Light-emitting material for organic electroluminescent device, organic electroluminescent device using same, and material for organic electroluminescent device

Abstract

Disclosed is a light-emitting material for organic electroluminescent (EL) devices which is composed of an asymmetric anthracene derivative of a specific structure. Also disclosed are a material for organic EL devices and an organic EL device wherein an organic thin film layer composed of one or more layers including at least a light-emitting layer is interposed between a cathode and an anode. At least one layer composed of the organic thin film layer contains the material for organic EL devices by itself or as a component of a mixture. Consequently, the organic EL device has a high efficiency and a long life. Also disclosed are a light-emitting material for organic EL devices and material for organic devices which enable to realize such an organic EL device.

Claims

1. A light emitting material for an organic electroluminescent device comprising an asymmetric anthracene derivative represented by formula (1): ##STR00017## wherein A.sup.1 represents 2-naphthyl group; A.sup.2 represents 2-naphthyl group, 1-pyrenyl group, 2-pyrenyl group, or 4-pyrenyl group; Ar.sup.1 and Ar.sup.2 each independently represent a hydrogen atom or a substituted or unsubstituted aromatic hydrocarbon ring group having ring carbon atoms of 6 to 50; R.sup.1 to R.sup.8 each independently represent a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon ring group having ring carbon atoms of 6 to 50, a substituted or unsubstituted aromatic hetero ring group having ring atoms of 5 to 50, a substituted or unsubstituted alkyl group having carbon atoms of 1 to 50, a substituted or unsubstituted cycloalkyl group having carbon atoms of 3 to 50, a substituted or unsubstituted alkoxy group having carbon atoms of 1 to 50, a substituted or unsubstituted aralkyl group having carbon atoms of 6 to 50, a substituted or unsubstituted aryloxy group having carbon atoms of 5 to 50, a substituted or unsubstituted arylthio group having carbon atoms of 5 to 50, a substituted or unsubstituted alkoxycarbonyl group having carbon atoms of 1 to 50, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group; R.sup.9 to R.sup.10 each independently represent a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon ring group having ring carbon atoms of 6 to 50, a substituted or unsubstituted alkyl group having carbon atoms of 1 to 50, a substituted or unsubstituted cycloalkyl group having carbon atoms of 3 to 50, a substituted or unsubstituted alkoxy group having carbon atoms of 1 to 50, a substituted or unsubstituted aralkyl group having carbon atoms of 6 to 50, a substituted or unsubstituted aryloxy group having carbon atoms of 5 to 50, a substituted or unsubstituted arylthio group having carbon atoms of 5 to 50, a substituted or unsubstituted alkoxycarbonyl group having carbon atoms of 1 to 50, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group, and none of R.sup.9 and R.sup.10 is alkenyl group; Ar.sup.1, Ar.sup.2, R.sup.9 and R.sup.10 each may be a plural number, and two neighboring groups thereof may form a saturated or unsaturated ring structure; the substituent groups at 9th and 10th positions of the anthracene at the core in formula (1) are different from each other; and a substituent for Ar.sup.1, Ar.sup.2, and R.sup.9 and R.sup.10 is a halogen atom, a hydroxyl group, a nitro group, a cyano group, an alkyl group, an aryl group, a cycloalkyl group, an alkoxy group, an aralkyl group, an aryloxy group, an arylthio group, an alkoxycarbonyl group, and a carboxyl group.

2. The light emitting material for the organic electroluminescent device according to claim 1, wherein Ar.sup.1 and Ar.sup.2 each independently represent any one of a hydrogen atom, 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, p-t-butylphenyl group, p-(2-phenylpropyl)phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylyl group, and 4″-t-butyl-p-terphenyl-4-yl group.

3. The light emitting material for the organic electroluminescent device according to claim 1, wherein Ar.sup.1 and Ar.sup.2 each independently represent any one of a hydrogen atom 1-naphthyl group, 2-naphthyl group, and 9-phenanthryl group.

4. The light emitting material for the organic electroluminescent device according to claim 1, wherein the asymmetric anthracene derivative comprises a naphtalene-1-yl group having a substituent at 4th position thereof and/or a substituted or unsubstituted condensed aromatic hydrocarbon ring group having ring carbon atoms of 12 to 20.

