TW201206943A - Polycyclic compound - Google Patents

Abstract

A polycyclic compound represented by formula (1) [wherein the ring structure C represents a benzene ring represented by formula (C1), a hetero[3,2-b]heteror ring represented by formula (C2), or a benzo[1,2-b:4,5-b']diheteror ring represented by formula (C3) (wherein P and Q independently represent a sulfur atom or the like); W, X, Y and Z independently represent a sulfur atom, N-(R15) or the like, wherein at least one residue selected from the group consisting of W, X, Y and Z represents N-(R15); the ring structures A and B independently represent an aromatic carbon ring or the like, wherein the ring structures A and B independently represent an aromatic hetero ring which may have a substituent when the ring structure C represents a benzene ring represented by formula (C1) and both X and Y represent N-(R15); and R15's independently represent an alkyl group or the like].

Description

201206943 VI. DESCRIPTION OF THE INVENTION: TECHNICAL FIELD OF THE INVENTION The present invention relates to polycyclic compounds. [Prior Art] The organic electro-crystal system is used as a component of an electronic newspaper, a large-screen flat panel display, or the like. Such an organic electromorphic system is composed of a member such as an organic semiconductor active layer, a substrate, an insulating layer, and an electrode. A compound which is known to impart an active layer to an organic semiconductor, such as the one described in 'J. Appl. Phys. 2002, 92, 5259', is a vacuum-evaporated film obtained for use in an organic semiconductor active layer. SUMMARY OF THE INVENTION The present invention provides, a polycyclic compound, which is of the formula (1)

4,5-b']diheterocyclic ring,

-5- 201206943 (In the formula, P and Q are independently a sulfur atom, an oxygen atom, a selenium atom or a ruthenium atom, and the benzene ring constituting the above ring may have a substituent) 'W, X, Y and Z are independently a sulfur atom and oxygen. Atom, selenium atom, germanium atom, S〇2, (rU^C-CR12), (R13)-Si-(R14) or N-(R15)' and selected from the group of W, X, Y and Z At least one of them is N-(R15), and the ring structure A and the ring structure B are independently an aromatic carbocyclic ring which may have a substituent or an aromatic heterocyclic ring which may have a substituent, and the ring structure C is a formula ( When the benzene ring represented by C1) and X and Y are N-(R15), the ring structure A and the ring structure B are independently an aromatic hetero ring which may have a substituent, and R11, R12, R13 and R14 are independently independent. a polycyclic compound represented by an alkyl group having 1 or more halogen atoms or a hydrogen atom, and R 15 is independently an alkyl group which may have one or more halogen atoms; [2] a polycyclic compound as described in [1], Wherein W, X, γ and z are independently a sulfur atom, an oxygen atom, a selenium atom or N-(R15), and at least one selected from the group consisting of W, X, γ and Z is N-(R15); [3] a polycyclic compound as described in [1] or [2], At least two selected from the group consisting of W, X, γ, and Z are N-(R15); [4] The polycyclic compound of any one of [1] to [3], wherein the ring The structure C is a hetero [3,2-b] heterocyclic ring represented by the formula (C2) or a benzoquinone [l,2-b: 4,5-b'] diheterocyclic ring represented by the formula (C3); The polycyclic compound according to [1], wherein the ring structure C is a benzene ring represented by (C1), and X and γ are independently n-(R15), and W and Z are independently a sulfur atom, an oxygen atom or selenium. The atomic ring structure A and the ring structure B are independently an aromatic heterocyclic ring which may have a substituent; 201206943 [6] The polycyclic compound according to [1], wherein the ring structure C is represented by the formula (C1) a benzene ring, and X and Y are independently a sulfur atom, an oxygen atom or a selenium atom, and W and Z are independently N-(R15); [7] A polycyclic ring as described in any one of [1] to [6] The compound, wherein the aromatic carbocyclic ring which may have a substituent is a benzene ring which may have a substituent or a naphthalene ring which may have a substituent, an aromatic heterocyclic ring which may have a substituent, and a thiophene ring which may have a substituent a benzo[b]thiophene ring which may have a substituent or a thieno[3] which may have a substituent , the 2-b] thiophene ring; [8] The polycyclic compound as described in [4] or [7], wherein the ring structure C is a thieno[b]thiophene ring, a benzo[1] group having a substituent , 2-b: 4,5-b'] dithiophene ring or benzo[l,2-b: 4,5-b']difuran ring which may have a substituent» [9] as [4], [ The polycyclic compound described in 7 or [8], wherein the ring structure C is a thieno[3,2-b]thiophene ring or an unsubstituted benzo[i,2-b: 4,5-b' a polycyclic compound as described in [4], [7], [8] or [9], wherein one of W and X is N-(R15), and the other is a sulfur atom. 'Oxygen atom or selenium atom, one of Y and Z is N-(R15), and the other is a sulfur atom, an oxygen atom or a selenium atom; [11] The polycyclic compound as described in [10], wherein X is N -(R15), W is a sulfur atom, Y is N-(R15), and z is a sulfur atom; [12] The polycyclic compound as described in [10], wherein w is N-(R15), and X is sulfur The atom, Z is N-(R15), and Y is a sulfur atom; [13] The polycyclic compound according to [5], wherein the ring structure A and the 201206943 ring structure B are independently a thiophene ring which may have a substituent; [14] as recorded in [5] or [13] a polycyclic compound wherein X and γ are the same N-(R15), and W and Z are a sulfur atom; [15] The polycyclic compound according to [6], wherein ring structure a and ring structure B are independently a benzene ring which may have a substituent, a naphthalene ring which may have a substituent or a thiophene ring which may have a substituent; [16] The polycyclic compound of [6] or [15], wherein ... and B are the same N-(R15), both X and Y are a sulfur atom or an oxygen atom; [17] a film which is a polycyclic compound as described in any one of [1] to [16]; [18] A film formed by the polycyclic compound as described in any one of [1] to [16]; [19] an organic transistor comprising the film according to [17]; [20] An organic transistor comprising the film according to [18]; [21] an organic semiconductor device comprising the organic transistor according to [19] or [20]; BEST MODE FOR CARRYING OUT THE INVENTION First, the polycyclic compound represented by the formula (1) of the present invention (hereinafter abbreviated as the compound (1)) will be described. The compound (1) is a compound formed of four 5-membered rings each containing W, X, γ, and Z, and a ring structure A, a ring structure B, and a ring structure C. Compound 201206943 (1) wherein W, X, Y and Z are independently a sulfur atom, an oxygen atom, a selenium atom, a germanium atom, S02, (RH)-C-(R12), (R13)-Si-(R14) or N. - (R15), and at least one selected from the group consisting of W, X, Y, and Z is N-(R15). R15 is an alkyl group which may have one or more halogen atoms, and specifically, for example, methyl, ethyl, η-propyl, isopropyl, η-butyl, s-butyl't-butyl, η-pentyl , neopentyl, η-hexyl, 2-ethylhexyl, cyclohexyl, n-heptyl, n-octyl, cyclooctyl, η-fluorenyl, η-fluorenyl, 2-hexylfluorenyl' η- ~|-^, η-dodecyl, η-tridecyl, η-tetradecyl, η-pentadecyl, η-hexadecyl, η-heptadecyl, η -octadecyl, η-nonadecyl, η-icosyl, η-icosyl, η-docosyl, η-tetracosyl, η-tetracosane Base, η-pentacosyl, η-hexadecyl, η-tetradecyl, n-dodecyl, η-tetradecyl ' η-tridecyl, etc. a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms and a group in which a part or all of hydrogen atoms of the above alkyl group are substituted by a halogen atom, preferably having a carbon number of 1 or more halogen atoms To 20 alkyl groups. W, X, Υ and Ζ are independently a sulfur atom, an oxygen atom, a selenium atom or Ν-(R15), and at least one selected from the group consisting of W, Υ and Ζ is preferably N-(R15), More preferably, W, X, Υ and Ζ are independent sulfur atoms, oxygen atoms, selenium atoms or N-(R15), and at least two selected from the group consisting of W, X, Y and Z are N-( R15). W, X, Y and Z are particularly preferred, independent sulfur atoms or N-(R15), and at least two selected from the group consisting of W, X, Y and Z are N-(R15). R11, R12, R13 and R14 are each independently an alkyl group or a hydrogen atom which may have one or more halogen atoms, and an alkyl group which may have one or more halogen atoms, such as the same group as the above-mentioned -9-201206943 R15. The viewpoint of the easy synthesis of the compound (1) is preferably that 'x is the same as γ' w is the same as z. In the formula (1), the ring structure A and the ring structure B are independently an aromatic carbocyclic ring which may have a substituent (hereinafter abbreviated as an aromatic ring) or an aromatic heterocyclic ring which may have a substituent (hereinafter abbreviated as a heterocyclic ring) ° ° Ring structure A and ring structure B of the aromatic ring is an aromatic ring ' ring structure A's aromatic ring is composed of 6 to 14 carbon atoms 'shared with 5 ring of 5 and 2 carbon atoms Carbon ring. The aromatic ring of ring structure B is composed of 6 to 14 carbon atoms and has a carbon ring containing a 5-membered ring and a carbon atom of Z. The aromatic ring may have one or more substituents. The unsubstituted aromatic ring is, for example, a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring or an anthracene ring, preferably a benzene ring and a naphthalene ring, more preferably a benzene ring. The heterocyclic ring of the ring structure A and the ring structure B is a ring having aromaticity and containing at least one hetero atom, and the hetero ring of the ring structure A is a ring having 5 to 12 atoms, and a total of 5 members containing W Ring with a carbon ring of 2 carbon atoms. The heterocyclic ring of the ring structure B is such that the number of atoms constituting the ring is 5 to 12, and a carbon ring containing a 5-membered ring and 2 carbon atoms is common. The heterocyclic ring may have one or more substituents. Heterogeneous atoms such as oxygen atoms, selenium atoms, sulfur atoms, and nitrogen atoms. The number of heterologous atoms contained in the heterocyclic ring is preferably one or two. Unsubstituted heterocyclic ring such as thiophene ring, furan ring, selenophene ring, pyroline ring, oxazole ring, thiazole ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, etc. Thieno[3,2-b]thiophene ring, furo[3,2-b]pyranyl ring, thieno[3,2-b]furan ring, benzo[b]thiophene ring, benzoquinone[b]咲-10- 201206943 A bicyclic heterocyclic ring such as a ring. The heterocyclic ring of ring structure A and ring structure B is preferably a thiophene ring, a furan ring, a selenophene ring, a pyrrole ring, a thiazole ring, a thieno[3,2-b]thiophene ring, a furo[3,2-b a furan ring, a thieno[3,2-b]furan ring, a benzo[b]thiophene ring and a benzo[b]furan ring, more preferably a carbon atom having 2 and 3 positions and a W or Z group a thiophene ring of a ring, a carbon atom having 2 and 3 positions and a thieno[3,2-b]thiophene ring containing a ring of W or Z, and a carbon atom having 2 and 3 positions and containing W or Z The benzo[b]thiophene ring of the ring is particularly preferably a thiophene ring having a carbon atom of 2 and 3 positions and a ring containing W or Z. The ring of the ring structure A and the ring structure B and the substituent of the hetero ring such as an alkyl group, an alkoxy group, an aryl group, an alkyl-substituted aryl group, an alkoxy-substituted aryl group, a heteroaryl group, an alkyl-substituted heteroaryl group Alkoxy substituted heteroaryl, alkenyl, alkynyl, alkylthio, alkylcarbonyl, alkoxycarbonyl, (trialkyl)decyl, (dialkyl)amine, halogen, cyano And nitro. Alkyl, alkoxy, aryl, alkyl substituted aryl, alkoxy substituted aryl, heteroaryl, alkyl substituted heteroaryl, alkoxy substituted heteroaryl, alkenyl, alkynyl, The alkylthio group, the alkylcarbonyl group, the alkoxycarbonyl group, the (trialkyl)decylalkyl group and the (dialkyl)amine group may have one or more halogen atoms. Among them, an alkyl group having one or more halogen atoms, an alkoxy group having one or more halogen atoms, an aryl group having one or more halogen atoms, and an alkyl group having one or more halogen atoms may be preferably used. The aryl group may have an alkoxy-substituted aryl group having one or more halogen atoms, may have a heteroaryl group of one or more halogen atoms, may have an alkyl-substituted heteroaryl group having one or more halogen atoms, and may have one or more The alkoxy-substituted heteroaryl group of the halogen atom may have -11 - 201206943 (trialkyl) fluorenyl group and a halogen atom of one or more halogen atoms, more preferably an alkyl group which may have one or more halogen atoms, and may have One of the alkoxy groups may have an aryl group having one or more halogen atoms, may have a heteroaryl group of a halogen atom, and may have one or more halogen atoms (trialkylene group and halogen atom, particularly preferably An alkoxy group having one or more halogen atoms, an aryl group having one atom, a heteroaryl group having one or more halogen atoms, and a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and iodine Preferred are a fluorine atom, a bromine atom and a bowl atom. The above alkyl group is, for example, a linear alkyl group or a branched chain. The alkyl group and the cyclic group are preferably a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms. For example, methyl, ethyl, η-propyl, isopropyl, η-butyl , S-butylbutyl, η-pentyl, neopentyl, η-hexyl '2-ethylhexyl, cycloη-heptyl, η-octyl, cyclooctyl, η-fluorenyl, η-fluorenyl , 2-hexyl, η-undecyl, η-dodecyl, η-tridecyl, η-tetradecyl-pentadecyl, η-hexadecyl, η-heptadecyl , η-octadecanecandecyl, η-eicosyl, η-tetradecyl, η-twencosyl-tetracosyl, η-tetracosyl, η-di Pentadecyl, η-alkyl, η-tetradecyl, η-octadecyl, η-dodecyltridecyl, preferably an alkyl group having 1 to 2 carbon atoms. More preferably, it is a C 1 alkyl group, and an alkyl group having one or more halogen atoms, such as a group in which all hydrogen atoms of the above alkyl group are substituted by a halogen atom. The alkoxy group is, for example, linear, branched or cyclic. The alkoxy group is a linear, branched or cyclic alkoxy group having 1 to 30 carbon atoms. The upper halogen atom I is a fluorenyl group. Atom, an alkyl group, a specific example group, a t-hexyl group, a decylalkyl group, a group, an n-alkyl group, a hexadecyl group, and a part of n- to 16 or, preferably, a specific example -12-201206943 Oxyl, ethoxy, η-propoxy, isopropoxy, η-butoxy, isobutoxy ' t-butoxy, η-pentyloxy, neopentyloxy, η-hexyloxy , 2-ethylhexyloxy, cyclohexyloxy, η-heptyloxy, η-octyloxy, cyclooctyloxy, decyloxy, decyloxy, 2-hexyldecyl, 3,7- Monomethyloctyloxy, η-undecyloxy, η-dodecyloxy, η-tridecyloxy, η-tetradecyloxy, η-pentadecanyloxy, η-ten Hexacarbonyloxy, η-heptadecanyloxy, η-octadecyloxy, η-nonadecanyloxy, η-icosyloxy, η-icosyloxy, η-Twenty a dialkoxy group, a II-docosyloxy group, a η-tetracosyloxy group, a η-tetradecyloxy group, an η-trihexayloxy group, an η-27-isthoxy group, η - 28 oxalate oxy, η - yttrium oxide, η - decyloxy, methoxymethoxy, methoxyethoxy, methoxymethoxymethoxy, Methoxy The ethoxyethoxy group and the polyethylene glycoloxy group are preferably an alkoxy group having 1 to 20 carbon atoms, more preferably an alkoxy group having 1 to 16 carbon atoms. An alkoxy group having one or more halogen atoms, such as a group in which a part or all of hydrogen atoms of the above alkoxy group are substituted by a halogen atom. The above aryl group is an aryl group having 6 to 20 carbon atoms such as a phenyl group or a naphthyl group, and more preferably a phenyl group or a naphthyl group. An aryl group having one or more halogen atoms such as a group in which a part or all of hydrogen atoms of the above aryl group are substituted by a halogen atom. The above heteroaryl group is preferably a monocyclic or bicyclic heteroaryl group such as a thiol group, a furyl group, a thiazolyl group, a thieno[3,2-b]thiol group, a furo[3,2-b] group. Furanyl, thieno[3,2-b]furanyl, benzo[b]thienyl, benzo[b]furanyl, more preferably thienyl, furyl, thieno[3,2-b Thiamine, benzo[b]thienyl and benzo[b]furanyl. A heteroaryl group having one or more halogen atoms, for example, a part or all of hydrogen atoms of the above heteroaryl group is substituted by a halogen atom from the group -13 to 201206943. The alkyl-substituted aryl group is a group in which one or more hydrogen atoms of the above aryl group are substituted with the above alkyl group. The alkoxy-substituted aryl group is a group in which one or more hydrogen atoms of the above aryl group are substituted by the above alkoxy group. The alkyl-substituted heteroaryl group is a group in which one or more hydrogen atoms of the above heteroaryl group are substituted with the above alkyl group. The alkoxy-substituted heteroaryl group is a group in which one or more hydrogen atoms of the above heteroaryl group are substituted by the above alkoxy group. The above alkenyl group, for example, a linear alkenyl group and a branched alkenyl group, is preferably a linear or branched alkenyl group having 2 to 30 carbon atoms. Specifically, for example, vinyl, 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, 1-cyclohexenyl, 1-heptenyl, 1-octenyl, 1- Decenyl, 1-decenyl, 1-undecylalkenyl, 1-dodecenyl, 1-tridecenyl, 1-tetradecenyl, 1-pentadecenyl, 1-hexadecenyl, 1-heptadecenyl, 1-octadecenyl, 1-nonadecenyl, 1-eicosyl, 1-eicosylalkenyl, 1 -tetradecenyl, 1-docosylcenyl, 1-tetracosylenyl, 1-pentadecenyl, 1-hexadecenyl, 1-branched Alkenyl, 1-teroctadecenyl, 1-terecosylenyl and 1-tridecenyl, preferably an alkenyl group having 2 to 20 carbon atoms, more preferably 2 to 16 carbon atoms Alkenyl. The alkenyl group having one or more halogen atoms is a group in which a part or all of hydrogen atoms of the above alkenyl group are substituted by a halogen atom. The above alkynyl group, for example, a linear alkynyl group and a branched alkynyl group, is preferably a linear or branched alkynyl group having 2 to 30 carbon atoms. Specifically, for example, an ethyl group, 1-prop-14-201206943 alkynyl, 1-butynyl, 1-pentyl, 1-hexynyl, 1-heptynyl, 1-octynyl, 1-indole Alkynyl, 1-nonynyl, 1-non-carbynyl, 1-dodecynyl, 1-tridecynyl, 1-tetradecynyl, pentadecynyl, 1_ Hexadecaynyl, 1-heptadecaynyl, 1-octadecynyl, nonadecanyl alkynyl, 1-epi-carbyl, 1-di-[-carbynyl, 1--ten Mono-alkynyl, 1-tetracosylalkynyl, 1-tetracosylalkynyl, 1-tetradecalkynyl, ^hexadecaalkynyl, 1-hexadecanylalkynyl, 1 a octacosyl alkynyl group, a bromo-non-octadecynyl group and a 1-triacontanyl group, preferably an alkynyl group having 2 to 20 carbon atoms is more preferably an alkynyl group having 2 to 16 carbon atoms. An alkynyl group having one or more halogen atoms such as a group in which a part or all of hydrogen atoms of the above alkynyl group are substituted by a halogen atom. The above alkylthio group, for example, a linear, branched or cyclic alkylthio group is more preferably a linear, branched or cyclic alkylthio group having 1 to 30 carbon atoms. Specifically, for example, methylthio, ethylthio, η-propylthio, isopropylthio, η-butylthio, isobutylthio, s-butylthio, t-butylthio, η-pentylthio , cyclopentylthio, η-hexylthio, 2-ethylhexylthio, cyclohexylthio, η-heptylthio, cycloheptylthio, η-octylthio, cyclooctylthio, η-壬Sulfur, η-sulfonylthio, 2-hexylsulfonylthio, η-~(--indolylthio, η-tetradecylthio, η-tritylthio, η-tetradecylthio, Η-pentadecanethio, η-hexadecanethio, η-seventeenth thiol, η_eighteen thiol, η·nine thiol, η - tenth thiol, η- T-dodecylthio, η-docosylthio, η-docosylthio, η-tetracosylthio, η-pentacosylthio ' η-hexadecanesulfide a group, an η-tetradecylthio group, a η-docosylthio group, a η-dodecylthio group and an η-triacontanyl group, and an alkylthio group having 2 to 20 carbon atoms, more preferably An alkylthio group having 2 or more carbon atoms. An alkylthio group having 1 or more halogen atoms, such as a moiety of the above alkylthio group or a group in which all of a hydrogen atom of 15-201206943 is substituted by a halogen atom. The above alkylcarbonyl group is, for example, a linear chain The alkylcarbonyl group and the branched alkylcarbonyl group are preferably a linear or branched alkylcarbonyl group having 2 to 30 carbon atoms, more preferably a linear or branched alkylcarbonyl group having 2 to 17 carbon atoms. Specifically, for example, methylcarbonyl, ethylcarbonyl, η-butanecarbonyl, η-hexylcarbonyl, η-octylcarbonyl, η-undecylcarbonyl, η-pentadecylcarbonyl, and η-icosylcarbonyl. Alkane having one or more halogen atoms A carbonyl group such as a group in which a part or all of hydrogen atoms of the above alkylcarbonyl group are substituted by a halogen atom, such as a linear alkoxycarbonyl group and a branched alkoxycarbonyl group, preferably a carbon number of 2 to 30. a linear or branched alkoxycarbonyl group, more preferably a linear or branched alkoxycarbonyl group having 2 to 17 carbon atoms. Specifically, for example, methoxycarbonyl, ethoxycarbonyl, η-butoxy a carbonyl group, a η-hexyloxycarbonyl group, a η-octyloxycarbonyl group, an η-dodecyloxycarbonyl group, an η-pentadecyloxycarbonyl group, and an η-icosyloxycarbonyl group. The alkoxycarbonyl group is a group in which a part or all of hydrogen atoms of the above alkoxycarbonyl group are substituted by a halogen atom. The above (trialkyl) nonyl group is, for example, 3 carbon atoms of 1 to 30. The alkyl group is bonded to a base of a halogen atom, and specifically, for example, a trimethylsulfanyl group, a triethylsulfanyl group, a tri-n-propyldecylalkyl group, a triisopropyldecylalkyl group, a tri-n-butyldecane group, Tris-butyl-decyl, tri-t-butyldecyl, tri-isobutyldecyl, t-butyl-dimethyldecyl, tri-n-pentyldecyl, tri-η- a hexyldecylalkyl group and a dimethyl-n-dodecyldecanealkyl group, preferably three alkyl groups having 1 to 6 carbon atoms bonded to a ruthenium atom. (Trialkyl group) having one or more halogen atoms The above-mentioned (dialkyl)amino group is, for example, 2 alkyl groups bonded to a base of a halogen atom, at least one of which is substituted by a halogen atom for at least one of the alkyl groups 16 to 201206943. The alkyl group having 1 to 30 carbon atoms is bonded to a group of a nitrogen atom, that is, a group in which two hydrogen atoms of the amine group are each substituted by an alkyl group having 1 to 30 carbon atoms. Preferably, two alkyl groups having 1 to 10 carbon atoms are bonded to the nitrogen atom. Specifically, for example, dimethylamino group, diethylamino group, di-η-propylamino group, diisopropylamino group, di-η-butylamino group, di-s-butylamino group, two T-butylamino, di-isobutylamino, t-butylisopropylamino, di-η-hexylamino, di-η-octylamino and di-η-decylamino . A (dialkyl)amino group having one or more halogen atoms, for example, a group in which a two alkyl group is bonded to a nitrogen atom, and a part or all of hydrogen atoms of at least one alkyl group are substituted by a halogen atom. Is a benzene ring represented by the formula (C1), a hetero [3,2-b] heterocyclic ring represented by the formula (C2) or a benzo[l,2-b: 4,5- represented by the formula (C3). B'] diheterocyclic ring.

