Material for organic electroluminescence device and electroluminescence device employing the same

Abstract

A material for organic electroluminescence devices comprising a compound having a specific structure and an organic electroluminescence device comprising an organic thin film layer which comprises one layer or a plurality of layers comprising at least a light emitting layer and disposed between a cathode and an anode, wherein at least one layer in the organic thin film layer comprises the material for organic electroluminescence devices, are provided. The material provides the organic electroluminescence device exhibiting a great efficiency of light emission, having no defect pixels, exhibiting excellent heat resistance and having a long life.

Claims

1. A material for organic electroluminescence devices, which comprises a compound represented by following general formula (3): ##STR00075## wherein.Iadd.: .Iaddend. R.sub.1 to R.sub.12 each independently represent hydrogen atom, a halogen atom, an alkyl group having 1 to 40 carbon atoms which may have substituents, a heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents, .Iadd.provided that the heterocyclic group is selected from the group consisting of 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 1-imidazolyl group, 2-imidazolyl group, 1-pyrazolyl group, 1-indolidinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group, 7-indolidinyl group, 8-indolidinyl group, 2-imidazopyridinyl group, 3-imidazopyridinyl group, 5-imidazopyridinyl group, 6-imidazopyridinyl group, 7-imidazopyridinyl group, 8-imidazopyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxanyl group, 5-quinoxanyl group, 6-quinoxanyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, β-carbolin-1-yl, β-carbolin-3-yl, 62 -carbolin-4-yl, β-carbolin-5-yl, β-carbolin-6-yl, β-carbolin-7-yl, β-carbolin-8-yl, β-carbolin-9-yl, 1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthfidinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1,7-phenanthrolin-2-yl group, 1,7-phenanthrolin-3-yl group, 1,7-phenanthrolin-4-yl group, 1,7-phenanthrolin-5-yl group, 1,7-phenanthrolin-6-yl group, 1,7-phenanthrolin-8-yl group, 1,7-phenanthrolin-9-yl group, 1,7-phenanthrolin-10-yl group, 1,8-phenanthrolin-2-yl group, 1,8-phenanthrolin-3-yl group, 1,8-phenanthrolin-4-yl group, 1,8-phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group, 1,8-phenanthrolin-9-yl group, 1,8-phenanthrolin-10-yl group, 1,9-phenanthrolin-2-yl group, 1,9-phenanthrolin-3-yl group, 1,9-phenanthrolin-4-yl group, 1,9-phenanthrolin-5-yl group, 1,9-phenanthrolin-6-yl group, 1,9-phenanthrolin-7-yl group, 1,9-phenanthrolin-8-yl group, 1,9-phenanthrolin-10-yl group, 1,10-phenanthrolin-2-yl group, 1,10-phenanthrolin-3-yl group, 1,10-phenanthrolin-4-yl group, 1,10-phenanthrolin-5-yl group, 2,9-phenanthrolin-1-yl group, 2,9-phenanthrolin-3-yl group, 2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group, 2,9-phenanthrolin-6-yl group, 2,9-phenanthrolin-7-yl group, 2,9-phenanthrolin-8-yl group, 2,9-phenanthrolin-10-yl group, 2,8-phenanthrolin-1-yl group, 2,8-phenanthrolin-3-yl group, 2,8-phenanthrolin-4-yl group, 2,8-phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group, 2,8-phenanthrolin-7-yl group, 2,8-phenanthrolin-9-yl group, 2,8-phenanthrolin-10-yl group, 2,7-phenanthrolin-1-yl group, 2,7-phenanthrolin-3-yl group, 2,7-phenanthrolin-4-yl group, 2,7-phenanthrolin-5-yl group, 2,7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group, 2,7-phenanthrolin-9-yl group, 2,7-phenanthrolin-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 10-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 10-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-furazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrol-3-yl group, 2-methylpyrrol-4-yl group, 2-methylpyrrol-5-yl group, 3-methylpyrrol-1-yl group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrol-5-yl group, 2-t-butylpyrrol-4-yl group, 3-(2-phenylpropyl)pyrrol-1-yl group, 2-methyl-1-indolyl group, 4-methyl-1-indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t-butyl-1-indolyl group, 4-t-butyl-1-indolyl group, 2-t-butyl-3-indolyl group, 4-t-butyl-3-indolyl group, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzo-thiophenyl group, 4-dibenzothiophenyl group, 1-dibenzosilolyl group, 2-dibenzosilolyl group, 3-dibenzosilolyl group, and 4-dibenzosilolyl group; .Iaddend..[.an alkoxyl group having 1 to 40 carbon atoms which may have substituents,.]. an aryl group having 6 to 60 carbon atoms which may have substituents, .Iadd.provided the aryl group is selected from the group consisting of phenyl group, 1-naphthyl group, 2-naphthyl group, phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl 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′-methylbiphenylyl group, 4″-t-butyl-p-terphenyl-4-yl group, o-cumenyl group, m-cumenyl group, p-cumenyl group, 2,3-xylyl group, 3,4-xylyl group, 2,5-xylyl group, and mesityl group; .Iaddend. an aryloxyl group having 6 to 60 carbon atoms which may have substituents, an aralkyl group having 7 to 60 carbon atoms which may have substituents, an alkenyl group having 2 to 40 carbon atoms which may have substituents, an alkylamino group having 1 to 40 carbon atoms which may have substituents, an aralkylamino group having 7 to 60 carbon atoms which may have substituents, an alkylsilyl group having 3 to 20 carbon atoms which may have substituents, an arylsilyl group having 8 to 40 carbon atoms which may have substituents, a ketoaryl group having 7 to 40 carbon atoms which may have substituents, a halogenated alkyl group having 1 to 40 carbon atoms which may have substituents, or cyano group, provided that each R.sub.8 to R.sub.12 do not represent an alkyl group having 1 to 40 carbon atoms which may have substituents, an aralkyl group having 7 to 60 carbon atoms which may have substituents, an alkenyl group having 2 to 40 carbon atoms which may have substituents, .[.or.]. a halogenated alkyl group having 1 to 40 carbon atoms which may have substituents.Iadd., or a halogen atom; provided that each R.sub.1 to R.sub.7 do not represent 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group; .Iaddend. .[.at least.]. one of R.sub.8 to R.sub.12 .[.representing hydrogen atom.]. .Iadd.represents the heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents, the aryl group having 6 to 60 carbon atoms which may have substituents, the aryloxyl group having 6 to 60 carbon atoms which may have substituents, the alkylamino group having 1 to 40 carbon atoms which may have substituents, the aralkylamino group having 7 to 60 carbon atoms which may have substituents, the alkylsilyl group having 3 to 20 carbon atoms which may have substituents, the arylsilyl group having 8 to 40 carbon atoms which may have substituents, the ketoaryl group having 7 to 40 carbon atoms which may have substituents, or cyano group; and the rest of R.sub.8 to R.sub.12 represent hydrogen atom, the heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents, the aryl group having 6 to 60 carbon atoms which may have substituents, the aryloxyl group having 6 to 60 carbon atoms which may have substituents, the alkylamino group having 1 to 40 carbon atoms which may have substituents, the aralkylamino group having 7 to 60 carbon atoms which may have substituents, the alkylsilyl group having 3 to 20 carbon atoms which may have substituents, the arylsilyl group having 8 to 40 carbon atoms which may have substituents, the ketoaryl group having 7 to 40 carbon atoms which may have substituents, or cyano group; .Iaddend. adjacent groups among groups represented by R.sub.1 to R.sub.4.[.,.]. .Iadd.and .Iaddend.among groups represented by R.sub.5 to R.sub.7 .[.and among groups represented by R.sub.8 to R.sub.12.]. may be bonded to each other to form a saturated or unsaturated cyclic structure.Iadd., and adjacent groups among groups represented by R.sub.8 to R.sub.12 are not bonded to each other, thereby failing to form a saturated or unsaturated cyclic structure.Iaddend.; and X represents sulfur atom, oxygen atom or a substituted silicon atom represented by SiRaRb, Ra and Rb each independently representing an alkyl group having 1 to 40 carbon atoms, provided that the compound excludes 1,3,5-tris(4-dibenzothiophenyl)benzene.

