TW201245216A - Compound for organic transistor - Google Patents

Abstract

A compound represented by formula (1) [wherein X, Y, W and Z independently represent a sulfur atom, an oxygen atom or a selenium atom; n represents 0 or 1; and P1, P2, Q1 and Q2 independently represent a group represented by formula (2) (wherein R represents a hydrogen atom, an alkyl group which may be substituted, an aryl group which may be substituted, or a silyl group which may be substituted), an aromatic hydrocarbon group which may be substituted, or an aromatic heterocyclic group which may be substituted, wherein at least one group selected from P1, P2, Q1 and Q2 represents the group represented by formula (2)], which can be used in a thin film that can act as an organic semiconductor active layer.

Description

201245216 VI. Description of the Invention: [Technical Field of the Invention] The present invention relates to a compound 'the method for producing the compound, a film containing the compound, an organic transistor containing the film, and the like. [Prior Art] Recently, an organic transistor has been used as an element of an electronic paper, a large-screen burnable display or the like. The organic electro-optic system is composed of a member such as an organic semiconductor active layer, a substrate, an insulating layer, and an electrode. For example, JP-A-2006-1 1 458 1 discloses vacuum vapor deposition and pentacene. The film serves as an organic transistor of an organic semiconductor active layer. In this case, a novel compound which requires a film of an organic semiconductor active layer is required. SUMMARY OF THE INVENTION The present invention provides a novel compound which can obtain a film of an organic semiconductor active layer. <1 &gt; A compound 'is represented by the following formula (1):

[wherein, X, Y, W and Z each independently represent a sulfur atom, an oxygen atom or a sun atom, and η represents 0 or 1, -5 - 201245216 P1, P2, Q1 and Q2 each independently represent the following formula (2) Base: —=R (2) (wherein R represents a hydrogen atom, a substituted alkyl group, an optionally substituted aryl group or a substituted fluorenyl group), a substituted aromatic hydrocarbon group or a The substituted aromatic heterocyclic group, wherein at least one of P1, P2, Q1 and Q2 is a group represented by the formula (2). <2> The compound according to <1>, wherein the group represented by the formula (2) is a group represented by the formula (3): (3) = -Si-R2

I R3 (wherein R1, R2 and R3 each independently represent an alkyl group having 1 to 16 carbon atoms or an aryl group having 6 to 12 carbon atoms). <3> The compound according to <1> or <2>, wherein X, γ, W and Z are each a sulfur atom. <4> The compound according to any one of <1> to <3> wherein P1 and P2 are the same group represented by the formula (2), and Qi and Q2 are the same and are an aromatic hydrocarbon group or an aromatic group. Heterocyclic group. The compound according to any one of the items <1> to <4>, wherein η is 0 -6 - 201245216 <6> the compound according to any one of <1> to <5>, Wherein Q1 and Q2 are the same and are thieno[3,2-b]thiophen-2-yl. <7> A method for producing a compound represented by the following formula (lb),

(wherein n' W, X, Y, Z, R and Q have the same meanings as defined below), which comprises a metal compound containing Q in the presence of a transition metal compound (wherein Q represents an aromatic hydrocarbon group) Or an aromatic heterocyclic group), a step of reacting with a compound represented by the following formula (ia):

(wherein X, Y, W and Z each independently represent a sulfur atom, an oxygen atom or a selenium atom, and R represents a hydrogen atom, a substituted alkyl group, a substituted aryl group or a substituted decyl group, η Indicates 0 or 1, and X^ each independently represents a halogen atom). <8> a compound represented by the following formula (1 a ),

201245216 (wherein, X, Y, W and z each independently represent a sulfur atom, an oxygen atom or a selenium atom, and R represents a hydrogen atom, a substituted alkyl group, a substituted aryl group or a substituted decyl group, η represents 〇 or 1, and χΐ each independently represents a halogen atom). <9> The compound according to the item <8>, wherein in the formula (?a), ruthenium, osmium, iridium and 2 are each a sulfur atom. <1 〇> The compound described in the item <8> or <9>, wherein n in the formula ( la ) is 〇. <11> The compound according to any one of the items <8> to <1>, wherein the oxime in the formula (la) is an iodine atom. <1 2 &gt; The compound described in any one of the items <8> to <1丨>, wherein R is represented by the following formula:

(wherein R, R2 and R3 each independently represent an alkyl group having a carbon number of 1616 or an aryl group having a carbon number of 6 to 12). <13> A method for producing a compound represented by the following formula (la);

-8 - 201245216 (wherein ^^尺~...~乂~丫 and / means the same meaning as the following 'χ1 each independently represents a halogen atom), and the method includes a compound represented by the following formula (1〇:

(wherein, w, x, Y & z each independently represent a sulfur atom, an oxygen atom or a selenium atom, and R represents a hydrogen atom, a substituted alkyl group, a substituted aryl group or a substituted decyl group 'n A step of reacting hydrazine or 1) with an alkyllithium, and a step of reacting the reaction product obtained in the foregoing step with a halogenating agent containing hydrazine as a halogen atom. <14> a compound represented by the following formula (1c),

(wherein, 1, 乂, 丫 and z each independently represent a sulfur atom, an oxygen atom or a selenium atom. 'R represents a decyl group which may be substituted, and η represents 〇 or 1). <15> The compound according to the item <14>, wherein W, X, Y and Z in the formula (丨c) are each a sulfur atom. <16> The compound according to the item <14> or <1 5>, wherein η in the formula (lc) is 〇. <17> A method for producing a compound represented by the following formula (lc), -9-201245216

R

(wherein n, W, X, Y, z and R have the same meanings as defined below), and the method comprises the compound represented by the following formula (Id) in the presence of a transition metal compound, a copper halide and an organic base, Human/wk"x2 MTUTi (1d) (wherein X, Y, W and z each independently represent a sulfur atom, an oxygen atom or a selenium atom, η represents 0 or 1, and X2 each independently represents a halogen atom), and is represented by the following formula ( 5) The steps of the compound reaction indicated: Η

(5) (wherein R represents a decyl group which may be substituted). <18> A compound represented by the following formula (id), , Na 2...) (wherein X, Y, W and Z each independently represent a sulfur atom, an oxygen atom-10-201245216 or a selenium atom, and η represents 0 or 1 , X2 means changing atoms). <19> A composition comprising a compound represented by the following formula (1) and an organic solvent: (1) P2^Z〇^Y^Q1 (wherein, X, Y, W and Z each independently represent a sulfur atom, An oxygen atom or a selenium atom, η represents 0 or 1, and P1, P2, Q1 and Q2 each independently represent a group represented by the following formula (2): —Ξ-R (2) (wherein R represents a hydrogen atom and can be substituted An alkyl group, a substituted aryl group or a substituted decyl group), a substituted aromatic hydrocarbon group or a substituted aromatic heterocyclic group, at least one of P^P^Q1 and Q2 is Formula (2) represents the base). <20> A method for producing a film comprising the steps of applying the composition described in the item <19> to a substrate, and drying the coating film applied on the substrate. <21> A film comprising the compound represented by the formula (1) as described in any one of items <1> to <6>. <22> A film comprising a compound represented by the formula (1) as described in any one of <1> to <6>. <23> An organic semiconductor device comprising the film according to the item <21> or <22 -11 - 201245216>. <24> An organic transistor comprising the film as described in <21> or <22>. [Embodiment] Hereinafter, the present invention will be described in detail. The present invention is a compound represented by the following formula (!) (compound (1)).

X, γ, w and Z in the compound (1) each independently represent a sulfur atom, an oxygen atom or a selenium atom. Preferably, each is a sulfur atom. π represents 0 or 1. When n is hydrazine, the compound (1) can be represented by the following formula:

When it is 1, the compound (1) can be represented by the following formula:

η is preferably 0. -12- 201245216 P1, P2, Q1 and Q2 each independently represent the base represented by the following formula (2):

R A substituted aromatic hydrocarbon group or a substituted aromatic heterocyclic group. At least one of P1, P2, Q1 and Q2 is a group represented by the formula (2). Preferably, the combination of P1, P2, Q1 and Q2 is exemplified by the fact that P1 and P2 are the same as those represented by the formula (2), and Q1 and Q2 are the same as the substituted aromatic hydrocarbon group or the substituted aromatic heterocyclic group. In the case where Q1 and Q2 are the same as those represented by the formula (2), and P1 and P2 are the same as the substituted aromatic group or the substituted aromatic heterocyclic group. First, the group represented by the formula (2) is described. The R group contained in the formula (2) represents a hydrogen atom, a substituted alkyl group, a substituted aryl group or a substituted decyl group. It is preferably a substituted alkyl group, a substituted aryl group or a substituted decyl group. The alkyl group in R may, for example, be a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, and specific examples thereof include a methyl group, an ethyl group, a n-propyl group, a n-butyl group, and a positive alkyl group. Amyl, n-hexyl, n-heptyl, n-octyl, n-decyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecane Base, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-icosyl, n-docosyl 'n-docosyl, positive twenty-three Alkyl, n-tetracosyl, n-pentadecyl, n-hexadecyl, n-hexadecyl, n-octadecyl, n-dodecyl, n-tridecyl Carbon number such as linear alkyl group having 1 to 30 carbon atoms, isopropyl group, second-13-201245216 butyl group, tert-butyl group, neopentyl group, 2-ethylhexyl group, 2-hexyldecyl group, etc. a branched alkyl group of ～30, a cycloalkyl group having a carbon number of 5 to 30, such as a cyclopentyl group or a cyclohexyl group. The alkyl group represented by R is preferably a methyl group, an ethyl group, a n-propyl group, an isopropyl group or a positive group. Butyl, t-butyl, tert-butyl, n-pentyl 'neopentyl, cyclopentyl, n-hexyl , 2-ethylhexyl, cyclohexyl, n-heptyl, n-octyl, cyclooctyl, n-decyl, n-decyl, 2-hexyldecyl, and the like, an alkyl group having 1 to 16 carbon atoms, represented by R The group may, for example, be an aryl group having 6 to 30 carbon atoms, and preferably an aryl group having 6 to 12 carbon atoms such as a phenyl group or a naphthyl group. The alkyl group and the aryl group represented by R may have one or more substituents, and examples of the substituent are as described later with P1. 2, ^^ or Q2 represents an aromatic hydrocarbon group and an aromatic heterocyclic group which may have the same substituents. When R is a decyl group which may be substituted, the group represented by the formula (2) may be represented by the following formula (3): R1 -=-Si - R2 (3)

I R3 (wherein R1, R2 and R3 each independently represent an alkyl group having 1 to 16 carbon atoms or an aryl group having 6 to 12 carbon atoms). The decyl group which may be substituted is preferably a group represented by the following formula: -14- 201245216 R1 —Si—R2

