JP2000204158A - Aromatic amine derivative and soluble conductive compounds - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an aromatic amine derivative having specific repeating unit, number average molecular weight in a specific range and high solubility, excellent in coating property and stability as a solution, useful as raw material for conductive polymer film having small charge storage or the like. SOLUTION: An aromatic amine derivative having repeating units expressed by formulae I and II [R1 is a monovalent hydrocarbon or an organoxy group; A and B are each a divalent group expressed by formula III or IV (R2-R11 are each H, OH, a monovalent hydrocarbon, an organoxy group, an acyl or the like); m and n are each a positive integer >=1 and m+n=3-3,000], and having number average molecular weight 250-100,000 is obtained. A soluble conductive compound can be obtained by forming a salt from this aromatic amine derivative and an electron-accepting dopant (preferably a Lewis acid, a proton acid, a transition metal compound or the like). The soluble conductive compound has high solubility and useful for an antistatic membrane or the like.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel aromatic amine derivative and a soluble conductive compound obtained by forming a salt of the derivative with an electron-accepting dopant. Since the soluble conductive compound of the present invention exhibits high solubility, it is useful for an antistatic coating, an electromagnetic wave shielding material and the like. .

[0002]

2. Description of the Related Art Heretofore, several methods for preventing static electricity and reducing resistance have been proposed. For example, a method of mixing a metal powder or a conductive metal oxide into a specific non-conductive polymer, a method of using an ionic surfactant, and the like are exemplified.

However, these methods have problems that, for example, a uniform coating film cannot be obtained, transparency is impaired, or ionic impurities increase so that they are not suitable for use in electronic devices.

On the other hand, examples of low-resistance polymer materials include so-called conductive polymers represented by polyaniline, polypyrrole, polythiophene and the like. Such a conductive polymer can be obtained by chemical oxidation polymerization using aniline, pyrrole, thiophene or a derivative thereof as a monomer material with an oxidizing agent, or electrochemical polymerization. It is known that a conductive polymer material obtained by such a method generally shows high conductivity by doping with an acid such as a Lewis acid. The conductive polymer obtained in this way is
It can be applied to antistatic agents, electromagnetic wave shielding agents, etc.

However, since the conductive polymer material polymerized by the above-described method generally has low solubility in a solvent, a film using a varnish dissolved or dispersed in an organic solvent is brittle, has a low mechanical strength, and has a low toughness. It was difficult to obtain a proper coating film.

That is, since such a so-called conductive polymer has low resistance, it has a practically excellent antistatic ability and also has an excellent performance in terms of charge accumulation and the like. However, it is not always satisfactory in terms of the solubility of the solution or the properties of the coating film, and a low-resistance polymer material having improved this point has been demanded.

[0007]

As described above, the conventional conductive polymer material has low solubility and may cause problems in forming. For this reason, there has been a demand for a polymer material which is more soluble in an organic solvent and exhibits high electric conductivity while maintaining various characteristics of the conductive polymer.

[0008] That is, an object of the present invention is to form a conductive polymer film or coating film which has high solubility as a solution and is excellent in coating properties and solution stability, and which has low antistatic properties or small charge accumulation. It is an object of the present invention to provide a soluble conductive compound which can be used and an aromatic amine derivative as a raw material thereof.

[0009]

Means for Solving the Problems The present inventors have made intensive studies to solve the above-mentioned problems, and as a result, completed the present invention. That is, the present invention provides a number average molecular weight of 250 to 10 having repeating units represented by the general formulas (1) and (2).
It relates to an aromatic amine derivative characterized by being 000.

[0010]

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(Wherein R ¹ represents an unsubstituted or substituted monovalent hydrocarbon group or an organooxy group, and A and B each independently represent a group represented by the general formula (3) or (4)

[0012]

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Wherein R ^{2 to} R ¹¹ are each independently a hydrogen atom, a hydroxyl group, an unsubstituted or substituted monovalent hydrocarbon group, an organooxy group, an acyl group or a sulfonic acid. M and n each independently represent a positive number of 1 or more and satisfy m + n = 3 to 3,000. The present invention also relates to a soluble conductive compound in which the aromatic amine derivative forms a salt with an electron-accepting dopant. Hereinafter, the present invention will be described in detail.

