JP2000008033A - Organic electroluminescent element material and organic electroluminescent element using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a light emission element capable of emitting a light by converting an electric energy to a light, providing luminescence properties, suitable for a display element, a display, a backlight, electrophotography, a lighting source, an indicator, a signboard, etc., comprising a specific compound. SOLUTION: This organic electroluminescent element material comprises a compound of formula I (R11 is H or a substituent group; R12 is H, a cation or a substituent group; Q11 and Q12 are each an atomic group necessary for forming a five-membered or six-membered ring and at least one of Q11 and Q12 is an atomic group for forming a six-membered ring) or formula II (R21 is H or a substituent group; R22 is H, a cation or a substituent group; X1 and X2 are each O, S, Se or the like; Q21 and Q22 are each an atomic group necessary for forming a five-membered ring) and is preferably usable in the field of an interior, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a material for a light emitting device (organic electroluminescence (EL) device) and a light emitting device which can emit light by converting electric energy into light, and relates to a display device, a display, a backlight, an electrophotograph, The present invention relates to a light emitting element that can be suitably used in fields such as an illumination light source, a sign, a signboard, and interior.

[0002]

2. Description of the Related Art At present, research and development on various display elements are active, and among them, organic EL elements are attracting attention as promising display elements because they can obtain high-luminance light emission at low voltage. For example, an EL element that forms an organic thin film by vapor deposition of an organic compound is known (Applied
Physics Letters, 51, 913, 1987
Year). The organic EL device described has a laminated structure of an electron transporting material and a hole transporting material, and its light emitting characteristics are greatly improved as compared with a conventional single layer type device.

[0003] As a means for improving the luminous efficiency of the stacked EL device, a method of doping a fluorescent dye is known. For example, Journal of Applied Physics 6
5, pp. 3610, 1989, the organic EL device doped with a coumarin dye has significantly improved luminous efficiency as compared with an undoped device. In this case, light of a desired wavelength can be extracted by changing the type of fluorescent compound to be used, but there are few compounds that emit blue or red light with high efficiency and have excellent durability.

Conventionally known blue light emitting materials include:
For example, condensed polycyclic aromatic compounds such as anthracene, pyrene, and perylene (for example, J. Chem. Phys., 44,
2902 (1966), Thin. Solid. Fil
ms, 99, 171 (1982)), tetraphenylbutadiene-based compounds (for example, JP-A-59-194).
No. 393), distyrylbenzene compounds (for example, European Patent Nos. 281381 and 398881).
No. 373582, U.S. Pat. No. 4,672,265,
No. 4725531, No. 4734338, No. 4741
Nos. 976 and 4776320, JP-A-61-3789.
No. 0, JP-A-1-245087 and JP-A-2-247277
No. 2-247278, No. 2-209988, No. 3-33184, No. 3-84089, No. 3-231
No. 970, No. 4-117485, No. 4-275268
And stilbene-based compounds (for example, JP-A-2-235).
No. 983, No. 3-47890, etc.), polyphenyl compounds (for example, compounds described in JP-A-3-33183, etc.), and polycarbonate compounds containing an aromatic tertiary amine skeleton as a repeating unit (for example, Compounds described in Japanese Unexamined Patent Application Publication No. 5-247559, metal complexes having a tropolone skeleton (for example, compounds described in Japanese Unexamined Patent Application Publication No. 9-157624), 2- (o-hydroxyphenyl) -benzoxazole derivatives or 2- (o-hydroxy Metal complexes having a phenyl) -benzthiazole derivative as a ligand (for example, JP-A-7-133483, JP-A-8-113)
No. 576, No. 8-301877, No. 8-306489
And the like, but these compounds have low luminous efficiency, have a problem in durability,
There were problems such as poor color purity and the like, and it was not practical.

In addition, the conventional organic EL device generally has a wide emission spectrum, and therefore, when reproducing a full-color image by emitting blue, green, and red light, the spectrum is superimposed to cause a problem in color reproduction. there were. In addition, in obtaining blue, green, and red using a color filter, there is a problem that the use efficiency of light emission is reduced due to the presence of spectral components of unused light. As a solution to such a problem, for example, a pyrromethene-BF ₂ complex (for example, JP-A Nos. 9-208946 and 9-28908).
No. 1) and materials having a narrow emission spectrum such as an acetylacetonate derivative-Eu ³⁺ complex are disclosed.
However, when the former compound is used, only green to red light emission is possible, and in the latter case, only red light emission is possible, and both compound groups have a problem that the emission luminance is low. Furthermore, although these function as dope materials,
Since there is almost no host function as an electron transporting material, and a device manufacturing process which is complicated and has poor reproducibility is required, development of a material having both an electron transporting function and a light emitting function has been desired.

On the other hand, an organic EL device that achieves high-luminance light emission is a device in which organic substances are stacked by vacuum deposition. However, from the viewpoints of simplification of the manufacturing process, workability, large area, and the like. It is desirable to produce the element by a coating method.
However, a device manufactured by a conventional coating method is inferior to a device manufactured by a vapor deposition method in terms of luminous luminance and luminous efficiency, and high luminance and highly efficient luminescence have been major issues.

[0007]

SUMMARY OF THE INVENTION It is a first object of the present invention to provide an organic EL device having a narrow emission spectrum width and high color purity.
An object of the present invention is to provide a material for an L element and an organic EL element. A second object is to provide a material for an organic EL device and an organic EL device which can emit light with high luminance and high efficiency by driving at a low voltage and have excellent stability when used repeatedly.

[0008]

This object has been achieved by the following means. (1) An organic electroluminescent device material, which is a compound represented by the following general formula (I).

[0009]

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(Wherein, R ₁₁ represents a hydrogen atom or a substituent; R ₁₂ represents a hydrogen atom, a cation or a substituent. Q ₁₁ and Q ₁₂ are each a 5- or 6-membered ring. It represents a necessary atom group, provided that at least one of Q ₁₁ and Q ₁₂ represents an atom group forming a 6-membered ring.) (2) It is a compound represented by the following general formula (II) Organic electroluminescent element material.