I R3 (wherein R1, !^, and R3 represent the same meaning as described above). Here, the alkyl group and the aryl group are the same as those of the alkyl group having 1 to 16 carbon atoms and the carbon number 6 to 12 exemplified as the above R. The group represented by the formula (3) is preferably a group represented by the formula (3) in which R1, R2 and R3 are the same as a methyl group, an ethyl group or an isopropyl group (i-C3H7-). The term "aromatic hydrocarbon group" of P1, P2, Q1 and Q2 means that one hydrogen atom contained in the aromatic hydrocarbon compound becomes a bond bond, and the term "aromatic hydrocarbon compound" means a ring structure having a ring structure formed of carbon atoms. a compound, and the ring structure has an aromatic hydrocarbon compound. The aromatic hydrocarbon compound is, for example, a monocyclic aromatic hydrocarbon compound such as benzene, a bicyclic aromatic hydrocarbon compound such as naphthalene, or a tricyclic aromatic hydrocarbon compound such as ruthenium or osmium having a carbon number of 6 to 20 Aryl and the like. The so-called aromatic heterocyclic group of pi'pZ'Q1 and Q2 means that one hydrogen atom contained in the aromatic heterocyclic compound becomes a bond of a bond, and the so-called aromatic heterocyclic compound means having a nitrogen atom or an oxygen atom. a cyclic compound having a ring structure formed by a hetero atom such as a sulfur atom or a selenium atom and a carbon atom, and the ring structure has an aromatic compound. The aromatic heterocyclic compound is exemplified by a monocyclic aromatic heterocyclic compound composed of one ring structure, a bicyclic aromatic heterocyclic compound composed of two ring structures, and a three ring structure. A tricyclic aromatic heterocyclic compound or the like. -15- i 201245216 The aromatic heterocyclic compound is exemplified by a monocyclic aromatic heterocyclic compound such as furan, thiophene, selenophene, pyrrole, oxazole, thiazole, pyridine, pyrazine, pyrimidine or pyridazine, for example, a bicyclic ring such as thieno[3,2-b]thiophene, furo[3,2-b]furan, thieno[3,2-b]furan, benzo[b]thiophene, benzo[b]furan An aromatic ring heterocyclic compound such as dithieno[3,2-b:2',3'-d]thiophene, benzo[1,2-1>:4,5-1)']dithiophene, benzene And [1,2· b:4,5-b'] a tricyclic aromatic heterocyclic compound such as difuran. The aromatic hydrocarbon group and the aromatic heterocyclic group represented by P1, P2, Q1 and Q2 may have one or more substituents. The substituent is exemplified by, for example, a fluorine atom, an alkyl group which may have a fluorine atom, an alkoxy group which may have a fluorine atom, an alkylthio group which may have a fluorine atom, an aryl group which may have a fluorine atom, and a heteroaryl group which may have a fluorine atom. The group is preferably a fluorine atom, an alkyl group, an alkoxy group or an alkylthio group, and is preferably a fluorine atom. The alkyl group which may have a fluorine atom is exemplified by the above-exemplified alkyl group having 1 to 30 carbon atoms or the hydrogen atom of the alkyl group is substituted with fluorine. It is preferably an alkyl group having 1 to 4 carbon atoms. The alkoxy group which may have a fluorine atom may, for example, be a linear, branched or cyclic alkoxy group having 1 to 30 carbon atoms, and examples thereof include a methoxy group, an ethoxy group, and a n-propoxy group. n-Butoxy, n-pentyloxy, n-hexyloxy, n-heptyloxy, n-octyloxy, n-decyloxy, n-decyloxy, n-decyloxy, n-dodecyloxy, n-ten Trialkoxy, n-tetradecyloxy, n-pentadecanyloxy, n-hexadecyloxy, n-heptadecanyloxy-n-octadecyloxy, n-nonadecanyloxy, positive Alkoxy, n-docosyloxy, n-docosyloxy, n-docosyloxy, n-docosyloxy, n-pentadecane-16-201245216 oxy, positive a linear alkoxy group having a carbon number of from 1 to 30, such as a hexadecyloxy 'n-hexadecanoyloxy group, a n-octadecyloxy group, a n-dodecyloxy group or a n-octadecyloxy group; Carbon number 3 such as isopropoxy group, isobutoxy group, tert-butoxy group, neopentyloxy group, 2-ethylhexyloxy group, 2-hexyldecyloxy '3,7-dimethyloctyloxy group ～30 a branched alkoxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cyclooctyloxy group and the like having a carbon number of 5 to 3 0 Alkyl groups of 2 to 30, such as an oxy group, a methoxymethoxy group, a methoxyethoxy group, a methoxymethoxymethoxy group, a methoxyethoxyethoxy group, and a polyethylene glycoloxy group. The (poly)alkyloxyalkyloxy group and the hydrogen atom of the alkoxy group exemplified above are substituted with a fluorine atom or the like. Preferred alkoxy groups are, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, n-pentyloxy, cyclopentyloxy , n-hexyloxy, 2-ethylhexyloxy, cyclohexyloxy, n-heptyloxy, n-octyloxy, cyclooctyloxy, nonyloxy, decyloxy, 2-hexyldecyloxy, 3 , 7-dimethyloctyloxy, n-undecyloxy, n-dodecyloxy, n-tridecyloxy, n-tetradecyloxy, n-pentadecanyloxy, n-heptadecaneoxy , n-octadecyloxy, n-nonadecanyloxy, n-eicosyloxy, methoxymethoxy, methoxyethoxy, methoxymethoxymethoxy, methoxy An alkoxy group having 1 to 20 carbon atoms such as an ethoxyethoxy group, more preferably a methoxy group, an ethoxy group, a n-propoxy group, a n-butoxy group, a n-pentyloxy group, a cyclopentyloxy group or a n-hexyloxy group. Base, 2-ethylhexyloxy, cyclohexyloxy, n-heptyloxy, n-octyloxy, cyclooctyloxy, nonyloxy, decyloxy, 2-hexyldecyloxy, 3,7·2 Methyloctyloxy, n-undecyloxy 'n-dodecyloxy, n-tridecyloxy, n-tetradecyloxy N-pentadecanyloxy, n-hexadecyloxy, methoxymethoxy, methoxyethoxy, methoxymethoxymethoxy, methoxy-17- 201245216 ethoxy ethoxy The alkoxy group having a carbon number of 6 or the like. The alkylthio group which may have a fluorine atom may, for example, be a linear, branched or cyclic alkylthio group having 1 to 30 carbon atoms, and is exemplified by methylthio, ethylthio, n-propylthio and n-butylsulfide. Base, n-pentylthio, n-hexylthio, n-heptylthio, n-octylthio, n-decylthio, n-decylthio, n-undecylthio, n-dodecylthio, n-tridecanesulfide Base, n-tetradecylthio, n-pentadecanethio, n-hexadecanethio, n-heptadecanethio, n-octadecylthio, n-nonadecanylthio, n-eicosylthio , n-hexadecanethio, n-docosylthio, n-docosylthio, n-tetradecylthio, n-pentadecanethio, n-hexadecanethio, positive a linear alkylthio group having 1 to 30 carbon atoms such as a heptacosylthio group, a n-dodecylsulfanyl group, a n-dodecylthio group or a n-tridecylthio group, for example, an isopropylthio group a branched alkane having a carbon number of 3 to 30 such as a thio group, an isobutylthio group, a second butylthio group, a third butylthio group, a 2-ethylhexylthio group, an n-heptylthio group or a 2-hexylsulfonylthio group Sulfur-based, such as cyclopentylthio, cyclohexylthio, cycloheptylthio, cyclooctylthio, etc. The cycloalkylthio group of 5 to 30 and the hydrogen atom of the above-exemplified alkylthio group are substituted with a group of a fluorine atom or the like. Preferred alkylthio groups are exemplified by, for example, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio't-butylthio, tert-butylthio, n-pentylthio, and hexyl Sulfur, 2-ethylhexylthio, cyclohexylthio, n-heptylthio, cycloheptylthio, n-octylthio, cyclooctylthio, n-decylthio, n-decylthio, 2-hexylfluorene Sulfur, n-undecylthio, n-dodecylthio, n-tridecylthio, n-tetradecylthio, n-pentadecanethio, n-hexadecanethio, n-heptadecane Alkanethio group having 2 to 20 carbon atoms such as a group, n-octadecylthio group, n-nonadecanylthio group and n-icosylthio group, more preferably ethylthio group, n-propylthio group-18-201245216, n-Butylthio, n-pentylthio, n-hexylthio, 2-ethylhexylthio, thio, n-heptylthio, cycloheptylthio, n-octylthio, cyclooctylthio, hexylthio, N-thiol, n-decylthio, 2-n-hexyl-n-decylthioundecylthio, n-dodecylthio, n-tridecylthio, n-tetradecyl, n-pentadecanethio And an aryl group having a carbon number of 2 to 16 such as n-hexadecanethio group and having a fluorine atom is exemplified as The aryl group or the aryl group of carbon number contained in the aforementioned example of the hydrogen atoms replaced by a fluorine atom and the like. More phenyl or naphthyl. The heteroaryl group which may have a fluorine atom is, for example, a monocyclic aromatic heterocyclic group such as a thienyl group, a furyl group or a group, and examples thereof include, for example, thieno[3,2·• phenyl, furo[3,2-b A bicyclic aromatic ring heterocyclic ring such as a furyl group, a thieno[3,2-b]furanyl group, a [b]thienyl group or a benzo[b]furanyl group is preferably a monocyclic ring such as a thienyl group or a furyl group. a diaromatic heterocyclic group such as an aromatic heterocyclic group, a thia[3,2-b]thienyl group, a benzo[b]thienyl group or a benzo[b]furanyl group, and a heteroaryl group as exemplified above The hydrogen atom is a fluorine atom or the like. The compound (1) can be exemplified as the compounds described in the following Tables 1 to 22. Cyclohexane 2·B, n-alkylthiothiol 1~30 is a thiazole b] thiabenzo group, phenocyclic ring is replaced by -19-201245216 [Table 1] R (im) R mn XY w Z Q - R- 1 0 ss -. - H- 2 0 ss - Same as above ch3- 3 0 ss - - Same as above c2h5- 4 0 ss - - Same as above 5 0 ss - - Same as above i-C3H7- 6 0 ss - - Same as above II- C4H9- 7 0 ss - - Same as above n_CsHi Factory 8 0 ss - - Same as above c-CsHij- 9 0 ss - - Same as above 11-C6H13- 10 0 ss - - Same as above C-C6H13- 11 0 ss - - Same as above n-C12H2S- 12 0 ss - - Ibid C6Hs- 13 0 ss - - Same as above (CH3^Si- 14 0 ss - - Same as above (C2Hs)3Si- 15 0 ss - - Same as above (i-C3H7)3Si- .16 0 ss - - Ibid (CH3)2(t-C4H9)Si- 17 0 ss - - Same as above (C6H5)3Si- 18 0 0 0 - - Same as above (CH3^Si- 19 0 0 0 - - Same as above (C2H5)3S Bu 20 0 0 0 - - Ii (i-C3H7)3Si- 21 0 Se Se - - Same as above (CH3)sSi- 22 0 Se Se - - Same as above (C2Hs)3Si- 23 0 Se Se - - Same as above (i-C3H7)3Si- 24 1 Ssss Same as above 25 1. ssss Same as above (C2Hs)3S Bu 26 1 ssss Same as above (i-C3H7)3Si- 27 1 0 0 0 0 Same as above (CHASi- 28 1 0 0 0 0 Same as above (C2H5) 3Si- 2 9 1 0 0 0 0 Same as above (i-C3H7)3Si- 30 1 Se s Valley Se Se Same as above (CH3^Si- 31 1 Se Se Se Se Same as above (C2Hs) 3Si- 32 1 Se Se Se Se Same as above (Bu C3H7) sS 卜-20- 201245216 [Table 2] R Π-m) R mn XYWZ Q- R- 40 0 s S-(CH3)3Si- 41 0 s S-- Same as above (C2H5^Si- 42 0 s S — — Ii (i-C3H7)3Si- 43 0 0 0 — — Same as above (CH3)3Si- 44 0 0 0 — Same as above (C2H5)3Si- 45 0 o 0 — Ii (i-C3H7)3Si- 46 0 Se Se - together with (CH3)3Si- 47 0 Se Se - same as above (C2Hs^Si- 48 0 Se Se Same as above (i-C3H7)3Si- 49 1 S s S s Same as above (CH3)3Si- 50 1 S sss Same as above (C2Hs^S- 51 1 S sss Same as above a-C3H7)3Si- 52 1 0 0 〇0 Same as above (C6H5)3Si- 53 1 0 0 0 0 Same as above (CH3)3S Bu 54 1 0 0 0 0 Same as above (CzHg^ Sir 55 1 Se Se Se Se Same as G-C3H7) 3Si- 56 1 Se Se Se Se Same as above (CH3) 3Si_ 57 1 Se Se Se Se Same as above (CzHs^Si- -21 - 201245216 [Table 3] R (im) mn XYWZ Q- R- 60 0 s S — — ΌΟ (CH3)3Si- 61 0 s S — — Same as above (C2H5)3Si- 62 0 , ss One-to-one (i-C3H7)3Si- 63 0 0 〇一— with Upper (ch3)3s 卜64 0 0 o — — Same as above (C2H6)3Si- 65 0 0 o — Same as above (i-C3H7)3Si- 66 0 Se Se — — Same as above (CH3)3Si- 67 0 Se Se — Same as above (C2Hs) 3Si- 68 0 Se Se - Same as above (i-C3H7)3Si- 69 1 SSS s Same as above. (CH3)3Si- 70 1 SSS s Same as above (C2H5)3Si- 71 1 SSS s Same as above (i-C3H7 ) 3Si- 72 1 〇〇0 0 Same as above (C6H5)3S Bu 73 1 0 0 0 0 Same as above (CH3)3Si- 74 1 0 〇0 0 Same as above (C2H5)3Si- 75 1 Se Se Se Se Same as above (i-C3H7 ) 3Si- 76 1 Se Se Se Se Same as above (CH3) 3S Bu 77 1 Se Se Se Se Same as above (C2H5) 3Si- -22- 201245216 [Table 4] RR〆m η X yw Z Q- R- 100 ό ss — One (CH3)3Si-101 0 ss — — Same as above (C2Hs)3Sr 102 0 ss — Same as above (i-C3H7)3S- 103 0 o 〇 — together with (CH3)3Si- 104 0 0 o — together (C2Hs ) 3Sr 105 0 0. 0 - Idiot (i-C3H7^Si-106 0 Se Se-Iso (CH3)3Si-107 0 Se Se - together with (C2Hs)3Si-108 0 Se Se - together ( i-C3H7^Si- 109 1 ss SS Same as above (CH3)3Si- 110 1 s S s S Same as above (C2H5)3Si- 111 1 sss S Same as above (i-C3H7) sS- 112 1 0 0 0 0 Same as above (C6H5)3S Bu 113 1 0 o 0 0 Same as above (CH3)3Si- 114 1 oo 0 0 Same as above (C2H5)3Sh 115 1 Se Se Se Se Same as above (i-C3H7)3Si- 116 1 Se Se Se Se Ibid (CH3)3Si-117 1 Se Se Se Se Ibid (C2H5)3Si- 201245216 [Table 5] R Η m η XY w Z Q- R- 120 0 s S — — (CHASi- 121 0 s S — — Same as above (C2H5)3Si- 122 0 s S — — Same as above (i-C3H7&gt;jSi-123 0 0 0 — together. (CH3)3Si- 124 0 0 0 — — Same as above (C2Hs)3Si- 125 0 0 0 — Same as above (i-C3H7)3Si- 126 0 Se Se — together with (CHa)3S Bu 127 0 Se Se One-to-one (C2Hs) 3Si- 128 0 Se Se One-to-one. (i- C3H7)3Si- 129 1 SS ss Same as above (CH3)3Si- 130 1 SS ss Same as above (C2Hs)3Si- 131 1 ssss Same as above (i-C3H7)3Si- 132 1 0 0 0 0 Same as above (C6Hs)3Si- 133 1 0 0 0 0 Same as above (CH3)3Si- 134 1 0 0 0 0 Same as above (C2Hs)3Si- 135 1 Se Se Se Se Same as above (i-C3H7^Si- 136 1 Se Se Se Se Same as above (CH3)3Si- 137 1 Se Se Se Se Ibid (C2Hs)3Si- -24- 201245216 [Table 6] R n Y ° p/ mn XYWZQ - R- 140 0 ss — one (CH3)3Si- 141 0 Ss — — Same as above (C2H5^Si- 142 0 ss — — Same as above G_C3H7) 3Si- 143 0 0 0 — — Same as above (CH3)3Si- 144 0 0 0 — Same as above (C2H5^Si- 145 0 0 0 — Same as above (i-C3H7)3Si- 146 0 Se Se — — Same as above (CH3)3S 147 0 Se Se — — Same as above (C2H5)sSi- 148 0 Se Se — — Same as above (i-C3H7)3Si- 149 1 sss S Same as above (CH3)3Si- 150 1 ssss Same as above (C2Hs^Si- 151 1 ssss Same as above (Bu C3H7)3S Bu 152 1 0 0 0 0 Same as above (C6Hs)bSi- 153 1 0 0 0 0 Same as above (CH3)3Si- 154 1 0 0 0 0 Same as above (C2Hs^Si- 155 1 Se Se Se Se Same as G-C3H7) 3Si- 156 1 Se Se Se Se Same as above (CH3)3Si- 157 1 Se Se Se Se Same as above (C2H5)3Si- -25- 201245216 [Table 7] R mn XYWZ Q- R- 160 0 s S — — xoo (CH3^Si- 161 0 .s S — — Same as above (C2Hs)3Si- 162 0 s S — — Same as above (i-C3H7)3S 163 0. 0 0 — — Same as above (CHa^Si- 164 0 0 0 — together. (C2Hs) 3S 165 0 0 0 — — Same as above (i-C3H7)3Si- 166 0 Se Se — Same as above (CHs ^Si- 167 0 Se Se — — Same as above (C2Hs)3Si- 168 0 Se Se — — Same as above (i-C3H7)3Si- 169 1 SSS s Same as above (〇USi- 170 1 SS ss Same as above (C2Hs) 3Si- 177.1 SS ss Same as above (i-C3H7)3Si- 172 1 0 0 0 0 Same as above (C6Hs)3Si- 173 1 0 0 0 0 Same as above ( CH3)jSi- 174 1 0 0 0 o Same as above (C2Hs)3Si- 175 1 Se Se Se Se Same as above (Bu (10) Office - 176 1 Se Se Se Se Ibid. (CH^Si- 177 1 Se Se Se Se Ibid (C2Hs) 3Si- -26- 201245216 [Table 8] R (im) wmn XYWZ o- R- 180 0 s S — — (CH3)3Si- 181 0 s S — — Same as above (QHAS 182 0 s S — — Same as above (i -C3H7)3S Bu 183 0 〇0 — — Same as above (CH3)3Si- 184 0 〇0 One-to-one (QH^Si- 185 0 〇0 One - Same as above (i-C3H7)3Si- .186 0 Se Se — — ibid. • (CH such as i- 187 0 Se Se - same as above (QHg^Si- 188 0 Se Se Io-i (i-C3H7) 3Si- 189 1 S s S s Same as above (CH3)3Si- 190 1 SS Ss Same as above (QH^Si- 191 1 S sss Same as above (i-C3H7)3Sr 192 1 〇〇0 0 Same as above (C6Hs)3Si- 193 1 0 0 0 0 Same as above (CHs^Si- 194 1 0 o 0 0 Same as above ( QH^sSi- 195 1 Se Se Se Se Ibid (i-C3H7)3Si- 196 1 Se Se Se Se Ibid. '(CH3)3Si- 197 1 Se Se Se Se Same as above (QHsJsS I- -27- 201245216 [Table 9] R (1-m) R mn XYWZ Q- R- 200 0. s S — — (CHa^Si- 201. 0 s S — Identical (C2H5)3Si- 202 0 s S一 — — Same as above (i-C3H7)3Si- 203 0 o 〇 — — Same as above (CH3^Si- 204 0 o 〇一一同上(C2Hs)3Si- 205 0 0 0 I—same as above (i-C3H7) 3Si- 206 0 Se Se I—Same as above (CtUSi- 207 0. Se Se – same as above (C2Hs) 3S 208 0 Se Se — Same as above (i-C3H7) 3Si- 209 1 SS S. s Up (CHJS Bu 210 1 SS s .s Same as above (C2H5)3S 211 1 SS ss Same as above (i-C3H7)3Si- 212 1 〇〇0 0 Same as above (C6H5)3Si- 213 1 〇0 0 0 Same as above (CHASi- 214 1 〇〇o 0 Same as above (C2H5)3Si-215. 1 Se Se Se Se Same as above (i-C3H7)3Si-216 1 Se Se Se Se Same as above (CFUSi-217 1 Se Se Se Se Ibid (C2H5)3Si--28- 201245216 [Table 1 ο]

