JP2009130142A - Organic el device and solution containing organic el material - Google Patents

Organic el device and solution containing organic el material Download PDF

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JP2009130142A
JP2009130142A JP2007303711A JP2007303711A JP2009130142A JP 2009130142 A JP2009130142 A JP 2009130142A JP 2007303711 A JP2007303711 A JP 2007303711A JP 2007303711 A JP2007303711 A JP 2007303711A JP 2009130142 A JP2009130142 A JP 2009130142A
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organic el
carbon atoms
yl
ar
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Kenichi Fukuoka
Chishio Hosokawa
Toshihiro Iwakuma
Kazuki Nishimura
Nobuhiro Yabunouchi
俊裕 岩隈
賢一 福岡
地潮 細川
伸浩 藪ノ内
和樹 西村
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Idemitsu Kosan Co Ltd
出光興産株式会社
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Abstract

<P>PROBLEM TO BE SOLVED: To provide an organic EL device capable of achieving high efficiency and long service life, and to provide a solution containing an organic EL material which is used to form a light-emitting layer of the organic EL device. <P>SOLUTION: The organic EL device 10 includes a positive electrode 12, a negative electrode 14 and an organic thin film layer 13 provided between the positive electrode 12 and the negative electrode 14, wherein the organic thin film layer 13 includes a light-emitting layer 16 including at least a first host, a second host and a dopant indicating light emission. The second host is any one of compounds represented by formula (1). The compound having hole transfer performance and represented by the formula (1) is used as the second host, so that holes can be easily injected into the light-emitting layer 16 and the service life of the organic EL element 10 can be prolonged. <P>COPYRIGHT: (C)2009,JPO&amp;INPIT

Description

  The present invention relates to an organic EL device having excellent light emission characteristics. In particular, the present invention relates to an organic EL element having excellent lifetime. Moreover, it is related with the organic electroluminescent material containing solution for forming the light emitting layer of an organic electroluminescent element.

An organic electroluminescent device (organic EL device) that has an organic light emitting layer between an anode and a cathode, and emits light from exciton energy generated by recombination of holes and electrons injected into the organic light emitting layer It has been known.
Such an organic EL element is expected as a light emitting element excellent in luminous efficiency, image quality, power consumption, and thin design, taking advantage of the self-luminous element.

In utilizing a light emitting material in an organic EL device, a doping method is known in which a host material is doped with a dopant material.
In order to efficiently generate excitons from injected holes and electrons and efficiently link the exciton energy to light emission, the exciton energy generated by the host is transferred to the dopant, and light is emitted from the dopant. It is.

Further improvements of the organic EL device include emission lifetime and emission efficiency, and various studies have been made.
For example, in order to increase internal quantum efficiency, phosphorescent materials that obtain light emission from triplet excitons have been developed. Recently, an organic element using phosphorescence emission has been reported (for example, see Patent Document 1).
By using such a phosphorescent material, an internal quantum efficiency of 75% or more and theoretically close to 100% can be realized, and an organic EL element with high efficiency and low power consumption can be obtained.

In order to perform intermolecular energy transfer from a phosphorescent host to a phosphorescent dopant (phosphorescent material) in a phosphorescent light emitting layer formed by doping a phosphorescent material, the excited triplet energy gap Eg (T) of the phosphorescent host is It needs to be larger than Eg (T).
CBP is typically known as a material having a large Eg (T).
When this CBP is used as a phosphorescent host, energy transfer from the phosphorescent host to a phosphorescent dopant exhibiting a predetermined emission wavelength (for example, green or red) is possible, and a highly efficient light-emitting element that exhibits phosphorescence emission can be obtained. .

However, when CBP is used as a phosphorescent host, the luminous efficiency is remarkably improved by phosphorescence emission, but the emission lifetime is very short, which is not suitable for practical use.
For this reason, development of materials that can be used as phosphorescent hosts other than CBP is underway (see, for example, Non-Patent Document 1).

On the other hand, various host materials for fluorescent dopants are known, and various fluorescent hosts excellent in luminous efficiency and emission lifetime in combination with fluorescent dopants have been proposed.
However, the fluorescent host has Eg (S) that is larger than the excited singlet energy gap Eg (S) of the fluorescent dopant, but Eg (T) of the fluorescent host is not necessarily large, so it is simply a phosphorescent host. Cannot be diverted.
For example, anthracene derivatives, pyrene derivatives, naphthacene derivatives and the like are well known as fluorescent hosts. However, for example, since an anthracene derivative has an Eg (T) of about 1.9 eV, Eg (T) is insufficient to obtain light emission in a visible light wavelength region of 450 nm to 750 nm, and is not suitable as a phosphorescent host.

Further, it is known that a long-life, high-efficiency organic EL element can be obtained by adding a dopant to a host made of a plurality of materials to form a light emitting layer.
For example, in Patent Document 2, a phosphorescent light-emitting layer is formed using a phosphorescent host containing two or more types of hole transport materials, thereby improving efficiency and lifetime.

US application 2002/182441 publication JP 2006-135295 A Applied Physics Letters 90,123509 (2007)

Since the organic EL element described in Patent Document 1 includes a phosphorescent light emitting layer, there is a problem in that although the light emission efficiency is high and the power consumption is small, the lifetime is short.
In Non-Patent Document 1, various materials are studied as a phosphorescent host. Until a phosphorescent host capable of efficiently transferring energy to a phosphorescent dopant and providing a practically long-lived phosphorescent light-emitting layer is found. It has not reached.
The organic EL element described in Patent Document 2 exhibits long-life and highly efficient light emission by using a phosphorescent host made of a plurality of materials. However, since the material constituting the phosphorescent host was CBP or a compound similar to CBP, the effect was not sufficient.
Accordingly, an object of the present invention is to provide a phosphorescent organic EL device having a high efficiency and a long lifetime. Moreover, it aims at providing the organic electroluminescent material containing solution for forming the light emitting layer of such an organic electroluminescent element.

  The inventors of the present invention have made extensive studies in order to solve such problems, and are represented by the following formulas (1) to (5) as the second host of the light emitting layer including the first host and the second host. It has been found that by using a compound, the carrier balance is improved and the lifetime of the phosphorescent device can be extended, and the present invention has been completed.

  The organic EL device of the present invention is an organic EL device comprising an anode, a cathode, and an organic thin film layer provided between the anode and the cathode, wherein the organic thin film layer is at least a first And a second host, and a dopant that emits light, and the second host is at least one of the compounds represented by the following formulas (1) to (5) It is characterized by that.

In formulas (1) to (5), Ar 1 to Ar 4 are a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthrene group. is there.
Ar 5 to Ar 13 are a substituted or unsubstituted aryl group having 5 to 40 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 40 carbon atoms, and a substituted or unsubstituted amino group to which an aromatic amino group is bonded. An aryl group having 8 to 40 carbon atoms, or a substituted or unsubstituted aryl group having 8 to 40 carbon atoms to which an aromatic heterocyclic group is bonded.
Ar 1 and Ar 2 , Ar 3 and Ar 4 , Ar 5 and Ar 6 , Ar 8 and Ar 9 , Ar 10 and Ar 11 , Ar 12 and Ar 13 may be bonded to each other to form a ring.
L 1 to L 4 are a single bond or a linking group having 1 to 30 carbon atoms.
R 1 to R 17 are each a hydrogen atom, a halogen atom, or an optionally substituted alkyl group having 1 to 40 carbon atoms, an optionally substituted heterocyclic group having 3 to 20 carbon atoms, or a substituent. A non-condensed aryl group having 6 to 40 carbon atoms which may have a condensed aryl group having 6 to 12 carbon atoms which may have a substituent, or a condensed group having 12 to 40 carbon atoms which may have a substituent A non-condensed mixed aryl group, an aralkyl group having 7 to 20 carbon atoms that may have a substituent, an alkenyl group having 2 to 40 carbon atoms that may have a substituent, and a substituent that may have 1 to 1 40 alkylamino groups, 7 to 60 carbon atoms aralkylamino groups which may have substituents, 3 to 20 carbon atoms alkylsilyl groups which may have substituents, and substituents C8-C40 arylsilyl group, C8-C40 arral optionally having a substituent Rushiriru group, a halogenated alkyl group which may 1 to 40 carbon atoms which may have a substituent.
X 1 to X 3 represent a sulfur atom, an oxygen atom, or a monoaryl-substituted nitrogen atom.

Here, the host used in the phosphorescent light-emitting element has a wide band gap and is hard to inject holes.
According to this invention, since the formulas (1) to (5) having hole transportability are used as the second host of the light emitting layer, it becomes easy to inject holes into the light emitting layer, and the organic EL The lifetime of the element can be extended.
Note that the content of the second host is desirably 50% or less, and more desirably 20% or less. If there are too many second hosts, holes will reach the electron transport layer, which will adversely affect efficiency and lifetime. The preferred dopant concentration is 5% or more, desirably 10% or more, and more desirably 50% or more.

Here, as a halogen atom of R < 1 > -R < 17 > in said Formula (1)-(5), a fluorine, chlorine, a bromine, an iodine etc. are mentioned, for example.

The alkyl group of the formula (1) ~ (5) R 1 carbon atoms which may have a substituent to R 17 1 to 40 in, for example, a methyl group, an ethyl group, a propyl group, an isopropyl radical, n -Butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl Group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 2-methylpentyl group Group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, 3-methylpentyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxy Til group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3- Trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, , 2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-amino Ethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group, 1,2,3-tricia Nopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 1,2-dinitroethyl group, 2,3-dinitro-t-butyl group, 1,2,3-trinitro A propyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, a 3,5-tetramethylcyclohexyl group and the like can be mentioned.

  Among these, a methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group are preferable. N-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group N-octadecyl group, neopentyl group, 1-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, cyclohexyl group, cyclooctyl group, 3,5-tetramethylcyclohexyl group, etc. Can be mentioned.

