¹ ~ R ²⁸ may bond with each other to form a hydrocarbon ring, aryl group ring or heteroaryl ring, R ²⁹ is hydrogen or aryl which may be substituted.

Y in the formula (A) is preferably -O-.

The "alkyl group" as the "alkyl group that may be substituted" in R ²¹ to R ²⁸ may be either straight chain or branched chain, for example, a straight chain alkyl group having 1 to 24 carbon atoms or a carbon number 3-24 branched chain alkyl groups. It is preferably an alkyl group with 1 to 18 carbons (branched chain alkyl with 3 to 18 carbons), more preferably an alkyl group with 1 to 12 carbons (branched alkyl with 3 to 12 carbons), and even more preferably The alkyl group having 1 to 6 carbons (branched chain alkyl group having 3 to 6 carbons) is particularly preferably an alkyl group having 1 to 4 carbons (branched alkyl group having 3 to 4 carbons).

Specific "alkyl groups" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neo Pentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1- Methylhexyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6- Dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl Base, n-tetradecyl, n-fifteen bases, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc.

Examples of the "cycloalkyl group" of the "cycloalkyl group which may be substituted" in R ²¹ to R ²⁸ include cycloalkyl groups having 3 to 24 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, and cycloalkyl groups having 3 to 20 carbon atoms. Cycloalkyl with ∼16 carbons, cycloalkyl with 3 to 14 carbons, cycloalkyl with 5 to 10 carbons, cycloalkyl with 5 to 8 carbons, cycloalkyl with 5 to 6 carbons, cycloalkyl with 5 carbons cycloalkyl etc.

Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and those having 1 to 3 carbon atoms. Alkyl (especially methyl) substituents of 4, or bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo [3.1.0] Hexyl, bicyclo[2.2.1]heptyl (norbornyl), bicyclo[2.2.2]octyl, adamantyl, bisadamantyl, decahydronaphthyl, decahydroazulene, etc.

The "aryl group" of the "aryl group which may be substituted" in R ²¹ to R ²⁸ includes, for example, an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 16 carbon atoms, and more preferably an aryl group having 6 to 16 carbon atoms. The aryl group having 6 to 12 carbon atoms is particularly preferably an aryl group having 6 to 10 carbon atoms.

Specific "aryl groups" include: phenyl as a monocyclic system, biphenyl group as a bicyclic system, naphthyl group as a condensed bicyclic system, terphenyl group as a tricyclic system (m-terphenyl group) , o-terphenylene, p-terphenylene), acenaphthyl, fluorenyl, phenanthrenyl, phenanthrenyl as condensed tricyclic ring system, triphenylene, pyrenyl, naphthacene tetraphenylene as condensed tetracyclic ring system, Perylene, pentacene and the like as condensed pentacyclic systems.

The "heteroaryl" of the "heteroaryl which may be substituted" in R ²¹ to R ²⁸ includes, for example, a heteroaryl having 2 to 30 carbons, preferably a heteroaryl having 2 to 25 carbons, and more It is preferably a heteroaryl group having 2 to 20 carbon atoms, more preferably a heteroaryl group having 2 to 15 carbon atoms, particularly preferably a heteroaryl group having 2 to 10 carbon atoms. Moreover, as a heteroaryl group, the heterocyclic ring which contains 1-5 heteroatoms selected from oxygen, sulfur, and nitrogen as a ring constituting atom other than carbon, etc. are mentioned, for example.

Specific "heteroaryl groups" include, for example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, Azolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl , benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridine Base, carbazolyl, acridyl, phenoxathiyl, phenoxazinyl, phenothiazinyl, phenazinyl, indolyl, furyl, benzofuryl, isobenzofuryl, dibenzo Furyl, thienyl, benzo[b]thienyl, dibenzothienyl, furanyl, thienyl, naphthobenzofuryl, naphthobenzothienyl, and the like.

The "alkoxy" of the "alkoxy that may be substituted" in R ²¹ to R ²⁸ includes, for example, straight-chain alkoxy having 1 to 24 carbons or branched alkoxy having 3 to 24 carbons. . Preferably it is an alkoxy group with 1 to 18 carbons (branched alkoxy group with 3 to 18 carbons), more preferably an alkoxy group with 1 to 12 carbons (branched alkoxy group with 3 to 12 carbons) , more preferably an alkoxy group with 1 to 6 carbons (branched alkoxy group with 3 to 6 carbons), particularly preferably an alkoxy group with 1 to 4 carbons (branched alkoxy group with 3 to 4 carbons) base).

Specific examples of "alkoxy" include: methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy base, hexyloxy, heptyloxy, octyloxy, etc.

The "aryloxy group" in the "aryloxy group that may be substituted" in R ²¹ to R ²⁸ is a group in which the hydrogen of the -OH group is replaced by an aryl group, and the aryl group can be cited as the above R ²¹ to R ²⁸ . The group described for the "aryl group".

The "arylthio group" of the "arylthio group that may be substituted" in R ²¹ to R ²⁸ is a group in which the hydrogen of the -SH group is replaced by an aryl group, and the aryl group can be cited as the above R ²¹ to R ²⁸ . The group described for the "aryl group".

As the "trialkylsilyl group" in R ²¹ to R ²⁸ , a group in which three hydrogens in the silyl group are independently substituted by an alkyl group can be cited, and the alkyl group can be cited as the above-mentioned R ²¹ to R ²⁸ . The group described for the "alkyl". Preferred alkyl groups for substitution are alkyl groups having 1 to 4 carbon atoms, specifically, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, cyclic Butyl, etc.

Specific "trialkylsilyl groups" include trimethylsilyl groups, triethylsilyl groups, tripropylsilyl groups, triisopropylsilyl groups, tributylsilyl groups, and tri-sec-butylsilane groups. group, tri-tert-butylsilyl group, ethyldimethylsilyl group, propyldimethylsilyl group, isopropyldimethylsilyl group, butyldimethylsilyl group, sec-butyldimethylsilyl group , tert-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilane base, tert-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, tert-butyldipropyl Silyl group, methyldiisopropylsilyl group, ethyldiisopropylsilyl group, butyldiisopropylsilyl group, sec-butyldiisopropylsilyl group, tert-butyldiisopropylsilyl group, etc. .

The "tricycloalkylsilyl group" in R ²¹ to R ²⁸ includes a group in which three hydrogens in the silyl group are independently substituted by a cycloalkyl group, and the cycloalkyl group can be cited as the R ²¹ to R 28 group. The group described by "cycloalkyl" in R ²⁸ . A preferred cycloalkyl group for substitution is a cycloalkyl group having 5 to 10 carbon atoms, specifically, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, Bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl base, adamantyl, decalinyl, decalinyl, etc.

As a specific "tricycloalkylsilyl group", a tricyclopentylsilyl group, a tricyclohexylsilyl group, etc. are mentioned.

As specific examples of a dialkylcycloalkylsilyl group substituted with two alkyl groups and one cycloalkyl group, and an alkyldicycloalkylsilyl group substituted with one alkyl group and two cycloalkyl groups, substituted There is a silyl group selected from the specific alkyl group and cycloalkyl group.

The "substituted amino group" of the "amino group which may be substituted" in R ²¹ to R ²⁸ includes, for example, an amino group in which two hydrogens are substituted with an aryl group or a heteroaryl group. An amino group whose two hydrogens are substituted by an aryl group is a diaryl group (two aryl groups can be bonded to each other via a linking group) substituted amino group, an amino group whose two hydrogens are substituted by a heteroaryl group is a diheteroaryl substituted amino group, and two An amino group whose hydrogen is substituted by an aryl group and a heteroaryl group is an arylheteroaryl group substituted amino group. As the aryl or heteroaryl group, the group described as the "aryl" or "heteroaryl" in R ²¹ to R ²⁸ may be cited.

Specific "substituted amino groups" include diphenylamino groups, dinaphthylamino groups, phenylnaphthylamino groups, dipyridylamino groups, phenylpyridylamino groups, and naphthylpyridylamino groups.

Examples of "halogen" in R ²¹ to R ²⁸ include fluorine, chlorine, bromine, and iodine.

Among the groups described as R ²¹ to R ²⁸ , several groups may be substituted as described above, and examples of substituents in such cases include alkyl groups, cycloalkyl groups, aryl groups, and heteroaryl groups. The alkyl, cycloalkyl, aryl or heteroaryl can be cited as "alkyl", "cycloalkyl", "aryl" or "heteroaryl" in R ²¹ to R ²⁸ base.

R ²⁹ in ">NR ²⁹ " as Y is hydrogen or an aryl group that may be substituted, and as the aryl group, the group described as the "aryl group" in R ²¹ to R ²⁸ can be cited, and , as the substituent, those described as the substituent for R ²¹ to R ²⁸ can be cited.

Adjacent groups among R ²¹ to R ²⁸ may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring. When not forming a ring is a group represented by the following formula (A-1), and when forming a ring, for example, groups represented by the following formula (A-2) to formula (A-14). In addition, at least one hydrogen in the group represented by any one of formula (A-1) to formula (A-14) can be represented by alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy , arylthio group, trialkylsilyl group, tricycloalkylsilyl group, dialkylcycloalkylsilyl group, alkyldicycloalkylsilyl group, diaryl group (two aryl groups can be mutually connected via a linking group) Bonding) substituted amino, diheteroaryl substituted amino, arylheteroaryl substituted amino, halogen, hydroxy, or cyano substituted.

[chem 73]

As the ring formed by the bonding of adjacent groups, if it is a hydrocarbon ring, for example, a cyclohexane ring is mentioned, and as an aryl ring or a heteroaryl ring, the "aryl group" in the above-mentioned R ²¹ to R ²⁸ is exemplified. " or the ring structure described in "heteroaryl" formed by condensation with one or two benzene rings in formula (A-1).

The group represented by the formula (A) is a group obtained by removing one hydrogen at any position of the formula (A), and * indicates the position. That is, the group represented by the formula (A) may have an arbitrary position as a bonding position. For example, it can be any ring formed by bonding with any carbon atom on the two benzene rings in the structure of formula (A) and adjacent groups among R ²¹ to R ²⁸ in the structure of formula (A) The atom above, or any position in R ²⁹ of ">NR ²⁹ " of Y in the structure of formula (A), or the group to which N (R ²⁹ is a bonding bond) of "> NR ²⁹ " is directly bonded . The same applies to the group represented by any one of formula (A-1) to formula (A-14).

As the group represented by the formula (A), for example, the group represented by any one of the formula (A-1) to the formula (A-14), preferably the group represented by the formula (A-1) to the formula (A-5 ) and any one of formula (A-12) to formula (A-14), more preferably a group represented by any one of formula (A-1) to formula (A-4) , is more preferably a group represented by any one of formula (A-1), formula (A-3) and formula (A-4), and is particularly preferably a group represented by formula (A-1).

As a group represented by formula (A), the following groups are mentioned, for example. The definitions of Y and * in the formula are the same as above.

[chem 74]

[chem 75]

In the compound represented by formula (3-H), the group represented by formula (A) is preferably the naphthalene ring in formula (3-X1) or formula (3-X2), the A form in which any one of a single bond and Ar ³ in the formula (3-X3) is bonded.

In addition, all or a part of hydrogens in the chemical structure of the anthracene compound represented by the formula (3-H) may be deuterium.

The main anthracene compound may be, for example, a compound represented by the following formula (3-H2).

[chem 76]

In formula (3-H2), Ar ^c is an aryl group that may be substituted or a heteroaryl group that may be substituted, R ^c is hydrogen, alkyl, or cycloalkyl, Ar ¹¹ , Ar ¹² , Ar ¹³ , Ar ¹⁴ , Ar ¹⁵ , A ¹⁶ , Ar ¹⁷ and Ar ¹⁸ are independently hydrogen, aryl that can be substituted, heteroaryl that can be substituted, diarylamino that can be substituted (two aryls can be connected via group), optionally substituted diheteroarylamino (two heteroaryl groups may be bonded to each other via a linking group), optionally substituted arylheteroarylamino (aryl and heteroaryl groups may be bonded to each other Bonded via a linking group), optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted An arylthio group or a silyl group that may be substituted, and at least one hydrogen in the compound represented by the formula (3-H2) may be substituted by halogen, cyano, or deuterium.

The "aryl that may be substituted", "heteroaryl that may be substituted", and "diarylamino that may be substituted" in formula (3-H2) (two aryl groups may be bonded to each other via a linking group) ", "Diheteroarylamino that can be substituted (two heteroaryl groups can be bonded to each other via a linking group)", "arylheteroarylamino that can be substituted (aryl and heteroaryl can be bonded to each other via a linking group) Linking group)", "optionally substituted alkyl", "optionally substituted cycloalkyl", "optionally substituted alkenyl", "optionally substituted alkoxy", "optionally substituted The definition of "aryloxy group", "arylthio group that may be substituted", or "silyl group that may be substituted" is the same as that shown in the formula (3-H), and the formula (3-H ) in the instructions.

The "aryl group which may be substituted" is also preferably a group represented by any one of the following formula (3-H2-X1) to formula (3-H2-X8).

[chem 77]

基、三亚苯基、芘基、蒽基或式(A)所表示的基。此外，在式(3-H2)的说明中，式(A)所表示的基与式(3-H)所表示的蒽化合物中所说明的基相同。In formula (3-H2-X1) to formula (3-H2-X8), * represents a bonding position. In formula (3-H2-X1) ~ formula (3-H2-X3), Ar ²¹ , Ar ²² and Ar ²³ are independently hydrogen, phenyl, biphenyl, terphenyl, quaternyl, Naphthyl, phenanthrenyl, fluorenyl, benzofluorenyl,

group, triphenylene group, pyrenyl group, anthracenyl group or a group represented by formula (A). In addition, in the description of the formula (3-H2), the groups represented by the formula (A) are the same as those described for the anthracene compound represented by the formula (3-H).

基、三亚苯基、芘基、或式(A)所表示的基。另外，式(3-H2-X1)～式(3-H2-X8)所表示的基的各个中的任一个或两个以上的氢可由碳数1～6的烷基(优选为甲基或叔丁基)取代。In formula (3-H2-X4) ~ formula (3-H2-X8), Ar ²⁴ , Ar ²⁵ , Ar ²⁶ , Ar ²⁷ , Ar ²⁸ , Ar ²⁹ , and Ar ³⁰ are independently hydrogen, phenyl, Biphenyl, terphenyl, naphthyl, phenanthrenyl, fluorenyl,

group, triphenylene group, pyrenyl group, or a group represented by formula (A). In addition, any one or two or more hydrogens in each of the groups represented by the formula (3-H2-X1) to the formula (3-H2-X8) can be formed from an alkyl group with 1 to 6 carbons (preferably methyl or tert-butyl) substitution.

基、三亚苯基、芘基、及式(A)所表示的基所组成的群组中的一个以上的取代基取代的三联苯基(特别是间三联苯基-5′-基)。Furthermore, as a preferred example of the "aryl group which may be substituted", there may be mentioned the group selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, fluorenyl,

A terphenyl group substituted with one or more substituents in the group consisting of a terphenylene group, a terphenylene group, a pyrenyl group, and a group represented by formula (A) (especially m-terphenylene-5'-yl).