[0011]

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(Wherein, R ₂₁ represents a hydrogen atom or a substituent; R ₂₂ represents a hydrogen atom, a cation or a substituent; X ₁ and X ₂ each represent an oxygen atom, a sulfur atom, a selenium atom, a CR _{x1 (R x2), NR x3} (R x1, R x2, R x3 each represent. a hydrogen atom or a substituent group) .Q ₂₁
And Q ₂₂ each represent an atom group necessary to form a 5-membered ring. (3) An organic electroluminescent device material, which is a complex formed from the compound represented by the general formula (I) in (1). (4) An organic electroluminescent device material, which is a complex formed from the compound represented by the general formula (II) in (2). (5) An organic electroluminescent device material, wherein the complex according to (3) or (4) contains a divalent or trivalent metal ion. (6) The metal ion of the complex in (5) is Be ²⁺ , Mg
²⁺ , Al ³⁺ , Ga ³⁺ , Zn ²⁺ , Cu ²⁺ , Co ²⁺ , C
An organic electroluminescent device material comprising e ³⁺ , Eu ³⁺ , Eu ²⁺ , and Tb ³⁺ . (7) In an organic electroluminescence element in which a light emitting layer or a plurality of organic compound thin films including the light emitting layer are formed between a pair of electrodes, at least one layer contains the organic electroluminescence element material according to (1) to (6). An organic electroluminescent device, characterized in that: (8) In an organic electroluminescence device in which a light emitting layer or a plurality of organic compound thin films including a light emitting layer are formed between a pair of electrodes, at least one layer is coated with the organic electroluminescence device material according to (1) to (6). An organic electroluminescence device characterized by being a layer formed by the following. (9) In an organic electroluminescence device in which a light emitting layer or a plurality of organic compound thin films including a light emitting layer are formed between a pair of electrodes, at least one layer of the organic electroluminescence device material described in (1) to (6) is dispersed in a polymer. An organic electroluminescence device, characterized in that it is a layer formed.

[0013]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail. First, the compound represented by formula (I) will be described. R ₁₁ represents a hydrogen atom or a substituent. As the substituent, for example, an alkyl group (preferably having 1 to 2 carbon atoms)
0, more preferably 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms, for example, methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, Cyclopentyl, cyclohexyl and the like can be mentioned. ), An alkenyl group (preferably having 2 to 20 carbon atoms, more preferably having 2 to 12 carbon atoms, particularly preferably having 2 to 8 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl, and 3-pentenyl. ), Alkynyl group (preferably having 2 to 2 carbon atoms)
20, more preferably 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, such as propargyl and 3-pentynyl. ), An aryl group (preferably having 6 to 30 carbon atoms, more preferably having 6 to 20 carbon atoms, particularly preferably having 6 to 12 carbon atoms, for example, phenyl, p-
Methylphenyl, naphthyl and the like can be mentioned. ), An amino group (preferably having 0 to 20 carbon atoms, more preferably 0 to 10 carbon atoms, particularly preferably 0 to 6 carbon atoms, and examples thereof include amino, methylamino, dimethylamino, diethylamino, and dibenzylamino. ), An alkoxy group (preferably having 1 to 20 carbon atoms, more preferably having 1 to 12 carbon atoms, particularly preferably having 1 to 8 carbon atoms, and examples thereof include methoxy, ethoxy, and butoxy), and aryloxy. Group (preferably having 6 to 2 carbon atoms)
It has 0, more preferably 6 to 16 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples include phenyloxy and 2-naphthyloxy. ), An acyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, for example, acetyl,
Benzoyl, formyl, pivaloyl and the like can be mentioned. ), An alkoxycarbonyl group (preferably having 2 carbon atoms)
-20, more preferably 2-16 carbon atoms, particularly preferably 2-12 carbon atoms, for example, methoxycarbonyl,
Ethoxycarbonyl and the like. ), An aryloxycarbonyl group (preferably having 7 to 20 carbon atoms, more preferably having 7 to 16 carbon atoms, and particularly preferably having 7 to 1 carbon atoms.
0, for example, phenyloxycarbonyl and the like. ), An acyloxy group (preferably having 2 to 2 carbon atoms)
It has 0, more preferably 2 to 16 carbon atoms, and particularly preferably 2 to 10 carbon atoms, and examples thereof include acetoxy and benzoyloxy. ), An acylamino group (preferably having 2 to 20 carbon atoms, more preferably having 2 to 16 carbon atoms, particularly preferably having 2 to 10 carbon atoms, and examples thereof include acetylamino and benzoylamino), and an alkoxycarbonylamino group. (Preferably having 2 to 20 carbon atoms,
More preferably, it has 2 to 16 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino. ), An aryloxycarbonylamino group (preferably having 7 to 20 carbon atoms, more preferably having 7 carbon atoms)
To 16, particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonylamino. ), A sulfonylamino group (preferably having 1 to 2 carbon atoms)
0, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, for example, methanesulfonylamino,
Benzenesulfonylamino and the like. ), A sulfamoyl group (preferably having 0 to 20, more preferably 0 to 16, and particularly preferably 0 to 12 carbon atoms, for example, sulfamoyl, methylsulfamoyl,
Dimethylsulfamoyl, phenylsulfamoyl and the like can be mentioned. ), A carbamoyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include carbamoyl, methylcarbamoyl, diethylcarbamoyl, and phenylcarbamoyl). An alkylthio group (preferably having 1 to 20 carbon atoms, more preferably having 1 to 1 carbon atoms)
6, particularly preferably 1 to 12 carbon atoms, for example, methylthio, ethylthio and the like. ), An arylthio group (preferably having 6 to 20 carbon atoms, more preferably 6 to 16 carbon atoms, particularly preferably having 6 to 12 carbon atoms, such as phenylthio, etc.), and a sulfonyl group (preferably having 1 carbon atom). ~ 20, more preferably 1 carbon atom
To 16, particularly preferably 1 to 12 carbon atoms, such as mesyl and tosyl. ), A sulfinyl group (preferably having 1 to 20 carbon atoms, more preferably 1 carbon atom)
To 16, particularly preferably 1 to 12 carbon atoms, for example, methanesulfinyl, benzenesulfinyl and the like. ), Ureido group (preferably having 1 to 20 carbon atoms,
More preferably, it has 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include ureide, methylureide, and phenylureide. ), A phosphoric amide group (preferably having 1 to 20 carbon atoms, more preferably having 1 carbon atom)
To 16, particularly preferably 1 to 12 carbon atoms, for example, diethylphosphoramide, phenylphosphoramide and the like. ), Hydroxy, mercapto, halogen (eg, fluorine, chlorine, bromine, iodine), cyano, sulfo, carboxyl, nitro, hydroxamic acid, sulfino, hydrazino,
An imino group, a heterocyclic group (preferably having 1 to 20 carbon atoms, more preferably having 1 to 12 carbon atoms, and examples of the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom, specifically, for example, imidazolyl, pyridyl, Frills, piperidyl,
Examples include morpholino, benzoxazolyl, benzimidazolyl, benzothiazolyl and the like. ). These substituents may be further substituted. When there are two or more substituents, they may be the same or different. If possible, the rings may be linked.

