Organic electroluminescent device

Abstract

An organic electroluminescent device having low driving voltage, high luminous efficiency, and a long lifetime is provided by combining various materials for an organic EL device, which are excellent, as materials for an organic electroluminescent device having high efficiency and high durability, in hole and electron injection/transport performances, electron blocking ability, stability in a thin-film state and durability, so as to allow the respective materials to effectively reveal their characteristics. In the organic electroluminescent device having at least an anode, a hole transport layer, a light emitting layer, an electron transport layer and a cathode in this order, the hole transport layer includes an arylamine compound represented by the following general formula (1), and the light emitting layer includes an amine derivative of the following general formula (2) having a condensed ring structure.
[Chemical Formula 1] ##STR00001##

Claims

1. An organic electroluminescent device comprising at least an anode, a hole transport layer, a light emitting layer, an electron transport layer and a cathode in this order, wherein the hole transport layer has a two-layer structure of a first hole transport layer and a second hole transport layer, and the second hole transport layer comprises an arylamine compound of general formula (1): ##STR00135## wherein Ar.sub.1 to Ar.sub.4 may be the same or different, and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group; and the light emitting layer comprises an amine derivative of general formula (2a-a), (2a-b), (2b-a), (2b-b), (2b-c), (2b-d), (2c-a) or (2c-b), having a condensed ring structure: ##STR00136## ##STR00137## wherein A.sub.1 represents a divalent group of a substituted or unsubstituted aromatic hydrocarbon, a divalent group of a substituted or unsubstituted aromatic heterocyclic ring, a divalent group of substituted or unsubstituted condensed polycyclic aromatics, or a single bond; Ar.sub.5 and Ar.sub.6 may be the same or different, and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, where Ar.sub.5 and Ar.sub.6 may bind to each other via a single bond, substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom to form a ring; X and Y may be the same or different, each representing an oxygen atom or a sulfur atom; R.sub.1 to R.sub.4 may be the same or different, and represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano, nitro, linear or branched alkyl of 1 to 6 carbon atoms that may have a substituent, cycloalkyl of 5 to 10 carbon atoms that may have a substituent, linear or branched alkenyl of 2 to 6 carbon atoms that may have a substituent, linear or branched alkyloxy of 1 to 6 carbon atoms that may have a substituent, cycloalkyloxy of 5 to 10 carbon atoms that may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, substituted or unsubstituted aryloxy, or a disubstituted amino group substituted with a group selected from an aromatic hydrocarbon group, an aromatic heterocyclic group, and a condensed polycyclic aromatic group, where R.sub.1 to R.sub.4 may bind to each other via a single bond, substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom to form a ring, and R.sub.1 to R.sub.4 and the benzene ring binding with R.sub.1 to R.sub.4 may bind to each other via substituted or unsubstituted methylene, an oxygen atom, a sulfur atom, or a mono-substituted amino group; R.sub.5 to R.sub.7 may be the same or different, represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano, nitro, linear or branched alkyl of 1 to 6 carbon atoms that may have a substituent, cycloalkyl of 5 to 10 carbon atoms that may have a substituent, linear or branched alkenyl of 2 to 6 carbon atoms that may have a substituent, linear or branched alkyloxy of 1 to 6 carbon atoms that may have a substituent, cycloalkyloxy of 5 to 10 carbon atoms that may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or substituted or unsubstituted aryloxy, wherein at least one of R.sub.5 to R.sub.7 is a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, and where R.sub.5 to R.sub.7 may bind to each other via a single bond, substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom to form a ring, and R.sub.5 to R.sub.7 and the benzene ring binding with R.sub.5 to R.sub.7 may bind to each other via substituted or unsubstituted methylene, an oxygen atom, a sulfur atom, or a mono-substituted amino group; and R.sub.8 and R.sub.9 may be the same or different, linear or branched alkyl of 1 to 6 carbon atoms that may have a substituent, cycloalkyl of 5 to 10 carbon atoms that may have a substituent, linear or branched alkenyl of 2 to 6 carbon atoms that may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or substituted or unsubstituted aryloxy, where R.sub.8 and R.sub.9 may bind to each other via a single bond, substituted or unsubstituted methylene, an oxygen atom, a sulfur atom, or a mono-substituted amino group to form a ring.

2. The organic electroluminescent device according to claim 1, wherein the electron transport layer comprises a compound of the following general formula (3) having an anthracene ring structure, ##STR00138## wherein A.sub.2 represents a divalent group of a substituted or unsubstituted aromatic hydrocarbon, a divalent group of a substituted or unsubstituted aromatic heterocyclic ring, a divalent group of substituted or unsubstituted condensed polycyclic aromatics, or a single bond; B represents a substituted or unsubstituted aromatic heterocyclic group; C represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group; D may be the same or different, and represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano, trifluoromethyl, linear or branched alkyl of 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group; and p represents 7 or 8, and q represents 1 or 2 while maintaining a relationship that a sum of p and q is 9.

3. The organic electroluminescent device according to claim 2, wherein the compound having an anthracene ring structure is a compound of the following general formula (3a) having an anthracene ring structure, ##STR00139## wherein A.sub.2 represents a divalent group of a substituted or unsubstituted aromatic hydrocarbon, a divalent group of a substituted or unsubstituted aromatic heterocyclic ring, a divalent group of substituted or unsubstituted condensed polycyclic aromatics, or a single bond; Ar.sub.7, Ar.sub.8, and Ar.sub.9 may be the same or different, and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group; R.sub.10 to R.sub.16 may be the same or different, and represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano, nitro, linear or branched alkyl of 1 to 6 carbon atoms that may have a substituent, cycloalkyl of 5 to 10 carbon atoms that may have a substituent, linear or branched alkenyl of 2 to 6 carbon atoms that may have a substituent, linear or branched alkyloxy of 1 to 6 carbon atoms that may have a substituent, cycloalkyloxy of 5 to 10 carbon atoms that may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or substituted or unsubstituted aryloxy, where R.sub.10 to R.sub.16 may bind to each other via a single bond, substituted or unsubstituted methylene, an oxygen atom, or a sulfur atom to form a ring; and X.sub.1, X.sub.2, X.sub.3, and X.sub.4 represent a carbon atom or a nitrogen atom, where only one of X.sub.1, X.sub.2, X.sub.3, and X.sub.4 is a nitrogen atom, and the nitrogen atom in this case does not have the hydrogen atom or the substituent for R.sub.10 to R.sub.13.

4. The organic electroluminescent device according to claim 2, wherein the compound having an anthracene ring structure is a compound of the following general formula (3b) having an anthracene ring structure, ##STR00140## wherein A.sub.2 represents a divalent group of a substituted or unsubstituted aromatic hydrocarbon, a divalent group of a substituted or unsubstituted aromatic heterocyclic ring, a divalent group of substituted or unsubstituted condensed polycyclic aromatics, or a single bond; Ar.sub.10, Ar.sub.11, and Ar.sub.12 may be the same or different, and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group.

5. The organic electroluminescent device according to claim 2, wherein the compound having an anthracene ring structure is a compound of the following general formula (3c) having an anthracene ring structure, ##STR00141## wherein A.sub.2 represents a divalent group of a substituted or unsubstituted aromatic hydrocarbon, a divalent group of a substituted or unsubstituted aromatic heterocyclic ring, a divalent group of substituted or unsubstituted condensed polycyclic aromatics, or a single bond; Ar.sub.13, Ar.sub.14, and Ar.sub.15 may be the same or different, and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group; and R.sub.17 represents a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, cyano, nitro, linear or branched alkyl of 1 to 6 carbon atoms that may have a substituent, cycloalkyl of 5 to 10 carbon atoms that may have a substituent, linear or branched alkenyl of 2 to 6 carbon atoms that may have a substituent, linear or branched alkyloxy of 1 to 6 carbon atoms that may have a substituent, cycloalkyloxy of 5 to 10 carbon atoms that may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or substituted or unsubstituted aryloxy.

6. The organic electroluminescent device according to claim 1, wherein the light emitting layer comprises an anthracene derivative.

7. The organic electroluminescent device according to claim 6, wherein the light emitting layer comprises a host material that is an anthracene derivative.

8. The organic electroluminescent device according to claim 2, wherein the light emitting layer comprises an anthracene derivative.

9. The organic electroluminescent device according to claim 3, wherein the light emitting layer comprises an anthracene derivative.

10. The organic electroluminescent device according to claim 4, wherein the light emitting layer comprises an anthracene derivative.

11. The organic electroluminescent device according to claim 5, wherein the light emitting layer comprises an anthracene derivative.

12. The organic electroluminescent device according to claim 8, wherein the light emitting layer comprises a host material that is an anthracene derivative.

13. The organic electroluminescent device according to claim 9, wherein the light emitting layer comprises a host material that is an anthracene derivative.

14. The organic electroluminescent device according to claim 10, wherein the light emitting layer comprises a host material that is an anthracene derivative.

Description

BRIEF DESCRIPTION OF THE DRAWING

(1) The FIGURE is a diagram illustrating the configuration of the organic EL devices of Examples 37 to 42 and Comparative Examples 1 and 2.

