JP2013185077A - 高分子化合物、それを用いた有機半導体材料、有機トランジスタ及び有機太陽電池 - Google Patents
高分子化合物、それを用いた有機半導体材料、有機トランジスタ及び有機太陽電池 Download PDFInfo
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- JP2013185077A JP2013185077A JP2012051578A JP2012051578A JP2013185077A JP 2013185077 A JP2013185077 A JP 2013185077A JP 2012051578 A JP2012051578 A JP 2012051578A JP 2012051578 A JP2012051578 A JP 2012051578A JP 2013185077 A JP2013185077 A JP 2013185077A
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 67
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- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 1
- 229920001665 Poly-4-vinylphenol Polymers 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
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- 238000010521 absorption reaction Methods 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-O butylazanium Chemical compound CCCC[NH3+] HQABUPZFAYXKJW-UHFFFAOYSA-O 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
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- 229920001577 copolymer Polymers 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- PFLORXVMVNHPEC-UHFFFAOYSA-N diphenyl-(2,3,4-trimethylphenyl)phosphane Chemical compound CC1=C(C)C(C)=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 PFLORXVMVNHPEC-UHFFFAOYSA-N 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 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
- 239000003999 initiator Substances 0.000 description 1
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
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- 239000011368 organic material Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000005005 perfluorohexyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
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- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
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- 239000004926 polymethyl methacrylate Substances 0.000 description 1
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- 229920005591 polysilicon Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012552 review 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
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical class S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
- 238000004381 surface treatment Methods 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
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- FMYXZXAKZWIOHO-UHFFFAOYSA-N trichloro(2-phenylethyl)silane Chemical compound Cl[Si](Cl)(Cl)CCC1=CC=CC=C1 FMYXZXAKZWIOHO-UHFFFAOYSA-N 0.000 description 1
- RCHUVCPBWWSUMC-UHFFFAOYSA-N trichloro(octyl)silane Chemical compound CCCCCCCC[Si](Cl)(Cl)Cl RCHUVCPBWWSUMC-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
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Images
