TW201217425A - Organic semiconductor compound - Google Patents

Abstract

The present invention provides a novel compound having a high electrical charge mobility. Specifically, provided is a compound containing a continuous unit configured from at least two successive structural units represented by the belowmentioned formula (1). (In the formula, Ar1 and Ar2 each independently is a bivalent aromatic group that may have a substituent group, at least one of Ar1 and Ar2 is a bivalent heterocyclic group that may have a substituent group, and Ar1 and Ar2 may be the same as or different from each other. Each G is a direct bond or a linking group, and each G may be the same as or different from the others. R1 and R2 each independently is a hydrogen atom or a monovalent hydrocarbon group having 1-20 carbon atoms and that may have a substituent group, and R1 and R2 may be the same as or different from each other.)

Description

201217425 VI. Description of the Invention: TECHNICAL FIELD The present invention relates to an organic semiconductor compound and an organic thin film containing the same. [Prior Art] In recent years, as an organic semiconductor material, a main chain type organic semiconductor compound typified by a main chain type polythiophene has been attracting attention. On the other hand, a side chain type organic semiconductor compound in which a plurality of unitary units as a side bond are stacked has a relatively good charge mobility (refer to Non-Patent Document 1). Q. Prior Art Non-Patent Document Non-Patent Document 1: P〇lymer j〇urnal (2〇1〇) 42, 1〇3123 SUMMARY OF THE INVENTION Problems to be Solved by the Invention An object of the present invention is to provide a novel side chain type compound having a higher charge mobility. Means for Solving the Problems According to the present invention, the following compounds and an organic film containing the same can be provided. • [1] A compound containing two or more consecutive units of structural units represented by the formula (1), I58119.doc 201217425 [I]

(1) (wherein, ^ and V are independently 2 which may have a substituent

At least one of Ar1 and Ar2, which is a divalent hetero group, and which may have a substituent

Ar2 may be the same or different from each other, "the base, Ar and each G are direct bonds or far α. v fly, , ° base, and each G can be the same

Different, J R1 and R2 are each independently a hydrogen atom or a monovalent hydrocarbon group having a carbon number of (10), and the R 丨 and R 2 may be the same or different from each other. [2] The compound of the above (1), wherein the compound contains a continuous unit of structural units represented by the above continuous formula (7), [Chem. 2]

(in the formula, 158119.doc 4. 201217425

Ar1 and Ar are each independently a divalent aromatic group which may have a substituent, and

At least one of Ar1 and Ar2 is a divalent heterocyclic group which may have a substituent, and a Ar2 may be the same or different, and each of R: and R2 is independently a hydrogen atom or the number of carbon atoms which may have a substituent is (IV). A monovalent hydrocarbon group, and R1 and R2 may be the same or different from each other. [3] The compound of (1) or [2], wherein the center thereof is a bivalent 5-membered ring heterocyclic group having a substituent. (4) The compound according to any one of (1) to [3], wherein the compound is a substituent which may have a substituent. [5] The compound of [4], wherein the compound contains a continuous form containing连续-1) The continuous unit of the structural unit represented, [Chemical 3]

(wherein R1, R2, R11 and R12 may each independently have a substituent, and R12, R2, R11 and R12 are each independently a hydrogen atom, and the number of carbon atoms is 1 to 2%, and Ri, r2, and Rn may be different. κ久汉, each independently a hydrogen atom or a beauty, 4 has a carbon number of the substituent R and 1^4 may be the same or different from each other) I581i9.doc 201217425 [6] Compounds such as [5], of which ru&amp And rm are each independently a monovalent hydrocarbon group which may have a substituent of a hydrogen atom, an anthracene heterocyclic group which may have a substituent, or a hydrocarbyloxy group which may have a substituent. [7] An organic film containing the compound according to any one of (1) to [6]. EFFECTS OF THE INVENTION The compound of the present invention has a higher charge mobility than the prior side chain type organic semiconductor compound. Therefore, it can be preferably used as a functional material constituting an organic thin film such as an organic thin film transistor element or an organic photoelectric conversion element, and electrical characteristics of an organic thin film transistor element, an organic photoelectric conversion element, and the like can be further improved. Further, since it has higher solubility in a solvent than the conventional main chain type organic semiconductor compound, it is advantageous in terms of a large area of the element, and can be preferably used as a coating method for carrying out a simple coating method. The material of the cloth liquid. [Embodiment] Hereinafter, the present invention will be described in detail. The present invention is not limited by the following description, and the elements of the present invention described below can be appropriately modified without departing from the spirit and scope of the invention. The compound of the present invention contains a contiguous unit comprising two or more consecutive structural units represented by the following formula (1). Here, "continuous" refers to a state in which structural units are directly bonded to each other and connected. 158119.doc 201217425 [Chemical 4]

(1) In the formula (1), hydrazine and hydrazine are each independently a divalent aromatic group which may have a substituent, and at least one of W and fluorene is a divalent heterocyclic group which may have a substituent, and P may be the same as each other Alternatively, each G may be a direct bond or a linker, and each G may be the same or different from each other. And the respective carbon atoms which may be a hydrogen atom or may have a substituent are a tetravalent hydrocarbon group, and r1 and R2 may be the same or different from each other. /乍 is a divalent aromatic group, and examples thereof include a divalent aromatic hydrocarbon group and a divalent heterocyclic group. Here, the divalent aromatic hydrocarbon group means a group in which two of the hydrogen atoms bonded to the ring of the aromatic tobacco compound are detached. The "bivalent heterocyclic group" means a group derived from two of the hydrogen atoms bonded to the ring of the heterocyclic compound. The carbon number of the divalent aromatic hydrocarbon group and the divalent heterocyclic group is usually from 6 to 60, preferably _, more preferably (d), further preferably (d), and particularly preferably six, and the carbon number here is not Contains the carbon number of the substituent. Specific examples of the aromatic hydrocarbon compound include an aromatic hydrocarbon compound selected from the group consisting of (A-1) to (A-19) and a compound aromatic compound selected from the group consisting of formula (4)) to formula (c. 158119.doc 201217425). Preferably, it is an aromatic smoky compound selected from the group consisting of formula (Al) to formula (a-15), an aromatic smoky compound selected from the group consisting of formula (C-1) and formula (C-2), more preferably selected from the formula (A). Further, the aromatic hydrocarbon compound of the formula (A_8) and the formula (A-13) is preferably an aromatic compound selected from the group consisting of the formula (A-1) to the formula (A-3) and the formula (A-13). The compound is preferably an aromatic hydrocarbon compound selected from the group consisting of the formula (A·1) to the formula (A-3). Specific examples of the heterocyclic compound are selected from the following formula (Α_2〇)~ a heterocyclic compound of Α_38), a heterocyclic compound selected from the group consisting of formula (Β-1)~((1·1〇) 弋(C 14) (C-24), preferably selected from the formula (8) 20) The heterocyclic compound of the formula (Α-38) and the formula (B-丨)~式(Β_1〇) is more preferably selected from the formula (Α-2〇)~式(Α·26), formula (Β -1) a heterocyclic compound of the formula (Β-4) and the formula (Β-8), further preferably selected from the formula (Α-20) to (式-23), (Β-1)~ a heterocyclic compound of the formula (Β-4) and the formula (Β-8), particularly preferably a heterocyclic compound selected from the formula (Β2) and the formula (Β-3), particularly preferably a heterocyclic compound of the formula: Further, a group derived from two of the hydrogen atoms bonded to the heterocyclic compound represented by the formula (Β-3) is referred to as thi〇phenylene. Base) (there is a case called thienylene) 1581I9.doc 201217425 [Chemical 5]

