JP2003128651A - Hydrocarbon compound, material for organic electroluminescent element and organic electroluminescent element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an organic electroluminescent element which has excellent emitting efficiency and emits light at high intensity, and also to provide a new hydrocarbon compound which is preferably used for the electroluminescent element. SOLUTION: This organic electroluminescent element includes between a pair of electrodes, at least one layer containing at least one hydrocarbon compound in which anthracent and fluorene rings which have respective groups having formula (I) [wherein, Ar1 and Ar2 are substituted or unsubstituted arylene group; and Z is a coupling group] are directly bonded to each other. This hydrocarbon compound is a compound in which anthracene and fluorene rings which have respective groups represented by formula (I) [wherein, Ar1 and Ar2 are each a substituted or unsubstituted arylene group; and Z is a coupling group] are directly bonded to each other.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to an organic electroluminescent device, a material for an organic electroluminescent device which can be suitably used for the light emitting device, and a novel hydrocarbon compound.

[0002]

2. Description of the Related Art Conventionally, an inorganic electroluminescent device has been used as a panel type light source such as a backlight, but a high AC voltage is required to drive the light emitting device. Recently, an organic electroluminescence device (organic electroluminescence device: organic EL device) using an organic material as a light emitting material has been developed [Appl. Phys. Lett., 51 , 913 (19
87)]. An organic electroluminescence device has a structure in which a thin film containing a compound having a light emitting function is sandwiched between an anode and a cathode, and electrons and holes are injected into the thin film to excite by recombination. This element emits light by generating light (exciton) and utilizing the light emitted when the exciton is deactivated. The organic electroluminescence device can emit light at a low DC voltage of about several V to several tens of V, and various colors (for example, red, blue, green) can be obtained by selecting the type of the fluorescent organic compound. Can emit light. The organic electroluminescent device having such characteristics is expected to be applied to various light emitting devices, display devices and the like. However, the emission brightness is generally low, which is not practically sufficient.

As a method for improving the light emission brightness, for example, an organic electroluminescent device using a light emitting layer using tris (8-quinolinolato) aluminum as a host compound, a coumarin derivative, and a pyran derivative as a guest compound (dopant) has been proposed. [J.Appl.Phys., 65 , 3610 (198
9)]. In addition, an organic electroluminescence device using an anthracene derivative as a material for a light emitting layer has been proposed (Japanese Patent Laid-Open No. H8 (1998) -8300).
-12600 gazette, Unexamined-Japanese-Patent No. 11-111458). Further, an organic electroluminescent device using an anthracene derivative as a guest compound of a light emitting layer has been proposed (Japanese Patent Laid-Open Nos. 10-36832 and 10-294).
179).

However, it cannot be said that these light emitting elements also have sufficient light emission brightness. At present, an organic electroluminescent device that emits light with higher brightness is desired.

[0005]

SUMMARY OF THE INVENTION An object of the present invention is to provide an organic electroluminescent device which has excellent luminous efficiency and emits light with high brightness. Another object of the present invention is to provide a material for an organic electroluminescent device which can be suitably used for the light emitting device. Furthermore, it is to provide a novel hydrocarbon compound.

[0006]

Means for Solving the Problems The inventors of the present invention have completed the present invention as a result of extensive studies on organic electroluminescent elements. That is, the present invention provides a hydrocarbon compound in which an anthracene ring having at least one group represented by the general formula (I) as a substituent (1) and a fluorene ring are directly bonded,

[0007]

[Chemical 9]

(Wherein Ar ₁ and Ar ₂ represent a substituted or unsubstituted arylene group, and Z represents a linking group),
(2) The hydrocarbon compound according to (1) above, wherein the fluorene ring is bonded at a position other than the 9-position, (3) the hydrocarbon compound represented by the general formula (1), X _1- (F ₁ ) _{j - (a 1) k - (} F 2) l - (a 2) m - (F 3) n -X 2 (1) [ wherein, a ₁ and a ₂ each independently represent a substituted or unsubstituted anthracene Represents a diyl group, F ₁ , F ₂ and F
₃ independently represents a substituted or unsubstituted fluorenediyl group, X ₁ and X ₂ each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic Represents an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted amino group, or a group represented by the general formula (I),

[0009]

[Chemical 10]

(In the formula, Ar ₁ and Ar ₂ represent a substituted or unsubstituted arylene group, Z represents a linking group.) J, m and n represent 0 or 1, and k and l represent 1 or 2 And when k is 2, A _{1 s} may be the same or different, and when l is 2, F 2 s may be the same or different, provided that at least X ₁ and X 2 One is a group represented by the general formula (I). ]
(4) A hydrocarbon compound represented by the general formula (2),

[0011]

[Chemical 11]

[Wherein R ₂₁ and R ₂₂ each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group; to ₂₀₁ to X ₂₂₄ are independently a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group Or a group represented by the general formula (I),

[0013]

[Chemical 12]

(In the formula, Ar ₁ and Ar ₂ represent a substituted or unsubstituted arylene group, and Z represents a linking group.) X
₂₀₁ at least one to X ₂₂₄ represents a group represented by the general formula (I). However, R ₂₁ , R ₂₂ and X _{201 to} X ₂₂₄ are not an anthryl group or a fluorenyl group. ] (5) The hydrocarbon compound represented by the general formula (3),

[0015]

[Chemical 13]

[Wherein R _{31 to} R ₃₄ each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group, and X to ₃₀₁ to X ₃₂₂ are independently a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group ,
Alternatively, it represents a group represented by the general formula (I),

[0017]

[Chemical 14]

(In the formula, Ar ₁ and Ar ₂ represent a substituted or unsubstituted arylene group, and Z represents a linking group.) X
₃₀₁ at least one to X ₃₂₂ represents a group represented by the general formula (I). However, R _{31 to} R ₃₄ and X _{301 to} X ₃₂₂ are not an anthryl group or a fluorenyl group. ] (6) The hydrocarbon compound represented by the general formula (4),

[0019]

[Chemical 15]

[Wherein R ₄₁ and R ₄₂ each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group; _{401 to} X ₄₁₆ each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group. Or a group represented by the general formula (I),

[0021]

[Chemical 16]

(In the formula, Ar ₁ and Ar ₂ represent a substituted or unsubstituted arylene group, and Z represents a linking group.) X
₄₀₁ at least one to X ₄₁₆ represents a group represented by the general formula (I). However, R ₄₁ , R ₄₂ and X _{401 to} X ₄₁₆ are not an anthryl group and a fluorenyl group. ] (7) Material for organic electroluminescent element according to the above (1) to (6),
(8) An organic electroluminescent device comprising at least one layer containing at least one kind of the organic electroluminescent device material according to (7) between a pair of electrodes, (9) (7)
The layer containing the material for organic electroluminescent element described in (8) above is a light emitting layer, (10) the layer containing the material for organic electroluminescent element according to (7) above, Furthermore, the organic electroluminescent device according to (8) or (9) above, which contains a luminescent organometallic complex, (11) the layer containing the material for organic electroluminescent device according to (7) above. Further, a layer containing the organic electroluminescent device according to (8) or (9), further comprising a triarylamine derivative, and (12) the material for organic electroluminescent device according to (7). The organic electroluminescent device according to (8) above, which is a hole injecting and transporting layer, (13) further including a hole injecting and transporting layer between the pair of electrodes.
To (11), the organic electroluminescent element according to any one of (1)
4) The organic electroluminescent element according to any one of the above (8) to (13), further having an electron injecting and transporting layer between a pair of electrodes.

[0023]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail below.

The present invention relates to a hydrocarbon compound in which an anthracene ring having at least one group represented by the general formula (I) as a substituent is directly bonded to a fluorene ring.

[0025]

[Chemical 17]

(In the formula, Ar ₁ and Ar ₂ represent a substituted or unsubstituted arylene group, and Z represents a linking group.) As the substituent according to the present invention, a group represented by the general formula (I). The hydrocarbon compound in which the anthracene ring and the fluorene ring having at least one are directly bonded (hereinafter abbreviated as the compound A according to the present invention) does not include a polymer, and preferably has a molecular weight of 2000 or less. And
More preferably, it is a compound having a molecular weight of 1,000 or less.

In the group represented by the general formula (I), Ar
₁ and Ar ₂ represent a substituted or unsubstituted arylene group, and Z represents a linking group.

The arylene group means a carbocyclic aromatic divalent group such as a phenylene group, a naphthylene group and an anthracenediyl group, a thiophendiyl group, a pyridinediyl group,
Represents a heterocyclic aromatic divalent group such as a quinolinediyl group.

The linking group means a single bond, --O--, --S.
It represents-, -CH = CH-, an alkylene group or an arylene group.

In the group represented by the general formula (I), Ar
₁ and Ar ₂ are preferably a substituted or unsubstituted carbocyclic aromatic divalent group having 6 to 25 carbon atoms or a substituted or unsubstituted heterocyclic aromatic divalent group having 3 to 25 carbon atoms. Yes, more preferably a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group, more preferably a substituted or unsubstituted 1,2-phenylene group,
It is a substituted or unsubstituted 1,2-naphthylene group or a substituted or unsubstituted 2,3-naphthylene group.

In the group represented by the general formula (I), Z is preferably a single bond, -O-, -S-, -CH = CH.
-, An alkylene group having 1 to 8 carbon atoms, or a substituted or unsubstituted phenylene group, and more preferably a single bond or -O.
-, -S-, an alkylene group having 1 to 4 carbon atoms, a substituted or unsubstituted phenylene group, more preferably a single bond, -O-, -S-, -CH = CH-, 1,2- It is an ethylene group or a substituted or unsubstituted 1,2-phenylene group.

The group represented by the formula (I) is preferably a substituted or unsubstituted N-carbazolyl group, a substituted or unsubstituted N-benzo [a] carbazolyl group, a substituted or unsubstituted N-benzo. [b] Carbazolyl group, substituted or unsubstituted N-benzo [c] carbazolyl group, substituted or unsubstituted N-dibenzo [a, i] carbazolyl group, substituted or unsubstituted N-dibenzo [b, h] carbazolyl Group, substituted or unsubstituted N-dibenzo [c, g] carbazolyl group, substituted or unsubstituted N-phenoxaziniyl group, substituted or unsubstituted N-phenothiaziniyl group, substituted or unsubstituted N
-Acridanyl group, substituted or unsubstituted N-dibenzo
a [b, f] azepinyl group, a substituted or unsubstituted 9,10-dihydro-N-dibenzo [b, f] azepinyl group, a substituted or unsubstituted N-tribenzo [b, d, f] azepinyl group,
More preferably, a substituted or unsubstituted N-carbazolyl group, a substituted or unsubstituted N-benzo [a] carbazolyl group, a substituted or unsubstituted N-benzo [b] carbazolyl group, a substituted or unsubstituted N-benzo [c] Carbazolyl group, substituted or unsubstituted N-dibenzo [a, i] carbazolyl group, substituted or unsubstituted N-dibenzo [b, h] carbazolyl group, substituted or unsubstituted N-dibenzo [c, g ] A carbazolyl group, a substituted or unsubstituted N-phenoxaziniiyl group, a substituted or unsubstituted N-phenothiaziniyl group, more preferably a substituted or unsubstituted N-carbazolyl group, a substituted or unsubstituted It is an N-phenoxaziniyl group or a substituted or unsubstituted N-phenothiaziniyl group.

The substituent of the group represented by formula (I) is preferably a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an alkyl group having 6 to 10 carbon atoms. An aryl group, more preferably a halogen atom, an alkyl group having 1 to 4 carbon atoms, and a carbon number of 1 to 4
Or an aryl group having 6 to 10 carbon atoms.

Specific examples of the group represented by the general formula (I) include N-carbazolyl group, 2-methyl-N-carbazolyl group, 3-methyl-N-carbazolyl group, 4-methyl-
N-carbazolyl group, 3-n-butyl-N-carbazolyl group, 3-n-hexyl-N-carbazolyl group, 3-n
-Octyl-N-carbazolyl group, 3,6-dimethyl-
N-carbazolyl group, 1,4-dimethyl-N-carbazolyl group, 3,6-diethyl-N-carbazolyl group, 2-
Methoxy-N-carbazolyl group, 3-methoxy-N-carbazolyl group, 3-ethoxy-N-carbazolyl group, 3
-Isopropyloxy-N-carbazolyl group, 3-n-
Butyloxy-N-carbazolyl group, 3-n-hexyloxy-N-carbazolyl group, 3-n-octyloxy-N-carbazolyl group, 3-n-decyloxycarbazolyl group, 3-phenyl-N-carbazolyl group , 3-
(4'-methylphenyl) -N-carbazolyl group, 3-
(4'-tert-butylphenyl) -N-carbazolyl group, 3,6-diphenyl-N-carbazolyl group, 3-chloro-N-carbazolyl group, N-benzo [a] carbazolyl group, N-benzo [b] Carbazolyl group, N-benzo [c] carbazolyl group, N-dibenzo [a, i] carbazolyl group, N
-Dibenzo [b, h] carbazolyl group, N-dibenzo [c, g] carbazolyl group, N-phenoxaziniyl group, 2-methyl-N-phenoxaziniyl group, 2-chloro-N-phenoxaziniyl group, 2-fluoro-N-phenoxaziniyl group, 2-trifluoromethyl-N-phenoxaziniyl group, N-phenothiaziniyl group, 2-methyl-N-phenothiaziniyl group, 2-chloro-N- Phenothiaziniyl group, 2-fluoro-N-phenothiaziniyl group, 2
-Trifluoromethyl-N-phenothiazinyl group, N
-Acridanyl group, N-dibenzo [b, f] azepinyl group,
2-methyl-N-dibenzo [b, f] azepinyl group, 3-methyl-N-dibenzo [b, f] azepinyl group, 4-methyl-
N-dibenzo [b, f] azepinyl group, 2-trifluoromethyl-N-dibenzo [b, f] azepinyl group, 3-trifluoromethyl-N-dibenzo [b, f] azepinyl group, 3-n
-Butyl-N-dibenzo [b, f] azepinyl group, 3-n-
Hexyl-N-dibenzo [b, f] azepinyl group, 3-n-
Octyl-N-dibenzo [b, f] azepinyl group, 3-n-
Decyl-N-dibenzo [b, f] azepinyl group, 3,6-dimethyl-N-dibenzo [b, f] azepinyl group, 2-methoxy-N-dibenzo [b, f] azepinyl group, 3-methoxy-
N-dibenzo [b, f] azepinyl group, 3-ethoxy-N-
Dibenzo [b, f] azepinyl group, 3-isopropyloxy-N-dibenzo [b, f] azepinyl group, 3-n-butyloxy-N-dibenzo [b, f] azepinyl group, 3-n-octyloxy-N -Dibenzo [b, f] azepinyl group, 3-n
-Decyloxy-N-dibenzo [b, f] azepinyl group, 3
-Phenyl-N-dibenzo [b, f] azepinyl group, 3-
(4′-methylphenyl) -N-dibenzo [b, f] azepinyl group, 2-chloro-N-dibenzo [b, f] azepinyl group, 3-chloro-N-dibenzo [b, f] azepinyl group, 1
0,11-dihydro-N-dibenzo [b, f] azepinyl group, 2-methyl-10,11-dihydro-N-dibenzo
[b, f] azepinyl group, 3-methyl-10,11-dihydro-N-dibenzo [b, f] azepinyl group, 4-methyl-1
0,11-dihydro-N-dibenzo [b, f] azepinyl group, 2-trifluoromethyl-10,11-dihydro-
N-dibenzo [b, f] azepinyl group, 3-trifluoromethyl-10,11-dihydro-N-dibenzo [b, f] azepinyl group, 3-n-butyl-10,11-dihydro-N
-Dibenzo [b, f] azepinyl group, 3-n-hexyl-1
0,11-dihydro-N-dibenzo [b, f] azepinyl group, 3-n-octyl-10,11-dihydro-N-dibenzo [b, f] azepinyl group, 3-n-decyl-10,1
1-dihydro-N-dibenzo [b, f] azepinyl group, 3,
6-dimethyl-10,11-dihydro-N-dibenzo
[b, f] azepinyl group, 2-methoxy-10,11-dihydro-N-dibenzo [b, f] azepinyl group, 3-methoxy-10,11-dihydro-N-dibenzo [b, f] azepinyl group, 3-ethoxy-10,11-dihydro-N-dibenzo [b, f] azepinyl group, 3-isopropyloxy-1
0,11-dihydro-N-dibenzo [b, f] azepinyl group, 3-n-butyloxy-10,11-dihydro-N
-Dibenzo [b, f] azepinyl group, 3-n-octyloxy-10,11-dihydro-N-dibenzo [b, f] azepinyl group, 3-n-decyloxy-10,11-dihydro-N-dibenzo [ b, f] azepinyl group, 3-phenyl-1
0,11-dihydro-N-dibenzo [b, f] azepinyl group, 3- (4'-methylphenyl) -10,11-dihydro-N-dibenzo [b, f] azepinyl group, 2-chloro-
10,11-dihydro-N-dibenzo [b, f] azepinyl group, 3-chloro-10,11-dihydro-N-dibenzo
Examples thereof include [b, f] azepinyl group and N-tribenzo [b, d, f] azepinyl group.