R

R mn XY wz Q- R- 220 0 ss — — P (CH3)3S 221 0 s S — — Same as above (C2Hs)3Si- 222 0 ss — — Same as above (i-C3H7)i3Si- 223 0 0 0 — Same as above (CH3)3Si- 224 0 0 0 One-to-one (C2Hs)3S 225 0 0 0 — — Same as above (i-C3H7)3Si- 226 0 Se Se One-to-one (CH3)3Si- 227 0 Se Se — ibid (C2H5)3S 228 0 Se Se — together (i-CsHy^Si- 229 1 s SS s Same as above (CH3)3Si- 230 1 s S ss Same as above (C2H5)3Si- 231 1 s .S ss Same as above (i-C3H7)sSi- 232 1 0 0 0 0 Same as above (C6Hs)3Si- 233 1- 0 0 0 0 Same as above (CH3)3Si- 234 1 0 0 0 0 Same as above (C2Hs)3Si- 235 1 Se Se Se Se Same as above (i-C3H7^Si-236 1 Se Se Se Se Same as above (CH3)3Si-237 1 Se Se Se Se Same as above (C2H5>3S 卜-29- 201245216 [Table 1 1] RR mn XYWZ Q- R- 240 0 s S -- —. 09 (CH3)3Si- 241 0 s S — — Same as above (¢23⁄43⁄43⁄4- , 242 0 s S — — Same as above (i-C3H7)3Si- 243 0 0 0 One-to-one (CH3)3Si - 244 0 0 0 — — Same as above (CzHs^Si- 245 0 0 0 I. — Same as above (i-C3H7)3Si- 246 0 Se Se — Same as above (CH3)3Si- 247 0 Se Se — Same as above (C2H5&gt;3Si- 248 0 Se Se – same as above (i-C3H7)3S 249 1 S -SS .s Same as above (CH3)3Si- 250 1 SS ss Same as above (C2Hs^Si- 251 1 SS ss Same as above ( i-C3H7)3Si- 252 1 0 0 0 0 Same as above (CsHg^Si- 253 1 0 〇0 0 Same as above (CH3)3Si- 254 1 0 0 0 0 Same as above (C2H5^Si- 255 1 Se Se Se Se Ibid ( i-C3H7)3Si-256 1 Se Se Se Se Same as above (CH3)3S 257 1 Se Se Se Se Ibid. (CzHs^Si-. -30- 201245216 [Table 1 2] m η XYWZ p- R- 260 0 Ss — A (CH3)3Si- 261 0 ss — — Same as above (C2H5)3Si- 262 0 ss — — Same as above (i-C3H7)3Si- 263 0 0 〇 — — Same as above (CH3)3Si- 264 0 0 o — — ibid (C2H5)3Si- 265 0 0 〇一— Ibid (i-C3H7)3Si- 266 0 Se Se — Same as above (CH3)3Si_ 267 0 Se Se — Same as above (C2H5)3Si- 268 0 Se Se — Same as above (i-C3H7)3Si- 269 1 S s S s Same as above (CH3)3Si- 270 1 s S ss Same as above (C2Hs)3Si- 271 1 ssss Same as above (i-C3H7)3Si- 272 1 0 o 0 0 Same as above ( C6H5)sSi- 273 1 0 o 0 0 Same as above (CH3)3Si- 274 1 0 o 0 0 Same as above (C2H5)3Si- 275 1 Se Se Se Se Same as above (i-C3H7)3Si-276 1 Se Se Se Se Same as above (CH3)3Si-277 1 Se Se Se Se Same as above (CzHs^Si- -31 - 201245216 [Table 1 3] m η XYWZ P- R-' 280 0 s S — — s (CH3)3S 281 0 s S — Same as above (C2Hs) 3Si- 282 0 s S — — Same as above (i-C3Hr^Si- 283 0 o .0 I—same as above (CH3)3Si- 284 0 0 0 Same as above (C2Hs)3Si-. 285 0 oL 0 — — Same as above (i-CaHr^Si- 286 0 Se Se – same as above (CH fine - 287 0 Se Se Io (C2Hs) 3Si- 288 0 Se Se — — Same as above (i-C3H7)3Si- 289 1 SSSS Same as above (CH^aSi- 290 1 SS ss Same as above (C2Hs)3Si- 291 1 SS ss Same as above (i-C3HAS: 292. 1 0 0 0 0 Same as above (C6H5)3Si- 293 1 0 0 0 0 Same as above (CH3)3Si- 294 1 0 0 0 0 Same as above (C2Hs)3Si- 295 1 Se Se Se Se Same as above (i-C3H7)3Si- 296 1 Se Se Se Se Same as above (CH3)3Si- 297 1 Se Se Se Se Ibid. (C2H5)3Si- -32- 201245216 [Table 1 4 ] m η XYWZ P- R- 300 0 s S-X» (CH3)3Si- 301 0 s S - Same as above (CzHg^Si- 302 0 s S - Same as above (i-C3H7) 3S 卜 303 0 0 0 — — Same as above (CH3)3Si- 304 0 0 0 — Same as above (C2H5)3S 卜 305 0 0 0 - together with (i-C3H7)3S 306 0 Se Se - same as above (CH3)3S 307 0 Se Se - together with (C2H5)3Si- 308 0 Se Se — Same as above G-c3h7)3s Bu 309 1 SSS s Same as above (CH3)3Si- 310 1 SS ss Same as above (QHASi- 311 1 SS ss Same as above a-C3H7) 3Si- 312 1 0 0 0 0 Same as above (C6Hs)3Si- 313 1 0 0 0 0 Same as above (CH3)3Si- 314 1 0 0 0 0 Same as above (C2H5)3Si- 315 1 Se Se Se Se Same as a-C3H7)3Si- 316 1 Se Se Se Se Same as above (CH3)3Si- 317 1 Se Se Se Se Ibid. (C2H5)3Si- -33- 201245216 [Table 1 5]

m η XY wz P- R- 320 0 s S — one (CH3)3Si- 321 0 ss — — as above (CzHs^Si- 322 0 ss — — as above G-C3H7) 3Si- 323 0 0 0 — together ( CH3)3Si- 324 0 0 0 — I. Ibid. (C2H5)3Si- 325 0 0 0 I—Same as G-C3H7)3Si- 326 0 Se Se — — Same as above (CH3)3Si- 327 0 Se Se — — Same as above ( C2H5)3Si- 328 0 Se Se I — Same as above G-C3H7) 3S 329 1 SSSS Same as above (CH3)3Si- 330 1 SS ss Same as above (C2Hs\S 331 1 SS ss Same as above (i-C3H7) 3S 332 1 0 0 0 0 Same as above (CeHAS 333 1 0 〇0 0 Same as above (CH3)3Si- 334 1 0 .0 0 0 Same as above (C2Hs)3Si- 335 1 Se Se Se Se Same as G-C3H7)3Si- 336 1 Se Se Se Se Same as above (CHs) 3Si- 337 1 Se Se Se Se Same as above (C2H5^Si- -34- 201245216 [Table 16] m η XYWZ P- R- 340 0 s S — — (CH3)3Si- 341 0 s S一— Same as above (C2H5^Si- 342 0 s S One-to-one (i-C3H7)3S Bu 343 0 0 0 — Same as above (CH3)3Si- 344 0 0 0 — Together (C^Hs^Si- 345 0 0 0 — together with (i-C3H7)3Si- 346 0 Se Se — together with (CH3)3Si- 347 0 Se Se — together (C2H5)3Si- 348 0 Se Se - together with (i-C3H7)3Si- 349 1 s SSS Same as above (CH3)3Si- 350 1 SS s S Same as above (C2H5\S 351 1 s S s S Same as above (i- C3H7)3Si- 352 1 0 0 0 0 Same as above (CgHs^Si- 353 1 0 0 0 0 Same as above (CH3)3Si- 354 1 〇〇0 0 Same as above (C2H5^Si- 355 1 Se Se Se Se Same as a-C3H7 ) 3Si- 356 1 Se Se Se Se Same as above (CH3) 3S Bu 357 1 Se Se Se Se Same as above (CzHs^Si- -35- 201245216 [Table 1 7] m η XYWZ P- R- 360 0 s S — — ( CH3)3Si- 361 0 s S — — Same as above (C2H5^Sr 362 0 s S — — Same as above G_c3h7) 3s Bu 363 0 0 0 — Together with (CH3)3Si- 364 0 0 0 — — Same as above (C2H5^Si- 365 0 0 0 — — Same as above G-C3H7) 3Si- 366 0 Se Se — — Same as above (CH3)3S 367 0 Se Se — Together with (C2H5)3Si- 368 0 Se Se — — Same as above a-C3H7)3Si- 369 1 SSS .s Same as above (CH3)3S 370 1 SS ss Same as above (C2H5>3S 371 1 SS ss Same as above (i-C3Hr)3Si- 372 1 〇0 0 0 Same as above (CeHsisSi- 373 1 0 0 0 0 Ibid. (CH3)3Si- 374 1 0 0 0 0 Same as above (CzHAS 375 1 Se Se Se Se Ibid. G-C3H7) 3Si- 376 1 Se S e Se Se Same as above (CH3)3Si- 377 1 Se Se Se Se Same as above (C2H5>3Si- -36- 201245216 [Table 1 8] m η XY w Z P- R- 380 0 s S — — ΌΟΟ (CH3) 3Si - 381 0 .s S — — Same as above (C2H5)3Si- 382 0 s S One-to-one (i-C3H7)3Si- 383 0 0 0 — together with (CH3)3S 384 0 0 0 — together (C2Hs ) 3S 卜 385 0 0 0 — — Same as above (i-C3H7)3Si-386 0 Se Se —. — Same as above (CH3)3S 387 0 Se Se — Same as above (C2Hs) 3Si- 388 0 Se Se — Together (卜C3H7)3S 389 1 SSSS Same as above (CH3)3S 390 1 s S ss Same as above (C2H5)3Si- 391 1 ssss Same as above (i-C3H7)3Si- 392 1 0 0 0 0 Same as above (C6Hs)3Si- 393 1 0 〇0 0 Same as above (CH3)3Si- 394 1 0 0 0 0 Same as above (C2H5)3S 395.1 Se Se Se Se Same as above (Bu C3H7)3Si- 396 1 Se Se Se Se Same as above (CH3)3S 397 1 Se Se Se Se Ibid (C2Hs)3Si- -37- 201245216 [Table 1 9] ra η XYW z p- R- 400 0 s S — — (CH3)3Si- 401 0 s S — — Same as above (C2Hs)3Si- 402 0 s S — — Same as above (Bu C3H7)3Sh 403 0 0 0 — — Same as above (ch3)3s Bu 404 0 0 0 Same as above (C2Hs)3Si- 405 0 0 0 — — Same as above (i-C3H7)3Si- 406 0 Se Se — — Same as above (CH3)3Si- 407 0 Se Se — — Same as above (C2Hs)3Si- 408 0 Se Se — — Same as above (i-C3H7)3Si- 409 1 SSS s Same as above (CH3)3Si- 410 1 ssss Same as above (C2Hs)3Si- 411 1 ssss Same as above (i-C3H7)3S Bu 412 1 0 0 0 0 Same as above (C6H5)3Si- 413 1. o 0 0 0 Same as above (CH3)3Si- 414 1 0 0 0 0 Same as above (C2H5)3S 415 1 Se Se Se Se Same as above (i-C3H7)3Si- 416 1 Se Se Se Se Same as above (CH3)3Si - 417 1 Se Se Se Se Ibid (C2H5)3S 卜-38- 201245216 [Table 2 Ο] mn XYWZ p- .R- 420 0 s S — — (CH3)3Si- 421 0 s S — — Same as above (C2Hs) 3S 卜 422 0 s S — together with (Bu C3H7) 3S Bu 423 0 0 0 — Together with (CH3)3Si- 424 0 0 0 — — Same as above ((10) Office - 425 0 0 0 — — Same as above (Bu C3H7) 3Sh 426 0 Se Se — — Same as above (CH3)3Si- 427 0 Se Se — — Same as above (C2Hs)3Si- 428 0 Se Se — Same as above (Bu C3H7) 3S Bu 429 1 SSS s Same as above (CH3)3Si- 430 1 SS Ss Same as above (C2Hs)3Si- 431 1 SS ss Same as above (Bu C3H7)3S Bu 432 1 0 0 0 0 Same as above (CgHs^Si- 433 1 0 0 0 0 Same as above (CH3)3Si- 434 1 0 0 0 0 Same as above (C2H5)3Si- 435 1 Se Se Se Se Same as above (Bu C3H7)3S Bu 436 1 Se Se Se Se Iso (CH3)3Si-. 437 1 Se Se Se Se Ibid (C2Hs)3Si- -39- 201245216 [Table 2 1 ] m η XYWZ p- R- 440 0 s S — — P (CH3^Si- 441 0 s S — — Same as above (C2H5)3Si- 442 0 s S — Same as above. (i-C3H7)3Si- 443 0 0 〇一一同 (CH3)3S- 444 0 0 0 — — Same as above (C2H5)3Si - 445 0 0 0 I - Same as above (Bu C3H7) 3S Bu 446 0 Se Se — Same as above (CH3)3Si- 447 0 Se Se — Same as above (C2Hs)3Si- 448 0 Se Se — — Same as above (i-C3H7)3S 449 1 SS . S s Same as above (CH3)3Si- 450 1 SS ss Same as above (C2H5)3Si- 451 1 SS ss Same as above (i-C3H7)3Si- 452 1 0 0 0 0 Same as above (C6H5)3Si- 453 1 0 0 0 0 Same as above (CH^Si- 454 1 0 0 0 0 Same as above (C2H5) 3S Bu 455 1 Se Se Se Se Same as above (i-C3H7) 3S Bu 456 1 Se Se Se Se Same as above (CH3>3S- 457 1 Se Se Se Se Ibid (C2Hs)3Si- -40- 201245216 [Table 2 2] m η XYWZ P- R- 460 0 s S -9 〇(CH3)3Si- 461 0 s S — Together (C2Hs&gt;3Si- 462 0 ss One-to-one (Bu C3H7) 3S Bu 463 0 0 0 — I. Ibid. (CHASh 464 0 o 0 – together (C2Hs&gt;jSi- 465 0 0 .0 — together Upper (Bu C3H7) 3Si- 466 0 Se Se — —· Same as above (CH3) 3Si- 467 0 Se Se — Same as above (C2Hs) 3Si- 468 0 Se Se — Same as above (Bu C3H7) 3Si- 469 1 SSSS Same as above ( CHASi- 470 1 s S s S Same as above (C2Hs)3Si- 471 1 s S s S Same as above (i-C3H7)3Si-. 472 1 0 0 0 0 Same as above (C6Hs)sSi- 473 1 0 0 0 0 Same as above (CH3 ) 3Si- 474 1 o 〇o 0 Same as above 475 1 Se Se Se Se Same as above (i-C3H7)3Si- 476 1 Se Se Se Se Same as above (CH3)3Si- 477 1 Se Se Se Se Same as above (C2Hs) bSi- The compound (1) of the invention preferably has the same P1 and P2 and is a group represented by the formula (2), and QI and Q2 are the same substituted aromatic hydrocarbon group or a substituted aromatic heterocyclic group) Compound 'that is, by the following formula

(1b) (hereinafter sometimes referred to as Q as representative 1 b )

R (wherein η, Ι, χ, γ, 'square and Q represent the same meaning as described above -41 - 201245216). The different examples of the compound (1) of the present invention are preferably a substituted aromatic hydrocarbon group or a substituted aromatic heterocyclic group (hereinafter sometimes referred to as P) of the P1 and p2 systems, and Q1 and Q2 is a compound which is the same and is a group represented by the formula (2), and a compound represented by the following formula (lb') (wherein, 11, ruthenium, osmium, iridium, 2, 11 and ? represent the same meaning as described above) . In particular, it is preferred that m in the table is a compound represented by the following numbers (1° 13, 14 4, 15, 40, 41, 42, 60, 61 '62, 100, 101 102, 120, 121, 122, 140) 141, 142, 160, 161, 162 1 80, 18 1 &gt; 182, 200, 201 '202, 220, 221, 222 '240 241 &gt; 242, 260, 26 1 , 262 , 2 80 , 281 , 282 3, 00, 301 3 02 '320 321 , 322 , 340 ' 341 , 342 , 360 , 361 , 362 3 80 , 381 3 82 , 400 &gt; 401 , 402 , 420 , 421 , 422 , 440 44 1 &gt; 442 , 460 ' 461 ' 462 〇 is more preferably the compound (1 ) represented by the following number in the table. 13 14, 15, 40, 41 The compound of the present invention; the substance (1) is excellent in solubility to an organic solvent. The tendency is that the compound (1) tends to be easy to manufacture, and the purification after the production tends to be easy. -42- 201245216 and the solution in which the compound (1) is dissolved in an organic solvent can be coated and Drying to form a film. The film obtained by coating the compound (1) and film-forming is as described later. The tendency to exhibit a film having a high carrier mobility is preferred. Next, a method for producing the compound (1) will be described. The production method when the compound (1) is the compound (1) may be, for example, included in the presence of a transition metal compound. A step of reacting a Q-containing metal compound (compound (4)) with a compound (compound la) represented by the following formula (丨a) (hereinafter sometimes referred to as a step):

(wherein 'n, W, X, Y, Z and R have the same meanings as defined above, and X1 each independently represents a halogen atom, more preferably an iodine atom, and X1 is preferably the same). The Q in the compound (4) may be the same as the above-mentioned Q1 and Q2, the substituted aromatic hydrocarbon group or the substituted aromatic heterocyclic group, and preferably a substituted aromatic heterocyclic group. The metal atom contained in the compound (4) may, for example, be a tin atom, a magnesium atom, a zinc atom or a boron atom. The compound (4) containing a Q atom and a tin atom may, for example, be a compound represented by the following formula (6) (compound (6)) or the like: -43- 201245216 R4 Q-Sn-R5 (6) \ R6 in the formula (6) , Q represents a substituted aromatic hydrocarbon group or a substituted aromatic heterocyclic group. In the formula (6), R4, R5 and R6 are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl Alkyl group having a carbon number of 1 to 10, such as a base group, a second butyl group, a tert-butyl group, a n-pentyl group, a cyclopentyl group, a n-hexyl group, a cyclohexyl group, an n-octyl group, and a n-decyl group, preferably a methyl group or a The group, n-propyl, n-butyl, n-hexyl is more preferably methyl, ethyl, n-propyl or n-butyl. The method for producing the compound (6) is, for example, a compound represented by the following formula (6-2): Q-X6 (6-2) (wherein Q represents the same meaning as described above, and X6 represents a chlorine atom or a bromine atom. a halogen atom such as an iodine atom or an alkoxy group having a carbon number of 1 to 10),

The solution with the solvent is cooled to below -40 ° C, preferably at -55 ° C to -110 ° C, more preferably in the range of -65 ° C to - l ° ° C, after the addition of the third butyl lithium The alkyl lithium reagent is then stirred at the above temperature range for 10 minutes to 5 hours. Further, a solution containing a compound represented by the formula (6-2) and a solvent is set.