As "heteroaryl group which may be substituted", groups represented by formula (A) are also mentioned. In addition, specific examples of "aryl that may be substituted" and "heteroaryl that may be substituted" include dibenzofuryl, naphthobenzofuryl, and phenyl-substituted dibenzofuryl. wait.

At least one hydrogen in the compound represented by formula (3-H2) may be substituted by halogen, cyano or deuterium. Examples of the "halogen" in this case include fluorine, chlorine, bromine, and iodine. Particularly preferred is a compound in which all hydrogens in the compound represented by the formula (3-H2) are replaced by deuterium.

In formula (3-H2), R ^c is hydrogen, alkyl, or cycloalkyl, preferably hydrogen, methyl, or tert-butyl, more preferably hydrogen.

In formula (3-H2), at least two of Ar ¹¹ to Ar ¹⁸ are preferably aryl groups which may be substituted or heteroaryl groups which may be substituted. That is, the anthracene compound represented by the formula (3-H2) preferably has at least three substitutions selected from the group consisting of aryl groups that may be substituted and heteroaryl groups that may be substituted bonded to the anthracene ring. base structure.

Among the anthracene compounds represented by the formula (3-H2), it is more preferable that two of Ar ¹¹ to Ar ¹⁸ are aryl groups that may be substituted or heteroaryl groups that may be substituted, and the other six are hydrogen or substituted Alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, or optionally substituted alkoxy. That is, the anthracene compound represented by the formula (3-H2) more preferably has three substituents selected from the group consisting of aryl groups that may be substituted and heteroaryl groups that may be substituted bonded to the anthracene ring. Structure.

Among the anthracene compounds represented by the formula (3-H2), it is more preferable that any two of Ar ¹¹ to Ar ¹⁸ are substituted aryl groups or substituted heteroaryl groups, and the other six are hydrogen, methyl or tert-butyl.

Furthermore, in the formula (3-H2), it is preferable that R ^c is hydrogen, and any six of Ar ¹¹ to Ar ¹⁸ are hydrogen.

The anthracene compound represented by formula (3-H2) is preferably the following formula (3-H2-A), formula (3-H2-B), formula (3-H2-C), formula (3-H2-D) Or an anthracene compound represented by the formula (3-H2-E).

[chem 78]

基、三亚苯基、芘基、或式(A)所表示的基，这些基中的至少一个氢可由苯基、联苯基、三联苯基、四联苯基、萘基、菲基、芴基、苯并芴基、

基、三亚苯基、芘基、或式(A)所表示的基取代。此处，当芴基及苯并芴基中的亚甲基的氢均由苯基取代时，这些苯基可相互通过单键键结。未键结Ar^c′、Ar^11′、Ar^12′、Ar^13′、Ar^14′、Ar^15′、Ar^17′及Ar^18′的蒽环的碳原子上可代替氢而键结甲基或叔丁基。In formula (3-H2-A), formula (3-H2-B), formula (3-H2-C), formula (3-H2-D) or formula (3-H2-E), Ar ^c' , Ar ^11' , Ar ^12' , Ar ^13' , Ar ^14' , Ar ^15' , Ar ^17' and Ar ^18' are independently phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthrenyl, fluorenyl, benzofluorenyl,

Base, triphenylene, pyrenyl, or the base represented by formula (A), at least one hydrogen in these bases can be phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthrenyl, fluorene base, benzofluorenyl,

group, triphenylene group, pyrenyl group, or a group represented by formula (A) is substituted. Here, when the hydrogens of the methylene groups in the fluorenyl group and the benzofluorenyl group are all substituted with phenyl groups, these phenyl groups may be bonded to each other via a single bond. The carbon atoms of the anthracene rings that are not bonded to Ar ^c' , Ar ^11' , Ar ^12' , Ar ^13' , Ar ^14' , Ar ^15' , Ar ^17' and Ar ^18' can replace hydrogen and bond methyl or tert-butyl.

When Ar ^c' , Ar ^11' , Ar ^12' , Ar ^13' , Ar ^14' , Ar ^15' , Ar ^17' and Ar ^18' are substituted or unsubstituted phenyl or substituted or unsubstituted In the case of a naphthyl group, it is preferably a group represented by any one of the formula (3-H2-X1) to formula (3-H2-X8).

Ar ^c' , Ar ^11' , Ar ^12' , Ar ^13' , Ar ^{14 ', Ar 15'} , Ar ^17' and Ar ^18' are more preferably independently phenyl, biphenyl (especially biphenyl -2-yl or biphenyl-4-yl), terphenyl (especially m-terphenyl-5'-yl), naphthyl, phenanthrenyl, fluorenyl, or the formula (A-1)～ The base represented by any one of the formulas (A-4), at this time, at least one hydrogen in these bases can be formed by phenyl, biphenyl, naphthyl, phenanthrenyl, fluorenyl, or the formula (A- 1) Substitution with a group represented by any one of formulas (A-4).

In addition, compounds represented by formula (3-H2-A), formula (3-H2-B), formula (3-H2-C), formula (3-H2-D) or formula (3-H2-E) At least one hydrogen in may be replaced by halogen, cyano or deuterium. In addition, it is preferably a deuterated form, and is preferably a form in which all anthracyclines are deuterated, or a form in which all hydrogen atoms are deuterated.

Particularly preferable examples of the anthracene compound represented by the formula (3-H2) include an anthracene compound represented by the following formula (3-H2-Aa).

[chem 79]

基、三亚苯基、芘基或所述式(A-1)～式(A-11)中的任一者所表示的基，这些基中的至少一个氢可由苯基、联苯基、三联苯基、萘基、菲基、芴基、苯并芴基、

基、三亚苯基、芘基或式(A-1)～式(A-11)中的任一者所表示的基取代。此处，当芴基及苯并芴基中的亚甲基的氢均由苯基取代时，这些苯基可相互通过单键键结。另外，未键结Ar^c′、Ar^14′及Ar^15′的蒽环的碳原子上可代替氢而取代有甲基或叔丁基。式(3-H2-Aa)所表示的化合物中的至少一个氢可由卤素或氰基取代，且式(3-H2-Aa)所表示的化合物中的至少一个氢由氘取代。In formula (3-H2-Aa), Ar ^c' , Ar ^14' and Ar ^15' are independently phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, fluorenyl, benzofluorenyl,

group, triphenylene group, pyrenyl group or the group represented by any one of the formula (A-1) ~ formula (A-11), at least one hydrogen in these groups can be phenyl, biphenyl, triple Phenyl, naphthyl, phenanthrenyl, fluorenyl, benzofluorenyl,

group, triphenylene group, pyrenyl group, or a group represented by any one of formula (A-1) to formula (A-11). Here, when the hydrogens of the methylene groups in the fluorenyl group and the benzofluorenyl group are all substituted with phenyl groups, these phenyl groups may be bonded to each other via a single bond. In addition, the carbon atoms of the anthracene ring to which Ar ^c' , Ar ^14' and Ar ^15' are not bonded may be substituted with a methyl group or a tert-butyl group instead of hydrogen. At least one hydrogen in the compound represented by formula (3-H2-Aa) may be replaced by halogen or cyano, and at least one hydrogen in the compound represented by formula (3-H2-Aa) is replaced by deuterium.

In formula (3-H2-Aa), Ar ^c' , Ar ^14' and Ar ^15' are preferably independently phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, fluorenyl, or the The base represented by any one of formula (A-1) to formula (A-4), at least one hydrogen in these bases can be represented by phenyl, naphthyl, phenanthrenyl, fluorenyl, or formula (A-1) Substitution with a group represented by any one of the formulas (A-4).

In the compound represented by the formula (3-H2-Aa), it is preferable that hydrogen bonded to at least the carbon at the 10-position of the anthracycline (the carbon to which Arc' is bonded is at the 9-position) is substituted with deuterium. That is, the compound represented by the formula (3-H2-Aa) is preferably a compound represented by the following formula (3-H2-Ab). In addition, in the formula (3-H2-Ab), D is deuterium, Ar ^c' , Ar ^14' and Ar ^15' have the same definitions as in the formula (3-H2-Aa). D in the formula (3-H2-Ab) represents that at least the position is deuterium, and any one or more hydrogens in the formula (3-H2-Ab) can be deuterium at the same time, and it is also preferably the formula (3-H2- The hydrogens in Ab) are all deuterium.

[chem 80]

In addition, specific examples of anthracene compounds include compounds represented by formula (3-131-Y) to formula (3-182-Y), formula (3-183-N), formula (3-184- Y)～Formula (3-284-Y), and Formula (3-500)～Formula (3-557), and Formula (3-600)～Formula (3-605), and Formula (3-606-Y )～the compound represented by the formula (3-626-Y). The hydrogen atoms in these formulas may be partially or completely substituted with deuterium, but particularly preferred forms of deuterium substitution are listed separately. Y in the formula can be -O-, -S-, >NR ²⁹ (the definition of R ²⁹ is the same as above) or >C(-R ³⁰ ) ₂ (R ³⁰ is a linkable aryl or alkyl group) Either, R ²⁹ is, for example, phenyl, and R ³⁰ is, for example, methyl. Regarding the formula number, for example, when Y is O, formula (3-131-Y) is set to formula (3-131-O), and when Y is -S- or >NR ²⁹ , it is respectively set to formula (3-131-S) or formula (3-131-N).

[chem 81]

[chem 82]

[chem 83]

[chem 84]

[chem 85]

[chem 86]

[chem 87]

[chem 88]

[chem 89]

[chem 90]

[chem 91]

[chem 92]

[chem 93]

[chem 94]

[chem 95]

[chem 96]

[chem 97]

[chem 98]

[chem 99]

[chemical 100]

In the above formula, D is deuterium.

Among the compounds, preferably formula (3-131-Y) ~ formula (3-134-Y), formula (3-138-Y), formula (3-140-Y) ~ formula (3-143-Y ), formula (3-150-Y), formula (3-153-Y) ~ formula (3-156-Y), formula (3-166-Y), formula (3-168-Y), formula (3 -173-Y), formula (3-177-Y), formula (3-180-Y) ~ formula (3-183-N), formula (3-185-Y), formula (3-190-Y) , formula (3-223-Y), formula (3-241-Y), formula (3-250-Y), formula (3-252-Y) ~ formula (3-254-Y), formula (3- 270-Y) ~ formula (3-284-Y), formula (3-501), formula (3-507), formula (3-508), formula (3-509), formula (3-513), formula (3-514), formula (3-519), formula (3-521), formula (3-538) ~ formula (3-547) or formula (3-600) ~ formula (3-605), and formula (3-606-Y) to the compound represented by the formula (3-626-Y). In addition, Y is preferably -O- or >NR ²⁹ , more preferably -O-. In addition, a deuterium-substituted form is also preferable.

The anthracene compound can be a compound having a reactive group at a desired position of the anthracene skeleton, and if it is an anthracene compound represented by formula (3-H), X, Ar ⁴ and a structure of formula (A), etc. A compound having a reactive group in part of its structure is used as a starting material, and it is produced using Suzuki coupling, Negishi coupling, or other known coupling reactions. As a reactive group of the said reactive compound, a halogen, boric acid, etc. are mentioned. As a specific production method, for example, the synthesis method in paragraphs [0089] to [0175] of International Publication No. 2014/141725 can be referred to.

<Fluorene compound>

The compound represented by formula (4-H) basically functions as a host.

[Chemical 101]

In formula (4-H),

R ¹ to R ¹⁰ are independently hydrogen, aryl, heteroaryl (the heteroaryl can be bonded to the fluorene skeleton in formula (4-H) via a linking group), diarylamino (two Aryl groups can be bonded to each other via a linking group), diheteroarylamino (two heteroaryl groups can be bonded to each other via a linking group), arylheteroarylamino (aryl and heteroaryl groups can be bonded to each other via a linking group) group), alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, at least one hydrogen in these may be substituted by aryl, heteroaryl, alkyl or cycloalkyl, and R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ or R ⁹ and R ¹⁰ can be independently bonded to form a condensed ring or Spiro rings, at least one hydrogen in the ring formed may be composed of aryl, heteroaryl (the heteroaryl may be bonded to the ring formed via a linker), diarylamino (two aryl can be bonded to each other via a linking group), diheteroarylamino (two heteroaryl groups can be bonded to each other via a linking group), arylheteroarylamino (aryl and heteroaryl can be bonded to each other via a linking group) Bonding), alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, at least one hydrogen in these can be substituted by aryl, heteroaryl, alkyl or cycloalkyl, the formula (4-H ) in the compound represented by at least one hydrogen may be replaced by halogen, cyano or deuterium.

The details of each group in the definition of formula (4-H) can refer to the description of the polycyclic aromatic compound of formula (1) mentioned above.

As the alkenyl group in ^R1 to ^R10 , for example, an alkenyl group having 2 to 30 carbon atoms is mentioned, preferably an alkenyl group having 2 to 20 carbon atoms, more preferably an alkenyl group having 2 to 10 carbon atoms, and even more preferably a carbon atom group. The alkenyl group having 2 to 6 carbon atoms is particularly preferably an alkenyl group having 2 to 4 carbon atoms. Preferred alkenyl groups are ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-butenyl, Pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl or 5-hexenyl.

In addition, as specific examples of the heteroaryl group, the following formula (4-Ar1), formula (4-Ar2), formula (4-Ar3), formula (4-Ar4) or formula (4-Ar5) can also be cited. A monovalent group represented by removing any hydrogen atom in the compound.

[chemical 102]

In formula (4-Ar1) to formula (4-Ar5), Y ¹ is independently O, S or NR, R is phenyl, biphenyl, naphthyl, anthracenyl or hydrogen, formula (4-Ar1) At least one hydrogen in the structure of formula (4-Ar5) may be substituted by phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

These heteroaryl groups may be bonded to the fluorene skeleton in formula (4-H) via a linking group. That is, the fluorene skeleton in the formula (4-H) and the heteroaryl group may be bonded not only directly but also through a linking group between them. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O-, or - OCH ₂ CH ₂ O- etc.

In addition, R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , R ⁵ and R ⁶ , R ⁶ and R ⁷ or R ⁷ and R ⁸ in formula (4-H) can be independently bonded Knot and form a fused ring, R ⁹ and R ¹⁰ may bond and form a spiro ring. The condensed ring formed by R ¹ to R ⁸ is a ring condensed on the benzene ring in formula (4-H), and is an aliphatic ring or an aromatic ring. It is preferably an aromatic ring, and examples of a structure including a benzene ring in formula (4-H) include a naphthalene ring, a phenanthrene ring, and the like. The spiro ring formed by R ⁹ and R ¹⁰ is a ring that is spiro-bonded on the five-membered ring in formula (4-H), and is an aliphatic ring or an aromatic ring. An aromatic ring is preferable, and a fluorene ring etc. are mentioned.

The compound represented by the formula (4-H) is preferably a compound represented by the following formula (4-H-1), formula (4-H-2) or formula (4-H-3), and is represented by the formula ( In 4-H), the compound formed by condensing the benzene ring formed by R ¹ and R ² bonded, the compound formed by the condensed benzene ring formed by R ³ and R ⁴ bonded in formula (4-H), in the formula (4-H) A compound in which none of R ¹ to R ⁸ is bonded.

