WO2020050546A1 - Compound for organic electric element, organic electric element using same, and electronic device thereof - Google Patents

Abstract

The present invention provides a compound represented by formula 1, an organic electric element comprising a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode, and an electronic device comprising the organic electric element. By comprising the compound represented by formula 1 in the organic material layer, it is possible to lower driving voltage of the organic electric element and improve luminous efficiency and lifespan thereof.

Description

Compound for organic electric element, organic electric element using same, and electronic device thereof

The present invention relates to a compound for an organic electric element, an organic electric element using the same, and an electronic device thereof.

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic electric device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often composed of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

Materials used as the organic material layer in the organic electric device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their function. In addition, the light-emitting material may be classified into a polymer type and a low-molecular type according to the molecular weight, and a fluorescent material derived from the singlet excited state of the electron and a phosphorescent material derived from the triplet excited state of the electron according to the light emission mechanism. have. In addition, the luminescent material may be divided into blue, green, and red luminescent materials and yellow and orange luminescent materials required to realize a better natural color according to the luminous color.

On the other hand, when only one material is used as the light emitting material, the maximum emission wavelength moves to a long wavelength due to intermolecular interaction, and the color purity is reduced or the efficiency of the device is reduced due to the light emission attenuation effect. In order to increase the luminous efficiency through, a host / dopant system may be used as a luminescent material. The principle is that when a small amount of the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with the light emitting layer, excitons generated in the light emitting layer are transported to the dopant to produce high-efficiency light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of a desired wavelength can be obtained according to the type of dopant used.

Currently, the portable display market is increasing in size as a large-area display, and accordingly, power consumption greater than that required in the existing portable display is required. Therefore, power consumption has become a very important factor for a portable display that has a limited power supply, such as a battery, and the problem of efficiency and life must also be solved.

Efficiency, life, and driving voltage are related to each other, and when the efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, crystallization of organic substances due to Joule heating generated during driving decreases, and as a result, It shows a tendency to increase the life. However, simply improving the organic layer does not maximize efficiency. This is because long life and high efficiency can be achieved at the same time when the energy level and T ₁ value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined. .

Therefore, it is necessary to develop a light emitting material that has high thermal stability and can efficiently achieve charge balance in the light emitting layer, and in particular, it is necessary to develop a host material for the light emitting layer.

An object of the present invention is to provide a compound capable of lowering the driving voltage of a device and improving the luminous efficiency and lifetime of the device, an organic electric device using the same, and an electronic device thereof.

In one aspect, the present invention provides a compound represented by the following formula.

In another aspect, the present invention provides an organic electric device using the compound represented by the formula and an electronic device thereof.

By using the compound according to the embodiment of the present invention, the driving voltage of the device can be lowered, and the luminous efficiency and lifetime of the device can be greatly improved.

1 is an exemplary view of an organic electroluminescent device according to the present invention.

[Description of codes]

100: organic electrical element 110: substrate

120: first electrode 130: hole injection layer

140: hole transport layer 141: buffer layer

150: light emitting layer 151: light emitting auxiliary layer

160: electron transport layer 170: electron injection layer

180: second electrode

The terms "aryl group" and "arylene group" used in the present invention have 6 to 60 carbon atoms, respectively, and are not limited thereto unless otherwise specified. In the present invention, an aryl group or an arylene group includes monocyclic, ring aggregates, conjugated multiple ring systems, spiro compounds, and the like.

The term "heterocyclic group" used in the present invention includes aromatic rings such as "heteroaryl group" or "heteroarylene group" as well as non-aromatic rings, and each carbon number containing one or more heteroatoms unless otherwise specified. It means a ring of 2 to 60, but is not limited thereto. The term "heteroatom" as used herein refers to N, O, S, P or Si, unless otherwise specified, and the heterocyclic group is a monocyclic, ring aggregate, heterozygous multiple ring system, spy containing heteroatoms. Means a compound and the like. In addition, the heterocycle used in the present invention may also include a compound containing a heteroatom group such as SO ₂ , P = O, and the like, instead of carbon forming a ring.

The term "fluorenyl group" or "fluorenylene group" used in the present invention means a monovalent or divalent functional group in which R, R 'and R "are both hydrogen in the following structures, unless otherwise specified. Substituted fluorenyl group "or" substituted fluorenylene group "means that at least one of the substituents R, R ', R" is a substituent other than hydrogen, and R and R' are bonded to each other to form a carbon to which they are attached. It includes the case where a compound was formed as a spy together.

The term "spiro compound" as used in the present invention has a 'spiro union', and a spiro linkage refers to a connection in which two rings share only one atom. At this time, the atoms shared in the two rings are called 'spyro atoms', and these are 'monospyro-', 'dispiro-', and 'trispyro' depending on the number of spy atoms in a compound. It is called a compound.

In the present specification, the 'group name' corresponding to an aryl group, an arylene group, a heterocyclic group, etc. exemplified as an example of each symbol and its substituent may describe 'the name of a group reflecting a singer', but is described as a 'parent compound name' You may. For example, in the case of 'phenanthrene', which is a type of aryl group, the monovalent 'group' is 'phenanthryl', and the bivalent group can be classified as a singer such as 'phenanthrylene', but the name of the group can be described. Regardless, the parent compound name may be described as 'phenanthrene'. Similarly, in the case of pyrimidine, it can be described as 'pyrimidine' regardless of the singer, or in the case of monovalent pyrimidinyl group, in the case of divalent pyrimidinylene, etc., as the 'group name' of the corresponding singer. have.

In addition, unless explicitly stated, the formula used in the present invention is applied in the same manner as the definition of a substituent based on the index definition of the following formula.

Here, when a is an integer of 0, the substituent R ¹ means non-existent, that is, when a is 0, it means that hydrogen is bonded to all of the carbons forming the benzene ring. The formula or compound may be omitted. In addition, when a is an integer of 1, one substituent R ¹ is bound to any one of carbons forming a benzene ring, and when a is an integer of 2 or 3, for example, it can be bonded as follows, and a is 4 to 6 Even in the case of an integer, it is bonded to the carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R ¹ may be the same or different.

In addition, unless otherwise specified in the present specification, the rings formed by bonding adjacent groups to each other are C ₆ ~ C ₆₀ aromatic ring groups; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; And combinations thereof.

Hereinafter, a stacked structure of an organic electric device including the compound of the present invention will be described with reference to FIG. 1.

 In describing the present invention, when it is determined that detailed descriptions of related known configurations or functions may obscure the subject matter of the present invention, detailed descriptions thereof will be omitted.

Also, if a component such as a layer, film, region, plate, etc. is said to be "above" or "on" another component, this is not only when the other component is "directly above", but also with another component in the middle. It should be understood that the case may be included. Conversely, it should be understood that when a component is said to be “just above” another part, it means that there is no other part in between.

