JP4377198B2 - Organic electroluminescence device - Google Patents

Description

  The present invention relates to a light emitting element capable of emitting light by converting electric energy into light.

As a means for enhancing the durability of an organic electroluminescence (EL) element, it is disclosed that an element containing two or more host materials has improved luminous efficiency and durability (Patent Document 1). The invention discloses that the light emitting layer host contains at least one electron transporting compound and at least one anthryl compound. Examples of the electron transporting compound include oxadiazole, triazole, quinoxaline, and quinoline derivatives as nitrogen-containing heterocyclic compounds, and quinolinol-based ligands as nitrogen-containing ligand complexes. Although the device durability was improved by using the compounds shown in these patents, it was not sufficient and further durability improvement was desired.
JP 2001-284050 A

  An object of the present invention is to provide a light emitting element having good light emitting characteristics and durability.

As a result of studying the above problems, the present inventors have reached the present invention by the following means.
1. An organic electroluminescent element having at least one organic layer including a light emitting layer between a pair of electrodes, the light emitting layer containing at least two kinds of host materials and at least one kind of fluorescent light emitting materials, at least one is an organic electroluminescent device, characterized in that it is a metal complex represented by the following formula (IV) of.
Formula (IV)

(Where X ^{twenty one} And X ^{twenty two} Represents a carbon atom or a nitrogen atom. Y ² Represents a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom. Z ² Represents a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom. However, (Y ² , Z ² ) Does not become (N, O) or (O, N). Q ^{twenty one} Represents an atomic group necessary for forming a 5-membered ring, 6-membered ring or 7-membered ring. Q ^{twenty two} Represents an atomic group necessary for forming a 5-membered ring, 6-membered ring or 7-membered ring. M ² Represents a metal ion. n ² Represents an integer of 1 or more. L ² Represents a ligand, m ² Represents an integer of 0 or more. The bond type between each atom may be any of a single bond, a double bond, a triple bond, and a coordination bond. )
Q forming a 2.5, 6 or 7 membered ring ^{twenty one} , Q ^{twenty two} Each form an aromatic ring, Y ² Is a nitrogen atom or an oxygen atom, and Z ² 2. The organic electroluminescence device according to 1, wherein is an nitrogen atom, an oxygen atom or a sulfur atom.
3. M ² Is Al ³⁺ , Zn ²⁺ , Be ²⁺ , Mg ²⁺ Or Cu ²⁺ 3. The organic electroluminescent device according to 1 or 2, wherein
4). M ² Is Al ³⁺ 3. The organic electroluminescence device according to 3, wherein
5). n ² Is 1-4 and m ² The organic electroluminescent element according to any one of 1 to 4, wherein is 0.
6). n ² 5. The organic electroluminescent device according to 5, wherein 3 is 3.
7. Q ^{twenty one} The ring formed by is a pyridine ring, pyrimidine ring, pyrazine ring, quinoline ring, quinoxaline ring, isoquinoline ring, phthalazine ring, pyrrole ring, indole ring, imidazole ring, benzimidazole ring, oxazole ring, benzoxazole ring, thiazole ring Benzothiazole ring, triazole ring, benzotriazole ring or imidazopyridine ring, ^{twenty two} The organic electroluminescent device according to any one of 1 to 6, wherein the ring formed by is a benzene ring, naphthalene ring, pyridine ring, thiophene ring or pyrazine ring.
8). Q ^{twenty one} The ring formed by is an imidazopyridine ring, ^{twenty two} 8. The organic electroluminescent element according to any one of 1 to 7, wherein the ring formed by is a benzene ring.
9. An organic electroluminescent device having at least one organic layer including a light emitting layer between a pair of electrodes, the light emitting layer containing at least two kinds of host materials and at least one kind of fluorescent light emitting materials, An organic electroluminescent element, wherein at least one of the materials is a metal complex represented by the following formula (III).
Formula (III)

(In the formula (III), X ¹¹ , X ¹² Each represents a carbon atom or a nitrogen atom. X ¹¹ And nitrogen atom, X ¹² And the carbon atom may be a single bond or a double bond. Z ¹¹ , Z ¹² Each represents an atomic group necessary for forming a 5-membered ring or a 6-membered ring. M ¹ Represents a metal ion. n ¹ Represents an integer of 1 or more. L ^H Represents a ligand, m ¹ Represents an integer of 0 or more. )
10. Z ¹¹ The ring formed by is a pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, quinoline ring, quinoxaline ring, isoquinoline ring, cinnoline ring, phthalazine ring, quinazoline ring, triazine ring, acridine ring, phenazine ring, phenanthroline ring, naphthyridine Ring, phenanthridine ring, pyrrole ring, indole ring, pyrazole ring, imidazole ring, benzimidazole ring, oxazole ring, benzoxazole ring, thiazole ring, benzothiazole ring, selenazole ring, benzoselenazole ring, indazole ring, isothiazole Ring, isoxazole ring, triazole ring, benzotriazole ring, tetrazole ring, oxadiazole ring, thiadiazole ring, thiatriazole ring, azaindole ring, imidazopyridine ring, purine ring or imidazo A down ring, wherein Z ¹² 10. The organic electroluminescent device according to 9, wherein the ring formed by is an aromatic ring.
11. Z ¹¹ The ring formed by pyridine ring, pyrimidine ring, pyrazine ring, quinoline ring, quinoxaline ring, isoquinoline ring, phthalazine ring, pyrrole ring, indole ring, imidazole ring, benzimidazole ring, oxazole ring, benzoxazole ring, thiazole ring, A benzothiazole ring, a triazole ring, a benzotriazole ring or an imidazopyridine ring, ¹² The organic electroluminescent device according to 9 or 10, wherein the ring formed by is benzene, naphthalene, anthracene, pyridine, thiophene, pyrazine or pyrimidine.
12 M ¹ Is Al ³⁺ , Zn ²⁺ , Be ²⁺ , Mg ²⁺ Or Cu ²⁺ The organic electroluminescent element according to any one of 9 to 11, wherein
13. M ¹ Is Al ³⁺ 13. The organic electroluminescent device according to 12, wherein
14 n ¹ Is 1-4 and m ¹ The organic electroluminescent element according to any one of 9 to 13, wherein is 0 or 1.
15. n ¹ Is 2 or 3, m ¹ 15. The organic electroluminescence device according to 14, wherein is zero.

16. The at least two kinds of host materials contained in the light emitting layer are any one of the metal complex represented by the formula (III) or (IV), a condensed aromatic carbocyclic compound, a polyarylene compound, and a triarylamine. The organic electroluminescent element according to any one of 1 to 15, wherein the organic electroluminescent element is a combination of two.
17. The at least two kinds of host materials are a combination of the metal complex represented by the formula (III) or (IV) and any one of a condensed aromatic carbocyclic compound and a polyarylene compound. 16. The organic electroluminescent device according to 16.
18. Any one of 1 to 17, wherein the fluorescent light-emitting material is a condensed aromatic compound which may have a substituent, and the substituent is an aryl group, a heteroaromatic ring group, a diarylamino group or an alkyl group. 2. The organic electroluminescent element according to item 1.
19. 19. The organic electroluminescent device according to 18, wherein the condensed aromatic compound is a condensed aromatic hydrocarbon compound.
20. The organic electroluminescent element according to any one of 1 to 19 , wherein the organic electroluminescent element contains an electron transport layer, and the electron transport layer contains a compound represented by the formula (E1).

(In the formula, R _E represents a hydrogen atom or a substituent. X _E represents —O—, —S—, ═N— or ═N—Ra, where Ra represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group, or a hetero group. Q _E represents a group of atoms necessary to form a heterocyclic ring by combining with N and X _E. )
21. 21. The organic electroluminescent element according to 20, wherein the electron transport layer contains a compound represented by the formula (E-II).

(Wherein, X _E is -O -, - S -., = N- or = N-Ra (Ra is hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group) are expressed .Z _E Represents an atomic group necessary for forming an aromatic ring, B represents a linking group, and m represents an integer of 2 or more.
22. 21. The organic electroluminescence device according to 20 , wherein the electron transport layer contains a compound represented by the formula (E-III).

(In the formula, R _E31 , R _E32 and R _E33 represent a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group.)
23. 21. The organic electroluminescent element according to 20 , wherein the electron transport layer contains a compound represented by the formula (E-IV).
Formula (E-IV)

(In the formula, R ^A1 , R ^A2 and R ^A3 each represent a hydrogen atom or an aliphatic hydrocarbon group. R ^A4 , R ^A5 and R ^A6 each represent a substituent. N ^A1 , n ^A2 and n ^A3. Each represents an integer of 0 to 3. X ^A1 , X ^A2, and X ^A3 each represent a nitrogen atom or C—R ^X (R ^X represents a hydrogen atom or a substituent) Y ^A1 , Y ^A2 And Y ^A3 each represents a nitrogen atom or C—R ^YX (R ^YX represents a hydrogen atom or a substituent).