The substituent is preferably an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, an acylamino group, an alkoxy group. Carbonylamino group, aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio group, arylthio group, sulfonyl group, sulfinyl group, ureido group, phosphoric amide group, halogen atom, cyano group, carboxyl group, nitro Group, a heterocyclic group,
More preferably an alkyl group, an alkenyl group, an aryl group, a halogen atom, a cyano group, a heterocyclic group, still more preferably an alkyl group, an aryl group, a cyano group, an aromatic heterocyclic group, particularly preferably an alkyl group, An aryl group and a cyano group.

R ₁₁ is preferably a hydrogen atom, an alkyl group (more preferably an alkyl group having 1 to 20, more preferably 1 to 12 carbon atoms, particularly preferably an alkyl group having 1 to 6 carbon atoms) and an aryl group (more preferably 1 to 6 carbon atoms). Preferably C6-30,
More preferably, it is an aryl group having 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, a cyano group, or an aromatic heterocyclic group (more preferably, a 5- or 6-membered aromatic heterocyclic ring).
It is.

R ₁₂ represents a hydrogen atom, a cation or a substituent. The cation may be an organic cation or an inorganic cation, for example, an alkali metal ion (eg, Li ⁺ , Na ⁺ , K ⁺ , Cs ⁺ ), an alkaline earth metal ion (eg, Be ²⁺ , Mg ²⁺ , Ca ^{2) +,} Etc.), ammonium (eg, ammonium, tetraethylammonium, etc.), phosphonium (eg, tetrabutylphosphonium, etc.) and the like. As the substituent represented by R ₁₂ , for example, those exemplified as the substituent of R ₁₁ can be applied, and preferred substituents are also the same. R ₁₂ is preferably a hydrogen atom, a cation or an alkyl group (more preferably 1 to 20 carbon atoms, still more preferably 1 to 1 carbon atoms).
2, particularly preferably an alkyl group having 1 to 6 carbon atoms), an aryl group (more preferably 6 to 30 carbon atoms, further preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms), and cyano. And an aromatic heterocyclic group (more preferably a 5- or 6-membered aromatic heterocyclic ring), more preferably a hydrogen atom.

R₁₁, R₁₂Preferably, R is a combination of
₁₁, R₁₂Are both hydrogen atoms, R ₁₁Is an alkyl group and R
₁₂Is a hydrogen atom, R₁₁Is an aryl group and R₁₂Is a hydrogen source
R for child₁₁Is a cyano group and R₁₂Is a hydrogen atom, R
₁₁Is an aromatic heterocyclic group and R₁₂Is a hydrogen atom,
More preferably, R₁₁, R₁₂Are both hydrogen atoms, R ₁₁
Is a cyano group and R₁₂Is a hydrogen atom.

Q ₁₁ and Q ₁₂ each represent an atom group necessary to form a 5- or 6-membered ring. However, Q ₁₁ and Q ₁₂
At least one of them represents an atomic group forming a 6-membered ring. In these 6-membered rings, a benzene ring, a naphthalene ring or the like may be condensed. 5 members or 6 formed by Q ₁₁ and Q ₁₂
As the member ring, for example, pyrrole, imidazoline, imidazole, benzimidazole, naphthimidazole,
Thiazoline, thiazole, benzthiazole, naphthothiazole, isothiazole, oxazoline, oxazole, benzoxazole, naphthoxazole, isoxazole, selenazoline, selenazole, benzselenazole, naphthoselenazole, indole, isoindole, indolenine, pyrazole, indazole, Pyridine, quinoline, isoquinoline, pyrazine, pyrimidine, pyridazine, purine, phthalazine, naphthyridine,
Quinoxaline, quinazoline, cinnoline, pteridine,
Carboline, phenanthridine, pteridine, phenanthroline, perimidine, tetrazaindene and the like, preferably pyridine, quinoline, isoquinoline, pyrazine, pyrimidine, pyridazine, purine, phthalazine, naphthyridine, quinoxaline, quinazoline,
More preferred are pyridine and quinoline. Q ₁₁ , Q ₁₂
The 5- or 6-membered ring formed by may have a substituent, and examples of the substituent include those described as the substituent of R ₁₁ . Among the compounds represented by the general formula (I), a compound represented by the general formula (Ia) is preferable.

