TWI650362B - 導電性材料及基板 - Google Patents
導電性材料及基板 Download PDFInfo
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- TWI650362B TWI650362B TW105106501A TW105106501A TWI650362B TW I650362 B TWI650362 B TW I650362B TW 105106501 A TW105106501 A TW 105106501A TW 105106501 A TW105106501 A TW 105106501A TW I650362 B TWI650362 B TW I650362B
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- Prior art keywords
- conductive material
- acid
- component
- group
- polymer
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- 239000004020 conductor Substances 0.000 title claims abstract description 79
- 239000000758 substrate Substances 0.000 title claims description 30
- 229920000642 polymer Polymers 0.000 claims abstract description 76
- 239000002019 doping agent Substances 0.000 claims abstract description 67
- 239000002105 nanoparticle Substances 0.000 claims abstract description 37
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 36
- 229920000547 conjugated polymer Polymers 0.000 claims abstract description 26
- 239000002245 particle Substances 0.000 claims abstract description 19
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052737 gold Inorganic materials 0.000 claims abstract description 18
- 239000010931 gold Substances 0.000 claims abstract description 18
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 18
- 239000000178 monomer Substances 0.000 claims description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 44
- -1 polycyclic aromatic compound Chemical class 0.000 claims description 41
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 26
- 239000006185 dispersion Substances 0.000 claims description 26
- 239000003960 organic solvent Substances 0.000 claims description 25
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 24
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 20
- 229930192474 thiophene Natural products 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000004185 ester group Chemical group 0.000 claims description 13
- 125000001033 ether group Chemical group 0.000 claims description 12
- 239000002243 precursor Substances 0.000 claims description 9
- 229920001400 block copolymer Polymers 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 claims description 7
- RKCAIXNGYQCCAL-UHFFFAOYSA-N porphin Chemical compound N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 RKCAIXNGYQCCAL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 abstract description 24
- 229910052709 silver Inorganic materials 0.000 abstract description 20
- 239000004332 silver Substances 0.000 abstract description 20
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- 239000002131 composite material Substances 0.000 description 23
- 230000000052 comparative effect Effects 0.000 description 20
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 20
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- 238000000108 ultra-filtration Methods 0.000 description 20
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- 238000002360 preparation method Methods 0.000 description 14
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 238000000576 coating method Methods 0.000 description 13