Glyon reagent such as isopropylmagnesium bromide is added at 40 ° C to -1 10 ° C, preferably at 20 ° C to -100 ° C, more preferably at a temperature range of 〇 ° C to -80 ° C Then, stir for 1 〇 minutes to 5 hours in the above temperature range. Alternatively, the compound represented by the formula (6-2) is allowed to react with the metal -44-201245216 magnesium, in the same manner as in the usual method of the Grignard reagent. 6 -1 ) When the anion of Q is thus produced, the following formula is added (compound:

(6-1) R4

(wherein, X5 represents a fluorine atom, a chlorine atom, or a brominated halogen atom; 'R4, R5, and R6 are the same as defined above; a method of reacting at 30 ° C to -8 ° C for 10 minutes to 5 hours, etc. When Q is a substituted aromatic heterocyclic group, it is exemplified to include a solution represented by the following formula (6-3): QH (6-3) (wherein -H represents bonding to an aromatic hybrid) Ring α, cooled to below -40 ° C, preferably -55 ° C ~- ll ° ° C, after a better temperature range, add alkyl butyl lithium and other alkyl lithium test temperature range stirring 1 〇 In the next, the compound is added to the obtained reactant, and the method is carried out at -1 ° C for 10 minutes to 5 hours. As for the compound (4) containing Q and magnesium atoms, it can be represented by a compound (compound (7)) or the like: or an iodine atom), and a halogen-free complex and a hydrogen at a solvent position) -6 5 〇C ～1 0 0 〇C 1, followed by the above formula ( 6-1) The reaction at 30 ° C is the following formula (7 - 45 - 201245216 Q g - χ 3 (7) In the formula (7), Q represents the same meaning as described above, and X3 is, for example, a fluorine atom or a chlorine atom. ,bromine The halogen atom of the iodine atom or the iodine atom is preferably a chlorine atom, a bromine atom or an iodine atom. The compound (7) is a compound represented by (6-2) as described in the method for producing the compound (6). The compound (4) containing a Q and a zinc atom may be exemplified by a compound represented by the following formula (8) (compound (8)), etc., as a reaction of a Grignard reagent such as isopropylmagnesium bromide or a metal magnesium: Q ~ η η — X 4 (8) In the formula (8), Q represents the same meaning as described above, and X4 is a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, preferably a chlorine atom, a bromine atom or iodine. The method for producing the compound (8) can be produced in the same manner as the compound (6) except that a zinc halide such as zinc chloride, zinc bromide or zinc iodide is used instead of the compound represented by the above formula (6-1). The compound (4) of the Q and the boron atom is exemplified by the compound represented by the following formula (9) (compound (9)) and the like: Q—Β R7

(9) -46- 201245216 In the formula (9), Q represents the same meaning as defined above, and R7 and R8 represent a hydroxyl group such as a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group or a n-butoxy group. And an alkoxy group having 1 to 10 carbon atoms such as n-hexyloxy group, for example, an aryloxy group having 6 to 20 carbon atoms such as a phenoxy group, a 1-naphthyloxy group or a 2-naphthyloxy group. Further, as for the ring structure in which R7 and R8 may be bonded and formed of R7, R8 and a boron atom, for example, 1,3,2·dioxaborolane, 4,4,5,5- may be mentioned. Tetramethyl-1,3,2-dioxaborolane, 5,5-dimethyl-1,3,2-dioxaborolane, 1,3,2-benzo Dioxaborole (561120 (1丨0\31501&gt;〇16) ring, 9-borabicyclo-3,3,1-anthracene ring. Compound (9) except the following formula (9-) 1) The compound represented by the formula (6-1) can be produced in the same manner as the compound (6).

X7-B R7

(9-1) (wherein R7 and R8 have the same meanings as defined above except for the hydroxyl group, and X7 represents the alkoxy group or aryloxy group described above). The metal compound (Q (4)) containing Q in this step is used in an amount of 1 to 10 moles, preferably 2 to 4, based on 1 mol of the compound (la). The proportion of Moer. The transition metal compound used in this step is exemplified by, for example, a palladium compound or a nickel compound. The palladium compound can also be a reaction with a phosphine compound. Commercially available products can also be used as the transition metal compound. Here, the palladium compound is exemplified by, for example, stilbene (dibenzylideneacetone) dipalladium-47-201245216 (〇) 'paran (dibenzylideneacetone) dipalladium (ruthenium) • chloroform adduct, palladium acetate (Π) , palladium chloride (ruthenium), (bicyclo [2.2.1] hept-2,5-diene) dichloropalladium (II), (2,2'-bipyridyl) dichloropalladium (II), bis (acetonitrile) Chloronitropalladium (ruthenium), bis(benzonitrile)dichloropalladium(II), bis(acetonitrile)dichloropalladium(II), dichloro(1,5-cyclooctadiene)palladium(II), Dichloro(ethylenediamine)palladium(Π), dichloro(Ν,Ν,Ν',Ν'-tetramethylenediamine) palladium(II), dichloro(1,1〇-phenanthroline)palladium (II), palladium ruthenium pyruvate (ruthenium), palladium (II) bromide, palladium (II) hexafluoroacetate, palladium iodide (Π), palladium (II) nitrate, palladium sulfate (II) ), palladium trifluoroacetate (Π). As the palladium compound, a commercially available product is usually used as it is. The palladium compound is used in an amount of usually 0.001 to 1 mol per mol of the palladium metal atom based on 1 mol of the compound (la). The phosphine compound is exemplified by, for example, triphenylphosphine, ginseng (2-methylphenyl)phosphine, ginseng (3-methylphenyl)phosphine, ginseng (4-methylphenyl)phosphine, and hexafluorophenyl. Phosphine, ginseng (4-fluorophenyl)phosphine, ginseng (2-methoxyphenyl)phosphine, ginseng (3-methoxyphenyl)phosphine, ginseng (4-methoxyphenyl)phosphine, ginseng (2,4,6-trimethylphenyl)phosphine, tris(3-chlorophenyl)phosphine, tris(4-chlorophenyl)phosphine, tri-n-butylphosphine, tri-tert-butylphosphine, tricyclic Hexylphosphine, 1,2-diphenylphosphinodecylethane, 1,3,2-diphenylphosphinium propane, 1,4-diphenylphosphinodecyl, 1,2-dicyclohexylphosphine Ethylethane, 1,3-dicyclohexylphosphinodecylpropane, 1,4-dicyclohexylphosphinodecylbutane, 1,2-dimethylphosphonium ethane, 1,3-dimethylphosphine Mercaptopropane, 1,4-dimethylphosphonium butane, 1,2-diethylphosphonium ethane, 1,3, diethylphosphonium propane, 1,4-diethylphosphine Mercaptan, 1,2-diisopropylphosphonium decylethane, 1,3-diisopropyl-48-201245216-based phosphinium propane, hydrazine, 4-diisopropylphosphonium decyl, Tris(2-furan), 2-(dicyclohexyl) Indenyl)biphenyl, 2-(di-t-butyl)biphenyl, 2-di-t-butylphosphonium-2'-methylbiphenyl, 2-(hexylphosphino-yl-2',6 '-Dimethoxy 1,1'-biphenyl, 2-(dicyclohexyl)-2'-(N,N-dimethylamino)biphenyl, 2-dicyclohexylphosphine 醯-methyl -biphenyl, 2-(dicyclohexylphosphino)-2',4',6'-triiso 1,1'-biphenyl, 1,1'-bis(diphenylphosphonium) ferrocene Iron, 1,1 '-diisopropylphosphonium) ferrocene. The phosphine compound can be used by a commercially available person in accordance with a conventional method. The phosphine compound is used in an amount of from 1 to 5 moles per atom, usually from 0.5 to 10 moles, more preferably from 1 to 5 moles. Further, the palladium compound which is reacted with the phosphine compound is exemplified by, for example, ruthenium (phosphine) palladium (ruthenium), bis(acetate) bis(triphenylphosphine)palladium bis[1,2-bis(diphenylphosphinofluorenyl). Ethane] palladium (ruthenium), ruthenium, 2, bis(phosphinyl) ethane]dichloropalladium (11), dibromobis(triphenylphosphine) II), dichlorobis(dimethylbenzene) Palladium (II), dichlorobis(diphenylphosphine)palladium(Π) 'dichlorobis(tricyclohexylphosphine) (11 dichlorobis(triethylphosphine)palladium(11), dichloro Bis(triphenylphosphine) II), dichlorobis[ cis (2-methylphenyl)phosphine], fluorene (tolylphosphine) palladium (ruthenium), ruthenium (tricyclohexylphosphine) fine (〇), two Chloro 1,1'-diphenylphosphinodecylferrocene) palladium (π). Commercial products can also be used as they are commercially available. As for the nickel compound, for example, dichlorobis(1,I'-diphenylphosphinoferrocene)nickel(II), dichlorobis(diphenylphosphinofluorenyl)nickel (11-morfylphosphonium-rs-sl. Phosphonium bismuth; -25-propyl bis (also known as palladium as triphenyl) ^ diphenyl palladium (methyl), palladium (based bis(, and fluorenyl-49-201245216 dichloronickel (II), two Nickel (II) iodide, dichloro(1,5-cyclooctadiene)nickel(II), dichloro[1,2·bis(diphenylphosphonium)ethane]nickel (H). Nickel compound The amount used is usually 0.001 to 1 mol per mol of the compound (1 a ), and the compound (9) is usually used in the presence of a base in the reaction. For example, lithium hydroxide, sodium hydroxide, potassium hydroxide, barium hydroxide, barium hydroxide, lithium pentoxide, sodium methoxide, potassium methoxide, lithium ethoxide, sodium ethoxide, potassium ethoxide, third butyl oxidation Sodium, potassium butoxide, lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, carbonic acid planing, sodium hydrogencarbonate, potassium hydrogencarbonate, sodium phosphate, potassium phosphate, diethylamine, triethylamine Diisopropylamine, piperidine, and the amount of the base to be used is a ratio of 1 to 50 moles per mole of the compound (9), preferably from 2 to 20 moles. This step is preferably carried out in the presence of a solvent. The solvent is exemplified by an aromatic hydrocarbon solvent such as benzene, toluene or xylene; diethyl ether, tetrahydrofuran, 1,4-dioxane 't-butyl methyl ether, cyclopentyl methyl ether, ethylene glycol dimethyl Ether solvent such as ether: decylamine solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or 1,3-dimethyl-2-imidazolidinone Dimethyl hydrazine, water. The solvent may be used singly or in combination of two or more. The solvent is preferably used for degassing. Further, the compound (la) or compound used in the production method of the compound (lb) may be used. (4) After partially or completely dissolving or suspending in a solvent, deaeration is carried out by introducing nitrogen gas or a reduced pressure, etc. The solvent is used in an amount of usually 0.5 to 200 parts by weight based on 1 part by weight of the compound (1 a ). The ratio is preferably a ratio of 〇〇 by weight. This step can be carried out in the presence of a phase transfer catalyst. The conversion catalyst can be exemplified by a quaternary ammonium salt such as a tetraalkylammonium halide, a tetraalkylammonium hydrogen sulfate or a tetraalkylammonium hydroxide, etc., preferably a tetra-n-butylammonium halide or a benzyl group. Triethylammonium halide, etc. The amount of the interphase transfer catalyst used is a ratio of 0.0001 to 1 mol per mol of the compound (1 a ), preferably 0.01 to 0.2 mol. This step can be carried out under the atmosphere. It is preferably carried out under an inert gas such as nitrogen or argon. The reaction temperature in this step is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 1 minute to 96 hours. The obtained organic layer may be concentrated by, for example, mixing the obtained reaction mixture with an aqueous sodium chloride solution and optionally adding an organic solvent insoluble in water, and if necessary, column chromatography, steaming, recrystallization, and cyclic condensation may be used. The compound (1 b ) is obtained by a purification means such as gel permeation chromatography or sublimation purification. X, Y, w, Ζ, η and R of the compound (la) used in this step have the same meanings as described above. The X, hydrazine, hydrazine and W of the compound (1 a ) are preferably the same, and are preferably all sulfur atoms. The oxime in the compound (U) is independently a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, and is preferably a bromine atom or an iodine atom, more preferably an iodine atom. The compound (la) can be exemplified as the compounds described in Tables 23 to 25. -51 - 201245216 [Table 2 3] R (1a, R mn XY wz xl- R- 1 0 ss - - I- H- 2 0 ss - - I- ch3- 3 0 ss - - I- C2Hs- 4 0 Ss - - I- n~C^H7- 5 0 ss - - I- I-C3H7- 6 0 ss - - I- n-C4H9- 7 0 ss -· 一卜 n-C5H„- 8 0 ss - - I- c-CsHn- 9 0 ss - - I- η~〇6Η13- 10 0 ss - - b c-C6H13- 11 0 ss - - I- n-C12H25- 12 0 ss - - I- c6h5- 13 0 Ss - - I- (ch3)3s 卜 14 0 ss - - I- (C2H5)3Si- 15 0 ss - - I- (i-C3H7)3Si- 16 0 ss - - I- (CH3)2(t- C4H9)Si- 17 0 ss - - I- (C6Hs)3Si- 18 0 0 .0 - - I- (CH3)3Si- 19 0 0 0 - I-(C2H5)3Si- 20 0 0 0 - - I - (Bu C3H7)3S Bu 21 0 Se Se - - 1- (CH3)3Si- 22 0 Se Se - - I- (C2H5)3Si- 23 0 Se Se - - I- (Bu C3H7) 3S Bu 24 1 ssss I-(CH3)3Si- 25 1 ssss I- (C2H5)3Si- 26 1 ssss I- (i-C3H7)3Si- 27 1 0 0 0 0 I- (CH3)3Si- 28 1 0 0 0 0 I- (C2Hs)3S 卜29 1 0 0 0 0 I-(i-C3H7)3Si- 30 1 Se Se Se Se I- (CH3)3Si- 31 1 Se Se Se Se I- (C2H5)3Sh 32 1 Se Se Se Se I- (i-C3H7)3Si- -52- 201245216 [Table 2 4] R (1(four) r/ m η XYW z x1- R- 33 0 s S ——— — Br- H- 34 0 ss - - Br- ch3- 35 0 ss — — Br- 36 0. ss — — Br- n_C3H7_ 37 0 ss - - Br- i-C3H7- 38 0 ss - - Br- 39 0 ss - - Br- n-C5H„- 40 0 ss - - Br- c-C5Hn- 41 0 ss - - Br- n-C6H13- 42 0 ss - - Br- c-C6H13- 43 0 ss - - Br- n-C12H25_ 44 0 ss - - Br- c6h5- 45 0 ss - - Br- (CH3)3Si- 46 0 ss - - Br- (C2H5)3Sh 47 0 Ss - - Br- (Bu C3H7) 3S Bu 48 0 ss - - Br- (CH3) 2(t-C4H9)Si- 49 0 ss - - Br- (C6H5)3Si- 50 0 0 0 - - Br- ( CH3)3Si- 51 0 0 0 - - Br- (C2H5)3Sh 52 0 0 0 -. - Br~ (i-C3H7)3Si- 53 0 Se Se - - Br- (CH3)3S Bu 54 0 Se Se - - Br- (C2Hs)3Sh 55 0 Se Se - - Br- (i-C3H7)3Si- 56 1 ssss Br- (CH3)3Si-. 57 1 ssss Br- (C2Hs)3Si- 58 1 ssss Br- (i -C3H7)3Si- 59 1 0 0 0 0 Br- (CH3)3Si- 60 1 0 0 0 0 Br- (C2H5)3S Bu 61 1 0 0 0 0 Br- (Bu C3H7)3S Bu 62 1 Se Se Se Se Br- (CH3) 3S BU 63 1 Se Se Se Se Br- (. 2^5)33 Bu 64 1 Se Se Se Se Br- (i-C3H7)3Si- -53- 201245216 [Table 2 5] RR mn XY wz x1- R- 65 0 ss — - ci- H- 66 0 ss - 琴 ci- ch3- 67 0 ss - - ci- Cans- 68 0 ss - - ci- ηΌβΗ/- 69 0 ss - - ci- 卜 c3h7- 70 0 ss - - ci- n - 71 0 ss one - ci - n-C5Hn- 72 0 ss - - ci- c-C5H„- 73 0 ss - - ci- n-C6H13- 74 0 ss - - ci- c-C6H13- 75 0 ss - - ci- n-C12H25- 760 ss - - ci - (CH3)2(t-C4H9)Si- 81 0 ss mono- ci- (C6Hs)3S 卜 82 0 0 0 - - ci- (CH3)3Si- 83 0 0 0 - - ci- (C2Hs)3Si- 84 0 0 0一- ci- (Bu C3H7)3S 卜 85 0 Se Se a- ci- (CH3)3Si- 86 0 Se Se a- ci- (C2Hs)3Si- 87 0 Se Se - - ci- C3H7)3S 卜88 1 ss S s ci- (CH3)3Si- 89 1 ss S s ci- (C2H5)3S 卜 90 1 ss S s ci- (i-C3H7)3Sr 91 1 0 0 0 0 ci- ( CH3)3S 卜92 1 0 0 0 0 ci- (C2H5)3Si- 93 1 0 0 0 0 ci- (Bu C3H7)3S Bu 94 1 Se Se Se Se ci- (CH3)3Si- 95 1 Se Se Se Se Ci- (C2H 5) 3Sh 96 1 Se Se Se Se ci- (Bu C3H7) 3S - 54 - 201245216 The production method of the compound (1 a ) is, for example, a compound (compound (lc)) represented by the following formula (lc) Alkyl lithium reaction,