5. An organic electroluminescent device comprising at least one organic thin film layer which comprises a light emitting layer and which is interposed between a pair of electrode consisting of an anode and a cathode, wherein the light emitting layer comprises the light emitting material for the organic electroluminescent device according to claim 1 singly or as a component of a mixture thereof.

6. The organic electroluminescent device according to claim 5, wherein the light emitting layer comprises additionally an arylamine compound.

7. The organic electroluminescent device according to claim 5, wherein the light emitting layer comprises additionally a styrylamine compound.

8. A material for an organic electroluminescence device comprising an asymmetric anthracene derivative represented by formula (1′): ##STR00018## wherein, A.sup.1′ and A.sup.2′ each independently represent a substituted or unsubstituted condensed aromatic hydrocarbon ring group having ring carbon atoms of 10 to 20, and at least one of the groups A.sup.1′ and A.sup.2′ represents a naphtalene-1-yl group having a substituent at 4th position thereof or a substituted or unsubstituted condensed aromatic hydrocarbon ring group having ring carbon atoms of 12 to 20; Ar.sup.1 and Ar.sup.2 each independently represent a hydrogen atom or a substituted or unsubstituted aromatic hydrocarbon ring having ring carbon atoms of 6 to 50; R.sup.1 to R.sup.8 each independently represent a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon ring group having ring carbon atoms of 6 to 50, a substituted or unsubstituted aromatic hetero ring group having ring atoms of 5 to 50, a substituted or unsubstituted alkyl group having carbon atoms of 1 to 50, a substituted or unsubstituted cycloalkyl group having carbon atoms of 3 to 50, a substituted or unsubstituted alkoxy group having carbon atoms of 1 to 50, a substituted or unsubstituted aralkyl group having carbon atoms of 6 to 50, a substituted or unsubstituted aryloxy group having carbon atoms of 5 to 50, a substituted or unsubstituted arylthio group having carbon atoms of 5 to 50, a substituted or unsubstituted alkoxycarbonyl group having carbon atoms of 1 to 50, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group; R.sup.9 to R.sup.10 each independently represent a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon ring group having ring carbon atoms of 6 to 50, a substituted or unsubstituted alkyl group having carbon atoms of 1 to 50, a substituted or unsubstituted cycloalkyl group having carbon atoms of 3 to 50, a substituted or unsubstituted alkoxy group having carbon atoms of 1 to 50, a substituted or unsubstituted aralkyl group having carbon atoms of 6 to 50, a substituted or unsubstituted aryloxy group having carbon atoms of 5 to 50, a substituted or unsubstituted arylthio group having carbon atoms of 5 to 50, a substituted or unsubstituted alkoxycarbonyl group having carbon atoms of 1 to 50, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group, and none of R.sup.9 and R.sup.10 is alkenyl group; Ar.sup.1, Ar.sup.2, R.sup.9 and R.sup.10 each may be a plural number, and two neighboring groups thereof may form a saturated or unsaturated ring structure; and the substituent groups at 9th and 10th positions of the anthracene at the core in formula (1′) are different from each other.

9. The light emitting material for the organic electroluminescent device according to claim 1, wherein each of Ar.sup.1, R.sup.9 and R.sup.10 is a hydrogen atom, and Ar.sup.2 is a substituted or unsubstituted aromatic hydrocarbon ring group having ring carbon atoms of 6 to 50.

10. The light emitting material for the organic electroluminescent device according to claim 1, wherein each of R.sup.9 and R.sup.10 is a hydrogen atom, Ar.sup.1 is different from Ar.sup.2, and each of Ar.sup.1and Ar.sup.2 is a substituted or unsubstituted aromatic hydrocarbon ring group having ring carbon atoms of 6 to 50.

11. The light emitting material for the organic electroluminescent device according to claim 1, wherein two neighboring R.sup.9′s form a saturated or unsaturated ring structure, Ar.sup.1 is a hydrogen atom, R.sup.10 is a hydrogen atom, Ar.sup.2 is a substituted or unsubstituted aromatic hydrocarbon ring group having ring carbon atoms of 6 to 50.

12. The organic electroluminescent device according to claim 5, wherein the light emitting material for the organic electroluminescent device is a host material.