◎ CA-1)

^ 0000 (A — 5) (A-6)

(A--9) (A-10)

(A-11)

(A-12)

Ooooo οοοί (A -13) (A-14)

0 (A-20) (A — 2*0 (A — 22) <A-23) (A_24>

158119.doc 201217425 [Chem. 6]

(B-5)

V Ο (Β—9) 158119.doc ◎ ¢3 (Β-2) (Β-3) (Β-4) ψ Η ψ Η (8-6) Ο (Β—10) (Β-7) (8 -8) 201217425 [Chem. 7]

Όφ (C-1)

At least one of Ar1 and Ar2 is a divalent heterocyclic group which may have a substituent, and preferably 158119.doc -11 - 201217425 is a divalent heterocyclic group in which both Ar1 and Ar2 are a divalent heterocyclic group.

Ar1 and Ar2 may be the same or different from each other, and are preferably the same. Examples of the substituent which Ar1 and Ar2 may have include a dentate atom, a monovalent radical (that is, a hydrocarbyl group) which may have a substituent, a sulfhydryl group, a sulfhydryl group, a thiol group, and the like. a hydrocarbonthio group of a substituent, a niobiumthio group which may have a substituent, a nicotinyl group which may have a substituent, a mercapto group, a hydrocarbyl group which may be substituted, a carboxyl group, an aldehyde group, a hydrocarbon which may have a substituent Alkyloxycarbonyl group which may have a substituent, a hydrocarbon carbonyloxy group which may have a substituent, a cyano group, a nitro group, an amine group, a hydrocarbon monosubstituted amine group which may have a substituent, a hydrocarbon disubstituted group which may have a substituent An amine group, a phosphino group, a hydrocarbon monosubstituted phosphino group which may have a substituent, a hydrocarbon disubstituted phosphino group which may have a substituent, a group represented by the formula: _p(=〇)(〇h)2, an amine formazan group, a hydrocarbon monosubstituted amine fluorenyl group which may have a substituent, a hydrocarbon disubstituted amine fluorenyl group which may have a substituent, a group represented by the formula: -B(0H)2, a boronic acid ester residue, a sulfo group, or may have a hydrocarbon sulfo group of a substituent, a hydrocarbon sulfonyl group which may have a substituent, a monovalent heterocyclic group which may have a substituent, and a hydrocarbon group having two or more ether bonds a hydrocarbon group having two or more ester bonds, a hydrocarbon group having two or more indoleamine bonds, a group represented by the formula: _C02M, a group represented by the formula: -Ρ03Μ, a formula represented by the formula: _p〇2m, and a formula: -p The base represented by 〇3M2, the formula represented by -0M, the formula: the base represented by -SM, the base represented by the formula .-B(0M)2, the formula: the base represented by -SO3M, and the formula: - a group represented by S02M (M represents a metal cation or an ammonium cation which may have a substituent. The same applies hereinafter), a group represented by the formula: -NR3M', a group represented by the formula -BR3M', and a formula: -PR3M' The base represented by the formula: -SR2M· (wherein R represents a monovalent hydrocarbon group, M represents an anion 158119.doc •12-201217425 ion), and has a quaternized nitrogen atom in the heterocyclic ring. The monovalent heterocyclic group which may have a substituent, etc., preferably a side atom, a hydrocarbon group which may have a substituent, a hydroxyl group, a hydrocarbyl group which may have a substituent, a carboxyl group, a domain group which may have a substituent, a cyano group , an amine group, a monosubstituted amine group which may have a substituent, a hydrocarbon disubstituted amine group which may have a substituent, a sulfo group, and a pot which may have a substituent The heterocyclic group 'more preferably is a halogen atom, a hydrocarbon group which may have a substituent, a hydroxyl group, a hydrocarbyl group which may have a substituent, a carboxyl group, a cyano group, an amine group, and a monovalent heterocyclic group which may have a substituent, and further It is preferably a substituted alkyl group, a hydrocarbyloxy group which may have a substituent, and a valent heterocyclic group which may have a substituent, and particularly preferably a nicotinyl group which may have a substituent. The case where A〆 and A" have no substituent is preferably the same as or higher than the case of having a hydrocarbon group as a substituent. Examples of the south atom of the substituent (substituted atom) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Preferably, the fluorine atom, the gas atom, and the bromine atom are more preferably a gas atom or a bromine atom. The monovalent hydrocarbon group as a substituent may, for example, be a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, a decyl group, a dodecyl group or a decyl group. Pentaalkyl, octadecyl, behenyl or the like having an alkyl group having 1 to 50 carbon atoms; cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclodecyl, cyclododecyl, a norbornyl group having a carbon number of 3 to 5 Å, such as a norbornyl group or an adamantyl group; a vinyl group, a propenyl group, a 3-butenyl group, a 2-butenyl group, a nonenyl group, a 2-hexenyl group, and 2 a nonyl group, a 2-dodecenyl group or the like having a number of 2 to 5 Å; a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-methylphenyl group, a 3-nonylphenyl group, 4-methylphenyl, 4-ethylphenyl, 4-propylphenyl, 4-isopropylphenyl, I58119.doc -13- 201217425 4-butylphenyl, 4_t-butylphenyl , 4•hexylphenyl, 4—cyclohexylphenyl, 4-adamantylphenyl, 4-phenylphenyl, etc., an aryl group having a carbon number of 6 to 5 Å; phenylmethyl, 1-phenylene Base, 2_phenylethyl, 丨_phenyl_丨-propyl, phenyl phenyl 2-propyl, 2-phenyl-2-propyl, 3-phenyl-1-propyl, 4- Phenyl-1-butyl, 5-benzene An aralkyl group having a carbon number of 7 to 5 Å, such as a pentyl group, a 6-phenyl-indole-hexyl group, preferably an aryl group having a carbon number of 1 to 5 Å and a carbon number of 6 to 5 Å. More preferably, it is an alkyl group having a carbon number of 1 to 12 and an aryl group having a carbon number of 6 to 18, and particularly preferably an alkyl group having a carbon number of 1 to 6 and an aryl group having a carbon number of 6 to 12. With respect to the monovalent hydrocarbon group, at least one of the hydrogen atoms in the group (particularly, ~3 hydrogen atoms, particularly i or 2 hydrogen atoms) may be substituted with a substituent as an example of a substituent. The flavonoid atoms such as a fluorine atom, a gas atom, and a bromine atom are listed; the carbon number such as a methoxy group, an ethoxy group, or a propoxy group is a bu. Alkoxy group; alkoxycarbonyl; cyano group. The hydrocarbon group of the substituent, the hydrocarbon sulfur group, the hydrocarbon disulfide group, the nicotinyl group, the hydrocarbon group, the alkoxy group, and the hydrocarbon group portion of the hydrocarbon group are used. The price of the smoke base is $, and 1 is shown as an example. At least a part of the aliquot of the gas atom may be an example of the above-mentioned "i-valent smoky group II: the same substitution" as the substituent, and the same group may be mentioned. The hydrocarbon mono-substituted amino group of the substituent The hydrocarbon disubstituted amine group, the "substituted scale 2: disubstituted phosphino group, the hydrocarbon monosubstituted amine methyl sulfonyl group, and the fluorenyl group of the fluorinated disubstituted amine hydrazide" are described as fluorene (tetra) groups, and are as follows: The a" at least a part of the hydrogen atoms in the hydrocarbon group portion of the group is substituted in the same manner as in the case of the above two examples of the above-mentioned monovalent hydrocarbon group. As an example of the substituted anthracene, the same group may be mentioned. 158119.doc 14· 201217425 Examples of the boronic acid ester residue as a substituent The group selected from the following formulas is exemplified.