[chem 103]

The definitions of R 1 to R ¹⁰ in formula (4-H-1), formula (4-H-2) and formula (4-H-3) are the same as the corresponding ^{R 1} to R ¹⁰ in formula (4-H) Similarly, the definitions of R ¹¹ to R ¹⁴ in formula (4-H-1) and formula (4-H-2) are also the same as those of R ¹ to R ¹⁰ in formula (4).

The compound represented by the formula (4-H) is further preferably a compound represented by the following formula (4-H-1A), formula (4-H-2A) or formula (4-H-3A), and the formulas are respectively (4-H-1), a compound in which R ⁹ and R ¹⁰ are bonded to form a spiro-fluorene ring in formula (4-H-2) or formula (4-H-3).

[chemical 104]

The definition of R ² to R ⁷ in formula (4-H-1A), formula (4-H-2A) and formula (4-H-3A) and formula (4-H-1), formula (4-H -2) and the corresponding R ² to R ⁷ in formula (4-H-3) are the same, and the definitions of R ¹¹ to R ¹⁴ in formula (4-H-1A) and formula (4-H-2A) It is also the same as R ¹¹ to R ¹⁴ in formula (4-H-1) and formula (4-H-2).

In addition, all or part of hydrogen in the compound represented by formula (4-H) may be substituted by halogen, cyano or deuterium.

As a more specific example of the fluorene compound which is the main body of this invention, the compound represented by the following structural formula is mentioned. In addition, Me represents a methyl group.

[chemical 105]

化合物>< dibenzo

Compound>

化合物例如为下述式(5-H)所表示的化合物。Dibenzo as main body

The compound is, for example, a compound represented by the following formula (5-H).

[chemical 106]

骨架键结)、二芳基氨基(两个芳基可相互经由连结基而键结)、二杂芳基氨基(两个杂芳基可相互经由连结基而键结)、芳基杂芳基氨基(芳基及杂芳基可相互经由连结基而键结)、烷基、环烷基、烯基、烷氧基或芳氧基，这些中的至少一个氢可由芳基、杂芳基、烷基或环烷基取代，另外，R¹至R¹⁶中的邻接的基彼此可键结而形成稠环，所形成的环中的至少一个氢可由芳基、杂芳基(所述杂芳基可经由连结基而与所述所形成的环键结)、二芳基氨基(两个芳基可相互经由连结基而键结)、二杂芳基氨基(两个杂芳基可相互经由连结基而键结)、芳基杂芳基氨基(芳基、杂芳基可相互经由连结基而键结)、烷基、环烷基、烯基、烷氧基或芳氧基取代，这些中的至少一个氢可由芳基、杂芳基、烷基或环烷基取代，式(5-H)所表示的化合物中的至少一个氢可由卤素、氰基或氘取代。In the formula (5-H), R ¹ to R ¹⁶ are independently hydrogen, aryl, heteroaryl (the heteroaryl can be connected with the dibenzo in the formula (5-H) via a linking group

Skeleton bonding), diarylamino (two aryl groups can be bonded to each other via a linking group), diheteroarylamino (two heteroaryl groups can be bonded to each other via a linking group), arylheteroaryl Amino (aryl and heteroaryl can be bonded to each other via a linking group), alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, at least one hydrogen in these can be represented by aryl, heteroaryl, Alkyl or cycloalkyl substitution, in addition, R ¹ to R ¹⁶ Adjacent bases can be bonded to each other to form a condensed ring, at least one hydrogen in the formed ring can be formed by aryl, heteroaryl (the heteroaryl group can be bonded to the formed ring via a linking group), diarylamino (two aryl groups can be bonded to each other via a linking group), diheteroarylamino (two heteroaryl groups can be bonded to each other via a linking group), linking group), arylheteroarylamino (aryl, heteroaryl can be bonded to each other via a linking group), alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy substitution, these At least one hydrogen in may be substituted by aryl, heteroaryl, alkyl or cycloalkyl, and at least one hydrogen in the compound represented by formula (5-H) may be substituted by halogen, cyano or deuterium.

The details of each group in the definition of formula (5-H) can refer to the description of the polycyclic aromatic compound of formula (1) mentioned above.

As the alkenyl group in the definition of the formula (5-H), for example, an alkenyl group having 2 to 30 carbon atoms, preferably an alkenyl group having 2 to 20 carbon atoms, more preferably an alkenyl group having 2 to 10 carbon atoms, and further It is preferably an alkenyl group having 2 to 6 carbon atoms, particularly preferably an alkenyl group having 2 to 4 carbon atoms. Preferred alkenyl groups are ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-butenyl, Pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

In addition, as specific examples of the heteroaryl group, the following formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) can also be cited. A monovalent group represented by removing any hydrogen atom in the compound.

[chemical 107]

In formula (5-Ar1) to formula (5-Ar5), Y ¹ is independently O, S or NR, R is phenyl, biphenyl, naphthyl, anthracenyl or hydrogen, formula (5-Ar1) At least one hydrogen in the structure of formula (5-Ar5) may be substituted by phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

骨架键结。即，式(5-H)中的二苯并

骨架与所述杂芳基不仅可直接键结，而且也可在这些之间经由连结基而键结。作为所述连结基，可列举：亚苯基、亚联苯基、亚萘基、亚蒽基、亚甲基、亚乙基、-OCH₂CH₂-、-CH₂CH₂O-、或-OCH₂CH₂O-等。These heteroaryl groups can be combined with the dibenzo in formula (5-H) via a linking group

Skeleton bonding. That is, the dibenzo in formula (5-H)

The skeleton and the heteroaryl group may be bonded not only directly but also via a linking group between them. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O- etc.

骨架键结)、甲基、乙基、丙基、或丁基。In the compound represented by formula (5-H), R ¹ , R ⁴ , R ⁵ , R ⁸ , R ⁹ , R ¹² , R ¹³ and R ¹⁶ are preferably hydrogen. In such cases, R ² , R ³ , R ⁶ , R ⁷ , R ¹⁰ , R ¹¹ , R ¹⁴ and R ¹⁵ in formula (5-H) are preferably independently hydrogen, phenyl, biphenyl , naphthyl, anthracenyl, phenanthrenyl, monovalent with the structure of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) (the monovalent group having said structure can be passed through phenylene, biphenylene, naphthylene, anthracene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O- and dibenzo in formula (5-H)

backbone bond), methyl, ethyl, propyl, or butyl.

The compound represented by formula (5-H) is more preferably R ¹ , R ² , R ⁴ , R ⁵ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹² , R ¹³ , R ¹⁵ and R ¹⁶ are hydrogen . In this case, at least one (preferably one or two, more preferably one) of R ³ , R ⁶ , R ¹¹ , and R ¹⁴ in formula (5-H) has a single bond intervening, phenylene , biphenylene, naphthylene, anthracene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O- or -OCH ₂ CH ₂ O- the formula (5-Ar1 ), the monovalent group of the structure of formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5), the at least one other than (that is, one with the structure other than the position substituted by the valent group) is hydrogen, phenyl, biphenyl, naphthyl, anthracenyl, methyl, ethyl, propyl or butyl, at least one hydrogen in these can be represented by phenyl, biphenyl, Naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl substitution.

In addition, as R ² , R ³ , R ⁶ , R ⁷ , R ¹⁰ , R ¹¹ , R ¹⁴ and R ¹⁵ in the formula (5-H), when selected, they have the formula (5-Ar1) to the formula (5-Ar5 ), in the case of a monovalent group of a structure represented by ), at least one hydrogen in the structure may be bonded to any one of R ¹ to R ¹⁶ in formula (5-H) to form a single bond.

化合物的更具体的例子，可列举以下的结构式所表示的化合物。此外，“tBu”表示叔丁基。The dibenzos that are the subject of the present invention

More specific examples of compounds include compounds represented by the following structural formulas. In addition, "tBu" represents a t-butyl group.

[chemical 108]

[chemical 109]

The materials for the light-emitting layer (host material and dopant material) can also be used as the following polymer compound or its polymer cross-linked body, or the following pendant type polymer compound or its pendant type polymer cross-linked body In the material for the light emitting layer, the polymer compound is a reactive compound obtained by substituting a reactive substituent in the material for the light emitting layer (host material and dopant material) and polymerized as a monomer The pendant polymer compound is formed by reacting the main chain polymer with the reactive compound.

<Light Emitting Layer Containing Auxiliary Dopant and Emissive Dopant>

The light-emitting layer in the organic electroluminescent device may contain a host compound as a first component, an auxiliary dopant (compound) as a second component, and an emitting dopant (compound) as a third component. The polycyclic aromatic compounds of the invention are also preferably used as emissive dopants. As an auxiliary dopant (compound), a thermally active delayed phosphor can be used.

In the following description, an organic electroluminescent element using a thermally activated delayed phosphor as an auxiliary dopant is sometimes referred to as a "TAF element" (Thermally Activated Delayed Fluorescence, TADF) assisted fluorescence (Assisting Fluorescence) ) prime sub). The "host compound" in the TAF element means that the lowest excited singlet energy level obtained from the shoulder peak on the short-wavelength side of the peak of the fluorescence spectrum is higher than that of the thermally active delayed phosphor as the second component and that of the third component. Compounds that emit dopants.

The so-called "thermally active delayed phosphor" refers to the reverse intersystem crossing from the lowest excited triplet state to the lowest excited singlet state by absorbing thermal energy, and radiation inactivation from the lowest excited singlet state, Compounds that delay fluorescence can thus be emitted. Here, the term "thermally activated delayed fluorescence" also includes a case where a higher-order triplet state is passed through in the excitation process from the lowest excited triplet state to the lowest excited singlet state. For example, the paper published by Monkman (Monkman) et al. of Durham (Durham) University (Nature-Communications (NATURE COMMUNICATIONS), 7: 13680, digital object unique identifier (digital object identifier, DOI): 10.1038 /ncomms13680), a paper published by Hosokai et al. from the National Institute of Advanced Industrial Technology (Hosokai et al., Science Advances, Sci.Adv. 2017; 3: e1603282), by Kyoto University A paper published by Sato et al. (Scientific Reports, 7:4820, DOI: 10.1038/s41598-017-05007-7) and a society publication also by Sato et al. of Kyoto University (Chemical Society of Japan 98th Spring annual meeting, publication number: 2I4-15, Mechanism of high-efficiency light emission in organic electroluminescence using diazaboranaphthoanthracene (DABNA) as a light-emitting molecule, Graduate School of Engineering, Kyoto University, etc. In the present invention, regarding a sample containing a target compound, the target compound was determined to be a "thermally active delayed phosphor" based on the observation of a slow fluorescence component when the fluorescence lifetime was measured at 300K. Here, the term "slow fluorescence component" refers to a component with a fluorescence lifetime of 0.1 μsec or more. The measurement of the fluorescence lifetime can be performed, for example, using a fluorescence lifetime measurement device (manufactured by Hamamatsu Photonics, C11367-01).

The polycyclic aromatic compound of the present invention can function as an emission dopant, and the "thermally active delayed phosphor" can function as an auxiliary dopant that assists the light emission of the polycyclic aromatic compound of the present invention.

FIG. 2 shows an energy level diagram of a light emitting layer of a TAF device using a general fluorescent dopant as an emitting dopant (ED). In the figure, the energy level of the ground state of the host (H) is E(1, G), and the lowest excited singlet energy level of the host obtained from the shoulder on the short-wavelength side of the fluorescence spectrum is E(1 , S, Sh), the lowest excited triplet energy level obtained from the shoulder peak on the short wavelength side of the phosphorescence spectrum of the host is E(1, T, Sh), and the auxiliary dopant ( The energy level of the ground state of AD) is E(2, G), and the lowest excited singlet energy level obtained from the shoulder peak on the short-wavelength side of the fluorescence spectrum of the auxiliary dopant as the second component is E(2, G). (2, S, Sh), assuming that the lowest excited triplet energy level obtained from the shoulder peak on the short wavelength side of the phosphorescence spectrum of the auxiliary dopant as the second component is E(2, T, Sh), The energy level of the ground state of the emissive dopant as the third component is E(3, G), and the lowest excitation singleton obtained from the shoulder peak on the short-wavelength side of the fluorescence spectrum of the emissive dopant as the third component is Let the heavy state energy level be E(3, S, Sh), and let the lowest excited triplet state energy level obtained from the shoulder peak on the short-wavelength side of the phosphorescence spectrum of the emitting dopant as the third component be E(3 , T, Sh), let holes be h ⁺ , electrons be e ^- , and fluorescence resonance energy transfer be FRET (Fluorence Resonance Energy Transfer). In the TAF element, in the case of using a general fluorescent dopant as the emitting dopant (ED), the energy converted from the auxiliary dopant (Up Conversion) is transferred to the lowest excited singlet state of the emitting dopant Energy level E (3, S, Sh) and emit light. However, a part of the lowest excited triplet level E(2,T,Sh) on the auxiliary dopant moves to the lowest excited triplet level E(3,T,Sh) of the emitting dopant, or in the emission dopant Intersystem crossing from the lowest excited singlet level E(3, S, Sh) to the lowest excited triplet level E(3, T, Sh) occurs on the agent, followed by thermal deactivation to the ground state E(3, G ). Due to the path, a part of the energy is not used for light emission, and waste of energy occurs.

On the other hand, in the organic electroluminescence device of this aspect, the energy transferred from the auxiliary dopant to the emission dopant can be efficiently used for light emission, thereby achieving high light emission efficiency. The reason for this is presumed to be the following light emission mechanism.

A preferred energy relationship in the organic electroluminescence element of this embodiment is shown in FIG. 3 . In the organic electroluminescence device of this aspect, the lowest excited triplet energy level E(3,T,Sh) of the compound having a boron atom as an emitting dopant is high. Thus, the lowest excited singlet energy upconverted by the auxiliary dopant, e.g. in the case of an intersystem crossing towards the lowest excited triplet level E(3,T,Sh) by the emissive dopant, is also emissively doped The lowest excited triplet energy level E(2, T, Sh) on the dopant is upconverted or recycled to the auxiliary dopant (thermally active delayed phosphor). Therefore, the generated excitation energy can be used for light emission without waste. In addition, it is expected that by distributing the functions of upconversion and light emission to two types of molecules in which each function is prominent, the residence time of high energy is reduced and the burden on the compound is reduced.

In this form, known compounds can be used as the host compound, for example, compounds having at least one of a carbazole ring and a furan ring can be used, and among them, at least one of a furyl group and a carbazole group and an A compound in which at least one of an aryl group and a heteroarylene group is bonded. Specific examples include mCP, mCBP, and the like.

From the viewpoint of promoting rather than hindering the generation of Thermally Activated Delayed Fluorescence (TADF) in the light-emitting layer, the lowest excited triplet energy of the host compound obtained from the shoulder peak on the short-wavelength side of the phosphorescence spectrum peak Level E(1,T,Sh) is preferably higher than the lowest excited triplet level E(2,T,Sh) of the emissive dopant or co-dopant having the highest lowest excited triplet level in the emissive layer , the lowest excited triplet energy level E(3, T, Sh), specifically, compared with E(2, T, Sh), E(3, T, Sh), the lowest excited triplet energy level of the host compound E(1, T, Sh) is preferably 0.01 eV or more, more preferably 0.03 eV or more, and still more preferably 0.1 eV or more. In addition, TADF-active compounds can also be used among the host compounds.

