TW201016663A - Organic electroluminescent element and aromatic amine derivative using the same - Google Patents

Abstract

An organic electroluminescent element having high luminesce efficiency and a long life span even if preserved in high temperature. and an aromatic amine derivative for realizing the same are provided. The aromatic amine derivative is represented by the following formula (1). [Formula 1] In the formula (1), Ar1 is represented by the following formula (2), and Ar2 is represented by the following formula (3). [Formula 2]

Description

201016663 VI. Description of the Invention: [Technical Field] The present invention relates to an aromatic amine derivative and an organic electroluminescence (EL) device using the same. More specifically, the present invention relates to an aromatic amine derivative which can improve the luminous efficiency of an organic EL element after storage at a high temperature and extend the life of the organic EL element. [Prior Art]

❹ The organic EL element is a self-luminous element which utilizes the principle of causing a fluorescent substance to emit light by applying an electric field to recombine energy by a hole injected from an anode and electrons injected from a cathode. since

CWTang et al. of Eastman's Kodak Company presented a report on the construction of low-voltage-driven organic EL elements by laminated elements (CWTang, SA Vanslyke, Applied Physics Letters (10), Vol. 51, p. 913, 1987 Since the year of the year, research on organic EL elements using organic materials as constituent materials has been popular. Regarding the element structure of the organic ELtg device, there are known a two-layer type including hole transport (injection layer and electron transport light-emitting layer, or a three-layer type including hole transport (electron transport (injection) layer). With regard to such a laminated U-shaped 7L piece, in order to improve the re-engagement of the hole and the electrons of the person to be injected, the person skilled in the art M is generated in the tree structure or the formation method ====== 5 201016663 These adverse effects must increase the glass transition temperature (Tg) of the same material. Therefore, the hole transporting material must have more aromatic filaments in the knife (for example, US Patent No. 432, 432 Wei Cai Cut (4) The family has a bribe, the United States has a structure of 8 to 12 benzene rings, but it has a good structure. Hole-transporting material ❹ ❹ : When forming a thin film to produce an organic EL element, there are the following problems: clogging at the outlet of the steamed mineral by = crystallization, or due to: = film defects - resulting in good organic a-component Rate decreases, etc. In addition, although the intramolecular has a higher (five) usually higher However, considering the =, there will be a phenomenon of decomposition or formation of a vaporized ore film when the seam is formed, so there is a problem of short life. The single-wheel material is known to have a material - then the bulletin, the Japanese too true Ml 曰Patent Publication No. 2004-103467, No. U-273_.) However, the life or efficiency of such components is particularly improved.

: There is a problem with the life or efficiency after saving J ==,. - The material is linked to the amine (Japanese Patent Special Publication No. 1M4, ed. Suspension No. 6), but this amine derivative = 6 201016663. Or 増 * life i rate =: r organic el component is more excellent: performance of the \ \ cattle material. Provide the title: research, its purpose is

After a long period of organic-greening, the luminous efficiency is also high, and the lifetime is also an organic EL element, and the aromatic amine which realizes the organic EL element, the inventors and the like have entered the society in order to achieve the above object, and it is expected to be == ==: For the electric society, the heart is stunned, and the person and the person S are forbearing, because the bismuth and the amino group bond are both oxidized or reduced, so that the structure of the amine-enhancing group can be obtained. A group having a moderate steric hindrance can reduce the interaction between the fractions to suppress crystallization, and can effectively increase lg °. Further, the inventors have found that the present invention has an asymmetric structure. In addition, since the compound can be reduced in the range of m, the compound can be inferior to the bond, and the blockiness of the compound and the interaction with the light-emitting layer are excellent, so that the life of the obtained organic EL device can be prolonged. And mention, _ is combined with '= life effect and high efficiency effect, thus completing = biological. That is, the present invention provides an aromatic amine derivative represented by the formula (1) (Ri)a

Yan 1

\ ...(1)

Ar2 (R2)b Further, the present invention provides an organic EL element having an organic thin film layer containing at least one layer or a layer of a light-emitting layer between the cathodes of the organic EL element, and at least the organic thin film layer One layer contains the above aromatic amine derivative as a component of a single or a mixture. [Effects of the Invention] The organic EL device using the aromatic amine derivative of the present invention has high efficiency and long life even after storage at a high temperature. The above and other objects, features, and advantages of the present invention will become more apparent <RTIgt; [Embodiment] The aromatic amine derivative of the present invention is represented by the formula (1). [Chemical 2] 8 201016663

[in the formula (1),

R1 to 1 represent a linear or branched ortho group composed of a hydrocarbon having 1 to 10 turns, a cycloalkyl group having a major number of 3 to 10, an alkoxy group having a carbon number of 1 to 10, and a carbon number of a trialkylsulfanyl group having 3 to 1 fluorene, a triarylsulfanyl group having a carbon number of 18 to 3 fluorene, an alkylarylsulfanyl group having a carbon number of 8 to 15, and an aryl group having a carbon number of 6 2 14 , a And b are independent of 〇~4, c and d are each independently 0~3, and adjacent K~R4 can be bonded to form saturated or unsaturated, &amp; and R4 are not bonded to form an aromatic ring), [The R' and R&quot; represent an alkyl group composed of a hydrocarbon having 1 to 12 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, and the chain 4 is further represented by the following formula (2).

Ah is represented by the following general formula (3)] [Chemical 3] (R5)e (R6)f (r7)9 (Ar3) (Ar4) - (2) 201016663 (R8)h - (4) (3) [Formula (2) and (3),

Al*3~Αγ6 are independently nuclear carbon numbers 6~u

Rs to Rs represent a hydrogen atom, a triacyl group having a carbon number of 1 to n arylene, a chain, a branched or a cyclic group, a carbon number of 3 to W, and a carbon number of 18 Alkoxy group, carbon number is ❹

The aryl group of the aryl group of the group of 8 to 15 carbon atoms, the branch = the triaryl group, or the phenyl group, the number 6 to 14 of the aryl group 6 and f are independently 1 to 4, g and h respectively Independently, it is 1~5. When e~f is greater than or equal to 2, the same may be different. A plurality of R5~r8 of the sub-group may be connected with a plurality of Rs~Rs to form a saturated ring (the number of which is 6) Silk), , + R8F is a nucleus carbon in the formula (7), (4) may or may not exist, when (4) is absent, (At&quot; 4) is not an arylene group having a nucleus number of 6] In the aromatic amine derivative represented by the formula (1), the heart sound indicates a linear bond or a branched alkyl group composed of a hydrocarbon having 1 to 1 G carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, and a carbon number. It is an alkoxy group of 丨~1〇, a trialkylalkylene group having a carbon number of 3 to 10, a triarylsulfonyl group having a carbon number of 18 to 3 fluorene, and an alkylarylalkyl group having a carbon number of 8 to 15. The nuclear carbon number is 6~丨4 aryl. 1^~114 is preferably a straight 201016663 chain or branched alkyl group consisting of a hydrocarbon having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, and an alkyl group having 1 to 6 carbon atoms. An oxy group, a trialkylsulfanyl group having a carbon number of 3 to 6, a triarylsulfanyl group having a carbon number of 18 to 21, an alkylarylsulfanyl group having a carbon number of 8 to 12, and a nucleus number of 6 to 10; The aryl group is more preferably a linear or branched alkyl group composed of a hydrocarbon having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, or an aryl group having 6 to 10 carbon atoms. .

Specific examples of the linear or branched alkyl group composed of a hydrocarbon having a carbon number of Ri to R4 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, a second butyl group, and a different one. Butyl, tert-butyl, n-pemyl, n-hexyl, n-heptyl, n-octyl (~-addition), 1-decylpentyl, 4- Methyl-2-pentyl, 2-ethylbutyl, n-heptyl, decylmethylhexyl, n-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-decyl U-nonyl), 2,2-dimethylheptyl, 2,6-dimethylpipenyl, 3,5,5-trimethylhexyl, n-decyl, and the like. Preferred are methyl ethyl, propyl, isopropyl, n-butyl, t-butyl, isobutyl, and tert-butyl. earth

Specific examples of the cycloalkyl group having a carbon number of 3 to 1 Torr in Ri to R4 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a 4-methylcyclohexyl group, and a 1-adamantane group. 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, bicyclo[2 2 2]octyl, and the like. The second is cyclopentyl, cyclohexyl, cycloheptyl. Specific examples of the alkoxy group having a carbon number of 1 to 1 Å in K to R4 include an oxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, an oxy group, and a third butyl group. Oxyl, n-pentyloxy, n-hexyloxy, n-octyloxy. Preferred are methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy 201016663, second butoxy, and third butoxy.

Specific examples of the trialkylsulfanyl group having a carbon number of 3 to 10 in the range of Ri to R4 include a trimethylsulfonyl group, a triethyldecyl group, a tripropyldecyl group, and a tert-butyl-dimethyldecane. Base. Preferred are trimethyldecylalkyl and triethylphosphoric acid.

Specific examples of the triaryl chopping group having a carbon number of 18 to 30 in Ri to R4 include triphenylsulfonylalkyl group, tris(4-methylphenyl)decylalkyl group, and tris(3-fluorenylphenyl)decane. A group, a tris(2-methylphenyl)decyl group, a trinaphthyl anthracenyl group or the like. Preferred are triphenyldecylalkyl and tris(4-methylphenyl)decylalkyl.

Specific examples of the alkylarylalkylene group having a carbon number of 8 to 15 in the range of Ri to R4 include a dimethylphenyl group, a diphenylmethyl group, and a dimethyl (4 methylphenyl) decyl group. Wait. Specific examples of the aryl group having a core number of 6 to 14 in 仏~!^ include: stupid group, 1-naphthyl group, 2-naphthyl group, 1-indolyl group, 2-mercapto group, 9-fluorene group , phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 4 methyl-based, 3-fluorenyl basic, 2·methylphenyl, 4 -ethyl stupyl, 3· ® ethylphenyl, 2-ethylphenyl, 4-n-propylphenyl, 4-isopropylphenyl, 2-isopropylphenyl, 4-n-butyl Phenyl, 4-isobutylphenyl, 4_t-butylphenyl, 2-t-butylphenyl, 4-tert-butylphenyl, 3-tert-butylphenyl, 2- Tributylphenyl, 4-n-pentylphenyl, 4-isopentylphenyl, 4, f-tripentylphenyl, 4-n-hexylphenyl, 4-n-heptylphenyl, 4-n-octyl Phenylphenyl, 4-(2,-ethylhexyl)phenyl, 4-trioctylphenyl, 4-cyclopentylphenyl, 4-cyclohexylphenyl, 4-(4'-fluorenyl) Hexyl), 3-cyclohexylphenyl, 2-cyclohexylphenyl; 12 201016663 4-ethyl-1-caiyl, 6-n-butyl-2-caiyl, 2.3-didecylphenyl, 2,4-dinonylphenyl, 2,5-dimethylphenyl, 3.4-dianonylphenyl, 3,5-dimethylbenzene , 2,6-dimethylphenyl, 2,3,5-tridecylphenyl, 3,4,5-tridecylphenyl, 2,4-diethylphenyl, 2,3,6 -trimethylphenyl, 2,4,6-tridecylphenyl, 2,6-diethylphenyl, 2,6-diisopropylphenyl, 2,6-diisobutylphenyl , 2,4-di(t-butyl)phenyl, 2.5-di(t-butyl)phenyl, 3,5-di(t-butyl)phenyl, 2,4-di-p-pentylbenzene Base, 2,3,5,6-tetradecylphenyl; fluorene 4-methoxyphenyl, 3-methoxyphenyl, 2-methoxyphenyl, 4-ethoxyphenyl, 2 -ethoxyphenyl, 3-n-propoxyphenyl, 4-isopropoxyphenyl, 2-isopropoxyphenyl, 4-n-butoxyphenyl, 4-isobutoxybenzene Base, 2·isobutoxyphenyl, 2-secondbutoxyphenyl, 4·n-pentyloxyphenyl, 4-isopentyloxyphenyl, 2-isopentyloxyphenyl, 2 - neopentyloxyphenyl, 4-n-hexyloxyphenyl, 2-(2'-ethylbutyl)oxyphenyl, 4-n-octyloxyphenyl, 4-cyclohexyloxyphenyl, 2-cyclohexyloxyphenyl; 2-decyloxy-1-methyl, 4-fluorenyl-1-methyl, 4-n-butyl-butyl-1-methyl, 5-ethoxy-1 -Qinyl, 6-ethoxy-2-methyl, 6-n-butoxy-2 -Qinyl, 7-methoxy-2-naphthyl, 7-n-butoxy-2-naphthyl; 2.3-dimethoxyphenyl, 2,4-dimethoxyphenyl, 2,5 -dimethoxyphenyl, 2,6-dimethoxyphenyl, 3,4-dimethoxyphenyl, 3,5-dimethoxyphenyl, 3,5-diethoxybenzene , 3,5-di-n-butoxyphenyl, 2-decyloxy-4-methylphenyl, 2-decyloxy-5-methylphenyl, 2-mercapto-4-oxo Phenylphenyl, 3-mercapto-4-methoxyphenyl, 3-mercapto-5-methoxyphenyl, 3-ethyl-5-decyloxyphenyl, 2-decyloxy-4 -ethoxyphenyl, 2-methoxy-6-ethoxy 13 201016663 phenyl: 3,4,5·trimethoxyphenyl; 4-fluorophenyl, 3-fluorophenyldifluorophenyl , 2,5-difluoro stupid 2'3-difluoro-based, ΐ S - poorly-poor soil 2,6--fluorophenyl, 3,4-difluoro-containing 3,5-fluoro-based , 3,4,5-trifluorophenyl; fluoro-based, 2-fluoro-4-mercaptophenyl, 7 Ο ◎, 314-methyl phenyl 4 methoxymethyl, 3 _ 2-methylbenzene m methylphenylphenyl, 5·fluoro·2·decyl stupyl, gas 1 methylphenyl, 4 like a] 3 base, 2·chloro-6-methyl, phenyl, 3 --4,6-Dimethylphenyl, 2: Fluorine, -Ga:·曱Basic 2-gas 3_fluoro-4-ethoxyphenyl; f-oxygen radical, 2-nitrox-6-methoxyphenyl, 3 5 fluorenylphenyl, 3·trifluoromethylphenyl, 2·trifluoromethylbenzamine, 3′5,(trifluoromethyl)phenyl; a lactyl 4-trifluoromethoxyphenyl; iso-p-(2-propenylpropyl)phenyl, 3 Methyl-2-cacoyl, *methyl i-Caiji a This is a substituted or unsubstituted phenyl or naphthyl group. The knife is J alone for 〇~4, and it is better. c and d are independently 〇~3, preferably 〇. In the aromatic amine derivative represented by the formula (1), a plurality of R1 〜 form a *bonded wire and an unsaturated ring (wherein &amp; 仏 is not bonded to the = scent ring). Specifically, the saturated or unsaturated formation of the 'R1~&amp; bond has the structure as described below. [Specific Example of Saturated, Unsaturated Ring of Carbazole Site] [Chemical 4] 201016663