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 13
- 239000011248 coating agent Substances 0.000 description 12
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 11
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 11
- 238000009826 distribution Methods 0.000 description 11
- 229910000358 iron sulfate Inorganic materials 0.000 description 11
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 11
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 10
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
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- 150000001450 anions Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- 150000002641 lithium Chemical group 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 125000004436 sodium atom Chemical group 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 5
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 239000002042 Silver nanowire Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
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- 239000007800 oxidant agent Substances 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
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- 239000002202 Polyethylene glycol Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 125000003118 aryl group Chemical group 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 2
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- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
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- 150000003851 azoles Chemical class 0.000 description 2
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- NNXMZFSCTRDIBY-UHFFFAOYSA-N (4-methylphenyl)methanedisulfonic acid Chemical compound CC1=CC=C(C(S(O)(=O)=O)S(O)(=O)=O)C=C1 NNXMZFSCTRDIBY-UHFFFAOYSA-N 0.000 description 1
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- BDMDVWJINBANSP-UHFFFAOYSA-N 1,4-dioxane propane-1,2-diol Chemical compound O1CCOCC1.C(C(C)O)O BDMDVWJINBANSP-UHFFFAOYSA-N 0.000 description 1
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Abstract
本發明係提供一種成膜性佳,膜形成時,可形成透明性、導電性高,撓性優異,平坦性良好之導電膜的導電性材料。
本發明係一種導電性材料,其係含有:(A)π共軛系聚合物、及(B)含有選自以下述一般式(1)表示之重複單位a1~a4之1種以上的重複單位,且重量平均分子量為1,000~500,000之範圍的摻雜劑聚合物、(C)粒徑為1~200nm之選自金、銀、及鉑之奈米粒子。
Description
本發明係有關導電性材料及藉由此導電性材料形成導電膜的基板。
具有共軛雙鍵之聚合物(π共軛系聚合物),此聚合物本身未顯示導電性,但是藉由摻雜適當的陰離子分子而展現導電性,成為導電性高分子材料(導電性聚合物組成物)。π共軛系聚合物使用聚乙炔(Polyacetylene)、聚噻吩、聚硒酚、聚碲吩、聚吡咯、聚苯胺等(雜)芳香族聚合物及此等混合物等,陰離子分子(摻雜劑)最常使用磺酸系的陰離子。此乃是因為強酸的磺酸與上述π共軛系聚合物有效地相互作用的緣故。
磺酸系之陰離子摻雜劑(dopant)係廣泛使用聚乙烯磺酸或聚苯乙烯磺酸(PSS)等之磺酸聚合物(專利文獻1)。又,磺酸聚合物中亦有註冊商標Nafion所代表的乙烯基全氟烷基醚磺酸,此係用於燃料電池用途。
聚苯乙烯磺酸(PSS)係因對於聚合物主鏈,磺
酸以單體單元連續地存在,故對於π共軛系聚合物之摻雜為高效率,又,摻雜後之π共軛系聚合物亦可提升對於水之分散性。此係因在PSS中過剩存在之磺酸基之存在,而保持親水性,顯著提升對於水之分散性的緣故。
將PSS作為摻雜劑之聚噻吩係因高導電性且可作為水分散液處理,故被期待作為取代ITO(銦-錫氧化物)之塗佈型導電膜材料。但是如上述,PSS為水溶性樹脂,且幾乎不溶解於有機溶劑中。因此,以PSS作為摻雜劑之聚噻吩,其親水性變高,但對於有機溶劑或有機基板之親和性低,故使分散於有機溶劑中,於有機基板上成膜困難。
又,將以PSS作為摻雜劑之聚噻吩,例如使用於有機EL照明用之導電膜的情形,如上述,以PSS作為摻雜劑之聚噻吩之親水性非常高,故導電膜中容易殘存大量水份,又形成之導電膜易由外部環境吸取水份。結果有機EL之發光體產生化學變化而降低發光能力,隨著時間經過,水份凝聚成為缺陷,故有縮短有機EL裝置整體壽命的問題。又,以PSS為摻雜劑之聚噻吩有在水分散液中之粒子大,膜形成後之膜表面之凹凸大,或使用於有機EL照明時,產生被稱為暗點(dark spot)之未發光部分的問題。
又,將PSS作為摻雜劑的聚噻吩係因在波長500nm附近的藍色區域具有吸收,故將該材料塗佈於於透明電極等之透明的基板上來使用的情形,為了使裝置產生