1 is an exemplary view of an organic electric device according to an embodiment of the present invention.

Referring to FIG. 1, an organic electric device 100 according to an embodiment of the present invention includes a first electrode 120, a second electrode 180, and a first electrode 120 formed on a substrate 110. Between the second electrode 180 includes an organic material layer containing the compound according to the present invention. At this time, the first electrode 120 may be an anode (anode), the second electrode 180 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 sequentially stacked on the first electrode 120. . At this time, at least one of these layers is omitted, a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, an electron transport auxiliary layer, a buffer layer 141, and the like may be further included, and the electron transport layer 160, etc. It can also serve as a hole blocking layer.

In addition, although not shown, the organic electric device according to an embodiment of the present invention may further include a protective layer or a light efficiency improving layer. The light efficiency improving layer may be formed on a surface that does not contact the organic material layer on both surfaces of the first electrode or a surface that does not contact the organic material layer on both surfaces of the second electrode.

The compound according to an embodiment of the present invention applied to the organic material layer is a hole injection layer 130, a hole transport layer 140, a light emitting auxiliary layer 151, an electron transport auxiliary layer, an electron transport layer 160, an electron injection layer ( 170), the host or dopant of the light emitting layer 150, or may be used as a material for the light efficiency improving layer. Preferably, the compound according to Formula 1 of the present invention can be used as a host for a light emitting layer.

On the other hand, even in the case of the same core, the band gap, electrical characteristics, and interfacial characteristics may vary depending on which substituent is attached to which position, and thus, the selection of the core and the combination of sub-substituents coupled thereto. It is necessary to study, especially when the energy level and T ₁ value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined, long life and high efficiency can be achieved simultaneously.

Therefore, in the present invention, by using the compound represented by the formula (1) as a host of the light emitting layer, the energy level and T ₁ value between each organic material layer, the properties of the material (mobility, interfacial properties, etc.) are optimized to optimize the life of the organic electric device. And it is possible to improve the efficiency at the same time.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. It may be manufactured using a deposition method such as PVD or CVD, for example, by depositing a metal or conductive metal oxide or an alloy thereof on a substrate to form the anode 120, and a hole injection layer 130 thereon , After forming an organic material layer including the hole transport layer 140, the light emitting layer 150, the electron transport layer 160 and the electron injection layer 170, can be prepared by depositing a material that can be used as the cathode 180 thereon have. In addition, the light emitting auxiliary layer 151 may be further formed between the hole transport layer 140 and the light emitting layer 150, and the electron transport auxiliary layer may be further formed between the light emitting layer 150 and the electron transport layer 160.

In addition, the organic material layer is a solution process or a solvent process (e.g., spin coating process), nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blade using various polymer materials It can be produced with fewer layers by a method such as a ding process, a screen printing process, or a thermal transfer method. Since the organic material layer according to the present invention can be formed in various ways, the scope of the present invention is not limited by the formation method.

The organic electric device according to an embodiment of the present invention may be a front emission type, a back emission type, or a double-sided emission type depending on the material used.

Further, the organic electroluminescent device according to an embodiment of the present invention may be selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device and a quantum dot display device.

Another embodiment of the present invention may include an electronic device including a display device including the above-described organic electric element of the present invention and a control unit for controlling the display device. At this time, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation, game machines, various TVs, and various computers.

Hereinafter, a compound according to an aspect of the present invention will be described.

The compound according to an aspect of the present invention is represented by Formula 1 below.

<Formula 1>

In Chemical Formula 1, each symbol may be defined as follows.

Y ₁ to Y ₄ are each independently N or CL ₁ -Ar ₁ , at least two of Y ₁ to Y ₄ are N, and a plurality of L ₁ are the same or different, and a plurality of Ar ₁ are the same or different, respectively. Do. Therefore, the hexagonal ring containing Y ₁ to Y ₄ may be a derivative of pyrimidine, pyrazine, pyridazine, triazine, or the like.

X ₁ is NL ₂ -Ar ₂ , O or S.

X ₂ and X ₃ are each independently a single bond, NL ₃ -Ar ₃ , O or S, except that X ₂ and X ₃ are both single bonds, and a plurality of L ₃ are the same or different, and multiple Ar ₃ of each is the same or different. n and m are each an integer of 0 or 1, and n + m is an integer of 1 or more. That is, at least one of n and m is 1.

L ₁ to L ₃ are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₃ ~ C ₆₀ aliphatic ring group; And C ₂ ~ C ₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si and P; may be selected from the group consisting of.

When L ₁ to L ₃ are arylene groups, preferably an arylene group of C ₆ to C ₃₀ , more preferably an arylene group of C ₆ to C ₁₈ , such as phenyl, biphenyl, terphenyl, and the like.

Ar ₁ to Ar ₃ are independently of each other C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; And -L'-N (R _a ) (R _b ).

When Ar ₁ to Ar ₃ are aryl groups, preferably C ₆ to C ₃₀ aryl groups, more preferably C ₆ to C ₁₈ aryl groups, such as phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, Triphenylene, and the like.

When Ar ₁ is a heterocyclic group, preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₂₈ heterocyclic group such as pyridine, pyrimidine, triazine, quinazoline, quinoline, carba Sol, phenylcarbazole, benzocarbazole, dibenzocarbazole, dibenzothiophene, benzothienopyridine, dibenzofuran, benzonaphthothiophene, benzonaphthofuran, indolocarbazole, indenocarbazole , Benzothieno carbazole, benzofurocarbazole, indenofluorene, fluorenobenzofuran, fluorenobenzothiophene, dibenzothienobenzofuran, and the like.

R ₁ is independently of each other hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ ~ C ₃₀ Alkoxy group; C ₆ -C ₃₀ aryloxy group; And -L'-N (R _a ) (R _b ), and adjacent groups may combine with each other to form a ring.

a is an integer of 0-4, and when a is an integer of 2 or more, a plurality of R _{1 s} are the same as or different from each other.

When R ₁ is an aryl group, preferably an aryl group of C ₆ to C ₃₀ , more preferably a C ₆ to C ₁₈ aryl group, such as phenyl, biphenyl, terphenyl, naphthyl, and the like.

L 'is a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₃ ~ C ₆₀ aliphatic ring group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; And combinations thereof.

R _a and R _b are independently of each other C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₃ ~ C ₆₀ aliphatic ring group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; And combinations thereof.

