JP2001335776A - Novel heterocyclic compound, light-emitting element material and light-emitting element using this material - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a light-emitting element material excellent in color purity, good in light emission character, and excellent in stability during repeated use, and a light-emitting element. SOLUTION: This light-emitting element material is a compound represented by general formula (I) L-(A)m (wherein A represents a heterocyclic group formed by condensation of two or more aromatic hetero rings, the heterocyclic group represented by A in (A)m may be the same or different. (m) represents an integer of 2 or larger, and L represents a connecting group.), and the light-emitting element uses this material.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a novel heterocyclic compound. More specifically, the present invention relates to a light emitting element material and a light emitting element that can emit light by converting electric energy into light, and is applicable to fields such as display elements, displays, backlights, electrophotography, illumination light sources, recording light sources, reading light sources, signs, signs, and interiors. The present invention relates to a light-emitting element that can be suitably used.

[0002]

2. Description of the Related Art At present, research and development on various display elements are active. Among them, an organic electroluminescence (EL) element has been attracting attention as a promising display element because it can emit light with high luminance at a low voltage. ing. For example, a light emitting device that forms an organic thin film by vapor deposition of an organic compound is known (Applied Physics Letters, Vol. 51, No. 91).
3, 1987). The light-emitting element described in this document uses a tris (8-hydroxyquinolinato) aluminum complex (Alq) as an electron transporting material and is laminated with a hole transporting material (amine compound) to form a conventional single-layered device. Compared with this, the light emission characteristics are greatly improved.

[0003] As a means for further improving the luminous efficiency of the stacked type light emitting device, a method of doping a fluorescent dye is known. For example, the light-emitting device doped with a coumarin dye described in Journal of Applied Physics, Vol. 65, p. 3610, 1989 has significantly improved luminous efficiency as compared with a non-doped device. In this case, light of a desired wavelength can be extracted by changing the type of the fluorescent compound to be used.
When lq is used, when the driving voltage is increased to obtain high luminance, green emission of Alq is observed in addition to emission of the doped fluorescent compound. Therefore, development of a host material that does not reduce color purity has been desired. Japanese Patent Application Laid-Open No. H10-92578 and U.S. Pat.
No. 779 discloses a specific indole derivative. However, in the compounds described above, there is a problem that a high driving voltage is required for high-luminance light emission. Was desired. Also, 3- (4-biphenylyl) -4 is used as a method for increasing luminous efficiency.
-Phenyl-5- (4-tert-butylphenyl)-
A method using a hole-blocking material such as 1,2,4-triazole (TAZ) and bathocuproine (BCP) has been reported. However, these known materials have durability, in particular, device deterioration due to storage at high temperature and continuous light emission. Was a big problem. In addition, conventional devices with good color purity and high luminous efficiency are those in which a small amount of fluorescent dye is doped into the charge transporting material, making it difficult to achieve reproducibility of device characteristics in manufacturing and the durability of the dye. Therefore, when used for a long time, there are problems such as a decrease in luminance and a change in color. As a means to solve this, the development of a material that has both a charge transport function and a light emitting function is desired. However, in the materials developed so far, when a fluorescent dye is used at a high concentration, a high luminance due to concentration quenching, association, etc. There was a problem that light emission was difficult.

On the other hand, organic light-emitting devices that achieve high-luminance light emission are devices in which organic substances are laminated by vacuum deposition. However, from the viewpoints of simplification of the manufacturing process, workability, and large area, etc. 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.

[0005]

SUMMARY OF THE INVENTION A first object of the present invention is to provide a light emitting device material and a light emitting device which have good light emitting characteristics and excellent stability when used repeatedly. A second object of the present invention is to provide a light-emitting element having excellent color purity and a material for a light-emitting element that enables the light-emitting element. A third object of the present invention is to provide a novel heterocyclic compound effective for various electronic devices and the like.

[0006]

This object has been achieved by the following means.

[1] A light emitting device material characterized by being a compound represented by the following general formula (I).

[0008]

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(In the formula, A represents a heterocyclic group in which two or more aromatic heterocycles are fused, and the heterocyclic groups represented by A may be the same or different. M represents an integer of 2 or more.) .
L represents a linking group. [2] A light emitting device material characterized by being a compound represented by the following general formula (II).

[0010]

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(Wherein B represents a heterocyclic group in which two or more 5- and / or 6-membered aromatic heterocycles are fused, and the heterocyclic groups represented by B may be the same or different. M represents an integer of 2 or more, and L represents a linking group.) [3] A light-emitting element material characterized by being a compound represented by the following general formula (III).

[0012]

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(Where X is O, S, Se, Te or N
Represents -R. R represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. Q ₃ represents an atom group necessary for forming an aromatic hetero ring. m represents an integer of 2 or more. L represents a linking group. [4] A light emitting device material characterized by being a compound represented by the following general formula (IV).

[0014]

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(Where X is O, S, Se, Te or N
Represents -R. R represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. Q ₄ represents an atom group necessary for forming a nitrogen-containing aromatic hetero ring. m represents an integer of 2 or more. L represents a linking group. [5] A light emitting device material characterized by being a compound represented by the following general formula (V).

[0016]

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(Wherein X ₅ represents O, S or NR. R represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. Q ₅ is a 6-membered nitrogen-containing aromatic compound) Represents an atom group necessary for forming a hetero ring, m represents an integer of 2 or more, and L represents a linking group.) [6] A compound represented by the following general formula (VI) Light emitting device material.

[0018]

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(Wherein X ₆ represents O, S or N—R. R represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. Q ₆ is a 6-membered nitrogen-containing aromatic compound. Represents an atomic group necessary for forming a heterocyclic ring; n represents an integer of 2 to 8; L represents a linking group) [7] A compound represented by the following formula (VII) Light-emitting element material.

[0020]

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(Wherein, R represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. Q ₇ represents an atom group necessary for forming a 6-membered nitrogen-containing aromatic heterocyclic ring. n represents an integer of 2 to 8. L represents a linking group.) [8] A light-emitting element material, which is a compound represented by the following general formula (VIII).

[0022]

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(Wherein Q ₈₁ , Q ₈₂ and Q ₈₃ each represent an atomic group necessary for forming a 6-membered nitrogen-containing aromatic heterocyclic ring. R ₈₁ , R ₈₂ and R ₈₃ each represent L ₁ , L ₂ and L ₃ each represent a linking group, and Y represents a nitrogen atom or a 1,3,5-benzenetriyl group, which represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. Represents.)

[9] A compound represented by the following general formula (IX).

[0024]

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(Wherein, Q ₉₁ , Q ₉₂ and Q ₉₃ each represent an atom group necessary for forming a 6-membered nitrogen-containing aromatic heterocycle. R ₉₁ , R ₉₂ and R ₉₃ each represent Represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group.) [10] A compound represented by the following general formula (X).

[0026]

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Wherein R ₁₀₁ , R ₁₀₂ and R ₁₀₃ are
Each represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. R ₁₀₄ , R ₁₀₅ and R ₁₀₆ are
Each represents a substituent. p ₁ , p ₂ and p ₃ each represent an integer of 0 to 3. [11] A light-emitting element material, which is a compound represented by the following general formula (XI).

[0028]

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(Wherein, Q ₃ represents an atom group necessary for forming an aromatic heterocyclic ring; R ₁₁ represents a hydrogen atom or a substituent; m represents an integer of 2 or more; L represents a linking group) [12] In a light-emitting element in which a light-emitting layer or a plurality of organic compound thin layers including a light-emitting layer are formed between a pair of electrodes, at least one of the light-emitting elements has a general formula (I) to (1) to (11).
A light-emitting element, which is a layer containing at least one compound represented by (XI). [13] In a light-emitting element in which a light-emitting layer or a plurality of organic compound thin layers including the light-emitting layer are formed between a pair of electrodes, at least one of the light-emitting elements is a compound represented by any one of the general formulas (I) to
A light-emitting element comprising a layer in which at least one compound represented by (XI) is dispersed in a polymer. [14] In a light-emitting element in which a light-emitting layer or a plurality of organic compound thin layers including the light-emitting layer are formed between a pair of electrodes, at least one layer between the light-emitting layer and the cathode has a general formula of [1] to [11]. A light-emitting element, which is a layer containing at least one of the compounds represented by (I) to (XI). [15] In a light-emitting element in which a light-emitting layer or a plurality of organic compound thin layers including the light-emitting layer are formed between a pair of electrodes, at least one layer between the blue light-emitting layer and the cathode is [1] to [1].
[1] A light-emitting element comprising a layer containing at least one compound represented by any one of the general formulas (I) to (XI) described above. [16] In a light-emitting element in which a light-emitting layer or a plurality of organic compound thin layers including a light-emitting layer is formed between a pair of electrodes,
A light-emitting element comprising a layer containing at least one of the compounds represented by the general formulas (I) to (XI) described in [1] to [11], containing a blue light-emitting material.