功能所需要的導電率,以固體成份濃度或膜厚來補足時,會有影響作為構件之透過率的問題。
專利文獻2提案一種藉由下述導電性高分子所形成之導電性聚合物組成物,其中前述導電性高分子包含:藉由選自噻吩、硒吩、碲吩、吡咯、苯胺、多環式芳香族化合物之重複單位所形成之π共軛系聚合物;與可以有機溶劑潤濕,且50%以上被陽離子中和的氟化酸聚合物,且顯示藉由以任意順序組合水、π共軛系聚合物之前驅體單體、氟化酸聚合物及氧化劑,成為導電性聚合物的水分散體。
但是如此以往的導電性聚合物,在合成隨後在分散液中粒子凝聚,添加成為高導電化劑之有機溶劑作為塗佈材料時,進一步促進凝聚,使過濾性變差。另外,未過濾之狀態進行旋轉塗佈時,因粒子凝聚物之影響而無法得到平坦的膜,結果產生塗佈不良的問題。
又,可撓性裝置之開發正盛行。適用於現在情況硬體之透明導電膜係廣泛使用ITO,但是ITO為結晶性膜,欲將此膜彎曲時,會發生龜裂。因此,必須趕緊開發取代ITO之可撓性的透明導電膜。使用以PSS作為摻雜劑之聚噻吩的膜,雖為可撓性且高透明的膜,但是除前述暗點的問題外,有相較於ITO時,導電性較低的問題。
專利文獻3揭示使用銀奈米線之透明導電膜。使用銀奈米線的透明導電膜係因導電性高,且也為高透明,故為適用於可撓性的裝置之導電性膜之候補之一。
但是銀奈米線僅在線部分可通電,故將此使用於有機EL照明時,僅線部分發光,產生未全面發光的問題。
[專利文獻1]日本特開2008-146913號公報
[專利文獻2]專利第5264723號
[專利文獻3]日本特開2009-224183號
如上述,使用以泛用性高之PEDOT-PSS等之PSS作為摻雜劑之聚噻吩系導電性聚合物的膜,雖具有與ITO同等之透明性,且相較於ITO更軟性,但是有導電性低的問題。又,以PSS作為摻雜劑的聚噻吩系導電性聚合物,使用於有機EL照明時,有發生暗點的問題。此外,使用銀奈米線的透明導電膜,雖具有透明性、導電性高、撓性優異的特性,但是使用於有機EL照明時,僅線部分發光,有顯微性(microscopic)不均勻發光的問題點。
本發明係有鑑於上述情況而完成者,本發明之目的係提供成膜性佳,膜形成時,可形成透明性、導電性高,撓性優異、平坦性良好之導電膜的導電性材料。
為了解決上述課題,本發明係提供一種導電性材料,其係含有:(A)π共軛系聚合物、及(B)含有選自以下述一般式(1)表示之重複單位a1~a4之1種以上的重複單位,且重量平均分子量為1,000~500,000之範圍的摻雜劑聚合物、(C)粒徑為1~200nm之選自金、銀、及鉑之奈米粒子者。
這種導電性材料時,成膜性佳,膜形成時,可形成透明性、導電性高,撓性優異、平坦性良好之導電
膜。
此時,前述(B)成分較佳為包含以下述一般式(2)表示之重複單位b者。
藉由含有這種重複單位b,可進一步提高導電性。
此時,前述(B)成分為嵌段共聚物為佳。
(B)成分為嵌段共聚物時,可進一步提高導電性。
又,此時,前述(A)成分為選自由吡咯、噻吩、硒吩、碲吩、苯胺、多環式芳香族化合物、及此等之衍生物所成群之1種以上的前驅物單體進行聚合者為佳。
這種單體時,聚合容易,又,在空氣中之安定性良好,故可容易合成(A)成分。
又,此時,前述導電性材料係在水或有機溶劑中具有分散性者為佳。
又,本發明係提供藉由前述導電性材料形成導電膜的基板。
如此,本發明之導電性材料可藉由塗佈於基板等進行成膜作為導電膜。
又,如此形成之導電膜係因導電性、透明性
優異,故可作為透明電極層產生機能者。
如上述,本發明之導電性材料為在含有超強酸之磺酸基之(B)成分的摻雜劑聚合物與(A)成分之π共軛系聚合物,形成複合體的導電性聚合物中,添加有作為(C)成分之金、銀、或鉑之奈米粒子的溶液,其過濾性及旋轉塗佈之成膜性成為良好者。又,藉由使用本發明之導電性材料製膜所形成的導電膜,藉由光照射產生之電漿子(plasmon)效果,金屬奈米顆粒彼此之自由電子產生共振被激發,此與金屬奈米顆粒間之導電性高分子之離子產生共振,與導電性高分子連動而提高導電性者。此外,由本發明之導電性材料所形成的導電膜係透明性、撓性、平坦性、及耐久性良好,且表面粗糙度低者。此外,這種導電性材料時,無論對於有機基板或無機基板,均為成膜性良好者。
又,以這種導電性材料所形成之導電膜係因導電性、透明性、平坦性、撓性等優異,故可作為透明電極層、特別是可撓性的透明電極產生機能者。
如上述,要求開發一種可形成透明性、導電性高,且撓性優異、平坦性良好之導電膜的導電膜形成用材料。
本發明人等對上述課題精心檢討的結果,發現藉由使用具有α位具有經氟化之磺酸基之重複單位的摻雜劑聚合物、或具有經氟化之苯磺酸之重複單位的摻雜劑聚合物,取代作為導電性高分子材料之摻雜劑被廣泛使用之聚苯乙烯磺酸(PSS),因超強酸之摻雜劑聚合物與π共軛系聚合物強烈相互作用,藉由π共軛系聚合物之可見光吸收區域位移(SHIFT)而提高透明性,藉由π共軛系聚合物與摻雜劑聚合物強烈進行離子鍵結,而提高對光或熱之安定性。又,發現可提高旋轉塗佈之成膜性,膜形成時之平坦性亦良好。組合有這種導電性聚合物與金、銀、或鉑之奈米粒子的導電性材料,相較於導電性聚合物單體的情形,導電性更高,相較於金或銀之奈米線單體的情形,製膜後之膜的平坦性更高,故可得到導電性、透明性與膜之平坦性等優異之特性,遂完成本發明。
亦即,本發明係一種導電性材料,其係含有:(A)π共軛系聚合物、及(B)含有選自以下述一般式(1)表示之重複單位a1~a4之1種以上的重複單位,且重量平均分子量為1,000~500,000之範圍的摻雜劑聚合物、(C)粒徑為1~200nm之選自金、銀、及鉑之奈米粒子,
(式中,R1、R3、R5、及R8各自獨立為氫原子或甲基,R2、R4、及R6各自獨立為單鍵、酯基、或可具有醚基、酯基之任一或此等之兩者之碳數1~12之直鏈狀、分枝狀、環狀之烴基之任一。R7為碳數1~4之直鏈狀、分枝狀之伸烷基,R7中之氫原子之中,1個或2個可被氟原子取代。R9為氟原子或三氟甲基。Z1、Z2、及Z3各自獨立為單鍵、伸苯基、伸萘基、醚基、酯基之任一,Z4為單鍵、醚基、酯基之任一。m為1~4之整數,a1、a2、a3、及a4為0≦a1≦1.0、0≦a2≦1.0、0≦a3≦1.0、0≦a4≦1.0,且0<a1+a2+a3+a4≦1.0)。
以下詳細說明本發明,但是本發明不限定於此等者。
本發明之導電性材料含有作為(A)成分之π共軛系聚合物。此(A)成分只要形成π共軛系連鏈(單鍵與雙鍵交替連續的構造)之前驅物單體(有機單體分子)進行聚合者即可。
如此前驅物單體,可列舉例如吡咯類、噻吩類、噻吩乙烯類、硒酚類、碲吩類、苯類、苯乙烯(phenylene vinylene)類、苯胺類等之單環式芳香族類;并苯類等之多環式芳香族類;乙炔類等,此等單體之單一聚合物或共聚合物可作為(A)成分使用。
上述單體中,就聚合之容易度,在空氣中之穩定性的觀點而言,較佳為吡咯、噻吩、硒酚、碲吩、苯胺、多環式芳香族化合物,及此等之衍生物,特佳為吡咯、噻吩、苯胺及此等衍生物,特別是噻吩類為最高導電性與可見光之透明性,故較佳,但並不限定於此等。
本發明之導電性材料含有作為(A)成分特別是聚噻吩的情形,因具有高導電性與可見光下之高透明性的特性,故可推廣至觸控面板或有機EL顯示器、有機EL照明等的用途。另一方面,本發明之導電性材料含有作為(A)成分之聚苯胺的情形,相較於含有聚噻吩的情形,因在可見光之吸收較大且導電性較低,故在顯示器相關之應用困難,但是因為低黏度且容易旋轉塗佈,而可思及EB顯影中,防止電子之帶電用之阻劑上層膜之面塗層之用途。