The light-emitting element of the present invention is excellent in light emission characteristics (color purity and external quantum efficiency (φ _EL )) and durability (small increase in drive voltage and decrease in luminance over time).

Hereinafter, the present invention will be described in detail. In the present specification, “to” indicates a range including numerical values described before and after that as a minimum value and a maximum value, respectively.
Although this invention is invention which concerns on said 1-23, below, other matters are also described.

  The present invention relates to an organic electroluminescent device in which a light emitting layer or a plurality of organic compound layers including a light emitting layer is formed between a pair of electrodes, the light emitting layer contains at least one fluorescent light emitting material and a host material, It has at least two or more. Paying attention to the electron transporting material mixed in the light emitting layer, as a result of various studies of nitrogen-containing heterocyclic compounds and nitrogen-containing ligands, the azine compound, azole compound, and metal complex of the present invention can be used to obtain luminous efficiency, Improved durability.

  The host material contained in the light emitting layer will be described. The element of the present invention has at least two host materials in the light emitting layer, and the compound used as the host material is a compound capable of injecting holes or electrons, and is further generated by recombination of the injected holes and electrons. It preferably has the ability to transfer energy from excitons to fluorescent materials.

  Specifically, the host material of the present invention is a 5- to 7-membered heterocyclic compound containing a nitrogen atom, an oxygen atom or a sulfur atom (for example, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinazoline, phthalazine, cinnoline, isoquinoline). , Pteridine, acridine, phenazine, pyrrole, furan, thiophene, tetrazole, pyrazole, imidazole, thiazole, oxazole, indazole, benzimidazole, benzotriazole, benzoxazole, benzothiazole, carbazole, indole, purine, triazolopyridazine, triazolopyrimidine , Tetrazaindene, pyralidine, pyrrolopyridine, thiadiazolopyridine, dibenzazepine, tribenzazepine, azafluoranthene, etc.), polyarylene compounds Fluorene compound, cyclopentadiene compound, condensed aromatic carbocyclic compound (preferably 2 to 10 rings, more preferably 2 to 8 rings, particularly preferably 2 to 6 rings, such as naphthalene, phenanthrene, anthracene, tetracene, pyrene , Pentacene, perylene, coronene, chrysene, picene, pericyclene, fluoranthene, and the like, and compounds described in JP-A No. 2001-192651.), Triarylamine compounds, nitrogen-containing heterocyclic compounds are coordinated Examples thereof include a metal complex having a child.

  More preferably as a host material of the present invention, a triarylamine compound, a carbazole compound, an indole compound, a pyrrole compound, a pyrazole compound, a thiophene compound, a polyarylene compound, a condensed aromatic carbocyclic compound, a hetero compound containing two or more heteroatoms Ring compounds and the like.

  At least one of the host materials of the present invention includes a compound having a monocyclic azine ring skeleton, a compound having an azole ring skeleton condensed with a heterocycle, a compound having an azine ring skeleton condensed with a heterocycle, and a metal ion with nitrogen. Or a metal complex having a ligand in which a carbocyclic ring or a heterocyclic ring coordinated with an oxygen anion, a sulfur anion or a nitrogen anion is connected to a metal ion by a single bond or a linking group.

The monocyclic azine compound is preferably a compound selected from the group of pyridine, pyrazine, pyrimidine, pyridazine, and triazine substituted with an aromatic carbocycle or aromatic heterocycle, and more preferably represented by the formula (I) Compounds and compounds described in WO03 / 007658A2. Formula (I) is synonymous with formula (C-II) described in JP-A No. 2002-319491, and a preferred range is also the same.
Formula (I)

(In the formula, R ₃₁ , R ₃₂ and R ₃₃ each represent a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group.)

The compound having an azole ring skeleton fused with the heterocycle is preferably a compound represented by the formula (II).
Formula (II)

(In the formula, R represents a hydrogen atom or a substituent. X represents —O—, —S—, ═N— or ═N—R _{A, where} R _A represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a hetero group; Q represents a group of atoms necessary to form an azole ring formed by bonding with N and X and a heterocyclic ring condensed therewith.)

In formula (II), R represents a hydrogen atom or a substituent. X represents O, S, N or N—R _A (R _A represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group). R and X, and R and Q may be combined to form a ring, if possible. Substituent A is mentioned as a substituent represented by R.

(Substituent A)
An alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n- Decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, For example, vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, For example, propargyl, 3-pentynyl, etc.), aryl groups (preferably having 6 to 30 carbon atoms, more preferably Prime number 6 to 20, particularly preferably 6 to 12 carbon atoms, such as phenyl, p-methylphenyl, naphthyl, etc.), amino group (preferably 0 to 30 carbon atoms, more preferably 0 to 0 carbon atoms). 24, particularly preferably having 0 to 20 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino, dinaphthylamino and the like, particularly preferably diphenylamino, ditolylamino, di A naphthylamino group), an alkoxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methoxy, ethoxy, butoxy, 2-ethylhexyl). Siloxy and the like), an aryloxy group (preferably having 6 to 6 carbon atoms). 0, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenoxy, 1-naphthoxy, 2-naphthoxy and the like, and a heterocyclic oxy group (preferably having 2 to 2 carbon atoms). 20, more preferably 3 to 16 carbon atoms, particularly preferably 4 to 12 carbon atoms, and examples thereof include pyridinooxy, pyrimidinooxy, pyridazinooxy, benzimidazolyloxy, and the like, and silyloxy groups (preferably having 3 to 40 carbon atoms, More preferably, it has 3 to 30 carbon atoms, particularly preferably 3 to 20 carbon atoms, and examples thereof include trimethylsilyloxy, t-butyldimethylsilyloxy, triphenylsilyloxy, etc.), acyl group (preferably 1 carbon atom). To 30, more preferably 1 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms. For example, acetyl, benzoyl, formyl, pivaloyl and the like can be mentioned. ), An alkoxycarbonyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, etc.), aryloxycarbonyl A group (preferably having 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, such as phenoxycarbonyl), an acyloxy group (preferably having 2 to 30 carbon atoms). More preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetoxy and benzoyloxy), acylamino groups (preferably 2 to 30 carbon atoms, more preferably 2 carbon atoms). -20, particularly preferably 2 to 10 carbon atoms, such as acetylamino, benzoylamino An alkoxycarbonylamino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino). An aryloxycarbonylamino group (preferably having a carbon number of 7 to 30, more preferably a carbon number of 7 to 20, particularly preferably a carbon number of 7 to 12, such as phenoxycarbonylamino), a sulfonylamino group (preferably Has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include methanesulfonylamino and benzenesulfonylamino.), A sulfamoyl group (preferably 0 carbon atoms). To 30, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 12 carbon atoms. For example, sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl, etc.), carbamoyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably carbon 1 to 12, for example, carbamoyl, methylcarbamoyl, diethylcarbamoyl, phenylcarbamoyl, etc.), alkylthio group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably carbon number). 1 to 12, for example, methylthio, ethylthio, etc.), arylthio groups (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio A heterocyclic thio group (preferably having a carbon number) 1-30, More preferably, it is C1-C20, Most preferably, it is C1-C12, for example, pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio etc. are mentioned. . ), A sulfonyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as mesyl and tosyl), a sulfinyl group (preferably carbon). 1 to 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfinyl, benzenesulfinyl, etc.), ureido group (preferably 1 to 30 carbon atoms, more Preferably it is C1-C20, Most preferably, it is C1-C12, for example, a ureido, methylureido, phenylureido etc. are mentioned), phosphoric acid amide groups (preferably C1-C30, More preferably It has 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms. Examples thereof include diethyl phosphoric acid amide and phenyl phosphoric acid amide. Hydroxy group, mercapto group, halogen atom (eg fluorine atom, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group Group, heterocyclic group (preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, and examples of the hetero atom include a nitrogen atom, an oxygen atom and a sulfur atom, specifically, for example, imidazolyl, pyridyl and quinolyl. , Furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, azepinyl, etc.), silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably Has 3 to 24 carbon atoms, such as trimethylsilyl, tri Enirushiriru and the like.), And the like. These substituents may be further substituted. Moreover, when there are two or more substituents, they may be the same or different. If possible, they may be linked to form a ring.

  The substituent represented by R is preferably an aliphatic hydrocarbon group, an aryl group or a heterocyclic group, more preferably an aryl group or an aromatic heterocyclic group, still more preferably an aryl group, 5 or 6 member. And particularly preferably an aryl group, a 5- or 6-membered aromatic heterocyclic group containing at least one of N, S, and O atoms, and most preferably an aryl group.

