ARYLAMINE COMPOUND AND ORGANIC ELECTROLUMINESCENT ELEMENT

Abstract

An objective of the invention is to provide, as a material for highly efficient, highly durable organic EL devices, an organic EL device material having excellent hole injectability and transportability, electron blockability, high stability in a thin-film state, and excellent durability, and also to provide a highly efficient, highly durable organic EL device by using this compound. The present invention concerns an arylamine compound represented by general formula (1). (In the formula, Ar.sub.1, Ar.sub.2, Ar.sub.3, and Ar.sub.4 each represent a substituted or unsubstituted aromatic hydrocarbon group, etc.; L.sub.1 and L.sub.2 each represent a divalent substituted or unsubstituted aromatic hydrocarbon group, etc.; R.sub.1 to R.sub.7 each represent a hydrogen atom, a deuterium atom, etc.; and m and n may be the same or different from one another, and each represent an integer from 0 to 2, wherein L.sub.1 represents a single bond when m is 0, and L.sub.2 represents a single bond when n is 0.)

Claims

1. An arylamine compound represented by general formula (1) below: ##STR00036## in the formula, Ar.sub.1, Ar.sub.2, Ar.sub.3, and Ar.sub.4 may be the same or different from one another, and each represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted fused polycyclic aromatic group; L.sub.1 and L.sub.2 may be the same or different from one another, and each represent a divalent substituted or unsubstituted aromatic hydrocarbon group, a divalent substituted or unsubstituted aromatic heterocyclic group, or a divalent substituted or unsubstituted fused polycyclic aromatic group; R.sub.1 to R.sub.7 may be the same or different from one another, and each represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms and optionally having a substituent, a cycloalkyl group having 5 to 10 carbon atoms and optionally having a substituent, a linear or branched alkenyl group having 2 to 6 carbon atoms and optionally having a substituent, a linear or branched alkyloxy group having 1 to 6 carbon atoms and optionally having a substituent, a cycloalkyloxy group having 5 to 10 carbon atoms and optionally having a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted fused polycyclic aromatic group, or a substituted or unsubstituted aryloxy group; and m and n may be the same or different from one another, and each represent an integer from 0 to 2, wherein L.sub.1 represents a single bond when m is 0, and L.sub.2 represents a single bond when n is 0.

2. The arylamine compound according to claim 1, wherein, in the general formula (1), R.sub.1 and R.sub.3 may be the same or different from one another, and each represent a hydrogen atom or a deuterium atom.

3. The arylamine compound according to claim 1, wherein, in the general formula (1), Ar.sub.3 and Ar.sub.4 may be the same or different from one another, and each represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted fluorenyl group.

4. The arylamine compound according to claim 1, wherein, in the general formula (1), R.sub.2 represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted fluorenyl group.

5. The arylamine compound according to claim 1, wherein, in the general formula (1), Ar.sub.3 and Ar.sub.4 are the same.

6. The arylamine compound according claim 1, wherein, in the general formula (1), Ar.sub.3, Ar.sub.4, and R.sub.2 are the same.

7. The arylamine compound according claim 1, wherein, in the general formula (1), L.sub.1 or L.sub.2 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalene group, or a substituted or unsubstituted biphenyl ene group.

8. The arylamine compound according to claim 1, wherein, in the general formula (1), a sum of the integers m and n is 0 or 1.

9. An organic electroluminescence device comprising: a pair of electrodes; and at least one organic layer sandwiched between the electrodes, wherein the organic layer contains the arylamine compound according claim 1.

10. The organic electroluminescence device according to claim 9, wherein the organic layer is a hole transport layer.

11. The organic electroluminescence device according to claim 9, wherein the organic layer is an electron blocking layer.

12. The organic electroluminescence device according to claim 9, wherein the organic layer is a hole injection layer.

13. The organic electroluminescence device according to claim 9, wherein the organic layer is a light-emitting layer.

14. An electronic device employing an electronic component comprising: a pair of electrodes; and at least one organic layer sandwiched between the electrodes, wherein the organic layer contains the arylamine compound according to claim 1.

Description

BRIEF DESCRIPTION OF DRAWINGS

[0069] FIG. 1 is a diagram illustrating Compounds (1) to (12) as preferable concrete examples of arylamine compounds represented by general formula (1).

[0070] FIG. 2 is a diagram illustrating Compounds (13) to (24) as preferable concrete examples of arylamine compounds represented by general formula (1).

[0071] FIG. 3 is a diagram illustrating Compounds (25) to (36) as preferable concrete examples of arylamine compounds represented by general formula (1).

[0072] FIG. 4 is a diagram illustrating Compounds (37) to (48) as preferable concrete examples of arylamine compounds represented by general formula (1).

[0073] FIG. 5 is a diagram illustrating Compounds (49) to (60) as preferable concrete examples of arylamine compounds represented by general formula (1).

[0074] FIG. 6 is a diagram illustrating Compounds (61) to (72) as preferable concrete examples of arylamine compounds represented by general formula (1).

[0075] FIG. 7 is a diagram illustrating Compounds (73) to (84) as preferable concrete examples of arylamine compounds represented by general formula (1).

[0076] FIG. 8 is a diagram illustrating Compounds (85) to (96) as preferable concrete examples of arylamine compounds represented by general formula (1).

[0077] FIG. 9 is a diagram illustrating Compounds (97) to (108) as preferable concrete examples of arylamine compounds represented by general formula (1).

[0078] FIG. 10 is a diagram illustrating Compounds (109) to (120) as preferable concrete examples of arylamine compounds represented by general formula (1).

[0079] FIG. 11 is a diagram illustrating Compounds (121) to (132) as preferable concrete examples of arylamine compounds represented by general formula (1).

[0080] FIG. 12 is a diagram illustrating Compounds (133) to (144) as preferable concrete examples of arylamine compounds represented by general formula (1).

[0081] FIG. 13 is a diagram illustrating Compounds (145) to (153) as preferable concrete examples of arylamine compounds represented by general formula (1).

[0082] FIG. 14 is a diagram illustrating a configuration of an organic EL device for Examples 32 to 60 and Comparative Examples 1 and 2.

DESCRIPTION OF EMBODIMENTS

[0083] The arylamine compounds of the present invention are novel compounds, but these compounds can be synthesized according to known methods (see, for example, Patent Literature 5).

[0084] FIGS. 1 to 12 illustrate concrete examples of preferred compounds among arylamine compounds represented by the general formula (1) that may be suitably used for the organic EL device of the present invention. Note, however, that the compounds are not limited to the illustrated compounds.

[0085] The arylamine compound represented by general formula (1) can be purified by known methods, such as column chromatography purification, adsorption purification with silica gel, activated carbon, activated clay, etc., recrystallization or crystallization using a solvent, sublimation purification, or the like. Compound identification can be achieved by NMR analysis. Physical properties to be measured may include such values as the melting point, glass transition point (Tg), work function, or the like. The melting point serves as an index of vapor deposition characteristics. The glass transition point (Tg) serves as an index of stability in a thin-film state. The work function serves as an index of hole injectability, hole transportability, or electron blockability.

[0086] The melting point and glass transition point (Tg) can be measured, for example, with a high-sensitivity differential scanning calorimeter (DSC3100SA from Bruker AXS) using a powder.

[0087] The work function can be found, for example, with an ionization potential measurement device (PYS-202 from Sumitomo Heavy Industries, Ltd.) by preparing a 100-nm thin film on an ITO substrate.

[0088] A structure of the organic EL device of the present invention may, for example, sequentially include, on a substrate, an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode. In other examples, an electron blocking layer may be provided between the hole transport layer and the light-emitting layer, or a hole blocking layer may be provided between the light-emitting layer and the electron transport layer. In such multilayer structures, a single organic layer may have functions of several layers; for example, a single organic layer may have functions of the hole injection layer and the hole transport layer, or functions of the electron injection layer and the electron transport layer. Further, it is possible to stack two or more organic layers having the same function; for example, the structure may include: two stacked hole transport layers; two stacked light-emitting layers; or two stacked electron transport layers.

[0089] For the anode in the organic EL device of the present invention, it is possible to use an electrode material having a large work function, such as ITO or gold. For the material for the hole injection layer in the organic EL device of the present invention, it is possible to use: a porphyrin compound typified by copper phthalocyanine; a starburst triphenylamine derivative; an arylamine compound including, in its molecule, two or more triphenylamine structures or carbazolyl structures which are linked by a single bond or a divalent group containing no hetero atom; an acceptor heterocyclic compound such as hexacyanoazatriphenylene; or a coating-type polymer material. These materials can form thin films by known methods, such as vapor deposition, spin coating, ink-jetting, etc.

