JP2010083785A5 - - Google Patents

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JP2010083785A5
JP2010083785A5 JP2008253319A JP2008253319A JP2010083785A5 JP 2010083785 A5 JP2010083785 A5 JP 2010083785A5 JP 2008253319 A JP2008253319 A JP 2008253319A JP 2008253319 A JP2008253319 A JP 2008253319A JP 2010083785 A5 JP2010083785 A5 JP 2010083785A5
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alkyl
replaced
carbon atoms
hydrogen
independently
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Claims (10)

下記式(I)で表される化合物。
Figure 2010083785

(式(I)中、R1およびR2は、それぞれ独立に水素、ハロゲン、シアノまたは炭素数1〜30のアルキルであり、
3およびR4は、それぞれ独立にハロゲン、シアノ、炭素数1〜30のアルキルまたはフェニルであり、前記フェニルにおいて、任意の水素はハロゲン、シアノまたは炭素数1〜30のアルキルで置き換えられてもよく、
Aは、ナフタレン環から任意の4個の水素を除いて誘導される4価の基またはアントラセン環から任意の4個の水素を除いて誘導される4価の基であり、前記アントラセン環において、9位および10位の水素は炭素数1〜30のアルキルで置き換えられてもよく、
Arは、それぞれ独立にアリーレンまたはヘテロアリーレンであり、前記アリーレンまたは前記ヘテロアリーレンにおいて、任意の水素はハロゲン、シアノまたは炭素数1〜30のアルキルで置き換えられてもよく、
前記いずれの炭素数1〜30のアルキルにおいても、任意の水素はハロゲンで置き換えられてもよく、任意の−CH2−は−O−、−S−、−COO−、−OCO−、−CH=CH−または−C≡C−で置き換えられてもよく、任意の炭素はケイ素に置き換えられてもよく、
jおよびkは独立して0〜3の整数である。)
A compound represented by the following formula (I).
Figure 2010083785

(In formula (I), R 1 and R 2 are each independently hydrogen, halogen, cyano, or alkyl having 1 to 30 carbon atoms;
R 3 and R 4 are each independently halogen, cyano, alkyl having 1 to 30 carbons or phenyl, and in the phenyl, any hydrogen may be replaced by halogen, cyano or alkyl having 1 to 30 carbons. Often,
A is a tetravalent group derived by removing any four hydrogen from tetravalent group or anthracene ring derived by removing any four hydrogen from Na Futaren ring, in the anthracene ring , 9- and 10-position hydrogens may be replaced with alkyl having 1 to 30 carbon atoms,
Ar is each independently arylene or heteroarylene, and in the arylene or heteroarylene, any hydrogen may be replaced by halogen, cyano, or alkyl having 1 to 30 carbons;
In any of the above alkyl groups having 1 to 30 carbon atoms, any hydrogen may be replaced with a halogen, and any —CH 2 — represents —O—, —S—, —COO—, —OCO—, —CH ═CH— or —C≡C—, any carbon may be replaced by silicon,
j and k are independently integers of 0 to 3. )
前記式(I)中、Arが、それぞれ独立に下記式(II)、下記式(III)または下記式(IV)で表されるヘテロアリーレンであることを特徴とする請求項1記載の化合物。
Figure 2010083785

(式(II)、(III)および(IV)中、R5、R6、R7、R8およびR9は、それぞれ独立に水素、ハロゲン、シアノまたは炭素数1〜20のアルキルであり、前記炭素数1〜20のアルキルにおいて、任意の水素はハロゲンで置き換えられてもよく、任意の−CH2−は−O−、−S−、−COO−、−OCO−、−CH=CH−または−C≡C−で置き換えられてもよく、任意の炭素はケイ素に置き換えられてもよい。)
The compound according to claim 1, wherein Ar in the formula (I) is each independently a heteroarylene represented by the following formula (II), the following formula (III), or the following formula (IV).
Figure 2010083785