2. An organic electroluminescence device comprising a cathode, an anode and an organic thin film layer which comprises one layer or a plurality of layers comprising at least a light emitting layer and is disposed between the cathode and the anode, wherein at least one layer in the organic thin film layer comprises a material for organic electroluminescence devices described in claim 1.

3. An organic electroluminescence device according to claim 2, wherein the light emitting layer comprises a host material and a phosphorescent light emitting material, and the host material comprises a material for organic electroluminescence devices described in claim 1.

4. An organic electroluminescence device according to claim 3, wherein light emitted from the phosphorescent light emitting material has a peak wavelength of 500 nm or shorter.

5. An organic electroluminescence device according to claim 3, wherein the phosphorescent light emitting material is a compound having a metal selected from Er, Os and Pt.

6. An organic electroluminescence device according to claim 3, wherein the phosphorescent light emitting material is a light emitting material having one or more carbene ligands coordinated to a metal center.

7. An organic electroluminescence device according to claim 2, wherein the material for organic electroluminescence devices is a host material comprised in the light emitting layer of the organic electroluminescence device.

8. An organic electroluminescence device according to claim 2, wherein the material for organic electroluminescence devices is a material comprised in a hole transport layer of the organic electroluminescence device.

9. An organic electroluminescence device according to claim 2, wherein the material for organic electroluminescence devices is a material comprised in an electron transport layer or a hole blocking layer of the organic electroluminescence device.

10. An organic electroluminescence device according to claim 2, wherein a reducing dopant is added into an interfacial region of the cathode and the organic thin film layer.

11. An organic electroluminescence device according to claim 2, wherein an electron injection layer is disposed between the light emitting layer and the cathode, and the electron injection layer comprises a cyclic derivative having one or more nitrogen atoms as a main component.

.Iadd.12. An organic electroluminescence device according to claim 2, wherein R.sub.1 to R.sub.12 each independently represent hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group. .Iaddend.

.Iadd.13. An organic electroluminescence device according to claim 2, wherein: the alkyl group represented by R.sub.1 to R.sub.12 is methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, cyclohexyl group, cyclooctyl group, or 3,5-dimethylcyclohexyl group; the aryl group represented by R.sub.1 to R.sub.12 is phenyl group, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-tolyl group, or 3,4-xylyl group; and the heterocyclic group represented by R.sub.1 to R.sub.12 is 2-pyridinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group, 7-indolidinyl group, 8-indolidinyl group, 2-imidazopyridinyl group, 3-imidazopyridinyl group, 5-imidazopyridinyl group, 6-imidazopyridinyl group, 7-imidazopyridinyl group, 8-imidazopyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzo-thiophenyl group, 4-dibenzothiophenyl group, 1-dibenzosilolyl group, 2-dibenzosilolyl group, 3-dibenzosilolyl group, or 4-dibenzosilolyl group. .Iaddend.

.Iadd.14. An organic electroluminescence device according to claim 2, wherein X represents oxygen atom. .Iaddend.

.Iadd.15. An organic electroluminescence device according to claim 2, wherein X represents sulfur atom. .Iaddend.