(wherein P and Q are independently a sulfur atom 'an oxygen atom, a selenium atom or a ruthenium atom, and the benzene ring constituting the above ring may have a substituent). In the formulae (C2) and (C3), p and q are preferably, The independent sulfur atom 'oxygen atom or selenium atom, more preferably a sulfur atom or an oxygen atom, particularly preferably a sulfur atom. The substituent of the benzene ring constituting the ring represented by the above formulas (C1) and (C3) is the same as the substituent of the ring structure A and the ring structure B, and the substituent is preferably the same as the ring structure A and the ring structure b. Preferred substituents. -17- 201206943 The ring represented by formula (C2) such as 'thieno[3,2_b]thiophene ring, furo[3,2-b]furan ring, selenyl[3,2_b]selenophene ring, thieno[ 32b] furan ring, thieno[3,2-b] selenophene ring and selenyl [3,2-b]furan ring, preferably benzophenan [3,2-b]thiophene ring (C3) The ring represented is such as 'benzo[i,2_b: 4,5 rush,] dithiophene ring, benzo[l,2-b: 4,5-b']difuran ring and benzo[ij-b: 4,5_b,] - a selenophene ring, preferably a benzo[ij-b: 4,5-b']dithiophene ring and a benzo[l,2-b:4,5-b']difuran ring More preferably, it is benzo: 4,5-b,] dipyrene ring. In the α-form (1), the ring structure C is a benzene ring represented by the formula (C1), and when X and oxime are independently N-(R15), the ring structure VIII and the ring structure Β are independently a scent having a substituent. The group heterocyclic ring 'in this case, W and z are preferably an independent sulfur atom, an oxygen atom or a selenium atom, and more preferably W and Z are independently a sulfur atom or an oxygen atom 'W and Z are particularly preferably a sulfur atom. Further, in this case, X and γ are preferably the same N-(R15p compound (1), and when ring structure C is a benzene ring represented by formula (C1), it is preferred that 'X and Y are independently a sulfur atom or an oxygen atom. Or a selenium atom, W and z are independently N-(R15) is preferred as 'X and γ are sulfur atoms or oxygen atoms, and 2 is independently N-(R15) is preferred, and X and Y are sulfur atoms. 2 is independently N_(Rl5). Further, at this time, W and Z are the same N-(R15). In the compound (1), the ring structure is represented by the formula (C2) [3, 2_ b The heterocyclic ring or the benzo[i,2_b : 4,5-b,] diheterocyclic ring represented by the formula (C3) is preferably 'W and one of X is N-(R15)' and the other is sulfur. Atom, oxygen atom or sun atom 'Y and Z are N-(R15), the other is a sulfur atom, • 18 - 201206943 oxygen atom or selenium atom, more preferably, W and χ one is ^(7)] 5), the other side is a sulfur atom or an oxygen atom, one of γ and Z is N-(R15), the other is a sulfur atom or an oxygen atom', particularly preferably, one of W and X is N-(R15), and One is a sulfur atom or an oxygen atom, γ is the same as X, and Z is the same as W. Compound (1), for example, ring structure C is a benzene ring represented by formula (C1), ring structure a and ring structure b are independently an aromatic hetero ring which may have a substituent, and 乂 and γ are independently N_(R15) ' w and Z are the compounds of a sulfur atom, an oxygen atom or a selenium atom (^); the ring structure C is a benzene ring represented by the formula (C1), the ring structure a and the ring structure b are the same 'and may have a substituent Aromatic heterocyclic ring, X and γ are the same N-(R15)' W and Z is a compound of sulfur atom, oxygen atom or selenium atom (1); ring structure C is a benzene ring represented by formula (C1) , a ring structure A and a ring structure B are the same 'and are aromatic heterocycles which may have a substituent, X and γ are the same N-(R15)'w and Z is a compound independently a sulfur atom or an oxygen atom (1) The ring structure C is a benzene ring represented by the formula (C1), the ring structure a and the ring structure b are the same 'and are aromatic heterocyclic rings which may have a substituent, and X and γ are the same N-(R15), W And Z is a sulfur atom compound (i); ring structure C is a benzene ring represented by formula (C1), ring structure a and ring structure b are thiophene rings which may have a substituent, and ¥ is independently n_(ri5 ), rM is carbon number 1 a compound (1) in which the W and Z are independently a sulfur atom, an oxygen atom or a selenium atom; the ring structure C is a benzene ring represented by the formula (C1), and the ring structure a and the ring structure b are the same 'and a thiophene ring which may have a substituent, X and γ are the same n_(Ri5) • 19-201206943 'R15 is an alkyl group having 1 to 30 carbon atoms' and a compound in which Z is independently a sulfur atom, an oxygen atom or a selenium atom ( 1); Ring structure C is a benzene ring represented by formula (C1), ring structure a and ring structure B are the same, and are thiophene rings which may have a substituent, and X and γ are the same N-(R15) ' R15 is a compound having a carbon number of 1 to 30, a compound (1) wherein W and z are each independently a sulfur atom or an oxygen atom; and a ring structure C is a benzene ring represented by the formula (C1), the ring structure a and the ring structure B are the same, and a thiophene ring which may have a substituent, X and γ are the same N-(R15) ' R15 is a C 1 to 30 alkyl group 'W and Z is a sulfur atom compound (1) Ring structure C is a formula (C1) The represented benzene ring, ring structure A and ring structure B are independently thiophene rings which may have a halogen atom, an alkyl group, a (trialkyl)decyl group, an aryl group or a heteroaryl group, and X and Y are independently N-(R15 ), R15 is carbon number 1 to 30 The compound (i) wherein the alkyl group 'W and Z are independently a sulfur atom, an oxygen atom or a selenium atom: The ring structure C is a benzene ring represented by the formula (ci), and the ring structure A and the ring structure B are the same 'and may have a halogen A thiophene ring of an atom, an alkyl group, a (trialkyl)decylalkyl group, an aryl group or a heteroaryl group, X and Y are the same N-(R15), and R15 is a fluorenyl group having a carbon number of 1 to 30 'W and Z independent a compound (1) which is a sulfur atom, an oxygen atom or a selenium atom: The ring structure C is a benzene ring represented by the formula (C1), and the ring structure A and the ring structure B are the same 'and may have a halogen atom, an alkyl group, (three) Alkyl, aryl or heteroaryl thiophene ring, X and γ are the same N-(Ri5), and Ri5 is a carbon number of 1 to 30. The W and Z are independently a sulfur atom or an oxygen atom. Compound (1) -20- 201206943 Ring structure C is a benzene ring represented by formula (Cl), ring structure A and ring structure B are the same ' and may have a halogen atom, an alkyl group, a (trialkyl) decyl group, a aryl group a thiophene ring of a heteroaryl group, X and Y are the same N-(Ri", Ri5 is a C 1 to 30 alkyl group 'W and Z is a sulfur atom compound (丨); Benzene ring represented by (Cl) The ring structure a and the ring structure B are independently a benzo[b]thiophene ring which may have a substituent, X and γ are independently N-(R15), R15 is an alkyl group having 1 to 30 carbon atoms, and W and Z are independently sulfur. a compound of an atom, an oxygen atom or a selenium atom (1); a ring structure C is a benzene ring represented by the formula (C1), and the ring structure A and the ring structure B are independently a halogen atom, an alkyl group, or a (trialkyl) decane. a benzo[b]thiophene ring of a aryl, aryl or heteroaryl group, X and Y are independently N-(R15), R15 is an alkyl group having 1 to 30 carbon atoms, and Z is independently a sulfur atom, an oxygen atom or a compound of a selenium atom (1); a ring structure C is a benzene ring represented by the formula (C1), and the ring structure a and the ring structure B are the same 'and may have a halogen atom, an alkyl group, a (trialkyl) nonyl group, and an aromatic group. a benzo[b]thiophene ring of a heteroaryl group, X and γ are the same n-(R15), R15 is an alkyl group having 1 to 30 carbon atoms, and Z is independently a sulfur atom, an oxygen atom or a selenium atom. Compound (1); ring structure C is a benzene ring represented by formula (C1), ring structure A and ring structure B are the same 'and may have a tooth atom, an alkyl group, a (trialkyl) decyl group, an aryl group or Heteroaryl benzo[b]thiophene ring, X and γ The same n-(R15), R15 is a compound having a carbon number of 1 to 30 'W and Z is independently a sulfur atom or an oxygen atom (1); -21 - 201206943 The ring structure C is represented by the formula (Cl) The benzene ring, ring structure A and ring structure B are the same 'and are benzo[b]thiophene rings which may have a halogen atom, an alkyl group, a (trialkyl)decyl group, an aryl group or a heteroaryl group, and X and γ are the same N-(r15), R15 is a compound having a carbon number of 1 to 30, and W and Z are a sulfur atom (1); ring structure C is a benzene ring represented by formula (C1), ring structure a and ring structure B is independently an aromatic carbocyclic ring which may have a substituent, and W and Z are independently N-(R15) 'X and Y are independently a compound of a sulfur atom, an oxygen atom or a selenium atom (1); The benzene ring represented by C1) is the same as the ring structure a and the ring structure B, and is an aromatic carbocyclic ring which may have a substituent. W and Z are the same N-(R15), and X and Y are independently a sulfur atom. Compound (1) of oxygen atom or selenium atom: Ring structure C is a benzene ring represented by formula (C1), ring structure A and ring structure B are the same 'and are aromatic carbon rings which may have a substituent, W and Z For the same >^-(1115), 乂 and independence a compound (1) which is a sulfur atom or an oxygen atom; a ring structure C is a benzene ring represented by the formula (C1), and the ring structure A and the ring structure B are the same, and are aromatic carbon rings which may have a substituent, and Z is the same N-(R15), X and Y are sulfur atom compounds (1); Ring structure C is a benzene ring represented by formula (C1), ring structure A and ring structure B are independently capable of having a substituent a benzene ring, wherein W and Z are independently N-(R15), R15 is an alkyl group having 1 to 30 carbon atoms, and X and Y are independently a compound of a sulfur atom, an oxygen atom or a selenium atom (1): ring structure C is a formula ( The benzene ring represented by C1) is the same as the ring structure A and the ring structure B, and is a benzene ring which may have a substituent, W and Z are the same N-(R15), and R15 is an alkyl group having 1 to 30 carbon atoms. X and Y are independently a sulfur atom, an oxygen atom or a compound of -22-201206943 selenium atom (1); ring structure C is a benzene ring represented by formula (C1), ring structure A and ring structure B are the same 'and may have a benzene ring of a substituent, wherein W and Z are the same N-(R15), R15 is an alkyl group having 1 to 30 carbon atoms, and X and γ are each independently a sulfur atom or an oxygen atom (1); Benzene ring represented by (C1), ring structure A and The ring structure B is the same, and is a benzene ring which may have a substituent, W and Z are the same N-(R15), R15 is an alkyl group having 1 to 30 carbon atoms, and X and γ are sulfur atoms; The benzene ring represented by the formula (C1), the ring structure a and the ring structure B are independently a benzene ring which may have a halogen atom, an alkyl group, a (trialkyl)decyl group, an aryl group or a heteroaryl group, and is independently Z and Z. Is N-(R15), Ris is a compound having a carbon number of 1 to 3 Å and X is independently a sulfur atom, an oxygen atom or a selenium atom. (1) » Ring structure C is a benzene represented by formula (C1) Ring, ring structure A and ring structure B are the same 'and are benzene rings which may have a halogen atom, an alkyl group, a (trialkyl)decyl group, an aryl group or a heteroaryl group, and W and Z are the same N-(R15) , R15 is a C 1 to 30 alkyl group, X and Y are independently a compound of a sulfur atom, an oxygen atom or a selenium atom (1 ); a ring structure C is a benzene ring represented by the formula (C1), a ring structure a and a ring Structure B is the same and is a benzene ring which may have a halogen atom, an alkyl group, a (trialkyl)decyl group, an aryl group or a heteroaryl group, and W and Z are the same N-(R15), and R15 is a carbon number of 1 to 30 alkyl, X and Y are independently a sulfur atom or an oxygen atom Compound (1); Ring structure C is a benzene ring represented by formula (C1), ring structure A and ring structure B are the same, and may have a halogen atom, an alkyl group, a (trialkyl)decyl group, an aryl-23 - 201206943 or a heterocyclic benzene ring 'W and Z are the same N-(R15), R15 is a C 1 to 30 alkyl group, X and Y are a sulfur atom compound (1); The benzene ring represented by the formula (C1), the ring structure A and the ring structure B are independently a naphthalene ring which may have a substituent 'W and Z is independently n-(R15), and R15 is an alkyl group having a carbon number of 1 to 30' X And the compound (1) in which γ is independently a sulfur atom, an oxygen atom or a selenium atom; the ring structure C is a benzene ring represented by the formula (C1), the ring structure A and the ring structure B are the same 'and a naphthalene ring which may have a substituent , W and Z are the same N-(R15), R15 is an alkyl group having 1 to 30 carbon atoms, and X and Y are independently a compound of sulfur atom, oxygen atom or selenium atom (1); ring structure C is formula (C1) The benzene ring represented by the ring structure A and the ring structure B are the same, and are a naphthalene ring which may have a substituent, W and Z are the same N-(R15), and R15 is an alkyl group having 1 to 30 carbon atoms, X And Y is independently a compound of a sulfur atom or an oxygen atom (1 ); C is a benzene ring represented by the formula (C1), the ring structure A and the ring structure B are the same, and are a naphthalene ring which may have a substituent, W and Z are the same N-(R15), and R15 is a carbon number of 1 to 30. Alkyl group, X and Y are compounds of a sulfur atom (1); ring structure C is a benzene ring represented by formula (C1), ring structure A and ring structure B independently may have a halogen atom, an alkyl group, (trioxane) a naphthyl group of an alkyl group, an aryl group and a heteroaryl group, wherein W and Z are independently N-(R15), R15 is a group having a carbon number of 1 to 1, and X and Y are independently a sulfur atom, an oxygen atom or a selenium atom. The compound (1) and the ring structure c are the same as the benzene ring represented by the formula (C1), and the ring structure A and the ring structure B are the same, and may have a halogen atom, an alkyl group, a (three-compartment) sand courtyard group, an aryl group. 24- 201206943 or heteroaryl naphthalene ring 'good and 2 are the same n_(Ri5), Rl5 is an alkyl group having 1 to 30 carbon atoms, and X and Y are independently a compound of a sulfur atom, an oxygen atom or a selenium atom ( 1): The ring structure C is a benzene ring represented by the formula (C1), and the ring structure a and the ring structure 8 are the same, and may have a halogen atom, an alkyl group, a (trialkyl)decyl group, an aryl group or a heteroaryl group. Naphthalene ring, W and Z are the same N-(R15) R15 is a compound having a carbon number of 30, X and Y are each a compound of a sulfur atom or an oxygen atom (丨); a ring structure C is a benzene ring represented by the formula (C1), and the ring structure a and the ring structure b are the same, and The naphthalene ring 'W and Z which may have a halogen atom, an alkyl group, an alkyl group, a (trialkyl) nonyl group, an aryl group or a heterocyclic group are the same N_(R15), and R15 is a hospital base 'X with a carbon number of 1 to 30 and Y is a sulfur atom compound (1); ring structure C is a benzene ring represented by formula (C1), ring structure a and ring structure b are independently a thiophene ring which may have a substituent, and W and Z are independently N-(R15 R15 is a C 1 to 30 alkyl group, and X and Y are each independently a sulfur atom, an oxygen atom or a selenium atom. (1): The ring structure C is a benzene ring represented by the formula (C1), and the ring structure a and The ring structure B is the same 'and is a thiophene ring which may have a substituent, W and Z are the same N-(R15), R15 is an alkyl group having 1 to 30 carbon atoms, and X and Y are independently a sulfur atom, an oxygen atom or selenium. Atom compound (1); Ring structure C is a benzene ring represented by formula (C1), ring structure a and ring structure B are the same, and are thiophene rings which may have a substituent, and W and Z are the same N-( R15), R15 is an alkyl group having 1 to 30 carbon atoms X and Y are each independently a sulfur atom or an oxygen atom (1); ring structure C is a benzene ring represented by formula (C1), ring structure A and ring structure B phase -25-201206943 are the same, and may have a substituent a thiophene ring, wherein w and z are the same N-(R15), R15 is an alkyl group having 1 to 30 carbon atoms, and X and γ are a sulfur atom; (1) ring structure c is benzene represented by formula (C1) Ring, ring structure A and ring structure B are independently thiophene rings which may have a halogen atom, an alkyl group, a (trialkyl)decyl group, an aryl group or a heteroaryl group, and W and Z are independently N-(R15), and R15 is a compound having a carbon number of 1 to 30, X and Y independently being a sulfur atom, an oxygen atom or a selenium atom (1 ): The ring structure C is a benzene ring represented by the formula (C1), and the ring structure a and the ring structure B are the same ' And the thiophene ring 'W and Z which may have a halogen atom 'alkyl group, a (trialkyl) decyl group, an aryl group or a heteroaryl group are the same N-(R15), and R15 is an alkyl group having 1 to 30 carbon atoms. a compound (1) wherein X and Y are independently a sulfur atom, an oxygen atom or a selenium atom; and a ring structure C is a benzene ring represented by the formula (C1), the ring structure A and the ring structure B are the same, and may have a halogen atom , alkyl, (trialkyl) fluorene a thiophene ring of an alkyl group, an aryl group or a heteroaryl group, wherein W and Z are the same N-(R15), R15 is an alkyl group having 1 to 30 carbon atoms, and X and Y are independently a compound of a sulfur atom or an oxygen atom ( 1) t ring structure c is a benzene ring represented by formula (Cl), ring structure A and ring structure B are the same, and may have a halogen atom, an alkyl group, a (trialkyl)decyl group, an aryl group or a heteroaryl group. a thiophene ring, wherein W and Z are the same N-(R15), R15 is an alkyl group having 1 to 3 carbon atoms, and X and Y are a sulfur atom (1); ring structure C is represented by formula (C2) Hetero[3,2-b]heterocycle, ring structure A and ring structure B are independently aromatic carbon rings which may have a substituent, and X and -26-201206943 are N-(R15), and One of which is a sulfur atom, an oxygen atom or a selenium atom, one of γ and z is N-(R15)' and the other is a sulfur atom, an oxygen atom or a selenium atom, and R15 is a compound having an alkyl group having 1 to 30 carbon atoms (1) The ring structure C is a heterocyclic [3,2-b] heterocycle represented by the formula (C2), and the ring structure a and the ring structure B are independently an aromatic carbocyclic ring which may have a substituent, and one of the w&x N-(R15), the other side is a sulfur atom or an oxygen atom, and γ and z are in the form of N-(R15)' The compound is a sulfur atom or an oxygen atom, and R15 is a compound (1) having an alkyl group having 1 to 30 carbon atoms; the ring structure C is a hetero [3,2-b] heterocyclic ring represented by the formula (C2), a ring structure a and The ring structure B is independently an aromatic carbocyclic ring which may have a substituent, and one of w&x is N-(R15)' and the other is a sulfur atom, one of γ and z is N-(R15), and the other is sulfur. A compound in which the atom ' R15 is an alkyl group having 1 to 30 carbon atoms (1) The ring structure C is a hetero [3,2-b] hetero ring represented by the formula (C2), and the ring structure A and the ring structure B may independently have The aromatic carbocyclic ring of the substituent, one of W and X is N-(R15), the other is a sulfur atom or an oxygen atom, γ is the same as X, and z is the same as W. 