[0019]

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(Wherein, R ₁₁ has the same meaning as that in formula (I), and the preferred range is also the same.
_11a and Q _12a each represent an atomic group forming a pyridine ring or a quinoline ring. The pyridine ring and quinoline ring formed by Q _11a and Q _12a may have a substituent, and examples of the substituent include those described as the substituent of R ₁₁ . Next, the compound represented by formula (II) will be described. R ₂₁ represents a hydrogen atom or a substituent. As the substituent, for example, those exemplified as the substituent for R ₁₁ in formula (I) can be applied. R ₂₁ is preferably a hydrogen atom or an alkyl group (more preferably 1 to 20 carbon atoms, still more preferably 1 to 12 carbon atoms, particularly preferably 1 to 12 carbon atoms).
To 6), an aryl group (more preferably 6 to 30 carbon atoms, still more preferably 6 to 20 carbon atoms, particularly preferably an aryl group having 6 to 12 carbon atoms), a cyano group, and an aromatic heterocyclic group ( More preferably, it is a 5- or 6-membered aromatic heterocycle).

R ₂₂ represents a hydrogen atom, a cation or a substituent. The cation may be an organic cation or an inorganic cation, for example, an alkali metal ion (eg, Li ⁺ , Na ⁺ , K ⁺ , Cs ⁺ ), an alkaline earth metal ion (eg, Be ²⁺ , Mg ²⁺ , Ca ^{2) +,} Etc.), ammonium (eg, ammonium, tetraethylammonium, etc.), phosphonium (eg, tetrabutylphosphonium, etc.) and the like. The substituent represented by R _22, for example, the general formula can be applied those described as the substituent groups for R ₁₁ in (I), also preferred substituents are also the same. R ₂₂ is preferably a hydrogen atom, a cation,
An alkyl group (more preferably an alkyl group having 1 to 20 carbon atoms, further preferably an alkyl group having 1 to 12 carbon atoms, particularly preferably 1 to 6 carbon atoms) and an aryl group (more preferably 6 to 20 carbon atoms)
30, more preferably an aryl group having 6 to 20 carbon atoms, particularly preferably an aryl group having 6 to 12 carbon atoms, a cyano group, or an aromatic heterocyclic group (more preferably a 5- or 6-membered aromatic heterocyclic ring). And more preferably a hydrogen atom.

R_{twenty one}, R_{twenty two}Preferably, R is a combination of
_{twenty one}, R_{twenty two}Are both hydrogen atoms, R _{twenty one}Is an alkyl group and R
_{twenty two}Is a hydrogen atom, R_{twenty one}Is an aryl group and R_{twenty two}Is a hydrogen source
R for child_{twenty one}Is a cyano group and R_{twenty two}Is a hydrogen atom, R
_{twenty one}Is an aromatic heterocyclic group and R_{twenty two}Is a hydrogen atom,
More preferably, R_{twenty one}, R_{twenty two}Are both hydrogen atoms, R _{twenty one}
Is a cyano group and R_{twenty two}Is a hydrogen atom.

X ₁ and X ₂ are an oxygen atom, a sulfur atom, a selenium atom, CR _x1 (R _x2 ), NR _x3 (R _x1 ,
R _x2 and R _x3 each represent a hydrogen atom or a substituent. )
Represents As the substituents represented by R _x1 , R _x2 and R _x3 , for example, those mentioned as the substituents of R ₁₁ in the general formula (I) can be applied. R _x1 and R _x2 are preferably a hydrogen atom or an alkyl group (more preferably 1 to 20 carbon atoms, still more preferably 1 to 12 carbon atoms, particularly preferably 1 to 12 carbon atoms).
An alkyl group having 6 carbon atoms), an aryl group (more preferably 6 to 30 carbon atoms, further preferably 6 to 20 carbon atoms, particularly preferably an aryl group having 6 to 12 carbon atoms), and an aromatic heterocyclic group (more preferably 5 Or 6-membered aromatic heterocycle)
And more preferably a hydrogen atom or an alkyl group,
More preferred are lower alkyl groups having 1 to 6 carbon atoms, and particularly preferred are methyl and ethyl. Preferably, R _x3 is a hydrogen atom, an alkyl group (more preferably an alkyl group having 1 to 20, more preferably 1 to 12, and particularly preferably 1 to 6 carbon atoms), an aryl group (more preferably an alkyl group having 1 to 6 carbon atoms). 6-30, more preferably 6-C
20, particularly preferably an aryl group having 6 to 12 carbon atoms),
An aromatic heterocyclic group (more preferably a 5- or 6-membered aromatic heterocyclic ring), more preferably a hydrogen atom or an alkyl group, even more preferably a lower alkyl group having 1 to 6 carbon atoms, Particularly preferred are methyl and ethyl. X ₁ and X ₂ are preferably an oxygen atom, a sulfur atom, C
R _x1 (R _x2 ) and NR _x3 , more preferably an oxygen atom, a sulfur atom and NR _x3 .

Q ₂₁ and Q ₂₂ each represent an atom group necessary for forming a 5-membered ring. These five-membered rings may be condensed with a benzene ring, a naphthalene ring or the like. Q _21, Q ₂₂
May be either a single ring or a condensed ring, for example, imidazoline, imidazole, benzimidazole, naphthimidazole, thiazoline, thiazole, benzothiazole, naphthothiazole, isothiazole, oxazoline, oxazole, benzoxazole , Naphthoxazole, isoxazole, selenazoline, selenazole, benzoselenazole, naphthoselenazole, indole, indolenine, pyrazole, indazole, purine, tetrazaindene, triazole, tetrazole, oxadiazole, thiadiazole, and the like, preferably Imidazole, benzimidazole, naphthoimidazole, thiazole, benzthiazole, naphthothiazole, oxazole, benzoxazole, na Tookisazoru or an indolenine, more preferably benzimidazole, naphthoimidazole, benzthiazole, naphthothiazole, benzoxazole, naphthoxazole, an indolenine.

Of the compounds represented by the general formula (II), a compound represented by the general formula (II-a) is preferable.