[0030]

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. A represents a heterocyclic group in which two or more aromatic heterocycles are fused, and the heterocyclic groups represented by A may be the same or different. The heterocyclic group represented by A is preferably a condensed 5- or 6-membered aromatic heterocyclic ring, more preferably 2 to 6, more preferably 2 to 3, and particularly preferably 2 to 3. Of aromatic heterocycles. The hetero atom in this case is preferably N, O, S, Se, or Te atom, more preferably N, O, or S atom, and further preferably N atom. Specific examples of the aromatic heterocyclic ring constituting the heterocyclic group represented by A include, for example, furan, thiophene, pyran, pyrrole, imidazole, pyrazole, pyridine,
Pyrazine, pyrimidine, pyridazine, thiazole, oxazole, isothiazole, isoxazole, thiadiazole, oxadiazole, triazole, selenazole, tellurazole and the like, preferably imidazole, pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, thiazole, oxazole. And more preferably imidazole, thiazole, oxazole, pyridine, pyrazine, pyrimidine and pyridazine.

Specific examples of the condensed ring represented by A include, for example, indolizine, purine, pteridine, carboline,
Pyrroloimidazole, pyrrolotriazole, pyrazoloimidazole, pyrazolotriazole, pyrazolopyrimidine, pyrazolotriazine, triazolopyridine, tetrazaindene, pyrroleimidazole, pyrrolotriazole, imidazoimidazole, imidazopyridine, imidazopyrazine, imidazopyrimidine, imidazopyridazine , Oxazolopyridine, oxazolopyrazine, oxazolopyrimidine, oxazolopyridazine, thiazolopyridine, thiazolopyrazine, thiazolopyrimidine, thiazolopyridazine, pyridinopyrazine, pyrazinopyrazine,
Pyrazinopyridazine, naphthyridine, imidazotriazine and the like, preferably imidazopyridine, imidazopyrazine, imidazopyrimidine, imidazopyridazine, oxazolopyridine, oxazolopyrazine, oxazolopyrimidine, oxazolopyridazine, thiazolopyridine, thiazolopyrazine And thiazolopyrimidine, thiazolopyridazine, pyridinopyrazine and pyrazinopyrazine, more preferably imidazopyridine, oxazolopyridine, thiazolopyridine, pyridinopyrazine and pyrazinopyrazine, particularly preferably imidazopyridine.

The heterocyclic group represented by A may be further condensed with another ring and may have a substituent. As a substituent of the heterocyclic group represented by A, for example, an alkyl group (preferably having 1 to 30 carbon atoms, more preferably having 1 to 2 carbon atoms)
0, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, iso-propyl, tert-butyl, n
-Octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl and the like. ), An alkenyl group (preferably having 2 to 30 carbon atoms,
More preferably, it has 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include vinyl, allyl, 2-butenyl, and 3-pentenyl. ), An alkynyl group (preferably having 2 to 30 carbon atoms, more preferably having 2 to 20 carbon atoms, particularly preferably having 2 to 10 carbon atoms, and examples thereof include propargyl and 3-pentynyl), and an aryl group (preferably). Has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 30 carbon atoms.
12, for example, phenyl, p-methylphenyl, naphthyl and the like. ), An amino group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 10 carbon atoms, for example, amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino , Ditolylamino and the like), an alkoxy group (preferably having 1 to 3 carbon atoms).
It has 0, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, and examples thereof include methoxy, ethoxy, butoxy, 2-ethylhexyloxy and the like. ),
An aryloxy group (preferably having 6 to 30 carbon atoms, more preferably having 6 to 20 carbon atoms, and particularly preferably having 6 to 1 carbon atoms)
2, for example, phenyloxy, 1-naphthyloxy, 2-naphthyloxy and the like. ), An acyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably having 2 to 12 carbon atoms, for example, acetyl, benzoyl, formyl, pivaloyl and the like), and alkoxycarbonyl A group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably having 2 to 12 carbon atoms, such as methoxycarbonyl and ethoxycarbonyl), and an aryloxycarbonyl group (preferably 7 to 3 carbon atoms
It has 0, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonyl. ), An acyloxy group (preferably having 2 to 30 carbon atoms, more preferably having 2 to 20 carbon atoms, particularly preferably having 2 to 10 carbon atoms, such as acetoxy and benzoyloxy), and an acylamino group (preferably 2-30 carbon atoms, more preferably 2 carbon atoms
-20, particularly preferably 2-10 carbon atoms, such as acetylamino and benzoylamino. ), An alkoxycarbonylamino group (preferably having 2 to 30 carbon atoms, more preferably having 2 to 20 carbon atoms, particularly preferably having 2 to 12 carbon atoms, for example, methoxycarbonylamino and the like), aryloxycarbonylamino Group (preferably having 7 to 30 carbon atoms, more preferably having 7 to 20 carbon atoms, and particularly preferably having 7 to 12 carbon atoms.
And for example, phenyloxycarbonylamino and the like. ), A sulfonylamino group (preferably having 1 to 30 carbon atoms, more preferably having 1 to 20 carbon atoms, particularly preferably having 1 to 12 carbon atoms, for example, methanesulfonylamino, benzenesulfonylamino, etc.), and sulfamoyl. Groups (preferably having 0 to 3 carbon atoms)
It has 0, more preferably 0 to 20 carbon atoms, and particularly preferably 0 to 12 carbon atoms, and examples thereof include sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, and phenylsulfamoyl. ), Carbamoyl group (preferably having 1 to 30 carbon atoms, more preferably having 1 to 2 carbon atoms)
0, particularly preferably 1 to 12 carbon atoms, for example, carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl and the like. ), An alkylthio group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably having 1 to 12 carbon atoms, such as methylthio and ethylthio, etc.), and an arylthio group (preferably carbon Numbers 6 to 30,
More preferably, it has 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio. ), A sulfonyl group (preferably having 1 to 30 carbon atoms, more preferably having 1 to 20 carbon atoms, and particularly preferably having 1 carbon atoms.
To 12, for example, mesyl, tosyl and the like. ), Sulfinyl group (preferably having 1 to 30 carbon atoms,
More preferably, it has 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfinyl and benzenesulfinyl. ), A ureido group (preferably 1 to 30 carbon atoms, more preferably 1 to 2 carbon atoms)
0, particularly preferably 1 to 12 carbon atoms, for example, ureide, methylureide, phenylureide and the like. ), A phosphoric amide group (preferably having 1 to 3 carbon atoms)
It has 0, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include diethylphosphoramide and phenylphosphoramide. ), A hydroxy group, a mercapto group, a halogen atom (for example, a fluorine atom,
Chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group, heterocyclic group (preferably having 1 to 30 carbon atoms, more preferably 1 to 1 carbon atoms
2, as a hetero atom, for example, a nitrogen atom, an oxygen atom, a sulfur atom, specifically, for example, imidazolyl, pyridyl, quinolyl, furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, Azepinyl and the like. ), A silyl group (preferably having 3 to 40 carbon atoms, more preferably having 3 to 30 carbon atoms, and particularly preferably having 3 carbon atoms.
To 24, for example, trimethylsilyl, triphenylsilyl 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, they may be linked to form a ring.

The substituent of the heterocyclic group represented by A is preferably an alkyl group, an alkenyl group, an alkynyl group,
Aryl group, amino group, alkoxy group, aryloxy group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, acyloxy group, acylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group,
A carbamoyl group, an alkylthio group, an arylthio group, a sulfonyl group, a halogen atom, a cyano group, or a heterocyclic group, more preferably an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an aryloxy group, a halogen atom, a cyano group, or a heterocyclic group. A ring group, more preferably an alkyl group, an aryl group, an alkoxy group, an aryloxy group, or an aromatic heterocyclic group, and particularly preferably an alkyl group, an aryl group, an alkoxy group, or an aromatic heterocyclic group. m represents an integer of 2 or more, preferably 2 to 8,
More preferably 2 to 6, even more preferably 2 to 4
And particularly preferably 2 or 3, and most preferably 3. L represents a linking group. The linking group represented by L is preferably a single bond, C, N, O, S, Si, G
e, etc., more preferably a single bond, alkylene, alkenylene, alkynylene, arylene, divalent heterocycle (preferably an aromatic heterocycle, more preferably an azole, thiophene, furan ring And a group comprising N and a combination thereof, and more preferably an arylene, a divalent aromatic heterocycle and a group comprising N and a combination thereof.

Specific examples of the linking group represented by L include the following in addition to a single bond.

[0035]

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[0036]

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[0037]

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[0038]

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The linking group represented by L may have a substituent. As the substituent, for example, those mentioned as substituents for the heterocyclic group represented by A can be applied. As the substituent of L, preferably an alkyl group, an alkenyl group, an alkynyl group,
Aryl group, alkoxy group, aryloxy group, acyl group, halogen atom, cyano group, heterocyclic group, silyl group, more preferably alkyl group, alkenyl group, alkynyl group, aryl group, alkoxy group, aryloxy group, A halogen atom, a cyano group, and an aromatic heterocyclic group are preferable, and an alkyl group, an aryl group, and an aromatic heterocyclic group are more preferable.

