AROMATIC AMINE DERIVATIVE, AND ORGANIC ELECTROLUMINESCENT ELEMENT COMPRISING THE SAME

Abstract

An aromatic amine derivative represented by the following formula (1) wherein at least one of Ar.sub.1 to Ar.sub.4 is a heterocyclic group represented by the following formula (2) wherein X.sub.1 is an oxygen atom or a sulfur atom.

##STR00001##

Claims

1-25. (canceled)

26. A composition comprising: an aromatic amine derivative represented by the following formula (Al), and pyrene derivative represented by the following formula (6): ##STR00091## wherein R.sub.101 to R.sub.108 are independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms or a cyano group, and Ar.sub.101 to Ar.sub.108 are independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, provided that at least one of Ar.sub.101 to Ar.sub.104 a heterocyclic group represented by the following formula (A2): ##STR00092## wherein R.sub.111 to R.sub.117 are independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms, a cyano group, a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 20 ring atoms, adjacent substituents of R.sub.111 to R.sub.117 may be bonded to each other to form a saturated or unsaturated ring, and X.sub.101 is an oxygen atom or a sulfur atom; ##STR00093## wherein Ar.sup.111 and Ar.sup.222 are independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms; L.sup.1 and L.sup.2 are independently a substituted or unsubstituted divalent aryl group having 6 to 30 ring carbon atoms or a heterocyclic group; m is an integer of 0 to 1, n is an integer of 1 to 4, s is an integer of 0 to 1, and t is an integer of 0 to 3; and L.sup.1 or Ar.sup.111 bonds to any position of the 1.sup.st to 5.sup.th positions of pyrene, and L.sup.2 or Ar.sup.222 bonds to any position of the 6.sup.th to 10.sup.th positions of pyrene.

27. The composition according to claim 26, wherein in R.sub.101 to R.sub.108, the halogen atom is selected from the group consisting of fluorine, chlorine, bromine and iodine, the alkyl group for the substituted or unsubstituted alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl and n-octyl, the cycloalkyl group for the substituted or unsubstituted cycloalkyl group is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, adamantyl and norbornyl, the substituted silyl group is selected from the group consisting of trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triisopropylsilyl and triphenylsilyl, and the aryl group for the substituted or unsubstituted aryl group is selected from the group consisting of phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzofluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, terphenyl and fluoranthenyl, and the heterocyclic group for the substituted or unsubstituted heterocyclic group is selected from the group consisting of pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, imidazolyl, furyl, benzofuranyl, isobenzofuranyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolyl, oxadiazolyl, furazanyl, thienyl and benzothiophenyl, and in R.sub.111 to R.sub.117, and in R.sub.111 to R.sub.117, the halogen atom is selected from the group consisting of fluorine, chlorine, bromine and iodine, the alkyl group for the substituted or unsubstituted alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl and n-octyl, the silyl group for the substituted or unsubstituted silyl group is selected from the group consisting of trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triisopropylsilyl and triphenylsilyl, the aryl group for the substituted or unsubstituted aryl group is selected from the group consisting of phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzofluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, terphenyl and fluoranthenyl, and the heterocyclic group for the substituted or unsubstituted heterocyclic group is selected from the group consisting of pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, imidazolyl, furyl, benzofuranyl, isobenzofuranyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3 -dibenzothiophenyl, 4-dibenzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolyl, oxadiazolyl, furazanyl, thienyl and benzothiophenyl.

28. The composition according to claim 27, wherein in R.sub.101 to R.sub.108, the halogen atom is fluorine, the alkyl group for the substituted or unsubstituted alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl and n-hexyl, the cycloalkyl group for the substituted or unsubstituted cycloalkyl group is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and 4-methylcyclohexyl, and the heterocyclic group for the substituted or unsubstituted heterocyclic group is selected from the group consisting of 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl and 9-carbazolyl, and in R.sub.111 to R.sub.117, the halogen atom is fluorine, the alkyl group for the substituted or unsubstituted alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl and n-hexyl, the alkenyl group for the substituted or unsubstituted alkenyl group is vinyl, the alkynyl group for the substituted or unsubstituted alkynyl group is ethynyl, and the heterocyclic group for the substituted or unsubstituted heterocyclic group is selected from the group consisting of 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl and 9-carbazolyl.

29. The composition of claim 26, wherein R.sub.101 to R.sub.108 are independently a hydrogen atom, or a group selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, n-hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl substituted by methyl and 1-naphthyl, Ar.sub.101 to Ar.sub.104 are independently a group selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted terphenyl, 2-fluorenyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 2-dibenzothiophenyl, pyridinyl and quinolyl, and R.sub.111 to R.sub.117 are independently a hydrogen atom, or a group selected from the group consisting of methyl, t-butyl, trimethylsilyl and phenyl.

30. The composition of claim 26, wherein R.sub.101 to R.sub.108 are independently a hydrogen atom, Ar.sub.101 to Ar.sub.104 are independently a group selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted terphenyl, 2-fluorenyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 2-dibenzothiophenyl, pyridinyl and quinolyl, R.sub.111 to R.sub.117 are independently a hydrogen atom, or a group selected from the group consisting of methyl, t-butyl, trimethylsilyl and phenyl, adjacent substituents of R.sub.111 to R.sub.117 may be bonded to each other to form a saturated or unsaturated ring, and X.sub.101 is an oxygen atom or a sulfur atom.

31. The composition of claim 26, wherein R.sub.111 to R.sub.117 are independently a hydrogen atom.

32. The composition of claim 26, wherein the substituents for any substituted groups in the formula (A1) are independently selected from the group consisting of alkyl, substituted or unsubstituted silyl, alkoxy, aryl, aryloxy, aralkyl, cycloalkyl, heterocyclic, halogen, alkyl halide, hydroxy, nitro, cyano and carboxy.