MODE FOR CARRYING OUT THE INVENTION

(2) The following presents specific examples of preferred compounds among the arylamine compounds of the general formula (1) preferably used in the organic EL device of the present invention. The present invention, however, is not restricted to these compounds.

(3) ##STR00018## ##STR00019## ##STR00020## ##STR00021## ##STR00022## ##STR00023## ##STR00024## ##STR00025## ##STR00026## ##STR00027## ##STR00028## ##STR00029## ##STR00030## ##STR00031## ##STR00032## ##STR00033## ##STR00034## ##STR00035## ##STR00036## ##STR00037##

(4) The following presents specific examples of preferred compounds among the amine derivatives of the general formula (2) having a condensed ring structure preferably used in the organic EL device of the present invention. The present invention, however, is not restricted to these compounds.

(5) ##STR00038## ##STR00039## ##STR00040## ##STR00041## ##STR00042## ##STR00043## ##STR00044## ##STR00045## ##STR00046##

(6) The following presents specific examples of preferred compounds among the compounds of the general formula (3a) having an anthracene ring structure preferably used in the organic EL device of the present invention. The present invention, however, is not restricted to these compounds.

(7) ##STR00047## ##STR00048## ##STR00049## ##STR00050## ##STR00051## ##STR00052## ##STR00053##

(8) The following presents specific examples of preferred compounds among the compounds of the general formula (3b) having an anthracene ring structure and preferably used in the organic EL device of the present invention. The present invention, however, is not restricted to these compounds.

(9) ##STR00054## ##STR00055## ##STR00056## ##STR00057## ##STR00058## ##STR00059## ##STR00060##

(10) The following presents specific examples of preferred compounds among the compounds of the general formula (3c) having an anthracene ring structure and preferably used in the organic EL device of the present invention. The present invention, however, is not restricted to these compounds.

(11) ##STR00061## ##STR00062## ##STR00063## ##STR00064## ##STR00065## ##STR00066## ##STR00067## ##STR00068## ##STR00069## ##STR00070## ##STR00071## ##STR00072## ##STR00073## ##STR00074## ##STR00075##

(12) The compounds described above having an anthracene ring structure can be synthesized by a known method (refer to Patent Documents 6 to 8, for example).

(13) In the organic EL device of the present invention, the following presents specific examples of preferred compounds among the arylamine compounds of the general formula (4) having two triphenylamine structures within a molecule and preferably used in the first hole transport layer in the case where the hole transport layer has a two-layer structure of the first hole transport layer and the second hole transport layer. The present invention, however, is not restricted to these compounds.

(14) ##STR00076## ##STR00077## ##STR00078## ##STR00079## ##STR00080## ##STR00081## ##STR00082## ##STR00083## ##STR00084##

(15) In the organic EL device of the present invention, the following presents specific examples of preferred compounds in the arylamine compounds preferably used in the first hole transport layer and having two triphenylamine structures within a molecule in the arylamine compounds having a structure in which two to six triphenylamine structures are joined within a molecule via a single bond or a divalent group that does not contain a heteroatom in the case where the hole transport layer has a two-layer structure of the first hole transport layer and the second hole transport layer, besides the arylamine compounds of the general formula (4) having two triphenylamine structures within a molecule. The present invention, however, is not restricted to these compounds.

(16) ##STR00085##

(17) In the organic EL device of the present invention, the following presents specific examples of preferred compounds among the arylamine compounds of the general formula (5) having four triphenylamine structures within a molecule and preferably used in the first hole transport layer in the case where the hole transport layer has a two-layer structure of the first hole transport layer and the second hole transport layer. The present invention, however, is not restricted to these compounds.

(18) ##STR00086## ##STR00087## ##STR00088## ##STR00089## ##STR00090## ##STR00091## ##STR00092## ##STR00093## ##STR00094##

(19) The arylamine compounds of the general formula (4) having two triphenylamine structures within a molecule, and the arylamine compounds of the general formula (5) having four triphenylamine structures within a molecule can be synthesized by a known method (refer to Patent Documents 9 to 11, for example).

(20) The arylamine compounds of the general formula (1) were purified by methods such as column chromatography; adsorption using, for example, a silica gel, activated carbon, or activated clay; recrystallization or crystallization using a solvent; and sublimation. The compounds were identified by an NMR analysis. A glass transition point (Tg) and a work function were measured as material property values. The glass transition point (Tg) can be used as an index of stability in a thin-film state, and the work function can be used as an index of hole transportability.

(21) Other compounds used for the organic EL device of the present invention were purified by methods such as column chromatography; adsorption using, for example, a silica gel, activated carbon, or activated clay; and recrystallization or crystallization using a solvent; and finally purified by sublimation.

(22) The glass transition point (Tg) was measured by a high-sensitive differential scanning calorimeter (DSC3100S produced by Bruker AXS) using powder.

(23) For the measurement of the work function, a 100 nm-thick thin film was fabricated on an ITO substrate, and an ionization potential measuring device (PYS-202 produced by Sumitomo Heavy Industries, Ltd.) was used.

(24) The organic EL device of the present invention may have a structure including an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode successively formed on a substrate, optionally with an electron blocking layer between the hole transport layer and the light emitting layer, a hole blocking layer between the light emitting layer and the electron transport layer, and an electron injection layer between the electron transport layer and the cathode. Some of the organic layers in the multilayer structure may be omitted, or may serve more than one function. For example, a single organic layer may serve as the hole injection layer and the hole transport layer, or as the electron injection layer and the electron transport layer. Further, the organic layers having a same function may have a laminate structure of two or more layers, for example, the hole transport layer may have a two-layer structure, the light emitting layer may have a two-layer structure, or the electron transport layer may have a two-layer structure. The hole transport layer preferably also has a two-layer structure of a first hole transport layer and a second hole transport layer as a structure of the organic EL device of the present invention.

(25) Electrode materials with high work functions such as ITO and gold are used as the anode of the organic EL device of the present invention. The hole injection layer of the organic EL device of the present invention may be made of, for example, material such as starburst-type triphenylamine derivatives and various triphenylamine tetramers; porphyrin compounds as represented by copper phthalocyanine; accepting heterocyclic compounds such as hexacyano azatriphenylene; and coating-type polymer materials, in addition to the arylamine compounds of the general formula (1). These materials may be formed into a thin film by a vapor deposition method or other known methods such as a spin coating method and an inkjet method.

(26) The arylamine compounds of the general formula (1) are used as the hole transport layer of the organic EL device of the present invention. These may be individually deposited for film forming, may be used as a single layer deposited mixed with other hole transporting materials, or may be formed as a laminate of individually deposited layers, a laminate of mixedly deposited layers, or a laminate of the individually deposited layer and the mixedly deposited layer. These materials may be formed into a thin-film by a vapor deposition method or other known methods such as a spin coating method and an inkjet method.

(27) Examples of a hole transporting material that can be mixed or can be used at the same time with the arylamine compounds of the general formula (1) can be benzidine derivatives such as N,N-diphenyl-N,N-di(m-tolyl)benzidine (TPD), N,N-diphenyl-N,N-di(-naphthyl)benzidine (NPD), and N,N,N,N-tetrabiphenylylbenzidine; 1,1-bis[4-(di-4-tolylamino)phenyl]cyclohexane (TAPC); arylamine compounds having a structure in which two triphenylamine structures are joined within a molecule via a single bond or a divalent group that does not contain a heteroatom such as the arylamine compounds of the general formula (4); arylamine compounds having a structure in which four triphenylamine structures are joined within a molecule via a single bond or a divalent group that does not contain a heteroatom such as the arylamine compounds of the general formula (5); and various triphenylamine trimers.

(28) The material used for the hole injection layer or the hole transport layer may be obtained by p-doping materials such as trisbromophenylamine hexachloroantimony, and radialene derivatives (refer to WO2014/009310, for example) into a material commonly used for these layers, or may be, for example, polymer compounds each having, as a part of the compound structure, a structure of a benzidine derivative such as TPD.

(29) In the case where the hole transport layer of the organic EL device of the present invention has a two-layer structure, the above hole transporting materials are used as the first hole transport layer, in addition to the arylamine compounds of the general formula (4) having two triphenylamine structures within a molecule, and the arylamine compounds of the general formula (5) having four triphenylamine structures within a molecule.

(30) The above hole transporting materials are used as the second hole transport layer in addition to the arylamine compounds of the general formula (1).

(31) Examples of material used for the electron blocking layer of the organic EL device of the present invention can be compounds having an electron blocking effect, including, for example, carbazole derivatives such as 4,4,4-tri(N-carbazolyl)triphenylamine (TCTA), 9,9-bis[4-(carbazol-9-yl)phenyl]fluorene, 1,3-bis(carbazol-9-yl)benzene (mCP), and 2,2-bis(4-carbazol-9-ylphenyl)adamantane (Ad-Cz); and compounds having a triphenylsilyl group and a triarylamine structure, as represented by 9-[4-(carbazol-9-yl)phenyl]-9-[4-(triphenylsilyl)phenyl]-9H-fluorene, in addition to the arylamine compounds of the general formula (1). These may be individually deposited for film forming, may be used as a single layer deposited mixed with other materials, or may be formed as a laminate of individually deposited layers, a laminate of mixedly deposited layers, or a laminate of the individually deposited layer and the mixedly deposited layer. These materials may be formed into a thin-film by using a vapor deposition method or other known methods such as a spin coating method and an inkjet method.