又,即使構成π共軛系聚合物之單體為無取代的狀態,(A)成分仍可獲得充分的導電性,但是為了更提升導電性,亦可使用被烷基、羧基、磺酸基、烷氧基、羥基、氰基、鹵素原子等取代的單體。
吡咯類、噻吩類、苯胺類之單體之具體例,
可列舉吡咯、N-甲基吡咯、3-甲基吡咯、3-乙基吡咯、3-正丙基吡咯、3-丁基吡咯、3-辛基吡咯、3-癸基吡咯、3-十二烷基吡咯、3,4-二甲基吡咯、3,4-二丁基吡咯、3-羧基吡咯、3-甲基-4-羧基吡咯、3-甲基-4-羧基乙基吡咯、3-甲基-4-羧基丁基吡咯、3-羥基吡咯、3-甲氧基吡咯、3-乙氧基吡咯、3-丁氧基吡咯、3-己氧基吡咯、3-甲基-4-己氧基吡咯;噻吩、3-甲基噻吩、3-乙基噻吩、3-丙基噻吩、3-丁基噻吩、3-己基噻吩、3-庚基噻吩、3-辛基噻吩、3-癸基噻吩、3-十二烷基噻吩、3-十八烷基噻吩、3-溴噻吩、3-氯噻吩、3-碘噻吩、3-氰基噻吩、3-苯基噻吩、3,4-二甲基噻吩、3,4-二丁基噻吩、3-羥基噻吩、3-甲氧基噻吩、3-乙氧基噻吩、3-丁氧基噻吩、3-己氧基噻吩、3-庚氧基噻吩、3-辛氧基噻吩、3-癸氧基噻吩、3-十二烷氧基噻吩、3-十八烷氧基噻吩、3,4-二羥基噻吩、3,4-二甲氧基噻吩、3,4-二乙氧基噻吩、3,4-二丙氧基噻吩、3,4-二丁氧基噻吩、3,4-二己氧基噻吩、3,4-二庚氧基噻吩、3,4-二辛氧基噻吩、3,4-二癸氧基噻吩、3,4-二(十二烷氧基)噻吩、3,4-乙烯二氧噻吩、3,4-乙烯二硫噻吩、3,4-丙烯二氧噻吩、3,4-丁烯二氧噻吩、3-甲基-4-甲氧基噻吩、3-甲基-4-乙氧基噻吩、3-羧基噻吩、3-甲基-4-羧基噻吩、3-甲基-4-羧基甲基噻吩、3-甲基-4-羧基乙基噻吩、3-甲基-4-羧基丁基噻吩、3,4-(2,2-二甲基丙烯二氧)噻吩、3,4-(2,2-二乙基丙烯二氧)噻吩、(2,3-二氫噻吩並[3,4-b][1,4]戴奧辛-2-基)甲醇;苯胺、2-甲基苯胺、3-甲基苯胺、2-乙基苯胺、
3-乙基苯胺、2-丙基苯胺、3-丙基苯胺、2-丁基苯胺、3-丁基苯胺、2-異丁基苯胺、3-異丁基苯胺、2-甲氧基苯胺、2-乙氧基苯胺、2-苯胺磺酸、3-苯胺磺酸等。
其中,選自由吡咯、噻吩、N-甲基吡咯、3-甲基噻吩、3-甲氧基噻吩、3,4-乙烯二氧噻吩之1種或2種所成之(共)聚合物,就電阻值、反應性的觀點而言,適宜使用。進一步,藉由吡咯、3,4-乙烯二氧噻吩所成之單一聚合物,因導電性高,故更佳。
又,實用上的理由,(A)成分中之此等重複單元(前驅物單體)之重複數,較佳為2~20之範圍、更佳為6~15之範圍。
又,(A)成分之分子量,較佳為130~5,000左右。
本發明之導電性材料含有作為(B)成分之摻雜劑聚合物。此(B)成分之摻雜劑聚合物係包含含有以下述一般式(1)表示之重複單位a1~a4之經氟化之磺酸的超強酸性聚合物。
提供重複單位a1之單體,具體而言,可例示如下述者。
提供重複單位a2之單體,具體而言,可例示如下述者。
提供重複單位a3之單體,具體而言,可例示如下述者。
提供重複單位a4之單體,具體而言,可例示
如下述者。
這種(B)成分時,提高材料之過濾性及成膜性、對有機溶劑.基板之親和性,且提高成膜後之透過率。
(B)成分進一步含有下述一般式(2)表示之重複單位b者為佳。藉由含有這種重複單位b,可進一步提高
導電性。
提供重複單位b之單體,具體而言,可例示如下述者。
前述X、X2為胺化合物的情形,可列舉日本特開2013-228447號公報段落[0048]所記載的(P1a-3)為例。
在此,如上述,a1、a2、a3、及a4為0≦a1≦1.0、0≦a2≦1.0、0≦a3≦1.0、0≦a4≦1.0,且0<a1+a2+a3+a4≦1.0,較佳為0.2≦a1+a2+a3+a4≦1.0。0<a1+a2+a3+a4≦1.0時(亦即,包含重複單位a1~a4之任一),可得到本發明效果,但是0.2≦a1+a2+a3+a4≦1.0時,可得到更佳的效果。
又,含有重複單位b的情形,從提高導電性的觀點,較佳為0.3≦b<1.0,更佳為0.3≦b≦0.8。
此外,重複單位a1+a2+a3+a4與重複單位b之比例,較佳為0.2≦a1+a2+a3+a4≦0.7且0.3≦b≦0.8,更佳為0.3≦a1+a2+a3+a4≦0.6且0.4≦b≦0.7。
又,(B)成分的摻雜劑聚合物也可含有重複單位a1~a4、重複單位b以外的重複單位c,此重複單位c可列舉例如苯乙烯系、乙烯基萘系、乙烯基矽烷系、苊烯、茚、乙烯基咔唑等。
提供重複單位c之單體,具體而言,可例示如下述者。
合成(B)成分之摻雜劑聚合物的方法,可列舉例如藉由將提供上述重複單位a1~a4、b、c之單體之中所期望之單體於有機溶劑中,添加自由基聚合起始劑,進行加熱聚合,得到(共)聚合物之摻雜劑聚合物的方法。
聚合時所使用的有機溶劑,可列示如甲苯、苯、四氫呋喃、二乙基醚、二噁烷、環己烷、環戊烷、甲基乙基酮、γ-丁內酯等。
自由基聚合起始劑可例示如2,2’-偶氮雙異丁腈(AIBN)、2,2’-偶氮雙(2,4-二甲基戊腈)、二甲基2,2’-偶氮雙(2-甲基丙酸酯)、過氧化苯甲醯、過氧月桂醯(Lauroyl peroxide)等。
反應溫度較佳為50~80℃,反應時間較佳為2~100小時、更佳為5~20小時。
(B)成分之摻雜劑聚合物中,提供重複單位a1~a4之單體可為1種類亦可2種類以上,為了提升聚合性時,組合甲基丙烯酸型與苯乙烯型之單體較佳。
又,使用2種類以上之提供重複單位a1~a4之單體的情形,各自單體可無規共聚,亦可嵌段共聚。作為嵌段共聚合聚合物(嵌段共聚合物)的情形,藉由使2種類以上之重複單位a1~a4所成之重複部分彼此凝聚形成海島構造,而可期待於摻雜劑聚合物周邊產生特殊的構造,提高導電率的優點。
又,提供重複單位a1~a4、b、c之單體可無規共聚,或各自亦可嵌段共聚。此時,藉由亦與上述重複
單元a1~a4的情形同樣,形成嵌段共聚物,可期待提高導電率的優點。
以自由基聚合進行無規共聚的情形,一般為藉由混合進行共聚合之單體或自由基聚合起始劑,經加熱進行聚合的方法。第1單體與自由基聚合起始劑存在下,開始聚合,然後,添加第2單體的情形,聚合物分子之一側成為第1單體進行了聚合的構造,另一側成為第2單體進行了聚合的構造。然而,此時,於中間部分混合有第1單體與第2單體之重複單位,與嵌段共聚物為不同形態。以自由基聚合形成嵌段共聚物時,較佳為使用活性自由基聚合。
被稱為RAFT聚合(Reverbsible Addition Fragmentation chain Transfer Polymerization)之活性自由基之聚合方法係因聚合物末端之自由基經常為活性,故藉由以第1單體開始聚合,在此第1單體被消耗的階段添加第2單體,可藉由第1單體之重複單位之嵌段與第2單體之重複單元之嵌段形成二嵌段共聚物。又,以第1單體開始聚合,在此第1單體被消耗之階段添加第2單體,接著,添加第3單體的情形,也可形成三嵌段共聚物。
進行RAFT聚合的情形,有形成分子量分布(分散度)狹窄之狹分散聚合物的特徵,特別是一次添加單體進行RAFT聚合的情形,可形成分子量分布更狹窄的聚合物。
另外,(B)成分之摻雜劑聚合物中,分子量分布
(Mw/Mn)較佳為1.0~2.0,特佳為1.0~1.5之狹分散。若狹分散時,可防止藉由使用其之導電性材料所形成之導電膜的透過率降低。