As the host compound, for example, a compound represented by any one of formula (H1), formula (H2) and formula (H3) can be used.

<Thermally active delayed phosphor (auxiliary dopant)>

The thermally active delayed phosphor (TADF compound) used in the TAF element is preferably a donor-acceptor type thermally active delayed phosphor (D-A type TADF compound) designed to use a donor called a donor. Electronic substituents and electron-accepting substituents called acceptors localize the highest occupied molecular orbital (Highest Occupied Molecular Orbital, HOMO) and the lowest unoccupied molecular orbital (Lowest Unoccupied Molecular Orbital, LUMO) , to produce efficient reverse intersystem crossing. Here, in this specification, an "electron-donating substituent" (donor) refers to a substituent and a partial structure in which a HOMO orbital partially exists in a thermally active delayed phosphor molecule, and an "electron-accepting substituent" The (acceptor) refers to a substituent and a partial structure in which a LUMO orbital partially exists in a thermoactive delayed phosphor molecule.

In general, thermally active delayed phosphors using donors or acceptors have large spin-orbit coupling (SOC: Spin Orbit Coupling) due to structural reasons, and the exchange interaction between HOMO and LUMO is small, and ΔE(ST) is small. Therefore, very fast reverse intersystem crossing speeds can be obtained. On the other hand, thermally active delayed phosphors using donors or acceptors have greater structural relaxation in the excited state (in a certain molecule, the stable structure in the ground state is different from that in the excited state, so if an external stimulus occurs From the conversion from the ground state to the excited state, the subsequent structure changes to a stable structure in the excited state), thereby providing a wide luminous spectrum, so when used as a luminescent material, the color purity may be reduced.

However, high color purity can be provided by using an appropriate emission dopant such as the polycyclic aromatic compound of the present invention as an auxiliary dopant together with a thermally active retarded phosphor using a donor or an acceptor.

The TADF material may be any compound whose emission spectrum at least partially overlaps with the absorption spectrum of the polycyclic aromatic compound of the present invention. The polycyclic aromatic compound of the present invention and the TADF material may both be included in the same layer, or may be included in adjacent layers.

As the thermally active delayed phosphor in the TAF element, for example, a compound in which a donor and an acceptor are bonded directly or via a spacer can be used. As the electron-donating group (donor structure) and electron-accepting group (acceptor structure) used in the thermally active delayed phosphor of the present invention, for example, Chemistry of Materials, 2017 can be used. , 29, 1946-1963 for the structure described. Examples of donor structures include carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, and benzothienocarbazole. Azole, phenylindolocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, Dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(tert-butylphenyl)amine, N ¹ -(4-(diphenylamino)phenyl)-N ⁴ , N ⁴ -diphenylbenzene-1,4-diamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydro-indenacridine and diphenyl-dihydrodibenzo Azasiloline, etc. Examples of acceptor structures include: sulfonyldiphenyl, benzophenone, phenylene bis(phenylphenone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile , terephthalonitrile, benzenetricyanonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzoxazole, benzobis(oxazole), quinoline, benzo Imidazole, dibenzoquinoxaline, heptaazepine, thioxanthone dioxide, dimethylanthrone, anthracedione, 5H-cyclopenta[1,2-b:5,4-b' ]bipyridine, fluorene dicarbonitrile, triphenyl triazine, pyrazine dicarbonitrile, pyrimidine, phenyl pyrimidine, methyl pyrimidine, pyridine dicarbonitrile, dibenzoquinoxaline dicarbonitrile, bis(phenyl Sulfonyl)benzene, dimethylthioxanthene dioxide, thianthracene tetroxide, and tris(dimethylphenyl)borane. In particular, the compound with thermally active delayed fluorescence in the TAF element preferably has a compound selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, m- A compound having at least one of phthalonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole and benzophenone as a partial structure.

The compound used as the second component of the light emitting layer in the TAF element is a thermally active delayed phosphor, and is preferably a compound whose light emission spectrum overlaps at least a part of the absorption peak of the light emitting dopant. Compounds that can be used as the second component (thermally active delayed phosphor) of the light emitting layer in the TAF device are exemplified below. However, compounds usable as thermally active delayed phosphors in the TAF element are not limited to those exemplified below. In the following formulae, Me represents a methyl group, tBu represents a tert-butyl group, and wavy lines represent bonding positions.

[chemical 110]

[chem 111]

[chem 112]

[chem 113]

[chem 114]

Furthermore, as a thermally active delayed phosphor, a compound represented by any one of the following formula (AD1), formula (AD2) and formula (AD3) can also be used.

[chem 115]

In the formula (AD1), formula (AD2) and formula (AD3), M is independently a single bond, -O-, >N-Ar or >CAr ₂ , in terms of the depth of the HOMO of the formed partial structure and From the viewpoint of the height of the lowest excited singlet level and the lowest excited triplet level, single bond, -O- or >N-Ar is preferable. J is a spacer structure separating the donor partial structure and the acceptor partial structure, and each independently is an arylene group having 6 to 18 carbon atoms, so that the donor partial structure and the acceptor partial structure From the viewpoint of the size of the conjugation that the partial structure bleeds out, it is preferably an arylene group having 6 to 12 carbon atoms. More specifically, phenylene, methylphenylene, and dimethylphenylene are mentioned. Q is each independently =C(-H)- or =N-, from the viewpoint of the shallowness of the LUMO of the formed partial structure and the height of the lowest excited singlet state energy level and the lowest excited triplet state energy level, Preferably =N-. Ar is independently hydrogen, an aryl group with 6 to 24 carbons, a heteroaryl group with 2 to 24 carbons, an alkyl group with 1 to 12 carbons, or a cycloalkyl group with 3 to 18 carbons. From the viewpoint of the depth of the HOMO of the structure and the height of the lowest excited singlet state energy level and the lowest excited triplet state energy level, hydrogen, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 2 to 14 carbon atoms, An alkyl group with 1 to 4 carbons or a cycloalkyl group with 6 to 10 carbons, more preferably hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, Triazinyl, carbazolyl, dimethylcarbazolyl, di-tert-butylcarbazolyl, benzimidazolyl or phenylbenzimidazolyl, more preferably hydrogen, phenyl or carbazolyl. m is 1 or 2. n is an integer of (6-m) or less, and is preferably an integer of 4 to (6-m) from the viewpoint of steric hindrance. Furthermore, at least one hydrogen in the compounds represented by the above formulas may be replaced by halogen or deuterium.

More specifically, the compound used as the second component of this form is preferably 4CzBN, 4CzBN-Ph, 5CzBN, 3Cz2DPhCzBN, 4CzIPN, 2PXZ-TAZ, Cz-TRZ3, BDPCC-TPTA, MA-TA, PA-TA, FA - TA, PXZ-TRZ, DMAC-TRZ, BCzT, DCzTrz, DDCzTRz, spiro AC-TRZ, Ac-HPM, Ac-PPM, Ac-MPM, TCzTrz, TmCzTrz and DCzmCzTrz.

The compound used as the second component of this form may be a donor-acceptor type TADF compound represented by D-A in which one donor D is directly bonded to one acceptor A or bonded via a linking group. A compound having a structure represented by the following formula (DAD1) that is bonded or bonded to one acceptor A via a linking group is a compound having better characteristics of an organic electroluminescence device, and is therefore preferable.

(D ¹ -L ¹ )nA ¹ (DAD1)

Compounds represented by the following formula (DAD2) are included in formula (DAD1).

D ² -L ² -A ² -L ³ -D ³ (DAD2)

In formula (DAD1) and formula (DAD2), D ¹ , D ² and D ³ each independently represent a donor group. As the donor group, the above-mentioned donor structure can be used. A ¹ and A ² each independently represent an acceptor group. The acceptor structure can be used as the acceptor group. L ¹ , L ² and L ³ each independently represent a single bond or a conjugated linking group. The conjugated linking group is a spacer structure separating the donor group and the acceptor group, and is preferably an arylene group having 6 to 18 carbon atoms, more preferably an arylene group having 6 to 12 carbon atoms. L ¹ , L ² and L ³ are more preferably each independently phenylene, methylphenylene or dimethylphenylene. n in the formula (DAD1) is not less than 2 and represents an integer not greater than the maximum number of substitutable A1. n can be selected in the range of 2-10, or can be selected in the range of 2-6, for example. When n is 2, it is a compound represented by formula (DAD2). The n pieces of D ¹ may be the same or different, and the n pieces of L ¹ may be the same or different. Preferable specific examples of the compounds represented by formula (DAD1) and formula (DAD2) include 2PXZ-TAZ and the following compounds, and the second component usable in the present invention is not limited to these compounds.

[chem 116]

In this aspect, the light emitting layer may be a single layer or may include multiple layers. In addition, the host compound, the thermally active delayed phosphor, and the polycyclic aromatic compound of the present invention may be contained in the same layer, or at least one of each component may be contained in multiple layers. The host compound, the thermally active delayed phosphor, and the polycyclic aromatic compound of the present invention contained in the light-emitting layer may each be one type, or a combination of multiple types, or any of them. The auxiliary dopant and the emitting dopant may be contained in the whole host compound as a host, or may be included in a part of the host compound as a host. The light-emitting layer doped with the auxiliary dopant and the emission dopant can be formed by the following method, the host compound, the auxiliary dopant and the emission dopant are formed into a film by the ternary co-evaporation method; A method in which a compound, an auxiliary dopant, and an emission dopant are mixed in advance and then vapor-deposited simultaneously; coating a composition for forming a light-emitting layer prepared by dissolving the host compound, the auxiliary dopant, and the emission dopant in an organic solvent ( Coating) wet film-forming method, etc.

The usage-amount of a host compound differs with the kind of host compound, What is necessary is just to decide according to the characteristic of the said host compound. The amount of the host compound used is preferably 40% to 99% by mass, more preferably 50% to 98% by mass, and still more preferably 60% to 95% by mass of the entire light-emitting layer material. If it is the said range, it is preferable from the point of efficient charge transport and efficient energy transfer to a dopant, for example.

The amount of the auxiliary dopant (thermally active retardation phosphor) used varies depending on the type of the auxiliary dopant, and may be determined according to the characteristics of the auxiliary dopant. The reference amount of the auxiliary dopant is preferably 1% by mass to 60% by mass, more preferably 2% by mass to 50% by mass, and still more preferably 5% by mass to 30% by mass of the entire light emitting layer material. If it is within the above-mentioned range, it is preferable in terms of efficiently transferring energy to the emission dopant, for example.

The amount of the emissive dopant (compound having a boron atom) used varies depending on the type of the emissive dopant, and may be determined according to the characteristics of the emissive dopant. The standard of the amount of the emission dopant used is preferably 0.001% by mass to 30% by mass, more preferably 0.01% by mass to 20% by mass, and still more preferably 0.1% by mass to 10% by mass of the entire material for the light emitting layer. If it is the said range, it is preferable at the point which can prevent a concentration quenching phenomenon, for example.

In terms of preventing the concentration quenching phenomenon, it is preferable that the emission dopant is used in a low concentration. From the viewpoint of the efficiency of the thermally active delayed fluorescence mechanism, it is preferable that the auxiliary dopant be used in a high concentration. Furthermore, from the viewpoint of the efficiency of the thermally active delayed fluorescence mechanism of the auxiliary dopant, it is preferable that the usage amount of the emission dopant is lower than the usage amount of the auxiliary dopant.

<2-1-3. Substrate in organic electroluminescence element>

The substrate 101 is a support for the organic EL element 100, and generally, quartz, glass, metal, plastic, or the like can be used. The substrate 101 is formed into a plate shape, a film shape, or a sheet shape depending on the purpose, and for example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like can be used. Among them, glass plates and plates made of transparent synthetic resins such as polyester, polymethacrylate, polycarbonate, and polysulfone are preferable. If it is a glass substrate, soda-lime glass, non-alkali glass, etc. can be used, and the thickness only needs to be sufficient to maintain mechanical strength, so it only needs to be 0.2 mm or more, for example. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. As for the material of the glass, since the eluted ions from the glass should be less, it is preferably an alkali-free glass. Since soda-lime glass with a barrier coat (barrier coat) such as _SiO2 is also commercially available, the above-mentioned glass can be used. Soda lime glass. In addition, in order to improve the gas barrier properties, a gas barrier film such as a fine silicon oxide film may be provided on at least one surface of the substrate 101, and a synthetic resin plate, film or sheet with low gas barrier properties may be used as the substrate 101. In this case, it is particularly preferable to provide a gas barrier film.

<2-1-4. Anode in organic electroluminescence element>

The anode 102 plays a role of injecting holes into the light emitting layer 105 . In addition, when either the hole injection layer 103 or the hole transport layer 104 is provided between the anode 102 and the light emitting layer 105, holes are injected into the light emitting layer 105 through these layers.

Examples of materials forming the anode 102 include inorganic compounds and organic compounds. Examples of inorganic compounds include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxides, tin oxides, indium-tin oxides (Indium Tin Oxide, ITO) , Indium Zinc Oxide, IZO, etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass or NESA glass, etc. Examples of the organic compound include polythiophenes such as poly(3-methylthiophene), conductive polymers such as polypyrrole and polyaniline, and the like. Moreover, it can select suitably and use from the substance used as the anode of an organic EL element.

The resistance of the transparent electrode is not limited as long as it can supply a sufficient current for the light emission of the light emitting element, but it is preferably low resistance from the viewpoint of power consumption of the light emitting element. For example, if it is an ITO substrate of 300 Ω/Y or less, it will function as an element electrode, but it is also possible to supply a substrate of about 10 Ω/Y at present, so it is particularly desirable to use, for example, 10 Ω/Y to 5 Ω/Y, preferably 50 Ω /Υ～5Ω/Υ low resistance product. The thickness of ITO can be arbitrarily selected according to the resistance value, but it is usually used between 50nm and 300nm.

<2-1-5. Hole injection layer and hole transport layer in organic electroluminescence element>

The hole injection layer 103 plays a role of efficiently injecting holes migrated from the anode 102 into the light emitting layer 105 or into the hole transport layer 104 . The hole transport layer 104 plays a role of efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 through the hole injection layer 103 to the light emitting layer 105 . The hole injection layer 103 and the hole transport layer 104 are formed by stacking and mixing one or more than two kinds of hole injection/transport materials, or are formed by a mixture of hole injection/transport materials and a polymer binder. . Alternatively, an inorganic salt such as iron(III) chloride may be added to the hole injection/transport material to form a layer.

As a hole injecting/transporting substance, it is necessary to efficiently inject/transport holes from the positive electrode between electrodes to which an electric field is applied, and it is desirable to have high hole injection efficiency and efficiently transport the injected holes. Therefore, it is preferable to use a substance having a small ionization potential, a high hole mobility, excellent stability, and less generation of impurities that become traps during production and use.