The monovalent heterocyclic group of the substituent removes residual atomic groups of i gas atoms from the heterocyclic compound. As an example of a heterocyclic compound, 吼 is mentioned. Ding, 1, 2... well, two, η 啡, ^ three,,. husband. a monocyclic heterocyclic compound such as a pyrrole, thiophene, pyrazole, imidazole, oxazole, thiazole, oxadiazole, thiadiazole or azadiazole; a heterocyclic ring constituting a monocyclic heterocyclic compound a condensed polycyclic heterocyclic compound obtained by condensing one or more; having a heterocyclic ring constituting a monocyclic heterocyclic compound by using a divalent group such as a fluorenylene group, an ethyl group or a benzyl group; or an aromatic ring A crosslinked polycyclic heterocyclic compound having a structure in which a heterocyclic ring constituting a monocyclic heterocyclic compound is crosslinked. The heterocyclic compound is preferably pyridine, hydrazine, 2_two tillage, two tillage, 1,4-two tillage, 1,3,5_three tillage, more preferably pyridine, U3, 5_three tillage. The hydrogen atom in the i-valent heterocyclic group may be substituted with a substituent, and examples of the substituent include a substituent related to the above-mentioned "valent hydrocarbon group". Examples of the hydrocarbon group having two or more scaly bonds as a substituent include a group represented by the following formula. [Chemistry 9]

—R-(OR')pH—R′-iOR'Jp-OH ~〇-(R'〇)pH -O'-iROJp-RH 158119.doc ·15· 201217425 wherein R' represents a substituent The divalent hydrocarbon group (that is, the hydrocarbyl pp is an integer of 2 or more. Each R' may be the same or different. Examples of the divalent hydrocarbon group represented by R include a methylene group, an ethyl group, and 1 , 2-extended propyl, 1,3-propanyl, 1,2-butyl, 1,3-butyl, 1,4-butyl, 1,5-amyl, 1,6 - a divalent saturated hydrocarbon group having a carbon number of 1 to 5 Å, such as a hexanyl group, a 1,9-extension fluorenyl group, a 112-extension 12-base group; a vinylidene group, a propylene group, a 3-butenyl group, and 2 a carbon number of 2 to 50 such as an extended alkenyl group and an extended ethynyl group such as a butenyl group, a 2-endopentenyl group, a 2-hexadecenyl group, a 2-extended alkenyl group, a 2-extended dodecenyl group, and the like. Valence-unsaturated hydrocarbon group; carbon number such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, fluorenyl, fluorenyl, fluorenyl, and adamantyl a 2 valence ring-shaped saturated hydrocarbon group of 3 to 5 fluorene; ^ a phenyl group, a 1,4-phenylene group, a stilbene group, a hexanyl group, a 2,6 extension group, a biphenyl _4,4,. The carbon number of the second base is 6, The aryl group or the like is preferably an ethyl group, and at least a part of the hydrogen atoms of the divalent hydrocarbon group may be substituted with a substituent, and examples of the substitution of the above-mentioned "valent smoky group" may be mentioned. Examples of the hydrocarbon group of the above ester bond include two substituents selected from the following formulas: [Chem. 10] 〇-r.~(cor.)ph

0 -(COR')p-H Ο -R'-

O

(〇Cf〇pH—(〇CR′) pH, where R and p have the same meaning as the above-mentioned human & the bivalent hydrocarbon group of R′ is as described above and illustrated. Examples of the hydrocarbon group having a substituent of 158119.doc • 16 - 201217425 having two or more indoleamine bonds as a substituent include a group selected from the group consisting of the following formulas.

