JPS6226268A - Organic semiconductor - Google Patents
Organic semiconductorInfo
- Publication number
- JPS6226268A JPS6226268A JP60165283A JP16528385A JPS6226268A JP S6226268 A JPS6226268 A JP S6226268A JP 60165283 A JP60165283 A JP 60165283A JP 16528385 A JP16528385 A JP 16528385A JP S6226268 A JPS6226268 A JP S6226268A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- compound shown
- reaction
- formulas
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000004065 semiconductor Substances 0.000 title claims abstract description 11
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims abstract description 27
- 150000002391 heterocyclic compounds Chemical class 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000005336 allyloxy group Chemical group 0.000 claims abstract description 3
- 125000002917 halogen containing inorganic group Chemical group 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000000101 thioether group Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 16
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 6
- 229930192474 thiophene Natural products 0.000 abstract description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract description 3
- 239000007795 chemical reaction product Substances 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000007791 liquid phase Substances 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 239000002216 antistatic agent Substances 0.000 abstract description 2
- 230000003647 oxidation Effects 0.000 abstract description 2
- 238000007254 oxidation reaction Methods 0.000 abstract description 2
- 239000002798 polar solvent Substances 0.000 abstract description 2
- 101100276976 Drosophila melanogaster Drak gene Proteins 0.000 abstract 1
- 229910004064 NOBF4 Inorganic materials 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003568 thioethers Chemical class 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- -1 cyan group Chemical group 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 4
- KJRRQXYWFQKJIP-UHFFFAOYSA-N 3-methylfuran Chemical compound CC=1C=COC=1 KJRRQXYWFQKJIP-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 239000004020 conductor Substances 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- BNANPEQZOWHZKY-UHFFFAOYSA-N 3-phenylfuran Chemical compound O1C=CC(C=2C=CC=CC=2)=C1 BNANPEQZOWHZKY-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical group CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JXBJLPSIBJBZAW-UHFFFAOYSA-N 1,3-dioxolane;4-methyl-1,3-dioxolan-2-one Chemical compound C1COCO1.CC1COC(=O)O1 JXBJLPSIBJBZAW-UHFFFAOYSA-N 0.000 description 1
- ATRJNSFQBYKFSM-UHFFFAOYSA-N 2,3-dibromothiophene Chemical compound BrC=1C=CSC=1Br ATRJNSFQBYKFSM-UHFFFAOYSA-N 0.000 description 1
- XCMISAPCWHTVNG-UHFFFAOYSA-N 3-bromothiophene Chemical compound BrC=1C=CSC=1 XCMISAPCWHTVNG-UHFFFAOYSA-N 0.000 description 1
- AZBHGKRVIRJVQG-UHFFFAOYSA-N 3-methylselenophene Chemical compound CC=1C=C[se]C=1 AZBHGKRVIRJVQG-UHFFFAOYSA-N 0.000 description 1
- NVWFUVMWGOXULH-UHFFFAOYSA-N 3-phenoxyfuran Chemical compound C=1C=CC=CC=1OC=1C=COC=1 NVWFUVMWGOXULH-UHFFFAOYSA-N 0.000 description 1
- DXSHUWUDKNEGFS-UHFFFAOYSA-N 3-phenoxythiophene Chemical compound C=1C=CC=CC=1OC=1C=CSC=1 DXSHUWUDKNEGFS-UHFFFAOYSA-N 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- YBGKQGSCGDNZIB-UHFFFAOYSA-N arsenic pentafluoride Chemical compound F[As](F)(F)(F)F YBGKQGSCGDNZIB-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- GSXCEVHRIVLFJV-UHFFFAOYSA-N thiophene-3-carbonitrile Chemical compound N#CC=1C=CSC=1 GSXCEVHRIVLFJV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Furan Compounds (AREA)
- Pyrrole Compounds (AREA)
- Photovoltaic Devices (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は特定の複素環化合物と特定の窒素酸化物と？反
応させて得られた新規な有機半導体に関するものである
。[Detailed Description of the Invention] [Field of Industrial Application] The present invention relates to a specific heterocyclic compound and a specific nitrogen oxide? This paper relates to a novel organic semiconductor obtained by the reaction.