(wherein, n, R, W, X, Y and Z represent the same meaning as defined above), a method of reacting a halogenating agent containing X1 as a halogen atom with a reaction product obtained. Examples of the alkyllithium include, for example, methyllithium, n-butyllithium, t-butyllithium, t-butyllithium, and phenyllithium, and preferably n-butyllithium, second butyllithium, and third. Butyl lithium. The alkyllithium is used in an amount of usually 1 to 10 moles, preferably 1 to 5 to 3 moles, per mole of the compound (lc). The halogenating agent is exemplified by halogen molecules such as Cl2, Br2, 12, iodine monochloride, N-chlorosuccinimide, N-bromosinium imine, N-iodosuccinimide, and the like. Wait. The halogenating agent is used in an amount of usually 1 to 10 moles, preferably 1.5 to 3 moles, per mole of the compound (lc). The halogenating agent may be directly added to the reaction product of the compound (lc) and the alkyllithium, or the halogenating agent may be dissolved or suspended in a solvent to be added to the reaction product. The solvent used in the production of the compound (1 a ) is exemplified by an aliphatic hydrocarbon solvent such as pentane, hexane or heptane, an aromatic hydrocarbon solvent such as toluene or xylene, diethyl ether, tetrahydrofuran or 1,4-dioxane. An ether solvent such as cyclopentyl methyl ether, ethylene glycol di-55-201245216 methyl ether or propylene glycol dimethyl ether, or a mixed solvent thereof. Preferred are benzene, hexane, toluene, diethyl ether, tetrahydrofuran and cyclopentyl methyl ether. The amount of the solvent to be used is usually 0.5 to 200 parts by weight, preferably 2 to 100 parts by weight, based on 1 part by weight of the compound (lc). The specific method for producing the compound (la) is as follows. First, the solution containing the compound (lc) and the solvent is cooled to -40 ° C or less 'better - 5 5 ° (: ~ -110 ° 〇, more preferably -65 ° (: ~ -100 ° (: temperature range Thereafter, an alkyl lithium is added, followed by stirring at the above temperature range for 10 minutes to 5 hours to obtain a reaction solution containing a lithium compound of the compound (lc). Further, the temperature may be raised to -40 ° C to 30 ° C in order to surely terminate the reaction. The mixture was stirred for 10 minutes to 5 hours. Next, the reaction solution was adjusted to room temperature (about 25 ° C) to -10 (temperature range of TC, and then a halogenating agent was added, and the mixture was stirred at the above temperature range for 0 minutes to 5 hours. Then, in order to surely terminate the reaction, the temperature may be raised to -4 (TC to room temperature, and stirred for 10 minutes to 5 hours. After mixing the aqueous solution containing a reducing agent such as sodium sulfite in the crude product containing the compound (1 a ) thus obtained, The liquid layer is obtained by mixing the organic layer with the organic solvent in which the water-insoluble organic solvent is added, and the obtained organic layer is washed with an aqueous solution of sodium chloride or water, and then concentrated. Column chromatography, distillation, recrystallization, circulating gel as needed The compound (1a) is obtained by a purification means such as chromatography, and the compound (U) used in the production method of the compound (la) is exemplified by the compound described in Table 26. In the compound described in Table 26, It is preferably a compound containing a halogen atom, that is, a compound represented by (lc-13) to (lc-32). -56- 201245216 [Table 2 6] R (1c-m) R mn XYW z R- 1 0 s S - - H- 2 0 ss - - ch3- 3 0 ss - - C2H5- 4 0 ss - — n_C3H7_ 5 0 ss - — b c3h7- 6 0 ss - - n_C4H9- 7 0 ss - - n-QHn- 8 0 ss - - c-C5Hn- 9 0 ss -n-C6H13- 10 0 ss - - c-C6H13- 11 0 ss - - n-C12H25- 12. 0 ss - - .6 only 5 - 13 0 ss - - (CH3)3Si- 14 0 ss - - (G2H5)3Si- 15 0 .s. s - - (i-C3H7)3Si- 16 ό ss - - (CH3)2(t-C4H9)Si- 17 0 ss - - (C6H5)3Si- 18 0 0 0 - (CH3)3Sh 19 0 0 0 - - (C2H 5)381- 20 0 0 0 - - (i-C3H7)3S Bu 21 0 Se Se -. - ( CH3)3Si- 22 0 Se Se - - (C2H5)3Si~ 23 0 Se Se - (Bu C3H7)3S Bu 24 1 ss S s (CH3)3S Bu 25 1 ssss (C2Hs)3S Bu 26 1 ssss (i -C3H7)3Si- 27 1 0 0 0 0 (CH3)3S Bu 28 1 0 0 0 0 (C2H5)3Si- 29 1 0 0 0 0 (i-C3H7)3Si- 30 1 Se Se Se Se (CH3)3Si- 31 1 Se Se Se Se (CsHASi - 32 1 Se Se Se Se . (i-C3H7) 3S 卜-57-201245216 The production method of the compound (1 c ) is, for example, in the presence of a transition metal compound, a copper halide and an organic base, and the following formula (Id) is given. (Compound (Id)), dd) (wherein, n, W, X, Y and Ζ represent the same meaning as defined above, and X2 each independently represents a halogen atom, preferably an iodine atom, and X2 is preferably the same a method of reacting with a compound represented by the following formula (5) (compound (5)), Η-ΞΖΙ-R (5) (wherein R represents a substituted alkyl group, a substituted aryl group or The substituted alkylene group is preferably the following formula R1 - 4 to R 2

I R3 (wherein R 1 , R 2 and R 3 each independently represent an alkyl group having 1 to 16 carbon atoms or an aryl group having 6 to 12 carbon atoms)). The compound (5) is used in an amount of usually 1 mole to 10 moles per mole of the compound (ld), preferably 2 to 4 moles. The transition metal compound in the production method of the compound (lc) can be exemplified as the transition metal compound used in the production method of the compound (lb). The amount of the transition metal compound used is 0.001 to 1 mol per mole of the transition metal atom contained in the compound (Id) 1 molar 'transition metal compound. The copper (I) halide used in the method for producing the compound (1 C ) is, for example, copper (I) chloride, copper (I) bromide or copper (I) iodide, preferably copper (I) bromide. Copper iodide (I). The amount of copper (I) halide used is usually from 0.001 to 1 mol per mol of the compound (1 d ). The organic base used in the production method of the compound (1C) may, for example, be a secondary amine such as diethylamine, diisopropylamine, piperidine, pyrrolidine or dicyclohexylamine, triethylamine or diisopropylethylamine. An organic amine such as a tertiary amine. The amount of the organic base used is at least 2 moles relative to the compound (id) 1 mole. Further, the organic base may be used as a solvent. In this case, the amount of the organic base to be used is usually 0.5 to 200 parts by weight, preferably 2 to 100 parts by weight, based on 1 part by weight of the compound (Id). The production of the compound (1 c ) is preferably carried out in a solvent. The solvent is exemplified by an aromatic hydrocarbon solvent such as benzene, toluene or xylene; diethyl ether, tetrahydrofuran, 1,4-dioxane, tert-butyl methyl ether, cyclopentyl methyl ether, ethylene glycol dimethyl Ether solvent such as ether; N,N-dimethylformamide, hydrazine, hydrazine dimethyl ethanoamine, hydrazine-methyl D ratio ketone, 1,3 dimethyl-2-imidine D- ketone and other guanamine solvent; dimethyl hydrazine. The solvent may be used singly or in combination of two or more. The solvent is preferably used for degassing. Also, the compound (1 c ) can also be used.

The compound (Id) or the compound (5) used in the manufacture of C-59-201245216 is dissolved or suspended in a solvent, and is introduced into a solvent such as nitrogen or reduced pressure, and a part relative to the compound (id) is 0.5 part by weight. ~200 parts by weight, preferably in a proportion of 2 to 100 parts by weight. The production of the compound (1 c ) can also be carried out in the atmosphere, or in an inert gas such as argon. The manufacture of the compound (lc) can further transfer the catalyst between the phases. The intermediate transfer catalyst may, for example, be a quaternary ammonium compound such as a tetraalkylammonium halide, an ammonium hydrogen phosphate or a tetraalkylammonium hydroxide, or a butylammonium halide or a benzyltriethylammonium halide. The amount of the phase transfer catalyst used is 0.0001 to 1 mol per mol of the compound (1 d ), preferably 〇.〇1 to 〇·2 mol. The reaction in the reaction of the compound (Id) with the compound (5) is in the range of 0 to 200 °C. The reaction time for the production of the compound (lc) is usually in the range of 1 minute. After completion of the reaction of the compound (1 d ) with the compound (5), for example, the resulting reaction mixture is mixed with water and then subjected to liquid separation to obtain an aqueous layer of an organic liquid which can be mixed with the organic layer which is optionally treated with a water-insoluble organic solvent. The obtained organic layer is further washed with sodium chloride water, and then concentrated, and subjected to purification methods such as column chromatography, distillation, and cyclic gel permeation chromatography as needed to obtain a compound (1 c : used in the production of the compound (lc). The compound (ld) is a compound described in Table 27, which will be described later. - Partial or degassing. It is usually preferred to introduce tetraalkylsulfide in the presence of nitrogen to a temperature of four plus one mole. ~96 small, can be re-crystallized by extracting liquid or water by branch, and 0 can be listed as -60-201245216, in Table 27, preferably a compound represented by formula (ld-3), a compound represented by (ld-6), a compound represented by formula (ld-9), a compound represented by formula (ld-12), a compound represented by formula (ld-15), and a formula (1d-1) The compound represented by X2, that is, the compound (Id) in which X2 is an iodine atom. [Table 2 7]

Χ2 ' Ζ&quot;η,Υ' m η XY w Z X2 1 0 ss — - Cl 2 0 ss - -— Br 3 0 ss - - I 4 0 0 0 - - Cl 5 0 0 0 - - Br. 6 0 0 0 - - I 7 0 Se Se - - Cl 8 0 Se Se - - Br 9 0 Se Se - - I 10 1 ssss Cl 11 1 s S ss Br 12 1 s S ss I 13 1 0 0 0 0 Cl 14 1 0 0 0 0 Br 15 1 〇0 0 0 I 16 1 Se Se Se Se 17 17 Se Se Se Se Br 18 1 Se Se Se Se· I

S-61 - 201245216 The method for producing the compound (Id) can be exemplified by including the compound represented by the following $ (le) (compound (1〇),

(wherein, n, W, X, Y and Z represent the same meanings as described above), and reacting with a halogenating agent containing X2 as a halogen atom to obtain a compound in which X and a carbon atom at the 0 position of the oxime are bonded to X2 (hereinafter It is sometimes referred to as an α-substituted compound, and the resulting α-substituted compound is reacted with a strong base such as lithium diisopropylguanidinium to transfer X 2 to a carbon atom bonded to the β-position of X and oxime. 1) The production method in the case of the compound (lb') is, for example, a compound (compound (la)) and a compound represented by the following formula (la') in the presence of a transition metal compound, a copper halide and an organic base. 5) The method of the reaction step:

(wherein, n, W, X, Y, Z and P represent the same meaning as defined above, and X2 each independently represents a halogen atom). Specifically, the compound (1') may be used in the same manner as in the production of the compound (lc), except that the compound (la') is used instead of the compound (Id) in the production of the compound (lc). The method for producing the compound (1 a') includes, for example, reacting a compound (compound (lc')) represented by the following formula (62, 201245216) (lc.) with an alkyllithium.