Examples of the heterocyclic group having 3 to 20 carbon atoms which may have a substituent of R 1 to R 17 in the formulas (1) to (5) include a 1-pyrrolyl group, a 2-pyrrolyl group, a 3- Pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 1-imidazolyl group, 2-imidazolyl group, 1-pyrazolyl group, 1-indolidinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group 7-indolidinyl group, 8-indolidinyl group, 2-imidazopyridinyl group, 3-imidazopyridinyl group, 5-imidazopyridinyl group, 6-imidazopyridinyl group, 7-imidazopyridinyl group 8-imidazolidinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5- Group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2- Furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzo Furanyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group Group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group, 5-quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group Group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, β-carbolin-1-yl, β-carbolin-3-yl, β-carbolin-4-yl, β-carbolin-5-yl, β -Carbolin-6-yl, β-carbolin-7-yl, β-carbolin-6-yl, β-carbolin-9-yl, 1-phenanthridinyl group, 2-phenanthridinyl group, 3-phen Nantridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9-phena Tridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1,7-phenanthrolin-2-yl group, 1,7 -Phenanthroline-3-yl group, 1,7-phenanthroline-4-yl group, 1,7-phenanthroline-5-yl group, 1,7-phenanthroline-6-yl group, 1,7-phenanthroline-8-yl Group, 1,7-phenanthroline-9-yl group, 1,7-phenanthroline-10-yl group, 1,8-phenanthroline-2-yl group, 1,8-phenanthroline-3-yl group, 1,8- Phenanthroline-4-yl group, 1,8-phenanthroline-5-yl group, 1,8-phenanthroline-6-yl group, 1,8-phenanthroline-7 -Yl group, 1,8-phenanthroline-9-yl group, 1,8-phenanthroline-10-yl group, 1,9-phenanthroline-2-yl group, 1,9-phenanthroline-3-yl group, 1, 9-phenanthroline-4-yl group, 1,9-phenanthroline-5-yl group, 1,9-phenanthroline-6-yl group, 1,9-phenanthroline-7-yl group, 1,9-phenanthroline-8- Yl group, 1,9-phenanthroline-10-yl group, 1,10-phenanthroline-2-yl group, 1,10-phenanthroline-3-yl group, 1,10-phenanthroline-4-yl group, 1,10 -Phenanthrolin-5-yl group, 2,9-phenanthroline-1-yl group, 2,9-phenanthroline-3-yl group, 2,9-phenanthroline-4-yl group 2,9-phenanthroline-5-yl group, 2,9-phenanthroline-6-yl group, 2,9-phenanthroline-7-yl group, 2,9-phenanthroline-8-yl group, 2,9-phenanthroline- 10-yl group, 2,8-phenanthroline-1-yl group, 2,8-phenanthroline-3-yl group, 2,8-phenanthroline-4-yl group, 2,8-phenanthroline-5-yl group, 2 , 8-phenanthroline-6-yl group, 2,8-phenanthroline-7-yl group, 2,8-phenanthroline-9-yl group, 2,8-phenanthroline-10-yl group, 2,7-phenanthroline-1 -Yl group, 2,7-phenanthroline-3-yl group, 2,7-phenanthroline-4-yl group, 2,7-phenanthroline-5-yl group, 2,7-phena Trolin-6-yl group, 2,7-phenanthroline-8-yl group, 2,7-phenanthroline-9-yl group, 2,7-phenanthroline-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 10-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 10-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-furazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrole- 1-yl group, 2-methylpyrrol-3-yl group, 2-methylpyrrole-4 -Yl group, 2-methylpyrrol-5-yl group, 3-methylpyrrol-1-yl group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrole-5 -Yl group, 2-t-butylpyrrol-4-yl group, 3- (2-phenylpropyl) pyrrol-1-yl group, 2-methyl-1-indolyl group, 4-methyl-1-indolyl group, 2 -Methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t-butyl 1-indolyl group, 4-t-butyl 1-indolyl group, 2-t-butyl 3-indolyl group, 4-t -Butyl 3-indolyl group, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3 -Diben Thiophenyl group, 4-dibenzothiophenyl group, 1-silafluorenyl group, 2-silafluorenyl group, 3-silafluorenyl group, 4-silafluorenyl group, 1-germafluorenyl group, 2-germafluorenyl group, 3-germaflule Examples include oleenyl group and 4-germafluorenyl group.

  Among these, 2-pyridinyl group, 1-indolidinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group, 7-indolidinyl group, 8-indolidinyl group, 2-imidazopyr are preferable. Zinyl group, 3-Imidazopyridinyl group, 5-Imidazopyridinyl group, 6-Imidazopyridinyl group, 7-Imidazopyridinyl group, 8-Imidazopyridinyl group, 3-Pyridinyl group, 4 -Pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3 -Isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzo Furanyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzothiophenyl group, 4-dibenzothiophenyl group, 1-silafluorenyl group, 2-silafluorenyl group, 3-silafluorenyl group, 4-silafluorenyl Group, 1-germafluorenyl group, 2-germafluorenyl group, 3-germafluorenyl group, 4-germafluorenyl group and the like.

Examples of the non-condensed aryl group having 6 to 40 carbon atoms that may have a substituent of R 1 to R 17 in the above formulas (1) to (5) include a phenyl group, a 2-biphenylyl group, a 3- Biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, pt-butylphenyl group, p- (2-phenylpropyl) ) Phenyl group, 4′-methylbiphenylyl group, 4 ″ -t-butyl-p-terphenyl-4-yl group, o-cumenyl group, m-cumenyl group, p-cumenyl group, 2,3-xylyl group 3,4-xylyl group, 2,5-xylyl group, A cytyl group, m-quaterphenyl group, etc. are mentioned.
Among these, a phenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-ter are preferable. Examples include phenyl-2-yl group, p-tolyl group, 3,4-xylyl group, m-quaterphenyl-2-yl group and the like.

Examples of the condensed aryl group having 6 to 12 carbon atoms that may have a substituent of R 1 to R 17 in the formulas (1) to (5) include a 1-naphthyl group and a 2-naphthyl group. .
The condensed non-condensed mixed aryl group having 12 to 40 carbon atoms which may have a substituent of R 1 to R 17 in the formulas (1) to (5) may have the above substituent. And a group formed by a combination of a -12 condensed aryl group and a non-condensed aryl group having 6 to 40 carbon atoms which may have the substituent.

Examples of the aralkyl group having 7 to 20 carbon atoms which may have a substituent of R 1 to R 17 in the formulas (1) to (5) include a benzyl group, a 1-phenylethyl group, and 2-phenylethyl. Group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, 2-β-naphthylisopropyl group, 1-pyrrolylmethyl Group, 2- (1-pyrrolyl) ethyl group, p-methylbenzyl group, m-methylbenzyl group, o-methylbenzyl group, p-chlorobenzyl group, m-chloro Nyl group, o-chlorobenzyl group, p-bromobenzyl group, m-bromobenzyl group, o-bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group M-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group, p-nitrobenzyl group, m-nitrobenzyl group, o-nitrobenzyl group, p -Cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-hydroxy-2-phenylisopropyl group, 1-chloro-2-phenylisopropyl group and the like.
Among these, benzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group are preferable. Etc.

Examples of the alkenyl group having 2 to 40 carbon atoms that may have a substituent of R 1 to R 17 in the formulas (1) to (5) include a vinyl group, an allyl group, a 1-butenyl group, 2- Butenyl, 3-butenyl, 1,3-butanedienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethyl Allyl group, 2-methylallyl group, 1-phenylallyl group, 2-phenylallyl group, 3-phenylallyl group, 3,3-diphenylallyl group, 1,2-dimethylallyl group, 1-phenyl-1-butenyl group , 3-phenyl-1-butenyl group and the like, and preferably styryl group, 2,2-diphenylvinyl group, 1,2-diphenylvinyl group and the like.

In the above formulas (1) to (5), R 1 to R 17 may have a substituent of 1 to 40 alkylamino groups, and may have a substituent of 7 to 60 carbon atoms aralkylamino group. Is represented by —NQ 1 Q 2, and specific examples of Q 1 and Q 2 are each independently the same as those described for the alkyl group, the aryl group, and the aralkyl group, and are preferable. The example is similar.
The alkyl silyl group of 3 to 20 carbon atoms which may have a substituent R 1 to R 17 in Formula (1) to (5), trimethylsilyl group, triethylsilyl group, t- butyl dimethyl silyl group, Examples thereof include a vinyldimethylsilyl group and a propyldimethylsilyl group.
The aryl silyl group of the formula (1) ~ (5) R 1 carbon atoms which may have a substituent to R 17 8 to 40 in, triphenylsilyl group, tri-biphenyl silyl group, di - terphenyl -Phenylsilyl group, phenyldimethylsilyl group, t-butyldiphenylsilyl group and the like.

Examples of the aralkylsilyl group having 8 to 40 carbon atoms which may have a substituent of R 1 to R 17 in the above formulas (1) to (5) include a tribenzylsilyl group, a benzyldimethylsilyl group, and t-butyldiethyl. A benzylsilyl group etc. are mentioned.
Examples of the halogenated alkyl group having 1 to 40 carbon atoms which may have a substituent of R 1 to R 17 in the above formulas (1) to (5) include, for example, at least one hydrogen atom of the alkyl group is a halogen atom. The thing substituted by the atom is mentioned, A preferable example is also the same.

Specific examples of the compounds represented by the formulas (1) to (5) are shown below, but are not limited to these exemplified compounds.
Examples of the compound represented by the formula (1) include the following.

  Examples of the compound represented by the formula (2) include the following.

  Examples of the compound represented by the formula (3) include the following.

  Examples of the compound represented by the formula (4) include the following.

  Examples of the compound represented by the formula (5) include the following.

In the formula (3), it is preferable that Ar 8 and Ar 9 do not form a ring structure.
In the case where Ar 8 and Ar 9 form a ring structure, the hole injection property is lowered, which is not preferable.
Moreover, the compound represented by said Formula (1)-(5) contained in a light emitting layer is not limited to one type. That is, the light emitting layer may contain a plurality of compounds represented by the formulas (1) to (5).

In the organic EL device of the present invention, the first host has a substituted or unsubstituted polycyclic fused aromatic skeleton having 10 to 30 nuclear atoms, and has the lowest excited triplet. The energy gap is preferably 2.1 eV or more and 2.7 eV or less, and the dopant is preferably a phosphorescent dopant exhibiting phosphorescence.
Furthermore, in the organic EL device of the present invention, the first host preferably has a substituted or unsubstituted polycyclic fused aromatic skeleton having 20 to 30 nucleus atoms.

According to the present invention, a phosphorescent dopant is added to the first host to constitute a light emitting layer that exhibits phosphorescence.
In this case, the phosphorescent dopant is a material that emits light by receiving energy transfer from the host, or a material that emits light by generating excitons directly on the phosphorescent dopant.
That is, since the triplet energy gap of the host is 2.1 eV or more and 2.7 eV or less, the energy for the phosphorescent dopant whose triplet energy cap is 2.7 eV or less, more efficiently 2.5 eV or less. It can be moved to cause phosphorescence.
Anthracene derivatives well known as fluorescent hosts are also unsuitable as a phosphorescent dopant for red light emission, but the triplet energy gap is 2.1 eV or more in the host of the present invention. A phosphorescent dopant that emits light can emit light.
However, although CBP, which is a well-known phosphorescent host, functions as a host for phosphorescent dopants having a wavelength shorter than that of green, the triplet energy gap of the host of the present invention is 2.7 eV or less. To phosphorescent dopants that emit green light only.
In the present invention, the host material skeleton is a polycyclic fused ring, whereby the stability of the molecule can be increased and the device life can be extended.
At this time, if the number of nucleus atoms in the skeleton is too small, the stability of the molecule is not sufficiently increased. Therefore, the number of atoms is set to 10 or more. On the other hand, if the number of polycyclic fused rings is too large, the HOMO-LUMO gap. And the triplet energy gap becomes less than the useful emission wavelength, so the number of nuclear atoms is 30 or less.
Thereby, it can be set as a suitable host as a host of the light emitting layer which shows a useful light emission wavelength.
The number of nucleus atoms in the polycyclic fused aromatic skeleton is more preferably 20-30.

