JP2009267257A - 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 high phosphorescence efficiency and long life, accompanies no pixel defect, and offers superior heat resistance; 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 is provided by using that material. In the formula (1), X denotes oxygen or sulfur, Y denotes a single bond, a carbonyl group, a 1-20C alkylene group that may have a substituent, oxygen, or sulfur, R<SP>1</SP>denotes a 1-20C alkyl group that may have a substituent or an aryl group having 6 to 18 ring-forming carbon atoms that may have a substituent, R<SP>2</SP>to R<SP>5</SP>each independently denote the 1-20C alkyl group that may have a substituent or an aryl group having 6 to 18 ring-forming carbon atoms that may have a substituent, m, p, and q separately denote an integer of 0 to 4, n denotes an integer of 0 to 3, and L<SP>1</SP>and L<SP>2</SP>each independently denote a bivalent bond group selected from a carbonyl group, an arylene group having 6 to 18 ring-forming carbon atoms that may have a substituent, a fluorenediyl group, etc. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to a material for an organic electroluminescence element and an organic electroluminescence element using the same, and more particularly, an organic electroluminescence element which can obtain phosphorescence emission with high efficiency and long life, has no pixel defects, and has excellent heat resistance. The present invention relates to a material for an organic electroluminescence element that realizes the above.

  An organic electroluminescence element (hereinafter, electroluminescence may be abbreviated as EL) is such that a fluorescent substance is generated by recombination energy of holes injected from an anode and electrons injected from a cathode by applying an electric field. It is a self-luminous element utilizing the principle of light emission. Since the report of low-voltage driven stacked organic EL elements, research on organic EL elements using organic materials as constituent materials has been actively conducted. In this multilayer element, tris (8-quinolinolato) aluminum is used for the light emitting layer, and a triphenyldiamine derivative is used for the hole transport layer. The advantages of the stacked structure are that it increases the efficiency of hole injection into the light-emitting layer, blocks the electrons injected from the cathode, increases the generation efficiency of excitons generated by recombination, and generates in the light-emitting layer For example, confining excitons. As in this example, the element structure of the organic EL element includes a hole transport (injection) layer, a two-layer type of an electron transport light emitting layer, or a hole transport (injection) layer, a light emitting layer, and an electron transport (injection) layer A three-layer type is well known. In such a stacked structure element, the element structure and the formation method are devised in order to increase the recombination efficiency of injected holes and electrons.

As light-emitting materials for organic EL elements, chelate complexes such as tris (8-quinolinolato) aluminum complex, light-emitting materials such as coumarin derivatives, tetraphenylbutadiene derivatives, distyrylarylene derivatives, oxadiazole derivatives, and the like are known. Has been reported to emit light in the visible region from blue to red, and the realization of a color display element is expected.
Conventionally, fluorescent light-emitting materials that emit light by singlet excitons have been used as light-emitting materials for organic EL elements. In recent years, it has also been proposed to use phosphorescent light-emitting materials that emit light by triplet excitons in addition to fluorescent light-emitting materials. (For example, Non-Patent Documents 1 and 2). 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. The organic EL element using can achieve a light emission efficiency of 3 to 4 times that of an organic EL element using only a fluorescent material. However, with blue phosphorescence, it is difficult to achieve high efficiency and long life, and development of a host material that achieves them is desired.

  Patent Document 1 describes a compound in which two carbazole skeletons are bonded to one dibenzofuran skeleton or dibenzothiophene skeleton (for example, compounds H-33 and H-34). However, in any compound, two carbazole skeletons are directly bonded to one dibenzofuran skeleton or dibenzothiophene skeleton at the N position. Patent Document 1 discloses a compound in which one carbazole skeleton is bonded to one dibenzofuran skeleton or a dibenzothiophene skeleton through a linking group at a position other than N and the other skeleton such as a carbazole skeleton at the N-position. Is not listed.

  Patent Document 2 describes a compound in which two carbazole skeletons are bonded to one dibenzofuran skeleton or dibenzothiophene skeleton (for example, compounds 23 and 24). However, the two carbazole skeletons are directly bonded to one dibenzofuran skeleton or dibenzothiophene skeleton through a linking group at the N site of the skeleton. Patent Document 2 discloses a compound in which one carbazole skeleton is bonded to one dibenzofuran skeleton or dibenzothiophene skeleton through a linking group at a position other than N and the other skeleton such as a carbazole skeleton at the N position. Is not listed.

  Patent Document 3 describes a compound in which two carbazole skeletons are bonded to one dibenzofuran skeleton (for example, Compound 43). However, the two carbazole skeletons are directly bonded to the dibenzofuran skeleton at sites other than N. Patent Document 3 discloses a compound in which one carbazole skeleton is bonded to one dibenzofuran skeleton or a dibenzothiophene skeleton via a linking group at a position other than N and the other skeleton such as a carbazole skeleton at the N position. Is not listed.

  Further, the compounds described in Patent Documents 1 to 3 have insufficient blue phosphorescence efficiency and lifetime.

WO2007 / 108459 WO2007 / 119816 WO2007 / 0777810 Applied Physics letters Vol. 74 No.3, pp442-444 Applied Physics letters Vol. 75 No. 1, pp4-6

  The present invention has been made in order to solve the above-described problems, and is an organic EL element having high efficiency and long life of phosphorescence, no pixel defects, and excellent heat resistance, and a material for an organic EL element realizing the same. The purpose is to provide.