(NCR()pH ~R, -'(CNRl)pH - (ΟΝΡ·)ρ-Η -R'-INCR-Jp-H - where 'R' and p have the same meaning as above. Here, R The divalent nicotine group represented by the above description and exemplified, R' may have a substituent. The metal cation represented by ruthenium is preferably a valence of 1 to 3, and examples thereof include Li, Na, ruthenium, and Cs. , Be, Mg, Ca, Ba, Ag, Al, Bi,

Ions of metals such as Cu, Fe, Ga, Mn, Pb, Sn, Ti, V, w, Y, Yb, Zn, and Zr. The ammonium cation represented by M may have a substituent. Examples of the substituent include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, and a third butyl group. 10 alkyl. Examples of the monovalent hydrocarbon group represented by R include an alkyl group, a cycloalkyl group, an aryl group, and an aralkyl group. Examples of the anion represented by Μ' include: 1?-, (:1-,; 61*-, 1-, OH., CIO·, C102-, Cl〇3·, C104·, SCN·, CN.,Ν03·, S042., HS〇4-, ρ〇43·, ΗΡ0 42_, Η2Ρ04-, bf4', ΡΙ?6-, CH3S〇3, CF3S〇3, four (.*»米β坐基a sulphonate anion, a benzoyl anion, a 2-methyl-8 hydroxyquinolinyl anion, a 2-phenyl hydroxyquinolinyl anion, etc. as a substituent having a tetra The arsenic of the nitrogen atom of the gradation is 158119.doc •17·201217425 The example of the ring group may be a group selected from the following formulas.

9 Ο RM RM· RM' ^ where R and M are as defined above. In the case where Ar1 and Ar2 have a plurality of substituents, a plurality of (usually two) substituents may be bonded to each other to form a divalent group to form a ring, and the number of atoms constituting the ring formed is preferably five. 1 ,, and preferably 5 to ～, especially preferably 6. In the case of the ring formed, the conjugation should be widely spread in the molecule, preferably in the presence of a π orbital, and it is preferred that the π orbital is more than two or more preferably forming an aromatic ring. Each G is a direct bond or a divalent linking group. Examples of the linking group include a divalent hydrocarbon group which may have a substituent, and a formula selected from the following formula (D_丨) to (D-7) The valence group "is preferably a direct bond, a divalent hydrocarbon group which may have a substituent, a formula (D), a formula (D6), and a formula (D_7), more preferably a direct bond, a divalent hydrocarbon group which may have a substituent, a group of the formula (1 > 1), the formula (D-2) and the formula (D-3), and further preferably a direct bond, a hetero substituent The divalent hydrocarbon group is particularly preferably a direct bond. [Chem. 13]

Φ-l) (D-2) (D-3) (D-4) (D-5) (Dg) p.7) 158119.doc -18 · 201217425 wherein Rd represents a hydrogen atom or a substituent, Substituents are as defined for the substituents which the ^ and Ar2 may have. Rd is preferably a valence saturated hydrocarbon group or a hydrogen atom having a carbon number of (d). Examples of the divalent hydrocarbon group which may have a substituent include a divalent group selected from the following formulae (E-1) to (E-5). [Chem. 14]

In the formula 2, a hydrogen atom or a substituent which is as shown as a substituent which may be possessed by ruthenium 2 is represented. It is preferably a monovalent saturated hydrocarbon group or a hydrogen atom having a carbon number of 1 to 20. Specific examples of the linking group G include a divalent group selected from the following formula (Fq) to formula (f. 32), and among these, since synthesis is easy, it is preferably a formula + (F-25) The basis of the formula, more preferably the formula (IM) ~ formula (F_14). 158119.doc -19- 201217425 [化15] -r Ψ Η CH3 (F-l) (F-2) P2H5 C2H5 (F-3) -Pr

n-Hex π-Oct n-CiaH25 SSS|vHex ^ivOct n-Ci2H25 T Ύ H5 H CHj H t-Bu (F-8) (F-9) (F-10) (F-ll) (F-4 (F-5) (F-6) t-Bu (F-7) t-Bu n-Oct n-CtjHjτ τ T n*Hex n-Pr H (F-12) (F-13) (F- 14)

n-Oct

«Μ

(F-21) (F-22) YN 〇C2H5 (F-26) (F-27) (F-28) (F-29) (F-30) Η H H3C CH3 (F-23) (F- 24) KH n-HexV( n-Oct (F-25) 0 n-Hex (F-32) (F-31) In the formula (Fl)~(F-32), n-Pr is propyl, n -Hex is a hexyl group, n-Oct is an octyl group, Ph is a phenyl group, and t-Bu is a third butyl group. When G is a direct bond, the compound of the present invention contains two or more consecutive contents. a contiguous unit of the structural unit represented by the formula (2). • 20· 158119.doc 201217425 [Chem. 16]

(2) In equation (2), Ar1, Ar2, ruler and! ^ is as defined in equation (1). In the structural unit of the formula (1) and the formula (2), ... and the rule 2 are a hydrogen atom or a monovalent hydrocarbon group having a carbon number of 1 to 2 Å which may have a substituent. Ri and R2 can be identical to each other. The monovalent smoke group is as shown in the substituents which Ar 1 and Ar 2 may have. R1 and R2 are preferably a monovalent saturated hydrocarbon group or a hydrogen atom having a carbon number, and more preferably a hydrogen atom. The compound of the present invention is preferably a continuous unit containing two or more structural units selected from the following formula (Kd) to formula (κ_12), and more preferably contains a compound selected from the formula (Κ-1) to (formula). Κ-4) and a continuous unit in which two or more structural units of the formula (Κ_7) to (Κ-10) are consecutively selected, and further preferably contain a selected from the group consisting of a formula (κ_1) and a formula (Κ-2). It is preferable that the structural unit of the formula (Κ-7) and the formula (Κ-8) has two or more consecutive units, and it is particularly preferable to contain a selected one of the formula (Κ), the formula (κ_7), and the formula (Κ-8). In the case of a continuous unit in which two or more structural units are continuous, it is particularly preferable to include a continuous unit including two or more consecutive structural units represented by the formula (Κ-1). 158119.doc 21 · 201217425 [Chem. 17]

CK-10)

R21 R2* (K-5)