[0090] For the material for the hole injection layer and the hole transport layer in the organic EL device of the present invention, it is possible to use, other than the arylamine compound of the present invention, a benzidine derivative, such as N,N′-diphenyl-N,N′-di(m-tolyl)-benzidine (abbreviated hereinbelow as “TPD”), N,N′ -diphenyl-N,N′-di(α-naphthyl)-benzidine (abbreviated hereinbelow as “NPD”), N,N,N′ ,N′-tetrabiphenylylbenzidine, etc., or 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (abbreviated hereinbelow as “TAPC”), or an arylamine compound including, in its molecule, two or more triphenylamine structures or carbazolyl structures which are linked by a single bond or a divalent group containing no hetero atom. These materials may each be formed into a film singly, or a plurality of types of these materials may be mixed and formed into a film, and each may be used as a single layer. It is possible to form a laminate structure constituted by layers each formed singly by the respective materials, or a laminate structure constituted by layers formed by mixing, or a laminate structure constituted by layers each formed singly by the respective materials and layers formed by mixing a plurality of types of materials. Further, for the material for the hole inj ection-transport layer, it is possible to use a coating-type polymer material, such as poly(3,4-ethylenedioxythiophene) (abbreviated hereinbelow as “PEDOT”)/poly(styrene sulfonate) (abbreviated hereinbelow as “PSS”). These materials can form thin films by known methods, such as vapor deposition, spin coating, ink-jetting, etc.

[0091] For the hole injection layer or the hole transport layer, it is possible to use: a material ordinarily used for such layers and p-doped with, for example, trisbromophenylamine hexachloroantimonate or a radialene derivative (see, for example, Patent Literature 6); or a polymer compound having, as a partial structure thereof, a benzidine derivative structure such as TPD.

[0092] For the material for the electron blocking layer in the organic EL device of the present invention, it is possible to use, other than the arylamine compound of the present invention, a compound having an electron blocking action, such as: a carbazole derivative, such as 4,4′,4″-tri(N-carbazolyl)triphenylamine (abbreviated hereinbelow as “TCTA”), 9,9-bis[4-(carbazol-9-yl)phenyl]fluorene, 1,3 -bi s(carb azol-9-yl)b enzene (abbreviated hereinbelow as “mCP”), 2,2-bis(4-carbazol-9-ylphenyl)adamantane (abbreviated hereinbelow as “Ad-Cz”), etc.; or a compound containing a triarylamine structure and a triphenylsilyl group typified by 9[4-(carbazol-9-yl)phenyl]-9[4-(triphenylsilyl)phenyl]-9H-fluorene, etc. These materials may also serve as a material for the hole transport layer. These materials may each be formed into a film singly, or a plurality of types of these materials may be mixed and formed into a film, and each may be used as a single layer. It is possible to form a laminate structure constituted by layers each formed singly by the respective materials, or a laminate structure constituted by layers formed by mixing, or a laminate structure constituted by layers each formed singly by the respective materials and layers formed by mixing a plurality of types of materials. These materials can form thin films by known methods, such as vapor deposition, spin coating, ink-jetting, etc.

[0093] For the material for the light-emitting layer in the organic EL device of the present invention, it is possible to use, other than the arylamine compound of the present invention, one of various metal complexes such as a metal complex of a quinolinol derivative, e.g., Alq3, an anthracene derivative, a bisstyrylbenzene derivative, a pyrene derivative, an oxazole derivative, a poly(para-phenylene vinylene) derivative, etc. The light-emitting layer may be constituted by a host material and a dopant material. For the host material, an anthracene derivative may preferably be used, and also, in addition to such light-emitting materials as the arylamine compound of the present invention, it is possible to use, for example, a heterocyclic compound having an indole ring as a partial structure of a fused ring, a heterocyclic compound having a carbazole ring as a partial structure of a fused ring, a carbazole derivative, a thiazole derivative, a benzimidazole derivative, a polydialkylfluorene derivative, etc. For the dopant material, it is possible to use quinacridone, coumarin, rubrene, perylene, a derivative of the above, a benzopyran derivative, a rhodamine derivative, an aminostyryl derivative, etc. These materials may each be formed into a film singly, or a plurality of types of these materials may be mixed and formed into a film, and each may be used as a single layer. It is possible to form a laminate structure constituted by layers each formed singly by the respective materials, or a laminate structure constituted by layers formed by mixing, or a laminate structure constituted by layers each formed singly by the respective materials and layers formed by mixing a plurality of types of materials. These materials can form thin films by known methods, such as vapor deposition, spin coating, ink-jetting, etc.

[0094] It is also possible to use a phosphorescent substance for the light-emitting material. For the phosphorescent substance, it is possible to use a phosphorescent substance such as a metal complex of iridium, platinum, etc. Examples may include green phosphorescent substances such as Ir(ppy).sub.3 etc., blue phosphorescent substances such as Flrpic, FIr6, etc., and red phosphorescent substances such as Btp.sub.2Ir(acac) etc. As regards host materials, examples of the hole injecting/transporting host material may include a carbazole derivative such as 4,4′-di(N-carbazolyl)biphenyl (abbreviated hereinbelow as “CBP”), TCTA, mCP, etc., as well as the arylamine compound of the present invention. Examples of the electron-transporting host material may include p-bis(triphenylsilyl)benzene (abbreviated hereinbelow as “UGH2”), 2,2′ ,2″ -(1,3,5-phenylene)-tris(1-phenyl-1H-benzimidazole) (abbreviated hereinbelow as “TPBI”), etc. By using such materials, it is possible to produce high-performance organic EL devices.

[0095] To avoid concentration quenching, doping of the host material(s) with a phosphorescent substance is preferably performed by co-vapor deposition within a range of 1 to 30 wt. % with respect to the entire light-emitting layer.

[0096] Further, for the light-emitting material, it is possible to use a material emitting delayed fluorescence, e.g., PIC-TRZ, CC2TA, PXZ-TRZ, a CDCB derivative such as 4CzIPN, etc. (see, for example, Non-Patent Literature 3). These materials can form thin films by known methods, such as vapor deposition, spin coating, ink-jetting, etc.

[0097] For the material for the hole blocking layer in the organic EL device of the present invention, it is possible to use a compound having a hole blocking action, with examples including phenanthroline derivatives such as bathocuproine (abbreviated hereinbelow as “BCP”), metal complexes of a quinolinol derivative such as BAlq, various rare-earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, etc. These materials may also serve as materials for the electron transport layer. These materials may each be formed into a film singly, or a plurality of types of these materials may be mixed and formed into a film, and each may be used as a single layer. It is possible to form a laminate structure constituted by layers each formed singly by the respective materials, or a laminate structure constituted by layers formed by mixing, or a laminate structure constituted by layers each formed singly by the respective materials and layers formed by mixing a plurality of types of materials. These materials can form thin films by known methods, such as vapor deposition, spin coating, ink-jetting, etc.

[0098] For the material for the electron transport layer in the organic EL device of the present invention, it is possible to use a metal complex of a quinolinol derivative such as Alq.sub.3,BAlq, etc., one of various metal complexes, a triazole derivative, a triazine derivative, an oxadiazole derivative, a pyridine derivative, a pyrimidine derivative, a benzimidazole derivative, a thiadiazole derivative, an anthracene derivative, a carbodiimide derivative, a quinoxaline derivative, a pyridoindole derivative, a phenanthroline derivative, a silole derivative, etc. These materials may each be formed into a film singly, or a plurality of types of these materials may be mixed and formed into a film, and each may be used as a single layer. It is possible to form a laminate structure constituted by layers each formed singly by the respective materials, or a laminate structure constituted by layers formed by mixing, or a laminate structure constituted by layers each formed singly by the respective materials and layers formed by mixing a plurality of types of materials. These materials can form thin films by known methods, such as vapor deposition, spin coating, ink-jetting, etc.

[0099] For the material for the electron injection layer in the organic EL device of the present invention, it is possible to use an alkali metal salt such as lithium fluoride, cesium fluoride, etc., an alkaline-earth metal salt such as magnesium fluoride etc., a metal complex of a quinolinol derivative such as quinolinol lithium etc., a metal oxide such as aluminum oxide etc., or a metal such as ytterbium (Yb), samarium (Sm), calcium (Ca), strontium (Sr), cesium (Cs), etc. The electron injection layer may, however, be omitted by suitable selection of the electron transport layer and the cathode.

[0100] For the electron injection layer and the electron transport layer, it is possible to use a material ordinarily used for such layers and n-doped with a metal such as cesium etc.

[0101] For the cathode in the organic EL device of the present invention, a metal having a low work function, such as aluminum etc., or an alloy having an even lower work function, such as magnesium silver alloy, magnesium indium alloy, aluminum magnesium alloy, etc., may be used as the electrode material.

EXAMPLE

[0102] Embodiments of the present invention will be described in further detail below according to working examples. Note, however, that the present invention is not limited to the following examples so long as they do not go beyond the gist of the invention.