  As a result of intensive studies to achieve the above object, the present inventors have found that the above object can be achieved by using a compound represented by the following formula (1) as an organic EL element material, The present invention has been solved.

（一般式（１）において、ＸはＯまたはＳであり；Ｙは単結合、カルボニル基、置換基を有してもよい炭素数１〜２０のアルキレン基、ＯまたはＳであり；Ｒ¹は置換基を有してもよい炭素数１〜２０のアルキル基または置換基を有してもよい環形成炭素数６〜１８のアリール基を表し；Ｒ²〜Ｒ⁵はそれぞれ独立して置換基を有してもよい炭素数１〜２０のアルキル基または置換基を有してもよい環形成炭素数６〜１８のアリール基を表し；ｍ、ｐおよびｑはそれぞれ独立して０〜４の整数を表し；ｎは０〜３の整数を表し；Ｌ¹とＬ²はそれぞれ独立してカルボニル基、置換基を有してもよい環形成炭素数６〜１８のアリーレン基、フルオレンジイル基、−ＣＲ⁶Ｒ⁷−、および−ＣＲ⁶Ｒ⁷−ＣＲ⁸Ｒ⁹−（式中、Ｒ⁶〜Ｒ⁹はそれぞれ独立して水素原子、置換基を有してもよい炭素数１〜２０のアルキル基または置換基を有してもよい環形成炭素数６〜１８のアリール基を表し、Ｒ⁶とＲ⁷およびＲ⁸とＲ⁹は互いに結合してそれらが結合している炭素原子と共に飽和または不飽和の環を形成してもよい）から選ばれる２価の結合基である。） That is, this invention is a material for organic electroluminescent elements represented by following formula (1).

(In General Formula (1), X is O or S; Y is a single bond, a carbonyl group, an optionally substituted alkylene group having 1 to 20 carbon atoms, O or S; R ¹ is Represents an alkyl group having 1 to 20 carbon atoms which may have a substituent or an aryl group having 6 to 18 ring carbon atoms which may have a substituent; R ^{2 to} R ⁵ each independently represents a substituent; Represents an alkyl group having 1 to 20 carbon atoms which may have a substituent or an aryl group having 6 to 18 ring carbon atoms which may have a substituent; m, p and q each independently represent 0 to 4 N represents an integer of 0 to 3; L ¹ and L ² each independently represent a carbonyl group, an arylene group having 6 to 18 ring carbon atoms which may have a substituent, or a fluorenediyl group , -CR ⁶ R ⁷ -, and ^{-CR 6 R 7 -CR 8 R 9} - ( wherein, R ⁶ to R ⁹ DE respectively A hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms or an optionally substituted aryl group having 6 to 18 ring carbon atoms, R ⁶ and R ⁷ and R ⁸ and R ⁹ may be bonded to each other to form a saturated or unsaturated ring together with the carbon atom to which they are bonded.

  Furthermore, 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 a material for an organic electroluminescence element represented by the above formula (1). It is an organic electroluminescent element containing this.

  According to the present invention, it is possible to provide an organic EL element having high efficiency and a long lifetime of phosphorescence, no pixel defects, excellent heat resistance, and a long lifetime, and an organic EL element material for realizing the organic EL element. .

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

  In the formula (1), X is O or S.

  Y is a single bond, a carbonyl group, an alkylene group having 1 to 20 carbon atoms (not including the carbon number of the substituent) which may have a substituent, O or S. Examples of the alkylene group include a methylene group, a methylmethylene group, a dimethylmethylene group, a phenylmethylene group, a methylphenylmethylene group, a diphenylmethylene group, and a 9,9-fluorenediyl group.

R ¹ is an alkyl group having 1 to 20 carbon atoms (not including the carbon number of the substituent) which may have a substituent or 6 to 18 ring carbon atoms which may have a substituent (of the substituent). An aryl group having no carbon number). Examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, and 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 and the like. Examples of the aryl group which may have a substituent include a phenyl group, a tolyl group, a xylyl group, a mesityl group, an o-biphenyl group, an m-biphenyl group, a p-biphenyl group, an o-terphenyl group, and an m-ter. Examples thereof include a phenyl group, a p-terphenyl group, a naphthyl group, and a phenanthryl group.

As the substituent of the alkyl group and aryl group represented by R ¹ , an alkyl group having 1 to 10 carbon atoms (methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t- Butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, etc.), C1-C10 hydroxyalkyl 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, etc.), carbon number 1 To 10 haloalkyl groups (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, etc.), C 1-10 Aminoalkyl group (aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diamyl group) Noisopropyl group, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group, etc., C2-C11 cyanoalkyl 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, etc.), carbon number 1 Nitroalkyl 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.), cycloalkyl group having 3 to 40 ring carbon atoms (cyclopropyl group, cyclobutyl group, cyclopentyl) Cyclohexyl group, 4-methylcyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, 2-norbornyl group, etc.), alkoxy group having 1 to 6 carbon atoms (methoxy group, ethoxy group, isopropoxy group) , N-propoxy group, s-butoxy group, t-butoxy group, pentoxy group, hexyloxy group and the like), cycloalkoxy groups having 3 to 10 ring carbon atoms (cyclopentoxy group, cyclohexyloxy group and the like), ring formation Aryl group having 6 to 40 carbon atoms (phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, naphthyl group, phenanthryl group) An amino group substituted with an aryl group having 6 to 40 ring carbon atoms (monophenylamino group, diphenyl) Amino groups, mononaphthylamino groups, dinaphthylamino groups, etc.), aryloxycarbonyl groups having an aryl group having 6 to 40 ring carbon atoms (phenoxycarbonyl group, naphthoxycarbonyl group, etc.), alkyls having 1 to 6 carbon atoms An alkoxycarbonyl group having a group (methoxycarbonyl group, ethoxycarbonyl group, isopropoxycarbonyl group, n-propoxycarbonyl group, s-butoxycarbonyl group, t-butoxycarbonyl group, pentoxycarbonyl group, hexyloxycarbonyl group, etc.), A cyano group, a nitro group, a halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom) and the like can be mentioned.

