WO2004085380A1

WO2004085380A1 - Benzene derivative having moiety of long linear conjugated system structure, method for preparation thereof and liquid crystalline material

Info

Publication number: WO2004085380A1
Application number: PCT/JP2004/003862
Authority: WO
Inventors: Yuichiro Haramoto
Original assignee: Nippon Chemical Industrial Co., Ltd.
Priority date: 2003-03-24
Filing date: 2004-03-22
Publication date: 2004-10-07
Also published as: JPWO2004085380A1; JP4574549B2

Abstract

A novel benzene derivative having a moiety of a long linear conjugated system structure, characterized by being represented by the general formula (1): (1) wherein R1 represents, for example, a group having an unsaturated bonding represented by the following general formula (2): (2) where R5 represents a hydrogen atom or a methyl group and B represents, for example, an alkylene group, R2, R3 and R4 represent an alkyl group, A represents an alkylene group, and X represents a halogen atom; a method for preparing the benzene derivative; and a liquid crystalline material comprising said compound. The benzene derivative compound is expected to have excellent electric charge transporting property without excitation by a light, in the electric charge transportation utilizing the molecular orientation in a liquid crystalline state.

Description

Description: Benzene derivative having a long linear conjugated structure, method for producing the same and liquid crystalline material

The present invention relates to an optical sensor, an organic electroluminescence element (EL element), a photoconductor, a spatial modulation element, a thin film transistor, a charge transport material of an electrophotographic photoreceptor, a photolithographic, a solar cell, a nonlinear optical material, and an organic material. The present invention relates to a novel benzene derivative having a long linear conjugated structure useful as a charge transporting material for semiconductor capacitors and other sensors, a method for producing the same, and a liquid crystalline material. Background art

In recent years, organic electroluminescent devices using an organic material as a hole transporting material or a charge transporting material constituting an electroluminescent device have been actively researched.

As such charge transport materials, compounds such as anthracene derivatives, anthraquinoline derivatives, imidazole derivatives, styryl derivatives, hydrazone derivatives, triphenylamine compounds, and poly-N-vinylcarbazole oxdiazazole have been known. Have been.

Liquid crystal compounds are applied to various devices as display materials, for example, clocks, calculators, televisions, personal computers, mobile phones, and the like. Liquid crystal materials are classified into two types: liquid crystal materials (temperature-transition liquid crystal) and lyotropic liquid crystals (concentration-transition liquid crystal), based on the means of imparting phase transition. In terms of molecular arrangement, these liquid crystals are classified into three types: smectic liquid crystals, nematic liquid crystals, and cholesteric liquid crystals. Liquid crystals have the same optical anisotropy as optically uniaxial crystals, as they are also called anisotropic liquids. Orthoscope observation is a normal observation between orthogonal Nicols, and is useful for discriminating the type of liquid crystal and determining the transition temperature of the liquid crystal phase. This observation makes each liquid crystal more smectic liquid crystal due to its characteristic birefringent optical pattern. Are classified into A, B, C, D, E, F, and G. Hanna et al. Have proposed a charge transport material using a liquid crystalline compound having a liquid crystal phase having a smectic phase and having a charge transporting ability. For example, a liquid crystalline charge transporting material having a smectic liquid crystal property and having a reduction potential in a range of −0.3 to −0.6 (V vs. SEC) with respect to a standard reference electrode (SCE) (Japanese Patent Application Laid-Open No. — 3164442), a liquid crystal charge transporting material in which a predetermined amount of fullerene C70 having a sensitizing effect is mixed with a liquid crystal compound exhibiting a smectic phase having self-orientation (Japanese Patent Application Laid-Open No. No. 162,648), a liquid crystal charge transporting material-dispersed polymer film in which a liquid crystal compound exhibiting a smectic phase is contained in an organic polymer matrix. No. 2118), a liquid crystalline charge transport material containing a mixture containing a smectic liquid crystalline compound (Japanese Patent Laid-Open No. 11-198971), and having a smectic liquid crystalline property. and an electron mobility or a liquid crystalline charge transport material hole mobility speed is ^{^{1 X 1 0 _ 5 cm 2}} / v · s or more (JP-1 0 3 1 2 7 1 1 No. Liquid crystalline charge transport including smectic liquid crystalline compounds having a functional group capable of forming a new bond between molecules or within a molecule and a functional group having hole and / or electron charge transport properties in one molecule. Materials (Japanese Patent Application Laid-Open No. 11-209761) have been proposed.

The smectic liquid crystalline compounds proposed above include 6 π-electron aromatic rings such as benzene ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring and troborone ring, naphthalene ring, azulene ring, benzofuran ring, indole ring, Indazole ring, benzothiazole ring, benzoxazole ring, benzimidazole ring, quinoline ring, isoquinoline ring, quinazoline ring, quinoxaline ring, etc. 1 π π-electron aromatic, or phenanthone ring, anthracene etc. It uses an smectic liquid crystal compound having an electronic aromatic ring to transport charges in a smectic Α phase liquid crystal state. However, the charge transport method described above is in need of photoexcitation region of its conductivity even without photoexcitation in ¹ 0- 1 ³ s Z cm, even when photoexcitation ¹ 0- 1 1 s / cm and Les intends insulator Value. Disclosure of the invention

The present inventors have proposed that a liquid crystalline compound having a smectic B phase as a liquid crystal phase be charged in a liquid crystal state of the smectic B phase or a solid state generated by a phase transition of the smectic B phase. A charge transport method in which pressure is applied (Japanese Patent Application Laid-Open No. 2000-3518786) has been proposed. The present invention has been made in view of such prior art, and an object of the present invention is to provide a novel charge transport method utilizing ^? Orientation of a liquid crystal state, in which excellent charge transport properties can be expected without photoexcitation. It is an object of the present invention to provide a benzene derivative having a very long linear conjugated structure, a method for producing the benzene derivative, and a liquid crystalline material containing the compound.