.Iadd.16. An organic electroluminescence device according to claim 2, wherein adjacent groups among groups represented by R.sub.1 to R.sub.4 and among groups represented by R.sub.5 to R.sub.7 are not bonded to each other, thereby failing to form a saturated or unsaturated cyclic structure. .Iaddend.

.Iadd.17. An organic electroluminescence device according to claim 2, wherein all of R.sub.1 to R.sub.12 which may have substituents do not have substituents. .Iaddend.

.Iadd.18. An organic electroluminescence device according to claim 2, wherein: one of R.sub.1 to R.sub.7 is the halogen atom, the alkyl group having 1 to 40 carbon atoms which may have substituents, the heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents, the aryl group having 6 to 60 carbon atoms which may have substituents, the aryloxyl group having 6 to 60 carbon atoms which may have substituents, the aralkyl group having 7 to 60 carbon atoms which may have substituents, the alkenyl group having 2 to 40 carbon atoms which may have substituents, the alkylamino group having 1 to 40 carbon atoms which may have substituents, the aralkylamino group having 7 to 60 carbon atoms which may have substituents, the alkylsilyl group having 3 to 20 carbon atoms which may have substituents, the arylsilyl group having 8 to 40 carbon atoms which may have substituents, the ketoaryl group having 7 to 40 carbon atoms which may have substituents, the halogenated alkyl group having 1 to 40 carbon atoms which may have substituents, or cyano group, and the rest of R.sub.1 to R.sub.7 are hydrogen atom. .Iaddend.

.Iadd.19. An organic electroluminescence device according to claim 2, wherein all of R.sub.1 to R.sub.7 are hydrogen atom. .Iaddend.

.Iadd.20. An organic electroluminescence device according to claim 2, wherein: one of R.sub.8 to R.sub.12 is the heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents, the aryl group having 6 to 60 carbon atoms which may have substituents, the aryloxyl group having 6 to 60 carbon atoms which may have substituents, the alkylamino group having 1 to 40 carbon atoms which may have substituents, the aralkylamino group having 7 to 60 carbon atoms which may have substituents, the alkylsilyl group having 3 to 20 carbon atoms which may have substituents, the arylsilyl group having 8 to 40 carbon atoms which may have substituents, the ketoaryl group having 7 to 40 carbon atoms which may have substituents, or cyano group, and the rest of R.sub.R to R.sub.12 are hydrogen atom. .Iaddend.

.Iadd.21. An organic electroluminescence device according to claim 2, wherein: R.sub.1 to R.sub.12 each independently represent hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group; and adjacent groups among groups represented by R.sub.1 to R.sub.4 and among groups represented by R.sub.5 to R.sub.7 are not bonded to each other, thereby failing to form a saturated or unsaturated cyclic structure. .Iaddend.

.Iadd.22. An organic electroluminescence device according to claim 2, wherein: R.sub.1 to R.sub.12 each independently represent hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group; adjacent groups among groups represented by R.sub.1 to R.sub.4 and among groups represented by R.sub.5 to R.sub.7 are not bonded to each other, thereby failing to form a saturated or unsaturated cyclic structure; and all of R.sub.1 to R.sub.12 which may have substituents do not have substituents. .Iaddend.

.Iadd.23. An organic electroluminescence device according to claim 2, wherein: R.sub.1 to R.sub.12 each independently represent hydrogen atom, an aryl group, or a heterocyclic group; adjacent groups among groups represented by R.sub.1 to R.sub.4 and among groups represented by R.sub.5 to R.sub.7 are not bonded to each other, thereby failing to form a saturated or unsaturated cyclic structure; and one of R.sub.1 to R.sub.7 is the halogen atom, the alkyl group having 1 to 40 carbon atoms which may have substituents, the heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents, the aryl group having 6 to 60 carbon atoms which may have substituents, the aryloxyl group having 6 to 60 carbon atoms which may have substituents, the aralkyl group having 7 to 60 carbon atoms which may have substituents, the alkenyl group having 2 to 40 carbon atoms which may have substituents, the alkylamino group having 1 to 40 carbon atoms which may have substituents, the aralkylamino group having 7 to 60 carbon atoms which may have substituents, the alkylsilyl group having 3 to 20 carbon atoms which may have substituents, the arylsilyl group having 8 to 40 carbon atoms which may have substituents, the ketoaryl group having 7 to 40 carbon atoms which may have substituents, the halogenated alkyl group having 1 to 40 carbon atoms which may have substituents, or cyano group, and the rest of R.sub.1 to R.sub.7 are hydrogen atom. .Iaddend.

.Iadd.24. An organic electroluminescence device according to claim 2, wherein: R.sub.1 to R.sub.12 each independently represent hydrogen atom, an aryl group, or a heterocyclic group; adjacent groups among groups represented by R.sub.1 to R.sub.4 and among groups represented by R.sub.5 to R.sub.7 are not bonded to each other, thereby failing to form a saturated or unsaturated cyclic structure; and all of R.sub.1 to R.sub.7 are hydrogen atom. .Iaddend.

.Iadd.25. An organic electroluminescence device according to claim 2, wherein: the alkyl group represented by R.sub.1 to R.sub.12 is methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, cyclohexyl group, cyclooctyl group, or 3,5-dimethylcyclohexyl group; the aryl group represented by R.sub.1 to R.sub.12 is phenyl group, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-tolyl group, or 3,4-xylyl group; the heterocyclic group represented by R.sub.1 to R.sub.12 is 2-pyridinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group, 7-indolidinyl group, 8-indolidinyl group, 2-imidazopyridinyl group, 3-imidazopyridinyl group, 5-imidazopyridinyl group, 6-imidazopyridinyl group, 7-imidazopyridinyl group, 8-imidazopyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzo-thiophenyl group, 4-dibenzothiophenyl group, 1-dibenzosilolyl group, 2-dibenzosilolyl group, 3-dibenzosilolyl group, or 4-dibenzosilolyl group; and adjacent groups among groups represented by R.sub.1 to R.sub.4 and among groups represented by R.sub.5 to R.sub.7 are not bonded to each other, thereby failing to form a saturated or unsaturated cyclic structure. .Iaddend.