[0014]

BEST MODE FOR CARRYING OUT THE INVENTION In the formula (2), R ¹ is an unsubstituted or substituted monovalent hydrocarbon group or an organooxy group. The monovalent hydrocarbon group preferably has 1 to 20 carbon atoms, particularly preferably 1 to 5 carbon atoms. Specific examples of the monovalent hydrocarbon group include alkyl such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, octyl, and decyl groups. Group, cyclopentyl group, cycloalkyl group such as cyclohexyl group, bicycloalkyl group such as bicyclohexyl group, vinyl group, 1-propenyl group, 2-propenyl group, isopropenyl group, 1-methyl-2-propenyl group, 1 or Alkenyl groups such as 2 or 3-butenyl group and hexenyl group, phenyl group, xylyl group, tolyl group, biphenyl group, aryl group such as naphthyl group, benzyl group,
Examples thereof include an aralkyl group such as a phenylethyl group and a phenylcyclohexyl group, and a monovalent hydrocarbon group in which part or all of the hydrogen atoms are substituted with a halogen atom, a hydroxyl group, an alkoxy group, or the like. Examples of the organooxy group include an alkoxy group, an alkenyloxy group, and an aryloxy group. Examples of the alkyl group, the alkenyl group, and the aryl group include the same groups as those described above.

Preferably, R ¹ has ^{1 to} 2 carbon atoms.
0, more preferably an alkyl group or an alkoxy group having 1 to 4 carbon atoms, or a phenyl group, a cyclohexyl group, a cyclopentyl group, a biphenyl group which may have a substituent of an alkyl group or an alkoxy group having 1 to 4 carbon atoms, respectively. , A bicyclohexyl group or a phenylcyclohexyl group, particularly an alkyl group or an alkoxy group. A and B are each independently a divalent group represented by the following general formula (3) or (4).

[0016]

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In the above formulas (3) and (4), R ^{2 to} R ¹¹
Are each independently a hydrogen atom, a hydroxyl group, an unsubstituted or substituted monovalent hydrocarbon group or an organooxy group, an acyl group or a sulfonic acid group, and the unsubstituted or substituted monovalent hydrocarbon group or the organooxy group has carbon atoms R for 1-20
^{The same} ones as described in ¹ can be mentioned.
Examples of the acyl group include those having 2 to 10 carbon atoms, such as an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, and a benzoyl group.

R ^{2 to} R ¹¹ are preferably a hydrogen atom,
An alkyl group, an alkoxy group, an alkoxyalkyl group, an alkenyl group, an acyl group, a sulfonic acid group, a hydroxyl group, a phenyl group which may have a substituent of an alkyl group or an alkoxy group having 1 to 4 carbon atoms, a cyclohexyl group, A cyclopentyl group, a biphenyl group, a bicyclohexyl group or a phenylcyclohexyl group.

More preferably, R ^{2 to} R ¹¹ are a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a C ^{1 to} C ²
0 alkoxy group, alkoxy group having 1 to 20 carbon atoms, alkyl group having 1 to 20 carbon atoms, alkoxyalkyl group having 2 to 4 carbon atoms, alkenyl group having 2 to 4 carbon atoms, acyl group having 2 to 4 carbon atoms, benzoyl A phenyl group, a cyclohexyl group, which may have a substituent, a sulfonic acid group, a hydroxyl group, and a substituent (the substituent is an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms); Examples thereof include a cyclopentyl group, a biphenyl group, a bicyclohexyl group and a phenylcyclohexyl group. Particularly, a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and a carbon atom having 1 to 4 carbon atoms of the alkoxy group are preferable. Wherein the alkyl group has 1 to 4 carbon atoms, an alkoxyalkyl group, a vinyl group,
-A propenyl group, an acetyl group, a benzoyl group, a sulfonic acid group, a hydroxyl group and a substituent (each of which has 1 carbon atom)
Represents an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms. ), A phenyl group, a cyclohexyl group, a biphenyl group, a bicyclohexyl group, or a phenylcyclohexyl group which may have a).