Example 1

Synthesis of bis(biphenyl-4-yl)-(3′,5′-diphenyl-1,1′:2,'1″-terphenyl-3″-yl)-amine (Compound (58)):

[0103] A reaction vessel was charged with 7.0 g of 2,4,6-triphenyl-bromobenzene, 12.4 g of bi s(biphenyl-4-yl)- [3 -(4,4,5, 5-tetramethyl- [1,3 ,2]-dioxab orolan-2-yl)-phenyl]-amine, 0.3 g of [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, and 3.6 g of sodium hydrogen carbonate, and the mixture was stirred under reflux overnight in a mixed solvent of THF/H.sub.2O. After the mixture was allowed to cool, ethyl acetate/H.sub.2O was added into the system. Then, the organic layer was taken out by extraction and liquid separation and was concentrated, to obtain a crude product. The obtained crude product was purified by column chromatography (adsorbent: silica gel; eluent: dichloromethane/n-heptane), to obtain 9.5 g of a white powder of bis(biphenyl-4-yl)-(3′,5′-diphenyl-1,1′:2,'1″-terphenyl-3″-yl)-amine (Compound (58)) (yield: 74.5%).

##STR00002##

[0104] The structure of the obtained white powder was identified by NMR.

[0105] The following 39 hydrogen signals were detected with .sup.1-NMR (CDCl.sub.3).

[0106] δ (ppm)=7.70 (2H), 7.67 (2H), 7.59 (4H), 7.51-7.29 (19H), 7.24 (4H), 7.00 (1H), 6.87 (6H), 6.67 (1H).

Example 2

Synthesis of (biphenyl-4-yl)-(3′,5′-diphenyl-1, 1′:2′,1′″-terphenyl-3′″-yl)-(4-naphthalen-1-yl-phenyl)-amine (Compound (59)):

[0107] A reaction vessel was charged with 10.0 g of 2,4,6-triphenyl-bromobenzene, 22.3 g of (biphenyl-4-yl)-(4-naphthal en-l-yl-phenyl)- [3 -(4,4,5,5-tetramethyl- [1,3,2]-dioxaborolan-2-yl)-phenyl]-amine, 0.4 g of [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, and 5.1 g of sodium hydrogen carbonate, and the mixture was stirred under reflux overnight in a mixed solvent of THF/H.sub.2O. After the mixture was allowed to cool, ethyl acetate/H.sub.2O was added into the system. Then, the organic layer was taken out by extraction and liquid separation and was concentrated, to obtain a crude product. The obtained crude product was purified by column chromatography (adsorbent: silica gel; eluent: dichloromethane/n-heptane), to obtain 16.0 g of a white powder of (biphenyl-4-yl)-(3′,5′-diphenyl-1,1′:2′,1′″-terphenyl-3″-yl)-(4-naphthalen-1-yl-phenyl)-amine (Compound (59)) (yield: 82.0%).

##STR00003##

[0108] The structure of the obtained white powder was identified by NMR.

[0109] The following 41 hydrogen signals were detected with 41-NMR (CDCl.sub.3).

[0110] δ (ppm)=8.00 (2H), 7.87 (1H), 7.71 (2H), 7.69 (2H), 7.61 (2H), 7.59-7.43 (10H), 7.42-7.22 (14H), 7.03 (1H), 6.98-6.86 (6H), 6.69 (1H).

Example 3

Synthesis of (biphenyl-4-yl)-(3 ‘ ,5’ -diphenyl-1, 1 ‘ :2’ ,1″-terphenyl-3″ -yl)-(4-naphthalen-2-yl-phenyl)-amine (Compound (60)):

[0111] A reaction vessel was charged with 11.0 g of 2,4,6-triphenyl-bromobenzene, 24.6 g of (biphenyl-4-yl)-(4-naphthal en-2-yl-phenyl)- [3 -(4,4,5, 5-tetramethyl- [1,3,2]-dioxab orolan-2-yl)-phenyl]-amine, 0.5 g of [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, and 5.6 g of sodium hydrogen carbonate, and the mixture was stirred under reflux overnight in a mixed solvent of THF/H.sub.2O. After the mixture was allowed to cool, ethyl acetate/H.sub.2O was added into the system. Then, the organic layer was taken out by extraction and liquid separation and was concentrated, to obtain a crude product. The obtained crude product was purified by column chromatography (adsorbent: silica gel; eluent: dichloromethane/n-heptane), to obtain 15.5 g of a white powder of (biphenyl-4-yl)-(3′,5′-diphenyl-1,1′ :2′,1″-terphenyl-3″-yl)-(4-naphthalen-2-yl-phenyl)-amine (Compound (60)) (yield: 72.0%).

##STR00004##

[0112] The structure of the obtained white powder was identified by NMR.

[0113] The following 41 hydrogen signals were detected with .sup.1-NMR (CDCl.sub.3).

[0114] δ (ppm)=8.00 (1H), 7.91 (1H), 7.89 (2H), 7.73 (1H), 7.67 (4H), 7.60-7.37 (12H), 7.37-7.27 (8H), 7.25-7.19 (4H), 6.99 (1H), 6.89 (2H), 6.85 (4H), 6.65 (1H).

Example 4

Synthesis of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-(4-phenanthren-9-yl-phenyl)-phenyl-amine (Compound (15)):

[0115] A reaction vessel was charged with 13.7 g of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-(4-phenanthren-9-yl-phenyl)-amine, 4.0 g of bromobenzene, 0.1 g of palladium(II) acetate, 0.1 g of tri-t-butylphosphine, and 4.1 g of sodium t-butoxide, and the mixture was stirred under reflux for 6 hours in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product. The obtained crude product was purified by crystallization with a dichloromethane/acetone mixed solvent, to obtain 6.7 g of a pale-yellow powder of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-y1)-(4-phenanthren-9-yl-phenyl)-phenyl-amine (Compound (15)) (yield: 43.8%).

##STR00005##

[0116] The structure of the obtained pale-yellow powder was identified by NMR.

[0117] The following 39 hydrogen signals were detected with .sup.1H-NMR (CDCl.sub.3).

[0118] δ (ppm)=8.79 (1H), 8.72 (1H), 8.02 (1H), 7.89 (1H), 7.72-7.56 (9H), 7.45 (2H), 7.37 (1H), 7.33-7.17 (14H), 6.98 (2H), 6.89 (3H), 6.83 (3H), 6.64 (1H).

Example 5

Synthesis of (3′,5′-diphenyl-1,1′:2′,1″,-terphenyl-3″-yl)-phenyl-(1, 1′:4′,1″-terphenyl-4-yl)-amine (Compound (31)):

[0119] A reaction vessel was charged with 10.0 g of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-phenyl-amine, 7.8 g of 4-bromo-[1,1′:4′,1″]terphenyl, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 3.0 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product. The obtained crude product was purified by crystallization with a toluene/acetone mixed solvent, to obtain 8.0 g of a white powder of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-phenyl-(1,1′:4′,1″-terphenyl-4-yl)-amine (Compound (31)) (yield: 54.0%).

##STR00006##

[0120] The structure of the obtained white powder was identified by NMR.

[0121] The following 39 hydrogen signals were detected with 41-NMR (CDCl.sub.3).

[0122] δ (ppm)=7.69-7.60 (10H), 7.45 (4H), 7.40 (2H), 7.36 (2H), 7.29 (6H), 7.17 (2H), 7.270 (4H), 6.95 (2H), 6.80 (5H), 6.77 (1H), 6.62 (1H).

Example 6

Synthesis of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-(4′-naphthalen-1-yl-biphenyl-4-yl)-phenyl-amine (Compound (32)):

[0123] A reaction vessel was charged with 12.0 g of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-phenyl-amine, 10.0 g of 1-(4′-bromo-biphenyl-4-yl)-naphthalene, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 2.9 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product. The obtained crude product was purified by crystallization with a toluene/acetone mixed solvent, to obtain 16.4 g of a white powder of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-phenyl-(4′-naphthalen-1-yl-biphenyl-4-yl)-amine (Compound (32)) (yield: 86.0%).

##STR00007##

[0124] The structure of the obtained white powder was identified by NMR.

[0125] The following 41 hydrogen signals were detected with .sup.1H-NMR (CDCl.sub.3).

[0126] δ (ppm)=8.00 (1H), 7.92 (1H), 7.87 (1H), 7.68 (4H), 7.65 (2H), 7.59-7.41 (10H), 7.36 (1H), 7.30 (2H), 7.29 (4H), 7.21 (4H), 7.18 (2H), 6.96 (2H), 6.82 (5H), 6.79 (1H), 6.63 (1H).

Example 7

Synthesis of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-(4′-naphthalen-2-yl-biphenyl-4-yl)-phenyl-amine (Compound (33)):

[0127] A reaction vessel was charged with 12.0 g of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-phenyl-amine, 10.0 g of 2-(4′-bromo-biphenyl-4-yl)-naphthalene, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 2.9 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product. The obtained crude product was purified by crystallization with a chlorobenzene/acetone mixed solvent, to obtain 14.9 g of a white powder of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-phenyl-(4′-naphthalen-2-yl-biphenyl-4-yl)-amine (Compound (33)) (yield: 78.4%).

##STR00008##

[0128] The structure of the obtained white powder was identified by NMR.

[0129] The following 41 hydrogen signals were detected with .sup.1H-NMR (CDCl.sub.3).