Conventionally, since a host corresponding to a phosphorescent dopant that can be widely applied to a phosphorescent dopant in a wide wavelength range from green to red is selected, CBP or the like having a wide triplet energy gap is used as the host.
However, the CBP has a problem that the triplet energy gap Eg (T) is wide but the lifetime is short.

In this respect, in the present invention, the number of nuclear atoms in the polycyclic fused aromatic skeleton is 10 to 30, and the lowest excited triplet energy gap is 2.1 eV or more and 2.7 eV or less. Although not applicable to a phosphorescent dopant host, it functions as a host for a phosphorescent dopant of 2.7 eV or less. Furthermore, if the triplet energy gap is too wide as in CBP, there is a problem that the energy gap difference is too large for the red phosphorescent dopant and the intermolecular energy transfer is not performed efficiently. According to the host of the invention, the energy gap is adapted to the red phosphorescent dopant, so that the energy can be efficiently transferred from the host exciton to the phosphorescent dopant, and a highly efficient light-emitting layer is formed. can do.
Thus, according to the present invention, a light-emitting layer having a high efficiency and a long lifetime can be formed.

Here, the triplet energy gap Eg (T) of the material is defined as an example based on the phosphorescence emission spectrum. For example, in the present invention, the triplet energy gap Eg (T) is defined as follows. It is done.
That is, each material is dissolved at 10 μmol / L in an EPA solvent (diethyl ether: isopentane: ethanol = 5: 5: 2 by volume ratio) to obtain a sample for phosphorescence measurement.
Then, the phosphorescence measurement sample is put in a quartz cell, cooled to 77K, irradiated with excitation light, and the wavelength of the emitted phosphorescence is measured.
A triplet energy gap Eg (T) is defined as a value obtained by drawing a tangent line to the short-wavelength rise of the obtained phosphorescence spectrum and converting the wavelength value at the intersection of the tangent line and the base line into energy.
For measurement, for example, a commercially available measuring device F-4500 (manufactured by Hitachi) can be used.
However, any value that can be defined as a triplet energy gap without departing from the gist of the present invention is acceptable, regardless of such rules.

  In the organic EL device of the present invention, the polycyclic fused aromatic skeleton is preferably contained in the chemical structural formula as a divalent or higher valent group.

Examples of the substituent of the polycyclic fused aromatic skeleton include, for example, a halogen atom, hydroxyl group, substituted or unsubstituted amino group, nitro group, cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl. Group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group, substituted Or an unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, or a carboxyl group is mentioned.
When the polycyclic fused aromatic skeleton has a plurality of substituents, they may form a ring.

  Examples of the halogen atom include fluorine, chlorine, bromine and iodine.

A substituted or unsubstituted amino group is represented by —NX 1 X 2, and examples of X 1 and X 2 are independently a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2 -Hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl Group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group Group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2, 3-dibromo-t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3- Diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1 , 2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group, 1,2,3- Tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t-butyl group 1,2,3-trinitropropyl group, phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 4- Styrylphenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-ter Phenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl Group, m-tolyl group, p-tolyl group, pt-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4 -Methyl-1-anthryl group, 4'-methylbiphenylyl group, 4 "-t-butyl-p-terphenyl-4-yl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group , 3-pyridinyl group, 4-pyridinyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuran group Nyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group, 5-quinoxalinyl group 6-quinoxalinyl group, 1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group, 7-phenanth Lysinyl group, 8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9- Acridinyl group, 1,7-phenanthrolin-2-yl group, 1,7-phenanthrolin-3-yl group, 1,7-phenanthrolin-4 Yl group, 1,7-phenanthrolin-5-yl group, 1,7-phenanthrolin-6-yl group, 1,7-phenanthrolin-8-yl group, 1,7-phenanthrolin- 9-yl group, 1,7-phenanthrolin-10-yl group, 1,8-phenanthrolin-2-yl group, 1,8-phenanthrolin-3-yl group, 1,8-phenance Lorin-4-yl group, 1,8-phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group, 1,8- Phenanthrolin-9-yl group, 1,8-phenanthrolin-10-yl group, 1,9-phenanthrolin-2-yl group, 1,9-phenanthrolin-3-yl group, 1, 9-phenanthrolin-4-yl group, 1,9-phenanthrolin-5-yl group, 1,9- Phenanthrolin-6-yl group, 1,9-phenanthrolin-7-yl group, 1,9-phenanthrolin-8-yl group, 1,9-phenanthrolin-10-yl group, 1, 10-phenanthrolin-2-yl group, 1,10-phenanthrolin-3-yl group, 1,10-phenanthrolin-4-yl group, 1,10-phenanthrolin-5-yl group, 2,9-phenanthrolin-1-yl group, 2,9-phenanthrolin-3-yl group, 2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl Group, 2,9-phenanthroline-6-yl group, 2,9-phenanthrolin-7-yl group, 2,9-phenanthrolin-8-yl group, 2,9-phenanthroline-10 -Yl group, 2,8-phenanthrolin-1-yl group, 2,8-phenane Lorin-3-yl group, 2,8-phenanthrolin-4-yl group, 2,8-phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group, 2,8- Phenanthrolin-7-yl group, 2,8-phenanthrolin-9-yl group, 2,8-phenanthrolin-10-yl group, 2,7-phenanthrolin-1-yl group, 2, 7-phenanthrolin-3-yl group, 2,7-phenanthrolin-4-yl group, 2,7-phenanthrolin-5-yl group, 2,7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group, 2,7-phenanthrolin-9-yl group, 2,7-phenanthrolin-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1 -Phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group 4-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group Group, 3-furazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrol-3-yl group, 2-methylpyrrol-4-yl group, 2-methyl Pyrrol-5-yl group, 3-methylpyrrol-1-yl group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrol-5-yl group, 2-t -Butylpyrrol-4-yl group, 3- (2-phenylpropyl) pyrrol-1-yl group, 2-methyl-1-indolyl group, 4-methyl-1 -Indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t-butyl-1-indolyl group, 4-t-butyl-1-indolyl group, 2-t-butyl- A 3-indolyl group, 4-t-butyl-3-indolyl group, etc. are mentioned.

  Examples of substituted or unsubstituted alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl, and n-hexyl. Group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1 Bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group, 1,2,3-tribromopropyl Group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1, 2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3 -Diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl Group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2 -Nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t-butyl group, 1,2,3-trinitropropyl group, etc. It is done.

  Examples of substituted or unsubstituted alkenyl groups include vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butanedienyl, 1-methylvinyl, styryl, 4 -Diphenylaminostyryl group, 4-di-p-tolylaminostyryl group, 4-di-m-tolylaminostyryl group, 2,2-diphenylvinyl group, 1,2-diphenylvinyl group, 1-methylallyl group, 1 , 1-dimethylallyl group, 2-methylallyl group, 1-phenylallyl group, 2-phenylallyl group, 3-phenylallyl group, 3,3-diphenylallyl group, 1,2-dimethylallyl group, 1-phenyl- Examples include 1-butenyl group and 3-phenyl-1-butenyl group.

  Examples of the substituted or unsubstituted cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, and the like.

  The substituted or unsubstituted alkoxy group is a group represented by -OY, and examples of Y include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2 -Dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2 -Chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3-trick Ropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group, 1 , 2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo -T-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3 -Diaminoisopropyl group, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2 Cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t-butyl group, 1,2,3-tri Examples thereof include a nitropropyl group.

  Examples of the substituted or unsubstituted aromatic hydrocarbon group include phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2- Phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2- Biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl -4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, pt-butyl group Nyl group, p- (2-phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylyl group, 4 "-T-butyl-p-terphenyl-4-yl group and the like.

  Examples of the substituted or unsubstituted aromatic heterocyclic group include 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-pyrrolyl group, Indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4- Isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6- Benzofuranyl group, 7-benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuranyl group, 4-isobenzo Ranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl Group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl Group, 5-quinoxalinyl group, 6-quinoxalinyl group, 1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group Group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2 Acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1,7-phenanthrolin-2-yl group, 1,7-phenanthrolin-3-yl group, 1,7-phenance Lorin-4-yl group, 1,7-phenanthrolin-5-yl group, 1,7-phenanthrolin-6-yl group, 1,7-phenanthrolin-8-yl group, 1,7- Phenanthrolin-9-yl group, 1,7-phenanthrolin-10-yl group, 1,8-phenanthrolin-2-yl group, 1,8-phenanthrolin-3-yl group, 1, 8-phenanthroline-4-yl group, 1,8-phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group, 1,8-phenanthrolin-9-yl group, 1,8-phenanth Lorin-10-yl group, 1,9-phenanthrolin-2-yl group, 1,9-phenanthrolin-3-yl group, 1,9-phenanthrolin-4-yl group, 1,9- Phenanthrolin-5-yl group, 1,9-phenanthrolin-6-yl group, 1,9-phenanthrolin-7-yl group, 1,9-phenanthrolin-8-yl group, 1, 9-phenanthrolin-10-yl group, 1,10-phenanthrolin-2-yl group, 1,10-phenanthrolin-3-yl group, 1,10-phenanthrolin-4-yl group, 1,10-phenanthrolin-5-yl group, 2,9-phenanthrolin-1-yl group, 2,9-phenanthrolin-3-yl group, 2,9-phenanthrolin-4-yl Group, 2,9-phenanthrolin-5-yl group, 2,9-phenanthroline- -Yl group, 2,9-phenanthrolin-7-yl group, 2,9-phenanthrolin-8-yl group, 2,9-phenanthrolin-10-yl group, 2,8-phenanthroline -1-yl group, 2,8-phenanthrolin-3-yl group, 2,8-phenanthrolin-4-yl group, 2,8-phenanthrolin-5-yl group, 2,8-phen group Nansulolin-6-yl group, 2,8-phenanthrolin-7-yl group, 2,8-phenanthrolin-9-yl group, 2,8-phenanthrolin-10-yl group, 2,7 -Phenanthrolin-1-yl group, 2,7-phenanthrolin-3-yl group, 2,7-phenanthrolin-4-yl group, 2,7-phenanthrolin-5-yl group, 2 , 7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group, 2, -Phenanthrolin-9-yl group, 2,7-phenanthrolin-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group 4-phenothiazinyl group, 10-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 10-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5- Oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-furazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrol-3-yl group, 2- Methylpyrrol-4-yl group, 2-methylpyrrol-5-yl group, 3-methylpyrrol-1- Yl group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrol-5-yl group, 2-t-butylpyrrol-4-yl group, 3- (2- Phenylpropyl) pyrrol-1-yl group, 2-methyl-1-indolyl group, 4-methyl-1-indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t- Examples thereof include a butyl-1-indolyl group, a 4-t-butyl-1-indolyl group, a 2-t-butyl-3-indolyl group, and a 4-t-butyl-3-indolyl group.

  Examples of substituted or unsubstituted aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, α-naphthylmethyl. Group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2- β-naphthylethyl group, 1-β-naphthylisopropyl group, 2-β-naphthylisopropyl group, 1-pyrrolylmethyl group, 2- (1-pyrrolyl) ethyl group, p-methylbenzyl group, m-methylbenzyl group, o -Methylbenzyl group, p-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromobenzyl group, m-bromobe Gil group, o-bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group M-aminobenzyl group, o-aminobenzyl group, p-nitrobenzyl group, m-nitrobenzyl group, o-nitrobenzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1 -Hydroxy-2-phenylisopropyl group, 1-chloro-2-phenylisopropyl group and the like.

