JP2009267255A - Material for organic electroluminescent element and organic electroluminescent element using the material - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide: an organic EL element which has low crystallinity, shows superior durability when subjected to vapor deposition, has high heat resistance and luminous efficiency, and retains a long life; and a material for achieving the organic EL element. <P>SOLUTION: The material for the organic EL element is represented by the general formula (1), and the organic EL element contains that material. In the formula (1), X denotes an oxygen atom or a sulfur atom, L<SP>1</SP>, L<SP>2</SP>, and L<SP>3</SP>each independently denote a single bond, an alkylene group, an allylene group, or a carbonyl group, and A<SP>1</SP>, A<SP>2</SP>, and A<SP>3</SP>separately denote a monovalent group, such as a carbazolyl group. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to a material for an organic electroluminescence device and an organic electroluminescence device using the same, and particularly, an organic material having low crystallinity, excellent durability during vapor deposition, high heat resistance and luminous efficiency, and a long life. The present invention relates to an electroluminescence element and a material for an organic electroluminescence element that realizes the electroluminescence element.

An organic electroluminescence element (hereinafter, electroluminescence may be abbreviated as EL) is a fluorescent substance that generates a recombination energy between holes injected from an anode and electrons injected from a cathode by applying an electric field. Is a self-luminous element utilizing the principle of light emission.
Conventionally, a fluorescent material that emits fluorescence by singlet excitons has been used as a light-emitting material used in an organic EL element. However, when electrons and holes are recombined in an organic EL device, it is considered that singlet excitons and triplet excitons are generated at a ratio of 1: 3 due to the difference in spin multiplicity. An organic EL element using a phosphorescent material that emits phosphorescence by triplet excitons can achieve a light emission efficiency that is 3 to 4 times that of an organic EL element that uses only a fluorescent material. Therefore, use of a phosphorescent light emitting material in addition to a fluorescent light emitting material has begun to be studied (see, for example, Non-Patent Document 1 and Non-Patent Document 2). In recent years, organic EL elements having high luminous efficiency and long life have been used. Development of phosphorescent materials that can be provided is underway. For example, a compound in which a carbazole ring derivative is substituted at one position such as a dibenzofuran ring (see, for example, Patent Document 1), an N-substituted carbazolyl group is present in a dibenzofuran ring, and the like. A compound in which the left and right benzene rings are substituted one by one (for example, see Patent Document 2), and a compound in which an aromatic heterocyclic group such as a carbazole ring is directly directly substituted on a dibenzofuran ring (for example, see Patent Document 3). For example, a compound in which a diphenylamino group, a pyrenyl group, or the like is directly substituted at three positions of a dibenzofuran ring is known (for example, see Patent Document 4).

Applied Physics letters, 1999, Vol. 74, No. 3, p. 442-444 Applied Physics letters, 1999, Vol. 75, No. 1, p. 4-6 International Publication No. 2007/198116 Pamphlet International Publication No. 2006/114966 Pamphlet JP 2008-21687 A International Publication No. 2006/128800 Pamphlet

However, the organic EL element materials described in Non-Patent Documents 1 and 2 and Patent Document 1 still do not satisfy the luminous efficiency and lifetime of the obtained organic EL element. The compound described in Patent Document 2 has high crystallinity due to high symmetry, and many of those having a molecular weight of 600 or less, and the heat resistance of the organic EL device is insufficient. Patent Document 3 describes a very wide range of compounds, but specific substituents such as A ¹ -L ^1- , A ² -L ² -and A ³ -L ^3- are specified as in the present invention. When a compound substituted at three positions such as a dibenzofuran ring is used under the above conditions, the luminous efficiency and lifetime are particularly excellent (see Examples 1 to 9 and Comparative Examples 1 to 3 in this specification). Is not described at all. Patent Document 4 describes compounds having substituents at three positions of the dibenzofuran ring as in the organic EL device material of the present invention (especially compound A-45 described in p.39 and (See A-46.) As in the present invention, a compound in which special substituents A ¹ -L ^1- , A ² -L ^2-, and A ³ -L ^3- are substituted under specific conditions is used. In particular, there is no description about the point that the luminous efficiency and the lifetime are particularly excellent (see Examples 1 to 9 and Comparative Examples 2 and 4 in the present specification).
The present invention has been made to solve such problems, solves the conventional problems, has lower crystallinity than conventional organic EL element materials, has excellent durability during vapor deposition, and has heat resistance. Another object of the present invention is to provide an organic EL element having high light emission efficiency and a long lifetime, and an organic EL element material for realizing the organic EL element.

  As a result of intensive studies to achieve the above object, the present inventors have achieved excellent heat resistance and high luminous efficiency by using a compound represented by the following general formula (1) as an organic EL element material. In addition, the present inventors have found that an organic EL element having a long lifetime can be obtained, and have solved the present invention.

［式中、Ｘは、酸素原子又は硫黄原子である。Ｌ¹、Ｌ²及びＬ³は、それぞれ独立して、単結合、炭素数１〜３０のアルキレン基、環形成炭素数６〜２０のアリーレン基又はカルボニル基を示す。
また、Ａ¹、Ａ²及びＡ³は、それぞれ独立して、下記一般式（２）又は（３）

（式中、＊は置換位置を示す。Ｙは、単結合、酸素原子又は硫黄原子であり、Ｚは、酸素原子、硫黄原子又はＮ−Ｒ¹基（Ｒ¹は、炭素数１〜２０のアルキル基又は環形成炭素数６〜１８のアリール基を示す。）である。）
で表される一価の基を示す。
但し、上記一般式（１）において、Ａ¹、Ａ²及びＡ³のうち、少なくとも１つは上記一般式（３）で表される基（但し、カルバゾリル基を除く。）である。］ That is, this invention is a material for organic electroluminescent elements represented by the following general formula (1).

[Wherein, X is an oxygen atom or a sulfur atom. L ¹ , L ² and L ³ each independently represent a single bond, an alkylene group having 1 to 30 carbon atoms, an arylene group having 6 to 20 ring carbon atoms or a carbonyl group.
A ¹ , A ² and A ³ are each independently represented by the following general formula (2) or (3)

(In the formula, * represents a substitution position. Y is a single bond, an oxygen atom or a sulfur atom, Z is an oxygen atom, a sulfur atom or an N—R ¹ group (R ¹ is a group having 1 to 20 carbon atoms). An alkyl group or an aryl group having 6 to 18 ring carbon atoms.)
The monovalent group represented by these is shown.
However, in the above general formula (1), at least one of A ¹ , A ² and A ³ is a group represented by the above general formula (3) (excluding the carbazolyl group). ]

  Furthermore, the present invention provides an organic electroluminescence device in which an organic thin film layer comprising at least one light emitting layer or a plurality of light emitting layers is sandwiched between a cathode and an anode, wherein at least one layer of the organic thin film layer is represented by the general formula (1). It is an organic electroluminescent element containing the material for organic electroluminescent elements represented.

  According to the present invention, it is possible to provide an organic EL device having low crystallinity, excellent durability during vapor deposition, high heat resistance and light emission efficiency, and having a long lifetime, and an organic EL device material for realizing the organic EL device. it can.

  The material for an organic electroluminescence element of the present invention is represented by the following general formula (1).

In said general formula (1), X is an oxygen atom or a sulfur atom, and an oxygen atom is preferable.
L ¹ , L ² and L ³ each independently represent a single bond, an alkylene group having 1 to 30 carbon atoms, an arylene group having 6 to 20 ring carbon atoms or a carbonyl group, A 6-20 arylene group is preferable and a single bond is more preferable.
Examples of the alkylene group having 1 to 30 carbon atoms include methylene, ethylene, propylene, trimethylene, butylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, nonamethylene, decamethylene, A decamethylene group, a dodecamethylene group, etc. are mentioned, A C1-C20 alkylene group is preferable, A C1-C10 alkylene group is more preferable, A C1-C5 alkylene group is more preferable.
Examples of the arylene group having 6 to 20 ring carbon atoms include a phenylene group, a biphenylene group, a naphthylene group, an acenaphthylenyl group, an anthranylene group, a phenanthrylene group, a phenalenyl group, a quinolylene group, an isoquinolylene group, an s-indacenylene group, an as -Indasenylene group, chrysenylene group, the following formula

(* Represents a substitution position) and the like, and an arylene group having 6 to 15 ring carbon atoms is preferable, an arylene group having 6 to 10 ring carbon atoms is more preferable, and 1,3- A phenylene group and a 1,4-phenylene group are preferred.

A ¹ , A ² and A ³ each independently represent a monovalent group represented by the following general formula (2) or (3).

In general formulas (2) and (3), * indicates a substitution position.
Y is a single bond, an oxygen atom or a sulfur atom, preferably a single bond or an oxygen atom.
Z is an oxygen atom, a sulfur atom or an N—R ¹ group.
R ¹ of N-R ¹ groups are alkyl groups or rings formed aryl group having 6 to 18 carbon atoms having 1 to 20 carbon atoms. Examples of the alkyl group having 1 to 20 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, various pentyl groups, and various pentyl groups. A hexyl group, various heptyl groups, various nonyl groups, various decyl groups, various undecyl groups, various dodecyl groups, and the like, preferably an alkyl group having 1 to 15 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, More preferred are alkyl groups having 1 to 5 carbon atoms. Examples of the aryl group having 6 to 18 ring carbon atoms include phenyl group, tolyl group, biphenylenyl group, naphthyl group, acenaphthylenyl group, anthryl group, aceanthryl group, phenanthryl group, phenalenyl group, fluorenyl group, and s-indacenyl. Group, an as-indacenyl group, and the like, an aryl group having 6 to 14 ring carbon atoms is preferable, and an aryl group having 6 to 10 ring carbon atoms is more preferable.
Here, in the above general formula (1), at least one of A ¹ , A ² and A ³ is represented by the above general formula (3), and the following general formula

In the formula, R ¹ is a group other than the carbazolyl group represented by the above definition.
Examples of such groups include the following groups.

(In the above formula, R ¹ is as defined above.)
In addition, if ^one of A ¹ , A ² and A ³ is represented by the general formula (3) and is a group other than the carbazolyl group, the remaining groups are represented by the general formula (2) or (3 As long as it is a group represented by), there is no other limitation, and it may be a carbazolyl group.

Among A ¹ -L ^1- , A ² -L ² -and A ³ -L ^3- defined as above, the substitution positions of A ¹ -L ¹ -and A ² -L ^2- are represented by the following formulae. It is preferable that they are the 6th and 8th positions in A, and the substitution position of A ³ -L ^3- is preferably the 2nd or 4th position in the following formula.

  A preferable specific organic EL element material is represented by the following general formula (1 ′) or (1 ″).

A more preferable organic EL element material is a case where, in the general formula (1 ′) or (1 ″), L ¹ , L ² and L ³ are all single bonds, specifically, the following general formula (1 '-I) or (1''-i).

In the general formulas (1 ′), (1′-i), (1 ″) and (1 ″ -i), A ¹ , A ² , A ³ , L ¹ , L ² , L ³ and X are As defined.
Specific examples of the organic EL element material represented by the general formula (1) defined as described above are as follows, but are not particularly limited thereto.

  The organic EL device material of the present invention represented by the general formula (1) preferably has a triplet energy level of 2.0 to 3.2 eV, preferably 2.5 to 3.2 eV. Is more preferable.

Next, the organic EL element of the present invention will be described.
The organic EL device of the present invention has one or more organic thin film layers including a light emitting layer between a cathode and an anode, and at least one of the organic thin film layers is represented by the general formula (1). Contains an organic EL element material.
As the structure of the multilayer organic EL element, for example, anode / hole transport layer (hole injection layer) / light emitting layer / cathode, anode / light emitting layer / electron transport layer (electron injection layer) / cathode, anode / positive Hole transport layer (hole injection layer) / light emitting layer / electron transport layer (electron injection layer) / cathode, anode / hole transport layer (hole injection layer) / light emitting layer / hole barrier layer / electron transport layer (electrons) Injected layer) / cathode, etc. are laminated.
In the organic EL device of the present invention, the light emitting layer preferably contains the organic EL device material represented by the general formula (1) as a host material, and further contains a phosphorescent material. Is more preferable. When the organic EL device of the present invention has a hole transport layer (hole injection layer), the hole transport layer (hole injection layer) can preferably contain the organic EL device material of the present invention. When the organic EL device of the present invention has an electron transport layer and / or a hole barrier layer, the electron transport layer and / or hole barrier layer can preferably contain the organic EL device material of the present invention.
As the phosphorescent material, iridium (Ir), osmium (Os), ruthenium (Ru), or platinum (Pt) is used because the phosphorescent quantum yield is high and the external quantum efficiency of the light-emitting element can be further improved. Are preferable, and metal complexes such as iridium complexes, osmium complexes, ruthenium complexes, and platinum complexes are more preferable. Among them, iridium complexes and platinum complexes are more preferable, and orthometalated iridium complexes are most preferable. Specific examples of metal complexes such as iridium complex, osmium complex, ruthenium complex and platinum complex are shown below.