(32) Examples of material used for the light emitting layer of the organic EL device of the present invention can be various metal complexes including, for example, quinolinol derivative metal complexes such as Alq.sub.3; anthracene derivatives; bis(styryl)benzene derivatives; pyrene derivatives; oxazole derivatives; and polyparaphenylene vinylene derivatives; in addition to the amine derivatives of the general formula (2) having a condensed ring structure. Further, the light emitting layer may be made of a host material and a dopant material. Examples of the host material can be thiazole derivatives, benzimidazole derivatives, and polydialkyl fluorene derivatives, in addition to the above light-emitting materials. Examples of the dopant material can be quinacridone, coumarin, rubrene, perylene, pyrene, derivatives thereof, benzopyran derivatives, indenophenanthrene derivatives, rhodamine derivatives, and aminostyryl derivatives in addition to the amine derivatives of the general formula (2) having a condensed ring structure. These may be individually deposited for film forming, may be used as a single layer deposited mixed with other materials, or may be formed as a laminate of individually deposited layers, a laminate of mixedly deposited layers, or a laminate of the individually deposited layer and the mixedly deposited layer.

(33) The dopant material in the light emitting layer of the organic EL device of the present invention is preferably the amine derivatives of the general formula (2) having a condensed ring structure.

(34) Further, the light-emitting material may be a phosphorescent material. Phosphorescent materials as metal complexes of metals such as iridium and platinum may be used. Examples of the phosphorescent materials include green phosphorescent materials such as Ir(ppy).sub.3, blue phosphorescent materials such as FIrpic and FIr6, and red phosphorescent materials such as Btp.sub.2Ir(acac). Here, carbazole derivatives such as 4,4-di(N-carbazolyl)biphenyl (CBP), TCTA, and mCP may be used as the hole injecting and transporting host material. Compounds such as p-bis(triphenylsilyl)benzene (UGH2), and 2,2,2-(1,3,5-phenylene)-tris(1-phenyl-1H-benzimidazole) (TPBI) may be used as the electron transporting host material. In this way, a high-performance organic EL device can be produced.

(35) In order to avoid concentration quenching, the doping of the host material with the phosphorescent light-emitting material should preferably be made by co-evaporation in a range of 1 to 30 weight percent with respect to the whole light emitting layer.

(36) Further, Examples of the light-emitting material may be delayed fluorescent-emitting material such as a CDCB derivative of PIC-TRZ, CC2TA, PXZ-TRZ, 4CzIPN or the like (refer to Non-Patent Document 3, for example).

(37) These materials may be formed into a thin-film by using a vapor deposition method or other known methods such as a spin coating method and an inkjet method.

(38) The hole blocking layer of the organic EL device of the present invention may be formed by using hole blocking compounds such as various rare earth complexes, triazole derivatives, triazine derivatives, and oxadiazole derivatives, in addition to the metal complexes of phenanthroline derivatives such as bathocuproin (BCP), and the metal complexes of quinolinol derivatives such as aluminum(III) bis(2-methyl-8-quinolinate)-4-phenylphenolate (BAlq). These materials may also serve as the material of the electron transport layer. These may be individually deposited for film forming, may be used as a single layer deposited mixed with other materials, or may be formed as a laminate of individually deposited layers, a laminate of mixedly deposited layers, or a laminate of the individually deposited layer and the mixedly deposited layer. These materials may be formed into a thin-film by using a vapor deposition method or other known methods such as a spin coating method and an inkjet method.

(39) Material used for the electron transport layer of the organic EL device of the present invention can be the compounds of the general formula (3) having an anthracene ring structure, far preferably, the compounds of the general formulas (3a), (3b), or (3c) having an anthracene ring structure. These may be individually deposited for film forming, may be used as a single layer deposited mixed with other electron transporting materials, or may be formed as a laminate of individually deposited layers, a laminate of mixedly deposited layers, or a laminate of the individually deposited layer and the mixedly deposited layer. These materials may be formed into a thin film by a vapor deposition method or other known methods such as a spin coating method and an inkjet method.

(40) Examples of the electron transporting material that can be mixed or can be used at the same time with the compounds of the general formula (3) having an anthracene ring structure can be various metal complexes, including, for example, metal complexes of quinolinol derivatives such as Alq.sub.3 and BAlq, triazole derivatives, triazine derivatives, oxadiazole derivatives, pyridine derivatives, pyrimidine derivatives, benzimidazole derivatives, thiadiazole derivatives, anthracene derivatives, carbodiimide derivatives, quinoxaline derivatives, pyridoindole derivatives, phenanthroline derivatives, and silole derivatives.

(41) Examples of material used for the electron injection layer of the organic EL device of the present invention can be alkali metal salts such as lithium fluoride and cesium fluoride; alkaline earth metal salts such as magnesium fluoride; and metal oxides such as aluminum oxide. However, the electron injection layer may be omitted in the preferred selection of the electron transport layer and the cathode.

(42) The cathode of the organic EL device of the present invention may be made of an electrode material with a low work function such as aluminum, or an alloy of an electrode material with an even lower work function such as a magnesium-silver alloy, a magnesium-indium alloy, or an aluminum-magnesium alloy.

(43) The following describes an embodiment of the present invention in more detail based on Examples. The present invention, however, is not restricted to the following Examples.

Example 1

Synthesis of 4-{(biphenyl-4-yl)-phenylamino}-4-{(9,9-dimethyl-9H-fluoren-2-yl)-phenylamino}-1,1:3,1-terphenyl (Compound 1-5)

(44) N-(biphenyl-4-yl)-N-(4-bromophenyl)aniline (8.0 g), N-(9,9-dimethyl-9H-fluoren-2-yl)-N-{3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-4-yl}aniline (11.4 g), potassium carbonate (7.5 g), water (64 ml), toluene (64 ml), ethanol (16 ml), and tetrakis(triphenylphosphine)palladium (0.8 g) were added into a nitrogen-substituted reaction vessel, and the mixture was heated and stirred at 70 C. for 16 hours. The mixture was cooled to a room temperature, and an organic layer was collected by liquid separation after adding ethyl acetate and water. After the organic layer was concentrated, recrystallization with a THF/acetone mixed solvent was carried out to obtain a white powder of 4-{(biphenyl-4-yl)-phenylamino}-4-{(9,9-dimethyl-9H-fluoren-2-yl)-phenylamino}-1,1:3,1-terphenyl (Compound 1-5; 9.54 g; yield 69%).

(45) ##STR00095##

(46) The structure of the obtained white powder was identified by NMR.

(47) .sup.1H-NMR (THF-d.sub.8) detected 44 hydrogen signals, as follows.

(48) (ppm)=7.86 (1H), 7.68-6.97 (37H), 1.41 (6H).

Example 2

Synthesis of 4-{(biphenyl-4-yl)-phenylamino}-4-{(naphthalene-1-yl)-phenylamino}-1,1:3,1-terphenyl (Compound 1-6)

(49) The reaction was carried out under the same conditions as those of Example 1, except that N-(biphenyl-4-yl)-N-(4-bromophenyl)aniline was replaced with N-(3-bromobiphenyl-4-yl)-N-(naphthalene-1-yl)aniline, and N-(9,9-dimethyl-9H-fluoren-2-yl)-N-{3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-4-yl}aniline was replaced with 4-{N-(9,9-dimethyl-9H-fluorene-2-yl)-phenylamino}-phenylboronic acid. As a result, a pale yellowish white powder of 4-{(biphenyl-4-yl)-phenylamino}-4-{(naphthalene-1-yl)-phenylamino}-1,1:3,1-terphenyl (Compound 1-6; 7.88 g; yield 62%) was obtained.

(50) ##STR00096##

(51) The structure of the obtained pale yellowish white powder was identified by NMR.

(52) .sup.1H-NMR (CDCl.sub.3) detected 42 hydrogen signals, as follows.

(53) (ppm)=7.98 (1H), 7.92 (1H), 7.84-7.75 (2H), 7.70-6.94 (32H), 1.49 (6H).

Example 3

Synthesis of 3,3-bis{(biphenyl-4-yl)-phenylamino}-1,1:4,1-terphenyl (Compound 1-21)

(54) 1,4-dibromobenzene (6.20 g), (biphenyl-4-yl)-{3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl}-phenylamine (25.1 g), potassium carbonate (10.8 g), water (39 ml), toluene (380 ml), and ethanol (95 ml) were added into a nitrogen-substituted reaction vessel and aerated with nitrogen gas under ultrasonic irradiation for 30 minutes. The mixture was heated after adding tetrakis(triphenylphosphine)palladium (0.95 g), and stirred for 18 hours under reflux. The mixture was cooled to a room temperature, and water (200 ml), and heptane (190 ml) was added. A precipitate was collected by filtration. The precipitate was dissolved under heat in 1,2-dichlorobenzene (1200 ml) and purified by adsorption with a silica gel (39 g) and further purified by adsorption with an activated clay (19 g). A crude product precipitated by adding methanol (725 ml) was collected by filtration. After the crude product was repeatedly crystallized with 1,2-dichloromethane/methanol mixed solvent, the product was washed under reflux with methanol (300 ml) to obtain a white powder of 3,3-bis{(biphenyl-4-yl)-phenylamino}-1,1:4,1-terphenyl (Compound 1-21; 15.22 g; yield 81%).

