TW201221540A - Condensed aromatic compound, organic semiconductor material and organic transistor element - Google Patents

Abstract

An objective of this invention is to provide an organic compound having sufficiently small reallocation energy. For attaining this objective, this invention provide a condensed aromatic compound represented by the following formula (2), or a high-polymer compound having a divalent group obtained by removing two hydrogen atoms from the condensed aromatic compound represented by the following formula (2) as a repeated unit. The divalent group may constitute a part of a repeated unit of the high-polymer compound. (in this formula, ring A, ring B and ring C respectively independently represents an aromatic ring, X<SP>1</SP>, X<SP>2</SP>, X<SP>3</SP>, X<SP>4</SP>, X<SP>5</SP>, X<SP>6</SP> and X<SP>7</SP> respectively independently carbon atom or nitrogen atom, R<SP>2</SP> respectively independently represents hydrogen atom, alkyl group, alkoxy group, alkylthio group, aryl group, heteroaryl group, aryloxy group, arylthio group, alkenyl group, alkynyl group, amino group, silyl group, halogen atom, acyl group, acyloxy group, amide group, carboxyl group, nitro group or cyano group, two R<SP>2</SP> may be coupled to each other to form a ring structure.)

Description

201221540 VI. Description of the Invention: [Technical Field] The present invention relates to an aromatic compound and an organic transistor element of the same material. [Prior Art] A condensation semiconductor compound used for shrinking an organic semiconductor material as an organic semiconductor Materials 0 Organic electroluminescence (EL) devices Various organic thin film devices such as organic transistor components, solar cells, and photosensors have been studied in recent years. Among them, the properties of the organic thin film device depend on the characteristics of the organic semiconductor material used therein, and therefore it is preferable to improve the charge mobility of the organic semiconductor material in order to improve the characteristics of the organic thin film device. Non-Patent Document 1 discloses that one of the characteristics of the organic semiconductor material that determines the charge mobility is its reorientation energy, and the lower the reorient energy, the higher the charge mobility of the organic semiconductor material. Non-Patent Document 2 discloses that an organic transistor element produced by using poly(3-hexylthiophene-2,5-diyl) as an organic semiconductor material can have a high charge mobility and a switching ratio. It is disclosed in Non-Patent Document 3 that a film of poly(9,9-dioctylfluorene-2,7-diyl) can exhibit a higher charge mobility and a weaker electric field dependency. However, the organic compound used in the past as an organic semiconductor material, the reorientation energy is not sufficiently small. Therefore, if the organic compound having a small energy for reorientation is used as the organic semiconductor material, a higher charge mobility can be achieved. [Prior Art Document] 5 323560 201221540 Non-Patent Document Non-Patent Document 1: Chemical review, 2004, Vol. 104, P. 4971 to 5003 Non-Patent Document 2: Applied Physics Letters, 1996, Vol. 69, p. 4108 ～4110 Non-Patent Document 3: Applied Physics Letters, 1998, Vol. 73, p. 1565 to 1567 [Disclosure] The present invention has been made to solve the above problems. An organic compound with a small enough energy to direct. [Means for Solving the Problem] That is, the present invention provides a compound represented by the following formula (1),

Wherein E is independently, and represents a hydrogen atom, an alkyl group, an alkoxy group, a sulfur-containing group, an aryl group, a heteroaryl group, an aryloxy group, an arylthio group, a dilute group, a fast group, an amine group, and a dream group. A halogen atom, a fluorenyl group, a decyloxy group, a arylamino group, a fluorenyl group, a nitro group, a cyano group, a boronic acid residue, a boronic acid ester residue or a tin alkyl group. Q1 represents a divalent group obtained by removing two argon atoms from a compound represented by the following formula (2), 323560 (2) 201221540

B

In the formula, the A ring, the B ring, and the C ring are each independent, and represent an aromatic ring. Χ1, χ2, 乂3, ^]6, and 7 are each independently 'representing a carbon atom or a nitrogen atom. Dimensions 2 are each independently 'representing hydrogen atom, alkyl group, alkoxy group, sulfur-burning group, aryl group, heteroaryl group, aryloxy group, arylthio group, aryl group, alkynyl group, amine group, Shishiji, dentate Atom, sulfhydryl, decyloxy, decylamino, carboxy, nitro or cyanamide. Among them, two R2's can be bonded to each other to form a ring structure. } When q1 is a complex number, these may be the same or different. Q2 is a formula: 丨 令, Rla and Rit are each independently 'representing a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group or an aryl group. } When the group shown, the group of the formula _CEC_ or the number of aromatic groups of two valences are used, these may be the same or different. η represents an integer of 1 or more: ml represents an integer of 0 to 10. The snake represents an integer of 1〇. However, when n nails cannot all be h or more, n of ml may be the same or different. η m2, which may be the same or different. Meanwhile, the present invention also provides a composition, film or organic semiconductor material containing the aforementioned compound. Further, the present invention provides an organic thin film element or an organic transistor element comprising the above film as an organic semiconductor material. Here, the "organic semiconductor material" in the present invention means a material in which 323560 7 201221540 contains an organic compound which functions as a semiconductor. Among them, the organic compound which exhibits the action of the semiconductor itself is also included in the organic semiconductor material. The "organic thin film element" in the present invention means an element having a film containing an organic compound. Further, the term "organic transistor element" as used in the present invention means a transistor element having a film containing an organic compound. [Effects of the Invention] Since the reorientation energy of the compound of the present invention is small enough, it has great use in the organic semiconductor material as an organic thin film element. [Embodiment] [Embodiment of the Invention] Hereinafter, preferred embodiments of the present invention will be described in detail with reference to the drawings. Further, in the description of the drawings, the same elements are denoted by the same reference numerals, and the description will be omitted when they are repeated. &lt;Compound&gt; The compound of the present invention is a low molecular or high molecular condensed aromatic compound having a structure in which a pyrrole ring is condensed by an aromatic ring, and a nitrogen atom contained in the pyrrole ring is simultaneously contained in the other two A planar chemical structure in an aromatic ring. This planar chemical structure facilitates the reduction of compound reorientation energy. More specifically, the compound of the present invention is a condensed aromatic compound represented by the above formula (2) or a condensed aromatic compound represented by the formula (2), wherein a divalent group of two hydrogen atoms is removed as a repeating unit. Polymer compound. The above-mentioned divalent group may be one of the repeating units constituting the polymer compound 8 323560 201221540. That is, the compound of the present invention is as shown in the formula (1)

E Q1·

M2.

