JP2015196756A - 導電性高分子組成物及び導電層並びに導電体 - Google Patents
導電性高分子組成物及び導電層並びに導電体 Download PDFInfo
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- JP2015196756A JP2015196756A JP2014074940A JP2014074940A JP2015196756A JP 2015196756 A JP2015196756 A JP 2015196756A JP 2014074940 A JP2014074940 A JP 2014074940A JP 2014074940 A JP2014074940 A JP 2014074940A JP 2015196756 A JP2015196756 A JP 2015196756A
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- bis
- methyl
- conductive polymer
- hydroxy
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- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 43
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- 125000005843 halogen group Chemical group 0.000 claims abstract description 17
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- 239000000126 substance Substances 0.000 claims description 9
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- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 6
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- MAGFQRLKWCCTQJ-UHFFFAOYSA-N 4-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-N 0.000 claims description 4
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 3
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- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
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- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
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Abstract
Description
X1は、アミド基、エーテル基、カルボニル基、キシレニル基、スルフィド基、スルホニル基、ジスルフィド基、シクロアルキレン基、フェニレン基又は下記式(2)で表される基である。
a及びbは、それぞれ独立して1以上3以下の整数である。kは、1以上3以下の整数である。jは1又は2である。また、a及びkは、下記式(I)を満たす。)
2≦a+k≦4 (I)
Y1は、水素原子、アルキル基、フルオロアルキル基、シクロアルキル基、フェニル基、アダマンチル基又は下記式(3)で表される基である。
ただし、Y1とR5とは互いに結合してシクロアルカン構造又はフルオレン構造を形成していてもよい。)
R8は、水素原子、アルキル基、シクロアルキル基、フェニル基又はベンジル基である。
cは、0以上3以下の整数である。)