(55) ##STR00097##

(56) The structure of the obtained white powder was identified by NMR.

(57) .sup.1H-NMR (CDCl.sub.3) detected 40 hydrogen signals, as follows.

(58) (ppm)=7.61 (2H), 7.56-6.83 (38H).

Example 4

Synthesis of 2,2-bis{(biphenyl-4-yl)-phenylamino}-1,1:4,1-terphenyl (Compound 1-22)

(59) The reaction was carried out under the same conditions as those of Example 3, except that (biphenyl-4-yl)-{3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl}-phenylamine was replaced with N-(biphenyl-4-yl)-N-{2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl}-phenylamine. As a result, a white powder of 2,2-bis{(biphenyl-4-yl)-phenylamino}-1,1:4,1-terphenyl (Compound 1-22; 11.11 g; yield 58%) was obtained.

(60) ##STR00098##

(61) The structure of the obtained white powder was identified by NMR.

(62) .sup.1H-NMR (THF-d.sub.8) detected 40 hydrogen signals, as follows.

(63) (ppm)=7.52 (4H), 7.40-7.20 (18H), 7.03 (8H), 6.90-6.75 (10H).

Example 5

Synthesis of 4-{bis(biphenyl-4-yl)amino}-2-{(9,9-dimethyl-9H-fluorene-2-yl)-phenylamino}-1,1:4,1-terphenyl (Compound 1-32)

(64) N-(biphenyl-4-yl)-N-(2-bromo-1,1:4,1-terphenyl-4-yl)aniline (10.0 g), 2-(phenylamino)-9,9-dimethyl-9H-fluoren (6.2 g), palladium acetate (0.081 g), tert-butoxy sodium (3.5 g), a toluene solution (0.146 g) containing 50% (w/v) tri-tert-butylphosphine, toluene (100 ml) were added into a nitrogen-substituted reaction vessel, and the mixture was heated and stirred at 100 C. overnight. After the insoluble matter was removed by filtration and the filtrate was concentrated, purification by column chromatography

(65) (support: silica gel, eluent: heptane/dichloromethane) was performed to obtain a white powder of 4-{bis(biphenyl-4-yl)amino}-2-{(9,9-dimethyl-9H-fluorene-2-yl)-phenylamino}-1,1:4,1-terphenyl (Compound 1-32; 4.77 g; yield 35%).

(66) ##STR00099##

(67) The structure of the obtained white powder was identified by NMR.

(68) .sup.1H-NMR (THF-d.sub.8) detected 44 hydrogen signals, as follows.

(69) (ppm)=7.61-7.48 (4H), 7.42-6.92 (32H), 6.81 (1H), 6.76 (1H), 1.28 (6H).

Example 6

Synthesis of 4,4-bis{(9,9-dimethyl-9H-fluorene-2-yl)-phenylamino}-1,1:3,1-terphenyl (Compound 1-34)

(70) 4,4-dibromo-1,1:3,1-terphenyl (8.81 g), 2-(phenylamino)-9,9-dimethyl-9H-fluoren (13.6 g), tert-butoxy sodium (5.12 g), tris(dibenzylideneacetone)dipalladium (0.33 g), a toluene solution (0.63 ml) containing 50% (w/v) tri-tert-butylphosphine were added into a nitrogen-substituted reaction vessel, and the mixture was heated and stirred for 2 hours under reflux.

(71) After allowing the mixture to cool, methanol was added, and a precipitate was collected by filtration. The precipitate was dissolved under heat in chlorobenzene, and purified by adsorption with a silica gel and further purified by adsorption with an activated clay. After the purified product was crystallized with chlorobenzene/methanol mixed solvent, the product was washed under reflux with methanol to obtain a white powder of 4,4-bis{(9,9-dimethyl-9H-fluorene-2-yl)-phenylamino}-1,1:3,1-terphenyl Compound 1-34; 16.25 g; yield 90%).

(72) ##STR00100##

(73) The structure of the obtained white powder was identified by NMR.

(74) .sup.1H-NMR (CDCl.sub.3) detected 48 hydrogen signals, as follows.

(75) (ppm)=7.84 (1H), 7.70-7.03 (35H), 1.48 (12H).

Example 7

Synthesis of 2-{(biphenyl-4-yl)-phenylamino}-4-{(9,9-dimethyl-9H-fluorene-2-yl)-phenylamino}-1,1:4,1-terphenyl (Compound 1-37)

(76) The reaction was carried out under the same conditions as those of Example 5, except that N-(biphenyl-4-yl)-N-(2-bromo-1,1:4,1-terphenyl-4-yl)aniline was replaced with N-(9,9-dimethyl-9H-fluorene-2-yl)-N-(2-bromo-1,1:4,1-terphenyl-4-yl)aniline, and 2-(phenylamino)-9,9-dimethyl-9H-fluoren was replaced with N-(biphenyl-4-yl)-N-phenylaniline. As a result, a white powder of 2-{(biphenyl-4-yl)-phenylamino}-4-{(9,9-dimethyl-9H-fluorene-2-yl)-phenylamino}-1,1:4,1-terphenyl (Compound 1-37; 11.7 g; yield 73%) was obtained.

(77) ##STR00101##

(78) The structure of the obtained white powder was identified by NMR.

(79) .sup.1H-NMR (CDCl.sub.3) detected 44 hydrogen signals, as follows.

(80) (ppm)=7.68 (1H), 7.64-6.84 (37H), 1.48 (6H).

Example 8

Synthesis of 4,4-bis{N-(9,9-dimethyl-9H-fluorene-2-yl)-phenylamino}-1,1:2,1-terphenyl (Compound 1-38)

(81) The reaction was carried out under the same conditions as those of Example 3, except that 1,4-dibromobenzene was replaced with 1,2-diiodobenzene, and (biphenyl-4-yl)-{3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl}-phenylamine was replaced with 4-{(9,9-dimethyl-9H-fluorene-2-yl)-phenylamino}-phenylboronic acid. As a result, a white powder of 4,4-bis{N-(9,9-dimethyl-9H-fluorene-2-yl)-phenylamino}-1,1:2,1-terphenyl (Compound 1-38; 6.6 g; yield 39%) was obtained.

(82) ##STR00102##

(83) The structure of the obtained white powder was identified by NMR.

(84) .sup.1H-NMR (CDCl.sub.3) detected 48 hydrogen signals, as follows.

(85) (ppm)=7.64 (2H), 7.58 (2H), 7.45-6.99 (32H), 1.38 (12H).

Example 9

Synthesis of 4,4-bis{N-bis(biphenyl-4-yl)amino}-1,1:2,1-terphenyl (Compound 1-39)

(86) The reaction was carried out under the same conditions as those of Example 3, except that 1,4-dibromobenzene was replaced with 1,2-diiodobenzene, and (biphenyl-4-yl)-{3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl}-phenylamine was replaced with 4-{bis(biphenyl-4-yl)amino}-phenylboronic acid. As a result, a white powder of 4,4-bis{N-bis(biphenyl-4-yl)amino}-1,1:2,1-terphenyl (Compound 1-39; 4.6 g; yield 24%) was obtained.

(87) ##STR00103##

(88) The structure of the obtained white powder was identified by NMR.

(89) .sup.1H-NMR (CDCl.sub.3) detected 48 hydrogen signals, as follows.

(90) (ppm)=7.57-7.28 (32H), 7.21 (8H), 7.11 (8H).

Example 10

Synthesis of 4,4-bis{(biphenyl-4-yl)-(naphthalene-1-yl)amino}-1,1:2,1-terphenyl (Compound 1-41)

(91) The reaction was carried out under the same conditions as those of Example 6, except that 4,4-dibromo-1,1:3,1-terphenyl was replaced with 4,4-dibromo-1,1:2,1-terphenyl, and 2-(phenylamino)-9,9-dimethyl-9H-fluoren was replaced with (biphenyl-4-yl)-(naphthalene-1-yl)amine. As a result, a white powder of 4,4-bis{(biphenyl-4-yl)-(naphthalene-1-yl)amino}-1,1:2,1-terphenyl (Compound 1-41; 5.0 g; yield 30%) was obtained.

(92) ##STR00104##

(93) The structure of the obtained white powder was identified by NMR.

(94) .sup.1H-NMR (CDCl.sub.3) detected 44 hydrogen signals, as follows.

(95) (ppm)=7.93-7.84 (4H), 7.79 (2H), 7.60-7.26 (24H), 7.25-6.92 (14H).

Example 11

Synthesis of 4,4-bis[{4-(naphthalene-1-yl)phenyl}-phenylamino]-1,1:2,1-terphenyl (Compound 1-42)

(96) The reaction was carried out under the same conditions as those of Example 6, except that 4,4-dibromo-1,1:3,1-terphenyl was replaced with 4,4-dibromo-1,1:2,1-terphenyl, and 2-(phenylamino)-9,9-dimethyl-9H-fluoren was replaced with {4-(naphthalene-1-yl)phenyl}-phenylamine. As a result, a white powder of 4,4-bis[{4-(naphthalene-1-yl)phenyl}-phenylamino]-1,1:2,1-terphenyl (Compound 1-42; 7.3 g; yield 43%) was obtained.