近年、ポリアセチレン、ポリパラフェニレン、ポリフエ
ニレンスルフイド、ポリチェニレン、ポリピロール等の
共役系ポリマーに五フッ化砒素、五フッ化アンチモン、
沃素、臭素等のドーピング剤？ドーピングしたポリマー
が良好な亀導性暑示し、ドープ量を変化させると絶縁体
から半導体、さらに導電体になることが見い出されて以
来、有機材料による優れた導電体ン見い出すべく、種々
有機化合物の探索が熱心になされている。In recent years, arsenic pentafluoride, antimony pentafluoride,
Doping agents such as iodine and bromine? Since it was discovered that doped polymers exhibit good thermal conductivity and can change from insulators to semiconductors and even conductors by changing the amount of doping, various organic compounds have been developed in order to find excellent conductors using organic materials. The search is being carried out enthusiastically.
本発明者等は有機材料による導電体について鋭意研究し
た結果、特定の複素環化合物と特定の窒素酸化物とを反
応させ得られた有機化合物は優れた半導体の性質を有す
ること馨見い出し、本発明に到達した。As a result of intensive research into conductors made of organic materials, the present inventors discovered that an organic compound obtained by reacting a specific heterocyclic compound with a specific nitrogen oxide has excellent semiconductor properties. reached.
従って、本発明の目的は、新規な有機半導体を提供する
にある。Therefore, an object of the present invention is to provide a novel organic semiconductor.
すなわち、本発明の要旨は
一般式 ＮＯｍＸ ・・・・・・・・・・・・
・・・・・・・・・（ＩＪＣ式中又はハロゲン含有の無
機基、ｍは／又はコの整数を表わす］で示される窒素酸
化物と一般式
Ｃ式中Ｒ１−Ｒ４は水素原子、アルキル基、アルコキシ
基、アリール基、アリロキシ基、チオエーテル基、アミ
ン基、ハロゲン原子、シアン基、ニトロ基を表わし、Ｙ
は；ＮＲ６、’ｓ□、〉Ｓ、＞Ｓｅ Ｙ：表わし、Ｒ５
は水素原子、アルキル基、アリール基を表わす。ノ
で示される複素環化合物との反応によって得られる有機
半導体に存する。That is, the gist of the present invention is the general formula NOmX...
・・・・・・・・・(In the IJC formula or a halogen-containing inorganic group, m represents an integer of /)] and the general formula C where R1-R4 are hydrogen atoms, alkyl group, alkoxy group, aryl group, allyloxy group, thioether group, amine group, halogen atom, cyan group, nitro group, Y
;NR6,'s□,>S,>Se Y: Representation, R5
represents a hydrogen atom, an alkyl group, or an aryl group. It consists in an organic semiconductor obtained by reaction with a heterocyclic compound shown in ().
本発明の有機半導体は単一または異なる二種艷以上の複
素環化合物を出発物質に用い、単一または異なる二種類
以上の窒素酸化物と反応させて得ることができる。The organic semiconductor of the present invention can be obtained by using a single or two or more different heterocyclic compounds as a starting material and reacting them with a single or two or more different nitrogen oxides.
以下本発明の詳細な説明する。The present invention will be explained in detail below.
前記一般式（Ｄで示される窒素酸化物としてＸ ｉｉ
ＢＦ４７ 、 ＢＯＩ、−１Ｓ ｂ Ｆ、−１ｓ ｂ
ｃ ｌ、−１ＰＦ６−１Ｐ Ｃ’ｌ、−２０１０４−１
ＡｓＦ、−１Ａ ｓ Ｃ１６−１などビ表わし、ｍは／
又はコの整数ビ表わす。As the nitrogen oxide represented by the general formula (D), X ii
BF47, BOI, -1S b F, -1s b
c l, -1PF6-1P C'l, -20104-1
AsF, -1A s C16-1, etc., m is /
Or represents the integer Bi of ko.
具体的１１１ＮＯＢＦ４、Ｎ Ｏ２Ｂ Ｆ４、Ｎ ＯＰ
Ｆ’６、Ｎ Ｏ２Ｐ Ｆ’、、Ｎ ＯＳ １） Ｆ６
、Ｎｏ□５ｔ）Ｆ、、Ｎ０ＯＩＯ４、Ｎｏ２ＣＩＯ４、
Ｎ０ＡｓＦ６、Ｎ０２ＡｓＦ、、Ｎ０８ｂＯ１，、Ｎｏ
□５ｂｃｌ、、ＮｏＰ（１，、ＮＯ□Ｐ Ｏ１，などで
好ましくはＩＪ ＯＢ Ｆ４、Ｎｏ□ＢＦ４． Ｎ０
ＰＦ、 、Ｎ０Ａ８Ｆ６ などである。Specific 111NOBF4, NO2B F4, N OP
F'6, N O2P F',, N OS 1) F6
,No□5t)F,,N0OIO4,No2CIO4,
N0AsF6, N02AsF,, N08bO1,, No
□5bcl,, NoP(1,, NO□P O1, etc., preferably IJ OB F4, No□BF4. N0
PF, , N0A8F6, etc.