[0026]

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(Wherein, R ₂₁ , X ₁ and X ₂ have the same meanings as those in formula (II), and the preferred ranges are also the same.) R ₂₃ , R ₂₄ , R ₂₅ and R ₂₆ Examples of the substituent represented by .R ₂₃ to R ₂₆ each represent a hydrogen atom or a substituent, for example, can be applied, those exemplified as the substituent for R ₁₁ in the general formula _{(I) .R 23, R 24} , R
₂₅ and R ₂₆ are preferably a hydrogen atom, R ₂₃ and R ₂₄ , R ₂₅
And R ₂₆ are linked to form a condensed ring (for example, benzene, naphthalene, anthracene, imidazoline, imidazole, benzimidazole, naphthimidazole, thiazolidine,
Thiazole, benzothiazole, naphthothiazole, isothiazole, oxazoline, oxazole, benzoxazole, naphthoxazole, isoxazole,
Selenazole, benzselenazole, naphthoselenazole, pyridine, quinoline, isoquinoline, indole,
Isoindole, indolenine, pyrazole, pyrazine, pyrimidine, pyridazine, indazole, purine,
Phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, phenanthridine, pteridine, phenanthroline, tetrazaindene, etc.), more preferably a hydrogen atom, R ₂₃ and R ₂₄ , R ₂₅ and R ₂₆ It is a compound in which a condensed aromatic ring is formed by linking, and more preferably a compound in which R ₂₃ and R ₂₄ and R ₂₅ and R ₂₆ are linked to form a benzene ring and a naphthalene ring. )

Among the compounds represented by the general formula (II), more preferred are the compounds represented by the general formula (II-b).

[0029]

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(Wherein, R ₂₁ , X ₁ , and X ₂ have the same meanings as those in formula (II), and the preferred ranges are also the same. R _b1 and R _b2 each represent a substituent.) the substituent represented by .R _b1, R _b2, can be applied, for example those in the general formula (I) exemplified as the substituents represented by R _11, and preferred ranges are also the same .n ₁ and n ₂ Represents an integer of 0 to 4, and n ₁ and n ₂ are 2
For more, R _b1, R _{b 2} may form a ring in the case may be the same or different from each other and can be. )

The compounds represented by the general formulas (I) and (II) may be low molecular weight compounds,
It may be a high molecular weight compound in which the residue represented by (II) is connected to the polymer main chain, or a high molecular weight compound having a skeleton of the general formula (I) or (II) in the main chain. In the case of a high molecular weight compound, it may be a homopolymer or a copolymer with another monomer. Further, the general formulas (I) and (II) are represented by a limit structural formula for convenience,
It may be its tautomer.

Specific examples of the compounds represented by formulas (I) and (II) of the present invention are shown below, but the present invention is not limited to these.

[0033]

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[0034]

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[0035]

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[0036]

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[0037]

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[0038]

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The metal ion of the complex formed from the compounds represented by formulas (I) and (II) is preferably a divalent or trivalent cation, more preferably Be ²⁺ , M 2
g ²⁺ , Al ³⁺ , Ga ³⁺ , Zn ²⁺ , Cu ²⁺ , Co ²⁺ , Ce
³⁺ , Eu ³⁺ , Eu ²⁺ , Tb ³⁺ , and more preferably A
l ³⁺ and Zn ²⁺ , and particularly preferably Zn ²⁺ . Hereinafter, specific examples of the complex having the compounds represented by formulas (I) and (II) of the present invention as ligands are shown, but the present invention is not limited thereto.

[0040]

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[0041]

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[0042]

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[0043]

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[0044]

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[0045]

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[0046]

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[0047]

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[0048]

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[0049]

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[0050]

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The complex formed from the compounds represented by formulas (I) and (II) and formulas (I) and (II) of the present invention can be synthesized by various methods.
nal of Organic Chemistry,
vol 54,786 (1988), vol.
436 (1998), Inorganic Chem.
issue, vol 35, 3 (1996), Jour
nal of Organometallic Che
mystry, vol 489, 107 (1995),
Journal of Physics, vol99,
6421 (1993), Journal of the
e Chemical Society, Dalton
Transactions, 16, 2457 (199)
2 years), Inorganica Chimica Ac
ta, vol 174, 169 (1990), Tran
site Metal Chemistry, vo
113,423 (1988), Journal of
the Chemical Society, Che
medical Communication, 490 (1
986), Analytica Chemical A
cta, vol 44, 115 (1969) and the like. The metal complex of the present invention can be synthesized from the compounds represented by the general formulas (I) and (II) and various metals or metal salts. The metal salt is not particularly limited, but a nitrate, a halogen salt such as a hydrochloride, a sulfate,
A carboxylate such as an acetate, a phosphonate, a sulfonate, a hydroxide, an alkoxide and the like are suitably used, and a nitrate, a hydrochloride, a sulfate, and an acetate are preferable. The molar ratio of the compounds represented by the general formulas (I) and (II) and the metal salt used in synthesizing the metal complex is appropriately selected according to the complex to be synthesized. ),
The compound represented by formula (II) is 0.1 to 10 moles, preferably 0.5 to 8 moles, and more preferably 0.5 to 6 moles. In addition, a base can be used in the synthesis of the complex. As the base, various inorganic or organic bases can be used. For example, metal hydroxides (eg, sodium hydroxide, potassium hydroxide, etc.), metal carbonates (eg, sodium carbonate, potassium carbonate, etc.), metal bicarbonates (Eg, sodium hydrogencarbonate, potassium hydrogencarbonate, etc.) and organic bases (eg, triethylamine, sodium alkoxide, etc.) are preferred. The amount of the base to be used is not particularly limited, but is preferably a compound represented by the general formula (I):
The amount is 0.01 to 30 equivalents, more preferably 1 to 10 equivalents, relative to the compound represented by (II). When synthesizing the metal complex, a solvent may be used. The solvent is not particularly limited, but may be water, alcohols (eg, methanol,
Ethanol, 2-propanol, etc., esters (eg, ethyl acetate, etc.), ethers (eg, diethyl ether, tetrahydrofuran, 1,4-dioxane, etc.), amides (eg, dimethylformamide, dimethylacetamide, etc.), nitriles (eg, Acetonitrile, etc.), ketones (eg, acetone, cyclohexanone, etc.), hydrocarbons (eg, hexane, benzene,
For example, toluene (eg, toluene), halogenated hydrocarbons (eg, dichloromethane, chloroform, 1,2-dichloroethane), and carboxylic acids (eg, acetic acid) can be used. Further, these solvents may be mixed and used. As a solvent preferably alcohols, ethers,
Ketones, more preferably alcohols,
Particularly preferred are methanol, ethanol and 2-propanol. The reaction temperature at the time of synthesizing the metal complex is not particularly limited, but is preferably 10 to 150 ° C., and preferably 1 to 150 ° C.
The temperature is 0 to 100 ° C, more preferably 10 to 80 ° C.