That is, the first invention to be provided by the present invention is represented by the following general formula (1)

{Wherein, R ¹ is a linear or branched alkyl group, an alkoxy group, or the following general formula (2)

CH ₂ = CB- (2)

(Wherein, R ⁵ represents a hydrogen atom or a methyl group, B represents an alkylene group, -co—0— (CH ₂ ) _N— C ₆ H ₄ —CH ₂ _, —CO—). A group having a saturated bond; R ² ,

R ³ and R ⁴ represent an alkyl group, A represents an alkylene group, and X represents an octogen atom. It is a benzene derivative with a long linear conjugated structure characterized by the formula The second invention which the present invention intends to provide is represented by the following general formula (3)

(Wherein, R ¹ has the same meaning as described above), and the following general formula (4) HZ. N- R ⁷ Z Θ (4)

(Wherein, R ² , R ³ and A have the same meaning as described above. RR ⁷ and R ^{8 each} represent a monovalent organic group, and Z represents a halogen atom.) An acid adduct of a phosphonium salt represented by the following formula: The following general formula (5)

( Five )

(Wherein, RR ² , R ³ and A have the same meanings as described above). A first step of obtaining an amine derivative represented by the following formula:

R ⁴ — X (6)

(Wherein, R ⁴ and X are as defined above.) Following general formula, characterized in that it comprises a second step of Ru is reacted with a halogenating compound represented by (1) R ³

(Wherein, RR ² , R ³ , R ⁴ , A and X have the same meanings as described above.) A benzene derivative having a long linear conjugated structure represented by the formula:

A third invention to be provided by the present invention is represented by the general formula (1). A liquid crystal material comprising a benzene derivative having a long linear conjugated structure or a compound derived therefrom. BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, the present invention will be described in detail.

The novel compound provided by the present invention is a benzene derivative having a long linear shared system structural part represented by the general formula (1).

In the formula of the benzene derivative having a long linear conjugated structure represented by the general formula (1), R ¹ is a linear or branched alkyl group, an alkoxy group, or a group represented by the general formula (2). A group having an unsaturated bond. The alkyl group has 1 to 18 carbon atoms, and specific examples include a methyl group, an ethyl group, a butyl group, a pentyl group, a hexyl group, an octyl group, a dodecyl group, a pendecyl group, an octadecyl group and the like. Among them, an alkyl group having 6 to 18 carbon atoms is particularly preferable. Further, the alkyl group is a general formula; CH ₃ — (CH ₂ ) _m —CH (CH ₃ ) — (CH ₂ ) _n —CH ₂ — (where n is 0 to 7 and m is 0 to 7) The branched alkyl group represented can improve the solubility in various solvents.

The alkoxy group is represented by a general formula: C _n H _{2n + 10} , wherein _n in the formula is preferably from! To 18, especially from 6 to 18 s.

Moreover, the general formula R ⁵ in the formula groups having represented unsaturated bond (2) represents a hydrogen atom or a methyl group, B is an alkylene group, - CO - 0 - (CH 2) n-, -C ₆ H ₄ One CH ₂ —, one CO—. The alkylene group may be linear or branched, and specifically preferably has 1 to 18 carbon atoms, for example, a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, Examples thereof include alkylene groups such as a pentamethylene group, an ethylethylene group, a propylene group, a butylene group, a hexylene group, an octadecylene group, a nonylene group, a decylene group, and a dodecylene group. Also, _{n of} —CO-1 0— (CH ₂ ) _n — is! Those of ~ 18 are particularly preferred.

Further, R ² , R ³ and R ^{4 in} the formula of the benzene derivative having a long linear conjugated structure represented by the general formula (1) represent an alkyl group, and the alkyl group has 1 to 1 carbon atoms. 18 specifically, methyl group, ethyl group, butyl group, pentyl group, Hexyl group, octyl group, dodecyl group, pendecyl group, octadecyl group, etc., among which an alkyl group having 1 to 5 carbon atoms is particularly preferred, and R ² , R ³ and R ⁴ are the same. Or a different group.

In the formula of the benzene derivative having a long linear conjugated structure represented by the general formula (1), A represents an alkylene group, and the alkylene group may be linear or branched. Preferably, specifically, those having 1 to 10 carbon atoms are preferred, for example, alkylene groups such as methylene group, ethylene group, propylene group, butylene group, hexylene group, octadecylene group, nonylene group, and decylene group. Among them, an alkylene group having 1 to 5 carbon atoms is particularly preferable.

In the formula of the benzene derivative having a long linear conjugated structure represented by the general formula (1), X represents a halogen atom such as bromine, chlorine, and iodine.

In the present invention, the benzene derivative having a long linear conjugated structure represented by the general formula (1) is a novel compound, and the compound has a cis-form, a trans-form, or a cis-form as a conformation. It may be a mixture of trans forms.

Next, a method for producing a benzene derivative having a long linear conjugated structure represented by the general formula (1) will be described.

The method for producing a benzene derivative having a long linear conjugated structure represented by the general formula (1) of the present invention basically comprises the following first and second steps. <First-step>

The first step is the following reaction formula (1)

Reaction formula (1)

(Wherein, RR ³ , R ⁴ , RR ⁷ , R ⁸ , A and Z have the same meanings as described above). This is a step of producing an amine derivative represented by the general formula (5). The benzaldehyde derivative represented by the general formula (3) of the first raw material used in the first step is obtained by, for example, the following reaction scheme (2)

Anti-Jt, Sum (2)

A- 1

(9)

A- 2X I

A— 3 steps (11)

(X 2), Θ

( 13 )

A— 4 processes

(13) (14)

-CH = CH- CHO (Wherein, R ¹ has the same meaning as described above. R represents a monovalent organic group, and X ¹ and X ^{2 each} represent a halogen atom.) By performing the steps (A-1) to (A-4) It can be manufactured.

The step A-1 is represented by the general formula (9) by reacting a halide (compound (7)) with hydroxybenzyl alcohol (compound (8)) in a solvent in the presence of a base. To obtain a compound.

R ^{1 in} the formula of the halide (compound (7)) is a benzaldehyde derivative represented by the general formula (3) as a reaction raw material in the first step and a long linear compound represented by the general formula (1). This is a group corresponding to R ¹ in the formula of the benzene derivative having a conjugated structure part, and X ^{1 in} the formula represents a halogen atom such as bromine, chlorine, and iodine.

In the reaction in the A-1 step, the halide (compound (7)) is 1 to 3 times, preferably 1 to 1.5 times, the mole of hydroxybenzyl alcohol (compound (8)). 1 to 3 moles, preferably 1 to 1.5 moles of a base such as potassium hydroxide, sodium ethoxide, sodium methoxide, etc. in an alcohol solvent such as methanol, ethanol, etc., at 0 to 100 ° C, preferably The reaction is carried out at 60 to 80 ° C for 1 to 20 hours, preferably 5 to 10 hours.