使用量は複素環化合物に対して久０／〜１０θ倍モルで
あり好ましくは０． ／〜１０倍モルである。The amount used is 0/~10θ times the amount of the heterocyclic compound, preferably 0. /~10 times the mole.
前記一般式（ＩＩＪで示される複素環化合物としてＲ１
、Ｒ４は水素原子、メチル基、エチル基、ｎ−プロピル
基、イソブチル基、ｎ−ブチル基、イソブチル基、Ｂｅ
Ｃ−ブチル基、ｔｅｒｔ−ブチル基、メトキシ基、エト
キシ基、ｎ−プロポキシ基、インプロポキシ基、ｎ−ブ
トキシ基、フェニル基、トルイル基、ナフチル基、フェ
ノキシ基、メチルフェノキシ基、ナフトキシ基、メチル
チオエーテル基、メチルチオエーテル基、アミン基、フ
ッ素原子、塩素原子、臭素原子、沃素原子、シアノ基、
二） ｏ基を表わし、Ｙは；ＮＲ５、ン○、）Ｓｌ、ｓ
ｅｙ表わし、Ｒ５は水素原子、メチル基、エチル基、ｎ
−プロピル基、イソブチル基、ｎ−ブチル基、イソブチ
ル基、５ｅａ−ブチル基、ｔ−ブチル基、フエニ＋基、
トルイル基、ナフチル基を表わす。As the heterocyclic compound represented by the general formula (IIJ), R1
, R4 is a hydrogen atom, methyl group, ethyl group, n-propyl group, isobutyl group, n-butyl group, isobutyl group, Be
C-butyl group, tert-butyl group, methoxy group, ethoxy group, n-propoxy group, impropoxy group, n-butoxy group, phenyl group, tolyl group, naphthyl group, phenoxy group, methylphenoxy group, naphthoxy group, methylthio Ether group, methylthioether group, amine group, fluorine atom, chlorine atom, bromine atom, iodine atom, cyano group,
2) Represents o group, Y is ;NR5, ○, )Sl, s
ey, R5 is a hydrogen atom, methyl group, ethyl group, n
-propyl group, isobutyl group, n-butyl group, isobutyl group, 5ea-butyl group, t-butyl group, pheny+ group,
Represents a tolyl group or a naphthyl group.
具体的にはビロー、１１／、ｎ−メチルビロール、ｎ−
エチルビロール、ｎ−フェニルビロール、３−メチルビ
ロール、ｎ−メチル３−メチルビａ−ル、３−クロルビ
ロール、３．ｑ−ジクロルビロー／Ｉ／％ ３−ブロム
ビロール、ｎ−１ｆル３−ブロムビロール、Ｊ−メトキ
シビロール、３−フェノキシビロール１．２−フロムチ
オフェン、３−ブロムチオフェン、３−メチルチオフェ
ン１、．７．ｔＩジブロムチオフェン、３−グジメチル
チオフエン、Ｊ−フェニルチオフェン１．？−１）キシ
チオフェン、ｊ、’ｌ−ジメトキシチオフェン、３−フ
ェノキシチオフェン、Ｊ−ニトロチオフェン、３−シア
ノチオフェン、３−アミノチオ７エｙ、ｊ −／チルチ
オエーテルチオフェン、３、ｌｌ−ジメチルチオエーテ
ルチオフェン、フラン、３−メチルフラン１．？、４１
−ジメチルフラン、３−フェニルフラン、Ｊ−メトキシ
フラン、３−フロムフラン、３−フェノキシフラン、セ
レノフェン、３−メチルセレノフェン、３．タージメチ
ルセレノフェン等であり好ましくはビロール、ｎ−メチ
ルビロール、３−メチルビロール、チオフェン、３−メ
チルチオフェン、フラン、３−メチルフランなどである
。Specifically, billow, 11/, n-methylvirol, n-
Ethylvirol, n-phenylvirol, 3-methylvirol, n-methyl 3-methylvirol, 3-chlorovirol, 3. q-dichlorovirol/I/% 3-bromovirol, n-1f-3-bromovirol, J-methoxyvirol, 3-phenoxyvirol 1, 2-furomthiophene, 3-bromothiophene, 3-methylthiophene 1,. 7. tI dibromothiophene, 3-gudimethylthiophene, J-phenylthiophene 1. ? -1) oxythiophene, j,'l-dimethoxythiophene, 3-phenoxythiophene, J-nitrothiophene, 3-cyanothiophene, 3-aminothio7ey, j-/tilthioetherthiophene, 3,ll-dimethylthioetherthiophene , furan, 3-methylfuran 1. ? , 41
-dimethylfuran, 3-phenylfuran, J-methoxyfuran, 3-fromfuran, 3-phenoxyfuran, selenophene, 3-methylselenophene, 3. Examples include terdimethylselenophene, and preferred examples include virol, n-methylvirol, 3-methylvirol, thiophene, 3-methylthiophene, furan, and 3-methylfuran.