Hereinafter, the method for synthesizing the compound of the present invention will be described with reference to specific examples. Synthesis Example 1 Synthesis of Exemplified Compound II-2 25.0 g of 2-aminothiophenol (0.20 mo
1) and 17.2 g (0.10 mol) of diethyl malonate
And heated and stirred at 200 ° C. for 3 hours under a nitrogen atmosphere. After cooling to room temperature, the mixture was washed with ethyl acetate / saturated saline, and the organic layer was dried over anhydrous magnesium sulfate. After evaporating the solvent under reduced pressure, the residue was recrystallized from ethyl acetate / n-hexane to give 21.0 g of compound II-2 (0.
0745 mol). 75% yield

Synthesis Example 2 Synthesis of Exemplified Compound K-1 1.41 g (4.99 mmol) of Exemplified Compound II-2 was dissolved in 30 ml of methanol, and stirred at room temperature, and 1.1 ml of a 28% methanol solution of sodium methoxide (5. After adding 36 mmol), a solution of 0.55 g (2.51 mmol) of zinc acetate dihydrate in 7 ml of methanol was added dropwise. After stirring at room temperature for 1 hour, the precipitated solid was collected by filtration and recrystallized from chloroform / methanol to obtain 1.12 g (1.78 mmol) of Exemplified Compound K-1 as a yellow solid. 71% yield

The light-emitting device of the present invention is a device in which a light-emitting layer or a plurality of organic compound thin films including the light-emitting layer are formed between a pair of anode and cathode electrodes. , An electron injection layer, an electron transport layer, a protective layer, and the like, and each of these layers may have another function. Various materials can be used for forming each layer.

The anode supplies holes to the hole injection layer, the hole transport layer, the light emitting layer, etc., and may be made of a metal, an alloy, a metal oxide, an electrically conductive compound, or a mixture thereof. It is possible to use a material having a work function of 4 eV or more. Specific examples include conductive metal oxides such as tin oxide, zinc oxide, indium oxide, and indium tin oxide (ITO), or metals such as gold, silver, chromium, and nickel, and furthermore, these metals and conductive metal oxides. Mixtures or laminates, inorganic conductive substances such as copper iodide and copper sulfide, organic conductive materials such as polyaniline, polythiophene, and polypyrrole, and laminates of these with ITO, and the like. Oxides,
In particular, ITO is preferable in terms of productivity, high conductivity, transparency, and the like. The thickness of the anode can be appropriately selected depending on the material, but is usually preferably in the range of 10 nm to 5 μm, more preferably 50 nm to 1 μm, and still more preferably 100 nm to 500 nm.

As the anode, one having a layer formed on a soda lime glass, a non-alkali glass, a transparent resin substrate or the like is usually used. When glass is used, it is preferable to use non-alkali glass in order to reduce ions eluted from the glass. Further, when soda lime glass is used, it is preferable to use a glass coated with a barrier coat such as silica. The thickness of the substrate is not particularly limited as long as it is sufficient to maintain the mechanical strength. When glass is used, the thickness is usually 0.2 mm or more, preferably 0.7 mm or more. Various methods are used for manufacturing the anode depending on the material. For example, in the case of ITO, an electron beam method, a sputtering method, a resistance heating evaporation method, a chemical reaction method (such as a sol-gel method), and a dispersion of indium tin oxide are used. The film is formed by a method such as coating. The anode can be cleaned or otherwise treated to lower the device's drive voltage,
It is also possible to increase the luminous efficiency. For example, in the case of ITO, UV-ozone treatment or the like is effective.

The cathode supplies electrons to the electron injection layer, the electron transport layer, the light emitting layer, and the like. The cathode has an adhesive property between the negative electrode such as the electron injection layer, the electron transport layer, and the light emitting layer, an ionization potential, and the like. It is selected in consideration of stability and the like. As the material of the cathode, a metal, an alloy, a metal oxide, an electrically conductive compound, or a mixture thereof can be used, and specific examples thereof include an alkali metal (eg, Li, Na, K, etc.) or a fluoride thereof, and an alkaline earth metal. Metals such as Mg, Ca
Etc.) or its fluorides, gold, silver, lead, aluminum,
Sodium-potassium alloy or a mixed metal thereof, lithium-aluminum alloy or a mixed metal thereof, magnesium-silver alloy or a mixed metal thereof, indium, rare earth metals such as ytterbium, and the like, preferably having a work function of 4 eV or less. The material is more preferably aluminum, a lithium-aluminum alloy or a mixed metal thereof, a magnesium-silver alloy or a mixed metal thereof, or the like. The thickness of the cathode can be appropriately selected depending on the material, but is usually preferably in the range of 10 nm to 5 μm, more preferably 50 nm to 1 μm, and still more preferably 100 nm to 1 μm. A method such as an electron beam method, a sputtering method, a resistance heating evaporation method, or a coating method is used for manufacturing the cathode, and a metal can be evaporated alone or two or more components can be simultaneously evaporated. Further, an alloy electrode can be formed by depositing a plurality of metals at the same time, or an alloy prepared in advance may be deposited. The sheet resistance of the anode and the cathode is preferably low, and is preferably several hundred Ω / □ or less.