Next, in step A-2, the compound (compound (9)) obtained in step A-1 and phosphorus halide (compound (10)) are reacted in a solvent to obtain the compound represented by the general formula (1). The compound represented by 1) is obtained.

X ^{2 in} the formula of the halogenated phosphorus (compound (10)) represents a halogen atom such as bromine, chlorine, and iodine.

The reaction in the step A-2 is carried out in an amount of 1 to 3 times, preferably 1 to 1.5 times, the amount of the phosphorus halide (compound (10)) based on the compound (compound (9)) obtained in the step A-1. The reaction is carried out in a solvent such as ethyl ether at 1 to 30 ° C., preferably 0 to 30 ° C. for 1 to 10 hours, preferably 1 to 5 hours at a molar ratio of twice.

Next, in the step A-3, the compound (compound (11)) obtained in the step A-2 and the phosphine compound (compound (12)) are reacted in a solvent to obtain a compound represented by the general formula (13). The compound represented is obtained.

R in the formula of the phosphine compound (compound (12)) represents a monovalent organic group; The type of R is not particularly limited as long as the compound represented by the general formula (11) can be phosphonidated, and specific compounds include, for example, triphenylphosphine trimethylphosphine, triethyl Trialkyl phosphines such as phosphine can be used.

The reaction in step A-3 is 1 to 3 times, preferably 1 to 1.5 times, the phosphine compound (compound (12)) based on the compound (compound (11)) obtained in step A-2. Perform the reaction at a molar ratio of 20 to 100, preferably 50 to 70 for 1 to 10 hours, preferably 3 to 5 hours in a solvent such as methylene chloride, chloroform, or dichloroethane. .

Then, in step A-4, the compound (13) obtained in step A-3 is reacted with terephthalaldehyde (compound (14)) in the presence of a base, whereby the reaction formula (1) 3) A benzaldehyde derivative represented by the formula is obtained.

In the reaction in the step A-4, the terephthalaldehyde (compound (14)) is used in an amount of 1 to 3 times, preferably 1 to 3 times the amount of the conjugate (compound (13)) obtained in the step A-3. 1.Molecules such as methanol, ethanol, etc. in a molar ratio of 1 to 5 times, preferably 1 to 3 times, the molar ratio of bases such as 5 times mol, sodium oxide, 7 potassium potassium, sodium ethoxide, sodium methoxide, etc. The reaction is carried out at 30 to 30 ° (: preferably 5 to 15 for 3 to 15 hours, preferably 5 to 10 hours in an alcohol solvent of the formula (I). Α— After 4 steps, the obtained benzaldehyde derivative (compound (3)) is heated in a solvent in the presence of iodine to selectively convert the benzaldehyde derivative (compound (3)) into a trans form. And continue to implement the first process However, since the reaction in the first step can be performed while maintaining the conformation, the trans form of the benzene derivative represented by the general formula (1) can be selectively obtained at a high yield.

In this case, the amount of iodine to be added is 0.001 to 0.1 times mol, preferably 0.005 to 0.01 times mol, of the benzaldehyde derivative (compound (3)). 1801801, preferably 130〜; L50. Solvents that can be used include, for example, benzene, toluene, o-xylene, m-xylene, p-xylene, benzene, o-dichlorobenzene, m-diethylene Benzene, p-dichlorobenzene, etc., and one or more of these solvents can be used.

The acid adduct of the phosphonium salt represented by the above general formula (4) as the other reaction raw material used in the first step is, for example, as shown in the following reaction scheme (3) Anti-JS scheme (3)

B-1 1 II

(15) (16)

(17)

Β-2 processes

B-1 3 (19)

(Four) (Wherein, R ² , R ³ , R ^s , R ⁷ , R ⁸ , A, and Z are as defined above, and Z ¹ represents a halogen atom.) Steps (B-1) to (B-3) It can be manufactured by carrying out the following.

In the step B-1, the halogenated amine compound (compound (15)) and hydroxybenzyl alcohol (compound (16)) are reacted in the presence of a base in a solvent to give the compound represented by the general formula (17). Is obtained.

R ² , R ^3, and A in the formula of the haguchigenated amine compound (compound (15)) represent a benzene derivative having a long linear conjugated structure represented by the general formula (1). of an R ^2, R ³ and a correspond to the radicals, also, Z ¹ in the formula are bromine, chlorine, a halogen atom and iodine.

The reaction in the B-1 step is performed in an amount of 1 to 3 times, preferably 1 to 1.5 times, the mole of the hydroxybenzyl alcohol (the compound (16)) to the halogenated amine compound (the compound (15)). 1 to 3 moles, preferably 1 to 1.5 moles of a base such as sodium, hydroxylated water, sodium methoxide, sodium methoxide, etc. in an alcohol solvent such as methanol or ethanol. The reaction is carried out at 100100 ° C., preferably 60-80 ° C., for 1-15 hours, preferably 5-10 hours. Next, in the B-2 step, the compound (compound (17)) obtained in the B-1 step is reacted with a sulfonyl halide (compound (18)) in a solvent to obtain the compound represented by the general formula (19). Is obtained.

Z in the formula of the sulfonyl halide (compound (18)) represents a halogen atom such as bromine, chlorine, and iodine.

The reaction in the B-2 step is performed in an amount of 1 to 3 times, preferably 1 to 1 times, the molar amount of the compound (compound (18)) based on the compound (compound (17)) obtained in the B-1 step. At a mixing ratio of 5 moles, for example, in a solvent such as methylene chloride, chloroform, or dichloromethane, at 120 to 100 ° C, preferably 0 to 50 ° C for 5 to 20 hours, preferably Incubate for 5-10 hours.

Next, in a B-3 step, the compound (compound (19)) obtained in the B-2 step and a phosphine compound (compound (21)) are reacted in a solvent to obtain a reaction raw material of the first step. To obtain an acid adduct of the phosphonium salt represented by the general formula (4) You.

R ^s , R ⁷ and R ^{8 in} the formula of the phosphine compound (compound (21)) represent monovalent organic groups, and the types of R ⁷ and R ⁸ are represented by the general formula (20) There is no particular limitation as long as the compound represented by the formula can be phosphonidated, and specific compounds include, for example, trialkylphosphines such as triphenylphosphine trimethylphosphine and triethylphosphine. it can.