33. The composition of claim 32, wherein the substituents for any substituted groups in the formula (A1) are independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triisopropylsilyl, triphenylsilyl, methoxy, ethoxy, phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzofluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, terphenyl, fluoranthenyl, phenoxy, benzyl, phenylethyl, 2-phenylpropane-2-yl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, adamantyl, norbornyl, pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, imidazolyl, furyl, benzofuranyl, isobenzofuranyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolyl, oxadiazolyl, furazanyl, thienyl, benzothiophenyl, fluorine, chlorine, bromine, iodine, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, trifluoromethyl, hydroxy, nitro, cyano and carboxy.

34. The composition according to claim 33, wherein the substituents for any substituted groups in the formula (A1) are independently selected from the group consisting of methyl, ethyl, isopropyl, 2,2-dimethylpropyl, t-butyl, trimethylsilyl, methoxy, phenyl, 2-phenylpropane-2-yl, cyclopentyl, cyclohexyl, fluorine, trifluoromethyl and cyano.

35. The composition according to claim 26, wherein Ar.sub.101 to Ar.sub.104 are independently a group selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a 2-dibenzofuranyl group, a 3-dibenzofuranyl group, and a 4-dibenzofuranyl group.

36. The composition according to claim 26, wherein the substituted or unsubstituted aryl groups for Ar.sup.111 and Ar.sup.222 in the formula (6), are independently a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms.

37. The composition according to claim 26, wherein the aryl groups for the substituted or unsubstituted aryl group for Ar.sup.111 and Ar.sup.222 in the formula (6), are independently selected from the group consisting of phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzofluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, terphenyl and fluoranthenyl.

38. The composition according to claim 26, wherein the aryl groups for the substituted or unsubstituted aryl group for Ar.sup.111 and Ar.sup.222 in the formula (6), are independently selected from the group consisting of a phenyl group, naphthyl group, phenanthryl group, fluorenyl group, biphenyl group, anthryl group and pyrenyl group.

39. The composition according to claim 26, wherein L.sup.1 and L.sup.2 in the formula (6) are independently a divalent aryl group composed of a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted fluorenylene group, and a combination of these substituents.

40. The composition according to claim 26, wherein m in the formula (6) is an integer of 0 to 1, and n in the formula (6) is an integer of 1 to 2.

41. The composition according to claim 26, wherein s in the formula (6) is an integer of 0 to 1, and tin the formula (6) is an integer of 0 to 2.

42. The composition according to claim 26, wherein the substituents for any substituted groups in the formula (6) are independently selected from the group consisting of alkyl, substituted or unsubstituted silyl, alkoxy, aryl, aryloxy, aralkyl, cycloalkyl, heterocyclic, halogen, alkyl halide, hydroxy, nitro, cyano and carboxy.

43. The composition according to claim 26, wherein the substituents for any substituted groups in the formula (6) are independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triisopropylsilyl, triphenylsilyl, methoxy, ethoxy, phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzofluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, terphenyl, fluoranthenyl, phenoxy, benzyl, phenylethyl, 2-phenylpropane-2-yl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, adamantyl, norbornyl, pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, imidazolyl, furyl, benzofuranyl, isobenzofuranyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolyl, oxadiazolyl, furazanyl, thienyl, benzothiophenyl, fluorine, chlorine, bromine, iodine, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, trifluoromethyl, hydroxy, nitro, cyano and carboxy.

44. The composition according to claim 26, wherein the substituents for substituted groups for L.sup.1 and L.sup.2 in the formula (6) are independently an alkyl group having 1 to 20 carbon atoms.

45. The composition according to claim 26, which comprises the aromatic amine derivative represented by the formula (A1) as a dopant material, and the pyrene derivative represented by the formula (6) as a host material.

Description

EXAMPLES

Production Example 1

[0162] Aromatic amine derivative D-1 was produced as follows:

##STR00069##

(1) Synthesis of Intermediate M1 (Reaction A)

[0163] In a stream of argon, 30.0 g of dibenzofuran and 300 mL of dehydrated tetrahydrofuran (THF) were put in a 1000 mL-recovery flask, and the resulting solution was cooled to −65° C. Then, 120 mL (1.65 M) of a hexane solution of n-butyllithium was added. The resulting mixture was heated gradually, and allowed to react at room temperature for 3 hours. After cooling to −65° C. again, 23.1 mL of 1,2-dibromoethane was added dropwise thereto, and the reaction mixture was heated gradually and a reaction was conducted for 3 hours at room temperature.

[0164] The reaction solution was separated and extracted by adding 2N hydrochloric acid and ethyl acetate, and then the organic phase was washed with clean water and saturated saline and dried with sodium sulfate, and concentrated to obtain a crude product. The crude product was purified with silica gel chromatography (methylene chloride), and solids obtained were dried under reduced pressure to obtain 43.0 g of white solids. The solids were identified as intermediate M1 by FD-MS (field desorption mass spectrometry) analysis.

(2) Synthesis of Intermediate M2 (Reaction B)

[0165] In a stream of argon, 11.7 g of intermediate M1, 10.7 mL of aniline, 0.63 g of tris(dibenzylideneacetone)dipalladium(0) [Pd.sub.2(dba).sub.3], 0.87 g of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl [BINAP], 9.1 g of sodium tert-butoxide and 131 mL of dehydrated toluene were put in a 300 mL-recovery flask. A reaction was conducted at 85° C. for 6 hours.

[0166] After cooling, the reaction solution was filtered through cellite. A crude product obtained was purified by silica gel column chromatography (n-hexane/methylene chloride (3/1)). Solids obtained were dried under reduced pressure to obtain 10.0 g of white solids. The solids were identified as intermediate M2 by FD-MS (field desorption mass spectrometry) analysis.