E (1) / / represents a hydrogen atom H alkoxy group, = a group 1 group, a heterofilament, a silk group, an arylthio group, a material, a fast group, a group, a silk, a functional atom, a fluorenyl 1 oxy group, Amine amino, a few groups, nitro, minus, meal county, Wei-based or tin-based. Wherein the "burning group" is any straight chain or branch, and may also be a ring-burning group. Hyun base contains the carbon number, - as usual! To 6Q, 1 to 2Q is better. The alkyl group is preferably a linear alkyl group or a branched alkyl group, and a linear alkyl group is more preferred. Specific examples of the alkyl group include, for example, a methyl group, an ethyl group, a n-propyl group, a n-butyl group, a n-butyl group, a n-decyl group, a straight-chain alkyl group such as an n-octadecyl group; a branched alkyl group such as a butyl group, a second butyl group, a tert-butyl group, a 2-ethylhexyl group, a 3,7-dioctyloctyl group; a cycloalkyl group such as a cyclohexyl group or an adamantyl group; The alkyl group may have a substituent, and examples of the substituent which the alkyl group may contain may be an alkoxy group, an aryl group, a heteroaryl group, a halogen atom or the like. Specific examples of the alkyl group having a substituent include a methoxyethyl group, a benzyl group, a trifluoromethyl group, and a perfluorohexyl group. The methoxy group may also have a carbon number of the substituent a' to remove the alkoxy group of the substituent, and is usually from 1 to 20. The alkoxy group can be any straight chain or branch, and the ring oxygen group can also be used. Specific examples of the alkoxy group include n-butoxy group, n-hexyloxy group, 2- 9 323560 201221540 ethylhexyloxy group, 3,7-dimethyloctyloxy group, n-dodecyloxy group and the like. Among the alkoxy groups, a linear alkoxy group such as n-butoxy group, n-hexyloxy group or n-dodecyloxy group is preferred. The alkylthio group may also have a substituent, and the carbon number of the alkylthio group of the substituent is removed, and is usually from 1 to 20. The alkylthio group may be any straight chain or branched, and the cycloalkylthio group may also be used. Specific examples of the alkylthio group include n-butylthio group, n-hexylthio group, 2-hexylthio group, 3,7-dimethyloctylthio group, n-dodecylthio group and the like. Among the alkylthio groups, a straight-chain alkylthio group such as n-butylthio group, n-hexylthio group or n-dodecylthio group is preferred. The aryl group is an atomic group in which one hydrogen atom directly bonded to an aromatic ring is removed from an aromatic hydrocarbon compound, and includes a benzene ring-containing group, a condensed ring-containing group, and a separate aromatic ring or a condensed ring. The basis of the direct bond. The aryl group has a carbon number ' generally from 6 to 60, more preferably from 6 to 20. Examples of the aryl group include a group, a benzyl group, a 1-4 group, a 2-nyl group, a 1-indenyl group, a 2-indenyl group, a 9-fluorenyl group, a 1-mercapto group, a 2-indenyl group, and a 4-fluorenyl group. , 2-diyl, 3-diyl, 4-diyl, 4-phenylphenyl, and the like. The aryl group may also contain a substituent. Examples of the substituent which may be contained in the aryl group include an alkyl group, an alkoxy group, a heteroaryl group, a halogen atom and the like. Examples of the aryl group having a substituent include 4-hexylphenyl, 3,5-dioxaoxyphenyl, pentafluorophenyl and the like. When the aryl group has a substituent, the substituent is preferably an alkyl group. The hydroxy group is an aromatic heterocyclic compound, and one atomic group which is directly bonded to the hydrogen atom of the aromatic ring, and includes: a ring containing a condensed ring, an independent heteroaromatic ring or a condensed ring of two or more. The basis of the direct bond. The number of carbons contained in the heteroaryl group 323560 10 201221540 is generally from 2 to 60, more preferably from 3 to 20. Examples of the heteroaryl group include a 2-furyl group, a 3-furyl group, a 2-thiophenyl group, a 3-thienyl group, a 2-dentyl group, a 3-fluorenyl group, a 2-glycol group, and a 2-sheet group. 2__saltyl, 2"-indenyl, yl, 4_«yl, 2-benzoyl, 2-benzothiophenyl, 2-thienothiophenyl, etc. Heteroaryl may also contain a substituent. Examples of the substituent contained in the heteroaryl group include, for example, an alkyl group, an alkoxy group, an aryl group, a dentate atom, etc. An example of a heteroaryl group having a substituent can be exemplified by 5-octyl group+ When the heteroaryl group has a substituent, the substituent is preferably an alkyl group. The aryloxy group may further have a substituent, and the carbon number of the aryloxy group of the substituent is removed. , and is generally 6 i 20. Examples of the aryloxy group may be exemplified by a phenoxy group, a buccaoxy group, a 2-naphthyloxy group, etc. The arylthio group may also have an arylthio group of a substituent 'alternate substituent. The carbon number is generally 6 to 20. Examples of the arylthio group include a phenylthio group, a fluorenyl-naphthylthio group, a 2-naphthylthio group, etc. The alkenyl group may further contain a substituent, and the substituent is removed. The carbon number of the base is generally 2 to 20. The example of the county is as follows: vinyl, bismuth, and the like. The alkynyl group may further have a substituent, and the carbon number of the alkynyl group which removes the substituent is usually from 2 to 20. Examples of the alkynyl group which may have a substituent include an ethynyl group, a b-alkynyl group, and a 2-benzene group. An ethynyl group, a triterpene ethynyl group, etc. The ruthenium group may further contain a substituent, and the carbon number of the amine group of the substituent is removed, and is generally from 40 to 40. Examples of the amine group which may have a substituent may be, for example, an amine. Base, methylamino, dimethylamino, diethylamino, diisopropylamine, dicyclohexylamino, pyrrolidinyl, piperidinyl, anilino, diphenylamino, anthracene-naphthyl, 2_ Naphthylamine 323560 11 201221540 base, β ratio β-fixed amine group, etc. Shi Xiji may also contain a substituent, and the carbon number of the Shishi unit of the substituent is removed, generally 0 to 60. It may contain a substituent; Examples of the base can be exemplified by: ♦ base,: 曱石夕基, 三乙石夕基, 三丙石夕基, 三isopropyl石夕基, 三丁丁矽基, triphenyl fluorenyl, three Examples of the halogen atom of the earth include a fluorine atom, a gas atom, a phosphorus atom, and an iodine atom. The brewing group may further contain a substituent to remove the phenyl fluorenyl group, the diphenyl fluorenyl group, and the bismuthene group. Replace The carbon number of the fluorenyl group is generally from 1 to 20. Examples of the fluorenyl group which may have a substituent include, for example, an ethyl group, a fluorenyl group, a butyl group, a trimethyl acetyl group, a benzoinyl group, and a third group. Fluorinyl group, pentafluorobenzyl group, etc. The oxime group may further contain a substituent, and the carbon number of the oxirane group of the substituent is removed, and is usually 2 to 20. Examples of the oxime group which may have a substituent may be used. For example, it may be exemplified by ethyl phenoxy, propenyloxy, butyl oxy, trimethyl ethoxycarbonyl, benzoyloxy, trifluoroacetoxy, pentafluorophenyloxy or the like. The amine group may also contain a substituent and an anthranyl group which may have a substituent, and examples thereof include a mercaptoamine group, an acetamino group, a propylamine group, a butylammonium group, a benzamidine group, Trifluoroacetamido, pentafluorophenylamine, dimethylamino, diethylamine, benzhydrylamine, and the like. The thiol group may also contain a substituent. Examples of the carboxyl group which may have a substituent include a mercapto group, a methoxycarbonyl group, an ethoxycarbonyl group, a phenoxycarbonyl group, a methylaminecarbonyl group, an ethylaminecarbonyl group, an anilinecarbonyl group and the like. The rotten acid residue is a group represented by -(Β)2. 12 323560 201221540 The borate residue is a group obtained by removing a hydroxyl group from a boronic acid diester, and examples thereof include a dialkyl ester residue, a diaryl ester residue, a di(aralkyl) ester residue, and the like. An example of a borate residue can be given by the following formula:

(wherein, Me represents a methyl group, and Et represents an ethyl group.) The group shown. The stannyl group may also have a substituent, and the carbon number of the tin alkyl group from which the substituent is removed is generally from 0 to 20. Examples of the tin alkyl group which may have a substituent include a trimethyltin group and a tributyltin group. From the viewpoint of the monomer for polymer compound production, E is preferably a halogen atom, a linoleic acid residue, a tartanic acid residue or a tin-burning group. In the formula (1), Q1 represents a divalent group obtained by removing two hydrogen atoms from the compound represented by the formula (2). 13 323560 (2) 8 201221540

In the formula (2), the A ring, the B ring and the C ring are each independently and represent an aromatic ring. X 乂, 义,义, ; (, ) (6 and 疒 are independent, meaning that the carbon atom or the nitrogen atom are independent of each other' represents hydrogen atom, 炫, methoxy, thiol, aryl, heteroaryl, aromatic Oxygen, arylthio, alkenyl, block, amine, shixi f, nansko, county, decyloxy, fluorene, silk, nitro or cyanide. The knot forms a cyclic structure. In the formula (2), the 'A ring, the B ring and the c ring are independent of each other, and represent an aromatic ring. Γ; the carbon number of the scented ring is preferably 2 to 6 Å, more preferably 2 to 22, and 3 to For example, the carbon number of the substituent is included. The copper pentene of the aromatic ring is produced by im, phenanthrene ring, copper tetraphenyl ring, yoke ring, substance, 嗟: Γ t ring, 曙 di-salt ring, 嗟 嗤 ring, (four) ring, Biting ring, trimorphine, ::: ring, biting s, ° than pyridine ring, and ring, mouth ring, light weight r * 4 %%, stupid ring, benzene ring, ring can also Containing an pheno (tetra) ring, a benzene (tetra) divalent, etc. In the aromatic formula (2), χΐ, γ2 ν3 carbon atoms or nitrogen atoms. χ1: x3, x:, χ6 and χ7 are each independently 'indicating at least 4 carbons, Among X4, χ5, χ6, and χ7, those in which atoms are destroyed are preferred. In the case of χ1, χ2, χ3, χ4, χ5, 323560 14 201221540 Χ6 and Χ7, it is preferred that at least (10) of the adjacent two are carbon atoms. In the formula (2), the anthracene ring is easily synthesized. The viewpoint is better for 6 members • benzene ring. When the anthracene ring is a benzene ring, the formula (2) is represented by the formula (3).