X represents O, S, N, or N—R _A. R _A represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. The aliphatic hydrocarbon group represented by R _A is a linear, branched or cyclic alkyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms, For example, methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 to 20 carbon atoms and more). Preferably it is C2-C12, Most preferably, it is C2-C8, for example, vinyl, allyl, 2-butenyl, 3-pentenyl etc.), an alkynyl group (preferably C2-C20, more) Preferably, it has 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, and examples thereof include propargyl and 3-pentynyl. Properly is an alkyl group.

The aryl group represented by R _A is a monocyclic or condensed ring aryl group, preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, still more preferably 6 to 12 carbon atoms, Examples include phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-methoxyphenyl, 3-trifluoromethylphenyl, pentafluorophenyl, 1-naphthyl, 2-naphthyl and the like. The heterocyclic group represented by R _A is a monocyclic or condensed heterocyclic group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, still more preferably 2 to 10 carbon atoms). And preferably an aromatic heterocyclic group containing at least one of a nitrogen atom, an oxygen atom, a sulfur atom and a selenium atom.

Specific examples of the heterocyclic group represented by R _A 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, benzo Examples include thiazole, benzotriazole, tetrazaindene, carbazole, azepine, etc., preferably furan, Thiophene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, more preferably furan, thiophene, pyridine, quinoline, further more preferably quinoline.

The aliphatic hydrocarbon group, aryl group, and heterocyclic group represented by R _A may have a substituent, and those exemplified as the group represented by R in the formula (II) are applicable as the substituent. The preferred substituents are also the same. R _A is preferably an alkyl group, an aryl group, or an aromatic heterocyclic group, more preferably an aryl group or an aromatic heterocyclic group, and still more preferably an aryl group.

  X is preferably O, N or N-Ra, more preferably N or N-Ra, particularly preferably N or N-Ar (Ar is an aryl group (preferably having 6 to 30 carbon atoms, more preferably). An aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms), an aromatic heterocyclic group (preferably 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, still more preferably 2 to 10 carbon atoms). Aromatic heterocyclic group), preferably an aryl group.

  Q represents an atomic group necessary to form a azole ring by combining with N and X, and further to form a heterocycle condensed with the azole ring. Specific examples of the azole ring formed by Q include imidazole ring, oxazole ring, thiazole ring, selenazole ring, tellurazole ring, triazole ring, tetrazole ring, oxadiazole ring, thiadiazole ring, oxatriazole ring and thiatriazole ring. , Pyrrole ring, thiophene ring, furan ring, pyrazole ring, imidazole ring, oxazole ring, thiazole ring, selenazole ring, tellurazole ring, triazole ring, tetrazole ring, oxadiazole ring, thiadiazole ring, oxatriazole ring, thiatriazole ring, A pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, a tetrazine ring, and the like are condensed. Preferably, an imidazole ring, an oxazole ring, a thiazole ring, and a triazole ring are combined with a pyridine ring, a pyrazine ring, and a pyrimidine ring. It is those emissions ring, a pyridazine ring is fused, more preferably, imidazopyridine, purine, triazolopyrimidine, include triazolopyridazine. The heterocyclic ring formed by Q may further form a condensed ring with another ring, and may have a substituent. As the substituent, those exemplified as the group represented by R can be applied. The substituent for Q is preferably an alkyl group, alkenyl group, alkynyl group, aryl group, amino group, alkoxy group, aryloxy group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, acyloxy group, acylamino group, sulfonylamino group , Sulfamoyl group, carbamoyl group, alkylthio group, arylthio group, sulfonyl group, halogen atom, cyano group, heterocyclic group, more preferably alkyl group, alkenyl group, aryl group, alkoxy group, aryloxy group, halogen atom, A cyano group and a heterocyclic group, more preferably an alkyl group, an aryl group, an alkoxy group, an aryloxy group and an aromatic heterocyclic group, particularly preferably an alkyl group, an aryl group, an alkoxy group and an aromatic heterocyclic group. It is.

  A preferred form of the compound represented by formula (II) is a compound represented by formula (IIA), formula (IID), or formula (IIE).

In formula (IIA), R has the same meaning as that in formula (II), and the preferred range is also the same. X represents —O—, —S— or ═N—R _A. R _A has the same meaning as that in formula (II), and the preferred range is also the same. X is preferably -O-, = N-R _A , more preferably = N-R _A , and particularly preferably = N-Ar (Ar is an aryl group (preferably having a carbon number of 6 to 30, more preferably Is an aryl group having 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms), an aromatic heterocyclic group (preferably 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, still more preferably 2 to 2 carbon atoms). 10 aromatic heterocyclic group), preferably an aryl group.

  Z represents an atomic group necessary for forming a heterocycle. Specific examples include pyrrole ring, thiophene ring, furan ring, pyrazole ring, imidazole ring, oxazole ring, thiazole ring, selenazole ring, tellurazole ring, triazole ring, tetrazole ring, oxadiazole ring, thiadiazole ring, oxatriazole ring. , A thiatriazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, a tetrazine ring, and the like, preferably a pyridine ring, a pyrazine ring, a pyrimidine ring, and a pyridazine ring, more preferably a pyridine ring, A pyrazine ring and a pyrimidine ring, more preferably a pyridine ring and a pyrimidine ring, and particularly preferably a pyridine ring. The heterocycle formed by Z may further form a condensed ring with another ring, and may have a substituent.

  As the substituent, for example, those exemplified as the group represented by R in the formula (II) can be applied, and the substituent of the aromatic ring formed by Z is preferably an alkyl group, an alkenyl group, an alkynyl group, an aryl group. Amino group, alkoxy group, aryloxy group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, acyloxy group, acylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group, carbamoyl group, Alkylthio group, arylthio group, sulfonyl group, halogen atom, cyano group, heterocyclic group, more preferably alkyl group, alkenyl group, aryl group, alkoxy group, aryloxy group, halogen atom, cyano group, heterocyclic group Yes, more preferably Group, an aryl group, an alkoxy group, an aryloxy group, an aromatic heterocyclic group, particularly preferably an alkyl group, an aryl group, an alkoxy group, an aromatic heterocyclic group.

  Further preferred forms of the compound represented by formula (IIA) are formula (IIB) and formula (IIC). Formula (IIB) is synonymous with Formula (B-III) described in JP-A No. 2002-319491, and the preferred range is also the same. Formula (B-IV) to ( XX). Formula (IIC) is synonymous with Formula (I) described in JP-A-2002-338579, and a preferred range is also the same.

  Formula (IID) and Formula (IIE) have the same meanings as Formula (I) and Formula (II) described in JP-A No. 2002-356489, and preferred ranges thereof are also the same.

  The metal complex contained as a host is coordinated with a nitrogen-containing heterocycle that coordinates to metal ions with nitrogen, a nitrogen-containing heterocycle that coordinates with metal ions with nitrogen, and a metal ion with oxygen anions, sulfur anions or nitrogen anions. It is a metal complex having a ligand in which carbocycles or heterocycles are linked by a single bond or a linking group. Nitrogen-containing heterocycles that coordinate to metal ions with nitrogen are preferably 5- to 7-membered nitrogen-containing heterocycles (for example, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinazoline, phthalazine, cinnoline, isoquinoline, pteridine, acridine. , Phenazine, pyrrole, tetrazole, pyrazole, imidazole, thiazole, oxazole, indazole, benzimidazole, benzotriazole, benzoxazole, benzothiazole, carbazole, indole, purine, triazolopyridazine, triazolopyrimidine, tetrazaindene, pyraridine, pyrrolo Pyridine, thiadiazolopyridine, dibenzazepine, tribenzazepine, azafluoranthene, etc.). Next, a carbocyclic or nitrogen ring coordinated to a metal ion by an oxygen anion, a sulfur anion or a nitrogen anion will be described. The nitrogen anion preferably represents a dissociated proton on the amino group of an amino group, an acylamino group or a sulfonylamino group, and examples of the carbocycle and heterocycle include those described for Ra. The linking group preferably represents a divalent group, and represents a methylene group, a methine group, an amino group, a carbonylamino group, or a sulfonylamino group.

  It has a nitrogen-containing heterocyclic ring coordinated with the metal ion represented by the formula (III) by nitrogen and a carbocyclic oxyanion or heterocyclic oxyanion coordinated with the metal ion by an oxygen anion linked by a single bond. The metal complex will be described.

In formula (III), the bond between X ¹¹ and the nitrogen atom and between X ¹² and the carbon atom is drawn with two lines, a solid line and a dotted line. This is a double bond even if the bond is a single bond. Represents that it may be.