P

(1C1) (wherein, n, W, X, Y, Z and R represent the same meaning as defined above), a method comprising the step of reacting a halogenating agent containing X2 as a halogen atom with the obtained reaction product. The method for producing the specific compound (la') may be carried out in the same manner as in the production method of the compound (1a), except that the compound (lc') is used instead of the compound (ic) in the production method of the compound (la). The method for producing the compound (1 c ') may, for example, be a step of reacting a metal compound containing P with the compound (Id) in the presence of a transition metal compound, specifically, as long as the compound (Id) is used instead of the compound (lb). The compound (la) in the production method may be used in the same manner as in the production method of the compound (lb), except that the compound represented by the metal compound containing Q is used as the metal compound containing p. Specific compounds () can be exemplified by the compounds described in Tables 28 to 38. -63- 201245216 [Table 2 8] mn XYWZ P- 1 0 s S — — 2 0 s S — 'Stop together 3 0 s S — — Same as above 4 0 0 0 — — Same as above 5 0 0 0 — Together with 6 0 0 0 — — . Same as above 70 Se Se — — Same as above 8 0 Se Se — Same as above 90 Se Se — together with 10 1 SSS s Same as above. 11 1 SS ss Same as above 12 1 SS ss Same as above 13 1 0 0 0 0 Ibid 14 1 0 0 0 0 Same as above 15 1 0 0 0 0 Same as above. 16 1 Se Se Se Se Same as above 17 1 Se Se Se Se Same as above 18 1 Se Se Se Se Ibid. -64- 201245216 [Table 2 9] no-) .m η XY w Z P- 20 0 s S — — 21 0 s S — — Same as above 22 0 s S — Same as above 23 0 0 0 — Together with 24 0 0 〇 — Same as above 25 0 0 0 1 1 Ibid 26 0 Se Se — together with 27 0 Se Se — together with 28 0 Se Se one by one 29 1 SSSS Same as above 30 1 SS s S Same as above 31 1 SS s S Same as above 32 1 0 0 0 0 Same as above 33 1 o 0 〇0 Same as above 34 1 〇0 0 〇 Same as above 35 1 Se Se Se Se Same as 36 1 Se Se Se Se Same as above 37 1 Se Se Se Se Ibid. -65- 201245216 [Table 3 Ο] π-) mn XYWZ P- 40 0 s S — XX) 41 0 s S — — Same as above 42 0 .s S — — Same as above 43 0 0 0 — — Same as above 44 0 o 0 — — Same as above 45 0 0 0 — — Same as above 46 0 Se Se — Same as above 70 0 Se Se — together with 48 0 Se Se — same as above 49 1 SSS s Same as above 50 1 SS ss Same as above 51 1 SS ss Same as above 52 .1 0 0 0 0 Same as above 53 1 0 0 0 0 Same as above 54 1 〇 0 0 0 Same as above 55 1 Se Se Se Se Same as above 56 1 Se Se Se Se Same as above 57 1 Se Se Se Se Ibid. -66- 201245216 [Table 3 1 ] mn XYW z P- 60 0 s S — -to 61 0 s S — — Same as above 62 0 s S — — Same as above 63 0 0 0 — — Same as above 64 0 0 0 — Together with 65 0 0 0 — Together with 66 0 Se Se — together with 67 0 Se Se — Same as above 68 0 Se Se — - Ibid 69 1 SSS s Same as above 70 1 s S ss Same as above 71 1 s S ss Same as above 72 1 0 0 0 0 Same as above 73 1 0 0 0 0. Same as above 74 1 0 0 0 0 Same as above 75 1 Se Se Se Se Same as above 76 1 Se Se Se Se Ibid. 77 1 Se Se Se Se Ibid. -67- 201245216 [Table 3 2] mn XYWZ P- 80 0 s S-81 0 s S — — Same as above 82 0 s S — Ibid. 83 0 0 0 — Same as above 84 0 0 0 — — Same as above 85 0 o 0 — — Same as above 86 0 Se Se — . — Same as above 87 0 Se Se — — Same as 88 0 Se Se — Same as above 89 1 SSS s Same as above 90 1 SS ss Same as above 91 1 SS ss Same as above 92 1 0 0 0 0 Same as above 93 1 0 0 0 0 Same as above 94 1 0 0 0 0 Same as above 95 1 Se Se Se Se Same as 96 1 Se Se Se Se Same as above 97 1 Se Se Se Se Ibid. -68- 201245216 [Table 3 3] m η XY w Z p- 100 0 s S - 101 0 ss One - Same as above 102 0 ss — — Same as above 103 0 0 0 — — Same as above 104 0 0 0 — — Same as above 105 0 o 0 — — Same as above 106 0 Se Se — Same as above 107 0 Se Se — Same as above 108 0 Se Se — — Same as above 109 1 ss S s Same as above 110 1 ssss Same as above 111 1 ssss Same as above 112 1 0 0 0 0 Same as above 113 1 0 0 〇0 Same as above 114 • 1 0 0 0 0 Same as above 115 1 Se Se Se Se Same as above 116 1 Se Se Se Se Same as above 117 1 Se Se Se Se Ibid. -69- 201245216 [Table 3 4] do-) m η . XYWZ P- 120 0 s S — — XXX^ 121 0 s S — Same as above 122 0 s S — Same as above 1 23 0 0 0 — — Same as above 124 0 o 〇一 — — Same as above 125 0 0 〇一 — Same as above 126 0 Se Se — Together with 127 0 Se Se — Same as above 128 0 Se Se — Same as above 129 1 SSS s Same as above 130 1 SS ss Same as above 131 1 SS ss Same as above 132 1 0 〇0 0 Same as above 133 1 o 0 0 0 Same as above 134 1 o 0 0 o Same as above 135 1 Se Se Se Se Same as above 136 1 Se Se Se Se Same as above 137 1 Se Se Se Se Ibid -70- 201245216 [Table 3 5] The more m η XYWZ P- 140 0 ss One PQ 141 0 s S One - Same as above 142 0 ss — Same as above 143 0 0 0 — — Same as above 144 0 0 0 — — Same as above 145 0 0 0 — — Same as above 146 0 Se Se — Same as above '147 0 Se Se — Same as above 148 0 Se Se — Together with 149 1 SSS s Same as above 150 1 SS ss Same as above 151 1 ssss Same as above 152 1 0 〇0 〇 Ibid 153 1 0 0 0 0 Same as above 154 1 0 0 0 0 Same as above 155 1 Se Se Se Se Same as above 156 1 Se Se Se Se Same as above 157 1 Se Se Se Se Same as above -71 - 201245216 [Table 3 6 ] (1-) m η XYWZ P - 160 0 s S — — po 161 0 s S One-to-one 162 0 s S — — same 163 0 0 0 — — Same as above 164 0 0 0 — — Same as above 165 0 o 0 — Same as above 166 0 Se Se — Same as above 167 0 Se Se — Same as above 168 0 Se Se — Same as above 169 1 SSS s Same as above 170 1 SSS s Same as above 171 1 SSS s Same as above 172 1 0 〇0 〇 Same as above 173 1 0 0 〇o Same as above 174 1 〇, 0 〇o Same as above 175 1 Se Se Se Se Same as above 176 1 Se Se Se Se Same as above 177 1 Se Se Se Se Same as above -72- 201245216 [Table 3 7] π-) mn XYWZ p- ISO 0 s S — — P 181 0 s S — — Same as above 182 0 s S — Same as above 183 0 0 0 — I Same as above 184 0 0 0 — — Same as above 185 0 0 0 — — Same as above 186 0 Se Se — Together with 187 0 Se Se — Same as above 188 0 Se Se One — Same as above 189 1 S s S s Same as above 190 1 SS ss Same as above 191 1 S sss Same as above 192 1 0 0 〇0 Same as above 193 1 0 0 0 o Same as above 194 1 0 0 0 o Same as above 195 1 Se Se Se Se Same as above 196 1 Se Se Se Se Same as above 197 1 Se Se Se Se Ibid. -73- 201245216 [Table 3 8 ] m η XYWZ P- 200 0 s S one by one..9〇201 0 s S — together with 202 0 s S — together 203 0 0 0 — — Same as above 204 0 0 0 — Same as above 205, 0 0 0 — Same as above 206 0 Se Se — together with 207 0 Se Se — together with 208 0 Se Se One. Same as above 209 1 SS s S Same as above 210 1 SS s S Same as above 211 1 SS s S Same as above 212 .1 0 0 0 0 Same as above 213 1 0 0 0 0 Same as above 214 1 0 0 0 〇 Same as above 215 1 Se Se Se Se Same as above 216 1 Se Se Se Se Same as 217 1 Se Se Se Se The compound (1) of the present invention can be used as an organic semiconductor material which is soluble in an organic solvent. The organic solvent for dissolving the compound (1) may, for example, be an aromatic such as benzene, toluene, xylene, tetrahydronaphthalene, mesitylene, chlorobenzene, o-dichlorobenzene, trichlorobenzene, fluorobenzene or anisole. a hydrocarbon solvent such as a halogenated aliphatic hydrocarbon solvent such as dichloromethane, chloroform, 1,2-dichloroethane, 1,1', 2,2'-tetrachloroethane, tetrachloroethylene or carbon tetrachloride, for example An ether solvent such as diethyl ether, dioxane or tetrahydrofuran, for example, an aliphatic hydrocarbon solvent such as pentane, hexane, heptane, octane or cyclohexane, for example, acetone, methyl ethyl ketone or methyl isobutyl -74- 201245216 A ketone solvent such as a ketone or a cyclohexanone, for example, an ester solvent such as ethyl acetate or butyl acetate, for example, a nitrile solvent such as acetonitrile, propionitrile, methoxyacetonitrile, glutaronitrile or benzonitrile, for example An aprotic polar solvent such as dimethyl sulfoxide, cyclobutyl hydrazine, N,N-dimethylformamide, hydrazine, hydrazine-dimethylacetamide or N-methyl-2-pyrrolidone. Preferred examples are toluene, xylene, tetrahydronaphthalene, mesitylene, chlorobenzene, o-dichlorobenzene, dichloromethane, chloroform, tetrahydrofuran and the like. The organic solvent may be used by mixing two or more kinds of solvents. The concentration of the compound (1) in the solution of the dissolved compound (1) is usually in the range of 0.001 to 50% by weight, preferably 0.01 to 10% by weight, more preferably 0.1 to 5% by weight. The compound (1) in the solution may be used alone, and may be organically different from the antioxidant, the stabilizer, and the compound (1) as long as it does not significantly impair the range of carrier mobility of the film (organic semiconductor active layer) described later. A semiconductor material, an organic insulating material, or the like is mixed. The organic semiconductor material different from the compound (1) may be a low molecular material or a high molecular material. The polymer material may also be one obtained by crosslinking a polymer. Preferred examples are polymeric materials. Specific examples are exemplified by polyacetylene and its derivatives, polythiophene and its derivatives, polythiophene ethylene and its derivatives, polyphenylene and its derivatives, polyphenylene phenylene and its derivatives, Polypyrrole and its derivatives, polyaniline and its derivatives, polydiamine and its derivatives, polyquinoline and its derivatives, dinaphthalene and its derivatives, tetracene and its derivatives, and Benzene 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 based on the total of the organic semiconductor material and the compound (n-75-201245216) which is different from the compound (1). The organic insulating material may be a low molecular sub-material. The polymer material may also be a polymer which is preferably listed as a molecular material. As a specific example, polycarbonate, polydimethyl siloxane, nylon, poly-copolymer , epoxy polymer, cellulose, polyoxyl polymer, polyethylene polymer, polyester polymer, polystyrene S polymer, gas polymer, raw fat, amine resin, unsaturated poly In the polycrystalline film formed by ester resin, benzene diene, epoxy resin, polyimide resin, polyamine resin, and various polymer units, the content of the compound (1) is relative to the compound; The total amount of 100% by weight is preferably 10% by weight or more. Further, the solution composition is obtained by adding a compound of 10 to 200 ° C, preferably about 20 to 150 ° C. Next, the film of the present invention is obtained. And organic semiquinone The material (1) has a carrier mobility of ruthenium, and is suitable as a material of the organic semiconductor device having the thin film layer. Further, the organic semiconductor device of the present invention is contained. The organic semiconductor device of the present invention can be exemplified as an example. It is a material of 20% by weight, and it can also be a high-crosslinking reaction. It is exemplified by polystyrene, quinone imine, cyclic olefin methylene, polyolefin compound, polyether polymer dissolving plastic, a phenolic resin diallyl carboxylic acid resin resin, a polyfluorene oxide compound, etc. The insulating material of the present invention is more than 5% by weight, and more preferably can be prepared by, for example, (1) dissolving in a solvent conductor device. It is to be noted that the film exhibits high film as an organic semiconductor, such as an organic transistor, an electro-optical cell, an electric cell, a solar cell, etc. Further, the organic transistor of the present invention can be used for, for example, electronic paper. The method for forming the film of the present invention in a flexible display, a 1C label, a sensor, or the like can be exemplified by, for example, a coating film forming process. Here, the so-called coating film forming process means having the former A film forming process in which the compound (1) is dissolved in a solvent and the resulting solution is applied onto a substrate or an insulator layer. The coating method is exemplified by a casting coating method, a dip coating method, a die coating method, and a roll. Coating method, bar coating method, spin coating method, inkjet method, screen printing method, lithography method, microcontact printing method, etc. These methods may be used singly or in combination of two or more. (1) The solution of the organic solvent is applied to the substrate or the insulating layer to form a coating film, and then the solvent contained in the coating film is removed to form a film on the substrate or the insulating layer. Natural drying treatment, heat treatment, pressure reduction treatment, ventilation treatment, or a combination of these treatments is employed, but from the viewpoint of ease of handling, natural drying treatment or heat treatment is preferred. A brief description of the conditions associated with the treatment is exemplified by the conditions of placing the substrate in the atmosphere or heating the substrate with a hot plate (e.g., 40 to 250 ° C, preferably 50 to 200 ° C). The film of the present invention can also be formed into a film by coating film formation using a dispersion in which the compound (1) is dispersed in a solvent. In this case, in the above-described coating film forming process, the solution can be easily replaced by changing the solution. In this case, the solvent may be water in addition to the above organic solvent. Therefore, the film of the present invention can be formed by the above-described coating film forming process, etc., and the method of forming the film of the present invention can be exemplified by supplying the compound (η to vacuum evaporation, sputtering). A method of forming a thin film in a vacuum process such as a method, a CVD method, or a molecular beam epitaxial growth method. The method of forming a thin film by vacuum evaporation is to heat (evaporate) and evaporate the compound (1) in a vortex or a metal crucible under vacuum. A method of depositing an organic semiconductor material on a substrate or an insulator material. The degree of vacuum during vapor deposition is usually less than lxiodpa, preferably less than lxi〇-3Pa. The substrate temperature during vapor deposition is usually from 0 ° C to 300 °. C is preferably 20. (: 〜200 ° C. The vapor deposition rate is, for example, in the range of 0.001 nm/sec to 10 nm/sec, etc., preferably in the range of 0.01 nm/sec to 1 nm/sec. The film thickness of the film containing the compound (1) obtained by the coating film forming process or the above vacuum process can be appropriately adjusted depending on, for example, the element structure of the organic transistor, but is preferably from 1 nm to 10 μm, more preferably from 5 nm to ΙμΓη. Organic transistor For example, there is an airport effect transistor (OFET). The structure of the organic field effect transistor is generally provided by arranging the source electrode and the drain electrode adjacent to the organic semiconductor active layer formed by the film of the present invention, and then interposing The insulating layer (dielectric layer) may be provided adjacent to the organic semiconductor active layer, and the gate electrode may be provided. For example, the element structure is as follows: (1) substrate/gate electrode/insulator layer/source electrode·dip electrode/organic Structure of semiconductor active layer (2) Structure of substrate/gate electrode/insulator layer/organic semiconductor active layer/source electrode and drain electrode (refer to Fig. 1) -78- 201245216 (3) Substrate/organic semiconductor active layer/ Structure of source electrode, drain electrode, insulator layer/gate electrode (4) structure of substrate/source electrode, drain electrode/organic semiconductor active layer/insulator layer/gate electrode (see Fig. 2), etc. The source electrode, the drain electrode, and the gate electrode may each be provided in plural. Further, a plurality of organic semiconductor active layers may be disposed in the same plane, or may be laminated, and then a specific example will be described. In the production of the organic transistor, the material for forming the source electrode, the drain electrode, and the gate electrode is not particularly limited as long as it is a conductive material, and platinum, gold, or the like can be used. Silver, nickel, chromium, copper, iron 'tin, antimony, lead, antimony, indium, palladium, iridium, osmium, iridium, aluminum, lanthanum, cerium, molybdenum, molybdenum oxide, tungsten, tin oxide, antimony, indium oxide, tin (ITO), fluorine-doped zinc oxide, zinc, carbon, graphite, crushed carbon, silver paste and carbon paste, lithium, barium, sodium, magnesium, potassium, calcium, barium, titanium, manganese, zirconium, gallium, germanium , sodium, sodium-potassium alloy, magnesium, lithium, aluminum 'magnesium/copper mixture, magnesium/silver mixture, magnesium/aluminum mixture, magnesium/indium mixture, aluminum/alumina mixture, lithium/aluminum mixture, etc., but preferably Platinum, gold, silver, molybdenum oxide, indium 'ITO, carbon. Alternatively, a conventional conductive polymer which is improved in conductivity by doping or the like, such as conductive polyaniline, conductive polypyrrole, conductive polythiophene, poly(ethylenedioxythiophene), and polystyrene sulfonate may be suitably used. Acid complexes and the like. Among them, it is preferred that the contact surface with the semiconductor layer has less resistance. These conductive materials may be used singly or in combination of two or more. Although the film thickness of the electrode varies depending on the material, it is preferably -79 to 201245216 of 0 · 1 nm to 10 μm, more preferably 5 5 nm to 5 μηι, and more preferably 1 nm to 3 μηι. Further, when the gate electrode also serves as a substrate, it may be thicker than the above film. The source electrode and the drain electrode used in the organic transistor of the present invention may be subjected to surface treatment. When the surface of the electrode which is in contact with the film (organic semiconductor active layer) of the present invention is subjected to a surface treatment, it tends to increase the crystal characteristics of the organic transistor containing the film. As the surface treatment, for example, saturation of a thiol group such as 1-octyl mercaptan, 1-perfluorooctyl mercaptan, 1-octadecyl mercaptan, or 1-perfluorooctadecyl mercaptan may be mentioned. a hydrocarbon compound such as a thiol group-containing aromatic compound such as phenylthiol or perfluorobenzenethiol, such as a thiol compound having a thiol group such as a thienylthiol or a perfluorothiophenylthiol; A method in which the electrode is subjected to a immersion treatment or the like in the solution together with an alcohol or the like to modify the surface of the electrode. The method of forming the electrode can be carried out by various methods using the above materials. Specifically, it is exemplified by a vacuum deposition method, a sputtering method, a coating method, a thermal transfer method, a printing method, a sol gel method, and the like. When forming a film or after film formation, it is preferable to pattern as needed. Various methods can be used for the method of patterning. Specifically, it is exemplified by a patterning of combined photoresist and a photolithography method of etching. Further, examples thereof include a printing method such as inkjet printing, screen printing, lithography, and letterpress printing, and a method of soft lithography such as a microcontact printing method. These methods may be used alone or in combination of two or more. Modeling. As the insulator layer, various insulating films can be used. The material of the insulating film can be exemplified by an inorganic oxide, an inorganic nitride, an organic compound or the like. The inorganic oxides are exemplified by cerium oxide, aluminum oxide, molybdenum oxide, titanium oxide-80-201245216, tin oxide, palladium oxide, palladium titanate titanate, strontium titanate titanate, lead zirconate titanate, lead titanate tantalum, titanium Barium strontium, barium titanate, barium magnesium fluoride, barium titanate, barium titanate, barium strontium strontium, strontium bismuth citrate, antimony trioxide, etc., preferably cerium oxide, aluminum oxide, molybdenum oxide, oxidation titanium. The inorganic nitrides are exemplified by tantalum nitride, aluminum nitride, and the like. The organic compound is exemplified by polyimine, polyamine, polyester, polyacrylate, photocurable resin obtained by photoradical polymerization or photocationic polymerization, copolymer containing acrylonitrile component, polyvinylphenol, poly The vinyl alcohol, the novolac resin, the cyanoethyl pullulan, etc. are preferably polyimine, polyvinylphenol, or polyvinyl alcohol. The materials of the insulator layers may be used singly or in combination of two or more. The thickness of the insulator layer varies depending on the material, but is preferably from 0.1 nm to 1 〇 Ο μιη 1 , more preferably from 0.5 nm to 50 μm, and even more preferably from 5 nm to 10 μm. The method of forming the insulator layer can be carried out by various methods using the above materials. Specifically, it is exemplified by spin coating, spray coating, dip coating, casting, bar coating, blade coating, screen printing, lithography, inkjet, vacuum evaporation, and molecular beam epitaxy. Dry process methods such as ion beam method, ion plating method, sputtering method, atmospheric piezoelectric slurry method, and CVD method. Further, a sol gel method or a method of forming an oxide film on a metal of alumite on aluminum, a metal such as a thermal oxide film of ruthenium or the like. The substrate material is exemplified by glass, paper, quartz, ceramic, resin, and the like. The material of the resin sheet is specifically exemplified by polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyether selenium (PES), polyether sulfimine, polyether ether ketone, Polyphenylene sulfide, polyacrylate, polyimine, polycarbonate (PC), cellulose triacetate (TAC), fiber -81 - 201245216, vitamin acetate propionate (CAP), and the like. The thickness of the substrate is preferably Ιμηι 10 mm, more preferably 5 μηι 5 mm. In the portion of the insulator layer or the substrate which is in contact with the film of the present invention (hereinafter sometimes referred to as an organic semiconductor active layer), the surface of the insulator layer or the substrate may be subjected to surface treatment. The surface characteristics of the organic transistor can be improved by surface-treating the insulator layer of the laminated organic semiconductor active layer. Specifically, the surface treatment is a hydrophobization treatment using hexamethylene diazane, octadecyltrichloromethane, octyltrichlorodecane or phenethyltrichloromethane, and hydrochloric acid, sulfuric acid, and the like. Acid treatment such as aqueous solution of hydrogen peroxide, treatment with alkali such as sodium hydroxide, potassium hydroxide, calcium hydroxide, ammonia, etc., ozone treatment, fluorination treatment, plasma treatment of oxygen or argon, etc., Lanmul Brogji ( Langmuir-Brodgett) formation of a film, formation of a film of another insulator or semiconductor, electrical treatment of a mechanical treatment, corona discharge, etc., rubbing treatment using a fiber or the like, etc. The method of performing surface treatment is exemplified by vacuum evaporation, for example. Method, sputtering method, coating method, printing method, lyotropic method, and the like. Further, a protective film made of a resin or an inorganic compound may be provided on the organic semiconductor active layer. By forming the protective film, the shadow H of the outside air can be suppressed, and the driving of the transistor can be stabilized. Since the film of the present invention contains the compound (1), it exhibits high carrier mobility. That is, the film of the present invention is useful as an organic semiconductor active layer in an organic transistor, and an organic transistor having an organic semiconductor active layer containing the film of the present invention is an organic semiconductor device which exhibits excellent crystal characteristics. The latter" -82- 201245216 The film of the present invention has a luminescent property and can be used as a luminescent film. The luminescent film means a film containing the film of the compound (1) and emitting light under conditions of light or electric stimulation. As the light-emitting film, a material which is a light-emitting element such as an organic light-emitting diode, a liquid crystal display element, an organic electroluminescence element, or an electronic paper can be used. The luminescent film of the present invention can be produced in the same manner as in the conventional methods, except that the compound (1) of the present invention is used as a material. The organic semiconductor device including the thin film of the present invention can be applied to sensors, RFIDs (Radio Frequency Identification Cards) and the like in addition to the above-described organic transistor and light-emitting element. EXAMPLES Hereinafter, the present invention will be described in more detail by way of examples. The confirmation of the reaction was carried out under the following conditions of gas chromatography (GC) and high-speed liquid chromatography (LC): 1 gas chromatography analyzer Shimadzu GC2010, manufactured by J&amp;W Scientific, DB-1, Diameter 0 · 2 5 mm, length 3 0 m 2. High-speed liquid chromatography analyzer Shimadzu LC 1 0ΑΤ Manufactured by column chemical substance evaluation mechanism, L-column ODS, inner diameter 4.6mm, length 15cm -83- 201245216 The high-speed liquid chromatography purification system was carried out using the following apparatus and column. Device LC-9 104C manufactured by Nippon Analytical Co., Ltd.) Pipe column manufactured by Japan Analytical Industries Co., Ltd., JAIGEL-1H-4 0, two inner diameters of 20 mm and a length of 60 cm. The identification of the product was measured by the following analysis apparatus. 1 · j-NMR : EX2 70 (manufactured by Sakamoto Electronics Co., Ltd.) 2. HRMS: JMS-T100GCC manufactured by JEOL Ltd.) 3. LC-HRMS: QSTAR XL (Applied Biosystem) Manufactured by mechanism, L-column ODS, inner diameter 4.6 mm, length 15 cm β Example 1: Preparation of 3,6-diiodothieno[3,2-b]thiophene (compound (ld-3))