13. A light emitting material for an organic electroluminescent device comprising an asymmetric anthracene derivative represented by formula (1): ##STR00019## wherein A.sup.1 represents 1anthryl group, 2-anthryl group, or 9-anthryl group; A.sup.2 represents 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2naphthacenyl group, or 9-naphthacenyl group; Ar.sup.1 represents a hydrogen atom or a substituted or unsubstituted aromatic hydrocarbon ring group, wherein the aromatic hydrocarbon ring group is selected from the group consisting of phenyl group, 1-naphthyl group, 1-anthryl group, 2anthryl group, 9-anthryl group, 1phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-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-2yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-totyl group, m-tolyl group, p-tolyl group, p-t-butylphenyl group, p-(2-phenylpropyl) phenyl group, 3methyl-2-naphythyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylyl group, and 4″-t-butyl-p-terphenyl-4-yl group; Ar.sup.2 represents a hydrogen atom or a substituted or unsubstituted aromatic hydrocarbon ring group having ring carbon atoms of 6 to 50; R.sup.1 to R.sup.8 each independently represent a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon ring group having ring carbon atoms of 6 to 50, a substituted or unsubstituted aromatic hereto ring group having ring atoms of 5 to 50, a substituted or unsubstituted alkyl group having carbon atoms of 1 to 50, a substituted or unsubstituted cycloalkyl group having carbon atoms of 3 to 50, a substituted or unsubstituted alkoxy group having carbon atoms of 1 to 50, a substituted or unsubstituted aralkyl group having carbon atoms of 6 to 50, a substituted or unsubstituted aryloxy group having carbon atoms of 5 to 50, a substituted or unsubstituted arylthio group having carbon atoms of 5 to 50, a substituted or unsubstituted alkoxycarbonyl group having carbon atoms of 1 to 50, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group; R.sup.9 represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon ring group wherein the aromatic hydrocarbon ring group is selected from the group consisting of phenyl group, 1-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-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, p-t-butylphenyl group, p-(2-phenylpropyl) phenyl group, 3methyl-2-naphythyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′methylbiphenylyl group, and 4″-t-butyl-p-terphenyl-4-yl group; a substituted or unsubstituted alkyl group having carbon atoms of 1 to 50, a substituted or unsubstituted cycloalkyl group having carbon atoms of 3 to 50, a substituted or unsubstituted alkoxy group having carbon atoms of 1 to 50, a substituted or unsubstituted aralkyl group having carbon atoms of 6 to 50, a substituted or unsubstituted aryloxy group having carbon atoms of 5 to 50, a substituted or unsubstituted arylthio group having carbon atoms of 5 to 50, a substituted or unsubstituted alkoxycarbonyl group having carbon atoms of 1 to 50, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group; R.sup.10 represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon ring group having ring carbon atoms of 6 to 50; a substituted or unsubstituted alkyl group having ring carbon atoms of 1 to 50, a substituted or unsubstituted cycloalkyl group having carbon atoms of 3 to 50, a substituted or unsubstituted cycloakyl group having carbon atoms of 3 to 50, a substituted or unsubstituted alkoxyl group having carbon atoms of 1 to 50a substituted or unsubstituted aralkyl group having carbon atoms of 6 to 50, a substituted or unsubstituted aryloxy group having carbon atoms of 5 to 50, a substituted or unsubstituted arylthio group having carbon atoms of 5 to 50, a substituted or unsubstituted alkoxycarbonyl group having carbon atoms of 1 to 50, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group; and none of R.sup.9 and R.sup.10 is alkenyl group; Ar.sup.1, Ar.sup.2, R.sup.9 and R.sup.10 each may be a plural number, and two neighboring groups thereof may form a aturated or unsaturated ring structure; the substituent groups at 9th and 10th positions of the anthracene at the core in formula (1) are different from each other; and a substituent for Ar.sup.1, Ar.sup.2, R.sup.9 and R.sup.10 is a halogen atom, a hydroxyl group, a nitro group, a cyano group, an alkyl group, an aryl group, a cycloalkyl group, an alkoxy group, an aralkyl group, an aryloxy group, an arylthio group, an alkoxycarbonyl group, and a carboxyl group.

14. The emitting material for the organic electroluminescent device according to claim 13, wherein: A.sup.1 represents 1-anthryl group and A.sup.2 represents 1-naphthyl group, 2-naphthyl 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, or 4-pyrenyl group; A.sup.1 represents 2-anthryl group and A.sup.2 represents 1-naphthyl group, 2-naphthyl group, 1-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, or 4-pyrenyl group; or A.sup.1 represents 9-anthryl group and A.sup.2 represents 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-naphthacenyl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, or 4-pyrenyl group.