The L ₁ to L ₃ , Ar ₁ to Ar ₃ , R ₁ , L ', R _a and R _b are each deuterium; halogen; A silane group unsubstituted or substituted with an alkyl group of C ₁ -C ₂₀ or an aryl group of C ₆ -C ₂₀ ; Siloxane groups; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio; C ₁ -C ₂₀ Alkoxy group; C ₆ -C ₂₀ Arylalkoxy group; C ₁ -C ₂₀ alkyl group; Alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ Aryl group; C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; A C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ aliphatic ring group; C ₇ -C ₂₀ Arylalkyl group; And C ₈ -C ₂₀ Aryl alkenyl group; It may be further substituted with one or more substituents selected from the group consisting of.

Preferably, the Chemical Formula 1 may be represented by one of the following Chemical Formulas I-1 to I-6.

<Formula I-1> <Formula I-2> <Formula I-3>

<Formula I-4> <Formula I-5> <Formula I-6>

In Formulas I-1 to I-6, X ₁ to X ₃ , R ₁ , a, Ar ₁ , and L ₁ are as defined in Formula 1.

Preferably, Ar ₁ may be represented by Formula A or Formula B below.

    <Formula A> <Formula B>

In Chemical Formula A and Chemical Formula B, each symbol may be defined as follows.

X ₄ is NL ₅ -Ar ₅ , O, S or C (R ₂ ) (R ₃ ).

A and B rings independently of each other C ₆ ~ C ₃₀ aromatic hydrocarbons; Or a C ₂ ~ C ₃₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, P. Preferably, the A ring and the B ring independently of each other C ₆ ~ C ₂₄ aromatic hydrocarbons; Or a C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, P.

At this time, the A ring and the B ring may be further substituted with one or more R ^a , respectively. Where R ^a is hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with an alkyl group of C ₁ -C ₂₀ or an aryl group of C ₆ -C ₂₀ ; Cyano group; Nitro group; C ₁ -C ₂₀ alkyl group; Alkenyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ Aryl group; Fluorenyl group; A C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C ₃ -C ₂₀ Aliphatic ring group; It may be selected from the group consisting of.

L ₅ is a single bond; C ₆ ~ C ₂₀ Arylene group; Fluorylene group; C ₃ ~ C ₂₀ aliphatic ring group; And C ₂ ~ C ₂₀ heterocyclic group including at least one heteroatom of O, N, S, Si and P; may be selected from the group consisting of.

Ar ₅ is a C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And -L'-N (R _a ) (R _b ).

R ₂ and R ₃ are independently of each other hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with an alkyl group of C ₁ -C ₂₀ or an aryl group of C ₆ -C ₂₀ ; Cyano group; Nitro group; C ₁ -C ₂₀ alkyl group; Alkenyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ Aryl group; Fluorenyl group; A C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C ₃ -C ₂₀ aliphatic ring group; is selected from the group consisting of, R ₂ and R ₃ may be bonded to each other to form a ring.

The L ', R _a and R _b are as defined in Formula 1.

Preferably, in Formula A and Formula B, the A ring and the B ring may be selected from the group consisting of the following Formulas B-1 to B-16.

(B-1) (B-2) (B-3) (B-4) (B-5) (B-6)

(B-7) (B-8) (B-9) (B-10) (B-11)

(B-12) (B-13) (B-14) (B-15) (B-16)

In Chemical Formulas B-1 to B-16, * represents a condensed position. That is, * denotes a position condensed with a 5-membered ring containing X ₄ or a 5-membered ring containing N.

V is independently of each other C (R ^a ) or N, and X ₅ is NL ₆ -Ar ₆ , O, S or C (R ₄ ) (R ₅ ).

R ^a is as defined in Formulas A and B above.

L ₆ is a single bond; C ₆ ~ C ₂₀ Arylene group; Fluorylene group; C ₃ ~ C ₂₀ aliphatic ring group; And C ₂ ~ C ₂₀ heterocyclic group including at least one heteroatom of O, N, S, Si and P; may be selected from the group consisting of.

Ar ₆ is a C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And -L'-N (R _a ) (R _b ).

R ₄ and R ₅ are independently of each other hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with an alkyl group of C ₁ -C ₂₀ or an aryl group of C ₆ -C ₂₀ ; Cyano group; Nitro group; C ₁ -C ₂₀ alkyl group; Alkenyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ Aryl group; Fluorenyl group; A C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C ₃ -C ₂₀ aliphatic ring group; may be selected from the group consisting of, R ₄ and R ₅ may be bonded to each other to form a ring.

The L ', R _a and R _b are as defined in Formula 1.

Preferably, Ar ₁ may be selected from the group consisting of the following Chemical Formulas 1-1 to 1-9.

<Formula 1-1> <Formula 1-2> <Formula 1-3>

<Formula 1-4> <Formula 1-5> <Formula 1-6>

<Formula 1-7> <Formula 1-8> <Formula 1-9>

In the above Chemical Formulas 1-1 to 1-9, each symbol may be defined as follows. * Represents the position to combine with L _1.

X ₆ is N, N- (L ₇ -Ar ₇ ), O or S, provided that in Formula 1-7 and Formula 1-8, X ₆ is N- (L ₇ -Ar ₇ ), O or S.

X ₇ and X ₈ are each independently a single bond, N, N- (L ₈ -Ar ₈ ), O or S, provided that in Formula 1-6 and Formula 1-9, X ₇ and X ₈ are independently of each other A bond, N- (L ₈ -Ar ₈ ), O or S, a plurality of L ₈ are the same or different, a plurality of Ar ₈ are the same or different, and X ₇ and X ₈ are all single bonds Is excluded, o and p are integers of 0 or 1, and at least one of o and p is an integer of 1.

R ₆ to R ₈ are hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with an alkyl group of C ₁ -C ₂₀ or an aryl group of C ₆ -C ₂₀ ; Siloxane groups; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio; C ₁ -C ₂₀ Alkoxy group; C ₆ -C ₂₀ Arylalkoxy group; C ₁ -C ₂₀ alkyl group; Alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ Aryl group; Fluorenyl group; A C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C ₃ -C ₂₀ Aliphatic ring group; It may be selected from the group consisting of.

b, c and f are each an integer of 0 to 4, d and e are each an integer of 0 to 6, and when each of them is an integer of 2 or more, each of R ^6, each of R ^{7, and} each of R ⁸ is the same or different.

L ₇ and L ₈ are each independently a single bond; C ₆ ~ C ₂₀ Arylene group; Fluorylene group; C ₃ ~ C ₂₀ aliphatic ring group; And C ₂ ~ C ₂₀ heterocyclic group including at least one heteroatom of O, N, S, Si and P; may be selected from the group consisting of.

Ar ₇ and Ar ₈ are independently of each other C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; And -L'-N (R _a ) (R _b ). Here, L ', R _a and R _b are as defined in Formula 1.

Specifically, the compound represented by Formula 1 may be one of the following compounds, but is not limited thereto.