In the corpse/τ inverse (κ·1)~(K-l2), 'R1 and R2 are as defined above (K-ι)~(K-12), and R", R12, R21&R22 are The hydrogen atom or the carbon group which may have a substituent is a 1- to 20-valent hydrocarbon group. Ru, R!2, R2!, and R22 may be the same or different from each other. The monovalent hydrocarbon group is preferably a monovalent saturated hydrocarbon group having a carbon number of 1, or a hydrogen atom, as the substituent which may be represented by Ari and Ar2, and more preferably a hydrogen atom. In the formula (κ-υ~ (κ-12), Ru, Rl4, Rl5 and the carbon number of the substituent are Buxin #d13, and the nf叮 number is 1 to 20. R 3 , R 14 , R 15 and R16 may be different from each other or different. The base having a carbon number of 1 to 20 for Ar1 is as "may be substituted". Rn, R] 4, Rl5 and r16 are more than J58JI9.doc -22 · 201217425 is preferably a hydrogen atom, or a group selected from a valent valent group which may have a substituent, a monovalent heterocyclic group which may have a substituent, and a hydrocarbyloxy group which may have a substituent, more preferably a hydrogen atom The number of carbon atoms having a substituent is a fluorene hydrocarbon group of the group 6, the carbon number which may have a substituent is a heterocyclic group, and the hydrocarbon group having a substituent having a carbon number of from 1 to 6 is preferably a hydrogen atom, a carbon number which may have a substituent, a monovalent heterocyclic group of 1 to 6, a hydrocarbon group having a carbon number of 丨~6, preferably a hydrogen atom, and a carbon which may have a substituent The hydrocarbon group having a number of 丨~6 is particularly preferably a hydrogen atom. The compound of the present invention contains a contiguous unit comprising two or more consecutive structural units represented by the formula (1). In other words, the compound of the present invention is a side chain type compound in which the compound _ comprises a continuous structure in which a complex number represented by the formula (1) is directly bonded to each other, and the continuous bond is formed: a side bond in the structural unit represented by the formula (1) G, Arl and Ar2 form a structure and a plurality of ring structures of adjacent side chains are stacked on each other. The ring structure of the (side chain) is stacked on each other, and refers to a ring close to a plurality of adjacent side chains. The plurality of ring structures are arranged such that the structures have mutually overlapping π orbitals. The shape of the moon is preferably three or more, more preferably four or more consecutive patterns (1). The structural unit represented by the present invention. In the compound of the present invention, the structural unit represented by the formula (1) is continuous and = the continuous structural unit of the structural unit represented by the formula (1) is bonded to each other. Any of the bond and tail-tail bonds, there is no special system, from the point of view of electrical characteristics, compared to the following head-tail bond 0 158119.doc -23- 201217425[化18]

(1-1) The compound of the present invention may have a plurality of structural units represented by the formula (1), and may not be a single species. In other words, when a plurality of structural units in which at least one of 'R1, R2, Ar1, At2, and G are different from each other in the structural unit represented by the formula (1) is connected to each other, 'including two or more consecutive In the continuous unit of the structural unit represented by the formula (1). As a method of confirming that the compound of the present invention contains a continuous unit containing two or more consecutive structural units represented by the formula (1), spectrometric measurement by W-NMR is exemplified. That is, it is only necessary to detect that the proton signal of Ar1 and/or ~ in the spectrum of the ?h_nmr shifts to the high magnetic field side as compared with the normal chemical shift. The displacement of the signal to the high magnetic field side is caused by the overlap of the π orbitals of the plurality of side keys adjacent to each other in the adjacent plurality of structural sheets A, and the square of the structural unit represented by the formula (1) When the structural unit of the formula (1) in the compound of the present invention which is different from the rule 2 is continuous, the carbon atom bonded to R1 and R2 becomes an asymmetric carbon atom, and it can be a structure. When the structural unit represented by the formula (1) is further continuous, ? is a more diverse type of continuous structure. In the compounds of the present invention, the structure is not limited. Further, in the case where the structural unit of the formula (1) is the same as the case of "158119.doc.24-201217425, the continuous structure of the structural unit represented by the formula (1) in the compound of the present invention is also similarly. The variety is diverse. In this case, there is no limit to the type of continuous structure. Among them, in the continuous structure, in order to express the sufficient overlap of the π orbitals, there are preferred types of continuous structures among the various continuous structures. The structural unit other than the structural unit represented by the formula in the structural unit of the compound of the present invention is not particularly limited, and if the structural unit represented by the formula (1) in the compound of the present invention is small, the side exists. The ratio in which the chains of π are overlapped with each other is reduced, and thus the conductivity is lowered. Therefore, the ratio of the structural unit of the formula (1) to the weight per unit weight of the compound of the present invention is preferably 6% by weight or more, more preferably 7% by weight or more, still more preferably 80% or more, and particularly preferably It is 9〇% or more. The structural unit other than the structural unit represented by the formula (1) in the structural unit of the compound of the present invention is preferably represented by the following formula (4): a unit and a structural unit represented by the following formula (6). More preferably: a structural unit represented. () 19 [Chem. 19]

(4) In the formula (4), Ar5 is a substituent which may have the same or different, and 158119.doc •25- 201217425 is equivalent. [Chem. 20]

In the formula (6), the number of carbon atoms in which R1 and R2 are a hydrogen atom or which may have a substituent may be the same or different. R21 and R25 are a group of 〜2〇, and may be the same as 1 to 20 of a monovalent hydrocarbon group, and R1 and R2 may each have a hydrogen atom or a carbon number which may have a substituent may be different.

The aromatic cigarette groups in the description of Ar2 are the same. 2 Aromatic group and 4 specific examples, the structural unit of the structural formula (Form 21) of the formula (1) to the formula (1) can be exemplified.

158119.doc -26- 201217425 In the structural unit of the formula (6), R21 and R25 are as shown in the substituents which Ar1 and Ar2 may have. Specific examples of the structural unit represented by the formula (6) include structural units of the following formulas (V-1) to (V-12). [化22]