'R15 is an alkyl group having 1 to 3 carbon atoms. The compound (1); the ring structure C is a hetero [3,2-b] heterocyclic ring represented by the formula (C2), the ring structure A and the ring structure B are the same, and are aromatic carbon rings which may have a substituent , one of W and X is N-(r15), the other is a sulphur pro- or an oxygen atom, γ is the same as X, 'Z is the same as W, and R15 is a compound (1) having an alkyl group having 1 to 30 carbon atoms; The ring structure C is a hetero [3,2-b] heterocycle represented by the formula (C2), and the ring structure A and the ring structure B are the same, and An aromatic carbocyclic ring having a substituent, one of W and X is N-(R15), the other is a sulfur atom, γ is the same as X, Z is the same as W phase -27-201206943, and R15 is a carbon number of 1 to 30. The alkyl group compound (1); the ring structure c is a hetero [3,2-b] heterocyclic ring represented by the formula (C2), and the ring structure A and the ring structure B are independently an aromatic heterocyclic ring which may have a substituent. One of W and X is N-(R15), the other is a sulfur atom, an oxygen atom or a selenium atom, one of Y and Z is N-(R15), and the other is a sulfur atom, an oxygen atom or a selenium atom, R15 a compound (1) having an alkyl group having 1 to 30 carbon atoms; a ring structure C is a hetero [3,2-b] hetero ring represented by the formula (C2), and the ring structure A and the ring structure B are independently a substituent group The aromatic heterocyclic ring, one of W and X is N-(R15), the other is a sulfur atom or an oxygen atom, one of γ and Z is N-(R15), and the other is a sulfur atom or an oxygen atom, R15 a compound (1) having an alkyl group having 1 to 30 carbon atoms; a ring structure C is a hetero [3,2-b] hetero ring represented by the formula (C2), and the ring structure A and the ring structure B are independently a substituent group An aromatic heterocyclic ring, one of w and X is N-(R15), and the other is a sulfur atom, γ A compound in which one of z is N_(Ri5), the other is a sulfur atom, and R15 is an alkyl group having 1 to 30 carbon atoms (1) » The ring structure C is a heteropoly group represented by the formula (C2) [3, 2-b] The heterocyclic ring, ring structure A and ring structure B are independently an aromatic hetero ring which may have a substituent, and one of W and X is N-(R15), the other is a sulfur atom or an oxygen atom, and γ is the same as X, z Like W, R15 is a compound (1) having an alkyl group having 1 to 30 carbon atoms; ring structure C is a hetero [3,2-b] heterocyclic ring represented by formula (C2), and ring structure A and ring structure B are the same. And an aromatic heterocyclic ring which may have a substituent, one of w and X is N-(R15), the other is a sulfur atom or an oxygen atom, γ is the same as X, B is the same as \¥, and R15 is a carbon number. a compound of 1 to 30 alkyl groups (丨); -28- 201206943 Ring structure C is a hetero [3,2-b] heterocycle represented by formula (C2), ring structure A and ring structure B are the same, and An aromatic heterocyclic ring having a substituent, wherein one of W and X is N-(R15)' and the other is a sulfur atom, Y is the same as X, z is the same as W, and R15 is a compound having an alkyl group having 1 to 30 carbon atoms. (1); Ring structure C is a heterocyclic [3,2-b] heterocycle represented by formula (C2), ring structure A and ring structure B is independently a benzene ring which may have a substituent, and one of W and X is N-(R15), the other is a sulfur atom, an oxygen atom or a selenium atom, and one of γ and Z is N-(R15), and the other is a sulfur atom, an oxygen atom or a selenium atom, R15 is a compound having an alkyl group having 1 to 30 carbon atoms; (1); a ring structure C is a hetero [3,2-b] heterocyclic ring represented by the formula (C2), ring structure A And ring structure B is independently a benzene ring which may have a substituent, and one of w and X is N-(R15)', and the other is a sulfur atom or an oxygen atom, and one of γ and Z is N-(R15), and the other is a sulfur atom or an oxygen atom, R15 is a compound (1) having an alkyl group having 1 to 30 carbon atoms; a ring structure c is a hetero [3,2-b] heterocyclic ring represented by the formula (C2), a ring structure A and a ring structure B is the same 'and a benzene ring which may have a substituent, one of w and X is Ν-β15)' The other is a sulfur atom or an oxygen atom, and one of γ and Z is N-(R15) 'The other is a sulfur atom or An oxygen atom, a compound (1) wherein Ri5 is an alkyl group having 1 to 30 carbon atoms; a ring structure C is a hetero [3,2-b] heterocyclic ring represented by the formula (C2), and the ring structure A and the ring structure B are the same ' And a benzene ring which may have a substituent, one of w and X is N-(R15), and the other side a sulfur atom, one of γ and z is N-(R15), and the other is a compound (1) in which a sulfur atom 'R15 is an alkyl group having 1 to 3 carbon atoms; and ring structure C is a compound represented by formula (C2) [3,2_b]heterocyclic ring, ring structure a and -29-201206943 ring structure B is the same, and is a benzene ring which may have a substituent, one of W and X is N-(R15), and the other is a sulfur atom or oxygen Atom, Y is the same as X, Z is the same as W, and R15 is a compound having an alkyl group having 1 to 30 carbon atoms (1); ring structure C is a hetero [3,2-b] heterocyclic ring represented by formula (C2). The ring structure A and the ring structure B are the same, and are a benzene ring which may have a substituent. One of W and X is N-(R15), the other is a sulfur atom, Y is the same as X, Z is the same as W, and R15 is carbon. a compound of the alkyl group of 1 to 30 (1); a ring structure C is a hetero [3,2-b] heterocycle represented by the formula (C2), the ring structure A and the ring structure B are the same ' and may have a halogen atom a benzene ring of an alkyl group, a (trialkyl)decyl group, an aryl group or a heteroaryl group, wherein one of W and X is N-(R15), the other is a sulfur atom or an oxygen atom, and Y is the same as X, Z and W is the same as the compound (1) wherein R15 is an alkyl group having 1 to 30 carbon atoms; the ring structure C is a hetero group represented by the formula (C2) [3, 2-b]heterocyclic ring, ring structure A and ring structure B are the same, and are a benzene ring which may have a substituent, one of w and X is N-(R15)' and the other is a sulfur atom, and γ is the same as X, z Like W, R15 is a compound of the alkyl group having 1 to 30 carbon atoms (1); ring structure C is a hetero [3,2-b] heterocycle represented by formula (C2), ring structure A and ring structure B are the same And a benzene ring which may have a halogen atom, an alkyl group, a (trimethylene) sulfonium group, an aryl group or a heteroaryl group, one of W and X is n-(R15), and the other is a sulfur atom 'Y and X is the same, Z is the same as W, and Ris is a compound (1) having an alkyl group having 1 to 30 carbon atoms; ring structure C is a hetero [3,2-b] hetero ring represented by formula (C2), ring structure A and Ring structure B is a naphthalene ring which may have a substituent, and it is considered that X is a square (R15), and the other is a sulfur atom, an oxygen atom or a selenium atom, and 2 is a square - 30-201206943 is N- (R15) 'The other side is a sulfur atom, an oxygen atom or a selenium atom, and is a compound (1) having an alkyl group having 1 to 30 carbon atoms; the ring structure C is a heteropoly group represented by the formula (C2) [3, 2-b] The heterocyclic ring, ring structure A and ring structure B are independently a naphthalene ring which may have a substituent, one of which is ... (R15), the other side A sulfur atom or an oxygen atom, a compound in which one of γ and Z is n-(R15)' and the other is a sulfur atom or an oxygen atom, and R15 is an alkyl group having 1 to 30 carbon atoms (1): Ring structure C is a formula (C2) The heterocyclic [3,2-b] heterocycle represented by the ring structure A and the ring structure B are the same, and are a naphthalene ring which may have a substituent, one of w and X is N-(R15), and the other is sulfur. One of the atoms or oxygen atoms, one of γ and z is N-(R15)', the other is a sulfur atom or an oxygen atom, and R15 is a compound of the fluorenyl group having 1 to 30 carbon atoms; (1); ring structure C is a formula (C2) The heterocyclic [3,2-b]heterocycle represented, the ring structure A and the ring structure B are the same, and is a naphthalene ring which may have a substituent, and one of w and X is N-(R15)' and the other is a sulfur atom. , one of γ and z is N-(R15), the other is a sulfur atom, and R15 is a compound of the alkyl group having 1 to 30 carbon atoms (1); the ring structure C is a heteropoly group represented by the formula (C2) [3, 2-b]heterocyclic ring, ring structure A and ring structure B are the same, and are a naphthalene ring which may have a substituent, one of w and X is N-(R15), the other is a sulfur atom or an oxygen atom, γ and X Similarly, z is the same as W, R15 is a compound having a carbon number of 1 to 30 (1); ring structure C is represented by formula (C2) a heterocyclic [3,2-b] heterocyclic ring having the same ring structure A and ring structure B, and being a naphthalene ring which may have a halogen atom, an alkyl group, a (trialkyl)decyl group, an aryl group or a heteroaryl group, And one of X is N-(R15), the other is a sulfur atom or an oxygen atom, Y is the same as X, Z is the same as W, and R15 is a compound (1) of carbon-31 - 201206943 alkyl having 1 to 30; The ring structure C is a heterocyclic [3,2-b] heterocyclic ring represented by the formula (C2), and the ring structure A and the ring structure B are the same, and are a naphthalene ring which may have a substituent, and one of W&x is N-( R15) 'The other side is a sulfur atom, Y is the same as X, z is the same as W, and R15 is a compound having an alkyl group having 1 to 30 carbon atoms (1); ring structure C is a hetero group represented by formula (C2) [3, 2-b]heterocyclic ring, ring structure A and ring structure B are the same, and are a naphthalene ring which may have a halogen atom, an alkyl group, a (trialkyl)decylalkyl group, an aryl group or a heteroaryl group, and one of W and X is N-(R15), the other is a sulfur atom, Y is the same as X, Z is the same as W, and R15 is a compound (1) having an alkyl group having 1 to 30 carbon atoms; ring structure C is a heterogeneous formula represented by formula (C2) [3,2-b]heterocyclic ring, ring structure A and ring structure B are independently a thiophene ring which may have a substituent, and one of w and X Ν-ίΚ·15), the other side is a sulfur atom, an oxygen atom or a selenium atom, one of γ and Z is N-(R15)' and the other is a sulfur atom, an oxygen atom or a selenium atom, and the carbon number is 1 to 30. Alkyl compound (1); ring structure C is a hetero [3,2-b] heterocycle represented by formula (C2), ring structure A and ring structure B are independently thiophene rings which may have a substituent, w and X One of them is N-(R15)' and the other is a sulfur atom or an oxygen atom. One of Y and Z is N-(R15), and the other is a sulfur atom or an oxygen atom. R15 is an alkyl group having 1 to 30 carbon atoms. Compound (1): Ring structure C is a hetero [3,2-b] heterocyclic ring represented by formula (C2), ring structure A and ring structure B are the same ' and are thiophene rings which may have a substituent, w and X One is N-(R15), the other is a sulfur atom or an oxygen atom, one of γ and z is N-(R15), the other is a sulfur atom or an oxygen atom, and R15 is an alkyl group having a carbon number of 1 to 30-32. Compound (1) of 201206943; ring structure C is a hetero [3,2-b] heterocycle represented by formula (C2), ring structure A and ring structure B are the same, and is a thiophene ring which may have a substituent, w And one of X is N-(R15), the other is a sulfur atom, and one of Y and Z N-(R15), the other one is a sulfur atom, and R15 is a compound (1) having an alkyl group having 1 to 30 carbon atoms; the ring structure C is a hetero [3,2-b] heterocyclic ring represented by the formula (C2). The ring structure A and the ring structure B are the same, and are thiophene rings which may have a substituent. One of w and X is N-(R15)' and the other is a sulfur atom or an oxygen atom, γ is the same as X, and z is the same as W. R15 is a compound (1) having an alkyl group having 1 to 30 carbon atoms; the ring structure C is a hetero [3,2-b] heterocyclic ring represented by the formula (C2), and the ring structure A and the ring structure B are the same and are a thiophene ring having a halogen atom, an alkyl group, a (trialkyl)decylalkyl group, an aryl group or a heteroaryl group, wherein one of W and X is N-(R15), the other is a sulfur atom or an oxygen atom, and Y is the same as X , Z is the same as W, R15 is a compound having an alkyl group having 1 to 3 carbon atoms (1); ring structure C is a hetero [3,2-b] heterocyclic ring represented by formula (C2), ring structure A and ring The structure B is the same and is a thiophene ring which may have a substituent. One of w and X is N-(R15), the other is a sulfur atom, γ is the same as X, z is the same as w, and R15 is a carbon number of 1 to 30. Alkyl compound (1); ring structure C is a hetero [3,2-b] heterocycle represented by formula (C2), ring structure a and ring structure B is the same and is a thiophene ring which may have a halogen atom, an alkyl group, a (trialkyl)silyl group, an aryl group or a heteroaryl group, and one of W and X is N-(R15), and the other is a sulfur atom. γ is the same as X, Z is the same as W, and R15 is a compound having a carbon number of 30 (1); ring structure C is a heterocyclic [3,2_b] heterocycle represented by formula (C2), ring structure a and -33 - 201206943 The ring structure B is the same and is a benzo[b]thiophene ring which may have a halogen atom, an alkyl group, a (trialkyl)decyl group, an aryl group or a heteroaryl group, and one of W and X is Ν-β15) The other is a sulfur atom or an oxygen atom, Y is the same as X, Z is the same as W, and R15 is a compound having an alkyl group having 1 to 30 carbon atoms (1); ring structure C is a heteropoly group represented by formula (C2) [3] , 2-b]heterocyclic ring, ring structure Α and ring structure B are the same, and may be a benzo[b]thienyl ring which may have a substituent, one of W and X is N-(R15), and the other is a sulfur atom, Y is the same as X, Z is the same as W, and R1 5 is a compound (1) having an alkyl group having 1 to 30 carbon atoms; ring structure C is a hetero [3,2-b] heterocyclic ring represented by formula (C2), ring The structure A and the ring structure B are the same, and may have a halogen atom, an alkyl group, a (trialkyl) nonyl group, An aryl or heteroaryl benzo[b]thiophene ring, one of W and .X is N-(R15), the other is a sulfur atom, Y is the same as X, Z is the same as W, and R15 is a carbon number of 1 to a compound of the alkyl group of 30 (1); a ring structure C is a benzo[l,2-b: 4,5-b'] diheterocyclic ring represented by the formula (C3), and the ring structure A and the ring structure B are independently An aromatic carbocyclic ring which may have a substituent. One of W and X is N-(R15), and the other is a sulfur atom, an oxygen atom or a selenium atom. One of Y and Z is N-(R15), and the other is a sulfur atom, an oxygen atom or a selenium atom, R15 is a compound having a carbon number of 1 to 30 (1); and ring structure C is a benzo[l,2-b: 4,5-b represented by the formula (C3) '] Diheterocyclic ring, ring structure A and ring structure B are independently an aromatic carbocyclic ring which may have a substituent, one of W and X is N-(R15), the other is a sulfur atom or an oxygen atom, Y and Z One of the compounds is N-(R15)', the other is a sulfur atom or an oxygen atom, and R15 is a compound having a carbon number of 1 to 30 (1); the ring structure C is a benzo[1, represented by the formula (C3). 2-b: 4,5-b']bicyclohetero-34-201206943, ring structure A and ring structure B are independently an aromatic carbocyclic ring which may have a substituent, W a compound (1) wherein one of X is N-(R15), the other is a sulfur atom, one of Y and Z is N-(R15), the other is a sulfur atom, and R15 is an alkyl group having 1 to 30 carbon atoms; The ring structure C is a benzo[i,2-b: 4,5-b'] diheterocyclic ring represented by the formula (C3), and the ring structure A and the ring structure B are independently an aromatic carbocyclic ring which may have a substituent. , one of W and X is N-(R15), the other is a sulfur atom or an oxygen atom, Y is the same as X, Z is the same as W, and R15 is a compound having a carbon number of 1 to 30 (1); C is a benzo[i,2-b: 4,5-b'] diheterocyclic ring represented by the formula (C3), and the ring structure A and the ring structure B are the same, and are aromatic carbon rings which may have a substituent. 'W and X are N-(R15), the other is a sulfur atom or an oxygen atom 'Y is the same as X'. Z is the same as W, and R15 is a compound having a carbon number of 1 to 30 (1); C is a benzo[i,2-b: 4,5-b'] diheterocyclic ring represented by the formula (C3), and the ring structure Λ and the ring structure B are independently an aromatic heterocyclic ring which may have a substituent, W And one of X is N-(R15)' and the other is a sulfur atom, an oxygen atom or a selenium atom, one of Y and Z is N-(R15), and the other is a sulfurogen. a compound (1) wherein an oxygen atom or a selenium atom 'R15 is an alkyl group having 1 to 30 carbon atoms; and a ring structure C is a benzo[i,2-b: 4,5-b, represented by the formula (C3). The diheterocyclic ring structure A and the ring structure B are independently an aromatic heterocyclic ring having a substituent. One of W and X is N_(Ri5), the other is a sulfur atom or an oxygen atom, and one of Y and Z is N-(R15)' wherein the other is a sulfur atom or an oxygen atom, and Ri5 is a compound having an alkyl group having 1 to 30 carbon atoms (1); -35-201206943 The ring structure C is a benzo[l] represented by the formula (C3) , 2-b: 4,5-b'] diheterocyclic ring, ring structure A and ring structure B are independently an aromatic heterocyclic ring which may have a substituent, and one of W and X is N-(R15), and the other side a sulfur atom, one of Y and Z is N-(R15), the other is a sulfur atom, and R15 is a compound (1) having an alkyl group having 1 to 30 carbon atoms; the ring structure C is a benzene represented by the formula (C3) And [l,2-b: 4,5-b'] diheterocyclic ring, ring structure A and ring structure B are independently an aromatic heterocyclic ring which may have a substituent, and one of W and X is N-(R15) The other side is a sulfur atom or an oxygen atom, Y is the same as X, Z is the same as W, and R15 is a compound (1) having an alkyl group having 1 to 30 carbon atoms; The structure c is a benzo[l,2-b: 4,5-b,]diheterocyclic ring structure represented by the formula (C3), and the ring structure A and the ring structure B are the same, and are aromatic impurities which may have a substituent. One of the rings 'W and X is N-(R15), the other is a sulfur atom or an oxygen atom 'Y is the same as X, 2: is the same as ", and R15 is a compound (1) having an alkyl group having 1 to 30 carbon atoms; The ring structure C is the same as the benzo[l,2-b: 4,5-b,]diheterocyclic ring structure A and the ring structure B represented by the formula (C3), and is an aromatic group which may have a substituent.