進行RAFT聚合的情形,需要鏈轉移劑,具體而言,可列舉2-氰基-2-丙基苯並硫代酸酯(thioate)、4-氰基-4-苯基二硫代碳酸酯基戊酸、2-氰基-2-丙基十二烷基三硫代碳酸酯、4-氰基-4-[(十二烷基磺醯基硫代羰基)磺醯基]戊酸、2-(十二烷基三硫代碳酸酯基)-2-甲基丙酸、氰甲基十二烷基硫代碳酸酯、氰基甲基甲基(苯基)硫代胺基甲酸酯(carbamothioate)、雙(硫代苯甲醯基)二硫醚、雙(十二烷基磺醯基硫代羰基)二硫醚。此等之中,特別是2-氰基-2-丙基苯並硫代酸酯為佳。
重複單位a1~a4、b、c之比例,較佳為0<a1+a2+a3+a4≦1.0、0<b<1.0、0≦c<1.0、更佳為0.1≦a1+a2+a3+a4≦0.9、0.1≦b≦0.9、0≦c≦0.8、又更佳為0.2≦a1+a2+a3+a4≦0.8、0.2≦b≦0.8、0≦c≦0.5。
又,a1+a2+a3+a4+b+c=1為佳。
(B)成分之摻雜劑聚合物係重量平均分子量為1,000~500,000之範圍者,較佳為2,000~200,000之範圍者。重量平均分子量未達1,000時,成為耐熱性差者,又與(A)成分之複合體溶液之均勻性惡化。此外,重量平均分子量超過500,000時,除導電性惡化外,因黏度上昇,作業性差,對水或有機溶劑之分散性會降低。
另外,重量平均分子量(Mw)係藉由使用溶劑
為水、二甲基甲醯胺(DMF)、四氫呋喃(THF)之凝膠滲透色譜法(GPC)所得之聚環氧乙烷、聚乙二醇、或聚苯乙烯換算的測量值。
另外,構成(B)成分之摻雜劑聚合物的單體,可使用具有磺酸基的單體,但是亦可將磺酸基之鋰鹽、鈉鹽、鉀鹽、銨鹽、鋶鹽作為單體使用進行聚合反應,聚合後使用離子交換樹脂變換成磺酸基。
本發明之導電性材料含有作為(C)成分之選自金、銀、及鉑的奈米粒子。(C)成分之選自金、銀、及鉑的奈米粒子係粒徑為1~200nm,更佳為2~100nm。選自金、銀、及鉑之奈米粒子,為了增加表面之化學安定性,可以氧化膜塗覆(coat)。氧化膜無特別限定,較佳為使用矽氧化膜。
(C)成分之含量係相對於(A)成分與(B)成分之合計量100質量份,較佳為0.001~200質量份、更佳為0.005~100質量份、又更佳為1~50質量份。
將光供給分散有金屬奈米粒子之溶液時,發現有吸收。此吸收係因金屬奈米粒子之自由電子彼此共振(resonance)而產生的。此現象稱為電漿子共振。例如粒徑10nm之銀奈米粒子在400nm附近具有藍色吸收,而呈現紅色,但是藉由增大粒徑,使吸收波長形成長波長化,在粒徑100nm時,變成520nm與420nm之2個寬峰(Broad)
的吸收。
由本發明之導電性材料所得之導電膜中,金、銀、及鉑奈米粒子係因不整齊存在,故藉由奈米粒子間之通電,導電性不會提高。藉由照射光,奈米粒子之外角電子產生激發,各自之粒子共振而產生吸收帶。奈米粒子間存在聚噻吩等之共軛導電性高分子時,奈米粒子間之共振激發成為觸發器(trigger),提高聚噻吩內之導電性。將此使用於有機EL時,開始發光同時可提高導電性,提高照度。
以濺鍍等製作的ITO可作為透明電極使用,但是因結晶性的膜,故欲將此彎曲時,結晶會崩壞,導電性會降低、龜裂。因此,將ITO使用於可撓性的裝置有困難。然而,由添加有本發明之選自金、銀、及鉑的奈米粒子之導電性材料所得的導電膜,即使彎曲也不會龜裂,或也不會導電性降低,故可作為可撓性裝置用的導電膜使用。
本發明之導電性材料係含有上述(A)成分的π共軛系聚合物、(B)成分的摻雜劑聚合物、及(C)成分的奈米粒子者,(B)成分之摻雜劑聚合物係藉由配位於(A)成分之π共軛系聚合物,而形成複合體。
本發明之導電性材料係在水或有機溶劑中具有分散性者為佳,對於無機或有機基板(在基板表面形成
無機膜或有機膜的基板),可形成良好的旋轉塗佈成膜性或膜之平坦性。
本發明之導電性材料(溶液)之製造方法無特別限定,例如可藉由在含有上述(A)成分的π共軛系聚合物與(B)成分之摻雜劑聚合物的導電性聚合物複合體(溶液)中,添加(C)成分之選自金、銀、及鉑之奈米粒子來製造。
(A)成分與(B)成分之複合體,例如可藉由在(B)成分之水溶液或(B)成分之水.有機溶劑混合溶液中,添加成為(A)成分之原料的單體(較佳為吡咯、噻吩、苯胺、或此等之衍生物單體),添加氧化劑及有時添加氧化觸媒,進行氧化聚合而得。
氧化劑及氧化觸媒可使用過硫酸銨(ammonium peroxodisulfate)、過硫酸鈉(sodium peroxodisulfate)、過硫酸鉀(Potassium peroxodisulfate)等過硫酸鹽(peroxodisulfate)、氯化鐵、硫酸鐵、氯化銅等過渡金屬化合物、氧化銀、氧化銫等金屬氧化物、過氧化氫、臭氧等過氧化物、過氧化苯甲醯等有機過氧化物、氧等。
進行氧化聚合時所使用之反應溶劑,可使用水或水與溶劑的混合溶劑。此處所使用之溶劑可與水混合,較佳為可溶解或分散(A)成分及(B)成分的溶劑。可列舉例如N-甲基-2-吡咯烷酮、N,N’-二甲基甲醯胺、N,N’-二甲基乙醯胺、二甲基亞碸、六亞甲基磷醯三胺等極性溶
劑;甲醇、乙醇、丙醇、丁醇等之醇類;乙二醇、丙二醇、二丙二醇、1,3-丁二醇、1,4-丁二醇、D-葡萄糖、D-山梨醇、異戊二醇、丁二醇、1,5-戊二醇、1,6-己二醇、1,9-壬二醇、及新戊二醇等之脂肪族多元醇類;碳酸乙烯酯、碳酸丙烯酯等之碳酸酯化合物;二噁烷、四氫呋喃等環狀醚化合物;二烷基醚、乙二醇單烷基醚、乙二醇二烷基醚、丙二醇單烷基醚、丙二醇二烷基醚、聚乙二醇二烷基醚、聚丙二醇二烷基醚等之鏈狀醚類;3-甲基-2-噁唑烷酮等之雜環化合物;乙腈、戊二腈、甲氧基乙腈、丙腈、苯甲腈等之腈化合物等。此等之溶劑可單獨使用,也可為兩種以上的混合物。此等可與水混合之溶劑的調配量,較佳為全部反應溶劑之50質量%以下。
又,(B)成分之摻雜劑聚合物以外,亦可併用可摻雜於(A)成分之π共軛系聚合物的陰離子。如此陰離子就調整源自π共軛系聚合物之脫摻雜特性、導電性材料之分散性、耐熱性、及耐環境特性等的觀點而言,有機酸較佳。有機酸可列舉有機羧酸、苯酚類、有機磺酸等。
有機羧酸可使用於脂肪族、芳香族、環狀脂肪族等中含有一個或兩個以上之羧基者。可列舉例如甲酸、乙酸、草酸、苯甲酸、鄰苯二甲酸、馬來酸、富馬酸、丙二酸、酒石酸、檸檬酸、乳酸、琥珀酸、一氯乙酸、二氯乙酸、三氯乙酸、三氟乙酸、硝基乙酸、三苯基乙酸等。
苯酚類可列舉甲酚、苯酚、二甲苯酚等之苯
酚類。
有機磺酸可使用在脂肪族、芳香族、環狀脂肪族等中含有一個或兩個以上磺酸基的有機磺酸。包含一個磺酸基之有機磺酸,可例示如甲烷磺酸、乙烷磺酸、1-丙烷磺酸、1-丁烷磺酸、1-己烷磺酸、1-庚烷磺酸、1-辛烷磺酸、1-壬烷磺酸、1-癸烷磺酸、1-十二烷磺酸、1-十四烷磺酸、1-十五烷磺酸、2-溴乙烷磺酸、3-氯-2-羥基丙烷磺酸、三氟甲烷磺酸、黏菌素(Colistin)甲烷磺酸、2-丙烯醯胺-2-甲基丙烷磺酸、胺基甲烷磺酸、1-胺基-2-萘酚-4-磺酸、2-胺基-5-萘酚-7-磺酸、3-胺基丙烷磺酸、N-環己基-3-胺基丙烷磺酸、苯磺酸、對甲苯磺酸、二甲苯磺酸、乙基苯磺酸、丙基苯磺酸、丁基苯磺酸、戊基苯磺酸、己基苯磺酸、庚基苯磺酸、辛基苯磺酸、壬基苯磺酸、癸基苯磺酸、十一烷基苯磺酸、十二烷基苯磺酸、十五烷基苯磺酸、十六烷基苯磺酸、2,4-二甲基苯磺酸、二丙基苯磺酸、4-胺基苯磺酸、鄰胺基苯磺酸、間胺基苯磺酸、4-胺基-2-氯甲苯-5-磺酸、4-胺基-3-甲基苯-1-磺酸、4-胺基-5-甲氧基-2-甲基苯磺酸、2-胺基-5-甲基苯-1-磺酸、4-胺基-2-甲基苯-1-磺酸、5-胺基-2-甲基苯-1-磺酸、4-乙醯胺-3-氯苯磺酸、4-氯-3-硝基苯磺酸、對氯苯磺酸、萘磺酸、甲基萘磺酸、丙基萘磺酸、丁基萘磺酸、戊基萘磺酸、二甲基萘磺酸、4-胺基-1-萘磺酸、8-氯萘-1-磺酸、萘磺酸福馬林聚縮合物、三聚氰胺磺酸福馬林聚縮合物等之含有磺酸基之磺酸化合物等。