(3) In the case of f 3), the /A ring, the C ring, ^^ and ^ are each represented as a separate atom, meaning hydrogen atom, alkyl group, alkoxy group, alkyl group, aryl group, heteroaryl group. Alkyl, aryloxy, arylthio, alkenyl, alkynyl, amine = alkaloid, dentate atom, fluorenyl, alkoxy, amidino, silk, exact or cyano. The benzene ring is adjacent to the bond on the atom to form a ring structure. Phase-mounted H in 'R ^ 'alkyl] alkoxy, thiol, aryl, heteroaryloxy aryl, alkenyl, alkynyl, aminyl, fluorenyl, halogen::...醯* The definitions and specific examples of the oxy group, the decylamino group and the carboxyl group are as follows: the alkyl group, the alkoxy group, the alkylthio group, the aryl group, the heteroaryl group = the aryloxyaryl fluorenyl group, the alkenyl group The definitions of the block group, the amine group, the Shishiji, the dentate ortho acid group, the brewing oxy group, the guanamine group, and the thiol group are the same as the specific examples. In the formula (3), from the viewpoint of lowering the reorientation energy of the compound, it is preferable that the (4) ring, the ring or the ten ring is the core of the /pole and the C ring system. The plug ring of 323560 201221540 is better. Among them, from the viewpoint of easiness of synthesis, it is preferable that Q1 is a group represented by the formula (4a) or a group represented by the formula (4b).

In the formulae (4a) and (4b), R2 and R3 are the same as defined above. R4 is independent of each other, and represents a hydrogen atom, a deuterium group, an alkoxy group, a sulfur-containing group, an aryl group, a heteroaryl group, an aryloxy group, an arylthio group, a aryl group, a fast group, an amine group, a sulfhydryl group, and a sulfonium atom. , fluorenyl, decyloxy, decylamino, carboxy, nitro or cyano. R4 represents a decyl group, an alkoxy group, a thiol group, an aryl group, a heteroaryl group, an aryloxy group, an arylthio group, an alkenyl group, an alkynyl group, an amine group, a fluorenyl group, a halogen atom, a fluorenyl group, an anthracene group The definition, specific examples of the group, the mercapto group, and the carboxyl group are the alkyl group, alkoxy group, sulfur group, aryl group, heteroaryl group, aryloxy group, arylthio group, alkenyl group represented by the above E. The definitions of the alkynyl group, the amine group, the fluorenyl group, the _ atom, the fluorenyl group, the decyloxy group, the decylamino group, and the carboxyl group are the same as the specific examples. The example of Q1 can be exemplified below. 16 323560 201221540

17 323560 201221540

In the formula (1), each of Q2 is independent, and represents -CRla=CRlb---C tri-C- or 2-valent aromatic group. 1^ and 1^ are each independently a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group or a cyano group.

The definition of the alkyl group, the aryl group or the heteroaryl group represented by Rla &amp; Rlb is specifically the same as the definition and specific examples of the group, aryl or heteroaryl group represented by the above E. The divalent aromatic group is an atomic group obtained by removing two hydrogen atoms from the aromatic ring, and includes a group containing a condensed ring group, an independent aromatic ring or a condensed ring of two or more direct bonds. Examples of the divalent aromatic group include a stretching phenyl group, a naphthyldiyl group, a fluorenyldiyl group, a phenanthrenyl group, a condensed tetraphenyldiyl group, a dienyl group, a fused pentabenzenediyl group, a flower diyl group, and a fluorenyl group. , oxadiazolediyl, thiadiazolediyl, carbazolediyl, thiaphthyldiyl, porphinyldiyl, di-septyldiyl, p-synaptodiyl, hydrazone , 洛洛二基, 乙二基基, selenophene diyl, 吼 "dibasic, 哄 哄 diyl, pyrimidine diyl, tritonin diyl, benzothiophenediyl, benzopyrrolediyl, Benzofuran diyl, fluorene diyl, isoindole diyl, porphin and porphinyl diyl, benzothiadiazole diyl, benzodithiophenediyl and the like. The divalent aromatic group may further contain a substituent. Q2 is preferably a divalent aromatic group; a benzenediyl group which may have a substituent, a second group which may have a substituent, a thiophenediyl group which may have a substituent, and a porphin porphindiyl group which may have a substituent Further, the benzodioxin diyl group which may have a substituent is more preferable; and the group represented by the following formula is more preferable.

(wherein R is independently a hydrogen atom or an alkyl group.) In the formula (1), η represents an integer of 1 or more; ml represents an integer of 0 to 10; and m2 represents an integer of 0 to 10. Only n of the ml cannot be 0. When η is 2 or more, n of ml may be the same or different. η m2, can be the same or different from 19 323560 201221540. From the viewpoint of increasing the crystallinity of the compound represented by the formula (1) and improving the performance of the crystal element containing the compound represented by the formula (1), it is preferred that ml is 1 or m2. From the viewpoint of producing an excellent film of the compound represented by the formula (1), it is preferred that n is 3 or more. The viewpoint of easily forming a film by increasing the solubility of the compound represented by the formula (1) in a solvent is preferably η of 3 or more and 10,000 or less, and more preferably 3 or more and 5,000 or less. From the viewpoint of improving the crystallinity of the compound represented by the formula (1) and improving the performance of the crystal element including the compound represented by the formula G), it is preferred that η is one. Examples of the compound represented by the formula (1) include the following compounds.