(3) Synthesis of Compound D-1 (Reaction C)

[0167] In a stream of argon, 8.6 g of intermediate M2, 5.9 g of 1,6-dibromo-3,8-diisopropylpyrene which had been synthesized by a known method, 2.5 g of sodium tert-butoxide, 150 mg of palladium acetate (II) [Pd(OAc).sub.2], 135 mg of tri-tert-butylphosphine and 90 mL of dehydrated toluene were put in a 300 mL-recovery flask. A reaction was conducted at 85° C. for 7 hours.

[0168] The reaction solution was filtered, and a crude product obtained was purified by silica gel chlormatography (toluene). Solids obtained were recrystallized from toluene, and solids obtained were dried under reduced pressure, whereby 9.3 g of yellowish white solids were obtained. Analysis by FD-MS (field disorption mass spectrometery) was conducted for the compound obtained. The UV absorption maximum wavelength λmax and the flurescence emission maximum wavelength λmax in the toluene solution are given below. [0169] FDMS, calcd for C.sub.58H.sub.44N.sub.2O.sub.2=800, found m/z=(M+) [0170] UV(PhMe); λmax=419 nm, FL(PhMe, λex=390 nm); λmax=452 nm

Production Example 2

[0171] Aromatic amine derivative D-2 was produced as follows:

##STR00070##

(1) Synthesis of Intermediate M3 (Reaction B)

[0172] An intermediate was synthesized in the same manner as in the synthesis of intermediate M2, except that 4-isopropylaniline was used instead of aniline. The intermediate obtained was identified as intermediate M3 by FD-MS (field desorption mass spectrometry) analysis.

(2) Synthesis of Compound D-2 (Reaction C)

[0173] A compound was synthesized in the same manner as in the synthesis of compound D-1, except that intermediate M3 was used instead of intermediate M2. Analysis by FD-MS (field disorption mass spectrometery) was conducted for the compound obtained. The UV absorption maximum wavelength λmax and the flurescence emission maximum wavelength in the toluene solution are given below. [0174] FDMS, calcd for C.sub.64H.sub.56N.sub.2O.sub.2=884, found m/z=884(M+) [0175] UV(PhMe); λmax=425 nm, FL(PhMe, λex=400 nm); λmax=457 nm

Production Example 3

[0176] Aromatic amine derivative D-3 was produced as follows:

##STR00071##

(1) Synthesis of Intermediate M4 (Reaction D)

[0177] In a stream of argon, 18.7 g of intermediate M1, 3.4 g of acetoamide, 0.81 of copper iodide (I), 15.7 g of potassium carbonate and 90 mL of xylene were put in a 300 mL-recovery flask. After stirring, 0.9 mL of N,N′-dimethylethylenediamine was put, and a reaction was conducted at 170° C. for 18 hours.

[0178] The reaction solution was filtered, and a crude product obtained was washed with toluene, clean water and methanol. Solids obtained were dried under reduced pressure, whereby 8.2 g of solids were obtained. The solids obtained were identified as intermediate M4 by FD-MS (field desorption mass spectrometry) analysis.

(2) Synthesis of Intermediate M5 (Reaction E)

[0179] 8.2 g of intermediate M4, 12.2 g of potassium hydroxide, 14 mL of clean water, 37 mL of toluene and 74 mL of ethanol were put in a 300 mL-recovery flask. A reaction was conducted at 110° C. for 8 hours.

[0180] The reaction solution was separated and extracted by adding ethyl acetate, and then the organic phase was washed with clean water and saturated saline and dried with sodium sulfate, and concentrated to obtain a crude product. The crude product was purified with silica gel chromatography (ethyl acetate/hexane (1/1)), and solids obtained were dried under reduced pressure to obtain 6.6 g of white solids. The solids were identified as intermediate M5 by FD-MS (field desorption mass spectrometry) analysis.

(3) Synthesis of Intermediate M6 (Reaction B)

[0181] An intermediate was synthesized in the same manner as in the synthesis of intermediate M2, except that intermediate M5 was used instead of aniline and 1-bromo-4-(trimethylsilyl)benzene was used instead of intermediate Ml. The intermediate obtained was identified as intermediate M6 by FD-MS (field desorption mass spectrometry) analysis.

(4) Synthesis of Compound D-3 (Reaction C)

[0182] A compound was synthesized in the same manner as in the synthesis of D-1, except that intermediate M6 was used instead of intermediate M2. Analysis by FD-MS (field disorption mass spectrometery) was conducted for the compound obtained. The UV absorption maximum wavelength λmax and the flurescence emission maximum wavelength in the toluene solution are given below. [0183] FDMS, calcd for C.sub.64H.sub.60N.sub.2O.sub.2Si.sub.2=944, found m/z=944(M+) [0184] UV(PhMe); λmax=419 nm, FL(PhMe, λex=390 nm); λmax=452 nm

Production Example 4

Synthesis of Compound D-29 (Reaction C)

[0185] Aromatic amine derivative D-29 was produced as follows:

##STR00072##

[0186] A compound was synthesized in the same manner as in the synthesis of D-1, except that 1,6-dibromopyrene was used instead of 1,6-dibromo-3,8-diisopropylpyrene. Analysis by FD-MS (field disorption mass spectrometery) was conducted for the compound obtained. The UV absorption maximum wavelength λmax and the flurescence emission maximum wavelength in the toluene solution are given below. [0187] FDMS, calcd for C.sub.52H.sub.32N.sub.2O.sub.2=716, found m/z=716(M+) [0188] UV(PhMe); λmax=420 nm, FL(PhMe, λex=390 nm); λmax=449 nm

Production Example 5

Synthesis of Compound D-30 (Reaction C)

[0189] Aromatic amine derivative D-30 was produced as follows:

##STR00073##

[0190] A compound was synthesized in the same manner as in the synthesis of D-1, except that 1,6-dibromopyrene was used instead of 1,6-dibromo-3,8-diisopropylpyrene and intermediate M3 was used instead of intermediate M2. Analysis by FD-MS (field disorption mass spectrometery) was conducted for the compound obtained. The UV absorption maximum wavelength λmax and the flurescence emission maximum wavelength in the toluene solution are given below. [0191] FDMS, calcd for C.sub.58H.sub.44N.sub.2O.sub.2=800, found m/z=800(M+) [0192] UV(PhMe); λmax=426 nm, FL(PhMe, λex=400 nm); λmax=455 nm

Production Example 6

Synthesis of Compound D-32

[0193] Aromatic amine derivative D-32 was produced as follows:

##STR00074##

(1) Synthesis of Intermediate M7 (Reaction B)

[0194] An intermediate was synthesized in the same manner as in the synthesis of intermediate M2, except that intermediate M5 was used instead of aniline. The intermediate obtained was identified as intermediate M7 by FD-MS (field desorption mass spectrometry) analysis.