(97) ##STR00105##

(98) The structure of the obtained white powder was identified by NMR.

(99) .sup.1H-NMR (CDCl.sub.3) detected 44 hydrogen signals, as follows.

(100) (ppm)=8.01 (2H), 7.91 (2H), 7.84 (2H), 7.53-6.98 (38H).

Example 12

Synthesis of 4,4-bis[{4-(naphthalene-1-yl)phenyl}-phenylamino]-1,1:3,1-terphenyl (Compound 1-45)

(101) The reaction was carried out under the same conditions as those of Example 6, except that 2-(phenylamino)-9,9-dimethyl-9H-fluoren was replaced with {4-(naphthalene-1-yl)phenyl}-phenylamine. As a result, a white powder of 4,4-bis[{4-(naphthalene-1-yl)phenyl}-phenylamino]-1,1:3,1-terphenyl (Compound 1-45; 16.7 g; yield 79%) was obtained.

(102) ##STR00106##

(103) The structure of the obtained white powder was identified by NMR.

(104) .sup.1H-NMR (CDCl.sub.3) detected 44 hydrogen signals, as follows.

(105) (ppm)=8.08 (2H), 7.94 (2H), 7.90-7.80 (3H), 7.65-7.00 (37H).

Example 13

Synthesis of 2,2-bis{(9,9-dimethyl-9H-fluorene-2-yl)-phenylamino}-1,1:3,1-terphenyl (Compound 1-47)

(106) The reaction was carried out under the same conditions as those of Example 3, except that 1,4-dibromobenzene was replaced with 1,3-diiodobenzene, and (biphenyl-4-yl)-{3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl}-phenylamine was replaced with 2-{(9,9-dimethyl-9H-fluorene-2-yl)-phenylamino}-phenylboronic acid. As a result, a white powder of 2,2-bis{(9,9-dimethyl-9H-fluorene-2-yl)-phenylamino}-1,1:3,1-terphenyl (Compound 1-47; 4.2 g; yield 25%) was obtained.

(107) ##STR00107##

(108) The structure of the obtained white powder was identified by NMR.

(109) .sup.1H-NMR (CDCl.sub.3) detected 48 hydrogen signals, as follows.

(110) (ppm)=7.60 (2H), 7.38-7.09 (14H), 6.95-6.71 (14H), 6.66-6.56 (4H), 6.35 (2H), 6.26 (12H).

Example 14

Synthesis of 2,2-bis{(9,9-dimethyl-9H-fluorene-2-yl)-phenylamino}-1,1:4,1-terphenyl (Compound 1-49)

(111) The reaction was carried out under the same conditions as those of Example 3, except that (biphenyl-4-yl)-{3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl}-phenylamine was replaced with 2-{(9,9-dimethyl-9H-fluorene-2-yl)-phenylamino}-phenylboronic acid. As a result, a white powder of 2,2-bis{(9,9-dimethyl-9H-fluorene-2-yl)-phenylamino}-1,1:4,1-terphenyl (Compound 1-49; 13.7 g; yield 76%) was obtained.

(112) ##STR00108##

(113) The structure of the obtained white powder was identified by NMR.

(114) .sup.1H-NMR (THF-d.sub.8) detected 48 hydrogen signals, as follows.

(115) (ppm)=7.53 (2H), 7.35-6.81 (30H), 6.76 (2H), 6.67 (2H), 1.29 (12H).

Example 15

Synthesis of 4,4-bis{(triphenylen-2-yl)-phenylamino}-1,1:4,1-terphenyl (Compound 1-88)

(116) The reaction was carried out under the same conditions as those of Example 6, except that 4,4-dibromo-1,1:3,1-terphenyl was replaced with 4,4-diiodo-1,1:4,1-terphenyl, and 2-(phenylamino)-9,9-dimethyl-9H-fluoren was replaced with (triphenylen-2-yl)-phenylamine. As a result, a white powder of 4,4-bis{(triphenylen-2-yl)-phenylamino}-1,1:4,1-terphenyl (Compound 1-88; 11.4 g; yield 74%) was obtained.

(117) ##STR00109##

(118) The structure of the obtained white powder was identified by NMR.

(119) .sup.1H-NMR (THF-d.sub.8) detected 44 hydrogen signals, as follows.

(120) (ppm)=8.72-8.62 (8H), 8.45 (2H), 8.36 (2H), 7.75 (4H), 7.70-7.21 (26H), 7.09 (2H).

Example 16

Synthesis of 4-{(biphenyl-4-yl)-phenylamino}-4-[{4-(1-phenyl-indol-4-yl)phenyl}-phenylamino]-1,1:4,1-terphenyl (Compound 1-91)

(121) The reaction was carried out under the same conditions as those of Example 1, except that N-(biphenyl-4-yl)-N-(4-bromophenyl)aniline was replaced with (4-bromo-1,1-biphenyl-4-yl)-{4-(1-phenyl-indol-4-yl)phenyl}-phenylamine, and N-(9,9-dimethyl-9H-fluoren-2-yl)-N-{3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-4-yl}aniline was replaced with {4-(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)phenyl}-(1,1-biphenyl-4-yl)-phenylamine. As a result, a pale yellowish white powder of 4-{(biphenyl-4-yl)-phenylamino}-4-[{4-(1-phenyl-indol-4-yl)phenyl}-phenylamino]-1,1:4,1-terphenyl (Compound 1-91; 6.80 g; yield 67%) was obtained.

(122) ##STR00110##

(123) The structure of the obtained pale yellowish white powder was identified by NMR.

(124) .sup.1H-NMR (THF-d.sub.8) detected 45 hydrogen signals, as follows.

(125) (ppm)=7.70 (4H), 7.68-7.50 (16H), 7.42-7.11 (23H), 7.05 (1H), 6.88 (1H).

Example 17

Synthesis of 4,4-bis{N-phenyl-N-(2-phenyl-biphenyl-4-yl)amino}-1,1:4,1-terphenyl (Compound 1-101)

(126) 4,4-diiodo-1,1:4,1-terphenyl (13.0 g), N-phenyl-N-(2-phenyl-biphenyl-4-yl)amine (20.0 g), a copper powder (0.18 g), potassium carbonate (11.3 g), 3,5-di-tert-butylsalicylic acid (0.7 g), sodium bisulfite (0.86 g), dodecylbenzene (30 ml) were added into a nitrogen-substituted reaction vessel, and the mixture was heated and stirred at 210 C. for 24 hours. The mixture was cooled, and a solid was collected by filtration after adding xylene (30 ml) and methanol (60 ml). Toluene (250 ml) and silica gel (20 g) were added to the obtained solid, and after heated up to 90 C., insoluble matter was removed by hot filtration. After adding ethyl acetate and methanol to the crude product obtained by concentration, a precipitated crystal was collected by filtration. Recrystallization with chlorobenzene and washing under reflux with methanol were carried out to obtain a white powder of 4,4-bis-{N-phenyl-N-(2-phenyl-biphenyl-4-yl)amino}-1,1:4,1-terphenyl (Compound 1-101; 16.9 g; yield 72%).

(127) ##STR00111##

(128) The structure of the obtained white powder was identified by NMR.

(129) .sup.1H-NMR (CDCl.sub.3) detected 48 hydrogen signals, as follows.

(130) (ppm)=7.68 (4H), 7.62-7.55 (4H), 7.39-7.06 (40H).

Example 18

Synthesis of 4,4-bis{N-phenyl-N-(2-phenyl-biphenyl-4-yl)amino}-1,1:2,1-terphenyl (Compound 1-103)

(131) The reaction was carried out under the same conditions as those of Example 6, except that 4,4-dibromo-1,1:3,1-terphenyl was replaced with 4,4-dibromo-1,1:2,1-terphenyl, and 2-(phenylamino)-9,9-dimethyl-9H-fluoren was replaced with N-phenyl-N-(2-phenyl-biphenyl-4-yl)amine. As a result, a white powder of 4,4-bis{N-phenyl-N-(2-phenyl-biphenyl-4-yl)amino}-1,1:2,1-terphenyl (Compound 1-103; 4.3 g; yield 42%) was obtained.

(132) ##STR00112##

(133) The structure of the obtained white powder was identified by NMR.

(134) .sup.1H-NMR (CDCl.sub.3) detected 48 hydrogen signals, as follows.

(135) (ppm)=7.50-7.39 (4H), 7.31-6.97 (44H).

Example 19

Synthesis of 4,4-bis{N-phenyl-N-(2-phenyl-biphenyl-4-yl)amino}-1,1:3,1-terphenyl (Compound 1-104)

(136) The reaction was carried out under the same conditions as those of Example 6, except that 2-(phenylamino)-9,9-dimethyl-9H-fluoren was replaced with N-phenyl-N-(2-phenyl-biphenyl-4-yl)amine. As a result, a white powder of 4,4-bis{N-phenyl-N-(2-phenyl-biphenyl-4-yl)amino}-1,1:3,1-terphenyl (Compound 1-104; 7.7 g; yield 53%) was obtained.