Z ¹¹ includes X ¹¹ and a nitrogen atom, and represents an atomic group necessary for forming a 5-membered ring or a 6-membered ring. The ring containing Z ¹¹ may have a substituent, and examples of the substituent include an alkyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, particularly preferably 1 to 1 carbon atoms). For example, methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 2 carbon atoms). To 20, more preferably 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, such as vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl groups (preferably 2 carbon atoms). -20, more preferably 2-12 carbon atoms, particularly preferably 2-8 carbon atoms, and examples thereof include propargyl and 3-pentynyl). A reel group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenyl, p-methylphenyl, naphthyl, etc.), a substituted carbonyl group; (Preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, and particularly preferably 1 to 12 carbon atoms. For example, acetyl, benzoyl, methoxycarbonyl, phenyloxycarbonyl, dimethylaminocarbonyl, phenylaminocarbonyl, etc. An amino group (preferably having 0 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as dimethylamino, methylcarbonylamino, ethylsulfonylamino, dimethyl) Aminocarbonylamino group, phthalimide group, etc.), A sulfonyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as mesyl, tosyl, etc.), sulfo group, carboxyl group, heterocyclic ring Group (there are an aliphatic heterocyclic group and an aromatic heterocyclic group. Preferably, it contains any one of an oxygen atom, a sulfur atom and a nitrogen atom, preferably 1 to 50 carbon atoms, more preferably 1 to 30 carbon atoms, Particularly preferably, it has 2 to 12 carbon atoms, and examples thereof include imidazolyl, pyridyl, furyl, piperidyl, morpholino, benzoxazolyl, triazolyl group, etc.), hydroxy group, alkoxy group (preferably having 1 to 20 carbon atoms, More preferably, it is C1-C16, Most preferably, it is C1-C12, for example, a methoxy group, a benzyloxy group, etc. are mentioned. A reeloxy group (preferably having 6 to 20 carbon atoms, more preferably 6 to 16 carbon atoms, and particularly preferably 6 to 12 carbon atoms, and examples thereof include a phenoxy group and a naphthyloxy group. ), Halogen atoms (preferably fluorine atoms, chlorine atoms, bromine atoms, iodine atoms), thiol groups, alkylthio groups (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, and particularly preferably 1 to 1 carbon atoms). 12 such as a methylthio group, and an arylthio group (preferably having 6 to 20 carbon atoms, more preferably 6 to 16 carbon atoms, and particularly preferably 6 to 12 carbon atoms, such as a phenylthio group). ), Cyano group, silyl group (preferably having 0 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 18 carbon atoms, such as trimethylsilyl group, triphenylsilyl group, t-butyldiphenyl And a silyl group). These substituents may be further substituted. The ring containing Z ¹¹ may form a condensed ring with other rings.

Examples of the ring containing Z ¹¹ include pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, quinoline ring, quinoxaline ring, isoquinoline ring, cinnoline ring, phthalazine ring, quinazoline ring, triazine ring, acridine ring, phenazine ring, phenanthroline Ring, naphthyridine ring, phenanthridine ring, pyrrole ring, indole ring, pyrazole ring, imidazole ring, benzimidazole ring, oxazole ring, benzoxazole ring, thiazole ring, benzothiazole ring, selenazole ring, benzoselenazole ring, indazole ring , Isothiazole ring, isoxazole ring, triazole ring, benzotriazole ring, tetrazole ring, oxadiazole ring, thiadiazole ring, thiatriazole ring, azaindole ring, imidazopyridine ring, purine Imidazoline ring, etc., preferably pyridine ring, pyrimidine ring, pyrazine ring, quinoline ring, quinoxaline ring, isoquinoline ring, phthalazine ring, pyrrole ring, indole ring, imidazole ring, benzimidazole ring, oxazole ring, benzoxazole ring , Thiazole ring, benzothiazole ring, triazole ring, benzotriazole ring, and imidazopyridine ring, and more preferably an imidazopyridine ring.

Z ¹² represents an atomic group necessary for forming a 5-membered ring or a 6-membered ring. The ring containing Z ¹² may have a substituent, and as the substituent, those mentioned as the substituent of the ring containing Z ¹¹ can be applied, and preferred ranges are also the same. Examples of the ring containing Z ¹² include cyclopentene, cyclohexene, benzene, naphthalene, anthracene, phenanthrene, pyrene, perylene, pyridine, quinoline, furan, thiophene, pyrazine, pyrimidine, thiazole, benzothiazole, naphthothiazole, oxazole, benzoxazole, Examples include naphthoxazole, isoxazole, selenazole, benzoselenazole, naphthselenazole, imidazole, benzimidazole, naphthimidazole, isoquinoline, pyrazole, triazole and the like. The ring containing Z ¹² is preferably an aromatic ring. For example, benzene, naphthalene, anthracene, pyridine, thiophene, pyrazine, and pyrimidine are preferable, benzene and naphthalene are more preferable, and benzene is more preferable. The substituent of Z ^{11 and} the substituent of Z ¹² may be bonded to form a ring.

M ¹ represents a metal ion. The metal ion is not particularly limited, but is preferably a metal ion included in the second to fourth periods of the periodic table (long period type), more preferably a divalent or trivalent metal ion, More preferable are Be ²⁺ , Mg ²⁺ , Al ³⁺ , Zn ²⁺ and Cu ²⁺ , and particularly preferable are Al ³⁺ and Zn ²⁺ .

L ^H represents a monodentate or polydentate ligand. Examples of the ligand include halogen ions (for example, Cl ⁻ , Br ⁻ , I ^{− and the} like), perchlorate ions, and alkoxy ions (preferably having 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, still more preferably 1 to 5, for example, methoxy ion, ethoxy ion, isopropoxy ion, acetylacetonate ion and the like, aryloxy ion (preferably having 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms, still more preferably 6). -8, for example, phenoxy ion, quinolinol ion, 2- (2-hydroxyphenyl) benzoazole ion, etc.), nitrogen-containing heterocycle (preferably having 1 to 20 carbon atoms, more preferably 2 to 10 carbon atoms, Preferably 3 to 8, and examples thereof include phenanthrene and bipyridyl) Cion (preferably having 1 to 20 carbon atoms, more preferably 2 to 10 carbon atoms, more preferably 3 to 8 carbon atoms such as acetoxy ion), ether compounds (preferably having 2 to 20 carbon atoms, particularly preferably 3 to 3 carbon atoms). 10 and more preferably 3 to 8 and examples thereof include tetrahydrofuran and the like, and hydroxy ions and the like. More preferred are alkoxy ions and aryloxy ions, and particularly preferred are aryloxy ions.

n ¹ represents an integer of 1 or more, and m ¹ represents an integer of 0 or more. The preferred range of n ¹ and m ¹ varies depending on the metal ion and is not particularly limited, but n ¹ is preferably ¹ to 4, more preferably 1 to 3, and particularly preferably 2 or 3. m ¹ is preferably 0 to 2, more preferably 0 or 1, and particularly preferably 0. The combination of the numbers of n ¹ and m ¹ is preferably a combination of numbers in which the metal complex represented by the formula (HI) becomes a neutral complex.

  Examples of the metal complex represented by the formula (III) include metal complexes of imidazopyridine derivatives described in JP-A No. 2000-302754, JP-A-8-301877, JP-A-8-306489, JP-A-9-279134, and JP-A-7 -13383, JP-A 2000-2000684, JP-A 2000-252066, JP-A 2000-247972, JP-A 2000-173777, etc., metal complexes of benzoxazole derivatives, JP-A 2000-302754, JP-A 2000-252067, etc. Metal complexes of oxazole derivatives described in JP-A-8-113576, JP-A-2000-200654, JP-A-2000-247964, JP-A-10-45722, JP-T-2000-515926, etc. 2001-131162, JP-A-20 0-302754, metal complexes of thiazole derivatives described in JP-A-2000-252067, etc., metal complexes of benzimidazole derivatives described in JP-A-2000-200684, JP-A-10-265478, JP-A-2000-302754, JP-A-2000 Metal complexes of imidazole derivatives as described in JP-A-2521067, metal complexes of benzotriazole derivatives and metal complexes of benzopyrazole derivatives as described in JP-A-9-111234, JP-A-2000-357588, JP-A-9-176629, etc. Metal complexes of hydroxyphenyl-substituted pyridine derivatives, metal complexes of hydroxy-substituted benzoquinoline derivatives described in JP-A-9-20886, JP-A 2000-12222, etc., metal complexes of hydroxy-substituted pyridoquinoline derivatives described in JP-A-9-20885 Metal complexes of hydroxyphenyl-substituted triazole derivatives described in JP-A No. 2000-100530, metal complexes of hydroxyphenyl-substituted oxadiazole or thiadiazole derivatives described in JP-A No. 10-259372, hydroxy compounds described in JP-A No. 2001-57292, etc. A metal complex of phenyl-substituted imidazopyridine can be suitably used.