.Iadd.26. An organic electroluminescence device according to claim 2, wherein: the alkyl group represented by R.sub.1 to R.sub.12 is methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, cyclohexyl group, cyclooctyl group, or 3,5-dimethylcyclohexyl group; the aryl group represented by R.sub.1 to R.sub.12 is phenyl group, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-tolyl group, or 3,4-xylyl group; the heterocyclic group represented by R.sub.1 to R.sub.12 is 2-pyridinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group, 7-indolidinyl group, 8-indolidinyl group, 2-imidazopyridinyl group, 3-imidazopyridinyl group, 5-imidazopyridinyl group, 6-imidazopyridinyl group, 7-imidazopyridinyl group, 8-imidazopyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzo-thiophenyl group, 4-dibenzothiophenyl group, 1-dibenzosilolyl group, 2-dibenzosilolyl group, 3-dibenzosilolyl group, or 4-dibenzosilolyl group; adjacent groups among groups represented by R.sub.1 to R.sub.4 and among groups represented by R.sub.5 to R.sub.7 are not bonded to each other, thereby failing to form a saturated or unsaturated cyclic structure; and all of R.sub.1 to R.sub.12 which may have substituents do not have substituents. .Iaddend.

.Iadd.27. An organic electroluminescence device according to claim 2, wherein: the aryl group represented by R.sub.1 to R.sub.12 is phenyl group, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-tolyl group, or 3,4-xylyl group; the heterocyclic group represented by R.sub.1 to R.sub.12 is 2-pyridinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group, 7-indolidinyl group, 8-indolidinyl group, 2-imidazopyridinyl group, 3-imidazopyridinyl group, 5-imidazopyridinyl group, 6-imidazopyridinyl group, 7-imidazopyridinyl group, 8-imidazopyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzo-thiophenyl group, 4-dibenzothiophenyl group, 1-dibenzosilolyl group, 2-dibenzosilolyl group, 3-dibenzosilolyl group, or 4-dibenzosilolyl group; adjacent groups among groups represented by R.sub.1 to R.sub.4 and among groups represented by R.sub.5 to R.sub.7 are not bonded to each other, thereby failing to form a saturated or unsaturated cyclic structure; and one of R.sub.1 to R.sub.7 is the halogen atom, the alkyl group having 1 to 40 carbon atoms which may have substituents, the heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents, the aryl group having 6 to 60 carbon atoms which may have substituents, the aryloxyl group having 6 to 60 carbon atoms which may have substituents, the aralkyl group having 7 to 60 carbon atoms which may have substituents, the alkenyl group having 2 to 40 carbon atoms which may have substituents, the alkylamino group having 1 to 40 carbon atoms which may have substituents, the aralkylamino group having 7 to 60 carbon atoms which may have substituents, the alkylsilyl group having 3 to 20 carbon atoms which may have substituents, the arylsilyl group having 8 to 40 carbon atoms which may have substituents, the ketoaryl group having 7 to 40 carbon atoms which may have substituents, the halogenated alkyl group having 1 to 40 carbon atoms which may have substituents, or cyano group, and the rest of R.sub.1 to R.sub.7 are hydrogen atom. .Iaddend.

.Iadd.28. An organic electroluminescence device according to claim 2, wherein: the aryl group represented by R.sub.1 to R.sub.12 is phenyl group, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-tolyl group, or 3,4-xylyl group; the heterocyclic group represented by R.sub.1 to R.sub.12 is 2-pyridinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group, 7-indolidinyl group, 8-indolidinyl group, 2-imidazopyridinyl group, 3-imidazopyridinyl group, 5-imidazopyridinyl group, 6-imidazopyridinyl group, 7-imidazopyridinyl group, 8-imidazopyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzo-thiophenyl group, 4-dibenzothiophenyl group, 1-dibenzosilolyl group, 2-dibenzosilolyl group, 3-dibenzosilolyl group, or 4-dibenzosilolyl group; adjacent groups among groups represented by R.sub.1 to R.sub.4 and among groups represented by R.sub.5 to R.sub.7 are not bonded to each other, thereby failing to form a saturated or unsaturated cyclic structure; and all of R.sub.1 to R.sub.7 are hydrogen atom. .Iaddend.

.Iadd.29. An organic electroluminescence device according to claim 2, wherein: the aryl group represented by R.sub.1 to R.sub.12 is phenyl group, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-tolyl group, or 3,4-xylyl group; the heterocyclic group represented by R.sub.1 to R.sub.12 is 2-pyridinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group, 7-indolidinyl group, 8-indolidinyl group, 2-imidazopyridinyl group, 3-imidazopyridinyl group, 5-imidazopyridinyl group, 6-imidazopyridinyl group, 7-imidazopyridinyl group, 8-imidazopyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzo-thiophenyl group, 4-dibenzothiophenyl group, 1-dibenzosilolyl group, 2-dibenzosilolyl group, 3-dibenzosilolyl group, or 4-dibenzosilolyl group; adjacent groups among groups represented by R.sub.1 to R.sub.4 and among groups represented by R.sub.5 to R.sub.7 are not bonded to each other, thereby failing to form a saturated or unsaturated cyclic structure; all of R.sub.1 to R.sub.7 are hydrogen atom; and one of R.sub.8 to R.sub.12 is the heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents, the aryl group having 6 to 60 carbon atoms which may have substituents, the aryloxyl group having 6 to 60 carbon atoms which may have substituents, the alkylamino group having 1 to 40 carbon atoms which may have substituents, the aralkylamino group having 7 to 60 carbon atoms which may have substituents, the alkylsilyl group having 3 to 20 carbon atoms which may have substituents, the arylsilyl group having 8 to 40 carbon atoms which may have substituents, the ketoaryl group having 7 to 40 carbon atoms which may have substituents, or cyano group, and the rest of R.sub.8 to R.sub.12 are hydrogen atom. .Iaddend.