  A substituted or unsubstituted aryloxy group is represented by —OZ, and examples of Z include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, 1 -Phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4 -Pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl Group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group , Pt-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′- Methylbiphenylyl group, 4 ″ -t-butyl-p-terphenyl-4-yl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-iso Benzofuranyl group, 7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1- Isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group, 5-quinoxalinyl group, 6-quinoxalinyl group, 1- Phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group Group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4 -Acridinyl group, 9-acridinyl group, 1,7-phenanthrolin-2-yl group, 1,7-phenanthrolin-3-yl group, 1,7-phenanthrolin-4-yl group, 1, 7-phenanthrolin-5-yl group, 1,7-phenanthrolin-6-yl group, 1,7-phenanthrolin-8-yl group, 1,7-phenanthrolin-9-yl group, 1,7-phenanthrolin-10-yl group, 1,8-phenanthrolin-2-yl group, 1,8-phenanthrolin-3-yl group, 1,8-phenanthrolin-4-yl Group, 1,8-phenanthrolin-5-yl group 1,8-phenanthroline-6-yl group, 1,8-phenanthrolin-7-yl group, 1,8-phenanthrolin-9-yl group, 1,8-phenanthrolin-10-yl Group, 1,9-phenanthrolin-2-yl group, 1,9-phenanthrolin-3-yl group, 1,9-phenanthrolin-4-yl group, 1,9-phenanthrolin-5 -Yl group, 1,9-phenanthroline-6-yl group, 1,9-phenanthrolin-7-yl group, 1,9-phenanthrolin-8-yl group, 1,9-phenanthroline -10-yl group, 1,10-phenanthrolin-2-yl group, 1,10-phenanthrolin-3-yl group, 1,10-phenanthrolin-4-yl group, 1,10-phen group Nansulolin-5-yl group, 2,9-phenanthrolin-1-yl group, 2,9 Phenanthrolin-3-yl group, 2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group, 2,9-phenanthrolin-6-yl group, 2, 9-phenanthroline-7-yl group, 2,9-phenanthrolin-8-yl group, 2,9-phenanthrolin-10-yl group, 2,8-phenanthrolin-1-yl group, 2,8-phenanthrolin-3-yl group, 2,8-phenanthrolin-4-yl group, 2,8-phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group Group, 2,8-phenanthroline-7-yl group, 2,8-phenanthrolin-9-yl group, 2,8-phenanthrolin-10-yl group, 2,7-phenanthroline-1 -Yl group, 2,7-phenanthroline-3-yl group, 2,7-phenanthroline -4-yl group, 2,7-phenanthrolin-5-yl group, 2,7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group, 2,7-phen group Nanthrolin-9-yl group, 2,7-phenanthrolin-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4 -Phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-flazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrol-3-yl group, 2-methyl group Rupyrrol-4-yl group, 2-methylpyrrol-5-yl group, 3-methylpyrrol-1-yl group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methyl Pyrrol-5-yl group, 2-t-butylpyrrol-4-yl group, 3- (2-phenylpropyl) pyrrol-1-yl group, 2-methyl-1-indolyl group, 4-methyl-1-indolyl group Group, 2-methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t-butyl-1-indolyl group, 4-t-butyl-1-indolyl group, 2-t-butyl-3- Indolyl group, 4-t-butyl-3-indolyl group and the like can be mentioned.

  A substituted or unsubstituted alkoxycarbonyl group is represented as —COOY, and examples of Y include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3-trimethyl Ropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group, 1 , 2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo -T-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3 -Diaminoisopropyl group, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2 Cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t-butyl group, 1,2,3-tri Examples thereof include a nitropropyl group.

  Furthermore, in the organic EL element of the present invention, the polycyclic fused aromatic skeleton has a substituent, and the substituent is preferably a substituted or unsubstituted aryl group or heteroaryl group.

  According to this invention, by introducing an aryl group or heteroaryl group as a substituent, it is possible to extend the life by adjusting the energy gap and preventing molecular association.

  And in the organic EL element of this invention, it is preferable that the said substituent does not have a carbazole skeleton.

Here, when a carbazole group is introduced as a substituent, the triplet energy gap becomes wide due to an increase in ionization potential and the like, so that it can be applied as a host to phosphorescent dopants with shorter wavelengths. The introduction of a group is not preferable because it leads to a shortened life.
In this respect, in the present invention, the carbazole group can be removed from the substituent, and the lifetime can be extended although the energy gap is narrowed.

  Furthermore, in the organic EL device of the present invention, the polycyclic fused aromatic skeleton is preferably selected from the group of substituted or unsubstituted phenanthrene diyl, chrysenediyl, fluoranthenediyl, and triphenylenediyl.

  In the organic EL device of the present invention, the polycyclic fused aromatic skeleton is preferably substituted with a group having phenanthrene, chrysene, fluoranthene, or triphenylene.

  Furthermore, in the organic EL element of the present invention, the polycyclic fused aromatic skeleton is preferably represented by any of the following formulas (6) to (9).

(In the formulas (6) to (9), Ar 1 to Ar 5 represent a substituted or unsubstituted condensed ring structure having 4 to 10 nuclear carbon atoms.)

Examples of the compound represented by the formula (6) include substituted or unsubstituted phenanthrene and chrysene.
Examples of the compound represented by the formula (7) include substituted or unsubstituted acenaphthylene, acenaphthene, fluoranthene, and the like.
Examples of the compound represented by the formula (8) include substituted or unsubstituted benzofluoranthene.
Examples of the compound represented by the formula (9) include naphthalene alone and derivatives.

  The polycyclic fused aromatic skeleton is preferably a phenanthrene simple substance or derivative represented by the following formula (21).

Examples of the substituent of the phenanthrene derivative include alkyl group, cycloalkyl group, aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxyl group, mercapto group, alkoxy group, alkylthio group, aryl ether group, aryl thioether group, aryl Group, heterocyclic group, halogen, haloalkane, haloalkene, haloalkyne, cyano group, aldehyde group, carbonyl group, carboxyl group, ester group, amino group, nitro group, silyl group, and siloxanyl group.
Examples of such phenanthrene derivatives include those of the following formulas (50A) and (50B).

In formula (50A), R 1 to R 10 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 5 to 30 nuclear carbon atoms, a branched or straight chain alkyl group having 1 to 30 carbon atoms. And a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, which is a single or a combination of plural groups.
Specific examples of the phenanthrene derivative represented by the formula (21) include the following.

  Furthermore, the polycyclic fused aromatic skeleton is preferably a simple substance or a derivative of chrysene represented by the following formula (22).

  Examples of such chrysene derivatives include those of the following formula (51A).

In formula (51A), R 1 to R 12 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 5 to 30 nuclear carbon atoms, a branched or straight chain alkyl group having 1 to 30 carbon atoms. And a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, which is a single or a combination of plural groups.
Specific examples of the chrysene derivative represented by the formula (22) include the following.

  The polycyclic fused aromatic skeleton is preferably a simple substance or a derivative of a compound (benzo [c] phenanthrene) represented by the following formula (23).

  Examples of such a benzo [c] phenanthrene derivative include those represented by the following formula (52A).

In formula (52A), R 1 to R 9 each independently represent a hydrogen atom, a substituted or unsubstituted aryl group having 5 to 30 nuclear carbon atoms, a branched or straight chain alkyl group having 1 to 30 carbon atoms. And a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, which is a single or a combination of plural groups.
Specific examples of the benzo [c] phenanthrene derivative represented by the formula (23) include the following.

  The polycyclic fused aromatic skeleton is preferably a simple substance or a derivative of a compound (benzo [c] chrysene) represented by the following formula (24).

  Examples of such a benzo [c] chrysene derivative include those represented by the following formula (53A).

In formula (53A), R 1 to R 11 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 5 to 30 nuclear carbon atoms, or a branched or straight chain alkyl group having 1 to 30 carbon atoms. And a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, which is a single or a combination of plural groups.
Specific examples of the benzo [c] chrysene derivative represented by the formula (24) include the following.

  Furthermore, the polycyclic fused aromatic skeleton is preferably a simple substance or a derivative of a compound represented by the following formula (25) (dibenzo [c, g] phenanthrene).

  Examples of derivatives of such compounds include the following.

  The polycyclic fused aromatic skeleton is preferably a simple substance or a derivative of fluoranthene represented by the following formula (26).

  Examples of such a fluoranthene derivative include those represented by the following formula (55A).

In formula (55A), X 12 to X 21 represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, or a substituted or unsubstituted aryl group.
The aryl group represents a carbocyclic aromatic group such as a phenyl group or a naphthyl group, for example, a heterocyclic aromatic group such as a furyl group, a thienyl group, or a pyridyl group.

X 12 to X 21 are preferably a hydrogen atom, a halogen atom (eg, fluorine atom, chlorine atom, bromine atom), a linear, branched or cyclic alkyl group having 1 to 16 carbon atoms (eg, methyl group, ethyl group). Group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, cyclopentyl group, n-hexyl Group, 3,3-dimethylbutyl group, cyclohexyl group, n-heptyl group, cyclohexylmethyl group, n-octyl group, tert-octyl group, 2-ethylhexyl group, n-nonyl group, n-decyl group, n-dodecyl Group, n-tetradecyl group, n-hexadecyl group, etc.), C1-C16 linear, branched or cyclic alkoxy group (for example, methoxy group, Xoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, n-pentyloxy group, neopentyloxy group, cyclopentyloxy group, n-hexyloxy group, 3,3- Dimethylbutyloxy group, cyclohexyloxy group, n-heptyloxy group, n-octyloxy group, 2-ethylhexyloxy group, n-nonyloxy group, n-decyloxy group, n-dodecyloxy group, n-tetradecyloxy group, n-hexadecyloxy group, etc.) or a substituted or unsubstituted aryl group having 4 to 16 carbon atoms (for example, phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethyl) Phenyl group, 4-n-propylphenyl group, 4-isopropylphenyl group, 4-n-butylphenyl Nyl group, 4-tert-butylphenyl group, 4-isopentylphenyl group, 4-tert-pentylphenyl group, 4-n-hexylphenyl group, 4-cyclohexylphenyl group, 4-n-octylphenyl group, 4- n-decylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3,4-dimethylphenyl group, 5-indanyl group, 1,2,3,4 -Tetrahydro-5-naphthyl group, 1,2,3,4-tetrahydro-6-naphthyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 3-ethoxyphenyl group, 4-ethoxy Phenyl group, 4-n-propoxyphenyl group, 4-isopropoxyphenyl group, 4-n-butoxyphenyl group, 4-n-pentyloxyphenyl group 4-n-hexyloxyphenyl group, 4-cyclohexyloxyphenyl group, 4-n-heptyloxyphenyl group, 4-n-octyloxyphenyl group, 4-n-decyloxyphenyl group, 2,3-dimethoxyphenyl group 2,5-dimethoxyphenyl group, 3,4-dimethoxyphenyl group, 2-methoxy-5-methylphenyl group, 3-methyl-4-methoxyphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4 -Fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 4-bromophenyl group, 4-trifluoromethylphenyl group, 3,4-dichlorophenyl group, 2-methyl-4-chlorophenyl group, 2-chloro-4-methylphenyl group, 3-chloro-4-methylphenyl group, 2-chloro -4-methoxyphenyl group, 4-phenylphenyl group, 3-phenylphenyl group, 4- (4'-methylphenyl) phenyl group, 4- (4'-methoxyphenyl) phenyl group, 1-naphthyl group, 2- Naphthyl group, 4-ethoxy-1-naphthyl group, 6-methoxy-2-naphthyl group, 7-ethoxy-2-naphthyl group, 2-furyl group, 2-thienyl group, 3-thienyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, etc.), more preferably a hydrogen atom, a fluorine atom, a chlorine atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or 6 to 12 carbon atoms. And more preferably a hydrogen atom, a fluorine atom, a chlorine atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a carbocyclic aromatic group having 6 to 10 carbon atoms. A.