R13及びR14は、それぞれ独立して、水素原子又はアルキル基である。
X2は、アミド基、エーテル基、カルボニル基、キシレニル基、スルフィド基、スルホニル基、ジスルフィド基、シクロアルキレン基、フェニレン基又は下記式(5)で表される基である。
d、e及びgは、それぞれ独立して1又は2である。fは0以上2以下の整数である。mは0以上2以下の整数である。ただし、f及びmは同時に0となることはない。nは0又は1である。また、d、e、f、g及びmは、下記式(II)及び(III)を満たす。)
2≦d+f+m≦4 (II)
2≦e+g≦3 (III)
Y2は、水素原子、アルキル基、フルオロアルキル基、シクロアルキル基、フェニル基、アダマンチル基又は下記式(6)で表される基である。
ただし、Y2とR15とは互いに結合してシクロアルカン構造又はフルオレン構造を形成していてもよい。)
R18は、水素原子、アルキル基、シクロアルキル基、フェニル基又はベンジル基である。
R19は、水素原子又はアルキル基である。
h及びiは、それぞれ独立して0以上2以下の整数であり、下記式(IV)を満たす。)
0≦h+i≦3 (IV)
導電性高分子組成物(X)は、導電性高分子化合物(A)、上記式(1)で表される多価フェノール化合物(B)及び上記式(4)で表されるメチロール化フェノール化合物(C)を含有する。当該導電性高分子組成物(X)は、ドーパント、溶媒、バインダー樹脂又は架橋剤をさらに含有することが好ましい。また、本発明の趣旨を損なわない限り、その他の任意成分を含有していてもよい。以下、各成分について説明する。
導電性高分子化合物(A)は、分子鎖中に共役二重結合を有する共役系高分子から構成される。
上記共役系高分子としては、例えばポリアセチレン、ポリジアセチレン、ポリパラフェニレン、ポリフルオレン、ポリアズレン、ポリパラフェニレンサルファイド、ポリピロール、ポリチオフェン、ポリイソチアナフテン、ポリアニリン、ポリパラフェニレンビニレン、ポリ(2,5−チエニレンビニレン)、複鎖型共役系高分子(ポリペリナフタレン等)、金属フタロシアニン系高分子、その他共役系高分子(ポリパラキシリレン等)、これらの共重合体等が挙げられる。
多価フェノール化合物(B)は、下記式(1)で表される化合物である。
X1は、アミド基、エーテル基、カルボニル基、キシレニル基、スルフィド基、スルホニル基、ジスルフィド基、シクロアルキレン基、フェニレン基又は下記式(2)で表される基である。
a及びbは、それぞれ独立して1以上3以下の整数である。kは、1以上3以下の整数である。jは1又は2である。また、a及びkは、下記式(I)を満たす。
2≦a+k≦4 (I)
Y1は、水素原子、アルキル基、フルオロアルキル基、シクロアルキル基、フェニル基、アダマンチル基又は下記式(3)で表される基である。
ただし、Y1とR5とは互いに結合してシクロアルカン構造又はフルオレン構造を形成していてもよい。
R8は水素原子、アルキル基、シクロアルキル基、フェニル基又はベンジル基である。
cは、0以上3以下の整数である。
4,6−ジヒドロキシフェニル)プロパン、1,1−ビス(4−ヒドロキシフェニル)シクロヘキサン、1,1−ビス(4−ヒドロキシ−3−フェニル)シクロヘキサン、1,1−ビス(3,4−ジヒドロキシ−6−メチルフェニル)シクロヘキサン、9,9−ビス(4−ヒドロキシフェニル)−9H−フルオレン、9,9−ビス(4−ヒドロキシ−3−メチルフェニル)−9H−フルオレン、9,9−ビス(3−アリル−4−ヒドロキシフェニル)−9H−フルオレン、9,9−ビス(3,4−ジヒドロキシ−6−メチルフェニル)−9H−フルオレン、1,1−ビス(4−ヒドロキシフェニル)−1−アダマンチルエタン、1,1−ビス(3,4−ジヒドロキシ−6−メチルフェニル)−1−アダマンチルエタン、1,1,1−トリス(4−ヒドロキシフェニル)エタン、1,1−ビス(4−ヒドロキシフェニル)−1−フェニルエタン、1,1−ビス(4−ヒドロキシ−3−メチルフェニル)−1−フェニルエタン、1,1−ビス(2,4−ジヒドロキシフェニル)−1−フェニルエタン、1,1−ビス(3,4−ジヒドロキシフェニル)−1−フェニルエタン、1,1−ビス(2,5−ジヒドロキシフェニル)−1−フェニルエタン、1,1−ビス(