[0130] δ (ppm)=8.09 (1H), 7.92 (2H), 7.87 (1H), 7.80 (3H), 7.68 (4H), 7.67 (2H), 7.50 (2H), 7.45 (1H), 7.43 (3H), 7.36 (1H), 7.32-7.26 (6H), 7.21 (4H), 7.18 (2H), 6.97 (1H), 6.96 (1H), 6.85-6.75 (6H), 6.62 (1H).

Example 8

Synthesis of (biphenyl-4-yl)-(3′,5′-diphenyl-1, 1′:2′,1-terphenyl-3″-yl)-(phenanthren-9-yl)-amine (Compound (61)):

[0131] A reaction vessel was charged with 10.0 g of 2,4,6-triphenyl-bromobenzene, 18.5 g of (b iphenyl-4-yl)-(phenanthren-9-yl)-[3 -(4,4,5, 5 -tetram ethyl-[1,3 ,2] -di oxab orol an-2-y1)-phenyl]-amine, 0.4 g of [1,1′ -bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, and 5.1 g of sodium hydrogen carbonate, and the mixture was stirred under reflux overnight in a mixed solvent of THF/H.sub.2O. After the mixture was allowed to cool, ethyl acetate/H.sub.2O was added into the system. Then, the organic layer was taken out by extraction and liquid separation and was concentrated, to obtain a crude product. The obtained crude product was purified by column chromatography (adsorbent: silica gel; eluent: dichloromethane/n-heptane), to obtain 7.0 g of a pale-yellow powder of (biphenyl-4-yl)-(3′, 5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-(phenanthren-9-yl)-amine (Compound (61)) (yield: 37.0%).

##STR00009##

[0132] The structure of the obtained pale-yellow powder was identified by NMR. The following 39 hydrogen signals were detected with .sup.1H-NMR (CDCl.sub.3).

[0133] δ (ppm)=8.72 (1H), 8.69 (1H), 7.90 (1H), 7.74 (1H), 7.65 (4H), 7.64 (2H), 7.58 (1H), 7.51 (3H), 7.48-7.32 (6H), 7.31-7.22 (9H), 7.19 (4H), 6.99 (1H), 6.82 (1H), 6.62 (3H), 6.52 (1H).

Example 9

Synthesis of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-(4-naphthalen-1-yl-phenyl)-(4-naphthalen-2-yl-phenyl)-amine (Compound (76)):

[0134] A reaction vessel was charged with 13.4 g of (4-naphthalen-2-yl-phenyl)-(3′,5′-diphenyl-1,1′ :2′ ,1″-terphenyl-3″-yl)-amine, 7.6 g of 1-(4-bromo-phenyl)-naphthalene, 0.1 g of palladium(II) acetate, 0.1 g of tri-t-butylphosphine, and 4.3 g of sodium t-butoxide, and the mixture was stirred under reflux for 6 hours in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product. The obtained crude product was purified by crystallization with a dichloromethane/acetone mixed solvent, to obtain 10.6 g of a white powder of (3%5′-diphenyl-1, 1′:2′,1″-terphenyl-3″-yl)-(4-naphthalen-1-yl-phenyl)-(4-naphthalen-2-yl-phenyl)-amine (Compound (76)) (yield: 59.2%).

##STR00010##

[0135] The structure of the obtained white powder was identified by NMR.

[0136] The following 43 hydrogen signals were detected with .sup.1H-NMR (CDCl.sub.3).

[0137] δ (ppm)=8.02 (2H), 7.91 (3H), 7.86 (2H), 7.75 (1H), 7.69 (2H), 7.67 (2H), 7.57 (2H), 7.54-7.41 (8H), 7.37 (1H), 7.33-7.22 (12H), 7.02 (1H), 6.97 (2H), 6.94 (1H), 6.90 (1H), 6.88 (2H), 6.67 (1H).

Example 10

Synthesis of bis(4-naphthalen-2-yl-phenyl)-(3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-amine (Compound (77)):

[0138] A reaction vessel was charged with 7.0 g of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-amine, 11.0 g of 2-(4-bromo-phenyl)-naphthalene, 0.6 g of tris(dibenzylideneacetone)dipalladium(0), 4.4 g of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, and 6.8 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product. The obtained crude product was purified by crystallization with a dichloromethane/acetone mixed solvent, to obtain 4.1 g of a white powder of bis(4-naphthalen-2-yl-phenyl)-(3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-amine (Compound (77)) (yield: 29.1%).

##STR00011##

[0139] The structure of the obtained white powder was identified by NMR.

[0140] The following 43 hydrogen signals were detected with .sup.1H-NMR (CDCl.sub.3).

[0141] δ (ppm)=8.01 (2H), 7.90 (4H), 7.86 (2H), 7.74 (2H), 7.68 (2H), 7.66 (2H), 7.54 (4H), 7.49 (4H), 7.43 (2H), 7.36 (2H), 7.32 (5H), 7.23 (4H), 7.00 (1H), 6.91 (3H), 6.88 (3H), 6.67 (1H).

Example 11

Synthesis of bis(4-naphthalen-1-yl-phenyl)-(3′,5′-diphenyl-1, 1′:2′,1″-terphenyl-3″ -yl)-amine (Compound (78)):

[0142] A reaction vessel was charged with 7.0 g of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-amine, 11.0 g of 1-(4-bromo-phenyl)-naphthalene, 0.6 g of tris(dibenzylideneacetone)dipalladium(0), 4.4 g of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, and 6.8 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product. The obtained crude product was purified by crystallization with a dichloromethane/acetone mixed solvent, to obtain 7.7 g of a white powder of bis(4-naphthalen-1-yl-phenyl)-(3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-amine (Compound (78)) (yield: 54.6%).

##STR00012##

[0143] The structure of the obtained white powder was identified by NMR.

[0144] The following 43 hydrogen signals were detected with 41-NMR (CDCl.sub.3).

[0145] δ (ppm)=8.06 (1H), 7.94 (1H), 7.88 (1H), 7.79 (2H), 7.73 (4H), 7.62 (2H), 7.58-7.47 (5H), 7.44 (2H), 7.37 (2H), 7.32-7.19 (22H), 7.12 (1H).

Example 12

Synthesis of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-(4-naphthalen-2-yl-phenyl)-(phenanthren-9-yl)-amine (Compound (79)):

[0146] A reaction vessel was charged with 13.4 g of (4-naphthalen-2-yl-phenyl)-(3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-amine, 6.9 g of 9-bromo-phenanthrene, 0.1 g of palladium(II) acetate, 0.1 g of tri-t-butylphosphine, and 4.3 g of sodium t-butoxide, and the mixture was stirred under reflux for 6 hours in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product. The obtained crude product was purified by column chromatography (adsorbent: silica gel; eluent: dichloromethane/n-heptane), to obtain 10.8 g of a pale-yellow powder of (3′,5′-diphenyl-1, 1′:2′,1″-terphenyl-3″-yl)-(4-naphthal en-2-yl-phenyl)-(phenanthren-9-yl)-amine (Compound (79)) (yield: 62.4%).

##STR00013##

[0147] The structure of the obtained pale-yellow powder was identified by NMR.

[0148] The following 41 hydrogen signals were detected with .sup.1H-NMR (CDCl.sub.3).

[0149] δ (ppm)=8.74 (1H), 8.70 (1H), 7.95 (1H), 7.92 (1H), 7.88 (1H), 7.86 (1H), 7.84 (1H), 7.75 (1H), 7.69 (1H), 7.66 (6H), 7.59 (1H), 7.49 (2H), 7.46 (1H), 7.43 (4H), 7.40 (1H), 7.35 (1H), 7.27 (6H), 7.20 (4H), 7.01 (1H), 6.84 (1H), 6.67 (2H), 6.65 (1H), 6.54 (1H).

Example 13

Synthesis of (biphenyl-4-yl)-phenyl-(3′,5′-diphenyl-1, 1′:2′,1″:3″-1″:3″-1′″-quaterphenyl-4′″-yl)-amine (Compound (96)):

[0150] A reaction vessel was charged with 7.5 g of 2,4,6-triphenyl-bromobenzene, 12.2 g of (biphenyl-4-yl)-phenyl- [3′-(4,4,5, 5-tetramethyl-[1,3 ,2]-dioxab orolan-2-yl)-biphenyl-4-yl ]-amine, 0.5 g of tetrakis(triphenylphosphine)palladium(0), and 4.0 g of potassium carbonate, and the mixture was stirred under reflux overnight in a mixed solvent of toluene/EtOH/H.sub.2O. After the mixture was allowed to cool, ethyl acetate/H.sub.2O was added into the system. Then, the organic layer was taken out by extraction and liquid separation and was concentrated, to obtain a crude product. The obtained crude product was purified by column chromatography (adsorbent: silica gel; eluent: toluene/n-heptane), to obtain 12.9 g of a white powder of (biphenyl-4-yl)-phenyl-(3′,5′-diphenyl-1,1′:2′,1″:3″-1″′-quaterphenyl-4″′-yl)-amine (Compound (96)) (yield: 94.4%).

##STR00014##

[0151] The structure of the obtained white powder was identified by NMR.

[0152] The following 39 hydrogen signals were detected with .sup.1-NMR (CDCl.sub.3).