15. The light emitting material for the organic electroluminescent device according to claim 13, wherein Ar.sup.1 Ar.sup.2 each independently represent any one of a hydrogen atom, 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-4yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-totyl group, m-tolyl group, p-tolyl group, p-t-butylphenyl group, p-(2-phenylpropyl) phenyl group, 3-methyl-2-naphythyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylyl group, and 4″-t-butyl-p-terphenyl-4-yl group.

16. The light emitting material for the organic electroluminescent device according to claim 13, wherein Ar.sup.1 Ar.sup.2 each independently represent any one of a hydrogen atom, 1-naphtyl group, 2-naphtyl group, and 9-phenanthryl group.

17. The light emitting material for the organic electroluminescent device according to claim 13, wherein the asymmetric anthracene derivative comprises a naphthalene-1-yl group having a substituent at 4th position thereof and/or a substituted or unsubstituted condensed aromatic hydrocarbon ring group having ring carbon atoms of 12 to 20.

18. An organic electroluminescent device comprising at least one organic thin film layer which comprises a light emitting layer and which is interposed between a pair of electrode consisting of an anode and a cathode, wherein the light emitting layer comprises the light emitting material for the organic electroluminescent device according to claim 13 singly or as a component of a mixture thereof.

19. The organic electroluminescent device according to claim 18, wherein the light emitting material for the organic electroluminescent device is a host material.

20. The organic electroluminescent device according to claim 18, wherein the light emitting layer comprises additionally an arylamine compound.

21. The organic electroluminescent device according to claim 18, wherein the light emitting layer comprises additionally a styrylamine compound.

22. A light emitting material for an organic electroluminescent device comprising an asymmetric anthracene derivative represented by formula (1): ##STR00020## wherein A.sup.1 represents 1-pyrenyl group, 2-pyrenyl group, or 4-pyrenyl group; A.sup.2 represents 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-pyrenyl group, 2-pyrenyl group, or 4-pyrenyl group; Ar.sup.1represents a hydrogen atom or a substituted or unsubstituted aromatic hydrocarbon ring group having ring carbon atoms of 6 to 50; Ar.sup.2 represents a hydrogen atom or a substituted or unsubstituted aromatic hydrocarbon ring group, wherein the aromatic hydrocarbon ring group is selected from the group consisting of 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, 2-biphenyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, p-t-butylphenyl group, p-(2-phenylpropyl) phenyl group, 3-methyl-2-naphythyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylyl group, and 4″-t-butyl-p-terphenyl-4-yl group; R.sup.1 R.sup.8 each independently represent a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon ring group having ring carbon atoms of 6 to 50, a substituted or unsubstituted aromatic hereto ring group having ring atoms of 5 to 50, a substituted or unsubstituted alkyl group having carbon atoms of 1 to 50, a substituted or unsubstituted cycloalkyl group having carbon atoms of 3 to 50, a substituted or unsubstituted alkoxy group having carbon atoms of 1 to 50, a substituted or unsubstituted aralkyl group having carbon atoms of 6 to 50, a substituted or unsubstituted aryloxy group having carbon atoms of 5 to 50, a substituted or unsubstituted arylthio group having carbon atoms of 5 to 50, a substituted or unsubstituted alkoxycarbonyl group having carbon atoms of 1 to 50, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group; R.sup.9 represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon ring group having ring carbon atoms of 6 to 50, a substituted or unsubstituted alkyl group having carbon atoms of 1 to 50, a substituted or unsubstituted cycloalkyl group having carbon atoms of 3 to 50, a substituted or unsubstituted alkoxyl group having carbon atoms of 1 to 50, a substituted or unsubstituted aralkyl group having carbon atoms of 6 to 50, a substituted or unsubstituted aryloxy group having carbon atoms of 5 to 50, a substituted or unsubstituted arylthio group having carbon atoms of 5 to 50, a substituted or unsubstituted alkoxycarbonyl group having carbon atoms of 1 to 50, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group; R.sup.10 represents a hydrogen atom or a substituted or unsubstituted aromatic hydrocarbon ring group wherein the aromatic hydrocarbon ring group is selected from the group consisting of 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, 2-biphenyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, p-t-butylphenyl group, p-(2-phenylpropyl) phenyl group, 3methyl-2-naphythyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylyl group, and 4″-t-butyl-p-terphenyl-4-yl group; a substituted or unsubstituted alkyl group having carbon atoms of 1 to 50, a substituted or unsubstituted cycloalkyl group having carbon atoms of 3 to 50, a substituted or unsubstituted alkoxy group having carbon atoms of 1 to 50, a substituted or unsubstituted aralkyl group having carbon atoms of 6 to 50, a substituted or unsubstituted aryloxy group having carbon atoms of 5 to 50, a substituted or unsubstituted arylthio group having carbon atoms of 5 to 50, a substituted or unsubstituted alkoxycarbonyl group having carbon atoms of 1 to 50, a substituted or unsubstituted silyl group a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group; and none of R.sup.9 and R.sup.10 is alkenyl group; Ar.sup.1,Ar.sup.2,R.sup.9 and R.sup.10 each may be a plural number, and two neighboring groups thereof may form a saturated or unsaturated ring structure; the substituent groups at 9th and 10th positions of the anthracene at the core in formula (1) are different from each other; and a substituent for Ar.sup.1,Ar.sup.2,R.sup.9 and R.sup.10 is a halogen atom, a hydroxyl group, a nitro group, a cyano group, an alkyl group, an aryl group, a cycloalkyl group, an alkoxy group, an aralkyl group, an aryloxy group, an arylthio group, an alkoxycarbonyl group, and a carboxyl group.