(2) Synthesis of Compound D-32 (Reaction C)

[0195] A compound was synthesized in the same manner as in the synthesis of D-1, except that intermediate M7 was used instead of intermediate M2. Analysis by FD-MS (field disorption mass spectrometery) was conducted for the compound obtained. The UV absorption maximum wavelength λmax and the flurescence emission maximum wavelength in the toluene solution are given below. [0196] FDMS, calcd for C.sub.70H.sub.48N.sub.2O.sub.2=980, found m/z=980(M+) [0197] UV(PhMe); λmax=419 nm, FL(PhMe, λex=390 nm); λmax=448 nm

Production Example 7

Synthesis of Compound D-46

[0198] Aromatic amine derivative D-46 was produced as follows:

##STR00075##

(1) Synthesis of Intermediate M8 (Reaction B)

[0199] An intermediate was synthesized in the same manner as in the synthesis of intermediate M2, except that 4-aminobenzonitrile was used instead of aniline. The intermediate obtained was identified as intermediate M8 by FD-MS (field desorption mass spectrometry) analysis.

(2) Synthesis of Compound D-46 (Reaction C)

[0200] A compound was synthesized in the same manner as in the synthesis of D-1, except that intermediate M8 was used instead of intermediate M2. Analysis by FD-MS (field disorption mass spectrometery) was conducted for the compound obtained. The UV absorption maximum wavelength λmax and the flurescence emission maximum wavelength in the toluene solution are given below. [0201] FDMS, calcd for C.sub.60H.sub.42N.sub.4O.sub.2=850, found m/z=850(M+) [0202] UV(PhMe); λmax=398 nm, FL(PhMe,λex=370 nm); λmax=444 nm

Production Example 8

Synthesis of Compound D-53

[0203] Aromatic amine derivative D-53 was produced as follows.

##STR00076##

(1) Synthesis of Intermediate M9 (Reaction B)

[0204] An intermediate was synthesized in the same manner as in the synthesis of intermediate M2, except that o-biphenylamine was used instead of aniline. The intermediate obtained was identified as intermediate M9 by FD-MS (field desorption mass spectrometry) analysis.

(2) Synthesis of Compound D-53 (Reaction C)

[0205] A compound was synthesized in the same manner as in the synthesis of D-1, except that intermediate M9 was used instead of intermediate M2 and 1,6-dibromopyrene was used instead of 1,6-dibromo-3,8-diisopropylpyrene. Analysis by FD-MS (field disorption mass spectrometery) was conducted for the compound obtained. The UV absorption maximum wavelength λmax and the flurescence emission maximum wavelength in the toluene solution are given below. [0206] FDMS, calcd for C.sub.60H.sub.40N.sub.2O.sub.2=868, found m/z=868(M+) [0207] UV(PhMe); λmax=429 nm, FL(PhMe, λex=400 nm); λmax=452 nm

Production Example 9

Synthesis of Compound D-54

[0208] Aromatic amine derivative D-54 was produced as follows:

##STR00077##

(1) Synthesis of Intermediate M10 (Reaction B)

[0209] An intermediate was synthesized in the same manner as in the synthesis of intermediate M2, except that 4-amino-3-phenylbenzonitrile was used instead of aniline. The intermediate obtained was identified as intermediate M10 by FD-MS (field desorption mass spectrometry) analysis.

(2) Synthesis of Compound D-54 (Reaction C)

[0210] A compound was synthesized in the same manner as in the synthesis of D-1, except hat 1,6-dibromopyrene was used instead of 1,6-dibromo-3,8-diisopropylpyrene and intermediate M10 was used instead of intermediate M2. Analysis by FD-MS (field disorption mass spectrometery) was conducted for the compound obtained. The UV absorption maximum wavelength λmax and the flurescence emission maximum wavelength in the toluene solution are given below. [0211] FDMS, calcd for C.sub.66H.sub.38N.sub.4O.sub.2=918, found m/z=918(M+) [0212] UV(PhMe); λmax=424 nm, FL(PhMe, λex=400 nm); λmax=449 nm

Production Example 10

Synthesis of Compound D-68 (Reaction C)

[0213] Aromatic amine derivative D-68 was produced as follows:

##STR00078##

[0214] A compound was synthesized in the same manner as in the synthesis of D-1, except that intermediate M9 was used instead of intermediate M2. Analysis by FD-MS (field disorption mass spectrometery) was conducted for the compound obtained. The UV absorption maximum wavelength λmax and the flurescence emission maximum wavelength in the toluene solution are given below. [0215] FDMS, calcd for C.sub.70H.sub.52N.sub.2O.sub.2=952, found m/z=952(M+) [0216] UV(PhMe); λmax=432 nm, FL(PhMe, λex=400 nm); λmax=456 nm

Production Example 11

Synthesis of Compound D-76

[0217] Aromatic amine derivative D-76 was produced as follows:

##STR00079##

(1) Synthesis of Intermediate M11 (Reaction B)

[0218] An intermediate was synthesized in the same manner as in the synthesis of intermediate M2, except that intermediate M5 was used instead of aniline and 1-bromonaphthalene was used instead of intermediate M1. The intermediate obtained was identified as intermediate M11 by FD-MS (field desorption mass spectrometry) analysis.