.Iadd.30. An organic electroluminescence device according to claim 2, wherein: the alkyl group represented by R.sub.1 to R.sub.12 is methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, cyclohexyl group, cyclooctyl group, or 3,5-dimethylcyclohexyl group; the aryl group represented by R.sub.1 to R.sub.12 is phenyl group, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-tolyl group, or 3,4-xylyl group; the heterocyclic group represented by R.sub.1 to R.sub.12 is 2-pyridinyl group, 2-indolidinyl group, 3-indolidinyl group, 5-indolidinyl group, 6-indolidinyl group, 7-indolidinyl group, 8-indolidinyl group, 2-imidazopyridinyl group, 3-imidazopyridinyl group, 5-imidazopyridinyl group, 6-imidazopyridinyl group, 7-imidazopyridinyl group, 8-imidazopyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzo-thiophenyl group, 4-dibenzothiophenyl group, 1-dibenzosilolyl group, 2-dibenzosilolyl group, 3-dibenzosilolyl group, or 4-dibenzosilolyl group; adjacent groups among groups represented by R.sub.1 to R.sub.4 and among groups represented by R.sub.5 to R.sub.7 are not bonded to each other, thereby failing to form a saturated or unsaturated cyclic structure; all of R.sub.1 to R.sub.7 are hydrogen atom; one of R.sub.8 to R.sub.12 is the heterocyclic group having 3 to 60 carbon atoms and having no skeleton structure of benzotriazole which may have substituents, the aryl group having 6 to 60 carbon atoms which may have substituents, the aryloxyl group having 6 to 60 carbon atoms which may have substituents, the alkylamino group having 1 to 40 carbon atoms which may have substituents, the aralkylamino group having 7 to 60 carbon atoms which may have substituents, the alkylsilyl group having 3 to 20 carbon atoms which may have substituents, the arylsilyl group having 8 to 40 carbon atoms which may have substituents, the ketoaryl group having 7 to 40 carbon atoms which may have substituents, or cyano group, and the rest of R.sub.8 to R.sub.12 are hydrogen atom; and X represents oxygen atom. .Iaddend.

Description

EXAMPLES

(1) The present invention will be described more specifically with reference to examples in the following.

Synthesis Example 1

Synthesis of D1

(2) ##STR00062##

(3) Into a 300 ml three-necked flask, 3.75 g (17.7 mmole) of 4-dibenzofuranboric acid and 1.02 g (0.885 mmole) of tetrakis-(triphenylphosphine)palladium were placed under the atmosphere of argon, and the flask was purged with argon. To the above mixture, 53.1 ml of 1,2-dimethoxyethane, 0.810 ml (6.73 mmole) of 1,4-dibromobenzene and 26.6 ml of a 2.0 M aqueous solution of sodium carbonate (53.1 mmole) were added, and the resultant mixture was heated under the atmosphere of argon in the refluxing condition for 8 hours. After the reaction fluid was filtered, the obtained solid substance was washed with water, methanol and methylene chloride, and 2.72 g (6.63 mmole; the yield: 98%) of Compound D1 was obtained. The obtained substance was identified to be the object compound in accordance with 90 MHz .sup.1H-NMR and FD-MS (the field desorption mass spectroscopy). The result of FD-MS is shown in the following.

(4) FD-MS: calcd. for C.sub.30H.sub.18O.sub.2=410; found: m/z=410 (M.sup.+, 100)

(5) The obtained compound was purified by sublimation at 190° C. The purity of the compound obtained after the purification by sublimation was 99.8%.

Synthesis Example 2

Synthesis of E1

(6) ##STR00063##

(7) Into a 300 ml three-necked flask, 3.42 g (15.0 mmole) of 4-dibenzothiopheneboric acid and 0.867 g (0.750 mmole) of tetrakis(triphenylphosphine)palladium were placed under the atmosphere of argon, and the flask was purged with argon. To the above mixture, 45.0 ml of 1,2-dimethoxyethane, 0.688 ml (5.70 mmole) of 1,4-dibromo-benzene and 22.5 ml of a 2.0 M aqueous solution of sodium carbonate (45.0 mmole) were added, and the resultant mixture was heated under the atmosphere of argon in the refluxing condition for 8 hours. After the reaction fluid was filtered, the obtained solid substance was washed with water, methanol and methylene chloride, and 1.64 g (3.71 mmole; the yield: 54%) of Compound E1 was obtained. The obtained substance was identified to be the object compound in accordance with 90 MHz .sup.1H-NMR and FD-MS (the field desorption mass spectroscopy). The result of FD-MS is shown in the following.

(8) FD-MS: calcd. for C.sub.30H.sub.18S.sub.2=442; found: m/z=442 (M.sup.+, 100)

(9) The obtained compound was purified by sublimation at 230° C.

(10) The purity of Compound 2 obtained after the purification by sublimation was 99.7%.

Synthesis Example 3

Synthesis of Compound E4

(11) The route of synthesis of Compound E4 is shown in the following.