  Specific examples of the metal complex represented by the formula (III) are listed below, but the present invention is not limited thereto.

Examples of compounds other than formula (III) include compounds represented by formula (IV).
Formula (IV)

(Wherein X ²¹ and X ²² represent a carbon atom or a nitrogen atom. Y ² represents a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom. Z ² represents a nitrogen atom, an oxygen atom, a sulfur atom or Represents a phosphorus atom, provided that the combination of (Y ² , Z ² ) is not (N, O) or (O, N) Q ²¹ is a 5-membered ring, 6-membered ring or 7-membered ring Q ²² represents an atomic group necessary for forming a 5-membered ring, a 6-membered ring, or a 7-membered ring, M ² represents a metal ion, and n ² represents an integer of 1 or more. L ² represents a ligand, and m ² represents an integer of 0 or more. The bond type between the atoms may be any of a single bond, a double bond, a triple bond, and a coordination bond.)

X ²¹ and X ²² are a carbon atom or a nitrogen atom. Y ² represents a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom, preferably a nitrogen atom, an oxygen atom or a sulfur atom. Z ² represents a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom, preferably a nitrogen atom, an oxygen atom or a sulfur atom. When Z ² represents a nitrogen atom, it may have a substituent on the nitrogen, and as a substituent on the nitrogen, an alkyl group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, Particularly preferably, it has 1 to 8 carbon atoms, and examples thereof include methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl and the like. A group (preferably having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, such as vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl Groups (preferably having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, such as propargyl, 3-pentini And aryl groups (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenyl, p-methylphenyl, naphthyl, etc.). Substituted carbonyl group (preferably having 1 to 40 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as acetyl, benzoyl, methoxycarbonyl, dimethylaminocarbonyl, phenylamino Carbonyl group, etc.), substituted sulfonyl groups (preferably having 1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as mesyl and tosyl). ), A heterocyclic group (preferably containing any one of an oxygen atom, a sulfur atom and a nitrogen atom, preferably having 1 to 20, more preferably 1 to 16 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include imidazolyl, pyridyl, furyl, piperidyl, and the like. These substituents may be further substituted. As a substituent on nitrogen, an alkyl group, an aryl group, and an aromatic heterocyclic group are preferable, and an alkyl group and an aryl group are more preferable.

In the formula (IV), the combination of (Y ² , Z ² ) does not become (N, O) or (O, N). In the formula (IV), all the bonds between the atoms are indicated by a single solid line, but this does not mean that the bonds are single bonds, and the bonds between the atoms are single bonds. , Any of a double bond and a coordination bond may be used.

Q ²¹ represents an atomic group necessary for forming a 5-membered ring, 6-membered ring or 7-membered ring.
The ring formed by Q ²¹ includes benzene ring, naphthalene ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, quinoline ring, quinoxaline ring, isoquinoline ring, cinnoline ring, phthalazine ring, quinazoline ring, triazine ring, acridine Ring, phenazine ring, phenanthroline ring, naphthyridine ring, phenanthridine ring, pyrrole ring, indole ring, pyrazole ring, imidazole ring, benzimidazole ring, oxazole ring, benzoxazole ring, thiazole ring, benzothiazole ring, selenazole ring, benzo Selenazole ring, indazole ring, isothiazole ring, isoxazole ring, triazole ring, benzotriazole ring, tetrazole ring, oxadiazole ring, thiadiazole ring, thiatriazole ring, azaindole ring, imi Zopirijin ring, purine ring, imidazoline ring, azepine ring, a furan ring, benzofuran ring, thiophene ring, aromatic ring such benzothiophene ring and mentioned above are all or partially reduced, and the like. The ring formed by Q ²¹ is preferably an aromatic ring, and preferably a pyridine ring, pyrimidine ring, pyrazine ring, quinoline ring, quinoxaline ring, isoquinoline ring, phthalazine ring, pyrrole ring, indole ring, imidazole ring, benzimidazole A ring, an oxazole ring, a benzoxazole ring, a thiazole ring, a benzothiazole ring, a triazole ring, a benzotriazole ring, and an imidazopyridine ring, and more preferably an imidazopyridine ring.

Q ²² represents an atomic group necessary for forming a 6-membered ring or a 5-membered ring.
The ring formed by Q ²² includes benzene ring, naphthalene ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, quinoline ring, quinoxaline ring, isoquinoline ring, cinnoline ring, phthalazine ring, quinazoline ring, triazine ring, acridine Ring, phenazine ring, phenanthroline ring, naphthyridine ring, phenanthridine ring, pyrrole ring, indole ring, pyrazole ring, imidazole ring, benzimidazole ring, oxazole ring, benzoxazole ring, thiazole ring, benzothiazole ring, selenazole ring, benzo Selenazole ring, indazole ring, isothiazole ring, isoxazole ring, triazole ring, benzotriazole ring, tetrazole ring, oxadiazole ring, thiadiazole ring, thiatriazole ring, azaindole ring, imi Zopirijin ring, purine ring, imidazoline ring, azepine ring, a furan ring, benzofuran ring, thiophene ring, benzothiophene ring, cyclohexane ring, cyclohexene ring, a pyrene ring, a perylene ring, and the like. The ring formed by Q ²² is preferably an aromatic ring, preferably a benzene ring, a naphthalene ring, a pyridine ring, a thiophene ring or a pyrazine ring, more preferably a benzene ring or a pyridine ring, still more preferably Benzene ring. The ring formed by Q ²¹ and Q ²² may have a substituent, and as the substituent, those exemplified as the substituent of each atom in formula (I) can be applied.

M ² represents a metal ion. Although it does not specifically limit as a metal ion, Preferably it is a metal ion contained in the 2nd period-4th period of a periodic table (long period type), More preferably, it is a bivalent or trivalent metal ion, More preferable are Be ²⁺ , Mg ²⁺ , Al ³⁺ , Zn ²⁺ and Cu ²⁺ , and particularly preferable are Al ³⁺ and Zn ²⁺ .

L ² represents a monodentate or multidentate ligand. Examples of the ligand include halogen ions (for example, Cl ⁻ , Br ⁻ , I ^{− and the} like), perchlorate ions, and alkoxy ions (preferably having 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, still more preferably 1 to 5, for example, methoxy ion, ethoxy ion, isopropoxy ion, acetylacetonate ion and the like, aryloxy ion (preferably having 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms, still more preferably 6). -8, for example, phenoxy ion, quinolinol ion, 2- (2-hydroxyphenyl) benzoazole ion, etc.), nitrogen-containing heterocycle (preferably having 1 to 20 carbon atoms, more preferably 2 to 10 carbon atoms, Preferably 3 to 8, and examples thereof include phenanthrene and bipyridyl) Cion (preferably having 1 to 20 carbon atoms, more preferably 2 to 10 carbon atoms, more preferably 3 to 8 carbon atoms such as acetoxy ion), ether compounds (preferably having 2 to 20 carbon atoms, particularly preferably 3 to 3 carbon atoms). 10 and more preferably 3 to 8 and examples thereof include tetrahydrofuran and the like, and hydroxy ions and the like. More preferred are alkoxy ions and aryloxy ions, and particularly preferred are aryloxy ions.

n ² represents an integer of 1 or more, and m ² represents an integer of 0 or more. The preferable range of n ² and m ² varies depending on the metal ion and is not particularly limited. However, n ² is preferably 1 to 4, more preferably 1 to 3, and particularly preferably 2 or 3. m ² is preferably 0 to 2, more preferably 0 or 1, and particularly preferably 0. The combination of the numbers of n ² and m ² is preferably a combination of numbers in which the metal complex represented by the formula (IV) becomes a neutral complex.
Specific examples of the metal complex represented by the formula (IV) are listed below, but the present invention is not limited thereto.

  Other preferable hosts are represented by the formula (I) described in JP-A No. 2002-1000047, and more preferably the formula (A-1), the formula (B-1), the formula (C-1), and the formula (D -1) and the following specific examples.

  The concentration of at least one host material of the present invention in the light emitting layer is preferably 1% by mass or more and 99% by mass or less, more preferably 5% by mass or more and 90% by mass or less, and more preferably 10% by mass or more. More preferably, it is 80 mass% or less. The remainder is phosphorescent light emitting material and other host materials.

  At least one host material in the light-emitting layer is a compound having a heterocyclic skeleton, more preferably, at least one host material is a compound containing two or more heteroatoms, and particularly preferably, at least one host material. Is a heterocyclic condensed ring compound having two or more heteroatoms in one ring.