(2) Synthesis of Compound D-76 (Reaction C)

[0219] A compound was synthesized in the same manner as in the synthesis of D-1, except that intermediate M11 was used instead of intermediate M2. Analysis by FD-MS (field disorption mass spectrometery) was conducted for the compound obtained. The UV absorption maximum wavelength λmax and the flurescence emission maximum wavelength in the toluene solution are given below. [0220] FDMS, calcd for C.sub.66H.sub.48N.sub.2O.sub.2=900, found m/z=900(M+) [0221] UV(PhMe); λmax=424 nm, FL(PhMe, λex=400 nm); λmax=451 nm

Production Example 12

Synthesis of Compound D-81 (Reaction C)

[0222] Aromatic amine derivative D-81 was produced as follows:

##STR00080##

[0223] A compound was synthesized in the same manner as in the synthesis of D-1, except that 1,6-dibromo-3,8-dicyclopropylpyrene was used instead of 1,6-dibromo-3,8-diisopropylpyrene. Analysis by FD-MS (field disorption mass spectrometery) was conducted for the compound obtained. The UV absorption maximum wavelength λmax and the flurescence emission maximum wavelength in the toluene solution are given below. [0224] FDMS,calcd for C.sub.58H.sub.40N.sub.2O.sub.2=796, found m/z=796(M+) [0225] UV(PhMe); λmax=426 nm, FL(PhMe, λex=400 nm); λmax=457 nm

Production Example 13

Synthesis of Compound D-83 (Reaction C)

[0226] Aromatic amine derivative D-83 was produced as follows:

##STR00081##

[0227] A compound was synthesized in the same manner as in the synthesis of D-1, except that 1,6-dibromo-3,8-dicyclopentylpyrene was used instead of 1,6-dibromo-3,8-diisopropylpyrene. Analysis by FD-MS (field disorption mass spectrometery) was conducted for the compound obtained. The UV absorption maximum wavelength λmax and the flurescence emission maximum wavelength in the toluene solution are given below. [0228] FDMS,calcd for C.sub.62H.sub.48N.sub.2O.sub.2=852, found m/z=852(M+) [0229] UV(PhMe); λmax=420 nm, FL(PhMe, λex=390 nm); λmax=453 nm

Production Example 14

Synthesis of Compound D-88 (Reaction C)

[0230] Aromatic amine derivative D-88 was produced as follows:

##STR00082##

[0231] A compound was synthesized in the same manner as in the synthesis of D-1, except that 1,6-dibromo-3,8-dicyclopentylpyrene was used instead of 1,6-dibromo-3,8-diisopropylpyrene and intermediate M6 was used instead of intermediate M2. Analysis by FD-MS (field disorption mass spectrometery) was conducted for the compound obtained. The UV absorption maximum wavelength λmax and the flurescence emission maximum wavelength in the toluene solution are given below. [0232] FDMS, calcd for C.sub.68H.sub.64N.sub.2O.sub.2Si.sub.2=996, found m/z=996(M+) [0233] UV(PhMe); λmax=419 nm, FL(PhMe, λex=390 nm); λmax=453 nm

Production Example 15

Synthesis of Compound D-89 (Reaction C)

[0234] Aromatic amine derivative D-89 was produced as follows:

##STR00083##

[0235] A compound was synthesized in the same manner as in the synthesis of D-1, except that 1,6-dibromo-3,8-dicyclobutylpyrene was used instead of 1,6-dibromo-3,8-diisopropylpyrene. Analysis by FD-MS (field disorption mass spectrometery) was conducted for the compound obtained. The UV absorption maximum wavelength λmax and the flurescence emission maximum wavelength in the toluene solution are given below. [0236] FDMS, calcd for C.sub.60H.sub.44N.sub.2O.sub.2=824, found m/z=824(M+) [0237] UV(PhMe); λmax=425 nm, FL(PhMe, λex=400 nm); λmax=456 nm

Production Example 16

Synthesis of Compound D-90 (Reaction C)

[0238] Aromatic amine derivative D-90 was produced as follows:

##STR00084##

[0239] A compound was synthesized in the same manner as in the synthesis of D-1, except that 1,6-dibromo-3,8-di-m-tolylpyrene was used instead of 1,6-dibromo-3,8-diisopropylpyrene. Analysis by FD-MS (field disorption mass spectrometery) was conducted for the compound obtained. The UV absorption maximum wavelength λmax and the flurescence emission maximum wavelength in the toluene solution are given below. [0240] FDMS, calcd for C.sub.66H.sub.44N.sub.2O.sub.2=896, found m/z=896(M+) [0241] UV(PhMe); λmax=432 nm, FL(PhMe, λex=400 nm); λmax=468 nm

Production Example 17

Synthesis of Compound D-96

[0242] Aromatic amine derivative D-96 was produced as follows:

##STR00085##

(1) Synthesis of Intermediate M12 (Reaction A)

[0243] An intermediate was synthesized in the same manner as in the synthesis of intermediate M1, except that dibenzothiophene was used instead of dibenzofuran. The intermediate obtained was identified as intermediate M12 by FD-MS (field desorption mass spectrometry) analysis.

(2) Synthesis of Intermediate M13 (Reaction B)

[0244] An intermediate was synthesized in the same manner as in the synthesis of intermediate M2, except that intermediate M12 was used instead of intermediate M1. The intermediate obtained was identified as intermediate M13 by FD-MS (field desorption mass spectrometry) analysis.

(3) Synthesis of Compound D-96 (Reaction C)

[0245] A compound was synthesized in the same manner as in the synthesis of D-1, except that 1,6-dibromopyrene was used instead of 1,6-dibromo-3,8-diisopropylpyrene and intermediate M13 was used instead of intermediate M2. Analysis by FD-MS (field disorption mass spectrometery) was conducted for the compound obtained. The UV absorption maximum wavelength λmax and the flurescence emission maximum wavelength in the toluene solution are given below. [0246] FDMS, calcd for C.sub.52H.sub.32N.sub.2S.sub.2=748, found m/z=748(M+) [0247] UV(PhMe); λmax=423 nm, FL(PhMe, λex=400 nm); λmax=455 nm

[0248] In Examples 1 to 112 explained below, synthesis was conducted in the same manner as in Production Examples 1 to 15 for compounds of which the production example is not given.