[Specific example of saturated, unsaturated ring in the 苐 site] [Chemical 5]

R' and R" represent a linear or branched alkyl group composed of a hydrocarbon having 1 to 12 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms. 15 201016663 R' and R&quot; A linear or branched alkyl group composed of a hydrocarbon having 1 to 6 carbon atoms or a cycloalkyl group having 5 to 7 carbon atoms. R' and R" are hydrocarbons having a carbon number of i to 12 Specific examples of the linear or branched alkyl group to be formed include a linear or branched burn group which is exemplified as a specific example of R i to 仏. Specific examples of the cycloalkyl group having 3 to 1 ring carbon atoms of R' and R" include a cycloalkyl group as a specific example of Ri to R4.

In the aromatic amine derivative of the present invention, An is represented by the following formula (2), and Ar*2 is represented by the following formula (3). (R7)g (A<) (R5)e (Re)f (A<)-(A<)

In the formula. (R8)h (3), Ah~ΑΓό are independent, and the arsenic scale with a carbon number of 6 to 14 is a straight or circular ring composed of a carbon atom having a carbon number of 1 to 1 Å. An alkyl group, an alkoxy group having a carbon number of 1 to 1 fluorene, a trialkylalkylene group having a carbon number of J 〜1 、, a triarylalkylene group having a carbon number of 18 to 30, and an alkyl group having a carbon number of 8 to 15 The base alkyl group has a nucleus carbon number of 6 to &lt; '14 ^ or a phenyl group. The soil e and f are 1 to 4 ' g, and h is 1 to 5. When e to f is greater than, the plurality of R 5 are present. ~R8 can be the same or not (five), multiple, r5~R8 16 201016663 can be bonded to form a saturated ring. Among them, the nuclear carbon in the general formula (2), (^5) exists or does not exist, m, when '(A1·4) is not an arylene group having a nucleus carbon number of 6. The genus 5 is in the general formula (2) and the general formula (3), and the ΑΓ3 to the private ones are each independently 6 to Η. Aryl. Private ~ 仏 better number, 6 10 arylene. t 数 ό ό , ~ , such as ~ ΑΓ 6 specific examples can be cited: stupid (b_ne), extraction

^aPh_ene), 蒽(秘racene), Philippine (Chongcai _), Aben (5)), bivalent silk, p-(2_phenylpropyl)benzene, naphthalene, 4 methyl naphthalene Residues. Preferably, the terpenoids 3 to 6 are bivalent residues which are stupid and naphthalene. ^ In the general formula (2), the presence or absence of '(iv) may be (y) not present, (Αι*4) is not an arylene group having a nucleus number of 6. In the general formula (2) and the general formula (1), a straight bond, a bond or a cyclic wire composed of a hydrocarbon having a nitrogen atom and a number of H), and a decyloxy group having a carbon number of 1 to 10 a triaryl-Wiki group having a carbon number of 3 to 1 G and having a carbon number of 18 to 3 G, a aryl group having a carbon number of 8 to 15, or an aryl group having a core number of 6 to 14 or Or biphenyl. Specific examples of the linear bond, the branched chain or the cyclic base of the hydrocarbon having a carbon number of R5 to R8 include a straight hydrocarbon composed of a hydrocarbon having a carbon number of 1 to 10 as a general-purpose (1) towel. The monovalent or branched alkyl group and cycloalkyl group exemplified by the chain or the decyl group and the ring filament having a carbon number of 3 to 1 G. Specific examples of the decyloxy group having a carbon number of 1 to 1Q in R5 to R8 include a specific example of the alkoxy group having a carbon number of 1 to ί of Ri to I in the formula (1). Listed alkoxy groups. Specific examples of the trialkylsulfonyl group having a carbon number of 3 to 10 in the range of 3 to 10 in the formula (1), and specific examples of the trialkylsulfanyl group having 3 to 10 carbon atoms in the formula (1) The trialkylsulfanyl group exemplified in the above. Specific examples of the triarylsulfanyl group having a carbon number of from 18 to 30, which is a triarylsulfanyl group having a carbon number of 18 to 30 in the formula (1), are exemplified by a triarylhetero group. Ο

- rum λ · 8 specific examples of the alkyl aryl decyl group of 8 to 15, the carbon number of R1 〜 〜 in the formula (1) is 8 to 15 of the basic soil (4) Broken base. Specific examples of the aryl group having a carbon number of 6 to 14 in the general formula include the aryl group as exemplified in the case of the nucleus having a nucleus carbon number of 6 to 14 in &amp; The weight of the W 14 (four) group is ^m2)+'. Preferably, the hydrogen atom and the alkoxy group of the mosquitoes 1 to 6 composed of a hydrocarbon having a number of 1 to 6 are carbon atoms, and the carbon number is 3~. H ring = burning base, money is ~14 aryl*, r5~R7 is more heterogeneous, and the hydrocarbon with a carbon number of 64 is composed of a straight chain, a non-wind atom, and a carbon number! The aryl group of 〜10 is a group of 1 and the number of carbon atoms is 6 and the number of carbon atoms or the number of carbon atoms is H, R6 is a carbon atom, and R is a group of R in the formula (3). The straight bond 8 composed of ~6 hydrocarbons is a surface atom, a (4) number of 1 methoxy group, a carbon number of 3 to 6 ^ or a ring of filaments, a carbon number of i, a dialkyl group, and a dialkyl group. The number of nucleus is 18, 2010, 16663 Η square or qing, 10 aryl or Α Α 疋 疋 疋 疋 疋 疋 疋 疋 疋 氢 氢 氢 氢 氢 氢 氢 氢 氢 氢 氢 氢 氢 氢 氢 氢 氢 氢Further, 'R8 is not a nucleus number A, and the number is an aryl group of 6 in the formula (2) and the formula (3). g or h are independently independent. Or ^ knife is independent of 1~4, when e~f is greater than or equal to 2, ❹ the same = different 'multiple R5, key shape:: two respectively: heart ~ R8 can be bonded to form a saturated ring heart The saturated ring formed by the 仏 bond can be exemplified by a plurality of [saturated ring specific structures] as described below. [Chemistry 7]

Specific examples of the general formula (2) include two of the following groups. Ethnic group (2) -1 : [Chem. 8] 19 201016663

Ethnic group (2) -2 : [Chemical 9]

20 201016663

[化 ίο] Me

Me Si — Me Me

Me

Ethnic group (2) -4 :

Me

Ut 11]

21 201016663

[化 12]

Ethnic Group (2) -6 : [Chem. 13]

Specific examples of the general formula (3) include a group containing the following group. Ethnic group (3) -1 : 22 201016663 [Chem. 14]

~〇 ~〇~Me Me ~〇~^Me Me Me

Me C2H5

0-CqH-|7- n

Ethnic group (3) -2: [Chem. 15]

^^3 ^^O-Me

Ethnic group (3) _4 : [Chem. 17] 23 201016663

In the aromatic amine derivative represented by the formula (1) of the present invention, the combination of the formula (2) and the formula (3) with respect to Ar^ and Ah' is preferably: Group (2) -1 And ethnic groups (3) -1, ethnic groups (2) -1 and ethnic groups (3) _2, ethnic groups (2) -1 and ethnic groups (3) -3, ethnic groups (2) -1 and ethnic groups (3) · 4, ethnic groups (2) -2 and ethnic groups (3) · Bu group (2) -2 and ethnic groups (3) -2, ethnic groups (2) -3 and ethnic groups (3) · 1, ethnic groups (2) -3 and ethnic groups (3 ) -2, ethnic group (2) -3 and ethnic group (3) -3, ethnic group (2) -3 and ethnic group (3) -4, ethnic group (2) -4 and ethnic group (3) - Bu group (2) - 4 and ethnic groups (3) -2, ethnic groups (2) -5 and ethnic groups (3) -1, ethnic groups (2) -5 and ethnic groups (3) -2, ethnic groups (2) -5 and ethnic groups (3) -3 , ethnic group (2) -5 and ethnic group (3) -4, ethnic group (2) -6 and ethnic group (3) -1, and ethnic group (2) -6 and ethnic group (3) • 2. More preferably: ethnic group (2) -1 and ethnic group (3) -1, ethnic group (2) -1 and ethnic group (3) -2, ethnic group (2) -1 and ethnic group (3) -4, ethnic group ( 2) _2 and ethnic groups (3) -1, ethnic groups (2) -4 and ethnic groups (3) -1, ethnic groups (2) -5 and ethnic groups (3) -1, ethnic groups (2) -5 and ethnic groups (3) -2, and ethnic groups (2) -5 and ethnic groups (3) -3. More preferably, the group (2) -1 and 24 201016663 group (3)-1, group (1)4 and the formula (1) of the present invention _

Arl and Ar2 are preferably a group of &amp; amine derivatives, and a group of Arl and Ar2. It is 22 to 34, and even better is 22 to 3 inches. Good 疋 22~36, better

In the aromatic amine compound represented by the formula (1), when the same group is used, 'in the case of r, it is preferably a straight or branched chain composed of a carbon number of = ', or The cycloalkyl group having a carbon number of C to 1 Å is more preferably a hydrocarbon having a carbon number of 3 to 12: a straight bond or a branched chain, or a ring-shaped base having a carbon number of 5 to 1 G. The preferred (four) of the formula (7) in the aromatic bribe represented by the general formula (1) of the present invention is a group represented by the formula (4), more preferably a formula (6) and a formula ( 7) The group indicated. [it 18] The preferred form of the general formula (3) in the aromatic amine derivative represented by the formula (1) of the present invention is a group represented by the formula (5). ❹ (4) (Rs)e (R6)f (R7)g _ M ^ ^ (R5)e (R6)f (R7>9

-(6) 25 201016663 ...(7) ...(5)

(R7)g (R8)h

In the general formula (4) and the general formula (5), the definitions of R5 to R8, e, f, g and h and R5 to R8, e, f, g in the general formula (2) and the general formula (3) Same as h. In the general formulae (6) and (7), R5 to R7, e, f and g have the same meanings as those of R5 to R7, e, f and g in the formula (2). Specific examples of the aromatic amine derivative represented by the formula (1) of the present invention include the following compounds. [Chem. 20]

26 201016663

[A-7] [A-83

27 201016663

[A-16] [A-17] [A-18]

[A-22] [A-23] [A-24] 28 201016663

[A-25]

[A-26] [A-27]

[A-31] [A-32] [A-33] ❹

29 201016663

[A-44]

❹

30 201016663

[A-49] [A-50][化 21]

31 201016663

[B-10] [B-11] [B-12] 32 201016663

[B-16] [B-17] [B-18]

[B-22] [B-23] [B-24] 33 201016663

[B-29]

[B-30]

[B-31]

[B-32]