Among the compounds represented by the general formula (I), a compound represented by the following general formula (II) is preferred.

[0041]

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In the formula, m and L have the same meanings as those in formula (I), and the preferred ranges are also the same. B represents a heterocyclic group in which two or more 5- and / or 6-membered aromatic heterocycles are fused, and the heterocyclic groups represented by B may be the same or different. The heterocyclic group represented by B is preferably a condensed 2 to 6 5-membered or 6-membered aromatic heterocyclic ring, more preferably 2 to 3 and particularly preferably 2 aromatic rings. Heterocycle fused. The hetero atom in this case is preferably N, O, S, Se, or Te atom, more preferably N, O, or S atom, and further preferably N atom. Specific examples of the aromatic heterocyclic ring constituting the heterocyclic group represented by B include, for example, furan, thiophene, pyran, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, thiazole, oxazole, isothiazole, and isothiazole. Oxazole, thiadiazole, oxadiazole, triazole, selenazole, tellurazole and the like, preferably imidazole, pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, thiazole, oxazole, more preferably imidazole, thiazole,
Oxazole, pyridine, pyrazine, pyrimidine and pyridazine.

Specific examples of the condensed ring represented by B include, for example, indolizine, purine, pteridine, carboline,
Pyrroloimidazole, pyrrolotriazole, pyrazoloimidazole, pyrazolotriazole, pyrazolopyrimidine, pyrazolotriazine, triazolopyridine, tetrazaindene, pyrroleimidazole, pyrrolotriazole, imidazoimidazole, imidazopyridine, imidazopyrazine, imidazopyrimidine, imidazopyridazine , Oxazolopyridine, oxazolopyrazine, oxazolopyrimidine, oxazolopyridazine, thiazolopyridine, thiazolopyrazine, thiazolopyrimidine, thiazolopyridazine, pyridinopyrazine, pyrazinopyrazine,
Pyrazinopyridazine, naphthyridine, imidazotriazine and the like, preferably imidazopyridine, imidazopyrazine, imidazopyrimidine, imidazopyridazine, oxazolopyridine, oxazolopyrazine, oxazolopyrimidine, oxazolopyridazine, thiazolopyridine, thiazolopyrazine And thiazolopyrimidine, thiazolopyridazine, pyridinopyrazine and pyrazinopyrazine, more preferably imidazopyridine, oxazolopyridine, thiazolopyridine, pyridinopyrazine and pyrazinopyrazine, particularly preferably imidazopyridine. The heterocyclic group represented by B may have a substituent. As the substituent, those exemplified as the substituent of the heterocyclic group represented by A in the general formula (I) can be applied. The same applies to the group.

Among the compounds represented by the general formula (I), more preferred are the compounds represented by the following general formulas (III) and (XI).

[0045]

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The general formula (III) will be described. m, L
Have the same meanings as those in formula (I), respectively, and their preferred ranges are also the same. X is O, S, S
represents e, Te or NR. R represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. Q ₃ represents an atom group necessary for forming an aromatic hetero ring. As the aliphatic hydrocarbon group represented by R, preferably an alkyl group (preferably having 1 to 20 carbon atoms, 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, etc., and an alkenyl group (preferably having 2 to 2 carbon atoms).
20, more preferably 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, for example, vinyl, allyl, 2-butenyl, 3-pentenyl and the like. ), An alkynyl 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 propargyl and 3-pentynyl).
And more preferably an alkyl group or an alkenyl group.

The aryl group represented by R preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms.
-Methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-methoxyphenyl, 3-trifluoromethylphenyl, pentafluorophenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 1-naphthyl, 2-naphthyl, 1-pyrenyl and the like. R
Is a monocyclic or condensed heterocyclic group (preferably having 1 to 20 carbon atoms, preferably having 1 to 1 carbon atoms).
2, more preferably a heterocyclic group having 2 to 10 carbon atoms), preferably an aromatic heterocyclic group containing at least one of a nitrogen atom, an oxygen atom, a sulfur atom and a selenium atom.
Specific examples of the heterocyclic group represented by R include, for example, pyrrolidine, piperidine, pyrrole, furan, thiophene,
Imidazoline, imidazole, benzimidazole, naphthoimidazole, thiazolidine, thiazole, benzothiazole, naphthothiazole, isothiazole, oxazoline, oxazole, benzoxazole, naphthoxazole, isoxazole, selenazole, benzselenazole, naphthoselenazole, pyridine, quinoline, Isoquinoline, indole, indolenine, pyrazole, pyrazine, pyrimidine, pyridazine, triazine, indazole, purine, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, phenanthridine, pteridine, phenanthroline, tetrazaindene, and the like, preferably. Is furan, thiophene, pyridine, quinoline, pyrazine, pyrimidine, pyridazine, Triazine, phthalazine, naphthyridine, quinoxaline, quinazoline, more preferably furan, thiophene, pyridine, quinoline,
Particularly preferred is quinoline.

The aliphatic hydrocarbon group, aryl group and heterocyclic group represented by R may have a substituent, and the substituent may be a substituent of the heterocyclic group represented by A in the general formula (I). What was mentioned as a group can be applied, and a preferable substituent is also the same. R is preferably an alkyl group, an aryl group, or an aromatic heterocyclic group, more preferably an aryl group or an aromatic heterocyclic group, and still more preferably an aryl group or an aromatic azole group.

X is preferably O, S, NR, more preferably O, NR, further preferably NR, and particularly preferably N-Ar (Ar is an aryl group, aromatic Group, more preferably an aryl group having 6 to 30 carbon atoms, an aromatic azole group having 2 to 30 carbon atoms, still more preferably an aryl group having 6 to 20 carbon atoms, and an aromatic azole having 2 to 16 carbon atoms. And particularly preferably an aryl group having 6 to 12 carbon atoms and an aromatic azole group having 2 to 10 carbon atoms).

Q ₃ represents an atom group necessary for forming an aromatic hetero ring. The aromatic hetero ring formed by Q ₃ is preferably a 5- or 6-membered aromatic hetero ring, more preferably a 5- or 6-membered nitrogen-containing aromatic hetero ring, and still more preferably a 6-membered nitrogen-containing aromatic hetero ring. It is an aromatic heterocycle. Specific examples of the aromatic hetero ring formed by Q _3, for example furan, thiophene, pyran, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, thiazole, oxazole, isothiazole, isoxazole, thiadiazole, oxa Examples thereof include diazole, triazole, selenazole and tellurazole, preferably pyridine, pyrazine, pyrimidine and pyridazine, more preferably pyridine and pyrazine, and further preferably pyridine.
The aromatic hetero ring formed by Q ₃ may further form a condensed ring with another ring, and may have a substituent. As the substituent, those exemplified as the substituent of the heterocyclic group represented by A in formula (I) can be applied, and the same applies to the preferable substituents.

Among the compounds represented by the general formula (III), more preferred are the compounds represented by the following general formula (IV).

[0052]

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In the formula, m and L have the same meanings as those in formula (I), and the preferred ranges are also the same. X has the same meaning as that in formula (III), and the preferred range is also the same. Q ₄ represents an atom group necessary for forming a nitrogen-containing aromatic hetero ring. The nitrogen-containing aromatic hetero ring formed by Q ₄ is preferably a 5- or 6-membered nitrogen-containing aromatic hetero ring, and more preferably a 6-membered nitrogen-containing aromatic hetero ring. Specific examples of the nitrogen-containing aromatic heterocyclic ring formed by Q ₄ include, for example, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, thiazole, oxazole, isothiazole, isoxazole, thiadiazole, oxadiazole, triazole , Selenazole, tellurazole and the like, preferably pyridine, pyrazine, pyrimidine and pyridazine, more preferably pyridine and pyrazine, and further preferably pyridine.
The aromatic hetero ring formed by Q ₄ may further form a condensed ring with another ring, and may have a substituent. As the substituent, those exemplified as the substituent of the heterocyclic group represented by A in formula (I) can be applied, and the same applies to the preferable substituents.

Among the compounds represented by the general formula (III), more preferred are the compounds represented by the following general formula (V).

[0055]

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In the formula, m and L have the same meanings as those in formula (I), respectively, and their preferred ranges are also the same. X ₅ represents O, S or NR. R is the general formula (I
It has the same meaning as that in II), and the preferred range is also the same. Q ₅ represents an atom group necessary for forming a 6-membered nitrogen-containing aromatic heterocycle. Specific examples of the 6-membered nitrogen-containing aromatic heterocyclic ring formed by Q ₅ include, for example, pyridine,
Pyrazine, pyrimidine, pyridazine, triazine and the like can be mentioned, preferably pyridine, pyrazine, pyrimidine and pyridazine, more preferably pyridine and pyrazine, further preferably pyridine. The 6-membered nitrogen-containing aromatic hetero ring formed by Q ₅ may further form a condensed ring with another ring, or may have a substituent. As the substituent, those exemplified as the substituent of the heterocyclic group represented by A in formula (I) can be applied, and the same applies to the preferable substituents.