  Preferred combinations of host materials include host material A (a compound having a monocyclic azine ring skeleton, a compound having an azole ring skeleton fused with a heterocycle, a compound having an azine ring skeleton fused with a heterocycle, a metal ion with nitrogen) Any of a metal complex having a ligand in which a nitrogen-containing heterocycle to be coordinated and a carbon ring or heterocycle to be coordinated to a metal ion with an oxygen anion, a sulfur anion or a nitrogen anion are connected by a single bond or a linking group) 1 and any one of amine compounds such as condensed aromatic carbocyclic compounds, polyarylene compounds, thiophene compounds, pyrrole compounds, triarylamines, and more preferably any one of the host materials A, Any of amine compounds such as condensed aromatic carbocyclic compounds, polyarylene compounds, and triarylamines 1, which is the bracts of the combination.

  The material (electron injection / transport material) constituting the electron injection / transport layer of the present invention will be described. The material for the electron injection layer and the electron transport layer of the present invention is any material that has one of the function of injecting electrons from the cathode, the function of transporting electrons, and the function of blocking holes injected from the anode. good.

  Examples of the electron transport material include an electron withdrawing group (preferably an electron withdrawing group having a Hammett σp value of 0.2 or more, and more preferably an aryl group, an aromatic heterocyclic group, a cyano group, a carbonyl group, Aromatic carbocyclic compounds substituted with thiocarbonyl group, oxycarbonyl group, acylamino group, carbamoyl group, sulfamoyl group, sulfonyl group, imino group, halogen atom etc. (preferably benzene, naphthalene, anthracene, phenanthate) Lathenes, tetracenes, pyrenes, pentacenes, perylenes, coronene, chrysene, picenes, pericyclenes, acenaphthenes, fluoranthenes, etc.), nitrogen-containing aromatic heterocycles (including 5- to 6-membered aromatic nitrogen-containing heterocycles, Hetero atoms as oxygen atoms, nitrogen atoms, sulfur atoms, silicon It may contain atoms and may form 2 to 10 condensed rings such as pyridine structure, pyrazine structure, pyrimidine structure, pyridazine structure, pyrrole structure, pyrazole structure, imidazole structure, oxazole structure, thiazole structure, triazole structure. And combinations thereof), and metal complexes.

  Specific examples of the electron transport material include triazole, oxazole, oxadiazole, imidazole, fluorenone, anthraquinodimethane, anthrone, diphenylquinone, thiopyran dioxide, carbodiimide, fluorenylidenemethane, distyrylpyrazine, naphthalene, Aromatic detracarboxylic anhydrides such as perylene, phthalocyanines, metal complexes of 8-quinolinol derivatives, metal phthalocyanines, various metal complexes represented by metal complexes having benzoxazole or benzothiazole as a ligand, organosilane compounds and derivatives thereof Etc.

  Preferably, the electron transport material is a compound represented by the formula (I) described in JP-A No. 2002-319491 (here, the compound represented by the formula (I) is represented as a compound represented by the formula (E1)). And a compound represented by the formula (A) described in JP-A No. 2002-1000047 (herein, the compound represented by the formula (A) is represented as a compound represented by the formula (E-IV)) It is.

(In the formula, R _E represents a hydrogen atom or a substituent. X _E represents —O—, —S—, ═N— or ═N—Ra, where Ra represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group, or a hetero group. Q _E represents a group of atoms necessary for forming a heterocycle by combining with N and X. The description of each group is given by the formula (JP-A-2002-319491). Same as I).

  A preferred form of the compound represented by formula (E1) is the following formula (E2) or formula (E-III).

In the formula, R _E and X _E have the same meanings as those in formula (E1). Z _E represents an atomic group necessary for forming an aromatic ring, and is the same as Z described in the formula (II) described in JP-A No. 2002-319491.

A more preferred form of the compound represented by the formula (E2) is the formula (E-II), in which R _E , X _E and B are those described in the formula (B-II) described in JP-A No. 2002-319491. The preferred ranges are also the same, and are compounds represented by formulas (B-III) to (BX) described in JP-A No. 2002-319491.

In formula (E-III), R _E31 , R _E32 and R _E33 represent a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group, and the formula (C-II) described in JP-A-2002-319491 The preferred range is also the same. Specific examples of the compound represented by the formula (E1) used in the present invention are specific examples (Compound Nos. 205 to 306, 367 to 381) described in JP-A No. 2002-319491, but the present invention is not limited thereto. Is not to be done.
Formula (E-IV)

In the formula, R ^A1 , R ^A2 and R ^A3 each represent a hydrogen atom or an aliphatic hydrocarbon group. R ^A4 , R ^A5 and R ^A6 each represent a substituent. n ^A1 , n ^A2 and n ^A3 each represent an integer of 0 to 3. X ^A1 , X ^A2 and X ^A3 each represent a nitrogen atom or C—R ^X (R ^X represents a hydrogen atom or a substituent). Y ^A1 , Y ^A2 and Y ^A3 each represent a nitrogen atom or C—R ^YX (R ^YX represents a hydrogen atom or a substituent), and are represented by the formula (A) described in JP-A No. 2002-1000047. The preferred range is also the same.

  A method for manufacturing a light emitting element of the present invention will be described. The method for forming the organic layer of the light emitting device of the present invention is not particularly limited, and methods such as resistance heating vapor deposition, electron beam, sputtering, molecular lamination method, coating method, ink jet method, and printing method are used. Resistance heating vapor deposition, coating method, and transfer method are preferable in terms of characteristics and production.

  The light-emitting device of the present invention is a device in which a light-emitting layer or a plurality of organic compound layers including a light-emitting layer is formed between a pair of anode and cathode electrodes. In addition to the light-emitting layer, a hole injection layer, a hole transport layer, and an electron injection It has a layer and an electron transport layer, and each of these layers may have other functions. Various appropriate materials can be used for forming each layer.

  The anode supplies holes to a hole injection layer, a hole transport layer, a light emitting layer, and the like, and a metal, an alloy, a metal oxide, an electrically conductive compound, or a mixture thereof can be used. Is a material having a work function of 4 eV or more. Specific examples include conductive metal oxides such as tin oxide, zinc oxide, indium oxide and indium tin oxide (ITO), metals such as gold, silver, chromium and nickel, and these metals and conductive metal oxides. Inorganic conductive materials such as copper iodide and copper sulfide, organic conductive materials such as polyaniline, polythiophene, and polypyrrole, and laminates of these with ITO, preferably conductive metals It is an oxide, and ITO is particularly preferable from the viewpoint of productivity, high conductivity, transparency, and the like. Although the film thickness of the anode can be appropriately selected depending on the material, it is usually preferably in the range of 10 nm to 5 μm, more preferably 50 nm to 1 μm, still more preferably 100 nm to 500 nm.

  As the anode, a layer formed on a soda-lime glass, non-alkali glass, a transparent resin substrate or the like is usually used. When glass is used, it is preferable to use non-alkali glass as the material in order to reduce ions eluted from the glass. Moreover, when using soda-lime glass, it is preferable to use what gave barrier coatings, such as a silica. The thickness of the substrate is not particularly limited as long as it is sufficient to maintain the mechanical strength, but when glass is used, a thickness of 0.2 mm or more, preferably 0.7 mm or more is usually used. Various methods are used for producing the anode depending on the material. For example, in the case of ITO, an electron beam method, a sputtering method, a resistance heating vapor deposition method, a chemical reaction method (sol-gel method, etc.), a coating of a dispersion of indium tin oxide, etc. A film is formed by this method. The anode can be subjected to cleaning or other treatments to lower the drive voltage of the element and increase the light emission efficiency. For example, in the case of ITO, UV-ozone treatment, plasma treatment, etc. are effective.

  The cathode supplies electrons to the electron injection layer, the electron transport layer, the light emitting layer, etc., and the adhesion, ionization potential, stability, etc., between the negative electrode and the adjacent layer such as the electron injection layer, electron transport layer, light emitting layer, etc. Selected in consideration of As a material for the cathode, a metal, an alloy, a metal halide, a metal oxide, an electrically conductive compound, or a mixture thereof can be used. Specific examples include an alkali metal (for example, Li, Na, K, etc.) and its fluoride. Or oxides, alkaline earth metals (eg, Mg, Ca, etc.) and fluorides or oxides thereof, gold, silver, lead, aluminum, sodium-potassium alloys or their mixed metals, lithium-aluminum alloys or their mixtures Examples thereof include metals, magnesium-silver alloys or mixed metals thereof, rare earth metals such as indium and ytterbium, preferably materials having a work function of 4 eV or less, more preferably aluminum, lithium-aluminum alloys or mixed metals thereof. , Magnesium-silver alloys or mixed metals thereof. The cathode can take not only a single layer structure of the compound and the mixture but also a laminated structure including the compound and the mixture. For example, a laminated structure of aluminum / lithium fluoride and aluminum / lithium oxide is preferable. The film thickness of the cathode can be appropriately selected depending on the material, but is usually preferably in the range of 10 nm to 5 μm, more preferably 50 nm to 1 μm, still more preferably 100 nm to 1 μm.