Example 1

[0249] On a glass substrate with a dimension of 25×75×1.1 mm, a 120 nm-thick transparent electrode formed of indium tin oxide was provided. This transparent electrode functions as an anode. After subjecting to UV-ozone cleaning, the glass substrate was mounted in a vacuum vapor deposition apparatus.

[0250] First, a 60 nm-thick film formed of N′,N″-bis[4-(diphenylamino)phenyl]-N′,N″-diphenylbiphenyl-4,4′-diamine was deposited as a hole-injecting layer. Then, a 20 nm-thick film formed of N,N,N′,N′-tetrakis(4-biphenyl)-4,4′-benzidine was deposited thereon as a hole-transporting layer. Subsequently, anthracene derivative EM2 as a host material and aromatic amine derivative D-1 as a doping material were co-deposited in a mass ratio of 40:2 to form a 40 nm-thick emitting layer.

[0251] Next, as an electron-injecting layer, a 20 nm-thick film formed of tris(8-hydroxyquinolinato)aluminum was deposited on this emitting layer.

[0252] Then, a 1 nm-thick film formed of lithium fluoride was deposited, and a 150 nm-thick film formed of aluminum was deposited, whereby an organic EL device was fabricated. The aluminum/lithium fluoride layer functions as a cathode.

[0253] For the organic EL device thus obtained, device performance (luminous efficiency) at a current density of 10 mA/cm.sup.2 and the 1931 CIE (x,y) chromaticity coordinates were measured by the following methods. The results are shown in Table 1. [0254] Luminance: Measured by means of a spectroradiometer (CS-1000, manufactured by Konica Minolta Holdings, Inc.). [0255] The 1931 CIE (x,y) chromaticity coordinates: Measured by means of a spectroradiometer (CS-1000, manufactured by Konica Minolta Holdings, Inc.). [0256] Luminous efficiency (L/J): L/J is the ratio of luminance to current density. Current and voltage were measured by means of SOURCE MEASURE UNIT 236 (manufactured by Keithley Instruments Inc.) and luminance was measured by means of a spectroradiometer. Current density was calculated based on a current value and an emission area, whereby L/J was obtained. Luminous efficiency (lm/W) was obtained by the following formula.

Luminous efficiency (lm/W)=L/J/Voltage×Circular constant

Example 2

[0257] An organic EL device was fabricated and evaluated in the same manner as in Example 1, except that aromatic amine derivative D-2 was used instead of aromatic amine derivative D-1. The results are shown in Table 1.

Example 3

[0258] An organic EL device was fabricated and evaluated in the same manner as in Example 1, except that aromatic amine derivative D-3 was used instead of aromatic amine derivative D-1. The results are shown in Table 1.

Comparative Example 1

[0259] An organic EL device was fabricated and evaluated in the same manner as in Example 1, except that the following compound H-1 was used instead of aromatic amine derivative D-1. The results are shown in Table 1.

##STR00086##

TABLE-US-00001 TABLE 1 Example 1 Example 2 Example 3 Com. Ex. 1 Host material EM2 EM2 EM2 EM2 Doping material D-1 D-2 D-3 H-1 Driving voltage (V) 6.0 5.8 5.9 6.1 CIEx 0.139 0.131 0.133 0.133 CIEy 0.112 0.143 0.120 0.186 Efficiency (lm/W) 4.0 4.2 3.9 3.2

[0260] From Table 1, it is apparent that, as compared with the known compound H-1, the dibenzofuran derivative used in Examples contributed to improvement in efficiency and a significant decrease in CIEy value (emitted at a significantly shorter wavelength). The reason therefor is assumed as follows. In the compound of the invention, in the dibenzofuranyl group or the dibenzothiophenyl group, a lone pair of the nitrogen atom exerts influence on the electron density of the aromatic ring which is bonded to the nitrogen atom, and a lone pair of the oxygen atom or the sulfur atom exerts influence on the aromatic ring which is not bonded to the nitrogen atom. As a result, electron-attracting effects of the oxygen atom or the sulfur atom which has larger electronegativity than that of a carbon atom are exhibited in the aromatic ring which is bonded to the nitrogen atom. Therefore, as compared with a compound such as H-1 which has only an aromatic hydrocarbon group, the compound of the invention allows an organic EL device to emit at a shorter wavelength.

Example 4

[0261] On a glass substrate with a dimension of 25×75×1.1 mm, a 120 nm-thick transparent electrode formed of indium tin oxide was provided. This transparent electrode functions as an anode. After cleaning by irradiating UV rays and ozone, this substrate was mounted in a vacuum vapor deposition apparatus.

[0262] First, a 50 nm-thick film formed of HT-1 having the following structure was deposited as a hole-injecting layer. Then, a 45 nm-thick film formed of N,N,N′,N′-tetrakis(4-biphenyl)-4,4′-benzidine was deposited thereon. Subsequently, anthracene derivative EM9 as a host material and aromatic amine derivative D-1 as a doping material were co-deposited in a mass ratio of 25:5 to form a 30 nm-thick emitting layer.

[0263] Next, as an electron-injecting layer, a 25 nm-thick film formed of ET-1 having the following structure was deposited on this emitting layer.

[0264] Then, a 1 nm-thick film formed of lithium fluoride was deposited, and a 150 nm-thick film formed of aluminum was deposited, whereby an organic EL device was fabricated. The aluminum/lithium fluoride layer functions as a cathode.

[0265] The organic EL device thus obtained was evaluated in the same manner as in Example 1. The results are shown in Table 2.