  Specific examples of the fluoranthene derivative represented by the formula (26) include the following.

  Examples of the substituted or unsubstituted benzofluoranthene include, for example, a simple substance or derivative of benzo [b] fluoranthene represented by the following formula (91), a simple substance of benzo [k] fluoranthene represented by the formula (92), or Derivatives.

In formula (91) and formula (92), X 1 to X 24 are a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, or substituted or unsubstituted aryl. Represents a group.
The aryl group represents a carbocyclic aromatic group such as a phenyl group or a naphthyl group, for example, a heterocyclic aromatic group such as a furyl group, a thienyl group, or a pyridyl group.

X 1 to X 24 are preferably a hydrogen atom, a halogen atom (eg, fluorine atom, chlorine atom, bromine atom), a linear, branched or cyclic alkyl group having 1 to 16 carbon atoms (eg, methyl group, ethyl group). Group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, cyclopentyl group, n-hexyl Group, 3,3-dimethylbutyl group, cyclohexyl group, n-heptyl group, cyclohexylmethyl group, n-octyl group, tert-octyl group, 2-ethylhexyl group, n-nonyl group, n-decyl group, n-dodecyl Group, n-tetradecyl group, n-hexadecyl group, etc.), linear, branched or cyclic alkoxy group having 1 to 16 carbon atoms (for example, methoxy group, ethoxy group, etc.) Group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, n-pentyloxy group, neopentyloxy group, cyclopentyloxy group, n-hexyloxy group, 3,3-dimethyl Butyloxy group, cyclohexyloxy group, n-heptyloxy group, n-octyloxy group, 2-ethylhexyloxy group, n-nonyloxy group, n-decyloxy group, n-dodecyloxy group, n-tetradecyloxy group, n -Hexadecyloxy group, etc., or a substituted or unsubstituted aryl group having 4 to 16 carbon atoms (for example, phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl) Group, 4-n-propylphenyl group, 4-isopropylphenyl group, 4-n-butylpheny Group, 4-tert-butylphenyl group, 4-isopentylphenyl group, 4-tert-pentylphenyl group, 4-n-hexylphenyl group, 4-cyclohexylphenyl group, 4-n-octylphenyl group, 4-n -Decylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3,4-dimethylphenyl group, 5-indanyl group, 1,2,3,4- Tetrahydro-5-naphthyl group, 1,2,3,4-tetrahydro-6-naphthyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 3-ethoxyphenyl group, 4-ethoxyphenyl Group, 4-n-propoxyphenyl group, 4-isopropoxyphenyl group, 4-n-butoxyphenyl group, 4-n-pentyloxyphenyl group, 4 -N-hexyloxyphenyl group, 4-cyclohexyloxyphenyl group, 4-n-heptyloxyphenyl group, 4-n-octyloxyphenyl group, 4-n-decyloxyphenyl group, 2,3-dimethoxyphenyl group, 2,5-dimethoxyphenyl group, 3,4-dimethoxyphenyl group, 2-methoxy-5-methylphenyl group, 3-methyl-4-methoxyphenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4- Fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 4-bromophenyl group, 4-trifluoromethylphenyl group, 3,4-dichlorophenyl group, 2-methyl-4-chlorophenyl group, 2 -Chloro-4-methylphenyl group, 3-chloro-4-methylphenyl group, 2-chloro- -Methoxyphenyl group, 4-phenylphenyl group, 3-phenylphenyl group, 4- (4'-methylphenyl) phenyl group, 4- (4'-methoxyphenyl) phenyl group, 1-naphthyl group, 2-naphthyl group 4-ethoxy-1-naphthyl group, 6-methoxy-2-naphthyl group, 7-ethoxy-2-naphthyl group, 2-furyl group, 2-thienyl group, 3-thienyl group, 2-pyridyl group, 3- And more preferably a hydrogen atom, a fluorine atom, a chlorine atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an aryl having 6 to 12 carbon atoms. More preferably a hydrogen atom, a fluorine atom, a chlorine atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a carbocyclic aromatic group having 6 to 10 carbon atoms. The

  Examples of the benzo [b] fluoranthene derivative represented by the formula (91) include the following.

  Examples of the benzo [k] fluoranthene derivative represented by the formula (92) include the following.

  The polycyclic fused aromatic skeleton is preferably a simple substance or a derivative of triphenylene represented by the following formula (27).

  Examples of such a triphenylene derivative include those represented by the following formula (56A).

In formula (56A), R 1 to R 6 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 5 to 30 nuclear carbon atoms, a branched or straight chain alkyl group having 1 to 30 carbon atoms. And a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, which is a single or a combination of plural groups.
Specific examples of the triphenylene derivative represented by the formula (27) include the following.

In the present invention, the polycyclic fused aromatic skeleton is preferably a simple substance or a derivative of naphthalene.
As a naphthalene derivative, the thing of following formula (57A) and (57B) is mentioned, for example.

In formula (57A), R 1 to R 8 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 5 to 30 nuclear carbon atoms, a branched or straight chain alkyl group having 1 to 30 carbon atoms, And a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, which is a single or a combination of plural groups.
Specific examples of naphthalene derivatives include the following.

  The polycyclic fused aromatic skeleton may contain a nitrogen atom, and for example, the following may be used.

  In the organic EL device of the present invention, the phosphorescent dopant preferably contains a metal complex composed of a metal selected from Ir, Pt, Os, Au, Cu, Re, and Ru and a ligand.

Specific examples of the dopant include, for example, PQIr (iridium (III) bis (2-phenylquinolyl-N, C 2 ′ ) acetylacetonate), Ir (ppy) 3 (fac-tris (2-phenylpyridine) iridium), The following compounds are mentioned.

Such phosphorescent dopants preferably have a maximum emission luminance wavelength of 470 nm to 700 nm, more preferably 480 nm to 680 nm, and even more preferably 500 nm to 650 nm.
A highly efficient light-emitting element can be obtained by forming a light-emitting layer by doping a phosphorescent dopant having such an emission wavelength into the host of the present invention.

  In the organic EL device of the present invention, the organic thin film layer preferably has an electron injection layer between the cathode and the light emitting layer, and the electron injection layer preferably contains a nitrogen-containing heterocyclic derivative.

The electron injection layer and the electron transport layer are layers that assist injection of electrons into the light emitting layer, and have a high electron mobility. The electron injection layer is provided to adjust the energy level, for example, to alleviate a sudden change in the energy level.
As an electron carrying layer, what contains at least any one of the nitrogen-containing heterocyclic derivative represented by following formula (201)-(203) is applicable.

In formulas (201) to (203), R has a hydrogen atom, an aryl group having 6 to 60 carbon atoms which may have a substituent, a pyridyl group which may have a substituent, or a substituent. An optionally substituted quinolyl group, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted alkoxy group having 1 to 20 carbon atoms, and n is 0 to 4 Is an integer,
R 1 has an aryl group having 6 to 60 carbon atoms which may have a substituent, a pyridyl group which may have a substituent, a quinolyl group which may have a substituent, and a substituent. An optionally substituted alkyl group having 1 to 20 carbon atoms or an alkoxy group having 1 to 20 carbon atoms,
R 2 and R 3 each independently have a hydrogen atom, an aryl group having 6 to 60 carbon atoms which may have a substituent, a pyridyl group which may have a substituent, or a substituent. An optionally substituted quinolyl group, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted alkoxy group having 1 to 20 carbon atoms,
L has an arylene group having 6 to 60 carbon atoms which may have a substituent, a pyridinylene group which may have a substituent, a quinolinylene group which may have a substituent or a substituent. A fluorenylene group which may be
Ar 1 is an arylene group having 6 to 60 carbon atoms which may have a substituent, a pyridinylene group which may have a substituent, or a quinolinylene group which may have a substituent,
Ar 2 has an aryl group having 6 to 60 carbon atoms which may have a substituent, a pyridyl group which may have a substituent, a quinolyl group which may have a substituent, and a substituent. It is a C1-C20 alkyl group which may have, or a C1-C20 alkoxy group which may have a substituent.
Ar 3 has an aryl group having 6 to 60 carbon atoms that may have a substituent, a pyridyl group that may have a substituent, a quinolyl group that may have a substituent, and a substituent. An optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted alkoxy group having 1 to 20 carbon atoms, or a group represented by —Ar 1 —Ar 2 (Ar 1 and Ar 2 Are the same as above.

  In the above formulas (201) to (203), R represents a hydrogen atom, an aryl group having 6 to 60 carbon atoms which may have a substituent, a pyridyl group which may have a substituent, or a substituent. A quinolyl group which may have a group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an alkoxy group which has 1 to 20 carbon atoms which may have a substituent.

  The aryl group having 6 to 60 carbon atoms is preferably an aryl group having 6 to 40 carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms, specifically, a phenyl group, a naphthyl group, an anthryl group, or phenanthryl. 1 consisting of a group, naphthacenyl group, chrycenyl group, pyrenyl group, biphenyl group, terphenyl group, tolyl group, t-butylphenyl group, (2-phenylpropyl) phenyl group, fluoranthenyl group, fluorenyl group, spirobifluorene A monovalent group consisting of a valent group, a perfluorophenyl group, a perfluoronaphthyl group, a perfluoroanthryl group, a perfluorobiphenyl group, 9-phenylanthracene, and a monovalent group consisting of 9- (1′-naphthyl) anthracene A monovalent group consisting of a group, 9- (2′-naphthyl) anthracene, 6-phenylchrysene A monovalent group consisting of 9- [4- (diphenylamino) phenyl] anthracene, and the like. Phenyl group, naphthyl group, biphenyl group, terphenyl group, 9- (10-phenyl) An anthryl group, 9- [10- (1′-naphthyl)] anthryl group, 9- [10- (2′-naphthyl)] anthryl group and the like are preferable.

As the alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 6 carbon atoms is preferable. Specifically, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, etc. Examples thereof include haloalkyl groups such as a fluoromethyl group, and those having 3 or more carbon atoms may be linear, cyclic or branched.
As a C1-C20 alkoxy group, a C1-C6 alkoxy group is preferable, and a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group etc. are mentioned specifically ,. Those having 3 or more carbon atoms may be linear, cyclic or branched.