  In the organic EL device of the present invention, it is preferable that the light-emitting layer contains a host complex and a phosphorescent material, and a metal complex having a maximum emission wavelength of 500 nm or less.

  The organic EL device of the present invention preferably has a reducing dopant in an interface region between the cathode and the organic thin film layer (for example, an electron injection layer or a light emitting layer). The reducing dopant is at least selected from alkali metals, alkali metal complexes, alkali metal compounds, alkaline earth metals, alkaline earth metal complexes, alkaline earth metal compounds, rare earth metals, rare earth metal complexes, rare earth metal compounds, and the like. One kind is mentioned.

As an alkali metal, the work function is 2.9 eV or less, Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV), Cs (work function: 1.95 eV) and the like are preferable. Of these, K, Rb, and Cs are more preferable, Rb or Cs is more preferable, and Cs is most preferable.
As alkaline earth metals, the work function is 2.9 eV or less, Ca (work function: 2.9 eV), Sr (work function: 2.0 to 2.5 eV), Ba (work function: 2.52 eV). Etc. are preferable.
As the rare earth metal, Sc, Y, Ce, Tb, Yb and the like having a work function of 2.9 eV or less are preferably exemplified.
Among the above metals, preferred metals are particularly high in reducing ability, and by adding a relatively small amount to the electron injection region, it is possible to improve the light emission luminance and extend the life of the organic EL element.

Examples of the alkali metal compound include alkali oxides such as Li ₂ O, Cs ₂ O, and K ₂ O, and alkali halides such as LiF, NaF, CsF, and KF. Among these, LiF, Li ₂ O, NaF is preferred.
Examples of the alkaline earth metal compound include BaO, SrO, CaO, and Ba _m Sr _1-m O (0 <m <1), Ba _m Ca _1-m O (0 <m <1), and the like obtained by mixing these. Of these, BaO, SrO, and CaO are preferable.
The rare earth metal _{compound, YbF 3, ScF 3, ScO} 3, Y 2 O 3, Ce 2 O 3, GdF 3, TbF 3 and the like, and among _{these, YbF 3, ScF 3, TbF} 3 are preferable.

  The alkali metal complex, alkaline earth metal complex, and rare earth metal complex are not particularly limited as long as each metal ion contains at least one of an alkali metal ion, an alkaline earth metal ion, and a rare earth metal ion. The ligands include quinolinol, benzoquinolinol, acridinol, phenanthridinol, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiaryloxadiazole, hydroxydiarylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxybenzotriazole, Hydroxyfulborane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, β-diketones, azomethines, and derivatives thereof are preferred, but not limited thereto.

As the addition form of the reducing dopant, it is preferable to form a layered or island-like shape in the interface region. As a forming method, a method in which a reducing dopant is deposited by a resistance heating vapor deposition method, an organic material as a light emitting material or an electron injection material for forming an interface region is simultaneously deposited, and the reducing dopant is dispersed in the organic material. The dispersion concentration in terms of molar ratio is preferably organic substance: reducing dopant = 100: 1 to 1: 100, more preferably 5: 1 to 1: 5.
In the case of forming the reducing dopant in layers, after forming the light emitting material or electron injecting material that is the organic layer at the interface in layers, the reducing dopant is vapor-deposited alone by resistance heating vapor deposition, preferably the layer thickness is 0. Formed at 1-15 nm.
When forming the reducing dopant in an island shape, after forming the light emitting material or electron injection material, which is an organic layer at the interface, in an island shape, the reducing dopant is vapor-deposited by resistance heating vapor deposition alone, preferably the thickness of the island It is formed at 0.05 to 1 nm.

  When the organic EL device of the present invention has an electron injection layer between the light emitting layer and the cathode, the electron transport material used for the electron injection layer is an aromatic heterocycle containing one or more heteroatoms in the molecule. Compounds are preferred, and nitrogen-containing ring derivatives are particularly preferred.

  As this nitrogen-containing ring derivative, for example, a nitrogen-containing ring metal chelate complex represented by the following general formula (A) is preferable.

R ^{2 to} R ⁷ each independently represent a hydrogen atom, a halogen atom, an amino group, a hydrocarbon group having 1 to 40 carbon atoms, an alkoxy group, an aryloxy group, an alkoxycarbonyl group, or a heterocyclic group, May be substituted.

Examples of the halogen atom represented by R ^{2 to} R ⁷ include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
Examples of the optionally substituted amino group represented by R ^{2 to} R ⁷ include an alkylamino group, an arylamino group, an aralkylamino group, and the like. Examples of the alkyl group of the alkylamino group include a methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, and 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, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, 3-methylpentyl 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, -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, 1 , 2-dinitroethyl group, 2,3-dinitro-t-butyl group, 1,2,3-trinitropropyl group and other alkyl groups having 1 to 40 carbon atoms, 20 alkyl groups are preferable, and an alkyl group having 1 to 10 carbon atoms is more preferable.
Examples of the aryl group of the arylamino group include a 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-butylphenol 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 Examples thereof include aryl groups having 6 to 40 ring carbon atoms such as -t-butyl-p-terphenyl-4-yl group, aryl groups having 6 to 20 ring carbon atoms are preferable, and ring forming carbon atoms are 6 10 to 10 aryl groups are more preferred.
As the aralkyl group of the aralkylamino group, for example, benzyl group, 1-phenylethyl group, 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-methyl Benzyl group, p-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromobenzyl group, m-butyl Mobenzyl 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 Examples include aralkyl groups having 7 to 40 carbon atoms such as -hydroxy-2-phenylisopropyl group and 1-chloro-2-phenylisopropyl group, preferably aralkyl groups having 7 to 20 carbon atoms, and aralkyl having 7 to 10 carbon atoms. Groups are preferred.

Examples of the hydrocarbon group having 1 to 40 carbon atoms represented by R ^{2 to} R ⁷ include a substituted or unsubstituted alkyl group, alkenyl group, cycloalkyl group, aryl group, and aralkyl group.
As an alkyl group, the same thing as the alkyl group of the above-mentioned alkylamino group is mentioned, A C1-C20 alkyl group is preferable and a C1-C10 alkyl group is more preferable.
Examples of the alkenyl group include vinyl group, allyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1,3-butanedienyl group, 1-methylvinyl group, styryl group, and 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-diphenyl Examples thereof include alkenyl groups having 2 to 40 carbon atoms such as allyl group, 1,2-dimethylallyl group, 1-phenyl-1-butenyl group, and 3-phenyl-1-butenyl group, and alkenyl groups having 2 to 20 carbon atoms. Are preferable, and an alkenyl group having 2 to 10 carbon atoms is preferable.
Examples of the cycloalkyl group include ring-forming carbon such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group and 2-norbornyl group. A cycloalkyl group having a number of 3 to 40 is exemplified, and a cycloalkyl group having a ring forming carbon number of 3 to 10 is preferable.
Examples of the aryl group include the same aryl groups as those described above for the arylamino group, preferably an aryl group having 6 to 20 ring carbon atoms, and more preferably an aryl group having 6 to 10 ring carbon atoms.
Examples of the aralkyl group include the same aralkyl groups as those described above, and an aralkyl group having 7 to 20 carbon atoms is preferable, and an aralkyl group having 7 to 10 carbon atoms is preferable.

Examples of the optionally substituted alkoxy group represented by R ^{2 to} R ⁷ include the same alkyl groups as those described above for the alkylamino group, preferably an alkoxy group having 1 to 20 carbon atoms, A C1-C10 alkoxy group is more preferable.
Examples of the optionally substituted aryloxy group represented by R ^{2 to} R ⁷ include those having an aryl group site similar to the aryl group of the aforementioned arylamino group, and an aryl group having 6 to 20 ring carbon atoms. An aryl group having 6 to 10 ring carbon atoms is more preferable.
Examples of the optionally substituted alkoxycarbonyl group represented by R ^{2 to} R ⁷ include the same alkyl group as the alkyl group of the aforementioned alkylamino group, preferably an alkoxycarbonyl group having 2 to 20 carbon atoms. An alkoxycarbonyl group having 2 to 10 carbon atoms is more preferable.
The optionally substituted heterocyclic group represented by R ^{2 to} R ⁷ is a monocyclic ring or a condensed ring, preferably having 1 to 20 ring forming carbon atoms, more preferably 1 to 12 ring forming carbon atoms, still more preferably. It is a heterocyclic group having 2 to 10 ring carbon atoms, and is an aromatic heterocyclic group containing at least one hetero atom of a nitrogen atom, an oxygen atom, a sulfur atom and a selenium atom. Examples of such heterocyclic groups include pyrrolidine, piperidine, piperazine, morpholine, thiophene, selenophene, furan, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyridazine, pyrimidine, triazole, triazine, indole, indazole, purine, thiazoline, thiazole. , Thiadiazole, oxazoline, oxazole, oxadiazole, quinoline, isoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, acridine, phenanthroline, phenazine, tetrazole, benzimidazole, benzoxazole, benzothiazole, benzotriazole, tetrazaindene , A group derived from carbazole, azepine and the like, preferably furan, thio , Pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, more preferably a group derived from furan, thiophene, pyridine, and quinoline, more preferably a quinolinyl group. .

M is aluminum (Al), gallium (Ga), or indium (In), and is preferably indium.
L ⁴ in the formula (A) is a group represented by the following formula (A ′) or (A ″).

(Wherein R ^{8 to} R ¹² each independently represent a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and groups adjacent to each other may form a cyclic structure. R ^{13 to} R ²⁷ each independently represent a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and groups adjacent to each other may form a cyclic structure. )

The hydrocarbon groups having 1 to 40 carbon atoms represented by R ^{8 to} R ^{12 in the} formula (A ′) and R ^{13 to} R ²⁷ in the formula (A ″) are all specific examples of R ^{2 to} R ⁷ . The same thing is mentioned.
Examples of the divalent group in the case where the adjacent groups in R ^{8 to} R ¹² and R ^{13 to} R ²⁷ form a cyclic structure include a tetramethylene group, a pentamethylene group, a hexamethylene group, and diphenylmethane-2. , 2'-diyl group, diphenylethane-3,3'-diyl group, diphenylpropane-4,4'-diyl group and the like.

  Specific examples of the nitrogen-containing ring metal chelate complex represented by the formula (A) are shown below, but are not limited to these exemplified compounds.

  Examples of the nitrogen-containing heterocyclic derivative include nitrogen-containing heterocyclic derivatives that are organic compounds having the following general formula and are not metal complexes. For example, a 5-membered or 6-membered ring containing the skeleton shown in (a) and a structure shown in the formula (b) can be mentioned.

(In 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. Furthermore, 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) .

  The nitrogen-containing group of the nitrogen-containing organic compound is selected from, for example, nitrogen-containing heterocyclic groups represented by the following general formula.

(In each formula, R ²⁸ 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 And when n is an integer of 2 or more, the plurality of R ²⁸ may be the same or different from each other.)

  Furthermore, preferred specific compounds include nitrogen-containing heterocyclic derivatives represented by the following formula.

(Wherein, HAr ^a is substituted a nitrogen-containing heterocyclic ring which may having 3 to 40 carbon atoms, L ^b represents a single bond, carbon atoms which may have a substituent having 6 to 40 An arylene group or a heteroarylene group having 3 to 40 carbon atoms that may have a substituent, and Ar ^b is a divalent aromatic hydrocarbon having 6 to 40 carbon atoms that may have a substituent. And Ar ^c 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.

HAr ^a is selected from, for example, the following group.

L ⁶ is selected from the following group, for example.

Ar ^c is exemplarily selected from the following group.

Ar ^b is, for example, selected from the following arylanthranyl groups.

(In the formula, R ^{29 to} R ⁴² each independently represents 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, An aryl group having 6 to 40 carbon atoms or a heteroaryl group having 3 to 40 carbon atoms which may have a substituent, and Ar ^d is an aryl having 6 to 40 carbon atoms which may have a substituent. Group or a heteroaryl group having 3 to 40 carbon atoms.)
In Ar ^b represented by the above formula, each of R ^{29 to} R ³⁶ is preferably a nitrogen-containing heterocyclic derivative which is a hydrogen atom.

  In addition, the following compounds (see JP-A-9-3448) are also preferably used.