R ^{2 to} R ⁵ each independently have an alkyl group having 1 to 20 carbon atoms (not including the carbon number of the substituent) which may have a substituent or 6 ring-forming carbon atoms which may have a substituent. Represents an aryl group of ˜18 (not including the carbon number of the substituent). Said alkyl group, aryl group and their substituents are selected from the alkyl groups, aryl groups and their substituents described for R ¹ .

  m, p, and q each independently represent an integer of 0 to 4, and n represents an integer of 0 to 3. Preferably, the sum of m and n and the sum of p and q are each independently an integer of 0 to 4.

L ¹ and L ² are each independently a carbonyl group, an arylene group having 6 to 18 ring carbon atoms that may have a substituent (not including the carbon number of the substituent), a fluorenediyl group, —CR ⁶ R ⁷ -, and ^{-CR 6 R 7 -CR 8 R 9} - is a divalent linking group selected from.

Examples of the arylene group include an o-phenylene group, an m-phenylene group, a p-phenylene group, and a biphenyldiyl group (for example, 2,2′-biphenyldiyl group, 3,3′-biphenyldiyl group, 4,4′- Biphenyldiyl group, 2,3′-biphenyldiyl group, 2,4′-biphenyldiyl group, 3,4′-biphenyldiyl group), terphenyldiyl group (for example, m-terphenyl-3,3 ″- Diyl group), naphthalenediyl group (for example, 1,4-naphthalenediyl group), phenanthrene diyl group (for example, 2,7-phenanthenediyl group) and the like. The substituent for the arylene group is selected from those described for R ¹ .

The fluorenediyl group is the following divalent group, and is preferably a 9,9-dimethylfluorene-2,7-diyl group or a 9,9-dimethylfluorene-2,5-diyl group.

In the above formula, R ¹⁰ and R ¹¹ each independently represents an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 18 ring carbon atoms. Said alkyl and aryl groups are selected from those described for R ¹ .

In —CR ⁶ R ⁷ — and —CR ⁶ R ⁷ —CR ⁸ R ⁹ —, R ^{6 to} R ⁹ each independently represent a hydrogen atom or a substituent having 1 to 20 carbon atoms (of the substituent). An alkyl group having no carbon number) or an aryl group having 6 to 18 ring carbon atoms (not including the carbon number of the substituent) which may have a substituent. R ⁶ and R ⁷ and R ⁸ and R ⁹ may be bonded to each other to form a saturated or unsaturated ring together with the carbon atom to which they are bonded. Said alkyl group, aryl group and their substituents are selected from those described for R ¹ . Preferred specific examples of —CR ⁶ R ⁷ — and —CR ⁶ R ⁷ —CR ⁸ R ⁹ — are shown below.

（式中、Ｘ、Ｙ、Ｒ¹、Ｒ²〜Ｒ⁵、ｍ、ｎ、ｐ、ｑ、Ｌ¹およびＬ²は前記と同様である。）

（式中、Ｘ、Ｙ、Ｒ¹、Ｒ²〜Ｒ⁵、ｍ、ｎ、ｐ、ｑ、Ｌ¹およびＬ²は前記と同様である。） L ¹ and L ² are preferably bonded to the 2nd and 8th positions of the dibenzofuran skeleton (X═O) or the dibenzothiophene skeleton (X═S). L ¹ is preferably bonded to the 3-position (6-position) of the carbazole skeleton. That is, the organic electroluminescent element material of the present invention is preferably represented by the following formula (2), more preferably by the following formula (3).

(In the formula, X, Y, R ¹ , R ^{2 to} R ⁵ , m, n, p, q, L ¹ and L ² are the same as described above.)

(In the formula, X, Y, R ¹ , R ^{2 to} R ⁵ , m, n, p, q, L ¹ and L ² are the same as described above.)

The compound of General formula (1) is compoundable as follows, for example.

  The organic EL device material of the present invention is preferably a host material used together with a phosphorescent material or an electron transport material used together with a phosphorescent material. The triplet energy level is preferably 2.0 to 3.2 eV, more preferably 2.5 to 3.2 eV.

Specific examples of the organic EL device material represented by the general formula (1) of the present invention are shown below, but the present invention is not limited to these exemplified compounds.

The organic EL device material of the present invention is preferably a host material contained in the light emitting layer of the organic EL device.
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 the cathode and the anode, and at least one of the organic thin film layers contains the material for an organic electroluminescence device of the present invention.
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, a metal selected from iridium (Ir), osmium (Os) and platinum (Pt) in that the phosphorescent quantum yield is high and the external quantum efficiency of the light emitting device can be further improved. Are preferable, and metal complexes such as iridium complexes, osmium complexes, and platinum complexes are more preferable, and iridium complexes and platinum complexes are more preferable. The metal complex is preferably an orthometalated metal complex in which a central metal atom and a carbon atom contained in the ligand are orthometal bonded, and more preferably an orthometalated iridium complex. As a more preferable form of the ortho-metalated metal complex, the following iridium complexes are exemplified.

