JP5879947B2 - 導電性組成物およびその用途 - Google Patents
導電性組成物およびその用途 Download PDFInfo
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- JP5879947B2 JP5879947B2 JP2011252131A JP2011252131A JP5879947B2 JP 5879947 B2 JP5879947 B2 JP 5879947B2 JP 2011252131 A JP2011252131 A JP 2011252131A JP 2011252131 A JP2011252131 A JP 2011252131A JP 5879947 B2 JP5879947 B2 JP 5879947B2
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- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 229910000358 iron sulfate Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- KKQAVHGECIBFRQ-UHFFFAOYSA-N methyl propyl carbonate Chemical compound CCCOC(=O)OC KKQAVHGECIBFRQ-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000035699 permeability Effects 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
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000007774 positive electrode material Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005546 reactive sputtering Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Non-Insulated Conductors (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
一般式[1]
一般式[2]
一般式[3]
) : 1 〜 1 0 , J , H u a n g . , e t a l . , . A d v a n c e d F u n c t i on a l M a t e r i a l s , 2 0 0 5 . 1 5 ( 2 ) : 2 9 0 〜 2 9 6 、およびJ , O uy a n g . , e t a l . , P o l y m e r , 2 0 0 4 . 4 5 ( 2 5 ) : 8 4 4 3 〜 8 45 0 に記載されている。
57 mlの脱イオン水中に、0.27gの表3の化合物(21)、6.53g のポリスチレンスルホン酸18%水溶液(Mn:70,000)、0.54gの過硫酸アンモニウムおよび、15mgの硫酸鉄(III)を加え、室温にて24 時間攪拌することにより、導電性樹脂(1) の水分散液を得た(固形分2.0%)。
表3の化合物(21)の代わりに、表3の化合物(22)〜(27)を用いた以外は、合成例1と同様にして導電性樹脂の水分散液を得た(固形分2.0%)。
表3の化合物(21)の代わりに、表3の化合物(21)と表3の化合物(25)の1:1(モル比)混合物を用いた以外は、合成例1と同様にして導電性樹脂の水分散液を得た(固形分2.0%)。
表3の化合物(21)の代わりに、表3の化合物(21)と表3の化合物(26)の1:1(モル比)混合物を用いた以外は、合成例1と同様にして導電性樹脂の水分散液を得た(固形分2.0%)。
表3の化合物(21)の代わりに、表3の化合物(21)と表3の化合物(30)の1:1(モル比)混合物を用いた以外は、合成例1と同様にして導電性樹脂の水分散液を得た(固形分2.0%)。
洗浄したPET板上に、導電性高分子の水分散液PEDOT/PSS(ポリ(3,4−エチレンジオキシ)−2,5−チオフェン/ポリスチレンスルホン酸、(Bayer社製BAYTRON P)を2.0gと、本発明の表1中の化合物(1)を表5に示す量、2−イソプロピルアルコール1.0gを混合させ、これを、バーコーター(No.8)を用いて、PET板上に塗工し、100℃にて3分間加熱乾燥させた。この導電性薄膜を、ロレスタを用いて、直流4端子法にて薄膜の伝導度を測定した。結果を表5に示す。