Wherein R ^{43 to} R ⁴⁶ are each independently a hydrogen atom, a substituted or unsubstituted aliphatic group, a substituted or unsubstituted aliphatic cyclic group, a substituted or unsubstituted carbocyclic aromatic ring group Represents a substituted or unsubstituted heterocyclic group, and X ¹ and X ² each independently represents an oxygen atom, a sulfur atom or a dicyanomethylene group.)

  In addition, the following compounds (see JP 2000-173774 A) are also preferably used.

In the formula, R ⁴⁷ , R ⁴⁸ , R ⁴⁹ and R ⁵⁰ are the same or different groups and are aryl groups represented by the following formulae.

Wherein R ⁵¹ , R ⁵² , R ⁵³ , R ⁵⁴ and R ⁵⁵ are the same or different from each other, and a hydrogen atom or at least one of them is a saturated or unsaturated alkoxyl group, alkyl group, amino group Or an alkylamino group.)

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

  Moreover, it is preferable that an electron carrying layer contains at least any one of the nitrogen-containing heterocyclic derivatives represented by the following general formulas (201) to (203).

In formulas (201) to (203), R ⁵⁶ 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, an alkyl group having 1 to 20 carbon atoms which may have a substituent or an alkoxy group having 1 to 20 carbon atoms which may have a substituent, wherein n is 0 to 0; 4 is an integer, and R ⁵⁷ is an aryl group having 6 to 60 carbon atoms which may have a substituent, a pyridyl group which may have a substituent, and quinolyl which may have a substituent. Group, an optionally substituted alkyl group having 1 to 20 carbon atoms or an alkoxy group having 1 to 20 carbon atoms, R ⁵⁸ and R ⁵⁹ each independently have a hydrogen atom and a substituent. An aryl group having 6 to 60 carbon atoms, a pyridyl group which may have a substituent, and a substituent. Which may be a quinolyl group, an alkyl group or an optionally substituted alkoxy group having 1 to 20 carbon atoms having 1 to 20 carbon atoms that may have a substituent, L ⁷ represents a single It has a bond, 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. Ar ^e may be an arylene group having 6 to 60 carbon atoms that may have a substituent, a pyridinylene group that may have a substituent, or a substituent. A good quinolinylene group, Ar ^f 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, and a substituent; A quinolyl group, which may have a substituent, 1 carbon atom Have an alkyl group or a substituent of 20 is also alkoxy group having 1 to 20 carbon atoms.
Ar ^g 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, an optionally substituted alkoxy group having 1 to 20 carbon atoms, or a group represented by -Ar ^e -Ar ^f (Ar ^e and Ar ^f Are the same as above.

In the formulas (201) to (203), R ⁵⁶ represents a hydrogen atom, an optionally substituted aryl group having 6 to 60 carbon atoms, an optionally substituted pyridyl group, They are a quinolyl group which may have a substituent, 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 group, naphthacenyl group, chrysenyl group, pyrenyl group, biphenyl group, terphenyl group, tolyl group, t-butylphenyl group, (2-phenylpropyl) phenyl group, fluoranthenyl group, fluorenyl group, spirobifluorene Monovalent group consisting of a valent group, perfluorophenyl group, perfluoronaphthyl group, perfluoroanthryl group, perfluorobiphenyl group, 9-phenylanthracene, monovalent group consisting of 9- (1′-naphthyl) anthracene A monovalent group consisting of a group, 9- (2′-naphthyl) anthracene, Monovalent group consisting of cene, monovalent group consisting of 9- [4- (diphenylamino) phenyl] anthracene, and the like. Phenyl group, naphthyl group, biphenyl group, terphenyl group, 9- (10-phenyl) ) 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, in addition to methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, and the like, trifluoro Examples thereof include haloalkyl groups such as a methyl 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 ⁵⁶ include a halogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, and an optionally substituted alkoxy group having 1 to 20 carbon atoms. , 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 3 carbon atoms which may have a substituent ˜40 heteroaryl groups and the like.
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 the formula (201), R ⁵⁷ 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 ⁵⁸ and R ⁵⁹ 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, preferred carbon numbers and substituents of these groups are the same as those described for ^R56 .

In Formulas (201) to (203), L ⁷ is a single bond, 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 which may have 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 ⁷ is the same as that described for R ⁵⁶ .

L ⁷ is

A group selected from the group consisting of
In the above formula (201), Ar ^e may have an optionally substituted arylene group having 6 to 60 carbon atoms, an optionally substituted pyridinylene group, or a substituent. It is a quinolinylene group. The substituent for each group represented by Ar ^e and Ar ^g is the same as that described for R ⁵⁶ .
In addition, Ar ^e is preferably any group selected from the condensed 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 indicated Ar ^e (103) is preferably a fused ring group represented by the following formula (111) - (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. 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 Formula (201), Ar ^f has a hydrogen atom, an aryl group having 6 to 60 carbon atoms that may have a substituent, a pyridyl group that may have a substituent, or a substituent. Or 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.
Specific examples, preferred carbon numbers and substituents of these groups are the same as those described for ^R56 .

In the above formulas (202) and (203), Ar ^g 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. which may be a quinolyl group which may have a substituent alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms that may have a substituent, or a -Ar ^e -Ar ^f (Ar ^e and Ar ^f are each the same as described above).
Specific examples, preferred carbon numbers and substituents of these groups are the same as those described for ^R56 .
Ar ^g is preferably any group selected from condensed 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 Ar ^g is preferably a condensed ring group represented by the following formulas (136) to (158).

In the above formulas (136) to (158), 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 ^f and Ar ^g 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), (9-1), and (9-7) are preferable.

  Moreover, as a nitrogen-containing ring derivative, a nitrogen-containing 5-membered ring derivative is also mentioned preferably. Examples of the nitrogen-containing 5-membered ring include an imidazole ring, a triazole ring, a tetrazole ring, an oxadiazole ring, a thiadiazole ring, an oxatriazole ring, and a thiatriazole ring. Examples of the nitrogen-containing 5-membered ring derivative include benzimidazole A ring, a benzotriazole ring, a pyridinoimidazole ring, a pyrimidinoimidazole ring, and a pyridazinoimidazole ring, and particularly preferably one represented by the following general formula (B).

In formula (B), L ^B represents a divalent or higher linking group, for example, carbon atom, a silicon atom, a nitrogen atom, a boron atom, an oxygen atom, a sulfur atom, a metal atom (e.g., barium atom, a beryllium atom) , Aromatic hydrocarbon rings, aromatic heterocyclic rings, etc., among which carbon atoms, nitrogen atoms, silicon atoms, boron atoms, oxygen atoms, sulfur atoms, aromatic hydrocarbon rings, aromatic heterocyclic groups are preferred. , A carbon atom, a silicon atom, an aromatic hydrocarbon ring, and an aromatic heterocyclic group are more preferable.
L aromatic hydrocarbon ring and an aromatic heterocyclic group ^B may have a substituent, and examples of the substituent include preferably an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an amino group, an alkoxy group , Aryloxy group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, acyloxy group, acylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio group, arylthio group, A sulfonyl group, a halogen atom, a cyano group, and an aromatic heterocyclic group, more preferably an alkyl group, an aryl group, an alkoxy group, an aryloxy group, a halogen atom, a cyano group, and an aromatic heterocyclic group, and more preferably Alkyl group, aryl group, alkoxy group An aryloxy group, an aromatic heterocyclic group, particularly preferably an alkyl group, an aryl group, an alkoxy group, an aromatic heterocyclic group.

Specific examples of L ^B, are listed below.

X ^B2 in the general formula (B) represents —O—, —S—, or —N (R ^B2 ) —. R ^B2 represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group.
The aliphatic hydrocarbon group for R ^B2 is a linear or branched alkyl group (preferably an alkyl group having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms, For example, methyl group, ethyl group, isopropyl group, t-butyl group, n-octyl group, n-decyl group, n-hexadecyl group, etc.), cycloalkyl group (preferably having 3 to 10 ring carbon atoms) For example, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, etc.), an alkenyl group (preferably having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 8 carbon atoms). An alkenyl group, for example, a vinyl group, an allyl group, a 2-butenyl group, a 3-pentenyl group, etc.), an alkynyl group (preferably having 2 to 20 carbon atoms, more preferred). 2 to 12 carbon atoms, and particularly preferably an alkynyl group having 2 to 8 carbon atoms, such as propargyl group, 3-pentynyl group and the like.), And alkyl group are preferred.

The aryl group of R ^B2 is a monocyclic ring or a condensed ring, preferably an aryl group having 6 to 30 ring carbon atoms, more preferably 6 to 20 ring carbon atoms, and further preferably 6 to 12 ring carbon atoms. For example, phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2-methoxyphenyl group, 3-trifluoromethylphenyl group, pentafluorophenyl group, 1-naphthyl group, 2- A naphthyl group etc. are mentioned, A phenyl group and 2-methylphenyl group are preferable.

The heterocyclic group of R ^B2 is a monocyclic ring or a condensed ring, and preferably has 1 to 20 ring carbon atoms, more preferably has 1 to 12 ring carbon atoms, and still more preferably has 2 to 10 ring carbon atoms. And an aromatic heterocyclic group containing at least one hetero atom of a nitrogen atom, an oxygen atom, a sulfur atom and a selenium atom. Examples of this heterocyclic group include, for example, pyrrolidine, piperidine, piperazine, morpholine, thiophene, selenophene, furan, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyridazine, pyrimidine, triazole, triazine, indole, indazole, purine, thiazoline , Thiazole, thiadiazole, oxazoline, oxazole, oxadiazole, quinoline, isoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, acridine, phenanthroline, phenazine, tetrazole, benzimidazole, benzoxazole, benzothiazole, benzotriazole, tetra Groups derived from Zaindene, carbazole, azepine, etc., preferably furan, Fen, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, more preferably furan, a group derived thiophene, pyridine and quinoline, further more preferably a quinolinyl group.

The aliphatic hydrocarbon group, aryl group and heterocyclic group represented by R ^B2 may have a substituent, and the substituent is preferably an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an amino group, Group, alkoxy group, aryloxy group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, acyloxy group, acylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio group , Arylthio group, sulfonyl group, halogen atom, cyano group, aromatic heterocyclic group, more preferably alkyl group, aryl group, alkoxy group, aryloxy group, halogen atom, cyano group, aromatic heterocyclic group More preferably, an alkyl group or an aryl group Alkoxy group, an aryloxy group, an aromatic heterocyclic group, particularly preferably an alkyl group, an aryl group, an alkoxy group, an aromatic heterocyclic group.
R ^B2 is preferably an aliphatic hydrocarbon group, an aryl group or a heterocyclic group, more preferably an aliphatic hydrocarbon group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, still more preferably). Is an aryl group, more preferably an aliphatic hydrocarbon group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, still more preferably 2 to 10 carbon atoms). Stuff).
X ^B2 is preferably —O— or N (R ^B2 ) —, and more preferably —N (R ^B2 ) —.

Z ^B2 represents an atomic group necessary for forming an aromatic ring. The aromatic ring formed by Z ^B2 may be either an aromatic hydrocarbon ring or an aromatic heterocyclic ring. Specific examples include, for example, a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring, Examples include pyrrole ring, furan ring, thiophene ring, selenophene ring, tellurophen ring, imidazole ring, thiazole ring, selenazole ring, tellurazole ring, thiadiazole ring, oxadiazole ring, pyrazole ring, preferably benzene ring, pyridine ring, A pyrazine ring, a pyrimidine ring, and a pyridazine ring, more preferably a benzene ring, a pyridine ring, and a pyrazine ring, still more preferably a benzene ring and a pyridine ring, and particularly preferably a pyridine ring.

The aromatic ring formed by Z ^B2 may further form a condensed ring with another ring and may have a substituent. The substituent is the same as those exemplified as the substituents of the group represented by the L ^B, preferably an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, an acyl group , Alkoxycarbonyl group, aryloxycarbonyl group, acyloxy group, acylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio group, arylthio group, sulfonyl group, halogen atom, cyano Group, a heterocyclic group, more preferably an alkyl group, an aryl group, an alkoxy group, an aryloxy group, a halogen atom, a cyano group, or a heterocyclic group, and still more preferably an alkyl group, an aryl group, an alkoxy group, an aryloxy group Group, aromatic complex It is a group, particularly preferably an alkyl group, an aryl group, an alkoxy group, an aromatic heterocyclic group.
n ^B2 is an integer of 1 to 4, preferably 2 to 3.

  Of the nitrogen-containing five-membered ring derivatives represented by the general formula (B), those represented by the following general formula (B ′) are more preferable.