The heterocyclic ring 'W and X' are in the form of N-(R15), the other is a sulfur atom, Y is the same as X', and Z is the same as W, and R15 is a compound having a carbon number of 1 to 30 (1), ring The structure C is a benzo[l,2-b:4,5-b']diheterocyclic ring structure represented by the formula (C3), and the ring structure b is independently a benzene ring which may have a substituent, W and X. The middle side is N_(R15), the other side is a sulfur atom, an oxygen atom or a selenium atom, one of Y and 2 is N-(R15), and the other side is a sulfur atom, an oxygen atom or a selenium atom-36-201206943 'R15 a compound (1) having an alkyl group having 1 to 30 carbon atoms; a ring structure C is a benzo[l,2-b:4,5-b,]diheterocyclic ring represented by the formula (C3), a ring structure A and The ring structure B is independently a benzene ring which may have a substituent, one of w and X is N-(R15), the other is a sulfur atom or an oxygen atom, one of γ and z is N-(R15), and the other is sulfur. a compound (1) wherein an atom or an oxygen atom, R15 is an alkyl group having 1 to 30 carbon atoms; and a ring structure C is a benzo[l,2-b:4,5-b']dimer represented by the formula (C3) The ring, the ring structure A and the ring structure B are the same, and are a benzene ring which may have a substituent, one of w and X is n-(rm), and the other is a sulfur atom or an oxygen source. a compound (1) in which one of Y and Z is N-(R15), the other is a sulfur atom or an oxygen atom, and R15 is an alkyl group having 1 to 30 carbon atoms; the ring structure C is represented by the formula (C3) Benzo[l,2-b: 4,5-b']bicyclohetero, ring structure A and ring structure B are the same, and is a benzene ring which may have a substituent, and one of W and X is N-(R15) , the other is a sulfur atom, one of Y and Z is Ν-β15), the other is a sulfur atom, and R15 is a compound having a carbon number of 1 to 30 (1): The ring structure C is represented by the formula (C3) Benzo[l,2-b: 4,5-b']bicyclohetero, ring structure A and ring structure B are the same, and is a benzene ring which may have a substituent, and one of W and X is N-(R15 The other is a sulfur atom or an oxygen atom, Y is the same as X, Z is the same as W, and R15 is a compound having 1 to 30 carbon atoms. (1) » Ring structure C is a benzene represented by formula (C3) [l,2-b: 4,5-b']diheterocyclic ring, ring structure A and ring structure B are the same, and may have a halogen atom, an alkyl group, a (trialkyl)decyl group, an aryl group or a heteroaryl group The benzene ring, one of W and X -37-201206943 is N-(R15), the other is a sulfur atom or an oxygen atom, Y is the same as X, and z is W phase , R15 is a compound having a carbon number of 1 to 30 (1); ring structure C is a benzo[l,2-b: 4,5-b'] diheterocyclic ring represented by the formula (C3), ring structure A and ring structure B are the same, and are a benzene ring which may have a halogen atom, an alkyl group, a (trialkyl)decyl group, an aryl group or a heteroaryl group, and one of W and X is N-(R15), and the other is a sulfur atom, one of Y and Z is N-(R15), the other is a sulfur atom, and R15 is a compound having an alkyl group having 1 to 30 carbon atoms; (1); ring structure C is a benzene represented by formula (C3) And [l,2-b: 4,5-b'] diheterocyclic ring, ring structure A and ring structure B are the same, and may have a halogen atom, an alkyl group, a (trialkyl)decyl group, an aryl group or a hetero a benzene ring of an aryl group, a compound of N and (R15) in W and X, a sulfur atom in the other, Y is the same as X, z is the same as W, and R15 is a compound having an alkyl group having 1 to 30 carbon atoms (1) The ring structure C is a benzo[l,2-b: 4,5-b'] diheterocyclic ring represented by the formula (C3), and the ring structure A and the ring structure B are independently a naphthalene ring which may have a substituent, W& One of x is N-(R15), the other is a sulfur atom, an oxygen atom or a selenium atom, one of γ and Z is N-(R15), and the other is a sulfur atom, an oxygen atom or a sun. The compound 'R15 is a compound having a carbon number of 1 to 30 (1); the ring structure C is a benzo[l,2-b:4,5-b,]diheterocyclic ring represented by the formula (C3) The structure A and the ring structure B are independently a naphthalene ring which may have a substituent, and one of the % and the parent is N-(R15), the other is a sulfur atom or an oxygen atom, and the γ and z are N-(R15), The other is a sulfur atom or an oxygen atom, and R15 is a compound (1) having an alkyl group having 1 to 3 carbon atoms; the ring structure C is benzene + [1, 2-b: 4, which is represented by the formula (C3). 5-b']bicyclohetero, ring structure A and ring structure B are the same, and may be a naphthalene ring having a substituent, w -38- 201206943 and one of X is N-(R15), and the other is a sulfur atom or An oxygen atom, a compound (1) in which Y and Z are N-(R15), the other is a sulfur atom or an oxygen atom, R15 is an alkyl group having 1 to 30 carbon atoms; and a ring structure C is a formula (C3) The benzo[1,2-b: 4,5-b'] diheterocyclic ring is represented by the same ring structure A and ring structure B, and is a naphthalene ring which may have a substituent, and one of W and X is N-( R15), the other is a sulfur atom, one of Y and Z is N-(R15), the other is a sulfur atom, and R15 is a compound of the alkyl group having 1 to 30 carbon atoms (1); The structure C is a benzo[l,2-b: 4,5-b'] diheterocyclic ring represented by the formula (C3), and the ring structure A and the ring structure B are the same, and are a naphthalene ring which may have a substituent, W And one of X is N-(R15), the other is a sulfur atom or an oxygen atom, Y is the same as X, Z is the same as W, and R15 is a compound having 1 to 30 carbon atoms (1) » Ring structure C is The benzo[l,2-b: 4,5-b'] diheterocyclic ring represented by the formula (C3), the ring structure A and the ring structure B are the same, and may have a halogen atom, an alkyl group, (trialkyl group) a naphthalene ring of a decyl group, an aryl group or a heteroaryl group, wherein one of W and X is N-(R15), the other is a sulfur atom or an oxygen atom, one of Y and Z is Να15), and the other is a sulfur atom or An oxygen atom, R15 is a compound (1) having a carbon number of 1 to 30; and ring structure C is a benzo[1,2-b:4,5_b']diheterocyclic ring structure represented by formula (C3) A and ring structure B are the same, and are a naphthalene ring which may have a halogen atom, an alkyl group, a (trialkyl)decyl group, an aryl group or a heteroaryl group, and one of W and X is N-(R15), and the other is a sulfur atom, a compound in which γ is the same as X, Z is the same as W, and R15 is an alkyl group having 1 to 30 carbon atoms; (1); -39- 201206943 ring Let c be a benzo[l,2-b: 4,5-b'] diheterocyclic ring represented by formula (C3), ring structure A and ring structure B independently as a thiophene ring which may have a substituent, w and X One of them is N-(R15)' and the other is a sulfur atom, an oxygen atom or a selenium atom. One of Y and Z is N-(R15), the other is a sulfur atom, an oxygen atom or a selenium atom, and R15 is a carbon number of 1. Compound (1) of alkyl group up to 30; ring structure C is a benzo[l,2-b: 4,5-b'] diheterocyclic ring represented by formula (C3), ring structure A and ring structure B independent In the thiophene ring which may have a substituent, one of W and X is N-(R15), the other is a sulfur atom or an oxygen atom, one of Y and Z is N-(R15), and the other is a sulfur atom or an oxygen atom. , R15 is a compound (1) having an alkyl group having 1 to 30 carbon atoms; and ring structure C is a benzo[l,2-b:4,5-b']diheterocyclic ring represented by formula (C3), ring structure A and ring structure B are the same, and are thiophene rings which may have a substituent, and one of them is N-(R15), the other is a sulfur atom or an oxygen atom, and one of Y and Z is N-(R15), The other is a sulfur atom or an oxygen atom, and R15 is a compound (1) having an alkyl group having 1 to 30 carbon atoms; the ring structure C is represented by the formula (C3) Benzo[l,2-b: 4,5-b']bicyclohetero, ring structure A and ring structure B are the same, and is a thiophene ring which may have a substituent, and one of W&X is N-(R15) The other is a sulfur atom, one of Y and Z is N-(R15), the other is a sulfur atom, and R15 is a compound having a carbon number of 1 to 30 (1); the ring structure C is a formula (C3) The benzo[l,2-b:4,5-b']bicycloheterocycle represented by the ring structure A and the ring structure B are the same, and is a thiophene ring which may have a substituent, and one of the W&X is N-( R15), the other is a sulfur atom or an oxygen atom, Y is the same as X, Z is the same as W, and R15 is a compound having an alkyl group having 1 to 30 carbon atoms (-40-201206943 1 ): Ring structure C is formula (C3) The benzo[l,2-b:4,5-b,]diheterocyclic ring structure A and the ring structure B are the same, and may have a halogen atom, an alkyl group, a (trialkyl)decyl group, A thiophene ring of an aryl or heteroaryl group, one of W and X is N-(R15)' and the other is a sulfur atom or an oxygen atom, one of γ and z is N-(R15), and the other is a sulfur atom or oxygen. a compound in which an atom, Ri5 is an alkyl group having 1 to 30 carbon atoms; and a ring structure C is a benzo[l,2-b:4,5-b represented by the formula (C3) The diheterocyclic ring structure A and ring structure B are the same, and are thiophene rings which may have a halogen atom, an alkyl group, a (trialkyl)decyl group, an aryl group or a heteroaryl group, and one of W and X is N- (R15), the other is a sulfur atom, one of γ and z is N-(R15), the other is a sulfur atom, and R15 is a compound of the alkyl group having 1 to 30 carbon atoms (1), and the ring structure C is a formula ( The benzo[l,2-b: 4,5-b'] diheterocyclic ring represented by C3) is the same as the ring structure A and the ring structure B, and is a thiophene ring which may have a substituent, and one of W and X is N-(R15), the other is a sulfur atom, Y is the same as X, Z is the same as W, and R15 is a compound (1) having an alkyl group having 1 to 30 carbon atoms; ring structure C is a benzene represented by formula (C3) And [l,2-b: 4,5-b'] diheterocyclic ring, ring structure A and ring structure B are the same, and may have a halogen atom, an alkyl group, a (trialkyl)decyl group, an aryl group or a hetero a thiophene ring of an aryl group, wherein one of W and X is N-(R15), the other is a sulfur atom, Y is the same as X, Z is the same as W, and R15 is a compound (1) having an alkyl group having 1 to 30 carbon atoms; The ring structure C is a benzo[l,2-b: 4,5-b'] diheterocyclic ring represented by the formula (C3), and the ring structure A and the ring structure B are independently Benzo[b]thiophene with a substituent 201206943 ring, one of W and X is N-(R15), the other is a sulfur atom, an oxygen atom or a selenium atom, and one of Y and Z is N-(R15), another One of which is a sulfur atom, an oxygen atom or a selenium atom, and R15 is a compound having an alkyl group having 1 to 30 carbon atoms; (1); ring structure C is a benzo[1,2_b: 4,5-b represented by formula (C3) ']Diheterocycle' ring structure A and ring structure B are independently a benzo[b]thiophene ring of the thiophene ring, and one of X is N-(R15), and the other is a sulfur atom or an oxygen atom, Y And one of Z is >|_(foot 15), the other is a sulfur atom or an oxygen atom, and R15 is a compound (1) having an alkyl group having 1 to 30 carbon atoms; the ring structure C is represented by the formula (C3) Benzo[1,2-b: 4,5-b,]diheterocyclic ring, ring structure A and ring structure B are the same, and may be a benzo[b]thiophene ring of W and a group of X N-(R15), the other one is a sulfur atom or an oxygen atom. One of Y and Z is N-(R15), the other is a sulfur atom or an oxygen atom, and R15 is a compound having an alkyl group of 1 to 30 carbon atoms. Ring structure C is a benzo[l,2-b: 4,5-b,]diheterocyclic ring structure A and ring structure B represented by formula (C3) Similarly, it is a benzo[b]thiophene ring which may have a substituent, one of W and X is N-(R15), the other is a sulfur atom, one of Y and Z is N-(R15), and the other is a sulfur atom, a compound (1) wherein Ri5 is an alkyl group having 1 to 30 carbon atoms; and a ring structure C is a benzo[i,2-b:4,5-b'] diheterocyclic ring represented by the formula (C3). The ring structure A and the ring structure B are the same, and are a benzo[b]thiophene ring which may have a substituent. One of W and X is N-(R15), the other is a sulfur atom or an oxygen atom, and Y is the same as X. 2 is the same as W, and Ris is a compound (1) having an alkyl group having 1 to 3 carbon atoms; and ring structure C is benzo[i,2-b: 4,5-b'] represented by formula (C3) Heterocycle-42-201206943, ring structure A and ring structure B are the same 'and are benzo[b]thiophene rings which may have a halogen atom, an alkyl group, a (trialkyl)decyl group, an aryl group or a heteroaryl group, And one of X is N-(R15), the other is a sulfur atom or an oxygen atom, Y and the redundant medium are N-(R15), the other is a sulfur atom or an oxygen atom, and R15 is a carbon number of 1 to 30. Alkyl compound (1 ); ring structure C is a benzo[l,2-b: 4,5-b'] diheterocyclic ring represented by formula (C3), ring structure A and ring structure B phase And a benzo[b]thiophene ring which may have a halogen atom, an alkyl group, a (trialkyl)decylalkyl group, an aryl group or a heteroaryl group, one of W and X is NjR15), and the other is a sulfur atom, One of Y and Z is Ν-β15)', the other is a sulfur atom, and R15 is a compound having an alkyl group having 1 to 30 carbon atoms; (1); ring structure C is a benzo[1,2 represented by formula (C3). -b: 4,5-b']bicyclohetero, ring structure A and ring structure B are the same, and may be a benzene group having a halogen atom, an alkyl group, a (trialkyl)decyl group, an aryl group or a heteroaryl group. [b] The thiophene ring, wherein one of W and X is N-(R15), the other is a sulfur atom, γ is the same as X, z is the same as w, and R15 is a compound (1) having an alkyl group having 1 to 30 carbon atoms. The compound (1) is a compound represented by the following formula (1-1) to formula (1-4 5), formula (2-1) to formula (2_65), and formula (3-1) to formula (3-90). . -43- 201206943