[0153] δ (ppm)=7.72 (2H), 7.71 (2H), 7.58 (2H), 7.47 (4H), 7.42 (2H), 7.37 (1H), 7.30 (2H), 7.27 (1H), 7.24-7.16 (11H), 7.14 (4H), 7.10-6.98 (7H), 6.80 (1H).

Example 14

Synthesis of (3′,5′-diphenyl-1, 1′:2′,1″:3″-1″′-quaterphenyl-4″′-yl)-(4-naphthalen-1-yl-phenyl)-phenyl-amine (Compound (100)):

[0154] A reaction vessel was charged with 10.0 g of (3′,5′-diphenyl-1,1′:2′,1″:3″-1′″-quaterphenyl-4″′-yl)-phenyl-amine, 5.7 g of 1-(4-bromo-phenyl)-naphthalene, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 2.1 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product. The obtained crude product was purified by column chromatography (adsorbent: silica gel; eluent: dichloromethane/n-heptane), to obtain 8.3 g of a white powder of (3′,5′-diphenyl-1,1′:2′,1″:3″-1″′-quaterphenyl-4″′-yl)-(4-naphthalen-1-yl-phenyl)-phenyl-amine (Compound (100)) (yield: 60.7%).

##STR00015##

[0155] The structure of the obtained white powder was identified by NMR.

[0156] The following 41 hydrogen signals were detected with .sup.1-NMR (CDCl.sub.3).

[0157] δ (ppm)=8.02 (1H), 7.90 (1H), 7.84 (1H), 7.72 (2H), 7.71 (2H), 7.51 (2H), 7.46 (4H), 7.38 (3H), 7.31 (2H), 7.24-7.01 (22H), 6.80 (1H).

Example 15

Synthesis of (3′,5′-diphenyl-1,1′:2′,1″:3″-1′″-quaterphenyl-4″′-yl)-(4-naphthalen-2-yl-phenyl)-phenyl-amine (Compound (101)):

[0158] A reaction vessel was charged with 10.0 g of (3′,5′-diphenyl-1,1′:2′,1″:3″-1′″-quaterphenyl-4′″-yl)-phenyl-amine, 6.2 g of 2-(4-bromo-phenyl)-naphthalene, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 2.1 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product. The obtained crude product was purified by column chromatography (adsorbent: silica gel; eluent: dichloromethane/n-heptane), to obtain 7.7 g of a white powder of (3′,5′-diphenyl-1,1′:2′,1′″:3″-1′″-quaterphenyl-4″′-yl)-(4-naphthalen-2-yl-phenyl)-phenyl-amine (Compound (101)) (yield: 56.3%).

##STR00016##

[0159] The structure of the obtained white powder was identified by NMR.

[0160] The following 41 hydrogen signals were detected with .sup.1H-HMR (CDCl.sub.3).

[0161] δ (ppm)=8.02 (1H), 7.89 (2H), 7.85 (1H), 7.73 (2H), 7.71 (3H), 7.61 (2H), 7.47 (4H), 7.37 (1H), 7.29 (2H), 7.25-7.13 (15H), 7.12-6.99 (7H), 6.80 (1H).

Example 16

Synthesis of (3′,5′-diphenyl-1, 1′:2′,1″:3″-1″′-quaterphenyl-4″′-yl)-(4-phenanthren-9-yl-phenyl)-phenyl-amine (Compound (102)):

[0162] A reaction vessel was charged with 11.0 g of (3′,5′-diphenyl-1,1′:2′,1″:3″-1′″-quaterphenyl-4′″-yl)-phenyl-amine, 8.0 g of 9-(4-bromo-phenyl)-phenanthrene, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 2.3 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product. The obtained crude product was purified by crystallization with a toluene/acetone mixed solvent, to obtain 12.6 g of a white powder of (3′,5′-diphenyl-1,1′:2′,1″:3″-1′″-quaterphenyl-4″′-yl)-(4-phenanthren-9-yl-phenyl)-phenyl-amine (Compound (102)) (yield: 78.5%).

##STR00017##

[0163] The structure of the obtained white powder was identified by NMR.

[0164] The following 43 hydrogen signals were detected with .sup.1H-NMR (CDCl.sub.3).

[0165] δ (ppm)=8.78 (1H), 8.72 (1H), 8.06 (1H), 7.90 (1H), 7.73 (2H), 7.71 (3H), 7.67 (2H), 7.62 (1H), 7.58 (1H), 7.46 (2H), 7.43 (2H), 7.37 (1H), 7.32 (2H), 7.24-7.17 (15H), 7.17-7.02 (7H), 6.81 (1H).

Example 17

Synthesis of (3′,5′-diphenyl-1,1′:2′,1″:3″-1′″-quaterphenyl-4′″-yl)-phenyl-(1,1′:4′,1″-terphenyl-4-yl)-amine (Compound (107)):

[0166] A reaction vessel was charged with 10.0 g of (3′,5′-diphenyl-1,1′:2′,1″:3″-1′″-quaterphenyl-4′″-yl)-phenyl-amine, 6.7 g of 4-bromo-[1,1′:4′,1″]terphenyl, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 2.1 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product. The obtained crude product was purified by column chromatography (adsorbent: silica gel; eluent: dichloromethane/n-heptane), to obtain 9.4 g of a pale-yellow powder of (3′,5′-diphenyl-1, 1′:2′,1″:3″-1′″-quaterphenyl-4″′-yl)-phenyl-(1,1′:4′,1″-terphenyl-4-yl)-amine (Compound (107)) (yield: 66.4%).

##STR00018##

[0167] The structure of the obtained pale-yellow powder was identified by NMR.

[0168] The following 43 hydrogen signals were detected with .sup.1H-NMR (CDCl.sub.3).

[0169] δ (ppm)=7.72 (2H), 7.71 (2H), 7.66 (4H), 7.64 (2H), 7.53 (2H), 7.46 (4H), 7.36 (2H), 7.28 (2H), 7.24-7.12 (15H), 7.11-6.99 (7H), 6.80 (1H).

Example 18

Synthesis of bis(biphenyl-4-yl)-(3′,5′-diphenyl-1,1′:2′,1″:3″-1′″-quaterphenyl-4″'-yl)-amine (Compound (115)):

[0170] A reaction vessel was charged with 10.0 g of biphenyl-4-yl-(3′,5′-diphenyl-1,1′:2′,1″:3″-1′″-quaterphenyl-4″'-yl)-amine, 4.5 g of 4-bromo-biphenyl, 0.7 g of tris(dibenzylideneacetone)dipalladium(0), 0.7 g of tri-t-butylphosphine, and 2.0 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product. The obtained crude product was purified by crystallization with a toluene/acetone mixed solvent, to obtain 10.5 g of a white powder of bis(biphenyl-4-yl)-3′,5′-diphenyl-1, 1′:2′,1′″:3″-1′″-quaterphenyl-4′-yl)-amine (Compound (115)) (yield: 84.5%).

##STR00019##

[0171] The structure of the obtained white powder was identified by NMR.

[0172] The following 43 hydrogen signals were detected with .sup.1H-NMR (CDCl.sub.3).

[0173] δ (ppm)=7.73 (2H), 7.72 (2H), 7.59 (4H), 7.51 (4H), 7.47 (2H), 7.43 (4H), 7.38 (1H), 7.32 (2H), 7.24-7.15 (15H), 7.14-7.01 (6H), 6.81 (1H).

Example 19

Synthesis of (biphenyl-4-yl)-(3′,5′-diphenyl-1,1′:2′,1″:3″-1′″-quaterphenyl-4′″-yl)-4-naphthalen-2-yl-phenyl)-amine (Compound (116)):

[0174] A reaction vessel was charged with 10.0 g of biphenyl-4-yl-(3′,5′-diphenyl-1,1′:2′,1″:3″-1′″-quaterphenyl-4′″-yl)-amine, 5.4 g of 2-(4-bromo-phenyl)-naphthalene, 0.7 g of tris(dibenzylideneacetone)dipalladium(0), 0.7 g of tri-t-butylphosphine, and 2.0 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product. The obtained crude product was purified by crystallization with a toluene/acetone mixed solvent, to obtain 9.1 g of a pale-yellow powder of (biphenyl-4-yl)-(3′,5′-diphenyl-1,1′:2′,1″:3″′-1′″-quaterphenyl-4′″-yl)-(4-naphthalen-2-yl-phenyl)-amine (Compound (116)) (yield: 68.8%).

##STR00020##

[0175] The structure of the obtained pale-yellow powder was identified by NMR.

[0176] The following 45 hydrogen signals were detected with .sup.1H-NMR (CDCl.sub.3).

[0177] δ (ppm)=8.03 (1H), 7.90 (2H), 7.86 (1H), 7.75 (2H), 7.72 (3H), 7.64 (2H), 7.60 (2H), 7.54-7.41 (8H), 7.38 (1H), 7.33 (1H), 7.25-7.17 (15H), 7.16-7.02 (6H), 6.81 (1H).