In another aspect, the present invention provides an organic electric device including a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer is one type represented by Chemical Formula 1 Single compound or two or more compounds.

The organic material layer includes at least one layer of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, and preferably, the compound is included in the light emitting layer.

Synthetic example

The compound represented by Chemical Formula 1 according to the present invention may be synthesized by reacting Sub 1 and Sub 2 or Sub 1 and Sub 3 as shown in Reaction Scheme 1 below, but is not limited thereto. Reaction Scheme 1 below shows that one of Y ₁ to Y ₄ in Formula 1 is C- (L ₁ -Ar ₁ ), wherein Ar ₁ is Formula A or Formula B.

<Scheme 1>

In Reaction Scheme 1, two of Y ₁ to Y ₄ are N, and one of the other is C bonded to L ₁ -Sub 2 or L ₁ -Sub 3, and the other is N or C- (L ₁ -Ar ₁ ), two of Y ₅ ~ Y ₈ are N, the other is C, which is bonded to L ₁ -Cl, the other is N or C- (L ₁ -Ar ₁ ), and the remaining symbols are chemical formulas. 1, as defined in Formula A and Formula B.

I. Sub 1 Synthesis Example

Sub 1 of Scheme 1 may be synthesized by the following Reaction Schemes 2 to 4, but is not limited thereto.

1. Synthesis of Sub 1-A

<Reaction Scheme 2>

Synthesis of Sub 1-A-3

Sub 1-A-1, Sub 1-A-2, K ₂ CO ₃ (3 eq) and Pd (PPh ₃ ) ₄ (0.05 eq) were dissolved in anhydrous THF and a small amount of water, and then at 80 ° C. for 12 hours. Refluxed. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with MC, and wiped with water. The organic layer was dried over MgSO ₄ and concentrated, followed by separation with a silica gel column to obtain Sub 1-A-3.

Synthesis of Sub 1-A-4

Sub 1-A-3 and triphenylphosphine (2.5 eq.) Were dissolved in o- dichlorobenzene and refluxed for 24 hours. When the reaction is completed, the solvent is removed using distillation under reduced pressure. Subsequently, the concentrate was removed by silica gel column and recrystallization to obtain Sub 1-A-4.

Synthesis of Sub 1-A

Sub 1-A-4, Sub 1-A-5, Pd ₂ (dba) ₃ (0.05 eq), P (t-Bu) ₃ (0.1 eq), NaO t -Bu (3 eq), toluene added Then, the mixture was stirred and refluxed at 100 ° C for 24 hours. After the reaction is completed, the mixture is extracted with ether and water, and the organic layer is dried over MgSO ₄ and concentrated. Thereafter, the concentrate was removed by silica gel column and recrystallization to obtain Sub 1-A.

1) Sub 1-43 Synthesis Example

(1) Sub 1-43-A synthesis

(2,4-dichlorofuro [3,2-d] pyrimidin-7-yl) boronic acid (15 g, 64.43 mmol) in 1-bromo-2-nitrobenzene (15.62 g, 77.32 mmol), K ₂ CO ₃ (26.71 g, 193.29 mmol), Pd (PPh ₃ ) ₄ (3.72 g, 3.22 mmol), THF (300 ml) and water (150 ml) were added, followed by the same method as for the synthesis of Sub 1-A-3. Sub 1-43-A (14.78 g, 74%) was obtained.

(2) Sub 1-43-B synthesis

After adding triphenylphosphine (29.6 g, 112.87 mmol) and o- dichlorobenzene (280 ml) to Sub 1-43-A (14 g, 45.15 mmol), proceed in the same way as the synthesis method for Sub 1-A-4. 1-43-B (5.65 g, 45%) was obtained.

(3) Sub 1-43-C synthesis

Bromobenzene (3.25 g, 20.68 mmol), Pd ₂ (dba) ₃ (0.82 g, 0.9 mmol), P (t-Bu) ₃ (0.4 g, 1.8 mmol) in Sub 1-43-B (5 g, 17.98 mmol) ), NaO t -Bu (5.18 g, 53.94 mmol) and toluene (200 ml) were added, followed by the same method as for the synthesis of Sub 1-A to give Sub 1-43-C (4.2 g, 66%). Got.

(4) Sub 1-43 synthesis

Sub 1-43-C (4 g, 11.29 mmol) with phenylboronic acid (1.65 g, 13.55 mmol), K ₂ CO ₃ (4.68 g, 33.88 mmol), Pd (PPh ₃ ) ₄ (0.65 g, 0.56 mmol), After adding THF (80 ml) and water (40 ml), the same method as for the synthesis of Sub 1-A-3 was performed to obtain Sub 1-43 (3.17 g, 71%).

2. Synthesis of Sub 1-B

<Scheme 3>

Synthesis of Sub 1-B-3

Sub 1-B-1, Sub 1-B-2, Pd (PPh ₃ ) ₄ (0.03 eq) and K ₂ CO ₃ (1.5 eq) were dissolved in anhydrous THF and EtOH, H ₂ O was added and 12 at 90 ° C. Time to reflux. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with MC, and wiped with water. The organic layer was dried over MgSO ₄ and concentrated, followed by separation with a silica gel column to obtain the desired Sub 1-B-3.

Synthesis of Sub 1-B

Sub 1-B-3 and Pd (OAc) ₂ (0.05 eq) 3-nitropyridine (0.05 eq), BzOOtBu (tert-butyl peroxybenzoate) (2 eq), C ₆ F ₆ (hexafluorobenzene), DMI (N, N '-dimethylimidazolidinone) is added and refluxed at 90 ° C for 3 hours. After the reaction was completed, the solvent was removed using distillation under reduced pressure, and the concentrated product was removed by impurity by silica gel column and recrystallization to obtain Sub 1-B.

2) Synthesis of Sub 1-23

(1) Sub 1-23-A synthesis

6-bromo-2,4-dichloro-7-phenyl-7H-pyrrolo [2,3-d] pyrimidine (20 g, 58.31 mmol) to (2-hydroxyphenyl) boronic acid (9.65 g, 69.97 mmol), K ₂ After adding CO ₃ (12.09 g, 87.46 mmol), THF (400 ml), EtOH (100 ml), and H ₂ O (100 ml), proceed in the same way as in the synthesis method of Sub 1-B-3 to sub 1 -23-A (8.1 g, 39%) was obtained.

(2) Sub 1-23-B synthesis

Sub 1-23-A (8 g, 22.46 mmol) with Pd (OAc) ₂ (0.25 g, 1.12 mmol), 3-nitropyridine (0.14 g, 1.12 mmol), BzOOtBu (tert-butyl peroxybenzoate) (8.72 g, 44.92 mmol), C ₆ F ₆ (hexafluorobenzene) (200 ml), DMI (N, N'-dimethylimidazolidinone) (130 ml) was added, and then proceeded in the same way as the synthesis method for Sub 1-B. Sub 1-23- B (3.05 g, 44%) was obtained.