The alkyl group having 1 to 4 carbon atoms is specifically a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an s-butyl group and a t-butyl group. The alkoxy group having a number of 1 to 4 is a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group,
Butoxy, s-butoxy and t-butoxy groups.

R ^{2 to} R ¹¹ may be the same or different from each other. In the above formula (1), m and n are each independently a positive number of 1 or more and satisfy m + n = 3 to 3000. The number average molecular weight of the aromatic amine derivative represented by the formula (1) is 250 to 100,000. As the aromatic amine derivative having a repeating unit of the above formulas (1) and (2), specifically, A and B are each independently the formula (3), and the following general formulas (1a) and (2a) )

[0022]

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(Wherein R ^{1 to} R ⁶ , m and n are the same as above). Further, one of A and B is Expression (3), the other is Expression (4), and the following Expressions (1a) and (2b) or (1b) and (2a)

[0024]

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(Wherein R ^{1 to} R ¹¹ , m and n are the same as above)
Wherein A and B are each independently represented by the formula (4), and the following general formulas (1b) and (2b)

[0026]

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(Wherein R ^{1 to} R ¹¹ , m and n are the same as above)
Having a repeating unit of

The aromatic amine derivative having repeating units of the above formulas (1a) and (2a) and the method for synthesizing the soluble conductive compound using the same are not particularly limited. Can be synthesized.

That is, the aniline derivative and the N-substituted aniline derivative, which are sufficiently purified raw materials from which impurities such as antioxidants have been removed by distillation or the like, are mixed, and the salt is mixed with 1 to 3 times as much acid as the raw materials. Is formed. At this time, the mixing ratio of the aniline derivative and the N-substituted aniline derivative is not particularly limited, but is usually 1:99 to 99-1 in a molar ratio.

Since the salt obtained here is soluble in water, it is dissolved in water two to ten times the amount of the raw material. After maintaining the temperature at 25 ° C., ammonium persulfate, cerium sulfate, iron chloride or copper chloride is added as an oxidizing agent. The amount of the oxidizing agent to be added is 0.5 to 4 mol, preferably 1 to 2 mol, based on the added raw material. After adding an oxidizing agent and reacting for 10 to 50 hours, the mixture is filtered, and the filter is sufficiently washed with a low-boiling water-soluble organic solvent such as acetone, methanol, ethanol or isopropanol to obtain a soluble conductive compound. it can. The acid used here is not particularly limited as long as it serves as an electron-accepting dopant for the aromatic amine derivative. As electron accepting dopants, Lewis acids,
Examples include a proton acid, a transition metal compound, an electrolyte salt, and a halogen compound.

The Lewis acids include FeCl ₃ , PF ₅ , A
sF ₅ , SbF ₅ , BF ₅ , BCl ₃ , BBr _{3 and the} like. Examples of protonic acids include HF, HCl, HNO ₅ ,
H ₂ SO _4, HClO ₄ and inorganic acids, benzenesulfonic acid, p- toluenesulfonic acid, dodecylbenzenesulfonic acid, polyvinyl sulfonic acid, methanesulfonic acid, 1-
Organic acids such as butanesulfonic acid, vinylphenylsulfonic acid, camphorsulfonic acid and the like can be mentioned.

As the transition metal compound, FeOCl, T
_{iCl 4, ZrCl 4, HfCl 4} , NbF 5, NbC
l _5, TaCl _5, MoF _5, and the like. LiSbF ₆ as the electrolyte salt, LiAsF _6, NaAsF _6, Na
_{SbF 6, KAsF 6, KSbF 6} , [(n-Bu) 4 N]
_{AsF 6, [(n-Bu} ) 4 N] SbF 6, [(n-E
t) ₄ N] AsF ₆ , [(n-Et) ₄ N] SbF _{6 and the} like.