前記一般式ＣＩ）で示される窒素酸化物と前記一般式（
ＩＩＪで示される複素環化合物との反応は固相、液相、
気相の任意の相で実施することが出来るが、両者が溶解
する任意の溶媒の存在下液相で反応するのが好ましい。Nitrogen oxide represented by the above general formula CI) and the above general formula (CI)
The reaction with the heterocyclic compound represented by IIJ can be carried out in solid phase, liquid phase,
Although the reaction can be carried out in any gas phase, it is preferable to carry out the reaction in a liquid phase in the presence of any solvent in which both are dissolved.
溶媒としては一般式ＣＩ）及び（Ｔｌ）の化合物が溶媒
と直接反応しないものなら適宜遇択できる。両者乞溶解
する溶媒として非プロトン性極性溶媒が好ましく具体的
にはアセトニトリル、ジオキサン、ニトロメタン、プロ
ピレンカーボネートジオキソラン、などであり水、アル
コール頚は９素酸化物と容易に反応するので使用できな
い。The solvent can be appropriately selected as long as the compounds of general formulas CI) and (Tl) do not react directly with the solvent. Preferred solvents that dissolve both are aprotic polar solvents, specifically acetonitrile, dioxane, nitromethane, propylene carbonate dioxolane, etc. Water and alcohol cannot be used because they easily react with the 9-element oxide.
反応温度は一５Ｏ℃〜１００℃であり好ましくは一２０
℃〜６０℃である。反応時間は反応温度と関連するが通
常Ｏ，Ｓ〜１００時間、好ましくは／、０−！；０時間
である。The reaction temperature is -50°C to 100°C, preferably -20°C.
℃~60℃. The reaction time is related to the reaction temperature, but is usually O,S to 100 hours, preferably /,0-! ;0 hours.
反応生成物は暗褐色〜黒色の粉末状物質であり溶媒存在
下での反応では反応終了後溶媒を通常の方法で除去する
か水、アルコール中に移し生成物χ戸板することができ
る。The reaction product is a dark brown to black powdery substance, and when the reaction is carried out in the presence of a solvent, after the reaction is completed, the solvent can be removed by a conventional method or the product can be poured into water or alcohol to remove the product.
本発明の有機半導体は製法が容易で且耐酸化性も優れて
おり実用的価値が極めて大である。The organic semiconductor of the present invention is easy to manufacture, has excellent oxidation resistance, and has extremely great practical value.
かくして本発明の有機半導体は帯電防止剤、光電変換素
子、元メモＩＪ−、センサー、固体ディスプレー、端末
機器など広い分野への適用が可能である。Thus, the organic semiconductor of the present invention can be applied to a wide range of fields such as antistatic agents, photoelectric conversion elements, original memo IJ-, sensors, solid-state displays, and terminal equipment.
以下に実施例馨挙げて本発明を具体的に説明する。 The present invention will be specifically explained below with reference to Examples.