158119.doc •27·201217425 The compound of the present invention is preferably a chain structure in which a main chain extends a long length from the viewpoint of ease of overlapping of π orbitals of adjacent side chains. That is, it is preferably a form generally called a polymer and an oligomer. In this case, the terminal group is bonded to the end of the main chain. Specific examples of the terminal group include a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a butyl group, and a phenyl group. The molecular weight of the compound of the present invention can be obtained by gel permeation chromatography (GPC, Gel Permeation Chromatography) in a number average molecular weight in terms of standard polystyrene. The value of the average molecular weight of the number of the compound of the present invention is preferably from 3 to 1,000,000, more preferably from 3004 to 10,000, still more preferably from 400 to 200,000, and particularly preferably from 4 to 10,000. 10,000, particularly preferably 400 to 4000. The compound of the present invention has a structure in which a plurality of main chains are bonded, and ring structures bonded to side chains of different main chains are cross-linked to each other. <Synthesis method> Examples of the method for synthesizing the compound of the present invention include a method of reacting a compound represented by the following formula (1-2). [Im. 23] I. ° ° (1-2) j (1-2), Arl, ΑΡϋ and G are as defined in formula (1). For the reaction conditions of the compound of the present invention using the compound represented by the formula (1-2) 158U9.doc • 28·201217425, the conditions for use in anionic polymerization, cationic polymerization or radical polymerization can be applied. . It is especially preferred to use it in anionic polymerization. Specific examples of the case of using anionic polymerization conditions include a compound reaction of an organic clock compound such as lithium (MeLi) or butyl lithium (n-BuLi) in a solvent such as tetrahydrofuran or dimethylformamide. The method. The present invention relates to an organic film containing the compound of the present invention. The compound of the present invention can function as any one of the electron-accepting β-electron supply compounds by selecting a side chain or a substituent, and thus can be preferably used as a charge injection for an organic semiconductor element such as a field effect transistor. A functional material of an organic film such as a layer, a charge transport layer, or an active layer. Here, as an example of an organic semiconductor 7G member to which the compound of the present invention can be preferably applied, a configuration of a field effect type organic thin tantalum transistor and a method for producing the same will be described. The field effect type organic thin film transistor is preferably a gate electrode including a source electrode and a drain electrode, an organic semiconductor layer which is a current path between the electrodes and containing the compound of the present invention, and a current amount for controlling a current path through the current path, And an insulating layer disposed between the organic semiconductor layer and the gate electrode. It is particularly preferable to provide a source electrode and a drain electrode in contact with the organic semiconductor layer containing the compound of the present invention, and further to form an interlayer electrode by holding an insulating layer in contact with the organic semiconductor layer. The field-effect type organic thin film transistor using the compound of the present invention can be produced, for example, by the previously known method of 158119.doc •29·201217425 as disclosed in Japanese Laid-Open Patent Publication No. Hei No. Hei 5-110069. According to the method, the field effect type transistor can be manufactured by forming a gate insulating film on a gate electrode including a terminal, forming a compound containing the present invention on the closed insulating film, and having an activation treatment An organic thin film having semiconductor characteristics, wherein the organic thin film having semiconductor characteristics is formed by activating the organic thin film while protecting the closed electrode, the terminal of the gate electrode is exposed, and a source electrode is formed on the organic thin film having semiconductor characteristics And the electrode of the drain. In the case of forming an organic film containing the compound of the present invention, any of the previously known formation methods can be selected as described above, and is preferably formed by a coating method using a coating liquid. As a method of forming by the coating method, a method of applying a coating liquid obtained by dispersing a compound of the present invention in a solvent or a dispersion medium, and a coating liquid formed on another support substrate are preferably used. Layer method, etc. Examples of the coating method include a spin coating method, a ring casting method, a micro gravure coating method, a gravure coating method, a bar coating method, a light coating method, and a bar coating method. , dipping coating method, spray coating method, screen printing method, soft board printing method, plate printing method, and inkjet printing method. In forming the organic thin film, an organic thin film is formed on the rubbed substrate by an appropriate solvent, an organic thin film is formed on the photoalignment film, or a solvent of the formed film is slowly evaporated, and formed at a high temperature. The film is subjected to a lamp annealing, stretching, application of a magnetic field or the like to increase the degree of the enthalpy of the enthalpy orbits in the adjacent plurality of side chains of the compound of the present invention contained in the organic film, that is, the degree of stacking, thereby obtaining better π·π interaction: The degree of stacking can be confirmed by using X-ray diffraction (Cai 158119.doc -30- 201217425 diffraction). In the continuous structure with increased stacking, the absolute value of the resonance integral between H0M0 (Highest Occupied Molecular Orbital) and/or LUMO (Lowest Unoccupied Molecular Orbital) becomes larger. Therefore, the carrier mobility can be made larger. EXAMPLES Hereinafter, the present invention will be described in more detail based on examples, but the present invention is not limited by the examples. <Synthesis Example 1 > Synthesis of Compound 1 Compound 1 was synthesized according to the following scheme. [Chem. 24] 1. n-BuLi 2. 3-thiophene furfural

3. /7-BuLi 4.12 5. Na2SQ3aq. Hlaq.

The atmosphere in a three-necked flask having a capacity of 500 mL was replaced with nitrogen (hereinafter, "the nitrogen substitution in the environment inside the flask" is sometimes referred to as "nitrogen replacement"). 3-desophenone (10.6 mL, 109 mmol) (manufactured by Aldrich) and Et2O (150 mL) were placed in a flask, cooled to -78 ° C, and then n-BuLi hexane solution (68 mL, 109 mmol). After stirring at -78 ° C for 3 hours, a solution of 3-° Cetric acid (9.6 mL, 1 09 mmol) (manufactured by Aldrich) in Et 2 O (150 mL) was added at -78 ° C. After stirring for 30 minutes, it was further stirred at room temperature for 30 minutes. The reaction mixture was cooled to -23 ° C, and 158119.doc -31 - 201217425 n-BuLi hexane solution (136 mL, 218 mmol) was added, and the mixture was stirred at - 23 ° C for 2 hours, and then searched at room temperature. After stirring for 1 hour, the reaction mixture was cooled to -23 C, and a solution of Ι2 (87·2 g, 343 mmol) (manufactured by Wako Pure Chemical Industries, Ltd.) dissolved in Et 2 〇 (600 mL) was added dropwise (about 30 minutes).授 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 30 The mixture was washed 7 times with water, dried with MgS 4, filtered, solvent distilled, and vacuum dried. The benzene-hexane mixed solution (volume ratio: 1/2) was washed once with 60 mL and washed with 30 mL for 3 times to obtain the compound 1 in a benzene-hexane-insoluble portion (3 0.09 g 'yield 62%). . On the other hand, the soluble fraction of benzene·hexane was purified by Shixi gum chromatography (CHfl2) to obtain Compound 1 (4.83 g, yield 9%). <Synthesis Example 2> Synthesis of Compound 2 Compound 2 was synthesized according to the following scheme. [Chem. 25]