The compound A according to the present invention is preferably a compound having a fluorene ring bonded to the anthracene ring at a position other than the 9-position, and more preferably a compound represented by the general formula (1). . _{X 1 - (F 1) j} - (A 1) k - (F 2) l - (A 2) m - (F 3) n -X 2 (1) [ wherein, A ₁ and A ₂ are each independently Represents a substituted or unsubstituted anthracene diyl group, and is represented by F ₁ , F ₂ and F
₃ independently represents a substituted or unsubstituted fluorenediyl group, X ₁ and X ₂ each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic Represents an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted amino group, or a group represented by the general formula (I),

[0036]

[Chemical 18]

(Wherein Ar ₁ and Ar ₂ represent a substituted or unsubstituted arylene group and Z represents a linking group) j, m
And n represent 0 or 1, k and l represent 1 or 2, and when k is 2, A _{1 s} may be the same or different, and when l is 2, F 2 s may be the same. They may be different, provided that at least one of X ₁ and X ₂ is a group represented by formula (I). ] In the compound represented by the general formula (1), X ₁ and X ₂
Are each independently a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted It represents a substituted amino group or a group represented by formula (I), at least one of which is a group represented by formula (I).

[0038]

[Chemical 19]

(In the formula, Ar ₁ and Ar ₂ represent a substituted or unsubstituted arylene group, and Z represents a linking group.) In the compound represented by the general formula (1), X ₁ and X ₂ The aryl group and aralkyl group of may have a substituent, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 16 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 16 carbon atoms. Group, aryl group having 3 to 25 carbon atoms, aralkyl group having 5 to 16 carbon atoms, 1 carbon atom
~ 20 N-monosubstituted amino group, C2-40 N,
It may be mono- or poly-substituted with a substituent such as an N-disubstituted amino group.

In the compound represented by the general formula (1), the amino group of X ₁ and X ₂ may have a substituent, and is an alkyl group having 1 to 20 carbon atoms or 3 to 3 carbon atoms. 20
May be mono-substituted or di-substituted with a substituent such as the aryl group or the C 4-20 aralkyl group.

The groups of X ₁ and X ₂ other than the group represented by the general formula (I) are preferably hydrogen atom, halogen atom, straight-chain, branched or cyclic alkyl group having 1 to 16 carbon atoms or carbon atom. A linear, branched or cyclic alkoxy group of the formulas 1 to 16,
A substituted or unsubstituted carbocyclic aromatic group having 6 to 25 carbon atoms, a substituted or unsubstituted heterocyclic aromatic group having 3 to 25 carbon atoms, a substituted or unsubstituted aralkyl group having 5 to 16 carbon atoms, It is an unsubstituted amino group or a substituted amino group having 1 to 24 carbon atoms, more preferably a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, and 1 to 10 carbon atoms. A linear, branched or cyclic alkoxy group, a substituted or unsubstituted carbocyclic aromatic group having 6 to 12 carbon atoms, a substituted or unsubstituted heterocyclic aromatic group having 4 to 12 carbon atoms, and 7 carbon atoms To 12 substituted or unsubstituted aralkyl group, or a substituted amino group having 1 to 20 carbon atoms, more preferably a hydrogen atom, a halogen atom, a straight chain, branched or cyclic alkyl group having 1 to 8 carbon atoms, Straight or branched chain having 1 to 8 carbon atoms Or a cyclic alkoxy group, a substituted or unsubstituted carbocyclic aromatic group having 6 to 10 carbon atoms, a substituted or unsubstituted heterocyclic aromatic group having 4 to 10 carbon atoms, and a substituted group having 7 to 10 carbon atoms Alternatively, it is an unsubstituted aralkyl group or a substituted amino group having 1 to 20 carbon atoms.

Specific examples of X ₁ and X ₂ other than the group represented by formula (I) include halogen atoms such as hydrogen atom, fluorine atom, chlorine atom and bromine atom, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group,
n-pentyl group, isopentyl group, neopentyl group, te
rt-pentyl group, cyclopentyl group, n-hexyl group,
1-methylpentyl group, 4-methyl-2-pentyl group,
3,3-dimethylbutyl group, 2-ethylbutyl group, cyclohexyl group, n-heptyl group, 1-methylhexyl group, cyclohexylmethyl group, 4-tert-butylcyclohexyl group, n-heptyl group, cycloheptyl group, n-
Octyl group, cyclooctyl group, tert-octyl group, 1
-Methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 2,6-dimethyl-4-heptyl group, 3,5,
5-trimethylhexyl group, n-decyl group, n-undecyl group, 1-methyldecyl group, n-dodecyl group, n-tridecyl group, 1-hexylheptyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group Group, n-
Straight-chain, branched or cyclic alkyl groups such as heptadecyl group, n-octadecyl group and n-eicosyl group,

Methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, n-pentyloxy group, neopentyloxy group, cyclopentyloxy group, n-hexyloxy group. Group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, cyclohexyloxy group, n-heptyloxy group, n-octyloxy group, 2-ethylhexyloxy group, n-nonyloxy group, n-decyloxy group, n-undecyloxy group, n-dodecyloxy group, n-tridecyloxy group, n-tetradecyloxy group, n-pentadecyloxy group, n-hexadecyloxy group, n-heptadecyloxy group, n- Linear, branched or cyclic alkoxy groups such as octadecyloxy group and n-eicosyloxy group Phenyl, 4-methylphenyl, 3-methylphenyl group, 2-methylphenyl group,
4-ethylphenyl group, 3-ethylphenyl group, 2-ethylphenyl group, 4-n-propylphenyl group, 4-isopropylphenyl group, 2-isopropylphenyl group,
4-n-butylphenyl group, 4-isobutylphenyl group, 4-sec-butylphenyl group, 2-sec-butylphenyl group, 4-tert-butylphenyl group, 3-tert-butylphenyl group, 2-tert- Butylphenyl group, 4-n-
Pentylphenyl group, 4-isopentylphenyl group, 4
-Neopentylphenyl group, 4-tert-pentylphenyl group, 4-n-hexylphenyl group, 4- (2'-ethylbutyl) phenyl group, 4-n-heptylphenyl group,
4-n-octylphenyl group, 4- (2'-ethylhexyl) phenyl group, 4-n-nonylphenyl group, 4-n
-Decylphenyl group, 4-n-undecylphenyl group,
4-n-dodecylphenyl group, 4-n-tetradecylphenyl group, 4-cyclohexylphenyl group, 4- (4 '
-Methylcyclohexyl) phenyl group, 4- (4'-te
rt-butylcyclohexyl) phenyl group, 3-cyclohexylphenyl group, 2-cyclohexylphenyl group,
2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 3, 4,5-trimethylphenyl group, 2,3,5,6-tetramethylphenyl group, 2,4
-Diethylphenyl group, 2,6-diethylphenyl group,
2,5-diisopropylphenyl group, 2,6-diisopropylphenyl group, 2,6-diisobutylphenyl group,
2,4-di-tert-butylphenyl group, 2,5-di-te
rt-butylphenyl group, 4,6-di-tert-butyl-2
-Methylphenyl group, 5-tert-butyl-2-methylphenyl group, 4-tert-butyl-2,6-dimethylphenyl group, 1-naphthyl group, 2-naphthyl group, 1,2,3,
4-tetrahydro-5-naphthyl group, 1,2,3,4-
Tetrahydro-6-naphthyl group, 4-ethyl-1-naphthyl group, 6-n-butyl-2-naphthyl group, 5-indanyl group,

4-methoxyphenyl group, 3-methoxyphenyl group, 2-methoxyphenyl group, 4-ethoxyphenyl group, 3-ethoxyphenyl group, 2-ethoxyphenyl group, 4-n-propyloxyphenyl group, 3- n-propyloxyphenyl group, 4-isopropyloxyphenyl group, 2-isopropyloxyphenyl group, 4-n-
Butyloxyphenyl group, 4-isobutyloxyphenyl group, 2-sec-butyloxyphenyl group, 4-n-pentyloxyphenyl group, 4-isopentyloxyphenyl group, 2-isopentyloxyphenyl group, 4-neopentyl Oxyphenyl group, 2-neopentyloxyphenyl group, 4-n-hexyloxyphenyl group, 4-
(2'-Ethylbutyl) oxyphenyl group, 4-n-heptyloxyphenyl group, 4-n-octyloxyphenyl group, 4-n-nonyloxyphenyl group, 4-n-decyloxyphenyl group, 4-n- Undecyloxyphenyl group, 4-n-dodecyloxyphenyl group, 4-n-
Tetradecyloxyphenyl group, 4-cyclohexyloxyphenyl group, 2-cyclohexyloxyphenyl group, 2,3-dimethoxyphenyl group, 2,4-dimethoxyphenyl group, 2,5-dimethoxyphenyl group, 3,4
-Dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 3,5-diethoxyphenyl group, 2-methoxy-4
-Methylphenyl group, 2-methoxy-5-methylphenyl group, 2-methyl-4-methoxyphenyl group, 3-methyl-4-methoxyphenyl group, 3-methyl-5-methoxyphenyl group, 2-methoxy-1 -Naphthyl group, 4-methoxy-1-naphthyl group, 4-n-butyloxy-1-
Naphthyl group, 5-ethoxy-1-naphthyl group, 6-methoxy-2-naphthyl group, 6-ethoxy-2-naphthyl group, 6-n-butyloxy-2-naphthyl group, 6-n-
Hexyloxy-2-naphthyl group, 7-methoxy-2-
Naphthyl group, 7-n-butyloxy-2-naphthyl group,

4-phenylphenyl group, 3-phenylphenyl group, 2-phenylphenyl group, 4- (4'-methylphenyl) phenyl group, 4- (3'-methylphenyl) phenyl group, 4- (4 ' -Ethylphenyl) phenyl group, 4- (4'-isopropylphenyl) phenyl group, 4- (4'-tert-butylphenyl) phenyl group,
4- (4'-n-hexylphenyl) phenyl group, 4-
(4'-n-octylphenyl) phenyl group, 4-
(4'-methoxyphenyl) phenyl group, 4- (4'-
n-butyloxyphenyl) phenyl group, 2- (2'-
Methoxyphenyl) phenyl group, 4- (4'-chlorophenyl) phenyl group, 3-methyl-4-phenylphenyl group, 3-methoxy-4-phenylphenyl group, 4-fluorophenyl group, 3-fluorophenyl group, 2 -Fluorophenyl group, 4-chlorophenyl group, 3-chlorophenyl group, 2-chlorophenyl group, 4-bromophenyl group, 2-bromophenyl group, 4-trifluoromethylphenyl group, 2,3-difluorophenyl group, 2, 4-difluorophenyl group, 2,5-difluorophenyl group,
2,6-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,3-dichlorophenyl group, 2,4-dichlorophenyl group, 2,
5-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2,5-dibromophenyl group, 2,4,6-trichlorophenyl group, 2-fluoro-4-methylphenyl group, 2-fluoro -5-methylphenyl group, 3-fluoro-2-methylphenyl group, 3-fluoro-4-methylphenyl group, 2-methyl-4-fluorophenyl group, 2-methyl-5-fluorophenyl group, 3-methyl -4-fluorophenyl group, 2
-Chloro-4-methylphenyl group, 2-chloro-5-methylphenyl group, 2-chloro-6-methylphenyl group,
3-chloro-4-methylphenyl group, 2-methyl-3-
Chlorophenyl group, 2-methyl-4-chlorophenyl group, 3-methyl-4-chlorophenyl group, 2-chloro-
4,6-Dimethylphenyl group, 2,4-dichloro-1-
Naphthyl group, 1,6-dichloro-2-naphthyl group, 2-
Methoxy-4-fluorophenyl group, 3-methoxy-4
-Fluorophenyl group, 2-fluoro-4-methoxyphenyl group, 2-fluoro-4-ethoxyphenyl group, 2
-Fluoro-6-methoxyphenyl group, 3-fluoro-
4-methoxyphenyl group, 3-fluoro-4-ethoxyphenyl group, 2-chloro-4-methoxyphenyl group, 3
-Chloro-4-methoxyphenyl group, 2-methoxy-5
A substituted or unsubstituted carbocyclic aromatic group such as -chlorophenyl group, 3-methoxy-4-chlorophenyl group, 3-methoxy-6-chlorophenyl group, 5-chloro-2,4-dimethoxyphenyl group,

4-quinolyl group, 3-quinolyl group, 4-methyl-2-quinolyl group, 4-pyridyl group, 3-pyridyl group, 2-pyridyl group, 4-methyl-2-pyridyl group, 5
-Methyl-2-pyridyl group, 6-methyl-2-pyridyl group, 6-fluoro-3-pyridyl group, 6-methoxy-3
-Pyridyl group, 6-methoxy-2-pyridyl group, 3-furyl group, 2-furyl group, 3-thienyl group, 2-thienyl group, 4-methyl-3-thienyl group, 5-methyl-2-thienyl group A substituted or unsubstituted heterocyclic aromatic group such as a 3-methyl-2-thienyl group, a 2-oxazolyl group, a 2-thiazolyl group, a 2-benzoxazolyl group, a 2-benzothiazolyl group, and a 2-benzimidazolyl group. , Benzyl group, phenethyl group, α-methylbenzyl group, α, α-
Dimethylbenzyl group, 1-naphthylmethyl group, 2-naphthylmethyl group, furfuryl group, 2-methylbenzyl group,
3-methylbenzyl group, 4-methylbenzyl group, 4-ethylbenzyl group, 4-isopropylbenzyl group, 4-te
rt-butylbenzyl group, 4-n-hexylbenzyl group,
4-n-nonylbenzyl group, 3,4-dimethylbenzyl group, 3-methoxybenzyl group, 4-methoxybenzyl group, 4-ethoxybenzyl group, 4-n-butyloxybenzyl group, 4-n-hexyloxybenzyl group Group, 4-n
-Nonyloxybenzyl group, 3-fluorobenzyl group,
4-fluorobenzyl group, 2-chlorobenzyl group, 4-
Substituted or unsubstituted aralkyl group such as chlorobenzyl group, amino group, N-methylamino group, N-ethylamino group, N-n-butylamino group, N-cyclohexylamino group, N-n-octylamino group, N-n-decylamino group, N-benzylamino group, N-phenylamino group,
N- (3-methylphenyl) amino group, N- (4-methylphenyl) amino group, N- (4-n-butylphenyl) amino group, N- (4-methoxyphenyl) amino group, N- (3 -Fluorophenyl) amino group, N- (4
-Chlorophenyl) amino group, N- (1-naphthyl) amino group, N- (2-naphthyl) amino group, N, N-dimethylamino group, N, N-diethylamino group, N, N-di-n-butyl Amino group, N, N-di-n-hexylamino group, N, N-di-n-octylamino group, N, N-di-n-decylamino group, N, N-di-n-dodecylamino group, N-methyl-N-ethylamino group, N-ethyl-
N-n-butylamino group, N-methyl-N-phenylamino group, N-n-butyl-N-phenylamino group, N,
N-diphenylamino group, N, N-di (3methylphenyl) amino group, N, N-di (4-methylphenyl) amino group, N, N-di (4-ethylphenyl) amino group,
N, N-di (4-tert-butylphenyl) amino group,
N, N-di (4-n-hexylphenyl) amino group,
N, N-di (4-methoxyphenyl) amino group, N, N
-Di (4-ethoxyphenyl) amino group, N, N-di (4-n-butyloxyphenyl) amino group, N, N-
Di (4-n-hexyloxyphenyl) amino group, N,
N-di (1-naphthyl) amino group, N, N-di (2-naphthyl) amino group, N-phenyl-N- (3-methylphenyl) amino group, N-phenyl-N- (4-methylphenyl) ) Amino group, N-phenyl-N- (4-octylphenyl) amino group, N-phenyl-N- (4-methoxyphenyl) amino group, N-phenyl-N- (4-ethoxyphenyl) amino group, N -Phenyl-N- (4-n
-Hexyloxyphenyl) amino group, N-phenyl-
N- (4-fluorophenyl) amino group, N-phenyl-N- (1-naphthyl) amino group, N-phenyl-N-
(2-naphthyl) amino group, N-phenyl-N- (4-
Examples thereof include a substituted or unsubstituted amino group such as phenylphenyl) amino group.