(137) ##STR00113##

(138) The structure of the obtained white powder was identified by NMR.

(139) .sup.1H-NMR (CDCl.sub.3) detected 48 hydrogen signals, as follows.

(140) (ppm)=7.81 (2H), 7.61-7.48 (14H), 7.39-7.06 (32H).

Example 20

(141) The glass transition points of the arylamine compounds of the general formula (1) were determined using a high-sensitive differential scanning calorimeter (DSC3100S produced by Bruker AXS).

(142) TABLE-US-00001 Glass transition point Compound of Example 1 117 C. Compound of Example 2 117 C. Compound of Example 3 103 C. Compound of Example 5 115 C. Compound of Example 6 124 C. Compound of Example 7 114 C. Compound of Example 8 119 C. Compound of Example 9 106 C. Compound of Example 10 127 C. Compound of Example 11 111 C. Compound of Example 12 122 C. Compound of Example 13 116 C. Compound of Example 14 117 C. Compound of Example 15 163 C. Compound of Example 16 125 C. Compound of Example 17 124 C. Compound of Example 18 115 C. Compound of Example 19 122 C.

(143) The arylamine compounds of the general formula (1) have glass transition points of 100 C. or higher, demonstrating that the compounds have a stable thin-film state.

Example 21

(144) A 100 nm-thick vapor-deposited film was fabricated on an ITO substrate using the arylamine compounds of the general formula (1), and a work function was measured using an ionization potential measuring device (PYS-202 produced by Sumitomo Heavy Industries, Ltd.).

(145) TABLE-US-00002 Work function Compound of Example 1 5.68 eV Compound of Example 2 5.65 eV Compound of Example 3 5.79 eV Compound of Example 4 5.83 eV Compound of Example 5 5.69 eV Compound of Example 6 5.65 eV Compound of Example 7 5.67 eV Compound of Example 8 5.64 eV Compound of Example 9 5.66 eV Compound of Example 10 5.69 eV Compound of Example 11 5.75 eV Compound of Example 12 5.76 eV Compound of Example 13 5.72 eV Compound of Example 14 5.72 eV Compound of Example 15 5.62 eV Compound of Example 16 5.67 eV Compound of Example 17 5.67 eV Compound of Example 18 5.75 eV Compound of Example 19 5.76 eV

(146) As the results show, the arylamine compounds of the general formula (1) have desirable energy levels compared to the work function 5.4 eV of common hole transport materials such as NPD and TPD, and thus possess desirable hole transportability.

Example 22

Synthesis of N5,N5,N9,N9-tetrakis{4-(tert-butyl)phenyl}spiro(fluorene-9,7-fluoreno[4,3-b]benzofuran)-5,9-diamine (Compound 2-1)

(147) 5,9-dibromospiro(fluorene-9,7-fluoreno[4,3-b]benzofuran) (5.0 g), bis{4-(tert-butyl)phenyl}amine (6.0 g), palladium acetate (0.08 g), sodium tert-butoxide (3.4 g), tri-tert-butylphosphine (0.07 g), and toluene (60 ml) were added into a nitrogen-substituted reaction vessel, and the mixture was heated and stirred for 2 hours under reflux. The mixture was cooled to a room temperature, dichloromethane and water were added, and an organic layer was collected by liquid separation. After the organic layer was concentrated, purification by column chromatography was performed to obtain a powder of N5,N5,N9,N9-tetrakis{4-(tert-butyl)phenyl}spiro (fluorene-9,7-fluoreno[4,3-b]benzofuran)-5,9-diamine (Compound 2-1; 3.1 g; yield 36%).

(148) ##STR00114##

Example 23

Synthesis of N2,N2,N7,N7-tetrakis{4-(tert-butyl)phenyl}spiro(dibenzo[5,6:7,8]fluoreno[4,3-b] benzofuran-5,9-fluorene)-2,7-diamine (Compound 2-2)

(149) The reaction was carried out under the same conditions as those of Example 22, except that 5,9-dibromospiro(fluorene-9,7-fluoreno[4,3-b]benzofuran) was replaced with 2,7-dibromospiro(dibenzo[5,6:7,8]fluoreno [4,3-b]benzofuran-5,9-fluorene). As a result, a powder of N2,N2,N7,N7-tetrakis{4-(tert-butyl)phenyl}spiro(dibenzo [5,6:7,8]fluoreno[4,3-b]benzofuran-5,9-fluorene)-2,7-diamine (Compound 2-2; 2.5 g; yield 31%) was obtained.

(150) ##STR00115##

Example 24

Synthesis of N5,N5,N9,N9-tetrakis{4-(tert-butyl)phenyl}spiro(benzo[5,6]fluoreno[4,3-b]benzofuran-7,9-fluorene)-5,9-diamine (Compound 2-3)

(151) The reaction was carried out under the same conditions as those of Example 22, except that 5,9-dibromospiro(fluorene-9,7-fluoreno[4,3-b]benzofuran) was replaced with 5,9-dibromospiro(benzo[5,6]fluoreno[4,3-b]benzofuran-7,9-fluorene). As a result, a powder of N5,N5,N9,N9-tetrakis{4-(tert-butyl)phenyl}spiro(benzo[5,6] fluoreno[4,3-b]benzofuran-7,9-fluorene)-5,9-diamine (Compound 2-3; 3.0 g; yield 36%) was obtained.

(152) ##STR00116##

Example 25

Synthesis of N6,N6,N10,N10-tetrakis{4-(tert-butyl)phenyl}spiro(fluorene-9,8-fluoreno[3,4-b]benzofuran)-6,10-diamine (Compound 2-4)

(153) The reaction was carried out under the same conditions as those of Example 22, except that 5,9-dibromospiro(fluorene-9,7-fluoreno[4,3-b]benzofuran) was replaced with 6,10-dibromospiro(fluorene-9,8-fluoreno[3,4-b]benzofuran). As a result, a powder of N6,N6,N10,N10-tetrakis{4-(tert-butyl)phenyl}spiro (fluorene-9,8-fluoreno[3,4-b]benzofuran)-6,10-diamine (Compound 2-4; 2.5 g; yield 34%) was obtained.

(154) ##STR00117##

Example 26

Synthesis of N5,N5,N9,N9-tetrakis{4-(tert-butyl)phenyl}spiro(fluoreno[4,3-b]benzofuran-7,9-xanthene)-5,9-diamine (Compound 2-5)

(155) The reaction was carried out under the same conditions as those of Example 22, except that 5,9-dibromospiro(fluorene-9,7-fluoreno[4,3-b]benzofuran) was replaced with 5,9-dibromospiro(fluoreno[4,3-b]benzofuran-7,9-xanthene). As a result, a powder of N5,N5,N9,N9-tetrakis{4-(tert-butyl)phenyl}spiro(fluoreno[4,3-b] benzofuran-7,9-xanthene)-5,9-diamine (Compound 2-5; 2.4 g; yield 28%) was obtained.

(156) ##STR00118##

Example 27

Synthesis of N5,N9-bis(biphenyl-4-yl)-N5,N9-bis{4-(tert-butyl)phenyl}-2-fluorospiro(fluorene-9,7-fluoreno[4,3-b]benzofuran)-5,9-diamine (Compound 2-6)

(157) The reaction was carried out under the same conditions as those of Example 22, except that 5,9-dibromospiro(fluorene-9,7-fluoreno[4,3-b]benzofuran) was replaced with 5,9-dibromo-2-fluorospiro(fluorene-9,7-fluoreno[4,3-b]benzofuran), and bis{4-(tert-butyl)phenyl}amine was replaced with (biphenyl-4-yl)-{4-(tert-butyl)phenyl}amine. As a result, a powder of N5,N9-bis(biphenyl-4-yl)-N5,N9-bis{4-(tert-butyl) phenyl}-2-fluorospiro(fluorene-9,7-fluoreno[4,3-b]benzofuran)-5,9-diamine (Compound 2-6; 2.4 g; yield 28%) was obtained.

(158) ##STR00119##

Example 28

Synthesis of N5,N9-bis{4-(tert-butyl)phenyl}-N5,N9-bis{4-(trimethylsilyl)phenyl}spiro(benzo[5,6]fluoreno[4,3-b]benzofuran-7,9-fluorene)-5,9-diamine (Compound 2-7)

(159) The reaction was carried out under the same conditions as those of Example 22, except that 5,9-dibromospiro(fluorene-9,7-fluoreno[4,3-b]benzofuran) was replaced with 5,9-dibromospiro(benzo[5,6]fluoreno[4,3-b]benzofuran-7,9-fluorene), and bis{4-(tert-butyl)phenyl}amine was replaced with {4-(tert-butyl)phenyl}-{4-(trimethylsilyl)phenyl}amine. As a result, a powder of N5,N9-bis{4-(tert-butyl)phenyl}-N5,N9-bis{4-(trimethylsilyl)phenyl}spiro(benzo[5,6]fluoreno[4,3-b]benzofuran-7,9-fluorene)-5,9-diamine (Compound 2-7; 3.0 g; yield 35%) was obtained.