(12) ##STR00064##

(13) Into a 300 ml three-necked flask, 6.04 g (26.5 mmole) of 4-dibenzothiopheneboric acid, 2.25 g (7.14 mmole) of 1,3,5tribromo-benzene and 2.30 g (1.99 mmole) of tetrakis(triphenylphosphine)-palladium were placed under the atmosphere of argon, and the flask was purged with argon. To the above mixture, 79.5 ml of 1,2-dimethoxy-ethane and 39.8 ml of a 2.0 M aqueous solution of sodium carbonate (79.5 mmole) were added, and the resultant mixture was heated under the atmosphere of argon in the refluxing condition for 16 hours. After the reaction fluid was filtered, the obtained solid substance was washed with water, methanol and methylene chloride, and 1.78 g (2.85 mmole; the yield: 40%) of Compound E4 was obtained. The obtained substance was identified to be the object compound in accordance with 90 MHz .sup.1H-NMR and FD-MS (the field desorption mass spectroscopy). The result of FD-MS is shown in the following.

(14) FD-MS; calcd. for C.sub.42H.sub.24S.sub.3=624; found: m/z=624 (M.sup.+, 100)

(15) The obtained compound was purified by sublimation at 260° C. The purity of the compound obtained after the purification by sublimation was 99.4%.

(16) Synthesis Example 4

(17) Synthesis of Compound E2

(18) The route of syntheis of Compound E2 is shown in the following.

(19) ##STR00065##

(20) Into a 300 ml three-necked flask, 4.04 g (17.7 mmole) of 4-dibenzothiopheneboric acid and 1.02 g (0.885 mmole) of tetrakis(triphenylphosphine)palladium were placed under the atmosphere of argon, and the flask was purged with argon. To the above mixture, 53.1 ml of 1,2-dimethoxyethane, 0.800 ml (6.73 mmole) of 1,2-dibromo-benzene and 26.6 ml of a 2.0 M aqueous solution of sodium carbonate (53.1 mmole) were added, and the resultant mixture was heated under the atmosphere of argon in the refluxing condition for 8 hours. After the reaction fluid was filtered, the obtained solid substance was purified in accordance with the silica gel column chromatography (the elution solvent: methylene chloride/hexane=1/3), and 1.92 g (4.34 mmole; the yield: 64%) of Compound E2 was obtained. The obtained substance was identified to be the object compound in accordance with 90 MHz .sup.1H-NMR and FD-MS (the field desorption mass spectroscopy). The result of FD-MS is shown in the following.

(21) FD-MS: calcd. for C.sub.30H.sub.18S.sub.2=442; found: m/z=442 (M.sup.+, 100)

(22) The obtained compound was purified by sublimation at 210° C.

(23) The purity of the compound obtained after the purification by sublimation was 99.4%.

Synthesis Example 5

Synthesis of Compound E3

(24) The route of synthesis of Compound E3 is shown in the following.

(25) ##STR00066##

(26) Into a 300 ml three-necked flask, 1.41 g (6.17 mmole) of 4-dibenzothiopheneboric acid, 1.20 g (2.59 mmole) of aryl dibromide and 0.356 g (0.309 mmole) of tetrakis(triphenylphosphine)palladium were placed under the atmosphere of argon, and the flask was purged with argon. To the above mixture, 18.5 ml of 1,2-dimethoxyethane and 9.25 ml of a 2.0 M aqueous solution of sodium carbonate (18.5 mmole) were added, and the resultant mixture was heated under the atmosphere of argon in the refluxing condition for 8 hours. To the reaction fluid, 100 ml of water and 100 ml of methylene chloride were added, and the organic layer was separated and dried with anhydrous magnesium sulfate. After the dried solution was concentrated under a reduced pressure using an evaporator, the formed solid substance was purified in accordance with the silica gel column chromatography (the elution solvent: methylene chloride/hexane=1/3), and 1.30 g (1.94 mmole; the yield: 75%) of Compound E3 was obtained. The obtained substance was identified to be the object compound in accordance with 90 MHz .sup.1H-NMR and FD-MS (the field desorption mass spectroscopy). The result of FD-MS is shown in the following.

(27) FD-MS: calcd. for C.sub.48H.sub.30S.sub.2=670; found: m/z=670 (M.sup.+, 100)

(28) The obtained compound was purified by sublimation at 210° C. The purity of Compound E3 obtained after the purification by sublimation was 99.5%.

Synthesis Example 6

Synthesis of Compound D3

(29) The route of synthesis of Compound D3 is shown in the following.

(30) ##STR00067##

(31) Into a 300 ml three-necked flask, 2.31 g (10.9 mmole) of 4-dibenzofuranboric acid, 2.12 g (4.57 mmole) of aryl dibromide and 0.630 g (0.545 mmole) of tetrakis(triphenylphosphine)palladium were placed under the atmosphere of argon, and the flask was purged with argon. To the above mixture, 32.7 ml of 1,2-dimethoxyethane and 16.4 ml of a 2.0 M aqueous solution of sodium carbonate (32.7 mmole) were added, and the resultant mixture was heated under the atmosphere of argon in the refluxing condition for 8 hours. To the reaction fluid, 100 ml of water and 100 ml of methylene chloride were added, and the organic layer was separated and dried with anhydrous magnesium sulfate. After the dried solution was concentrated under a reduced pressure using an evaporator, the formed solid substance was purified in accordance with the silica gel column chromatography (the elution solvent: methylene chloride/hexane=1/3), and 1.90 g (2.97 mmole; the yield: 65%) of Compound D3 was obtained. The obtained substance was identified to be the object compound in accordance with 90 MHz .sup.1H-NMR and FD-MS (the field desorption mass spectroscopy). The result of FD-MS is shown in the following.

(32) FD-MS: calcd. for C.sub.48H.sub.30O.sub.2=638; found: m/z=638 (M.sup.+, 100)

(33) The obtained compound was purified by sublimation at 200° C. The purity of Compound D3 obtained after the purification by sublimation was 99.7%.