Among the compounds represented by the general formula (III), more preferred are the compounds represented by the following general formula (VI).

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In the formula, L has the same meaning as in formula (I), and the preferred range is also the same. X ₆ has the same meaning as X ₅ in formula (V), and the preferred range is also the same. Q ₆ has the same meaning as Q ₅ in formula (V), and the preferred range is also the same. n represents an integer of 2 to 8, preferably 2 to 6, more preferably 2 to 4, still more preferably 2 or 3, and particularly preferably 3. Among the compounds represented by the general formula (III), more preferred are the compounds represented by the following general formula (VII).

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In the formula, L has the same meaning as in formula (I), and the preferred range is also the same. R has the same meaning as that in formula (III), and the preferred range is also the same. Q ₇ has the same meaning as Q ₅ in formula (V), and the preferred range is also the same. n is a general formula (V
It has the same meaning as that in I), and the preferred range is also the same.

Among the compounds represented by the general formula (III), more preferred are the compounds represented by the following general formula (VIII).

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In the formula, R ₈₁ , R ₈₂ and R ₈₃ have the same meanings as R in formula (III), and their preferred ranges are also the same. Q ₈₁ , Q ₈₂ and Q ₈₃ each have the same meaning as Q ₅ in formula (V), and their preferred ranges are also the same. L ₁ , L ₂ and L ₃ have the same meanings as L in formula (I), respectively. L ₁ , L ₂ , and L ₃ are preferably a single bond, an arylene, a divalent aromatic heterocycle, or a linking group composed of a combination thereof;
More preferably, it is a single bond, a connecting group consisting of benzene, naphthalene, anthracene, pyridine, pyrazine, thiophene, furan, oxazole, thiazole, oxadiazole, thiadiazole, triazole, and a combination thereof. , Thiophene and a linking group consisting of a combination thereof,
Particularly preferred is a single bond, a benzene and a linking group comprising a combination thereof, and most preferred is a single bond. L ₁ , L ₂ and L ₃ may have a substituent, and as the substituent, those mentioned as the substituent of the heterocyclic group represented by A in the general formula (I) can be applied.

Y represents a nitrogen atom or a 1,3,5-benzenetriyl group. The latter may have a substituent at the 2,4,6-position, and examples of the substituent include an alkyl group and an aryl group. And a halogen atom. Y is preferably a nitrogen atom or an unsubstituted 1,3,5-benzenetriyl group, and more preferably an unsubstituted 1,3,5-benzenetriyl group. Among the compounds represented by the general formula (III), a compound represented by the following general formula (IX) is particularly preferred.

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In the formula, R ₉₁ , R ₉₂ and R ₉₃ each have the same meaning as R in formula (III), and the preferred range is also the same. Q ₉₁ , Q ₉₂ and Q ₉₃ each have the same meaning as Q ₅ in formula (V), and their preferred ranges are also the same. Among the compounds represented by the general formula (III), most preferred are the compounds represented by the following general formula (X).

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In the formula, R ₁₀₁ , R ₁₀₂ and R ₁₀₃ each have the same meaning as R in formula (X), and the preferred range is also the same. R ₁₀₄ , R ₁₀₅ and R
₁₀₆ represents a substituent, and as the substituent, those mentioned as the substituent of the heterocyclic group represented by A in formula (I) can be applied, and preferred substituents are also the same. Where possible, the substituents may be linked together to form a ring. p ₁ , p ₂ and p ₃ each represent an integer of 0 to 3, preferably 0 to 2, more preferably 0 or 1, and still more preferably 0.

Next, the general formula (XI) will be described.
m and L have the same meanings as those in formula (I), respectively, and their preferred ranges are also the same. Q ₃ has the same meaning as that in formula (III), and the preferred range is also the same. R ₁₁ represents a hydrogen atom or a substituent. R ₁₁
As the substituent represented by, for example, those exemplified as the substituent of the heterocyclic group represented by A in the general formula (I) can be applied. The substituent represented by R ₁₁ is preferably an aliphatic hydrocarbon group, an aryl group, or an aromatic heterocyclic group, more preferably an alkyl group (preferably having 1 carbon atom).
-20, more preferably 1-12, particularly preferably 1-8, for example methyl, ethyl, iso
-Propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl and the like. ), 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, 2-methylphenyl, 3-methylphenyl, and 4-methylphenyl) , 4-methoxyphenyl, 3-
Trifluoromethylphenyl, pentafluorophenyl, 1-naphthyl, 2-naphthyl and the like. ), An aromatic heterocyclic group (preferably having 1 to 2 carbon atoms)
0, preferably an aromatic heterocyclic group having 1 to 12 carbon atoms, more preferably an aromatic heterocyclic group having 2 to 10 carbon atoms, more preferably an aromatic heterocyclic group containing at least one of a nitrogen atom, an oxygen atom, a sulfur atom and a selenium atom. It is a ring group. As the aromatic heterocycle, for example, pyrrolidine, piperidine, pyrrole, furan, thiophene, imidazoline, imidazole, benzimidazole, naphthimidazole, thiazolidine,
Thiazole, benzothiazole, naphthothiazole, isothiazole, oxazoline, oxazole, benzoxazole, naphthoxazole, isoxazole,
Selenazole, benzselenazole, naphthoselenazole, pyridine, quinoline, isoquinoline, indole,
Indolenine, pyrazole, pyrazine, pyrimidine, pyridazine, triazine, indazole, purine, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, phenanthridine, pteridine,
Phenanthroline, tetrazaindene, carbazole and the like, preferably furan, thiophene, pyridine, quinoline, pyrazine, pyrimidine, pyridazine, triazine, phthalazine, naphthyridine, quinoxaline,
Quinazoline, more preferably furan, thiophene, pyridine and quinoline, and still more preferably quinoline. ), And more preferably an aryl group or an aromatic heterocyclic group. The substituent represented by R ₁₁ may be further substituted, and if possible, may combine to form a ring.

Among the compounds represented by the general formula (XI),
More preferred are compounds represented by the following formula (XII).

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In the formula, m and L have the same meanings as those in formula (I), and the preferred ranges are also the same. Q ₁₂ has the same meaning as Q ₄ in formula (IV), and the preferred range is also the same. R ₁₁ has the general formula (X
It has the same meaning as that in I), and the preferred range is also the same.

Among the compounds represented by the general formula (XI),
More preferred are compounds represented by the following formula (XIII).

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In the formula, m and L have the same meanings as those in formula (I), and the preferred ranges are also the same. Q ₁₃ has the same meaning as Q ₅ in formula (V),
The same applies to the preferred range. R ₁₁ has the general formula (XI)
And the preferred range is also the same.

Of the compounds represented by the general formula (XI),
Particularly preferred are compounds represented by the following formula (XIV).

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In the formula, L ₁ , L ₂ , L ₃ and Y have the same meanings as those in formula (VIII), and the preferred ranges are also the same. Q ₁₄₁ , Q ₁₄₂ and Q
₁₄₃ has the same meaning as Q ₅ in formula (V), and the preferred range is also the same. R ₁₄₁ , R ₁₄₂ and R ₁₄₃ each have the same meaning as R ₁₁ in formula (XI), and the preferred range is also the same.

Among the compounds represented by the general formula (XI),
Most preferably, it is a compound represented by the following formula (XV).

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In the formula, Q ₁₅₁ , Q ₁₅₂ and Q ₁₅₃ have the same meanings as Q ₅ in formula (V), respectively, and their preferred ranges are also the same. R ₁₅₁ , R ₁₅₂ and R ₁₅₃
Has the same meaning as R ₁₁ in formula (XI), and the preferred range is also the same.

The following are specific examples of the compound represented by formula (I) of the present invention, but the present invention is not limited to these.

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The compounds of the present invention represented by formulas (I) to (XV) are described in JP-B-44-23025 and JP-B-48-884.
No. 2, JP-A-53-6331, JP-A-10-9257
8, U.S. Patent Nos. 3,449,255 and 5,766
No. 779, J.A. Am. Chem. Soc. , 94,24
14 (1972), Helv. Chim. Acta, 6
3, 413 (1980), Liebigs Ann. C
hem. , 1423 (1982).