34 201016663

n-CeH^j-O CB-37] [Β-38] [Β-39]

[Β-47]

[Β-48] [Β-46] 35 201016663

[B-49] [B-50] [B-51]

[B-55] [B-56] [B-57]

[B-58] [B-59] [B-60] 36 201016663

[B-64] [B-65] [B-66]

[B-70] [B-71] [B-72] 37 201016663

[化22]

[Β-75]

〇 38 201016663

39 201016663

[c-1 3]

[C-14] [C-15]

[C-21]

[C-22]

40 201016663

[C-28] [C-29] [C-30]

[C-34] [C-35] [C-36] 201016663

[C-38]

[C-39] [C-37]

[C-43] [C-44]

42 201016663

[C-49] [C-50] [Chem. 23]

[D-7] [D-8] [D-9] 43 201016663

[D-1 2]

[D-19] [D-20] [D-21] 44 201016663

[D-31] [D-32] [D-33] 45 201016663

[D-34]

[D-35] The present invention is produced by the method of the general formula (1) using the aromatic derivative itself, the male scent of the genus. For example, ❹ 2 Γ7 , ο 〇^ 5 ^-7- , , -9,^ 2-^-7-^-9,9-^^-9H-g ), substituted or unsubstituted materials The reaction is carried out to produce a compound represented by the formula (I)-A), and then a compound represented by the formula (1-A) is reacted with a compound represented by the formula (2-A), whereby the compound of the formula (1) is produced. An aromatic amine derivative represented. [Chem. 24]

(1-A) In the formula (1-A), the Yi table is not in the "Ki~K4, R', R", and a~d and Ri~R4, R in the formula (1) ', R', and a ~ d table have different meanings. [化25] /Ari

HN (2-A)

Ar2 46 201016663 In the formula (2-A), Ari and μ have the same meanings as Ari and Ar2 in the formula (1). In addition, '2,7-dihalogenated anthracene derivatives can also be obtained (for example, 2,7-diiodo-9,9-monoalkyl, 2-bromo-7-fluorene-9,9-dialkyl-9-- ^, 2-gas-7-moth-9,9-dialkyl-9Η-薙) is reacted with a compound of the formula (2_Α) to produce a compound represented by the formula (1-Β), and then The compound represented by the formula (1) is reacted with a compound represented by the formula (ρΒ) and a substituted or unsubstituted taste β to produce a compound represented by the formula (1). [Chem. 26]

In the general formula (1-Β), 'Yl represents a halogen atom, and R3, ι, κ, R', and ArA Ar2 have the same meanings as RrimArj Ar2 in the formula (1). Further, 2, 7_ The reaction of a derivative with a substituted or unsubstituted carbazole or a compound represented by the formula (2-A) can be carried out, for example, by a palladium catalyst [for example, palladium acetate/ Triterpene butylphosphine, bis(dibenzylideneacetone)dipalladium/dicyclohexylphenylphosphine, tris(diphenylideneacetone)dipalladium/di(t-butyl)_2_biphenylphosphine] And in the presence of a base (for example, potassium carbonate, sodium carbonate, cesium earbene, sodium butoxide, potassium butoxide), the 2J didentate derivative, and substituted Or an unsubstituted carbazole or a compound of the axe of the formula (2_a); or a copper catalyst (for example, 47 201016663 (copperpowde O, copper chloride, desert copper) for recording (for example, &lt;acidation, carbolic acid_) in the presence of '2,7-didentate derivative, and substituted or unsubstituted #钱人(2_A) The aromatic amine derivative represented by the formula (1) of the present invention can be preferably used as a material for an organic EL device. The organic electroluminescence device of the present invention is between a cathode and an anode. Having one or more organic thin film layers containing a light-emitting layer" and at least one layer of the organic thin film layer contains any of the aromatic amine derivatives represented by the above formula (υ). In the organic EL element of the present invention It is preferable that the above-mentioned hole injection layer or hole transport layer contains the aromatic amine derivative represented by the above formula (1). Hereinafter, the configuration of the organic EL device of the present invention will be described. A representative configuration of the EL element is exemplified by the following structure: Port (1) Anode/Light-emitting layer/cathode (2) Anode/hole injection layer/light-emitting layer/cathode Ο Anode/light-emitting layer/electron injection layer/cathode ( 4) Anode/hole injection layer/light-emitting layer/electron injection layer/cathode (5) anode/organic semiconductor layer/light-emitting layer/cathode (6) anode/organic semiconductor layer/electronic barrier layer/light-emitting layer/cathode (7) Anode/organic semiconductor layer/light emitting layer/attachment Good layer/cathode (8) Anode/hole injection layer/hole transport layer/light-emitting layer/electron injection layer/cathode (9) Anode/insulation/light-emitting layer/insulation layer/cathode 48 〇❹ 201016663 &quot;ο? Anode/Inorganic Semiconductor Layer/Insulation Layer/Light Emitting Layer/Insulation Layer/Cathode (Imium Anode/Organic Semiconductor Layer/Insulation Layer/Light Emitting Layer/Insulation Layer/Cathode Insulation Layer Two Anode/Insulation Layer' Electrostatic Infusion Layer/Core Transmission The layer/light-emitting layer/electron is not=this is preferably the configuration of (8), but in the organic a-component of the present invention, the aromatic amine derivative represented by the present invention can be used for the above organic film. It is preferable that the layer ϊϋ contains the aromatic amine derivative in the light-emitting band among the constituent elements. The content of the formula (1) == Hesheng^ can be selected from 3G mol% to 1GG mol%. Electric 2:: Amine derivatives can be better used (4) Note 8 layers or acoustic layer and hole transport layer is to help inject holes into the illuminating layer and electricity 'is equal to n _ big ' _ _ small 'usually small Material = can be transferred to the hole in the hole 1G4v / em ~ 1 () 6v to the hole movement rate is better than at least 1 () _4. In the electric field, S ° 49 201016663 The aromatic amine derivative of the present invention can be preferably used as a hole transporting material because of its small ionization energy and large hole mobility. Further, since the aromatic amine derivative of the present invention contains a polar group in the molecule, it has good adhesion to an anode and is not easily affected by cleaning conditions of the substrate, etc., so that it can be suitably used as a hole injecting material. In view of the above, the inventors of the present invention considered that the organic EL device using the aromatic amine derivative of the present invention has a long life.

The hole injection layer or the hole transport layer can be used by, for example, a vacuum evaporation method, a spin coating method (spin (3) method), a cast method, a Langmuir method (Langmuir). A known method such as the -Blodgett method 'LB method> is obtained by forming a film of the aromatic amine derivative of the present invention into a film. The film thickness at the time of forming the hole injection layer or the hole transport layer is not particularly limited, and is usually 5 nm to 5 μm. If the hole transport belt contains the aromatic amine derivative of the present invention, the hole injection layer or the hole transport layer may be composed of one layer of one or two or more of the above materials, and it is difficult to form electricity. The human layer and the hole transport layer may be a hole injection layer and a hole transport layer formed by laminating a hole injection layer and a hole transport layer containing different kinds of compounds. Further, the organic semiconductor layer is a layer for assisting in injecting holes or electrons into the light-emitting layer, and suitably has a conductivity of 1 〇 -1 () s / cm or more. As the material of such an organic semiconductor layer, an electrically conductive dendrimer such as an oligomeric material electrically oligomer having an arylamine, an arylamine-containing dendrimer or the like can be used. 50 201016663 The organic EL element is usually produced on a light-transmitting substrate (translucent substrate). The light-transmitting substrate is a substrate supporting an organic EL element. The light-transmitting property of the substrate is preferably such that the transmittance of light in a visible light region having a wavelength of 4 〜 to 7 〇〇 nm is 5% or more. It is preferable to use a smooth substrate 0. Preferred examples of such a light-transmitting substrate include a glass plate, a synthetic resin plate, and the like. Examples of glass plates include, in particular, Nathan glass (s〇da_ijme), glass containing 钡_录, lead glass (1 from (1 coffee 85), aluminosilicate glass, smashed A plate formed of borosilicate glass, barium borosilicate glass, quartz, etc. Further, examples of the synthetic tree slab include: poly succinic acid resin (p〇ly Carb〇nate resin), acrylic acid system A plate of an acryl resin, a polyethylene terephthalate resin, a polyether sulfide resin, a polyfluorene resin, or the like. The function of injecting a hole into the hole transport layer or the light-emitting layer, ❹ effective 疋 has a work function of 4.5 eV or more. Specific examples of the anode material used in the present invention include: indium tin oxide (indimn) Tin oxide, ITO), indium zinc oxide (IZO), indium tin cerium oxide (ITCO), mixture of IZO and cerium oxide (izco), indium oxide And oxidation Mixture (indium cerium oxide ' ICO), a mixture of oxidized and oxidized alumium zinc oxide (AZO), tin oxide (NESA), gold, silver, platinum, copper, etc. 51 201016663 ^Extreme use of steamed ore The method is such that the electrode material is formed into a film by sputtering or the like. Thus, when the light from the luminescent layer is emitted from the anode, it is preferred that the light transmittance of the anode is greater than the position. The sheet resistance (this (10) reS1StanCe) is preferably less than or equal to several hundred Ω/cm 2 . The film thickness of the anode depends on the material 'but usually from the range of (7) leg to 丨 (four), preferably from l The selection is made in the range of 〇nm~2〇〇nm.

As the electrode material, a metal having a small work function (less than or equal to 4 eV), an alloy, a conductive compound, and the like can be used. Specific examples of such an electrode material include ································································ Indium, rare earth metals, etc. The cathode can be obtained by forming the electrode material into a film by evaporation or sputtering. Here, when light from the luminescent layer is emitted from the cathode, the light transmittance of the cathode is preferably greater than 10%. Further, the film resistance of the cathode is preferably equal to or less than several hundred Ω/crn2. The film thickness of the cathode is usually 1 〇 nmM μηη, preferably 疋50 nm to 200 nm. In general, since an organic EL element applies an electric field to an ultrathin membrane, it is easy to cause pixel defects due to electric leakage ((4)) or short circuit (also (8). In order to prevent this phenomenon, a package can be inserted between the electrodes. Examples of the material of the insulating layer m-edge layer of the insulating film layer include: oxidized IS, fluorinated chain, lithium oxide, cesium fluoride, cerium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, nitriding Aluminum, titanium oxide, cerium oxide, 52 201016663 bismuth telluride, tantalum nitride, nitriding, molybdenum oxide, cerium oxide, oxidized, etc. A mixture of two or more of these compounds may be insulated A layer or a laminate in which each of the two or more compounds is formed into a layer, and is used as an insulating layer. In the organic EL device of the present invention, the light-emitting layer has: (i) an injection function. · When an electric field is applied, a hole is injected from the anode or the hole injection layer, and a function of injecting electrons from the cathode or the electron injection layer into the luminescent layer; (Π) transmission function: using an electric field force to inject Electric charge (electron and electricity) (iii) function of movement; (iii) illuminating function: providing a recombination place of electrons and holes, and thereby illuminating the function. Examples of the method of forming the luminescent layer include vapor deposition, spin coating, LB, etc. The luminescent layer is particularly preferably a molecularly deposited film. The so-called molecularly deposited film refers to a film formed by deposition of a material compound in a gas phase state, or formed by solidification of a material compound in a solution state or a liquid phase state. Membrane. In general, the molecular deposition film and the thin film (molecular accumulation film) formed by the LB method can be distinguished by a difference in agglomerated structure, high-order structure, or a function difference caused thereby. The light-emitting layer can also be formed by dissolving a binding agent such as a resin and a compound as a material in a solvent to form a solution, and then forming the solution into a film by spin coating or the like. The luminescent layer may also contain a luminescent material containing a pyrene derivative and an amine compound or other known metal complex. 53 201016663 Metal complex is preferred a metal complex containing at least one metal selected from the group consisting of Ir, Ru, Pd, pt, 0s, and Re. The preferred 疋' of the ligand has a pyridine skeleton selected from the group consisting of At least one of a bipyridyl skeleton and a phenanthroline skeleton. Ο 具体 Specific examples of such a metal complex include tris(2-phenylpyridinium)pyrene, tris(2-phenyl) Acridine) ruthenium, tris(2-phenylpyridine)palladium, bis(2-phenylpyridine)platinum, tris(2-phenylacridine), tris(2-phenylpyridine)iridium, octaethylplatinum Porphyrin, octaphenylplatinium porphyrin, octaethylpalladium porphyrin, octaphenylpalladium porphyrin or the like, but is not limited to such a complex. An appropriate metal complex can be selected depending on the desired luminescent color, element properties, and host compound. Further, a luminescent light-emitting doping material or a fluorescent doping material can be used for the light-emitting layer of the organic EL device of the present invention. The phosphorescent dopant material is a compound that can emit light by a triplet exciton. The phosphorescent dopant material is not particularly limited as long as it can emit light by a triplet exciton, and preferably contains at least one metal selected from the group consisting of Ir, Ru, Pd, Pt, Os, and Re. The metal complex is more preferably a porphyrin metal complex or an orthometalated metal complex. The lindane metal complex is preferably a lin-platinum complex. The phosphorescent dopant materials may be used singly or in combination of two or more. There are a plurality of ligands which can form an ortho-metallated metal complex. Preferred ligands include: 2-phenylpyridine derivative, 7,8-benzoquinone (7) , 8-benzoquinoline) derivative, 2-(2-«septenyl) 54 201016663 Derivative of 2_(2_thienyl)pyridine, derivatized with 1-naphthylpyrididine (2-(l-naphthyl)Pyridine) , 2 phenylquinoline j2-PhenylquinGline) derivatives, and the like. These derivatives may have substituents as needed. The above-mentioned derivative which is a fluoride and has a trifluoromethyl group is a preferred blue-based dopant material. Further, the ortho-metallated metal complex may have a ligand other than the above ligand such as aeetylaeet or pieric acid, and as an auxiliary ligand 〇 luminescence The content of the layering material _ light-emitting level doping material is not particularly limited 'appropriately selected as needed, and the content is, for example, $0" wt% to 7 〇 wt% (weight ratio) (preferably 1 wt%) ~3〇wt%. If the content of the scale-emitting dopant material is less than a wt%, the light emission is weak, and the effect of the dopant material cannot be sufficiently exerted; if the content of the scale-emitting dopant material exceeds 70 wt%, it is called The phenomenon of concentration qiienchmg becomes apparent, resulting in a decrease in component performance. Further, the light-emitting layer may contain a hole transporting material, an electron transporting material, or a polymer binder as needed. Further, the film thickness of the luminescent layer is preferably 5 nm to 50 nm, more preferably 疋7 nm 5 〇 nm, and most preferably i 〇 nm 〜 5 〇 nm. If the film f of the light-emitting layer is small = 5 nm, it is difficult to form a light-emitting layer, and it is difficult to adjust the chromaticity. If the thickness of the light-emitting layer exceeds 50 nm, the driving voltage rises. The fluorescent dopant material is preferably a compound selected from the following compounds according to a desired luminescent color: an amine compound, an aromatic compound, a tris(8-hydroxyquinoline) aluminum complex, and the like. Compound, coumarin (c〇umarin) 55 201016663 Derivative, tetraphenyl-t-diene derivative, bis-vinyl arylene derivative, oxadiazole, and the like. Particularly preferred are arylamine compounds and aryldiamine compounds, and the towels thereof are more preferably benzophenone aerogels, styryldiamine compounds, aromatic amine compounds, aryl-diamine compounds, and more preferably condensed. Township bribes. This (4) New_material can be used alone or in combination with a variety of fluorescent dopant materials. In the organic EL device of the present invention, it is preferred to contain a styrene amine.