In the compound represented by the general formula (1),
A ₁ and A ₂ each independently represent a substituted or unsubstituted anthracene diyl group, and F ₁ , F ₂ and F ₃ each independently represent a substituted or unsubstituted fluorenediyl group.

When A ₁ , A ₂ , F ₁ , F ₂ and F ₃ have a substituent, examples of the substituent include a halogen atom,
Straight chain, branched or cyclic alkyl group, straight chain, branched or cyclic alkoxy group, substituted or unsubstituted aryl group,
Examples thereof include a substituted or unsubstituted aralkyl group, and a substituted or unsubstituted amino group.

The aryl group means a carbocyclic aromatic group such as phenyl group and naphthyl group, furyl group, thienyl group,
Represents a heterocyclic aromatic group such as a pyridyl group.

When A ₁ , A ₂ , F ₁ , F ₂ and F ₃ have a substituent, specific examples of the substituent include the halogen atom, the straight chain and the branched chain mentioned as the specific examples of X ₁ and X _2. Or a cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted carbocyclic aromatic group, a substituted or unsubstituted heterocyclic aromatic group, a substituted or unsubstituted aralkyl group, substituted or An unsubstituted amino group or a group represented by general formula (I) can be given.

[0051]

[Chemical 20]

(In the formula, Ar ₁ and Ar ₂ represent a substituted or unsubstituted arylene group, and Z represents a linking group.)

A ₁ and A ₂ are, for example, a substituted or unsubstituted anthracene-1,4-diyl group, a substituted or unsubstituted anthracene-1,5-diyl group, a substituted or unsubstituted anthracene-1,8 group. -Diyl group, substituted or unsubstituted anthracene-1,9-diyl group, substituted or unsubstituted anthracene-1,10-diyl group, substituted or unsubstituted anthracene-2,3-diyl group, substituted or unsubstituted Anthracene-2,6-diyl group, substituted or unsubstituted anthracene-2,7-diyl group, substituted or unsubstituted anthracene-2,9-diyl group, substituted or unsubstituted anthracene-2,10-diyl Group, a substituted or unsubstituted anthracene-9,10-diyl group, preferably a substituted or unsubstituted anthracene-1,4-
Diyl group, substituted or unsubstituted anthracene-1,5-
Diyl group, substituted or unsubstituted anthracene-2,6-
Diyl group, substituted or unsubstituted anthracene-2,7-
Diyl group, substituted or unsubstituted anthracene-9,10
It is a -diyl group, and more preferably a substituted or unsubstituted anthracene-9,10-diyl group.

F ₁ , F ₂ and F ₃ are, for example, a substituted or unsubstituted fluorene-1,3-diyl group, a substituted or unsubstituted fluorene-1,6-diyl group, a substituted or unsubstituted fluorene- 1,7-diyl group, substituted or unsubstituted fluorene-1,8-diyl group, substituted or unsubstituted fluorene-2,6-diyl group, substituted or unsubstituted fluorene-2,7-diyl group, substituted Or an unsubstituted fluorene-3,6-diyl group, preferably a substituted or unsubstituted fluorene-1,6-diyl group, a substituted or unsubstituted fluorene-1,7-diyl group, a substituted or unsubstituted Fluorene-1,8-diyl group, substituted or unsubstituted fluorene-2,6-diyl group, substituted or unsubstituted fluorene-2,7-diyl group, substituted or unsubstituted fluorene- 3,6-diyl group, more preferably a substituted or unsubstituted fluorene-1,8-diyl group, a substituted or unsubstituted fluorene-2,7-diyl group, a substituted or unsubstituted fluorene-3. , 6-diyl group, and more preferably a substituted or unsubstituted fluorene-2,7-diyl group.

In the compound represented by the general formula (1),
j, m and n represent 0 or 1, and k and l represent 1 or 2. Preferably, k is 1, j and n are 0, l is 1 and k + m is 2, j + l + n is 2, k is 1 and m is 0, and j, m
And n is 0, and k and l are 1.

The compound represented by the general formula (1) is represented by j, k,
The following structures can be roughly classified according to the values of l, m and n. _{X 1 -A 1 -F 2 -X 2} (1a) X 1 -F 1 -A 1 -F 2 -X 2 (1b) X 1 -A 1 -F 2 -A 2 -X 2 (1c) X 1 _{-A 1 -F 2 -F 2 -X 2} (1d) X 1 -A 1 -A 1 -F 2 -X 2 (1e) X 1 -F 1 -A 1 -F 2 -A 2 -X 2 ( _{1f) X 1 -F 1 -A 1} -F 2 -F 2 -X 2 (1g) X 1 -F 1 -A 1 -A 1 -F 2 -X 2 (1h) X 1 -A 1 -F 2 _{-F 2 -A 2 -X 2 (1i} ) X 1 -A 1 -A 1 -F 2 -A 2 -X 2 (1j) X 1 -A 1 -A 1 -F 2 -F 2 -X 2 ( _{1k) X 1 -A 1 -F 2} -F 2 -F 3 -X 2 (1l) X 1 -F 1 -A 1 -F 2 -A 2 -F 3 -X 2 (1m) X 1 -F 1 _{-A 1 -F 2 -F 2 -A 2} -X 2 (1n) X 1 -F 1 -A 1 -A 1 -F 2 -A 2 -X 2 (1o) X 1 -F 1 -A 1 - _{A 1 -F 2 -F 2 -X 2} (1 _{) X 1 -A 1 -A 1 -F} 2 -F 2 -A 2 -X 2 (1q) X 1 -F 1 -A 1 -F 2 -F 2 -F 3 -X 2 (1r) X 1 - _{A 1 -A 1 -F 2 -A 1} -F 3 -X 2 (1s) X 1 -A 1 -A 1 -F 2 -F 2 -F 3 -X 2 (1t) X 1 -F 1 -A _{1 -A 1 -F 2 -F 2 -A} 2 -X 2 (1u) X 1 -F 1 -A 1 -F 2 -F 2 -A 2 -F 3 -X 2 (1v) X 1 -F 1 _{-A 1 -A 1 -F 2 -A 2} -F 3 -X 2 (1w) X 1 -F 1 -A 1 -A 1 -F 2 -F 2 -F 3 -X 2 (1x) X 1 - A ₁ -A ₁ -F ₂ -F ₂ -A ₂ -F ₃ -X ₂ (1y) X ₁ -F ₁ -A ₁ -A ₁ -F ₂ -F ₂ -A ₂ -F ₃ -X ₂ ( 1z) [In the formula, A ₁ , A ₂ , F ₁ , F ₂ , F ₃ , X ₁ and X ₂ have the same meanings as in the case of the general formula (1). ]

Of these structures, (1
a), (1b), (1c), (1d), (1f), (1
g), (1i), (1l), (1m), (1n), (1
r), (1v) and (1y),
More preferably, (1a), (1b), (1c), (1
f), (1g), (1i), (1m), and (1v)
And more preferably (1a),
It is a structure represented by (1b), (1c) and (1m).

Further, as preferred forms of the compound represented by the general formula (1), compounds represented by the following general formula (2), the following general formula (3) and the following general formula (4) can be mentioned. it can.

[0059]

[Chemical 21]

[Wherein R ₂₁ and R ₂₂ each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group; to ₂₀₁ to X ₂₂₄ are independently a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group Or a group represented by the general formula (I),

[0061]

[Chemical formula 22]

(In the formula, Ar ₁ and Ar ₂ represent a substituted or unsubstituted arylene group, and Z represents a linking group.) X
₂₀₁ at least one to X ₂₂₄ represents a group represented by the general formula (I). However, R ₂₁ , R ₂₂ and X _{201 to} X ₂₂₄ are not an anthryl group or a fluorenyl group. ]

[0063]

[Chemical formula 23]

[Wherein R _{31 to} R ₃₄ each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group; to ₃₀₁ to X ₃₂₂ are independently a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group ,
Alternatively, it represents a group represented by the general formula (I),

[0065]

[Chemical formula 24]

(In the formula, Ar ₁ and Ar ₂ represent a substituted or unsubstituted arylene group, and Z represents a linking group.) X
₃₀₁ at least one to X ₃₂₂ represents a group represented by the general formula (I). However, R _{31 to} R ₃₄ and X _{301 to} X ₃₂₂ are not an anthryl group or a fluorenyl group. ]

[0067]

[Chemical 25]

[Wherein R ₄₁ and R ₄₂ each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group; _{401 to} X ₄₁₆ each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group. Or a group represented by the general formula (I),

[0069]

[Chemical formula 26]

(In the formula, Ar ₁ and Ar ₂ represent a substituted or unsubstituted arylene group, and Z represents a linking group.) X
₄₀₁ at least one to X ₄₁₆ represents a group represented by the general formula (I). However, R ₄₁ , R ₄₂ and X _{401 to} X ₄₁₆ are not an anthryl group and a fluorenyl group. ]

In the compounds represented by the general formula (2), the general formula (3) and the general formula (4), R ₂₁ , R ₂₂ , and R ₃₁ to
R ₃₄ , R ₄₁ and R ₄₂ each independently represent a hydrogen atom, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group. However, R ₂₁ , R ₂₂ , R _{31 to} R ₃₄ , R ₄₁ and R
₄₂ is not an anthryl group or a fluorenyl group.

The aryl group means a carbocyclic aromatic group such as a phenyl group and a naphthyl group, a furyl group, a thienyl group,
Represents a heterocyclic aromatic group such as a pyridyl group.

R ₂₁ , R ₂₂ , R _{41 to} R ₄₄ , R ₅₁ and R ₅₂
Is preferably a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 16 carbon atoms, a substituted or unsubstituted carbocyclic aromatic group having 6 to 25 carbon atoms, a substituted or unsubstituted carbon group having 3 to 25 carbon atoms, or Unsubstituted heterocyclic aromatic group or carbon number 5 to 1
A substituted or unsubstituted aralkyl group having 6 carbon atoms, more preferably a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted carbocyclic aromatic group having 6 to 12 carbon atoms. Group, a substituted or unsubstituted heterocyclic aromatic group having 4 to 12 carbon atoms, or a substituted or unsubstituted aralkyl group having 7 to 12 carbon atoms, more preferably a hydrogen atom or 1 to 8 carbon atoms. A linear, branched or cyclic alkyl group, a substituted or unsubstituted carbocyclic aromatic group having 6 to 10 carbon atoms, a substituted or unsubstituted heterocyclic aromatic group having 4 to 10 carbon atoms, or a carbon number 7 to 10 substituted or unsubstituted aralkyl groups. R ₂₁ , R ₂₂ , R ₃₁ ~
Specific examples of R ₃₄ , R ₄₁ and R ₄₂ include a hydrogen atom, or a linear, branched or cyclic alkyl group, a substituted or unsubstituted carbocyclic aromatic group mentioned as specific examples of X ₁ and X _2. A substituted or unsubstituted heterocyclic aromatic group, or a substituted or unsubstituted aralkyl group.

In the compounds represented by the general formula (2), the general formula (3) and the general formula (4), X _{201 to} X ₂₂₄ , X
_{301 to} X ₃₂₂ and X _{401 to} X ₄₁₆ each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aryl group, a substituted group Or an unsubstituted amino group or a group represented by general formula (I),

[0075]

[Chemical 27]

(In the formula, Ar₁And Ar₂Is replaced or not
It represents a substituted arylene group, and Z represents a linking group. ) X
₂₀₁~ X₂₂₄At least one of the X₃₀₁~ X₃₂₂At least
One more, X₄₀₁~ X₄₁₆At least one of the general formulas
It represents a group represented by (I). However, X ₂₀₁~ X₂₂₄, X
₃₀₁~ X₃₂₂And X₄₀₁~ X₄₁₆Is an anthryl group and
Not a fluorenyl group.

The aryl group means a carbocyclic aromatic group such as a phenyl group and a naphthyl group, a furyl group, a thienyl group,
Represents a heterocyclic aromatic group such as a pyridyl group.

X _{201 to} X ₂₂₄ , X _{301 to} X ₃₂₂ and X ₄₀₁
To X ₄₁₆ , groups other than the group represented by the general formula (I) are preferably a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 16 carbon atoms, and a carbon atom having 1 to 16 carbon atoms. Linear, branched or cyclic alkoxy group, substituted or unsubstituted carbocyclic aromatic group having 6 to 25 carbon atoms, 3 to 25 carbon atoms
A substituted or unsubstituted heterocyclic aromatic group, an unsubstituted amino group, or a substituted amino group having 1 to 24 carbon atoms,
More preferably, a hydrogen atom, a halogen atom, and a carbon number of 1 to
10 straight-chain, branched or cyclic alkyl groups, 1 to 1 carbon atoms
10 linear, branched or cyclic alkoxy groups, 6 carbon atoms
To a substituted or unsubstituted carbocyclic aromatic group, or a substituted or unsubstituted heterocyclic aromatic group having 4 to 12 carbon atoms, or a substituted amino group having 1 to 20 carbon atoms, and more preferably , Hydrogen atom, halogen atom, carbon number 1
8 straight-chain, branched or cyclic alkyl group, having 1 to 8 carbon atoms
Linear, branched or cyclic alkoxy group having 6 to 1 carbon atoms
0 substituted or unsubstituted carbocyclic aromatic group, or a substituted or unsubstituted heterocyclic aromatic group having 4 to 10 carbon atoms,
Alternatively, it is a substituted amino group having 1 to 20 carbon atoms.

X _{201 to} X ₂₂₄ , X _{301 to} X ₃₂₂ and X ₄₀₁
To X ₄₁₆ , specific examples of the groups other than the group represented by the general formula (I) include a hydrogen atom, or a halogen atom, which is a specific example of X ₁ and X ₂ , a linear, branched or cyclic alkyl group. A linear, branched or cyclic alkoxy group, a substituted or unsubstituted carbocyclic aromatic group, a substituted or unsubstituted heterocyclic aromatic group, or a substituted or unsubstituted amino group.

Specific examples of the compound A according to the present invention include:
For example, the following compounds can be mentioned, but the present invention is not limited thereto.

[0081]

[Chemical 28]

[0082]

[Chemical 29]

[0083]

[Chemical 30]

[0084]

[Chemical 31]

[0085]

[Chemical 32]

[0086]

[Chemical 33]

[0087]

[Chemical 34]

[0088]

[Chemical 35]

[0089]

[Chemical 36]

[0090]

[Chemical 37]

[0091]

[Chemical 38]

[0092]

[Chemical Formula 39]

[0093]

[Chemical 40]

[0094]

[Chemical 41]

[0095]

[Chemical 42]

[0096]

[Chemical 43]

[0097]

[Chemical 44]

[0098]

[Chemical formula 45]

[0099]

[Chemical formula 46]

[0100]

[Chemical 47]

[0101]

[Chemical 48]

[0102]

[Chemical 49]

[0103]

[Chemical 50]

[0104]

[Chemical 51]

[0105]

[Chemical 52]

[0106]

[Chemical 53]

[0107]

[Chemical 54]

[0108]

[Chemical 55]

[0109]

[Chemical 56]

[0110]

[Chemical 57]

[0111]

[Chemical 58]

[0112]

[Chemical 59]

[0113]

[Chemical 60]

[0114]

[Chemical formula 61]

[0115]

[Chemical formula 62]

[0116]

[Chemical formula 63]

[0117]

[Chemical 64]

[0118]

[Chemical 65]

[0119]

[Chemical formula 66]

[0120]

[Chemical formula 67]

[0121]

[Chemical 68]

[0122]

[Chemical 69]

[0123]

[Chemical 70]

[0124]

[Chemical 71]

[0125]

[Chemical 72]

[0126]

[Chemical formula 73]

[0127]

[Chemical 74]

[0128]

[Chemical 75]

[0129]

[Chemical 76]

[0130]

[Chemical 77]

[0131]

[Chemical 78]

[0132]

[Chemical 79]

[0133]

[Chemical 80]

[0134]

[Chemical 81]

[0135]

[Chemical formula 82]

[0136]

[Chemical 83]

[0137]

[Chemical 84]

[0138]

[Chemical 85]

[0139]

[Chemical 86]

[0140]

[Chemical 87]

[0141]

[Chemical 88]

[0142]

[Chemical 89]

[0143]

[Chemical 90]

[0144]

[Chemical Formula 91]

[0145]

[Chemical Formula 92]

[0146]

[Chemical formula 93]

[0147]

[Chemical 94]

[0148]

[Chemical 95]

[0149]

[Chemical 96]

[0150]

[Chemical 97]

[0151]

[Chemical 98]

[0152]

[Chemical 99]

[0153]

[Chemical 100]

[0154]

[Chemical 101]

[0155]

[Chemical 102]

[0156]

[Chemical 103]

[0157]

[Chemical 104]

[0158]

[Chemical 105]

[0159]

[Chemical formula 106]

[0160]

[Chemical formula 107]

[0161]

[Chemical 108]

[0162]

[Chemical 109]

[0163]

[Chemical 110]

[0164]

[Chemical 111]

[0165]

[Chemical 112]

[0166]

[Chemical 113]

[0167]

[Chemical 114]

[0168]

[Chemical 115]

[0169]

[Chemical formula 116]

[0170]

[Chemical 117]

[0171]

[Chemical 118]

[0172]

[Chemical formula 119]

[0173]

[Chemical 120]

[0174]

[Chemical 121]

[0175]

[Chemical formula 122]

[0176]

[Chemical 123]

[0177]

[Chemical formula 124]

[0178]

[Chemical 125]

[0179]

[Chemical formula 126]

[0180]

[Chemical 127]

[0181]

[Chemical 128]

[0182]

[Chemical formula 129]

[0183]

[Chemical 130]

[0184]

[Chemical 131]

[0185]

[Chemical 132]

[0186]

[Chemical 133]

[0187]

[Chemical 134]

[0188]

[Chemical 135]

[0189]

[Chemical 136]

[0190]

[Chemical 137]

[0191]

[Chemical 138]

[0192]

[Chemical 139]

[0193]

[Chemical 140]

[0194]

[Chemical 141]

[0195]

[Chemical 142]

The compound A according to the present invention is preferably the exemplified compound numbers A-1 to A-40, B-1 to B-40, C.
-1 to C-45, F-1 to F-30, G-1 to G-2
5, I-1 to I-40, and compounds represented by M-1 to M-25, and more preferably, exemplary compound number A
-1 to A-40, B-1 to B-40, C-1 to C-4
5, F-1 to F-30, I-1 to I-40, and M-
1 to M-25, more preferably A-1 to A-40, B-1 to B-40, C-1 to C.
The compounds represented by -45 and M-1 to M-25.