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 2

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1-1. Synthesis of Compound 2a 50.8 g of 2-chloro-3-nitropyridine (0.32 g)
0 mol), 90.8 g (0.657 mol) of potassium carbonate, 7.90 g (0.0416 mol) of copper (I) iodide, and 300 ml of toluene were stirred at room temperature under a nitrogen atmosphere. 45.7 g (0.
490 mol). After heating under reflux for 5 hours, the reaction solution was filtered, and the filtrate was concentrated under reduced pressure. After purification by silica gel column chromatography (developing solvent: chloroform), recrystallization was performed with chloroform / hexane to obtain 45.7 g (0.21 mol) of compound 2a. 66% yield

1-2. Synthesis of Compound 2b Compound 1a (17.0 g, 0.0790 mol) was dissolved in tetrahydrofuran (170 ml), and stirred under a nitrogen atmosphere at room temperature, to which sodium hydrosulfite 69.0 g (0.396 mol) / water was added. 220 ml of the solution were added dropwise. After stirring for 1 hour, 170 ml of ethyl acetate was added, and then a solution of 13.6 g (0.162 mol) of sodium hydrogen carbonate / 140 ml of water was added dropwise. Further, a solution of 10.0 g (0.0358 mol) of 4,4'-biphenyldicarbonyl chloride / 100 ml of ethyl acetate was added dropwise, and the solution was added at room temperature for 5 minutes.
Stirred for hours. The precipitated solid was collected by filtration and washed with water and then with ethyl acetate to give 16.0 g of compound 2b.
(0.0277 mol). 77% yield

1-3. Synthesis of Exemplified Compound 2 300 ml of xylene was added to 10.0 g (0.0173 mol) of compound 2b and 2.3 g (0.0121 mol) of p-toluenesulfonic acid monohydrate, and the mixture was heated and refluxed in a nitrogen atmosphere for 6 hours. Azeotropic dehydration. After cooling the reaction solution to room temperature, the precipitated solid was collected by filtration and recrystallized from dimethylformamide / acetonitrile to obtain 5.20 g (9.62 mmol) of Exemplified Compound 2. Yield 5
7% Melting point: 298-300 ° C

Synthesis Example 2 Synthesis of Exemplified Compound 18

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2-1. Synthesis of Compound 18b Compound 1a (15.0 g, 0.0697 mol) was dissolved in tetrahydrofuran (150 ml), and stirred under a nitrogen atmosphere at room temperature. Then, sodium hydrosulfite 60.9 g (0.345 mol) / water was added. 200 ml of the solution were added dropwise. After stirring for 2 hours, 150 ml of ethyl acetate was added, and then a solution of 12.0 g (0.143 mol) of sodium hydrogen carbonate / 120 ml of water was added dropwise. Furthermore, trimesic acid chloride5.
A solution of 2 g (0.0196 mol) / 50 ml of ethyl acetate was added dropwise and stirred at room temperature for 3 hours. After adding saturated saline to the reaction solution and extracting with ethyl acetate, the organic phase was washed with saturated saline and the organic phase was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (developing solvent: chloroform / methanol = 10/1 (vol / vol)), and then recrystallized from dimethylformamide / acetonitrile to give compound 18b. 1 g (5.76 mmol)
Obtained. Yield 29%.

2-2. Synthesis of Exemplified Compound 18 3.70 g (5.20 mmol) of compound 18b, p-
100 ml of xylene was added to 0.7 g (3.68 mmol) of toluenesulfonic acid monohydrate, and the mixture was heated under reflux for 3 hours under a nitrogen atmosphere and azeotropically dehydrated. After the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure, purified by silica gel column chromatography (developing solvent: chloroform / methanol = 20/1 (vol / vol)), and then recrystallized from chloroform / methanol. As a result, 1.70 g (2.58 mmol) of Exemplified Compound 18 was obtained. Yield 50%. Melting point: 279-281 ° C

Synthesis Example 3 Synthesis of Exemplified Compound 19 3-1. Synthesis of Compound 19a 2-Chloro-3-nitropyridine 50.0 g (0.31
5 mol), 90.8 g (0.657 mol) of potassium carbonate, 7.90 g (0.0416 mol) of copper (I) iodide, and 300 ml of toluene were stirred at room temperature under a nitrogen atmosphere. -45.0 g toluidine
(0.420 mol) was added. After heating and refluxing for 8 hours,
The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. After purification by silica gel column chromatography (developing solvent: chloroform), recrystallization from chloroform / hexane gave 51.0 g (0.222 mol) of compound 19a.
Obtained. 71% yield

3-2. Synthesis of Compound 19b 32.5 g (0.142 mol) of Compound 19a was dissolved in 320 ml of tetrahydrofuran, and 124 g (0.712 mol) of sodium hydrosulfite / 320 ml of water were stirred at room temperature under a nitrogen atmosphere. Was added dropwise and then 100 ml of methanol were added. After stirring for 1 hour, ethyl acetate 38
0 ml, then add sodium bicarbonate 24.
A solution of 4 g (0.290 mol) / 55 ml of water was added dropwise. Further, 10.5 g of trimesic acid chloride (0.
(0396 mol) / 100 ml of ethyl acetate was added dropwise and stirred at room temperature for 3 hours. After adding saturated saline to the reaction solution and extracting with ethyl acetate, the organic phase was washed with saturated saline and the organic phase was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and silica gel column chromatography (developing solvent: chloroform / methanol = 10)
/ 1 (vol / vol)) to obtain 10.2 g (0.0135 mol) of compound 19b. Yield 34%.

3-3. Synthesis of Exemplified Compound 19 3.30 g (4.38 mmol) of compound 19b, p-
50 ml of xylene was added to 0.5 g (2.63 mmol) of toluenesulfonic acid monohydrate, and the mixture was heated under reflux for 3 hours under a nitrogen atmosphere and azeotropically dehydrated. After cooling the reaction solution to room temperature, the solvent was distilled off under reduced pressure, and silica gel column chromatography (developing solvent: chloroform / methanol =
After purification by 20/1 (vol / vol)), recrystallization from chloroform / methanol gave 1.97 g (2.81 mmol) of Exemplified Compound 19. Yield 6
4%. Melting point: 258-259 ° C

Synthesis Example 4 Synthesis of Exemplified Compound 20 4-1. Synthesis of Compound 20a 2-Chloro-3-nitropyridine 45.5 g (0.28
6 mol), 81.1 g (0.587 mol) of potassium carbonate, 7.10 g (0.0373 mol) of copper (I) iodide, and 300 ml of toluene were stirred at room temperature under a nitrogen atmosphere. 40.0 g (0.268 mol) of -tert-butylaniline were added. After heating under reflux for 8 hours, the reaction solution was filtered, and the filtrate was concentrated under reduced pressure.
After purification by silica gel column chromatography (developing solvent: chloroform), recrystallization from chloroform / hexane gave 52.0 g of compound 20a.
(0.192 mol). 72% yield

4-2. Synthesis of Compound 20b 34.8 g (0.128 mol) of Compound 20a was dissolved in 350 ml of tetrahydrofuran, and stirred at room temperature under a nitrogen atmosphere. 112 g (0.643 mol) of sodium hydrosulfite / 320 ml of water Was added dropwise and then 90 ml of methanol were added. After stirring for 1 hour, ethyl acetate 350
Milliliters, and then add sodium bicarbonate 22.0
g (0.262 mol) / 50 ml of water was added dropwise. Further, 9.5 g of trimesic acid chloride (0.03
A solution of (58 mol) / 90 ml of ethyl acetate was added dropwise, and the mixture was stirred at room temperature for 2 hours. After adding saturated saline to the reaction solution and extracting with ethyl acetate, the organic phase was washed with saturated saline and the organic phase was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and silica gel column chromatography (developing solvent: chloroform / methanol = 10 /
1 (vol / vol)) to obtain 12.0 g (0.0136 mol) of compound 20b. Yield 3
8%.

4-3. Synthesis of Exemplified Compound 20 Compound 20b (3.00 g, 3.41 mmol), p-
50 ml of xylene was added to 0.3 g (1.58 mmol) of toluenesulfonic acid monohydrate, and the mixture was heated under reflux for 3 hours under a nitrogen atmosphere and azeotropically dehydrated. After cooling the reaction solution to room temperature, the precipitated solid was collected by filtration, and chloroform /
By recrystallization from methanol, 2.06 g (2.49 mmol) of Exemplified Compound 20 was obtained. 73% yield. Melting point: 300 ° C or higher

Synthesis Example 5 Synthesis of Exemplified Compound 21 5-1. Synthesis of compound 21a 2-Chloro-3-nitropyridine 50.0 g (0.31 g)
5 mol), 90.8 g (0.657 mol) of potassium carbonate, 7.90 g (0.0416 mol) of copper (I) iodide, and 300 ml of toluene were stirred at room temperature under a nitrogen atmosphere. -45.0 g toluidine
(0.420 mol) was added. After heating and refluxing for 8 hours,
The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. After purification by silica gel column chromatography (developing solvent: chloroform), recrystallization from chloroform / hexane gave 46.3 g (0.202 mol) of compound 21a.
Obtained. 64% yield

5-2. Synthesis of Compound 21b 32.5 g (0.142 mol) of Compound 21a was dissolved in 320 ml of tetrahydrofuran, and 124 g (0.712 mol) of sodium hydrosulfite / 320 ml of water was stirred at room temperature under a nitrogen atmosphere. Was added dropwise and then 100 ml of methanol were added. After stirring for 1 hour, ethyl acetate 38
0 ml, then add sodium bicarbonate 24.
A solution of 4 g (0.290 mol) / 55 ml of water was added dropwise. Further, 10.5 g of trimesic acid chloride (0.
(0396 mol) / 100 ml of ethyl acetate was added dropwise and stirred at room temperature for 3 hours. After adding saturated saline to the reaction solution and extracting with ethyl acetate, the organic phase was washed with saturated saline and the organic phase was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and silica gel column chromatography (developing solvent: chloroform / methanol = 10)
/ 1 (vol / vol)) to obtain 8.5 g (0.0112 mol) of compound 21b. Yield 2
8%.