(3) Sub 1-23 synthesis

Sub 1-23-B (3 g, 8.47 mmol) with phenylboronic acid (1.24 g, 10.16 mmol), K ₂ CO ₃ (3.51 g, 25.41 mmol), Pd (PPh ₃ ) ₄ (0.49 g, 0.42 mmol), After adding THF (60 ml) and water (30 ml), the same method as for the synthesis of Sub 1-A-3 was performed to obtain Sub 1-43 (2.55 g, 76%).

3) Synthesis of Sub 1-C

<Reaction Scheme 4>

Synthesis of Sub 1-C-3

Sub 1-C-2 to Sub 1-C-1, Pd ₂ (dba) ₃ (0.05 equivalent), DPEPhos (Oxydi-2,1-phenylene) bis (diphenylphosphine) (0.15 equivalent), t-BuONa (1.1 equivalent ), toluene was added and refluxed at 60 ° C for 2 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with MC, and wiped with water. The organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was separated by a silica gel filter to obtain Sub 1-C-3.

Synthesis of Sub 1-C

After adding Pd (OAc) ₂ (0.05 eq), P (t-Bu) ₃ (0.1 eq), K ₂ CO ₃ (3 eq) and DMA to Sub 1-C-3, stir and reflux. Cool the reactant to room temperature, extract with MC and wipe with water. The organic layer was dried over MgSO ₄ and concentrated, and impurities were removed by silica gel column and recrystallization to obtain Sub 1-C.

3. Sub 1-17 Synthesis Example

(1) Sub 1-17-A synthesis

Benzenethiol (11.4 g, 103.81 mmol), Pd ₂ (dba) ₃ (4 g, 4.33 mmol) to 6,7-dibromo-2,3-dichlorofuro [2,3-b] pyrazine (30 g, 86.51 mmol), After adding DPEPhos (Oxydi-2,1-phenylene) bis (diphenylphosphine) (7 g, 12.98 mmol), t-BuONa (9.1 g, 95.16 mmol), toluene, the same method as for the synthesis of Sub 1-C-3 Proceed to obtain Sub 1-17-A (20.1 g, 62%).

(2) Sub 1-17-B synthesis

Sub 1-17-A (19 g, 50.53 mmol) with Pd (OAc) ₂ (0.6 g, 2.53 mmol), P (t-Bu) ₃ (1 g, 5.1 mmol), K ₂ CO ₃ (21 g, 151.59 mmol), DMA was added, and then proceeded in the same manner as the synthesis method of Sub 1-C to obtain Sub 1-17-B (5.4 g, 0.36%).

(3) Sub 1-17 synthesis

Sub 1-17-B (4 g, 13.55 mmol) with phenylboronic acid (1.98 g, 16.26 mmol), K ₂ CO ₃ (5.62 g, 40.66 mmol), Pd (PPh ₃ ) ₄ (0.78 g, 0.68 mmol), After adding THF (80 ml) and water (40 ml), the same method as for the synthesis of Sub 1-A-3 was performed to obtain Sub 1-17 (3.24 g, 71%).

The compounds belonging to Sub 1 are as follows, but are not limited thereto, and the FD-MS values of these compounds are shown in Table 1.

[Table 1]

Ⅱ. Synthesis Example of Sub 2

Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 5, but is not limited thereto.

<Scheme 5>

1. Sub 2-15 Synthesis Example

(1) Sub 2-15a synthesis

2-bromo-9-phenyl-9H-carbazole (50 g, 155.18 mmol), bis (pinacolato) diboron (51.23 g, 201.73 mmol), KOAc (45.69 g, 465.54 mmol), PdCl ₂ (dppf) (5.68 g, 7.76 mmol) was dissolved in DMF (1 L) solvent, and refluxed at 120 ° C. for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ and wiped with 1N HCl. The organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was recrystallized using CH ₂ Cl ₂ and methanol solvent to obtain the product (36.09 g, 81%).

(2) Sub 2-15b synthesis

Sub 1-15a (30 g, 104.48 mmol), 1-bromo-2-nitrobenzene (27.44 g, 135.83 mmol), K ₂ CO ₃ (43.32 g, 313.45 mmol), Pd (PPh ₃ ) ₄ (6.04 g, 5.22 mmol) was placed in a round bottom flask, dissolved in THF (600 mL) and water (300 mL), and refluxed at 80 ° C. for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ and wiped with water. The organic layer was dried over MgSO ₄ and concentrated, followed by separation with a silica gel column to obtain the product (26.27 g, 69%).

(3) Sub 2-15 synthesis

Sub 1-15b (10 g, 27.44 mmol) and triphenylphosphine (17.99 g, 68.61 mmol) were dissolved in o- dichlorobenzene (200 mL) and refluxed at 180 ° C. for 24 hours. After the reaction was completed, the solvent was removed using distillation under reduced pressure, and the concentrated product was separated by impurities by silica gel column and recrystallization to obtain the desired product (6.39 g, 70%).

2. Sub 2-30 Synthesis Example

(1) Sub 2-30a synthesis

5-bromobenzo [b] naphtha [1,2-d] thiophene (50 g, 159.64 mmol) in bis (pinacolato) diboron (52.7 g, 207.53 mmol), KOAc (47 g, 478.91 mmol), PdCl ₂ (dppf) (5.84 g, 7.98 mmol) was added and then proceeded in the same manner as in the synthesis method of Sub 2-15a to obtain the product (35.52 g, 80%).

(2) Sub 2-30b synthesis

1-bromo-2-nitrobenzene (27.44 g, 135.83 mmol), K ₂ CO ₃ (43.32 g, 313.45 mmol), Pd (PPh ₃ ) ₄ (6.04 g, 5.22) to Sub 2-30a (30 g, 104.48 mmol) mmol), THF (600 mL), and water (300 mL) were added, followed by the same procedure as in Sub 2-15b to obtain the product (27.11 g, 73%).

(3) Sub 2-30 synthesis

After adding triphenylphosphine (18.45 g, 70.34 mmol) and o- dichlorobenzene (200 mL) to Sub 2-30b (10 g, 28.14 mmol), proceed in the same manner as in the synthesis method for Sub 2-15 to give the product (6.27 g, 67%).

Compounds belonging to Sub 2 are the same as the following compounds, but are not limited thereto, and Table 2 shows the FD-MS values of these compounds.

[Table 2]

III. Synthesis Example of Sub 3

Sub 3 of Scheme 1 may be synthesized by the following Reaction Scheme 6, but is not limited thereto.

<Scheme 6>

1. Sub 3-50 Synthesis Example

(1) Sub 3-50a synthesis

2-bromodibenzo [b, d] thiophen-3-ol (25 g, 89.56 mmol), (2-chloro-6-fluorophenyl) boronic acid (20.3 g, 116.42 mmol), K ₂ CO ₃ (37.13 g, 268.67 mmol ), Pd (PPh ₃ ) ₄ (5.17 g, 4.48 mmol) was put in a round bottom flask, dissolved in THF (500 mL) and water (250 mL), and refluxed at 80 ° C. for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ and wiped with water. The organic layer was dried over MgSO ₄ and concentrated, followed by separation with a silica gel column to obtain the product (16.2 g, 55%).

(2) Sub 3-50b synthesis

Sub 3-50a (20 g, 60.83 mmol) and K ₂ CO ₃ (21.02 g, 152.07 mmol) were placed in a round bottom flask, and then NMP was added and refluxed at 110 ° C. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ and wiped with water. The organic layer was dried over MgSO ₄ and concentrated, followed by separation with a silica gel column to obtain the product (11.46 g, 61%).

(3) Sub 3-50 synthesis

Sub 3-50b (10 g, 32.39 mmol), bis (pinacolato) diboron (10.69 g, 42.1 mmol), KOAc (9.54 g, 97.16 mmol), PdCl ₂ (dppf) (1.18 g, 1.62 mmol) in DMF (250 mL) After dissolving in a solvent, the mixture was refluxed at 120 ° C for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ and wiped with 1N HCl. The organic layer was dried over MgSO ₄ and concentrated, and the resulting organic material was recrystallized using CH ₂ Cl ₂ and methanol solvent to obtain the product (7.93 g, 77%).

(1) Sub 3-53a synthesis

(9-chlorodibenzo [b, d] thiophen-2-yl) boronic acid (30 g, 114.28 mmol), 1-bromo-2-nitrobenzene (30 g, 148.57 mmol), K ₂ CO ₃ (47.38 g, 342.84 mmol), Pd (PPh ₃ ) ₄ (6.6 g, 5.71 mmol) was placed in a round bottom flask, dissolved in THF (600 mL) and water (300 mL), and then heated at 80 ° C. for 12 hours. During reflux. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ and wiped with water. The organic layer was dried over MgSO ₄ and concentrated, followed by separation with a silica gel column to obtain the product (27.57 g, 71%).

(2) Sub 3-53b synthesis

Sub 3-53a (20 g, 58.86 mmol) and triphenylphosphine (38.60 g, 147.15 mmol) were dissolved in o- dichlorobenzene (400 mL) and refluxed at 200 ° C. for 24 hours. After the reaction was completed, the solvent was removed using distillation under reduced pressure, and the concentrated product was separated by impurities by silica gel column and recrystallization to obtain the product (11.23 g, 62%).

(3) Sub 3-53c synthesis

After dissolving Sub 3-53b (10 g, 32.49 mmol) in toluene, bromobenzene (5.87 g, 37.36 mmol), Pd ₂ (dba) ₃ (1.49 g, 1.62 mmol), P (t-Bu) ₃ (0.66 g) , 3.25 mmol), NaO t -Bu (9.37 g, 97.47 mmol), toluene was added, and the mixture was refluxed with stirring at 100 ° C for 24 hours. After the reaction was completed, the mixture was extracted with ether and water, and then the organic layer was dried over MgSO ₄ and concentrated, and impurities were separated by silica gel column and recrystallization to obtain the product (9.73 g, 78%).

 (4) Sub 3-53 synthesis

Sub 3-53c (9 g, 23.44 mmol), bis (pinacolato) diboron (7.74 g, 30.48 mmol), KOAc (6.9 g, 70.33 mmol), PdCl ₂ (dppf) (0.86 g, 1.17 mmol) in DMF (180 mL) After dissolving in a solvent, the same procedure as in Sub 3-50 was performed to obtain a product (7.84 g, 85%).

Compounds belonging to Sub 3 are the same as the following compounds, but are not limited thereto, and FD-MS values of these compounds are shown in Table 3 below.

[Table 3]

Ⅲ. Synthesis Example of Final Compound

Synthesis of 1-23

Sub 2-30 (5.52 g, 17.07 mmol), NaO t -Bu (4.28 g, 44.54 mmol), Pd ₂ (dba) ₃ (0.68 g, 0.74 mmol) to Sub 1-35 (5 g, 14.85 mmol), After adding P (t-Bu) ₃ (0.3 g, 1.48 mmol), toluene (200 mL), The mixture was stirred and refluxed at 100 ° C for 24 hours. After the reaction is completed, the mixture is extracted with ether and water, and the organic layer is dried over MgSO ₄ and concentrated. After that, the impurities were separated by recrystallization from the silica gel column to obtain 6.57 g of product (yield: 71%).

Synthesis of 1-76

Sub 2-32 (3.43 g, 11.17 mmol), NaO t -Bu (2.8 g, 29.13 mmol), Pd ₂ (dba) ₃ (0.44 g, 0.49 mmol) to Sub 1-12 (4 g, 9.71 mmol), After adding P (t-Bu) ₃ (0.2 g, 0.97 mmol), toluene (160 mL), Proceeding in the same manner as in the synthesis method of 1-23, the product 5.11 g (yield: 77%) was obtained.

Synthesis of 1-87

Sub 2-13 (2.88 g, 10.76 mmol), NaO t -Bu (2.7 g, 28.06 mmol), Pd ₂ (dba) ₃ (0.43 g, 0.47 mmol) to Sub 1-34 (3 g, 9.35 mmol), After adding P (t-Bu) ₃ (0.2 g, 0.94 mmol), toluene (120 mL), Proceeding in the same manner as in the experimental method of 1-23, 3.51 g (yield: 68%) of the final compound was obtained.

Synthesis of 1-107

Sub 3-51 (6.72 g, 17.82 mmol), Pd (PPh ₃ ) ₄ (0.86 g, 0.74 mmol), K ₂ CO ₃ (6.16 g, 44.54 mmol) to Sub 1-26 (5 g, 14.85 mmol), Add THF (100 ml), EtOH (30 ml), H ₂ O (30 ml) and reflux at 90 ° C. for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with MC, and wiped with water. The organic layer was dried over MgSO ₄ and concentrated to remove impurities with a silica gel column to obtain 6.96 g (74%) of the product.

The FD-MS values of the compounds 1-1 to 1-134 of the present invention prepared according to the above synthesis examples are shown in Table 4 below.

[Table 4]

Manufacturing evaluation of organic electric devices

[Example 1] Red organic electroluminescent device (host)

N ^1- (naphthalen-2-yl) -N ⁴ , N ⁴ -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl) -N ¹ -phenylbenzene on ITO layer (anode) formed on glass substrate After vacuum-depositing -1,4-diamine to a thickness of 60 nm to form a hole injection layer, 4,4-bis [N- (1-naphthyl) -N-phenylamino] biphenyl is formed on the hole injection layer. Was vacuum-deposited to a thickness of 60 nm to form a hole transport layer.