2,3,4−トリヒドロキシフェニル)−1−フェニルエタン、1,1−ビス(3,4−ジヒドロキシ−6−メチルフェニル)−1−フェニルエタン、1,1−ビス(2,4−ジヒドロキシ−3−メチルフェニル)−1−フェニルエタン、1,1−ビス(2,4−ジヒドロキシ−5−メチルフェニル)−1−フェニルエタン、1,1−ビス(3−ヘキシル−4,6−ジヒドロキシフェニル)−1−フェニルエタン、1,1−ビス(3−クロロ−4,6−ジヒドロキシフェニル)−1−フェニルエタン、1,1−ビス(4−ヒドロキシ−3−メチルフェニル)−1−(4−ヒドロキシフェニル)エタン、1,1−ビス(2,4−ジヒドロキシフェニル)−1−(4−ヒドロキシフェニル)エタン、1,1−ビス(3,4−ジヒドロキシフェニル)−1−(4−ヒドロキシフェニル)エタン、1,1−ビス(2,5−ジヒドロキシフェニル)−1−(4−ヒドロキシフェニル)エタン、1,1−ビス(2,3,4−トリヒドロキシフェニル)−1−(4−ヒドロキシフェニル)エタン、1,1−ビス(3,4−ジヒドロキシ−6−メチルフェニル)−1−(4−ヒドロキシフェニル)エタン、1,1−ビス(2,4−ジヒドロキシ−3−メチルフェニル)−1−(4−ヒドロキシフェニル)エタン、1,1−ビス(2,4−ジヒドロキシ−5−メチルフェニル)−1−(4−ヒドロキシフェニル)エタン、1,1−ビス(3−ヘキシル−4,6−ジヒドロキシフェニル)−1−(4−ヒドロキシフェニル)エタン、1,1−ビス(3−クロロ−4,6−ジヒドロキシフェニル)−1−(4−ヒドロキシフェニル)エタン、1,1−ビス(4−ヒドロキシフェニル)−1−(2,4−ジヒドロキシフェニル)エタン、1,1−ビス(4−ヒドロキシ−3−メチルフェニル)−1−(2,4−ジヒドロキシフェニル)エタン、1,1,1−トリス(2,4−ジヒドロキシフェニル)エタン、1,1−ビス(3,4−ジヒドロキシフェニル)−1−(2,4−ジヒドロキシフェニル)エタン、1,1−ビス(2,5−ジヒドロキシフェニル)−1−(2,4−ジヒドロキシフェニル)エタン、1,1−ビス(2,3,4−トリヒドロキシフェニル)−1−(2,4−ジヒドロキシフェニル)エタン、1,1−ビス(3,4−ジヒドロキシ−6−メチルフェニル)−1−(2,4−ジヒドロキシフェニル)エタン、1,1−ビス(2,4−ジヒドロキシ−3−メチルフェニル)−1−(2,4−ジヒドロキシフェニル)エタン、1,1−ビス(2,4−ジヒドロキシ−5−メチルフェニル)−1−(2,4−ジヒドロキシフェニル)エタン、1,1−ビス(3−ヘキシル−4,6−ジヒドロキシフェニル)−1−(2,4−ジヒドロキシフェニル)エタン、1,1−ビス(3−クロロ−4,6−ジヒドロキシフェニル)−1−(2,4−ジヒドロキシフェニル)エタン、1,4−ビス[(4−ヒドロキシフェニル)メチル]ベンゼン、1,4−ビス[(4−ヒドロキシ−3−メチルフェニル)メチル]ベンゼン、1,4−ビス[(2,4−ジヒドロキシフェニル)メチル]ベンゼン、1,4−ビス[(3,4−ジヒドロキシフェニル)メチル]ベンゼン、1,4−ビス[(2,5−ジヒドロキシフェニル)メチル]ベンゼン、1,4−ビス[(2,3,4−トリヒドロキシフェニル)メチル]ベンゼン、1,4−ビス[(3,4−ジヒドロキシ−6−メチルフェニル)メチル]ベンゼン、1,4−ビス[(2,4−ジヒドロキシ−3−メチルフェニル)メチル]ベンゼン、1,4−ビス[(2,4−ジヒドロキシ−5−メチルフェニル)メチル]ベンゼン、1,4−ビス[(3−ヘキシル−4,6−ジヒドロキシフェニル)メチル]ベンゼン、1,4−ビス[(3−クロロ−4,6−ジヒドロキシフェニル)メチル]ベンゼン、ビス(4−ヒドロキシフェニル)ケトン、(2−ヒドロキシフェニル)(4−ヒドロキシフェニル)ケトン、(2,4−ジヒドロキシフェニル)(4−ヒドロキシフェニル)ケトン、(2,3,4−トリヒドロキシフェニル)(4−ヒドロキシフェニル)ケトン、ビス(4−ヒドロキシフェニル)スルホン、(2−ヒドロキシフェニル)(4−ヒドロキシフェニル)スルホン、ビス(4−ヒドロキシ−3−メチルフェニル)スルホン、ビス(4−ヒドロキシ−2,5−ジメチルフェニル)スルホン、ビス(3−アリル−4−ヒドロキシフェニル)スルホン、ビス(3−クロロ−4−ヒドロキシフェニル)スルホン、ビス(4−ヒドロキシ−3−スルホフェニル)スルホン、ビス(4−ヒドロキシフェニル)スルフィド、ビス(4−ヒドロキシ−3−メチルフェニル)スルフィド、ビス(3−カルボキシ−4−ヒドロキシフェニル)スルフィド、ビス(4−ヒドロキシフェニル)エーテル、N−(4−ヒドロキシフェニル)−4−ヒドロキシベンズアミド、ビス(4−ヒドロキシフェニル)ジスルフィド、2,6−ビス[(4−ヒドロキシフェニル)メチル]−4−メチルフェノール、2,6−ビス[(4−ヒドロキシ−3−メチルフェニル)メチル]−4−メチルフェノール、2,6−ビス[(2,4−ジヒドロキシフェニル)メチル]−4−メチルフェノール、2,6−ビス[(3,4−ジヒドロキシフェニル)メチル]−4−メチルフェノール、2,6−ビス[(2,5−ジヒドロキシフェニル)メチル]−4−メチルフェノール、2,6−ビス[(2,3,4−トリヒドロキシフェニル)メチル]−4−メチルフェノール、2,6−ビス[(3,4−ジヒドロキシ−6−メチルフェニル)メチル]−4−メチルフェノール、2,6−ビス[(2,4−ジヒドロキシ−3−メチルフェニル)メチル]−4−メチルフェノール、2,6−ビス[(2,4−ジヒドロキシ−5−メチルフェニル)メチル]−4−メチルフェノール、2,6−ビス[(3−ヘキシル−4,6−ジヒドロキシフェニル)メチル]−4−メチルフェノール、2,6−ビス[(3−クロロ−4,6−ジヒドロキシフェニル)メチル]−4−メチルフェノール、4,6−ビス[(4−ヒドロキシフェニル)メチル]−2−メチルフェノール、4,6−ビス[(4−ヒドロキシ−3−メチルフェニル)メチル]−2−メチルフェノール、4,6−ビス[(2,4−ジヒドロキシフェニル)メチル]−2−メチルフェノール、4,6−ビス[(3,4−ジヒドロキシフェニル)メチル]−2−メチルフェノール、4,6−ビス[(2,5−ジヒドロキシフェニル)メチル]−2−メチルフェノール、4,6−ビス[(2,3,4−トリヒドロキシフェニル)メチル]−2−メチルフェノール、4,6−ビス[(3,4−ジヒドロキシ−6−メチルフェニル)メチル]−2−メチルフェノール、4,6−ビス[(2,4−ジヒドロキシ−3−メチルフェニル)メチル]−2−メチルフェノール、4,6−ビス[(2,4−ジヒドロキシ−5−メチルフェニル)メチル]−2−メチルフェノール、4,6−ビス[(3−ヘキシル−4,6−ジヒドロキシフェニル)メチル]−2−メチルフェノール、4,6−ビス[(3−クロロ−4,6−ジヒドロキシフェニル)メチル]−2−メチルフェノール、2,6−ビス[(4−ヒドロキシフェニル)メチル]−4−tert−ブチルフェノール、2,6−ビス[(4−ヒドロキシ−3−メチルフェニル)メチル]−4−tert−ブチルフェノール、2,6−ビス[(2,4−ジヒドロキシフェニル)メチル]−4−tert−ブチルフェノール、2,6−ビス[(3,4−ジヒドロキシフェニル)メチル]−4−tert−ブチルフェノール、2,6−ビス[(2,5−ジヒドロキシフェニル)メチル]−4−tert−ブチルフェノール、2,6−ビス[(2,3,4−トリヒドロキシフェニル)メチル]−4−tert−ブチルフェノール、2,6−ビス[(3,4−ジヒドロキシ−6−メチルフェニル)メチル]−4−tert−ブチルフェノール、2,6−ビス[(2,4−ジヒドロキシ−3−メチルフェニル)メチル]−4−tert−ブチルフェノール、2,6−ビス[(2,4−ジヒドロキシ−5−メチルフェニル)メチル]−4−tert−ブチルフェノール、2,6−ビス[(3−ヘキシル−4,6−ジヒドロキシフェニル)メチル]−4−tert−ブチルフェノール、2,6−ビス[(3−クロロ−4,6−ジヒドロキシフェニル)メチル]−4−tert−ブチルフェノール、2,6−ビス[(4−ヒドロキシフェニル)メチル]−4−シクロヘキシルフェノール、2,6−ビス[(4−ヒドロキシ−3−メチルフェニル)メチル]−4−シクロヘキシルフェノール、2,6−ビス[(2,4−ジヒドロキシフェニル)メチル]−4−シクロヘキシルフェノール、2,6−ビス[(3,4−ジヒドロキシフェニル)メチル]−4−シクロヘキシルフェノール、2,6−ビス[(2,5−ジヒドロキシフェニル)メチル]−4−シクロヘキシルフェノール、2,6−ビス[(2,3,4−トリヒドロキシフェニル)メチル]−4−シクロヘキシルフェノール、2,6−ビス[(3,4−ジヒドロキシ−6−メチルフェニル)メチル]−4−シクロヘキシルフェノール、2,6−ビス[(2,4−ジヒドロキシ−3−メチルフェニル)メチル]−4−シクロヘキシルフェノール、2,6−ビス[(2,4−ジヒドロキシ−5−メチルフェニル)メチル]−4−シクロヘキシルフェノール、2,6−ビス[(3−ヘキシル−4,6−ジヒドロキシフェニル)メチル]−4−シクロヘキシルフェノール、2,6−ビス[(3−クロロ−4,6−ジヒドロキシフェニル)メチル]−4−シクロヘキシルフェノール、4,6−ビス[(4−ヒドロキシフェニル)メチル]−2−シクロヘキシルフェノール、4,6−ビス[(4−ヒドロキシ−3−メチルフェニル)メチル]−2−シクロヘキシルフェノール、4,6−ビス[(2,4−ジヒドロキシフェニル)メチル]−2−シクロヘキシルフェノール、4,6−ビス[(3,4−ジヒドロキシフェニル)メチル]−2−シクロヘキシルフェノール、4,6−ビス[(2,5−ジヒドロキシフェニル)メチル]−2−シクロヘキシルフェノール、4,6−ビス[(2,3,4−トリヒドロキシフェニル)メチル]−2−シクロヘキシルフェノール、4,6−ビス[(3,4−ジヒドロキシ−6−メチルフェニル)メチル]−2−シクロヘキシルフェノール、4,6−ビス[(2,4−ジヒドロキシ−3−メチルフェニル)メチル]−2−シクロヘキシルフェノール、4,6−ビス[(2,4−ジヒドロキシ−5−メチルフェニル)メチル]−2−シクロヘキシルフェノール、4,6−ビス[(3−ヘキシル−4,6−ジヒドロキシフェニル)メチル]−2−シクロヘキシルフェノール、4,6−ビス[(3−クロロ−4,6−ジヒドロキシフェニル)メチル]−2−シクロヘキシルフェノール等が挙げられる。
多価フェノール化合物(B)は、例えばフェノール類とアルデヒド類との縮合反応により製造することができる。このような縮合反応は公知であり、酸触媒又は塩基触媒の存在下で行われる。
メチロール化フェノール化合物(C)は、下記式(4)で表される化合物である。
R13及びR14は、それぞれ独立して、水素原子又はアルキル基である。
X2は、アミド基、エーテル基、カルボニル基、キシレニル基、スルフィド基、スルホニル基、ジスルフィド基、シクロアルキレン基、フェニレン基又は下記式(5)で表される基である。
d、e及びgは、それぞれ独立して1又は2である。fは0以上2以下の整数である。mは0以上2以下の整数である。ただし、f及びmは同時に0となることはない。nは0又は1である。また、d、e、f、g及びmは下記式(II)及び(III)を満たす。
2≦d+f+m≦4 (II)
2≦e+g≦3 (III)
Y2は、水素原子、アルキル基、フルオロアルキル基、シクロアルキル基、フェニル基、アダマンチル基又は下記式(6)で表される基である。
ただし、Y2とR15とは互いに結合してシクロアルカン構造又はフルオレン構造を形成していてもよい。
R18は、水素原子、アルキル基、シクロアルキル基、フェニル基又はベンジル基である。
R19は、水素原子又はアルキル基である。
h及びiは、それぞれ独立して0以上2以下の整数であり、下記式(IV)を満たす。
0≦h+i≦3 (IV)
メチロール化フェノール化合物(C)は、例えば上記フェノール類又は上記多価フェノール化合物(B)とホルムアルデヒドとの反応により製造することができる。このような反応は公知であり、塩基触媒の存在下で行われる。
ドーパントは、導電性高分子組成物(X)の導電性を向上させるものである。このドーパントは、導電性高分子化合物(A)を酸化又は還元し得るものであるため、導電性高分子化合物(A)を構成する共役系高分子の溶媒への分散性が向上する。導電層は、塗布、乾燥等により形成されることが多いため、溶媒への共役系高分子の分散性が向上することで、均一な導電性を有する導電層を形成することが可能となる。
溶媒は、導電性高分子組成物(X)中に導電性高分子化合物(A)を溶解又は分散させ、かつ多価フェノール化合物及びメチロール化フェノール化合物(C)を溶解させる。
上記ケトン類としては、例えばアセトン等が挙げられる。