And / or arylamine as S light doping material. The abbreviated amine compound and/or arylamine is preferably a compound represented by the following formula (1). [化27]

(10)

_ Ar9"U In the formula (10), Αι:7 to A1·9 is a substituted or unsubstituted ring-shaped stone having an inverse number of 6 to 40. u is an integer of 1 to 4, in which a better integer of 疋1 to 2 is set. Any one of Ar7 to Αγ9 may be a group containing a styrene group. When any of f Αι*7 to Αι·8 has a styryl group, at least one of the preferred 疋Ars or Arp is substituted with a styrene group. Examples of the aromatic group in which the ring forms a carbon number of 6 to 40 include: phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, e〇r〇nenyl, biphenyl, hydrazine Terphenyl, pyrazylyl, fiiranyl, thienyl, benzoquinthiol, oxadiazolyl, distyl fluorenyl, fluorenyl 〇nd〇 Lyl), carazolyl, pyridyl, alum quinolyl, fluorenyl 56 201016663 (fluomnthenyl ), indenyl fluorenyl, fluorenyl (this), perylenyl, [grass (above) + fast] base (chrysenyi), picenyl, diphenyienyi, z^bicenyi, phenyl fluorenyl, phenyl fluorenyl, bisindenyl or An arylene group represented by the formula (C) and the formula (D). Among them, preferred are naphthylfluorenyl, [grass + super), fluorenyl or arylene represented by the formula (D). [化 28]

In the formula (c), r is an integer of 1 to 3. Further, examples of preferred substituents for substituting the above aryl group and arylene group include a group having 1 to 6 carbon atoms (ethyl group, methyl group, isopropyl group, and positive group).

Alkoxy group (ethoxy, methoxy, isopropoxide, positive) of di-butyl, tert-butyl, pentyl, hexyl, cyclopentyl, cyclohexanyl) a propoxy group, a second butoxy group, a third butoxy group, a pentyloxy group, a hexyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, etc.), an aryl group having a carbon number of 5 to 40, and a carbon 15 The amine group substituted with a fluorene group, an aryl group having a carbon number of 〜, a group, a S group having a carbon number of 1 to 6, a cyano group, an anky group, a ruthenium atom or the like. 'The main material is listed as a compound, a phenanthrene compound, a fluorene compound, a condensed tetraphenylene Uetracene compound, a triphenyl compound, [grass (above) + fast] 57 201016663 (chrysene) compound, anthraquinone compound, cockroach (coronene) a polycyclic aromatic compound such as a compound, an anthracene compound, a phthaloperylene compound, a naphthaloperylene compound, a naphthacene compound, a pentacene compound, an oxadiazole or a bisphenylhydrazine. Oxazoline, bisstyryl, cyclopentadiene, quinoline metal complex, tris(8-hydroxyquinoline)aluminum complex, tris(4-methylquinoline)aluminum complex, three (5-phenyl-8-quinolin) aluminum complex, aminoquinoline metal complex, benzoquinone metal complex, tris-(p-triphenyl-4-yl)amine, 1- Aryl-2,5-mono(2-anthracenyl)-pyrazine derivatives, beta-pyrane, quinacridone, rubrene, distyrylbenzene-derived , diphenylethylene arylene derivative, oxime derivative, laughing derivative, pyrazoline derivative, coumarin , pyranyl pigment, phthalocyanine pigment, naphthalocyanine dye, croconium pigment, squalipur dye, oxon leek pigment, fluorescent Prime pigment, rhodium (rhddamine) pigment, pyrylium pigment, lanthanide pigment, lanthanide pigment, polythiophene pigment, or rare earth complex phosphor, rare earth Phosphorescent luminescent complexes (for example, Ir complexes) and polymer materials such as polyvinyl carbazole, poly chlorpyrifos, polyethylenedioxythiophene (PEDOT), etc. They may be used alone or in combination of two or more. The host material which can be used in combination with the compound of the present invention is preferably a compound represented by the following formula (11) to formula (17). An anthracene derivative represented by the following formula (11). 58 201016663 ...(11) Ο

In place of ίίϊΓ1), Α&quot; and Α22 are divided into aromatic ring groups which are substituted or not delayed by 6~6〇. ^~&amp; are independently a hydrogen atom, a substituted or unsubstituted aryl group having a carbon number of 6 to 5 Å, a substituted or unsubstituted aromatic group having 5 to 5 G atoms, and a substituted Or unsubstituted carbon number 丨~, such as alkyl, substituted = unsubstituted cycloalkyl, substituted or unsubstituted carbon number = alkoxy, substituted or unsubstituted carbon number 6 to 5 〇 aralkyl, substituted or unsubstituted aryloxy group having 5 to 50 atoms, substituted or unsubstituted arylthio group having 5 to 50 atoms, substituted or not The substituted alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylene group, a carboxyl group, a dentate atom, a cyano group, a nitro group or a hydroxyl group. An anthracene derivative represented by the following formula (12). [化 30] 59 201016663

^31 R32 (12) ^35 R34 In the formula (12), the substituted or unsubstituted carbon number 3G to R39 are each independently a hydrogen atom.

The substituted group number is 〜5 (J's aromatic ring group, modified or unsubstituted aromatic heterocyclic group having a carbon number of 1 to 5 Å, substituted or unsubstituted, substituted or untreated a calcined, substituted or unsubstituted naphthenic or unsubstituted carbon number Α having a carbon number of 1 to 5 G oxy groups, substituted 5 to 5 Å, substituted or unsubstituted a 5 to 50 thiol, substituted, substituted, substituted, substituted, unsubstituted, substituted or unsubstituted 'monooxyl group, 1 to 50, substituted or unsubstituted A fluorenyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group. An anthracene derivative represented by the following formula (13).

In the formula (13), the flank 4 〇 to R49 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group which may be substituted, an alkoxy group, an aryloxy group, an alkylamine group 201016663, an alkenyl group. (alkenyl), an arylamine group or a heterocyclic ring which may be substituted. i and j respectively represent integers of 1 to 5, and when 1 and ] are larger than or equal to each other, R40 or ILn may be the same or different. In addition, the stools or 'can be bonded to each other to form a loop, and ', and, and %^^ R47, R48 and R49 can be bonded to each other to form a loop. 6, (four) quasi). (R material can be replaced

An anthracene derivative represented by the following formula (14). [化32]

k, 卜m and η respectively represent integers of 1 to 5, and when k, cucurbit and n are greater than or equal to 2, R5. The other, r51, and / or R56 may be the same or different from each other. Further, 'r52, Rs3, R54 or 55 may be bonded to each other to form a ring, and the ruler 52 and the core 3, R57 and R58 may be bonded to each other to form a ring. 201016663 L2 represents not a single bond, -Ο-, -s-, -N(R)_ (r is an alkyl group or an aryl group which may be substituted), an alkylene group or an arylene group. A Spir〇nu〇rene derivative represented by the following formula (15). [化 33] ΑΓ31 ΑΓ32

ΑΓ33 ΑΓ34 '(15) Ο In the formula (15), ArM to Ar34 are each independently a substituted or unsubstituted biphenyl group or a substituted or unsubstituted naphthyl group. A compound represented by the following formula (16). [34] ΑΓ44 Α"41

^63 A Γ43 A "46 (16) represents a hydrogen atom, substituted or unsubstituted" = R1 R6~R6 〆 别 independently represents a ring of a gas, a carbon number of 3~ό, a carbon number of 1 to 6 alkyl groups, -18 aryloxy groups, carbon number 7 to 18"; 6 methoxy group, 5 carbon atom of alkoxy group, arylamine having a carbon number of 5 to 16 62 201016663 Base, base, cyano group, carbon number h _ group or element atom 0

The first compound represented by the following formula (17) [Chem. 35]

You, \ and R74, are not a gas atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic wire, a substituted silk substituted aryl group or

a substituted or unsubstituted heterocyclic group. It is the same as the difference between the different phases and R74. R74 may be the same or not, and may be the same as or different from the same base phase. 73 and

Ar7I&amp;Ar72 represents that the benzene ring is a total of three or more substituted condensed polycyclic aromatic groups, or the benzene ring and the heterocyclic ring are two-solid or more substituted or unsubstituted carbon (IV) a condensed polycyclic heterocyclic group bonded to a group. ~ and eight ~ can be the same or different. v represents an integer from 1 to 10. Among the above main materials, an anthracene derivative is preferred, and more preferably a single 63 201016663 • anthracene derivative, particularly preferably an asymmetric anthracene. The host compound suitable for phosphorescence luminescence composed of a compound containing a ruthenium ring is a compound having a function of transferring energy from an excited state to a spheroidal light-emitting compound, and as a result, the phosphorescent compound emits light. The host compound is not particularly limited as long as it can transfer exciton energy to the phosphorescent compound, and can be appropriately selected depending on the purpose. The host compound may have any heterocyclic ring or the like in addition to the carbazole ring. Specific examples of such a host compound include: a carbazole derivative, a triazole derivative, an oxazole derivative, an oxadiazole derivative, an imidazole derivative, a polyaryl-burning artisan bamboo organism, and a π ratio β sitting bamboo a biological, alpha pyrazine(pyraz〇i〇ne) derivative, a phenylenediamine derivative, an arylamine derivative, an amine substituted chalcone derivative, a styrylpurine derivative, 〇〇 (flu〇ren〇ne) derivative, hydrazone derivative, laughing derivative, silazane derivative, aromatic tertiary amine compound, styrylamine compound, aromatic dimethine a base compound, a porphyrin compound, a quinodimethane derivative, an anthrone bamboo organism, a diphenylquinone-derived quinone, a thiopyrandioxide derivative, a carbon di-i-imine ( Metals of carbodiimide derivatives, mercapto methane derivatives, distyryl pyrazine derivatives, heterocyclic tetracarboxylic anhydrides such as naphthoquinone, phthalocyanine derivatives, and 8-quinolinol derivatives a complex or metal phthalocyanine to benzoxazole or benzoquinone Highly conductive such as various metal complex polyalkylene compounds, poly(N-vinylcarbazole) derivatives, aniline copolymers, thiophene oligomers, and polythiophenes represented by metal complexes as ligands A molecular oligomer, a polythiophene derivative, a polyphenylene derivative, a polyphenylene vinylene 64 derivative such as a polyphenylenevinylene derivative, or a polymer compound such as a polyfluorene derivative. The host compound may be used singly or in combination of two or more kinds. Specific examples include the following compounds. [化36]

Ο

Secondly, the electron injecting layer and the electron transporting layer are layers which assist in injecting electrons into the light emitting layer and transport them to the light emitting region, and are electron mobility. Further, the adhesion improving layer is a layer formed of a material which is particularly excellent in adhesion to the cathode in the electron injecting layer. Further, it is known that in an organic EL device, light emitted from an electrode (in this case, a cathode) is reflected, so that interference between light directly emitted from the anode and light emitted through the electrode is generated. In order to effectively utilize the interference effect, the film thickness of the electron transport layer 65 201016663 can be appropriately selected within a range of several nm to several. When the film thickness of the electron transporting layer is particularly thick, in order to avoid an increase in voltage, it is preferable that the electron mobility is at least 10_5 cm 2 /Vs when an electric field of 104 V/cm to 1 〇 6 v/cm is applied. The material for the electron injecting layer is preferably a metal complex of 8-hydroxyquinoline or a derivative thereof, or an oxadiazole derivative. As a specific example of the above-mentioned 8-hydroxyquinoline or 8-hydroxyquinoline-derived metal complex, a chelating agent containing oxin (usually 8-hydroxyquinoline or 8-hydroxyquinoline) can be used. A metal chelate compound of the compound, such as a three (8-ray) 嶋 electron injecting material. On the other hand, the oxadiazole derivative may be an electron transfer compound represented by the following formula. [化37]

"85 • Ar87-〇-A "8 again)

A

◎

N—N Δ “eg ^ Ar81, Ar82, Ar83, Ar85, Αγ86, Αγ89 respectively represent t or an unsubstituted aryl group, which may be the same or different from each other.