20 323560 201221540

21 323560 201221540 &lt;Production method of compound&gt; The compound of the present invention can be synthesized by a generally known method when it is a low molecular compound. When the compound of the present invention is a polymer compound, the production method thereof is not particularly limited, and examples thereof include a method of performing a reductive coupling reaction with a Ni catalyst, a method using a Stille coupling reaction, a method using a Suzuk i coupling reaction, and the like. . The method of using the Stille coupling reaction and the Suzuki coupling reaction is preferred from the viewpoint that the ease of synthesis of the compound and the exchange of the copolymerization compound are easy. The method using the Suzuk i coupling reaction can be exemplified by having the formula: E!-T 丨-E2 (100) [wherein T1 represents Q1 or Q2. E1 and E2, each independently, represent a boronic acid residue or a boronic acid ester residue. One or more compounds shown in the formula: E3-T2-E4 (200) [wherein T2 represents Q2 when T1 is Q1; when T1 is Q2, it represents Q, E3, and E4, and each is independent, indicating A halogen atom or a reductive acid residue. A method for producing a step of reacting one or more compounds shown in the presence of a ruthenium ε catalyst and a base. In the formula (200), examples of the halogen atom represented by Ε3 and Ε4 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. The bromine atom and the iodine atom are preferred, and the bromine atom is more preferable because of the ease of synthesis of the polymer compound. In the formula (200), the sulfonic acid residue represented by Ε3 and Ε4 means the atomic group after the acidic hydrogen is removed by the sulfonic acid (-S〇3H), and specific examples thereof may be as follows: (Example: 曱 续 酸 酸 、 、 、 、 、 、 、 、 芳 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 22 An ester group (for example, a phenyl sulfonate group) and a trifluorosulfonate group. The method using the Stille coupling reaction can be exemplified by having the formula: E5-T3-E6 (300) [wherein, T3 represents Q1 or Q2. E5 and E6 are each independently and represent a trialkyltin alkyl group. One or more compounds shown in the formula: E7-T4-E8 (400) [wherein T4 represents Q2 when T3 is Q1; and Q1 when T3 is Q2. E7 and E8, each independently, represent a halogen atom. A method for producing a step of reacting one or more compounds shown in the presence of an Is catalyst. In the formula (300), examples of the trialkylstannyl group represented by E5 and E6 include a group represented by -S11R3 and the like. Wherein R represents an alkyl group. In the formula (400), examples of the halogen atom represented by E7 and E8 include a fluorine atom, a chlorine atom, a desert atom, and a broken atom. In terms of ease of synthesis of the polymer compound, a bromine atom or an iodine atom is preferred, and a bromine atom is more preferable. &lt;Composition&gt; The composition of the present invention is a species containing the compound of the present invention, and examples of the composition of the present invention include a composition containing two or more compounds represented by the formula (1) A composition containing a compound different from the compound represented by the formula (1) and one or more compounds represented by the formula (1). Examples of the compound different from the compound represented by the formula (1) include organic semiconductor materials other than the compound represented by the formula (1). The composition of the present invention may also be a liquid composition comprising a compound represented by the formula (1) of 23 323560 201221540 and a solvent. &lt;Film&gt; Next, a film comprising the compound of the formula (1) of the present invention will be described. Since the compound represented by the formula (1) is an organic compound, the film may be referred to as an "organic film" hereinafter. The preferred thickness of the organic film of the present invention varies depending on the element using the organic film, but is generally in the range of 1 nm to 100//m, preferably 2 nm to 100 nm, more preferably 5 nm to 500 nm, and 20 nm to 200 nm. Better. An organic thin film of such a thickness can form an organic thin film element having good charge transportability and sufficient strength. The organic film may contain one type of the compound represented by the above formula (1), or two or more types. When the organic film contains a component other than the compound represented by the above formula (1), the compound represented by the above formula (1) is preferably contained in an amount of 10% by mass or more, more preferably 30% by mass or more. When the content of the compound represented by the above formula (1) is less than 30% by mass, film formation becomes difficult, and thus it is difficult to produce a favorable charge mobility. Examples of the components other than the compound represented by the above formula (1) include organic semiconductor materials other than the compound represented by the above formula (1). The organic film of the present invention can be produced by any method. For example, the compound represented by the formula (1) can be dissolved in an organic solvent to form a solution, and then formed into a film. The organic solvent used in the production of the organic film of the present invention is preferably an organic solvent which can dissolve or disperse the components contained in the organic film well. If necessary, it may be heated to dissolve the component contained in the organic film 24 323560 201221540 in an organic solvent. Examples of organic solvents can be exemplified by saturated hydrocarbons such as octyl alcohol and cyclohexane; benzene, benzene, hexanol, gamma, chloroform, dioxin, tetrachlorination, and benzene; Saturated smoke; hydrocarbon; chlorobenzene, odorant, etc., halogenated saturated isopropanol, butyl SE筮, one phase of unsaturated hydrocarbon; ethanol, propanol, alcohol, third butanol, etc.; A = N, N, Nf, etc. _; N, N-dimethylformamidine, acetophenone, &quot; basal porphyrin oxides: A view of the dissolution of the ground, with unsaturated hydrocarbons, (four) ^ shell It is better to make the compound good, dichloroform or dichloro. The aforementioned coffee &quot; kinds of early alone can also be used in combination of two or more. Top coating: hair = = system: 'The substrate removal operation can be performed with the aforementioned solution or the like. Example of _== After coating, solution: plate coating method, gravure coating method, bar coating method, roll coating method, line method, /3/X coating method, nozzle coating method, screen printing The printing method, the flexographic printing capillary method, the nozzle ink printing method, the dispensing printing method, the nozzle coating method, and the coating operation can also be carried out under heating. In addition to being capable of being coated with a high concentration coating liquid to form a homogeneous crucible, a material which is difficult to apply at room temperature or the like can be used. At the same time, the organic film can be further imparted with a grinding method, a photo-alignment method, a sexual kicking method, a pull coating method, or the like to further enhance its charge transport. &lt;Organic film element 323560 25 201221540 The present invention Since the organic thin film contains a compound represented by the formula (1) having a low reorientation energy, it has excellent charge transport properties, and thus can be used for producing an organic thin film device such as an organic semiconductor element or an organic solar cell. The compound of the present invention and the composition containing the same are particularly useful as a charge transport material for an organic semiconductor device. The reorientation energy is equivalent to four times the energy barrier associated with the structural change of the hole movement. The smaller the amount, the more likely the high hole mobility. &lt;Organic Oxygen Element&gt; The organic transistor element includes a compound having the following composition: a source electrode and a drain electrode, and a current path between the electrodes includes a compound represented by the formula (1). An active layer, and a gate electrode that controls the amount of current through the current path. Examples of the organic transistor element having such a configuration include a field effect type organic transistor element and an electrostatic induction type organic transistor element. The field effect type organic transistor element generally has an organic transistor element having the following structure: a source electrode and a drain electrode, and an active layer containing the compound represented by the formula (1) as a current path between the electrodes, and control A gate electrode that passes a current amount of the current path, and an insulating layer disposed between the active layer and the gate electrode. In particular, an organic transistor element in which a source electrode and a drain electrode are provided to be connected to an active layer and a gate electrode is provided sandwiching an insulating layer connected to the active layer is preferable. The electrostatic induction type organic transistor device generally has an organic transistor element having a structure in which a source electrode and a drain electrode, an active layer including a compound represented by the formula (1), and a control of a current path between the electrodes; Passing 26 323560 201221540 passes the gate electrode of the current amount of the current path, and the gate electrode is disposed in the active layer. Among them, an organic transistor element in which a source electrode, a drain electrode, and the above-described gate electrode are disposed to be connected to the active layer is particularly preferable. The gate electrode may have a configuration in which a current path from the source electrode to the drain electrode can be formed, and a current amount flowing through the current path can be controlled by a voltage applied to the gate electrode, and examples thereof include a comb type. electrode. Fig. 1 is a schematic cross-sectional view showing an example of an organic transistor element (field effect type organic transistor element) of the present invention. The organic transistor element 100 shown in FIG. 1 includes a substrate 1, a source electrode 5 and a gate electrode 6 formed at a predetermined interval on the substrate 1, to cover the source electrode 5 and the drain electrode. 