  For production of the cathode, methods such as an electron beam method, a sputtering method, a resistance heating vapor deposition method, and a coating method are used, and a metal can be vapor-deposited alone or two or more components can be vapor-deposited simultaneously. Furthermore, a plurality of metals can be vapor-deposited simultaneously to form an alloy electrode, or a previously prepared alloy may be vapor-deposited. The sheet resistance of the anode and the cathode is preferably low, and is preferably several hundred Ω / □ or less.

  The luminescent material of the present invention is a fluorescent compound. Further, a phosphorescent compound that emits light from triplet excitons may be used in combination. For example, benzoxazole derivatives, benzimidazole derivatives, benzothiazole derivatives, styrylbenzene derivatives, polyphenyl derivatives, diphenylbutadiene derivatives, tetraphenylbutadiene derivatives, naphthalimide derivatives, coumarin derivatives, condensed aromatic compounds, perinone derivatives, oxadiazole derivatives, Oxazine derivatives, aldazine derivatives, pyralidine derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives, quinacridone derivatives, pyrrolopyridine derivatives, thiadiazolopyridine derivatives, cyclopentadiene derivatives, styrylamine derivatives, diketopyrrolopyrrole derivatives, aromatic dimethylidin compounds, Represented by metal complexes of 8-quinolinol derivatives, metal complexes of pyromethene derivatives, rare earth complexes, and transition metal complexes Seed metal complexes, polythiophene, polyphenylene, polymeric compounds such as polyphenylene vinylene, organic silane derivatives, the compounds of the present invention, and the like.

  The light-emitting material of the present invention is preferably a condensed aromatic compound, a styryl compound, a diketopyrrolopyrrole compound, an oxazine compound, a pyromethene metal complex, a transition metal complex, or a lanthanoid complex. Preferably, the condensed aromatic hydrocarbon compound is naphthacene, pyrene, chrysene, triphenylene, benzo [c] phenanthrene, benzo [a] anthracene, bentacene, perylene, fluoranthene, acenaphthofluoranthene, dibenzo [a, j] anthracene , Dibenzo [a, h] anthracene, benzo [a] naphthacene, hexacene, anthanthrene and the like, and condensed aromatic heterocycles include naphtho [2,1-f] isoquinoline, α-naphthaphenanthridine, Examples thereof include nantrooxazole, quinolino [6,5-f] quinoline, benzothiophanthrene and the like. These may have an aryl group, a heteroaromatic ring group, a diarylamino group, or an alkyl group as a substituent.

  Although the film thickness of a light emitting layer is not specifically limited, Usually, the thing of the range of 1 nm-5 micrometers is preferable, More preferably, it is 5 nm-1 micrometer, More preferably, it is 10 nm-500 nm.

  The method for forming the light emitting layer is not particularly limited, but resistance heating vapor deposition, electron beam, sputtering, molecular lamination method, coating method (spin coating method, casting method, dip coating method, etc.), inkjet method, printing method , LB method, transfer method and the like are used, preferably resistance heating vapor deposition and coating method.

  The material of the hole injection layer and the hole transport layer may be any one having a function of injecting holes from the anode, a function of transporting holes, or a function of blocking electrons injected from the cathode. Good. Specific examples include carbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, styrylanthracene derivatives. , Fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidin compounds, porphyrin compounds, polysilane compounds, poly (N-vinylcarbazole) derivatives, aniline compounds Examples include copolymers, thiophene oligomers, conductive polymer oligomers such as polythiophene, organic silane derivatives, carbon films, and the compounds of the present invention. The film thicknesses of the hole injection layer and the hole transport layer are not particularly limited, but are usually preferably in the range of 1 nm to 5 μm, more preferably 5 nm to 1 μm, and still more preferably 10 nm to 500 nm. . The hole injection layer and the hole transport layer may have a single layer structure composed of one or more of the materials described above, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.

  As a method for forming the hole injection layer and the hole transport layer, a vacuum deposition method, an LB method, a method in which the hole injection / transport material is dissolved or dispersed in a solvent (a spin coating method, a casting method, a dip coating method). Etc.), an inkjet method, a printing method, and a transfer method are used. In the case of the coating method, it can be dissolved or dispersed together with the resin component. Examples of the resin component include polyvinyl chloride, polycarbonate, polystyrene, polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, and poly (N -Vinyl carbazole), hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate, ABS resin, polyurethane, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, and the like.

  Although the film thickness of an electron injection layer and an electron carrying layer is not specifically limited, The thing of the range of 1 nm-5 micrometers is preferable normally, More preferably, it is 5 nm-1 micrometer, More preferably, it is 10 nm-500 nm. The electron injection layer and the electron transport layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.

  As a method for forming the electron injection layer and the electron transport layer, a vacuum deposition method, an LB method, a method in which the electron injection transport material is dissolved or dispersed in a solvent (a spin coating method, a casting method, a dip coating method, etc.), An ink jet method, a printing method, a transfer method, or the like is used. In the case of the coating method, it can be dissolved or dispersed together with the resin component. As the resin component, for example, those exemplified in the case of the hole injection transport layer can be applied.

As a material for the protective layer, any material may be used as long as it has a function of preventing substances that promote device deterioration such as moisture and oxygen from entering the device. Specific examples thereof include metals such as In, Sn, Pb, Au, Cu, Ag, Al, Ti, and Ni, MgO, SiO, SiO ₂ , Al ₂ O ₃ , GeO, NiO, CaO, BaO, and Fe ₂ O. ₃ , metal oxides such as Y ₂ O ₃ and TiO ₂ , metal fluorides such as MgF ₂ , LiF, AlF ₃ and CaF ₂ , SiO _x N _y , polyethylene, polypropylene, polymethyl methacrylate, polyimide, polyurea, polytetra Copolymers obtained by copolymerizing fluoroethylene, polychlorotrifluoroethylene, polydichlorodifluoroethylene, a copolymer of chlorotrifluoroethylene and dichlorodifluoroethylene, and a monomer mixture containing tetrafluoroethylene and at least one comonomer. Polymer, fluorine-containing copolymer having a cyclic structure in the copolymer main chain, water absorption of 1% or less The above water-absorbing substances, moisture-proof substances having a water absorption rate of 0.1% or less, and the like are mentioned.

  There is no particular limitation on the method for forming the protective layer. For example, vacuum deposition, sputtering, reactive sputtering, MBE (molecular beam epitaxy), cluster ion beam, ion plating, plasma polymerization (high frequency excitation ions) Plating method), plasma CVD method, laser CVD method, thermal CVD method, gas source CVD method, coating method, printing method, and transfer method can be applied.

  The organic electroluminescent element of the present invention can be suitably used in the fields of display elements, displays, backlights, electrophotography, illumination light sources, recording light sources, exposure light sources, reading light sources, signs, signboards, interiors, optical communications, and the like.

  Examples of the present invention will be described below, but the embodiments of the present invention are not limited thereto.

Comparative Example The cleaned ITO substrate was put into a vapor deposition apparatus, copper phthalocyanine was deposited to 10 nm, and α-NPD was deposited to 40 nm thereon to form a hole transport layer. On top of this, H-2 as the first host, Alq as the second host, and D-1 as the light emitting material are 0.4 nm / sec, 0.1 nm / sec and 0.01 nm / sec, respectively, and the film thickness is 50 nm. The light emitting layer was formed by co-evaporation so that On top of that, Alq was deposited by 30 nm. A patterned mask (a mask with a light emission area of 2 mm x 2 mm) is placed on the organic thin film. After depositing 5 nm of lithium fluoride in the vapor deposition system, 500 nm of aluminum is vapor deposited, and then without adding a desiccant. Was sealed to produce an EL element (element No. 101). The light emitting material was changed to D-2 by the same operation as described above, and the EL element was produced by setting the vapor deposition rate of the light emitting material to 0.02 nm / second (element No-102).

Example After depositing NPD by the same operation as described above, the first host, the second host and the light emitting material described in Table 1 were respectively 0.4 nm / second, 0.1 nm / second, and 0.01 nm / second: D- The light emitting layer was formed by co-evaporation at 1 (or 0.02 nm / second: D-2) so that the film thickness was 50 nm. On top of that, after depositing an electron transport material shown in Table 1 to 30 nm, depositing lithium fluoride in the same manner as above, depositing aluminum, sealing without adding a desiccant, and making EL elements (elements 103 to 106). ).