Examples of the substituent for each group represented by R include a halogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted alkoxy group having 1 to 20 carbon atoms, A C6-C40 aryloxy group which may have a substituent, a C6-C40 aryl group which may have a substituent, or a C3-C3 which may have a substituent 40 heteroaryl groups and the like can be mentioned.
Examples of the halogen atom include fluorine, chlorine, bromine and iodine.
Examples of the alkyl group having 1 to 20 carbon atoms, the alkoxy group having 1 to 20 carbon atoms, and the aryl group having 6 to 40 carbon atoms are the same as those described above.

Examples of the aryloxy group having 6 to 40 carbon atoms include a phenoxy group and a biphenyloxy group.
Examples of the heteroaryl group having 3 to 40 carbon atoms include pyrrolyl group, furyl group, thienyl group, silolyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuryl group, imidazolyl group, pyrimidyl group, carbazolyl group, selenophenyl group Oxadiazolyl group, triazolyl group and the like.
n is an integer of 0 to 4, preferably 0 to 2.

In Formula (201), R 1 may have an aryl group having 6 to 60 carbon atoms which may have a substituent, a pyridyl group which may have a substituent, or a substituent. They are a quinolyl group, an optionally substituted alkyl group having 1 to 20 carbon atoms or an alkoxy group having 1 to 20 carbon atoms.
Specific examples of these groups, preferred carbon numbers and substituents are the same as those described for R.

In the formulas (202) and (203), R 2 and R 3 each independently have a hydrogen atom, an aryl group having 6 to 60 carbon atoms which may have a substituent, or a substituent. May be a pyridyl group, an optionally substituted quinolyl group, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted group having 1 to 20 carbon atoms. An alkoxy group;
Specific examples of these groups, preferred carbon numbers and substituents are the same as those described for R.

In the above formulas (201) to (203), L has an optionally substituted arylene group having 6 to 60 carbon atoms, an optionally substituted pyridinylene group, and a substituent. It may be a quinolinylene group or a fluorenylene group which may have a substituent.
The arylene group having 6 to 60 carbon atoms is preferably an arylene group having 6 to 40 carbon atoms, more preferably an arylene group having 6 to 20 carbon atoms, specifically, a hydrogen atom 1 from the aryl group described above for R. And divalent groups formed by removing the individual. The substituent for each group represented by L is the same as that described for R.

  L is

A group selected from the group consisting of
In Formula (201), Ar 1 may have an arylene group having 6 to 60 carbon atoms which may have a substituent, a pyridinylene group which may have a substituent, or a substituent. It is a quinolinylene group. Substituents for each group represented by Ar 1 and Ar 3 are the same as those described for R.
Ar 1 is preferably any group selected from fused ring groups represented by the following formulas (101) to (110).

In the formulas (101) to (110), each condensed ring has a halogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, and an optionally substituted carbon number 1. Having an alkoxy group of -20, an aryloxy group having 6 to 40 carbon atoms which may have a substituent, an aryl group having 6 to 40 carbon atoms which may have a substituent, or a substituent. Bonding groups consisting of heteroaryl groups having 3 to 40 carbon atoms may be bonded, and when there are a plurality of the bonding groups, the bonding groups may be the same as or different from each other. Specific examples of these groups are the same as those described above.
In the formula (110), L ′ represents a single bond, or

A group selected from the group consisting of
The formula (103) represented by Ar1 is preferably a condensed ring group represented by the following formulas (111) to (125).

  In the formulas (111) to (125), each condensed ring has a halogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, and an optionally substituted carbon number 1. Having an alkoxy group of -20, an aryloxy group having 6 to 40 carbon atoms which may have a substituent, an aryl group having 6 to 40 carbon atoms which may have a substituent, or a substituent. Further, a linking group composed of a heteroaryl group having 3 to 40 carbon atoms may be bonded, and when there are a plurality of the linking groups, the linking groups may be the same as or different from each other. Specific examples of these groups are the same as those described above.

In the above formula (201), Ar 2 may have an optionally substituted aryl group having 6 to 60 carbon atoms, an optionally substituted pyridyl group, and an optionally substituted group. A quinolyl group, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted alkoxy group having 1 to 20 carbon atoms.
Specific examples of these groups, preferred carbon numbers and substituents are the same as those described for R 1.

In the formulas (202) and (203), Ar 3 has an aryl group having 6 to 60 carbon atoms which may have a substituent, a pyridyl group which may have a substituent, and a substituent. An optionally substituted quinolyl group, an optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted alkoxy group having 1 to 20 carbon atoms, or —Ar 1 —Ar 2. (Ar 1 and Ar 2 are each the same as described above).
Specific examples of these groups, preferred carbon numbers and substituents are the same as those described for R.
Ar 3 is preferably any group selected from fused ring groups represented by the following formulas (126) to (135).

In the formulas (126) to (135), each condensed ring has a halogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, and an optionally substituted carbon number 1. Having an alkoxy group of -20, an aryloxy group having 6 to 40 carbon atoms which may have a substituent, an aryl group having 6 to 40 carbon atoms which may have a substituent, or a substituent. Bonding groups consisting of heteroaryl groups having 3 to 40 carbon atoms may be bonded, and when there are a plurality of the bonding groups, the bonding groups may be the same as or different from each other. Specific examples of these groups are the same as those described above.
In the formula (135), L ′ is the same as described above.
In the above formulas (126) to (135), R ′ is a hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted group having 6 to 40 carbon atoms. Or a heteroaryl group having 3 to 40 carbon atoms which may have a substituent. Specific examples of these groups are the same as those described above.
The general formula (128) represented by Ar3 is preferably a condensed ring group represented by the following formulas (129) to (151).

In the formulas (129) to (151), each condensed ring has a halogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, and an optionally substituted carbon number 1 Having an alkoxy group of -20, an aryloxy group having 6 to 40 carbon atoms which may have a substituent, an aryl group having 6 to 40 carbon atoms which may have a substituent, or a substituent. Bonding groups consisting of heteroaryl groups having 3 to 40 carbon atoms may be bonded, and when there are a plurality of the bonding groups, the bonding groups may be the same as or different from each other. Specific examples of these groups are the same as those described above. R ′ is the same as described above.
Ar 2 and Ar 3 are each independently

A group selected from the group consisting of
Specific examples of the nitrogen-containing heterocyclic derivative represented by the above formulas (201) to (203) of the present invention are shown below, but the present invention is not limited to these exemplified compounds.
In the table below, HAr represents the formulas (201) to (203).

Indicates.

  Among the above specific examples, in particular, (1-1), (1-5), (1-7), (2-1), (3-1), (4-2), (4-6) , (7-2), (7-7), (7-8), (7-9), and (9-7) are preferable.

  Moreover, as a material used for an electron injection layer or an electron carrying layer, 8-hydroxyquinoline or the metal complex of its derivative, an oxadiazole derivative, and a nitrogen-containing heterocyclic derivative are suitable. As a specific example of the metal complex of 8-hydroxyquinoline or a derivative thereof, a metal chelate oxinoid compound containing a chelate of oxine (generally 8-quinolinol or 8-hydroxyquinoline), for example, tris (8-quinolinol) aluminum is used. Can do. And as an oxadiazole derivative, the electron transfer compound represented by the following general formula is mentioned.

In the formula, Ar 17 , Ar 18 , Ar 19 , Ar 21 , Ar 22 and Ar 25 each represent an aryl group with or without a substituent, and Ar 17 and Ar 18 , Ar 19 and Ar 21 , Ar 22 and Ar 25 may be the same or different. Ar 20 , Ar 23 and Ar 24 each represent an arylene group with or without a substituent, and Ar 23 and Ar 24 may be the same or different.

  Examples of the aryl group in the above formula include a phenyl group, a biphenyl group, an anthranyl group, a perylenyl group, and a pyrenyl group. Examples of the arylene group include a phenylene group, a naphthylene group, a biphenylene group, an anthranylene group, a peryleneylene group, and a pyrenylene group. And as a substituent to these, a C1-C10 alkyl group, a C1-C10 alkoxy group, a cyano group, etc. are mentioned. As this electron transfer compound, those having good thin film forming properties are preferably used. Specific examples of these electron transfer compounds include the following.

  Examples of the nitrogen-containing heterocyclic derivative include nitrogen-containing heterocyclic derivatives composed of organic compounds having the following general formula and not a metal complex. For example, a 5-membered ring or 6-membered ring containing the skeleton shown in (A) and a structure shown in Formula (B) can be given.

In the formula (B), X represents a carbon atom or a nitrogen atom. Z 1 and Z 2 each independently represents an atomic group capable of forming a nitrogen-containing heterocycle.

  Preferably, the organic compound which has a nitrogen-containing aromatic polycyclic group which consists of a 5-membered ring or a 6-membered ring. Further, in the case of such a nitrogen-containing aromatic polycyclic group having a plurality of nitrogen atoms, the nitrogen-containing aromatic polycyclic organic compound having a skeleton obtained by combining the above (A) and (B) or (A) and (C) .

  A nitrogen-containing heterocyclic derivative wherein the nitrogen-containing group of the nitrogen-containing organic compound is selected from nitrogen-containing heterocyclic groups represented by the following general formula.

  In the formula, R is an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3 to 40 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms, and n is 0 to 5 A plurality of R may be the same or different from each other when n is an integer of 2 or more.

  Furthermore, as a preferable specific compound, a nitrogen-containing heterocyclic derivative represented by the following general formula.

In the formula, HAr is a nitrogen-containing heterocycle having 3 to 40 carbon atoms which may have a substituent, and L is a single bond or an arylene group having 6 to 40 carbon atoms which may have a substituent. Or it is a C3-C40 heteroarylene group which may have a substituent, Ar < 1 > is a C6-C40 bivalent aromatic hydrocarbon group which may have a substituent. , Ar 2 is an aryl group having 6 to 40 carbon atoms which may have a substituent or a heteroaryl group having 3 to 40 carbon atoms which may have a substituent.

  A nitrogen-containing heterocyclic derivative wherein HAr is selected from the group consisting of:

  A nitrogen-containing heterocyclic derivative wherein L is selected from the group consisting of:

A nitrogen-containing heterocyclic derivative wherein Ar 2 is selected from the group consisting of:

A nitrogen-containing heterocyclic derivative in which Ar 1 has an arylanthranyl group represented by the following.

In the formula, R 1 to R 14 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 40 carbon atoms, or a substituent. An aryl group having 6 to 40 carbon atoms or a heteroaryl group having 3 to 40 carbon atoms which may have a group, and Ar3 is an aryl group having 6 to 40 carbon atoms which may have a substituent or It is a C3-C40 heteroaryl group.

A nitrogen-containing heterocyclic derivative in which R 1 to R 8 are all hydrogen atoms in Ar 1 .

  In addition, the following compounds described in JP-A-9-3448 include organic compounds that satisfy the above-described element constituent conditions.