6 is an insulating layer formed on the substrate 1, an insulating layer 3 formed on the active layer 2, and insulated in such a manner as to cover the insulating layer 3 on the field between the source electrode 5 and the drain electrode 6. A gate electrode 4 is formed on layer 3. Fig. 2 is a schematic cross-sectional view showing another example of the organic transistor element (field effect type organic transistor element) of the present invention. The organic transistor element 110 shown in FIG. 2 includes a substrate 1 and a source electrode 5 formed on the substrate 1 and an active layer 2 and a source formed on the substrate 1 so as to cover the source electrode 5 The electrode electrode 5 holds the gate electrode 6 formed on the active layer 2 at predetermined intervals, the insulating layer 3 formed on the active layer 2 and the gate electrode 6, and covers between the source electrode 5 and the drain electrode 6. The gate electrode 4 is formed on the insulating layer 3 in the manner of the insulating layer 3 in the field. Fig. 3 is a schematic cross-sectional view showing another example of the organic transistor element (field effect type organic transistor element) of the present invention. As shown in Fig. 3, there is a 27 323 560 201221540 electromechanical crystal τ 120 120' which has a substrate 丨 and a gate electrode 4 formed on the substrate i to cover the interpole electrode 4 to form an insulating layer on the substrate. a source electrode 5 and a secret electrode 6 formed on the insulating layer 3 in a manner to cover a portion of the insulating layer 3 on which the gate electrode 4 is formed, and a source electrode 5 and a gate electrode The active layer 2 formed on the extrudate 3 in the manner of the portion of the electrode 6. Fig. 4 is a schematic cross-sectional view showing another example of the organic transistor element (field effect type organic transistor element) of the present invention. The organic transistor element 130' shown in FIG. 4 is provided with a substrate 1, a pole electrode 4 formed on the substrate 1, and a substrate formed on the substrate 1 so as to cover the gate electrode 4. 3 a source electrode 5 formed on the insulating layer 3 so as to cover a portion of the insulating layer 3 on which the gate electrode 4 is formed, and an active layer 2 formed on the insulating layer 3 so as to cover the source electrode portion The line electrode 6 is formed on the insulating layer 3 at a predetermined interval from the source electrode 5 in such a manner as to cover the portion of the impurity layer 2. Fig. 5 is a schematic cross-sectional view showing another example of the organic transistor element (70 pieces of the electrostatic induction type organic transistor) of the present invention. As shown in Fig. 5, an organic transistor element 140 is provided with a source electrode 5 formed on a substrate i, an active layer 2 formed on the source electrode 5, and a predetermined interval on the active crucible 2 The plurality of gate electrodes 4 formed and the active layer 2a formed on the active layer 2 so as to form the active layer 2 may be the same as or different from the material constituting the active layer 2) And the secret electrode 6 formed on the active layer 2a±. Fig. 6 is a schematic cross-sectional view showing another example of the organic transistor element of the present invention (field effect type organic 323560 28 201221540 • transistor element). The electromechanical crystal element 150 shown in Fig. 6 has a substrate 丨, an active layer 2 formed on the substrate 2、, a source electrode 5 and a drain formed on the active layer 2 at predetermined intervals. The electrode 6, the insulating layer 3 formed on the active layer 2 so as to cover a portion of the source electrode 5 and the drain electrode 6, and the insulating layer 3 each covering the source electrode 5 underneath are in the field of A gate electrode 4 formed on the insulating layer 3 in a manner in which a portion of the insulating layer 3 of the gate electrode 6 is formed is formed below. Fig. 7 is a schematic cross-sectional view showing another example of the organic transistor element (field effect type organic transistor element) of the present invention. The organic transistor element 160 shown in FIG. 7 includes a substrate 丨, a gate electrode 4 formed on the substrate 、, and a rim layer 3 formed on the substrate 覆盖 so as to cover the gate electrode 4, The active layer 2 formed to cover the field of the insulating layer 3 having the gate electrode 4 formed thereon, the source electrode 5 formed on the active layer 2 in such a manner as to cover a portion of the active layer 2, and the active layer 2 are covered The drain electrode 6 is formed on the active layer 2 in part and at a predetermined interval from the source electrode 5. Fig. 8 is a schematic cross-sectional view showing another example of the organic transistor element (field effect type organic electrode element) of the present invention. The organic electric sa body element 170' shown in Fig. 8 includes a gate electrode 4, an insulating layer 3 formed on the gate electrode 4, an active layer 2 formed on the insulating layer 3, and an active layer 2 The source electrode 5 and the electrodeless electrode 6 are formed while maintaining a predetermined interval. In this case, the gate electrode 4 also serves as the substrate 1. In the above organic transistor device of the present invention, the active layer 2 and/or 323560 29 201221540 active layer 2a is composed of a film containing the compound of the present invention, and a current between the source electrode 5 and the drain electrode 6 is formed. Path (channel). At the same time, the gate electrode 4 can control the amount of current passing through the current path (channel) via application of a voltage. Such a field effect type organic transistor element can be produced by a known method, for example, in the method described in Japanese Laid-Open Patent Publication No. Hei 5-100069. The electrostatic induction type organic transistor element can be produced by a known method as disclosed in Japanese Laid-Open Patent Publication No. 2004-006476. The material of the substrate 1 may be any material that does not interfere with the characteristics of the organic transistor element. A substrate, a glass substrate, a flexible film substrate, or a plastic substrate can be used. The material of the insulating layer 3 may be any material having high electrical insulating properties, and may be used: Si〇x, SiNx, Ta2〇5, polyimine, polyvinyl alcohol, polyvinylphenol, organic glass, photoresist, etc. However, from the viewpoint of low voltage, it is preferable to use a material having a high permittivity. When the active layer 2 is formed on the insulating layer 3, in order to improve the interface characteristics between the insulating layer 3 and the active layer 2, the surface of the insulating layer 3 may be treated with a surface treating agent such as a decane coupling agent to perform surface modification to form the active layer 2 . When there is an airport effect transistor, the charge of electrons and holes is generally near the interface between the insulating layer and the active layer. Therefore, the state of the interface has a large influence on the mobility of the transistor. Because of this, there has been a proposal to control the interface with a decane coupling agent in terms of improving the interface state to improve the characteristics (for example, Surface Chemistry, 2007, Vol. 28, No. 5, p. 242-248). 30 323560 201221540 Examples of decane coupling agents include alkyl chloro decanes (octyltrichloro decane (0TS), octadecyl trichloro decane (ODTS), phenethyl trioxane, etc.), A mercaptoamine compound such as an alkyl alkoxysilane, a fluoroalkylchlorodecane, a fluoroalkyl alkane oxide or a hexamethylene diazoxide (HMDS). The surface of the insulating layer may also be subjected to ozone uv treatment or 〇2 plasma treatment before being treated with the surface treatment agent. By such a treatment, the surface energy of the tantalum oxide film or the like used as the insulating layer can be controlled, and the orientation of the film constituting the active layer on the insulating layer can be improved by surface treatment, thereby obtaining high charge transportability ( Mobility). In the gate electrode 4' can also be used: gold, platinum, silver, copper, chromium, palladium, ing, turn, low-resistance Shixi polymer, low-resistance amorphous austenite compound metal, and tin oxide Indium oxide, indium, tin oxide (ITG) and other materials. These materials may be used alone or in combination of two or more. The gate electrode 4 can also be doped with a high concentration doped 11 substrate. High-density doped dream substrate, == as _remaining energy, and also (4) is the nature of the substrate. When the gate electrode 4 has the performance as a substrate, the i-based it is connected to the gate electrode 4 In the electromechanical crystal element, it is better to omit your radial electrode 5 and bungee ray, especially from gold m to low-resistance material (four) ... ... steel, chromium, palladium, aluminum, indium, in good use. These materials may be used alone or in combination of two or more. In the above organic transistor device, the source electrode 5 and the drain electrode 6, the 323560 31 201221540 and the active layer 2 may be interposed by other compounds. Layer. Examples of such a layer include a low molecular compound having electron transport property, a low molecular compound having hole transportability, a metal test, an alkaline earth metal, a rare earth metal, a complex of such a metal and an organic compound, Oxidizing sulfur compounds such as iodine, bromine, gas, gasification, sulphuric acid, sulfuric acid, sulfur dioxide, sulfate, etc., nitric oxide compounds such as nitric acid, nitrogen dioxide, nitrate, halogenated acid such as perchloric acid and hypochlorous acid A layer formed of an arylthiol compound such as a compound, an alkanethiol compound, an aryl thiol or a fluorinated alkyl aryl thiol. At the same time, it is preferable that the organic transistor element of the above type is a protective element after it is formed to form a protective film on the organic transistor element. Thus, the crystal element blocks the atmosphere, and thus the deterioration of the characteristics of the organic transistor element can be suppressed. Further, in the case of an organic electric element, the organic electroforming film is reduced in the forming step.卞 办 丌 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 忒 = It is preferred to form a protective film under exposure to the atmosphere (for example, under the machine). An organic electro-type transistor having a dimethyl structure of this type can be used as a main-field-effect organic electroluminescence display, a liquid crystal display device of the 阵 阵 阵 及 及 及 及 及 及 及 及 机场 机场 机场 机场 机场 机场The active compound having the above-mentioned actual compound and having the modified-two-shot active layer has the active layer of the rim of the present invention, so that the field effect mobility of the 323560 32 201221540 can be improved. Therefore, it is possible to manufacture a display or the like having a sufficient reaction speed. EXAMPLES Hereinafter, the present invention will be described in more detail, but the present invention is not limited thereto. (NMR analysis) The measurement of NMR was carried out by dissolving the compound in deuterated chloroform in a 匪r apparatus (manufactured by Varian Co., Ltd., INOVA300 type). (Weight average molecular weight) The weight average molecular weight was determined by colloidal filtration chromatography (Gpc, manufactured by Shimadzu Corporation, trade name: LC-lOAvp). The polymer compound to be measured was first dissolved in tetrahydrofuran at a concentration of 0.5% by weight, and then injected into GPC at 5 Torr. The mobile phase of GPC was tetrahydrofuran and flowed at a flow rate of mL 6 mL/min. The column was connected in series with TSKgel Super HM-H (manufactured by Tosoh Corporation of Japan) and TSKgel Super H2000 (manufactured by Tosoh Corporation of Japan). The detector used a refractive index detector (manufactured by Sakamoto Shimadzu Corporation: RID-10A). Synthesis Example 1 (Synthesis of each N-(2,6-di-diphenyl) π ratio η)