導電性高分子の水分散液として、ポリチオフェン誘導体(ポリ(チオフェン−3−[2−(2−メトキシエトキシ)エトキシ]−2,5−ジイル)、スルホン化 2% in ethylene glycol monobutyl ether/water, 3:2, electronic grade(Aldrch社製)を使用した以外は、実施例1と同様に薄膜を作成した。この導電性薄膜を、ロレスタを用いて、直流4端子法にて薄膜の伝導度を測定した。結果を表6に示す。
導電性高分子の水分散液として、表3の導電性高分子(1)を使用した以外は、実施例1と同様に薄膜を作成した。この導電性薄膜を、ロレスタを用いて、直流4端子法にて薄膜の伝導度を測定した。また、60℃の環境で100時間保存させた後の薄膜の伝導度を測定した。結果を表7に示す。
導電性高分子の水分散溶液として、表4の導電性高分子(1)を使用し、2次ドーパントとして表1の化合物(2)を添加した以外は、実施例1と同様に薄膜を作成した。この導電性薄膜を、ロレスタを用いて、直流4端子法にて薄膜の伝導度を測定した。また、60℃の環境で100時間保存させた後の薄膜の伝導度を測定した。結果を表8に示す。
導電性高分子の水分散溶液として、表4の導電性高分子(1)を使用し、2次ドーパントとして表1の化合物(3)を添加した以外は、実施例1と同様に薄膜を作成した。この導電性薄膜を、ロレスタを用いて、直流4端子法にて薄膜の伝導度を測定した。また、60℃の環境で100時間保存させた後の薄膜の伝導度を測定した。結果を表9に示す。
導電性高分子の水分散溶液として、表10に記載の表4の導電性高分子を使用し、2次ドーパントとして表1の化合物(1)を0.025g(導電性高分子固形分に対して50%)添加した以外は、実施例1と同様に薄膜を作成した。この導電性薄膜を、ロレスタを用いて、直流4端子法にて薄膜の伝導度を測定した。また、60℃の環境で100時間保存させた後の薄膜の伝導度を測定した。結果を表10に示す。
実施例1において、表1中の化合物(1)のかわりに、下記化合物(A)を用いて導電性膜を作成した以外は実施例1と同様に薄膜を作成した。この導電性薄膜を、ロレスタを用いて、直流4端子法にて薄膜の伝導度を測定した。また、60℃の環境で100時間保存させた後の薄膜の伝導度を測定した。結果を表11に示す。
洗浄したガラス板上に、導電性高分子の水分散液として、表3の導電性高分子(1)を2.0gと、本発明の表1中の化合物(1)を25mgおよび、2−イソプロピルアルコール1.0gを混合させ、これを、スピンコーターを用いて塗布し、100℃にて5分間加熱乾燥させ、透明電極を作成した。この透明電極の上に、α−NPDを真空蒸着して膜厚20nmの正孔輸送層を得た。次いで、トリス(8−ヒドロキシキノリナート)アルミニウム錯体を真空蒸着して膜厚40nmの発光層を得た。さらにその上に、LiFを0.2nm蒸着した後、Alを蒸着して膜厚150nmの電極を形成して有機EL素子を作成した。この素子について通電試験を行ったところ、最大発光輝度30cd/m2の緑色発光が得られた。
Claims (4)
- 導電性高分子が、下記一般式[2]で表されるユニットおよび/または下記一般式[3]で表されるユニットを有することを特徴とする請求項1記載の導電性組成物。
一般式[2]
(式[2]中、R1およびR2は、互いに独立して、水素原子、ハロゲン原子、置換もしくは未置換の1価の脂肪族炭化水素基、置換もしくは未置換の1価の芳香族炭化水素基、置換もしくは未置換の1価の脂肪族複素環基、置換もしくは未置換の1価の芳香族複素環基、シアノ基、置換もしくは未置換のアルコキシル基、置換もしくは未置換のアリ−ルオキシ基、置換もしくは未置換のアルキルチオ基、置換もしくは未置換のアリ−ルチオ基、置換アミノ基、アシル基、アルコキシカルボニル基、アリ−ルオキシカルボニル基、アルキルスルホニル基、または、アリ−ルスルホニル基を表す。)
一般式[3]
(式[3]中、R3およびR4は、互いに独立して、水素原子、ハロゲン原子、置換もしくは未置換の1価の脂肪族炭化水素基、置換もしくは未置換の1価の芳香族炭化水素基、置換もしくは未置換の1価の脂肪族複素環基、置換もしくは未置換の1価の芳香族複素環基、シアノ基、置換もしくは未置換のアルコキシル基、置換もしくは未置換のアリ−ルオキシ基、置換もしくは未置換のアルキルチオ基、置換もしくは未置換のアリ−ルチオ基、置換アミノ基、アシル基、アルコキシカルボニル基、アリ−ルオキシカルボニル基、アルキルスルホニル基、または、アリ−ルスルホニル基を表す。) - 請求項1または2記載の導電性組成物を用いて得られる導電膜。
- 請求項1または2記載の導電性組成物を用いて得られる透明電極。
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