23. The light emitting material for an organic electroluminescent device according to claim 22, wherein: A.sup.1 represents 1-pyrenyl group and A.sup.2 represents 1-anthryl group, 2-anthryl group, 9-anthryl group, 2-pyenyl group, or 4-pyrenyl group; A.sup.1 represents 2-pyrenyl group and A.sup.2 represents 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-pyrenyl group, or 4-pyrenyl group; or A.sup.1 represents 4-pyrenyl group and A.sup.2 represents 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-pyrenyl group, or 2-pyrenyl group.

24. The light emitting material for an organic electroluminescent device according to claim 22, wherein Ar.sup.1 and Ar.sup.2 each independently represent any one of a hydrogen atom, 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, p-t-butylphenyl group, p-(2-phenylpropyl) phenyl group, 3-methyl-2-naphythyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylyl group, and 4″-t-butyl-p-terphenyl-4-yl group.

25. The light emitting material for the organic electroluminescent device according to claim 22, wherein Ar.sup.1 and Ar.sup.2 each independently represent any one of a hydrogen atom, 1-naphtyl group, 2-naphtyl group, and 9-phenanthryl group.

26. The light emitting material for the organic electroluminescent device according to claim 22, wherein the asymmetric anthracene derivative comprises a naphthalene-1-yl group having a substituent at 4th position thereof and/or a substituted or unsubstituted condensed aromatic hydrocarbon ring group having ring carbon atoms of 12 to 20.

27. An organic electroluminescent device comprising at least one organic thin film layer which comprises a light emitting layer and which is interposed between a pair of electrode consisting of an anode and a cathode, wherein the light emitting layer comprises the light emitting material for the organic electroluminescent device according to claim 18 singly or as a component of a mixture thereof.

28. The organic electroluminescent device according to claim 27, wherein the light emitting material for the organic electroluminescent device is a host material.

29. The organic electroluminescent device according to claim 27, wherein the light emitting layer comprises additionally an arylamine compound.

30. The organic electroluminescent device according to claim 27, wherein the light emitting layer comprises additionally a styrylamine compound.

Description

EXAMPLE

(1) This invention will be described in further detail with reference to Examples, which does not limit the scope of this invention.

Synthesis Example 1

Synthesis of 1-bromo-4-phenylnaphthalene

(2) 15 g of 1,4-dibromonaphthalene on the market, 7.7 g of phenylboronic acid and 1.8 g of tetrakis(triphenylphophine)palladium were mixed, followed by argon displacement. After adding 200 ml of toluene and 90 ml of 2M sodium carbonate aqueous solution thereto, it was refluxed on heating for 7 hours. After standing to cool, the organic layer was extracted by toluene, and then it was washed by water and saturated salt water. Subsequently the organic layer was dried by using sodium sulfate anhydride, and then the solvent was removed by distillation. The product was refined through a silica gel chromatography and then 8.9 g of 1-4-bromo-4-phenylnaphthalene of white crystal was obtained (Yield: 60%).