As materials for forming the hole injection layer 103 and the hole transport layer 104, compounds conventionally used as charge transport materials for holes among photoconductive materials, p-type semiconductors, hole injection layers of organic EL elements, and Arbitrary compounds are selected from known compounds used in the hole transport layer. Specific examples of these compounds are carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), bis(N-arylcarbazole) or bis(N-alkylcarbazole) and other biscarbazole derivatives , triarylamine derivatives (4,4′,4″-tris(N-carbazolyl)triphenylamine, polymers with aromatic tertiary amino groups on the main chain or side chains, 1,1-bis (4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-bis(3-methylphenyl )-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1' -Diamine, N ⁴ , N ^4′ -diphenyl- ^{N 4} , N ^4′ -bis(9-phenyl-9H-carbazol-3-yl)-[1,1′-biphenyl]- 4,4'-diamine, N ⁴ , N ⁴ , N ^4' , N ^4' -tetrakis[1,1'-biphenyl]-4-yl-[1,1'-biphenyl]-4, 4′-diamine, 4,4′,4″-tris(3-methylphenyl(phenyl)amino)triphenylamine and other triphenylamine derivatives, starburst amine derivatives, etc.), di Styrene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives or thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (such as 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonnitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilane, etc. . Among the polymer systems, polycarbonate or styrene derivatives, polyvinylcarbazole, polysilane, etc. having the above-mentioned monomers on the side chain are preferable, but as long as it forms a thin film required for the production of a light-emitting element and can be The compound capable of injecting holes from the anode and then transporting holes is not particularly limited.

In addition, it is also known that the conductivity of organic semiconductors is strongly affected by doping. Such an organic semiconductor matrix material includes a compound having a good electron donating property or a compound having a good electron accepting property. In order to dope electron-donating substances, tetracyanoquinodimethane (Tetracyanoquinodimethane, TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinodimethane (2,3,5 , 6-tetrafluorotetracyano-1, 4-benzoquinodimethane, F4TCNQ) and other strong electron acceptors (for example, refer to the literature "M. Pfeiffer, A. Bayer, T. Fritz, K. Leo (M.Pfeiffer, A .Beyer, T.Fritz, K.Leo), "Appl.Phys.Lett.", 73(22), 3202-3204(1998)" and the literature "J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo (J.Blochwitz, M.Pfeiffer, T.Fritz, K.Leo), Appl.Phys.Lett., 73 (6), 729-731 (1998)"). They generate so-called holes by electron transfer processes in electron-donating base substances (hole-transporting substances). The conductivity of the base substance varies considerably depending on the number and mobility of holes. As a host substance having hole transport properties, for example, benzidine derivatives (N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)benzidine (N,N '-bis(3-methylphenyl)-N, N'-bis(phenyl)benzidine, TPD) etc.) or starburst amine derivatives (4,4',4"-tris(N,N-diphenylamino ) triphenylamine (4,4′,4″-tris(N,N-diphenylamino)triphenylamine, TDATA), etc.), or specific metal phthalocyanines (especially zinc phthalocyanine (ZnPc) etc.) (Japanese Patent Laid-Open 2005- Bulletin No. 167175). The polycyclic aromatic compound of the present invention can also be used as a material for forming a hole injection layer or a material for forming a hole transport layer.

<2-1-6. Electron blocking layer in organic electroluminescence element>

An electron blocking layer that prevents diffusion of electrons from the light emitting layer may be provided between the hole injection/transport layer and the light emitting layer. Formation of an electron blocking layer can use the compound represented by any one of said formula (H1), formula (H2), and formula (H3). The polycyclic aromatic compound of the present invention can be used as a material for forming an electron blocking layer.

<2-1-7. Electron injection layer and electron transport layer in organic electroluminescence element>

The electron injection layer 107 plays a role of efficiently injecting electrons transferred from the cathode 108 into the light emitting layer 105 or into the electron transport layer 106 . The electron transport layer 106 plays a role of efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 via the electron injection layer 107 to the light emitting layer 105 . The electron transport layer 106 and the electron injection layer 107 are formed by laminating or mixing one or two or more electron transport/injection materials, or a mixture of an electron transport/injection material and a polymer binder.

The electron injection/transport layer is a layer responsible for injecting electrons from the cathode and transporting electrons. It is desirable that the electron injection efficiency is high and the injected electrons be efficiently transported. Therefore, it is preferable to use a substance that has a high electron affinity, a high electron mobility, excellent stability, and is less likely to generate impurities that become traps during production and use. However, in consideration of the transport balance between holes and electrons, when the role of effectively preventing holes from the anode from flowing to the cathode side without recombination is mainly exerted, even if the electron transport ability is not so high, the It has the same effect of improving luminous efficiency as a material with high electron transport ability. Therefore, the electron injection/transport layer in this embodiment may also include the function of a layer capable of efficiently preventing hole transfer.

As the material (electron transport material) forming the electron transport layer 106 or the electron injection layer 107, a compound conventionally used as an electron transport compound in photoconductive materials, an electron injection layer and an electron transport layer of an organic EL element can be used. Arbitrarily selected from known compounds used are used.

As the material used in the electron transport layer or the electron injection layer, it is preferable to contain at least one compound selected from the following compounds: compounds containing one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus Aromatic ring or heteroaromatic ring compounds; pyrrole derivatives and fused ring derivatives thereof; and metal complexes having electron-accepting nitrogen. Specifically, condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives represented by 4,4'-bis(diphenylvinyl)biphenyl, purple Cyclic ketone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone or diphenoquinone, phosphorus oxide derivatives, aryl nitrile derivatives and indole derivatives, etc. Examples of metal complexes having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, amethymine complexes, tropolone metal complexes, and flavones. Alcohol metal complexes and benzoquinoline metal complexes, etc. These materials can be used alone or mixed with different materials.

In addition, as specific examples of other electron transport compounds, pyridine derivatives, naphthalene derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, phenanthroline derivatives, perionone derivatives, coumarin derivatives, ketone derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (1,3-bis[(4- tert-butylphenyl) 1,3,4-oxadiazolyl]phenylene, etc.), thiophene derivatives, triazole derivatives (N-naphthyl-2,5-diphenyl-1,3,4- triazole, etc.), thiadiazole derivatives, metal complexes of 8-hydroxyquinoline (oxine) derivatives, oxine-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives , indole (benzazole) compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (2,2'- Bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (tri(N-phenylbenzene imidazol-2-yl) benzene, etc.), benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, quinoline derivatives, terpyridine and other oligopyridine derivatives, bipyridine derivatives, terpyridine derivatives (1,3-bis(2,2′:6′,2″-terpyridine-4′-yl)benzene, etc.), naphthyridine derivatives (bis(1-naphthyl)-4-(1,8 -naphthyridin-2-yl) phenylphosphine oxide, etc.), aldehyde azine derivatives, pyrimidine derivatives, aryl nitrile derivatives, indole derivatives, phosphine oxide derivatives, bistyryl derivatives, silole Derivatives and oxazoline derivatives, etc.

In addition, metal complexes having electron-accepting nitrogen can also be used, for example, hydroxyquinoline-based metal complexes, hydroxyphenyloxazole complexes and other hydroxyazole complexes, and imine complexes , cycloheptatrienolone metal complexes, flavonol metal complexes and benzoquinoline metal complexes, etc.

Said materials can be used alone or mixed with different materials.

Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, and aryl nitrile derivatives are preferred. , triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, hydroxyquinoline metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives and oxazoline derivatives.

The polycyclic aromatic compound of the present invention can also be used as a material for forming an electron injection layer or a material for forming an electron transport layer.

A substance capable of reducing the material forming the electron transport layer or the electron injection layer may also be contained in the electron transport layer or the electron injection layer. As long as the reducing substance has certain reducing properties, various substances can be used, for example, it can be preferably used selected from alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, Oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals and organic complexes of rare earth metals at least one of the group.

As a preferable reducing substance, alkali metals such as Na (work function 2.36eV), K (work function 2.28eV), Rb (work function 2.16eV) or Cs (work function 1.95eV), or Ca (work function 2.9 Alkaline earth metals such as eV), Sr (work function 2.0 eV to 2.5 eV), or Ba (work function 2.52 eV), are particularly preferably those whose work function is 2.9 eV or less. Among these, a more preferable reducing substance is K, Rb or Cs which is an alkali metal, more preferably Rb or Cs, and most preferably Cs. These alkali metals have particularly high reducing power, and by adding a relatively small amount of these alkali metals to the material forming the electron transport layer or electron injection layer, it is possible to improve the luminance or prolong the life of the organic EL device. In addition, as a reducing substance having a work function of 2.9 eV or less, a combination of two or more of these alkali metals is also preferable, and a combination including Cs is particularly preferable, such as Cs and Na, Cs and K, Cs and Rb, or Cs and Na and K combination. By including Cs, the reduction ability can be efficiently exhibited, and by adding to the material forming the electron transport layer or the electron injection layer, it is possible to improve the emission luminance or prolong the life of the organic EL element.

<2-1-8. Cathode in organic electroluminescent element>

The cathode 108 plays a role of injecting electrons into the light emitting layer 105 via the electron injection layer 107 and the electron transport layer 106 .

The material forming the cathode 108 is not particularly limited as long as it is capable of efficiently injecting electrons into the organic layer, and the same material as that forming the anode 102 can be used. Among them, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium or alloys thereof (magnesium-silver alloy, magnesium - aluminum-lithium alloys such as indium alloys, lithium fluoride/aluminum, etc.), etc. In order to enhance the electron injection efficiency and improve device characteristics, lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective. Generally speaking, however, these low work function metals are unstable in the atmosphere in most cases. In order to improve this point, for example, a method of doping an organic layer with a trace amount of lithium, cesium, or magnesium and using a highly stable electrode is known. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide can also be used. However, it is not limited to these.

Furthermore, the following can be cited as a preferable example: in order to protect the electrodes, metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, and inorganic materials such as silicon dioxide, titanium dioxide, and silicon nitride, etc. substances, polyvinyl alcohol, vinyl chloride, hydrocarbon-based polymers, etc. for lamination. The method for producing these electrodes is not particularly limited as long as it is a method that can achieve conduction, such as resistance heating, electron beam vapor deposition, sputtering, ion plating, and coating.

<2-1-9. Adhesives that can be used in each layer>

The materials used in the above hole injection layer, hole transport layer, light-emitting layer, electron transport layer, and electron injection layer can form each layer independently, and can also be dispersed in polyvinyl chloride, polyvinyl chloride as a polymer binder. Carbonate, polystyrene, poly(N-vinylcarbazole), polymethylmethacrylate, polybutylmethacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin , phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, acrylonitrile-butadiene-styrene (Acrylonitrile Butadiene Styrene, ABS) resin, polyurethane resin and other solvent-soluble resins, or phenol Resins, xylene resins, petroleum resins, urea resins, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, silicone resins and other curable resins.

<2-1-10. Manufacturing method of organic electroluminescent device>

Each layer constituting an organic EL element can be formed by using methods such as evaporation, resistance heating evaporation, electron beam evaporation, sputtering, molecular lamination, printing, inkjet, spin coating, casting, or coating. The material constituting each layer is formed as a thin film. The film thickness of each layer formed in this manner is not particularly limited and can be appropriately set according to the properties of the material, but is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured with a crystal oscillator type film thickness measuring device or the like. When thinning is performed using a vapor deposition method, the vapor deposition conditions vary depending on the type of material, the target crystal structure and association structure of the film, and the like. The vapor deposition conditions are usually preferably at a boat heating temperature of +50°C to +400°C, a vacuum degree of 10 ^-6 Pa to 10 ^-3 Pa, a vapor deposition rate of 0.01nm/sec to 50nm/sec, and a substrate temperature of -150°C to + 300° C. and a film thickness of 2 nm to 5 μm are appropriately set.

Next, as an example of a method of producing an organic EL device, an organic EL device comprising an anode/hole injection layer/hole transport layer/light emitting layer containing a host material and a dopant material/electron transport layer/electron injection layer/cathode The method of making the components will be described. On a suitable substrate, a thin film of an anode material is formed by vapor deposition or the like to produce an anode, and then thin films of a hole injection layer and a hole transport layer are formed on the anode. On the thin film, the host material and the dopant material are co-evaporated to form a thin film as a light-emitting layer, and an electron transport layer and an electron injection layer are formed on the light-emitting layer, and then formed by vapor deposition and the like. A thin film of the substance is used as a cathode, thereby obtaining the target organic EL element. In addition, in the production of the organic EL element, the production order may be reversed, and the cathode, electron injection layer, electron transport layer, light emitting layer, hole transport layer, hole injection layer, and anode may be produced in this order.

When applying a DC voltage to the organic EL element obtained in the above manner, it is sufficient to apply a positive polarity to the anode and a negative polarity to the negative electrode. If a voltage of about 2V to 40V is applied, the Luminescence was observed from the transparent or translucent electrode side (anode or cathode, and both). In addition, the organic EL element emits light even when a pulse current or an alternating current is applied. In addition, the waveform of the applied alternating current may be arbitrary.

<2-1-11. Application example of organic electroluminescent element>

Organic EL elements can also be applied to display devices, lighting devices, and the like.

A display device or a lighting device including an organic EL element can be manufactured by a known method such as connecting an organic EL element to a known driving device, and a known driving method such as DC driving, pulse driving, or AC driving can be appropriately used to drive.

As the display device, for example, panel displays such as color flat panel displays, flexible displays such as flexible color organic electroluminescent (EL) displays, etc. 321546, Japanese Patent Laid-Open No. 2004-281086, etc.). Moreover, as a display method of a display, any one of a matrix method and a segment method, etc. are mentioned, for example. In addition, matrix display and segment display can coexist in the same panel.

In a matrix, pixels for display are two-dimensionally arranged in a grid or a mosaic, and characters or images are displayed by a collection of pixels. The shape or size of a pixel is determined according to the application. For example, for displaying images and characters on personal computers, monitors, and televisions, quadrilateral pixels with one side of 300 μm or less are generally used, and in the case of large displays such as display panels, pixels with one side of mm order are used. In the case of monochrome display, it is only necessary to arrange pixels of the same color. In the case of color display, red, green, and blue pixels are arranged side by side for display. In the above cases, there are typically triangle type and stripe type. Also, as the driving method of the matrix, either a line-sequential driving method or an active matrix may be used. Line-sequential driving has the advantage of being simple in structure, but in consideration of operating characteristics, active matrix may be superior, so the driving method must be differentiated according to the application.

In the segment method (type), a pattern is formed to display predetermined information, and the predetermined area is made to emit light. For example, time and temperature displays in digital clocks and thermometers, operating status displays in audio equipment and induction cookers, and panel displays in automobiles can be cited.

As the lighting device, for example, lighting devices such as indoor lighting, backlights of liquid crystal display devices, etc. (for example, refer to Japanese Patent Application Laid-Open No. Bulletin, etc.). Backlights are mainly used to improve the visibility of display devices that do not emit light, and are used in liquid crystal display devices, clocks, audio devices, automotive panels, display panels, signs, and the like. In particular, as a backlight for personal computers where thinning is a problem in liquid crystal display devices, considering that it is difficult to reduce the thickness of conventional methods due to the inclusion of fluorescent lamps or light guide plates, backlights using organic EL elements have thin, Lightweight feature.

<2-2. Other organic devices>

The polycyclic aromatic compound of the present invention can be used not only in the organic electroluminescence element, but also in the manufacture of organic field effect transistors or organic thin film solar cells.

An organic field effect transistor is a transistor that uses an electric field generated by a voltage input to control current, and is provided with a gate electrode in addition to a source electrode and a drain electrode. An organic field-effect transistor is a transistor that generates an electric field when a voltage is applied to a gate electrode, and can arbitrarily block the flow of electrons (or holes) flowing between a source electrode and a drain electrode to control current flow. Field effect transistors are easier to miniaturize than single transistors (bipolar transistors), and are often used as elements constituting integrated circuits and the like.

Regarding the structure of an organic field-effect transistor, generally, only a source electrode and a drain electrode are arranged in contact with the organic semiconductor active layer formed using the polycyclic aromatic compound of the present invention, and then an insulating layer in contact with the organic semiconductor active layer is interposed. (dielectric layer) to provide the gate electrode. As the element structure, the following structures are mentioned, for example.

(1) Substrate/gate electrode/insulator layer/source electrode and drain electrode/organic semiconductor active layer

(2) Substrate/gate electrode/insulator layer/organic semiconductor active layer/source electrode and drain electrode

(3) Substrate/organic semiconductor active layer/source electrode and drain electrode/insulator layer/gate electrode

(4) Substrate/source electrode and drain electrode/organic semiconductor active layer/insulator layer/gate electrode

The organic field effect transistor constructed in the above manner can be used as a liquid crystal display of an active matrix driving method, or a pixel driving switching element of an organic electroluminescence display, and the like.

An organic thin film solar cell has a structure in which an anode such as ITO, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode are laminated on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compound of the present invention can be used as a material for a hole transport layer, a p-type semiconductor layer, an n-type semiconductor layer, or an electron transport layer depending on its physical properties. In an organic thin film solar cell, the polycyclic aromatic compound of the present invention can function as a hole transport material or an electron transport material. The organic thin film solar cell may suitably include a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, etc. in addition to the above layers. In the organic thin film solar cell, known materials used in the organic thin film solar cell can be appropriately selected and used in combination.

<3. Wavelength conversion material>

The polycyclic aromatic compounds of the present invention are useful as wavelength conversion materials.

Currently, we are actively studying the application of multicolor technology based on color conversion methods to liquid crystal displays, organic EL displays, lighting, etc. The so-called color conversion is to convert the luminescence from a luminous body into light with a longer wavelength, for example, it means converting ultraviolet light or blue light into green light or red luminescence. The wavelength conversion material having the color conversion function is formed into a film and combined with, for example, a blue light source, so that the three primary colors of blue, green, and red can be extracted from the blue light source, that is, white light can be extracted. A full color display (full color display) can be fabricated by combining such a white light source that combines a blue light source with a wavelength conversion film having a color conversion function as a light source unit, and combining it with a liquid crystal driver and a color filter. In addition, if there is no liquid crystal driving part, it can be directly used as a white light source, for example, it can be used as a white light source for light-emitting diode (light-emitting diode, LED) lighting and the like. In addition, by using a blue organic EL element as a light source and combining it with a wavelength conversion film that converts blue light into green light and red light, a full-color organic EL display that does not use a metal mask can be fabricated. Furthermore, a low-cost full-color micro-LED display can be produced by using a blue micro-LED as a light source in combination with a wavelength conversion film that converts blue light into green light and red light.

The polycyclic aromatic compound of the present invention can be used as the wavelength conversion material. The wavelength conversion material containing the polycyclic aromatic compound of the present invention can be used to convert ultraviolet light or light from a light source or a light-emitting element that generates blue light with a shorter wavelength into a light suitable for use in a display device (a display device using an organic EL element). Or liquid crystal display device) blue light or green light with high color purity. The color to be converted can be adjusted by appropriately selecting the substituent of the polycyclic aromatic compound of the present invention, the binder resin used in the wavelength conversion composition described later, and the like. The wavelength conversion material is produced as a composition for wavelength conversion containing the polycyclic aromatic compound of the present invention. In addition, a wavelength conversion film can also be formed using the composition for wavelength conversion.

The composition for wavelength conversion may contain a binder resin, other additives, and a solvent in addition to the polycyclic aromatic compound of the present invention. As the binder resin, for example, resins described in paragraphs 0173 to 0176 of International Publication No. 2016/190283 can be used. As other additives, compounds described in paragraphs 0177 to 0181 of International Publication No. 2016/190283 can be used. As the solvent, the description of the solvent contained in the composition for forming a light-emitting layer can be referred to.

The wavelength conversion film includes a wavelength conversion layer formed by curing the wavelength conversion composition. As a method for producing the wavelength conversion layer from the wavelength conversion composition, known film formation methods can be referred to. The wavelength conversion film may include only the wavelength conversion layer formed from the composition containing the polycyclic aromatic compound of the present invention, and may also include other wavelength conversion layers (for example, a wavelength conversion layer that converts blue light into green light or red light, A wavelength conversion layer that converts blue or green light into red light). Furthermore, the wavelength conversion film may also include a base layer or a barrier layer for preventing the color conversion layer from deteriorating due to oxygen, moisture, or heat.

[Example]

Hereinafter, although an Example demonstrates this invention more concretely, this invention is not limited to these Examples.

Synthesis Example (1): Synthesis of Compound (1-1)

[chem 117]

Under nitrogen atmosphere, intermediate (X-1) (57.8g), 1-tert-butyl-3,4,5-trichlorobenzene (23.8g), dichlorobis[di-tert-butyl Base (4-dimethylaminophenyl) phosphino] palladium (II) (Pd-132, 0.909g), sodium tert-butoxide (NaOtBu, 14.4g) and toluene (500ml) were put into a flask and heated at 110°C Heat for 5 hours. After completion of the reaction, water and ethyl acetate were added to the reaction liquid and stirred, and the organic layer was separated and washed with water. Then, the crude product obtained by concentrating the organic layer was purified by a silica gel short column (eluent: heptane) to obtain 69.2 g of an intermediate (X-2).

[chem 118]

Under nitrogen atmosphere, intermediate (X-2) (39.0g), intermediate (X-3) (25.9g), Pd-132 (0.719g) as palladium catalyst, NaOtBu (7.21g) and toluene ( 300ml) was put into a flask and heated at 110°C for 3 hours. After completion of the reaction, water and ethyl acetate were added to the reaction liquid and stirred, and the organic layer was separated and washed with water. Then, the crude product obtained by concentrating the organic layer was purified using a silica gel short path column (eluent: toluene/heptane=1/9 (volume ratio)), thereby obtaining 55.2 g of an intermediate (X-4 ).

[chem 119]

Under nitrogen atmosphere ^, and at 0 ℃, add ^1.60M tert-Butyllithium pentane solution ( ^tBuLi , 12.5ml). After completion of the dropwise addition, the temperature was raised to 70° C. and stirred for 0.5 hours, and components having a boiling point lower than tert-butylbenzene were distilled off under reduced pressure. After cooling to -50°C, boron tribromide (2.51 g) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. Then, cool to 0°C again and add N,N-diisopropylethylamine (EtN ⁱ Pr ₂ , 1.29 g), stir at room temperature until the heat generation ends, then raise the temperature to 100°C and heat and stir for 1 hour . The reaction liquid was cooled to room temperature, and then an aqueous sodium acetate solution cooled in an ice bath and ethyl acetate were sequentially added for liquid separation. After concentrating the organic layer, purification was performed with a silica gel short path column (eluent: chlorobenzene). The obtained crude product was recrystallized from toluene to obtain 3.10 g of compound (1-1).

[chemical 120]

The compound (1- 1).

In addition, the structure was also confirmed by proton nuclear magnetic resonance ( ¹ H-nuclear magnetic resonance, ¹ H-NMR).

¹ H-NMR (CDCl ₃ ): δ=8.6(s, 1H), 7.9(d, 1H), 7.7(s, 1H), 7.6(m, 6H), 7.5(d, 2H), 7.4(m, 3H), 7.3(s, 1H), 7.3(d, 1H), 7.0(t, 1H), 7.0(d, 2H), 7.0(s, 1H), 6.3(s, 1H), 6.1(s, 1H ), 2.5(s, 3H), 2.2(s, 3H), 1.8-1.7(m, 8H), 1.6(s, 3H), 1.5(s, 3H), 1.5(s, 6H), 1.4(s, 9H), 1.3(s, 3H), 1.3(s, 3H), 1.2(s, 9H), 1.1(d, 6H), 1.0(s, 9H), 0.9(s, 18H).

Synthesis Example (2): Synthesis of Compound (1-4)

Compound (1-4) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-4).

The target compound (1-4) of m/z (M+H)=1248.86 was confirmed by MALDI-TOF-MS.

[chem 121]

Synthesis Example (3): Synthesis of Compound (1-7)

Compound (1-7) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-7).

The target compound (1-7) of m/z (M+H)=1287.86 was confirmed by MALDI-TOF-MS.

In addition, the structure was also confirmed by ¹ H-NMR.

¹ H-NMR (CDCl ₃ ): δ=8.6 (s, 1H), 7.9 (d, 1H), 7.8-7.7 (m, 2H), 7.7 (s, 1H), 7.7 (d, 1H), 7.5- 7.4(m, 4H), 7.4-7.3(m, 4H), 7.1-7.0(m, 3H), 6.8(d, 1H), 6.7(br, 1H), 6.4(br, 1H), 6.3(br, 1H), 2.2(s, 3H), 2.2(s, 3H), 1.9-1.7(m, 11H), 1.6-1.5(m, 4H), 1.5(m, 9H), 1.4(s, 6H), 1.4 (s, 6H), 1.3(s, 3H), 1.3(s, 3H), 1.3(s, 9H), 1.2(s, 3H), 1.2(s, 3H), 1.1(s, 9H), 1.0( s, 18H).

[chemical 122]

Synthesis Example (4): Synthesis of Compound (1-9)

Compound (1-9) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-9).

The target compound (1-9) with m/z (M+H)=1341.91 was confirmed by MALDI-TOF-MS.

[chem 123]

Synthesis Example (5): Synthesis of Compound (1-15)

Compound (1-15) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-15).

The target compound (1-15) of m/z (M+H)=1225.75 was confirmed by MALDI-TOF-MS.

[chem 124]

Synthesis Example (6): Synthesis of Compound (1-16)

Compound (1-16) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-16).

The target compound (1-16) with m/z (M+H)=1159.67 was confirmed by MALDI-TOF-MS.

[chem 125]

Synthesis Example (7): Synthesis of Compound (1-17)

Compound (1-17) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-17).

The target compound (1-17) of m/z (M+H)=1384.86 was confirmed by MALDI-TOF-MS.

[chem 126]

Synthesis Example (8): Synthesis of Compound (1-19)

Compound (1-19) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-19).

The target compound (1-19) with m/z (M+H)=1188.73 was confirmed by MALDI-TOF-MS.

[chem 127]

Synthesis Example (9): Synthesis of Compound (1-22)

Compound (1-22) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-22).

The target compound (1-22) of m/z (M+H)=1098.59 was confirmed by MALDI-TOF-MS.

[chem 128]

Synthesis Example (10): Synthesis of Compound (1-23)

Compound (1-23) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-23).

The target compound (1-23) of m/z (M+H)=1267.76 was confirmed by MALDI-TOF-MS.

[chem 129]

Synthesis Example (11): Synthesis of Compound (1-24)

Compound (1-24) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-24).

The target compound (1-24) of m/z (M+H)=1255.80 was confirmed by MALDI-TOF-MS.

[chemical 130]

Synthesis Example (12): Synthesis of Compound (1-31)

Compound (1-31) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-31).

The target compound (1-31) with m/z (M+H)=1142.76 was confirmed by MALDI-TOF-MS.

[chem 131]

Synthesis Example (13): Synthesis of Compound (1-36)

Compound (1-36) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-36).

The target compound (1-36) of m/z (M+H)=1135.67 was confirmed by MALDI-TOF-MS.

[chem 132]

Synthesis Example (14): Synthesis of Compound (1-39)

Compound (1-39) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-39).

The target compound (1-39) with m/z (M+H)=1209.69 was confirmed by MALDI-TOF-MS.

[chem 133]

Synthesis Example (15): Synthesis of Compound (1-46)

Compound (1-46) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-46).

The target compound (1-46) of m/z (M+H)=1217.84 was confirmed by MALDI-TOF-MS.

[chem 134]

Synthesis Example (16): Synthesis of Compound (1-47)

Compound (1-47) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-47).

The target compound (1-47) of m/z (M+H)=1268.89 was confirmed by MALDI-TOF-MS.

[chem 135]

Synthesis Example (17): Synthesis of Compound (1-48)

Compound (1-48) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-48).

The target compound (1-48) with m/z (M+H)=1173.72 was confirmed by MALDI-TOF-MS.

[chem 136]

Synthesis Example (18): Synthesis of Compound (1-50)

Compound (1-50) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-50).

The target compound (1-50) with m/z (M+H)=1201.91 was confirmed by MALDI-TOF-MS.

[chem 137]

Synthesis Example (19): Synthesis of Compound (1-60)

Compound (1-60) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-60).

The target compound (1-60) of m/z (M+H)=1231.80 was confirmed by MALDI-TOF-MS.

In addition, the structure was also confirmed by ¹ H-NMR.

¹ H-NMR (CDCl ₃ ): δ=8.5 (d, 1H), 7.9 (s, 1H), 7.8 (d, 2H), 7.7 (d, 1H), 7.7-7.6 (m, 4H), 7.5 ( q, 3H), 7.4-7.3(m, 2H), 7.3(d, 1H), 7.0(d, 1H), 7.0(d, 2H), 6.6(d, 1H), 6.4(s, 1H), 6.3 (d, 1H), 6.3(s, 1H), 2.5(s, 3H), 2.3(s, 3H), 1.9-1.8(m, 4H), 1.8(s, 3H), 1.7(s, 3H), 1.5(s, 2H), 1.5(s, 3H), 1.5(s, 3H), 1.4(s, 6H), 1.4-1.3(m, 18H), 1.2(s, 9H), 1.1(s, 3H) , 1.1(s, 3H), 0.9(s, 9H), 0.9(s, 9H).

[chem 138]

Synthesis Example (20): Synthesis of Compound (1-61)

Compound (1-61) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-61).

The target compound (1-61) of m/z (M+H)=1293.82 was confirmed by MALDI-TOF-MS.

In addition, the structure was also confirmed by ¹ H-NMR.

¹ H-NMR (CDCl ₃ ): δ=8.56 (s, 1H), 7.87 (d, 2H), 7.65-7.50 (m, 6H), 7.45-7.41 (m, 4H), 7.32 (d, 1H), 7.21-7.18(m, 6H), 6.98-6.94(m, 3H), 6.59(s, 2H), 6.27(s, 2H), 2.29(s, 2H), 1.84-1.80(m, 4H), 1.73( s, 3H), 1.66(s, 4H), 1.49(t, 8H), 1.37(s, 6H), 1.35(s, 3H), 1.33(s, 9H), 1.29(dd, 6H), 1.19(s , 9H), 1.08(m, 6H), 0.92(s, 9H), 0.90(s, 9H).

[chem 139]

Synthesis Example (21): Synthesis of Compound (1-62)

Compound (1-62) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-62).

The target compound (1-62) of m/z (M+H)=1267.80 was confirmed by MALDI-TOF-MS.

