JPWO2014156773A1 - 芳香族複素環化合物、その製造方法、有機半導体材料及び有機半導体デバイス - Google Patents
芳香族複素環化合物、その製造方法、有機半導体材料及び有機半導体デバイス Download PDFInfo
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- JPWO2014156773A1 JPWO2014156773A1 JP2015508323A JP2015508323A JPWO2014156773A1 JP WO2014156773 A1 JPWO2014156773 A1 JP WO2014156773A1 JP 2015508323 A JP2015508323 A JP 2015508323A JP 2015508323 A JP2015508323 A JP 2015508323A JP WO2014156773 A1 JPWO2014156773 A1 JP WO2014156773A1
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- organic semiconductor
- aromatic heterocyclic
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
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- 239000002798 polar solvent Substances 0.000 description 1
- 229920000301 poly(3-hexylthiophene-2,5-diyl) polymer Polymers 0.000 description 1
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- 239000004926 polymethyl methacrylate Substances 0.000 description 1
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- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
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- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- LNKHTYQPVMAJSF-UHFFFAOYSA-N pyranthrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC3=C(C=CC=C4)C4=CC4=CC=C1C2=C34 LNKHTYQPVMAJSF-UHFFFAOYSA-N 0.000 description 1
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- 125000004076 pyridyl group Chemical group 0.000 description 1
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- KRLLUZSLSSIQKH-UHFFFAOYSA-N pyrrolo[3,2-c]carbazole Chemical compound C12=CC=CC=C2N=C2C1=C1N=CC=C1C=C2 KRLLUZSLSSIQKH-UHFFFAOYSA-N 0.000 description 1
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- 230000035484 reaction time Effects 0.000 description 1
- FMKFBRKHHLWKDB-UHFFFAOYSA-N rubicene Chemical compound C12=CC=CC=C2C2=CC=CC3=C2C1=C1C=CC=C2C4=CC=CC=C4C3=C21 FMKFBRKHHLWKDB-UHFFFAOYSA-N 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
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- 229910002027 silica gel Inorganic materials 0.000 description 1
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- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000002174 soft lithography Methods 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
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- 238000005507 spraying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
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- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
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- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
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- RSNQKPMXXVDJFG-UHFFFAOYSA-N tetrasiloxane Chemical compound [SiH3]O[SiH2]O[SiH2]O[SiH3] RSNQKPMXXVDJFG-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- ALYPESYVXOPFNK-UHFFFAOYSA-N thieno[2',3':4,5]thieno[3,2-b]thieno[2',3':4,5]thieno[2,3-d]thiophene Chemical compound C1=CSC2=C1SC1=C2SC2=C1SC1=C2SC=C1 ALYPESYVXOPFNK-UHFFFAOYSA-N 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- PGXOVVAJURGPLL-UHFFFAOYSA-N trinaphthylene Chemical group C1=CC=C2C=C3C4=CC5=CC=CC=C5C=C4C4=CC5=CC=CC=C5C=C4C3=CC2=C1 PGXOVVAJURGPLL-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- AKQNYQDSIDKVJZ-UHFFFAOYSA-N triphenylsilane Chemical compound C1=CC=CC=C1[SiH](C=1C=CC=CC=1)C1=CC=CC=C1 AKQNYQDSIDKVJZ-UHFFFAOYSA-N 0.000 description 1