In general formula (B ′), R ^B71 , R ^B72 and R ^B73 are the same as R ^B2 in general formula (B), respectively, and the preferred ranges are also the same.
Z ^B71 , Z ^B72 and Z ^B73 are the same as Z ^B2 in the general formula (B), respectively, and the preferred ranges are also the same.
L ^B71, L ^B72 and L ^B73 each represent a linking group, those divalent examples of L ^B can be mentioned in the general formula (B), preferably a single bond, a divalent aromatic hydrocarbon ring A linking group composed of a group, a divalent aromatic heterocyclic group, and a combination thereof, and more preferably a single bond. L ^B71, L ^B72 and L ^B73 may have a substituent, examples of the substituent are the same as those exemplified as the substituents of the group represented by L ^B in the foregoing formula (B), also The same applies to preferable substituents.
Y ^B represents a nitrogen atom, a 1,3,5-benzenetriyl group or a 2,4,6-triazinetriyl group. The 1,3,5-benzenetriyl group may have a substituent at the 2,4,6-position, and examples of the substituent include an alkyl group, an aromatic hydrocarbon ring group, and a halogen atom. It is done.

  Specific examples of the nitrogen-containing 5-membered ring derivative represented by General Formula (B) or General Formula (B ′) are shown below, but are not limited to these exemplified compounds.

As the compound constituting the electron injection layer and the electron transport layer, in addition to the organic EL device material of the present invention, an electron-deficient nitrogen-containing 5-membered ring or an electron-deficient nitrogen-containing 6-membered ring skeleton, and a substituted or unsubstituted Examples thereof include compounds having a structure in which an indole skeleton, a substituted or unsubstituted carbazole skeleton, and a substituted or unsubstituted azacarbazole skeleton are combined. Suitable electron-deficient nitrogen-containing 5-membered ring or electron-deficient nitrogen-containing 6-membered ring skeleton includes, for example, pyridine, pyrimidine, pyrazine, triazine, triazole, oxadiazole, pyrazole, imidazole, quinoxaline, pyrrole skeleton, and Examples thereof include molecular skeletons such as benzimidazole and imidazopyridine in which they are condensed with each other. Among these combinations, pyridine, pyrimidine, pyrazine, triazine skeleton, and carbazole, indole, azacarbazole, and quinoxaline skeleton are preferable. The aforementioned skeleton may be substituted or unsubstituted.
Specific examples of the electron transporting compound are shown below, but are not particularly limited thereto.

  The electron injection layer and the electron transport layer may have a single layer structure composed of one or more of the above materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions. The material of these layers preferably has a π-electron deficient nitrogen-containing heterocyclic group.

In addition to the nitrogen-containing ring derivative, it is preferable to use an insulator or a semiconductor as an inorganic compound as a constituent of the electron injection layer. If the electron injection layer is made of an insulator or a semiconductor, current leakage can be effectively prevented and the electron injection property can be improved.
As such an insulator, it is preferable to use at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides and alkaline earth metal halides. If the electron injection layer is composed of these alkali metal chalcogenides or the like, it is preferable in that the electron injection property can be further improved. Specifically, preferable alkali metal chalcogenides include, for example, Li ₂ O, K ₂ O, Na ₂ S, Na ₂ Se, and Na ₂ O, and preferable alkaline earth metal chalcogenides include, for example, CaO, BaO, and SrO. , BeO, BaS and CaSe. Further, preferable alkali metal halides include, for example, LiF, NaF, KF, LiCl, KCl, and NaCl. Examples of preferable alkaline earth metal halides include fluorides such as CaF ₂ , BaF ₂ , SrF ₂ , MgF ₂ and BeF ₂ , and halides other than fluorides.
As the semiconductor, for example, an oxide containing at least one element selected from the group consisting of Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta, Sb, and Zn. Products, nitrides, oxynitrides and the like, and these may be used alone or in combination of two or more. In addition, the inorganic compound constituting the electron injection layer is preferably a microcrystalline or amorphous insulating thin film. If the electron injection layer is composed of these insulating thin films, a more uniform thin film is formed, and pixel defects such as dark spots can be reduced. Examples of such inorganic compounds include alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides.
Moreover, the above-mentioned reducing dopant can be preferably contained in the electron injection layer in the present invention.
In addition, although the film thickness of an electron injection layer or an electron carrying layer is not specifically limited, Preferably, it is 1-100 nm.

  An aromatic amine compound, for example, an aromatic amine derivative represented by the following general formula (I) is suitably used for the hole injection layer or the hole transport layer (including the hole injection transport layer).

In the general formula (I), Ar ^{1 to} Ar ⁴ represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.

  Examples of the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms 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 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-tril 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, fluoranthenyl group, fluorenyl group and the like are mentioned, and aryl groups having 6 to 30 ring carbon atoms are preferable, ring formation An aryl group having 6 to 20 carbon atoms is more preferable.

  Examples of the substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms include 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl 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, 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-isobenfuran group Zofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 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-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-phenanthridinyl group 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl 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-phenance Lorin-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 -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-phena Throlin-3-yl group, 2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group, 2,9-phenanthrolin-6-yl group, 2,9- Phenanthrolin-7-yl group, 2,9-phenanthrolin-8-yl group, 2,9-phenanthrolin-10-yl group, 2,8-phenanthrolin-1-yl group, 2, 8-phenanthroline-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- 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 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-y 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 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- Examples thereof include a butyl 1-indolyl group, a 2-t-butyl 3-indolyl group, and a 4-t-butyl 3-indolyl group. Preferred examples include a phenyl group, a naphthyl group, a biphenyl group, an anthranyl group, a phenanthryl group, a pyrenyl group, a chrycenyl group, a fluoranthenyl group, and a fluorenyl group. A heteroaryl group having 5 to 30 ring atoms is preferred, and a ring A heteroaryl group having 5 to 20 forming atoms is more preferred.

L ⁵ is a divalent linking group. Specifically, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 50 ring atoms, or two or more arylene groups or heteroarylene groups. It is a divalent group obtained by bonding with a single bond, an ether bond, a thioether bond, an alkylene group having 1 to 20 carbon atoms, an alkenylene group having 2 to 20 carbon atoms or an amino group. Examples of the arylene group having 6 to 50 ring carbon atoms include 1,4-phenylene group, 1,2-phenylene group, 1,3-phenylene group, 1,4-naphthylene group, 2,6-naphthylene group, 1 , 5-naphthylene group, 9,10-anthranylene group, 9,10-phenanthrenylene group, 3,6-phenanthrenylene group, 1,6-pyrenylene group, 2,7-pyrenylene group, 6,12 -Chrysenylene group, 4,4'-biphenylene group, 3,3'-biphenylene group, 2,2'-biphenylene group, 2,7-fluorenylene group and the like, and arylene groups having 6 to 30 ring carbon atoms are included. An arylene group having 6 to 20 ring carbon atoms is more preferable. Examples of the heteroarylene group having 5 to 50 ring atoms include a 2,5-thiophenylene group, a 2,5-silolylene group, and a 2,5-oxadiazolylene group. Preferably, 1,4-phenylene group, 1,2-phenylene group, 1,3-phenylene group, 1,4-naphthylene group, 9,10-anthranylene group, 6,12-chrysenylene group, 4,4′-biphenylene Group, 3,3′-biphenylene group, 2,2′-biphenylene group, 2,7-fluorenylene group, heteroarylene groups having 5 to 30 ring atoms are preferable, and 5 to 20 ring atoms are preferable. A heteroarylene group is more preferred.

When L ⁵ is a linking group composed of two or more arylene groups or heteroarylene groups, adjacent arylene groups or heteroarylene groups may be bonded to each other via a divalent group to form a new ring. . Examples of such a divalent group forming a ring include a tetramethylene group, a pentamethylene group, a hexamethylene group, a diphenylmethane-2,2′-diyl group, a diphenylethane-3,3′-diyl group, and diphenyl. Examples include propane-4,4′-diyl group.

Examples of the substituent for Ar ^{1 to} Ar ⁴ and L ⁵ include a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, substituted or unsubstituted Substituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted carbon number 7 -50 aralkyl group, substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, substituted or unsubstituted heteroaryloxy group having 5 to 50 ring atoms, substituted or unsubstituted ring carbon atoms 6-50 arylthio group, substituted or unsubstituted heteroarylthio group having 5 to 50 ring atoms, substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms Amino group, halogen group, cyano group, nitro group, hydroxyl group substituted with a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms Group.

Examples of the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms as the substituent for Ar ^{1 to} Ar ⁴ and L ⁵ include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, and a 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-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, fluoranthenyl group, fluorenyl group, etc. An aryl group having 6 to 30 carbon atoms is preferable, and an aryl group having 6 to 20 ring carbon atoms is more preferable.

Examples of the substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms as substituents for Ar ^{1 to} Ar ⁴ and L ⁵ include 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, and pyrazinyl. Group, 2-pyridinyl 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 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-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 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 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, 3-carbazolyl group, 4-carbazolyl group Group, 9-carbazolyl group, 1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthryl Nyl group, 6-phenanthridinyl 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-phenanthrolin-4-yl group, 1, -Phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group, 1,8-phenanthrolin-9-yl group, , 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-phenanthroline-10-yl group, 1,10-phenanthrolin-2-yl group, 1,10-phenanthrolin-3-yl group, 1,10-phenanthroline- 4-yl group, 1,10-phenanthrolin-5-yl group, 2,9-phena Nsulolin-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-phenanthroline-6-yl group, 2,8-phenanthrolin-7-yl group, 2,8-phenanthrolin-9-yl group, 2,8-phenanthrolin-10-yl group Group, 2,7-phenanthrolin-1-yl group, 2,7-phenanthrolin-3- 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-pheno Thiazinyl 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 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, and heteroaryl having 5 to 30 ring atoms. Group is preferred, ring A heteroaryl group having 5 to 20 forming atoms is more preferred.

Examples of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms as the substituent for Ar ^{1 to} Ar ⁴ and L ⁵ include, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s- Butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxy Isobutyl 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-di Iodoisopropyl 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, -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-tricyano Propyl 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 and the like, an alkyl group having 1 to 30 carbon atoms is preferable, an alkyl group having 1 to 10 carbon atoms is more preferable, and an alkyl group having 1 to 5 carbon atoms is more preferable.

Examples of the substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms as the substituent for Ar ^{1 to} Ar ⁴ and L ⁵ include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and 4-methyl. Examples thereof include a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, a 2-norbornyl group, and the like. A cycloalkyl group having 3 to 30 ring carbon atoms is preferable, and a cycloalkyl group having 3 to 10 ring carbon atoms is preferable. An alkyl group is more preferred.

Examples of the alkyl group moiety of a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms as a substituent for Ar ^{1 to} Ar ⁴ and L ⁵ include, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, and 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-di- Chloro-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-amino Isobutyl 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- A butyl group, a 1,2,3-trinitropropyl group, etc. are mentioned, A C1-C30 alkoxy group is preferable, A C1-C10 alkoxy group is more preferable, A C1-C5 alkoxy group is Further preferred.

Examples of the substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms as the substituent for Ar ^{1 to} Ar ⁴ and L ⁵ include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, and 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-naphthyl group Isopropyl 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, -Chlorobenzyl group, p-bromobenzyl group, m-bromobenzyl group, o-bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group, m-hydroxy Benzyl 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, preferably an aralkyl group having 7 to 30 carbon atoms, 7-20 aralkyl groups are more preferred.

Examples of the aryl group moiety of the substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms as the substituent for Ar ^{1 to} Ar ⁴ and L ⁵ include a phenyl group, a 1-naphthyl group, and a 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-turf Enyl-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 and the like, and ring-forming carbon An aryloxy group having 6 to 30 carbon atoms is preferable, and an aryloxy group having 6 to 20 ring carbon atoms is more preferable.

Examples of the heteroaryl group part of the substituted or unsubstituted heteroaryloxy group having 5 to 50 ring atoms as the substituents for Ar ^{1 to} Ar ⁴ and L ⁵ include a 2-pyrrolyl group, a 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-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-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 1-phenanthridine Group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group, 7-phenanthridinyl group Ensridinyl 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 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-phenanthroline -10-yl group, 1,8-phenanthrolin-2-yl group, 1,8-phenanthrolin-3-yl group, 1,8-phenanthrolin-4-yl group, 1,8-phen group Nansulolin-5-yl group, 1,8-fur Nansulolin-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-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-phenanthro Rin-3-yl group, 2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group, 2,9-phenanthrolin-6-yl group, 2,9- Phenanthrolin-7-yl group, 2,9-phenanthrolin-8-yl group, 2,9-phenanthrolin-10-yl group, 2,8-phenanthrolin-1-yl group, 2, 8-phenanthroline-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, 3-furazanyl group, 2 -Thienyl group, 3-thienyl group, 2-methylpyrrol-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- Examples thereof include a t-butyl 3-indolyl group, a heteroaryloxy group having 5 to 30 ring atoms is preferable, and a heteroaryloxy group having 5 to 20 ring atoms is more preferable.