In addition, the structure was also confirmed by ¹ H-NMR.

¹ H-NMR (CDCl ₃ ): δ=8.58 (d, 1H), 8.24 (d, 1H), 7.85-7.76 (m, 6H), 7.69-7.65 (m, 2H), 7.54-7.44 (m, 4H) ), 7.45(d, 1H), 7.34(s, 1H), 7.33-7.27(m, 1H), 7.23(dd, 1H), 7.02(t, 1H), 6.99(d, 2H), 6.54(d, 1H), 6.34(s, 1H), 6.05(s, 1H), 5.96(s, 1H), 2.29(s, 3H), 1.88-1.61(m, 12H), 1.55-1.42(m, 6H), 1.40 -1.25(m, 24H), 1.20(s, 9H), 1.11-1.05(m, 6H), 0.94-0.85(s, 18H).

[chem 140]

Synthesis Example (22): Synthesis of Compound (1-63)

Compound (1-63) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-63).

The target compound (1-63) with m/z (M+H)=1405.94 was confirmed by MALDI-TOF-MS.

[chem 141]

Synthesis Example (23): Synthesis of Compound (1-67)

Compound (1-67) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-67).

The target compound (1-67) of m/z (M+H)=1239.77 was confirmed by MALDI-TOF-MS.

[chem 142]

Synthesis Example (24): Synthesis of Compound (1-68)

Compound (1-68) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-68).

The target compound (1-68) of m/z (M+H)=1213.76 was confirmed by MALDI-TOF-MS.

[chem 143]

Synthesis Example (25): Synthesis of Compound (1-71)

Compound (1-71) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-71).

The target compound (1-71) of m/z (M+H)=1205.79 was confirmed by MALDI-TOF-MS.

In addition, the structure was also confirmed by ¹ H-NMR.

¹ H-NMR (CDCl ₃ ): δ=8.63 (s, 1H), 7.97 (d, 2H), 7.85-7.82 (m, 3H), 7.78-7.66 (m, 5H), 7.63-7.56 (m, 2H) ), 7.47-7.37(m, 5H), 6.91-6.90(m, 1H), 6.64(s, 5H), 1.77-1.65(m, 11H), 1.57-1.50(m, 9H), 1.47(s, 9H ), 1.39(s, 6H), 1.37-1.33(m, 9H), 1.13-1.03(m, 15H), 0.77(s, 18H).

[chem 144]

Synthesis Example (26): Synthesis of Compound (1-73)

Compound (1-73) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-73).

The target compound (1-73) of m/z (M+H)=1213.76 was confirmed by MALDI-TOF-MS.

[chem 145]

Synthesis Example (27): Synthesis of Compound (1-77)

Compound (1-77) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-77).

The target compound (1-77) of m/z (M+H)=1287.87 was confirmed by MALDI-TOF-MS.

[chem 146]

Synthesis Example (28): Synthesis of Compound (1-79)

Compound (1-79) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-79).

The target compound (1-79) with m/z (M+H)=1428.92 was confirmed by MALDI-TOF-MS.

[chem 147]

Synthesis Example (29): Synthesis of Compound (1-80)

Compound (1-80) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-80).

The target compound (1-80) with m/z (M+H)=1504.96 was confirmed by MALDI-TOF-MS.

[chem 148]

Synthesis Example (30): Synthesis of Compound (1-85)

Compound (1-85) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-85).

The target compound (1-85) with m/z (M+H)=1229.94 was confirmed by MALDI-TOF-MS.

[chem 149]

Synthesis Example (31): Synthesis of Compound (1-86)

Compound (1-86) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-86).

The target compound (1-86) of m/z (M+H)=1050.76 was confirmed by MALDI-TOF-MS.

[chem 150]

Synthesis Example (32): Synthesis of Compound (1-87)

Compound (1-87) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-87).

The target compound (1-87) of m/z (M+H)=1217.79 was confirmed by MALDI-TOF-MS.

[chem 151]

Synthesis Example (33): Synthesis of Compound (1-89)

Compound (1-89) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-89).

The target compound (1-89) with m/z (M+H)=1223.79 was confirmed by MALDI-TOF-MS.

[chem 152]

Synthesis Example (34): Synthesis of Compound (1-90)

Compound (1-90) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-90).

The target compound (1-90) with m/z (M+H)=1412.94 was confirmed by MALDI-TOF-MS.

[chem 153]

Synthesis Example (35): Synthesis of Compound (1-91)

Compound (1-91) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-91).

The target compound (1-91) of m/z (M+H)=1515.03 was confirmed by MALDI-TOF-MS.

[chem 154]

Synthesis Example (36): Synthesis of Compound (1-92)

Compound (1-92) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-92).

The target compound (1-92) of m/z (M+H)=1213.96 was confirmed by MALDI-TOF-MS.

[chem 155]

Synthesis Example (37): Synthesis of Compound (1-93)

Compound (1-93) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-93).

The target compound (1-93) with m/z (M+H)=1201.81 was confirmed by MALDI-TOF-MS.

[chem 156]

Synthesis Example (38): Synthesis of Compound (1-94)

Compound (1-94) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-94).

The target compound (1-94) with m/z (M+H)=1034.78 was confirmed by MALDI-TOF-MS.

[chem 157]

Synthesis Example (39): Synthesis of Compound (1-95)

Compound (1-95) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-95).

The target compound (1-95) of m/z (M+H)=1217.84 was confirmed by MALDI-TOF-MS.

[chem 158]

Synthesis Example (40): Synthesis of Compound (1-96)

Compound (1-96) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-96).

The target compound (1-96) of m/z (M+H)=1332.88 was confirmed by MALDI-TOF-MS.

[chem 159]

Synthesis Example (41): Synthesis of Compound (1-97)

Compound (1-97) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-97).

The target compound (1-97) of m/z (M+H)=1267.86 was confirmed by MALDI-TOF-MS.

[chem 160]

Synthesis Example (42): Synthesis of Compound (1-98)

Compound (1-98) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-98).

The target compound (1-98) with m/z (M+H)=1180.87 was confirmed by MALDI-TOF-MS.

[chem 161]

Synthesis Example (43): Synthesis of Compound (1-99)

Compound (1-99) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-99).

The target compound (1-99) of m/z (M+H)=1009.58 was confirmed by MALDI-TOF-MS.

[chem 162]

Synthesis Example (44): Synthesis of Compound (1-100)

Compound (1-100) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-100).

The target compound (1-100) of m/z (M+H)=1277.84 was confirmed by MALDI-TOF-MS.

[chem 163]

Synthesis Example (45): Synthesis of Compound (1-101)

Compound (1-101) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-101).

The target compound (1-101) of m/z (M+H)=1272.82 was confirmed by MALDI-TOF-MS.

[chem 164]

Synthesis Example (46): Synthesis of Compound (1-102)

Compound (1-102) was obtained in the same procedure as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-102).

The target compound (1-102) of m/z (M+H)=1189.81 was confirmed by MALDI-TOF-MS.

[chem 165]

Other compounds of the present invention can be synthesized by appropriately changing the starting compound and using the method according to the above-mentioned synthesis examples.

<Evaluation method of basic physical properties>

<Sample preparation>

When evaluating the absorption characteristics and emission characteristics (fluorescence and phosphorescence) of a compound to be evaluated, there are cases where the compound to be evaluated is dissolved in a solvent and evaluated in a solvent, and evaluation is performed in a thin film state . Furthermore, in the case of evaluating in a thin film state, there are cases where only the compound to be evaluated is thinned and evaluated in accordance with the use form of the compound to be evaluated in the organic EL device, and the compound to be evaluated is dispersed in In the case of evaluation by using a suitable substrate material and making it into a thin film. Here, a thin film obtained by vapor-depositing only the compound to be evaluated is called a "single film", and a thin film obtained by applying a coating solution containing a compound to be evaluated and a matrix material and drying it is called a "coated film" .

As the matrix material, commercially available PMMA (polymethyl methacrylate) or the like can be used. In this example, PMMA and the compound to be evaluated were dissolved in toluene, and then a thin film was formed on a quartz transparent support substrate (10 mm×10 mm) by spin coating to prepare a sample.

In addition, thin film samples when the host material is the host compound were prepared as follows. A transparent support substrate made of quartz (10mm×10mm×1.0mm) was fixed on the substrate holder of a commercially available vapor deposition device (manufactured by Changzhou Sangyo Co., Ltd.), and a molybdenum vaporizer containing the main compound was installed. After putting the boat for plating and the boat for vapor deposition made of molybdenum containing the dopant material, the vacuum chamber was decompressed to 5×10 ⁻⁴ Pa. Next, the boat for vapor deposition containing the host compound and the boat for vapor deposition containing the dopant material are simultaneously heated, so that the host compound and the dopant material have an appropriate film thickness. By vapor deposition, a mixed thin film (sample) of the host compound and the dopant material is formed. Here, the vapor deposition rate is controlled according to the set mass ratio of the host compound and the dopant material.

<Evaluation of absorption characteristics and emission characteristics>

The measurement of the absorption spectrum of a sample was performed using the ultraviolet-visible-near-infrared spectrophotometer (Shimadzu Corporation, UV-2600). In addition, the measurement of the fluorescence spectrum or phosphorescence spectrum of a sample was performed using the spectrofluorophotometer (manufactured by Hitachi High-Tech Co., Ltd., F-7000).

For the measurement of the fluorescence spectrum, the photoluminescence (photoluminescence) is measured by exciting at an appropriate excitation wavelength at room temperature. The measurement of the phosphorescence spectrum was carried out in a state where the sample was immersed in liquid nitrogen (at a temperature of 77K) using an attached cooling unit. In order to observe the phosphorescence spectrum, an optical chopper was used to adjust the delay time from the irradiation of the excitation light to the start of the measurement. A sample is excited at an appropriate excitation wavelength to measure photoluminescence.

In addition, the fluorescence quantum yield (PLQY) was measured using an absolute PL quantum yield measuring device (manufactured by Hamamatsu Photonics Co., Ltd., C9920-02G).

Next, evaluation of basic physical properties of the polycyclic aromatic compound of the present invention will be described.

<Evaluation of fluorescence lifetime (delayed fluorescence)>

The fluorescence lifetime was measured at 300K using a fluorescence lifetime measuring device (manufactured by Hamamatsu Photonics Co., Ltd., C11367-01). Specifically, among the maximum emission wavelengths measured at an appropriate excitation wavelength, a luminescent component with a fast fluorescence lifetime and a luminescent component with a slow fluorescence lifetime are observed. In the measurement of the fluorescence lifetime at room temperature of a general organic EL material that emits fluorescence, the triplet component is inactivated by heat, and thus the slow emission component in which the triplet component derived from phosphorescence participates is hardly observed. The fact that a slow-emitting component is observed in the compound to be evaluated means that triplet energy with a long excitation lifetime is shifted to singlet energy by thermal activation and observed as delayed fluorescence.

<Calculation of energy gap (Eg)>

From the long-wavelength end A (nm) of the absorption spectrum obtained by the above method, Eg=1240/A was calculated.

<Measurement of ionization potential (Ip)>

The transparent support substrate (28mm × 26mm × 0.7mm) with vapor-deposited ITO (indium tin oxide) was fixed on the substrate holder of a commercially available vapor deposition device (manufactured by Changzhou Sangyo Co., Ltd.), and placed in The vacuum chamber was decompressed to 5×10 ⁻⁴ Pa after the molybdenum vapor deposition boat containing the target compound was placed. Next, the boat for vapor deposition is heated to evaporate the target compound to form a single film (Neat film) of the target compound.

Using the obtained individual film as a sample, the ionization potential of the target compound was measured using a photoelectron spectrometer (Sumitomo Heavy Industries, Ltd. PYS-201).

<Calculation of Electron Affinity (Ea)>

The electron affinity can be estimated from the difference between the ionization potential measured by the above method and the energy gap calculated by the above method.

<Determination of lowest excited singlet level E(S, Sh) and lowest excited triplet level E(T, Sh)>

For a single film of the target compound formed on a glass substrate, the fluorescence spectrum is observed at 77K with the second absorption peak on the long-wavelength side of the self-absorption spectrum as excitation light, and the shoulder peak on the short-wavelength side of the peak of the fluorescence spectrum is Find the lowest excited singlet energy level E(S, Sh). In addition, for a single film of the target compound formed on a glass substrate, the phosphorescence spectrum was observed at 77K with the second absorption peak on the long-wavelength side of the self-absorption spectrum as excitation light. Find the lowest excited triplet energy level E(T, Sh) from the shoulder peak.

<Evaluation of organic EL elements>

As described above, the compound of the present invention is characterized by an appropriate energy gap (Eg), a high lowest triplet excitation energy (ET), and a small AEST, so it can be expected to be used in, for example, light-emitting layers and charge transport layers, especially in luminous layer.

<Evaluation items and evaluation methods>

As evaluation items, there are driving voltage (V), emission wavelength (nm), International Commission on Illumination (Commission Internationale de L'Eclairage, CIE) chromaticity (x, y), external quantum efficiency (%), maximum wavelength of emission spectrum ( nm) and half-value width (nm), etc. The above-mentioned evaluation items can use the values at the time of appropriate emission luminance.

The quantum efficiency of a light-emitting element includes an internal quantum efficiency and an external quantum efficiency. The internal quantum efficiency indicates the ratio of pure conversion of external energy injected into the light-emitting layer of the light-emitting element as electrons (or holes) into photons. On the other hand, the external quantum efficiency is calculated based on the amount of photons released to the outside of the light-emitting element, and a part of the photons generated in the light-emitting layer is absorbed or continuously reflected by the inside of the light-emitting element and is not released to the outside of the light-emitting element, Therefore the external quantum efficiency is lower than the internal quantum efficiency.

The measurement methods of spectral radiance (luminescence spectrum) and external quantum efficiency are as follows. A voltage was applied using a voltage/current generator R6144 manufactured by Advantest, whereby the element was made to emit light. Spectral radiance in the visible light region was measured from a direction perpendicular to the light-emitting surface using a spectroradiance meter SR-3AR manufactured by TOPCON. Assuming that the light-emitting surface is a fully diffused surface, the value obtained by dividing the measured value of the spectral radiance of each wavelength component by the wavelength energy and multiplying it by π is the number of photons at each wavelength. Next, the number of photons was accumulated over the entire observed wavelength range, and was set as the total number of photons released from the device. The value obtained by dividing the applied current value by the elementary charge (elementary charge) was set as the number of carriers injected into the element, and the value obtained by dividing the total number of photons released from the element by the number of carriers injected into the element Values are external quantum efficiencies. In addition, the half-value width of the emission spectrum is obtained as the width between the upper and lower wavelengths at which the intensity becomes 50% around the maximum emission wavelength.

Next, production and evaluation of an organic EL device using the polycyclic aromatic compound of the present invention will be described.

<Structure of organic EL element>

An organic EL device is produced using the polycyclic aromatic compound of the present invention.

The material structure of each layer in the organic EL element of Example 1-Example 46 and Comparative Example 1-Comparative Example 8 is shown in Table 1 below.