The compound A according to the present invention can be produced, for example, by the following method. That is, for example,
The halogenoanthracene derivative is combined with a fluorenylboric acid derivative, for example, a palladium compound [eg, tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) palladium dichloride] and a base (eg, sodium carbonate, sodium hydrogen carbonate, triethylamine). In the presence of [for example, the method described in Chem. Rev., 95 , 2457 (1995) can be referred to].

Compound A according to the present invention is, for example,
An anthrylboric acid derivative is combined with a halogenofluorene derivative, for example, a palladium compound [eg, tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) palladium chloride] and a base (eg, sodium carbonate, sodium hydrogen carbonate,
Triethylamine) [eg, Ch
The method described in em. Rev., 95 , 2457 (1995) can be referred to].

The compound represented by the general formula (1) according to the present invention can be produced, for example, by the following method. That is, for example, a boric acid compound represented by the following general formula (5) is replaced with a compound represented by the following general formula (6):
For example, the reaction is performed in the presence of a palladium compound [eg, tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) palladium dichloride] and a base (eg, sodium carbonate, sodium hydrogen carbonate, triethylamine) [eg, Chem .R
ev., 95 , 2457 (1995) can be referred to].

X ₁ − (F ₁ ) _j − (A ₁ ) _k −B (OH) ₂ (5) Y ₁ − (F ₂ ) _l − (A ₂ ) _m − (F ₃ ) _n −X ₂ ( 6) [In the above formula, A ₁ , A ₂ , F ₁ , F ₂ , F ₃ , X ₁ , X ₂ , j,
k, l, m and n have the same meanings as in formula (1), and Y ₁ represents a halogen atom.] In formula (6), Y ₁ represents a halogen atom, and preferably a chlorine atom. Represents a bromine atom and an iodine atom.

Further, the compound represented by the general formula (1) is
For example, a compound represented by the following general formula (7) is combined with a boric acid compound represented by the following general formula (8), for example, a palladium compound [eg, tetrakis (triphenylphosphine) palladium, bis (triphenyl) [Phosphine) dipalladium chloride] and a base (eg, sodium carbonate, sodium hydrogen carbonate, triethylamine) [eg, Chem. Rev., 95 , 245].
The method described in 7 (1995) can be referred to].

X ₁ − (F ₁ ) _j − (A ₁ ) _k −Y ₂ (7) (HO) ₂ B− (F ₂ ) _l − (A ₂ ) _m − (F ₃ ) _n −X ₂ ( 8) [In the above formula, A ₁ , A ₂ , F ₁ , F ₂ , F ₃ , X ₁ , X ₂ , j,
k, l, m and n have the same meanings as in formula (1), and Y ₂ represents a halogen atom.] In formula (7), Y ₂ represents a halogen atom, and preferably a chlorine atom. Represents a bromine atom and an iodine atom.

The compounds represented by the general formulas (5) and (8) include, for example, compounds represented by the general formulas (7) and (6), for example, n-butyllithium, It can be produced by reacting a lithio compound or a Grignard reagent which can be adjusted by the action of metallic magnesium with, for example, trimethoxyboron, triisopropoxyboron and the like.

Further, among the compounds represented by the general formula (1), A ₁ is a substituted or unsubstituted anthracene-9,10
The compound which is a -diyl group can be produced, for example, by the following method. That is, for example, a compound represented by the general formula (6) or the following general formula (9) is reacted with, for example, n-butyllithium or a magnesium metal, a thio compound or a Grignard reagent, and a substituted or unsubstituted By dehydrating and aromatizing a compound obtained by reacting anthraquinone in the presence of an acid (for example, hydriodic acid), in the compound represented by the general formula (1), A1 is substituted or unsubstituted. Of the anthracene-9,10-diyl group, wherein k is 1 can be produced.

X _1- (F ₁ ) _j -Y ₃ (9) [In the above formula, F ₁ , X ₁ and j have the same meanings as in formula (1), and Y ₃ is a halogen atom. In the general formula (9), Y ₃ represents a halogen atom, preferably a chlorine atom, a bromine atom, or an iodine atom.

Similarly, the compounds represented by the general formula (6) and the general formula (9) are substituted with a lithio compound or a Grignard reagent which can be prepared by reacting, for example, n-butyllithium or magnesium metal. By subjecting a compound obtained by reacting an unsubstituted bianthron to dehydration aromatization in the presence of an acid (for example, hydriodic acid), among the compounds represented by the general formula (1), A ₁ is A compound which is a substituted or unsubstituted anthracene-9,10-diyl group and k is 2 can be produced.

The compound A of the present invention may be produced in the form of a solvate with a solvent (eg, an aromatic hydrocarbon solvent such as toluene) optionally used.
The compound A according to the present invention includes such a solvate and, of course, also includes a non-solvate containing no solvent.

In the organic electroluminescent device of the present invention, not only the solvate-free compound A of the present invention but also such a solvate can be used.

When the compound A according to the present invention is used in an organic electroluminescence device, a purification method such as a recrystallization method, a column chromatography method, a sublimation purification method, or a combination of these methods is used to increase the purity. It is preferred to use the compounds mentioned.

The organic electroluminescent element usually comprises a pair of electrodes, and at least one luminescent layer containing at least one luminescent component sandwiched between the electrodes. Considering the respective function levels of hole injection and hole transport, electron injection and electron transport of the compound used for the light emitting layer, the hole injection transport layer and / or the electron containing a hole injection transport component may be added as desired. An electron injecting and transporting layer containing an injecting and transporting component can also be provided.

For example, when the compound used for the light emitting layer has a good hole injecting function, a hole transporting function and / or an electron injecting function, and an electron transporting function, the light emitting layer is a hole injecting and transporting layer and / or an electron. It is possible to have a structure of a device that also serves as an injecting and transporting layer. Of course, in some cases, it is possible to have a structure of a type element (one-layer type element) in which neither the hole injecting and transporting layer nor the electron injecting and transporting layer is provided.

Each of the hole injecting and transporting layer, the electron injecting and transporting layer, and the light emitting layer may have a single-layer structure or a multi-layered structure. The layers may be formed by separately providing a layer having an injection function and a layer having a transport function in each layer.

In the organic electroluminescence device of the present invention, the compound A of the present invention is preferably used as a hole injecting / transporting component, a light emitting component or an electron injecting / transporting component, and used as a hole injecting / transporting component or a light emitting component. Is more preferable,
More preferably, it is used as a light emitting component.

In the organic electroluminescent device of the present invention, the compound A of the present invention may be used alone or in combination of two or more.

The structure of the organic electroluminescent element of the present invention is not particularly limited, and may be, for example, (A) anode /
Hole injecting / transporting layer / light emitting layer / electron injecting / transporting layer / cathode type element (FIG. 1), (B) anode / hole injecting / transporting layer / light emitting layer / cathode type element (FIG. 2), (C) anode / light emitting Layer / electron injection / transport layer / cathode type element (FIG. 3), (D) anode / light emitting layer / cathode type element (FIG. 4). Further, the device is of a type in which the light emitting layer is sandwiched between electron injecting and transporting layers (E) anode / hole injecting / transporting layer / electron injecting / transporting layer / light emitting layer / electron injecting / transporting layer / cathode type device (FIG. 5). You can also do it.
The (D) type element structure includes an element of a type in which a light emitting component is sandwiched between a pair of electrodes in a single layer form, and further, for example, (F) a hole injecting and transporting component, light emission Element (FIG. 6) of a type in which a component and an electron injecting and transporting component are mixed and sandwiched between a pair of electrodes, and (G) a pair of electrodes in a single layer form in which a hole injecting and transporting component and a light emitting component are mixed. There are an element of a type sandwiched between them (FIG. 7) and an element of a type sandwiched between a pair of electrodes in a single layer form (H) in which a luminescent component and an electron injecting and transporting component are mixed (FIG. 8).

The organic electroluminescence device of the present invention is not limited to these device constitutions, and a plurality of hole injecting and transporting layers, light emitting layers and electron injecting and transporting layers may be provided in each type of device. You can In each type of device, between the hole injecting and transporting layer and the light emitting layer,
A mixed layer of the hole injecting and transporting component and the light emitting component and / or a mixed layer of the light emitting and electron injecting and transporting components may be provided between the light emitting layer and the electron injecting and transporting layer.

A more preferable structure of the organic electroluminescent element is as follows.
(A) type element, (B) type element, (C) type element, (E) type element, (F) type element, (G) type element or (H) type element, and more preferably (A) ) Type element, (B) type element, (C) type element, (F) type element, or (H) type element.

As the organic electroluminescent element of the present invention, for example, (A) anode / hole injecting / transporting layer / light emitting layer / electron injecting / transporting layer / cathode type element shown in FIG. 1 will be described.
In FIG. 1, 1 is a substrate, 2 is an anode, 3 is a hole injecting and transporting layer, 4 is a light emitting layer, 5 is an electron injecting and transporting layer, 6 is a cathode,
Reference numeral 7 indicates a power source.

The electroluminescent device of the present invention is preferably supported on the substrate 1. The substrate is not particularly limited, but is preferably transparent or translucent, for example, a glass plate or a transparent plate. Plastic sheet (eg polyester, polycarbonate, polysulfone, polymethylmethacrylate, polypropylene, polyethylene, etc. sheet), translucent plastic sheet,
Examples thereof include those made of quartz, transparent ceramics, or a composite sheet combining these. Further, on the substrate, for example, a color filter film, a color conversion film,
It is also possible to control the emission color by combining a dielectric reflection film.

For the anode 2, it is preferable to use a metal, an alloy or an electrically conductive compound having a relatively large work function as an electrode material.

Examples of the electrode material used for the anode include gold, platinum, silver, copper, cobalt, nickel, palladium, vanadium, tungsten, tin oxide, zinc oxide, and I.
Examples thereof include TO (indium tin oxide), polythiophene, and polypyrrole. These electrode substances may be used alone or in combination.

The anode can be formed on the substrate by using these electrode substances by a method such as a vapor deposition method or a sputtering method. The anode may have a single layer structure or a multilayer structure.

The sheet electric resistance of the anode is preferably set to several hundred Ω / □ or less, more preferably about 5 to 50 Ω / □. Although the thickness of the anode depends on the material of the electrode substance used, it is generally set to about 5 to 1000 nm, more preferably about 10 to 500 nm.

The hole injecting and transporting layer 3 is a layer containing a compound having a function of facilitating the injection of holes from the anode and a function of transporting the injected holes.

The hole injecting and transporting layer is composed of the compound A according to the present invention.
And / or other compounds having a hole injecting and transporting function (eg, phthalocyanine derivative, triarylmethane derivative, triarylamine derivative, oxazole derivative, hydrazone derivative, stilbene derivative, pyrazoline derivative, polysilane derivative, polyphenylene vinylene and its derivative, At least one of polythiophene and its derivative and poly-N-vinylcarbazole derivative) can be used for formation.

A compound having a hole injecting and transporting function is
They may be used alone or in combination.

Other compounds having a hole injecting and transporting function used in the present invention include triarylamine derivatives (eg, 4,4'-bis [N-phenyl-N- (4 "
-Methylphenyl) amino] biphenyl, 4,4'-bis [N-phenyl-N- (3 "-methylphenyl) amino] biphenyl, 4,4'-bis [N-phenyl-N-
(3 "-methoxyphenyl) amino] biphenyl, 4,
4'-bis [N-phenyl-N- (1 "-naphthyl) amino] biphenyl, 3,3'-dimethyl-4,4'-bis [N-phenyl-N- (3" -methylphenyl) amino] Biphenyl, 1,1-bis [4 '-[N, N-di (4 "-methylphenyl) amino] phenyl] cyclohexane, 9,10-bis [N- (4'-methylphenyl) -N- (4 "-N-Butylphenyl) amino] phenanthrene, 3,8-bis (N, N-diphenylamino) -6-phenylphenanthridine, 4-methyl-
N, N-bis [4 ", 4 '"-bis [N', N'-di (4-methylphenyl) amino] biphenyl-4-yl] aniline, N, N'-bis [4- (diphenyl Amino) phenyl] -N, N'-diphenyl-1,3-diaminobenzene, N, N'-bis [4- (diphenylamino) phenyl] -N, N'-diphenyl-1,4-diaminobenzene, 5 , 5 "-bis [4- (bis [4-methylphenyl] amino) phenyl] -2,2 ': 5',
2 "-terthiophene, 1,3,5-tris (diphenylamino) benzene, 4,4 ', 4" -tris (N-carbazolyyl) triphenylamine, 4,4', 4 "-
Tris [N- (3 ′ ″-methylphenyl) -N-phenylamino] triphenylamine, 4,4 ′, 4 ″ -Tris [N, N-bis (4 ″ ′-tert-butylbiphenyl-
4 ""-yl) amino] triphenylamine, 1,3,5
-Tris [N- (4'-diphenylaminophenyl)-
N-phenylamino] benzene), polythiophene and its derivatives, and poly-N-vinylcarbazole derivatives are preferred.

When the compound A according to the present invention and another compound having a hole injecting / transporting function are used in combination, the proportion of the compound A according to the present invention in the hole injecting / transporting layer is preferably:
It is adjusted to about 0.1 to 40% by weight.

The light emitting layer 4 has a function of injecting holes and electrons,
It is a layer containing a compound having a function of transporting them and a function of generating excitons by recombination of holes and electrons.

The light emitting layer is composed of the compound A according to the present invention and / or
Or other compound having a light emitting function (for example, acridone derivative, quinacridone derivative, diketopyrrolopyrrole derivative, polycyclic aromatic compound [for example, rubrene, anthracene, tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenylcyclo) Pentadiene, pentaphenylcyclohexadiene, 9,10-
Diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis (9'-ethynylanthracenyl) benzene, 4,4'-bis (9 "-ethynylanthracenyl) biphenyl], triaryl Amine derivatives [for example, the compounds described above can be mentioned as compounds having a hole injecting / transporting function], organometallic complexes [for example, tris (8-quinolinolato) aluminum, bis (10-benzo [h] quinolinolato) beryllium, Zinc salt of 2- (2′-hydroxyphenyl) benzoxazole, zinc salt of 2- (2′-hydroxyphenyl) benzothiazole, zinc salt of 4-hydroxyacridine, zinc salt of 3-hydroxyflavone, 5-hydroxyflavone Beryllium salt, 5-hydroxyflavone aluminum salt, 2-f Iridium salt of phenylpyridine], stilbene derivative [eg 1,1,4,4-tetraphenyl-1,3-butadiene, 4,4′-bis (2,2-diphenylvinyl) biphenyl, 4,4′-
Bis [(1,1,2-triphenyl) ethenyl] biphenyl, coumarin derivative [eg, coumarin 1, coumarin 6, coumarin 7, coumarin 30, coumarin 106, coumarin 138, coumarin 151, coumarin 152, coumarin 153, coumarin 307 , Coumarin 311, coumarin 314, coumarin 334, coumarin 338, coumarin 3
43, coumarin 500], pyran derivative [eg DC
M1, DCM2], oxazone derivative [for example, Nile Red], benzothiazole derivative, benzoxazole derivative, benzimidazole derivative, pyrazine derivative, cinnamic acid ester derivative, poly-N-vinylcarbazole and its derivative, polythiophene and its derivative, Polyphenylene and its derivatives, polyfluorene and its derivatives, polyphenylene vinylene and its derivatives, polybiphenylene vinylene and its derivatives, polyterphenylene vinylene and its derivatives, polynaphthylene vinylene and its derivatives, polythienylene vinylene and its derivatives) It can be formed by using one kind.