In the reaction in the step B-3, the phosphine compound (compound (21)) is 1 to 3 times, preferably 1 to 1.1 times, the compound (compound (19)) obtained in the step B-2. The reaction is carried out at 30 to 100 ° C., preferably 60 to 80 ° C., preferably 1 to 10 hours, preferably 1 to 5 hours at a mixing ratio of 5 times in a solvent such as chloroform.

In the first step of the present invention, a benzaldehyde derivative represented by the general formula (3) is reacted with an acid adduct of a phosphonium salt represented by the general formula (4) in a solvent in the presence of a base.

The amount of the phosphonium salt represented by the general formula (4) is 1 to 3 times, preferably 1 to 1.5 times the mol of the benzaldehyde derivative represented by the general formula (3). '

Examples of the base that can be used in the first step include metal hydrides such as sodium hydrogen hydride, amines such as trimethylamine and triethylamine, and hydroxides such as 7 acid potassium and sodium hydroxide. Alkoxides such as alkali, sodium methoxide, potassium methoxide, sodium methoxide, potassium methoxide, and the like, piperidine, pyridine, potassium cresolate, alkyllithium, and the like are used, and these are used alone or in combination of two or more. However, the present invention is not particularly limited to these.

The amount of the base to be added is 1 to 4 moles, preferably 2 to 3 moles, based on the benzaldehyde derivative represented by the general formula (3).

Examples of the reaction solvent include one or two of ethers such as dioxane, tetrahydrofuran and dibutyl ether, nitriles such as acetonitrile and propionitrile, alcohols such as methanol and ethanol, dimethylformamide, acetone and water. More than one species can be used. The reaction conditions are as follows. C, preferably 15-25 ° C, and the reaction is carried out for 1-20 hours, preferably 5-15 hours.

After completion of the reaction, if desired, purification operations such as filtration, washing, and recrystallization are performed to obtain the desired amine derivative represented by the above general formula (5).

In the production process of the present invention, in performing the second step, the amine derivative represented by the general formula (5) obtained in the first step is further heated in a solvent in the presence of iodine. By the treatment, the amine derivative (compound (5)) can be selectively made into a trans form, and the reaction can be carried out while maintaining its conformation even if the second step is subsequently carried out. The desired trans form of the benzene derivative can be selectively obtained in high yield.

In this case, the amount of iodine to be added is 0.00 :! based on the amine derivative (compound (5)). It is from 0.01 to 1 mole, preferably from 0.005 to 0.001 mole, and the heat treatment temperature is from 100 to 180 ° C, preferably from 130 to 150. C. Examples of the solvent that can be used include p-xylene and the like. One or more of these solvents can be used.

(Second step)

The second step is represented by the following reaction formula (4)

(1)

(Wherein RR ² , R ³ , RA and X are as defined above) This is a step of obtaining a benzene derivative having a long linear conjugated structure represented by the general formula (1).

R ⁴ and X in the formula of the halogenated compound (compound (6)) as a reaction raw material in the second step are benzenes having a long linear conjugated structure represented by the general formula (1). Each of R ⁴ and X in the formula of the zen derivative corresponds to R ⁴ and R ⁴ represents an alkyl group. The alkyl group has 1 to 18 carbon atoms, and specifically includes a methyl group, an ethyl group, a butyl group, a pentyl group, a hexyl group, an octyl group, a dodecyl group, a pendecyl group, and an octadecyl group. Among them, an alkyl group having 1 to 5 carbon atoms is particularly preferable. X represents a halogen atom such as bromine, chlorine, and iodine.

In the reaction in the second step, the amine derivative represented by the general formula (5) is reacted with the halogenated compound represented by the general formula (6) in a solvent.

The addition amount of the halide represented by the general formula (6) is at least 10 to 500 times, preferably at least 400 to 50 times the amount of the amine derivative represented by the general formula (5). It is 0 times mol.

Examples of the reaction solvent include ethers such as dioxane, tetrahydrofuran and dibutyl ether, nitriles such as acetate nitrile and propionitrile, alcohols such as methanol and ethanol, dimethylformamide, acetone and water. Used alone or in combination.

The reaction is carried out at a reaction temperature of 0 to 100 ° C., preferably 30 to 60 ° C., and a reaction time of 10 to 30 hours, preferably 20 to 30 hours. .

After completion of the reaction, if desired, purification operations such as washing and recrystallization are performed to obtain the desired benzene derivative having a long linear conjugated structure represented by the general formula (1).

The thus obtained benzene derivative having a long linear conjugated structure represented by the general formula (1) is a compound exhibiting novel liquid crystallinity.

Next, the liquid crystal material of the present invention will be described.

The liquid crystalline material of the present invention comprises a benzene derivative having a long linear conjugated structure represented by the general formula (1) or a compound derived from the benzene derivative having the long linear conjugated structure. It contains.

Here, benzene having a long linear conjugated structure represented by the general formula (1) A compound that is derived from a derivative means that when R ^{1 in} the formula of the benzene derivative having the long linear conjugated structural part is a group having an unsaturated bond represented by the general formula (2), A homopolymer, a copolymer, a high molecular weight compound cross-linked by a cross-linking agent, or a high molecular weight compound obtained by an addition reaction with a high molecular compound having a hydrosilyl group (hereinafter, `` polymer '' ]

Here, the polymer has at least the following general formula (23) or the following general formula (24)

(Wherein, R ² , R ³ , R ⁴ , R ⁵ , A, B and X have the same meanings as described above).

The polymer may have a repeating unit derived from acrylic acid, methacrylic acid, styrene or the like as a copolymer component. In the case of a copolymer, the repeating unit represented by the above general formula (22) or the above general formula (23) accounts for 50 mol% or more, preferably 70 mol% or more, more preferably, in the copolymer. 80 mol% or more. The number average molecular weight of the polymer is in the range of 100 to tens of millions, preferably in the range of tens of thousands to millions. The polymer can be produced by the following method. For example, in order to produce a homopolymer, a copolymer of the general formula (1), or a high molecular weight compound crosslinked by a crosslinking agent, a desired monomer or a desired monomer and a crosslinking agent are used as a polymerization initiator. It can be produced by carrying out a polymerization reaction in the presence of a radical polymerization method such as a dissolution method, a suspension polymerization method, an emulsion polymerization method, or a bulk polymerization method.