上記エチレングリコール類としては、例えばエチレングリコールメチルエーテル等が挙げられる。
上記プロピレングリコール類としては、例えばプロピレングリコールメチルエーテル、プロピレングリコールエチルエーテル、プロピレングリコールブチルエーテル、プロピレングリコールプロピルエーテル等が挙げられる。
上記アミド類としては、例えばN,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド等が挙げられる。
上記ピロリドン類としては、例えばN−メチルピロリドン、N−エチルピロリドン等が挙げられる。
バインダー樹脂は、導電性高分子組成物(X)から形成される導電層の耐傷性、表面硬度等を高める。また、バインダー樹脂は、導電層を基材の表面等に形成する場合において、導電層と基材の密着性を向上させ得る。
架橋剤は、導電性高分子化合物(A)等を架橋でき、その結果、得られる当該導電層の耐傷性、硬度及び基材に対する密着性を向上させることができる。また、架橋により安定性に優れた導電層が形成されることで、導電層の導電性も向上する場合がある。
当該導電性高分子組成物(X)が有してもよいその他の任意成分としては、例えば導電性向上成分、界面活性剤、増粘剤、染料、硬化触媒、レオロジーコントロール剤、樹脂微粒子、無機微粒子、シランカップリング剤、消泡剤、表面調整剤、紫外線吸収剤、酸化防止剤、防腐剤、防カビ剤、可塑剤等が挙げられる。
当該導電性高分子組成物(X)は、導電性高分子化合物(A)、多価フェノール化合物(B)、メチロール化フェノール化合物(C)、必要に応じてドーパント、バインダー樹脂、架橋剤等を任意の順序で溶媒と混合することにより製造できる。各成分の混合には公知の撹拌機を用いることができる。
本発明の導電層は、導電性高分子組成物(X)から形成される。また、本発明の導電体は、当該導電層が複数積層されたものであり、例えば基材の表面等に形成される導電性膜等とすることができる。
導電層10及び11は、当該導電性高分子組成物(X)から形成される。導電層10及び11の平均厚みの上限としては、50μmが好ましく、10μmがより好ましい。一方、上記平均厚みの下限としては、0.01μmが好ましく、0.05μmがより好ましい。上記平均厚みが上記上限を超えると、導電層10及び11の乾燥が不十分となり、強度が低下するおそれがある。逆に、上記平均厚みが上記下限未満の場合、導電層10及び11の抵抗が上昇するおそれがある。
上記基材Zとしては、特に限定されず、用途に応じて適宜選択できる。この基材Zとしては、例えば高分子化合物、木材、紙材、セラミックス、ガラス等が挙げられる。
導電層10及び11の形成方法としては、例えば導電性高分子組成物(X)を基材Zの表面等に塗布する工程、及び塗膜を乾燥する工程を主に備える方法が挙げられる。
図2の配線基板Wは、2つの絶縁層Y1及びY2の間に配線20が形成され、ビア導体23側の絶縁層Y2の表面に配線21及びパッド22が形成されたものである。絶縁層間の配線20とパッド22とはビア導体23を介して導電接続されている。配線20、21、及びパッド22は当該導電性高分子組成物(X)から形成される導電層であり、ビア導体23は導電性高分子組成物(X)から形成される導電体である。
<実施例1>
多価フェノール化合物(成分(B))0.239g、メチロール化フェノール化合物(成分(C))0.161gを溶媒20.800g(水5.200g及びイソプロピルアルコール15.600gの混合溶媒)に加え、25℃で溶解させた。その後導電性高分子化合物(成分(A))の水分散液30.769g(成分(A)の含有量0.400g)を加えて室温で混合することで導電性高分子組成物を調製した。成分(B)及び成分(C)としては、後述する(B−1)及び(C−1)を用いた。
成分(B)、成分(C)、架橋剤及び硬化触媒として表1に示す成分を用い、各成分の使用量を表1に記載の通りとした他は、実施例1と同様に導電性高分子組成物を調製した。実施例及び比較例で用いた化合物を以下に示す。
導電性高分子化合物(A)としては、ポリ(4−スチレンスルホン酸)をドープしたポリ(3,4−エチレンジオキシチオフェン)(アルドリッチ社の「PEDOT/PSS 1.3wt%dispersion in H2O,conductive grade(製品番号:483095)」)を用いた。