Evaluation Using a source measure unit 2400 made by Toyo Technica on an organic thin film, a constant DC current is applied to the EL element to cause the comparative example and the element of the present invention to emit light, and the brightness is measured by Topcon's luminance meter BM-8. The wavelength was measured using a spectrum analyzer PMA-11 manufactured by Hamamatsu Photonics, and the luminous efficiency was determined. Next, storage durability was evaluated. First, after measuring the drive current at the time of light emission with an emission luminance of 1000 cd / m ² , the device was stored for 96 hours under heating at 80 ° C. Then, it was driven with the same current as before heating, and the luminance maintenance rate before and after heating was measured. The results are shown in Table 1 below.

  Compared with the element 101 and the element 102 containing Alq as the second host, the elements of the present invention (elements 103 to 106) using the heterocyclic host of the present invention as the second host have good luminous efficiency and luminance maintenance rate. Show. Furthermore, the element using the heterocyclic electron transport material of the present invention instead of Alq as the electron transport material exhibits further excellent luminous efficiency and luminance maintenance rate. Also. The light emitting device of the present invention is also excellent in durability. As described above, the element of the present invention has an excellent luminous efficiency and an element excellent in durability, particularly storage durability.

Claims (23)

An organic electroluminescent device having at least one organic layer including a light emitting layer between a pair of electrodes, the light emitting layer containing at least two kinds of host materials and at least one kind of fluorescent light emitting materials, at least one material is organic electroluminescent device, characterized in that it is a metal complex represented by the following formula (IV).
Formula (IV)

( Wherein X ²¹ and X ²² represent a carbon atom or a nitrogen atom. Y ² represents a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom. Z ² represents a nitrogen atom, an oxygen atom, a sulfur atom or Represents a phosphorus atom, provided that the combination of (Y ² , Z ² ) is not (N, O) or (O, N) Q ²¹ is a 5-membered ring, 6-membered ring or 7-membered ring Q ²² represents an atomic group necessary for forming a 5-membered ring, a 6-membered ring, or a 7-membered ring, M ² represents a metal ion, and n ² represents an integer of 1 or more. L ² represents a ligand, and m ² represents an integer of 0 or more. The bond type between the atoms may be any of a single bond, a double bond, a triple bond, and a coordination bond.) Q forming a 5-, 6-, or 7-membered ring ^{twenty one} , Q ^{twenty two} Each form an aromatic ring, Y ² Is a nitrogen atom or an oxygen atom, and Z ² Is a nitrogen atom, an oxygen atom, or a sulfur atom, The organic electroluminescent element of Claim 1 characterized by the above-mentioned. M ² Is Al ³⁺ , Zn ²⁺ , Be ²⁺ , Mg ²⁺ Or Cu ²⁺ The organic electroluminescent element according to claim 1 or 2, wherein M ² Is Al ³⁺ The organic electroluminescent element according to claim 3, wherein n ² Is 1-4 and m ² 5 is 0, The organic electroluminescent element according to claim 1.   n ² The organic electroluminescent element according to claim 5, wherein is 3.   Q ^{twenty one} The ring formed by is a pyridine ring, pyrimidine ring, pyrazine ring, quinoline ring, quinoxaline ring, isoquinoline ring, phthalazine ring, pyrrole ring, indole ring, imidazole ring, benzimidazole ring, oxazole ring, benzoxazole ring, thiazole ring Benzothiazole ring, triazole ring, benzotriazole ring or imidazopyridine ring, ^{twenty two} The organic electroluminescent device according to claim 1, wherein the ring formed by is a benzene ring, a naphthalene ring, a pyridine ring, a thiophene ring, or a pyrazine ring.   Q ^{twenty one} The ring formed by is an imidazopyridine ring, ^{twenty two} The organic electroluminescent element according to claim 1, wherein the ring formed by is a benzene ring. An organic electroluminescent device having at least one organic layer including a light emitting layer between a pair of electrodes, the light emitting layer containing at least two kinds of host materials and at least one kind of fluorescent light emitting materials, at least one material is organic electroluminescent device, characterized in that it is a metal complex represented by the following formula (III).
Formula (III)

(In the formula (III), X ¹¹ and X ¹² each represent a carbon atom or a nitrogen atom. The bond between X ¹¹ and the nitrogen atom and between X ¹² and the carbon atom may be a single bond or a double bond. Z ¹¹ and Z ¹² each represent an atomic group necessary for forming a 5-membered ring or a 6-membered ring, M ¹ represents a metal ion, n ¹ represents an integer of 1 or more, and L ^H represents a ligand. M ¹ represents an integer of 0 or more.)   Z ¹¹ The ring formed by is a pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, quinoline ring, quinoxaline ring, isoquinoline ring, cinnoline ring, phthalazine ring, quinazoline ring, triazine ring, acridine ring, phenazine ring, phenanthroline ring, naphthyridine Ring, phenanthridine ring, pyrrole ring, indole ring, pyrazole ring, imidazole ring, benzimidazole ring, oxazole ring, benzoxazole ring, thiazole ring, benzothiazole ring, selenazole ring, benzoselenazole ring, indazole ring, isothiazole Ring, isoxazole ring, triazole ring, benzotriazole ring, tetrazole ring, oxadiazole ring, thiadiazole ring, thiatriazole ring, azaindole ring, imidazopyridine ring, purine ring or imidazo A down ring, wherein Z ¹² The organic electroluminescent element according to claim 9, wherein the ring formed by is an aromatic ring.   Z ¹¹ The ring formed by pyridine ring, pyrimidine ring, pyrazine ring, quinoline ring, quinoxaline ring, isoquinoline ring, phthalazine ring, pyrrole ring, indole ring, imidazole ring, benzimidazole ring, oxazole ring, benzoxazole ring, thiazole ring, A benzothiazole ring, a triazole ring, a benzotriazole ring or an imidazopyridine ring, ¹² The organic electroluminescent device according to claim 9 or 10, wherein the ring formed by is benzene, naphthalene, anthracene, pyridine, thiophene, pyrazine or pyrimidine. M ¹ Is Al ³⁺ , Zn ²⁺ , Be ²⁺ , Mg ²⁺ Or Cu ²⁺ The organic electroluminescent element according to any one of claims 9 to 11, wherein M ¹ Is Al ³⁺ The organic electroluminescent element according to claim 12, wherein n ¹ Is 1-4 and m ¹ The organic electroluminescent element according to claim 9, wherein is 0 or 1.   n ¹ Is 2 or 3, m ¹ The organic electroluminescent element according to claim 14, wherein is zero.   The at least two kinds of host materials contained in the light emitting layer are any one of the metal complex represented by the formula (III) or (IV), a condensed aromatic carbocyclic compound, a polyarylene compound, and a triarylamine. The organic electroluminescent element according to claim 1, wherein the organic electroluminescent element is a combination of two.   The at least two kinds of host materials are a combination of the metal complex represented by the formula (III) or (IV) and any one of a condensed aromatic carbocyclic compound and a polyarylene compound. The organic electroluminescent element according to claim 16.   The fluorescent light emitting material is a condensed aromatic compound which may have a substituent, and the substituent is an aryl group, a heteroaromatic ring group, a diarylamino group or an alkyl group. Organic electroluminescent element of any one of these.   The organic electroluminescent device according to claim 18, wherein the condensed aromatic compound is a condensed aromatic hydrocarbon compound. Further comprising an electron transport layer, the electron transporting layer of the organic electroluminescent device according to any one of claims 1 to 19, characterized by containing a compound represented by the formula (E1).

(In the formula, R _E represents a hydrogen atom or a substituent. X _E represents —O—, —S—, ═N— or ═N—Ra, where Ra represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group, or a hetero group. Q _E represents a group of atoms necessary to form a heterocyclic ring by combining with N and X _E. ) The organic electroluminescent element according to claim 20, wherein the electron transport layer contains a compound represented by the formula (E-II).

(Wherein, X _E is -O -, - S -., = N- or = N-Ra (Ra is hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group) are expressed .Z _E Represents an atomic group necessary for forming an aromatic ring, B represents a linking group, and m represents an integer of 2 or more. The organic electroluminescent element according to claim 20, wherein the electron transport layer contains a compound represented by the formula (E-III).

(In the formula, R _E31 , R _E32 and R _E33 represent a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group.) The organic electroluminescent element according to claim 20, wherein the electron transport layer contains a compound represented by the formula (E-IV).
Formula (E-IV)

(In the formula, R ^A1 , R ^A2 and R ^A3 each represent a hydrogen atom or an aliphatic hydrocarbon group. R ^A4 , R ^A5 and R ^A6 each represent a substituent. N ^A1 , n ^A2 and n ^A3. Each represents an integer of 0 to 3. X ^A1 , X ^A2, and X ^A3 each represent a nitrogen atom or C—R ^X (R ^X represents a hydrogen atom or a substituent) Y ^A1 , Y ^A2 And Y ^A3 each represents a nitrogen atom or C—R ^YX (R ^YX represents a hydrogen atom or a substituent).