(1-1) (1-2) (1-3) (1-4) (1-5)

-44- 201206943

-45- 201206943

(1-26) (1-27) (1-28) (1-29) (1-30)

-46- 201206943

(1-41) (1-42) (1-43) (1-44) (1-45)

(2-1) (2-2) (2-3) (2-4) (2-5)

(2-8) >30π61 (2-6) (2-, , S Q Q iPr - Ns^s sQ sQ (2-11) (2-12)

(2-13)

C2h5" CzHs c6h13( > CeH-c4h9^\,n,s C8H17々N i C4H

47 201206943

F F

(2-21) (2-22)

Cl Cl

(2-25)

-48- 201206943

-49 201206943

(2-41) (2.42)(CH3)3 ^ (4)) "

(2-46) (2-47) (2-48) -50- 201206943

-51 - 201206943

-52 201206943

(3-6) p-7) (3-8) (3-9) (3-10)

P-11) P-12) (3-13) P-14) (3-15)

(3-16) G3-17) (3-18) 0-19) (3-20) -53- 201206943

(3-26) (3-27) (3-28) (3-29) (3-30)

(3-31) (3-32) (3-33) (3-34) (3-35) -54- 201206943

(3-41) (3-42) (3-43) 0-44) (3-45) -55- 201206943

(3-52) -56- 201206943

P-61> (3-62) (3-63) (3-64) (3-65) -57- 201206943

(3-71) (3-72) (3-73) (3-74) (3-75) -58- 201206943

(3-76) P-77) (3-78) (3-79) (3-80)

-59- 201206943

(3-86) (3-87) (3-88) (3-89)

Cl

(3-90) Among them, preferred are formulas (1-1), (1-2), (1-3), (1-4), (1-5), (1-6), (1-7) ), (1-14), (1-16), (1-17), (1-18), (1-19), (1-20), (1-21), (1-22), (1-23), (1-26), (1-29), (1-31), (1-32), (1-33), (1-34), (1-35), (1 -36), ( 1- 37 ), ( 1-41 ), (1-44) , (1-45) , (2-1) , (2- 2) ' (2-3) , (2-4 ), (2-5), (2-6), (2-7), (2-8), (2-9), (2-10), (2-11), (2-12), ( 2- 13) , ( 2-14) , ( 2-15) , ( 2-17) , ( 2-19 ) , ( 2-20 ) , ( 2-2 1) , ( 2-22 ) , ( 2-24), (2-26), (2-27), (2-28), (2-29), (2-30), (2-3 1), (2-33), (2 -35), (2-36), (2-38), (2-40), (2-42), (2-43), (2-45), (2-46), (2-47 ), ( -60- 201206943 2-48 ), ( 2-51), ( 2-52 ), (: 2-53 ), (3-1 ), ( 3- 2 ), (3 .3 丨), (3-4) 丨, (3-5), (3-6), (3-7), (3-8)' (3-11) ^ (3-12), ( 3-16), (3-17), (3-18), (3-19), (3-20), (3-21), (3-22), (3-23), (3 - 26), (3-27), (3-28), (3-29), (3-30), (3-31), (3-32), (3-33), (3-34) , ( 3-35 ) ( 3-36), ( 3-37 ) ' ( 3-38), (3-41 ), ( 3-42 ) ( 3-46), ( 3-47), ( 3- 48 ), (3-49 ), ( 3-50 ), ( 3-51), ( 3-52), ( 3-53 ) ' (3-54 ), ( 3-55 ), ( 3-57) , ( 3-61 ), ( 3-62 ), (3-63 ), ( 3-64 ), ( 3-65), ( 3-66 ), ( 3-67 ), (3-68 ), ( 3-69 ) , ( 3-70), ( 3-71 ), ( 3-72 ), (3-76 ), ( 3-77 ) , ( 3-78), ( 3-79 ), ( 3- Compounds represented by 81), (3-82), (3-83), (3-84), (3-85), (3-86), (3-87), and (3-88)> More preferably (1-1), (1-2), (1-3), (1-4), (1-6) '(1 -14), (1-16), (1-17 ), (1-18 ) ' (1-19 ) ' (1 -2 1 ) , (1-31 ) , (1-32 ) , (1 -33 ) , ( 1-34 ) , (1 -36 ) , (1 -44 ) , (2-1 ), (2-2 )- ' (2-3 ), ( 2-4 ) ' ( :2 丨-5 ) , ( 2 6 ) , ( 2-7 ), ( 2 - 8 ) , ( 2-9 ) , ( 2 -10 ) , ( 2-14 ) , ( 2-19 ) , ( 2-20 ) , ( 2-21 ) , ( 2 -28 ) ' (2-29), (2-47), (3-1), (3-2), (3-3)' (3-4), (3-5), (3 -6), (3 -7 ) , (3-8 ) '丨[3- 11) , ( 3-16 ), (3-17 ), (3- 18) , (3- 19 -61 - 201206943 ) X ( 3. •20 ), (3-21 ) ' ( 3-22 ) 1 , (3-23 ) ( 3 -26 ) > ( 3- •28 ) , (3-29 ) ' ( 3-30 ) , (3-31 ) > ( 3. -32 ) ( 3- •33 ) (3-34 ) ' ( 3-35 ) , (3-36 ) > ( 3. -37 ) ( 3- •38 ) , (3- 41 ) ' ( 3-5 1 ) , (3-52 ) ( 3· -53 ) , ( 3- •54 ) (3-55 ) ' ( 3-61 ) > (3-62 ) % ( 3. -63 ) , ( 3. .64 ) (3-65 ) ' ( 3-66 ) , (3-67 ) , ( 3-68 ) , ( 3- 69 ) , (3-70 ) ' ( 3-71 ), a compound represented by (3-72), (3- •8 1 ), (3-83), (3-84), and (3-85). The compound (1) can be formed into a vacuum step as described later, and since the compound (1) has excellent solubility with respect to an organic solvent, mr can be formed into a film even by coating on a substrate or the like. , /- narration of organic solvents such as > water t methanol, ethanol isopropyl alcohol, butanol and other alcohol solvents; benzene, toluene, xylene% chlorophenyl hydrazine - di- benzene, three: gas benzene, fluorobenzene, etc. Aromatic hydrocarbon solvent t di-methane methane chloroform, 1,2-dichloroethane 1,1', 2,2,- tetrachloroethane tetrachloroethylene, carbon tetrachloride, etc. Ether solvent of diethyl ether, dioxane, tetrahydrofuran, anisole 1, etc.; pentane>hexain> fat of heptane, octane, cyclohexane, etc.; hydrocarbon solvent; acetone, methyl ethyl Ketone, methyl isobutyl ketone, cyclohexanone, etc.: ketone solvent; ethyl acetate butyl acetate ester solvent: acetonitrile, propionitrile, methoxy acetonitrile, glutaronitrile, benzonitrile, etc. * and dimethyl hydrazine, cyclobutyl hydrazine, N, N-dimethylformamide N, N-dimethylacetamide, N-methyl-2-pyridinone, etc. a polar solvent, preferably an aromatic hydrocarbon; a solvent, a halogenated aliphatic hydrocarbon Solvent and ether solvent> More preferably, toluene, xylene, hydrazine-di: chlorobenzene, dichlorocarbyl, chloroform or tetrahydrofuran can be used in combination of two or more kinds: organic solvent. -62-201206943 Compound (1) The concentration of the compound (1) is usually from 0 to 〇〇1 to 50% by weight, preferably from 0.01 to 10% by weight, more preferably from 0.1 to 5% by weight, based on the solution obtained by dissolving in an organic solvent. The above solution may contain an additive such as an antioxidant or a stabilizer in a range that does not significantly impair the carrier mobility of the film (organic semiconductor active layer) to be described later. The above solution can be, for example, generally from 1 Torr to 2 Torr. (: It is preferably prepared by dissolving the compound (1) in an organic solvent at 20 to 15 ° C. The method for producing the compound (1) will be described below. The ring structure C is represented by the formula (C1). The compound (1) wherein the benzene ring, X and γ are N-(R5) can be, for example, by the formula (2):

(In the formula, the ring structure A, the ring structure B' w and Z are each the same as defined above, and the ring structure C is a compound represented by the formula (C1), and R2 and R3 are each independently a halogen atom) The compound (2)) is obtained by reacting an amine compound (hereinafter abbreviated as the amine compound (4)) represented by the formula (4): R1 5 -NH 2 (4) (r15 is as defined above). The halogen atoms represented by R2 and R3 are bromine and iodine. -63- 201206943 The compound (2) is as the following compound.

SiMe3

SiMe3

-64 201206943

The reaction of the compound (2) with the amine compound (4) is preferably carried out in an organic solvent. The organic solvent may be an organic solvent inactive with respect to the above reaction, an aromatic hydrocarbon solvent such as toluene or xylene, a halogenated aromatic hydrocarbon solvent such as chlorobenzene or hydrazine-dichlorobenzene, or hexane or heptane. An aliphatic hydrocarbon solvent, a halogenated aliphatic hydrocarbon solvent such as chloroform or 1,2-dichloroethane, an alcohol solvent having 1 to 4 carbon atoms such as methanol, isopropanol or t-butanol, and tetrahydrofuran or dioxane. The ether solvent such as dimethoxyethane is preferably an aromatic hydrocarbon solvent or an aliphatic hydrocarbon solvent. More preferably, it is an aromatic hydrocarbon solvent, and particularly preferably toluene and xylene. Two or more organic solvents may be used in combination. The amine compound (4) is used in an amount of usually 1 to 50 moles, preferably 2 to 2 moles, more preferably 2 to 15 moles, per mole of the compound (2). When the compound (2) is dissolved in an organic solvent, the amount of the solvent to be used is such that the compound (2) in the resulting solution is generally 0.0001 to 20 mol, preferably 〇〇〇1 to 1 per liter of the solvent. It is better to use 〇1 to 5 moles. The reaction of the compound (2) with the amine compound (4) is preferably carried out in the presence of a palladium catalyst and a base. -65- 201206943 The amount of palladium catalyst used is generally 0.0001 to 0.3 mol, preferably 0.0001 to 0.2 mole of palladium catalyst in terms of palladium atom, relative to compound (2) 1 mol. The ligand is brought into contact with the palladium compound in an organic solvent. The palladium catalyst obtained by contacting the ligand with the palladium compound in an organic solvent before the reaction can be used for the reaction. Further, the ligand may be contacted with the palladium compound in the reaction system to prepare a palladium catalyst in the reaction system. The ligand may be a single-site ligand, a plurality of ligands and a polyacetylene ligand which are soluble in palladium and are soluble in an organic solvent, preferably a single-site ligand, more preferably a single-seat. Phosphine ligand. Single-site phosphine ligands such as tris(η-butyl)phosphine, tri(t-butyl)phosphine, tricyclohexylphosphine, triphenylphosphine, tris(p-tolyl)phosphine, trinaphthylphosphine, Diphenylnaphthalenephosphine and dicyclohexylnaphthalene scale are preferably tris(t-butyl)phosphine. Two-seat ligands such as 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,2-bis(diphenylphosphino)ethane, 1,3-double ( Diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, 1,1'-(diphenylphosphino)ferrocene, 4,5-bis(diphenylphosphino) )-9,9-dimethylxanthene, 2,2'-bis(diphenylphosphino)diphenyl ether, 5,5'·bis(diphenylphosphino)-4,4'-di a two-seat phosphine ligand having two phosphorus atoms, such as 1,3-benzoxoxazole, and 2-(N,N-dimethylamino)-2'-(dicyclohexylamino) A biphenylaminophosphine ligand having one nitrogen atom and one phosphorus atom such as biphenyl. A commercially available ligand may be used, and a ligand produced by a known method may be used. The amount of the ligand used is generally 0.5 to 20 moles of the fine atom of the palladium compound 1 to -66 to 201206943, such as 'palladium acetate, palladium chloride, dichlorobis(acetonitrile) palladium, Palladium acetamacetate, dichloro(cycloxin-丨,5-diene) palladium, dibromobis(benzonitrile) pin, di-anthracene-chlorobis(κ-allyl)dipalladium, dichlorobis( Pyridine) a divalent palladium compound such as palladium, dichlorobis(triphenylphosphine)palladium, dichlorobis(diphenylphosphino)ferrocene]palladium-dichloromethane complex, and tris(dibenzylidene) A valence palladium compound such as diacetone, tris(dibenzylideneacetone)dipalladium-chloroform complex or tetrakis(triphenylphosphine)palladium, preferably tris(dibenzylideneacetone)dipalladium And tris(dibenzylideneacetone) dipalladium-chloroform complex. A commercially available palladium compound or a palladium compound produced by a known method can be used. An alkali metal hydroxide such as an alkali metal such as calcium hydroxide; an alkali metal carbonate such as potassium carbonate, sodium carbonate or cesium carbonate; an alkaline earth metal carbonate such as magnesium carbonate, calcium carbonate or cesium carbonate; lithium phosphate and phosphoric acid An alkali metal phosphate such as potassium or sodium phosphate; and an alkali metal alkane such as sodium methoxide, sodium ethoxide, sodium t-butoxide, potassium methoxide, potassium ethoxide, potassium t-butoxide or lithium t-butoxide The oxide 'preferably an alkali metal carbonate and an alkali metal alkoxide, more preferably an alkali metal alkoxide' is an alkali metal alkoxide having a carbon number of 1 to 6. Two or more bases may be used in combination. The base is used in an amount of usually 0.1 to 25 moles, preferably 1 to 20 moles, more preferably 2 to 1 mole, per mole of the compound (2). When the amount of the base is 0.1 mol or more based on the compound (2), it is preferred to reduce the amount of the unreacted amine compound (4). The reaction temperature is usually from 〇 °c to the reflux temperature of the reaction mixture, preferably from -67 to 201206943 of from 40 to 200 °C. The reaction time is usually from 1 minute to 120 hours. After the reaction for a certain period of time, the reaction can be quenched, for example, by adding water or dilute hydrochloric acid to the reaction mixture. After the reaction is quenched, the compound (1) can be taken out by a post-treatment step such as extraction, washing, or the like. The compound (1) taken out can be purified by a general purification step such as recrystallization or sublimation 'various chromatography. The compound (2) can be produced, for example, by the method described in JP-A-2008-08 1494. The ring structure C is a benzene ring represented by the formula (C1), and the compound (1) wherein W and Z are independently N-(R5) can be, for example, by the formula (3)

(In the formula, the ring structure A' ring structure B, X and Y are the same as defined above, and the ring structure C is a benzene ring represented by the formula (C1), and R4 and R5 are independently a halogen atom) (hereinafter abbreviated as Compound (3)) is obtained by reacting with amine compound (4). The halogen atoms represented by R4 and R5 are, for example, bromine and iodine. The compound (3) is as the following compound. -68- 201206943