/ two 'A. 7. Al&gt;88 represents a substituted or unsubstituted arylene group which may be the same or different. The succinyl group may be exemplified by a phenyl group, a biphenyl group, a fluorenyl group, a aryl group, and a group. In addition, the arylene group may be exemplified by a phenylene group, a naphthylene group, and a subunit group: a base carbon: a substituent: a compound having a carbon number of two is preferably a group having two:= Wait. The electron transfer ❹ 〇 * ' and is transmitted to the lower layer of the luminescent layer to the luminescent layer

1〇4 v/c^10?L The hole mobility is better than at least urW/v.s. In the case of an electric field, it is possible to use a single organism: in a hole transport belt, a hole transport layer, or the present invention = a hole injection layer or a mixture. + There is no particular limitation on the formation of the hole injection of the aromatic amine derivative and other material layers and the electric scent. The material charge transporting material having the above-mentioned preferred properties is used as a hole in the electrically conductive material. The injection layer and the hole transmission layer fs 2:: The hole for the organic EL element is invented, and will have any material using the electric transmission wheel. This material is called a hole transfer material. &quot;This force, the aromatic amine derivatives that can be used in the hole transport layer to lift the hole transport layer can be listed 67 201016663 [Chem. 38]

2 7 h Interest 213+ such as ^»211

207 208J ^Αι Αγ211~Αγ

Tjv^v 203, cool I204j

P 213 ' Ar, ◎ /b , , , ...*χΓ221 ～ Ar Ώ. The substituted or unsubstituted carbon number is 6 223 and Ar2〇3~Ah8 are taken or unsubstituted, respectively, with an atomic number of 5:50. The aromatic hydrocarbon group or the substituted heterocyclic group having a substitution of t, W, and y of 〇3′′ and 50%, respectively. Examples of the p, q, s, substituted or unsubstituted carbon compounds include a fluorenyl group, a 1-phenanthrenyl group, a 2-phenanthrenyl group, and a phenanthrene group. -naphthyl J 1-fluorenyl, 2-indenyl, 9-phenyl, 2-fused tetraphenyl, 9, f, 4:, yl, 9-phenanthryl, 1-fused tetra-2, 3, stupid Base, 4_biphenyl, bis-yl, 4-youtyl, phenyl-3-yl, p-triphenyl-2-yl, cross-linked tris, ·--4-yl, conjugated tris-triphenyl-2 a group, an o-tolyl group, an m-, a m-triphenyl-3-yl group, a naphthyl group, a 4m-S group, a 4'-fluorenyl group, a 4, a triphenyl-4-yl group. Specific examples of the aromatic heterocyclic group having 5 to 5 ring atoms substituted or unsubstituted by the mono-butyl group may be exemplified by I squary group, 2. thiol group, 3 d specific group, % group, &gt; Bibi, 3_(tetra), 4-吼, 弓, 2, 2, 2 (4): 68 201016663 3-mercapto, 4-indenyl, 5-nonyl, 6-fluorenyl, 7 - mercapto, 1-isoindenyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isodecyl, 6-isodecyl, 7-iso Sulfhydryl, 2-furyl, 3-furyl, 2-phenylfurfuryl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7 -Benzylfuranyl, 1-isobenzofuranyl, 3-isophthalazylfuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isophenylhydrazine Furanyl, quinolyl, 3-quinolyl, 4-quinolinyl, 5-cylinyl, 6-fluorenyl, 7-fluorenyl, 8-mercapto, 1-isoindolyl , 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolinyl, 6-isoquinolinyl, 7-isoquinolyl, 8-isoquinolinyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-啥11 oxalinyl, 1-morphine咬-phenanthridinyl, 2-morphyl, 3-phenylidinyl, 4-cyridinyl, 6-cyridinyl, 7-cyridinyl, 8-cyridinyl, 9-brown, 10-Brown bite, 1-° rid-acridinyl, 2-° 丫 base, 3-acridinyl, 4-acridinyl, 9-acridinyl, 1,7-morpholine- 2-yl, 1,7-morpholin-3-yl, 1,7-morpholin-4-yl, 1,7-morpholin-5-yl, 1,7-morpholin-6-yl, 1, 7-morpholin-8-yl, 1,7-morpholin-9-yl, 1,7-morpholin-10-yl, 1,8-morpholin-2-yl, Q 1,8-morpholine- 3-yl, 1,8-morpholin-4-yl, 1,8-morpholin-5-yl, 1,8-morpholin-6-yl, 1,8-morpholin-7-yl, 1, 8-morpholin-9-yl, 1,8-morpholin-10-yl, 1,9-morpholin-2-yl, 1,9-morpholin-3-yl, 1,9-morpholin-4 -yl, 1,9-morpholin-5-yl, 1,9-morpholin-6-yl, 1,9-morpholin-7-yl, 1,9-morpholine-8-yl, 1,9 -morpholin-10-yl, 1,10-morpholin-2-yl, 1,10-morpholin-3-yl, 1,10-morpholin-4-yl, 1,10-morpholin-5- , 2,9- phenanthroline-1-yl, 2,9-morpholin-3-yl, 2,9-morpholin-4-yl, 2,9-morpholin-5-yl, 2,9- Porphyrin-6-yl, 2,9-morpholin-7-yl, 2,9-morpholin-8-yl, 2,9-morpholin-10-yl, 2,8-morpholin-1·yl , 2,8-morpholine- 3-based, 2,8-69 201016663 morphine-4-yl, 2,8-morphine _5-yl, 2 8 · morphine _6•yl, 2 8 morphine, 2,8 morphine 9 ·Base, 2,8-_Linluji, 2,7-morphine small base, 2,7-morphine _3_ base, 2,7-morphine·4_ base, 2,7-morphine-5 ·Base, 2,7_#琳-6_yl, 2 7_sprayinyl, 2,7-phenoline-9-yl, 2,7-phenanthroline, 1〇-yl, quinoxazinyl (l -phenazinyl), 2-cyanozinyl, 丨-phenothiazinyl, 2-phutthiazinyl, 3-morphothazinyl, 4-phenylthiazinyl, 10-phenyl-beta-B-yl , 1 〇 〇 〇 ( (l _phen 〇 XaZjnyl), 2 徘. Oxazinyl, 3-morphoxazinyl, 4-morphoxazinyl, 1-indolezinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2 -oxadiazolyl, 5-oxadioxyl, 3-indole 3-fiirazanyl, 2-nonylphenyl, 3-nonylphenyl, 2-methylpyrrolidin-1-yl, 2· Methylpyrrol-3-yl, 2·mercaptopyrrol-4-yl, 2-methylpyrrole-5-yl, 3-mercaptopyrrole-1·yl, 3-methylpyrrol-2-yl, 3- Methylpyrrole-4-yl, 3-mercaptopyrrole-5-yl, 2-t-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl 1-indenyl, 4-mercapto-1-indenyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butylhydrazine 4-tert-butyl 1-indenyl, 2-tert-butyl-3-»indenyl, 4-tert-butyl 3-indenyl. Further, a compound represented by the following formula can be used in the hole injection layer and the hole transport layer. [化39] 201016663 233

(Α1234

Af231

Ah3!~Ah34 are substituted or unsubstituted carbon numbers Ο

An aromatic hydrocarbon group of Q or a substituted or unsubstituted aromatic heterocyclic group having 5 atomic number. —50 5 5 L is a linking group which is a single bond, a substituted or unsubstituted aryl group of ～50, or a substituted or unsubstituted primary heterocyclic group of 6 to 50. χ is an integer of 〇~5. Among them, specific examples of the substituted or unsubstituted aromatic furnace group having a carbon number of 6 to 5 Å and the substituted or unsubstituted aromatic = ring group having 5 to 5 Å are exemplified. The same group as above. Further, specific examples of the material of the hole injection layer and the hole transport layer include, for example, a triazole derivative, an oxadiazole derivative, an imidazole derivative, a polyarylalkane derivative, and a pyrazoline derivative. And pyrazolone derivatives, stupid diamine derivatives, arylamine derivatives, chalcone derivatives substituted with amine groups, azole derivatives, styryl hydrazine derivatives, anthrone derivatives, hydrazine A derivative, an anthracene derivative, a decazane derivative, a polydecane system, an aniline copolymer, a conductive southern molecular oligomer (especially a thiophene oligomer), or the like. The above-mentioned materials can be used as the material of the hole injection layer and the hole transport layer, and it is preferred that the porphyrin compound and the aromatic tertiary amine compound are 71 201016663 = styrene amine compound ' particularly good The use of an aromatic tertiary amine compound can also be exemplified by (4) having a condensed NPD, and three triphenylamine units (tri-linked into a starburst type (magnetic _ _ _ group) - N-phenylamine group) A triphenylamine (hereinafter abbreviated as MTDATA) or the like, and a nitrogen-containing heterocyclic derivative represented by the following formula may be used in the hole injection layer and the hole transport layer. [40]

In the above formula, Rl21 to Rl26 each represent a substituted or unsubstituted alkyl group substituted or unsubstituted, substituted or unsubstituted aralkyl group, substituted or unsubstituted heterocyclic group. Any of the groups. Wherein, r121 R R126 may be the same or different. In addition, Ri2i and Ri22, R(2) and

Rl24 Rl25 and Rl26, R121 and R126, R122 and R123, R124 and R form a fused ring. In addition, a compound which is represented by the following formula may be used in the hole>main layer and the hole transport layer. 72 201016663 [化 41]