含有兩個以上之磺酸基的有機磺酸,可列舉例如乙烷二磺酸、丁烷二磺酸、戊烷二磺酸、癸烷二磺酸、間苯二磺酸、鄰苯二磺酸、對苯二磺酸、甲苯二磺酸、二甲苯二磺酸、氯苯二磺酸、氟苯二磺酸、苯胺-2,4-二磺酸、苯胺-2,5-二磺酸、二乙基苯二磺酸、二丁基苯二磺酸、萘二磺酸、甲基萘二磺酸、乙基萘二磺酸、十二烷基萘二磺酸、十五烷基萘二磺酸、丁基萘二磺酸、2-胺基-1,4-苯二磺酸、1-胺基-3,8-萘二磺酸、3-胺基-1,5-萘二磺酸、8-胺基-1-萘酚-3,6-二磺酸、蒽二磺酸、丁基蒽二磺酸、4-乙醯胺-4’-異硫氰酸芪-2,2’-二磺酸、4-乙醯胺-4’-異硫氰酸芪-2,2’-二磺酸、4-乙醯胺-4’-馬來醯亞胺芪-2,2’-二磺酸(4-acetamide-4’-maleimidyl stilbene-2,2’-disulfonate)、1-乙醯氧基芘-3,6,8-三磺酸、7-胺基-1,3,6-萘三磺酸、8-胺萘-1,3,6-三磺酸、及3-胺基-1,5,7-萘三磺酸等。
此等(B)成分以外之陰離子,可於(A)成分之聚合前,添加至包含(A)成分之原料單體、(B)成分、氧化劑及/或氧化聚合觸媒之溶液中,又,亦可添加至包含聚合後之(A)成分與(B)成分之導電性聚合物複合體(溶液)中。
如此所得之(A)成分與(B)成分之複合體,可視需要使用均質器或球磨機等進行細粒化來使用。
於細粒化時使用可賦予高剪切力之混合分散機為佳。混合分散機可列舉例如均質器、高壓均質器、珠磨機等,其中高壓均質器較佳。
高壓均質器之具體例,可列舉吉田機械興業公司製造之Nanovater、Powrex公司製造之micro-fluidizer、杉野機械公司製造之ULTIMAIZER等。
使用高壓均質器之分散處理,可列舉例如使施予分散處理前之複合體溶液以高壓對向衝突之處理、以高壓通過孔或狹縫之處理等。
於細粒化之前或後亦可藉由過濾、超過濾、透析等之手法除去雜質,使用陽離子交換樹脂、陰離子交換樹脂、螯合物樹脂等進行純化。
另外,導電性材料溶液中之(A)成分與(B)成分之合計含量,較佳為0.05~5.0質量%。(A)成分與(B)成分之合計含量為0.05質量%以上時,可得到充分的導電性,若5.0質量%以下時,容易得到均勻的導電性塗膜。
(B)成分之含量係相對於(A)成分1莫耳,(B)成分中之磺酸基成為0.1~10莫耳之範圍的量為佳,成為1~7莫耳之範圍的量更佳。(B)成分中之磺酸基為0.1莫耳以上時,對(A)成分之摻雜效果高,可確保充分的導電性。又,(B)成分中之磺酸基為10莫耳以下時,(A)成分之含量為適度者,可得到充分的導電性。
本發明中,為了提升對基板等被加工體的濕潤性,亦可添加界面活性劑。這種界面活性劑可列舉非離子系、陽
離子系、陰離子系之各種界面活性劑。具體而言,可列舉例如聚氧乙烯烷基醚、聚氧乙烯烷基苯基醚、聚氧乙烯羧酸酯、山梨糖醇酐酯、聚氧乙烯山梨糖醇酐酯等之非離子系界面活性劑、烷基三甲基氯化銨、烷基苄基氯化銨等之陽離子系界面活性劑、烷基或烷基烯丙基硫酸鹽、烷基或烷基烯丙基磺酸鹽、二烷基磺酸基琥珀酸等之陰離子系界面活性劑、胺基酸型、甜菜鹼型等之兩性離子型界面活性劑、乙炔醇系界面活性劑、羥基被聚環氧乙烷或被聚環氧丙烷化之乙炔醇系界面活性劑等。
本發明中,為了提升導電性材料之導電率之目的,除了主劑外,亦可添加作為高導電化劑之有機溶劑。這種添加溶劑可列舉極性溶劑,具體而言,可列舉乙二醇、二乙二醇、三乙二醇、聚乙二醇、二甲基亞碸(DMSO)、二甲基甲醯胺(DMF)、N-甲基-2-吡咯烷酮(NMP)、環丁碸、碳酸乙烯酯及此等之混合物。添加量較佳為1.0~30.0質量%,特佳為3.0~10.0質量%。
本發明中,導電性材料之水溶液中之pH呈酸性。為了將此中和,可添加在日本特開2006-96975公報中之段落[0033]~[0045]所記載之含氮芳香族性環式化合物、日本專利5264723之段落[0127]所記載之陽離子,將pH控
制在中性。藉由將溶液之pH控制在中性附近,使用於印刷機的情形,可防止生鏽。
如以上說明之本發明之導電性材料時,過濾性及旋轉塗佈之成膜性良好,可形成透明性高、表面粗糙度低的導電膜。
如上述所得之導電性材料(溶液)可藉由塗佈於基板等之被加工體而形成導電膜。導電性材料(溶液)之塗佈方法,可列舉例如藉由旋轉塗佈機等之塗佈、塗佈棒、浸漬、雙輥筒塗佈(comma coat)、噴塗、輥塗、網版印刷、凸版印刷、凹版印刷、噴墨印刷等。塗佈後,藉由熱風循環爐、熱板等之加熱處理,並進行IR、UV照射等可形成導電膜。
如此,本發明之導電性材料係藉由於基板等進行塗佈、成膜可製得導電膜。又,如此所形成之導電膜係因導電性、透明性優異,故可具有作為透明電極層產生功能者。
又,本發明提供藉由上述本發明之導電性材料形成導電膜的基板。
基板可列舉玻璃基板、石英基板、光罩空白基板、樹脂基板、矽晶圓、砷化鎵晶圓、磷化銦晶圓等之化合物半
導體晶圓、可撓性基板等。又,亦可塗佈於光阻膜上作為抗靜電上塗層使用。
如上述,包含含有超強酸之磺酸基之(B)成分之摻雜劑聚合物與(A)成分之π共軛系聚合物之複合體及(C)成分之金、銀、或鉑奈米粒子之本發明之導電性材料時,可形成過濾性及旋轉塗佈之成膜性佳,又,形成膜時,透明性、撓性、平坦性、耐久性、及導電性良好,且表面粗糙度低的導電膜。又,這種導電性材料時,對於有機基板、無機基板之任一者,其成膜性均良好者。
又,藉由這種導電性材料所形成之導電膜,因導電性、透明性等優異,故可作為透明電極層之機能者。
以下,使用合成例、調製例、比較調製例、實施例、及比較例,具體地說明本發明,但是本發明並不限定於此等。
氮環境下,將於64℃攪拌之甲醇中,混合有單體與2,2’-偶氮雙(異丁酸)二甲酯之溶液攪拌8小時,冷卻置室溫後,在激烈攪拌下滴下至乙酸乙酯中。生成之固體成分以過濾取得,將於50℃下真空乾燥15小時所得之白色聚
合物溶解於純水中,使用離子交換樹脂將單體之陽離子交換成氫原子而變換成磺酸基。
利用這種方法合成下述所示之摻雜劑聚合物1~8。
重量平均分子量(Mw)=29,900
分子量分布(Mw/Mn)=1.91
重量平均分子量(Mw)=31,000
分子量分布(Mw/Mn)=1.89
重量平均分子量(Mw)=24,000
分子量分布(Mw/Mn)=1.76
重量平均分子量(Mw)=39,300
分子量分布(Mw/Mn)=1.91
重量平均分子量(Mw)=41,100
分子量分布(Mw/Mn)=1.98
重量平均分子量(Mw)=53,000
分子量分布(Mw/Mn)=1.81
重量平均分子量(Mw)=53,000
分子量分布(Mw/Mn)=1.81
重量平均分子量(Mw)=21,000
分子量分布(Mw/Mn)=1.30
於30℃下混合3.82g之3,4-乙烯二氧噻吩及於1,000mL之超純水中溶解有12.5g之摻雜劑聚合物1的溶液。