The reaction of the compound (3) with the amine compound (4) is preferably carried out in an organic solvent. The organic solvent may be an organic solvent which is inactive with respect to the above reaction, an aromatic hydrocarbon solvent such as toluene or xylene, a halogenated aromatic hydrocarbon solvent such as chlorobenzene or hydrazine-dichlorobenzene, hexane, heptane or the like. An aliphatic hydrocarbon solvent such as methoxyethane, a halogenated aliphatic hydrocarbon solvent such as chloroform or 1,2-dichloroethane, or an alcohol solvent having 1 to 4 carbon atoms such as methanol, isopropanol or t-butanol. The ether solvent such as tetrahydrofuran or dioxane is preferably an aromatic hydrocarbon solvent or an aliphatic hydrocarbon solvent, more preferably an aromatic hydrocarbon solvent, and particularly preferably toluene and xylene. Two or more organic solvents may be used in combination. The amine compound represented by the formula (4) is used in an amount of usually 1 to 50 moles, preferably 2 to 20 moles, more preferably 2 to 15 moles, per mole of the compound (3). When the compound (3) is dissolved in an organic solvent, the amount of the solvent to be used is generally 'per 10 liters of the compound (3) in the resulting solution per liter of the solvent, preferably 〇〇〇1 to 1 〇 Mo Er, more preferably 〇〇 1 to 5 Mo. The reaction of the compound (3) with the amine compound (4) is preferably carried out in the presence of a palladium catalyst and the test. -69- 201206943 The amount of rhodium catalyst used is generally 0.0001 to 0.3 mol, preferably 0.0001 to 0.2 molA palladium catalyst, based on the compound (3) 1 mol. It is obtained by contacting a ligand with a palladium compound in an organic solvent. A palladium catalyst obtained by contacting a ligand with a palladium compound in an organic solvent before the reaction can be used. Further, the ligand may be contacted with the palladium compound in the reaction system to prepare a palladium catalyst in the reaction system. The ligand is, for example, the same as the ligand used for the reaction of the above compound (2) with the amine compound (4). The palladium compound is also the same as the palladium compound used for the reaction of the above compound (2) with the amine compound (4). The base is also the same as the base used for the reaction of the above compound (2) with the amine compound (4). The amount of the base used is generally from 0.1 to 25 moles, preferably from 1 to 20 moles, more preferably from 2 to 10 moles, relative to the compound (3). When 1 mol is 0.1 mol or more, it is preferred to reduce the amount of the unreacted amine compound. The reaction temperature of the compound (3) with the amine compound (4) is generally ruthenium. The reflux temperature of the reaction mixture is preferably 40 to 20 (TC. The reaction time is generally from 1 minute to 120 hours. After a certain reaction time, the reaction can be carried out, for example, by adding water or dilute hydrochloric acid to the reaction mixture. After quenching, the compound (1) can be taken out by a general post-treatment step such as extraction, washing, etc. The compound (1) taken out can be re-refined by a general refining step such as recrystallization, sublimation or various chromatography. 70-201206943 The compound (3) can be, for example, by the formula (5):

(In the formula, 'ring structure A, ring structure B, ring structure C, X and γ are the same as defined in formula (3), R0 and R7 are independently a hydrogen atom or a halogen atom, but any of R6&R7 is a hydrogen atom) The compound (hereinafter abbreviated as compound (5)) is reacted with a halogenating agent. The halogen atoms represented by R6 and R7 are, for example, a bromine atom and an iodine atom. The compound (5) is as the following compound.

Compound (5) is, for example, Synth. Met. 2002, 130, 139, J. Org. Chem. 2003, 68, 9813, J. Am. Chem. Soc. 2007, 1 29, 1 23 86 ' Org. Lett 2008, l〇5 43 23 'Manufactured by the method described in J. Org. Chem. 2005, 7 0, 1 02 92, etc. The reaction of the compound (5) with a halogenating agent is preferably carried out in an organic solvent. The organic solvent is, for example, the same as the organic solvent used for the reaction of the compound (3) with the amine compound (4), preferably toluene, chloroform, carbon tetrachloride, and -71 - 201206943 N,N-dimethylformamidine. amine. Halogenating agents such as 'N-bromosuccinimide, 2-bromoacetamide, bromine, iodine, combination of iodine-periodic acid, a combination of monoiodide-periodic acid, and benzyltrimethylammonium The combination of chloroiodide-zinc chloride (II) is preferably a combination of N-bromosuccinimide, 'as and iodine-periodic acid. The halogenating agent is used in an amount of from 1 to 50 mol per mol of the compound (5), preferably from 5 to 2 mol, more preferably from 1 to 10 mol. The compound (5) When dissolved in an organic solvent, the amount of the solvent to be used is generally 'in terms of the compound (5) per 1 liter of the solvent relative to the solvent, 0.0001 to 20 mol, preferably 0.001 to 1 mol, more preferably When the reaction is difficult to be 0.01 to 5 moles, an additive such as benzoquinone or azobisbutyronitrile may be added to the catalyst reaction system. The reaction temperature is usually -78 ° C to the reflux temperature of the reaction mixture. It is preferably from -20 ° C to 50 ° C. The reaction time is usually from 1 minute to 48 hours. After a certain period of reaction, for example, water or dilute hydrochloric acid can be added to the reaction mixture to quench the reaction. The compound (3) can be taken out by a general post-treatment step such as extraction, washing, etc. The compound (3) taken out can be further purified by a general purification step such as recrystallization, sublimation or various chromatography. The compound (5) can be, for example, JP-A-2008-08 1494 A method of manufacturing a carrier. Ring C is configured of formula (C1) represented by the benzene ring, W, and Z are independently Ν-β5) represented by the compound (1) may, for example, by 'the formula (6) -72-201206943

(In the formula, the ring structure A, the ring structure B, X and Y are the same as defined above, and the ring structure C is a benzene ring represented by the formula (C1)) (hereinafter, abbreviated as the compound (6)) is cyclized. The obtained compound is obtained by reacting a compound represented by the formula (7): R1 5 -X1 (7) (wherein R15 is as defined above, and X1 is a halogen atom) (hereinafter abbreviated as the compound (7)). The halogen atom represented by X1 is, for example, a bromine atom and an iodine atom. The cyclization reaction of the compound (6) can be carried out, for example, according to Org. Lett., 2010, 12, 3164' in the presence of a phosphonate such as triethyl phosphonate, by heating the compound (6). The reaction of the compound obtained by the cyclization reaction of the compound (6) with the compound (7) is generally carried out under the conditions of an alkylation reaction with an amine group. The compound (6) is as the following compound. -73- 201206943

Compound (6) can be, for example, by formula (X) R50

(X) (wherein, X and Y are the same as defined above, and ring structure C is a benzene ring represented by formula (Cl), and R5Q and R51 are independently a halogen atom)

The compound represented (hereinafter abbreviated as compound (X)), and formula (Y-74-201206943 R52

N〇2 (wherein, ring structure A is the same as defined above, and R52 and R53 are independently a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms or an aryloxy group having 6 to 20 carbon atoms; Or a Suzuki coupling reaction in which a compound represented by R52 and R53 and a boron atom bonded thereto form a boron-containing ring (hereinafter, abbreviated as a compound (Y)). The halogen atom represented by R5() and R51 is, for example, a chlorine atom, a bromine atom and an iodine atom. The alkyl group having 1 to 10 carbon atoms represented by R52 and R53 is, for example, methyl, ethyl, η-propyl, isopropyl, η-butyl, sec-butyl, tert-butyl, η-pentyl. , neopentyl, cyclopentyl, η-hexyl, cyclohexyl, η-heptyl, η-octyl, η-fluorenyl, η-fluorenyl, 1,2-dimethylpropyl, etc. , branched or cyclic alkyl. Alkoxy groups having 1 to 10 carbon atoms are, for example, methoxy, ethoxy, η-propoxy, η-butoxy and η-hexyloxy. The aryloxy group having 6 to 20 carbon atoms is phenoxy, 1-naphthyloxy and 2-naphthyloxy. A boron ring in which R52 and R53 are bonded and formed with a boron atom bonded thereto, such as 1,3,2-dioxaborolan, 4,4,5,5-tetramethyl-1,3,2- Dioxolane, 5,5-dimethyl.-1,3,2-dioxacycloborane, 1,3,2-benzodioxolane and 9-boron Ring 3,3,1-decane ring. The Suzuki coupling reaction of the compound (X) with the compound (Υ) can be carried out under known conditions. The compound (X) can be, for example, benzo[l,2-b:4,5-b']bicyclo and n-butyllithium--75- according to the method described in Chem. Mater. 2010, 22, 5314. 201206943 After the reaction, the obtained product was reacted with tetrahalomethane. The ring structure c is a hetero[3,2-b]heterocyclic ring represented by the formula (C2) or a benzo[l,2-b:4,5-b']diheterocyclic compound represented by the formula (C3). (1) For example, by equation (8):

(wherein, ring structure A, ring structure B, W and Z are the same as defined above, and ring structure C is a heterocyclic [3,2_b] heterocyclic ring represented by formula (C2) or a benzo[l] represented by formula (C3). , a compound represented by 2-b: 4,5-b']bicyclo"R8 and R9 independently as a halogen atom) (hereinafter abbreviated as compound (8)) is reacted with an amine compound (4). Further, the 'ring structure C is a heterocyclic [3,2-b] heterocyclic ring represented by the formula (C2) or a benzo[1,2-b:4,5-b,] diheterocyclic ring represented by the formula (C3). The compound (1) can also be obtained by the formula (9):

(In the formula, 'ring structure A, ring structure B, W and Z are as defined above, and ring structure C is a heterocyclic [3,2-b] heterocyclic ring represented by formula (C2) or benzene represented by formula (C3) And [l,2-b: 4,5-b'] diheterocyclic ring, R8 and R9 are the same as defined above). The compound (hereinafter abbreviated as compound (9)) is reacted with the amine compound (4). . R8 and R9 do not represent a tooth atom such as a 'bromine atom and a Yao atom. -76- 201206943 The compound (8) and the compound (9) are as the following compounds.

The reaction of the compound (8) with the amine compound (4), and the reaction of the compound (9) with the amine compound (4) can be carried out by reacting the compound (2) with the amine compound (4). The amine compound (4) is used in an amount of usually 1 to 50 moles, preferably 2 to 20 moles, more preferably -77 to 201206943 2 to 1 5 with respect to the compound (8) or the compound (9). Moor. When the compound (8) or the compound (9) is dissolved in an organic solvent, the amount of the solvent to be used is generally 'the compound (8) in the obtained solution is 0.0001 to 2 mol per 1 liter or the compound (9) relative to the solvent. Preferably, it is from 0.001 to 10 moles, more preferably from 001 to 5 moles. The above reaction is preferably carried out in the presence of a palladium catalyst and a base. The palladium catalyst is generally used in an amount of 0.0001 to 0.3 mol, preferably 0.0001 to 0.2 mol per palladium atom, based on the compound (8) or the compound (9). 'In the organic solvent, the ligand is brought into contact with the palladium compound. A palladium catalyst obtained by contacting a ligand with a palladium compound in an organic solvent before the reaction can be used. Further, the ligand may be contacted with the palladium compound in the reaction system to prepare a palladium catalyst in the reaction system. The ligand is, for example, the same as the ligand used for the reaction of the above compound (2) with the amine compound (4). The palladium compound is also, for example, palladium used for the reaction with the above compound (2) and the amine compound (4). The compound is the same. The base is also the same as the base used for the reaction of the above compound (2) with the amine compound (4). The amount of the base to be used is usually 0.1 to 25 moles, preferably 1 to 20 moles, more preferably 2 to 10 moles, per mole of the compound (8) or the compound (9). When the amount of the base used is 0.1 mol or more based on the compound (8) or the compound (9), the amount of the base tends to decrease the amount of the unreacted amine compound.

The reaction temperature of the compound (3) with the amine compound (4) is usually from 0 °C to -78 to 201206943 to the reflux temperature of the reaction mixture, preferably from 40 to 200 °C. The reaction time is usually from 1 minute to 120 hours. After the reaction for a certain period of time, the reaction can be quenched, for example, by adding water or dilute hydrochloric acid to the reaction mixture. After the reaction is quenched, the compound (1) can be taken out by a usual post-treatment step such as extraction or washing. The compound (1) taken out can be re-refined by a general purification step such as recrystallization, sublimation or various chromatography. The compound (8) can be, for example, by the formula (1 〇 ):

(In the formula, the ring structure A, the ring structure B, the ring structure c, W and Z are the same as defined above. R2Q and R21 are independently a hydrogen atom or a halogen atom, but any of r2〇 and r2i are gas atoms) (hereinafter, abbreviated as compound (i 〇)) is obtained by reacting with a halogenating agent. Compound (9) can be, for example, by formula (1)

(In the formula, the ring structure A, the ring structure B, the ring structure C, Χ, γ, r2, and r21 are as defined above), the compound (hereinafter abbreviated as the compound (丨i)) is reacted with a halogenating agent. -79- 201206943 The halogen atom represented by R2Q and R21 is, for example, a bromine atom and an iodine atom. The compound (10) and the compound (1 1 ) are as the following compounds.