Example 20

Synthesis of (biphenyl-4-yl)-(3′,5′-diphenyl-1,1′:2′,1″:3″-1″′-quaterphenyl-4″′-y1)-(4-naphthalen-1-yl-phenyl)-amine (Compound (117)):

[0178] A reaction vessel was charged with 10.0 g of biphenyl-4-yl-(3′,5′-diphenyl-1,1′:2′,1″:3″-1′″-quaterphenyl-4″′-yl)-amine, 5.4 g of 1-(4-bromo-phenyl)-naphthalene, 0.7 g of tris(dibenzylideneacetone)dipalladium(0), 0.7 g of tri-t-butylphosphine, and 2.3 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product. The obtained crude product was purified by column chromatography (adsorbent: silica gel; eluent: dichloromethane/n-heptane), to obtain 12.5 g of a pale-yellow powder of (biphenyl-4-yl)-(3′,5′-diphenyl-1,1′:2′,1″:3″-1″′-quaterphenyl-4″'-yl)-(4-naphthalen-1-yl-phenyl)-amine (Compound (117)) (yield: 94.5%).

##STR00021##

[0179] The structure of the obtained pale-yellow powder was identified by NMR.

[0180] The following 45 hydrogen signals were detected with .sup.1H-NMR (CDCl.sub.3).

[0181] δ (ppm)=8.04 (1H), 7.91 (1H), 7.85 (1H), 7.73 (2H), 7.72 (2H), 7.61 (2H), 7.56-7.35 (13H), 7.32 (1H), 7.28-7.15 (17H), 7.11 (1H), 7.08 (1H), 7.07 (2H), 6.81 (1H).

Example 21

Synthesis of (biphenyl-4-yl)-(3′,5′-diphenyl-1,1′:2′,1″:3″-1″′-quaterphenyl-4″′-yl)-(phenanthren-2-yl)-amine (Compound (118)):

[0182] A reaction vessel was charged with 10.0 g of biphenyl-4-yl-(3′,5′-diphenyl-1,1′:2′,1″:3″-1′″-quaterphenyl-4″'-yl)-amine, 4.9 g of 2-bromo-phenanthrene, 0.7 g of tris(dibenzylideneacetone)dipalladium(0), 0.7 g of tri-t-butylphosphine, and 2.3 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product. The obtained crude product was purified by crystallization with a toluene/acetone mixed solvent, to obtain 8.7 g of a pale-yellow powder of (biphenyl-4-yl)-(3′,5′-diphenyl-1,1′:2′,1″:3″-1″′-quaterphenyl-4″-yl)-(phenanthren-2-yl)-amine (Compound (118)) (yield: 67.9%).

##STR00022##

[0183] The structure of the obtained pale-yellow powder was identified by NMR.

[0184] The following 43 hydrogen signals were detected with .sup.11-1-NMIR (CDCl.sub.3).

[0185] δ (ppm)=8.59 (1H), 8.56 (1H), 7.85 (1H), 7.72 (2H), 7.71 (2H), 7.68 (1H), 7.63 (1H), 7.60 (2H), 7.54 (5H), 7.45 (5H), 7.38 (1H), 7.32 (1H), 7.25-7.12 (15H), 7.11 (1H), 7.05 (1H), 7.04 (2H), 6.81 (1H).

Example 22

Synthesis of (biphenyl-4-yl)-(3′,5′-diphenyl-1,1′:2′,1″:3″-1″′-quaterphenyl-4″′-ly)-(phenanthren-9-yl)-amine (Compound (119)):

[0186] A reaction vessel was charged with 10.0 g of biphenyl-4-yl-(3′,5′-diphenyl-1,1′:2′,1″:3″-1′″-quaterphenyl-4″′-yl)-amine, 4.9 g of 9-bromo-phenanthrene, 0.7 g of tris(dibenzylideneacetone)dipalladium(0), 0.7 g of tri-t-butylphosphine, and 2.3 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product. The obtained crude product was purified by column chromatography (adsorbent: silica gel; eluent: dichloromethane/n-heptane), to obtain 7.9 g of a pale-yellow powder of (biphenyl-4-yl)-(3′,5′-diphenyl-1,1′:2′,1″:3″-1″′-quaterphenyl-4′″-yl)-(phenanthren-9-yl)-amine (Compound (119)) (yield: 61.6%).

##STR00023##

[0187] The structure of the obtained pale-yellow powder was identified by NMR.

[0188] The following 43 hydrogen signals were detected with 41-NMR (CDCl.sub.3).

[0189] δ (ppm)=8.76 (1H), 8.72 (1H), 8.06 (1H), 7.78 (1H), 7.71 (2H), 7.69 (2H), 7.66 (2H), 7.64 (1H), 7.59 (1H), 7.55 (2H), 7.51 (1H), 7.46 (1H), 7.44 (3H), 7.39 (2H), 7.36 (1H), 7.28 (1H), 7.22-7.12 (13H), 7.07 (3H), 7.01 (1H), 6.97 (2H), 6.77 (1H).

Example 23

Synthesis of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-(4′-phenanthren-9-yl-biphenyl-4-yl)-phenyl-amine (Compound (127)):

[0190] A reaction vessel was charged with 10.0 g of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-phenyl-amine, 9.5 g of 9-(4′-bromo-biphenyl-4-yl)-phenanthrene, 0.1 g of palladium(II) acetate, 0.2 g of tri-t-butylphosphine, and 2.4 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product. The obtained crude product was purified by crystallization with a toluene/acetone mixed solvent, to obtain 14.6 g of a white powder of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-phenyl-(4′-phenanthren-9-yl-biphenyl-4-yl)-amine (Compound (127)) (yield: 86.3%).

##STR00024##

[0191] The structure of the obtained white powder was identified by NMR.

[0192] The following 43 hydrogen signals were detected with 41-NMR (CDCl.sub.3).

[0193] δ (ppm)=8.79 (1H), 8.74 (1H), 8.01 (1H), 7.91 (1H), 7.73 (1H), 7.69 (3H), 7.67 (3H), 7.65 (2H), 7.62 (3H), 7.56 (1H), 7.47 (2H), 7.44 (2H), 7.36 (1H), 7.29 (6H), 7.20 (6H), 6.97 (2H), 6.83 (5H), 6.79 (1H), 6.63 (1H).

Example 24

Synthesis of (biphenyl-4-yl)-(3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-(4-phenanthren-9-yl-phenyl)-amine (Compound (130)):

[0194] A reaction vessel was charged with 12.5 g of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-(4-phenanthren-9-yl-phenyl)-amine, 5.4 g of 4-bromo-biphenyl, 0.1 g of palladium(II) acetate, 0.1 g of tri-t-butylphosphine, and 3.7 g of sodium t-butoxide, and the mixture was stirred under reflux for 6 hours in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product. The obtained crude product was purified by crystallization with a dichloromethane/acetone mixed solvent, to obtain 9.3 g of a white powder of (biphenyl-4-yl)-(3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-(4-phenanthren-9-yl-phenyl)-amine (Compound (130)) (yield: 60.1%).

##STR00025##

[0195] The structure of the obtained white powder was identified by NMR.

[0196] The following 43 hydrogen signals were detected with 41-NMR (CDCl.sub.3).

[0197] 6 (ppm) =8.79 (1H), 8.73 (1H), 8.03 (1H), 7.90 (1H), 7.70 (2H), 7.68 (2H), 7.67 (2H), 7.63 (1H), 7.61 (1H), 7.58 (2H), 7.44 (6H), 7.37 (1H), 7.33 (3H), 7.31-7.21 (11H), 7.01 (1H), 6.94 (3H), 6.89 (3H), 6.67 (1H).

Example 25

Synthesis of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-(4-naphthalen-1-yl-phenyl)-(1,1′:4′,1″-terphenyl-4-yl)-amine (Compound (132)):

[0198] A reaction vessel was charged with 8.0 g of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-(1,1′:4′,1″-terphenyl-4-yl)-amine, 4.3 g of 1-(4-bromo-phenyl)-naphthalene, 0.1 g of palladium(II) acetate, 0.1 g of tri-t-butylphosphine, and 1.6 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product. The obtained crude product was purified by crystallization with a toluene/acetone mixed solvent, to obtain 7.9 g of a white powder of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-(4-naphthalen-1-yl-phenyl)-(1, 1′:4′,1″-terphenyl-4-yl)-amine (Compound (132)) (yield: 74.5%).

##STR00026##

[0199] The structure of the obtained white powder was identified by NMR.

[0200] The following 45 hydrogen signals were detected with .sup.1H-NMR (CDCl.sub.3).

[0201] δ (ppm)=8.01 (1H), 7.91 (1H), 7.85 (1H), 7.71-7.62 (10H), 7.56-7.41 (10H), 7.36 (2H), 7.32-7.21 (12H), 7.01 (1H), 6.94 (3H), 6.88 (3H), 6.67 (1H).