As the halogen compound, Cl ₂ , Br ₂ ,
I ₂ , ICl, ICl ₃ , IBr, IF and the like.
Among these electron accepting dopants, preferred are ferric chloride as a Lewis acid, inorganic acids such as hydrochloric acid and perchloric acid as protonic acids, and organic acids such as P-toluenesulfonic acid and camphorsulfonic acid. Can be

In the case of an aromatic amine derivative having no dopant, the desired aromatic amine derivative can be obtained by washing the soluble conductive compound obtained by the above-mentioned method with an alkali. Here, the alkali is not particularly limited, but ammonia, sodium hydrogen carbonate and the like are desirable. As described above, the aromatic amine derivative of the present invention can be easily obtained by treating a soluble conductive compound with an alkali.

The aromatic amine derivative thus obtained can be easily dissolved in a conductive polymer compound by doping a Lewis acid, a proton acid, a transition metal compound, or an electrolyte salt as the electron accepting dopant described above. Compound. The amount of the electron acceptor that forms the dopant is generally such that the dopant is one or less per nitrogen atom in the repeating unit having a conjugated structure containing nitrogen as a basic atom. preferable.

Further, after forming the coating film of the aromatic amine derivative of the present invention, doping can be performed by exposing to a hydrochloric acid vapor or an iodine vapor. In the aromatic amine derivative having the repeating units of the formulas (1a) and (2a), m and n each independently represent 1
It is preferably at least 2, more preferably at least 4, and m + n is preferably from 4 to 3000, more preferably from 8 to 20.
00 and a number average molecular weight of 250
It is from 10,000 to 10,000, preferably from 600 to 70,000, and more preferably from 1,000 to 70,000.

Further, (1a) and (2b) or (1b)
And (2a) or a method of obtaining an aromatic amine derivative having a repeating unit of (1b) and (2b) and a soluble conductive compound from the aromatic amine derivative are also represented by the above formula (1).
The same applies to the case of the aromatic amine derivative having the repeating unit of (a) and (2a), and the range of m and n includes the preferred range, and Are the same as those of the aromatic amine derivatives, but with the formula (1)
The number average molecular weight of the aromatic amine derivative having a) and (2b) or the repeating units of the formulas (1b) and (2a) is 3
00 to 10,000, preferably 700 to 80,00
0, more preferably 1600-70,000,
The number average molecular weight of the aromatic amine derivative having the repeating units of the formulas (1b) and (2b) is 350 to 10,000,
Preferably from 800 to 80,000, more preferably 1,
600-70,000.

The thus obtained soluble conductive compound of the present invention can be used as a common organic solvent, for example, a chlorinated solvent such as chloroform, dichloroethane and chlorobenzene.
It is soluble in polar solvents such as amide solvents such as N, N-dimethylformamide and N, N-dimethylacetamide and phenol solvents in an amount of 2 to 10% by weight. However, in order to obtain a sufficiently stable varnish without gelling, N, N-dimethylformamide is most desirable. In this case, the solubility is usually 5 to 7% by weight.

Even if a solvent cannot be obtained alone by itself, another solvent may be added within a range where a homogeneous solvent can be obtained. Examples include ethyl cellosolve, butyl cellosolve, ethyl carbitol, butyl carbitol, ethyl carbitol acetate, ethylene glycol and the like.

When a polymer conductive compound coating film is formed on a substrate, a solution of the obtained soluble conductive compound is added for the purpose of further improving the adhesion between the polymer conductive compound film and the substrate. It is of course preferable to add an additive such as a coupling agent.

The coating method for forming the polymer conductive composite of the present invention includes a dipping method, a spin coating method,
Examples include a transfer printing method, roll coating, and brush coating, but are not particularly limited. Hereinafter, the present invention will be described in more detail by way of Examples, but the present invention is not limited thereto.