2,5-Dibromothieno[3,2-b]thiophene is prepared by reacting N-bromosuccinate with thieno[3,2-b]thiophene (cf. Dalton Trans., 2005, 8 Page 74) Next, lithium diisopropylamide is reacted with 2,5-dibromothieno[3,2-b]thiophene to prepare 3,6-dibromothieno[3,2-b] Crystallization of thiophene (Ref. -84- 201245216

Org. Lett·, 2007, 9 volumes, 1 005 pages). Crystals of 3,6-dibromothieno[3,2-b]thiophene (5.00 g, 1 6.8 mmol) were placed in a reaction vessel equipped with a stirrer and a thermometer, and the inside of the vessel was replaced with nitrogen. Next, 17 〇ml of diethyl ether was added to the vessel, and after dissolving the crystal at room temperature (about 25 ° C), the solution was cooled to -78 °C. Then, a hexane solution (23.5 ml, 36.9 mmol) of n-butyllithium (manufactured by Kanto Chemical Co., Ltd., 1.57 M) was added to the solution in one minute while maintaining the temperature at _78 ° C, and further at the same temperature. After stirring for 2 hours, a reaction liquid was obtained. Further, a solution obtained by dissolving iodine (1 g. 2 g, 40.3 mmol) in 100 ml of dehydrated diethyl ether was added to the reaction liquid adjusted to -78 ° C for 15 minutes, and stirred at the same temperature for 2 hours. . The reaction solution was allowed to warm to room temperature, and stirred at the same temperature for 3 hours, and then added to a saturated aqueous solution of ammonium chloride, and then diethyl ether was added. The organic layer was separated, washed with a saturated aqueous solution of sodium sulfite and saturated aqueous sodium chloride, and dried over sodium sulfate. The obtained product was purified by silica gel chromatography (mobile layer; hexane) to give 3,6-diiodothieno[3,2-b]thiophene (compound (Id-3), 6.1 lg, 15.6 mmol. ) yellow crystals. The physical properties of the compound (1 d - 3 ) are as follows. 'H-NMR (5, CDC13): 7.48 (s, 2H) Example 2: 3,6-bis[2-(trimethyldecyl)ethynyl]thieno[3,2-b]thiophene (compound) (ic_13)) Manufacturing

-85- 201245216 Mix 3,6-diiodothieno[3,2-15]thiophene (4.00 §, 1 0.2 mmol) in a reaction vessel equipped with a stir bar, thermometer, and condenser under a nitrogen atmosphere. After 143 ml of propylamine and 10 ml of toluene were added, the resulting mixture was stirred at room temperature, and nitrogen gas was blown through an injection needle for 30 minutes. Then 'bis(triphenylphosphine)palladium dichloride (0.22 g, 0.3 mmo 1 ), cuprous iodide (0.12 g, 0-6 mmol) and trimethyldecyl acetylene (2.31) at room temperature under nitrogen atmosphere g, 23.5 mmol) was added to the reaction vessel, and the mixture was heated to 60 ° C and stirred at the same temperature for 5 hours. Then, after cooling to room temperature, water and chloroform were added. The organic layer was separated, washed with water and dried over magnesium sulfate. The obtained product was purified by silica gel chromatography (mobile layer; hexane) to give 3,6-bis[2-(trimethyldecyl)ethynyl]thieno[3,2-b]thiophene in a yield of 95%. Compound (lc-13), 3.24 g, 9.74 mmol) of white crystals. The compound (lc-13) is a compound corresponding to the compound of m = 13 in Table 26, and the physical properties of the compound (lc-13) are as follows. 1 H-NMR (6, CDC13 ) : 0.26 ( s, 1 8H ) , 7.54 ( s, 2H) 贲 Example 3: 3,6-bis[2-(trimethyldecyl)ethynyl l·2, Manufacture of 5-diiodothieno[3,2-b]thiophene (compound (la-13))

Feeding 3,6-bis[2-(trimethyldecyl)ethynyl]thieno[3,2-b]thiophene obtained in Example 2 -86-201245216 in a reaction vessel equipped with a stirrer and a thermometer The crystals of the compound (lc-13), 2.40 g, 7.22 mmol) were subjected to nitrogen substitution in the inside of the vessel, and then dehydrated diethyl ether 50 m was added, and the crystal was dissolved at room temperature. After the obtained solution was cooled to -78 ° C, a solution of a third butyl lithium (manufactured by Kanto Chemical Co., Ltd., 1.55 M) in a positive chamber (1 ml, 16.6 mmol) was added at the same temperature for 10 minutes. After stirring at a temperature for 10 minutes, the temperature was raised to 〇 ° C and stirred at the same temperature for 1 hour to obtain a reaction liquid. Further, iodine (4.40 g, 17.3 mmol) was dissolved in 90 ml of dehydrated diethyl ether to prepare an iodine solution. The iodine solution was added to the reaction solution at 0 ° C for 10 minutes, and the mixture was heated to room temperature and stirred at the same temperature for 1 hour. The reaction mixture was added to ice water, and the obtained organic layer was washed with saturated aqueous sodium sulfate and saturated aqueous sodium chloride, and dried over sodium sulfate. The obtained product was purified by silica gel chromatography (mobile layer:hexane) to yield 3,6-bis[2-(trimethyldecyl)ethynyl]-2,5-diiodothiophene [3] in a yield of 87%. , 2-b] Thiophene (3.68 g, 6.30 mmol) of yellow crystals. The compound (la-13) was a compound corresponding to m = 13 of Table 23. The physical properties of the compound (la-1 3 ) are as follows. 1 H-NMR (6, CDC13): 0.28 (s, 1 8H) Example 4: 2,5-bis(thieno[3,2-13]thiophen-2-yl)-3,6-bis[2 -(Trimethyldecyl)ethynyl]thieno[3,2-b]thiophene (compound (1-13)) -87- 201245216

(1-13) A crystal of b]pyr (1.50 g, 10.7 mmol) was fed into a reaction vessel equipped with a stirrer and a thermometer to displace the reaction gas. Next, the dehydrated tetrahydrofuran l〇〇ml was added to the room temperature to dissolve the crystals, and the resulting solution was cooled to a temperature of 5 minutes to the third butyl lithium (Kantong | |) Zhengjiyuan solution (6.21 ml, 9.63) Add) to the solution, and then stir at the same temperature for 1 hour, then add tri(n-butyl)tin chloride (2.61 ml, and warm to room temperature, stir for 3 hours at the same temperature for installation) In a separate reaction vessel of the stirrer, the 3,6-bis[2-(trimethylhydrazine)-2,5-diiodothieno[3,2-b]thiophene obtained in Example 3 was mixed at a nitrogen temperature. Compound (la-: 4.81 mmol), ginseng (dibenzylideneacetone) 0.48 mmol), tris(2-furyl)phosphine (0.22 g, dehydrated tetrahydrofuran), obtained a mixture. The mixture was added to the above reaction solution and stirred for another 22 hours. The saturated aqueous sodium chloride solution and the mixture were mixed. The organic layer was separated, washed with water, and the solvent was evaporated under reduced pressure of sulfur. The crude product was taken into the thieno [3,2-container inside the vessel via nitrogen, • 78t. Manufactured in the same B, 1.55M in cold After being dissolved at -7 8 t at 5 9.63 mmol), the reaction liquid atmosphere was obtained and the benzyl group) ethynyl group 13), 2.8 1 g, IG (0 · 44 g, 0-96 mmol) and in the same temperature chloroform After being added to the magnesium sulfate to be dried, the product is obtained by high-speed liquid chromatography (moving layer; chloroform) in a cycle of -88-201245216, and the solvent is distilled off, and then recrystallized from toluene to obtain 2 in a yield of 25%. 5-bis(thienoindole, 2-b)thiophen-2-yl)-3,6-bis[2-(trimethyldecyl)ethynyl]thieno[3,2-b]thiophene (compound ( 1-13), 0.72 g ' 1.18 mmol) of yellow crystals. The compound (1-13) is a compound corresponding to m=13 of Table 1. The physical properties of the compound (1 -1 3 ) are as follows.