To produce a high molecular weight compound by subjecting a polymer compound having a hydrosilyl group to an addition reaction with a benzene derivative having a long linear conjugated structure represented by the general formula (1), A polymer compound having a silyl group and a benzene derivative having a long linear conjugated structure represented by the above general formula (1) are combined with chloroplatinic acid, an alcohol solution of chloroplatinic acid, a complex of platinum and an olefin complex, and rhodium. It can be produced by performing the reaction in the presence of a rhodium-based catalyst such as a complex of carbonyl and carbonyl.

The liquid crystalline material according to the present invention is a benzene derivative having a long linear conjugated structure represented by the general formula (1), a composition containing the benzene derivative having the long linear conjugated structure, It is a material exhibiting a liquid crystallinity of a smectic phase as a liquid crystal phase composed of the polymer or a composition containing the polymer.

The composition containing the benzene derivative having a long linear conjugated structure represented by the general formula (1) comprises a benzene derivative having a long linear conjugated structure represented by the general formula (1). At least 30% by weight or more, preferably 50% by weight or more, more preferably 90% by weight or more, which is caused by a liquid crystal compound having a long linear conjugated structure represented by the general formula (1). It shows the liquid crystal state of the smectic phase.

Other components in the composition are components that adjust the phase transition temperature of a benzene derivative having a long linear conjugated structure represented by the general formula (1), and include, for example, other liquid crystal compounds, One or more compounds having both ends having an alkyl group or an alkoxy group at both ends having another long linear conjugate system can be used. The compound which is a group or an alkoxy group may or may not be a liquid crystal compound. These other components can be used alone or in combination of two or more. A composition containing a benzene derivative having a long linear conjugated structure represented by the general formula (1) can be prepared as follows. That is, after dissolving a benzene derivative having a long linear conjugated structure represented by the general formula (1) and a desired component described above in a solvent, the solvent is removed by heating, reducing pressure, or the like, or the general formula ( It can be prepared by mixing a benzene derivative having a long linear conjugated structure represented by the formula (1) and the above-mentioned components, and melting by heating, or performing sputtering, vacuum deposition, or the like.

Further, the composition containing the polymer contains the polymer at least 30% by weight or more, preferably 50% by weight or more, more preferably 80% by weight or more, and the general formula (1) This shows the liquid crystal state of the smectic phase caused by the liquid crystal compound of a benzene derivative having a long linear conjugated structure represented by the following formula.

Other components in such a composition are components that adjust the phase transition temperature of the polymer, and include, for example, other liquid crystal compounds, and alkyl groups or alkoxy groups at both ends having another long linear conjugated system. One or more compounds may be used, and a compound having a long linear conjugate system of other components and having an alkyl group or an alkoxy group at both ends is a liquid crystalline compound. It does not have to be. These other components can be used alone or in combination of two or more.

This polymer composition can be prepared as follows. That is, after dissolving the polymer and the desired component in a solvent, the solvent is removed by heating, depressurizing, or the like, or the polymer and the desired component are mixed and calo-heat-fused, or sputtering, vacuum It can be prepared by performing evaporation or the like.

The liquid crystalline material according to the present invention may be, for example, charge-transported by applying a voltage to the liquid crystalline material in a liquid crystal state or applying a voltage to the liquid crystalline material in a solid state generated by a phase transition of the liquid crystal state. Examples of charge transport materials that perform the following are photosensors, organic electroluminescent devices (EL devices), photoconductors, spatial modulation devices, thin film transistors, charge transport materials for electrophotographic photoreceptors, photolithography, and the sun. It can be used for batteries, nonlinear optical materials, organic semiconductor capacitors, and other sensors. Example

Hereinafter, the present invention will be described in detail with reference to Examples, but the present invention is not limited thereto.

①Preparation of benzaldehyde derivative as reaction raw material used in the first step

Synthesis Examples 1-1.10 Synthesis of 1-decene (Compound (27))

According to the following reaction formula (5), 10-promo-1-decene (compound (27) ·) was synthesized. Reaction (5)

CH ₂ = CH (CH ₂ ) ₈ OH + PBr ₃ > ■ CH ₂ = CH (CH ₂ ) ₈ Br

(25) (26) (27)

24.67 g (0.15 M) of 9-decene-1-ol (compound (25)) was dissolved in 180 ml of getyl ether, and the system was replaced with nitrogen and cooled in an ice bath. Then, at a liquid temperature of 5 t or less, 22.56 g (0.075 M) of phosphorus tribromide (compound (26)) was added dropwise. After the dropwise addition, the mixture was stirred at 15 ° C for 17 hours, cooled in an ice bath, and 95 ml of methanol was added dropwise at a liquid temperature of 5 ° C or less. After dropping, 190 g of an aqueous solution of sodium hydrogen carbonate (1M) was added dropwise at a liquid temperature of 5 ° C. or lower, stirring was stopped, and the mixture was separated. Next, the organic layer is concentrated, and the obtained concentrate is distilled (85 ° C, 1.8 Hg). 18.83 g (yield: 57.2%) of 10-promo 1-decene (I-dani-yado (27)), which is the target product Got.

_{· - NMR ((5 CDC1 3} ) 1.2 1.5 (m, 10H, - (CH 2) 5 -) 1.8 ~ 1.9 (m, 2H, - CH 2 2.0 2.1 (m, 2H, -CH 2 - 3.4 (t, 2H, -CH ₂ Br) 4.9

5.0 (m, 2H, CH ₂ =) 5.7 5.9 (m, 1H, = CH-)

Synthesis Example 1-2 Synthesis of 9-decenoxybenzyl alcohol (compound (29)) 9-decenoxybenzyl alcohol (compound (29)) was synthesized according to the following reaction formula (6). Reaction formula (6)

(29)

12.80 g (0.10 M) of 4-hydroxybenzyl alcohol (compound (8)) was dissolved in 190 ml of ethanol, sodium hydroxide 4.Og (0.10) was added, and the mixture was heated to 65 ° C.

After heating, 10-bromo-1-decene (Compound (28)) prepared in Synthesis Example 1-1

24.14 g (0.11) was added dropwise, and the mixture was aged at a liquid temperature of 76 ° C. for 6 hours. Then the salts were decanted off and the reaction was concentrated. After concentration, the mixture was diluted with 350 ml of getyl ether and washed twice with 100 ml of pure water. After washing with 7R, the organic layer was concentrated, and the obtained crude crystals were recrystallized twice with 25 ml of hexane. The crystals were washed again with hexane and dried, and 16.88 g of 9-decenoxybenzyl alcohol (compound (29)) (Yield 64.3) was obtained.