PEDOT/PSSのモル数(mol)=PEDOT含有量(g)/PEDOT最小単位の分子量142(g/mol)
実施例において用いた多価フェノール化合物を以下に示す。
B−1:ビス(4−ヒドロキシフェニル)スルホン(小西化学工業社の「BS−PN」、分子量250)
B−2:ビス(4−ヒドロキシフェニル)エーテル(酒井興業社の「P−O−P」、分子量202)
B−3:ビス(3,4−ジヒドロキシ−6−メチルフェニル)メタン(旭有機材工業社の「BI4MC−F」、分子量260)
実施例及び比較例において用いたメチロール化フェノール化合物を以下に示す。
C−1:2,6−ジヒドロキシメチル−4−メチルフェノール(旭有機材工業社の「26DMPC」、分子量168)
C−2:2,2−ビス(4−ヒドロキシ−3,5−ジヒドロキシメチルフェニル)プロパン(旭有機材工業社の「TM−BIP−A」、分子量348)
溶媒としては、水とイソプロピルアルコール(和光純薬工業社、沸点82.5℃)(表1中に「IPA」と記載)との混合溶媒を使用した。
実施例において用いた架橋剤を以下に示す。
D−1:ジエチレングリコールジグリシジルエーテル(ナガセケムテックス社の「EX−850L」、エポキシ当量122g/eq)
D−2:トリメチロールプロパントリグリシジルエーテル(坂本薬品工業社の「SR−TMP」、エポキシ当量137g/eq)
硬化触媒としては、2−メチルイミダゾール(四国化成工業社の「2MZ−H」、分子量82)を用いた。
上記実施例及び比較例の導電性高分子組成物500μLを、それぞれ80℃に加温したガラス基材(3.8cm×2.6cm)上に塗布し、80℃にて5分間乾燥した後、さらに140℃で10分間乾燥することにより導電性膜を形成した。
<体積抵抗率>
実施例及び比較例の導電性膜の体積抵抗率は、抵抗率計(三菱化学アナリテック社の「Loresta−GP MCP−T610」)を用いて室温にて測定した。体積抵抗率の計算の際、使用した導電性高分子組成物中の固形分の比重を1g/cm3として導電性膜の厚みを計算した。この結果を表2に示す。
実施例及び比較例の導電性膜の鉛筆硬度はJIS−K5600−5−4:1999に準拠し測定した。引っかき試験後導電層を目視で観察し、導電性膜が塑性変形し永久くぼみが認められる状態を「すり傷」とし、すり傷が生じなかった最も堅い鉛筆の硬度を「すり傷硬度」とした。また、導電性膜が凝集破壊し、一部がガラス基材から剥離した状態又は一部が破壊された状態を「破れ」とし、破れが生じなかった最も堅い鉛筆の硬度を「破れ硬度」とした。この結果を表2に示す。
実施例及び比較例の導電性膜の耐傷付性について、以下の方法で測定した。ペーパータオル(日本製紙クレシア社の「キムワイプ(登録商標)」)に100gf/cm2の荷重をかけ、導電性膜の表面を20往復擦った後、目視により導電性膜の傷を以下の基準に基づいて評価した。この結果を表2に示す。
A:傷なし
B:数10本の傷あり
C:無数の傷あり
10、11 導電層
20、21 配線(導電体の一例)
22 パッド(導電体の一例)
23 ビア導体(導電体の一例)
26 スルーホール
3 ビア導体
30 スルーホール
31 金属層
32 導電体
W 配線基板
Z 基材
Y1、Y2 絶縁層
Claims (20)
- 導電性高分子化合物、下記式(1)で表される多価フェノール化合物及び下記式(4)で表されるメチロール化フェノール化合物を含有し、熱により硬化し得る導電性高分子組成物。
X1は、アミド基、エーテル基、カルボニル基、キシレニル基、スルフィド基、スルホニル基、ジスルフィド基、シクロアルキレン基、フェニレン基又は下記式(2)で表される基である。
a及びbは、それぞれ独立して1以上3以下の整数である。kは、1以上3以下の整数である。jは1又は2である。また、a及びkは、下記式(I)を満たす。)
2≦a+k≦4 (I)
Y1は、水素原子、アルキル基、フルオロアルキル基、シクロアルキル基、フェニル基、アダマンチル基又は下記式(3)で表される基である。
ただし、Y1とR5とは互いに結合してシクロアルカン構造又はフルオレン構造を形成していてもよい。)