Synthesis Example 2

Synthesis of 1-bromo-4-(naphthelene-2-yl) naphthalene

(3) The procedure of Synthesis Example 1 was repeated except that 2-naphthalene boronic acid in place of phenylboronic acid was used, and then 7.5 g of 1-bromo-4-(naphthalene-2-0 naphthalene of white crystal was obtained (yield: 43%).

Synthesis Example 3

Synthesis of 2-(biphenyl-2-yl)-6-bromonaphthelene

(4) 15 g of 2,6-dibromonaphthalene on the market, 12.5 g of 2-biphenylboronic acid and 1.8 g of tetrakis(triphenylphophine)palladium were mixed, followed by argon displacement. After adding 250 ml of toluene and 90 ml of 2M sodium carbonate aqueous solution thereto, it was refluxed on heating for 7 hours. After standing to cool, the organic layer was extracted by toluene, and then it was washed by water and saturated salt water. Subsequently the organic layer was dried by using sodium sulfate anhydride, and then the solvent was removed by distillation. The product was refined through a silica gel chromatography and then 10.9 g of 2-(biphenyl-2-yl)-6-bromonaphthalene of white crystal was obtained (yield: 58%).

Synthesis Example 4

Synthesis of 9-(naphthalene-2-yl) anthracene

(5) 22.5 g of 9-bromoanthracene, 15.8 g of 2-naphthelene boronic acid and 2.0 g of tetrakis(triphenylphophine)palladium were mixed, followed by argon displacement. After adding 150 ml of toluene and 140 ml of 2M sodiumcarbonate aqueous solution thereto, it was refluxed on heating for 7 hours. After standing to cool, the crystal precipitated was filtrated it was washed by ethanol and toluene. The crystal obtained was recrystallized in toluene, followed by filtering and drying, and then 23.1 g of 9-(naphthalene-2-yl)anthracene was obtained (yield: 87%).

Synthesis Example 5

Synthesis of 9-bromo-10-(naphthalene-2-yl) anthracene

(6) 23.1 g of 9-(naphthalene-2-yl) anthracene was dispersed into 250 ml of DMF (dimethylformamide), and then 14.9 g of NBS (N-bromosuccinimide) in DMF solution (150 ml) was dropped therein. After stirred at room temperature for 7 hours, it was left over a night. 200 ml of water was added thereto, and then the crystal precipitated was separated by filtration. Subsequently it was washed by ethanol adequately, followed by drying, and 28.8 g of 9-bromo-10-(naphthalene-2-yl)anthracene of beige color crystal was obtained (Yield: 99%).

Synthesis Example 6

Synthesis of 10-(naphthalene-2-yl) anthracene-9-boronic acid

(7) Under argon atmosphere, 150 ml of dehydrated toluene and 150 ml of dehydrated ether were added to 28.8 g of 9-bromo-10-(naphthalene-2-yl)anthracene, and it was cooled to −63 deg C. 58 ml of 1.58M-n-butyllithium/hexane solution was dropped therein. Subsequently, it was stirred at −63 deg C. for 30 minutes, followed by heating up to −10 deg C. It was cooled to −70 deg C. again, and 23.4 ml of trimethyl boronic acid ester/dehydrated ether solution was dropped therein stepwise. After it was stirred at −70 deg C. for 2 hours, it was heated to room temperature steadily.

(8) After left over a night, it was acidified by 10% hydrochloric aqueous solution, followed by two time extractions by toluene. The organic layer obtained was washed by saturated salt water and then dried by using sodium sulfate anhydride. After the solvent was removed by distillation, the crystal obtained was recrystallized in toluene/hexane, followed by drying, and then 17 g of 10-(naphthalene-2-yl)anthracene-9-boronic acid was obtained (yield: 65%).