Identification data>

_{R (5 CDC1 3) 1.3 1.6} (m, 10H, - (CH 2) 5 -) 1 · 7 1.8 (m, 2H, - CH 2 - 2.0 2.1 (m, 2H, -CH 2 - 3.9 (t, 2H ,-CH ₂ 0-) 4 6 (d, 2H,-CH ₂ OH) 4.9 5.0 (m, 2H, CH ₂ 5.7 5.9 (m, 1H, = CH 6.8 6.9 (m, 2H,-OPh 7.2 7.3 ( m, 2H, -PhCH _2- )

-FAB -MASS (Xe): 263 (MH +)

Synthesis Example 1-3: Synthesis of 9-decenoxybenzylbutemide (compound (30)) According to the following reaction formula (7), 9-decenoxybenzylbutemide (compound (30)) was synthesized. Reaction formula (7)

PBr ₃

(29) (26)

(30) Synthesis Example 1 16.05 g (0.061 M) of 9-decenoxybenzyl alcohol (compound (29)) prepared in 1-2 was dissolved in 85 ml of getyl ether, and the solution was cooled to 0 ° C. After cooling, 6.76 g (0.022M) of phosphorus tribromide (compound (26)) was added dropwise at 5 ° C or less, and the mixture was aged at 5 ° C for 2 hours and at 15 for 1.5 hours. After aging, the solution was cooled to 5 ° C., and 38 ml of methanol was added dropwise at 5 below. After dropping, aqueous sodium hydrogen carbonate solution

73.4 g of (lM) was added dropwise at 10 ° C or lower, and the layers were separated. After liquid separation, the organic layer was concentrated by washing with 32 ml of pure water to obtain 18.19 g (yield 91.6%) of 9-decenoxybenzyl bromide (compound (30)).

^{• 1 HN R ((5,} CDC1 3); 1 · 3~1.5 (m, 10H, - (CH 2) 5 -), 1 · 7~1 · 8 (m, 2H, - CH 2 -), 2.0 ~2.1 (m, 2H, - CH 2 -), 3.9 (t, 2H, - CH 2 0-), 4.5 (s, 2H, -CH 2 Br), 4.9~5.0 (m, 2H, CH 2 =) , 5.7 to 5.9 (m, 1H, = CH-), 6.8 to 6.9 (m, 2H,-OPh-), 7.2 to 7.3 (m, 2H, -PhCH _2- )

-FAB-MASS (Xe): 325 (M +)

Synthesis Example 1-4; Synthesis of 9-decenoxybenzyltriphenylphosphonium bromide (Compound (32))

According to the following reaction formula (8), 9-decenoxybenzyltriphenylphosphonium bromide (compound (32)) was synthesized. Reaction formula (8)

P (Ph) ₃

(30) (31)

-9 » ₃

(32) 17.23 g (0.053 M) of 9-decenoxybenzyl bromide (Compound (30)) prepared in Synthesis Example 1-3, 13.92 g (0.053 M) of triphenylphosphine (Compound (31)), Cloguchi form 53 ml was charged, and the mixture was heated to a liquid temperature of 60 ° C. and aged 1.511. After aging, the reaction solution was concentrated to obtain crude crystals. After washing with getyl ether, filtration and drying, 9-decenoxybenzyltriphenylphosphonium bromide (compound (3

2)) 29.19 g (93.7% yield) was obtained.

Ran _{R (S, CDC1 3) H-} ; 1.3~1.5 (m, 10H, - (CH 2) 5 -), 1.7~1.8 (m, 2H, - CH 2 -), 2.0~2.1 (m, 2H, -CH _2- ), 3.8 (t, 2H,-CH ₂ 0-), 4.9 ~

5.0 (m, 2H, CH ₂ =), 5.2 (d, 2H, -CH ₂ P-), 5.7 ~ 5.9 (m, 1H, = CH-),

5.2 (d, 2H, - CH 2 P -), 6.6 (d, 2H, - OPh -), 7 · 0 (dd, 2H, - PhCH 2 -), 7.6~ 7.8 (m, 15H, (Ph) 3 )

• ³¹ P-MR ((5, CDCI3): 28. Oppm

-FAB -MASS (Xe): 507 (M-Br)

Synthesis Example 1-5 Synthesis of 9-decenoxystilbenaldehyde (compound (33)) According to the following reaction formula (9), 9-decenoxystilbenaldehyde (compound (3)

3)) was synthesized. Reaction formula (9)

(32) (14)

(33) 9 prepared in Synthesis Example 1-4

Phenylphosphonium bromide (compound (32)) 23.07 g (0.039 M), terephthalaldehyde (compound

(14)) 5.91 g was dissolved in 315 ml of ethanol, and the solution was cooled to 12 ° C. 25.64 g of ethanol solution of sodium methoxide (21 wt%, aldrich) was added dropwise at 0 ° C. or lower. Liquid temperature Ot: Aged 1.5ϋ at the following temperature, and aged at liquid temperature 10 15 ° C for 2 hours. After aging, 39 g of pure water was added dropwise, the precipitated crystals were filtered, and the crystals were washed with 50 ml of an aqueous solution of 60 ethanol and 30 ml of ethanol. After washing, drying was performed to obtain 7.12 g of a compound of formula (33) and a yield of 50.0.

^{• X H- R (6, CDC1} 3); 1.3 1.5 (m, 10H, - (CH 2) 5 -), 1 · 7 1.8 (m, 2H, - CH 2 -), 2.0 2.1 (m, 2H, -CH _2- ), 3.9 4.0 (m, 2H, -CH ₂ 0-), 4.9 ~

5.0 (m, 2H, CH ₂ =), 5.7 5.9 (m, 1H, = CH-), 6/5 7.9 (m, 10H, Ph,-CH = CH-)

• FAB -MASS (Xe): 363 (MH +)

Next, 14 ml of p-xylene and 8.2 mg of iodine were added to 4.34 g (0.012 M) of the obtained 9-decenoxystilbenaldehyde (compound (33)), and the mixture was heated to 140 and aged for 4 hours. After aging, the solution was cooled to room temperature, and the precipitated crystals were filtered and washed with 25 ml of ethanol. After washing, the crystals were dried and added with 88 ml of porphyrin and stirred at room temperature for 20 minutes. After stirring, the insolubles were removed by filtration, and the mother liquor was concentrated to give 2.35 g of the trans-form of 9-decenoxystilbenaldehyde (compound (33)). To obtain a yield ^54.1.