Subsequently, on the hole transport layer, Compound 1-1 of the present invention was used as a host material, and bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate was used as a dopant material, but the dopants were doped so that the weight ratio was 95: 5 to 30 nm thickness. The light emitting layer of was deposited.

Next, (1,1'-biphenyl-4-olato) bis (2-methyl-8-quinolinolato) aluminum is vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, and on the hole blocking layer Tris (8-quinolinol) aluminium was formed to a thickness of 40 nm to form an electron transport layer.

Thereafter, LiF was deposited on the electron transport layer to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm to form a cathode.

[Example 2] to [Example 26]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention shown in Table 5 below was used instead of Compound 1-1 as the host material of the light emitting layer.

[Comparative Example 1] to [Comparative Example 4]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that one of the following Comparative Compounds A to D was used as the host material for the light emitting layer.

<Comparative Compound A> <Comparative Compound B> <Comparative Compound C> <Comparative Compound D>

The electro-luminescence (EL) characteristics of the organic electroluminescent devices of Examples 1 to 26 and Comparative Examples 1 to 4 manufactured as described above were measured by photoresearch's PR-650 by applying a direct bias DC voltage and measuring 2500 cd / m. ² T95 life was measured at a reference luminance through a life measurement equipment manufactured by Max Science. Measurement results are shown in Table 5 below.

[Table 5]

As can be seen from the results of Table 5, the organic electroluminescent device using the material for an organic electroluminescent device of the present invention as a phosphorescent host of the light emitting layer has significantly improved efficiency and lifespan than Comparative Compounds A to D, and the driving voltage was lowered.

Comparative compound B, in which pyrrolopyrimidine is condensed in benzofuran, Comparative compound C, in which pyrrolopyridine is condensed in indole, or pyrrolopyridine is condensed in benzothiophene than comparative compound A (CBP), which is generally used as a host material. The device results of Comparative Compound D were excellent, and the device results were better when the compounds of the present invention were used than Comparative Compounds B to D. Accordingly, the driving voltage and efficiency of the device according to the number of amines (the number of nitrogens included in the outer hexagonal ring), the type of substituents bonded to the N-containing outer ring, and the number and bonding positions of the substituents bound to the N-containing outer ring And it can be seen that the life, etc. are changed.

When the comparative compound C or D was used as the host, the driving voltage was lower and the efficiency was improved when the comparative compound B was used.

And when comparing the compounds of the present invention and comparative compounds C and D, the energy level (enegy) of the compound according to the number of N in the hexagonal ring containing N of the four-ring core, the bonding position of the substituted substituents and the number of substituents, etc. level), and the band gap of the compound of the present invention is easier to transport holes and electrons than the comparative compound, and thus it is determined that the luminous efficiency is increased.

That is, in Formula 1, when two of Y ₁ to Y ₄ are N, and the other two are CL ₁ -Ar ₁ as a host, device characteristics are improved compared to a case where a comparative compound is used, particularly Ar ₁ In the case of Formula A, it has an effect of lowering the driving voltage by having an energy level that is easy for hole movement. In the case of Formula B, charge balance in the light emitting layer is increased by having an appropriate T ₁ value and a deep HOMO value at the same time. It seems to maximize the luminous efficiency.

The data of each type of compound measured using the DFT method (B3LYP / 6-31g (D)) of the Gaussian program is shown in Table 6 below.

<B Type> <C Type> <D Type>

Type B is when the H attached to the carbon of the N-containing hexagonal ring (pyridine ring) is not substituted with another substituent, and C is the case where one heterocycle (carbazole) is attached to the carbon of the pyrimidine ring. , D type is a compound of the present invention in which an aryl type (phenyl) and a heterocycle (carbazole) are bonded to each carbon of the pyrimidine ring. That is, the number and type of the substituents substituted for the pyrimidine moiety in the B type and the C type are different from that of the compound D of the present invention. Due to the difference between the presence and absence of such substituent bonds, physical properties of each compound are changed as shown in Table 6 below.

[Table 6]

Referring to Table 6, since the LUMO value of the D type is the smallest (deep), it seems to be most advantageous for electron transport, and the D Type of the present invention is narrower than the B and C type. deep) T ₁ value, which is advantageous for realizing high efficiency and lifetime. This can be confirmed through the device data results in Table 5.

The above description is merely illustrative of the present invention, and those skilled in the art to which the present invention pertains will be capable of various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed herein are not intended to limit the present invention, but to explain the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The scope of protection of the present invention should be interpreted by the following claims, and all technologies within the equivalent range should be interpreted as being included in the scope of the present invention.

CROSS-REFERENCE TO RELATED APPLICATION

This patent application is filed in US Patent Law 119 for Patent Application No. 10-2018-0106577 filed in Korea on September 06, 2018 and Patent Application No. 10-2019-0105340 filed in Korea on August 27, 2019. Priority is claimed pursuant to Articles Article 121 to Article 365 (35 USC §19 to §121, §365), all of which are incorporated into this patent application by reference. In addition, if this patent application claims priority to countries other than the United States for the same reason as above, all the contents are incorporated into this patent application as a reference.

Claims (12)

A compound represented by formula (1): <Formula 1>

In Chemical Formula 1, Y ₁ to Y ₄ are each independently N or C- (L ₁ -Ar ₁ ), at least two of Y ₁ to Y ₄ are N, and a plurality of L ₁ are the same or different, and a plurality of Ar ₁ is Each is the same or different, X ₁ is N- (L ₂ -Ar ₂ ), O or S, X ₂ and X ₃ are each independently a single bond, N- (L ₃ -Ar ₃ ), O or S, except that X ₂ and X ₃ are both single bonds, and a plurality of L ₃ are the same or each Different, and a plurality of Ar ₃ are the same or different, n and m are each integers of 0 or 1, and at least one of n and m is 1, R ₁ is independently of each other hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ ~ C ₃₀ Alkoxy group; C ₆ -C ₃₀ aryloxy group; And -L'-N (R _a ) (R _b ), a is an integer from 0 to 4, and when a is an integer of 2 or more, a plurality of R _{1 s} are the same as or different from each other, L ₁ to L ₃ are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₃ ~ C ₆₀ aliphatic ring group; And O, N, S, Si, and C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom; is selected from the group consisting of, Ar ₁ to Ar ₃ are independently of each other C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; And -L'-N (R _a ) (R _b ), L 'is a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₃ ~ C ₆₀ aliphatic ring group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; And combinations thereof, R _a and R _b are independently of each other C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₃ ~ C ₆₀ aliphatic ring group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; And combinations thereof, The L ₁ to L ₃ , Ar ₁ to Ar ₃ , R ₁ , L ', R _a and R _b are each deuterium; halogen; A silane group unsubstituted or substituted with an alkyl group of C ₁ -C ₂₀ or an aryl group of C ₆ -C ₂₀ ; Siloxane groups; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio; C ₁ -C ₂₀ Alkoxy group; C ₆ -C ₂₀ Arylalkoxy group; C ₁ -C ₂₀ alkyl group; Alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ Aryl group; C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; A C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ aliphatic ring group; C ₇ -C ₂₀ Arylalkyl group; And C ₈ -C ₂₀ Aryl alkenyl group; It may be further substituted with one or more substituents selected from the group consisting of. According to claim 1, Formula 1 is a compound characterized in that represented by one of the formulas I-1 to I-6: <Formula I-1> <Formula I-2> <Formula I-3>