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

  The organic EL device of the present invention preferably has a hole transport layer (hole injection layer), and the hole transport layer (hole injection layer) preferably contains the organic EL device material of the present invention. The organic EL device of the invention preferably has an electron transport layer and / or a hole barrier layer, and the electron transport layer and / or the hole barrier layer preferably contains the organic EL device material of the present invention.

  The organic EL device of the present invention preferably has a reducing dopant in the interface region between the cathode and the organic thin film layer. The reducing dopant was 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. There is at least one kind.

Examples of the alkali metal include 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. A function of 2.9 eV or less is particularly preferable. Of these, K, Rb, and Cs are preferred, Rb and Cs are more preferred, and Cs is most preferred.
Examples of the alkaline earth metal include Ca (work function: 2.9 eV), Sr (work function: 2.0 to 2.5 eV), Ba (work function: 2.52 eV), and the like. The thing below 9 eV is especially preferable.
Examples of rare earth metals include Sc, Y, Ce, Tb, Yb, and the like, and those having a work function of 2.9 eV or less are particularly preferable.
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, and LiF, Li ₂ O, and NaF are preferable.
Examples of the alkaline earth metal compound include BaO, SrO, CaO, and Ba _x Sr _1-x O (0 <x <1), Ba _x Ca _1-x O (0 <x <1) mixed with 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, 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. In addition, the ligand includes quinolinol, benzoquinolinol, acridinol, phenanthridinol, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxydiaryl oxadiazole, hydroxydiaryl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, 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 formation method, a method in which a reducing dopant is deposited in the organic material by simultaneously depositing a light emitting material forming an interface region or an organic material that is an electron injection material while depositing a reducing dopant by a resistance heating vapor deposition method is preferable. The dispersion concentration is organic matter: reducing dopant = 100: 1 to 1: 100, preferably 5: 1 to 1: 5 in molar ratio.
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.

The organic EL device of the present invention preferably has an electron injection layer between the light emitting layer and the cathode, and the electron injection layer contains a nitrogen-containing ring derivative as a main component.
As the electron transport material used for the electron injection layer, an aromatic heterocyclic compound containing at least one hetero atom in the molecule is preferably used, and a nitrogen-containing ring derivative is particularly preferable.

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

R ^{2 to} R ⁷ are each independently 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 include the same ones as described above. Examples of the amino group which may be substituted include those similar to the alkylamino group, arylamino group and aralkylamino group.
Examples of the hydrocarbon group having 1 to 40 carbon atoms include a substituted or unsubstituted alkyl group, alkenyl group, cycloalkyl group, aryl group, aralkyl group, and the like. Examples of the alkyl group, alkenyl group, cycloalkyl group, alkoxy group, aryl group, heterocyclic group, aralkyl group, and aryloxy group include those described above, and the alkoxycarbonyl group is represented as —COOY ′. , Y ′ includes the same alkyl groups as those described above.

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

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

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 which may have a substituent, and Ar ^b is a divalent aromatic hydrocarbon having 6 to 40 carbon atoms which 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. It is a good quinolinylene group, Ar ^f is an optionally substituted aryl group having 6 to 60 carbon atoms, an optionally substituted pyridyl group, and an optionally substituted quinolyl group. Group having 1 to 20 carbon atoms which may have a substituent. Have Kill group or substituent is an alkoxy group which may 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. Substituents for each group represented by Ar ^e and Ar ^g are the same as those described for R.
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 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. A quinolyl group, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted alkoxy group having 1 to 20 carbon atoms.
Specific examples, 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).

  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 5-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.

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

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 heterocyclic 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, 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-tol 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 Examples include '-methylbiphenylyl group, 4 "-t-butyl-p-terphenyl-4-yl group, fluoranthenyl group, fluorenyl group and the like.

  Examples of the substituted or unsubstituted heterocyclic 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-isobenzofuran group Nyl 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 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-phen 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 -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, 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-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. 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.

  L is a 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 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, Examples include 12-chrysenylene group, 4,4′-biphenylene group, 3,3′-biphenylene group, 2,2′-biphenylene group, 2,7-fluorenylene group and the like. Examples of the arylene 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, and 2,7-fluorenylene group.

  When L is a linking group comprising 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 the divalent group forming the ring include a tetramethylene group, a pentamethylene group, a hexamethylene group, a diphenylmethane-2,2′-diyl group, a diphenylethane-3,3′-diyl group, a diphenylpropane-4, 4'-diyl group, etc. are mentioned.

Examples of the substituent for Ar ^{1 to} Ar ⁴ and L include a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, substituted or unsubstituted An alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted 7 to 50 carbon atoms. 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 having 6 to 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, substituted or unsubstituted With an amino group, halogen group, cyano group, nitro group, hydroxyl group, etc. substituted by an unsubstituted aryl group having 6 to 50 carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms is there.

  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, 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′- Examples thereof include a methylbiphenylyl group, a 4 ″ -t-butyl-p-terphenyl-4-yl group, a fluoranthenyl group, and a fluorenyl group.