(In the formulas (II), (III) and (IV), R 5 , R 6 , R 7 , R 8 and R 9 are each independently hydrogen, halogen, cyano or alkyl having 1 to 20 carbon atoms, In the alkyl having 1 to 20 carbon atoms, arbitrary hydrogen may be replaced by halogen, and arbitrary —CH 2 — represents —O—, —S—, —COO—, —OCO—, —CH═CH—. Or -C≡C- and any carbon may be replaced by silicon.)
前記式(I)中、R3およびR4が、それぞれ独立に炭素数1〜20のアルキルまたはフェニルであり、
前記炭素数1〜20のアルキルにおいて、任意の−CH2−は−O−、−S−、−COO−、−OCO−、−CH=CH−または−C≡C−で置き換えられてもよく、
前記フェニルにおいて、任意の水素はハロゲン、シアノまたは炭素数1〜30のアルキルで置き換えられてもよく、前記炭素数1〜30のアルキルにおいて、任意の水素はハロゲンで置き換えられてもよく、任意の−CH2−は−O−、−S−、−COO−、−OCO−、−CH=CH−または−C≡C−で置き換えられてもよく、任意の炭素はケイ素に置き換えられてもよく、
Arが、それぞれ独立に下記式(II)で表されるヘテロアリーレンであり、
jおよびkが1であることを特徴とする請求項1記載の化合物。
Figure 2010083785

(式(II)中、R5は水素または炭素数1〜20のアルキルであり、前記炭素数1〜20のアルキルにおいて、任意の−CH2−は−O−、−S−、−COO−、−OCO−、−CH=CH−または−C≡C−で置き換えられてもよい。)
In the formula (I), R 3 and R 4 are each independently alkyl or phenyl having 1 to 20 carbon atoms,
In the alkyl having 1 to 20 carbon atoms, arbitrary —CH 2 — may be replaced by —O—, —S—, —COO—, —OCO—, —CH═CH— or —C≡C—. ,
In the phenyl, any hydrogen may be replaced with halogen, cyano, or alkyl having 1 to 30 carbons. In the alkyl having 1 to 30 carbons, any hydrogen may be replaced with halogen. —CH 2 — may be replaced with —O—, —S—, —COO—, —OCO—, —CH═CH— or —C≡C—, and any carbon may be replaced with silicon. ,
Ar is each independently a heteroarylene represented by the following formula (II):
The compound according to claim 1, wherein j and k are 1.
Figure 2010083785

(In the formula (II), R 5 is hydrogen or alkyl having 1 to 20 carbon atoms, and in the alkyl having 1 to 20 carbon atoms, any —CH 2 — is —O—, —S—, —COO—. , -OCO-, -CH = CH-, or -C≡C-.
前記式(I)中、R1およびR2が、それぞれ独立に水素または炭素数1〜20のアルキルであり、
3およびR4が、それぞれ独立に炭素数1〜20のアルキルまたはフェニルであり、
前記フェニルにおいて、任意の水素は炭素数1〜20のアルキルで置き換えられてもよく、
前記いずれの炭素数1〜20のアルキルにおいても、任意の−CH2−は−O−、−S−、−COO−、−OCO−、−CH=CH−または−C≡C−で置き換えられてもよく、
jおよびkが0であることを特徴とする請求項1記載の化合物。
In the formula (I), R 1 and R 2 are each independently hydrogen or alkyl having 1 to 20 carbons,
R 3 and R 4 are each independently alkyl or phenyl having 1 to 20 carbon atoms,
In the phenyl, any hydrogen may be replaced with alkyl having 1 to 20 carbons,
In any of the above alkyl groups having 1 to 20 carbon atoms, arbitrary —CH 2 — is replaced by —O—, —S—, —COO—, —OCO—, —CH═CH— or —C≡C—. You can,
The compound according to claim 1, wherein j and k are 0.
下記式(I−4)または下記式(I−5)で表される請求項1記載の化合物。
Figure 2010083785

(式(I−4)および(I−5)中、R3およびR4は、それぞれ独立に炭素数1〜20のアルキルであり、前記炭素数1〜20のアルキルにおいて、任意の−CH2−は−O−、−S−、−COO−、−OCO−、−CH=CH−または−C≡C−で置き換えられてもよい。)
The compound of Claim 1 represented by a following formula (I-4) or a following formula (I-5).
Figure 2010083785