Synthesis Example 7

Synthesis of Compound E22

(34) The route of synthesis of Compound E22 is shown in the following.

(35) ##STR00068##

(36) Into a 300 ml three-necked flask, 4.33 g (19.0 mmole) of 4-dibenzothiopheneboric acid, 3.75 g (8.00 mmole) of an aryl dibromide and 1.10 g (0.950 mmole) of tetrakis(triphenylphosphine)palladium were placed under the atmosphere of argon, and the flask was purged with argon. To the above mixture, 57.0 ml of 1,2-dimethoxyethane and 28.5 ml of a 2.0 M aqueous solution of sodium carbonate (57.0 mmole) were added, and the resultant mixture was heated under the atmosphere of argon in the refluxing condition for 16 hours. After the reaction fluid was filtered, the obtained solid substance was washed with water, methanol and methylene chloride, and 1.70 g (2.53 mmole: the yield: 32%) of Compound E22 was obtained. The obtained substance was identified to be the object compound in accordance with 90 MHz .sup.1H-NMR and FD-MS (the field desorption mass spectroscopy). The result of FD-MS is shown in the following.

(37) FD-MS: calcd. for C.sub.46H.sub.28N.sub.2S.sub.2=672; found: m/z=672 (M.sup.+, 100)

(38) The obtained compound was purified by sublimation at 350° C. The purity of Compound E22 obtained after the purification by sublimation was 99.3%.

Synthesis Example 8

Synthesis of Compound D22

(39) The route of synthesis of Compound D22 is shown in the following.

(40) ##STR00069##

(41) Into a 300 ml three-necked flask, 4.87 g (22.9 mmole) of 4-dibenzofuranboric acid, 4.50 g (9.65 mmole) of aryl dibromide and 1.32 g (1.15 mmole) of tetrakis(triphenylphosphine)palladium were placed under the atmosphere of argon, and the flask was purged with argon. To the above mixture, 68.7 ml of 1,2-dimethoxyethane and 34.4 ml of a 2.0 M aqueous solution of sodium carbonate (68.7 mmole) were added, and the resultant mixture was heated under the atmosphere of argon in the refluxing condition for 16 hours. After the reaction fluid was filtered, the obtained solid substance was washed with water, methanol and methylene chloride, and 2.78 g (4.34 mmole; the yield: 45%) of Compound D22 was obtained. The obtained substance was identified to be the object compound in accordance with 90 MHz .sup.1H-NMR and FD-MS (the field desorption mass spectroscopy). The result of FD-MS is shown in the following.

(42) FD-MS: calcd. for C.sub.46H.sub.28N.sub.2O.sub.2=640; found: m/z=640 (M.sup.+, 100)

(43) The obtained compound was purified by sublimation at 330° C. The purity of Compound D22 obtained after the purification by sublimation was 99.5%.

Synthesis Example 9

Synthesis of Compound G15

(44) The route of synthesis of Compound G15 is shown in the following.

(45) ##STR00070##

(46) Into a 300 ml three-necked flask, 2.31 g (10.9 mmole) of 4-dibenzofuranboric acid, 2.48 g (10.9 mmole) 4-dibenzothiopheneboric acid, 4.21 g (9.07 mmole) of aryl dibromide and 1.26 g (1.09 mmole) of tetrakis(triphenylphosphine)palladium were placed under the atmosphere of argon, and the flask was purged with argon. To the above mixture, 65.4 ml of 1,2-dimethoxyethane and 32.7 ml of a 2.0 M aqueous solution of sodium carbonate (65.4 mmole) were added, and the resultant mixture was heated under the atmosphere of argon in the refluxing condition for 16 hours. To the reaction fluid, 100 ml of water and 100 ml of methylene chloride were added, and the organic layer was separated and dried with anhydrous magnesium sulfate. After the dried solution was concentrated under a reduced pressure using an evaporator, the formed solid substance was purified in accordance with the silica gel column chromatography (the elution solvent: methylene chloride/hexane=1/3), and 1.49 g (2.27 mmole; the yield: 25%) of Compound G15 was obtained. The obtained substance was identified to be the object compound in accordance with 90 MHz .sup.1H-NMR and FD-MS (the field desorption mass spectroscopy). The result of FD-MS is shown in the following.

(47) FD-MS: calcd. for C.sub.48H.sub.30OS=654; found: m/z=654 (Mt, 100)

(48) The obtained compound was purified by sublimation at 200° C. The purity of Compound G15 obtained after the purification by sublimation was 99.2%.

Syntheis Example 10

Synthesis of Coupound H2

(49) The route of synthesis of Compound H2 is shown in the following.

(50) ##STR00071##

(51) Into a 300 ml three-necked flask, 4.44 g (19.5 mmole) of 4-dibenzothiopheneboric acid, 2.78 g (8.18 mmole) of 4,4′-dibromo-benzophenone and 1.13 g (0.975 mmole) of tetrakis (triphenylphosphine)-palladium were placed under the atmosphere of argon, and the flask was purged with argon. To the above mixture, 58.5 ml of 1,2-dimethoxyethane and 29.3 ml of a 2.0 M aqueous solution of sodium carbonate (58.5 mmole) were added. and the resultant mixture was heated under the atmosphere of argon in the refluxing condition for 8 hours. After the reaction fluid was filtered, the obtained solid substance was washed with water, methanol and toluene, and 3.31 g (6.05 mmole; the yield: 74%) of Compound H2 was obtained. The obtained substance was identified to be the object compound in accordance with 90 MHz .sup.1H-NMR and FD-MS (the field desorption mass spectroscopy). The result of FD-MS is shown in the following.