H-NMR ( δ , CDC13 ) : 0.36 ( s, 18H) , 7.27 ( d, 2H ), 7.42 ( d, 2H ), 7.8 1 ( s, 2H ) LC-HRMS ( APPI+ ): Calculation of C28H25S i2S6値608.98 1 4 ;Measured 値608.9805 Example 5: Manufacture of 3,6-bis[2-(triisopropyldecyl)ethynyl]thieno[3,2-b]thiophene (compound (lc-15)) iPr3Si

(1c-15). Except that trimethyldecyl acetylene was changed to triisopropyldecyl acetylene, the same operation as in Example 2 was carried out to obtain 3,6-bis[2-(3) in a yield of 98%. Isopropyl decyl) ethynyl]thieno[3,2-b]thiophene (white crystallization of compound ( lc-15)) The compound (ic_15) is a compound corresponding to m = 15 in Table 26. The physical properties of the compound (1 c_丨5 ) are as follows. 'H-NMR ( ά , CDC13 ) : 1 .05-1 . 19 ( m, 42H ) , 7.53 (s, 2H). -89- 201245216 Example 6: 3,6-bis[2-(triisopropyldecyl)ethynyl]·2,5-diiodothieno[3,2-b]thiophene (compound (la-15) )) manufacturing

Except that the compound (lc-13) was changed to the compound (lc-15), the same operation as in Example 3 was carried out, and 3,6-bis[2-(triisopropyldecylalkyl)acetylene was obtained in a yield of 95%. Yellow crystal of -2,5-diiodothieno[3,2-b]thiophene (compound (la-15)). The compound (la-15) is a compound corresponding to m = 15 of Table 23. The physical properties of the compound (la-15) are as follows: 'H-NMR (6, CDC13): 1 · 0 7 to 1 · 2 1 (s, 4 2 Η ) 苡 Example 7: 2,5-bis (thieno[ 3,2-b]thiophen-2-yl)*3,6-bis[2-(triisopropyldecyl)ethynyl]thieno[3,2-b]thiophene (1·15) Manufacturing

Except that the compound (1 a· 13 3 ) was changed to the compound (la-1 5 ) in the same manner as in Example 4, using #-90 - 201245216, 2,5-bis (thieno[3, 2-b]thiophen-2-yl)·3,6-bis[2-(triisopropyldecyl)ethynyl]thieno[3,2-b]thiophene (compound (1 -1 5 )) Yellow crystals. The compound (1-15) is a compound corresponding to m = 15 of Table 1. The physical properties of the compound (1-1 5 ) are as follows. 'H-NMR ( δ , CDC13 ) · 1.14-1.29 ( m, 42H ) , 7.25 (d, 2H) , 7.41 ( d, 2H ), 7.88 ( s, 2H) LC-HRMS ( APPI+ ): for C4〇H49Si2S6 Calculation 値777.1 692; Measured 値777.1 686 Example 8: 3,6·bis[2-(triethyldecyl)ethynyl]thieno[3,2-1?]thiophene (compound (1^14) Manufacturing

Except that trimethyldecyl acetylene was changed to triethyldecyl acetylene, the same operation as in Example 2 was carried out, whereby 3,6-bis[2-(triethyldecyl)acetylene was obtained in a yield of 98%. a yellow oil of thieno[3,2-b]thiophene (compound (lc-14)). The compound (c-14) is a compound corresponding to 14 of Table 26. The physical properties of the compound (1 c· 14 ) are as follows.

*H-NMR (5, CDC13): 0.70 (q, 1 2H), 1·07 (t, l8H), 7.54 (s, 2H) Example 9: 3,6-bis[2-(triethyldecane) Manufacture of iodothio[3,2-b]thiophene (compound (ia_i4))

Except that the compound (1 c-1 3 ) was changed to the compound (! c·丨4 ), the same operation as in Example 3 was carried out to obtain 3,6-bis[2-(triethyldecane) in a yield of 99%. Yellow crystal of ethynyl]-2,5-diiodothieno[3,2-b]thiophene (compound (la-14)). Compound (la_14) is a compound corresponding to m = 14 of Table 23. The physical properties of the compound (ia-14) are as follows.

'H-NMR (5, CDC13): 0.71 (q, 12H), 1.09 (t, 18H) Example 10: 2,5-bis(thieno[3,2-b]thiophen-2-yl)-3 Manufacture of 6-bis[2·(triethyldecyl)ethynyl]thieno[3,2-b]thiophene (compound (1-14))

Except that the compound (1 a-1 3 ) was changed to the compound (1 a-1 4 ), the same operation as in Example 4 was carried out to obtain 2,5-bis (thieno[3,2- in a yield of 41%). b]thiophen-2-yl)-3,6-bis[2-(triethyldecyl)ethynyl]thia-92- 201245216 benzo[3,2-b]thiophene (compound (1-14 )) Yellow crystals. The compound (1-14) is a compound corresponding to m = 14 in Table 1. The physical properties of the compound (1-H) are as follows. *H-NMR ( δ , CDC13 ) : 0.78 ( q,12H), 1.13 ( t, 18H), 7.25 ( d,2H) , 7.41 ( d, 2H ), 7.85 (s, 2H) LC-HRMS ( APPI+ ) : Calculation for C 3 4 H 3 7 S i 2 S 6 値 6 93.07 5 3 ; Measured 値 6 9 3.0 7 5 8 Example 11: 2,5-bis (dithieno[3,2-13:2 ',3'-(1)thiophen-2-yl)-3,6-bis[2-(trimethyldecyl)ethynyl]thieno[3,2-b]thiophene (compound (1-40) Manufacturing

The reaction was carried out in the same manner as in Example 4 except that the thieno[3,2-b]thiophene was changed to dithieno[3,2-b:2',3'-d]thiophene. After completion of the reaction, the reaction solution was cooled to room temperature and filtered, and the filtrate was washed with water, ethanol and hexanes, and dried to obtain 2,5·bis(dithieno[3] in a yield of 56%. , 2-1?: 2',3'-Pyrylthiophen-2-yl)-3,6-bis[2-(trimethyldecyl)ethynyl]thieno[3,2-b]thiophene (compound) Orange crystal of (1-40)). The compound (Bu 4〇) is a compound corresponding to m = 40 of Table 2. The physical properties of the compound (1 - 40) are as follows. -93- 201245216

'H-NMR ( &lt;5, CDC13) : 0.38 ( s, 1 8H ), 7.3 1 ( d, 2H ), 7.42 ( d, 2H ), 7.8 1 ( s, 2H ) HRMS ( EI+ ): for C32H24Si2S8 Calculated 値719.9182; 値7 1 9.9 1 4 8 Example 12: 2,5-bis(dithieno[3,2-1?:2,3,-£1]thiophen-2-yl)-3 Manufacture of 6-bis[2-(triethyldecyl)ethynyl]thieno[3,2-b]thiophene (compound (1-41))

In addition to changing the thieno[3,2-b]thiophene to dithieno[3,2-b:2,,3'-d]thiophene' and changing the compound (la-13) to the compound obtained in Example 9 ( 1 a-1 4 ), except that recrystallization from toluene was omitted, the same operation as in Example 4 was carried out, whereby 2,5-bis(dithieno[3,2-b:2' was obtained in a yield of 52%. , 3'-d]thiophen-2-yl)-3,6-bis[2·(triethyldecyl)ethynyl] benzophenan [3,2-b]thiophene (compound (i_41 )) yellow crystallization. The compound (1-41) is a compound corresponding to m = 41 in Table 2. The physical properties of the compound (ΙΑ1) are as follows. 'H-NMR ( δ , CDC13 ) : 0.80 ( q, 12H ) , 1.15 ( t, *8Η) , 7.29 ( d, 2H) , 7.40 ( d, 2H ) , 7.84 ( s, 2H) HRMS ( EI+): Calculation of C38H36Si2S8 値804.0 1 2 1 ; -94- 201245216 Measured 値804.0 1 03 Example 13: Film and organic transistor using the film as an organic semiconductor layer were fabricated on a glass substrate using a lift-off process or lithography The chrome and gold are vapor-deposited in sequence, and the source and drain electrodes are arranged. At this time, the thickness of the chromium layer was 5 nm, and the thickness of the gold layer was 40 nm. After the electrodes were placed, the substrate was ultrasonically washed in the order of acetone and isopropyl alcohol, dried, and then cleaned with oxygen plasma, and then heated at 80 ° C for 5 minutes to carry out a dehydration operation. The channel width is now 2 mm and the channel length is 100 μm. The channel portion was subjected to phenethyltrichloromethane treatment, and after the electrode portion was subjected to pentafluorobenzenethiol treatment, the compound (1-15) produced in Example 7 was added dropwise at 0.6 wt/vol% under a nitrogen atmosphere. The hydrogen naphthalene solution was formed into an organic layer by a spin coating method, and then a solution containing a fluoropolymer was dropped on the organic layer to form an insulating layer by a spin coating method. The film thickness of the compound (1-15) at this time was 25 nm, and the film thickness of the insulating layer was 300 nm. A mask was used on the insulating layer, and chromium and aluminum were sequentially vapor-deposited to form a gate electrode, and an organic transistor as shown in Fig. 2 was fabricated. At this time, the thickness of the chromium layer was 5 nm, and the thickness of the underlayer was 200 nm. Next, the electrical characteristics of the obtained organic crystal device were measured. As a result, at a certain gate voltage (Vg), the curve of the drain current (Id) with respect to the drain voltage (Vd) is good, and the saturation region is high at the high gate voltage. Further, when the negative gate voltage applied to the gate electrode is increased, since the negative drain current is also increased, it is confirmed that the organic transistor having the film of the compound (1 -1 5 ) as the organic semiconductor layer is p-type. Organic transistor. Furthermore, -95-201245216, the saturation field-effect mobility μ of the carrier of the organic transistor is calculated by using the formula of the drain current Id in the saturation region indicating the electrical characteristics of the organic transistor.

Id=( W/2L ) μΟι ( Vg-V, ) 2 . · · ( a) Here, L and W are the gate length and gate width of the organic transistor, respectively, and Ci is the gate insulating film per unit area. The capacitance, Vg is the gate voltage, and Vt is the threshold voltage of the gate voltage. Using the formula (a), the field effect mobility μ of the carrier of the organic transistor in which the thin film was formed as the organic semiconductor layer was calculated, and the field effect mobility of the carrier was 〇.〇68 cm 2 /Vs. [Industrial Applicability] The present invention provides a novel compound which can obtain an organic semiconductor active layer. BRIEF DESCRIPTION OF THE DRAWINGS Fig. 1 is a cross-sectional view showing the same state of an organic transistor of the present invention. Figure 2 is a cross-sectional view showing the same state of the organic transistor of the present invention. [Description of main component symbols] 1 1, 21: Substrate 1 2, 2 5: Gate electrode 13, 24: Gate insulating film 14, 22: Source electrode 15, 23: Dip electrode 16, 26: Organic semiconductor activity Layer-96-

Claims (1)

201245216 VII. Scope of application for patents: 1 · a compound ', which is expressed by the following formula (1): [wherein, X, Y, W and Z each independently represent a sulfur atom, an oxygen atom or a selenium atom' η represents 〇 or 1' P1, p2, Qi and q2 each independently represent a group represented by the following formula (2): —= R (2) (wherein R represents a hydrogen atom's substituted alkyl group, a substituted aryl group or a substituted fluorenyl group), a substituted aromatic hydrocarbon group or a substituted aromatic a ring group, wherein at least one of P1, P2, Q1 and Q2 is a group represented by the formula (2). 2. The compound of claim 1 wherein the group represented by formula (2) is a group represented by formula (3): R1 —=—Si—R 2 (3) R3 (wherein R 1 , R 2 and R3 each independently represents an alkyl group having 1 to 16 carbon atoms or an aryl group having 6 to 12 carbon atoms. 3. For the compound of claim 1 or 2, wherein Χ, Υ, ..., and Ζ are all sulfur atoms. 4. The compound of any one of claims 1 to 3, wherein Ρ1 and Ρ2 are The same and the group represented by the formula (2), Q1 and Q2 are the same -97-y 201245216 and are a substitutable aromatic hydrocarbon group or a substituted aromatic heterocyclic group 〇5. The compound of any one of items 1 to 4, wherein η is 0 〇6. The compound of any one of claims 1 to 5, wherein Q1 and Q2 are the same and are thieno[3,2-b Thiophen-2-yl. 7. A method for producing a compound represented by the following formula (lb), (wherein 11, 11, 乂, 丫, 2, 11 and (3 represents the same meaning as described below), which comprises a metal compound containing Q in the presence of a transition metal compound (where Q represents a step of reacting a substituted aromatic hydrocarbon group or a substituted aromatic heterocyclic group with a compound represented by the following formula (la): (wherein X, Y, W and Z each independently represent a sulfur atom, an oxygen atom or a selenium atom, and R represents a hydrogen atom, a substituted alkyl group, a substituted aryl group or a substituted decyl group, η Indicates 0 or Ι, Χ1 each independently represents a halogen atom). 8. A compound represented by the following formula (la), R -98- 201245216 (wherein x, Y, w and z each independently represent a sulfur atom, an oxygen atom or a selenium atom, and R represents a hydrogen atom, a substituted alkyl group, a substituted aryl group or may be substituted The alkyl group 'n represents 0 or 1, and X1 each independently represents a halogen atom). 9. The compound of claim 8, wherein W, X, γ and Z in the formula (1a) are each a sulfur atom. 1 0. A compound according to claim 8 or 9, wherein η in the formula (1a) is 0. A compound according to any one of claims 8 to 10, wherein X1 in the formula (la) is an iodine atom. A compound according to any one of claims 8 to 11, wherein R is represented by the following formula: R1 - SI - R2 I R3 (wherein R1, R2 and R3 each independently represent a carbon number An alkyl group or an aryl group having 6 to 12 carbon atoms). 13. A method for producing a compound represented by the following formula (U), (wherein, n, R, W, X, Y &amp; z represent the same meanings as described below. 'X1 each independently represents a halogen atom), and the method comprises a compound represented by the following formula (lc): -99- 201245216 (wherein, W, X, Y and Z each independently represent a sulfur atom, an oxygen atom or a selenium atom, and R represents a hydrogen atom, a substituted alkyl group, a substituted aryl group or a substituted decyl group, η A step of reacting 0 or 1) with an alkyllithium, and a step of reacting the reaction product obtained in the foregoing step with a halogenating agent containing X1 as a halogen atom. 14. A compound represented by the following formula (lc), (wherein, W, X, Y and Z each independently represent a sulfur atom 'an oxygen atom or a selenium atom, R represents a substituted alkylene group, and η represents 0 or 1). 1 5 · A compound of claim 14 wherein all of W, X, Y and Z in the formula (丨c) are sulfur atoms. 1 6 · A compound according to claim 14 or 15 wherein η in the formula (1 c ) is 0. 17. A method for producing a compound represented by the following formula (U), (wherein n, W, X, Y, Z and R have the same meanings as defined below), and the method comprises a compound represented by the following formula (Id) in the presence of a transition metal compound, a copper halide and an organic base, -100- 201245216 X2 (1d) (wherein, X, Y, W and Z each independently represent a sulfur atom 'an oxygen atom or a selenium atom, η represents 〇 or ι, χ 2 each independently represents a halogen atom), and a compound represented by the following formula (5) Step of the reaction: Η-ΞΖ R (5) (wherein 'R represents a decyl group which may be substituted). 18. A compound represented by the following formula (id), XW X2 X2^W (1d) (wherein, X, Y, W and Z each independently represent a sulfur atom, an oxygen atom or a selenium atom, and η represents 0 or 1, Χ2 represents an iodine atom). 1 9. A composition comprising a compound represented by the following formula (1) and an organic solvent: pa^Z^Y^Q1 (wherein, X'Y, W and Z each independently represent a sulfur atom, an oxygen atom or a selenium An atom, η represents 0 or 1, and P1, P2, Q1 and Q2 each independently represent a group represented by the following formula (2): —=-R (2) (wherein R represents a hydrogen atom, a substituted base, a substituted aryl group or a substituted fluorenyl group), a substituted aromatic hydrocarbon group or a substituted aromatic heterocyclic ring-101-in '201245216 wherein at least one of P1, P2, Q1 and Q2 The base is the base represented by the formula (2). A method for producing a film comprising the steps of applying a composition as disclosed in claim 19 to a substrate, and drying the coating film applied to the substrate. A film comprising a compound represented by formula (1) according to any one of claims 1 to 6 of the patent application. A film comprising a compound represented by the formula (1) according to any one of claims 1 to 6 of the patent application. 23. An organic semiconductor device comprising the film of claim 21 or 22 of the patent application. An organic transistor comprising a film as in claim 21 or 22 of the patent application. -102-