Compound 1 (39.〇g, 87 mm〇l) and CH2C12 (900 mL) were placed in a 2-L flask of 2 L volume with nitrogen substitution, and a solution of chromic acid 0 was added to the solution (28.2 g). , 13 1 mmol) (manufactured by Aldrich). After dropping for 12 hours at room temperature, the dichloromethane was removed under reduced pressure until the amount of the solvent became half. Purification was carried out by means of Shixi gum chromatography (Ci^Cl2) to obtain Compound 158119.doc -32 - 201217425 2 (35.0 g, yield 90%). <Synthesis Example 3> Compound 3 was synthesized according to the following scheme. [Chem. 26]

Copper powder (15 〇g, 236 mmol) (manufactured by Aldrich) was placed in a 3-mL flask of 300 mL capacity, degassed and replaced with nitrogen, and compound 2 (3 5.0 g, 79 mmol) of ruthenium ruthenium was added. Aldehyde (200 mL) solution. It was heated by an oil bath at 150 ° C for 15 hours and cooled to room temperature. The transition reaction mixture was extracted with ether, washed with water, dried with MgS 4 and removed by vacuum. The solvent was removed and vacuum dried. Purification by gelatin chromatography (solvent: chloroform-benzene mixture (volume ratio: W1)) was carried out to obtain Compound 3 (11.8 g, yield 78%). <Synthesis Example 4> Synthesis of Compound 5 Compound 5 was synthesized according to the following scheme. [化27]

Add THF to a 500 mL 3-neck flask and place compound 3 (5 〇g, % mmol). Perform degassing and replace with nitrogen, 158119.doc -33· 201217425 (tetrahydrofuran, tetrahydrofuran) (250 mL) for dissolution. . After cooling to 〇 ° C, a 3.0 溴 solution of methylmagnesium bromide (manufactured by Aldrich) (13 mL, 39 mmol) was added and stirred for 2 hours. Water and 1 N hydrochloric acid 'extracted with ethyl acetate' were added to the reaction mixture, washed with water, dried with MgS 4 , and then removed by a transition to remove MgS04, and the solvent was removed by vacuum drying to obtain a compound. 5 (5.35 g, yield 99%). <Synthesis Example 6> Synthesis of Compound 6 Compound 6 was synthesized according to the following scheme. [化 28]

A solution of compound 5 and p-toluenesulfonic acid (p-TsOH) (137 mg, 0-72 mmol) in benzene (400 mL) was stirred at 70 ° C for 40 min. Cool with ice water, add water (about 20 mL), extract with hexane (400 mL), wash with water, dry with MgS〇4, and remove MgS〇4 by filtration. Vacuum drying was carried out. Compound 6 (683 mg, yield 50%) was obtained as a yellow solid by silica gel chromatography (solvent:hexane). <Examples 1 and 2> The compounds of Examples 1 and 2 of the present invention were obtained according to the following scheme. 158119.doc -34- 201217425 [Chem. 29]

1) MeLi 2) Etl

The THF solution of the compound 6 was placed in a dry nitrogen-substituted 25 mL ampoule tube, cooled to -78 ° C, and a 1.0 Torr MeLi diethyl ether solution was added as a starter to carry out a reaction for 24 hours. Ethyl iodide (EtI) (manufactured by Wako Pure Chemical Industries, Ltd.) was added as a terminator. The THF insoluble portion and the THF soluble portion were separated by centrifugation. The polymerization conditions and results are shown in Table 1. [Table 1] (Table 1) [6] 〇 [1] 〇 EtI Yield THF insoluble THF soluble fraction (M) (M) (mmol) (%) Part (%) Μη Mw/Mn Example 1 0.20 0.040 2.0 &gt;99 13 87 900 1.29 Example 2 0.20 0.10 2.5 &gt;99 〜0 &gt;99 520 1.28 In Table 1, [6] 〇 indicates the concentration of the compound 6 in the reaction solution at the start of the reaction, [1] 〇 represents The concentration of the initiator in the reaction solution at the start of the reaction, and EtI represents the amount of iodoethane of the terminator (the same is true in the following table). The yield was determined by 1H-NMR. Μη (number average molecular weight) and Mw (weight average molecular weight) are obtained by GPC in terms of polystyrene. In the measurement of TOF-MS (Time of Flight-Mass Spectrometry), the peak value of the molecular weight corresponding to the 2 to 18 polymer was confirmed in Example 1, and it was confirmed in Example 2 that the equivalent was obtained. The fraction of the 2 mer to 8 mer is 158119.doc -35- 201217425. &lt;Example 3&gt; The compound of Example 3 of the present invention was obtained according to the following scheme. [化30]

The cyclopentan [2,l-b;3,4-b']dithiophene and THF were placed in a dry, nitrogen-substituted ampere tube of a volume of 25 mL, and n-BuLi was added dropwise. After standing at room temperature for 10 minutes, the starting compound 7 was obtained. This was cooled to -78 ° C, and a solution of the compound 6 in THF was added dropwise, whereby the polymerization was started. After 24 hours, the polymerization was terminated by the addition of sterol hydrochloride. The polymerization conditions and results are summarized in Table 2. [Table 2] (Table 2) [6] 〇 (M) [1] 〇 (M) Yield (%) THF insoluble portion (%) THF soluble portion (%) Μη Mw/Mn Example 3 0.20 0.4 &gt 99 to 0 &gt; 99 390 1.28 The yield was determined by 1H-NMR. Μη (number average molecular weight) and Mw (weight average molecular weight) are obtained by GPC in terms of polystyrene. In the TOF-MS measurement, the peak value of the molecular weight corresponding to the 2 to 25 polymer was confirmed. (NMR spectrum) The compounds obtained in Examples 1 and 3 were fractionated by fractionation of 158,119.doc -36 to 201217425 by GPC, and ih_Nmr was measured. Synthesis of cyclopenta[2,l-b;3,4-b.]dithiophene Cyclopentadithiophene was synthesized according to the following scheme. [化31]