Examples of the aryl group portion of the substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms as the substituent for Ar ^{1 to} Ar ⁴ and L ⁵ include a phenyl group, a 1-naphthyl group, a 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-terfe group Nyl-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 and the like, and ring-forming carbon An arylthio group having 6 to 30 carbon atoms is preferable, and an arylthio group having 6 to 20 ring carbon atoms is more preferable.

Examples of the heteroaryl group portion of the substituted or unsubstituted heteroarylthio group having 5 to 50 ring atoms as the substituent for Ar ^{1 to} Ar ⁴ and L ⁵ include a 2-pyrrolyl group, a 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-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-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 1-phenanthridinyl Group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group, 7-phena Thridinyl 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 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-phenanthroline -10-yl group, 1,8-phenanthrolin-2-yl group, 1,8-phenanthrolin-3-yl group, 1,8-phenanthrolin-4-yl group, 1,8-phen group Nansulolin-5-yl group, 1,8-phen Nsulolin-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-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-phenanthroli -3-yl group, 2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group, 2,9-phenanthrolin-6-yl group, 2,9- Phenanthrolin-7-yl group, 2,9-phenanthrolin-8-yl group, 2,9-phenanthrolin-10-yl group, 2,8-phenanthrolin-1-yl group, 2, 8-phenanthroline-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 A group, a 2,7-phenanthrolin-3-yl group, a 2,7-phenanthrolin-4-yl group, , 7-phenanthroline-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, 3-furazanyl group, 2- Thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrol-3-yl group, 2-methylpyrrole- -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 -A butyl 3-indolyl group etc. are mentioned, A heteroarylthio group with 5-30 ring forming atoms is preferable, and a heteroarylthio group with 5-20 ring forming atoms is more preferable.

Examples of the alkyl group moiety of a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms as a substituent for Ar ^{1 to} Ar ⁴ and L ⁵ include, for example, a methyl group, an ethyl group, a propyl group, an 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-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-triamino Propyl 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. are mentioned, C2-C30 alkoxycarbonyl group is preferable, C2-C10 alkoxycarbonyl group is more preferable, C2-C2 More preferred is an alkoxycarbonyl group of 5.

Substituted by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms as a substituent for Ar ^{1 to} Ar ⁴ and L ⁵ Examples of the aryl group moiety and heteroaryl group moiety of the amino group include a 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 Group, p-tolyl group, p-t-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 Furanyl 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-quino Salinyl group, 6-quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl Group, 4-phenanthridinyl group, 6-phenanthridinyl 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-phenanthroline 8-yl group, 1,7-phenanthroline-9-yl group, 1,7-phenanthrolin-10-yl group, 1,8-phenanthrolin-2-yl group, 1,8-phenance Lorin-3-yl group, 1,8-phenanthrolin-4-yl group, 1,8-phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group, 1,8- Phenanthrolin-7-yl group, 1,8-phenanthroline-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-phenanthroline-5-yl group, 2,9-phenanthrolin-6-yl group, 2,9-phenanthrolin-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-phenanthroline -4-yl group, 2,8-phenanthrolin-5-yl group, 2,8-phen group Nsulolin-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-phenanthroline-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 -Feno Sasinyl 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-methylpyrrol-4-yl group, 2-methylpyrrol-5-yl group, 3-methylpyrrol-1-yl group, 3-methylpyrrol-2-yl 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 3-indolyl group, 4-t-butyl 3-indolyl group and the like can be mentioned.

  Specific examples of the compound of the general formula (I) are shown below, but are not limited thereto.

  Moreover, the aromatic amine of the following general formula (II) is also suitably used for formation of a hole injection layer or a hole transport layer.

In the general formula (II), the definitions of Ar ^{5 to} Ar ⁷ are the same as the definitions of Ar ^{1 to} Ar ^{4 in} the general formula (I). Specific examples of the compound of the general formula (II) are shown below, but are not limited thereto.

  In the present invention, the anode of the organic EL element plays a role of injecting holes into the hole transport layer or the light emitting layer, and it is effective to have a work function of 4.5 eV or more. Examples of the anode material used in the present invention include indium tin oxide alloy (ITO), tin oxide (NESA), gold, silver, platinum, and copper. The cathode is preferably a material having a low work function for the purpose of injecting electrons into the electron injection layer or the light emitting layer. The cathode material is not particularly limited, and specifically, indium, aluminum, magnesium, magnesium-indium alloy, magnesium-aluminum alloy, aluminum-lithium alloy, aluminum-scandium-lithium alloy, magnesium-silver alloy and the like can be used.

There is no restriction | limiting in particular in the formation method of each layer of the organic EL element of this invention, The formation method by a conventionally well-known vacuum evaporation method, a spin coating method, etc. can be used. The organic thin film layer containing the compound represented by the general formula (1) used for the organic EL device of the present invention is a vacuum deposition method, a molecular beam deposition method (MBE method) or a dipping method of a solution dissolved in a solvent, It can be formed by a known method such as a spin coating method, a casting method, a bar coating method, or a roll coating method.
The film thickness of each organic layer of the organic EL device of the present invention is not particularly limited. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur. Conversely, if it is too thick, a high applied voltage is required and the efficiency is deteriorated. Therefore, the range of several nm to 1 μm is usually preferable.

  EXAMPLES Hereinafter, the present invention will be specifically described with reference to examples, but the present invention is not limited thereto.

アルゴン雰囲気下、内容積１Ｌの反応器に、２，８−ジカルバゾリルジベンゾフラン１０．５ｇ（２１ｍｍｏｌ）及びＴＨＦ（６３０ｍｌ）を仕込み、０℃にてｔｅｒｔ−ブチルリチウム１４．８ｍｌ（１．４９ｍｏｌ／Ｌ溶液；２２．０５ｍｍｏｌ）を添加してから３０分撹拌した。その後、ヨウ素５．６０ｇ（２２．０５ｍｍｏｌ）を加え、さらに２時間撹拌した。反応終了後、水を添加してから濃縮し、次いでジクロロメタンで抽出した。これを無水硫酸マグネシウムで乾燥させた後、ろ過し、ろ液を濃縮して得られる固体を酢酸エチル（３０ｍｌ）により３回再結晶し、２，８−ジカルバゾリル−４−ヨードジベンゾフラン９．４４ｇ（収率７２％、白色固体）を得た。 <Synthesis Example 1> Compound (1-1)
[Synthesis of 2,8-dicarbazolyl-4-iododibenzofuran]

Under an argon atmosphere, 10.5 g (21 mmol) of 2,8-dicarbazolyl dibenzofuran and THF (630 ml) were charged into a reactor having an internal volume of 1 L, and 14.8 ml (1.49 mol) of tert-butyllithium at 0 ° C. / L solution; 22.05 mmol) was added, followed by stirring for 30 minutes. Thereafter, 5.60 g (22.05 mmol) of iodine was added, and the mixture was further stirred for 2 hours. After completion of the reaction, water was added and concentrated, followed by extraction with dichloromethane. This was dried over anhydrous magnesium sulfate, filtered, and the solid obtained by concentrating the filtrate was recrystallized three times with ethyl acetate (30 ml), and 9.44 g of 2,8-dicarbazolyl-4-iododibenzofuran ( Yield 72%, white solid).

アルゴン雰囲気下、内容積１００ｍｌのフラスコに、２，８−ジカルバゾリル−４−ヨードジベンゾフラン３．１２ｇ（５ｍｍｏｌ）、２−ジベンゾフランボロン酸１．１７ｇ（５．５ｍｍｏｌ）、２ｍｏｌ／Ｌの炭酸ナトリウム水溶液５ｍｌ（１０ｍｍｏｌ）、ジメトキシエタン１０ｍｌ及びトルエン１０ｍｌを仕込み、テトラキス（トリフェニルホスフィン）パラジウム０．２９ｇ（０．２５ｍｍｏｌ）を添加してから９時間還流させた。反応終了後、トルエンで抽出し、無水硫酸マグネシウムで乾燥した後、ろ過し、濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒；ヘキサン／トルエン＝６／４）で精製し、白色固体を得た。さらに該白色固体を３６０℃で昇華精製し、純度９９．８％の上記化合物（１−１）を２．６６ｇ（収率８０％）得た。
得られた化合物のＬＣ／ＭＳを測定したところ、化合物（１−１）のＣ₄₈Ｈ₂₈Ｎ₂Ｏ₂＝６６４に対し、ｍ／ｚ＝６６４が得られたことから、この化合物を目的物と同定した。 [Synthesis of Compound (1-1)]

Under an argon atmosphere, in a flask with an internal volume of 100 ml, 3.12 g (5 mmol) of 2,8-dicarbazolyl-4-iododibenzofuran, 1.17 g (5.5 mmol) of 2-dibenzofuranboronic acid, 5 ml of 2 mol / L aqueous sodium carbonate solution (10 mmol), 10 ml of dimethoxyethane, and 10 ml of toluene were added, 0.29 g (0.25 mmol) of tetrakis (triphenylphosphine) palladium was added, and the mixture was refluxed for 9 hours. After completion of the reaction, the mixture was extracted with toluene, dried over anhydrous magnesium sulfate, filtered and concentrated. The obtained residue was purified by silica gel column chromatography (developing solvent; hexane / toluene = 6/4) to obtain a white solid. Further, the white solid was purified by sublimation at 360 ° C. to obtain 2.66 g (yield 80%) of the compound (1-1) having a purity of 99.8%.
When LC / MS of the obtained compound was measured, m / z = 664 was obtained with respect to C ₄₈ H ₂₈ N ₂ O ₂ = 664 of compound (1-1). Was identified.

アルゴン雰囲気下、内容積２００ｍｌのフラスコに、２，８−ジブロモベンゾフラン４．８８ｇ（１５ｍｍｏｌ）、３−カルバゾリルフェニルボロン酸９．４７ｇ（３３ｍｍｏｌ）、２ｍｏｌ／Ｌの炭酸ナトリウム水溶液３０ｍｌ（６０ｍｍｏｌ）、ジメトキシエタン３０ｍｌ及びトルエン３０ｍｌを仕込み、テトラキス（トリフェニルホスフィン）パラジウム０．８７ｇ（０．７５ｍｍｏｌ）を添加してから９時間還流させた。反応終了後、ジクロロメタンで抽出し、無水硫酸マグネシウムで乾燥した後、ろ過し、濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒；ヘキサン／トルエン＝５／５）で精製し、さらにこれを酢酸エチルから再結晶し、白色固体の上記化合物（６−ａ）８．１０ｇ（収率８３％）を得た。 <Synthesis Example 2> Compound (1-6)
[Synthesis of Compound (6-a)]

Under an argon atmosphere, a flask with an internal volume of 200 ml was charged with 4.88 g (15 mmol) of 2,8-dibromobenzofuran, 9.47 g (33 mmol) of 3-carbazolylphenylboronic acid, 30 ml (60 mmol) of a 2 mol / L aqueous sodium carbonate solution. Then, 30 ml of dimethoxyethane and 30 ml of toluene were charged, 0.87 g (0.75 mmol) of tetrakis (triphenylphosphine) palladium was added, and the mixture was refluxed for 9 hours. After completion of the reaction, the mixture was extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered and concentrated. The obtained residue was purified by silica gel column chromatography (developing solvent; hexane / toluene = 5/5), and further recrystallized from ethyl acetate to obtain 8.10 g (yield) of the above compound (6-a) as a white solid. 83%).

合成例１の２，８−ジカルバゾリル−４−ヨードジベンゾフランの合成において、原料として２，８−ジカルバゾリルジベンゾフランの代わりに化合物（６−ａ）を用いたこと以外は同様にして実験を行なうことにより、化合物（６−ｂ）５．１２ｇ（収率５３％）を得た。 [Synthesis of Compound (6-b)]

In the synthesis of 2,8-dicarbazolyl-4-iododibenzofuran of Synthesis Example 1, the experiment is performed in the same manner except that the compound (6-a) is used instead of 2,8-dicarbazolyl dibenzofuran as a raw material. This gave 5.12 g (yield 53%) of compound (6-b).