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- 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
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- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Thin Film Transistor (AREA)
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Abstract
【解決手段】次の(1)及び(2)を繰り返し単位として有する高分子化合物。(1)ベンゼン核の対称位置で2個のチオフェン系化合物が点対称の向きで縮合している化合物からなる繰り返し単位、(2)1,4位にカルボニル基を有する6員環化合物誘導体又は1,3位にカルボニル基を有する5員環化合物誘導体等が特定の位置でチオフェン系化合物又はフラン系化合物又はピロール系化合物又はフェニレン系化合物等に縮合している化合物からなる繰り返し単位。
【選択図】なし
Description
[式中、
Ar1は、芳香環又は芳香族複素環を示す。
E1及びE2は、それぞれ独立に、酸素原子、硫黄原子、=C(A1)2で表される基又は=N(A2)で表される基を示し、A1及びA2は、それぞれ独立に、シアノ基、ニトロ基、−CORA又は−CO2RBを示し、RA及びRBは、それぞれ独立に、水素原子、アルキル基、アリール基又は1価の芳香族複素環基を示し、A1、A2、RA又はRBが複数ある場合、それぞれ同一でも異なっていてもよい。
Zは、式(Z−1)で表される基、式(Z−2)で表される基又は式(Z−3)で表される基を示す。]
[式中、
Ar2は、芳香環又は芳香族複素環を示す。
R1、R2、R3及びR4は、それぞれ独立に、水素原子、アルキル基、アリール基、1価の芳香族複素環基又はハロゲン原子を示す。]
[式中、
R5及びR6は、それぞれ独立に、水素原子、アルキル基、アルコキシ基、アルキルチオ基、アリール基、1価の芳香族複素環基又はハロゲン原子を示す。
Y1及びY2は、それぞれ独立に、窒素原子又は=C(R7)−で表される基を示し、R7は、水素原子、アルキル基、アルコキシ基、アルキルチオ基、アリール基、1価の芳香族複素環基又はハロゲン原子を示す。]
本発明の高分子化合物は、上記式(1)で表される構造単位と、上記式(2)で表される構造単位とを有する。
式(1)で表される構造単位は、高分子化合物中に一種のみ含まれていても二種以上含まれていてもよい。
式(2)で表される構造単位は、高分子化合物中に一種のみ含まれていても二種以上含まれていてもよい。
次に、本発明の高分子化合物の製造方法の好適な実施形態について説明する。
本発明の高分子化合物は、有機半導体材料として用いた場合、例えば、有機半導体素子の有機層の形成材料として用いた場合に、高い電荷輸送性(特に、ホール輸送性)を発揮することができる。有機半導体素子としては、有機トランジスタ、有機太陽電池、有機エレクトロルミネッセンス素子等が挙げられる。本発明の高分子化合物は、中でも、有機トランジスタの電荷輸送材料として特に有用である。
有機半導体素子に適用される有機半導体材料は、本発明の高分子化合物の一種を単独で含むものであってもよく、二種以上を組み合わせて含むものであってもよい。また、有機半導体材料は、本発明の高分子化合物に加え、電荷輸送性を有する低分子化合物又は高分子化合物等の他の成分を更に含んでいてもよい。有機半導体材料が、他の成分を含む場合は、本発明の高分子化合物を30質量%以上含むことが好ましく、50質量%以上含むことがより好ましい。
上述した有機半導体材料を用いた有機トランジスタとしては、ソース電極及びドレイン電極と、これらの電極間の電流経路となり、本発明の高分子化合物を含む活性層(「有機半導体層」ということもある。)と、電流経路を通る電流量を制御するゲート電極とを備えた構成を有するものが挙げられる。このような構成を有する有機トランジスタとしては、電界効果型有機トランジスタ、静電誘導型有機トランジスタ等が挙げられる。
図10は、好適な実施形態に係る有機太陽電池の模式断面図である。図10に示す有機太陽電池200は、基板1と、基板1上に形成された第1の電極7aと、第1の電極7a上に形成された活性層2と、活性層2上に形成された第2の電極7bと、を備える。活性層2は、本発明の高分子化合物を含有する有機薄膜である。本発明の高分子化合物は、優れたホール輸送性を有することからドナー性化合物として機能する。
まず、後述する実験において行った各測定の条件について説明する。核磁気共鳴(NMR)スペクトルは、JEOL(日本電子株式会社)製の商品名JMN−270(1H測定時400MHz)を用いて測定した。ケミカルシフトは百万分率(ppm)で表している。内部標準0ppmには、テトラメチルシラン(TMS)を用いた。結合定数(J)は、ヘルツで示しており、略号s、d、t、q、m及びbrは、それぞれ、一重線(singlet)、二重線(doublet)、三重線(triplet)、四重線(quartet)、多重線(multiplet)及び広幅線(broad)を表す。マイクロウェーブ照射下での反応は、Biotage AB社製のInitiatorTM Ver.2.5を用い、出力400W、2.45GHzで行った。
化合物のゲルパーミエーションクロマトグラフィ(GPC)による精製では、GPCシステムCO−8020(東ソー株式会社製)を用いた。
<化合物Cの合成>
化合物Bを文献(G.barbarella,L.Favaretto,A.Bongini.,J.Org.Chem.,1998,63,5497)に記載の方法で合成した。次いで、反応容器内を窒素ガス雰囲気下とした後、反応容器に化合物A(1g,3.03mmol)、塩化チオニル(SOCl2)(2.16g,18.2mmol)、ジメチルホルムアミド(DMF)(触媒量)を入れて、70℃で1時間攪拌を行った。SOCl2を減圧留去した後、ジクロロメタン(10mL)に溶かして0℃で塩化アルミニウム(AlCl3)、化合物B(1.15g,4.55mmol)の順で加えて2時間攪拌した。その後、シリカゲルカラムクロマトグラフィ(ヘキサン:酢酸エチル=20:1)で分離精製し、黄色の固体(化合物C)を得た(収量:1.23g、収率:74%)。
1H NMR(400MHz,CDCl3):δ(ppm) 3.32(t,4H),1.75−1.69(m,4H),1.43−1.31(m,12H),0.89(t,6H).