##STR00087##

Examples 5 to 42 and Comparative Example 2

[0266] Organic EL devices were fabricated and evaluated in the same manner as in Example 4, except that the host material and the doping material were changed to those shown in Table 2. The results are shown in Table 2.

[0267] The external quantum yield was measured as follows:

[0268] Current with a current density of 10 mA/cm.sup.2 was allowed to pass through each of the organic EL devices thus obtained. Emission spectrum was measured by means of a spectroradiometer (CS-1000, manufactured by Konica Minolta Holdings, Inc) and the external quantum yield was calculated by the following expression (1):

[00001]$\begin{array}{cc}E.Q.E.=\frac{N_P}{N_E}\times 100=\frac{\frac{\left(\pi /{10}^9\right)\int \varphi \left(\lambda \right).Math.d\lambda }{\mathrm{hc}}}{\frac{J/10}{e}}\times 100=\frac{\frac{\left(\pi /{10}^9\right).Math.\left(\varphi \left(\lambda \right).Math.\left(\lambda \right)\right)}{\mathrm{hc}}}{\frac{J/10}{e}}\times 100\left(\%\right)& \mathrm{Expression}\left(1\right)\end{array}$ [0269] N.sub.P: Number of photons [0270] N.sub.E:Number of electrons [0271] π: Circular constant=3.1416 [0272] λ: Wavelength (nm) [0273] φ: Emission intensity (W/sr.Math.m.sup.2.Math.nm) [0274] h: Planck's constant=6.63×10.sup.−34 (J.Math.s) [0275] c: Speed of light=3×10.sup.8(m/s) [0276] J: Current density (mA/cm.sup.2) [0277] e: Electric charge =1.6×10.sup.−-19(C)

TABLE-US-00002 TABLE 2 External Host Doping quantum yield Examples material material CIEx CIEy (%) 4 EM9 D-1 0.136 0.100 6.3 5 EM13 D-1 0.136 0.103 7.3 6 EM28 D-1 0.136 0.104 7.3 7 EM29 D-1 0.136 0.103 7.2 8 EM31 D-1 0.136 0.105 7.3 9 EM32 D-1 0.136 0.105 7.2 10 EM69 D-1 0.136 0.104 6.8 11 EM70 D-1 0.136 0.101 6.8 12 EM73 D-1 0.137 0.103 6.9 13 EM125 D-1 0.137 0.106 6.5 14 EM133 D-1 0.137 0.107 6.5 15 EM364 D-1 0.139 0.118 6.2 16 EM367 D-1 0.135 0.104 6.7 17 EM9 D-2 0.128 0.130 6.5 18 EM13 D-2 0.128 0.133 7.2 19 EM28 D-2 0.128 0.134 7.2 20 EM29 D-2 0.128 0.133 7.1 21 EM31 D-2 0.128 0.135 7.2 22 EM32 D-2 0.128 0.135 7.1 23 EM69 D-2 0.128 0.134 6.9 24 EM70 D-2 0.128 0.131 6.8 25 EM73 D-2 0.129 0.133 6.8 26 EM125 D-2 0.129 0.136 6.6 27 EM133 D-2 0.129 0.137 6.6 28 EM364 D-2 0.131 0.148 6.3 29 EM367 D-2 0.127 0.134 6.7 30 EM9 D-3 0.130 0.108 6.4 31 EM13 D-3 0.131 0.111 7.3 32 EM28 D-3 0.131 0.112 7.3 33 EM29 D-3 0.131 0.111 7.2 34 EM31 D-3 0.131 0.113 7.3 35 EM32 D-3 0.131 0.113 7.2 36 EM69 D-3 0.130 0.112 7.1 37 EM70 D-3 0.130 0.109 6.9 38 EM73 D-3 0.131 0.111 6.9 39 EM125 D-3 0.131 0.114 6.7 40 EM133 D-3 0.131 0.115 6.7 41 EM364 D-3 0.133 0.126 6.3 42 EM367 D-3 0.130 0.112 6.7 Com. Ex. 2 EM2 H-1 0.133 0.185 5.9

Examples 43 to 71 and Comparative Example 3

[0278] Organic EL devices were fabricated and evaluated in the same manner as in Example 1, except that the host material and the doping material were changed to those shown in Table 3. The results are shown in Table 3.

[0279] The external quantum yield was measured by the same method as mentioned above.

##STR00088##

TABLE-US-00003 TABLE 3 External Doping quantum yield Examples Host material material Voltage(V) CIEx CIEy (%) 43 EM2 D-1 6.0 0.139 0.112 6.2 44 EM2 D-2 5.8 0.131 0.143 6.8 45 EM2 D-3 5.9 0.133 0.120 6.4 46 EM2 D-10 5.8 0.134 0.151 6.9 47 EM2 D-16 5.8 0.135 0.158 6.7 48 EM2 D-17 6.1 0.135 0.150 6.5 49 EM2 D-29 6.0 0.132 0.110 6.1 50 EM2 D-30 5.8 0.136 0.134 6.6 51 EM2 D-32 6.1 0.131 0.110 6.0 52 EM2 D-35 5.9 0.133 0.135 6.7 53 EM2 D-36 5.9 0.133 0.121 6.5 54 EM2 D-37 6.1 0.132 0.140 6.5 55 EM2 D-38 6.0 0.138 0.114 6.2 56 EM2 D-42 6.0 0.130 0.129 6.8 57 EM2 D-46 5.8 0.129 0.102 6.1 58 EM2 D-50 5.8 0.129 0.094 6.1 59 EM2 D-53 6.0 0.137 0.125 6.7 60 EM2 D-54 6.0 0.137 0.122 6.9 61 EM2 D-59 6.1 0.132 0.093 5.9 62 EM2 D-65 6.0 0.132 0.110 6.1 63 EM2 D-68 6.0 0.137 0.130 6.6 64 EM2 D-76 6.1 0.131 0.131 6.0 65 EM2 D-83 6.0 0.139 0.114 6.1 66 EM2 D-84 6.0 0.137 0.120 6.5 67 EM2 D-85 6.0 0.137 0.099 6.0 68 EM2 D-86 6.0 0.130 0.125 6.8 69 EM2 D-88 6.0 0.139 0.114 6.3 70 EM2 D-90 5.7 0.139 0.169 7.0 71 EM2 D-94 5.9 0.135 0.165 6.8 Com. Ex. 3 EM2 H-2 5.9 0.137 0.180 4.1