ο ο The above η”~r136 are represented by materials such as a substituent group, a sulfonyl group, a carbonyl group, a trimethyl group, a ferrocyanyl group, a nitrate, etc., and a charge acceptor material. Specifically, it is as shown above. 7 is used as a hole injection. In addition to the compound of the bismuth-based fluorene-based compound as a material of the light-emitting layer, P-type Si, p-type, etc. can also be used as the hole injection layer and The material of the hole transport layer...., bn The aromatic amine derivative of the present invention can be formed into a film by a known method such as a vacuum deposition method, a spin coating method, a casting method, or the like to obtain a hole injection. The film thickness of the layer and the hole transport layer. The hole injection layer and the hole transport layer are not particularly limited, and are usually 5 nm to 5 μm. As long as the hole transport belt contains the aromatic amine of the present invention, The hole injection layer and the hole transport layer may be formed of one layer of two or more of the above materials, or may be formed by a hole injection layer and a hole formed by different kinds of compounds. Laminated layers to obtain hole injection layers and holes 73 201016663 Correction, can also set the money semiconductor layer, as a light to help the hole into the layer of the light-emitting layer, the age of the conductor layer is suitable for 岐 has a conductivity of 1〇-1. S / cm. As the material of the organic semiconductor layer, a conductive polymer such as a thiophene-containing oligomer or an arylamine-containing oligomer, a conductive dendrimer such as an arylamine-containing dendrimer, or the like can be used. In the method of the organic EL device of the present invention, for example, an anode, a light-emitting layer, an electric + injection layer, and a cathode can be formed by using the above materials and methods. Alternatively, an organic EL device can be fabricated from the cathode to the anode. In the following, an example of the production of an organic EL device in which an anode/hole injection layer/light-emitting layer/electron injection layer/cathode is sequentially provided on a light-transmitting substrate will be described. First, a vapor deposition method or a sputtering method is used. A film made of an anode material is formed on a suitable light-transmitting substrate as a cathode in such a manner that the film thickness is less than or equal to 丨μιη, preferably in the range of lOrnn to 200 nm. Then, the anode is provided. Hole injection layer. The hole injection layer can be formed by the method of “slotting method, spin coating method, lining method, LB method” as described in ©. It is easy to obtain a homogeneous film and it is not easy to produce pinholes. In other respects, it is preferred to form a hole injection layer by a vacuum evaporation method. When a hole injection layer is formed by a vacuum evaporation method, the steaming bonding conditions are based on the compound used (the material of the hole injection layer). ), the crystal structure or recombination structure of the target hole injection layer is different. Generally, it is preferable that the temperature of the steam source is 5 〇 t: ~450 ° C, and the degree of vacuum is 1 〇 -7 T 〇 Rr~i〇-3 Torr, evaporation rate 0.01 nm/s~50 nm/s, substrate temperature-5〇乞~3〇〇201016663 °C 'The film thickness is suitably selected within the range of 5 nm to 5 μm. Next, a light-emitting layer is provided on the hole injection layer. The light-emitting layer can also be obtained by forming a thin film of a light-emitting material by a method such as a vacuum deposition method, a sputtering method, a spin coating method or a scale method using the light-emitting material of the present invention. In the case where a homogeneous film is easily obtained and pinholes are less likely to occur, it is preferred to form a light-emitting layer by a vacuum deposition method. 〇 When a light-emitting layer is formed by a vacuum distillation method, the distillation conditions vary depending on the compound to be used, and in general, it is preferably selected from the same conditions as those for forming the hole injection layer. The film thickness of the light-emitting layer is preferably in the range of 10 nm to 40 nm. Thereafter, an electron injecting layer is provided on the light emitting layer. At this time, similarly to the hole injection layer and the light-emitting layer, since it is necessary to obtain a homogeneous film, it is preferable to form an electron-injecting layer by a vacuum test. The color condition can be selected from the range of conditions of the hole injection layer and the light-emitting layer. Then, the cathode is laminated, whereby an organic EL element can be obtained. The cathode is a metal shaft, and it can be protected by vapor deposition, _ method, etc. From the viewpoint of not being damaged at the time of film formation, it is preferable to form a cathode by a true vapor deposition method. Treatment = = The method of the '3' and the spin coating method in the organic element of the present invention. The organic thin film layer for the compound can be obtained by dissolving the compound represented by the above formula (1) by using the following method: = 75 201016663 steaming method 'MBE (molecular beam epitaxy method)' • A dipping method of a solution obtained by a solvent, and a coating method such as a spin coating method, a casting method, a bar coating method, or a roll coating method. The thickness of each organic layer of the organic EL device of the present invention is not particularly limited, and in general, in order to prevent occurrence of defects such as pinholes and to improve efficiency, it is preferably in the range of several nm to 1 // m. Further, when a DC voltage is applied to the organic EL element, when the anode 〇 is set to a positive (+) polarity, the cathode is set to a negative (-) polarity, and a voltage of 5 V to 40 V is applied, light emission can be observed. Further, if the polarity is reversed, no current flows even when a voltage is applied, and no light is emitted at all. Further, when an alternating voltage is applied, uniform light emission can be observed only when the anode has a positive (+) polarity and the cathode has a negative (-) polarity. The waveform of the applied alternating current can be an arbitrary waveform. [Examples] Hereinafter, the present invention will be described in more detail based on Synthesis Examples and Examples. The structural formula of 0 intermediates 1 to 14 is as follows. [化42] 76 201016663

Intermediate 8 intermediate 7

Intermediate 9

Intermediate 11 intermediate 12

Br intermediate 13

Br intermediate 14 Synthesis Example 1 (Synthesis of Intermediate 1) 77 201016663 Add 4 g of bromobiphenyl, 23 g of iodine, 9.4 g of periodic acid dihydrate to a 1000 mL three-necked flask under argon flow. 42 mL of water, 360 mL of acetic acid, and 11 mL of sulfuric acid were stirred at 65 ° C for 30 minutes and then reacted at 9 ° C for 6 hours. The reaction was poured into ice water and filtered. It was washed with water and then with methanol, whereby 67 g of a white powder was obtained. The white powder was identified as Intermediate 1 by FD-MS (field desorption mass spectrometry). Synthesis Example 2 (Synthesis of Intermediate 2) 相同 The same reaction as in Synthesis Example 1 was carried out except that 2-bromo-9,9-dimethylindole was used instead of 4·bromobiphenyl to obtain 61 g of a white powder. The white powder was identified as Intermediate 2 by FD-MS analysis. Synthesis Example 3 (Synthesis of Intermediate 3) 45 g of an intermediate 1, a saliva 21 g, a cuprous iodide 240 mg, and a potassium sulphate 56 were added to a 500 mL three-necked flask under an argon flow. g, 1,4-dioxanthine 160 mL, anti-_1,2·cyclohexanediamine 2.5 m was reacted at 130 ° C for 24 hours. After completion of the reaction, the mixture was extracted with toluene and dried over magnesium sulfate. The dried product was concentrated under reduced pressure, and the obtained crude product was purified using a column. Recrystallization was carried out using toluene, and crystals were obtained by filtration, followed by drying to obtain 33 g of Intermediate 3 as a white powder. Synthesis Example 4 (Synthesis of Intermediate 4) In a three-necked flask, 250 g of m-triphenyl (manufactured by Aldrich Co., Ltd.), 50 g of hydroiodic acid dihydrate, 75 g of iodine, 750 ml of acetic acid, and 25 ml of concentrated sulfuric acid were added. At 70. (: The reaction was carried out for 3 hours. After the reaction, 5 L of methanol was injected, and then the mixture was stirred for 1 hour. The reaction solution was filtered, and the obtained crystal was purified using column chromatography 78 201016663 (column chromatography) using acetonitrile. Recrystallization was carried out to obtain an intermediate 4 (3,_phenyl-4-broken biphenyl) 64 g as a white powder and 17 g of 3-phenyl-5-broken biphenyl. By FD-MS and H-NMR (H-nuclear magnetic resonance, analysis of H-magnetic resonance), identified as intermediate 4. Synthesis Example 5 (Synthesis of Intermediate 5) Under argon, 39.9 g of Intermediate 2 (100 mmol), benzene Base boric acid 12.4 g (i〇5 mmol), tetrakis(triphenylphosphine)palladium(〇) 2.31 g (2.00 〇mmol), 300 mL of hydrazine was added, and 150 mL of a 2 Μ sodium carbonate aqueous solution was added, and the mixture was heated under reflux for 10 hours. Immediately after the completion of the reaction, the mixture was filtered, and then the aqueous layer was removed. The organic layer was dried with sodium sulfate and then concentrated. The residue was purified by silica gel column chromatography to obtain white crystals of 28.3 g. The rate was 81%. The white powder was identified as intermediate 5 by FD-MS analysis. Example 6 (Synthesis of Intermediate 6) The same reaction as in Synthesis Example 5 was carried out except that Intermediate 1 was used instead of Intermediate 2, and 1-naphthylboronic acid was used instead of phenylboronic acid to obtain 30.2 g of a white powder. The white powder was identified as intermediate 6 by FD-MS analysis. Synthesis Example 7 (Synthesis of Intermediate 7) Except that Intermediate 1 was used instead of Intermediate 2, and 4-biphenylboronic acid was used instead of Phenylboronic acid. The same reaction as in Synthesis Example 5 was carried out to obtain 32.1 g of a white powder. The white powder was identified by FD-MS analysis to be 79 201016663 Intermediate 7. Synthesis Example 8 (Synthesis of Intermediate 8) • In an argon atmosphere Adding anhydrous THF (anhydr〇us tetrahydrofuran, anhydrous tetrahydrofuran) 400 mL to the by-product 3-phenyl-5-iodobiphenyl 29.6 g (100 mmol) obtained in Synthesis Example 4, under _4〇〇c Stirring was carried out and 63 mL (100 mmol) of a 1.6 hexane solution of n-butyllithium was added during the stirring. The reaction solution was heated to 〇〇c while stirring for 1 hour. The reaction solution was again cooled to _78 °. C, dropwise addition of trimethyl borate 26.0 〇g (250 mmol) of 50 mL Dry THF was added. The reaction was stirred for 5 hours at room temperature. N hydrochloric acid was added Shu 2〇〇 mL stirred for 1 hour, then the aqueous layer was removed. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained solid was washed with hydrazine to obtain 19.2 g of a boronic acid compound. Identification was performed by fd-MS analysis. In a murine environment, '8-g molybdenum phthalate 28.3 g (1 〇〇 mmol), the above boric acid compound 28·5 g (105 mmol), tetrakis(triphenylphosphine) (〇) 2 31 gU.OOmmol) Add 'Toluene 3 〇〇 mL, 2 M sodium carbonate aqueous solution Q 150 mL' and heat to reflux for 1 hr. Immediately after the completion of the reaction, the mixture was filtered, and then the aqueous layer was removed. The organic layer was dried over sodium sulfate and concentrated. The residue was purified on a silica gel column chromatography to give a white powder (26.2 g). The white powder was identified as Intermediate 8 by FD_MS analysis. Synthesis Example 9 (Synthesis of Intermediate 9) Except that Intermediate 1 was used instead of Intermediate 2, 4 butyl phenylboronic acid was used instead of phenyl Micro-Bus, and the same anti-201016663 as in Combination 5 was obtained. Powder 32.1 g. The white powder was identified as the intermediate 9 by FD_MS analysis. Synthesis Example 10 (Synthesis of Intermediate 10) The same reaction as in Synthesis Example 5 was carried out except that 4-bromoiodobenzene was used instead of Intermediate 2, and 2-phenylphenylboronic acid was used instead of phenylboronic acid to obtain a white powder. 23.6 g. The white powder was identified as intermediate 10 by FD_MS analysis. Synthesis Example 11 (Synthesis of Intermediate η) The synthesis example was carried out except that 4-bromoiodobenzene was used instead of the intermediate 2, and 9,9-dimethyl-9Η 苐-2-side acid was used instead of the phenylboronic acid. 5 identical reaction 'obtained 28.9 g of white powder. The white powder was identified as the intermediate U by FD-MS analysis. Synthesis Example 12 (Synthesis of Intermediate 12) The same reaction as in Synthesis Example 5 was carried out except that 3-dichlorobenzene was used instead of Intermediate 2, and 2-phenylphenyl arsenic acid was used instead of stupid acid. Liquid 21.3 g. The white powder was identified as intermediate 12 by FD-MS analysis. Synthesis Example 13 (Synthesis of Intermediate 13) The same reaction as in Synthesis Example 5 was carried out except that 3-bromoiodobenzene was used instead of Intermediate 2, and 4-phenylphenylboronic acid was used instead of phenylboronic acid to obtain a white powder. 24·1 g. The white powder was identified as Intermediate 13 by FD-MS analysis. Synthesis Example 14 (Synthesis of Intermediate 14) Except that 3-bromoindole was used instead of Intermediate 2, and 2-Cera Boric Acid was used. 81 201016663 ◎

The same reaction as in Synthesis Example 5 was carried out, except for phenylboronic acid, to obtain 21.5 g of a white powder. The white powder was identified as the intermediate 14 by FD-MS analysis. The structural formula of the intermediates Ami to Ami 6 is as follows. [化43] 82 201016663