Synthesis Example 7

Synthesis of 9-phenanthrene boronic acid

(9) 80 ml of dehydrated toluene and 160 ml of dehydrated THF (tetrahydrofuran) were added to 38.6 g of 9-bromophenanthrene, and was cooled to −40 deg C. After 106 ml of 1.58M n-butyllithium hexane solution was dropped, it was stirred at −40 deg C. for 30 minutes and heated to −10 deg C. It was cooled to −70 deg C. again, and 50.0 ml of trimethyl boronic acid ester/dehydrated ether solution was dropped therein stepwise. Subsequently, it was stirred at −70 deg C. for 2 hours and then heated to room temperature steadily. After left over a night, it was acidified by 10% hydrochloric aqueous solution, followed by two time extractions by toluene. The organic layer obtained was washed by saturated salt water and then dried by using sodium sulfate anhydride. After the solvent was removed by distillation, the crystal obtained was recrystallized in toluene/hexane, followed by drying, and then 21.5 g of 9-phenanthrene boronic acid of pale brown color crystal was obtained (yield: 64%).

Synthesis Example 8

Synthesis of 10-(phenanthrene-9-yl) anthracene-9-boronic acid

(10) The procedures of Synthesis Example 4 to 6 were repeated, except that 9-phenanthrene boronic acid in place of 2-naphthalene boronic acid as the starting material was used, and then 10-(phenanthrene-9-yl)anthracene-9-boronic acid was obtained.

Production Example 1

Synthesis of AN7

(11) 5.0 g of 1-bromo-4-phenylnaphthalene, 7.38 g of 10-(naphthalene-2-yl) anthracene-9-boronic acid and 0.61 g of tetrakis(triphenylphophine)palladium were mixed, and followed by argon displacement. After adding 100 ml of DME (dimethoxyethane) and 30 ml of 2M sodium carbonate aqueous solution thereto, it was refluxed on heating for 10 hours.

(12) After standing to cool, the crystal precipitated was filtrated, it was washed by water, methanol and then toluene. The crystal obtained was recrystallized in toluene, followed by filtering and drying, and then 6.37 g of AN7 of cream color crystal was obtained (yield: 71%).

(13) The measurement result of the compound by FD-MS (Field Desorption Mass Spectrometry analysis) showed m/z (measured value)=506 to C.sub.40H.sub.26=506, therefore the objective compound (AN7) was confirmed.

Production Example 2

Synthesis of AN8

(14) The procedure of Production Example 1 was repeated except that 1-bromo-4-(naphthalene-2-yl)naphthalene in place of 1-bromo-4-phenylnaphthelene was used, and then AN8 of cream color crystal was obtained (yield: 63%).

(15) The measurement result of the compound by FD-MS showed m/z=556 to C.sub.44H.sub.28=556, therefore the objective compound (AN8) was confirmed.

Production Example 3

Synthesis of AN11

(16) The procedure of Production Example 1 was repeated, except that 2-bromonaphthalene and 10-(phenanthrene-9-yl)anthracene-9-boronic acid in place of 1-bromo-4-phenylnaphthelene and 10-(naphthalene-2-yl) anthracene-9-b oronic acid respectively were used, and then AN11 of cream color crystal was obtained (yield: 67%).

(17) The measurement result of the compound by FD-MS showed m/z=480 to C.sub.38H.sub.24=480.

Production Example 4

Synthesis of AN13

(18) The procedure of Production Example 1 was repeated except that 2-(biphenyl-2-yl)-6-bromonaphthalene and 10-(phenanthrene-9-yl)anthracene-9-boronic acid in place of 1-bromo-4-phenylnaphthelene and 10-(naphthalene-2-yl)anthracene-9-boronic acid respectively were used, and then AN13 of cream color crystal was obtained (yield: 67%).

(19) The measurement result of the compound by FD-MS showed m/z=632 to C.sub.50H.sub.32=632.

Production Example 5

Synthesis of AN44

(20) The procedure of Production Example 1 was repeated except that 1-bromonaphthelene in place of 1-bromo-4-naphthalene was used, and then AN44 of cream color crystal was obtained (yield: 69%).

(21) The measurement result of the compound by FD-MS showed m/z=430 to C.sub.34H.sub.22=430.

Production Example 6

Synthesis of AN6

(22) The procedure of Production Example 1 was repeated except that 2-bromo-6-phenylnaphthelene in place of 1-bromo-4-naphthalene was used, and then AN6 of cream color crystal was obtained (yield: 54%).

(23) The measurement result of the compound by FD-MS showed m/z=506 to C.sub.40H.sub.26=506.