- VEDJZFSRVVQBIL-UHFFFAOYSA-N trisilane Chemical compound [SiH3][SiH2][SiH3] VEDJZFSRVVQBIL-UHFFFAOYSA-N 0.000 description 1
- ZQTYRTSKQFQYPQ-UHFFFAOYSA-N trisiloxane Chemical compound [SiH3]O[SiH2]O[SiH3] ZQTYRTSKQFQYPQ-UHFFFAOYSA-N 0.000 description 1
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Abstract
Description
1) Rの少なくとも1つが、水素原子以外の1価の置換基であること。
2) Rの少なくとも1つが、ハロゲン原子、水酸基、置換又は未置換の炭素数1〜30の脂肪族炭化水素基、置換又は未置換の炭素数1〜30のアルコキシ基、アミノ基、炭素数1〜30の置換アミノ基、チオール基、炭素数1〜30の置換スルホニル基、シアノ基、置換又は未置換の炭素数6〜48の芳香族炭化水素基、置換又は未置換の炭素数2〜48の芳香族複素環基、置換又は未置換の炭素数8〜50芳香族炭化水素置換アルキニル基、置換又は未置換の炭素数4〜50の芳香族複素環置換アルキニル基、置換又は未置換の炭素数8〜50の芳香族炭化水素置換アルケニル基、置換又は未置換の炭素数4〜50の芳香族複素環置換アルケニル基、置換又は未置換の炭素数5〜30のアルキルシリルアルキニル基、置換又は未置換の炭素数3〜30のアルキルシリル基、置換又は未置換のケイ素数1〜30のシロキサン基、置換又は未置換のケイ素数1〜30のシロキサンアルキル基、及び置換又は未置換のケイ素数1〜30のポリシラン基からなる群れから選ばれる1価の基であること。
ここで、Rは一般式(1)のRと同意であり、Yは、一般式(7)のX1と反応して、X1-Yとして離脱しX1をRに置換可能とする基である。
一般式(2)で示される芳香族複素環化合物を、芳香族複素環化合物(2)というが、芳香族複素環化合物(1)に含まれるので、芳香族複素環化合物(1)で代表することがある。
一般式(7)において、Xは一般式(1)のXと同意である。X1は、それぞれ独立に、ハロゲン原子、水酸基、-B(OH)2、スルホニル基、トリフルオロメタンスルホナート、ノナフルオロブタンスルホナート、フルオロスルホン酸エステル、トシラートから選ばれる反応性基又は一般式(1)のRを示し、少なくとも1つはR以外の反応性基を示す。e、gは1〜4の整数、f、hは1〜2の整数である。一般式(8)において、Rは一般式(1)のRの1価の基と同意であり、Yは一般式(7)のX1と反応して、X1-Yとして離脱しX1をRに置換可能とする基である。
本発明の有機半導体材料の特性を、図2に示す構成の有機電界効果トランジスタを作成し、評価を行った。まず、約300nmの厚みの熱成長酸化ケイ素層を有するシリコンウェハ(nドープ)を、硫酸−過酸化水素水溶液で洗浄し、イソプロピルアルコールで煮沸した後、乾燥した。得られた熱成長酸化ケイ素層を有するシリコンウェハ(nドープ)上に、化合物(A201)のクロロベンゼン溶液(2Wt%)をスピンコート法により製膜した後80℃で熱処理を行う事により厚さ5 0 n m の化合物(A201)の薄膜を形成した。更に、この膜の表面にマスクを用いて金を蒸着してソースおよびドレイン電極を形成した。ソースおよびドレイン電極は幅100μm、厚さ200nmで、チャネル幅W=2mm、チャネル長L = 50 μm の有機電界効果トランジスタを作製した。
Id=(W/2L)μCi(Vg−Vt)2 (I)
化合物(A201)、(B106)と同様に、(A101)、(A216)、(A218)、(A221)、(A226)、(A501)、(A702)、(A805)を合成した。実施例4において、化合物(A201)のクロロベンゼン溶液(2wt%)の代わりに、(A101)、(A216)、(A218)、(A221)、(A226)、(A501)、(A702)、又は(A805)のクロロベンゼン溶液(2wt%)を用いた他は同様の操作を行い、有機電界効果トランジスタを作製し、得られた素子を実施例4と同様にトランジスタ特性を評価した。結果を表1に示す。
実施例4において、化合物(A201)のクロロベンゼン溶液(2wt%)の代わりに、(B101)、(B106)、(B147)、(B151)、(B166)、又は(B172)のクロロベンゼン溶液(2wt%)を用いた他は同様の操作を行い、有機電界効果トランジスタを作製し、得られた素子を実施例4と同様にトランジスタ特性を評価した。結果を表2に示す。
実施例4において、化合物(A201)のクロロベンゼン溶液(2wt%)の代わりに、下記化合物(H1)のクロロベンゼン溶液(2wt%)を使用した他は同様の操作を行い、有機電界効果トランジスタを作製した。得られた素子を実施例4と同様にトランジスタ特性を評価したところ、電界効果移動度は、1.1×10−2cm2/Vsであった。
Claims (11)
- Rの少なくとも1つが、1価の置換基である請求項1に記載の芳香族複素環化合物。
- 一般式(1)において、Rの少なくとも1つが、ハロゲン原子、水酸基、置換又は未置換の炭素数1〜30の脂肪族炭化水素基、置換又は未置換の炭素数1〜30のアルコキシ基、アミノ基、置換アミノ基、チオール基、置換スルホニル基、シアノ基、置換又は未置換の炭素数6〜48の芳香族炭化水素基、置換又は未置換の炭素数2〜48の芳香族複素環基、置換又は未置換の炭素数8〜50芳香族炭化水素置換アルキニル基、置換又は未置換の炭素数4〜50の芳香族複素環置換アルキニル基、置換又は未置換の炭素数8〜50の芳香族炭化水素置換アルケニル基、置換又は未置換の炭素数4〜50の芳香族複素環置換アルケニル基、置換又は未置換の炭素数5〜30のアルキルシリルアルキニル基、置換又は未置換の炭素数3〜30のアルキルシリル基、置換又は未置換のケイ素数1〜30のシロキサン基、置換又は未置換のケイ素数1〜30のシロキサンアルキル基、及び置換又は未置換のケイ素数1〜30のポリシラン基からなる群れから選ばれる1価の基である請求項1に記載の芳香族複素環化合物。
- 下記一般式(7)で示される芳香族複素環化合物と下記一般式(8)で示される化合物を反応させ、一般式(7)におけるX1をRに置換した化合物とすることを特徴とする請求項2に記載の芳香族複素環化合物の製造方法。
R―Y (8)
ここで、Rは一般式(1)のRと同意であり、Yは一般式(7)のX1と反応して、X1-Yとして離脱してX1をRに置換可能とする基である。 - 請求項1〜4のいずれかに記載の芳香族複素環化合物を含有することを特徴とする有機半導体材料。
- 請求項6に記載の有機半導体材料から形成されたことを特徴とする有機半導体膜。
- 請求項6に記載の有機半導体材料を有機溶媒に溶解し、調製された溶液を塗布・乾燥する工程を経て、形成されたことを特徴とする有機半導体膜。
- 請求項6に記載の有機半導体材料を用いることを特徴とする有機半導体デバイス。
- 請求項6に記載の有機半導体材料を半導体層に用いることを特徴とする有機薄膜トランジスタ。
- 請求項6に記載の有機半導体材料を半導体層に用いることを特徴とする有機光起電力素子。
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