合成例１の化合物（１−１）の合成において、原料として２，８−ジカルバゾリル−４−ヨードジベンゾフランの代わりに化合物（６−ｂ）を用いたこと以外は同様にして実験を行なうことにより、化合物（１−６）３．３４ｇ（収率６２％）を得た。
得られた化合物のＬＣ／ＭＳを測定したところ、化合物（１−６）のＣ₆₀Ｈ₃₆Ｎ₂Ｏ₂＝８１６に対しｍ／ｚ＝８１６が得られたことから、この化合物を目的物と同定した。 [Synthesis of Compound (1-6)]

In the synthesis of the compound (1-1) of Synthesis Example 1, an experiment was conducted in the same manner except that the compound (6-b) was used instead of 2,8-dicarbazolyl-4-iododibenzofuran as a raw material. 3.34 g (yield 62%) of compound (1-6) was obtained.
When LC / MS of the obtained compound was measured, m / z = 816 was obtained with respect to C ₆₀ H ₃₆ N ₂ O ₂ = 816 of compound (1-6). Identified.

アルゴン雰囲気下、内容積１００ｍｌのフラスコに、２，８−ジブロモジベンゾフラン４．８８ｇ（１５ｍｍｏｌ）、３−（Ｎ−フェニルカルバゾール）ボロン酸１０．３４ｇ（３６ｍｍｏｌ）、２ｍｏｌ／Ｌの炭酸ナトリウム水溶液３０ｍｌ（６０ｍｍｏｌ）、ジメトキシエタン３０ｍｌ及びトルエン３０ｍｌを仕込み、テトラキス（トリフェニルホスフィン）パラジウム０．８７ｇ（０．７５ｍｍｏｌ）を添加してから９時間還流させた。反応終了後、ジクロロメタンで抽出し、無水硫酸マグネシウムで乾燥した後、ろ過し、濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒；ヘキサン／トルエン＝５／５）で精製し、さらにこれを酢酸エチルで再結晶し、白色固体の上記化合物（１１−ａ）７．６１ｇ（収率７８％）を得た。
得られた化合物のＬＣ／ＭＳを測定したところ、化合物（１１−ａ）のＣ₄₈Ｈ₃₀Ｎ₂Ｏ＝６５０に対し、ｍ／ｚ＝６５０が得られたことから、この化合物を目的物と同定した。 <Synthesis Example 3> Compound (1-11)
[Synthesis of Compound (11-a)]

Under an argon atmosphere, in a flask having an internal volume of 100 ml, 4.88 g (15 mmol) of 2,8-dibromodibenzofuran, 10.34 g (36 mmol) of 3- (N-phenylcarbazole) boronic acid, 30 ml of a 2 mol / L aqueous sodium carbonate solution ( 60 mmol), 30 ml of dimethoxyethane and 30 ml of toluene were added, and 0.87 g (0.75 mmol) of tetrakis (triphenylphosphine) palladium was added, followed by refluxing for 9 hours. After completion of the reaction, the mixture was extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered and concentrated. The obtained residue was purified by silica gel column chromatography (developing solvent: hexane / toluene = 5/5), and further recrystallized from ethyl acetate to obtain 7.61 g (yield) of the above compound (11-a) as a white solid. 78%).
When LC / MS of the obtained compound was measured, m / z = 650 was obtained with respect to C ₄₈ H ₃₀ N ₂ O = 650 of the compound (11-a). Identified.

アルゴン雰囲気下、内容積５００ｍｌのフラスコに、化合物（１１−ａ）７．４８ｇ（１１．５ｍｍｏｌ）及びＴＨＦ２３０ｍｌを仕込み、０℃にて、１．５８ｍｏｌ／Ｌのｔｅｒｔ−ブチルリチウムのペンタン溶液７．６ｍｌ（ｔｅｒｔ−ブチルリチウム１２．０８ｍｍｏｌ相当）を加え、２時間撹拌した。その後、ヨウ素３．０６ｇ（１２．０８ｍｍｏｌ）を加え、０℃で１時間撹拌した後、室温に戻して２時間撹拌した。反応終了後、水を添加して攪拌してからジクロロメタンで抽出し、無水硫酸マグネシウムで乾燥した後、ろ過し、濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒；ヘキサン／トルエン＝５／５）で精製し、さらに酢酸エチルで再結晶することにより、淡黄色固体の化合物（１１−ｂ）６．４３ｇ（収率７２％）を得た。
得られた化合物のＬＣ／ＭＳを測定したところ、化合物（１１−ｂ）のＣ₄₈Ｈ₂₉ＩＮ₂Ｏ＝７７６に対し、ｍ／ｚ＝７７６が得られたことから、この化合物を目的物と同定した。 [Synthesis of Compound (11-b)]

In an argon atmosphere, 7.48 g (11.5 mmol) of compound (11-a) and 230 ml of THF were charged into a flask having an internal volume of 500 ml, and a pentane solution of 1.58 mol / L tert-butyllithium at 0 ° C. 6 ml (corresponding to 12.08 mmol of tert-butyllithium) was added and stirred for 2 hours. Thereafter, 3.06 g (12.08 mmol) of iodine was added and stirred at 0 ° C. for 1 hour, and then returned to room temperature and stirred for 2 hours. After completion of the reaction, water was added and stirred, then extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered and concentrated. The obtained residue was purified by silica gel column chromatography (developing solvent; hexane / toluene = 5/5), and further recrystallized from ethyl acetate to give 6.43 g (yield) of a pale yellow solid compound (11-b). 72%).
When LC / MS of the obtained compound was measured, m / z = 776 was obtained with respect to C ₄₈ H ₂₉ IN ₂ O = 776 of the compound (11-b). Identified.

アルゴン雰囲気下、内容積１００ｍｌのフラスコに、化合物（１１−ｂ）６．３６ｇ（８．２ｍｍｏｌ）、２−ジベンゾフランボロン酸２．０９ｇ（９．８４ｍｍｏｌ）、２ｍｏｌ／Ｌの炭酸ナトリウム水溶液８．２ｍｌ（１６．４ｍｍｏｌ）、ジメトキシエタン１６ｍｌ及びトルエン１６ｍｌを仕込み、テトラキストリフェニルホスフィンパラジウム０．４７ｇ（０．４１ｍｍｏｌ）を添加してから９時間還流させた。反応終了後、トルエンで抽出し、無水硫酸マグネシウムで乾燥した後、ろ過し、濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒；ヘキサン／トルエン＝５／５）で精製し、白色固体を得た。さらに該白色固体を３９０℃で昇華精製し、純度９９．７％の上記化合物（１−１１）３．５５ｇ（収率５３％）を得た。
得られた化合物のＬＣ／ＭＳを測定したところ、化合物（１−１１）のＣ₆₀Ｈ₃₆Ｎ₂Ｏ₂＝８１６に対し、ｍ／ｚ＝８１６が得られたことから、この化合物を目的物と同定した。 [Synthesis of Compound (1-11)]

Under an argon atmosphere, in a flask with an internal volume of 100 ml, 6.36 g (8.2 mmol) of compound (11-b), 2.09 g (9.84 mmol) of 2-dibenzofuranboronic acid, 8.2 ml of a 2 mol / L aqueous sodium carbonate solution (16.4 mmol), 16 ml of dimethoxyethane and 16 ml of toluene were added, and 0.47 g (0.41 mmol) of tetrakistriphenylphosphine palladium was added, followed by refluxing for 9 hours. After completion of the reaction, the mixture was extracted with toluene, dried over anhydrous magnesium sulfate, filtered and concentrated. The obtained residue was purified by silica gel column chromatography (developing solvent; hexane / toluene = 5/5) to obtain a white solid. Further, the white solid was purified by sublimation at 390 ° C. to obtain 3.55 g (yield 53%) of the above compound (1-11) having a purity of 99.7%.
When LC / MS of the obtained compound was measured, m / z = 816 was obtained with respect to C ₆₀ H ₃₆ N ₂ O ₂ = 816 of compound (1-11). Was identified.

アルゴン雰囲気下、内容積５００ｍｌのフラスコに、２，８−ジブロモジベンゾフラン４．８８ｇ（１５ｍｍｏｌ）及び脱水テトラヒドロフラン１５０ｍｌを仕込み、０℃にて、リチウム−２，２，６，６−テトラメチルピペリジン／ＴＨＦ溶液（２０ｍｌ／１５．７５ｍｍｏｌ）をキャヌラによって加え、２時間撹拌した。その後、さらにヨウ素４．００ｇ（１５．７５ｍｍｏｌ）を加え、０℃で１時間撹拌した。反応終了後、ジクロロメタンで抽出し、無水硫酸マグネシウムで乾燥した後、ろ過し、濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒；ヘキサン／トルエン＝７／３）で精製し、さらにヘキサンで再結晶することにより、淡黄色固体の化合物（１２−ａ）３．０５ｇ（収率４５％）を得た。
得られた化合物のＬＣ／ＭＳを測定したところ、化合物（１２−ａ）のＣ₁₂Ｈ₅Ｂｒ₂ＩＯ＝４５０に対し、ｍ／ｚ＝４５０が得られたことから、この化合物を目的物と同定した。 <Synthesis Example 4> Compound (1-12)
[Synthesis of Compound (12-a)]

Under an argon atmosphere, a flask having an internal volume of 500 ml was charged with 4.88 g (15 mmol) of 2,8-dibromodibenzofuran and 150 ml of dehydrated tetrahydrofuran, and at 0 ° C., lithium-2,2,6,6-tetramethylpiperidine / THF. The solution (20 ml / 15.75 mmol) was added via canula and stirred for 2 hours. Thereafter, 4.00 g (15.75 mmol) of iodine was further added, and the mixture was stirred at 0 ° C. for 1 hour. After completion of the reaction, the mixture was extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered and concentrated. The obtained residue was purified by silica gel column chromatography (developing solvent; hexane / toluene = 7/3), and further recrystallized from hexane to give 3.05 g (yield) of a pale yellow solid compound (12-a) 45%).
When LC / MS of the obtained compound was measured, m / z = 450 was obtained with respect to C ₁₂ H ₅ Br ₂ IO = 450 of compound (12-a). Identified.

アルゴン雰囲気下、内容積１００ｍｌのフラスコに、化合物（１２−ａ）３．０２ｇ（６．７ｍｍｏｌ）、２−ジベンゾフランボロン酸５．１５ｇ（２４．３ｍｍｏｌ）、２ｍｏｌ／Ｌの炭酸ナトリウム水溶液２０．１ｍｌ（４０．２ｍｍｏｌ）、ジメトキシエタン（１４ｍｌ）及びトルエン１４ｍｌを仕込み、テトラキス（トリフェニルホスフィン）パラジウム０．３９ｇ（０．３４ｍｍｏｌ）を添加してから９時間還流させた。反応終了後、トルエンで抽出し、無水硫酸マグネシウムで乾燥した後、ろ過し、濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒；ヘキサン／トルエン＝４／６）で精製し、白色固体を得た。該白色固体を３７０℃で昇華精製し、純度９９．８％の化合物（１−１２）２．６４ｇ（収率５９％）を得た。
得られた化合物のＬＣ／ＭＳを測定したところ、化合物（１−１２）のＣ₄₈Ｈ₂₆Ｏ₄＝６６６に対し、ｍ／ｚ＝６６６が得られたことから、この化合物を目的物と同定した。 [Synthesis of Compound (1-12)]

Under an argon atmosphere, in a flask with an internal volume of 100 ml, 3.02 g (6.7 mmol) of compound (12-a), 5.15 g (24.3 mmol) of 2-dibenzofuranboronic acid, 20.1 ml of a 2 mol / L aqueous sodium carbonate solution (40.2 mmol), dimethoxyethane (14 ml) and 14 ml of toluene were charged, and 0.39 g (0.34 mmol) of tetrakis (triphenylphosphine) palladium was added, followed by refluxing for 9 hours. After completion of the reaction, the mixture was extracted with toluene, dried over anhydrous magnesium sulfate, filtered and concentrated. The obtained residue was purified by silica gel column chromatography (developing solvent; hexane / toluene = 4/6) to obtain a white solid. The white solid was purified by sublimation at 370 ° C. to obtain 2.64 g (yield 59%) of compound (1-12) having a purity of 99.8%.
When LC / MS of the obtained compound was measured, m / z = 666 was obtained with respect to C ₄₈ H ₂₆ O ₄ = 666 of compound (1-12). did.