• 2 4 In a two-necked flask of 30 mL, compound 3 (5 〇〇 mg, 2.6 mmol) and diethylene glycol (1 〇 mL) (manufactured by Wako Pure Chemical Industries, Ltd.) were placed and degassed for nitrogen replacement. Add hydrazine monohydrate (1.3 mL, 26 mm 〇l) (manufactured by Wako Pure Chemical Industries, Ltd.). It was heated in an oil bath at 130 ° C for 2 hours and cooled to room temperature. Add potassium hydroxide, heat in an oil bath of 18 (rc for 2 hours, and cool to room temperature. Add water to the reaction mixture, extract with ether, wash with water, dry with MgS〇4, and filter by The MgS〇4 was removed, and the solvent was removed, and vacuum drying was carried out. Purification by using Shiqi gum chromatography (solvent: hexane) was carried out to obtain Compound 4 (33 mg, yield 71%). 1 and Fig. 2. Fig. 1 is a view showing the H-NMR spectrum of the compound of Example ,, and Fig. 2 is a view showing the iH-NMR spectrum of Example 3. In each of the figures, η represents the degree of polymerization. 2 is clear that the proton signal of the heterocyclic ring of the side chain shifts to a higher magnetic field side than the spectrum of the cyclopenta b1]dithiophene shown in the uppermost part of FIG. 2, which means that a plurality of heterocyclic rings are stacked to make π orbital It is also known that, in the compound of Example 3 in which the terminal group is a hydrogen atom, if the degree of polymerization is 4 or more, the signal of all protons of the side chain heterocyclic ring is shifted to the higher magnetic field side. Displacement, thus having a heterocyclic ring at both ends that is not flipped and all of the side chains The structure in which the rings are integrally stacked with each other. (Luminescence behavior) The luminescence behavior of the compound obtained by the same method as in Example 1 by ultraviolet irradiation was investigated. Ultraviolet light having a peak at a wavelength of 38 〇 nm was obtained. Spectrum of the wavelength region (electrochemical behavior) &lt;Example 4&gt; The cyclic voltammetry of the compound obtained in the same manner as in Example 1 was carried out. After the bubble, the nitrogen flow t' was carried out under the following measurement conditions. [Measurement conditions] Solvent: THF 'Sample concentration: 〇.〇1 μ (per monomer unit), supporting electrolyte: (n-Bu) 4NCl〇4 (TBAP)0.1 Μ Reference electrode: Ag/AgCl(sat.KCl), working electrode: Pt disk (area: about 0.001 cm2), opposite electrode: pt line scanning speed: 100 mVs-1 Although cyclic voltammetry shows 2 Oxidation wave, but no reduction wave was observed, and no oxidation wave was observed in the second scan. However, if the scanning range is narrowed to the vicinity of the second oxidation wave, the reduction wave which is considered to correspond to the second oxidation wave can be observed. If the scan is repeated A new redox wave was observed on the lower potential side of the original redox wave. A black film of 158119.doc -38 - 201217425 was produced on the working electrode after the measurement. The reason is that Oxidative coupling and cross-linking with each other (evaluation of conductivity) The heterocyclic ring of the side chain is coated with a compound of the fourth embodiment on a comb-shaped electrode having a width of 5 μm between the electrodes and doped with 5 〇. % or 1%% of the toluene is as warm as '' and applying a voltage of 80 V, then in a 5〇% doped sample / still 7 A current, flowing in a 100% doped sample Called 〇6^ current. (The compound of the present invention has a structure in which a plurality of heterocyclic rings of a side chain are stacked, and has a structure in which a terminal group is a heterocyclic ring in which a hydrogen atom is located at both ends, and is stacked, and thus has a side chain which is earlier than the above. The organic semiconductor compound has a higher charge mobility, and thus can be preferably used as a material for an organic thin film transistor element, an organic photoelectric conversion element, etc., and can further improve electrical characteristics of a thin film transistor element, an organic photoelectric conversion element, and the like. Further, since it has higher solubility in a solvent than the conventional main chain type organic semiconductor compound, it is advantageous in terms of a large area of the element, and can be preferably used as a coating method for carrying out a simple coating method. Further, if a strong electric field is applied to the compound of the present invention, it can be cross-linked to each other between molecules. Therefore, it can also be applied to patterning by using it. For example, an organic thin film transistor element using the compound of the present invention can be used. Used as a switching element. If an organic thin film transistor element using the compound of the present invention is formed by a coating method such as an inkjet method By combining electromechanical light-emitting elements, it is possible to produce a device having a large-area light-emitting area, such as a soft display, which is more excellent in electrical characteristics by a simpler method. 158119.doc -39- 201217425 [Simplified Schematic] FIG. Figure (1) of the iH-NMR spectrum Fig. 2 shows the diagram of the ^-NMR spectrum (2). 158119.doc 40-

Claims (1)

201217425 VII. Patent application scope·· A compound comprising a continuous unit of a structural unit [Chemical Formula 1] comprising two or more consecutive R2 represented by the formula (1) (Atoms T, VIII' and Ar2 are respectively independent. At least _^ may have a divalent aromatic group having a substituent, and she may be the same: no: a divalent heterocyclic ring having a substituent - each G is directly Bonding or linking group, and each G may be the same or different from each other. R and R are each independently a hydrogen atom or a monovalent hydrocarbon group having a carbon number of 20, and R1 and r2 may be the same or different. ). 2. The compound of claim 1, wherein the compound contains a contiguous unit comprising two or more consecutive structural units represented by the formula (2), 158119.doc 201217425 [Chemical 2] R2 (2) In the formula, Ar1 and Ar2 are each independently a divalent aromatic group which may have a substituent, and at least one of Ar1 and Ar2 is a divalent heterocyclic group which may have a substituent, and Afl and Ar2 may be the same as each other. R and R may be reduced to a hydrogen source + or a monovalent hydrocarbon group having a carbon number of 1 to 20 which may have a substituent, and Ri and R 2 may be the same or different from each other. A compound wherein Afl and Ar2 are each independently a divalent 5-membered ring heterocyclic group which may have a substituent. 4. The compound of claim 3, wherein the core 2 is independently a thienyl group which may have a substituent. 5. The compound of claim 4, wherein the compound contains a continuous unit of a structural unit represented by the formula (K-1) containing two or more consecutive achievements, [Chemical 3] (K-1) 158119.doc 201217425 T RI, R2, R &quot; 12 base disc and R are each independently a hydrogen atom or a monovalent hydrocarbon group which may have a substitution number of 1 to 20, and may be the same or different. ^, 妙, and R and R14 are each independently a hydrogen atom or a group of 1 to 20, and the carbon number R and the ruler of the Ri3j r14 octabase may be the same or different. And a compound according to claim 5, wherein R, 3 and r14 each independently have a substituent; a valent hydrocarbon group, which may have a substituent: a substituent, or a hydrocarbyloxy group which may have a substituent. Base 7. An organic film containing a compound as claimed. 158119.doc