Identification data>

· -Y R ((5, CDCI3); 1.3 ~ 1.5 (m, 10H,-(CH ₂ ) _5- ), 1.7 ~ 1.8 (m

_{CH 2 -), 2.0~2.1 (m} , 2H, - CH- -), 3.9 (t, 2H, -CH 2 0-), 4.9~

5.0 (m, 2H, CH ₂ =), 5.7 to 5.9 (m, 1H, = CH-), 6.9 (d, 2H,-OPh-),

7.0 (lH, d, -CH = CH-), 7.2 (lH, d, -CH = CH-), 7.5 (d, 2H, Ph),

7.6 (d, 2H, Ph), 7.8 (d, 2H, Ph)

• FAB -MASS (Xe): 363 (MH +)

②Preparation of acid adduct of phosphonium salt to be used as reaction material in the first step

Synthetic Example 2-1 Synthesis of 3--yl (Compound (35))

According to the following reaction formula (10)

(Compound (35)) was synthesized.

MS equation (10)

(35) 21.75 g (0.17 M) of p-hydroxybenzyl alcohol (Compound (16)) and 6.88 g of sodium hydroxide are dissolved in 150.45 g of ethanol, and 22.75 g of 3-dimethylaminopropyl chloride (Compound (34)) is dissolved. It was dropped. After dropping, heat the calo so that the liquid temperature becomes 70, and ripen it for 5 hours. After aging, the salt is decanted off and the reaction mixture is concentrated. After concentration, add 173.81 g of dichloromethane and dissolve, and wash with 71.66 g of pure water. After liquid separation, the mixture was washed with 86.20 g of a 1% aqueous sodium oxide solution, and the organic layer was concentrated to give 3-dimethylaminopropoxybenzyl alcohol (compound (35)). 17.90 g and a yield of 50.3% were obtained.

- - image _{R ((5, CDC1 3)} ; 1.93 (dddd, 2H, -CH 2 -), 2.23 (s, 6H, - CH 3), 2.42 (dd, 2H, -NCH 2 -), 3.98 (dd _{, 2H, - CH 2 0-)} , 4.59 (s, 2H, -CH 2 OH), 6.89 (d, 2H, Ph), 7.27 (d, 2H, Ph)

• FAB- MASS (Xe): 210 (MH +)

Synthesis Example 2-2; Synthesis of 3-dimethylaminopropoxybenzyl chloride hydrochloride (Compound (37))

According to the following reaction formula (11)

Hydrochloride (Compound (37)) was synthesized. (Anti) S Take (11)

(37) Dilute 4.35 g of thionyl chloride (compound (36)) with 20.40 g of chloroform and cool at a liquid temperature of 5 so that the temperature becomes as follows. After cooling, while maintaining the liquid temperature at 10 or less, 19.59 g of a chloroform solution containing 8.37 g (0.040 M) of 3-dimethylaminopropoxybenzyl alcohol (compound (35)) prepared in Synthesis Example 2-1 was dissolved. Drip. After dropping, heat the solution to 45 ° C and ripen it for 4 hours. After aging, the reaction solution was concentrated and the resulting crude crystals were recrystallized from 26.36 g of acetone to give 3-dimethylamido.

5.95 g of ride hydrochloride (compound (37)) was obtained in a yield of 56.3¾.

■ H- Ran R ((5, CDCl,) ; 2.38~2.45 (m, 2H, - CH 2 -), 2.85 (s, 3H, -CH 3), 2.86 (s, 3H, -CH ₃ ), 3.24 (dd, 2H, -NCH _2- ), 410 (dd, 2H, -CH ₂ 0-), 4.56 (s, 2H, -CH ₂ C1), 6.82 to 6.87 (m, 2H, Pti), 7.26 to 7.34 (m, 2H, Ph)

• FAB-MASS (Xe): 228 (-Cl)

Synthesis Example 2-3: Synthesis of 3-dimethylaminopropoxybenzyl chloride hydrochloride (Compound (38))

According to the following reaction formula (12), 3-dimethylaminopropoxybenzyldiphenylphosphonium chloride hydrochloride (compound (38)) was synthesized. Reaction (12)

(37) (31)

(38) 5.81 g (0.022 M) of 3-dimethylaminopropoxybenzyl chloride hydrochloride (Compound (37)) and 5.77 g of triphenylphosphine (Compound (31)) prepared in Synthesis Example 2-2 were collected in The solution was dissolved at 33.14 g, and the solution was heated to 70 ° C. and aged for 4 hours. After aging, the mixture was cooled and the reaction solution was concentrated to obtain 11.97 g of 3-dimethylaminopropoxybenzyltriphenylphosphonium chloride hydrochloride (compound (38)) and a crude yield of 103.3%.

Identification data>

- - Ran R ((5, CDCI3); 2.22~2.31 (m, 2H, - CH 2 -), 2.91 (d, 6H, -CH 3), 3.30~3.41 (m, 2H, - NCH 2 -), 3.86 (dd, 2H, -CH ₂ 0-), 5.27 (s, 2H, -CH ₂ P), 6.56 (d, 2H, Ph), 6.94 (dd, 2H, Ph), 7.64 to 7.73 (m, 2H) , Ph), Ί

7.84 (m, 2H, Ph)

-FAB-MASS (Xe): 454 (-72) Example 1

Of Amines Derivatives (Compound (40))

An amine derivative (compound (40)) was synthesized according to the following reaction formula (13). Anti-J formula (13)

, 33) (38)

(40) Dissolve 2.67 g of 3-dimethylaminopropoxybenzyltriphenyl phosphonum chloride hydrochloride (compound (38)) prepared in Synthesis Example 2-3 in 42.05 g of chloroform and adjust the solution temperature to 5 ° C. Cooling. After cooling, 4.89 g of an ethanol solution of sodium ethoxide (compound (39)) (21 wt%, aldrich) was added dropwise, and then 9-decenoxystilbenaldehyde prepared in Synthesis Example 15 (compound (33) Drops 20.65 g of a form with a closed mouth in which 1.523 (0.00421 ^) of the trans-form of (1) was dissolved. After dropping, ripen at 15 ° C for 7 hours. After aging, the precipitated crystals were filtered, washed with pure water and ethanol, and dried to obtain 0.65 g of an amine derivative (compound (40)).