[0042]

EXAMPLES Example 1 (Copolymerization of phenetidine and N-butylaniline) 500
6.86 g of phenetidine (0.05 mol)
l), 7.46 g of N-butylaniline (0.05 mol)
1) and 11.0 g of hydrochloric acid was gradually added thereto. Further, 110 g of water was added thereto, and phenetidine and N-butylaniline hydrochloride were dissolved while stirring slowly. When these were dissolved, 22.82 g (0.1 mol) of ammonium persulfate dissolved in 50 g of water was added.
The mixture was stirred and reacted for 4 hours. After completion of the reaction, 100
After putting in 0 cc of acetone, unreacted substances were washed off, solids were separated by filtration, washed with acetone, and dried at 80 ° C. under reduced pressure to obtain 4.61 g of green powder.

The obtained soluble conductive compound of the present invention was dispersed in 300 cc of aqueous ammonia (5%), stirred well, and the doped hydrochloric acid was removed to obtain a compound which is an aromatic amine derivative of the present invention. . The molecular weight of this N, N-dimethylformamide solution (0.3% by weight) was measured by gel permeation chromatography (GPC) to find that the number average molecular weight was 12,000. In addition, the obtained compound was confirmed by IR to confirm that this powder was an aromatic amine derivative which was a target copolymer.

According to NMR, the ratio of N-butylaniline to phenetidine in the molecule was 1: 3. Further, peaks of N-butylaniline and phenetidine were confirmed by pyrolysis gas chromatography. IR: 3350 cm ^-1 (νNH), 1320 cm ^-1 (ν
CN), 1220 cm ^-1 (νCO), 820 cm
^-1 (1,4-disubstituted benzene) The obtained powdery copolymer containing hydrochloric acid dopant is
A coating film was formed on a glass substrate by spin coating using an N-dimethylformamide solution (5% by weight solution), and the surface resistance was measured by a two-terminal method. The result was 3.0 × 10 ⁹ Ω.
/ □.

The compound from which the doped hydrochloric acid had been removed was dispersed in a 1M ferric chloride solution and redoped, and the surface resistance of the coating film produced in the same manner as above was measured. It was 35 × 10 ⁸ Ω / □.

Examples 2-3 and Comparative Examples 1-2 As shown in Table 1, the molar ratio between phenetidine and N-butylaniline was changed to synthesize a copolymer having a hydrochloric acid dopant in the same manner as in Example 1. Was measured and the surface resistance of the coating film produced using the N, N-dimethylformamide solution of the obtained copolymer was measured. The results are shown in Table 1 together with Example 1.

[0047]

Table 1 Synthesis and properties of phenetidine and N-butylaniline copolymerフ ェ Phenetidine N-butylani Yield Surface resistance Solubility ^{* 1} (mol) Phosphorus (mol) (g) (Ω / □) wt% ─────────────────────比較 Comparative Example 1 0.10 4.31 8.2 × 10 ⁹ 2 Example 2 0.07 0.03 2.84 8.0 × 10 ⁸ 7 Example 1 0.05 0.05 4.61 3.0 × 10 ⁹ 7 Example 3 0.09 0.01 1.43 2.9 × 10 ¹⁰ 7 Comparative Example 40 0.1 7.70 1.2 × 10 ¹⁰ 7 ──────────────────────────────── * 1 Stable without gelation at the concentration used for measurement It is the concentration that dissolves.

Example 4 (Copolymerization of phenetidine and N-ethylaniline) 500
6.86 g of phenetidine (0.05 mol)
l), 6.86 g of N-ethylaniline (0.05 mol)
1) and 11.0 g of hydrochloric acid was gradually added thereto. Further, 110 g of acetonitrile was added thereto, and phenetidine and N-ethylaniline hydrochloride were dissolved while stirring slowly.

When these were dissolved, 22.82 g (0.1 mol) of ammonium persulfate dissolved in 50 g of water
l) was added, and the mixture was stirred and reacted for 40 hours. After the completion of the reaction, the reaction product was placed in 1000 c of acetone, and the unreacted product was washed off. Thereafter, the mixture was separated by filtration, washed with acetone again, and the solid content was separated by filtration and dried at 80 ° C. under reduced pressure to obtain 6.20 g of a green powder.