実ｉＡψＩＪ−／
３００ｍ１丸底７７ ス：ｒ ニＮ０ＢＦ４ ／ ／、
Ａ ｇ ｇＣＯ，１０モ／Ｌ／）乞採りモレキュラー
シーブグＡで脱水したジオキザン７０ｍ１ｆ加工Ｎ０Ｂ
Ｆ４ｔ７） スラリー液を調製し、スラリー液を攪拌し
なから型温窒紫気流下でチオフェンざ一６Ｊｇｗ滴下し
た。滴下とともに反応液は緑色から黒色に変化しコ時間
纜拌を継続した後、室温で一夜放置したところ黒色の塊
状物が生成した。これを大証のメタノール中に移し沈澱
物乞戸別した後メタ／−ｙｖ２００ｒｔｃｌで３回洗浄
を繰返した後６０℃、減圧下で乾燥すると３．ｇ２ｇの
黒色粉末状物質を得た。Real iAψIJ-/300m1 round bottom 77 S:r NiN0BF4//,
A g gCO, 10 mo/L/) Dioxane 70 m1f processed by dehydration using Molecular Seabug A
F4t7) A slurry liquid was prepared, and 6 Jgw of thiophene was added dropwise to the slurry liquid under a stream of heated nitrogen gas while stirring the slurry liquid. As the reaction liquid was added dropwise, the color changed from green to black, and after continued stirring for a while, it was left to stand at room temperature overnight, and black lumps were formed. After transferring this to OSE methanol and separating the precipitate, it was washed three times with meta/-yv200rtcl and dried at 60°C under reduced pressure.3. 2 g of a black powdery substance was obtained.
得られた黒色物の元素分析はｃｙｑ、ｑｂ％、Ｎ２．２
７％、Ｎ ３．６弘％、？ｇ、ｇ７％、Ｓ３Ｊ、３Ｊ％
であり炭素ｔｌＩと仮定するとＣ４，００Ｈ２，Ｈ８Ｓ
ｌ、００ ＮＯ，２５’０．４５ に相当するものを
得た。これはチオフェンに窒素酸化物（ＮＯＢＦ４Ｊ
が反応したものであること７示している。The elemental analysis of the obtained black substance was cyq, qb%, N2.2
7%, N 3.6%,? g, g7%, S3J, 3J%
and assuming carbon tlI, C4,00H2,H8S
1,00 NO,25'0.45 was obtained. This is thiophene with nitrogen oxide (NOBF4J
7 shows that this is a reaction.
一点伍による電気伝導度の測定７行なったと分にこまか
く粉砕した後Ｉ径／３順のディスク状に加圧成形（、？
）ン／ｄ）し、このディスクの表と裏に導電性樹脂（ド
ータイトタ５０）で銅線？接着固定しドライボックス中
にこのディスクサンプルを保存しエレクトロメータＣタ
ケダ理研ＴＲ−１；Ａｒ１ ＪＹ使用して測定した。After 7 measurements of electrical conductivity at one point, the pieces were finely ground and then pressure-molded into disks with diameters of I/3.
)n/d) And conductive resin (dot titan 50) and copper wires are placed on the front and back of this disk? This disk sample was fixed with adhesive and stored in a dry box, and measured using an electrometer C Takeda Riken TR-1; Ar1 JY.
実施例−一
フランｔ、ｙｏｇを使用した以外は実施例／の場合と同
様にしてＮ０ＢＦ４と反応させたところ、反応液は直ち
に黒色化した。２日間室温で放置した後大量のメタノー
ル中にあけ、２００ｒｒｔｌのメタノールで左回洗浄後
ＡＯ℃減圧下で乾燥すると７．０．３９の黒色物を得た
。元素分析の結果ａｓｔ、ｇダ％、Ｎ３．コロ％、Ｎ’
１．３１％、Ｆ！、、２ダ鴫であり炭素ｔダと仮定する
とＣ４■Ｈ２，６４Ｎ（Ｌ２５ ”０４３ に相当す
るものを得た。Example - A reaction with N0BF4 was carried out in the same manner as in Example except that furan t and yog were used, and the reaction solution immediately turned black. After being left at room temperature for 2 days, the mixture was poured into a large amount of methanol, washed once with 200 rrtl of methanol, and dried under reduced pressure at AO°C to obtain a black substance of 7.0.39. Elemental analysis results ast, gda%, N3. Coro%, N'
1.31%, F! ,, assuming that it is 2 daz and carbon is t da, we obtained something equivalent to C4■H2,64N (L25''043).
この黒色物の電気伝導度は１４．ｌ、×１０″″１０Ｓ
ｃｒｒＬ−’であった。The electrical conductivity of this black material is 14. l, ×10″″10S
It was crrL-'.