The material of the light emitting layer is capable of injecting holes from an anode or a hole injection layer or a hole transport layer when applying an electric field, and also injecting electrons from a cathode or an electron injection layer or an electron transport layer. Any material can be used as long as it can form a layer having a function, a function of transferring injected charges, and a function of providing a field of recombination of holes and electrons to emit light. Preferably, the light-emitting layer contains the compound of the present invention, but other light-emitting materials of the compound of the present invention can also be used. For example, benzoxazole derivatives,
Benzimidazole derivatives, benzothiazole derivatives,
Styrylbenzene derivatives, polyphenyl derivatives, diphenylbutadiene derivatives, tetraphenylbutadiene derivatives, naphthalimide derivatives, coumarin derivatives, perylene derivatives, perinone derivatives, oxadiazole derivatives, aldazine derivatives, pyrazine derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives, Quinacridone derivatives, pyrrolopyridine derivatives, thiadiazolopyridine derivatives, cyclopentadiene derivatives, styrylamine derivatives, aromatic dimethylidin compounds, various metal complexes represented by metal complexes of 8-quinolinol derivatives and rare earth complexes, polythiophene, polyphenylene, polyphenylene And polymer compounds such as vinylene. Although the thickness of the light emitting layer is not particularly limited, it is usually 1n.
m to 5 μm, more preferably 5 to 5 μm.
nm to 1 μm, more preferably 10 nm to 500
nm. The method for forming the light-emitting layer is not particularly limited, but a method such as resistance heating evaporation, electron beam, sputtering, molecular lamination, coating (spin coating, casting, dip coating, etc.), and LB method And preferably a resistance heating evaporation and coating method.

The material of the hole injection layer and the hole transport layer has any one of a function of injecting holes from the anode, a function of transporting holes, and a function of blocking electrons injected from the cathode. Anything should do. Specific examples thereof include carbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, and styryl anthracene derivatives , Fluorenone derivative, hydrazone derivative, stilbene derivative, silazane derivative, aromatic tertiary amine compound, styrylamine compound, aromatic dimethylidin compound, porphyrin compound, polysilane compound,
Examples thereof include poly (N-vinylcarbazole) derivatives, aniline-based copolymers, thiophene oligomers, and conductive polymer oligomers such as polythiophene. The thicknesses of the hole injection layer and the hole transport layer are not particularly limited, but are usually preferably in the range of 1 nm to 5 μm, more preferably 5 nm to 1 μm, and still more preferably 10 nm to 5 μm.
00 nm. The hole injection layer and the hole transport layer may have a single-layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions. Examples of the method for forming the hole injection layer and the hole transport layer include a vacuum deposition method, an LB method, and a method in which the hole injection / transport agent is dissolved or dispersed in a solvent and coated (spin coating method, casting method, dip coating method). Etc.) are used. In the case of the coating method, it can be dissolved or dispersed together with the resin component. Examples of the resin component include polyvinyl chloride, polycarbonate, polystyrene, polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, and poly (N -Vinyl carbazole), hydrocarbon resins, ketone resins, phenoxy resins, polyamides, ethyl cellulose, vinyl acetate, ABS resins, polyurethanes, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, silicone resins, and the like.

The material of the electron injecting layer and the electron transporting layer is not limited as long as it has a function of injecting electrons from the cathode, a function of transporting electrons, or a function of blocking holes injected from the anode. Good. Specific examples thereof include triazole derivatives, oxazole derivatives, oxadiazole derivatives,
Heterocyclic tetracarboxylic anhydrides such as fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, naphthalene perylene, and phthalocyanine derivatives And various metal complexes typified by metal complexes of 8-quinolinol derivatives, metal phthalocyanines, and metal complexes having benzoxazole or benzothiazole as ligands. The thickness of the electron injection layer and the electron transport layer is not particularly limited, but is usually 1 nm to 5 μm.
m, more preferably 5 nm to 1
μm, and more preferably 10 nm to 500 nm. The electron injection layer and the electron transport layer may have a single layer structure composed of one or more of the above-mentioned materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions. Examples of the method for forming the electron injection layer and the electron transport layer include a vacuum deposition method, an LB method, and a method in which the electron injection and transport agent is dissolved or dispersed in a solvent and coated (spin coating, casting, dip coating, and the like). Is used. In the case of the coating method, it can be dissolved or dispersed together with the resin component. As the resin component, for example, those exemplified in the case of the hole injection transport layer can be applied.

As the material of the protective layer, any material may be used as long as it has a function of preventing the element which promotes the deterioration of the element such as moisture and oxygen from entering the element. As a specific example,
In, Sn, Pb, Au, Cu, Ag, Al, Ti, N
metal such as i, MgO, SiO, SiO ₂ , Al ₂ O ₃ ,
GeO, NiO, CaO, BaO, Fe 2 O 3, Y 2 O
_3, a metal oxide such as TiO _2, MgF _2, LiF, Al
F ₃ , metal fluoride such as CaF ₂ , polyethylene, polypropylene, polymethyl methacrylate, polyimide,
Polyurea, polytetrafluoroethylene, polychlorotrifluoroethylene, polydichlorodifluoroethylene, copolymer of chlorotrifluoroethylene and dichlorodifluoroethylene, copolymerizing a monomer mixture containing tetrafluoroethylene and at least one comonomer Copolymer obtained, a fluorine-containing copolymer having a cyclic structure in the copolymer main chain, a water-absorbing substance having a water absorption of 1% or more,
A moisture-proof substance having a water absorption of 0.1% or less can be used. There is no particular limitation on the method for forming the protective layer. For example, a vacuum deposition method, a sputtering method, a reactive sputtering method,
BE (molecular beam epitaxy) method, cluster ion beam method, ion plating method, plasma polymerization method (high frequency excitation ion plating method), plasma CVD method, laser CVD method, thermal CVD method, gas source CVD method, coating method Applicable.

[0062]

EXAMPLES The present invention will be specifically described below with reference to examples.
However, the present invention is not limited thereto. Example 1 After etching and cleaning a glass substrate with ITO, copper phthalate
Nine-diphenyl-N, N-
(Α-naphthyl) -1,1-biphenyl-4,4-dia
Min, 35 nm, compounds shown in Table 1 at 50 nm, Tris
(8-quinolinolato) aluminum (III) to 10 nm
Vacuum deposition (8 × 10 ^-6~ 1 × 10^-Five
Torr). On top of this, a pattern of 5mm x 5mm
A mask that has been brushed, and add magnesium: silver = 10: 1
After co-evaporation of 250 nm, 300 nm of silver was evaporated (8
× 10^-6~ 1 × 10^-FiveTorr). Toyo Technica saw
Using a measure unit 2400, apply ITO
Pole, direct current constant voltage is applied to the EL element using Mg: Ag as the cathode.
And emits light, and the brightness is measured by the brightness meter BM-
8. Emission wavelength and chromaticity coordinates are specified by Hamamatsu Photonics.
The measurement was performed using a torque analyzer PMA-11. result
Are shown in Table 1.

[0063]

[Table 1]

[0064]

Embedded image

From the results shown in Table 1, it was found that the device using the compound of the present invention emitted blue light with high luminance and high color purity.

Example 2 40 mg of poly (N-vinylcarbazole), 1 mg of the compound shown in Table 2, and 12 mg of PBD (pt-butylphenylbiphenyloxadiazole) were dissolved in 3 ml of 1,2-dichloroethane and washed. Spin coating was performed on an ITO substrate. The film thickness at this time was about 120 nm. Then, a mask patterned to 5 mm × 5 mm was set, and magnesium: silver = 10: 1 was added to 250 mm in a vapor deposition apparatus.
After co-evaporation of silver, 300 nm of silver was evaporated (8 × 10
⁻⁶ to 1 × 10 ⁻⁵ Torr). This device was evaluated in the same manner as in Example 1. Table 2 shows the results.

[0067]

[Table 2]

From the above results, in the device using the compound of the present invention, good emission characteristics (emission luminance and hue) can be obtained even in a coating method in which the emission luminance is usually low, and the device is particularly excellent in blue purity. An element was obtained.

[0069]

According to the present invention, organic E having excellent blue purity can be obtained.
An L element is obtained. In particular, good light-emitting characteristics can be obtained even by a coating method with low luminance, and an element can be produced which is advantageous in terms of manufacturing cost.

────────────────────────────────────────────────── ───

[Procedure amendment]

[Submission date] August 6, 1998 (1998.8.6)

[Procedure amendment 1]

[Document name to be amended] Statement

[Correction target item name] 0062

[Correction method] Change

[Correction contents]

[0062]

EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited thereto. Example 1 ITO-coated glass substrate is etched, washed, thickness 5nm copper phthalocyanine, N, N '- diphenyl -N,
N '- di (1 - naphthyl) -1,1' - biphenyl -
4,4 '- diamine 35 nm, a compound of Table 1 5
0 nm, tris (8-quinolinolato) aluminum (II
Vacuum deposition (8 × 10
⁻⁶ to 1 × 10 ⁻⁵ Torr). 5mm x 5m on this
Place a patterned mask on m: magnesium:
After co-depositing silver = 10: 1 at 250 nm, silver 300 nm
Was deposited (8 × 10 ⁻⁶ to 1 × 10 ⁻⁵ Torr). Using a source measure unit 2400 manufactured by Toyo Technica, a constant DC voltage is applied to the EL element using ITO as an anode and Mg: Ag as a cathode to emit light, and the luminance is measured by a luminance meter BM-8 manufactured by Topcon Corporation. The degree coordinates were measured using a spectrum analyzer PMA-11 manufactured by Hamamatsu Photonics. Table 1 shows the results.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification code FI Theme coat ゛ (Reference) H05B 33/10 H05B 33/10 33/14 33/14 B

Claims (9)

[Claims] 1. An organic electroluminescent device material comprising a compound represented by the following general formula (I). Embedded image (In the formula, R ₁₁ represents a hydrogen atom or a substituent.
₁₂ represents a hydrogen atom, a cation or a substituent. Q ₁₁ and Q ₁₂ each represent an atom group necessary to form a 5- or 6-membered ring. However, at least one of Q ₁₁ and Q ₁₂ represents an atomic group forming a 6-membered ring. ) 2. An organic electroluminescent device material, which is a compound represented by the following general formula (II). Embedded image (Wherein, R ₂₁ represents a hydrogen atom or a substituent.
₂₂ represents a hydrogen atom, a cation or a substituent. X ₁ and X ₂ are an oxygen atom, a sulfur atom, a selenium atom,
CR _x1 (R _x2 ) and NR _x3 (R _x1 , R _x2 and R _x3 each represent a hydrogen atom or a substituent). Q ₂₁ and Q
₂₂ represents an atom group necessary for forming a 5-membered ring. ) 3. An organic electroluminescent device material, which is a complex formed from the compound represented by the general formula (I) in claim 1. 4. An organic electroluminescent device material, which is a complex formed from the compound represented by the general formula (II) according to claim 2. 5. The organic electroluminescent device material according to claim 3, wherein the complex contains a divalent or trivalent metal ion. 6. The complex according to claim 5, wherein the metal ion is B.
e²⁺, Mg²⁺, Al ³⁺, Ga³⁺, Zn²⁺, Cu²⁺, Co
²⁺, Ce³⁺, Eu³⁺, Eu²⁺, Tb³⁺Is characterized by
Organic electroluminescent element material. 7. An organic electroluminescence device in which a light emitting layer or a plurality of organic compound thin films including the light emitting layer is formed between a pair of electrodes, at least one of which is provided.
7. An organic electroluminescence device, which is a layer containing the organic electroluminescence device material according to any one of items 1 to 6. 8. An organic electroluminescence device in which a light emitting layer or a plurality of organic compound thin films including a light emitting layer is formed between a pair of electrodes, at least one of which is provided.
7. An organic electroluminescent device, which is a layer formed by applying the organic electroluminescent device material according to any one of items 6 to 6. 9. An organic electroluminescence device in which a light emitting layer or a plurality of organic compound thin films including a light emitting layer is formed between a pair of electrodes, at least one of which is provided.
7. An organic electroluminescence device, comprising a layer in which the organic electroluminescence device material according to any one of items 6 to 6 is dispersed in a polymer.