[Table 1]

[Table 2]

Example 1 Compound (1-1) Example 2 Compound (1-4) Example 3 Compound (1-7) Example 4 Compound (1-9) Example 5 Compound (1-15) Example 6 Compound (1-16) Example 7 Compound (1-17) Example 8 Compound (1-19) Example 9 Compound (1-22) Example 10 Compound (1-23) Example 11 Compound (1-24) Example 12 Compound (1-31) Example 13 Compound (1-36) Example 14 Compound (1-39) Example 15 Compound (1-46) Example 16 Compound (1-47) Example 17 Compound (1-48) Example 18 Compound (1-50) Example 19 Compound (1-60) Example 20 Compound (1-61) Example 21 Compound (1-62) Example 22 Compound (1-63) Example 23 Compound (1-67) Example 24 Compound (1-68) Example 25 Compound (1-71) Example 26 Compound (1-73) Example 27 Compound (1-77) Example 28 Compound (1-79) Example 29 Compound (1-80) Example 30 Compound (1-85) Example 31 Compound (1-86) Example 32 Compound (1-87) Example 33 Compound (1-89) Example 34 Compound (1-90) Example 35 Compound (1-91) Example 36 Compound (1-92) Example 37 Compound (1-93) Example 38 Compound (1-94) Example 39 Compound (1-95) Example 40 Compound (1-96) Example 41 Compound (1-97) Example 42 Compound (1-98) Example 43 Compound (1-99) Example 44 Compounds (1-100) Example 45 Compound (1-101) Example 46 Compound (1-102) Comparative example 1 Comparative Compounds (1) Comparative example 2 Comparative Compounds (2) Comparative example 3 Comparative Compounds (3) Comparative example 4 Comparative Compounds (4) Comparative Example 5 Comparative Compounds (5) Comparative example 6 Comparative Compound (6) Comparative Example 7 Comparative Compound (7) Comparative Example 8 Comparative Compound (8)

"HI", "HAT-CN", "HT-1", "HT-2", "BH", "ET-1", "ET-2", "Liq" in Table 1 and Table 2 are shown below ", "comparative compound (1)", "comparative compound (2)", "comparative compound (3)", "comparative compound (4)", "comparative compound (5)", "comparative compound (6)", Chemical structures of "comparative compound (7)" and "comparative compound (8)".

[chem 166]

[chem 167]

(Example 1)

A glass substrate (manufactured by Opto Science Co., Ltd.) of 26 mm×28 mm×0.7 mm in which ITO having a thickness of 180 nm by sputtering was polished to 150 nm was used as a transparent support substrate. The transparent support substrate was fixed on the substrate holder of a commercially available evaporation device (manufactured by Showa Vacuum Co., Ltd.), and installed with HI, HAT-CN, HT-1, HT-2, BH , compound (1-1), ET-1 and ET-2 boats for vapor deposition made of molybdenum, and boats for vapor deposition of aluminum nitride containing Liq, LiF and aluminum respectively.

The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was depressurized to 5×10 ^-4 Pa, first, HI was heated to make a film thickness of 40 nm, and then HAT-CN was heated to make a film thickness of 5 nm. Then, HT-1 was heated and vapor-deposited so that the film thickness became 45nm, and then, HT-2 was heated and vapor-deposited so that the film thickness became 10nm. A cavity layer comprising four layers was formed. Next, BH and the compound (1-1) were simultaneously heated and vapor-deposited so that the film thickness became 25 nm to form a light-emitting layer. The vapor deposition rate was adjusted so that the mass ratio of BH to compound (1-1) was approximately 97:3. Furthermore, ET-1 was heated and vapor-deposited so as to have a film thickness of 5 nm, and then ET-2 and Liq were simultaneously heated and vapor-deposited so as to have a film thickness of 25 nm. Two layers of electron shells. The vapor deposition rate was adjusted so that the mass ratio of ET-2 to Liq was approximately 50:50. The vapor deposition rate of each layer is 0.01 nm/sec to 1 nm/sec. Thereafter, LiF was vapor-deposited at a deposition rate of 0.01 nm/sec to 0.1 nm/sec so that the film thickness became 1 nm by heating, and then aluminum was heated so that the film thickness became 100 nm. Vapor deposition is performed to form a cathode to obtain an organic EL element.

(Example 2 to Example 46 and Comparative Example 1 to Comparative Example 8)

Except having used the compound described in Table 2 instead of compound (1-1), it carried out similarly to Example 1, and obtained the organic EL element of Example 2-Example 46 and Comparative Example 1-Comparative Example 8.

<Evaluation items and evaluation methods>

The evaluation items include drive voltage (V), emission wavelength (nm), CIE chromaticity (x, y), external quantum efficiency (%), maximum wavelength (nm) and half-value width (nm) of the emission spectrum, and the like. For these evaluation items, values at the time of luminescence of 1000 cd/m ² can be used, for example.

The quantum efficiency of a light-emitting element includes an internal quantum efficiency and an external quantum efficiency. The internal quantum efficiency indicates the ratio of purely converting external energy injected into the light-emitting layer of the light-emitting element as electrons (or holes) into photons. On the other hand, the external quantum efficiency is calculated based on the amount of photons released to the outside of the light-emitting element, and a part of the photons generated in the light-emitting layer is absorbed or continuously reflected by the inside of the light-emitting element and is not released to the outside of the light-emitting element, Therefore the external quantum efficiency is lower than the internal quantum efficiency.

The measurement methods of spectral radiance (luminescence spectrum) and external quantum efficiency are as follows. Using a voltage/current generator R6144 manufactured by Advantest, a voltage to make the brightness of the device 1000 cd/m ² was applied to make the device emit light. Using a spectroradiance meter SR-3AR manufactured by TOPCON, the spectral radiance in the visible light region was measured from the vertical direction to the light-emitting surface. Assuming that the light-emitting surface is a fully diffused surface, the value obtained by dividing the measured spectral radiance of each wavelength component by the wavelength energy and multiplying it by π is the number of photons at each wavelength. Next, the number of photons is integrated over the entire observed wavelength region, and is set as the total number of photons emitted from the device. The value obtained by dividing the applied current value by the elementary charge (elementary charge) was set as the number of carriers injected into the element, and the value obtained by dividing the total number of photons released from the element by the number of carriers injected into the element Values are external quantum efficiencies. In addition, the half-value width of the emission spectrum is obtained as the width between the upper and lower wavelengths at which the intensity becomes 50% around the maximum emission wavelength.

For the organic EL elements of Examples 1 to 46 and Comparative Examples 1 to 8, a DC voltage was applied using the ITO electrode as the anode and the LiF/aluminum electrode as the cathode, and the characteristics when emitting light at 1000 cd/m ² were measured.

The results are shown in Table 3.

[table 3]

[industrial availability]

The polycyclic aromatic compound of the present invention can be effectively used as a material for an organic device, particularly as a material for a light-emitting layer for forming a light-emitting layer of an organic electroluminescence device. By using the polycyclic aromatic compound of the present invention as a dopant for a light-emitting layer, an organic electroluminescent device with low voltage and high luminous efficiency can be obtained.

Claims (13)

1. A polycyclic aromatic compound having one or more structures comprising structural units represented by the following formula (1);

In formula (1), Ring A and ring B are independently substituted or unsubstituted aryl rings or substituted or unsubstituted heteroaryl rings; C ring is a ring represented by formula (C), In formula (C), X ^c is >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, the >NR, the >C(-R) ₂ and the > R of Si(-R) ₂ are independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted In a substituted cycloalkyl group, the >C(-R) ₂ and the >Si(-R) ₂ Rs can be bonded to each other to form a ring, Any adjacent two ^ZCs are carbons directly bonded to either ^Y1 or ^X2 , respectively, Other Z ^C are independently N or ^CRC , R ^C are independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted di Arylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted Alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or An unsubstituted arylthio group or a substituted silyl group, the two aryl groups of the diarylamino group can be bonded to each other via a linking group, and the two heteroaryl groups of the diheteroarylamino group can be bonded to each other via a linking group The aryl group of the arylheteroarylamino group and the heteroaryl group can be bonded to each other through a linking group, and the two aryl groups of the diarylboryl group can be bonded to each other through a single bond or a linking group. bond, Two adjacent R ^C can be bonded to each other to form an aryl ring or a heteroaryl ring, the formed aryl ring and heteroaryl ring are respectively unsubstituted or substituted by at least one R ^C2 , R ^C2 and R ^C For the same meaning, wherein, R ^C2 is not hydrogen, and two adjacent R ^C2 will not be bonded to each other to form an aryl ring or a heteroaryl ring; ^Y1 is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, and the R of the Si-R and the Ge-R is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl; X ¹ and X ² are independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, and R in the >NR is hydrogen, substituted or Unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, said >C(-R) ₂ , and the R of >Si(-R) ₂ are independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or For a substituted or unsubstituted cycloalkyl group, the two Rs of the >C(-R) ₂ and the >Si(-R) ₂ can be bonded to each other to form a ring. In addition, the R of the >NR And/or said >C(-R) ₂ R can be bonded to A ring and/or B ring, or A ring and/or C ring through a linking group or a single bond, Wherein, at least one of X ¹ or X ² is >NG, and G is a group represented by formula (G), In formula (G), Z ^g is independently N or CR ^g , and R ^g is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diaryl Amino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkane substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted A substituted arylthio group or a substituted silyl group, the two aryl groups of the diarylamino group can be bonded to each other via a linking group, and the two heteroaryl groups of the diheteroarylamino group can be bonded to each other via a linking group Bonding, the aryl and heteroaryl groups of the arylheteroarylamino group can be bonded to each other via a linking group, and the two aryl groups of the diarylboryl group can be bonded to each other via a single bond or a linking group , Two adjacent R ^g can be bonded to each other to form an aryl ring or a heteroaryl ring, and the formed aryl ring and heteroaryl ring are respectively unsubstituted or substituted by at least one R ^g2 , R ^g2 and R ^g For the same meaning, wherein, R ^g2 is not hydrogen, and two adjacent R ^g2 will not be bonded to each other to form an aryl ring or a heteroaryl ring, * indicates the bonding position with N; At least one of the aryl ring or heteroaryl ring in the structure may be condensed by at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one _-CH2- in the cycloalkane may be represented by - O-substitution; At least one hydrogen in the structure may be replaced by cyano, halogen, or deuterium. 2. The polycyclic aromatic compound according to claim 1, wherein the structural unit represented by formula (1) is a structural unit represented by formula (2);

In formula (2), In ring a and ring b, Z is independently N or CR ¹¹ , or Z=Z is independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S , or >Se, the R of the >NR, the >C(-R) ₂ and the >Si(-R) ₂ are independently hydrogen, substituted or unsubstituted aryl, substituted or Unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, the >C(-R) ₂ and the >Si(-R) ₂ Two R can be bonded to each other to form a ring, R ¹¹ of said CR ¹¹ are independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted Substituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted Substituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl groups, The two aryl groups of the diarylamino group can be bonded to each other via a linking group, the two heteroaryl groups of the diheteroarylamino group can be bonded to each other via a linking group, and the arylheteroarylamino group can be bonded to each other via a linking group. The aryl group and the heteroaryl group can be bonded to each other via a linking group, and the two aryl groups of the diaryl boron group can be bonded to each other via a single bond or a linking group, Two adjacent R ¹¹ can be bonded to each other and form an aryl ring or a heteroaryl ring together with the a ring or the b ring, and the formed aryl ring and heteroaryl ring are respectively unsubstituted, or are composed of at least one R ^11b Substitution, R ^11b and R ¹¹ have the same meaning, wherein, R ^11b is not hydrogen, and two adjacent R ^11b will not be bonded to each other to form an aryl ring or a heteroaryl ring, C ring is the ring represented by formula (C); ^Y1 is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, and the R of the Si-R and the Ge-R is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl; X ¹ and X ² are independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, and R in the >NR is hydrogen, substituted or Unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, said >C(-R) ₂ , and the R of >Si(-R) ₂ are independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or For a substituted or unsubstituted cycloalkyl group, the two Rs of the >C(-R) ₂ and the >Si(-R) ₂ can be bonded to each other to form a ring. In addition, the R of the >NR And/or the R of >C(-R) ₂ can be bonded to a ring and/or b ring, or a ring and/or C ring through a linking group or a single bond, wherein X ¹ or X ² At least one is >NG, and the G of >NG is a group represented by formula (G); At least one of the aryl ring or heteroaryl ring in the structure may be condensed by at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one _-CH2- in the cycloalkane may be represented by - O-substitution; At least one hydrogen in the structure may be replaced by cyano, halogen, or deuterium. 3. The polycyclic aromatic compound according to claim 2, wherein the structural unit represented by formula (2) is a structural unit represented by formula (2a-1);

In formula (2a-1), Y ¹ , X ¹ , X ² , X ^C have the same meanings as Y ¹ , X ¹ , X ² , and X ^C in formula (2), and R ^11b , R ^C2 have the same meanings as formula ( 2) R ^11b and R ^C2 have the same meaning respectively, n1 is an integer from 0 to 4, n2 is an integer from 0 to 4, n3 is an integer from 0 to 3, at least one of the aryl or heteroaryl rings in the structure may be condensed with at least one cycloalkane, At least one hydrogen in the structure may be replaced by cyano, halogen, or deuterium. 4. The polycyclic aromatic compound according to claim 3, represented by any one of the following formulae,

In the formula, Me is methyl, tBu is tert-butyl, and D is deuterium. 5. The polycyclic aromatic compound according to claim 2, wherein the structural unit represented by formula (2) is a structural unit represented by formula (2a-2);

In formula (2a-2), Y ¹ , X ¹ , X ² , X ^C have the same meanings as Y ¹ , X ¹ , X ² , and X ^C in formula (2), and R ^11b , R ^C2 have the same meanings as formula ( 2) R ^11b and R ^C2 have the same meaning respectively, X ³ and X ⁴ are independently a single bond, >O, >NR, >C(-R) ₂ , or >S, wherein X ³ and X ⁴ are not single bonds at the same time, n1 is an integer of 0 to 4, n2 is an integer of 0 to 4, n3 is an integer of 0 to 3, n4 is an integer of 0 to 2, at least one of the aryl or heteroaryl rings in the structure may be condensed with at least one cycloalkane, At least one hydrogen in the structure may be replaced by cyano, halogen, or deuterium. 6. The polycyclic aromatic compound according to claim 5, represented by any one of the following formulae,

In the formula, Me is methyl, tBu is tert-butyl, and D is deuterium. 7. The polycyclic aromatic compound according to claim 2, represented by the following formula,

8. A material for an organic device, comprising the polycyclic aromatic compound according to any one of claims 1 to 7. 9. An organic electroluminescence element, comprising: a pair of electrodes, comprising an anode and a cathode; and a light-emitting layer, configured between the pair of electrodes, the light-emitting layer containing as described in any one of claims 1 to 7 The polycyclic aromatic compounds mentioned above. 10 . The organic electroluminescence device according to claim 9 , wherein the light emitting layer contains a host and the polycyclic aromatic compound as a dopant. 11 . 11. The organic electroluminescent element according to claim 10, wherein the host is an anthracene compound, a fluorene compound, or a dibenzo

compound. 12. A display device comprising the organic electroluminescence element according to any one of claims 9 to 11. 13. A lighting device, comprising the organic electroluminescence element according to any one of claims 9 to 11.

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