中间 Intermediate Am 4

Intermediate Am2

Intermediate Am7 Intermediate Am8

Intermediate Am Θ

Intermediate Am13 Intermediate Am10 Intermediate Am11

Intermediate Am 14

Intermediate Am 16 Synthesis Example 15 (Synthesis of Intermediate Ami) Add 4_bromo-p-triphenyl 30.7 g, aniline 9.1 g, and third butoxide sodium 13.0 g (manufactured by Hiroshima Kasei Co., Ltd.) under a stream of argon (Dibenzylidene 83 201016663 Acetone) Two (0) 460 mg (manufactured by Aldrich Co., Ltd.), tris(t-butyl)phosphine 210 mg, and dehydrated phenylbenzene 500 mL were reacted at 80 ° C for 8 hours. After cooling, 2.5 L of water was added, and the mixture was filtered with celite, and the filtrate was extracted with benzene and dried over anhydrous magnesium sulfate. The dried product was concentrated under reduced pressure, and the obtained crude product was purified by column column, and recrystallized with toluene. The crystals were obtained by filtration and dried to give a pale yellow powder of 15.7 g. The pale yellow powder was identified as the intermediate Ami 0 〇 Synthesis Example 16 by FD-MS analysis (synthesis of the intermediate Am2). The same procedure as in Synthesis Example 15 was carried out except that the intermediate 4 was used instead of the 4-bromo-terphenylbenzene. The reaction 'obtained white powder 16.3 g. The white powder was identified as an intermediate Αηι2 by FD-MS analysis. Synthesis Example 17 (Synthesis of Intermediate Am3) The same reaction as in Synthesis Example 15 was carried out except that Intermediate 5 was used instead of 4·bromo-terphenylbenzene. The white powder was identified as the intermediate Atn3 by FD MS analysis. ❹ Synthesis Example 18 (Synthesis of Intermediate Am4) The same reaction as in Synthesis Example 15 was carried out except that Intermediate 6 was used instead of 4_____triphenylbenzene, and a white powder of 15 9 g was obtained. The white powder was identified as the intermediate Am4 by fd ms analysis. Synthesis Example 19 (Synthesis of Intermediate Am5) A white powder of 22.4 g obtained in the same manner as in Synthesis Example 15 was obtained, except that 1-bromo-naphthalene was used instead of 4-di-co-trimer, and biphenyl was used instead of aniline. By the analysis of the positive broadcast, the self-color powder was determined to be 84 201016663 intermediate Am5. Synthesis Example 20 (Synthesis of Intermediate Am6) The same reaction as in Synthesis Example 15 was carried out except that Intermediate 7 was used instead of 4_____. The white powder was identified as the intermediate Am6 by FD_MS analysis. Synthesis Example 21 (Synthesis of Intermediate Αηι 7) The same reaction as in Synthesis Example 15 was carried out except that the intermediate 8 was used instead of the 4-bromo-p-triphenylbenzene to obtain 22.5 g of a white powder. The white powder was identified as the intermediate Am7 by fd-MS W analysis. Synthesis Example 22 (Synthesis of Intermediate Am8) The same reaction as in Synthesis Example 15 was carried out except that the intermediate 9 was used instead of 4·bromo-co-trimer, to obtain 4 g of a white powder. The white powder was identified as the intermediate Am8 by FD_MS analysis. Synthesis Example 23 (Synthesis of Intermediate Am9) Under argon atmosphere, 32.7 g (100 mmol) of bis(4-bromophenyl)amine, 41.6 g (21 mmol) of 2-biphenylboronic acid, and four (three) To phenylphosphine)palladium(0)i 15 〇g (LOOmmol), 750 mL of toluene and 300 mL of a 2 M sodium carbonate aqueous solution were added, and the mixture was heated under reflux for 15 hours. Immediately after the completion of the reaction, the mixture was filtered, and then the aqueous layer was removed. The organic layer was dried with sodium sulfate and concentrated. The residue was purified by a silica gel column chromatography to afford 30.3 g of glassy solid. The white powder was identified as the intermediate Am9 by FD-MS analysis. Synthesis Example 24 (Synthesis of Intermediate Ami0) The same reaction as in Synthesis Example 15 of 85 201016663 was carried out except that the intermediate 1 〇 was used instead of 4-bromo-p-triphenyl, to obtain 13 2 g of a white powder. The white powder was identified by the fd_ms analysis as the intermediate Aml. Synthesis Example 25 (Synthesis of Intermediate Amll) The same reaction as in Synthesis Example 15 was carried out except that the intermediate 11 was used instead of the 4-bromo-pairs, to obtain a white powder 148 &amp; The powder is the intermediate Amll. Synthesis Example 26 (Synthesis of Intermediate Ami2) The same reaction as in Synthesis Example 15 was carried out except that the intermediate 10 was used instead of 4-bromo-p-triphenyl, and 4-aminoguanidino-p-terphenyl was used instead of aniline. White powder 22.5 g. The white powder was identified as the intermediate Aml2 by FD-MS analysis. Synthesis Example 27 (Synthesis of Intermediate Ami3) The same reaction as in Synthesis Example 15 was carried out except that the intermediate 12 was used instead of the 4-bromo-co-trimer, and a white powder was obtained for 6 d ms analysis, and the white powder was identified as Intermediate Aml3. Synthesis Example 28 (Synthesis of Intermediate Aml4) The same reaction as Helang 15 was carried out except that the intermediate 12 was used instead of the 4-bromo-para-triphenyl group, and the 4-amino group was used in place of the phenylhydrazine. , 20.9 g of white powder was obtained. The white powder was identified as the intermediate Aml4 by fd-MS analysis. Synthesis Example 29 (Synthesis of Intermediate Ami5) The same reaction as in Synthesis Example 15 was carried out except that the intermediate 13 was used instead of the 4-bromo-terphenylbenzene to obtain 4 3 g of a white powder. The white powder was identified by the fd_mS analysis as the intermediate Aml5. 86 201016663 Synthesis Example 30 (Synthesis of Intermediate Aml6) The same reaction as in Synthesis Example 15 was carried out except that Intermediate 14 was used instead of 4-bromo-terphenylbenzene to obtain 10.4 g of a white powder. The white powder was identified as the intermediate Aml6 by FD-MS analysis. The structural formulas of the compounds H1 to H16 which are the aromatic amine derivatives of the present invention produced in Synthesis Examples 1 to 16 are shown below. Compound H1~H8 : [Chem. 44] 〇

87 201016663

88 201016663

H1 1

H13

H10

Synthesis Example 1 (Synthesis of Compound HI) 89 201016663 Under argon gas flow, 8.0 g of intermediate 3, 6.4 g of intermediate Ami, third sodium butoxide 2.6 g (manufactured by Hiroshima Kasei Co., Ltd.), and three (two sub-sections) were added. Base acetone) two (0) 92 mg (manufactured by Aldrich), tris(t-butyl)phosphine 42 mg, and dehydrated toluene 100 mL 'at 80. The armpit reaction was carried out for 8 hours. After cooling, 500 mL of water was added, and the mixture was filtered with diatomaceous earth, and the filtrate was extracted with toluene and dried over anhydrous magnesium sulfate. The dried product was concentrated under reduced pressure, and the obtained crude product was purified by column chromatography, and then recrystallized with toluene. The crystals were removed by filtration and dried to give a pale yellow benzene powder of 7.1 g. The pale yellow powder was identified as compound H1 by FD-MS analysis. Then, the compound was subjected to sublimation purification under vacuum (2×1 (T4Pa), and then subjected to sublimation purification, and obtained in high performance liquid chromatography (HPLC) analysis. No impurity peak was confirmed. High-purity compound hi. Synthesis Example 2 (Synthesis of Compound H2) The same reaction as in Synthesis Example 1 was carried out except that the intermediate Am2 was used instead of the intermediate Ami, to obtain 6.6 g of a pale yellow powder. MS analysis, the light yellow powder was identified as compound H2. Then, the compound was subjected to sublimation purification under vacuum (2×10·4 Pa), and the result was sublimed and purified, and no impurity peak was confirmed in the HPLC analysis. Compound H2. Synthesis Example 3 (Synthesis of Compound H3) The same reaction as in Synthesis Example 1 was carried out except that the intermediate Am3 was used instead of the intermediate Aml to obtain 7.31 g of a pale yellow powder. By FD-MS analysis The yellowish powder was identified as compound H3. Then, the compound was sublimed and purified under vacuum at 90 201016663 (2×1 (T4 Pa), and the result was sublimed pure. After that, the impurity No. high purity compound H3 was not confirmed in the HPLC analysis. 'Synthesis Example 4 (Synthesis of Compound H4) The same reaction as in Synthesis Example 1 was carried out except that the intermediate Am4 was used instead of the intermediate Aml. 'A light yellow powder 7.9 &amp; group two shirt was obtained. The frog was analyzed by FD-MS and the yellowish powder was identified as compound H4. The compound was sublimed and purified under vacuum (2×10 −4 Pa). After one sublimation purification, no impurity = high purity compound H4 was observed in the hplc analysis. ^ Synthesis Example 5 (Synthesis of Compound H5) The same procedure as in Synthesis Example 1 was carried out except that the intermediate Am5 was used instead of the intermediate Ami. The reaction was carried out to obtain 8.3 g of a pale yellow powder. The pale yellow powder was identified as compound H5 by FD-MS analysis, and the compound was subjected to sublimation purification under vacuum (2×1 (T Pa). After a sublimation purification, it was confirmed that no high-purity compound H5 was obtained in the HPLC analysis. Synthesis Example 6 (Synthesis of Compound H6) The intermediate Am6 was used instead of the intermediate Ami. Further, the same reaction as in Synthesis Example 1 was carried out to obtain 7.9 g of a pale yellow powder. FD-MS analysis confirmed that the pale yellow powder was Compound H6. Then, the compound was subjected to sublimation purification under vacuum (2×10 −4 Pa), ^ Fruits = After sublimation purification, no peaks were obtained in the HPLC analysis: high purity compound H6. '91 201016663 Synthesis Example 7 (Synthesis of Compound Η7) The same reaction as in Synthesis Example 1 was carried out except that the intermediate Am7 was used instead of the intermediate Aml to obtain a pale yellow powder 6.5 FD-MS analysis to identify the pale yellow powder. After compound H7, the compound was subjected to sublimation purification under vacuum (2×10·4 Pa), and after sublimation purification, it was confirmed that high purity compound H7 was not confirmed by HPLC analysis. #

Ο Synthesis Example 8 (Synthesis of Compound H8) The same reaction as in Synthesis Example 1 was carried out except that the intermediate Am8 was used instead of the intermediate Ami to obtain a pale yellow powder 6.2 &amp;:&amp;, FD-MS analysis 'identification The pale yellow powder is the compound H8. Then, the compound was subjected to sublimation purification under vacuum (2×10·4 Pa), and as a result, one sublimation purification was carried out, and an impurity peak = high purity compound H8 was not confirmed in the HPLC analysis. Synthesis Example 9 (Synthesis of Compound H9) The same reaction as in Synthesis Example 1 was carried out except that the intermediate Am9 was used instead of the intermediate Ami to obtain a pale yellow powder of 5·9 g. The pale yellow powder was identified as compound H9 by FD-MS analysis. Then, the compound was subjected to sublimation purification under vacuum (2xl 〇 _ 4 Pa), and as a result, after sublimation purification, no impurity peak = Southern purity compound H9 was observed in the HPLC analysis. Synthesis Example 10 (Synthesis of Compound H10) The same reaction as in Synthesis Example 1 was carried out except that the intermediate AmlO was used instead of the intermediate Ami to obtain 4.6 g of a pale yellow powder. The light yellow powder was identified as the compound Η1〇 by ^ 92 201016663 FD-MS analysis. Then, the compound was subjected to sublimation purification under vacuum (2x1 〇·4 Pa), and the mixture was subjected to sublimation purification, and it was confirmed that no high purity compound H10 was obtained in the HPLC analysis. Synthesis Example 11 (Synthesis of Compound H11) The same reaction as in Synthesis Example 1 was carried out except that the intermediate Am11 was used instead of the intermediate AnU to obtain a pale yellow powder 5.4 &amp; 〇 0 弟番 rn Ο

FD-MS analysis, identification of the light yellow powder for the compound jjiie lack% Court,; ^

The compound was subjected to sublimation purification under vacuum (2×1 (T4Pa), and as a result, after purification by the second sublimation, it was confirmed that the high-purity compound H11 was not confirmed in the HPLC analysis. Synthesis Example 12 (Synthesis of Compound H12) Substance Aml2 was used instead of the intermediate Aml. The same reaction as in Synthesis Example 1 was carried out to obtain a pale yellow powder, and the FD-MS analysis was carried out to identify the pale yellow powder as the compound h12. ^ Under vacuum (2 x 10 4 Pa) Sublimation purification of the compound, after sublimation purification, was not confirmed in the HPLC analysis: high purity compound H12. Synthesis Example 13 of stomach # (synthesis of compound H13) In addition to using the intermediate Aml3 instead of the intermediate In the same manner as in Aml, the same reaction as in Synthesis Example 1 was carried out to obtain a pale yellow powder, which was subjected to FD-MS analysis, and the pale yellow powder was identified as compound m3. Sublimation purification of the compound was carried out under vacuum (2χ10-4 Pa). After the sublimation purification was carried out, it was not confirmed in the HPLC analysis that &amp; quality 93 201016663 high-purity compound Η13. Synthesis Example 14 (synthesis of compound Η14) The same reaction as in the synthesis example 1 was carried out except for the intermediate Aml, and the pale yellow powder was obtained in the same manner as in the above, and the yt FD-MS analysis was carried out to identify the pale yellow powder as a compound. 2xl0·4 Pa) Sublimation purification of the compound, after the purification of one sublimation, no high-purity compound H14 was obtained in the HPLC analysis.