実施例−３
ビロール６、ダよｇｔ使用した以外は実施例／の場合と
同様にしてＮ ＯＥ Ｎ４と反応させたところ黒色粉末
９．０２９乞得た。Example 3 A reaction with NOE N4 was carried out in the same manner as in Example except that Virol 6 and Dayogt were used to obtain a black powder of 9.029 g.
元素分析値はＣグ２．３３％、Ｎ３．ｌ、３％、Ｎ１４
．２ｇ％、Ｆ／？、、？？チであり炭素をダと仮定する
と
Ｃ４，００Ｈ４，１０ＮＬ３１ Ｆｔｔｓに相当するも
のン得た。この黒色粉末の電気伝導度はざ、ｚｙ：１ｏ
−ｅであった。Elemental analysis values are Cg 2.33%, N3. l, 3%, N14
．． 2g%, F/? ,,? ? Assuming that carbon is 1 and carbon is 2, we obtained a material corresponding to C4,00H4,10NL31 Ftts. The electrical conductivity of this black powder is zy:1o
-e.
実施例−ダ〜−／Ａ
チオフェンの代りに各種の複素環化合物を便用して得ら
れた結果を表−７に示した。Example-Da-/A Table 7 shows the results obtained by using various heterocyclic compounds in place of thiophene.
表、−／Table, -/
Claims (1)
・・・・（ I ）（式中Ｘはハロゲン含有の無機基、ｍ
は１又は２の整数を表わす） で示される窒素酸化物と 一般式 ▲数式、化学式、表等があります▼・・・・・・・・・
・・・・・・（II）（式中Ｒ＾１〜Ｒ＾４は水素原子、
アルキル基、アルコキシ基、アリール基、アリロキシ基
、チオエーテル基、アミノ基、ハロゲン原子、シアノ基
、ニトロ基、を表わし、Ｙは▲数式、化学式、表等があ
ります▼、▲数式、化学式、表等があります▼、▲数式
、化学式、表等があります▼、▲数式、化学式、表等が
あります▼を表わし、Ｒ＾５は水素原子、アルキル基、
アリール基を表わす） で示される複素環化合物とを反応させることによつて得
られる有機半導体。[Claims] General formula NO_mX...
...(I) (in the formula, X is a halogen-containing inorganic group, m
represents an integer of 1 or 2) Nitrogen oxides and general formulas ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・・・・
・・・・・・(II) (In the formula, R^1 to R^4 are hydrogen atoms,
It represents an alkyl group, an alkoxy group, an aryl group, an allyloxy group, a thioether group, an amino group, a halogen atom, a cyano group, a nitro group, and Y has ▲a mathematical formula, a chemical formula, a table, etc.▼, ▲a mathematical formula, a chemical formula, a table, etc. There are ▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and R^5 is a hydrogen atom, an alkyl group,
An organic semiconductor obtained by reacting a heterocyclic compound represented by (representing an aryl group).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60165283A JPS6226268A (en) | 1985-07-26 | 1985-07-26 | Organic semiconductor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60165283A JPS6226268A (en) | 1985-07-26 | 1985-07-26 | Organic semiconductor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6226268A true JPS6226268A (en) | 1987-02-04 |
Family
ID=15809385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60165283A Pending JPS6226268A (en) | 1985-07-26 | 1985-07-26 | Organic semiconductor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6226268A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2005027145A1 (en) * | 2003-09-11 | 2006-11-24 | ナガセケムテックス株式会社 | Radiation sensitive resin composition |
| CN103000809A (en) * | 2012-12-20 | 2013-03-27 | 东北师范大学 | Method for improving performance of organic field effect transistors |
-
1985
- 1985-07-26 JP JP60165283A patent/JPS6226268A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2005027145A1 (en) * | 2003-09-11 | 2006-11-24 | ナガセケムテックス株式会社 | Radiation sensitive resin composition |
| JP4621870B2 (en) * | 2003-09-11 | 2011-01-26 | ナガセケムテックス株式会社 | Radiation sensitive resin composition |
| CN103000809A (en) * | 2012-12-20 | 2013-03-27 | 东北师范大学 | Method for improving performance of organic field effect transistors |
| CN103000809B (en) * | 2012-12-20 | 2015-06-03 | 东北师范大学 | Method for improving performance of organic field effect transistors |
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