(160) ##STR00120##

Example 29

Synthesis of N5,N9-bis{4-(tert-butyl)phenyl}-N5,N9-bis{4-(trimethylsilyl)phenyl}spiro(fluorene-9,7-fluoreno[4,3-b]benzothiophene)-5,9-diamine (Compound 2-8)

(161) The reaction was carried out under the same conditions as those of Example 22, except that 5,9-dibromospiro(fluorene-9,7-fluoreno[4,3-b]benzofuran) was replaced with 5,9-dibromospiro(fluorene-9,7-fluoreno[4,3-b]benzothiophene), and bis{4-(tert-butyl)phenyl}amine was replaced with {4-(tert-butyl)phenyl}-{4-(trimethylsilyl)phenyl}amine. As a result, a powder of N5,N9-bis{4-(tert-butyl)phenyl}-N5,N9-bis{4-(trimethylsilyl)phenyl}spiro(fluorene-9,7-fluoreno[4,3-b]benzothiophene)-5,9-diamine (Compound 2-8; 3.2 g; yield 37%) was obtained.

(162) ##STR00121##

Example 30

Synthesis of N5,N9-bis(biphenyl-4-yl)-N5,N9-bis{4-(tert-butyl)phenyl}spiro(benzo[4,5]thieno[2,3:5,6] fluoreno[4,3-b]benzofuran-7,9-fluorene)-5,9-diamine (Compound 2-9)

(163) The reaction was carried out under the same conditions as those of Example 22, except that 5,9-dibromospiro(fluorene-9,7-fluoreno[4,3-b]benzofuran) was replaced with 5,9-dibromospiro(benzo[4,5]thieno [2,3:5,6]fluoreno[4,3-b]benzofuran-7,9-fluorene), and bis{4-(tert-butyl)phenyl}amine was replaced with {4-(tert-butyl)phenyl}-(biphenyl-4-yl)amine. As a result, a powder of N5,N9-bis(biphenyl-4-yl)-N5,N9-bis{4-(tert-butyl)phenyl}spiro(benzo[4,5]thieno[2,3:5,6]fluoreno[4,3-b]benzofuran-7,9-fluorene)-5,9-diamine (Compound 2-9; 2.8 g; yield 34%) was obtained.

(164) ##STR00122##

Example 31

Synthesis of N5,N5,N9,N9-tetrakis{4-(tert-butyl)phenyl}-12,12-dimethyl-12H-spiro(fluorene-9,7-indeno[1,2-a]fluorene)-5,9-diamine (Compound 2-10)

(165) The reaction was carried out under the same conditions as those of Example 22, except that 5,9-dibromospiro(fluorene-9,7-fluoreno[4,3-b]benzofuran) was replaced with 5,9-dibromo-12,12-dimethyl-12H-spiro(fluorene-9,7-indeno[1,2-a]fluorene). As a result, a powder of N5,N5,N9,N9-tetrakis{4-(tert-butyl)phenyl}-12,12-dimethyl-12H-spiro(fluorene-9,7-indeno[1,2-a]fluorene)-5,9-diamine (Compound 2-10; 1.8 g; yield 49%) was obtained.

(166) ##STR00123##

Example 32

Synthesis of N6,N10-bis(biphenyl-4-yl)-N6,N10-bis{4-(tert-butyl)phenyl}-5-methyl-5H-spiro(fluorene-9,8-indeno[2,1-c]carbazole)-6,10-diamine (Compound 2-11)

(167) The reaction was carried out under the same conditions as those of Example 22, except that 5,9-dibromospiro(fluorene-9,7-fluoreno[4,3-b]benzofuran) was replaced with 6,10-dibromo-5-methyl-5H-spiro(fluorene-9,8-indeno[2,1-c]carbazole), and bis{4-(tert-butyl)phenyl}amine was replaced with {4-(tert-butyl)phenyl}-(biphenyl-4-yl)amine. As a result, a powder of N6,N10-bis(biphenyl-4-yl)-N6,N10-bis{4-(tert-butyl)phenyl}-5-methyl-5H-spiro(fluorene-9,8-indeno [2,1-c]carbazole)-6,10-diamine (Compound 2-11; 2.3 g; yield 41%) was obtained.

(168) ##STR00124##

Example 33

Synthesis of N6,N6,N10,N10-tetrakis{4-(tert-butyl)phenyl}spiro(benzo[4,5]furo[2,3:5,6]fluoreno[3,4-b]benzofuran-8,9-fluorene)-6,10-diamine (Compound 2-22)

(169) The reaction was carried out under the same conditions as those of Example 22, except that 5,9-dibromospiro(fluorene-9,7-fluoreno[4,3-b]benzofuran) was replaced with 6,10-dibromospiro(benzo[4,5]furo [2,3:5,6]fluoreno[3,4-b]benzofuran-8,9-fluorene). As a result, a powder of N6,N6,N10,N10-tetrakis{4-(tert-butyl)phenyl}spiro(benzo[4,5]furo[2,3:5,6]fluoreno[3,4-b]benzofuran-8,9-fluorene)-6,10-diamine (Compound 2-22; 1.5 g; yield 41%) was obtained.

(170) ##STR00125##

Example 34

Synthesis of N6,N6,N10,N10-tetrakis{4-(tert-butyl)phenyl}-8,8-diphenyl-benzo[4,5]furo[2,3:5,6]fluoreno[3,4-b]benzofuran-6,10-diamine (Compound 2-23)

(171) The reaction was carried out under the same conditions as those of Example 22, except that 5,9-dibromospiro(fluorene-9,7-fluoreno[4,3-b]benzofuran) was replaced with 6,10-dibromo-8,8-diphenyl-benzo[4,5]furo[2,3:5,6]fluoreno[3,4-b]benzofuran. As a result, a powder of N6,N6,N10,N10-tetrakis{4-(tert-butyl)phenyl}-8,8-diphenyl-benzo[4,5]furo[2,3:5,6] fluoreno[3,4-b]benzofuran-6,10-diamine (Compound 2-23; 3.2 g; yield 49%) was obtained.

(172) ##STR00126##

Example 35

Synthesis of N6,N10-bis{4-(tert-butyl)phenyl}-N6,N10-bis{4-(trimethylsilyl)phenyl}spiro(benzo[4,5] furo[2,3:5,6]fluoreno[3,4-b]benzofuran-8,9-fluorene)-6,10-diamine (Compound 2-24)

(173) The reaction was carried out under the same conditions as those of Example 22, except that 5,9-dibromospiro(fluorene-9,7-fluoreno[4,3-b]benzofuran) was replaced with 6,10-dibromospiro(benzo[4,5]furo [2,3:5,6]fluoreno[3,4-b]benzofuran-8,9-fluorene), and bis{4-(tert-butyl)phenyl}amine was replaced with {4-(tert-butyl)phenyl}-{4-(trimethylsilyl)phenyl}amine. As a result, a powder of N6,N10-bis{4-(tert-butyl)phenyl}-N6,N10-bis{4-(trimethylsilyl)phenyl}spiro(benzo[4,5]furo [2,3:5,6]fluoreno[3,4-b]benzofuran-8,9-fluorene)-6,10-diamine (Compound 2-24; 2.3 g; yield 43%) was obtained.

(174) ##STR00127##

Example 36

Synthesis of N6,N6,N10,N10-tetrakis{4-(tert-butyl)phenyl}-8,8-bis{4-(tert-butyl)phenyl}-benzo[4,5]furo[2,3:5,6]fluoreno[3,4-b]benzofuran-6,10-diamine (Compound 2-25)

(175) The reaction was carried out under the same conditions as those of Example 22, except that 5,9-dibromospiro(fluorene-9,7-fluoreno[4,3-b]benzofuran) was replaced with 6,10-dibromo-8,8-bis{4-(tert-butyl)phenyl}-benzo[4,5]furo[2,3:5,6]fluoreno[3,4-b]benzofuran. As a result, a powder of N6,N6,N10,N10-tetrakis{4-(tert-butyl)phenyl}-8,8-bis{4-(tert-butyl)phenyl}-benzo[4,5] furo[2,3:5,6]fluoreno[3,4-b]benzofuran-6,10-diamine (Compound 2-25; 8.2 g; yield 54%) was obtained.

(176) ##STR00128##

Example 37

(177) The organic EL device, as shown in FIG. 1, was fabricated by vapor-depositing a hole injection layer 3, a first hole transport layer 4, a second hole transport layer 5, a light emitting layer 6, an electron transport layer 7, an electron injection layer 8, and a cathode (aluminum electrode) 9 in this order on a glass substrate 1 on which an ITO electrode was formed as a transparent anode 2 beforehand.