5-3. Synthesis of Exemplified Compound 21 3.30 g (4.38 mmol) of compound 21b, p-
50 ml of xylene was added to 0.5 g (2.63 mmol) of toluenesulfonic acid monohydrate, and the mixture was heated under reflux for 7 hours under a nitrogen atmosphere and azeotropically dehydrated. After cooling the reaction solution to room temperature, the solvent was distilled off under reduced pressure, and silica gel column chromatography (developing solvent: chloroform / methanol =
After purification by 20/1 (vol / vol)), recrystallization from chloroform / acetonitrile gave 2.02 g (2.88 mmol) of Exemplified Compound 21. Yield 66%. Melting point: 250 ° C

Synthesis Example 6 Synthesis of Exemplified Compound 24 6-1. Synthesis of Compound 24a 59.0 g of 2-chloro-3-nitropyridine (0.34
7 mol), 105 g (0.760 mol) of potassium carbonate,
While stirring 9.40 g (0.0494 mol) of copper (I) iodide and 300 ml of toluene at room temperature under a nitrogen atmosphere, 75.0 g of 8-aminoquinoline (0.
520 mol). After heating under reflux for 16 hours, the reaction solution was filtered, and the filtrate was concentrated under reduced pressure. After purification by silica gel column chromatography (developing solvent: chloroform), recrystallization from chloroform / hexane gave 27.0 g (0.102 mol) of compound 24a. 29% yield

6-2. Synthesis of Compound 24b 25.0 g (93.9 mmol) of Compound 24a was dissolved in 220 ml of tetrahydrofuran, and stirred under a nitrogen atmosphere at room temperature. Then, 82.2 g (0.472 mol) of sodium hydrosulfite / water was added. 420
Milliliter of the solution was added dropwise and then 70 ml of methanol was added. After stirring for 1 hour, ethyl acetate 3
Add 80 ml, then add sodium bicarbonate 2
A solution of 4.4 g (0.290 mol) / 55 ml of water was added dropwise. 7.55 g of trimesic acid chloride
A solution of (28.4 mmol) / 100 ml of ethyl acetate was added dropwise, and the mixture was stirred at room temperature for 3 hours. After adding saturated saline to the reaction solution and extracting with ethyl acetate, the organic phase was washed with saturated saline and the organic phase was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: chloroform / methanol = 10/1 (vol / vol)) to obtain 7.86 g (9.09 mmol) of compound 24b. Yield 32%.

6-3. Synthesis of Exemplified Compound 24 Compound 24b 5.00 g (5.78 mmol), p-
100 ml of xylene was added to 0.5 g (2.63 mmol) of toluenesulfonic acid monohydrate, and the mixture was heated under reflux for 5 hours under a nitrogen atmosphere and azeotropically dehydrated. After the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure, purified by silica gel column chromatography (developing solvent: chloroform / methanol = 20/1 (vol / vol)), and then recrystallized with chloroform / acetonitrile. As a result, 1.87 g (2.31 mmol) of Exemplified Compound 24 was obtained.
Yield 40%. Melting point: 384 ° C

Synthesis Example 7

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7-1. Synthesis of Compound 101b Compound 2a (50.0 g, 0.232 mol) was dissolved in tetrahydrofuran (500 ml), and sodium hydrosulfite sodium 200 g (1.149 mol) / water (700 ml) was stirred at room temperature under a nitrogen atmosphere. Was added dropwise. Further, 20 ml of methanol was added, and the mixture was stirred for 1 hour. Next, 500 ml of ethyl acetate was added and sodium hydrogencarbonate 40 ml was added.
g (0.476 mol) / 400 ml of water was added. Further, 5-bromoisophthaloyl chloride
A solution of 4 g (0.232 mol) / 150 ml of ethyl acetate was added dropwise and stirred at room temperature for 5 hours. The mixture was extracted with ethyl acetate, washed sequentially with water and saturated saline, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. After purification by silica gel column chromatography (developing solvent: chloroform), recrystallization from chloroform / hexane gave 29.6 g (0.051) of compound 101b.
Mol). Yield 22%.

7-2. Synthesis of Compound 101c 30 g (0.05 mol) of Compound 101b was dissolved in 1 liter of xylene, and 4.7 g (0.025 mol) of p-toluenesulfonic acid monohydrate was added.
The azeotropic dehydration was performed while heating and refluxing for an hour. After cooling the reaction solution to room temperature, the precipitated solid was collected by filtration, and ethanol /
Compound 101c was obtained by recrystallization from chloroform.
Was obtained in an amount of 16.3 g (0.03 mol). Yield 58%.

7-3. Synthesis of Exemplified Compound 101 500 mg (0.92 mmol) of Compound 101c
332 mg (1.01 mmol) of compound 101d were suspended in 20 ml of ethylene glycol dimethyl ether and 10 ml of water. 214.5 milligrams of sodium carbonate (2.02
Mmol), 15 mg of palladium carbon and 12 mg of triphenylphosphine, and the mixture was refluxed for 2 hours. After stopping the heating, the catalyst was removed by hot filtration, the filtrate was extracted with ethyl acetate, dried over magnesium sulfate, and the solvent was distilled off. The residue was recrystallized from chloroform to give Exemplified Compound 101 (180 mg, 0.27 mmol). Yield 29%.

Next, a light emitting device containing the compound of the present invention will be described. The method for forming the organic layer of the light-emitting element containing the compound of the present invention is not particularly limited, but includes methods such as resistance heating evaporation, electron beam, sputtering, molecular lamination, coating, inkjet, and printing. Is used, resistance heating evaporation,
Coating methods are preferred.

When the compound of the present invention is used as a material for a light-emitting device, it may be used in any of a hole injection / transport layer, an electron injection / transport layer, and a light-emitting layer. It is preferable to use them.

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 is 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 injecting layer, the hole transporting layer, the light emitting layer and the like, 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, a layer formed on a soda lime glass, an alkali-free 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 producing 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 coating of a dispersion of indium tin oxide are used. The film is formed by the following method. 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, plasma treatment and the like are effective.

The cathode supplies electrons to the electron injecting layer, the electron transporting layer, the light emitting layer and the like. The cathode has good adhesion and ionization potential between the negative electrode such as the electron injecting layer, the electron transporting layer and the light emitting layer. It is selected in consideration of stability and the like. As a material of the cathode, a metal, an alloy, a metal oxide, an electrically conductive compound, or a mixture thereof can be used. Specific examples thereof include alkali metals (eg, Li, Na, K, Cs
Or its fluorides, oxides, alkaline earth metals (eg, Mg, Ca, etc.) or its fluorides, oxides,
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, the material has a work function of 4 eV or less, and 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 10 n
m to 5 μm, more preferably 5 to 5 μm.
0 nm to 1 μm, more preferably 100 nm to 1 μm.
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, it is possible to form an alloy electrode 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.

As the material of the light emitting layer, holes can be injected from the anode or the hole injection layer or the hole transport layer when an electric field is applied, and electrons can be injected from the cathode or the electron injection layer or the 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. The compound used for the light emitting layer may be any of those that emit light from an excited singlet state and those that emit light from an excited triplet state.For example, in addition to the compounds of the present invention, for example, benzoxazole derivatives, benzimidazole derivatives, benzothiazole derivatives, styryl Benzene derivative, polyphenyl derivative, diphenylbutadiene derivative, tetraphenylbutadiene derivative, naphthalimide derivative, coumarin derivative, perylene derivative, perinone derivative, oxadiazole derivative, aldazine derivative, pyrazine derivative, cyclopentadiene derivative, bisstyrylanthracene derivative, quinacridone Derivative, pyrrolopyridine derivative, thiadiazolopyridine derivative, cyclopentadiene derivative, styrylamine derivative, aromatic dimethylidin compound, 8-quinolyl Metal complexes of Lumpur derivatives, transition metal complexes (e.g., tris (2-phenylpyridine) iridium (III) such as ortho-metalated complexes, etc.)
And various metal complexes represented by rare earth complexes, and polymer compounds such as polythiophene, polyphenylene, polyphenylenevinylene, and polyfluorene. Although the thickness of the light emitting layer is not particularly limited, it is usually 1 nm to
It is preferably in the range of 5 μm, more preferably 5 nm
１1 μm, more preferably 10 nm to 500 nm.
It is. The method for forming the light emitting layer is not particularly limited, but resistance heating deposition, electron beam, sputtering,
Methods such as a molecular lamination method, a coating method (such as a spin coating method, a casting method, and a dip coating method), an inkjet method, a printing method, and an LB method are used, and resistance heating evaporation and a coating method are preferable.