In the formula, each of R 1 to R 4 independently represents a hydrogen atom, a substituted or unsubstituted aliphatic group, a substituted or unsubstituted aliphatic cyclic group, a substituted or unsubstituted carbocyclic aromatic ring group, A substituted or unsubstituted heterocyclic group is represented, and X 1 and X 2 each independently represents an oxygen atom, a sulfur atom or a dicyanomethylene group.

  The following compounds described in JP-A-2000-173774 include organic compounds that satisfy the above-described element constituent conditions.

However, in said general formula, R < 1 >, R < 2 >, R < 3 > and R < 4 > are mutually the same or different groups, Comprising: It is an aryl group represented by the following general formula.

However, in said general formula, R < 5 >, R < 6 >, R <7> , R < 8 > and R < 9 > are mutually the same or different groups, Comprising: A hydrogen atom or those at least 1 is a saturated or unsaturated alkoxyl group, an alkyl group , An amino group or an alkylamino group.

  Further, it may be a polymer compound containing the nitrogen-containing heterocyclic group or nitrogen-containing heterocyclic derivative.

  Although the film thickness of an electron carrying layer or an electron injection layer is not specifically limited, Preferably, it is 1-100 nm.

  In the organic EL device of the present invention, it is preferable that a reducing dopant is added to an interface region between the cathode and the organic thin film layer.

According to such a configuration, it is possible to improve the light emission luminance and extend the life of the organic EL element.
Here, the reducing dopant is defined as a substance capable of reducing the electron transporting compound. Accordingly, various materials can be used as long as they have a certain reducibility, such as alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metals. At least selected from the group consisting of oxides, alkaline earth metal halides, rare earth metal oxides or rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, rare earth metal organic complexes One substance can be preferably used.

More specifically, preferable reducing dopants include Li (work function: 2.9 eV), Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2). .16 eV) and Cs (work function: 1.95 eV), at least one alkali metal selected from the group consisting of Ca (work function: 2.9 eV), Sr (work function: 2.0 to 2.5 eV) And at least one alkaline earth metal selected from the group consisting of Ba (work function: 2.52 eV), and those having a work function of 2.9 eV or less are particularly preferred.
Among these, a more preferable reducing dopant is at least one alkali metal selected from the group consisting of K, Rb and Cs, more preferably Rb or Cs, and most preferably Cs. These alkali metals have particularly high reducing ability, and the addition of a relatively small amount to the electron injection region can improve the light emission luminance and extend the life of the organic EL element. Further, as a reducing dopant having a work function of 2.9 eV or less, a combination of two or more alkali metals is also preferable. Particularly, a combination containing Cs, such as Cs and Na, Cs and K, Cs and Rb, or Cs. And a combination of Na and K. By including Cs in combination, the reducing ability can be efficiently exhibited, and by adding to the electron injection region, the emission luminance and the life of the organic EL element can be improved.

The organic EL material-containing solution of the present invention is an organic EL material-containing solution for forming the light emitting layer of the organic EL element described above, and includes the first host, the second host, the dopant, Is dissolved in a solvent.
According to such an organic EL material-containing solution, the above-described mixed color light emitting layer can be formed easily and at low cost by a coating method such as an ink printing method or a nozzle jet method.

  Although there is no restriction | limiting in particular as an organic solvent which concerns on this invention, For example, alcohol (methanol, ethanol, etc.), carboxylic acid esters (ethyl acetate, propyl acetate, etc.), nitriles (acetonitrile, etc.), ethers (isopropyl ether, THF), aromatic hydrocarbons (cyclohexylbenzene, toluene, xylene, etc.), halogenated alkyls (methylene chloride, etc.), saturated hydrocarbons (heptane, etc.). Of these, preferred are carboxylic acid esters, nitriles, ethers, aromatic hydrocarbons, alkyl halides, saturated hydrocarbons, and more preferred are carboxylic acid esters, ethers, aromatic hydrocarbons. It is kind.

  Examples of the solvent for the organic EL material-containing solution include biphenyl derivatives and cyclic ketones.

Examples of the biphenyl derivative include alkyl-substituted biphenyl, and specific examples thereof include methylbiphenyl, ethylbiphenyl, diethylbiphenyl, isopropylbiphenyl, diisopropylbiphenyl, n-propylbiphenyl, n-pentylbiphenyl, methoxybiphenyl, and the like. Can be mentioned.
In addition, as for carbon number of the alkyl group of alkyl substituted biphenyl, it is more preferable that it is 1-5. In this case, it is possible to achieve both appropriate viscosity and solubility.
For example, ethyl biphenyl, isopropyl biphenyl, and the like can be suitably used as the solvent for the organic EL material-containing solution of the present invention.

The solvent composition may be 100% biphenyl derivative, or a mixed solution in which a viscosity adjusting liquid or the like is mixed.
In the case of a mixed solution, 20% or more may be a biphenyl derivative, 50% or more may be a biphenyl derivative, and 75% or more may be a biphenyl derivative. From the viewpoint of taking advantage of the viscosity and solubility of the biphenyl derivative, a higher proportion of the biphenyl derivative is preferable.

Examples of the cyclic ketone include cyclic alkyl ketones such as a cyclopentanone derivative, a cyclohexanone derivative, a cycloheptanone derivative, and a cyclooctanone derivative. These cyclic ketones may be used alone as a solvent, or may be used as a mixture.
In particular, the solvent preferably contains a cyclohexanone derivative as a cyclic ketone.
Preferred cyclohexanone derivatives include 2-acetylcyclohexanone, 2-methylcyclohexanone, 3-methylcyclohexanone, 4-methylcyclohexanone, 2-cyclohexylcyclohexanone, 2- (1-cyclohexenyl) cyclohexanone, 2,5-dimethylcyclohexanone, 3, 4-dimethylcyclohexanone, 3,5-dimethylcyclohexanone, 4-ethylcyclohexanone, pulegone, menthone, 4-pentylcyclohexanone, 2-propylcyclohexanone, 3,3,5-trimethylcyclohexanone, Tujon.
Of these, cyclohexanone is preferred.

Further, as the cyclic ketone, those containing a nitrogen-containing ring are also preferable. For example, caprolactam, N-methylcaprolactam, 1,3-dimethyl-2-imidazolidine, 2-pyrrolidone, 1-acetyl-2-pyrrolidone, 1- Examples include butyl-2-pyrrolidone, 2-piperidone, 1,5-dimethyl-2-piperidone.
The cyclic ketone compound is preferably selected from the group of cyclohexanone, cyclopentanone, and cycloheptanone (including these derivatives).

As a result of various studies, the inventors have found that a cyclohexanone derivative dissolves a low-molecular organic EL material at a higher concentration than other solvents, and the soluble compounds are not limited to a narrow range, and a wide variety of low-molecular compounds It has been found that an organic EL material-containing solution using an organic EL material can be prepared.
Then, by using a cyclohexanone derivative as a solvent, an organic EL material-containing solution containing a sufficient amount of a high-performance low-molecular organic EL material that could not be used due to low solubility in conventional solvents was prepared. I found out that I can do it.
Furthermore, since the cyclohexanone derivative has a high boiling point (156 ° C .: cyclohexanone) and a high viscosity (2 cP: cyclohexanone), it is suitable for a coating process such as an inkjet method. And since the cyclohexanone derivative is well mixed with an alcohol solvent as a viscosity adjusting liquid, particularly a diol solvent, it can be made into a high viscosity solution by adjusting the viscosity. This is also an excellent advantage as a solvent for a low-molecular organic EL material that does not change.

  Hereinafter, embodiments of the present invention will be described.

[Organic EL device]
In FIG. 1, schematic structure of the organic EL element of this embodiment is shown.
The organic EL element 10 includes a transparent substrate 11, an anode 12, a cathode 14, and an organic thin film layer 13 disposed between the anode 12 and the cathode 14.
The organic thin film layer 13 includes the above-described first host, the second host, and a light emitting layer 16 containing a phosphorescent dopant, and a light emitting layer such as a hole injection layer 15 between the light emitting layer 16 and the anode 12. An electron transport layer 17, an electron injection layer 18, and the like may be provided between 16 and the cathode 14.
Further, an electron blocking layer may be provided on the anode 12 side of the light emitting layer 16, and a hole blocking layer may be provided on the cathode 14 side of the light emitting layer 16.
Thereby, electrons and holes can be confined in the light emitting layer 16, and the exciton generation probability in the light emitting layer 16 can be increased.

[Example]
EXAMPLES Next, although an Example and a comparative example are given and this invention is demonstrated in more detail, this invention is not restrict | limited to the description content of these Examples at all.
In Table 2, below, physical property values of each material are described. The physical property values were measured as follows.
Eg (T) was defined based on the phosphorescence emission spectrum.
That is, each material is dissolved at 10 μmol / L in an EPA solvent (diethyl ether: isopentane: ethanol = 5: 5: 2 by volume ratio) to obtain a sample for phosphorescence measurement.
Then, the phosphorescence measurement sample is placed in a quartz cell and cooled to 77K.
This is irradiated with excitation light, and the wavelength of the emitted phosphorescence is measured.
A tangent line is drawn with respect to the rising edge on the short wavelength side of the obtained phosphorescence spectrum, and the wavelength value of the intersection of the tangent line and the base line is obtained.
A value obtained by converting the obtained wavelength value into energy is defined as Eg (T).
A commercially available measuring device F-4500 (manufactured by Hitachi) was used for the measurement.

The affinity level Af (electron affinity) refers to the energy released or absorbed when one electron is given to the molecule of the material, and is defined as positive in the case of emission and negative in the case of absorption.
The affinity level Af is defined by the ionization potential Ip and the optical energy gap Eg (S) as follows.
Af = Ip-Eg (S)
Here, the ionization potential Ip means the energy required to remove and ionize electrons from the compound of each material, and is, for example, a value measured with an ultraviolet photoelectron spectrometer (AC-3, Riken instrument). is there.
The optical energy gap Eg (S) refers to the difference between the conduction level and the valence level. Eg (S) is, for example, a value obtained by converting the wavelength value at the intersection of the long wavelength side tangent of the absorption spectrum of the diluted toluene solution of each material and the baseline (zero absorption) into energy.

(Example 1)
A glass substrate with an ITO transparent electrode having a thickness of 25 mm × 75 mm × 1.1 mm (manufactured by Geomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes.
The glass substrate with the transparent electrode line after the cleaning is mounted on the substrate holder of the vacuum evaporation apparatus, and first, 4,4 ′ having a thickness of 50 nm is formed on the surface where the transparent electrode line is formed so as to cover the transparent electrode. A -bis [N- (1-naphthyl) -N-phenylamino] biphenyl film (hereinafter abbreviated as “NPD film”) was formed by resistance heating vapor deposition. This NPD film functions as a hole injection / transport layer.
Next, the following compound D and compound A were formed as a first host and a second host on the NPD film to a thickness of 40 nm by resistance heating vapor deposition. Here, the compound A was vapor-deposited so as to have a mass ratio of 5% with respect to the entire host including the first host and the second host. Simultaneously with such a host, Ir (piq) 3 was deposited as a phosphorescent dopant in a mass ratio of 5% with respect to the host. This film functions as a light emitting layer.
Next, a compound J having a thickness of 40 nm was formed as an electron transport layer on the light emitting layer.
Thereafter, LiF was deposited at 1 nm. On the LiF film, metal Al was deposited to a thickness of 150 nm to form a metal cathode, thereby forming an organic EL element.