The compound (10) and the compound (1 1 ) can be, for example, according to Synth. Met. 2002, 130, 139, J. Org. Chem. 2003, 68, 9813, J. Am. Chem. Soc. 2007, 129, 1 23 86 , Org. Lett. 2008, 1 0, 43 23 and other methods are manufactured. The reaction of the compound (10) with a halogenating agent, and the reaction of the compound (11) with a halogenating agent are preferably carried out in an organic solvent. The organic solvent is, for example, the same organic solvent as the organic solvent used for the reaction of the above compound (5) with a halogenating agent, preferably toluene, chloroform, tetrachloro-80-201206943 carbon and N,N-dimethylformamide . The halogenating agent is used in an amount of usually 0.1 to 50 moles, preferably 〇 5 to 2 moles, more preferably 10 moles per mole of the compound (i 0 ) or the compound (n ). When the compound (10) or the compound (11) is dissolved in an organic solvent, the amount of the solvent to be used is generally 0.0001 to 20 mol per 1 liter of the compound (10) or the compound (11) in the resulting solution. It is preferably 0.001 to 10 moles, more preferably 0.01 to 5 moles. Halogenating agents such as hydrazine-bromo quinone imine, 2-bromoacetamide, bromine, iodine, iodine-periodic acid combination, monoethyl iodine-peracetic acid combination, and benzyltrimethylammonium A combination of chloroiodide-zinc chloride (II) or the like is preferably a combination of bismuth-bromosuccinimide, bromine and iodine-periodic acid. When it is difficult to carry out the reaction, an additive such as benzoquinone or azobisbutyronitrile may be added to the catalyst amount reaction system. The reaction temperature is usually -78 ° C to the reflux temperature of the reaction mixture, preferably -20 ° C to 50 ° C. The reaction time is usually from 1 minute to 48 hours. After a reaction for a certain period of time, the reaction can be quenched, for example, by adding water to the reaction mixture. After the reaction is quenched, the compound (1) can be taken out by a usual post-treatment step such as extraction or washing. The compound (1) to be taken out can be further purified by a general purification method such as recrystallization, sublimation or various chromatography methods, and the compound (8) and the compound (9) can be produced, for example, by the method described in JP-A-2008-08 1494. . The compound (1) of the present invention is soluble in an organic solvent. Therefore, the solution of the compound (1) and the organic solvent can be used to produce a film (organic semiconductor active layer) of the present invention described later by coating film formation. And better. An organic solvent capable of dissolving the compound (1), such as benzene, toluene, xylene, tetraphosphorus, chlorobenzene, 0-dichlorobenzene, trichlorobenzene, fluorobenzene, anisole, etc., an aromatic hydrocarbon solvent, dichloro Halogenated aliphatic hydrocarbon solvent of methane, chloroform, 1,2-dichloroethane, 1,1', 2,2'-tetrachloroethane, tetrachloroethylene, carbon tetrachloride, etc., diethyl ether, two An ether solvent such as an alkylene or tetrahydrofuran; an aliphatic hydrocarbon solvent such as pentane, hexane, heptane, octane or cyclohexane; acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc. An ketone solvent, an ester solvent such as ethyl acetate or butyl acetate; a nitrile solvent such as acetonitrile, propionitrile, methoxyacetonitrile, glutaronitrile or benzonitrile; and dimethyl hydrazine, cyclazone, and N, An aprotic polar solvent such as N-dimethylformamide, N,N-dimethylacetamide or N-methyl-2-pyrrolidone. Among them, toluene, xylene, tetraphosphorus, chlorobenzene, hydrazine-dichlorobenzene, dichloromethane, chloroform and tetrahydrofuran are preferred. Two or more organic solvents may be used in combination. The concentration of the compound (1) in the solution of the dissolved compound (1) is usually 0.001 to 50% by weight, preferably 〇1 to 1% by weight, more preferably 〇1 to 5% by weight. The solution may contain only the compound (1), and may contain an antioxidant, a stabilizer, an organic semiconductor material different from the compound (1), an organic insulating material, etc., within a range that does not significantly impair the carrier mobility of the film described later. . The organic semiconductor material different from the compound (1) may be a low molecular material' or a polymer material. The polymer material may be obtained by crosslinking the polymer -82-201206943. It is preferably a polymer material. Specifically, for example, polyacetylene and its derivatives, polythiophene and its derivatives, polythiophene vinyl ester and its derivatives, polyphenylene ester and its derivatives, polyphenylene vinyl ester and its derivatives, poly Pyrrole and its derivatives, polyaniline and its derivatives, polytriarylamine and its derivatives, polyquinoline and its derivatives 'peperene and its derivatives, Ding and its derivatives, pentene and its derivatives , phthalocyanine and its derivatives. In the film of the present invention, the content of the compound (1) is preferably 10% by weight or more, more preferably 20% by weight or more based on 100% by weight based on the total of the organic semiconductor material different from the compound (1) and the compound (1). . The aforementioned organic insulating material may be a low molecular material or a high molecular material. The polymer material may be obtained by crosslinking a polymer. It is preferably a high molecular material. Specifically, for example, 'polystyrene, polycarbonate, polydimethyl siloxane, nylon, polyimine, cyclic olefin copolymer, epoxy polymer, cellulose, polymethylene oxide, polyolefin polymer Polyethylene polymer, polyester polymer, polyether polymer, polyamine polymer, fluorine polymer, biodegradable plastic, phenol resin, amine resin, unsaturated polyester resin, A copolymer obtained by combining a diallyl phthalate resin, an epoxy resin, a polyimide resin, a polyurethane resin, a polyoxyalkylene resin, and various polymer units. In the film of the present invention, the content of the compound (1) is preferably 10% by weight or more, and more preferably 20% by weight or more based on 100% by weight of the total of the organic insulating material and the compound (丨). The solution containing the compound (1) and an organic solvent can be obtained by, for example, dissolving the compound (1) in a solvent at 10 ° C to 200 ° C, preferably at 20 ° C to 150 ° C. -83-201206943 Next, the film and organic semiconductor device of the present invention will be described. The film of the present invention is a film containing the compound (1), preferably a film formed only of the compound (1). The thickness of the film is generally from 111111 to 10 lm, preferably from 5 nm to 1; / rn. When the film of the present invention has luminosity, it can be used as a luminescent film at this time. The term "luminescent film" refers to a film that emits light under conditions of light or electrical stimulation. The luminescent film is suitably used as a material of a light-emitting element, and a light-emitting element having a light-emitting film is one of the inventions, and the light-emitting element of the present invention is suitably used as a material such as an organic light-emitting diode. The light-emitting element 〃 refers to a device using a light-emitting film. Further, when the film of the present invention has the same conductivity as that of a semiconductor, it is preferably used as a conductive film. The "conductive film" refers to a film having electrical conductivity under conditions of light or electrical stimulation. A conductive film having the same conductivity as that of a semiconductor can be used as an organic semiconductor active layer. The conductive film is suitably used as a material such as an organic semiconductor device such as an organic transistor described later. The method for forming a film of the present invention is, for example, a coating film forming process. The coating film forming process means the film forming process of the step of applying the solution (1) to a substrate or an insulator layer after the compound (1) is dissolved in a solvent as described above. The coating method is, for example, casting, dip coating, die coating, roll coating, bar coating, spin coating, spray coating, screen printing, offset printing, and microcontact printing. These methods may be used alone or in combination of two or more. -84-201206943 A solution containing the compound (1) and an organic solvent is applied onto a substrate or an insulating layer to form a coating film, and then the solvent contained in the coating film is removed. A thin film is formed on the substrate or on the insulating layer. The organic solvent can generally be removed by natural drying, heat drying, reduced pressure drying, air drying, and the like. Further, two or more of these may be combined to be dried to remove the organic solvent. From the standpoint of ease of handling, it is preferred to dry naturally or heat dry. The removal of the organic solvent is preferably carried out by placing the substrate or heating the substrate with a hot plate (for example, 40 ° C to 250 ° (:, preferably 50 ° C to 200 ° C). The film of the present invention can also be used. It is formed by coating film formation processing using the dispersion of the compound (1) dispersed in a solvent. At this time, the coating film formation process using the solution of the compound (1) described above is carried out. In addition to the above organic solvent, Water can be used as a solvent. The film of the present invention can be formed by a simple method such as coating film formation or the like described above. The film of the present invention can also utilize the compound (1), using a vacuum evaporation method, a sputtering method, or a CVD method. And a method of forming a film by a vacuum step by a molecular line epitaxial growth method, etc. Forming a film by vacuum evaporation is a method of heating a compound (1) in a crucible or a metal dish under vacuum, and evaporating the compound (1) A method of vapor deposition on a substrate or an insulator material. The degree of vacuum during vapor deposition is generally the following, preferably 1 x 1 〇 · 3 Ρ a or less. The substrate temperature during vapor deposition is generally 〇 ° C to 300 ° C, preferably 2 (TC to 200 ° C. evaporation rate It is generally Ο-001 nm/sec to 10 nm/sec, preferably 0.01 nm/sec to 1 nm/sec. The compound-85-201206943 (n-yield) obtained by the above-mentioned coating film forming process or the above vacuum step The film thickness of the film can be appropriately adjusted depending on the element structure of the organic semiconductor device, but is preferably from 1 nm to 10 / Ζ m, more preferably from 5 nm to 1 μm. The organic transistor of the present invention contains, as an organic semiconductor, active. The film of the present invention for use in the layer. The organic crystal crystal has a high carrier mobility, preferably a carrier mobility of nr6cm2/vs or more, because it contains the compound (1) of the present invention. The carrier mobility can be used as a parameter. After measuring the 汲 current and the thyristor voltage, the analyzer calculates the 〇I d= (W/2 L) μ C i (Vg-V t) 2 (a) from the measurement result and the following formula (a). Id is the 汲 current in the saturation region of the electrical characteristics, L is the channel length of the organic transistor, W is the channel width of the organic transistor, Ci is the capacity per unit area of the gate insulating film, Vg is the gate voltage, and Vt is The critical 値 voltage of the gate voltage). The organic transistor of the present invention is an organic electric field effect transistor. The electric field effect transistor generally has a structure in which an organic semiconductor active layer (hereinafter abbreviated as a semiconductor layer) is connected to the source electrode and the germanium electrode, and the source electrode and the germanium electrode or the semiconductor layer are connected to the insulating layer (dielectric layer). And the insulating layer is connected to the gate electrode. The element structure of the organic transistor is as follows: (1) to (4) structure 〇 (1) substrate / gate electrode / insulator layer / source electrode - germanium electrode / semiconductor layer formation structure (2) Substrate/gate electrode/insulator layer/semiconductor layer/source electrode-汲电-86- 201206943 Polar formation structure; (3) Substrate/semiconductor layer+source electrode-汲 electrode/insulator layer/gate electrode formation (4) A structure in which a substrate/source electrode (or germanium electrode)/semiconductor layer+insulator layer+gate electrode/germanium electrode (or source electrode) is formed. When two or more layers of the semiconductor layer are present in each structure, a semiconductor layer or a semiconductor layer may be provided in the same plane. In each of the above structures, two or more source electrodes, a germanium electrode, and a gate electrode may be present. In the organic transistor of the present invention, the material constituting the source electrode, the ytterbium electrode, and the gate electrode may be a conductive material generally used in the field of organic transistors, and specific examples thereof include lead, gold, silver, nickel, chromium, and copper. , iron, tin, antimony, lead, molybdenum, indium, palladium, tantalum, niobium, tantalum, aluminum, niobium, tantalum, molybdenum, tungsten, tin oxide-bismuth, indium oxide-tin (ITO), fluorine rubber zinc oxide, zinc, Carbon, graphite, crystalline carbon, silver paste and carbon paste, lithium, barium, sodium, magnesium, potassium, calcium, barium, titanium, manganese, chromium, gallium, antimony, sodium, sodium-potassium alloy, magnesium, lithium, aluminum, Magnesium/copper mixture, magnesium/silver mixture, magnesium/aluminum mixture, magnesium/indium mixture, aluminum/aluminum oxide mixture, lithium/aluminum mixture, and molybdenum oxide, preferably uranium, gold, silver, copper, aluminum, nickel , indium, ITO, carbon and molybdenum oxide. Further, a known conductive polymer having a conductivity such as doping, a conductive polyaniline, a conductive polypyrrole, a conductive polythiophene, a poly(ethylene dioxythiophene) and a polystyrenesulfonic acid complex are used. Among them, it is preferable to reduce the electric resistance of the contact surface with the semiconductor layer. Two or more types of electrode materials can be used in combination. The film thickness of the electrode varies depending on the material, and is generally from 1 nm to 10 # m, and -87 to 201206943 is preferably from 5 nm to 5/z m, more preferably from 1 nm to 3/z m. When used as a substrate, the film thickness of the gate electrode may be larger than the film thickness. The method of forming the electrode film is as known in various methods. An empty vapor deposition method, a sputtering method, a coating method, a thermal transfer method, a printing method, and the like. The method which is preferably carried out at the time of film formation or after film formation may be various methods. Specifically, for example, a combined photoresist photolithography method, etc., such as a printing method such as inkjet printing, screen printing, or offset printing, or a soft lithography method such as a microcontact printing method, can be combined with two or more drawing methods for drawing. . The source electrode and the ruthenium surface treatment used in the organic transistor of the present invention are in contact with the film of the present invention (when the surface of the organic semiconductor electrode is subjected to surface treatment, it is preferred to enhance the crystal characteristics of the film body.) a saturated benzenethiol or perfluorobenzene having a thiol group (-SH), such as the above 1-octyl mercaptan, 1-perfluorooctyl mercaptan, or 1-octadecylthiooctadecyl mercaptan A solution of a thiol compound having a thiol group such as a thiol-containing aromatic thiol or a perfluorothiophene thiol, which is dissolved in an alcohol solvent, may be used for inorganic oxidation. The organic compound is an insulating film. Inorganic oxides such as oxidized chopped, oxidized, oxytitanium, tin oxide, palladium oxide, barium titanate, barium titanate titanate, lead titanate tantalum, barium titanate, titanium Barium strontium, magnesium strontium fluoride, strontium strontium sulphate, barium bismuth molybdate, barium strontium bismuth citrate and antimony trioxide, antimony, aluminum oxide, oxidized giant and titanium oxide. Another example is tantalum nitride, a gate electrode and a body, for example. , true method, sol condensation diagram, drawing diagram and etching plate printing, convex method, etc. Further, the electrode of the electrode can be electrically immersed in an alcohol, a 1-perfluorocarbon compound, or a thiophene ring. Various types of membranes, such as oxides, oxidized, barium titanate, barium titanate, and titanium are preferably inorganic nitrides of -88 - 201206943. Organic compound film such as polystyrene, polyimide, polyamine, polyester, polyacrylate, photoradical polymerization or photocationic polymerization photocurable resin, copolymerization with structural units derived from acrylonitrile The material, polyvinyl phenol, polyvinyl alcohol, furfural varnish resin and cyanoethyl polytriglucose (Pullulan) are preferably polystyrene, polyimide, polyvinyl phenol and polyvinyl alcohol. Two or more insulating layer materials can be used. The film thickness of the insulating layer varies depending on the material, and is generally from 0.1 nm to 100 / / m, preferably from 5 5 nm to 50 / / m, more preferably from 5 nm to 10 / z m. As the method of forming the insulating layer, various methods known in the art can be used. Specifically, for example, a coating method such as spin coating, spray coating, dip coating, casting, bar coating, draw coating, screen printing, offset printing, inkjet printing, vacuum evaporation, molecular line epitaxy, and ion Dry method such as group beam method, ion gold plating method, sputtering method, atmospheric pressure plasma method, CVD method, or the like. Further, as the sol-gel method or the aluminum oxide film treatment method on aluminum, the thermal oxide film of ruthenium is equal to the method of forming an oxide film on the metal. The substrate is a plate or a sheet made of a substrate material such as glass, paper, quartz, ceramic, or soft resin. Resin tablets such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyether maple (PES), polyether phthalimide, polyether ether ketone, poly benzene Base sulfide, polyacrylate, polyimine, polycarbonate (PC), cellulose triacetate (T AC ) and cellulose acetate propionate (CAP). The thickness of the substrate is preferably from 1/zm to 10mm, more preferably from 5/m to 5mm. The surface layer of the insulator layer and the substrate can be used for the surface layer of the insulator layer and the substrate. The surface characteristics of the element can be improved by surface treatment on the insulator layer of the laminated semiconductor layer. For the surface treatment, for example, drainage treatment using hexamethyldioxane, octadecyltrichlorosilane, octyltrichlorodecane or phenethyltrichloromethane, or hydrochloric acid, sulfuric acid, hydrogen peroxide water or the like is used. Acid treatment, alkali treatment using sodium hydroxide, potassium hydroxide, calcium hydroxide, ammonia, etc., ozone treatment, fluorination treatment, plasma treatment using oxygen or argon, formation of a Lamyra projection film, other insulators, etc. For example, a semiconductor film formation process, a mechanical process, an electrical treatment such as corona discharge, a brushing treatment using a fiber or the like, or a combination of two or more types of treatment methods may be used. The surface treatment is carried out, for example, a vacuum deposition method, a sputtering method, a coating method, a printing method, a sol-gel method, or the like. A protective film formed of a resin or an inorganic compound may be disposed on the semiconductor layer. The effect of the external gas can be suppressed by forming a protective film, and the transistor can be driven to stabilize. The organic transistor of the present invention can be used for liquid crystal display elements, organic electroluminescent elements, electronic paper, sensors, and RFID (radio frequency identification cards). Such as organic devices. [Embodiment] Hereinafter, the present invention will be specifically described by way of Examples, but the present invention is not limited to the Examples. Further, it was confirmed by gas chromatography analysis and/or high-speed liquid chromatography analysis that -90-201206943 reaction proceeded. The conditions of each analysis are as follows. <Gas Chromatography Analysis> Apparatus: GC2010 manufactured by Shimadzu Corporation: DB-1 manufactured by J&W Sainti Co., Ltd. (inner diameter: 0.25 mm, length: 30 m) <High-speed liquid chromatography>

Apparatus: LC10AT column manufactured by Shimadzu Corporation: L-column ODS (inner diameter: 4.6 mm, length: 15 cm) manufactured by Chemical Substance Evaluation Co., Ltd. The high-speed liquid chromatography purification system was carried out by using the following apparatus and column. Device: LC-250HS column manufactured by Nippon Analytical Industries Co., Ltd.: JAIGEL-ODS-AP-50L (inner diameter: 50 mm, length: 25 cm) manufactured by Sakamoto Analytical Co., Ltd. The resulting product is based on W-NMR, HRMS, and/or The measurement result of LC-HRMS was confirmed. Apparatus for measuring by j-NMR: Apparatus for measuring the DPX300 by the EX270 or BRUKER company manufactured by JEOL Ltd.: JMS-T100GC manufactured by JEOL Ltd. LC-HRMS measuring device: QSTAR XL manufactured by Applied Biosystems Co., Ltd. (column: chemical substance) Evaluation mechanism L-column ODS (inner diameter: 4.6 mm, length: 15 cm) -91 - 201206943 [Example 1: Production of 3,6-dibromo-2,5-diiodothiophene [3,2-b Thiophene] 2.5-dibromothieno[3,2-b]thiophene is prepared by reacting thieno[3,2-b]thiophene with quinone imine N-bromosuccinate (refer to Dalton Trans., 2005, 874). 3.6-Dibromothieno[3,2-b]thiophene is obtained by reacting 2,5-dibromothieno[3,2-b]thiophene with lithium diisopropyl decylamine (refer to 〇r g. Lett·, 2007, 9, 1 005 ). 3,6-dibromothieno[3,2-1)]thiophene 12.0 (^, iodine 8.188, iodic acid 3.54 g, sulfuric acid 0.39 g, carbon tetrachloride 132 ml, acetic acid 264 ml, and water 41 ml were placed in stirring The mixture was stirred in a 1 000 mL four-necked flask of a thermometer and a condenser. The resulting mixture was stirred at 45 ° C for 20 hours under nitrogen. 0.45 g of iodine and 0.20 g of iodic acid were added to the resulting mixture, followed by stirring at 45 ° C under nitrogen. After 10 hours, the obtained reaction mixture was cooled to room temperature and then filtered. The obtained solid was washed with water and methanol, and then dried under reduced pressure, and recrystallized to give a yield of 88% of the following formula: 3,6- White crystal of bromo-2,5-diiodothieno[3,2-b]thiophene 1 9.5 g.

The result of W-NMR (5, CDC13) measurement did not detect 1H-peak enthalpy. [Example 2: Production of 3,6-dibromo-2,5-bis(3-bromobenzo[b]thiophen-2-yl)-thiophene well [3,2-b]thiophene] 2,3- Dibromobenzo[b]thiophene 22.5 g (manufactured by Erdori Co., Ltd.) was placed in -92 - 201206943 A 500 mL four-necked flask equipped with a stir bar, a thermometer, a condenser, and a dropping funnel. After replacing the inside of the flask with nitrogen, a solution of 230 ml of dehydrated tetrahydrofuran was added by a syringe at room temperature. After the obtained solution was cooled to _3 〇〇c, 76.3 ml of a tetrahydrofuran solution (concentration: 1.00 M' manufactured by Tokyo Chemical Co., Ltd.) of isopropylmagnesium bromide was added thereto at the same temperature for 45 minutes. After stirring the resulting mixture for 30 minutes at the same temperature, the resulting solution was cooled to _50 〇c, and a solution of zinc chloride in diethyl ether was added at the same temperature for 20 minutes (concentration: i 〇〇m, manufactured by Erduri) ) 76.3ml. After the resulting mixture was stirred at the same temperature for 10 minutes, the mixture was gradually warmed to room temperature, and the solvent was evaporated under reduced pressure to give white crystals. 3,6-dibromo-2,5-diiodothio[3,2-15]thiophene 14.0 § and tetrakisphenylphosphine 2.7 g (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the obtained crystal, and the inside of the flask was replaced with nitrogen. Then, dehydrated tetrahydrofuran 2 3 0 m 1 was added using a syringe. The resulting mixture was stirred under reflux for 7 hours. After the resulting solution was cooled to room temperature, 1 equivalent of hydrochloric acid and toluene were added. After filtering the obtained mixture, the obtained solid was washed with water and methanol, and dried to give 3,6-dibromo-2,5-bis(3-bromobenzo[b]thiophen-2-yl)-thieno[ The yield of the yellow crystal of 3,2-b]thiophene relative to 3,6-dibromo-2,5-diiodopyrano[3,2-b]thiophene was 73%.

HRMS ( EI+ ) : found 719.6175 ( calcd. for C22H8Br4S4 : 7 1 9.6201 ) [Example 3] -93- 201206943 3,6-Dibromo-2,5-bis(3-bromobenzo[b] under nitrogen 9.00 g of thiophen-2-yl)-thieno[3,2-b]thiophene, 2.29 g of tris(dibenzylideneacetone)dipalladium, racemic-2,2'-bis(diphenylphosphino) linkage 6.23 g of naphthalene, 25.48 g of dodecylamine, 450 g of sodium tert-butoxide, and 450 ml of dehydrated toluene were placed in a l〇〇〇mL four-necked flask equipped with a stir bar, a thermometer and a condenser. Nitrogen environment The resulting mixture was heated to reflux and refluxed for 24 hours. After the resulting reaction mixture was cooled to room temperature, water was added and extracted with toluene. The resulting organic layer was dried over magnesium sulfate and filtered. The obtained filtrate was concentrated under reduced pressure, and purified by silica gel chromatography using a solvent mixture of hexane and toluene which added 0.2% by volume of triethylamine. The solid obtained by recrystallization from toluene was purified by high-speed liquid chromatography (moving layer: a mixed solvent of tetrahydrofuran and acetonitrile) to obtain a white-yellow crystal of 2.44 g of the compound represented by the following formula. The yield was 25%.