將藉此所得之混合溶液保持於30℃,邊攪拌邊緩慢地添加溶解於100mL之超純水中之8.40g之過硫酸鈉與2.3g之硫酸鐵之氧化觸媒溶液,攪拌4小時使其反應。
於所得之反應液中添加1,000mL之超純水,並使用超過濾法除去約1,000mL之溶液。重複此操作3次。
並且,於進行了上述過濾處理之處理液中添加200mL之稀釋成10質量%之硫酸及2,000mL之離子交換水,使用超過濾法除去約2,000mL的處理液,於此中添加2,000mL之離子交換水,使用超過濾法除去約2,000mL之液體。重複此操作3次。
進一步,於所得之處理液中添加2,000mL之離子交換水,使用超過濾法除去約2,000mL的處理液。重複此操作5次,使用孔徑0.45μm之再生纖維素過濾器(ADVANTEC公司製)進行過濾,得到1.3質量%之藍色的導電性聚合物複合體分散液1。
超過濾條件係如下所述。
超過濾膜之截留分子量(cutoff molecular weight):30K
交叉流式
供給液流量:3,000mL/分鐘
膜分壓:0.12Pa
另外,其他之調製例亦以同樣條件進行超過濾。
除了將12.5g之摻雜劑聚合物1變更為10.0g之摻雜劑聚合物2,將3,4-乙烯二氧噻吩之調配量變更為2.41g,將過硫酸鈉之調配量變更為5.31g,將硫酸鐵之調配量變更為1.50g外,與調製例1相同的方法進行調製,得到導電性聚合物複合體分散液2。
除了將12.5g之摻雜劑聚合物1變更為12.0g之摻雜劑聚合物3,將3,4-乙烯二氧噻吩之調配量變更為2.72g,將過硫酸鈉之調配量變更為6.00g,將硫酸鐵之調配量變更為1.60g外,與調製例1相同的方法進行調製,得到導電性聚合物複合體分散液3。
除了將12.5g之摻雜劑聚合物1變更為11.8g之摻雜劑聚合物4,將8.40g之過硫酸鈉變更為4.50g之過硫酸銨,將3,4-乙烯二氧噻吩之調配量變更為2.04g,將硫酸鐵之調配量變更為1.23g外,與調製例1相同的方法進行調製,得到導電性聚合物複合體分散液4。
除了將12.5g之摻雜劑聚合物1變更為11.0g之摻雜劑聚合物5,將8.40g之過硫酸鈉變更為5.31g之過硫酸銨,將3,4-乙烯二氧噻吩之調配量變更為2.41g,將硫酸鐵之調配量變更為1.50g外,與調製例1相同的方法進行調製,得到導電性聚合物複合體分散液5。
將12.5g之摻雜劑聚合物1變更為13.0g之摻雜劑聚合物6,將8.40g之過硫酸鈉變更為5.31g之過硫酸銨,將3,4-乙烯二氧噻吩之調配量變更為2.41g,將硫酸鐵之調配量變更為1.50g外,與調製例1相同的方法進行調製,得到導電性聚合物複合體分散液6。
將12.5g之摻雜劑聚合物1變更為12.8g之摻雜劑聚合物7,將8.40g之過硫酸鈉變更為5.31g之過硫酸銨,將3,4-乙烯二氧噻吩之調配量變更為2.41g,將硫酸鐵之調配量變更為1.50g外,與調製例1相同的方法進行調製,得到導電性聚合物複合體分散液7。
將12.5g之摻雜劑聚合物1變更為11.0g之摻雜劑聚
合物8,將8.40g之過硫酸鈉變更為5.31g之過硫酸銨,將3,4-乙烯二氧噻吩之調配量變更為2.41g,將硫酸鐵之調配量變更為1.50g外,與調製例1相同的方法進行調製,得到導電性聚合物複合體分散液8。
於30℃下混合3.87g之3,4-乙烯二氧噻吩及於1,000mL之超純水中溶解有10.0g之摻雜劑聚合物2的溶液。
將藉此所得之混合溶液保持於30℃,邊攪拌邊緩慢地添加溶解於100mL之超純水中之8.40g之過硫酸鈉與2.3g之硫酸鐵之氧化觸媒溶液,攪拌4小時使其反應。
於所得之反應液中添加1,000mL之超純水,並使用超過濾法除去約1,000mL之溶液。重複此操作3次。
並且,於進行了上述過濾處理之處理液中添加200mL之稀釋成10質量%之硫酸及2,000mL之離子交換水,使用超過濾法除去約2,000mL的處理液,於此處理液中添加2,000mL之離子交換水,使用超過濾法除去約2,000mL之液體。重複此操作3次。
進一步,於所得之處理液中添加2,000mL之離子交換水,使用超過濾法除去約2,000mL的處理液。重複此操作5次,使用孔徑0.45μm之再生纖維素過濾器(ADVANTEC公司製)進行過濾,得到1.3質量%之藍色的導電性聚合物複合體分散液9。
於30℃下混合4.62g之(2,3-二氫噻吩並[3,4-b][1,4]戴奧辛-2-基)甲醇與在1,000mL之超純水中溶解有10.0g之摻雜劑聚合物2的溶液。
將藉此所得到之混合溶液保持於30℃,邊攪拌邊緩慢地添加已溶解於100mL之超純水中之8.40g之過硫酸鈉及2.3g之硫酸鐵之氧化觸媒溶液,攪拌4小時使其反應。
於所得到之反應液中添加1,000mL之超純水,並使用超過濾法除去約1,000mL之溶液。重複此操作3次。
並且,於已進行上述過濾處理之處理液中添加200mL之稀釋至10質量%之硫酸及2,000mL之離子交換水,使用超過濾法除去約2,000mL之處理液,於此處理液中添加2,000mL之離子交換水,使用超過濾法除去約2,000mL之液體。重複此操作3次。
進一步,於所得之處理液中添加2,000mL之離子交換水,使用超過濾法除去約2,000mL之處理液。重複此操作5次,使用孔徑0.45μm之再生纖維素過濾器(ADVANTEC公司製)進行過濾,得到1.3質量%之藍色的導電性聚合物複合體分散液10。
於30℃下混合4.16g之3,4-丙烯二氧硫代噻吩與在
1,000mL之超純水中溶解有10.0g之摻雜劑聚合物2的溶液。
將藉此所得到之混合溶液保持於30℃,邊攪拌邊緩慢地添加已溶解於100mL之超純水中之8.40g之過硫酸鈉及2.3g之硫酸鐵之氧化觸媒溶液,攪拌4小時使其反應。
於所得到之反應液中添加1,000mL之超純水,並使用超過濾法除去約1,000mL之溶液。重複此操作3次。
並且,於已進行上述過濾處理之處理液中添加200mL之稀釋至10質量%之硫酸及2,000mL之離子交換水,使用超過濾法除去約2,000mL之處理液,於此處理液中添加2,000mL之離子交換水,使用超過濾法除去約2,000mL之液體。重複此操作3次。
進一步,於所得之處理液中添加2,000mL之離子交換水,使用超過濾法除去約2,000mL之處理液。重複此操作5次,使用孔徑0.45μm之再生纖維素過濾器(ADVANTEC公司製)進行過濾,得到1.3質量%之藍色的導電性聚合物複合體分散液11。
於30℃下混合5.0g之3,4-乙烯二氧噻吩及經250mL之離子交換水稀釋之83.3g之聚苯乙烯磺酸水溶液
(Aldrich製18.0質量%)的溶液。除此之外,與調製例1相同的方法進行調製,得到1.3質量%之藍色的比較導電性聚合物複合體分散液1(PEDOT-PSS分散液)。
下述表1中之銀奈米粒子1、銀奈米粒子2、金奈米粒子1、及鉑奈米粒子1之詳細如以下所示。
銀奈米粒子1為使用粒徑10nm之銀奈米粒子以0.002質量%的濃度分散於水中的溶液,銀奈米粒子2為使用粒徑20nm之銀奈米粒子以0.002質量%的濃度分散於水中的溶液。又,金奈米粒子1為使用粒徑20nm之金奈米粒子以0.005質量%的濃度分散於水中的溶液,鉑奈米粒子1為使用粒徑20nm之鉑奈米粒子以0.005質量%的濃度分散於水中的溶液。
實施例及比較例係使用此等作為奈米粒子。
將調製例1~11所得之1.3質量%之導電性聚合物複合體分散液1~11、有機溶劑、Dupont公司製之界面活性劑FS-31、奈米粒子分別如表1所記載的組成進行混合,然後,使用孔徑0.45μm之再生纖維素過濾器(ADVANTEC公司製)過濾調製導電性材料,分別當作實施例1~14。表1中,DMSO表示二甲基亞碸。