First, 2,6-dibromoaniline 48 g (0.19 mol), 2, 5-decyloxytetrahydrocarbamate 28 g (0.2 mol) and acetic acid were added to the flask. The reaction 33 323560 201221540 solution was then heated to 120 ° C while being disturbed for 4 hours. Thereafter, the reaction solution was further concentrated, and the concentrated solution was dropped into a mixture of 500 mL of water and 500 mL of decyl alcohol to form a precipitate. The precipitate was filtered and dried to give N-(2,6-dibromophenyl). Bilo. The amount produced was 52 g and the yield was 91%. Α-ΝΜΚΟΟΟΜΗζ, CDCla) &lt;5 7. 65(d, 2H), 7. 15 (t, 1H), 6. 69 (m, 2H), 6. 39 (m, 2H) Synthesis Example 2 (N- (2,6-bis(3-nonyl)phenyl). Synthesis of bilo

First, the gas in the flask was replaced with nitrogen, and then the flask was added with b (2,6-di-diphenyl)'» than 嘻23 denier (78 〇1), and 3~° thiophene was acid 舀24舀 ( 19. 19 mol), decyltrimethylammonium chloride (trade name: Aliquat 336 (registered trademark), manufactured by Aldrich Co., Ltd.) 1.6 g, di- gas bis(triphenylphosphine), i·6 g (2.3 mmol) and Toluene 300 mL, and the reaction solution was refluxed. Further, 150 mL of a 2 mol/L sodium carbonate aqueous solution was added dropwise to the reaction solution. After the dropwise addition, the reaction solution was refluxed for another 8 hours. Thereafter, the aqueous layer of the reaction solution was removed and washed three times with water. The resulting benzene solution was further concentrated, and methanol was added dropwise to form a precipitate. After the precipitate was filtered and dried, it was made into (N-(2,6-bis(3-thienyl)phenylpyrrole. The yield was 20 g, and the yield was 84%. 34 323560 201221540 ^- NMRCSOOMHz^DCh) δ1 〇ttn .r 冲...&quot;川... , 2Η), 7.45", 1Η), 7.18 (m, 2H), 6.91 (m, 2H), 6. 72 (m 9u, p Example ( Synthesis of Compound 1) ^^ ,, , ' 2H)'6· 42(ro, 2H), 6.15(m, 2H)

The gas in the flask was firstly purged with nitrogen N-(2 6-bis(3-thiophene), then πτηη alumina was added to the flask. Pyrrole 3.k (9.8raraol), gasified iron (III) 13 g (78 mmol), nitromethyl ρ 1 Λ τ ^ . 1 〇 mL and diphenyl benzene 500 mL. Thereafter, the reaction &gt; the trough was again propagated to q (, 4 β) at a temperature (25 ° C). t A r 筏 mix for 3 hours. The reaction solution was washed with water for 3: a person, and then the xylene in the sputum broth was evaporated to prepare a solid. The m body was adsorbed to the (four) column and washed with n-hexane to recover the n-hexane solution. Thereafter, the evaporation was once burned to prepare Compound 1. The yield was 0.40 g, and the yield was 14%. j-NMRQOOMHz, CDC13) 5 7. 94(d,2H), 7.75(d,2H), 7.61 (t,1H), 7.44(d,2H), 7. 12(s,2H Synthesis Example 3 (Synthesis of N-(2,6-bis(3-thienyl)-4-dodecylphenyl) ° ratio) 35 323560 201221540 C12H25

A 9i2H25 MeO-^/^N^-OMe

NBS DMF nh2 nh2 b(〇h)2 0 PdCI2(PPh3)2 ?12H25 Aliquat 336 XX Νβ2〇〇3 / H2O ^ -^ A stupid sJ ύ is first added 4-dodecylaniline 31g in the burning pot ( 0. 12 mol), N,N-dimethylformamide 150 mL. The reaction solution was cooled to 〇 °c, and 100 mL of a N,N-dimercaptocaramine solution containing N-methyl sulphonimine 2. 6 mol/L was added dropwise while stirring. After the completion of the dropwise addition, the reaction was further stirred at room temperature (25 ° C) for 1 hour. Thereafter, the reaction solution was poured into 7 mL of water, and then 700 mL of a gas mixture was added thereto, and the organic layer was extracted. The organic layer was washed three times with water, and then the organic layer was concentrated to give 2,6-dibromo-4-dodecanilide. It was made in an amount of 45 g. Further, 45 g of 2,6-dibromo-4-dodecylaniline, 20 g (0.15 mol) of 2,5-dimethoxytetrahydrofuran, and 400 mL of acetic acid were placed in the flask. The reaction solution was further heated to 12 (TC, and stirred for 4 hours. Thereafter, the reaction solution was concentrated] and a concentrated reaction solution was added dropwise to a mixture of 300 mL of water and 200 mL of methanol to prepare a precipitate. After the precipitates were filtered and dried, N-(2,6-di-di-4-pyrylphenyl group ratio p was prepared. The amount of the precipitate was 42 g. 36 323560 201221540, the gas of the flask was nitrogen. After the substitution, N-(2,6-dibromo-4-dodecylphenyl)pyrrole 4〇g, 3-thiopheneboronic acid 23g (0·18 mol), gasified mercaptotrioctyl group were added to the flask. Ammonium (trade name: Aliquat 336 (registered trademark) 'Manufactured by Aldrich Co., Ltd.) 3. 〇g, dichlorobis(triphenylphosphine)palladium (PdCl2(PPh3)2)l. 〇g and toluene 3〇〇mL, and The reaction solution was refluxed, and 170 mL of a 2 mol/L sodium carbonate aqueous solution was added dropwise to the reaction solution. After the dropwise addition, the reaction solution was refluxed for 8 hours. Thereafter, the aqueous layer of the reaction solution was removed and washed twice with water. Then, the toluene in the toluene solution is evaporated to prepare a solid, and then the solid is adsorbed to the tannin extract in the tannin tube column, and refined by n-hexane. The n-hexane solution was recovered again, and then n-hexane was evaporated to obtain N-(2,6-bis(3-thienyl)-4-dodecylphenyl)phosphonium. The amount thereof was 32 g. The yield is 79%. W-NMRQOOMHz, CDC13) 5 7. 36(s, 2H), 7. 16 (m, 2H), 6. 90 (m, 2H), 6. 71 (m, 2H), 6 41(m,2H) ' 6· 12(m,2H), 2. 70 (t,2H),1·71(m,2H),1· 2-1· 4(m,18H),0· 88(t,3H) Example 2 (Synthesis of Compound 2)

After the gas in the flask was replaced with nitrogen, it was added to the flask.