Synthesis Example 15 (Synthesis of Compound H15) The same reaction as in Example 1 was carried out except that the intermediate Aml5 was used instead of the intermediate Ami to obtain a light yellow powder 5.8-'FD-MS analysis to identify the pale yellow powder. It is a compound Η15. After the a bit was absent, the compound was subjected to sublimation purification under vacuum (2xl 〇 -4 Pa), and as a result, after purification by sublimation, it was confirmed that the impurity peak = high purity compound H15 was not observed in the HPLC analysis. Synthesis Example 16 (Synthesis of Compound H16) The same reaction as in Synthesis Example 1 was carried out, except that the intermediate Aml6 was used instead of the intermediate Aml, to obtain a pale yellow powder (4.2 g). The pale yellow powder was identified as compound H16 by FD-MS analysis. Then, the compound was subjected to sublimation purification under vacuum (2×1 (T4 Pa), and as a result, after sublimation purification, no impurity peak was obtained in the HPLC analysis = high purity compound H16 ° Synthesis Comparative Example 1 (Comparison of Comparative Compound 4) The same reaction as in Synthesis Example 1 was carried out except that N,N-diphenylamine was used instead of the intermediate Ami to obtain a pale yellow powder of 3.6 g. The pale yellow powder was identified by FD-MS analysis. The compound 4 was compared. Then, the compound was subjected to sublimation purification under vacuum (2×1 〇·4 Pa), and as a result, high-purity comparative compound 4 in which impurity peaks were not completely removed was obtained by one sublimation purification. Synthesis Comparative Example 2 (Comparative Example 5 Synthesis: The same reaction as in Synthesis Example 1 was carried out except that N-(4-methoxyphenyl)-N-phenylamine was used instead of the intermediate Ami to obtain 3.6 g of pale yellow yttrium powder. MS analysis, the light yellow powder was identified as Comparative Compound 5. Then, the compound was sublimed and purified under vacuum (2χ1〇_4 pa), and the impurity peak was completely removed by one sublimation purification. Southern purity comparison compound 5. Example 1 (Production of organic EL device) A 25 mm x 75 mm x 1.1 mm thick glass substrate (made by Geomatic) with an ITO transparent electrode was subjected to ultrasonic wave/month in isopropyl alcohol for 5 minutes. Washing, and then performing ultraviolet (UV) ozone Q (ozone) cleaning for 30 minutes. The cleaned glass substrate with the transparent electrode wire is mounted on the substrate holder of the vacuum distillation apparatus. The H232 film having a film thickness of 60 nm was formed as a hole injection layer by vapor-forming the following compound H232' on the side on which the transparent electrode line was formed so as to cover the transparent electrode. '' On the H232 film, The above compound hi (Synthesis Example 1) was distilled to form a hole transport layer having a film thickness of 2 〇 nm, and then the following compound 95 201016663 EMI was distilled to form a light-emitting layer having a film thickness of 40 nm. The following styrene-based amine compound D1 of the molecule has a weight ratio of EM1 to D1 of 40: 2. Al The following Alq is formed into a film having a film thickness of 1 〇 nm on the film. Layer function. After that Li (Li source of Li: manufactured by Sae Getter Co., Ltd.) as a reducing dopant material was subjected to binary vaporization with Alq to form an Alq:Li film (film thickness: 1 〇 nm) as an electron injection layer (cathode). An organic EL element was formed by vaporizing the metal A1 on the Alq: Li film to form a metal cathode. Then, the obtained organic EL element was stored at i〇5 ° C for 8 hours, and then the 'luminescence efficiency was measured' to observe the luminescent color. . The luminance was measured using a CS1000 manufactured by Minolta, and the luminous efficiency at 1 mA mA/cm 2 was calculated. Further, the half life of the light emission at the initial luminance of 5000 cd/m2, room temperature, and direct-current (DC) constant current driving was measured. The results are shown in Table 1. [化46] Q Ο Ν-〇-〇-Ν &quot;Η232 5 ύ

96 201016663

Example 2 to Example 4 (Production of Organic EL Element) The same procedure as in Example 1 was carried out except that the compound H2, the compound H3 and the compound H5' described above were used as the hole transporting material instead of the compound H1. An organic EL element is produced.

. In the same manner as in Example 1, the obtained organic EL device was stored at 105 C for 8 hours, and then the luminous efficiency was measured, and the luminescent color was observed, and the initial luminance was measured at 5000 cd/m 2 , room temperature, and DC constant current driving. The half life of the product is shown in Table 1. Example 5 (Production of Organic EL Element) Instead of using the following arylamine compound D2 amine compound D1, the EL element was used in the same manner as in the case of a vinyl group. Me is a methyl group. In the same manner as in Example 1, the obtained organic EL device was stored at 105 ° C for 8 hours, and then the luminous efficiency was measured, and the luminescence was observed. Then, the initial luminance was measured at 5000 cd/m 2 , room temperature, and DC constant current driving. The half life of the underlying luminescence is shown in Table 1. Machine 97 201016663 [化 47]

Me

...D2 Ν· 0

Me 1 to Comparative Example 5 (Production of Organic EL Element) Comparative Example An organic EL device was produced in the same manner as in Example 1 except that Comparative Compound 1 to Comparative Compound 5 were used instead of Compound HI 〇 as a hole transport material. Further, in the same manner as in Example 1, the obtained organic EL device was stored at 105 ° C for 8 hours, and then the luminous efficiency was measured, and the luminescent color was observed, and the initial luminance was measured at 5000 cd/m 2 , room temperature, and DC constant current driving. The half life of the underlying luminescence is shown in Table 1. [化 48] ❹ 98 201016663

Comparative compound 3

Comparative compound 4 99 201016663

Comparative Example 5 Comparative Example 6 (Production of Organic EL Element) An organic EL element was produced in the same manner as in Example 5 except that the above Comparative Compound 4 was used instead of the compound H1 as a hole transporting material. In the same manner as in Example 1, the obtained organic EL device was stored at 105 ° C for 8 hours, and then the luminescence efficiency was measured, and the luminescent color was observed, and the initial luminance was measured at 5 cd/m 2 , room temperature, and DC. The half life of the luminescence driven by the current was measured, and the results are shown in Table 1. [Table 1] Example Hole transport material Luminous efficiency (cd/A) Example 1 H1 6.3 Example 2 H2 6.2 Example 3 H3 6.4 Example 4 H5 6.3 Example 5 H2 6.3 Comparative Example 1 Comparative Compound 1 4.2 Comparison Example 2 Comparative Compound 2 5.4 Comparative Example 3 Comparative Compound 3 5.6 Comparative Example 4 Comparative Compound 4 3.9 Comparative Example 5 Comparative Compound 5 3.1 Comparative Example 6 Comparative Compound 4 4.0 Luminescent Color

Color blue color blue color blue blue blue blue bluish blue half life (hours) 430 470 440 390 460 130 240 190 160 90 160 100 201016663 Example 6 (manufacture of organic EL elements) An organic EL device was produced in the same manner as in Example 1 except that the following charge acceptor compound was formed into a film of 10 nm between H232 and the film thickness of H232 was changed to 50 nm. Further, in the same manner as in Example 1, the obtained organic EL device was stored at 10 ° C for 8 hours, and the luminous efficiency was measured to observe the luminescent color. Further, the half-life of light emission at the initial luminance of 5000 cd/m2, room temperature, and DC constant current driving was measured. As a result, the luminous efficiency was 5.4 cd/A, the luminescent color was blue, and the half life was 410 hours. [化49]

NC CN ,&gt;/fly

N N \ / V·................/ • •• Charge Receptor Compound NC./--4(》-CN /==N N=:<

NC CN Comparative Example 7 (Production of Organic EL Element) An organic EL element was produced in the same manner as in Example 6 except that the above Comparative Compound 4 was used instead of the compound hi as a hole transporting material. Further, in the same manner as in Example 1, the obtained organic EL device was stored at 105 C for 8 hours, and then the luminous efficiency was measured to observe the luminescent color. Further, the half-life of light emission at an initial luminance of 5000 cd/m2, room temperature, and DC constant current driving was measured. As a result, the luminous efficiency was 3 5 cd/A, and the luminescent color was blue, and the semi-agricultural life was hour. [Industrial Applicability] 101 201016663 After the preservation, the aromatic amine derivative can realize an organic EL device which has a high light attack rate and a long lifetime even at a high temperature. The present invention is disclosed as above, and the invention is limited to the present invention. The second embodiment of the invention is as follows: the scope of the patent application is defined as follows: 〇 None [Main component symbol description] None 〇 102

Claims (1)

201016663 VII. Patent application scope: h An aromatic amine derivative represented by the following general formula (1): [Chemical 1] …(1) [In the formula (R), Ri to R4 represents a linear or branched alkyl group composed of a cigarette having a carbon number of 1 to 10, a cycloalkyl group having a carbon number of 3 to 10, and a carbon number of 丄10. Alkoxy group, trialkylsulfanyl group having a carbon number of 3 to 10, triarylsulfanyl group having a carbon number of 18 to 30, alkylarylsulfanyl group having a carbon number of 8 to 15, and a carbon number of 6 to 14 The aryl group, a and b are each independently 〇~4, c and d are independently 〇~3, and adjacent R1~R^ bonds form a saturated or unsaturated ring (where 'R3 and ruler 4 are not Bonding to form an aromatic ring), two, a linear or branched alkyl group having a carbon number of 12, or a cycloalkyl group having a carbon number of 3 to 10, and An is represented by the following formula (2) , Ah is represented by the following general formula (3)] [Chemical 2] (R5)e (Re)f (R?)g (Ar3) - (Ar4) - (Ar5) 103 _(3) 201016663 (Re)h (Α<) [In the formulas (2) and (3), Ah~Ah are independently Rs~han8 having a nuclear carbon number of 6 to μ, a hydrogen atom, an n-arylene group having a carbon number, an Ο 链 chain, a straight or 3 to 10 trialkylalkylene group having a branched or cyclic alkyl group and a carbon number of i~1〇, having a carbon number of 18 ～3 oxy, an alkylarylalkylene group having a carbon number of 8 to 15, a triarylalkylene group, or a biphenyl group, and an aryl group 6 having an X number of 6 to 14 and € are independently 1~4, g and h are each independently 1~5. When e~f is greater than or equal to 2, the same or different existence exists, and K·5~Rs are respectively formed by R·5~Re. An aromatic group as described in the above-mentioned item It is represented by the following general formula (5), and is represented by the following general formula (4), and Ar2 [Chemical 3J τ 104 201016663 (4) -0 (5) The definition of h is the same as [in the formulas (4) and (1), R5 to R8 and e are the same as the above formula (2) and the above formula (3)]. The aromatic amine derivative according to Item 1, wherein in the above formula (1), Ari is represented by the following formula: and Ar2 is represented by the formula (1): ^ ^ [Chemical 4] ( Re)h _(5) -(5 (Rs)e (^e)f (^7)9 (6) ❹ (R7)g (7) The definitions of the formulae (5) to (7) towels 'R5 to r8 and e to h are the same as those of the above formula (2) and the above formula (3). 5. The aromatic bribe according to claim 1, wherein R8 of the above formula (3) is a hydrogen atom. 8. If you apply for the aromatic bribe as described in item 4 of the patent scope, 105 In 201016663, r8 of the above formula (5) is a hydrogen atom. The above-mentioned ST, the aromatic amine derivative according to item 4, the organism, the aromatic amine derivative described in the first or second item, or the material for the organic electroluminescence device. The aromatic amine derivative described in the first item of the item 2 of the BioHit is a hole transporting material for an organic electroluminescence device. Between 2 and ::, the inflammation holds an organic thin film layer containing one or more layers containing at least a light-emitting layer; and at least the layer of the organic thin film layer contains the fragrance of the i-th item = the second item of the patent scope a family bribe organism as a component of a single or a mixture of 0 ^!·!, an organic electroluminescent element, between the electrode and the anode of the organic electroluminescent element, having a layer or layers containing at least a light-emitting layer An organic thin film layer; and the organic thin film layer has a hole transport layer, wherein the hole transport layer each has an aromatic amine derivative as described in the scope of claim 2 or 2 as a component of a single or a mixture. 12. An organic electroluminescent device, wherein: (4) having an organic thin film layer comprising at least a light-emitting layer or a plurality of layers between the cathode and the anode; and the organic thin film layer having a plurality of layers a hole transport layer, wherein the hole transport layer of the hole transport layer directly contacting the light-emitting layer contains an aromatic amine derivative as described in claim 106 201016663 or item 2 as a single or mixed electroluminescent element. The layer of the organic electroluminescent element=the layer containing at least the luminescent layer or the Ο0 containing film layer has an electric power layer, and the hole injection layer i has the patent item 1 or the The aromatic amine derivative according to the above item, wherein the organic electroluminescent element according to the above item 1 is. The first layer contains a styrene amine compound and/or an arylamine amine core 5 == the organic electroluminescent element described in the first item and the "customer layer has a multilayer hole injection layer or a hole The transport layer has at least a layer of charge in the hole injection layer or the hole transport layer, =11!^14 Electroluminescence element 107 201016663 IV. Designated representative diagram (1) The representative representative figure of the case is: no. (2) A brief description of the symbol of the representative figure: None 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: 4