In the organic electroluminescent element of the present invention, it is preferable that the light emitting layer contains the compound A of the present invention.

In the organic electroluminescent element of the present invention, the compound A of the present invention may be used alone in the light emitting layer, or may be used in combination with another compound having a light emitting function.

When the compound A of the present invention is used in combination with another compound having a light emitting function, the proportion of the compound A of the present invention in the light emitting layer is preferably 0.001 to 9
9.999% by weight, more preferably 0.01-9
About 9.99% by weight, more preferably 0.1-9
It is adjusted to about 9.9% by weight.

As another compound having a light emitting function used in the present invention, a light emitting organometallic complex is preferable. For example, J. Appl. Phys., 65 , 3610 (1989), JP-A-5-214
As described in Japanese Patent No. 332, the light emitting layer can be composed of a host compound and a guest compound (dopant).

The compound A according to the present invention can be used as a host compound to form a light emitting layer, and can also be used as a guest compound to form a light emitting layer.

When the light emitting layer is formed by using the compound A according to the present invention as a guest compound, examples of the host compound include the above-mentioned other compounds having a light emitting function, and the light emitting property is preferable. It is an organometallic complex or the above-mentioned triarylamine derivative.

In this case, the compound A according to the present invention is used for the luminescent organometallic complex or the triarylamine derivative.
Is preferably used in an amount of about 0.001 to 40% by weight, more preferably about 0.01 to 30% by weight, and particularly preferably about 0.1 to 20% by weight.

The light-emitting organometallic complex used in combination with the compound A of the present invention is not particularly limited, but a light-emitting organoaluminum complex is preferable, and light emission having a substituted or unsubstituted 8-quinolinolato ligand is provided. Organic aluminum complexes are more preferred. Examples of preferable luminescent organic metal complexes include luminescent organic aluminum complexes represented by the general formulas (a) to (c).

(Q) ₃ -Al (a) (In the formula, Q represents a substituted or unsubstituted 8-quinolinolate ligand) (Q) ₂ -Al-OL (b) (in the formula, Q Represents a substituted 8-quinolinolato ligand, O
-L is a phenolate ligand, L represents a C6-C24 hydrocarbon group containing a phenyl moiety) (Q) _2- Al-O-Al- (Q) ₂ (c) (wherein Q represents a substituted 8-quinolinolate ligand)

Specific examples of the luminescent organometallic complex include, for example, tris (8-quinolinolato) aluminum, tris (4-methyl-8-quinolinolato) aluminum, tris (5-methyl-8-quinolinolato) aluminum, tris ( 3,4-Dimethyl-8-quinolinolato) aluminum, tris (4,5-dimethyl-8-quinolinolato) aluminum, tris (4,6-dimethyl-8-quinolinolato) aluminum, bis (2-methyl-8-quinolinolato) (Phenolato) aluminum, bis (2-methyl-8-quinolinolato) (2-
Methylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3-methylphenolate) aluminum, bis (2-methyl-8-quinolinolate)
(4-Methylphenolate) aluminum, bis (2-
Methyl-8-quinolinolato) (2-phenylphenolato) aluminum, bis (2-methyl-8-quinolinolato) (3-phenylphenolato) aluminum,
Bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum, bis (2-methyl-8)
-Quinolinolate) (2,3-dimethylphenolate)
Aluminum, bis (2-methyl-8-quinolinolato) (2,6-dimethylphenolate) aluminum,
Bis (2-methyl-8-quinolinolato) (3,4-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3,5-dimethylphenolate) aluminum, bis (2-methyl-8-) Quinolinolato) (3,5-di-tert-butylphenolate) aluminum, bis (2-methyl-8-quinolinolato)
(2,6-diphenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,4,6-
Triphenylphenolate) aluminum, bis (2-
Methyl-8-quinolinolate) (2,4,6-trimethylphenolate) aluminum, bis (2-methyl-8)
-Quinolinolate) (2,4,5,6-tetramethylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinolate) (2-naphtholate ) Aluminum, bis (2,4-dimethyl-8-quinolinolato) (2-phenylphenolato) aluminum, bis (2,4-dimethyl-8-quinolinolato)
(3-Phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (4-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (3,5-dimethylphenylphenolate Aluminum), bis (2,4-dimethyl-8-quinolinolate) (3,5-di-tert-butylphenylphenolato) aluminum, bis (2-methyl-8-quinolinolato) aluminum-μ-oxo-
Bis (2-methyl-8-quinolinolato) aluminum, bis (2,4-dimethyl-8-quinolinolato) aluminum-μ-oxo-bis (2,4-dimethyl-8)
-Quinolinolato) aluminum, bis (2-methyl-)
4-Ethyl-8-quinolinolato) aluminum-μ-
Oxo-bis (2-methyl-4-ethyl-8-quinolinolato) aluminum, bis (2-methyl-4-methoxy-8-quinolinolato) aluminum-μ-oxo-
Bis (2-methyl-4-methoxy-8-quinolinolato) aluminum, bis (2-methyl-5-cyano-8)
-Quinolinolato) aluminum-μ-oxo-bis (2-methyl-5-cyano-8-quinolinolato) aluminum, bis (2-methyl-5-trifluoromethyl-8-quinolinolato) aluminum-μ-oxo-bis (2 -Methyl-5-trifluoromethyl-8-quinolinolato) aluminum can be mentioned. Of course,
The light emitting organometallic complex may be used alone or in combination.

The electron injecting and transporting layer 5 is a layer containing a compound having a function of facilitating the injection of electrons from the cathode and a function of transporting the injected electrons.

The electron injecting and transporting layer is composed of the compound A according to the present invention.
And / or other compound having an electron injecting and transporting function (for example, an organometallic complex [eg, tris (8-quinolinolato) aluminum, bis (10-benzo [h] quinolinolato) beryllium, a beryllium salt of 5-hydroxyflavone, 5 -Aluminum salt of hydroxyflavone], an oxadiazole derivative [for example, 1,3-bis [5 '-(4 "-tert-butylphenyl) -1',
3 ', 4'-oxadiazol-2'-yl] benzene], triazole derivative [eg, 3- (4'-tert.
-Butylphenyl) -4-phenyl-5- (4 "-phenylphenyl) -1,2,4-triazole], triazine derivative, perylene derivative, quinoline derivative, quinoxaline derivative, diphenylquinone derivative, nitro-substituted fluorenone derivative, thio Pyrandioxide derivative) can be used.

The compound having an electron injecting and transporting function is
They may be used alone or in combination.

When the compound A according to the present invention and another compound having an electron injecting / transporting function are used in combination, the proportion of the compound A according to the present invention in the electron injecting / transporting layer is preferably:
It is adjusted to about 0.1 to 40% by weight.

In the present invention, the electron injecting and transporting layer is formed by using the compound A of the present invention and an organometallic complex [for example, compounds represented by the above general formulas (a) to (c)] together. Is preferred.

For the cathode 6, it is preferable to use a metal, an alloy or an electrically conductive compound having a relatively small work function as an electrode material.

Examples of the electrode material used for the cathode include lithium, lithium-indium alloy, sodium, sodium-potassium alloy, calcium, magnesium, magnesium-silver alloy, magnesium-indium alloy, indium, ruthenium, titanium, manganese, Examples thereof include yttrium, aluminum, aluminum-lithium alloy, aluminum-calcium alloy, aluminum-magnesium alloy, and graphite thin film. These electrode substances may be used alone or in combination.

The cathode can be formed on the electron injecting and transporting layer by using these electrode materials by a method such as a vapor deposition method, a sputtering method, an ionization vapor deposition method, an ion plating method and a cluster ion beam method. . Further, the cathode may have a single-layer structure or a multi-layer structure.

The sheet electric resistance of the cathode is several hundred Ω / □.
It is preferable to set the following. Although the thickness of the cathode depends on the material of the electrode material used, it is generally 5 to 1000 n.
m, more preferably about 10 to 500 nm.

It is preferable that at least one of the anode and the cathode is transparent or semi-transparent in order to efficiently extract the light emitted from the organic electroluminescent element.
Anode material so that the transmittance of emitted light is 70% or more,
It is more preferable to set the thickness.

In the organic electroluminescent element of the present invention, at least one layer thereof may contain a singlet oxygen quencher.

The singlet oxygen quencher is not particularly limited, and examples thereof include rubrene, nickel complex and diphenylisobenzofuran, and rubrene is particularly preferable.

The layer containing the singlet oxygen quencher is not particularly limited, but is preferably a light emitting layer or a hole injecting / transporting layer, and more preferably a hole injecting / transporting layer. . For example, when the hole injecting and transporting layer contains a singlet quencher, it may be uniformly contained in the hole injecting and transporting layer. It may be contained near the electron injecting and transporting layer (having a function).

The content of singlet oxygen quencher is 0.01 to 50% by weight, preferably 0.0 to 50% by weight based on the total amount of the layer (for example, hole injecting and transporting layer) contained.
5 to 30% by weight, more preferably 0.1 to 20% by weight
Is.

The method for forming the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting layer is not particularly limited, and examples thereof include a vacuum vapor deposition method, an ionization vapor deposition method, a solution coating method (for example, a spin coating method, a cast method). Method, dip coating method,
It can be prepared by forming a thin film by a bar coating method, a roll coating method, a Langmuir-Brosette method, an inkjet method).

When each layer is formed by the vacuum vapor deposition method,
The conditions for vacuum deposition are not particularly limited, but may be 1 ×
It is carried out under a vacuum of about 10 ^-4 Pa, a boat temperature (deposition source temperature) of about 50 to 600 ° C., a substrate temperature of about -50 to 300 ° C., and a deposition rate of about 0.005 to 50 nm / sec. Is preferred.

In this case, each layer such as the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting layer is continuously formed under vacuum to manufacture an organic electroluminescent device having further excellent characteristics. You can

When each layer such as the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting layer is formed by a plurality of compounds by the vacuum deposition method, the temperature of each boat containing the compounds is individually controlled, Co-deposition is preferred.

When each layer is formed by the solution coating method,
The component forming each layer or the component and the binder resin are dissolved or dispersed in a solvent to prepare a coating liquid.

The binder resin which can be used in each of the hole injecting and transporting layer, the light emitting layer and the electron injecting and transporting layer is poly-N.
-Vinylcarbazole, polyarylate, polystyrene, polyester, polysiloxane, polymethylacrylate, polymethylmethacrylate, polyether, polycarbonate, polyamide, polyimide, polyamideimide, polyparaxylene, polyethylene, polyphenylene oxide, polyethersulfone, polyaniline and the like. Polymer compounds such as derivatives, polythiophene and its derivatives, polyphenylene vinylene and its derivatives, polyfluorene and its derivatives, polythienylene vinylene and its derivatives can be mentioned. The binder resins may be used alone or in combination.

When each layer is formed by the solution coating method,
The components forming each layer or the components and the binder resin are mixed with a suitable organic solvent (a hydrocarbon solvent such as hexane, octane, decane, toluene, xylene, ethylbenzene, 1-methylnaphthalene, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone). Ketone solvents such as, dichloromethane, chloroform, tetrachloromethane, dichloroethane, trichloroethane,
Halogenated hydrocarbon solvents such as tetrachloroethane, chlorobenzene, dichlorobenzene, chlorotoluene,
Ester solvents such as ethyl acetate, butyl acetate and amyl acetate, alcohol solvents such as methanol, propanol, butanol, pentanol, hexanol, cyclohexanol, methyl cellosolve, ethyl cellosolve and ethylene glycol, dibutyl ether, tetrahydrofuran, dioxane, anisole. Ether solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1-methyl-2-imidazolidinone, polar solvents such as dimethylsulfoxide) and / Alternatively, a thin film can be formed by dissolving or dispersing in water to obtain a coating solution and using various coating methods.

The dispersing method is not particularly limited, but it can be dispersed in the form of fine particles using a ball mill, a sand mill, a paint shaker, an attritor, a homogenizer or the like.

The concentration of the coating solution is not particularly limited, and can be set within a concentration range suitable for producing a desired thickness depending on the coating method to be used, and generally 0.1 to 50% by weight. %, Preferably a solution concentration of about 1 to 30% by weight.

When a binder resin is used, the amount of the binder resin used is not particularly limited, but in general, for each component forming each layer (in the case of forming a one-layer type element, each 5 to 99.
The amount is set to about 9% by weight, preferably about 10 to 99.9% by weight, and more preferably about 15 to 90% by weight.

The film thickness of the hole injecting / transporting layer, the light emitting layer, and the electron injecting / transporting layer is not particularly limited, but is generally preferably set to about 5 nm to 5 μm.

A protective layer (sealing layer) may be provided on the manufactured element for the purpose of preventing contact with oxygen or moisture.
In addition, the element can be protected by enclosing it in an inert substance such as paraffin, liquid paraffin, silicone oil, fluorocarbon oil, or zeolite-containing fluorocarbon oil.

The material used for the protective layer is, for example,
Organic polymer materials (for example, fluorinated resin, epoxy resin, silicone resin, epoxy silicone resin, polystyrene, polyester, polycarbonate, polyamide, polyimide, polyamideimide, polyparaxylene, polyethylene, polyphenylene oxide), inorganic materials (for example, diamond) Examples include thin films, amorphous silica, electrically insulating glass, metal oxides, metal nitrides, metal carbonides, and metal sulfides, as well as photocurable resins. The material used for the protective layer can be used alone. Alternatively, a plurality of them may be used in combination. The protective layer may have a monolayer structure or a multilayer structure.

Further, for example, a metal oxide film (eg, aluminum oxide film) or a metal fluoride film can be provided on the electrode as a protective layer.

An interface layer (intermediate layer) made of, for example, an organic phosphorus compound, polysilane, an aromatic amine derivative, or a phthalocyanine derivative can be provided on the surface of the anode.

Further, an electrode such as an anode may be used by treating its surface with, for example, acid, ammonia / hydrogen peroxide or plasma.

The organic electroluminescent device of the present invention is generally used as a DC drive type device, but can also be used as an AC drive type device. Further, the organic electroluminescent element of the present invention may be a passive drive type such as a segment type or a simple matrix drive type, or an active drive type such as a TFT (thin film transistor) type or a MIM (metal-insulator-metal) type. May be The drive voltage is generally about 2 to 30V.

The organic electroluminescent element of the present invention can be used, for example, in a panel type light source, various light emitting elements, various display elements, various markers, various sensors and the like.

[0273]

EXAMPLES The present invention will be described in more detail with reference to production examples and examples, but of course the present invention is not limited thereto.

Production Example 1 Production of Compound of Exemplified Compound No. A-5 3.33 g of 9-bromo-10-phenylanthracene
7- (N-carbazolyl) -9,9-dimethylfluoren-2-ylboric acid 4.03 g, sodium carbonate 2.1
2 g and tetrakis (triphenylphosphine) palladium 0.35 g were heated to reflux for 5 hours in toluene (100 ml) and water (50 ml). After toluene was distilled off from the reaction mixture, the precipitated solid was filtered.
This solid was processed by silica gel column chromatography (eluent: toluene). After the toluene was distilled off under reduced pressure, the residue was recrystallized from a mixed solvent of toluene and acetone to give the compound of Exemplified Compound A-5 as yellow crystals.
26 g were obtained. Mass analysis: m / z = 611 Elemental analysis: (as C ₄₇ H ₃₃ N) C H N Calculated value (%) 92.27 5.44 2.29 Measured value (%) 92.20 5.38 2.42 Melting point: 250 ° C. or higher This compound was sublimated under the conditions of 330 ° C. and 1 × 10 ⁻⁴ Pa. Absorption maximum (in toluene) 390nm

Production Examples 2-35 In Production Example 1, various halides were used instead of using 9-bromo-10-phenylanthracene, and 7- (N-carbazolyl) -9,9-dimethylfluorene- Various compounds were prepared according to the method described in Preparation Example 1 except that various boric acid derivatives were used instead of using 2-ylboric acid. (Table 1) (Table 1
In Table 3), the halides and boric acid derivatives used, and the compounds produced are shown by exemplary compound numbers. The maximum absorption (nm) in toluene is also shown. The produced compounds were yellow to orange-yellow crystals, and the melting points of these compounds were 250 ° C or higher.