N-(2,6-bis(3-thienyl)-4-dodecylphenyl)pyrrole 7. 6g (0· 016mol), iron chloride (iji) 2ig (〇· i3m〇l), steric Base carb i i mL 37 323560 201221540 and toluene 5 GGmL. The reaction solution was further incubated at room temperature (hunger) for 4 hours. Thereafter, the reaction solution was contracted, and 5 mL of water was injected. The chloroform was added to extract the gas-like solution of the organic layer, and the gas-like solution was washed with water for 2 - person. Thereafter, the gas in the gas imitation solution was evaporated to give a solid. Then, the solid is adsorbed to the Shiqi gum in the Shixi rubber pipe column, and refined by the hexaplox, and the normal hexane solution is recovered. After that, it evaporated into the courtyard. The solid formed therein was recrystallized by hot isopropanol to prepare Compound 2. 9%。 The yield was 2. 2g, the yield was 2.9%. H-NMR (300MHz, CDCh) 6 7. 65 to 7.70 (m, 4H), 7. 38 (m, 2H), 7. 02 (s, 2H), 2. 85 (t, 2H), 1 77(m, 2H), 1. ll. 4(m, 18H), 0.88(t, 3H) Example 3 (Synthesis of Compound 3)

0. 50 g (1.1 mmol) of the compound 2, 100 mL of a gas mixture was added to the flask, and the reaction solution was cooled to -78 ° C and stirred. Then, N-non-ammonium iodide 〇.48 g (2.1 mmol) was added to the reaction solution, and the mixture was stirred at -78 °C for 3 hours. Then, the temperature of the reaction solution was gradually lowered to room temperature (25 ° C). Thereafter, the reaction solution of the gas-like solution was washed twice with water (5 〇mL). The gas in the chloroform solution was evaporated to give a solid. Then, the 38 323560 201221540 was applied to the silicone rubber in the squeezing tube column, and refined by n-hexane purification, and the n-hexane solution was recovered. After evaporation of n-hexane. That is, Compound 3 was prepared. The yield was 0.20 g, and the yield was 26%. j-NMRQOOMHz, CDCh) 5 7·78(d, 2H), 7. 65(s, 2H), 7. 49 (d, 2H) ' 2. 86(t, 2H), 1. 77(m, 2H ), 1. 2-1. 3 (m, 18H), 0. 87 (t, 3H) Example 4 (Synthesis of Compound 4)

Eight n*, Ί夂·# mouth and TOU Dingdaokou/V rn J (〇15ΐΜ〇1) compound 3, 2, 2,-bipyridyl 0.059g should be Pang JT1), tetrahydrogenethane 7mL 'and room Disturbance at temperature (25 ° C).言之紫飞i plus human double (1,4~cyclooctadiene) recorded (Q)G· 1Gg (G· 38mmo1 with chlorobenzene as a display (four)· = ^ dissolved, benzene solution re-passed) benzene solution concentrated And refining is carried out by dropping 3 columns. The compound 4 after purification is prepared. The compound 4* can be made into 1.3×l〇3. The weight average molecular weight of the fluorene ethylene is 323560 39 201221540 (Compound 5 Synthesis)

Compound 3 PdCI2(dppf) NaOH aq.

9-BBN

THF After the gas in the flask was replaced with nitrogen, 1-dodecene was added to the flask. 21 g (1.2 mmol), 0. 5M 9-borobicyclo[3.3.1]decane The solution of the tetrahydrofuran solution was 2.5 mL, and the reaction solution was stirred at room temperature (25 ° C. for 10 hours. Then, the reaction solution was further added with 〇. 6 〇g (〇. 83 mmol) of the compound 3. Next, two were added. Chloro[1,丨,-bis(diphenylphosphino)ferrocene] (PdCl2(dppf)) 6.8 mg. After the reaction solution was refluxed, a 5 M aqueous sodium hydroxide solution was added thereto, 66 mL. The reaction solution was further refluxed for 10 hours, and then the reaction solution was poured into water, and toluene was added, and then the benzene layer was extracted. After that, the benzene solution was washed twice with water, and the ruthenium solution was evaporated. 'A solid is formed. The solid is then adsorbed to the tannin extract in the column of the rubber hose and rinsed with n-hexane to recover the n-hexane solution. Thereafter, the n-hexane is evaporated to prepare the compound 25. The amount is 0. 20g, the yield is 30%. - W-NMROOOMHz, CDCh) &lt;5 7. 72(d, 2H), 7. 66(d, 2H), 7. 〇5(s, 2H) 2. 85 (m, 6H), 1·80 (m, 6H), 1. 2 to 1.5 (m, 54H), 〇. 95 40 323560 201221540 (m, 9H) * Example 6 • (Compound 6 Synthesis)

After the gas in the flask was replaced with nitrogen, 0. 20 g (0.25 mmol) of compound 5 and chlorobenzene 50 mL were added to the flask. Further, gasification iron (111) 0.4 (^(2.5111111〇1) was added to the reaction liquid, and then reacted at 120 ° (: 6 hours). Thereafter, the reaction solution was washed twice with water, and The chlorobenzene solution is purified through a ruthenium tube column, and the chlorobenzene solution is further concentrated and dropped into decyl alcohol. The precipitate is filtered to obtain a compound 6. The amount of the compound 6 is 44 mg. The weight average molecular weight of ethylene was 4.4 x 103. Example 7 (Evaluation of the manufacture of the organic transistor element 1 and evaluation of its characteristics) A solution containing the compound 4 containing a charge transporting compound was prepared to have a structure as shown in Fig. 8. The organic transistor element 1. First, a surface thermal oxidation operation is performed by doping a η-type ruthenium substrate with a high concentration as a gate electrode to form a tantalum oxide film of 200 nm. A thermal oxide film is formed by this operation (below) The substrate, also known as the thermal oxide film, was soaked in acetone for 10 minutes for ultrasonic cleaning, and then subjected to ozone-UV treatment for 30 minutes with an ozone-UV processor. Thereafter, the thermal oxide film was again placed in the atmosphere. 201221540 Methyl H (HMDS) tu read coating will be hot The film is subjected to a surface modification operation. Next, the compound 4 is dissolved in chloroform and passed through a filtration membrane to prepare a coating liquid. The concentration of the compound 4 in the coating liquid is 〇·5% by weight. The coating liquid is applied by spin coating on the oxide film which has been subjected to the surface modification operation described above to form an organic film containing the compound 4. Thereafter, the film is vaporized by a vacuum method using a metal cover. Forging molybdenum oxide (Μο〇3) to form a source electrode and a drain electrode to form an organic transistor element 1. Then, the gate voltage Vg and the source/no-pole voltage Vsd of the organic transistor element i are made. Under the change, the crystal characteristics were measured. The mobility was 9xl〇-6cra2/Vs. Synthesis Example 4 (synthesis of poly(9,9,-dioctyl-2,7-diyl))

CeHi7 CeH17

Ni(cod)2 gr

THF After replacing the gas in the flask with nitrogen, 2,7-dibromo-9'9,-dioctyl 0.5〇2 (〇9111]111〇1), 2,2, in the flask was added to the flask. Pyridine was set to 0. 31 g (2. Gmmol) and tetrahydrocyanate was 5 Q mL. The reaction solution was scrambled and heated to 60 ° C' and then added to bis(cyclohexanediphenyl). 44 g (2 () mm 〇 1). Thereafter, it was allowed to react at 60 C for 1 minute. Further, methanol was added to the reaction solution to form a precipitate. Thereafter, the precipitate was dissolved in toluene and washed twice with water. Further, it was purified by using a toluene solution as a column (4) into a column of 323560 42 201221540. After that, the solution is concentrated, and the precipitate is precipitated into poly(9,9,~dioctyl) methanol. The weight average molecular weight of the -6-converted polystyrene is 7 to 2 groups. . The compound Dingli was 1. 9χΐ〇3 〇Comparative Example 1 (The manufacture of the organic transistor element 2 and the characteristics thereof were changed to the poly 2 evaluation except that the compound 4 was changed to the poly 2 evaluation), and the same operation as in Example 7 was carried out. After the first 2'7-two base), the electromechanical crystal element 2 is placed on the organic transistor element. When the voltage Vsd between the electrodes is changed, the voltage of the voltage and the source/tantalum crystal are measured, and the crystallinity is not shown. As a result, there is no calculation example 1. ° (Quantitative calculation of the reorient energy) The energy is calculated according to the formula (5) contained in Thej〇urnai〇f. [Math 1] L 朴二j(10) When the neutral state is stabilized, the state is given to the positive 5: the energy of the mouth] + [the stability of the cation free radical state = the energy of the compound when the u charge is zero ]—[The energy of the compound in the neutral state of the ampoule &amp; [the energy of the compound in the stable structure of the cationic radical state] (5) The compound of the present invention (such as the compound represented by the formula (6)), (9,9,-dialkyl group '2,7-diyl) (as shown in formula (7)), poly(3-throated sin% 2,5-yl) (as shown in formula (8) The compound is calculated by the density functional method 43 323560 201221540 (using the B3LYP density functional and the 6-31G* basis function) to calculate the reorient energy at equation (5). The calculation uses a quantum chemical calculation program Gaussian 09 Reision A 02 ° to calculate a compound having a degree of polymerization (tl) having a distance between the terminal carbon atoms of each compound in the neutral state of less than 30 A and closest to 30 A. And a reorientation energy of a compound having a degree of polymerization (t2) having a distance between the terminal carbon atoms in the neutral state of 30 A or more and a value closest to 30 A, and then obtaining the distance by the interpolation method The value of the compound at a terminal carbon atom in the neutral state at 30 A is compared and compared. The calculation results are shown in Table 1.