A powder excluding the hydrochloric acid dopant was obtained in the same manner as in Example 1, and the number average molecular weight was measured to be 21,000. By IR, this powder was found to be the desired copolymer (aromatic amine derivative) Was confirmed. According to NMR, the ratio of N-ethylaniline to phenetidine in the molecule was 1: 3. Further, peaks of N-ethylaniline and phenetidine were confirmed by pyrolysis gas chromatography. IR: 3350 cm ^-1 (νNH), 1320 cm ^-1 (ν
CN), 1220 cm ^-1 (νCO), 820 cm
^-1 (1,4-disubstituted benzene)

Examples 5 to 6 and Comparative Examples 3 to 4 As shown in Table 2, the molar ratio between phenetidine and N-ethylaniline was changed to synthesize a copolymer having a hydrochloric acid dopant in the same manner as in Example 1. Was measured, and the surface resistance of a film prepared using an N, N-dimethylformamide solution of the obtained copolymer was measured. The results are shown in Table 2 together with Example 4.

[0052]

Table 2 Synthesis and properties of phenetidine and N-ethylaniline copolymer ─ Phenetidine N-ethylani Yield Surface resistance Solubility (mol) Phosphorus (mol) (g) (Ω / □) wt% ─────────────────────── ───────── Comparative Example 3 0.10 5.20 7.0 × 10 ⁷ 2 Example 5 0.07 0.03 4.10 3.52 × 10 ⁸ 5 Example 4 0. 05 0.05 6.20 5.12 × 10 ⁸ 5 Example 6 0.09 0.01 3.95 8.88 × 10 ⁸ 5 Comparative Example 70 0.1 4.27 8.31 × 10 ¹⁰ 5 ────────────────────────────────

Example 7 (Copolymerization of phenetidine and N-butylaniline) 500
6.86 g of phenetidine (0.05 mol)
l), 7.46 g of N-butylaniline (0.05 mol)
1) and 11.0 g of hydrochloric acid was gradually added thereto. Further, 300 g of water was added thereto, and phenetidine and N-butylaniline hydrochloride were dissolved while stirring slowly. When these were dissolved, 22.82 g (0.1 mol) of ammonium persulfate dissolved in 50 g of water was added, and the mixture was stirred and reacted at a reaction temperature of 35 ° C. for 12 hours. After the reaction,
The reactants were put in 1000 cc of acetone, and unreacted substances were washed off. Thereafter, the mixture was filtered, washed with acetone, the solid content was separated by filtration, and dried at 80 ° C. under reduced pressure to obtain a green powder 3.3.
8 g were obtained.

The resulting compound was analyzed by IR and FDMASS to make n-butylaniline at both terminals, and n + m was 4,
It was a copolymer compound composed of 5,6,7,8-mer. IR: 3350 cm ^-1 (νNH), 1320 cm ^-1 (ν
CN), 1220 cm ^-1 (νCO), 820 cm
^-1 (1,4-disubstituted benzene)

[0055]

The polymer conductive compound soluble in an organic solvent obtained by oxidative polymerization of the aniline derivative, which is an inexpensive raw material of the present invention, is useful as a coating agent for various electronic devices. is there. Also, it is useful as a light emitting material of an organic electroluminescence element.

Continued on the front page F-term (reference) 4H006 AA01 AB91 AB92 4J043 PA04 PB08 PC016 PC026 PC116 QC03 QC04 RA02 SB03 UB241 ZA21 ZA44 ZB11 5E321 BB57 GG01 GG05

Claims (12)