  Examples of the substituted or unsubstituted heterocyclic 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-isobenzofuranyl group Group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group 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 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-phenane Lydinyl 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-phenane Throlin-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-phenanthroline 3-yl group, 2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group, 2,9-phenanthrolin-6-yl group, 2,9-phenance Lorin-7-yl group, 2,9-phenanthrolin-8-yl group, 2,9-phenanthrolin-10-yl group, 2,8-phenanthrolin-1-yl group, 2,8- Phenanthrolin-3-yl group, 2,8-phenanthrolin-4-yl group, 2,8-phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group, 2, 8-phenanthroline-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, 10-pheno Thiazinyl 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-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.

  Examples of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n- Pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1, 3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1, 2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, Momethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group, 1,2, 3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo-t- Butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropyl Group, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, -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. Is mentioned.

  Examples of the substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1- Examples include a norbornyl group and a 2-norbornyl group.

  A substituted or unsubstituted C1-C50 alkoxy group is group represented by -OY. Examples of Y include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, and 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-butyl group Moethyl 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-tri Iodopropyl 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-dicyano Til 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 and the like.

  Examples of the substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms include 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-methylbenzyl group, p-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromobenzyl M-bromobenzyl group, o-bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group, p -Aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group, p-nitrobenzyl group, m-nitrobenzyl group, o-nitrobenzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyano Examples include benzyl group, 1-hydroxy-2-phenylisopropyl group, 1-chloro-2-phenylisopropyl group and the like.

  A substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms is represented as —OY ′, and examples of Y ′ include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, 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 Examples include a -1-anthryl group, a 4′-methylbiphenylyl group, a 4 ″ -t-butyl-p-terphenyl-4-yl group, and the like.

  A substituted or unsubstituted heteroaryloxy group having 5 to 50 ring atoms is represented as -OZ ', and examples of Z' include 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-isoben Furanyl 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-phenanthridinyl group, 8-phenanthridinyl group Group, 9-phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1,7-phenanthroline 2-yl group, 1,7-phenanthrolin-3-yl group, 1,7-phenanthrolin-4-yl group, 1,7-phenanthrolin-5-yl group, 1,7-phen group Nansulolin-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-phen Nansulolin-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-phenanthroline-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-phenanthro N-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-phenanthrolin-3-yl group, 2, 8-phenanthroline-4-yl group, 2,8-phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group, 2,8-phenanthrolin-7-yl group, 2,8-phenanthroline-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 Group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group 4-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-flazanyl group, 2-thienyl group, 3-thienyl group, 2-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 group, 3-methylpyrrol-4-yl group, 3-methylpyrrol-5-yl group, 2-t-butylpyrrole- 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.

  A substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms is represented by —SY ″, and examples of Y ″ include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, 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, -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 can be mentioned.

  A substituted or unsubstituted heteroarylthio group having 5 to 50 ring atoms is represented by —SZ ″, and examples of Z ″ include 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-isobenzofuran group Ranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl Group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl Group, 5-quinoxalinyl group, 6-quinoxalinyl group, 1-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-phenanthroline- 2-yl group, 1,7-phenanthrolin-3-yl group, 1,7-phenanthrolin-4-yl group, 1,7-phenanthrolin-5-yl group, 1,7-phenanth Lorin-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-phena Nsulolin-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-phenanthroline-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-phenanthroli -4-yl group, 2,9-phenanthrolin-5-yl group, 2,9-phenanthrolin-6-yl group, 2,9-phenanthrolin-7-yl group, 2,9-phen group Nansulolin-8-yl group, 2,9-phenanthrolin-10-yl group, 2,8-phenanthrolin-1-yl group, 2,8-phenanthrolin-3-yl group, 2,8 -Phenanthrolin-4-yl group, 2,8-phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group, 2,8-phenanthrolin-7-yl group, 2 , 8-phenanthroline-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, , 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-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-furazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrole- 1-yl group, 2-methylpyrrol-3-yl group, 2-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-butylpyrrole-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- Examples include 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.

  A substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms is represented as —COOZ, and examples of Z include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, and 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-triaminopropyl group, cyanomethyl group, Noethyl 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, Examples include 2,3-trinitropropyl group.

  An amino group substituted with a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms is represented by -NPQ. Examples 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. Group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4 -Biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl Group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, pt-butylphenyl group, p- (2- Phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylyl group, 4 ″ -t-butyl-p- Terphenyl-4-yl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoyl group Drill 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-phenanth Lydinyl 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-phenanthroline-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-phenanthroline-5-yl group, 1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group, 1,8-phenanthrolin-9-yl group, 1,8-phenanthroline-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-phenance Rin-2-yl group, 1,10-phenanthrolin-3-yl group, 1,10-phenanthrolin-4-yl group, 1,10-phenanthrolin-5-yl group, 2,9- Phenanthrolin-1-yl group, 2,9-phenanthrolin-3-yl group, 2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group, 2, 9-phenanthroline-6-yl group, 2,9-phenanthrolin-7-yl group, 2,9-phenanthrolin-8-yl group, 2,9-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-y 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-phenanth Lorin-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- Xazolyl 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-butyl 1-indolyl group, 4-t-butyl 1-indolyl group, 2-t-butyl 3-indole group Group, and a 4-t-butyl 3-indolyl group and the like.