(In the formulas (I-4) and (I-5), R 3 and R 4 are each independently alkyl having 1 to 20 carbon atoms, and in the alkyl having 1 to 20 carbon atoms, any —CH 2 -May be replaced by -O-, -S-, -COO-, -OCO-, -CH = CH- or -C≡C-).
下記式(I−6)または下記式(I−7)で表される請求項1記載の化合物。
Figure 2010083785

(式(I−6)および(I−7)中、R12およびR13は、それぞれ独立に水素または炭素数1〜20のアルキルであり、
3およびR4は、それぞれ独立に炭素数1〜20のアルキルまたはフェニルであり、
前記フェニルにおいて、任意の水素は炭素数1〜20のアルキルで置き換えられてもよく、
前記いずれの炭素数1〜20のアルキルにおいても、任意の−CH2−は−O−、−S−、−COO−、−OCO−、−CH=CH−または−C≡C−で置き換えられてもよい。)
The compound of Claim 1 represented by a following formula (I-6) or a following formula (I-7).
Figure 2010083785

(In the formulas (I-6) and (I-7), R 12 and R 13 are each independently hydrogen or alkyl having 1 to 20 carbons,
R 3 and R 4 are each independently alkyl or phenyl having 1 to 20 carbon atoms,
In the phenyl, any hydrogen may be replaced with alkyl having 1 to 20 carbons,
In any of the above alkyl groups having 1 to 20 carbon atoms, arbitrary —CH 2 — is replaced by —O—, —S—, —COO—, —OCO—, —CH═CH— or —C≡C—. May be. )
請求項1〜のいずれか1項記載の化合物から形成される薄膜。 The thin film formed from the compound of any one of Claims 1-6 . 請求項記載の薄膜からなる有機半導体膜。 An organic semiconductor film comprising the thin film according to claim 7 . 請求項記載の有機半導体膜を含む有機トランジスタ。 An organic transistor comprising the organic semiconductor film according to claim 8 . ゲート電極、ソース電極、ドレイン電極、ゲート絶縁膜および請求項記載の有機半導体膜を含む有機電界効果型トランジスタ。 An organic field effect transistor comprising a gate electrode, a source electrode, a drain electrode, a gate insulating film, and the organic semiconductor film according to claim 8 .
JP2008253319A 2008-09-30 2008-09-30 Compound having molecular structure high in planarity and organic transistor using the same Pending JP2010083785A (en)

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EP2586810A4 (en) * 2010-06-25 2014-01-29 Oceans King Lighting Science Conjugated polymer based on benzodithiophene and thienopyrazine, preparation method and uses thereof
KR20140007396A (en) * 2011-01-31 2014-01-17 스미또모 가가꾸 가부시키가이샤 Nitrogen-containing condensed ring compound, nitrogen-containing condensed ring polymer, organic thin film, and organic thin film element
KR101860084B1 (en) 2012-07-06 2018-05-23 삼성전자주식회사 Organic photoelectric material and organic photoelectronic device and image sensor
US20150333263A1 (en) 2012-12-07 2015-11-19 Merck Patent Gmbh Polymer comprising a naphthalene group and its use in organic electronic devices

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JP4500082B2 (en) * 2004-03-29 2010-07-14 旭化成株式会社 Method for producing condensed polycyclic aromatic compound fine particles, and method for producing condensed polycyclic aromatic compound thin film
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JP5272345B2 (en) * 2006-08-28 2013-08-28 東ソー株式会社 Heteroacene derivatives, tetrahaloterphenyl derivatives and methods for producing them
JP2008103464A (en) * 2006-10-18 2008-05-01 Konica Minolta Holdings Inc Organic semiconductor material, organic semiconductor film, organic semiconductor device and organic thin film transistor
US8232546B2 (en) * 2006-10-25 2012-07-31 Hiroshima University Fused polycyclic aromatic compound, process for producing the same, and use thereof
US20110087034A1 (en) * 2008-02-06 2011-04-14 Sumitomo Chemical Company Limited Organic Semiconductor Material

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