[Claims] 1. A number average molecular weight of 250 to 100,0 having a repeating unit represented by the general formulas (1) and (2).
An aromatic amine derivative, which is 00. Embedded image (In the formula, R ¹ represents an unsubstituted or substituted monovalent hydrocarbon group or an organooxy group, and A and B each independently represent a group represented by the general formula (3) or (4). Wherein R ^{2 to} R ¹¹ are each independently a hydrogen atom, a hydroxyl group, an unsubstituted or substituted monovalent hydrocarbon group or an organooxy group, an acyl group or a sulfonic acid group. , M and n are each independently a positive number of 1 or more, and satisfies m + n = 3 to 3000. ) 2. A and B of the aromatic amine derivative each independently represent the general formula (3), and the following general formula (1a)
Number average molecular weight of 250 having repeating units of (a) and (2a)
The aromatic amine derivative according to claim 1, which has a molecular weight of from 1 to 100,000. Embedded image (Wherein, R ^{1 to} R ⁵ , m and n are the same as described in the above formulas (1) to (3)) 3. The aromatic amine derivative according to claim 2, wherein R ¹ is an alkyl group having 1 to 20 carbon atoms or an alkoxy group having 1 to 20 carbon atoms. 4. R ^{2 to} R ⁵ each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, An alkyl group having 1 to 20 carbon atoms, an alkoxyalkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an acyl group having 2 to 4 carbon atoms, a benzoyl group, a sulfonic acid group, and a hydroxyl group; A phenyl group, a cyclohexyl group, a cyclopentyl group, which may have an alkyl group of 1 to 4 or an alkoxy group of 1 to 4 carbon atoms;
4. The aromatic amine derivative according to claim 2, which is a biphenyl group, a bicyclohexyl group or a phenylcyclohexyl group. 5. The aromatic amine derivative A or B is represented by the formula (3), the other is represented by the formula (4), and the following formula (1a)
The aromatic amine derivative according to claim 1, having a number average molecular weight of 300 to 100,000 having a repeating unit of (1) and (2b) or (1b) and (2a). Embedded image (Wherein, R ^{1 to} R ¹¹ , m, and n are the above formulas (1) to (3)
Same as described in) 6. The aromatic amine derivative according to claim 5, wherein R ¹ is an alkyl group having 1 to 20 carbon atoms or an alkoxy group having 1 to 20 carbon atoms. 7. R ^{2 to} R ¹¹ each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, An alkyl group having 1 to 20 carbon atoms, an alkoxyalkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an acyl group having 2 to 4 carbon atoms, a benzoyl group, a sulfonic acid group, and a hydroxyl group; A phenyl group, a cyclohexyl group, a cyclopentyl group, which may have an alkyl group of 1 to 4 or an alkoxy group of 1 to 4 carbon atoms;
The aromatic amine derivative according to claim 5, which is a biphenyl group, a bicyclohexyl group, or a phenylcyclohexyl group. 8. The aromatic amine derivatives A and B each independently represent the formula (4), and the following general formulas (1b) and (2)
Number average molecular weight 350 to 10 having a repeating unit of b)
2. The aromatic amine derivative according to claim 1, which has a molecular weight of 000.
Formula (7) (Wherein, R ^{1 to} R ¹¹ , m, and n are the above formulas (1) to (3)
Same as described in) 9. The aromatic amine derivative according to claim 8, wherein R ¹ is an alkyl group having 1 to 20 carbon atoms or an alkoxy group having 1 to 20 carbon atoms. 10. R ^{2 to} R ¹¹ each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, and 1 to 20 carbon atoms.
An alkoxy group, an alkoxy group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an alkoxyalkyl group having 2 to 4 carbon atoms, an acyl group having 2 to 4 carbon atoms, a benzoyl group , A sulfonic acid group, a hydroxyl group, and a phenyl group, a cyclohexyl group, and a cyclopentyl, each of which may have a substituent (the substituent is an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms). Group,
The aromatic amine derivative according to claim 8 or 9, which is a biphenyl group, a bicyclohexyl group, or a phenylcyclohexyl group. 11. A soluble conductive compound obtained by forming a salt of the aromatic amine derivative according to claim 1 with an electron-accepting dopant. 12. The soluble conductive compound according to claim 11, wherein the electron-accepting dopant is selected from a Lewis acid, a proton acid, a transition metal compound, an electrolyte salt, and a halogen compound.