<高分子化合物Gの合成>
化合物Fを文献(J.Hou,M−H Park,S.Zhang,Y.Yao,Y. Yang,Macromolecules,2008,41,6012)に記載の方法で合成した。次いで、ふた付き試験管に化合物C(99mg,0.18mmol)、化合物F(140mg,0.18mmol)、Pd2(dba)3(3mg,2%mol)、tri−o−tolylposphine(4mg,2%mol)、toluene(4ml,0.05M)を入れ、ふた付き試験官内の気体をアルゴンガスで置換した後、120oCで2日間反応を行った。再沈殿を行った後、メタノール、ヘキサン、クロロホルムの順にSoxhletで分離精製し、深赤色固体として高分子化合物Gを得た(収量:110mg、収率:73%)。
Mn=25200 PDI=2.1 λmax=539nm(溶液) λmax=580nm(フィルム) Eg=1.91eV
1H NMR(400MHz,CDCl3):δ(ppm) 7.60−7.26(br,2H),4.3(br,4H),3.2(br,4H),1.91−0.87(br,52H).
<高分子化合物Iの合成>
化合物Hを文献(Y.Ie,M.Nitani,H.Tada,Y.Aso,Org.Electron.,2010,11,1740)に記載の方法で合成した。次いで、ふた付き試験管に化合物H(110mg,0.2mmol)、化合物F(160mg, 0.2mmol)、Pd2(dba)3(4mg,2%mol)、tri−o−tolylposphine(5mg, 8%mol)、toluene(4ml,0.05M)を入れ、ふた付き試験管内の気体をアルゴンガスで置換した後、120oCで2日間反応を行った。再沈殿を行った後、メタノール、ヘキサン、クロロホルムの順にSoxhletで分離精製し、深赤色固体として高分子化合物Iを得た(収量:130mg、収率:78%)。
Mn=26100 PDI=1.9 λmax=543nm(溶液) λmax=564nm(フィルム) Eg=1.74eV
1H NMR(400MHz,CDCl3):δ(ppm) 7.82−7.26(br,4H),4.2(br,4H),3.1(br,4H),1.95−0.88(br,52H).
Claims (7)
- 式(1)で表される構造単位と、式(2)で表される構造単位と、を有する高分子化合物。
[式中、
Ar1は、芳香環又は芳香族複素環を示す。
E1及びE2は、それぞれ独立に、酸素原子、硫黄原子、=C(A1)2で表される基又は=N(A2)で表される基を示し、A1及びA2は、それぞれ独立に、シアノ基、ニトロ基、−CORA又は−CO2RBを示し、RA及びRBは、それぞれ独立に、水素原子、アルキル基、アリール基又は1価の芳香族複素環基を示し、A1、A2、RA又はRBが複数ある場合は、それぞれ同一でも異なっていてもよい。
Zは、式(Z−1)で表される基、式(Z−2)で表される基又は式(Z−3)で表される基を示す。]
[式中、
Ar2は、芳香環又は芳香族複素環を示す。
R1、R2、R3及びR4は、それぞれ独立に、水素原子、アルキル基、アリール基、1価の芳香族複素環基又はハロゲン原子を示す。]
[式中、
R5及びR6は、それぞれ独立に、水素原子、アルキル基、アルコキシ基、アルキルチオ基、アリール基、1価の芳香族複素環基又はハロゲン原子を示す。
Y1及びY2は、それぞれ独立に、窒素原子又は=C(R7)−で表される基を示し、R7は、水素原子、アルキル基、アルコキシ基、アルキルチオ基、アリール基、1価の芳香族複素環基又はハロゲン原子を示す。] - 請求項1〜4のいずれか一項に記載の高分子化合物を含む、有機半導体材料。
- ソース電極と、
ドレイン電極と、
前記ソース電極と前記ドレイン電極との間の電流経路となる、請求項5に記載の有機半導体材料を含む活性層と、
前記電流経路を通る電流を制御するゲート電極と、
を備える有機トランジスタ。 - 一対の電極と、
該電極の間に設けられた請求項5に記載の有機半導体材料を含む層と、
を備える有機太陽電池。
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