Example 26

Synthesis of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-(4-naphthalen-2-yl-phenyl)-(1,1′:4 ′,1″-terphenyl-4-yl)-amine (Compound (133)):

[0202] A reaction vessel was charged with 8.0 g of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-(1,1′:4′,1″-terphenyl-4-yl)-amine, 4.0 g of 2-(4-bromo-phenyl)-naphthalene, 0.1 g of tris(dibenzylideneacetone)dipalladium(0), 0.1 g of tri-t-butylphosphine, and 1.5 g of sodium t-butoxide, and the mixture was stirred under reflux for 3 hours in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product. The obtained crude product was purified by crystallization with a toluene/acetone mixed solvent, to obtain 8.5 g of a pale-red powder of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-(4-naphthal en-2-yl-phenyl)-(1, 1′:4′,1″-terphenyl-4-yl)-amine (Compound (133)) (yield: 80.3%).

##STR00027##

[0203] The structure of the obtained pale-red powder was identified by NMR.

[0204] The following 45 hydrogen signals were detected with .sup.1H-NMIR (CDCl.sub.3). 6 (ppm) =8.00 (1H), 7.91 (1H), 7.89 (1H), 7.86 (1H), 7.73 (1H), 7.70-7.62 (10H), 7.53 (2H), 7.51-7.40 (8H), 7.35 (2H), 7.30 (6H), 7.22 (4H), 6.99 (1H), 6.91 (2H), 6.86 (4H), 6.66 (1H).

Example 27

Synthesis of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″ -yl)-(3 -naphthalen-1-yl-phenyl)-(1,1′:4′,1″-terphenyl-4-yl)-amine (Compound (134)):

[0205] A reaction vessel was charged with 8.0 g of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-(1,1′:4′,1″-terphenyl-4-yl)-amine, 4.3 g of 1-(3-bromo-phenyl)-naphthalene, 0.1 g of palladium(II) acetate, 0.1 g of tri-t-butylphosphine, and 1.6 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product. The obtained crude product was purified by crystallization with a toluene/acetone/n-heptane mixed solvent, to obtain 6.0 g of a white powder of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-(3-naphthalen-l-yl-phenyl)-(1,1′:4′,1″-terphenyl-4-yl)-amine (Compound (134)) (yield: 56.6%).

##STR00028##

[0206] The structure of the obtained white powder was identified by NMR.

[0207] The following 45 hydrogen signals were detected with .sup.1H-NMR (CDCl.sub.3).

[0208] δ (ppm)=7.87 (3H), 7.68-7.59 (10H), 7.50 (1H), 7.48-7.32 (11H), 7.29 (1H), 7.14 (4H), 7.09 (7H), 6.99 (2H), 6.91 (1H), 6.88 (1H), 6.87 (1H), 6.84 (2H), 6.63 (1H).

Example 28

Synthesis of (3′,5 ′-diphenyl-1,1′:2′,1″-terphenyl-3″ -yl)-(3 -naphthal en-2-yl-phenyl)-(1,1′:4′,1″-terphenyl-4-yl)-amine (Compound (135)):

[0209] A reaction vessel was charged with 8.0 g of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-(1,1′:4′,1″-terphenyl-4-yl)-amine, 4.3 g of 2-(3-bromo-phenyl)-naphthalene, 0.1 g of palladium(II) acetate, 0.1 g of tri-t-butylphosphine, and 1.6 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product. The obtained crude product was purified by crystallization with a toluene/acetone mixed solvent, to obtain 6.5 g of a white powder of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-(3 -naphthal en-2-yl-phenyl)-(1, 1′:4′,1″-terphenyl-4-yl)-amine (Compound (135)) (yield: 61.4%).

##STR00029##

[0210] The structure of the obtained white powder was identified by NMR.

[0211] The following 45 hydrogen signals were detected with .sup.1H-NMR (CDCl.sub.3).

[0212] δ (ppm)=7.93 (1H), 7.87 (2H), 7.85 (1H), 7.70-7.61 (11H), 7.53-7.39 (8H), 7.35 (2H), 7.31 (2H), 7.28 (1H), 7.25-7.15 (10H), 6.99 (1H), 6.87 (2H), 6.83 (2H), 6.81 (1H), 6.65 (1H).

Example 29

Synthesis of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-(2-naphthalen-1-yl-phenyl)-(1,1′: 4′,1″-terphenyl-4-yl)-amine (Compound (136)):

[0213] A reaction vessel was charged with 8.0 g of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-(1,1′:4′,1″-terphenyl-4-yl)-amine, 4.3 g of 1-(2-bromo-phenyl)-naphthalene, 0.1 g of palladium(II) acetate, 0.1 g of tri-t-butylphosphine, and 1.5 g of sodium t-butoxide, and the mixture was stirred under reflux overnight in a toluene solvent. After the mixture was allowed to cool, a filtrate obtained by filtering was concentrated, to obtain a crude product. The obtained crude product was purified by crystallization with a toluene/acetone mixed solvent, to obtain 5.2 g of a pale-yellow powder of (3′,5′-diphenyl-1,1′:2′,1″-terphenyl-3″-yl)-(2-naphthalen-1-yl-phenyl)-(1,1′:4′,1″-terphenyl-4-yl)-amine (Compound (136)) (yield: 48.7%).

##STR00030##

[0214] The structure of the obtained pale-yellow powder was identified by NMR.

[0215] The following 45 hydrogen signals were detected with .sup.1H-NMR (CDCl.sub.3).

[0216] δ (ppm)=7.66 (3H), 7.63 (2H), 7.59 (5H), 7.45 (5H), 7.38-7.23 (14H), 7.22-7.11 (6H), 7.01 (1H), 6.89 (1H), 6.78 (3H), 6.66 (1H), 6.56 (1H), 6.43 (1H), 6.09 (2H).

Example 30

[0217] Using a high-sensitivity differential scanning calorimeter (D SC3100SA from Bruker AXS), the melting point and the glass transition point were measured for each of the arylamine compounds obtained in Examples 1 to 29. The results are shown in Table 1.

TABLE-US-00001 TABLE 1 Melting point Glass transition point Compound of Example 1 214° C. 105° C. Compound of Example 2 — 116° C. Compound of Example 3 — 112° C. Compound of Example 4 — 119° C. Compound of Example 5 — 105° C. Compound of Example 6 — 114° C. Compound of Example 7 — 110° C. Compound of Example 8 — 131° C. Compound of Example 9 — 121° C. Compound of Example 10 — 116° C. Compound of Example 11 — 126° C. Compound of Example 12 — 136° C. Compound of Example 13 — 116° C. Compound of Example 14 — 124° C. Compound of Example 15 — 124° C. Compound of Example 16 — 140° C. Compound of Example 17 — 129° C. Compound of Example 18 — 133° C. Compound of Example 19 — 136° C. Compound of Example 20 — 137° C. Compound of Example 21 — 146° C. Compound of Example 22 — 151° C. Compound of Example 23 — 130° C. Compound of Example 24 — 130° C. Compound of Example 25 — 126° C. Compound of Example 26 — 123° C. Compound of Example 27 — 117° C. Compound of Example 28 — 117° C. Compound of Example 29 — 126° C.

[0218] The results show that the arylamine compounds obtained in Examples 1 to 29 each have a glass transition point of 100° C. or higher. This indicates that these compounds are stable in a thin-film state.

Example 31

[0219] A 100-nm-thick vapor deposition film was formed on an ITO substrate by using the respective arylamine compounds obtained in Examples 1 to 27, and the work function was measured using an ionization potential measurement device (PYS-202 from Sumitomo Heavy Industries, Ltd.). The results are shown in Table 2.

TABLE-US-00002 TABLE 2 Work function Compound of Example 1 5.76 eV Compound of Example 2 5.75 eV Compound of Example 3 5.74 eV Compound of Example 4 5.83 eV Compound of Example 5 5.77 eV Compound of Example 6 5.79 eV Compound of Example 7 5.77 eV Compound of Example 8 5.79 eV Compound of Example 9 5.76 eV Compound of Example 10 5.72 eV Compound of Example 11 5.79 eV Compound of Example 12 5.78 eV Compound of Example 13 5.77 eV Compound of Example 14 5.78 eV Compound of Example 15 5.74 eV Compound of Example 16 5.78 eV Compound of Example 17 5.71 eV Compound of Example 18 5.71 eV Compound of Example 19 5.69 eV Compound of Example 20 5.72 eV Compound of Example 21 5.70 eV Compound of Example 22 5.72 eV Compound of Example 23 5.79 eV Compound of Example 24 5.77 eV Compound of Example 25 5.78 eV Compound of Example 26 5.68 eV Compound of Example 27 5.79 eV Compound of Example 28 5.74 eV Compound of Example 29 5.75 eV

[0220] The results show that the arylamine compounds obtained in Examples 1 to 27 exhibit a more suitable energy level compared to the work function of approximately 5.4 eV of typical hole-transporting materials such as NPD, TPD, etc., and thus have favorable hole transportability.

Example 32

[0221] As illustrated in FIG. 13, an organic EL device was prepared by vapor-depositing a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, an electron transport layer 7, an electron injection layer 8, a cathode 9, and a capping layer 10 in this order onto a glass substrate 1 having formed thereon a reflective ITO electrode as a transparent anode 2 in advance.