The material of the hole injection layer and the hole transport layer has 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, conductive polymer oligomers such as polythiophene, and carbon films. The thickness of the hole injection layer and the hole transport layer is not particularly limited, but is usually preferably in the range of 1 nm to 5 μm,
It is more preferably 5 nm to 1 μm, and still more preferably 10 nm to 500 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.), an inkjet method, a printing method, and the like. 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. Preferably, the compound of the present invention is contained in the electron injection layer and / or the electron transport layer, but other materials of the compound of the present invention can also be used. Specific examples thereof include triazole derivatives, oxazole derivatives, oxadiazole derivatives, fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, and distyryl derivatives. Pyrazine derivatives, heterocyclic tetracarboxylic anhydrides such as naphthalene perylene, phthalocyanine derivatives, 8
-Metal complexes of quinolinol derivatives, metal phthalocyanines, and various metal complexes represented by metal complexes having benzoxazole or benzothiazole as ligands. The thickness of the electron injecting layer and the electron transporting layer is not particularly limited, but is 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 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 injecting layer and the electron transporting layer include a vacuum evaporation method, an LB method, a method in which the electron injecting and transporting agent is dissolved or dispersed in a solvent and coated (spin coating, casting, dip coating, etc.), An ink jet method, a printing method, or the like is used. In the case of the coating method, it can be dissolved or dispersed together with the resin component.
What was illustrated 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 a substance such as moisture or oxygen which promotes element deterioration 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
, TiO _{2 and} other metal oxides, 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, An inkjet method, a printing method, or the like can be applied.

[0158]

EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited thereto. Embodiment 1 FIG. On a cleaned glass substrate with an ITO electrode, a copper phthalocyanine film having a thickness of 15 nm and N, N'-bis (1-
Naphthyl) -N, N'-diphenylbenzidine (NP
D) was 40 nm in film thickness, and the compound described in Table 1 was 60 nm in film thickness.
In this order, vacuum deposition (1.0 × 10 ^{−3 to} 1.3 × 10 ⁻³ P
a) A patterned mask (a mask having a light-emitting area of 4 mm × 5 mm) is set thereon, and magnesium: silver = 10: 1 is co-deposited at 250 nm, and then silver 300
nm was vapor-deposited (1.0 × 10 ^{−3 to} 1.3 × 10 ⁻³ Pa) to produce a light-emitting element. The fabricated device was sealed in a dry glove box. Using Toyo Technica Source Measure Unit Model 2400, ITO as anode, Mg: A
g is used as a cathode, a DC constant voltage is applied to the light emitting element to emit light, and the luminance is measured by a luminance meter BM-8 manufactured by Topcon Corporation, and the emission wavelength and chromaticity coordinates (CIE chromaticity coordinates) are measured by a spectrum analyzer PMA-11 manufactured by Hamamatsu Photonics. It measured using. Relative luminance (luminance after aging assuming that the luminance immediately after the production of the element was 100) was expressed as a relative value (driving the luminance after driving the produced element for 3 days at 85 ° C. and 70% RH). (Voltage 10 V)) and the presence or absence of a dark spot (non-light emitting portion) on the light emitting surface was visually evaluated. Table 1 shows the results.

[0159]

[Table 1]

[0160]

Embedded image

From the results shown in Table 1, it can be seen that the use of the compound of the present invention can emit blue light with high luminance and good color purity even in an undoped device. In addition, it can be seen that there is little decrease in luminance and generation of dark spots after storage at high temperature, and the durability is excellent.

Embodiment 2 FIG. After the ITO substrate was washed in the same manner as in Example 1, copper phthalocyanine was vacuum-formed so as to have a thickness of 5 nm, NPD had a thickness of 40 nm, blue light-emitting material A had a thickness of 20 nm, and the compounds shown in Table 2 had a thickness of 40 nm. Vapor deposition (1.0 × 10 ^{−3 to} 1.3 × 10 ⁻³ Pa) was performed. On top of this, a patterned mask (a mask having a light emitting area of 4 mm × 5 mm) is provided, and magnesium: silver = 10: 1 is added to the mask.
After co-evaporation of 50 nm, silver of 300 nm was evaporated (1.0 ×
10 ^{−3 to} 1.3 × 10 ⁻³ Pa) to produce a light emitting device. The fabricated device was sealed in a dry glove box. The same evaluation as in Example 1 was performed on the manufactured device. Table 2 shows the results.

[0163]

[Table 2]

[0164]

Embedded image

From the results shown in Table 2, it can be seen that when the compound of the present invention is used, an undoped element functions as an electron transporting material, and blue light emission with high luminance and good color purity is possible. In addition, it can be seen that there is little decrease in luminance and generation of dark spots after storage at high temperature, and the durability is excellent.

Embodiment 3 FIG. An ITO substrate is used in the same manner as in the first embodiment.
After cleaning, copper phthalocyanine has a thickness of 5 nm and NPD has a thickness of 5 nm.
40 nm, perylene and the compounds described in Table 3
Deposition rate 0.004 nm / sec, film thickness 6 at 0.4 nm / sec
Co-deposition (1.0 × 10 ^-3~ 1.3 × 10
^-3Pa). . On top of this, a patterned mask
A mask with an optical area of 4 mm x 5 mm)
After co-depositing nesium: silver = 10: 1 at 250 nm, silver
Deposit 300 nm (1.0 × 10^-3~ 1.3 × 10^-3P
a) A light-emitting device was manufactured. The fabricated device was dried.
Sealed in glove box. About the fabricated device
Luminance and chromaticity at drive voltage of 8V and 15V (Luminance is
Brightness meter BM-8, chromaticity is Hamamatsu Photonics
Measured using the Vector Analyzer PMA-11)
Table 3 shows the results.

[0167]

[Table 3]

[0168]

Embedded image

As is clear from the results shown in Table 3, it can be seen that the device using the compound of the present invention can emit light with high luminance even in a system doped with a fluorescent compound. In the device using Alq as the host, the blue purity decreases when the driving voltage is increased. On the other hand, in the device using the compound of the present invention as the host, almost no change in the color purity is observed, and high luminance with high color purity is obtained. It turns out that light emission is possible.

Embodiment 4 FIG. 40 mg of poly (N-vinylcarbazole), 10.0 mg of blue light-emitting material B, 2.0 mg of green light-emitting material G, 0.5 mg of red light-emitting material R, and 12.0 mg of the compound shown in Table 4 were treated with 1,2-dichloroethane 3 m.
1 and spin-coated on a washed ITO substrate. The thickness of the generated organic thin film was about 110 nm. A mask (a mask having a light-emitting area of 4 mm × 5 mm) patterned on the organic thin film is provided, and then Al:
A light-emitting element was manufactured by co-evaporation at a Li = 100: 2 ratio to have a thickness of 200 nm. This device was evaluated in the same manner as in Example 1. Table 4 shows the results.

[0171]

[Table 4]

[0172]

Embedded image

As is clear from the results shown in Table 4, the device using the compound of the present invention can be driven at a low voltage and emit light with high luminance even in the coating method in which the light emission luminance is lower than that of the comparative compound. I understand. Comparative compound 2 (PB
In the device using D), generation of a dark spot was remarkably observed, whereas in the device of the present invention, good planar light emission was shown. Furthermore, it can be seen that good white light emission is possible when the compounds of the present invention are used in combination with blue, green and red light emitting materials.

Embodiment 5 FIG. After cleaning the ITO substrate in the same manner as in Example 1, NPD was deposited to a thickness of 50 nm, and 4,4′-bis (carbazol-9-yl) biphenyl and tris (2-phenylpyridine) iridium (III) were each deposited at a deposition rate of 0.1 nm. Co-deposition at 4 nm / sec and 0.025 nm / sec to a film thickness of 20 nm.
and LiF is deposited to a thickness of 1 nm (1.0 × 1
0 ^{-3 to} 1.3 × 10 ^-3 Pa). A patterned mask (a mask having a light-emitting area of 4 mm × 5 mm) was set thereon, and aluminum was deposited to a thickness of 200 nm (1.0 mm).
× 10 ^{−3 to} 1.3 × 10 ⁻³ Pa) to produce a device.
As a result of evaluating the fabricated device, the maximum brightness was 9 in green.
High luminance and high efficiency light emission of 8,000 cd / m ² and external quantum efficiency of 14% were obtained.