(Examples 2-4, Comparative Examples 1-5)
An organic EL device was produced in the same manner as in Example 1 except that the compound constituting the host was changed as shown in Table 1 below.

(Evaluation of organic EL elements)
A direct current (1 mA / cm 2 ) was passed through the organic EL device produced as described above to emit light, and emission chromaticity, luminance (L), and voltage were measured.
Based on this, the current efficiency (L / J) was determined. In addition, a continuous DC current test was performed at an initial luminance of 5000 nit (cd / m 2 ) to measure the half-life of each organic EL element.
The results are shown in Table 2 below, and the ionization potential (Ip), affinity level (Af), excited singlet energy gap (Eg (S)), excited triplet energy gap (Eg (T)) of each material. )) Is shown in Table 3 below.

As is apparent from Tables 1 and 2, the organic EL elements of Examples 1 to 4 using the first host and the second host of the present invention as hosts have a long emission lifetime.
On the other hand, the organic EL elements of Comparative Examples 1 and 3-5 in which the host is composed of one compound and the host are composed of two compounds, but the first and second host materials of the present invention are applied. The organic EL element of the comparative example 2 which is not performed has a short lifetime compared with Examples 1-4.
In Examples 1 and 2, the life of 1000 hours was increased by adding Compound A and Compound C as the second host to Comparative Example 3.

[Modification]
Note that the present invention is not limited to the above description, and modifications within a range not departing from the gist of the present invention are included in the present invention.

For example, the following changes are also preferable modifications of the present invention.
In the present invention, the light emitting layer preferably further contains a charge injection auxiliary material.
When a light emitting layer is formed using a host material having a wide Eg (T) as described above, the difference between the Ip of the host material and the Ip of the hole injection / transport layer, etc. increases, and The injection becomes difficult, and the drive voltage for obtaining sufficient luminance may increase.
In such a case, in addition to the second host, in addition to the second host, the hole injection / transport charge injection auxiliary agent is contained in the light emitting layer, thereby facilitating hole injection into the light emitting layer and lowering the driving voltage. be able to.

As the charge injection auxiliary agent, for example, a general hole injection / transport material or the like can be used.
Specific examples include triazole derivatives (see US Pat. No. 3,112,197), oxadiazole derivatives (see US Pat. No. 3,189,447, etc.), imidazole derivatives (Japanese Patent Publication No. 37-16096). Polyarylalkane derivatives (US Pat. Nos. 3,615,402, 3,820,989, 3,542,544, JP-B-45-555). 51-10983, JP-A-51-93224, 55-17105, 56-4148, 55-108667, 55-156953, 56-36656 See the publication)
Pyrazoline derivatives and pyrazolone derivatives (US Pat. Nos. 3,180,729, 4,278,746, JP-A-55-88064, JP-A-55-88065, JP-A-49-105537) No. 55-51086, No. 56-80051, No. 56-88141, No. 57-45545, No. 54-112737, No. 55-74546, etc.), phenylenediamine derivatives (U.S. Pat. No. 3,615,404, JP-B 51-10105, JP-A 46-3712, JP-A 47-25336, JP-A 54-53435, and 54-110536 And 541-119925), arylamine derivatives (US Pat. No. 3,567,450, 3,1). No. 0,703, No. 3,240,597, No. 3,658,520, No. 4,232,103, No. 4,175,961 No. 4,012,376, JP-B-49-35702, JP-A-39-27577, JP-A-55-144250, JP-A-56-119132, JP-A-56-22437, West German Patent No. 1,110,518), amino-substituted chalcone derivatives (see US Pat. No. 3,526,501 etc.), oxazole derivatives (US Pat. No. 3,257,203 etc.) ), Styrylanthracene derivatives (see JP-A-56-46234, etc.), fluorenone derivatives (see JP-A-54-110837, etc.), hydrazone derivatives (US No. 3,717,462, JP-A-54-59143, 55-52063, 55-52064, 55-46760, 55-85495, 57- No. 11350, No. 57-148749, JP-A-2-311591, etc.), Stilbene derivatives (JP-A Nos. 61-210363, 61-228451, 61-14642, etc.) 61-72255, 62-47646, 62-36674, 62-10652, 62-30255, 60-93455, 60-94462, 60 -174749, 60-175052, etc.), silazane derivatives (US Pat. No. 4,950,950), Lisilane-based (JP-A-2-204996), aniline-based copolymer (JP-A-2-282263), conductive polymer oligomers (particularly thiophene oligomers) disclosed in JP-A-1-211399, etc. Can be mentioned.

Examples of the hole-injecting material include the above materials, but porphyrin compounds (disclosed in JP-A-63-295695), aromatic tertiary amine compounds and styrylamine compounds (US patents) No. 4,127,412, JP-A-53-27033, 54-58445, 54-149634, 54-64299, 55-79450, 55- 144250, JP-A-56-119132, JP-A-61-295558, JP-A-61-98353, and JP-A-63-295695), particularly aromatic tertiary amine compounds are preferred.
In addition, for example, 4,4′-bis (N- (1-naphthyl) -N-phenylamino having two condensed aromatic rings described in US Pat. No. 5,061,569 in the molecule. ) Biphenyl (hereinafter abbreviated as NPD), and 4,4 ′, 4 ″ -tris (N- () in which three triphenylamine units described in JP-A-4-308688 are linked in a starburst type. 3-methylphenyl) -N-phenylamino) triphenylamine (hereinafter abbreviated as MTDATA) and the like.
Further, hexaazatriphenylene derivatives described in Japanese Patent Publication Nos. 3614405, 3571977 or US Pat. No. 4,780,536 can also be suitably used as the hole injecting material.
In addition, inorganic compounds such as p-type Si and p-type SiC can also be used as the hole injection material.

  The present invention can be used for organic EL elements used in display devices and the like. Moreover, it can utilize as an organic electroluminescent material containing solution for forming the light emitting layer of an organic electroluminescent element.

It is a figure which shows schematic structure of the organic EL element which concerns on one Embodiment of this invention.

Explanation of symbols

DESCRIPTION OF SYMBOLS 10 ... Organic EL element 12 ... Anode 13 ... Organic thin film layer 14 ... Cathode 16 ... Light emitting layer 18 ... Electron injection layer

Claims (12)

  1. An organic EL device comprising an anode, a cathode, and an organic thin film layer provided between the anode and the cathode,
    The organic thin film layer is
    A light emitting layer including at least a first host, a second host, and a dopant that emits light;
    The organic EL device, wherein the second host is at least one of compounds represented by the following formulas (1) to (5).





    (In the formulas (1) to (5), Ar 1 to Ar 4 are a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted phenanthrene group. It is.
    Ar 5 to Ar 13 are a substituted or unsubstituted aryl group having 5 to 40 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 40 carbon atoms, and a substituted or unsubstituted amino group to which an aromatic amino group is bonded. An aryl group having 8 to 40 carbon atoms, or a substituted or unsubstituted aryl group having 8 to 40 carbon atoms to which an aromatic heterocyclic group is bonded.
    Ar 1 and Ar 2 , Ar 3 and Ar 4 , Ar 5 and Ar 6 , Ar 8 and Ar 9 , Ar 10 and Ar 11 , Ar 12 and Ar 13 may be bonded to each other to form a ring.
    L 1 to L 4 are a single bond or a linking group having 1 to 30 carbon atoms.
    R 1 to R 17 are each a hydrogen atom, a halogen atom, or an optionally substituted alkyl group having 1 to 40 carbon atoms, an optionally substituted heterocyclic group having 3 to 20 carbon atoms, or a substituent. A non-condensed aryl group having 6 to 40 carbon atoms which may have a condensed aryl group having 6 to 12 carbon atoms which may have a substituent, or a condensed group having 12 to 40 carbon atoms which may have a substituent A non-condensed mixed aryl group, an aralkyl group having 7 to 20 carbon atoms that may have a substituent, an alkenyl group having 2 to 40 carbon atoms that may have a substituent, and a substituent that may have 1 to 1 40 alkylamino groups, 7 to 60 carbon atoms aralkylamino groups which may have substituents, 3 to 20 carbon atoms alkylsilyl groups which may have substituents, and substituents C8-C40 arylsilyl group, C8-C40 arral optionally having a substituent Rushiriru group, a halogenated alkyl group which may 1 to 40 carbon atoms which may have a substituent.
    X 1 to X 3 represent a sulfur atom, an oxygen atom, or a monoaryl-substituted nitrogen atom. )
  2. The organic EL device according to claim 1,
    The first host has a substituted or unsubstituted polycyclic fused aromatic skeleton having 10 to 30 nuclear atoms, and a minimum excited triplet energy gap of 2.1 eV or more and 2.7 eV And
    The said dopant is a phosphorescence dopant which shows phosphorescence emission. The organic EL element characterized by the above-mentioned.
  3. The organic EL device according to claim 2,
    The first host has a substituted or unsubstituted polycyclic fused aromatic skeleton having 20 to 30 nuclear atoms. An organic EL device, wherein:
  4. In the organic EL device according to claim 2 or 3,
    The organic EL device, wherein the polycyclic fused aromatic skeleton is contained in the chemical structural formula as a divalent or higher valent group.
  5. In the organic EL device according to claim 2 or 3,
    The polycyclic fused aromatic skeleton has a substituent,
    The organic EL device, wherein the substituent is a substituted or unsubstituted aryl group or heteroaryl group.
  6. The organic EL device according to claim 5,
    The said substituent does not have a carbazole skeleton. The organic EL element characterized by the above-mentioned.
  7. The organic EL device according to claim 4,
    The polycyclic fused aromatic skeleton is selected from the group consisting of substituted or unsubstituted phenanthrene diyl, chrysenediyl, fluoranthenediyl, and triphenylenediyl.
  8. The organic EL device according to claim 7,
    The organic EL device, wherein the polycyclic fused aromatic skeleton is substituted with a group having phenanthrene, chrysene, fluoranthene, or triphenylene.
  9. In the organic EL device according to claim 2 or 3,
    The polycyclic fused aromatic skeleton is represented by any one of the following formulas (6) to (9).

    (In the formulas (6) to (9), Ar 1 to Ar 5 represent a substituted or unsubstituted condensed ring structure having 4 to 10 nuclear carbon atoms.)
  10. In the organic EL element according to any one of claims 2 to 9,
    The phosphorescent dopant has a wavelength of maximum light emission luminance of 470 nm or more and 700 nm or less. An organic EL element, wherein:
  11. In the organic EL element according to any one of claims 1 to 10,
    The organic thin film layer has an electron injection layer between the cathode and the light emitting layer,
    The electron injection layer includes a nitrogen-containing heterocyclic derivative. An organic EL device, wherein:
  12. An organic EL material-containing solution for forming a light emitting layer of the organic EL element according to any one of claims 1 to 11,
    The organic EL material-containing solution, wherein the first host, the second host, and the dopant are dissolved in a solvent.
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