Then, the filtrate was concentrated, and 8.45 g of p-xylene was added to and dissolved in the obtained concentrate. 2.5 mg of iodine was added, and the mixture was heated under reflux at 150 for 4 hours. Thereafter, the reaction solution was cooled, and the precipitated crystals were filtered, washed with ethanol, and dried. After drying, 0.26 g of the amine derivative (compound (40)), the combined amount of the amine derivative (0.91 g) and the yield of the amine derivative (40.4%) was 40.4%. Compound (40)) Was obtained.

• - image _{R (6, CDC1 3);} 1.32~1.70 (m, 12H, - (CH,) 6 -), 1.78 (ddd, 2H, - CH 2 -), 1.92~2.07 (m, 4H, -CH _2- ), 2.29 (s, 6H, -CH ₃ ), 2.41 ~

2.61 (m, 2H, -NCH ₂ -)> 3.97 (dd, 2H, -CH ₂ 0-), 4.04 (dd, 2H, -CH ₂ 0-), 4.91 to 5.34 (m, 2H, CH ₂ =) , 5.74 to 5.88 (m, 2H, = CH-), 6.86 to 7.92 (m, 4H, Ph), 6.94 (d, 2H,-CH = CH-), 705 (d, 2H,-CH = CH) -), 7.40 to 7.45 (m, 8H, Ph),

• FAB-MASS (Xe): 538 (MH +)

Synthesis of benzene derivative (compound (42))

A benzene derivative (compound (42)) was synthesized according to the following reaction formula (14). Anti-IS Take (14) Er

The trans-isomer of the amine derivative (compound (40)) obtained above was charged with 0.74 g (1.37 mM) and 59.25 g of ethyl bromide (compound (41)), and heated to a bath temperature of 40 °. It is aged for 30 hours and the precipitated crystals are filtered off. The obtained crude crystals were washed with 6.88 g of acetone and dried, and then the benzene derivative (compound) was obtained in a yield of 0.56 g and a yield of 62.9%. A trans form of the product (42)) was obtained.

R ((5 DMSO 120 ° C) 1.27 1.50 (m, 13H,-(CH ₂ ) ₅ -,-CH ₃ 1.70 1.79 (m, 2H, -CH _2- ) l.S2 ~ 2.07 (m, 2H,- CH _2- ) 2.15 ~ 2.27

_{(m, 2H, -CH 2 -} ) 3.06 (s, 6H, -CH 3), 3 · 43 (ddd, 2H, - CH 2 -) 3 · 43

3.50 (m, 2H, -NCH ₂ -)> 4.01 (dd, 2H, -CH ₂ 0-) 4.13 (dd, 2H, -CH ₂ 0-) 4.91 5.20 (m, 2H, CH ₂ =) 5.74 5.88 ( m, 2H, = CH 6.91 6.99 (m, 4H, Ph) 7.02 (d, 2H, -CH = CH 7.04 (d, 2H, -CH = CH-) 7.14 (d, 2H,-CH = CH 7.15 (d , 2H,-CH = CH 7.47 7.54 (m, 8H, Ph)

-FAB -MASS (Xe): 567 (-Br)

• IR (KBr, cm-1) 3022 (aromatic C-H stretching vibration), 2925 2853 (aliphatic C-H stretching vibration), 1642 (C = C stretching vibration), 1602 ~ 1473 (C = C, C = N bone motion), 1249 (C-0-C anti-symmetric stretching vibration), 966 (-CC-out-of-plane bending vibration), 835 (aromatic C-H in-plane bending vibration)

Further, the obtained benzene derivative (compound (42)) was sandwiched between two glass substrates, heated to a temperature higher than the liquid crystal phase-isotropic liquid transition temperature, and the transmitted light was observed with a polarizing microscope. It was confirmed that the compound was a liquid crystalline compound having a smectic phase as a liquid crystal phase that took a vertical alignment with the substrate. Industrial applicability

As described above, the benzene derivative having a long linear conjugated structure represented by the general formula (1) of the present invention is a novel compound, and the benzene derivative having the long linear conjugated structure is a liquid crystal. A liquid crystal material containing a compound having a smectic phase as a phase and a benzene derivative having a long linear conjugated structure portion or a compound derived from the derivative may be, for example, a voltage applied to the liquid crystal material in a liquid crystal state. As a charge transporting material that transports charges by applying a voltage or applying a voltage in a solid state generated by a liquid crystal phase transition, for example, an optical sensor, an organic electroluminescence element (EL element) , Photoconductors, spatial modulation devices, thin film transistors, charge transport materials for electrophotographic photoreceptors, photolithography, solar cells, It is expected that IJ can be used for nonlinear optical materials, organic semiconductor capacitors, and other sensors.

Claims

The scope of the claims

1. The following general formula (1)

CH ₂ = CB- (2 no

(Wherein, R ⁵ is a hydrogen atom or a methyl group, B is an alkylene group, —co—0— (CH ₂ ) _N ,

— Indicates C ₆ H ₄ — CH ₂ — and one CO—. ) Represents a group having an unsaturated bond represented by R ² ,

R ³ and R ⁴ represent an alkyl group, A represents an alkylene group, and X represents a halogen atom. It is a benzene derivative with a long linear conjugated structure characterized by the formula 2. The following general formula (3)

(Wherein, R ¹ has the same meaning as described above.) And a benzaldehyde derivative represented by the following general formula (4):

HZ Z ㊀

(Wherein, R ² , R ³ and A have the same meanings as described above; R ⁶ , R ⁷ and R ^{8 each} represent a monovalent organic group, and Z represents a halogen atom.) Is reacted in the presence of a base to obtain the following general formula (5)

( Five )

(Wherein, the R \ R \ R ³ and A as defined above.) The first step of obtaining a Amin derivative represented by, then the Amin derivative with the following general formula (6)

R ⁴ -X (6)

Wherein R ⁴ and X have the same meanings as defined above, and a second step of reacting the compound with a halogenated compound represented by the following general formula (1):

(Wherein R \ R ² , R ³ , R ⁴ , A and X have the same meanings as described above.) A method for producing a benzene derivative having a long linear conjugated structure represented by the formula:

3. A liquid crystalline material comprising a benzene derivative having a long linear conjugated structure represented by the general formula (1) or a compound derived therefrom.