<Formula I-4> <Formula I-5> <Formula I-6>

In Formulas I-1 to I-6, X ₁ to X ₃ , R ₁ , a, Ar ₁ , and L ₁ are as defined in claim 1. According to claim 1, Ar ₁ is a compound characterized in that represented by the following formula A or formula B: <Formula A> <Formula B>

In the above formula A and B, X ₄ is NL ₅ -Ar ₅ , O, S or C (R ₂ ) (R ₃ ), A and B rings independently of each other C ₆ ~ C ₃₀ aromatic hydrocarbons; Or C ₂ ~ C ₃₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, P, A ring and B ring may be further substituted with one or more R ^a , which are the same or different from each other, L ₅ is a single bond; C ₆ ~ C ₂₀ Arylene group; Fluorylene group; C ₃ ~ C ₂₀ aliphatic ring group; And C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; is selected from the group consisting of, Ar ₅ is a C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And -L'-N (R _a ) (R _b ), R ₂ , R ₃ and R ^a are independently of each other hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with an alkyl group of C ₁ -C ₂₀ or an aryl group of C ₆ -C ₂₀ ; Cyano group; Nitro group; C ₁ -C ₂₀ alkyl group; Alkenyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ Aryl group; Fluorenyl group; A C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C ₃ -C ₂₀ aliphatic ring group; is selected from the group consisting of, R ₂ and R ₃ may be bonded to each other to form a ring, The L ', R _a and R _b are as defined in claim 1. According to claim 3, The A ring and the B ring are compounds selected from the group consisting of the following formulas B-1 to B-16: (B-1) (B-2) (B-3) (B-4) (B-5) (B-6)

(B-7) (B-8) (B-9) (B-10) (B-11)

(B-12) (B-13) (B-14) (B-15) (B-16)

In Chemical Formulas B-1 to B-16, * represents a condensation position, V is independently of each other C (R ^a ) or N, X ₅ is NL ₆ -Ar ₆ , O, S or C (R ₄ ) (R ₅ ), R ^a , R ₄ and R ₅ are independently of each other hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with an alkyl group of C ₁ -C ₂₀ or an aryl group of C ₆ -C ₂₀ ; Cyano group; Nitro group; C ₁ -C ₂₀ alkyl group; Alkenyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ Aryl group; Fluorenyl group; A C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C ₃ -C ₂₀ Aliphatic ring group; is selected from the group consisting of, R ₄ and R ₅ may be bonded to each other to form a ring, L ₆ is a single bond; C ₆ ~ C ₂₀ Arylene group; Fluorylene group; C ₃ ~ C ₂₀ aliphatic ring group; And C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; is selected from the group consisting of, Ar ₆ is a C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; And -L'-N (R _a ) (R _b ), The L ', R _a and R _b are as defined in claim 1. According to claim 1, The Ar ₁ is a compound characterized in that it is selected from the group consisting of Formula 1-1 to Formula 1-9: <Formula 1-1> <Formula 1-2> <Formula 1-3>

<Formula 1-4> <Formula 1-5> <Formula 1-6>

<Formula 1-7> <Formula 1-8> <Formula 1-9>

In the above Chemical Formulas 1-1 to 1-9, * represents a position where L ₁ is bonded, X ₆ is N, N- (L ₇ -Ar ₇ ), O or S, provided that in Formula 1-7 and Formula 1-8, X ₆ is N- (L ₇ -Ar ₇ ), O or S, X ₇ and X ₈ are each independently a single bond, N, N- (L ₈ -Ar ₈ ), O or S, provided that in Formula 1-6 and Formula 1-9, X ₇ and X ₈ are independently of each other A bond, N- (L ₈ -Ar ₈ ), O or S, a plurality of L ₈ are the same or different, a plurality of Ar ₈ are the same or different, and X ₇ and X ₈ are all single bonds Is excluded, o and p are integers of 0 or 1, and at least one of o and p is an integer of 1, R ₆ to R ₈ are hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with an alkyl group of C ₁ -C ₂₀ or an aryl group of C ₆ -C ₂₀ ; Siloxane groups; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio; C ₁ -C ₂₀ Alkoxy group; C ₆ -C ₂₀ Arylalkoxy group; C ₁ -C ₂₀ alkyl group; Alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ Aryl group; Fluorenyl group; A C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C ₃ -C ₂₀ Aliphatic ring group; is selected from the group consisting of, b, c and f are integers of 0 to 4, d and e are integers of 0 to 6, respectively, and when each of these is an integer of 2 or more, each of R ^6, each of R ^{7, and} each of R ⁸ is the same or different from each other, L ₇ and L ₈ are each independently a single bond; C ₆ ~ C ₂₀ Arylene group; Fluorylene group; C ₃ ~ C ₂₀ aliphatic ring group; And C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; is selected from the group consisting of, Ar ₇ and Ar ₈ are independently of each other C ₆ ~ C ₂₀ aryl group; Fluorenyl group; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₂₀ aliphatic ring group; C ₃ ~ C ₂₀ aliphatic ring and C ₆ ~ C ₂₀ aromatic ring fused ring group; And -L'-N (R _a ) (R _b ), The L ', R _a and R _b are as defined in claim 1. According to claim 1, The compound represented by Formula 1 is one of the following compounds:

. In the organic electric device including a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, The organic material layer is an organic electric device comprising a single compound or two or more compounds represented by the formula (1) of claim 1. The method of claim 7, The organic material layer comprises at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer. The method of claim 8, The compound is an organic electrical device, characterized in that included in the light emitting layer. The method of claim 7, The organic layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process. A display device comprising the organic electroluminescent element of claim 7; And An electronic device comprising; a control unit for driving the display device. The method of claim 11, The organic electric device is an electronic device, characterized in that selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device and a quantum dot display device.

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