In the conjugated polymer, it is generally known that when the degree of polymerization is increased, the effective conjugate length at which the absorption wavelength hardly changes is known. Therefore, for the compound represented by the formula (6), the compound represented by the formula (7), and the compound represented by the formula (8), each of the polymerization degrees t having a distance between the terminal carbon atoms of 15 A or more is selected. 7 to 17, and then calculate the value of the redirect energy of each t. The relationship between the polymerization degree t and the weight 323560 201221540 directional energy is adjusted by the formula (9), and the reorientation energy (λ) of the compound represented by the formula (6) to the formula (8) when the degree of polymerization is infinite can be obtained. . [Math 2] [Redirect Energy] = λ + axexp (-bxt2 - ext) (9) In the formula (9), a, b, and c represent the fitting parameters. The value of the second power of the correlation function of the range of the precision density to be matched is 0.995 or more. The calculation results are shown in Table 1. [Table 1] The reorientation energy of the compound (the distance between the terminal carbon atoms in the stability structure of the t value and the neutral state in the parentheses) The compound t=tl compound t=t2 The compound in the neutral state The compound represented by the compound λ (6) of 30 A is 4.14 keal/mol (t=2, 20.373 A) 3.10 keal/mol (t=3 &gt; 31.300 A) 3.23 keal/mol 1.16 keal/mol (7) Compound 4.93 keal/mol (t=3,23.718 A) 4.02 keal/mol (t=4,32.125 A) 4.25 keal/mol 1.51 keal/mol (8) indicates that the compound is 7.40 keal/mol (t=8,29.460) A) 6.80 keal/mol (t=9,33.800 A) 7.33 keal/mol 2. 96 keal/mol From the results, it is known that the reorientation energy of the compound of the present invention is smaller than that of polyfluorene and poly&quot; . BRIEF DESCRIPTION OF THE DRAWINGS Fig. 1 is a schematic cross-sectional view showing an example of an organic transistor element of the present invention. Fig. 2 is a schematic cross-sectional view showing another example of the organic transistor element of the present invention. Fig. 3 is a cross-sectional view showing a mold of another example of the organic transistor element of the present invention, model 45 323560 201221540. Fig. 4 is a schematic cross-sectional view showing another example of the organic transistor element of the present invention. Fig. 5 is a schematic cross-sectional view showing another example of the organic transistor element of the present invention. Fig. 6 is a schematic cross-sectional view showing another example of the organic transistor element of the present invention. Fig. 7 is a schematic sectional view showing another example of the organic transistor element of the present invention. Fig. 8 is a schematic cross-sectional view showing another example of the organic transistor element of the present invention. [Main component symbol description] 1 substrate 2, 2a active layer 3 insulating layer 4 gate electrode 5 source electrode 6 drain electrode 100, 110, 120, 130, 140, 150, 160, 170 organic transistor component 46 323560

Claims (1)

201221540 VII. Patent application scope: - 1. A compound represented by the following formula (1), (1) [wherein 'E is independently' denotes a hydrogen atom, a thiol's alkoxy group, a sulfur-burning group, an aryl group, a heteroaryl group, an aryloxy group, an arylthio group, an alkenyl group, an alkynyl group, an amine group , fluorenyl, dentate atom, fluorenyl, decyloxy, decylamino, carboxyl, nitro, cyano, boronic acid residue, boronic acid ester residue or tin alkyl; Ql is represented by the following formula (2) The divalent group after removing two hydrogen atoms in the compound shown; when Q1 is plural, the same may be the same or different; q2 is of the formula: -CRla=CRlb- {wherein, RU and heart are independent, A group represented by a hydrogen atom, a pyridyl group, an aryl group, or a murine group, a formula '(4), a base or a divalent number: when several, these Q2s may be the same or different; an integer from η to ίο· The number, ml represents an integer from ° to 10; m2 represents an integer from 0 to 1U, but the η of η's ml can be phase two: 0; "2 or more different", ^ 不冋, n M2 can be the same or 323560 201221540 {wherein A ring, β ring and C ring are independent of each other, indicating an aromatic ring; χΐ, XXX, χ, x and X are each independently, meaning a carbon atom or an atom, and R2 is independent, meaning a hydrogen atom, an alkyl group. , alkoxy, alkylthio, aryl, heteroaryl, aryloxy, arylthio, alkenyl, alkynyl, amine, fluorenyl, imine, fluorenyl, decyloxy, decylamino , a carboxyl group, a nitro group or a cyano group; wherein two of R 2 may be bonded to each other to form a cyclic structure}. 2. The compound according to the invention of claim 3, wherein Q1 is a divalent group obtained by removing two hydrogen atoms from the compound represented by the following formula (3), = (3), A ring, C ring, χ2, χ6, r2, each means as described above, R is independent, meaning hydrogen atom, alkyl group, alkoxy group, thiol group, aryl group, miscellaneous Aryl, aryloxy, arylthio, alkenyl, block, amine, fragment, dentate atom, fluorenyl, decyloxy, decyl, ruthenium, nitro or subtractive; benzene ring phase The two R3 bonded to the adjacent carbon atom may be bonded to each other to form a cyclic structure]. 3. The compound of claim 2, wherein the A ring and the C ring are each independently an aromatic heterocyclic ring. 4. The compound of claim D, wherein the t'A ring and the c ring are each independently an porphin ring, a ring or a ring. 323560 2 201221540 5. The compound as described in the fourth application of the patent application, wherein the group represented by the following formula (4a) or (4b), R3 R3 [wherein R 2 and r 3 represent the same meaning as defined above; R 4 each independently represents a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, a heteroaryl group, an aryloxy group, an arylthio group, an alkenyl group. , alkynyl, amine, fluorenyl, halogen atom, fluorenyl, decyloxy, decylamino, carboxy, nitro or cyano]. 6. The compound according to any one of claims 1 to 5, wherein 'ml is 1, and m2 is hydrazine. 7. The compound of any one of clauses 6 to 6, wherein _' η is an integer from 3 to 1 〇 〇 〇 。. 8. The compound of any one of clauses 6 to 6, wherein η is 1. The compound according to any one of claims 1 to 8, wherein the oxime is independent, and represents a γ atom, a boronic acid residue, a boronic acid ester residue or a tin alkyl group. 10. A composition comprising a compound as described in any one of claims -9 to 9. The film of the invention is a compound according to any one of the items i to 9 of the patent. 323560 201221540 12. An organic semiconductor material containing a compound according to any one of claims 1 to 9. An organic thin film element comprising the film as described in claim 11 of the patent application form as an organic semiconductor material. An organic transistor element comprising the film according to claim 11 of the patent application as an organic semiconductor material. 4 323560