將比較調製例1所得之1.3質量%之比較導電性聚合物複合體分散液1、水、有機溶劑、Dupont公司製之界面活性劑FS-31如表1所記載的組成進行混合,然後,使用孔徑0.45μm之再生纖維素過濾器(ADVANTEC公司製)過濾調製導電性材料,當作比較例1。
將調製例1所得之1.3質量%之導電性聚合物複合體分散液1、水、有機溶劑、Dupont公司製之界面活性劑FS-31,如表1所記載的組成進行混合,然後,使用孔徑0.45μm之再生纖維素過濾器(ADVANTEC公司製)過濾調製導電性材料,當作比較例2。
將水、有機溶劑、Dupont公司製之界面活性劑FS-31、銀奈米粒子1,如表1所記載的組成進行混合,然後,使用孔徑0.45μm之再生纖維素過濾器(ADVANTEC公司製)過濾調製導電性材料,當作比較例3。
如以下評價上述調製之實施例及比較例之導電性材料。
首先,於直径4英寸(100mm)之SiO2晶圓上滴下導電
性材料1.0mL後,10秒後使用旋轉器整體旋轉塗佈。實施例1~14、比較例1、2中之旋轉塗佈條件進行調節使膜厚成為100±5nm。僅比較例3之銀奈米粒子之溶液塗佈,考慮銀奈米粒子之粒徑,而形成60nm的膜厚。塗佈後,藉由使用精密恆溫器,以120℃、進行5分鐘烘烤,除去溶劑得到導電膜。
所得之導電膜之導電率(S/cm)係由SiO2晶圓之下側,邊照射100W之白色螢光燈,邊使用Hiresta-UP MCP-HT450、Loresta-GP MCP-T610(均為三菱化學公司製)所測量之表面電阻係數(Ω/□)與膜厚之實測值求得。結果如表1所示。
藉由以可改變入射角之分光橢圓測厚儀(VASE)測量之波長636nm下之折射率(n,k),計算FT=100nm時,對波長550nm之光線之透過率。結果如表1所示。
如表1所示,將包含作為π共軛系聚合物之聚噻吩、含有選自重複單位a1~a4之1種以上的重複單位的摻雜劑聚合物、及金、銀、及鉑之奈米粒子之實施例1~14,以旋轉塗佈器塗佈時,可得到平坦且均勻的塗膜。又,確認藉由添加金、銀、或鉑奈米粒子,而提高導電性。又,得知撓性或對λ=550nm之可見光之透過率亦良好。
另一方面,包含僅含有聚苯乙烯磺酸之摻雜
劑聚合物,而不含奈米粒子的比較例1,雖導電性高,但是在膜上產生條紋。又,包含含有重複單位a1之摻雜劑聚合物,而不含奈米粒子的比較例2,雖可得到平坦且均勻的塗膜,但是為導電性差者。又,僅含有銀奈米粒子的比較例3,在膜上產生條紋,且為導電性差者。
如上述,得知本發明之導電性材料時,旋轉塗佈之成膜性佳,可形成透明性、導電性高、撓性優異、平坦性佳的導電膜。
另外,本發明不限定於上述實施形態者。上述實施形態為例示,具有與本發明之申請專利範圍所記載之技術思想實質上相同的構成,且發揮同樣的作用效果者,即使任何形態者均包含在本發明之技術範圍內。
Claims (20)
- 一種導電性材料,其係含有:(A)π共軛之聚合物、及(B)摻雜劑聚合物,其含有選自分別於下述一般式(1)表示之重複單位“A1”~“A4”之1種以上的重複單位,且重量平均分子量在1,000~500,000之範圍中、(C)奈米粒子,其係選自由金奈米粒子、銀奈米粒子、及鉑奈米粒子所成群組且具有之粒徑為1~200nm,
- 如申請專利範圍第1項之導電性材料,其中前述(B)成分進一步含有以下述一般式(2)表示之重複單位“B1”,
- 如申請專利範圍第2項之導電性材料,其中前述(B)成分為嵌段共聚物。
- 如申請專利範圍第3項之導電性材料,其中前述(A)成分為藉由將選自由吡咯、噻吩、硒吩、碲吩、苯胺、多環式芳香族化合物、及其衍生物所成群之1種以上的前驅物單體聚合形成之聚合物。
- 如申請專利範圍第4項之導電性材料,其中前述導電性材料係在水或有機溶劑中具有分散性者。
- 如申請專利範圍第3項之導電性材料,其中前述導電性材料係在水或有機溶劑中具有分散性者。
- 如申請專利範圍第2項之導電性材料,其中前述(A)成分為藉由將選自由吡咯、噻吩、硒吩、碲吩、苯胺、多環式芳香族化合物、及其衍生物所成群之1種以上的前驅物單體聚合形成之聚合物。
- 如申請專利範圍第7項之導電性材料,其中前述導電性材料係在水或有機溶劑中具有分散性者。
- 如申請專利範圍第2項之導電性材料,其中前述導電性材料係在水或有機溶劑中具有分散性者。
- 一種基板,其具有藉由使用如申請專利範圍第2項之導電性材料而形成於其上之導電膜。
- 如申請專利範圍第10項之基板,其中前述導電膜係作為透明電極層之功能。
- 如申請專利範圍第1項之導電性材料,其中前述 (B)成分為嵌段共聚物。
- 如申請專利範圍第12項之導電性材料,其中前述(A)成分為藉由將選自由吡咯、噻吩、硒吩、碲吩、苯胺、多環式芳香族化合物、及其衍生物所成群之1種以上的前驅物單體聚合形成之聚合物。
- 如申請專利範圍第13項之導電性材料,其中前述導電性材料係在水或有機溶劑中具有分散性者。
- 如申請專利範圍第12項之導電性材料,其中前述導電性材料係在水或有機溶劑中具有分散性者。
- 如申請專利範圍第1項之導電性材料,其中前述(A)成分為藉由將選自由吡咯、噻吩、硒吩、確吩、苯胺、多環式芳香族化合物、及其衍生物所成群之1種以上的前驅物單體聚合形成之聚合物。
- 如申請專利範圍第16項之導電性材料,其中前述導電性材料係在水或有機溶劑中具有分散性者。
- 如申請專利範圍第1項之導電性材料,其中前述導電性材料係在水或有機溶劑中具有分散性者。
- 一種基板,其具有藉由使用如申請專利範圍第1項之導電性材料而形成於其上之導電膜。
- 如申請專利範圍第19項之基板,其中前述導電膜係作為透明電極層之功能。
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JP6709134B2 (ja) * | 2016-09-16 | 2020-06-10 | 富士フイルム株式会社 | ポリマー、固体電解質、固体電解質組成物、無機固体電解質組成物、固体電解質含有シート、二次電池、全固体二次電池、固体電解質含有シートの製造方法、無機固体電解質含有シートの製造方法、二次電池の製造方法および全固体二次電池の製造方法 |
KR102601451B1 (ko) | 2016-09-30 | 2023-11-13 | 엘지디스플레이 주식회사 | 전극 및 이를 포함하는 유기발광소자, 액정표시장치 및 유기발광표시장치 |
JP6661212B2 (ja) * | 2017-02-22 | 2020-03-11 | 信越化学工業株式会社 | 導電性ポリマー複合体及び基板 |
JP6845191B2 (ja) * | 2017-10-19 | 2021-03-17 | 信越化学工業株式会社 | 生体電極組成物、生体電極、及び生体電極の製造方法 |
JP6920000B2 (ja) * | 2017-10-26 | 2021-08-18 | 信越化学工業株式会社 | 生体電極組成物、生体電極、及び生体電極の製造方法 |
JP6850279B2 (ja) * | 2017-11-21 | 2021-03-31 | 信越化学工業株式会社 | 生体電極組成物、生体電極、及び生体電極の製造方法 |
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