[0222] More specifically, a glass substrate 1 having formed thereon, in order, a 50-nm-thick ITO film, a 100-nm-thick silver-alloy reflective film, and a 5-nm-thick ITO film was subjected to ultrasonic cleaning in isopropyl alcohol for 20 minutes, and then dried for 10 minutes on a hot plate heated to 250° C. Then, after UV ozone treatment for 2 minutes, the glass substrate having the ITO was mounted to a vacuum vapor deposition apparatus, in which the pressure was reduced to 0.001 Pa or lower.

[0223] Next, a hole injection layer 3 was formed so as to cover the transparent anode 2 and so that the film thickness was 10 nm, by performing binary vapor deposition of an electron acceptor (Acceptor-1) having the following structural formula and a compound (HTM-1) having the following structural formula at a rate at which the vapor deposition rate ratio between Acceptor-1 and HTM-1 was 3:97.

[0224] On this hole injection layer 3, the compound (HTM-1) having the following structural formula was formed as a hole transport layer 4 having a film thickness of 140 nm.

[0225] On this hole transport layer 4, Compound (58) of Example 1 was formed as an electron blocking layer 5 having a film thickness of 5 nm.

[0226] On this electron blocking layer 5, a light-emitting layer 6 was formed so that the film thickness was 20 nm, by performing binary vapor deposition of a compound (EMD-1) having the following structural formula and a compound (EMH-1) having the following structural formula at a rate at which the vapor deposition rate ratio between EMD-1 and EMH-1 was 5:95.

[0227] On this light-emitting layer 6, an electron transport layer 7 was formed so that the film thickness was 30 nm, by performing binary vapor deposition of a compound (ETM-1) having the following structural formula and a compound (ETM-2) having the following structural formula at a rate at which the vapor deposition rate ratio between ETM-1 and ETM-2 was 50:50.

[0228] On this electron transport layer 7, lithium fluoride was formed as an electron injection layer 8 having a film thickness of 1 nm.

[0229] On this electron injection layer 8, a magnesium-silver alloy was formed as a cathode 9 having a film thickness of 12 nm.

[0230] Finally, a compound (CPL-1) having the following structure was formed as a capping layer 10 having a film thickness of 60 nm.

[0231] Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

##STR00031## ##STR00032## ##STR00033##

Example 33

[0232] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (59) of Example 2 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 34

[0233] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (60) of Example 3 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 35

[0234] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (15) of Example 4 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 36

[0235] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (31) of Example 5 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 37

[0236] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (32) of Example 6 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 38

[0237] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (33) of Example 7 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 39

[0238] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (61) of Example 8 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 40

[0239] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (76) of Example 9 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 41

[0240] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (77) of Example 10 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 42

[0241] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (78) of Example 11 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature.

[0242] Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 43

[0243] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (79) of Example 12 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 44

[0244] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (96) of Example 13 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 45

[0245] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (100) of Example 14 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 46:

[0246] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (101) of Example 15 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 47

[0247] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (102) of Example 16 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 48

[0248] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (107) of Example 17 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 49

[0249] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (115) of Example 18 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 50

[0250] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (116) of Example 19 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 51

[0251] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (117) of Example 20 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 52

[0252] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (118) of Example 21 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 53

[0253] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (119) of Example 22 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 54

[0254] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (127) of Example 23 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 55

[0255] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (130) of Example 24 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 56

[0256] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (132) of Example 25 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 57

[0257] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (133) of Example 26 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 58

[0258] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (134) of Example 27 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Example 59

[0259] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (135) of Example 28 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

[0260] Example 60

[0261] An organic EL device was produced according to the same conditions, except that, in Example 32, Compound (136) of Example 29 was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

Comparative Example 1

[0262] For comparison, an organic EL device was produced according to the same conditions, except that, in Example 32, a compound (HTM-2) having the following structural formula (see, for example, Patent Literature 5) was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

##STR00034##

Comparative Example 2

[0263] For comparison, an organic EL device was produced according to the same conditions, except that, in Example 32, a compound (HTM-3) having the following structural formula was used instead of Compound (58) of Example 1 as the material for the electron blocking layer 5. Properties of the produced organic EL device were measured in the atmosphere at atmospheric temperature. Measurement results of light emission properties when a direct-current voltage was applied to the produced organic EL device are collectively shown in Table 3.

##STR00035##

[0264] Device life was measured using the organic EL devices produced in Examples 32 to 60 and Comparative Examples 1 and 2. The results are collectively shown in Table 3. Device life was measured as follows. Constant current driving was performed, with the light emission luminance at the start of light emission (i.e., initial luminance) being 1000 cd/m.sup.2, and the time it took for the light emission luminance to attenuate to 950 cd/m.sup.2 (95% attenuation: amounting to 95% when the initial luminance is considered 100%) was measured.

TABLE-US-00003 TABLE 3 (@10 mA/cm.sup.2) Device life Electron Voltage Luminance Luminous Power 95% blocking layer [V] [cd/m.sup.2] efficiency efficiency attenuation Example 32 Compound 58 3.45 1011 10.11 9.21 282 Example 33 Compound 59 3.47 1001 10.01 9.18 311 Example 34 Compound 60 3.43 1036 10.36 9.40 365 Example 35 Compound 15 3.46 940 9.40 8.51 339 Example 36 Compound 31 3.44 1005 10.06 9.20 283 Example 37 Compound 32 3.47 1022 10.24 9.28 294 Example 38 Compound 33 3.44 1022 10.23 9.36 378 Example 39 Compound 61 3.46 940 9.40 8.51 339 Example 40 Compound 76 3.46 1070 10.71 9.74 276 Example 41 Compound 77 3.43 1018 10.18 9.34 443 Example 42 Compound 78 3.49 1102 11.05 9.95 291 Example 43 Compound 79 3.48 1027 10.27 9.27 267 Example 44 Compound 96 3.46 954 9.55 8.67 272 Example 45 Compound 100 3.39 1052 10.52 9.76 310 Example 46 Compound 101 3.41 994 9.94 9.14 348 Example 47 Compound 102 3.41 1056 10.56 9.74 285 Example 48 Compound 107 3.34 1067 10.67 9.61 434 Example 49 Compound 115 3.43 964 9.64 8.83 401 Example 50 Compound 116 3.42 1041 10.42 9.58 632 Example 51 Compound 117 3.41 1024 10.24 9.44 295 Example 52 Compound 118 3.44 1002 10.02 9.16 284 Example 53 Compound 119 3.47 943 9.43 8.54 272 Example 54 Compound 127 3.47 1040 10.44 9.45 275 Example 55 Compound 130 3.47 1058 10.59 9.60 306 Example 56 Compound 132 3.38 986 9.86 9.10 389 Example 57 Compound 133 3.43 937 9.37 8.61 363 Example 58 Compound 134 3.40 987 9.87 9.13 292 Example 59 Compound 135 3.44 1014 10.15 9.29 353 Example 60 Compound 136 3.43 1011 10.12 9.24 311 Comparative HTM-2 3.49 915 9.15 8.23 245 Comparative HTM-3 3.54 897 8.97 8.19 269

[0265] As shown in Table 3, the organic EL devices employing the arylamine compounds of the present invention have low driving voltages. Further, while the luminous efficiency when a current having a current density of 10 mA/cm.sup.2 was passed was 8.97 to 9.15 cd/A for the organic EL devices of Comparative Examples 1 and 2, the organic EL devices of Examples 32 to 60 had high efficiency of 9.37 to 11.05 cd/A. Furthermore, while the organic EL devices of Comparative Examples 1 and 2 had a power efficiency of 8.19 to 8.23 lm/W, the organic EL devices of Examples 32 to 60 had high efficiency of 8.51 to 9.95 lm/W. Furthermore, while the organic EL devices of Comparative Examples 1 and 2 had a device life (95% attenuation) of 245 to 269 hours, the organic EL devices of Examples 32 to 60 had comparable or longer lifetime of 267 to 632 hours.

[0266] These results reveal that, since the organic EL devices of the present invention use arylamine compounds having high hole mobility and excellent electron blockability, it is possible to achieve organic EL devices having higher luminous efficiency and longer lifetime while maintaining low driving voltage, compared to conventional organic EL devices.

INDUSTRIAL APPLICABILITY

[0267] The organic EL device according to the present invention, which uses an arylamine compound having a specific structure, has improved luminous efficiency, and also, the organic EL device can be improved in durability. Thus, for example, application can be expanded to home electrical appliances and lightings. Further, the arylamine compound of the present invention is not only usable for organic EL devices, but also usable in the field of electronic devices, such as electrophotographic photoreceptors, image sensors, photoelectric conversion devices, solar cells, etc. [0268] 1: Glass substrate [0269] 2: Transparent anode [0270] 3: Hole injection layer [0271] 4: Hole transport layer [0272] 5: Electron blocking layer [0273] 6: Light-emitting layer [0274] 7: Electron transport layer [0275] 8: Electron injection layer [0276] 9: Cathode [0277] 10: Capping layer