[0276]

[Table 1]

[0277]

[Table 2]

[0278]

[Table 3]

Production Example 36 Production of Compound of Exemplified Compound No. B-1 7.75 g of 10- (N-carbazolyl) anthracen-9-ylboronic acid, 4.46 g of 2,7-diiodo-9,9-dimethylfluorene, carbonic acid 4.24 g of sodium and 0.70 g of tetrakis (triphenylphosphine) palladium were added to toluene (100 ml) and water (50 m).
Heated to reflux in 1) for 5 hours. After toluene was distilled off from the reaction mixture, the precipitated solid was filtered. This solid was processed by silica gel column chromatography (eluent: toluene). After toluene was distilled off under reduced pressure, the residue was recrystallized from a mixed solvent of toluene and acetone to obtain 6.78 g of the compound of Exemplified compound B-1 as yellow crystals. Mass analysis: m / z = 876 Elemental analysis: (as C ₆₇ H ₄₄ N ₂ ) C H N Calculated value (%) 91.75 5.06 3.19 Measured value (%) 91.54 5.00 3. 46 Melting point: 250 ° C. or higher Incidentally, this compound sublimated under the conditions of 380 ° C. and 1 × 10 ⁻⁴ Pa. Absorption maximum (in toluene) 420nm

Production Examples 37 to 50 In Production Example 36, various boric acid derivatives were used instead of using 10- (N-carbazolyl) anthracen-9-ylboric acid, and 2,7-diiodo-9,9 was used. -Various compounds were prepared according to the method described in Preparation 36, except that various dihalogeno compounds were used instead of using dimethylfluorene. (Table 2) (Table 4)
Boric acid derivative and dihalogeno compound used for
In addition, the produced compounds are shown by the exemplified compound numbers. The maximum absorption (nm) in toluene is also shown.
The produced compound is a yellow to orange-yellow crystal,
The melting points of those compounds were 250 ° C. or higher.

[0281]

[Table 4]

Example 1 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed on a substrate holder of a vapor deposition apparatus, and then the vapor deposition tank was depressurized to 4 × 10 ⁻⁴ Pa. First, on the ITO transparent electrode, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited at a vapor deposition rate of 0.2 nm / sec to a thickness of 75 nm to form holes. Then, bis (2-methyl-8-quinolinolate) (4-phenylphenolate) aluminum and the compound of Exemplified Compound No. A-5 were deposited on the injection transport layer from different vapor deposition sources at a vapor deposition rate of 0. 2 nm / sec
Co-deposited to a thickness of 50 nm (weight ratio 100: 0.5)
Then, it was used as a light emitting layer. Next, tris (8-quinolinolato) aluminum is deposited at a deposition rate of 0.2 nm / sec.
It was vapor-deposited to a thickness of nm to form an electron injecting and transporting layer. On top of that, magnesium and silver are deposited at a deposition rate of 0.2 nm / se.
An organic electroluminescent device was produced by using c as a cathode by co-evaporating to a thickness of 200 nm (weight ratio 10: 1). In addition, vapor deposition is
It was carried out while maintaining the reduced pressure state of the vapor deposition tank. When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 53 mA / cm ² flowed. Brightness 2
A blue-green light emission of 460 cd / m ² was confirmed.

Examples 2 to 50 In Example 1, instead of using the compound of Exemplified Compound A-5 in forming the light emitting layer, Exemplified Compound No. A was used.
-9 compound (Example 2), exemplified compound number A-10 compound (Example 3), exemplified compound number A-13 compound (Example 4), exemplified compound number A-21 compound (Example 5) ), A compound of Exemplified Compound No. B-1 (Example 6),
Exemplified Compound No. B-6 compound (Example 7), Exemplified Compound No. B-9 compound (Example 8), Exemplified Compound No. C
-1 compound (Example 9), exemplified compound No. C-5 compound (Example 10), exemplified compound No. C-11 compound (Example 11), exemplified compound No. C-13 compound (Example 12) ), A compound of Exemplified Compound No. C-44 (Example 13), a compound of Exemplified Compound No. D-1 (Example 1)
4), the compound of Exemplified Compound No. D-14 (Example 1
5), a compound of Exemplified Compound No. E-1 (Example 16),
Exemplified Compound No. E-6 compound (Example 17), Exemplified Compound No. E-21 compound (Example 18), Exemplified Compound No. F-1 compound (Example 19), Exemplified Compound No. F
-5 compound (Example 20), exemplified compound number F-15
Compound (Example 21), exemplified compound No. G-3 compound (Example 22), exemplified compound No. G-7 compound (Example 23), exemplified compound No. G-9 compound (Example 2)
4), a compound of Exemplified Compound No. H-1 (Example 25),
Exemplified Compound No. I-3 compound (Example 26), Exemplified Compound No. I-4 compound (Example 27), Exemplified Compound No. I-5 compound (Example 28), Exemplified Compound No. J-
1 compound (Example 29), exemplified compound No. J-5 compound (Example 30), exemplified compound No. J-6 compound (Example 31), exemplified compound No. K-5 compound (Example 32) Compound of Exemplified Compound No. K-6 (Example 3
3), a compound of Exemplified Compound No. K-8 (Example 34),
Exemplified compound number L-2 compound (Example 35), Exemplified compound number L-6 compound (Example 36), Exemplified compound number M-1 compound (Example 37), Exemplified compound number M-
8 compound (Example 38), exemplified compound number M-9 compound (Example 39), exemplified compound number N-6 compound (Example 40), exemplified compound number N-13 compound (Example 41) Compound of Exemplified Compound No. O-1 (Example 4
2), a compound of Exemplified Compound No. O-4 (Example 43),
Exemplified compound number O-7 compound (Example 44), Exemplified compound number O-21 compound (Example 45), Exemplified compound number P-2 compound (Example 46), Exemplified compound number P
-5 compound (Example 47), exemplified compound number P-9 compound (Example 48), exemplified compound number Q-2 compound (Example 49), exemplified compound number Q-6 compound (Example 50) An organic electroluminescent device was produced by the method described in Example 1 except that (1) was used. When a DC voltage of 12 V was applied to each element in a dry atmosphere, blue to blue-green light emission was confirmed. Further study its characteristics,
The results are shown in (Table 3) (Tables 5 to 7).

Comparative Example 1 In Example 1, bis (2-methyl-) was used in the formation of the light emitting layer without using the compound of Exemplified Compound No. A-5.
An organic electroluminescent device was produced by the method described in Example 1, except that only 8-quinolinolato) (4-phenylphenolato) aluminum was used to form a light emitting layer by vapor deposition to a thickness of 50 nm. In this device, in a dry atmosphere, 1
When a DC voltage of 2 V was applied, blue light emission was confirmed. Further, its characteristics were examined, and the results are shown in (Table 3).

Comparative Example 2 In Example 1, instead of using the compound of Exemplified Compound No. A-5 in the formation of the light emitting layer, N-methyl-
An organic electroluminescent device was produced by the method described in Example 1 except that 2-methoxyacridone was used. When a DC voltage of 12 V was applied to this element in a dry atmosphere, blue light emission was confirmed. Further study its characteristics,
The results are shown in (Table 3).

[0286]

[Table 5]

[0287]

[Table 6]

[0288]

[Table 7]

Example 51 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed on a substrate holder of a vapor deposition apparatus, and then the vapor deposition tank was depressurized to 4 × 10 ⁻⁴ Pa. First, on the ITO transparent electrode, 4,4 ′, 4 ″ -tris [N
50- (3 ′ ″-methylphenyl) -N-phenylamino] triphenylamine was deposited at a deposition rate of 0.1 nm / sec.
It vapor-deposited to a thickness of nm to form a first hole injecting and transporting layer. Next, 4,4 ′,-bis [N-phenyl-N- (1 ″ -naphthyl) amino] biphenyl and the compound of Exemplified Compound No. A-5 were evaporated from different evaporation sources at a deposition rate of 0.2 nm / se.
Co-deposition to a thickness of 20 nm with c (weight ratio 100: 5.0)
As a result, the light emitting layer also served as the second hole injecting and transporting layer. Then, tris (8-quinolinolato) aluminum was vapor-deposited thereon at a vapor deposition rate of 0.2 nm / sec. To a thickness of 50 nm to form an electron injecting and transporting layer. Furthermore, magnesium and silver were deposited on the substrate at a deposition rate of 0.2 nm / sec for 200 n.
An organic electroluminescence device was prepared by co-evaporating to a thickness of m (weight ratio 10: 1) to form a cathode. The vapor deposition was carried out while keeping the vacuum state of the vapor deposition tank. When a direct current voltage of 15 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 61 mA / cm ² flowed. Brightness 2580 cd
A blue-green light emission of / m ² was confirmed.

Examples 52 to 100 In Example 51, instead of using the compound of Exemplified Compound A-5 in forming the light emitting layer, the compound of Exemplified Compound No. A-9 (Example 52) and Exemplified Compound No. A were used. -1
0 compound (Example 53), exemplified compound No. A-13 compound (Example 54), exemplified compound No. A-21 compound (Example 55), exemplified compound No. B-1 compound (Example 56) Compound of Exemplified Compound No. B-6 (Example 5
7), a compound of Exemplified Compound No. B-9 (Example 58),
Exemplified Compound No. C-1 compound (Example 59), Exemplified Compound No. C-5 compound (Example 60), Exemplified Compound No. C-11 compound (Example 61), Exemplified Compound No. C
-13 compound (Example 62), exemplified compound number C-4
4 compound (Example 63), exemplified compound No. D-1 compound (Example 64), exemplified compound No. D-14 compound (Example 65), exemplified compound No. E-1 compound (Example 66) Compound of Exemplified Compound No. E-6 (Example 6
7), the compound of Exemplified Compound No. E-21 (Example 6)
8), a compound of Exemplified Compound No. F-1 (Example 69),
Exemplified Compound No. F-5 compound (Example 70), Exemplified Compound No. F-15 compound (Example 71), Exemplified Compound No. G-3 compound (Example 72), Exemplified Compound No. G
-7 compound (Example 73), exemplified compound number G-9 compound (Example 74), exemplified compound number H-1 compound (Example 75), exemplified compound number I-3 compound (Example 76) ), The compound of Exemplified Compound No. I-4 (Example 7
7), a compound of Exemplified Compound No. I-5 (Example 78),
Exemplified Compound No. J-1 compound (Example 79), Exemplified Compound No. J-5 compound (Example 80), Exemplified Compound No. J-6 compound (Example 81), Exemplified Compound No. K-
5 compound (Example 82), exemplified compound number K-6 compound (Example 83), exemplified compound number K-8 compound (Example 84), exemplified compound number L-2 compound (Example 85) Compound of Exemplified Compound No. L-6 (Example 8
6), the compound of Exemplified Compound No. M-1 (Example 87),
Exemplified Compound No. M-8 compound (Example 88), Exemplified Compound No. M-9 compound (Example 89), Exemplified Compound No. N-6 compound (Example 90), Exemplified Compound No. N-
13 compound (Example 91), exemplified compound No. O-1 compound (Example 92), exemplified compound No. O-4 compound (Example 93), exemplified compound No. O-7 compound (Example 94) Compound of Exemplified Compound No. O-21 (Example 9
5), a compound of Exemplified Compound No. P-2 (Example 96),
Exemplified Compound No. P-5 compound (Example 97), Exemplified Compound No. P-9 compound (Example 98), Exemplified Compound No. Q-2 compound (Example 99), Exemplified Compound No. Q-
An organic electroluminescent device was produced by the method described in Example 51 except that the compound of Example 6 (Example 100) was used.
When a DC voltage of 15 V was applied to each element in a dry atmosphere, blue to blue-green light emission was confirmed. Further, its characteristics were examined, and the results (Table 4) (Tables 8 to 9)
It was shown to.

[0291]

[Table 8]

[0292]

[Table 9]

Example 101 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed on a substrate holder of a vapor deposition apparatus, and then the vapor deposition tank was depressurized to 4 × 10 ⁻⁴ Pa. First, on the ITO transparent electrode, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited at a vapor deposition rate of 0.2 nm / sec to a thickness of 75 nm to form holes. Then, bis (2-methyl-8-quinolinolate) (4-phenylphenolate) aluminum and the compound of Exemplified Compound No. A-5 were deposited on the injection transport layer from different vapor deposition sources at a vapor deposition rate of 0. 2 nm / sec
Co-deposited to a thickness of 50 nm (weight ratio 100: 1.0)
Then, it was used as a light emitting layer. Next, tris (8-quinolinolato) aluminum is deposited at a deposition rate of 0.2 nm / sec.
It was vapor-deposited to a thickness of nm to form an electron injecting and transporting layer. On top of that, magnesium and silver are deposited at a deposition rate of 0.2 nm / se.
An organic electroluminescent device was produced by using c as a cathode by co-evaporating to a thickness of 200 nm (weight ratio 10: 1). In addition, vapor deposition is
It was carried out while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 54 mA / cm ² flowed. Brightness 2
A blue-green light emission of 420 cd / m ² was confirmed.

Example 102 In Example 101, bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-5 were used in Example 101 instead of the compound (2-Methyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. A-21 were used to co-evaporate to a thickness of 50 nm (weight ratio 100 : 2.0), and an organic electroluminescent device was produced by the method described in Example 101 except that the light emitting layer was used. The prepared organic electroluminescent device was placed in a dry atmosphere for 1
When a DC voltage of 2 V was applied, a current of 56 mA / cm ² flowed. Blue-green light emission with a luminance of 2370 cd / m ² was confirmed.

Example 103 In Example 101, a bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-5 were used instead of bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum in the formation of the light emitting layer. (2-Methyl-8-quinolinolato) (4-phenylphenolato) aluminum and a compound of Exemplified Compound No. B-1 were co-deposited to a thickness of 50 nm (weight ratio 100: 1.0) to obtain a light emitting layer. An organic electroluminescent element was produced by the method described in Example 101 except that the above was applied. When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 56 mA.
A current of / cm ² was applied. Blue-green light emission with a luminance of 2420 cd / m ² was confirmed.

Example 104 In Example 101, instead of using bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-5 in the formation of the light emitting layer, tris was used. Using (8-quinolinolato) aluminum and a compound of Exemplified Compound No. C-1,
Co-deposited to a thickness of 50 nm (weight ratio 100: 3.0),
An organic electroluminescent element was produced by the method described in Example 101 except that the light emitting layer was used. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 55 mA / cm ² flowed. Brightness 2370 cd
A blue-green light emission of / m ² was confirmed.

Example 105 In Example 101, instead of using bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-5 in forming the light emitting layer, tris was used. Using (8-quinolinolato) aluminum and the compound of Exemplified Compound No. D-1,
Co-deposited to a thickness of 50 nm (weight ratio 100: 6.0),
An organic electroluminescent element was produced by the method described in Example 101 except that the light emitting layer was used. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 54 mA / cm ² flowed. Brightness 2360 cd
A blue-green light emission of / m ² was confirmed.

Example 106 In Example 101, bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-5 were used instead of bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum in forming the light emitting layer. (2-Methyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. E-1 were used to co-evaporate to a thickness of 50 nm (weight ratio 100 : 2.0), and an organic electroluminescent device was produced by the method described in Example 101 except that the light emitting layer was used. The prepared organic electroluminescent device was subjected to 12
When a DC voltage of V was applied, a current of 54 mA / cm ² flowed. Blue-green light emission with a luminance of 2450 cd / m ² was confirmed.

Example 107 In Example 101, instead of using bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-5 in forming the light emitting layer, tris was used. Using (8-quinolinolato) aluminum and a compound of Exemplified Compound No. F-1,
Co-deposition to a thickness of 50 nm (weight ratio 100: 10.0)
Then, an organic electroluminescent element was produced by the method described in Example 101 except that the light emitting layer was used. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 55 mA / cm ² flowed. Brightness 2420
Blue-green light emission of cd / m ² was confirmed.

Example 108 In Example 101, bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-5 were used instead of bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum in forming the light emitting layer. (2,4-Dimethyl-8-quinolinolato) aluminum-μ-oxo-bis (2,2
Example 101 except that 4-dimethyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. G-3 were co-deposited to a thickness of 50 nm (weight ratio 100: 1.0) to form a light emitting layer. An organic electroluminescence device was produced by the method described in 1. When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 56 mA /
An electric current of cm ² was applied. Blue-green light emission with a luminance of 2410 cd / m ² was confirmed.

Example 109 In Example 101, a bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-5 were used instead of the bis (2-methyl-8-quinolinolato) (4-phenylphenolate) aluminum in the formation of the light emitting layer. (2-Methyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. H-1 were used to co-evaporate to a thickness of 50 nm (weight ratio 100 : 2.0), and an organic electroluminescent device was produced by the method described in Example 101 except that the light emitting layer was used. The prepared organic electroluminescent device was subjected to 12
When a DC voltage of V was applied, a current of 53 mA / cm ² flowed. Blue-green light emission with a luminance of 2350 cd / m ² was confirmed.