111^1^111(5/??1«, tetrahydrofuran-(18): 0-86〇, 61〇, 1.25~1,65 (m, 36H), 2.00~2.13(m,4H), 4.67 ( t N , C12H25

, 4H) ' 7.25 ( t - 2H ) , 7.39 (t, 2H), 7.86 (d, 2H ), 7.95 ( d, 2H ) LC-HRMS ( APPI + ) : found 767.3 5 5 3 ( calcd for C46H59N2S4 : 767.3556) [Thin film and organic transistor using the film as an organic semiconductor active layer-94-201206943 Production Example 1] The chromium and gold were vapor-deposited on a glass substrate in this order using an emission step or photolithography, and a source and a germanium electrode were provided. The thickness of the chromium layer is 5 nm and the thickness of the gold layer is 40 nm. The substrate was ultrasonically washed with acetone and isopropyl alcohol, dried, washed with oxygen plasma, and heated at 80 ° C for 5 minutes. The channel width is 2mm and the channel length is 50//m. The channel portion was treated with phenethyltrichloromethane, and after the electrode portion was subjected to pentafluorobenzenethiol treatment, a 0.5 wt/vol% tetraphosphorus solution of the compound produced in the above [Example 3] was dropped into the nitrogen atmosphere, and then A thin film (organic semiconductor active layer) is formed by spin coating. Next, a solution containing a fluorine-based polymer was dropped on the film, and an insulating layer was formed by spin coating. The film thickness at this time was 25 nm, and the thickness of the insulating layer was 300 nm. An organic oxide crystal as shown in Fig. 2 was fabricated by using a mask on the insulating layer and sequentially depositing chrome and aluminum to form a gate electrode. The thickness of the chromium layer was 5 nm, and the thickness of the aluminum layer was 2 0 Onm 〇 The electrical characteristics of the obtained organic transistor were measured. As a result, in the gate voltage (Vg), the curve of the 汲 current (Id) with respect to the 汲 voltage (Vd) is good, and the higher 汲 voltage has a saturation region. Further, when the negative gate electrode applied to the gate electrode is increased, a negative erbium current is also increased, so that the obtained organic transistor is a p-type organic transistor. Further, the carrier mobility of the organic transistor was calculated by the above formula (a), and as a result, the carrier mobility was 0.25 cm 2 /Vs. [Example 4: Production of 5,5'-dibromobenzo[l,2-b; 4,5-b']dithiophene] Referring to the method described in Chem. Mater, 2010, 22, 5314, - 95-201206943 The following method produces 5,5'-dibromobenzo[l,2-b:4,5-b']dithiophene β to give benzo[l,2-b; 4,5-b'] The crystal of a thiophene o.ggg is added to the reaction vessel provided with a stirrer and a thermometer to replace the inside of the vessel with nitrogen. 220 ml of dehydrogenated tetrahydrofuran was added to the vessel, and the crystal was dissolved at room temperature (about 25 ° C). After cooling the resulting solution to -7 8 ° C, a solution of t-butyllithium in hexane (concentration: 1.5 9 M, manufactured by Kanto Chemical Co., Ltd.) 8.73 ml was maintained at about -7 8 ° C for 5 minutes » at the same temperature. After the resulting mixture was stirred for 1 hour, the reaction mixture A was obtained. A solution obtained by dissolving 4.60 g of carbon tetrabromide (manufactured by Tokyo Chemical Industry Co., Ltd.) in 20 ml of dehydrated tetrahydrofuran in 10 minutes was adjusted to _78. (In the reaction mixture A, the resulting mixture was stirred for another 4 hours at the same temperature. After the resulting reaction mixture was warmed to room temperature, chloroform and water were added thereto, and the mixture was stirred well, and filtered by a filter coated with a light. The mixture was separated to remove the insoluble matter. After the obtained filtrate was separated, the obtained organic layer was dried over magnesium sulfate. After filtration, the obtained filtrate was concentrated under reduced pressure to give 5,5'-dibromobenzene represented by the following formula. [1,2-1»: 4,5-1) '] Yellow-brown crystal of dithiophene 2.018.

t> Br 'H-NMR ( δ /ppm ' CDC13 ) : 7.34 ( s > 2H ) , 8.03 (s, 2H) [Example 5: Production of 5,5,-bis(2-nitrophenyl)benzene And H,2-b; 4,5-b']dithiophene] 5,5,-dibromobenzo[1,2-15;4,5-1)']dithiophene 1.708, 2 - (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitro 201206943 benzene 3.65g (manufactured by Wako Pure Chemical Industries, Ltd.), palladium acetate O.llg (made by Erdori), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl 0.40g (manufactured by Erdori Co., Ltd.), tripotassium phosphate 15.55g and tetrahydrofuran 170mL Stirring, thermometer and condenser in a four-necked flask. After heating to reflux under a nitrogen atmosphere, it was refluxed for 4 hours. After the resulting reaction mixture was cooled to room temperature, the solvent was removed under reduced pressure. Water was added to the concentrated residue and filtered. The obtained solid was washed with water and methanol, and dried under reduced pressure to give 5,5'-bis(2-nitrophenyl)benzo[1,2-b; 4,5- represented by the following formula. b'] The brown crystal of dithiophene was 1.69 g. Yield: 80%.

• H-NMR ( δ /ppm > CDC13 ) : 7.34 ( s · 2H ) > 7.52 to 7.71 (m, 6H), 7_85 (d, 2H), 8.25 (s, 2H) [Example 6] , 5'-bis(2-nitrophenyl)benzo[l,2-b; 4,5-b']dithiophene 1.60 g was placed in a four-necked flask equipped with a stirrer, a thermometer and a condenser. The inside of the flask was replaced with nitrogen. After adding l〇〇mL of triethyl phosphite, the resulting mixture was heated to reflux under a nitrogen atmosphere, and refluxed for 5 hr. The resulting reaction mixture was cooled to room temperature and filtered. The solid obtained was washed with methanol, and dried under reduced pressure to give 0.51 g of yellow brown crystals of the compound of the formula. Yield: 37%. -97- 201206943

j-NMRC <5/ppm, tetrahydrofuran-d8): 7.17 (txd, 2H), 7.27 (txd, 2H) ' 7.55 ( d > 2H ) , 7.73 (d, 2H), 8.46 ( s, 2H ) , 1 1 · 1 3 ( s, 2H ) [Example 7] The compound obtained in the above [Example 6] was 〇.43 g, 1-iodohexane 1.49 g (manufactured by Tokyo Chemical Industry Co., Ltd.), 40% by weight of tetrabutylammonium hydrogen 0.08 g of an aqueous oxide solution (manufactured by Tokyo Chemical Industry Co., Ltd.), 9.34 g of a 1% by weight aqueous sodium hydroxide solution, and 26 mL of tetrahydrofuran were placed in a four-necked flask equipped with a stir bar, a thermometer, and a condenser. The resulting mixture was heated to reflux under a nitrogen atmosphere and refluxed for 4 hours. After the resulting reaction mixture was cooled to room temperature, water and toluene were added for liquid separation. The resulting organic layer was dried over magnesium sulfate and filtered. After the obtained filtrate was concentrated under reduced pressure, the obtained residue was purified by silica gel column chromatography using a solvent mixture of a mixture of hexane and toluene of triethylamine in a volume ratio of 0.2%. The obtained solid was recrystallized (solvent: toluene) to give a yellow crystal of the compound represented by the following formula: 13 g. Yield: 21%.

• H-NMRC (5/ppm, tetrahydrofuran-d8): 0·91 (t, 6H), 1.28 to 1.61 (m, 12H), 1.95 to 2.10 (m, 4H), 4.79 (t

, 7.63 ( d, 2H , 4H ) , 7.19 ( t, 2H ) , 7.34 ( t, 2H ) -98 - 201206943 ), 7.71 ( d, 2H), 8 · 71 ( s, 2H ) LC-HRMS ( APPI + ) : found 5 3 7.23 92 ( calcd. for C34H37N2S2 : 53 7.23 92 ) [Production Example 2 of film and organic transistor using the film as an active layer of an organic semiconductor] η-type ruthenium substrate with high concentration doping gate electrode The surface of Fig. 2, 31), was thermally oxidized to form a tantalum oxide film of 300 nm (Fig. 2, 32). Secondly, the chrome layer and the gold layer were laminated on the tantalum oxide film by photolithography, and a source electrode (33 in Fig. 2) and a tantalum electrode (Fig. 2, 34) having a channel length of 100 μm and a channel width of 1 mm were fabricated. The obtained substrate was ultrasonically washed with acetone for 10 minutes, and then irradiated with ozone for 30 minutes. Next, the substrate irradiated with UV was immersed in a toluene solution containing phenylethyltrichloromethane for 2 minutes, and the surface of the substrate was subjected to decane treatment. After preparing a xylene solution of the compound produced in the above [Example 7] at a concentration of 0.7% by weight, the xylene solution was filtered through a membrane filter to prepare a coating liquid. The obtained coating liquid was applied onto the surface of the tantalum oxide film, the source electrode and the tantalum electrode of the substrate after the decane treatment by a spin coating method. The substrate coated with the coating liquid facing up is dried on a hot plate at 50 ° C for 30 minutes in a nitrogen atmosphere to form a film having a thickness of about 25 nm (organic semiconductor active layer, 3 of FIG. 2 ) The organic transistor described in Fig. 2 is obtained. The source/turn-to-turn voltage Vsd of the organic transistor was set to -40 V, and the transistor characteristics were measured by changing the gate voltage Vg from 20 V to -40 V. -99-201206943 The carrier mobility of the organic transistor was calculated from the measurement characteristics obtained by the measurement to be 6.1 x 10 -5 cm 2 /Vs. [Embodiment 8]

After cooling 30 mL of a solution of 3-bromo-2-iodothieno[3,2-b]thiophene (10 mmol) in tetrahydrofuran to _78 ° C, η-butyllithium (1.6 M, hexane solution) was added dropwise. lOmmol), the resulting mixture was stirred for an additional 1 hour. BujSnCl (10 mmol) was added dropwise to the resulting solution, and the resulting mixture was stirred, and the mixture was warmed to 25 t and then stirred for 1 hour. Bis(triphenyls)palladium (1 mmol) and 1,4-dibromo-2,5-diiodobenzene (5111111〇1) were added to the resulting solution, and the resulting mixture was stirred at 65 ° C for 8 hours. After concentration, the residue was purified by silica gel column chromatography to give a compound represented by the following formula.

[Embodiment 9] 100-201206943

The compound (5 mmol) obtained in the above [Example 8], η-dodecylamine (25 mmol), tris(dibenzylideneacetone)dipalladium (1 mmol), sodium tert-butoxide were refluxed under a nitrogen atmosphere. (50 mmol) A mixture of '(±)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (4 mmol) and toluene (100 mL) for 2 h. After the resulting reaction mixture was cooled to room temperature, water was added and extracted with chloroform. The obtained organic layer was dried over magnesium sulfate, filtered, and evaporated. The obtained mixture was purified by silica gel column chromatography to give a compound represented by formula (2-7). The compound represented by the sublimation formula (2-7) is refined. [Production Example 3 of Film and Organic Oxide Crystal Using the Film as Organic Semiconductor Active Layer] The doping of the SiO2 thermal oxide film of 200 nm after the treatment of the octyl trichloromethane treatment with the metal cover for forming the organic semiconductor layer On the board, you need to cover the board. Next, in a chamber in which the degree of vacuum is set to 1×1 (Γ3 Pa or less), the circuit board is placed in a tungsten vessel in which the compound represented by the formula (2-7) obtained in the embodiment 9 is placed, and the vessel is heated while the vessel is heated. The circuit board is heated to room temperature (24 ° C) or more and below 15 ° C to form an organic semiconducting -101 - 201206943 bulk layer formed of a film of the compound represented by the formula (2-7) in a portion without a metal cover. After the metal cover is removed, a metal cover for forming the source electrode and the germanium electrode is placed on the surface of the organic semiconductor layer, and a metal layer having a film thickness of 40 nm is formed on the organic semiconductor layer by the same vacuum evaporation method to form a source. The electrode and the ruthenium electrode can be used to produce the organic transistor shown in Fig. 1. [Production Example 4 of film and organic transistor using the film as an active layer of an organic semiconductor] The formula (2-7) obtained in Example 9 is represented. The compound was dissolved in hydrazine-xylene to prepare a solution having a concentration of the compound represented by the formula (2-7) of 0.3% by weight. The metal cover for forming the organic semiconductor layer was placed in the treatment with phenethyltrichloromethane. Doped with Si02 thermal oxide film On the board, the circuit board is covered with a cover. Next, the solution is applied onto the circuit board by spin coating to form a film formed of the compound represented by the formula (2-7). The formed film is kept at 80t. After the next 30 minutes, an organic semiconductor layer formed of a film of the compound represented by the formula (2-7) can be formed in a portion without a metal cover. Next, after removing the metal cover, a metal cover for the source electrode and the germanium electrode is formed. On the surface of the organic semiconductor layer, a metal layer having a thickness of 40 nm is formed on the organic semiconductor layer by the same vacuum deposition method to form a source electrode and a germanium electrode, and the organic transistor shown in Fig. 1 can be produced. UTILITY OF THE INVENTION The present invention can provide a polycyclic compound capable of imparting a film-102-201206943 suitable for an organic semiconductor active layer. [Simplified Schematic] FIG. 1 is a polycyclic ring containing the organic semiconductor layer containing the present invention. Fig. 2 is a schematic view showing an embodiment of an organic transistor of a film of a compound. Fig. 2 is another example of an organic transistor containing a film of the polycyclic compound of the present invention for an organic semiconductor layer. Outline of the form. [Description of main component symbols] 1 1 : Substrate 1 2 : Gate electrode 1 3 : Gate insulating film 1 4 : Source electrode 1 5 : Strontium electrode 16 : Organic semiconductor layer 31 : 矽 Substrate 3 2 : Antimony oxidation Film 3 3 : source electrode 3 4 : germanium electrode 35 : organic semiconductor active layer - 103-

Claims (1)

201206943 VII. Application for Patent Park: 1. A polycyclic compound, which is of formula (1) (wherein, the ring structure c is a benzene ring represented by the formula (C1), a hetero [3,2-b] heterocyclic ring represented by the formula (C2) or a benzo[i,2- represented by the formula (C3). b: 4,5-b'] diheterocyclic ring; (wherein P and Q are independently a sulfur atom, an oxygen atom, a selenium atom or a ruthenium atom, and the benzene ring constituting the above ring may have a substituent) W, X, Y and Z are independently a sulfur atom, an oxygen atom, a selenium atom, Helium atom, S〇2, (R1 b-CjR12), (R13)-Si-(R14) or N-(R15), and at least one selected from the group consisting of W, X, Y and Z is N -(R15); Ring structure A and ring structure B are independently an aromatic carbocyclic ring which may have a substituent or an aromatic hetero ring which may have a substituent, and ring structure C is a benzene ring represented by formula (C1), When X and Y are N-(R15), the ring structure A and the ring structure B are independently an aromatic hetero ring which may have a substituent; and RM, R12, R13 and R14 are independently an alkane having one or more halogen atoms. A polycyclic compound represented by a group or a hydrogen atom, and R15 is independently an alkyl group which may have one or more halogen atoms. 2. A polycyclic compound as claimed in claim 1, wherein W, X, Y and Z are independently a sulfur atom, an oxygen atom, a selenium atom or N-(R15)'-104-201206943 and 1, 乂, 丫And at least one selected from the group consisting of z and n_(rm) 〇3. The polycyclic compound of claim 2, wherein at least 2 of the groups selected by W, X, γ, and z are selected. One is n-(r15). 4. The polycyclic compound of claim 1, wherein the ring structure C is a heterocyclic [3,2_b] heterocyclic ring represented by the formula (C2) or a benzo[1,2 represented by the formula (C3). -b: 4,5-b,] diheterocyclic. 5. The polycyclic compound of claim 1, wherein ring structure C is a benzene ring represented by formula (C1), X and γ are independently n_(R15) 'W and Z is independently a sulfur atom or an oxygen atom. Or a selenium atom, a ring structure a and a ring structure B are independently an aromatic hetero ring which may have a substituent. 6. The polycyclic compound of claim 1, wherein ring structure C is a benzene ring represented by formula (C1), and X and Y are independently a sulfur atom, an oxygen atom or a selenium atom, and W and Z are independently N-(R15). 7. The polycyclic compound according to any one of claims 1 to 6, wherein the aromatic carbocyclic ring which may have a substituent is a benzene ring which may have a substituent or a naphthalene ring which may have a substituent. The aromatic heterocyclic ring which may have a substituent is a thiophene ring which may have a substituent, a benzo[b]thiophene ring which may have a substituent or a thieno[3,2-b]thiophene ring which may have a substituent. 8. The polycyclic compound of claim 4, wherein ring structure C is a thieno[b]thiophene ring, a benzo[l,2-b:4,5-b']di which may have a substituent A thiophene ring or a benzo[l,2-b:4,5-b']difuran ring which may have a substituent. 9. The polycyclic compound of claim 4, wherein ring -105-201206943, structure C is a thieno[3,2-b]thiophene ring or an unsubstituted benzo[l,2-b:4, 5-b']dithiophene ring. 10. The polycyclic compound of claim 4, wherein one of W and X is N-(r^), and the other is a sulfur atom, an oxygen atom or a selenium atom. One of Y and Z is n- (R15), the other side is a sulfur atom, an oxygen atom or a selenium atom. A polycyclic compound according to the first aspect of the invention, wherein X is N-(R15), W is a sulfur atom, and γ is n-(R15)' Z is a sulfur atom. A polycyclic compound according to the first aspect of the invention, wherein W is N-(R15), X is a sulfur atom, and z is N-(R15)'Y is a sulfur atom. 3. The polycyclic compound of claim 5, wherein the ring structure A and the ring structure B are independently a thiophene ring which may have a substituent. 14. The polycyclic compound of claim 5, wherein X and Y are the same N-(R15), and W and Z are sulfur atoms. 15. The polycyclic compound of claim 6, wherein the ring structure A and the ring structure B are independently a benzene ring which may have a substituent, a naphthalene ring which may have a substituent or a thiophene ring which may have a substituent. 16. The polycyclic compound of claim 6, wherein w and Z are the same N-(R15), and both X and Y are a sulfur atom or an oxygen atom. A film comprising a polycyclic compound according to any one of claims 1 to 16 of the patent application. A film formed of only a polycyclic compound as disclosed in any one of claims 1 to 6 of the patent application. 1 9. An organic transistor comprising: 20.18 of the scope of the patent application No. -106-201206943: 2 1. The film of the 19th or the I. An organic transistor comprising a film as described in the patent application. An organic semiconductor device comprising an organic transistor as claimed in claim 20. 107- •βιί