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 _{1 to} Ar ₃ 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. Specific examples of the anode material used in the present invention include indium tin oxide alloy (ITO), tin oxide (NESA), gold, silver, platinum, copper, and the like. 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.

The formation method of each layer of the organic EL element of the present invention is not particularly limited. Conventionally known methods such as vacuum deposition and spin coating can be used. The organic thin film layer containing the compound represented by the formula (1) used in the organic EL device of the present invention is formed by vacuum evaporation, molecular beam evaporation (MBE), a solution dipping method dissolved in a solvent, spin It can be formed by a known method such as a coating method, a casting method, a bar coating method, a roll coating method or the like.
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.

  Next, the present invention will be described in further detail using synthesis examples and examples. However, the present invention is not limited to the following synthesis examples and examples.

The evaluation method of the organic EL element is as follows.
(1) External quantum efficiency (%)
The external quantum efficiency at a luminance of 1000 cd / m ² under a dry nitrogen gas atmosphere at 23 ° C. was measured using a luminance meter (Spectral Luminance Radiometer CS-1000 manufactured by Minolta).
(2) Half life (hours)
A continuous energization test (DC) was performed at an initial luminance of 1000 cd / m ² , and the time until the initial luminance was halved was measured.

Synthesis Example 1 (Synthesis of Compound (1))
(1) Synthesis of compound (1-a)

Under an argon atmosphere, 3- (N-phenylcarbazole) boronic acid (20 mmol, 5.74 g), 3-bromoiodobenzene (24 mmol, 6.79 g), 2M aqueous solution of Na ₂ CO ₃ (40 mmol, 20 ml), dimethyl ether ( 40 ml) and toluene (40 ml) were mixed with Pd [PPh ₃ ] ₄ (1 mmol, 1.16 g) and refluxed for 9 hours. After completion of the reaction, the mixture was extracted with toluene in a separatory funnel, dried over anhydrous magnesium sulfate, then filtered and concentrated. The concentrate was purified by silica gel column chromatography to obtain a white solid (yield 5.89 g, yield 74%).
From the LC / MS measurement results of the obtained compound, this compound was identified as the target product.
LC / MS: Calculated for C ₂₄ H ₁₆ BrN = 397, measured m / z = 397

(2) Synthesis of compound (1-b)

Under a argon atmosphere, a mixed solution of compound (1-a) (14.7 mmol, 5.85 g) and dehydrated tetrahydrofuran (THF) (73 ml) was cooled to −78 ° C., and 1.56M hexane of n-butyllithium was added thereto. The solution (15.4 mmol, 9.89 ml) was added and stirred for 15 minutes. Thereafter, triisopropylborane (29.4 mmol, 5.53 g) was added, and the mixture was allowed to stand at room temperature and stirred for 5 hours. After completion of the reaction, the solution was concentrated to about half, 1N hydrochloric acid was added thereto to adjust the pH to about 2, and the mixture was stirred at room temperature for 1 hour. The mixture was extracted with dichloromethane using a separatory funnel, dried over anhydrous magnesium sulfate, passed through a short silica column, and concentrated. Hexane was added thereto to precipitate a sample, dispersed and washed, and then collected by filtration to obtain a white solid (yield 4.86 g, yield 91%).
(3) Synthesis of compound (1-c)

Under an argon atmosphere, 2,8-dibromodibenzofuran (20 mmol, 6.51 g), 4- (N-carbazolyl) phenylboronic acid (20 mmol, 5.74 g), 2M aqueous solution of Na ₂ CO ₃ (40 mmol, 20 ml), dimethyl ether (40 ml) and toluene (40 ml) were mixed with Pd [PPh ₃ ] ₄ (1 mmol, 1.16 g) and refluxed for 9 hours. After completion of the reaction, the mixture was extracted with dichloromethane using a separatory funnel, dried over anhydrous magnesium sulfate, filtered and concentrated. The concentrate was purified by silica gel column chromatography to obtain a white solid (yield 4.98 g, yield 51%).
From the LC / MS measurement results of the obtained compound, this compound was identified as the target product.
LC / MS: Calculated value of C ₃₀ H ₁₈ BrNO = 487, measured value m / z = 487

(4) Synthesis of compound (1)

Under an argon atmosphere, compound (1-c) (10 mmol, 4.88 g), compound (1-b) (12 mmol, 4.36 g), 2M aqueous solution of Na ₂ CO ₃ (20 mmol, 10 ml), dimethyl ether (20 ml), Pd [PPh ₃ ] ₄ (0.5 mmol, 0.58 g) was added to a mixed solution of toluene and toluene (20 ml), and the mixture was refluxed for 9 hours. After completion of the reaction, the mixture was extracted with toluene in a separatory funnel, dried over anhydrous magnesium sulfate, filtered and concentrated. The concentrate was purified by silica gel column chromatography to obtain a white solid (yield 4.00 g, yield 55%).
From the LC / MS measurement results of the obtained compound, this compound was identified as the target product.
_{LC / MS: C 54 H 34} N 2 O calc = 726, measured value m / z = 726

Synthesis Example 2 (Synthesis of Compound (3))
(1) Synthesis of compound (3-a)