Example 110 In Example 101, bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-5 were used instead of bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum in forming the light emitting layer. (2,4-Dimethyl-8-quinolinolato) aluminum-μ-oxo-bis (2,2
Example 101, except that 4-dimethyl-8-quinolinolato) aluminum and a compound of Exemplified Compound No. I-3 were co-deposited to a thickness of 50 nm (weight ratio 100: 4.0) to form a light emitting layer. An organic electroluminescence device was produced by the method described in 1. When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 54 mA /
An electric current of cm ² was applied. Blue-green light emission with a luminance of 2360 cd / m ² was confirmed.

Example 111 In Example 101, instead of using bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-5 in the formation of the light emitting layer, tris was used. Using (8-quinolinolato) aluminum and a compound of Exemplified Compound No. J-1,
Co-deposited to a thickness of 50 nm (weight ratio 100: 3.0),
An organic electroluminescent element was produced by the method described in Example 101 except that the light emitting layer was used. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 56 mA / cm ² flowed. Brightness 2440 cd
A blue-green light emission of / m ² was confirmed.

Example 112 In Example 101, instead of using bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-5 in the formation of the light emitting layer, tris was used. Using (8-quinolinolato) aluminum and a compound of Exemplified Compound No. K-5,
Co-deposited to a thickness of 50 nm (weight ratio 100: 6.0),
An organic electroluminescent element was produced by the method described in Example 101 except that the light emitting layer was used. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 57 mA / cm ² flowed. Brightness 2390 cd
A blue-green light emission of / m ² was confirmed.

Example 113 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed on a substrate holder of a vapor deposition apparatus, and then the vapor deposition tank was depressurized to 4 × 10 ⁻⁴ Pa. First, on the ITO transparent electrode, 4,4 ′, 4 ″ -tris [N
-(3 '''-methylphenyl) -N-phenylamino]
Triphenylamine is deposited at a deposition rate of 0.1 nm / sec.
It vapor-deposited to a thickness of nm to form a first hole injecting and transporting layer. Then, on it, 4,4'-bis [N-phenyl-N-
(3 ″ -methylphenyl) amino] biphenyl was vapor-deposited at a vapor deposition rate of 0.2 nm / sec to a thickness of 45 nm to form a second hole injecting and transporting layer. Then, bis (2-
Methyl-8-quinolinolato) (4-phenylphenolatoaluminum) and the compound of Exemplified Compound No. A-5 were deposited from different vapor deposition sources at a vapor deposition rate of 0.2 nm / sec.
Co-deposition (weight ratio 100: 2.0) was performed to a thickness of 0 nm to form a light emitting layer. Next, tris (8-quinolinolato) aluminum was vapor-deposited at a vapor deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injecting and transporting layer. On top of that,
20 magnesium and silver at a deposition rate of 0.2 nm / sec
An organic electroluminescence device was produced by co-evaporating to a thickness of 0 nm (weight ratio 10: 1) to form a cathode. The vapor deposition was carried out while keeping the vacuum state of the vapor deposition tank. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 55 mA / cm ² flowed. Brightness 2760
Blue-green light emission of cd / m ² was confirmed.

Example 114 In Example 113, bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-5 were used instead of the bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum in the formation of the light emitting layer. (2,4-Dimethyl-8-quinolinolato) aluminum-μ-oxo-bis (2,2
Example 113, except that 4-dimethyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. B-6 were co-deposited to a thickness of 50 nm (weight ratio 100: 1.0) to form a light emitting layer. An organic electroluminescence device was produced by the method described in 1. When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 53 mA /
An electric current of cm ² was applied. Blue-green light emission with a luminance of 2580 cd / m ² was confirmed.

Example 115 In Example 113, bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-5 were used instead of bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum in the formation of the light emitting layer. (2-Methyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum and a compound of Exemplified Compound No. C-11 were used to co-evaporate to a thickness of 50 nm (weight ratio 100 : 3.0), and an organic electroluminescent element was manufactured by the method described in Example 113 except that the light emitting layer was used. The prepared organic electroluminescent device was placed in a dry atmosphere for 1
When a DC voltage of 2 V was applied, a current of 56 mA / cm ² flowed. Blue-green light emission with a luminance of 2,620 cd / m ² was confirmed.

Example 116 In Example 113, instead of using bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-5 in forming the light emitting layer, tris was used. Using (8-quinolinolato) aluminum and a compound of Exemplified Compound No. D-14, co-evaporation was performed to a thickness of 50 nm (weight ratio 100: 2.0).
Then, an organic electroluminescent element was produced by the method described in Example 113 except that the light emitting layer was used. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 54 mA / cm ² flowed. Brightness 2440
Blue-green light emission of cd / m ² was confirmed.

Example 117 In Example 113, bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-5 were used instead of using the compound of Example Compound A-5 in the formation of the light emitting layer. (2-Methyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. E-6 were used to co-evaporate to a thickness of 50 nm (weight ratio 100 : 4.0), and an organic electroluminescence device was produced by the method described in Example 113 except that the light emitting layer was used. The prepared organic electroluminescent device was subjected to 12
When a DC voltage of V was applied, a current of 57 mA / cm ² flowed. Blue-green light emission with a luminance of 2560 cd / m ² was confirmed.

Example 118 In Example 113, instead of using bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-5 in forming the light emitting layer, tris was used. Using (8-quinolinolato) aluminum and a compound of Exemplified Compound No. G-7,
Co-deposited to a thickness of 50 nm (weight ratio 100: 2.0),
An organic electroluminescent element was produced by the method described in Example 113 except that the light emitting layer was used. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 56 mA / cm ² flowed. Brightness 2560 cd
A blue-green light emission of / m ² was confirmed.

Example 119 In Example 113, bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-5 were used instead of bis (2-methyl-8-quinolinolato) (4-phenylphenolate) aluminum in the formation of the light emitting layer. (2,4-Dimethyl-8-quinolinolato) aluminum-μ-oxo-bis (2,2
Example 113 except that 4-dimethyl-8-quinolinolato) aluminum and a compound of Exemplified Compound No. K-8 were co-deposited to a thickness of 50 nm (weight ratio 100: 2.0) to form a light emitting layer. An organic electroluminescence device was produced by the method described in 1. When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 55 mA /
An electric current of cm ² was applied. Blue-green light emission with a luminance of 2570 cd / m ² was confirmed.

Example 120 In Example 113, bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-5 were used instead of bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum in forming the light emitting layer. (2,4-Dimethyl-8-quinolinolato) aluminum-μ-oxo-bis (2,2
Example 113, except that 4-dimethyl-8-quinolinolato) aluminum and a compound of Exemplified Compound No. M-1 were co-deposited to a thickness of 50 nm (weight ratio 100: 3.0) to form a light emitting layer. An organic electroluminescence device was produced by the method described in 1. When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 57 mA /
An electric current of cm ² was applied. Blue-green light emission with a luminance of 2630 cd / m ² was confirmed.

Example 121 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed on a substrate holder of a vapor deposition apparatus, and then the vapor deposition tank was depressurized to 4 × 10 ⁻⁴ Pa. First, on the ITO transparent electrode, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited at a vapor deposition rate of 0.2 nm / sec to a thickness of 75 nm to form holes. Then, bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and a compound of Exemplified Compound No. A-10 were deposited on the injection transport layer from different vapor deposition sources at a vapor deposition rate of 0. 2 nm / se
Co-deposition to a thickness of 50 nm with c (weight ratio 100: 2.0)
Then, it was used as a light emitting layer. Next, 1,3-bis [5 '-(4 "
-Tert-butylphenyl) -1 ', 3', 4'-oxadiazol-2'-yl] benzene with a deposition rate of 0.2
It was vapor-deposited to a thickness of 50 nm at nm / sec to form an electron injecting and transporting layer. Further, magnesium and silver were co-deposited at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form a cathode, and an organic electroluminescence device was produced. The vapor deposition was carried out while keeping the vacuum state of the vapor deposition tank. The prepared organic electroluminescent device was subjected to 12
When a DC voltage of V was applied, a current of 55 mA / cm ² flowed. Blue-green light emission with a luminance of 2360 cd / m ² was confirmed.

Example 122 In Example 121, instead of using bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-10 in forming the light emitting layer, tris was used. (8-quinolinolato)
Using aluminum and a compound of Exemplified Compound No. E-6, co-evaporated to a thickness of 50 nm (weight ratio 100: 4.0).
Then, an organic electroluminescent element was produced by the method described in Example 121 except that the light emitting layer was used. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 56 mA / cm ² flowed. Brightness 2410
Blue-green light emission of cd / m ² was confirmed.

Example 123 In Example 121, instead of using bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum and the compound of Exemplified Compound A-10 in forming the light emitting layer, (2-Methyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum and a compound of Exemplified Compound No. L-6 were used to co-evaporate to a thickness of 50 nm (weight ratio 100 : 3.0), and an organic electroluminescent device was produced by the method described in Example 121 except that the light emitting layer was used. The prepared organic electroluminescent device was placed in a dry atmosphere for 1
When a DC voltage of 2 V was applied, a current of 53 mA / cm ² flowed. Blue-green light emission with a luminance of 2340 cd / m ² was confirmed.

Example 124 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned with a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed on a substrate holder of a vapor deposition apparatus, and then the vapor deposition tank was depressurized to 4 × 10 ⁻⁴ Pa. First, on the ITO transparent electrode, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited at a vapor deposition rate of 0.2 nm / sec to a thickness of 75 nm to form holes. Then, the compound of Exemplified Compound No. C-1 was vapor-deposited at a rate of 0.2 nm / sec.
Was evaporated to a thickness of 50 nm to form a light emitting layer. Next, tris (8-quinolinolato) aluminum was vapor-deposited at a vapor deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injecting and transporting layer. On top of that, magnesium and silver,
An organic electroluminescent device was prepared by co-evaporating to a thickness of 200 nm (weight ratio: 10: 1) at a vapor deposition rate of 0.2 nm / sec to form a cathode. The vapor deposition was carried out while keeping the vacuum state of the vapor deposition tank. When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 56 mA / cm.
^Two currents flowed. Blue-green light emission with a luminance of 2700 cd / m ² was confirmed.

Example 125 As described in Example 124, except that the compound of Exemplified Compound No. J-6 was used instead of the compound of Exemplified Compound C-1 in forming the light emitting layer. The organic electroluminescent element was produced by the method. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 54 mA / cm ² flowed. Blue-green light emission with a luminance of 2560 cd / m ² was confirmed.

Example 126 As described in Example 124, except that the compound of Exemplified compound No. N-6 was used instead of the compound of Exemplified compound C-1 in the formation of the light emitting layer. The organic electroluminescent element was produced by the method. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 56 mA / cm ² flowed. Blue-green light emission with a luminance of 2530 cd / m ² was confirmed.

Example 127 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned with a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed on a substrate holder of a vapor deposition apparatus, and then the vapor deposition tank was depressurized to 4 × 10 ⁻⁴ Pa. First, on the ITO transparent electrode, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited at a vapor deposition rate of 0.2 nm / sec to a thickness of 75 nm to form holes. Then, a compound of Exemplified Compound No. A-5 was vapor-deposited at a rate of 0.2 nm / sec.
Was evaporated to a thickness of 50 nm to form a light emitting layer. Then, on it, 1,3-bis [5 '-(4 "-tert-butylphenyl) -1', 3 ', 4'-oxadiazole-2'
-Yl] benzene at a deposition rate of 0.2 nm / sec.
It was vapor-deposited to a thickness of nm to form an electron injecting and transporting layer. On top of that, magnesium and silver are deposited at a deposition rate of 0.2 nm / se.
An organic electroluminescent device was produced by using c as a cathode by co-evaporating to a thickness of 200 nm (weight ratio 10: 1). In addition, vapor deposition is
It was carried out while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 14 V was applied to the produced organic electroluminescence device in a dry atmosphere, a current of 46 mA / cm ² flowed. Brightness 1
A blue-green light emission of 850 cd / m ² was confirmed.

Example 128 As described in Example 127, except that the compound of Exemplified Compound No. C-1 was used in place of the compound of Exemplified Compound A-5 in Example 127 to form the light emitting layer. The organic electroluminescent element was produced by the method. When a DC voltage of 14 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 45 mA / cm ² flowed. Blue-green light emission with a brightness of 1780 cd / m ² was confirmed.

Example 129 As described in Example 127, except that the compound of Exemplified Compound No. D-14 was used in place of the compound of Exemplified Compound A-5 in the formation of the light emitting layer in Example 127. The organic electroluminescent element was produced by the method. When a DC voltage of 14 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 58 mA / cm ² flowed.
Blue-green light emission with a luminance of 1460 cd / m ² was confirmed.

Example 130 A glass substrate having a 200 nm thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed on a substrate holder of a vapor deposition apparatus, and then the vapor deposition tank was depressurized to 4 × 10 ⁻⁴ Pa. First, on the ITO transparent electrode, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited at a vapor deposition rate of 0.2 nm / sec to a thickness of 75 nm to form holes. Then, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. A-10 were deposited on the injection transport layer from different vapor deposition sources at a vapor deposition rate of 0.
Co-deposition at a thickness of 50 nm at 2 nm / sec (weight ratio 10
0: 1.0) to obtain a light emitting layer which also serves as an electron transport layer. Furthermore, magnesium and silver are vapor-deposited at a rate of 0.2 n
Co-deposition at a thickness of 200 nm at m / sec (weight ratio 10:
The organic electroluminescent element was produced by using 1) as a cathode. still,
The vapor deposition was carried out while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 54 mA / cm ² flowed. Blue-green light emission with a luminance of 2310 cd / m ² was confirmed.

Example 131 In Example 130, tris (8-quinolinolato) aluminum and the exemplified compound A- were used in the formation of the light emitting layer.
Instead of using the compound of No. 10, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. B-6 were co-evaporated to a thickness of 50 nm (weight ratio 100:
1.0), and an organic electroluminescence device was produced by the method described in Example 130 except that the light emitting layer was used. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 52 mA / cm ² flowed. Blue-green light emission with a luminance of 2360 cd / m ² was confirmed.

Example 132 In Example 130, tris (8-quinolinolato) aluminum and the exemplified compound A- were used in the formation of the light emitting layer.
Instead of using 10 compounds, bis (2-methyl-
8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum and a compound of Exemplified Compound No. C-44 were co-evaporated to a thickness of 50 nm (weight ratio 100: 2.0). Then, an organic electroluminescent element was produced by the method described in Example 130 except that the light emitting layer was used. When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 55 mA.
A current of / cm ² was applied. Blue-green light emission with a luminance of 2320 cd / m ² was confirmed.

Example 133 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned with a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed on a substrate holder of a vapor deposition apparatus, and then the vapor deposition tank was depressurized to 4 × 10 ⁻⁴ Pa. First, a compound of Exemplified Compound No. A-21 was vapor-deposited on an ITO transparent electrode at a vapor deposition rate of 0.2 nm / sec to a thickness of 55 nm to form a light emitting layer. Then, on it, 1,3-bis [5 '-(4 "-tert-butylphenyl) -1',
3 ′, 4′-oxadiazol-2′-yl] benzene was vapor-deposited at a vapor deposition rate of 0.2 nm / sec to a thickness of 75 nm to form an electron injecting and transporting layer. Further, magnesium and silver were co-deposited at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form a cathode, and an organic electroluminescence device was produced. The vapor deposition was carried out while keeping the vacuum state of the vapor deposition tank. In the produced organic electroluminescent element,
When a DC voltage of 14V was applied in a dry atmosphere, it was 6
A current of 1 mA / cm ² flowed. Blue-green light emission with a luminance of 1520 cd / m ² was confirmed.

Example 134 Example 133 is the same as Example 133, except that the compound of Exemplified compound No. C-13 was used instead of the compound of Exemplified compound A-21 in the formation of the light emitting layer.
An organic electroluminescence device was produced by the method described in 1. When a DC voltage of 14 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 59 mA / cm ² flowed. Blue-green light emission with a luminance of 1480 cd / m ² was confirmed.