(52) FD-MS: calcd. for C.sub.37H.sub.22OS.sub.2=546; found: m/z=546 (M.sup.+, 100)

(53) The obtained compound was purified by sublimation at 320° C. The purity of Compound H2 obtained after the purification by sublimation was 99.0%.

Synthesis Example 11

Synthesis of Compound H1

(54) The route of synthesis of Compound H1 is shown in the following.

(55) ##STR00072##

(56) Into a 300 ml three-necked flask, 4.59 g (21.6 mmole) of 4-dibenzofuranboric acid, 3.09 g (9.09 mmole) of 4,4′-dibromo-benzophenone and 1.25 g (1.08 mmole) of tetrakis (triphenylphosphine)-palladium were placed under the atmosphere of argon, and the flask was purged with argon. To the above mixture, 64.8 ml of 1,2-dimethoxy-ethane and 32.4 ml of a 2.0 M aqueous solution of sodium carbonate (64.8 mmole) were added, and the resultant mixture was heated under the atmosphere of argon in the refluxing condition for 8 hours. After the reaction fluid was filtered, the obtained solid substance was washed with water, methanol and toluene, and 2.67 g (5.18 mmole; the yield: 57%) of Compound H1 was obtained. The obtained substance was identified to be the object compound in accordance with 90 MHz .sup.1H-NMR and FD-MS (the field desorption mass spectroscopy). The result of FD-MS is shown in the following.

(57) FD-MS: calcd. for C.sub.37H.sub.22O.sub.3=514; found: m/z=514 (M.sup.+, 100)

(58) The obtained compound was purified by sublimation at 315° C. The purity of Compound H1 obtained after the purification by sublimation was 99.2%.

Example 1

Preparation of an Organic EL Device

(59) A glass substrate of 25 mm×75 mm×1.1 mm thickness having an ITO transparent electrode (manufactured by GEOMATEC Company) 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 the transparent electrode was attached to a substrate holder of a vacuum vapor deposition apparatus. On the surface of the cleaned substrate at the side having the transparent electrode, a film of HTM (the formula shown in the following) having a thickness of 100 nm was formed in a manner such that the formed film covered the transparent electrode. The formed film of HTM worked as the hole injection and transport layer. Following the formation of the hole injection and transport layer, Compound D1 as the host compound and Complex P expressed by the formula shown in the following were vapor deposited simultaneously on the formed film of HTM in accordance with the resistance heating method so that a film having a thickness of 30 nm was formed. The concentration of Complex P was 7% by weight. The formed film of the host compound and Compound D1 worked as the light emitting layer. Following the formation of the light emitting layer, a film having a thickness of 25 nm of ETM1 shown in the following was formed and, then, a film having a thickness of 5 nm of ETM2 shown in the following was formed on the formed film of ETM1. The layers of ETM1 and ETM2 worked as the electron transport layer and the electron injection layer, respectively. Then, LiF was vapor deposited at a rate of 1 Å/min to form a film having a thickness of 0.1 nm so that an electron injection electrode (the cathode) was formed. On the formed LiF layer, metallic aluminum was vapor deposited to form a film having a thickness of 150 nm so that a metal cathode having a thickness of 150 nm was formed. Thus, an organic EL device was prepared.

(60) (Evaluation of the Light Emitting Property of the Organic EL Device)

(61) The organic EL device prepared as described above was driven under a direct current (the current density J=1 mA/cm.sup.2) to emit light. The luminance (L) was measured, and the efficiency of light emission (L/J) was obtained. The results are shown in Table 1.

(62) ##STR00073##

Examples 2 to 9

(63) Organic EL devices were prepared in accordance with the same procedures as those conducted in Example 1 except that compounds described in the column of the host compound in Table 1 were used as the host compound in place of Compound D1. The efficiency of light emission of the obtained organic EL devices each was measured in accordance with the same procedure as that conducted in Example 1. The results are shown in Table 1.

Comparative Examples 1 to 3

(64) Organic EL devices were prepared in accordance with the same procedures as those conducted in Example 1 except that compounds described in International Patent Publication No. WO 2004/096945, Japanese Patent Application Laid-Open No. Heisei 5 (1993)-109485 and Japanese Patent Application Laid-Open No. 2004-214050 were used as the host compound in Comparative Examples 1, 2 and 3, respectively, in place of Compound D1. The formulae are shown in the following. The efficiency of light emission of the obtained organic EL devices was measured in accordance with the same procedure as that conducted in Example 1. The results are shown in Table 1.

(65) ##STR00074##

(66) TABLE-US-00001 TABLE 1 J (mA/ L (cd/ L/J Host compound cm.sup.2) m.sup.2) (cd/A) D1 1.0 400 40 E1 1.0 284 28 E4 1.0 310 31 E2 1.0 295 30 E3 1.0 456 46 D3 1.0 482 48 D22 1.0 405 41 E22 1.0 325 33 G15 1.0 358 36 H1 1.0 328 33 H2 1.0 444 44 Comparative 1.0  20 2.0 Example 1 Comparative 1.0  32 3.2 Example 2 Comparative 1.0 139 14 Example 3

(67) The results in Table 1 show that the organic EL devices using the compound of the present invention in the light emitting layer exhibited greater efficiencies of light emission. It is shown that the compound of the present invention is useful for application to organic EL devices.

INDUSTRIAL APPLICABILITY

(68) As described specifically in the above, the organic EL device exhibiting a great efficiency of light emission, having no defect pixels, exhibiting excellent heat resistance and having a long life can be obtained when the material for organic EL devices of the present invention comprising the compound represented by any one of general formulae (1) to (14) is used and, therefore, the organic EL device of the present invention is very useful as the light source for various electronic instruments.