Under an argon atmosphere, 2,8-dibromodibenzofuran (30 mmol, 5.05 g), 3- (N-phenoxazinyl) phenylboronic acid (30 mmol, 9.09 g), 2M aqueous solution of Na ₂ CO ₃ (60 mmol, 30 ml), dimethyl ether Pd [PPh ₃ ] ₄ (1.5 mmol, 1.73 g) was added to a mixed solution of (60 ml) and toluene (60 ml), and the mixture was refluxed for 9 hours. After completion of the reaction, the mixture was extracted with dichloromethane using a separatory funnel, dried over anhydrous magnesium sulfate, filtered and concentrated. The concentrate was purified by silica gel column chromatography to obtain a white solid (yield 8.17 g, yield 54%).
From the LC / MS measurement results of the obtained compound, this compound was identified as the target product.
_{LC / MS: C 30 H 18} BrNO 2 Calculated = 503, measured value m / z = 503

(2) Synthesis of compound (3)

Under an argon atmosphere, compound (3-a) (6 mmol, 3.03 g), compound (1-b) (6.6 mmol, 2.40 g), 2M aqueous solution of Na ₂ CO ₃ (12 mmol, 6 ml), dimethyl ether (12 ml) ) And toluene (12 ml), Pd [PPh ₃ ] ₄ (0.30 mmol, 0.35 g) was added and refluxed for 9 hours. After completion of the reaction, the mixture was extracted with toluene in a separatory funnel, dried over anhydrous magnesium sulfate, filtered and concentrated. The concentrate was purified by silica gel column chromatography to obtain a white solid (yield 3.30 g, yield 74%).
From the LC / MS measurement results of the obtained compound, this compound was identified as the target product.
LC / MS: Calculated value of C ₅₄ H ₃₄ N ₂ O ₂ = 742, measured value m / z = 742

Synthesis Example 3 (Synthesis of Compound (6))
(1) Synthesis of compound (6-a)

Under an argon atmosphere, a mixed solution of dibenzofuran (30 mmol, 5.05 g) and dehydrated THF (150 ml) was cooled to 0 ° C., and lithium-2,2,6,6-tetramethylpiperidine / A THF solution (33 mmol / 33 ml) was added using a cannula and stirred for 2 hours. Then, iodine (33 mmol, 8.38 g) was added and stirred at 0 ° C. for 1 hour. Thereafter, lithium-2,2,6,6-tetramethylpiperidine / THF solution (33 mmol / 33 ml) was added again using a cannula, and the mixture was stirred for 2 hours. Then, iodine (33 mmol, 8.38 g) was added and stirred at 0 ° C. for 1 hour. After completion of the reaction, the mixture was extracted with dichloromethane using a separatory funnel, dried over anhydrous magnesium sulfate, filtered and concentrated. The concentrate was recrystallized from hexane to obtain a light brown solid (yield 5.54 g, yield 44%).
From the LC / MS measurement results of the obtained compound, this compound was identified as the target product.
LC / MS: Calculated value of C ₁₂ H ₆ I ₂ O = 420, measured value m / z = 420

(2) Synthesis of compound (6-b)

Under an argon atmosphere, compound (6-a) (15 mmol, 6.30 g), 3- (N-carbazolyl) phenylboronic acid (15 mmol, 4.30 g), 2M aqueous solution of Na ₂ CO ₃ (30 mmol, 15 ml), dimethyl ether Pd [PPh ₃ ] ₄ (0.75 mmol, 0.87 g) was added to a mixed solution of (30 ml) and toluene (30 ml), and the mixture was refluxed for 9 hours. After completion of the reaction, the mixture was extracted with dichloromethane using a separatory funnel, dried over anhydrous magnesium sulfate, filtered and concentrated. The concentrate was purified by silica gel column chromatography to obtain a white solid (yield 4.02 g, yield 50%).
From the LC / MS measurement results of the obtained compound, this compound was identified as the target product.
LC / MS: Calculated value of C ₃₀ H ₁₈ INO = 535, measured value m / z = 535

(3) Synthesis of compound (6)

Under argon atmosphere, compound (6-b) (7.4 mmol, 3.96 g), compound (1-b) (8.14 mmol, 2.96 g), 2M aqueous solution of Na ₂ CO ₃ (15 mmol, 7.5 ml) , Pd [PPh ₃ ] ₄ (0.38 mmol, 0.43 g) was added to a mixed solution of dimethyl ether (15 ml) and toluene (15 ml), and the mixture was refluxed for 9 hours. After completion of the reaction, the mixture was extracted with toluene in a separatory funnel, dried over anhydrous magnesium sulfate, filtered and concentrated. The concentrate was purified by silica gel column chromatography to obtain a white solid (yield 3.55 g, yield 66%).
From the LC / MS measurement results of the obtained compound, this compound was identified as the target product.
LC / MS: Calculated value for C ₅₄ H ₃₄ N ₂ O = 726, measured value m / z = 726

Synthesis Example 4 (Synthesis of Compound (39))

  Compound (39) was synthesized in the same manner as in Synthesis Example 1, except that 2,8-dibromodibenzothiophene was used instead of 2,8-dibromodibenzofuran.