Example 72

[0280] A glass substrate (GEOMATEC CO., LTD.) of 25 mm×75 mm×1.1 mm with an ITO transparent electrode (anode) was subjected to ultrasonic cleaning with isopropyl alcohol for 5 minutes, and cleaned with ultraviolet rays and ozone for 30 minutes. The resultant glass substrate with transparent electrode lines was mounted on a substrate holder in a vacuum vapor deposition apparatus. First, compound A-1 shown below was formed into a film in a thickness of 50 nm on the surface of the transparence electrode on which the transparence electrode lines were formed so as to cover the transparent electrode. Subsequent to the formation of the A-1 film, compound A-2 shown below was formed thereon into a film in a thickness of 45 nm.

[0281] Further, on this A-2 film, compound EM31 as a host material and compound D-1 of the invention as a doping material were formed into a film in a thickness of 25 nm with a film thickness ratio of 20:1, whereby a blue emitting layer was formed.

[0282] On this film, as an electron-transporting layer, ET-2 having the following structure was formed into a 25 nm-thick film by deposition. Thereafter, LiF was formed into a 1 nm-thick film. Metal Al was deposited in a thickness of 150 nm as a metal cathode, thereby fabricating an organic EL device.

[0283] The resulting organic emitting device was evaluated in the same manner as in Example 1. The external quantum yield was measured by the same method as mentioned above. The results are shown in Table 4.

##STR00089##

Examples 73 to 112 and Comparative Examples 4 and 5

[0284] Organic EL devices were fabricated and evaluated in the same manner as in Example 72, except that the host material and the doping material were changed to those shown in Table 4. The external quantum yield was measured by the same method as mentioned above. The results are shown in Table 4.

##STR00090##

TABLE-US-00004 TABLE 4 External Doping quantum yield Examples Host material material Voltage(V) CIEx CIEy (%) 72 EM31 D-1 3.6 0.138 0.095 8.0 73 EM31 D-2 3.5 0.138 0.120 8.2 74 EM31 D-29 3.6 0.137 0.093 7.6 75 EM31 D-30 3.5 0.139 0.108 7.8 76 EM31 D-38 3.6 0.138 0.100 7.9 77 EM31 D-42 3.6 0.138 0.116 8.1 78 EM31 D-46 3.4 0.137 0.084 7.2 79 EM31 D-50 3.4 0.137 0.080 7.0 80 EM31 D-53 3.6 0.138 0.100 8.1 81 EM31 D-54 3.5 0.138 0.098 7.8 82 EM31 D-65 3.6 0.139 0.101 7.9 83 EM31 D-68 3.6 0.138 0.105 8.1 84 EM31 D-83 3.5 0.137 0.102 8.0 85 EM31 D-85 3.6 0.137 0.102 7.9 86 EM31 D-86 3.6 0.138 0.114 8.1 87 EM31 D-90 3.4 0.140 0.159 7.7 88 EM116 D-1 3.6 0.137 0.090 7.4 89 EM116 D-2 3.6 0.138 0.110 7.8 90 EM116 D-29 3.7 0.138 0.088 7.0 91 EM116 D-30 3.6 0.139 0.100 7.4 92 EM116 D-38 3.5 0.138 0.096 7.5 93 EM116 D-42 3.6 0.138 0.102 7.5 94 EM116 D-46 3.7 0.138 0.080 6.8 95 EM116 D-50 3.6 0.137 0.079 6.6 96 EM116 D-53 3.6 0.137 0.097 7.4 97 EM116 D-54 3.7 0.138 0.090 7.4 98 EM116 D-65 3.6 0.138 0.097 7.5 99 EM116 D-68 3.6 0.138 0.101 7.7 100 EM116 D-83 3.6 0.138 0.096 7.5 101 EM116 D-85 3.7 0.139 0.095 7.4 102 EM116 D-86 3.6 0.139 0.104 7.7 103 EM116 D-90 3.5 0.138 0.145 7.3 104 EM205 D-1 3.6 0.138 0.096 8.1 105 EM205 D-2 3.6 0.137 0.122 8.2 106 EM205 D-46 3.5 0.138 0.088 7.4 107 EM205 D-50 3.5 0.137 0.081 7.1 108 EM205 D-53 3.6 0.138 0.100 8.2 109 EM205 D-54 3.6 0.138 0.100 8.0 110 EM205 D-68 3.6 0.138 0.104 8.1 111 EM205 D-83 3.6 0.139 0.103 8.2 112 EMP1 D-1 3.2 0.143 0.115 6.8 Com. Ex. 4 EMP1 H-2 3.2 0.143 0.201 5.8 Com. Ex. 5 EM31 H-2 3.6 0.137 0.178 5.2

[0285] From Tables 1 to 4, it can be understood that the devices of Examples maintained high efficiency and exhibited high color reproducibility. As a result, the invention can realize a display device which exhibit high color reproducibility at low power consumption.

INDUSTRIAL APPLICABLITY

[0286] The organic EL device of the invention can be suitably used as a planar emitting body such as a flat panel display of a wall-hanging television, backlight of a copier, a printer, or a liquid crystal display, light sources for instruments, a display panel, a navigation light, and the like.

[0287] Although only some exemplary embodiments and/or examples of this invention have been described in detail above, those skilled in the art will readily appreciate that many modifications are possible in the exemplary embodiments and/or examples without materially departing from the novel teachings and advantages of this invention. Accordingly, all such modifications are intended to be included within the scope of this invention.

[0288] The documents described in the specification are incorporated herein by reference in its entirety.