Embodiment 6 FIG. After cleaning the ITO substrate in the same manner as in Example 1, Baytron P (PEDOT-PSS) was used.
The solution (polydioxyethylene-polystyrene sulfonic acid doped material / manufactured by Bayer) was spin-coated at 2000 rpm for 60 seconds, and then vacuum-dried at 100 ° C. for 1 hour.
A hole transporting film was produced (film thickness: about 100 nm). A solution of 20 mg of poly (9,9-dioctylfluorene) dissolved in 2 ml of chloroform was spin-coated thereon (1000 rpm, 20 seconds) (film thickness: about 70 n).
m). On this, Exemplified Compound 18 was vacuum-deposited (1.0 × 10 ^{−3 to} 1.3 × 10 ⁻³ Pa) with a thickness of 30 nm. Next, a mask (a mask having a light-emitting area of 4 mm × 5 mm) patterned on the organic thin film was provided, and a cathode was deposited in the same manner as in Example 1 to produce a device (device of the present invention). In addition, an element was prepared as a comparative element, except that Exemplified Compound 18 was omitted in the element manufacturing step. As a result of evaluating the EL characteristics of both devices, the comparative device had a maximum luminance of 93.
cd / m ² and external quantum efficiency of 0.1% or less,
The device of the present invention has a maximum luminance of 1680 cd / m ² and an external quantum efficiency of 1.3%, and it is clear that the compound of the present invention functions effectively as an electron transport material even when a π-conjugated polymer is used as a light emitting material. Was.

Embodiment 7 FIG. After cleaning the ITO substrate in the same manner as in Example 1, Baytron P (PEDOT-PSS) was used.
The solution (polydioxyethylene-polystyrene sulfonic acid doped material / manufactured by Bayer) was spin-coated at 2000 rpm for 60 seconds, and then dried under vacuum at 100 ° C. for 2 hours.
A hole transporting film was produced (film thickness: about 100 nm). On top of this, poly (N-vinylcarbazole) 40 mg, PBD
A solution obtained by dissolving 12 mg and 1 mg of tris (2-phenylpyridine) iridium (III) in 3 ml of chloroform was spin-coated (1500 rpm, 20 rpm).
Sec) (film thickness: about 80 nm). On top of this, Exemplified Compound 21
Is vacuum-deposited with a film thickness of 20 nm (1.0 × 10 ^{−3 to} 1.3 × 1).
0 ^-3 Pa), and LiF is deposited to a thickness of about 1 nm (1.0
× 10 ^{−3 to} 1.3 × 10 ⁻³ Pa). A patterned mask (a mask having a light-emitting area of 4 mm × 5 mm) is provided thereon, and aluminum is deposited to a thickness of 200 nm (1.
(0 × 10 ^{−3 to} 1.3 × 10 ⁻³ Pa) to produce a device (device of the present invention). In addition, an element was prepared as a comparative element, except that Exemplified Compound 21 was omitted in the element manufacturing step. As a result of evaluating the fabricated device, the external quantum efficiency at a light emission luminance of 1000 cd / m ² was 5.2% in the comparative device, whereas the external quantum efficiency was 10.2% in the device of the present invention, and the triplet was obtained. It has been clarified that the compound of the present invention effectively functions as an electron transport material also in a coating type device using tris (2-phenylpyridine) iridium (III) which is said to emit light from excitons.

[0177]

The compound of the present invention makes it possible to produce a high-luminance blue light-emitting device having good color purity in both doped and undoped devices, and to provide a device capable of emitting light in a wide wavelength range. . In addition, good light-emitting characteristics can be obtained even with a coating method with low luminance, and an element can be manufactured which is advantageous in terms of manufacturing cost. Furthermore, an organic light-emitting element having good durability and having a small change in chromaticity due to a difference in driving voltage can be obtained.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C07D 519/00 311 C07D 519/00 311 C07F 7/08 C07F 7/08 R 7/30 7/30 F H05B 33/14 H05B 33/14 B 33/22 33/22 B // C08F 12/26 C08F 12/26 226/06 226/06 F term (reference) 3K007 AB01 AB12 AB17 AB18 CA01 CB01 CB03 4C072 MM02 MM03 MM10 UU05 4H049 VN01 VN02 VP01 VQ60 VQ84 VR24 VU29 VW01 4J100 AB07P AQ26Q BC43P BC65Q BC73P BD15P CA01 CA04 DA01 JA32

Claims (16)

[Claims] 1. A light emitting device material comprising a compound represented by the following general formula (I). Embedded image (In the formula, A represents a heterocyclic group in which two or more aromatic heterocycles are condensed, and the heterocyclic groups represented by A may be the same or different. M represents an integer of 2 or more; L represents Represents a linking group.) 2. A light emitting device material, which is a compound represented by the following general formula (II). Embedded image (In the formula, B represents a heterocyclic group in which two or more 5-membered and / or 6-membered aromatic heterocycles are fused, and the heterocyclic groups represented by B may be the same or different. Represents an integer of 2 or more, and L represents a linking group.) 3. A light emitting device material comprising a compound represented by the following general formula (III). Embedded image (Wherein, X represents O, S, Se, Te or NR).
R represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. Q ₃ represents an atom group necessary for forming an aromatic hetero ring. m represents an integer of 2 or more. L represents a linking group. ) 4. A light emitting device material comprising a compound represented by the following general formula (IV). Embedded image (Wherein, X represents O, S, Se, Te or NR).
R represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. Q ₄ represents an atom group necessary for forming a nitrogen-containing aromatic hetero ring. m represents an integer of 2 or more. L
Represents a linking group. ) 5. A light-emitting device material, which is a compound represented by the following general formula (V). Embedded image (In the formula, X ₅ represents O, S or N—R. R represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. Q ₅ represents a 6-membered nitrogen-containing aromatic heterocyclic ring. Represents an atomic group necessary for formation, m represents an integer of 2 or more, and L represents a linking group.) 6. A light emitting device material, which is a compound represented by the following general formula (VI). Embedded image (In the formula, X ₆ represents O, S or N—R. R represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. Q ₆ represents a 6-membered nitrogen-containing aromatic heterocyclic ring. Represents an atomic group necessary for formation, and n represents an integer of 2 to 8. L
Represents a linking group. ) 7. A light-emitting device material, which is a compound represented by the following general formula (VII). Embedded image (In the formula, R represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group, or a heterocyclic group. Q ₇ represents an atomic group necessary for forming a 6-membered nitrogen-containing aromatic heterocyclic ring; n is 2 Represents an integer of from 1 to 8. L represents a linking group.) 8. A light emitting device material, which is a compound represented by the following general formula (VIII). Embedded image (Wherein Q ₈₁ , Q ₈₂ and Q ₈₃ each represent an atom group necessary for forming a 6-membered nitrogen-containing aromatic heterocycle.
R ₈₁ , R ₈₂ and R ₈₃ each represent a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. L ₁ ,
L ₂ and L ₃ each represent a linking group. Y represents a nitrogen atom or a 1,3,5-benzenetriyl group. ) 9. A compound represented by the following general formula (IX). Embedded image (Wherein, Q ₉₁ , Q ₉₂ and Q ₉₃ each represent an atom group necessary for forming a 6-membered nitrogen-containing aromatic heterocycle.
R ₉₁ , R ₉₂ and R ₉₃ each represent a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. ) 10. A compound represented by the following general formula (X). Embedded image (Wherein, R ₁₀₁ , R ₁₀₂ and R ₁₀₃ each represent a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. R ₁₀₄ , R ₁₀₅ and R ₁₀₆ each represent a substituent. P ₁ , p ₂ and p ₃ each represent an integer of 0 to 3.) 11. A light-emitting element material, which is a compound represented by the following general formula (XI). Embedded image (In the formula, Q ₃ represents an atom group necessary for forming an aromatic hetero ring. R ₁₁ represents a hydrogen atom or a substituent.
Represents the above integer. L represents a linking group. ) 12. A light-emitting element in which a light-emitting layer or a plurality of organic compound thin layers including a light-emitting layer is formed between a pair of electrodes, at least one of which is represented by any one of the general formulas (I) to (XI) according to claim 1 to 11. A light-emitting element comprising a layer containing at least one of the compounds represented by the formula. 13. A light-emitting element having a light-emitting layer or a plurality of organic compound thin layers including a light-emitting layer formed between a pair of electrodes, wherein at least one of the light-emitting elements is represented by any one of the general formulas (I) to (XI) according to claim 1. A light-emitting element comprising a layer in which at least one of the compounds represented by the formula is dispersed in a polymer. 14. A light-emitting element having a light-emitting layer or a plurality of organic compound thin layers including the light-emitting layer formed between a pair of electrodes, wherein at least one layer between the light-emitting layer and the cathode is provided.
A light-emitting element comprising a layer containing at least one compound represented by any one of the general formulas (I) to (XI) described in 11. 15. A light-emitting element having a light-emitting layer or a plurality of organic compound thin layers including a light-emitting layer formed between a pair of electrodes, wherein at least one layer between the blue light-emitting layer and the cathode is formed. A light-emitting element, which is a layer containing at least one compound represented by any one of formulas (I) to (XI). 16. A light-emitting element having a light-emitting layer or a plurality of organic compound thin layers including the light-emitting layer formed between a pair of electrodes, represented by the general formulas (I) to (XI) according to claims 1 to 11. A light-emitting element comprising a layer containing at least one compound and a blue light-emitting material.