Example 1
A 25 mm × 75 mm × 1.1 mm glass substrate with an ITO transparent electrode (manufactured by Geomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes. The glass substrate with the transparent electrode line after the cleaning is mounted on the substrate holder of the vacuum deposition apparatus, and the compound (HT) is first deposited by resistance heating deposition on the surface where the transparent electrode line is formed so as to cover the transparent electrode. (Film thickness 60 nm). The film forming rate was 1 Å / s. This HT film functions as a hole injection / transport layer.
Next, on the HT film, the compound (1) (host compound) was deposited by resistance heating to form a 30 nm thick H1 film. At the same time, as a phosphorescent dopant, the compound (BD) was deposited so as to be 10% by mass with respect to the compound (1). The film forming rates were 1 Å / s and 0.11 Å / s, respectively. This film functions as a phosphorescent light emitting layer.
Next, a compound (HB) was deposited by resistance heating vapor deposition on this phosphorescent light emitting layer to form a 10 nm thick HB film. The film forming rate was 1 kg / s. This HB film functions as a hole blocking layer.
Tris (8-quinolinol) aluminum (Alq) complex was vapor-deposited on the HB film at a film formation rate of 1 Å / s (film thickness: 30 nm). This film functions as an electron injection layer.
Then, LiF was vapor-deposited on the Alq film at a film formation rate of 0.1 Å / s (film thickness 0.5 nm). On this LiF film, metal Al was vapor-deposited at a film formation rate of 1 Å / s to form a metal cathode (film thickness 100 nm) to obtain an organic EL element.

Examples 2-4
An organic EL device was produced in the same manner as in Example 1 except that the compound (3), (6) or (39) was used instead of the compound (1).

Comparative Examples 1-7
An organic EL device was produced in the same manner as in Example 1 except that the comparative compounds (1) to (7) were used instead of the compound (1).

  From Table 1, it can be seen that the compounds (1), (3), (6) and (39) of the present invention have higher efficiency and longer life than the comparative compounds (1) to (7).

  As described above in detail, when the organic EL element material represented by the general formula (1) of the present invention is used, the organic EL has high luminous efficiency, no pixel defects, excellent heat resistance, and a long lifetime. An element is obtained. For this reason, the organic EL element of the present invention is extremely useful as a display, a light source and the like for various electronic devices.

Claims (14)

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

(In General Formula (1), X is O or S; Y is a single bond, a carbonyl group, an optionally substituted alkylene group having 1 to 20 carbon atoms, O or S; R ¹ is Represents an alkyl group having 1 to 20 carbon atoms which may have a substituent or an aryl group having 6 to 18 ring carbon atoms which may have a substituent; R ^{2 to} R ⁵ each independently represents a substituent; Represents an alkyl group having 1 to 20 carbon atoms which may have a substituent or an aryl group having 6 to 18 ring carbon atoms which may have a substituent; m, p and q each independently represent 0 to 4 N represents an integer of 0 to 3; L ¹ and L ² each independently represent a carbonyl group, an arylene group having 6 to 18 ring carbon atoms which may have a substituent, or a fluorenediyl group , -CR ⁶ R ⁷ -, and ^{-CR 6 R 7 -CR 8 R 9} - ( wherein, R ⁶ to R ⁹ DE respectively A hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms or an optionally substituted aryl group having 6 to 18 ring carbon atoms, R ⁶ and R ⁷ and R ⁸ and R ⁹ may be bonded to each other to form a saturated or unsaturated ring together with the carbon atom to which they are bonded. The material for organic electroluminescent elements according to claim 1 represented by the following general formula (2).

(In the formula, X, Y, R ¹ , R ^{2 to} R ⁵ , m, n, p, q, L ¹ and L ² are the same as described above.) The material for organic electroluminescent elements according to claim 1, represented by the following general formula (3).

(In the formula, X, Y, R ¹ , R ^{2 to} R ⁵ , m, n, p, q, L ¹ and L ² are the same as described above.) The arylene group is an o-phenylene group, m-phenylene group, p-phenylene group, 2,2'-biphenyldiyl group, 3,3'-biphenyldiyl group, 4,4'-biphenyldiyl group, 2,3 ' -Biphenyldiyl group, 2,4'-biphenyldiyl group, 3,4'-biphenyldiyl group, m-terphenyl-3,3 ''-diyl group, 1,4-naphthalenediyl group, 2,7-phenanthrene The organic electroluminescent element material according to any one of claims 1 to 3, which is a group selected from diyl groups. The energy level of triplet is 2.0-3.2eV, The organic electroluminescent element material of any one of Claims 1-4. The organic electroluminescent element material according to any one of claims 1 to 5, wherein the organic thin film layer includes one or more organic thin film layers including a light emitting layer between a cathode and an anode. An organic electroluminescence element to be contained. The organic electroluminescence element according to claim 6, wherein the light emitting layer contains the material for an organic electroluminescence element as a host material. The organic electroluminescent device according to claim 6 or 7, wherein the light emitting layer contains a host material and a phosphorescent material, and the host material is the material for an organic electroluminescent device. The organic electroluminescence device according to claim 8, wherein the phosphorescent material is a compound containing a metal selected from iridium (Ir), osmium (Os), and platinum (Pt). The organic electroluminescent element according to claim 9, wherein the metal-containing compound is an orthometalated metal complex. The organic electroluminescence device according to claim 6, further comprising a reducing dopant in an interface region between the cathode and the organic thin film layer. The organic electroluminescent element according to any one of claims 6 to 10, 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. The organic electro according to any one of claims 6 to 10, further comprising a hole transport layer between the light emitting layer and the anode, wherein the hole transport layer contains the material for an organic electroluminescence element. Luminescence element. The organic electroluminescence device according to any one of claims 6 to 10, further comprising an electron transport layer between the light emitting layer and the cathode, wherein the electron transport layer contains the material for an organic electroluminescence device. .