アルゴン雰囲気下、内容積１００ｍｌのフラスコに、２，８−ジカルバゾイル−４−ヨードジベンゾフラン３．７４ｇ（６ｍｍｏｌ）、４−ジベンゾフランボロン酸１．５２ｇ（７．２ｍｍｏｌ）、２ｍｏｌ／Ｌの炭酸ナトリウム水溶液６ｍｌ（１２ｍｍｏｌ）、ジメトキシエタン（１２ｍｌ）及びトルエン１２ｍｌを仕込み、テトラキス（トリフェニルホスフィン）パラジウム０．３５ｇ（０．３ｍｍｏｌ）を添加してから９時間還流させた。反応終了後、トルエンで抽出し、無水硫酸マグネシウムで乾燥した後、ろ過し、濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒；ヘキサン／トルエン＝５／５）で精製し、白色固体を得た。該白色固体を３６０℃で昇華精製し、純度９９．８％の化合物（１−１５）３．０７ｇ（収率７７％）を得た。
得られた化合物のＬＣ／ＭＳを測定したところ、化合物（１−１５）のＣ₄₈Ｈ₂₈Ｎ₂Ｏ₂＝６６４に対し、ｍ／ｚ＝６６４が得られたことから、この化合物を目的物と同定した。 <Synthesis Example 5> Compound (1-15)
[Synthesis of Compound (1-15)]

Under an argon atmosphere, in a flask with an internal volume of 100 ml, 3.74 g (6 mmol) of 2,8-dicarbazoyl-4-iododibenzofuran, 1.52 g (7.2 mmol) of 4-dibenzofuranboronic acid, 6 ml of a 2 mol / L aqueous sodium carbonate solution. (12 mmol), dimethoxyethane (12 ml) and 12 ml of toluene were charged, and 0.35 g (0.3 mmol) of tetrakis (triphenylphosphine) palladium was added, followed by refluxing for 9 hours. After completion of the reaction, the mixture was extracted with toluene, dried over anhydrous magnesium sulfate, filtered and concentrated. The obtained residue was purified by silica gel column chromatography (developing solvent; hexane / toluene = 5/5) to obtain a white solid. The white solid was purified by sublimation at 360 ° C. to obtain 3.07 g (yield 77%) of compound (1-15) having a purity of 99.8%.
When LC / MS of the obtained compound was measured, m / z = 664 was obtained with respect to C ₄₈ H ₂₈ N ₂ O ₂ = 664 of compound (1-15). Was identified.

<Synthesis Example 6> Compound (1-37)
[Synthesis of Compound (1-37)]
In the synthesis of Compound (1-12) of Synthesis Example 4, an experiment was conducted in the same manner as in Synthesis Example 4 except that 4-dibenzofuranboronic acid was used instead of 2-dibenzofuranboronic acid. 37) was obtained.

<Synthesis Example 7> Compound (1-46)
[Synthesis of Compound (1-46)]
In Synthesis Example 1, an experiment was conducted in the same manner as in Synthesis Example 1 except that 2,8-dicarbazolyl dibenzothiophene was used instead of 2,8-dicarbazolyl dibenzofuran as a raw material. 1-46) was obtained.

アルゴン雰囲気下、内容積１００ｍｌのフラスコに、２−ブロモジベンゾフラン４．９４ｇ（２０ｍｍｏｌ）、カルバゾール４．０１ｇ（２４ｍｍｏｌ）、リン酸カリウム１２．７４ｇ（６０ｍｍｏｌ）、ヨウ化銅１．９０ｇ（１０ｍｍｏｌ）及び脱水１，４−ジオキサン２０ｍｌを仕込み、ｔｒａｎｓ−１，２−ジアミノシクロヘキサン３．４３ｇ（３０ｍｍｏｌ）を添加してから９時間還流させた。反応終了後、トルエンを加えて希釈し、不溶物をろ過して除去し、ろ液を濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒；ヘキサン／トルエン＝６／４）で精製し、さらにヘキサンで再結晶することにより、白色固体の化合物（６２−ａ）４．５３ｇ（収率６８％）を得た。
得られた化合物のLC/MSを測定したところ、化合物（６２−ａ）のＣ₂₄Ｈ₁₅ＮＯ＝３３３に対し、ｍ／ｚ＝３３３が得られたことから、この化合物を目的物と同定した。 <Synthesis Example 8> Compound (1-62)
[Synthesis of Compound (62-a)]

Under an argon atmosphere, in a flask with an internal volume of 100 ml, 4.94 g (20 mmol) of 2-bromodibenzofuran, 4.01 g (24 mmol) of carbazole, 12.74 g (60 mmol) of potassium phosphate, 1.90 g (10 mmol) of copper iodide and 20 ml of dehydrated 1,4-dioxane was charged, 3.41 g (30 mmol) of trans-1,2-diaminocyclohexane was added, and the mixture was refluxed for 9 hours. After completion of the reaction, toluene was added for dilution, insoluble matters were removed by filtration, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (developing solvent; hexane / toluene = 6/4), and further recrystallized from hexane to give 4.53 g (yield 68) of a white solid compound (62-a). %).
When LC / MS of the obtained compound was measured, m / z = 333 was obtained with respect to C ₂₄ H ₁₅ NO = 333 of the compound (62-a). Thus, this compound was identified as a target product. .

アルゴン雰囲気下、内容積５００ｍｌのフラスコに、化合物（６２−ａ）４．５０ｇ（１３．５ｍｍｏｌ）及び脱水テトラヒドロフラン１３５ｍｌを仕込み、０℃にて、リチウム−２，２，６，６−テトラメチルピペリジン／ＴＨＦ溶液（１５ｍｌ／１４．８５ｍｍｏｌ）をキャヌラてに加え、２時間攪拌した。その後、さらにヨウ素３．７７ｇ（１４．８５ｍｍｏｌ）を加え、０℃で１時間撹拌した。その後、再度、０℃にてリチウム−２，２，６，６−テトラメチルピペリジン／ＴＨＦ溶液（１４．８５ｍｍｏｌ／１５ｍｌ）をキャヌラにて加え、２時間撹拌し、ヨウ素３．７７ｇ（１４．８５ｍｍｏｌ）を加え、０℃で１時間撹拌した。反応終了後、ジクロロメタンで抽出し、無水硫酸マグネシウムで乾燥した後、ろ過し、濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒；ヘキサン／トルエン＝５／５）で精製し、さらに酢酸エチルで再結晶することにより、淡黄色固体の化合物（６２−ｂ）３．１６ｇ（収率４０％）を得た。
得られた化合物のＬＣ／ＭＳを測定したところ、化合物（６２−ｂ）のＣ₂₄Ｈ₁₃Ｉ₂ＮＯ＝５８５に対し、ｍ／ｚ＝５８５が得られたことから、この化合物を目的物と同定した。 [Synthesis of Compound (62-b)]

In an argon atmosphere, a flask with an internal volume of 500 ml was charged with 4.50 g (13.5 mmol) of compound (62-a) and 135 ml of dehydrated tetrahydrofuran, and at 0 ° C., lithium-2,2,6,6-tetramethylpiperidine. / THF solution (15 ml / 14.85 mmol) was added to the cannula and stirred for 2 hours. Thereafter, 3.77 g (14.85 mmol) of iodine was further added, and the mixture was stirred at 0 ° C. for 1 hour. Thereafter, lithium-2,2,6,6-tetramethylpiperidine / THF solution (14.85 mmol / 15 ml) was added again at 0 ° C. with a cannula and stirred for 2 hours, and 3.77 g (14.85 mmol) of iodine was added. ) And stirred at 0 ° C. for 1 hour. After completion of the reaction, the mixture was extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered and concentrated. The obtained residue was purified by silica gel column chromatography (developing solvent; hexane / toluene = 5/5), and further recrystallized from ethyl acetate to obtain 3.16 g (yield) of a pale yellow solid compound (62-b). 40%).
When LC / MS of the obtained compound was measured, m / z = 585 was obtained with respect to C ₂₄ H ₁₃ I ₂ NO = 585 of the compound (62-b). Identified.

アルゴン雰囲気下、内容積１００ｍｌのフラスコに、化合物（６２−ｂ）３．１６ｇ（５．４ｍｍｏｌ）、２−ジベンゾフランボロン酸２．７５ｇ（１２．９６ｍｍｏｌ）、２ｍｏｌ／Ｌの炭酸ナトリウム水溶液５．４ｍｌ（１０．８ｍｍｏｌ）、ジメトキシエタン（１１ｍｌ）及びトルエン１１ｍｌを仕込み、テトラキストリフェニルホスフィンパラジウム０．３１ｇ（０．２７ｍｍｏｌ）を添加してから９時間還流させた。反応終了後、トルエンで抽出し、無水硫酸マグネシウムで乾燥した後、ろ過し、濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒；ヘキサン／トルエン＝４／６）で精製し、白色固体を得た。該白色固体を３８０℃で昇華精製し、純度９９．８％の化合物（１−６２）２．７０ｇ（収率７５％）を得た。
得られた化合物のＬＣ／ＭＳを測定したところ、化合物（１−６２）のＣ₄₈Ｈ₂₇ＮＯ₃＝６６５に対し、ｍ／ｚ＝６６５が得られたことから、この化合物を目的物と同定した。 [Synthesis of Compound (1-62)]

Under an argon atmosphere, in a flask having an internal volume of 100 ml, 3.16 g (5.4 mmol) of compound (62-b), 2.75 g (12.96 mmol) of 2-dibenzofuranboronic acid, 5.4 ml of 2 mol / L aqueous sodium carbonate solution (10.8 mmol), dimethoxyethane (11 ml) and 11 ml of toluene were charged, and 0.31 g (0.27 mmol) of tetrakistriphenylphosphine palladium was added, followed by refluxing for 9 hours. After completion of the reaction, the mixture was extracted with toluene, dried over anhydrous magnesium sulfate, filtered and concentrated. The obtained residue was purified by silica gel column chromatography (developing solvent; hexane / toluene = 4/6) to obtain a white solid. The white solid was purified by sublimation at 380 ° C. to obtain 2.70 g (yield 75%) of compound (1-62) having a purity of 99.8%.
When LC / MS of the obtained compound was measured, m / z = 665 was obtained with respect to C ₄₈ H ₂₇ NO ₃ = 665 of the compound (1-62). did.

アルゴン雰囲気下、内容積５００ｍｌのフラスコに、３−ブロモジベンゾフラン７．４１ｇ（３０ｍｍｏｌ）及び脱水テトラヒドロフラン１５０ｍｌを仕込み、０℃にてリチウム−２，２，６，６−テトラメチルピペリジン／ＴＨＦ溶液（３３ｍｌ／３３ｍｍｏｌ）を加え、２時間撹拌した。その後、さらにヨウ素８．３８ｇ（３３ｍｍｏｌ）を加え、０℃で１時間撹拌した。その後再度、０℃にてリチウム−２，２，６，６−テトラメチルピペリジン／ＴＨＦ溶液（３３ｍｍｏｌ／３３ｍｌ）を加え、２時間撹拌し、ヨウ素８．３８ｇ（３３ｍｍｏｌ）を加え、０℃で１時間撹拌した。反応終了後、ジクロロメタンで抽出し、無水硫酸マグネシウムで乾燥した後、ろ過し、濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒；ヘキサン／トルエン＝５／５）で精製し、さらにヘキサンで再結晶することにより、淡褐色固体の化合物（７４−ａ）６．４４ｇ（収率４３％）を得た。
得られた化合物のＬＣ／ＭＳを測定したところ、化合物（７４−ａ）のＣ₁₂Ｈ₅ＢｒＩ₂Ｏ＝４９８に対し、ｍ／ｚ＝４９８が得られたことから、この化合物を目的物と同定した。 <Synthesis Example 9> Compound (1-74)
[Synthesis of Compound (74-a)]

In an argon atmosphere, a flask having an internal volume of 500 ml was charged with 7.41 g (30 mmol) of 3-bromodibenzofuran and 150 ml of dehydrated tetrahydrofuran, and a lithium-2,2,6,6-tetramethylpiperidine / THF solution (33 ml) at 0 ° C. / 33 mmol) was added and stirred for 2 hours. Thereafter, 8.38 g (33 mmol) of iodine was further added, and the mixture was stirred at 0 ° C. for 1 hour. Thereafter, again, a lithium-2,2,6,6-tetramethylpiperidine / THF solution (33 mmol / 33 ml) was added at 0 ° C., and the mixture was stirred for 2 hours, and 8.38 g (33 mmol) of iodine was added. Stir for hours. After completion of the reaction, the mixture was extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered and concentrated. The obtained residue was purified by silica gel column chromatography (developing solvent; hexane / toluene = 5/5), and further recrystallized from hexane to give 6.44 g of a light brown solid compound (74-a) (yield) 43%).
When LC / MS of the obtained compound was measured, m / z = 498 was obtained with respect to C ₁₂ H ₅ BrI ₂ O = 498 of compound (74-a). Identified.