R8は、水素原子、アルキル基、シクロアルキル基、フェニル基又はベンジル基である。
cは、0以上3以下の整数である。)
R13及びR14は、それぞれ独立して、水素原子又はアルキル基である。
X2は、アミド基、エーテル基、カルボニル基、キシレニル基、スルフィド基、スルホニル基、ジスルフィド基、シクロアルキレン基、フェニレン基又は下記式(5)で表される基である。
d、e及びgは、それぞれ独立して1又は2である。fは0以上2以下の整数である。mは0以上2以下の整数である。ただし、f及びmは同時に0となることはない。nは0又は1である。また、d、e、f、g及びmは、下記式(II)及び(III)を満たす。)
2≦d+f+m≦4 (II)
2≦e+g≦3 (III)
Y2は、水素原子、アルキル基、フルオロアルキル基、シクロアルキル基、フェニル基、アダマンチル基又は下記式(6)で表される基である。
ただし、Y2とR15とは互いに結合してシクロアルカン構造又はフルオレン構造を形成していてもよい。)
R18は、水素原子、アルキル基、シクロアルキル基、フェニル基又はベンジル基である。
R19は、水素原子又はアルキル基である。
h及びiは、それぞれ独立して0以上2以下の整数であり、下記式(IV)を満たす。)
0≦h+i≦3 (IV) - 上記式(1)におけるa及びbが1又は2であり、かつkが1である請求項1に記載の導電性高分子組成物。
- 上記式(4)におけるfが1又は2であり、かつmが0又は1である請求項1に記載の導電性高分子組成物。
- 上記式(4)において、mが0の場合にfが2であるか、若しくはmが1の場合にfが1又は2である請求項2に記載の導電性高分子組成物。
- 上記式(1)におけるR1〜R4が、それぞれ独立して、水素原子、アルキル基又はアルコキシ基であり、X1が、エーテル基、カルボニル基、スルフィド基、スルホニル基又は上記式(2)で表される基であり、
上記式(2)におけるR5が、水素原子、アルキル基又はフルオロアルキル基であり、Y1が、水素原子、アルキル基、フルオロアルキル基又は上記式(3)で表される基であり、
上記式(3)におけるR6〜R8が、それぞれ独立して、水素原子又はアルキル基であり、cが、0以上2以下であり、
上記式(4)におけるR9〜R12が、それぞれ独立して、水素原子、アルキル基又はアルコキシ基であり、X2が、エーテル基、カルボニル基、スルフィド基、スルホニル基又は上記式(5)で表される基であり、
上記式(5)におけるR15が、水素原子、アルキル基又はフルオロアルキル基であり、Y2が、水素原子、アルキル基、フルオロアルキル基又は上記式(6)で表される基であり、
上記式(6)におけるR16〜R19が、それぞれ独立して、水素原子又はアルキル基である請求項1から請求項4のいずれか1項に記載の導電性高分子組成物。 - 上記導電性高分子化合物を酸化又は還元し得るドーパントをさらに含有する請求項1から請求項10のいずれか1項に記載の導電性高分子組成物。
- 上記導電性高分子化合物がポリチオフェン又はその誘導体であり、上記ドーパントが有機スルホン酸、有機スルホン酸金属塩又は有機スルホン酸アニオンである請求項11に記載の導電性高分子組成物。
- 上記導電性高分子化合物がポリ(3,4−エチレンジオキシチオフェン)であり、上記ドーパントがポリ(4−スチレンスルホン酸)である請求項12に記載の導電性高分子組成物。
- 溶媒をさらに含有し、上記溶媒が水及びアルコールの混合溶媒である請求項1から請求項13のいずれか1項に記載の導電性高分子組成物。
- バインダー樹脂をさらに含有する請求項1から請求項14のいずれか1項に記載の導電性高分子組成物。
- 架橋剤をさらに含有し、この架橋剤がエポキシ化合物又はオキセタン化合物である請求項1から請求項15のいずれか1項に記載の導電性高分子組成物。
- 請求項1から請求項16のいずれか1項に記載の導電性高分子組成物から形成される導電層。
- 加熱硬化することにより形成される請求項17に記載の導電層。
- 請求項17又は請求項18に記載の導電層が複数積層された導電体。
- 導電性膜である請求項19に記載の導電体。
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