Production Example 7

Synthesis of AN12

(24) The procedure of Production Example 1 was repeated except that 2-bromo-6-phenylnaphthelene and 10-(phenanthrene-9-yl)anthracene-9-boronic acid in place of 1-bromo-4-naphthalene and 10-(naphthalene-2-yl)anthracene-9-boronic acid respectively were used, and then AN13 of cream color crystal was obtained (yield; 60%).

(25) The measurement result of the compound by FD-MS showed m/z=556 to C.sub.44H.sub.28=556.

Example 1

Fabrication of an Organic EL Device

(26) A glass substrate (manufactured by GEOMATEC Company) of 25 mm×75 mm×1.1 mm thickness having an ITO transparent electrode was cleaned by application of ultrasonic wave in isopropyl alcohol for 5 minutes and then by exposure to ozone generated by ultraviolet light for 30 minutes. The cleaned glass substrate having an ITO transparent electrode line was fixed to a substrate holder of a vacuum deposition apparatus, and on the surface, where the ITO transparent electrode line was fixed, of the substrate, a film (hereinafter referred to as TPD232 film) having film thickness of 60 nm of the following N,N′-bis(N,N′-diphenyl-4-aminophenyl)-N,N-diphenyl-4,4′-diamino-1,1′-biphenyl was formed so as to cover the transparent electrode. The TPD232 film performs as a hole injecting layer.

(27) Subsequently, a layer having layer thickness of 20 nm of the following N,N,N′,N′-tetra(4-biphenyl)-diaminobiphenylene was formed (hereinafter referred to as TBDB layer). The layer performs as a hole transporting layer.

(28) Subsequently, a film having a film thickness of 40 nm of the aforementioned compound AN-7 was formed as a hole transporting layer by a vapor deposition. Concurrently, as a light emitting material, the following amino compound D1 containing a styryl group was deposited at the ratio by weight between AN7 and D1 of 40:3 by a vapor deposition. The film performs as a light emitting layer. On the film, a film having a Alq film thickness of 10 nm was formed. The film performs as an electron injecting layer.

(29) Further, a film (film thickness: 10 inn) of Alq:Li (the source of lithium: manufactured by SAES GETTERS Company) as an electron injecting layer or a cathode was formed by binary vapor deposition of Li as a reductive dopant and the following Alq. On the Alq:Li film, Al metal was deposited to form a metal cathode; therefore, an organic EL device was fabricated.

(30) The current efficiency of the organic EL device was measured, and also the half lifetime thereof was measured at an initial luminance of 1,000 nits. The results are shown in Table 1.

(31) ##STR00014##

Examples 2 to 7

Fabrication of Organic EL Devices

(32) Organic EL devices were fabricated similar to the example 1 except that the compounds described in Table 1 were used in place of the compound AN7, and then the current efficiencies and half lifetimes of the devices obtained were tested by the similar method to Example 1. The results are shown in Table 1.

Examples 8

Fabrication of Organic EL Device

(33) Organic EL device was fabricated similar to the example 1 except that the compound AN11 in place of the compound AN7 and the amine compound D2 in place of the amine compound D1 were used as the material for the light, emitting layer, and then the current efficiency and half lifetime of the device obtained were tested by the similar method to Example 1. The results are shown in Table 1.

(34) ##STR00015##

Comparative Example 1

(35) Organic EL devices were fabricated similar to the example 1 except that and was used in place of the compound AN7, and then the current efficiency and half lifetime of the device obtained was tested by the similar methods to Example 1. The results are shown in Table 1.

(36) ##STR00016##

(37) TABLE-US-00001 TABLE 1 Compound of Current Half Light-Emitting Efficiency Lifetime Layer (cd/A) (hours) Example 1 AN7/D1 10.9 4,200 Example 2 AN8/D1 1.3 4,200 Example 3 AN11/D1 11.0 5,800 Example 4 AN13/D1 10.8 3,700 Example 5 AN44/D1 10.0 3,000 Example 6 AN6/D1 10.1 3,300 Example 7 AN12/D1 10.8 4,900 Example 8 AN11/D2 10.3 3,700 Comparative an-/D1 9.0 2,200 Example 1

(38) As shown in Table 1, the organic EL devices of Examples 1 to 8 exhibited a higher current efficiency and a longer lifetime than those of the device of Comparative Example 1.