アルゴン雰囲気下、内容積１００ｍｌのフラスコに、化合物（７４−ａ）２．９９ｇ（６ｍｍｏｌ）、２−ジベンゾフランボロン酸４．５８ｇ（２１．６ｍｍｏｌ）、２ｍｏｌ／Ｌの炭酸ナトリウム水溶液１８ｍｌ（３６ｍｍｏｌ）、ジメトキシエタン１２ｍｌ及びトルエン１２ｍｌを仕込み、テトラキストリフェニルホスフィンパラジウム０．３５ｇ（０．３０ｍｍｏｌ）を添加してから９時間還流させた。反応終了後、トルエンで抽出し、無水硫酸マグネシウムで乾燥した後、ろ過し、濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒；ヘキサン／トルエン＝３／７）で精製し、白色固体を得た。該白色固体を３８０℃で昇華精製し、純度９９．７％の化合物（１−７４）２．９６ｇ（収率７４％）を得た。
得られた化合物のＬＣ／ＭＳを測定したところ、化合物（１−７４）のＣ₄₈Ｈ₂₆Ｏ₄＝６６６に対し、ｍ／ｚ＝６６６が得られたことから、この化合物を目的物と同定した。 [Synthesis of Compound (1-74)]

Under an argon atmosphere, in a flask with an internal volume of 100 ml, 2.99 g (6 mmol) of compound (74-a), 4.58 g (21.6 mmol) of 2-dibenzofuranboronic acid, 18 ml (36 mmol) of a 2 mol / L aqueous sodium carbonate solution, 12 ml of dimethoxyethane and 12 ml of toluene were charged, 0.35 g (0.30 mmol) of tetrakistriphenylphosphine palladium was added, and the mixture was refluxed for 9 hours. After completion of the reaction, the mixture was extracted with toluene, dried over anhydrous magnesium sulfate, filtered and concentrated. The obtained residue was purified by silica gel column chromatography (developing solvent; hexane / toluene = 3/7) to obtain a white solid. The white solid was purified by sublimation at 380 ° C. to obtain 2.96 g (yield 74%) of the compound (1-74) having a purity of 99.7%.
When LC / MS of the obtained compound was measured, m / z = 666 was obtained with respect to C ₄₈ H ₂₆ O ₄ = 666 of compound (1-74). did.

アルゴン雰囲気下、内容積１００ｍｌのフラスコに、化合物（７４−ａ）２．９９ｇ（６ｍｍｏｌ）、４−ジベンゾフランボロン酸４．５８ｇ（２１．６ｍｍｏｌ、２ｍｏｌ／Ｌの炭酸ナトリウム水溶液１８ｍｌ（３６ｍｍｏｌ）、ジメトキシエタン１２ｍｌ及びトルエン１２ｍｌを仕込み、テトラキストリフェニルホスフィンパラジウム０．３５ｇ（０．３０ｍｍｏｌ）を添加してから９時間還流させた。反応終了後、トルエンで抽出し、無水硫酸マグネシウムで乾燥した後、ろ過し、濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒；ヘキサン／トルエン＝５／５）で精製し、白色固体を得た。得られた白色固体を３８０℃で昇華精製し、純度９９．８％の化合物（１−８１）２．８０ｇ（収率７０％）を得た。
得られた化合物のＬＣ／ＭＳを測定したところ、化合物（１−８１）のＣ₄₈Ｈ₂₆Ｏ₄＝６６６に対し、ｍ／ｚ＝６６６が得られたことから、この化合物を目的物と同定した。 <Synthesis Example 10> Compound (1-81)
[Synthesis of Compound (1-81)]

Under an argon atmosphere, in a flask with an internal volume of 100 ml, 2.99 g (6 mmol) of compound (74-a), 4.58 g (21.6 mmol) of 2-dibenzofuranboronic acid, 18 ml (36 mmol) of a 2 mol / L aqueous sodium carbonate solution, dimethoxy After charging 12 ml of ethane and 12 ml of toluene and adding 0.35 g (0.30 mmol) of tetrakistriphenylphosphine palladium, the mixture was refluxed for 9 hours, extracted with toluene, dried over anhydrous magnesium sulfate, filtered The obtained residue was purified by silica gel column chromatography (developing solvent; hexane / toluene = 5/5) to obtain a white solid, which was purified by sublimation at 380 ° C. 99.8% of the compound (1-81) 2.80 g (yield 70%) was obtained.
When LC / MS of the obtained compound was measured, m / z = 666 was obtained with respect to C ₄₈ H ₂₆ O ₄ = 666 of compound (1-81). did.

<Example 1> Manufacture of organic EL element A glass substrate with ITO transparent electrode (manufactured by Geomatic Co., Ltd.) having a size of “25 mm × 75 mm × thickness 1.1 mm” was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV was applied. Ozone cleaning was performed for 30 minutes.
The glass substrate with the transparent electrode line after washing is mounted on the substrate holder of the vacuum deposition apparatus, and the following compound (HT) having a thickness of 60 nm is first formed on the surface on which the transparent electrode line is formed so as to cover the transparent electrode. ) Was formed by resistance heating vapor deposition. The film forming rate was 1 Å / s. This compound (HT) film functions as a hole injection / transport layer.
Next, the compound (1-1) produced in Synthesis Example 1 was deposited on the HT film by resistance heating vapor deposition to a thickness of 30 nm. At the same time, the following compound (BD) [10% by mass relative to the compound (1-1)] was deposited as a phosphorescent dopant. The film forming rates were 1 Å / s and 0.11 Å / s, respectively. This film functions as a phosphorescent light emitting layer.
Next, the following compound (HB) was formed on the phosphorescent light emitting layer by resistance heating vapor deposition so that the film forming rate was 1 Å / s and the thickness was 10 nm. This compound (HB) film functions as a hole blocking layer.
A tris (8-quinolinol) aluminum (Alq) complex having a film thickness of 30 nm was formed on this film at a film formation rate of 1 Å / s. This is because the Alq complex film functions as an electron injection layer.
Thereafter, LiF was formed at a film thickness of 0.5 nm and a film formation rate of 0.1 Å / s. On this LiF film, metal aluminum was deposited at a film formation rate of 1 レ ー ト / s to 100 nm to form a metal cathode, thereby forming an organic EL light emitting device.

<Example 2 to Example 10>
In Example 1, the organic EL device was prepared in the same manner as in Example 1 except that the compound (1-1) produced in Synthesis Example 1 was changed to the host material shown in Table 1 below produced in Synthesis Examples 2-10. Manufactured.

<Comparative Examples 1 to 4>
In Example 1, an organic EL device was produced in the same manner as in Example 1 except that the compound (1-1) produced in Synthesis Example 1 was changed to the host shown in Table 1 below.

^*：電圧及び外部量子効率は、輝度が１０００［ｃｄ／ｍ²］時の値である。
半減寿命は、初期輝度１０００［ｃｄ／ｍ²］にて測定した値である。

^* : Voltage and external quantum efficiency are values when the luminance is 1000 [cd / m ² ].
The half life is a value measured at an initial luminance of 1000 [cd / m ² ].

  From Table 1, in the compound (H1) or compound (H4) having two or four substituents on the dibenzofuran ring, the luminous efficiency and the organic EL device material of the present invention having three substituents are compared. It can be seen that the life is inferior. Moreover, even if three substituents are attached to the dibenzofuran ring, all the substituents are groups represented by the general formula (2) or (3), and at least one of the substituents is the general formula (3). In the compound (H2) and the compound (H4) that do not satisfy the condition of being a group represented by the formula (excluding the carbazolyl group), the luminous efficiency and lifetime are inferior compared with the organic EL device material of the present invention. I understand.

  When the organic EL device material of the present invention is used, an organic EL device having low crystallinity, excellent durability during vapor deposition, high heat resistance and luminous efficiency, and a long life can be obtained. For this reason, the organic EL element of the present invention is extremely useful as a light source for various electronic devices.

Claims (15)

The material for organic electroluminescent elements represented by the following general formula (1).

[Wherein, X is an oxygen atom or a sulfur atom. L ¹ , L ² and L ³ each independently represent a single bond, an alkylene group having 1 to 30 carbon atoms, an arylene group having 6 to 20 ring carbon atoms or a carbonyl group.
A ¹ , A ² and A ³ are each independently represented by the following general formula (2) or (3)

(In the formula, * represents a substitution position. Y is a single bond, an oxygen atom or a sulfur atom, Z is an oxygen atom, a sulfur atom or an N—R ¹ group (R ¹ is a group having 1 to 20 carbon atoms). An alkyl group or an aryl group having 6 to 18 ring carbon atoms.)
The monovalent group represented by these is shown.
However, in the above general formula (1), at least one of A ¹ , A ² and A ³ is a group represented by the above general formula (3) (excluding the carbazolyl group). ] In the general formula (1), the substitution positions of A ¹ -L ¹ -and A ² -L ² -are the 6th and 8th positions in the following formula, and the substitution position of A ³ -L ^3- is the following formula: The organic electroluminescent element material according to claim 1, which is in the 2nd or 4th position.

A material for an organic electroluminescence element represented by the following general formula (1 ′).

[Wherein, X is an oxygen atom or a sulfur atom. L ¹ , L ² and L ³ each independently represent a single bond, an alkylene group having 1 to 30 carbon atoms, an arylene group having 6 to 20 ring carbon atoms or a carbonyl group.
A ¹ , A ² and A ³ are each independently represented by the following general formula (2) or (3)

(In the formula, * represents a substitution position. Y is a single bond, an oxygen atom or a sulfur atom, Z is an oxygen atom, a sulfur atom or an N—R ¹ group (R ¹ is a group having 1 to 20 carbon atoms). An alkyl group or an aryl group having 6 to 18 ring carbon atoms.)
The monovalent group represented by these is shown.
However, in the general formula (1 ′), at least one of A ¹ , A ² and A ³ is a group represented by the general formula (3) (excluding a carbazolyl group). ] The material for organic electroluminescent elements represented by the following general formula (1 '').

[Wherein, X is an oxygen atom or a sulfur atom. L ¹ , L ² and L ³ each independently represent a single bond, an alkylene group having 1 to 30 carbon atoms, an arylene group having 6 to 20 ring carbon atoms or a carbonyl group.
A ¹ , A ² and A ³ are each independently represented by the following general formula (2) or (3)

(In the formula, * represents a substitution position. Y is a single bond, an oxygen atom or a sulfur atom, Z is an oxygen atom, a sulfur atom or an N—R ¹ group (R ¹ is a group having 1 to 20 carbon atoms). An alkyl group or an aryl group having 6 to 18 ring carbon atoms.)
The monovalent group represented by these is shown.
However, in the general formula (1 ″), at least one of A ¹ , A ² and A ³ is a group represented by the general formula (3) (excluding a carbazolyl group). ] The organic electroluminescent element material according to claim ¹ , wherein L ¹ , L ² and L ³ are each a single bond or a phenylene group.   In the organic electroluminescent element in which the organic thin film layer which consists of the organic thin film layer which consists of a single layer or multiple layers which has at least a light emitting layer between a cathode and an anode, at least one layer of the said organic thin film layer is any one of Claims 1-5. An organic electroluminescence device comprising a material for an organic electroluminescence device.   The organic electroluminescent element of Claim 6 which contains the organic electroluminescent element material of any one of Claims 1-5 as a host material in the said light emitting layer.   The organic electroluminescent device according to claim 6, wherein the light emitting layer contains a phosphorescent material and contains the organic electroluminescent device material according to claim 1 as a host material.   The organic electroluminescent element according to claim 8, wherein the phosphorescent material is a compound containing iridium (Ir), osmium (Os), ruthenium (Ru), or platinum (Pt).   The organic electroluminescence device according to claim 8, wherein the phosphorescent material is an orthometalated metal complex in which a central metal atom and a carbon atom contained in a ligand are orthometal bonded.   The organic electroluminescence device according to claim 7, wherein the excited triplet energy level of the host material is 2.0 to 3.2 eV.   The organic electroluminescent element according to claim 6, comprising a reducing dopant in an interface region between the cathode and the organic thin film layer.   The organic electroluminescence device according to claim 6, further comprising an electron injection layer between the light emitting layer and the cathode, wherein the electron injection layer contains a nitrogen-containing ring derivative.   In Claim 6, which has an electron carrying layer between the said light emitting layer and a cathode, and this electron carrying layer contains the organic electroluminescent element material of any one of Claims 1-5. The organic electroluminescent element of description.   A hole transport layer is provided between the light emitting layer and the anode, and the hole transport layer contains the material for an organic electroluminescence device according to any one of claims 1 to 5. 6. The organic electroluminescence device according to 6.