Example 135 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas and further UV / ozone washed. Next, poly-N-vinylcarbazole (weight average molecular weight 1
50000), a compound of Exemplified Compound No. A-13, coumarin 6 [“3- (2′-benzothiazolyl) -7-diethylaminocoumarin” (green light emitting component)], and D
CM-1 ["4- (dicyanomethylene) -2-methyl-
6- (4′-dimethylaminostyryl) -4H-pyran ”(orange luminescent component)] in a weight ratio of 1
400% by dip coating method using a 3% by weight dichloroethane solution contained in a ratio of 00: 5: 3: 2.
nm emission layer was formed. Next, after fixing the glass substrate having this light emitting layer to the substrate holder of the vapor deposition apparatus, the vapor deposition tank was depressurized to 4 × 10 ⁻⁴ Pa. Furthermore, 3- (4'-tert-butylphenyl) -4-phenyl-5- (4 "-phenylphenyl) -1,2,4-triazole was deposited on the light emitting layer at a deposition rate of 0.2 nm / sec. After vapor deposition to a thickness of 20 nm, tris (8-quinolinolato) aluminum is further vapor-deposited thereon at a deposition rate of 0.2 nm / sec.
To a thickness of 30 nm to form an electron injecting and transporting layer. Furthermore, magnesium and silver are vapor-deposited at a rate of 0.2 n
Co-deposition at a thickness of 200 nm at m / sec (weight ratio 10:
The organic electroluminescent element was produced by using 1) as a cathode. When a DC voltage of 12 V was applied to the produced organic electroluminescence device in a dry atmosphere, a current of 71 mA / cm ² flowed. White light emission with a luminance of 1390 cd / m ² was confirmed.

Examples 136 to 143 Instead of using the compound of Exemplified Compound No. A-13 in Example 135, the compound of Exemplified Compound No. B-9 (Example 136), the compound of Exemplified Compound No. C-1 ( Example 137), compound of Exemplified Compound No. D-1 (Example 138), compound of Exemplified Compound No. E-6 (Example 13)
9), the compound of Exemplified Compound No. J-6 (Example 14
0), the compound of Exemplified Compound No. K-8 (Example 14
1), the compound of Exemplified Compound No. L-2 (Example 14
2), a compound of Exemplified Compound No. O-4 (Example 143)
An organic electroluminescence device was produced by the method described in Example 135 except that was used. When a direct current voltage of 12 V was applied to each element in a dry atmosphere, white light emission was observed. Furthermore, the characteristics are examined, and the result ((5th
Table) (Table 10).

[0329]

[Table 10]

Example 144 A glass substrate having a 200 nm thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas and further UV / ozone washed. Next, poly-N-vinylcarbazole (weight average molecular weight 1
50000), 1,3-bis [5 '-(4 "-tert-butylphenyl) -1', 3 ', 4'-oxadiazol-2'-yl] benzene and compound of exemplary compound number C-5 Was used to form a light-emitting layer having a thickness of 300 nm by a dip coating method using a 3% by weight dichloroethane solution containing the light-emitting layer at a ratio of 100: 30: 3. After fixing to the substrate holder of the vapor deposition apparatus, the vapor deposition tank was depressurized to 4 × 10 ⁻⁴ Pa. Furthermore, magnesium and silver were deposited on the light emitting layer at a vapor deposition rate of 0.2 nm / sec to a thickness of 200 nm. An organic electroluminescent device was produced by vapor deposition (weight ratio 10: 1) to serve as a cathode, and the produced organic electroluminescent device was subjected to 1 in a dry atmosphere.
When a DC voltage of 5 V was applied, a current of 67 mA / cm ² flowed. Blue-green light emission with a luminance of 1610 cd / m ² was confirmed.

Example 145 In Example 144, except that the compound of Exemplified Compound No. E-21 was used instead of the compound of Exemplified Compound No. C-5 in forming the light emitting layer.
An organic electroluminescence device was produced by the method described in 4. When a DC voltage of 15 V was applied to the produced organic electroluminescence device in a dry atmosphere, a current of 67 mA / cm ² flowed. Blue light emission with a luminance of 1560 cd / m ² was confirmed.

Comparative Example 3 Instead of using the compound of Exemplified Compound No. C-5 in forming the light emitting layer in Example 144, 1,1,
An organic electroluminescent device was produced by the method described in Example 144 except that 4,4-tetraphenyl-1,3-butadiene was used. When a direct current voltage of 15 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 86 m.
A current of A / cm ² flowed. Blue light emission with a luminance of 760 cd / m ² was confirmed.

Example 146 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas and further UV / ozone washed. Next, on the ITO transparent electrode, polycarbonate (weight average molecular weight 50,000),
4,4'-bis [N-phenyl-N- (3 "-methylphenyl) amino] biphenyl, bis (2-methyl-8-
Quinolinolato) aluminum-μ-oxo-bis (2
-Methyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. C-1 were each added in a weight ratio of 10
Using a 3% by weight dichloroethane solution contained in a ratio of 0: 40: 60: 1, by a dip coating method, 30
A 0 nm light emitting layer was formed. Next, after fixing the glass substrate having this light emitting layer to the substrate holder of the vapor deposition device,
The pressure of the vapor deposition tank was reduced to 4 × 10 ⁻⁴ Pa. Further, magnesium and silver were co-evaporated (weight ratio 10: 1) to a thickness of 200 nm at a vapor deposition rate of 0.2 nm / sec on the light emitting layer to form a cathode, thereby producing an organic electroluminescence device. When a DC voltage of 15 V was applied to the produced organic electroluminescence device in a dry atmosphere, a current of 62 mA / cm ² flowed. Brightness 980
Blue-green light emission of cd / m ² was confirmed.

Example 147 Example 146 except that the compound of Exemplified Compound No. I-3 was used in place of the compound of Exemplified Compound No. C-1 in the formation of the light emitting layer in Example 146.
An organic electroluminescence device was produced by the method described in 1. When a DC voltage of 15 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 59 mA / cm ² flowed. Blue light emission with a luminance of 950 cd / m ² was confirmed.

Example 148 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed on a substrate holder of a vapor deposition apparatus, and then the vapor deposition tank was depressurized to 4 × 10 ⁻⁴ Pa. First, a compound of Exemplified Compound No. A-5 was vapor-deposited on an ITO transparent electrode at a vapor deposition rate of 0.2 nm / sec to a thickness of 75 nm to form a hole injecting and transporting layer. Then, tris (8-quinolinolato) aluminum is vapor-deposited thereon with a deposition rate of 0.2.
It was vapor-deposited at a thickness of 50 nm at a rate of nm / sec to obtain a light emitting layer which also serves as an electron injecting and transporting layer. Further, magnesium and silver were co-deposited at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form a cathode, and an organic electroluminescence device was produced. The vapor deposition was carried out while keeping the vacuum state of the vapor deposition tank. When a direct current voltage of 12 V was applied to the produced organic electroluminescent element in a dry atmosphere, it was 51 m.
A current of A / cm ² flowed. Green light emission with a luminance of 2420 cd / m ² was confirmed.

Example 149 In Example 148, except that the compound of Exemplified compound number B-6 was used instead of the compound of Exemplified compound number A-5 in the formation of the hole injecting and transporting layer.
An organic electroluminescent device was produced by the method described in Example 148. In the prepared organic electroluminescent device, in a dry atmosphere,
When a DC voltage of 12 V was applied, a current of 53 mA / cm ² flowed. Green light emission with a luminance of 2380 cd / m ² was confirmed.

Example 150 In Example 148, except that the compound of Exemplified Compound No. C-1 was used instead of the compound of Exemplified Compound No. A-5 in forming the hole injecting and transporting layer.
An organic electroluminescent device was produced by the method described in Example 148. In the prepared organic electroluminescent device, in a dry atmosphere,
When a DC voltage of 12 V was applied, a current of 54 mA / cm ² flowed. Green light emission with a luminance of 2360 cd / m ² was confirmed.

Example 151 In Example 148, except that the compound of Exemplified Compound No. D-1 was used instead of the compound of Exemplified Compound No. A-5 in the formation of the hole injecting and transporting layer.
An organic electroluminescent device was produced by the method described in Example 148. In the prepared organic electroluminescent device, in a dry atmosphere,
When a DC voltage of 12 V was applied, a current of 53 mA / cm ² flowed. Green light emission with a luminance of 2380 cd / m ² was confirmed.

Example 152 In Example 148, except that the compound of Exemplified Compound No. F-5 was used instead of the compound of Exemplified Compound No. A-5 in forming the hole injecting and transporting layer.
An organic electroluminescent device was produced by the method described in Example 148. In the prepared organic electroluminescent device, in a dry atmosphere,
When a DC voltage of 12 V was applied, a current of 52 mA / cm ² flowed. Green light emission with a luminance of 2400 cd / m ² was confirmed.

Example 153 A glass substrate having a 200 nm thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed on a substrate holder of a vapor deposition apparatus, and then the vapor deposition tank was depressurized to 4 × 10 ⁻⁴ Pa. First, on the ITO transparent electrode, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited at a vapor deposition rate of 0.2 nm / sec to a thickness of 75 nm to form holes. Then, tris (2-phenylpyridine) iridium and the compound of Exemplified Compound No. A-5 were deposited on the above injecting and transporting layer from different vapor deposition sources at a vapor deposition rate of 0.2.
Co-evaporation to a thickness of 50 nm at nm / sec (weight ratio 100:
3) and it was set as the light emitting layer. Next, tris (8-quinolinolato) aluminum was deposited at a deposition rate of 0.2 nm / sec.
It vapor-deposited to a thickness of 0 nm to form an electron injecting and transporting layer. Furthermore, magnesium and silver are vapor-deposited at a rate of 0.2 nm /
An organic electroluminescence device was prepared by co-evaporating to a thickness of 200 nm in sec (weight ratio 10: 1) to form a cathode. The vapor deposition was carried out while keeping the vacuum state of the vapor deposition tank. When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, green light emission was confirmed.

Example 154 Example 153, except that the compound of Exemplified Compound No. A-6 was used in place of the compound of Exemplified Compound No. A-5 in the formation of the light emitting layer in Example 153.
An organic electroluminescence device was produced by the method described in 1. When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, green light emission was confirmed.

Example 155 In Example 153, except that the compound of Exemplified Compound No. C-1 was used instead of the compound of Exemplified Compound No. A-5 in the formation of the light emitting layer in Example 153.
An organic electroluminescence device was produced by the method described in 1. When a direct current voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, green light emission was confirmed.

[0343]

According to the present invention, it is possible to provide an organic electroluminescent device having excellent emission brightness. Furthermore, it has become possible to provide a hydrocarbon compound suitable for the light emitting device.

[Brief description of drawings]

FIG. 1 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 2 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 3 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 4 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 5 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 6 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 7 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 8 is a schematic structural diagram of an example of an organic electroluminescent device.

[Description of Reference Signs] 1: Substrate 2: Anode 3: Hole injection / transport layer 4: Light emitting layer 4 ′: Light emitting layer (layer in which light emitting component and hole injection / transporting component are mixed) 4 ″: Light emitting layer (light emitting component and Layer in which electron injecting and transporting component is mixed) 4 ''': Light emitting layer (layer in which light emitting component, hole injecting and transporting component and electron injecting and transporting component are mixed) 5: Electron injecting and transporting layer 6: Cathode 7: Power supply

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁷ Identification code FI theme code (reference) C09K 11/06 645 C09K 11/06 645 655 655 660 660 660 690 690 H05B 33/14 H05B 33/14 B 33 / 22 33/22 D (72) Inventor Yoshiyuki Toya 580-32, Nagaura, Sodegaura, Chiba Prefecture Mitsui Chemicals Co., Ltd. (72) Masakatsu Nakatsuka, 580-32, Nagaura, Sodegaura, Chiba Mitsui Chemicals Co., Ltd. F Term (Reference) 3K007 AB02 AB03 DB03 4C036 AA02 AA11 AA14 AA17 4C056 AA02 AB01 AC03 AD05 AE03 EA01 EB01 EC02 EC12 4C063 AA01 BB06 CC16 DD08 EE10 4C204 BB05 BB09 CB25 EB01 FB07 FB16 GB01 GB02

Claims (14)

[Claims] 1. A hydrocarbon compound in which an anthracene ring and a fluorene ring each having at least one group represented by formula (I) as a substituent are directly bonded. [Chemical 1] (In the formula, Ar ₁ and Ar ₂ represent a substituted or unsubstituted arylene group, and Z represents a linking group.) 2. The hydrocarbon compound according to claim 1, wherein the fluorene ring is bonded at a position other than the 9-position. 3. A hydrocarbon compound represented by the general formula (1). _{X 1 - (F 1) j} - (A 1) k - (F 2) l - (A 2) m - (F 3) n -X 2 (1) [ wherein, A ₁ and A ₂ are each independently Represents a substituted or unsubstituted anthracene diyl group, and is represented by F ₁ , F ₂ and F
₃ independently represents a substituted or unsubstituted fluorenediyl group, X ₁ and X ₂ each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic Represents an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted amino group, or a group represented by the general formula (I): (In the formula, Ar ₁ and Ar ₂ represent a substituted or unsubstituted arylene group, Z represents a linking group.) J, m and n represent 0 or 1, k and l represent 1 or 2, When k is 2, A _{1 s} may be the same or different, and when l is 2, F 2 s may be the same or different, provided that at least one of X ₁ and X ₂ is It is a group represented by the general formula (I). ] 4. A hydrocarbon compound represented by the general formula (2) [Chemical 3] [Where R_{twenty one}And R_{twenty two}Are each independently a hydrogen atom,
Linear, branched or cyclic alkyl group, substituted or unsubstituted
Aryl groups, or substituted or unsubstituted aralkyl
Represents a group, X₂₀₁~ X₂₂₄Are each independently a hydrogen atom,
Halogen atom, straight chain, branched or cyclic alkyl group, direct
Chain, branched or cyclic alkoxy group, substituted or unsubstituted
An aryl group, a substituted or unsubstituted amino group, or
Represents a group represented by the general formula (I), [Chemical 4] (In the formula, Ar₁And Ar₂Is a substituted or unsubstituted ally
Represents a len group, and Z represents a linking group. ) X₂₀₁~ X₂₂₄At least one of is represented by the general formula (I)
Represents a group represented by However, R _{twenty one}, R_{twenty two}And X₂₀₁~ X₂₂₄Is
It is not an anthryl or fluorenyl group. ] 5. A hydrocarbon compound represented by the general formula (3):
object. [Chemical 5] [Where R₃₁~ R₃₄Are each independently a hydrogen atom,
Chain, branched or cyclic alkyl group, substituted or unsubstituted
Aryl group or substituted or unsubstituted aralkyl group
Represents X₃₀₁~ X₃₂₂Are each independently a hydrogen atom,
Rogen atom, straight chain, branched or cyclic alkyl group, straight chain
Chain, branched or cyclic alkoxy group, substituted or unsubstituted
An aryl group, a substituted or unsubstituted amino group, or
Represents a group represented by the general formula (I), [Chemical 6] (In the formula, Ar₁And Ar₂Is a substituted or unsubstituted ally
Represents a len group, and Z represents a linking group. ) X₃₀₁~ X₃₂₂At least one of is represented by the general formula (I)
Represents a group represented by However, R ₃₁~ R₃₄And X₃₀₁~ X₃₂₂Is
It is not an anthryl or fluorenyl group. ] 6. A hydrocarbon compound represented by the general formula (4):
object. [Chemical 7] [Where R₄₁And R₄₂Are each independently a hydrogen atom,
Linear, branched or cyclic alkyl group, substituted or unsubstituted
Aryl groups, or substituted or unsubstituted aralkyl
Represents a group, X₄₀₁~ X₄₁₆Are each independently a hydrogen atom,
Halogen atom, straight chain, branched or cyclic alkyl group, direct
Chain, branched or cyclic alkoxy group, substituted or unsubstituted
An aryl group, a substituted or unsubstituted amino group, or
Represents a group represented by the general formula (I), [Chemical 8] (In the formula, Ar₁And Ar₂Is a substituted or unsubstituted ally
Represents a len group, and Z represents a linking group. ) X₄₀₁~ X₄₁₆At least one of is represented by the general formula (I)
Represents a group represented by However, R ₄₁, R₄₂And X₄₀₁~ X₄₁₆Is
It is not an anthryl or fluorenyl group. ] 7. The material for an organic electroluminescence device according to claim 1. 8. An organic electroluminescence device comprising at least one layer containing at least one kind of the material for organic electroluminescence device according to claim 7 between a pair of electrodes. 9. The organic electroluminescent device according to claim 8, wherein the layer containing the material for organic electroluminescent device according to claim 7 is a light emitting layer. 10. The organic electroluminescent device according to claim 8, wherein the layer containing the material for organic electroluminescent device according to claim 7 further contains a luminescent organometallic complex. 11. The organic electroluminescent device according to claim 8, wherein the layer containing the material for organic electroluminescent device according to claim 7 further contains a triarylamine derivative. 12. The organic electroluminescent device according to claim 8, wherein the layer containing the material for organic electroluminescent device according to claim 7 is a hole injecting and transporting layer. 13. The organic electroluminescent device according to claim 8, further comprising a hole injecting and transporting layer between the pair of electrodes. 14. The organic electroluminescence device according to claim 8, further comprising an electron injecting and transporting layer between the pair of electrodes.