(178) Specifically, the glass substrate 1 having ITO (film thickness of 150 nm) formed thereon was subjected to ultrasonic washing in isopropyl alcohol for 20 minutes and then dried for 10 minutes on a hot plate heated to 200 C. After UV ozone treatment for 15 minutes, the glass substrate with ITO was installed in a vacuum vapor deposition apparatus, and the pressure was reduced to 0.001 Pa or lower. Compound HIM-1 of the structural formula below was then formed in a film thickness of 5 nm as the hole injection layer 3 so as to cover the transparent anode 2. The first hole transport layer 4 was formed on the hole injection layer 3 by forming the arylamine compounds (4-1) of the structural formula below having two triphenylamine structures within a molecule in a film thickness of 45 nm. The second hole transport layer 5 was formed on the first hole transport layer 4 by forming the compound (1-21) of Example 3 in a film thickness of 5 nm. Then, the light emitting layer 6 was formed on the second hole transport layer 5 in a film thickness of 25 nm by dual vapor deposition of the compound (2-4) of Example 25 and Compound EMH-1 of the structural formula below at a vapor deposition rate ratio of the compound (2-4): EMH-1=5:95. The electron transport layer 7 was formed on the light emitting layer 6 in a film thickness of 30 nm by dual vapor deposition of the compound (3a-1) of the structural formula below having an anthracene ring structure and Compound ETM-1 of the structural formula below at a vapor deposition rate ratio of the compound (3a-1): ETM-1=50:50. The electron injection layer 8 was formed on the electron transport layer 7 by forming lithium fluoride in a film thickness of 1 nm. Finally, the cathode 9 was formed by vapor-depositing aluminum in a thickness of 100 nm. The characteristics of the thus fabricated organic EL device were measured in the atmosphere at an ordinary temperature. Table 1 summarizes the results of emission characteristics measurements performed by applying a DC voltage to the fabricated organic EL device.

(179) ##STR00129## ##STR00130##

Example 38

(180) An organic EL device was fabricated under the same conditions used in Example 37, except that the second hole transport layer 5 was formed by forming the compound (1-37) of Example 7 in a film thickness of 5 nm, instead of using the compound (1-21) of Example 3. The characteristics of the organic EL device thus fabricated were measured in the atmosphere at an ordinary temperature. Table 1 summarizes the results of emission characteristics measurements performed by applying a DC voltage to the fabricated organic EL device.

(181) ##STR00131##

Example 39

(182) An organic EL device was fabricated under the same conditions used in Example 37, except that the second hole transport layer 5 was formed by forming the compound (1-45) of Example 12 in a film thickness of 5 nm, instead of using the compound (1-21) of Example 3. The characteristics of the organic EL device thus fabricated were measured in the atmosphere at an ordinary temperature. Table 1 summarizes the results of emission characteristics measurements performed by applying a DC voltage to the fabricated organic EL device.

(183) ##STR00132##

Example 40

(184) An organic EL device was fabricated under the same conditions used in Example 37, except that the light emitting layer 6 was formed by forming the compound (2-10) of Example 31 in a film thickness of 25 nm, instead of using the compound (2-4) of Example 25, by dual vapor deposition of the compound (2-10) and Compound EMH-1 of the structural formula above at a vapor deposition rate ratio of the compound (2-10): EMH-1=5:95. The characteristics of the organic EL device thus fabricated were measured in the atmosphere at an ordinary temperature. Table 1 summarizes the results of emission characteristics measurements performed by applying a DC voltage to the fabricated organic EL device.

(185) ##STR00133##

Example 41

(186) An organic EL device was fabricated under the same conditions used in Example 40, except that the second hole transport layer 5 was formed by forming the compound (1-37) of Example 7 in a film thickness of 5 nm, instead of using the compound (1-21) of Example 3. The characteristics of the organic EL device thus fabricated were measured in the atmosphere at an ordinary temperature. Table 1 summarizes the results of emission characteristics measurements performed by applying a DC voltage to the fabricated organic EL device.

Example 42

(187) An organic EL device was fabricated under the same conditions used in Example 40, except that the second hole transport layer 5 was formed by forming the compound (1-45) of Example 12 in a film thickness of 5 nm, instead of using the compound (1-21) of Example 3. The characteristics of the organic EL device thus fabricated were measured in the atmosphere at an ordinary temperature. Table 1 summarizes the results of emission characteristics measurements performed by applying a DC voltage to the fabricated organic EL device.

Comparative Example 1

(188) For comparison, an organic EL device was fabricated under the same conditions used in Example 37, except that the first hole transport layer 4 was formed by forming the arylamine compound (4-2) of the structural formula below having two triphenylamine structures within a molecule in a film thickness of 45 nm, instead of using the compound (4-1) of the structural formula having two triphenylamine structures within a molecule, then the second hole transport layer 5 was formed by forming the arylamine compound (4-2) of the structural formula below having two triphenylamine structures within a molecule in a film thickness of 5 nm, instead of using the compound (1-21) of Example 3. The characteristics of the organic EL device thus fabricated were measured in the atmosphere at an ordinary temperature. Table 1 summarizes the results of emission characteristics measurements performed by applying a DC voltage to the fabricated organic EL device.

(189) ##STR00134##

Comparative Example 2

(190) For comparison, an organic EL device was fabricated under the same conditions used in Example 40, except that the first hole transport layer 4 was formed by forming the arylamine compound (4-2) of the structural formula having two triphenylamine structures within a molecule in a film thickness of 45 nm, instead of using the compound (4-1) of the structural formula having two triphenylamine structures within a molecule, then the second hole transport layer 5 was formed by forming the arylamine compound (4-2) of the structural formula having two triphenylamine structures within a molecule in a film thickness of 5 nm, instead of using the compound (1-21) of Example 3. The characteristics of the organic EL device thus fabricated were measured in the atmosphere at an ordinary temperature. Table 1 summarizes the results of emission characteristics measurements performed by applying a DC voltage to the fabricated organic EL device.

(191) Table 1 summarizes the results of the device lifetime measurements performed with the organic EL devices fabricated in Examples 37 to 42 and Comparative Examples 1 to 2. A device lifetime was measured as the time elapsed until the emission luminance of 2,000 cd/m.sup.2 (initial luminance) at the start of emission was attenuated to 1,900 cd/m.sup.2 (corresponding to attenuation to 95% when taking the initial luminance as 100%) when carrying out constant current driving.

(192) TABLE-US-00003 TABLE 1 Current Power Device First hole Second hole Electron Luminance efficiency efficiency lifetime transport transport Light emitting Transport Voltage [V] [cd/m.sup.2] [cd/A] [lm/W] (Attenuation layer layer layer layer (@10 mA/cm.sup.2) (@10 mA/cm.sup.2) (@10 mA/cm.sup.2) (@10 mA/cm.sup.2) to 95%) Ex. 37 Compound Compound Compound Compound 4.11 746 7.45 5.70 105 h 4-1 1-21 2-4/ 3a-1/ EMH-1 ETM-1 Ex. 38 Compound Compound Compound Compound 4.14 764 7.64 5.80 132 h 4-1 1-37 2-4/ 3a-1/ EMH-1 ETM-1 Ex. 39 Compound Compound Compound Compound 4.25 788 7.88 5.83 123 h 4-1 1-45 2-4/ 3a-1/ EMH-1 ETM-1 Ex. 40 Compound Compound Compound Compound 4.14 741 7.41 5.63 134 h 4-1 1-21 2-10/ 3a-1/ EMH-1 ETM-1 Ex. 41 Compound Compound Compound Compound 4.13 775 7.74 5.89 135 h 4-1 1-37 2-10/ 3a-1/ EMH-1 ETM-1 Ex. 42 Compound Compound Compound Compound 4.26 752 7.52 5.55 127 h 4-1 1-45 2-10/ 3a-1/ EMH-1 ETM-1 Com. Compound Compound Compound Compound 4.07 585 5.86 4.52 47 h Ex. 1 4-2 4-2 2-4/ 3a-1/ EMH-1 ETM-1 Com. Compound Compound Compound Compound 4.07 585 5.86 4.53 54 h Ex. 2 4-2 4-2 2-10/ 3a-1/ EMH-1 ETM-1

(193) As shown in Table 1, the current efficiency upon passing a current with a current density of 10 mA/cm.sup.2 was 7.41 to 7.88 cd/A for the organic EL devices in Examples 37 to 42, which was higher than 5.86 cd/A for the organic EL devices in Comparative Examples 1 to 2. Further, the power efficiency was 5.55 to 5.89 lm/W for the organic EL devices in Examples 37 to 42, which was higher than 4.52 to 4.53 lm/W for the organic EL devices in Comparative Examples 1 to 2. Table 1 also shows that the device lifetime (attenuation to 95%) was 105 to 135 hours for the organic EL devices in Examples 37 to 42, showing achievement of a far longer lifetime than 47 to 54 hours for the organic EL devices in Comparative Examples 1 to 2.

(194) In the organic EL devices of the present invention, the combination of specific arylamine compounds and specific amine derivatives having a condensed ring structure (and specific compounds having an anthracene ring structure) can improve carrier balance inside the organic EL devices. Further, the organic EL devices of the present invention can achieve high luminous efficiency and a long lifetime, compared to the conventional organic EL devices by combining those compounds in carrier balance matching characteristics of the light-emitting material.

INDUSTRIAL APPLICABILITY

(195) In the organic EL devices of the present invention with the combination of specific arylamine compounds and specific amine derivatives having a condensed ring structure (and specific compounds having an anthracene ring structure), luminous efficiency and durability of an organic EL device can be improved to attain potential applications for, for example, home electric appliances and illuminations.

DESCRIPTION OF REFERENCE NUMERAL

(196) 1 Glass substrate 2 Transparent anode 3 Hole injection layer 4 First hole transport layer 5 Second hole transport layer 6 Light emitting layer 7 Electron transport layer 8 Electron injection layer 9 Cathode