JPWO2016059972A1 - 有機半導体組成物、光起電力素子、光電変換デバイスおよび光起電力素子の製造方法 - Google Patents
有機半導体組成物、光起電力素子、光電変換デバイスおよび光起電力素子の製造方法 Download PDFInfo
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- JPWO2016059972A1 JPWO2016059972A1 JP2015549876A JP2015549876A JPWO2016059972A1 JP WO2016059972 A1 JPWO2016059972 A1 JP WO2016059972A1 JP 2015549876 A JP2015549876 A JP 2015549876A JP 2015549876 A JP2015549876 A JP 2015549876A JP WO2016059972 A1 JPWO2016059972 A1 JP WO2016059972A1
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- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
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- YJBKVPRVZAQTPY-UHFFFAOYSA-J tetrachlorostannane;dihydrate Chemical compound O.O.Cl[Sn](Cl)(Cl)Cl YJBKVPRVZAQTPY-UHFFFAOYSA-J 0.000 description 1
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- 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
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
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- 239000010936 titanium Substances 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- MLCPSWPIYHDOKG-BUHFOSPRSA-N trans-isoindigo Natural products O=C\1NC2=CC=CC=C2C/1=C1/C2=CC=CC=C2NC1=O MLCPSWPIYHDOKG-BUHFOSPRSA-N 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 1
- UKTDFYOZPFNQOQ-UHFFFAOYSA-N tributyl(thiophen-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CS1 UKTDFYOZPFNQOQ-UHFFFAOYSA-N 0.000 description 1
- 229940030010 trimethoxybenzene Drugs 0.000 description 1
- SZEMGTQCPRNXEG-UHFFFAOYSA-M trimethyl(octadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C SZEMGTQCPRNXEG-UHFFFAOYSA-M 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
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- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- SRWMQSFFRFWREA-UHFFFAOYSA-M zinc formate Chemical compound [Zn+2].[O-]C=O SRWMQSFFRFWREA-UHFFFAOYSA-M 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- WDHVIZKSFZNHJB-UHFFFAOYSA-L zinc;butanoate Chemical compound [Zn+2].CCCC([O-])=O.CCCC([O-])=O WDHVIZKSFZNHJB-UHFFFAOYSA-L 0.000 description 1
- ZPEJZWGMHAKWNL-UHFFFAOYSA-L zinc;oxalate Chemical compound [Zn+2].[O-]C(=O)C([O-])=O ZPEJZWGMHAKWNL-UHFFFAOYSA-L 0.000 description 1
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 description 1
- XDWXRAYGALQIFG-UHFFFAOYSA-L zinc;propanoate Chemical compound [Zn+2].CCC([O-])=O.CCC([O-])=O XDWXRAYGALQIFG-UHFFFAOYSA-L 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/24—Thiols, sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C321/28—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
- C07C49/67—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having two rings, e.g. tetralones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/04—Carbon
- C08K3/045—Fullerenes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/01—Hydrocarbons
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/07—Aldehydes; Ketones
-
- C—CHEMISTRY; METALLURGY
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Abstract
Description
本発明の有機半導体組成物について説明する。
電子供与性有機半導体とは、p型半導体特性を示すか、または正孔輸送性を有する有機化合物であり、これらの特性を有する化合物であれば特に限定されない。p型半導体特性を示すか、または正孔輸送性を有する有機化合物としては、例えば、ポリチオフェン系重合体、2,1,3−ベンゾチアジアゾール−チオフェン系共重合体、キノキサリン−チオフェン系共重合体、チエノチオフェンーベンゾジチオフェン系共重合体、チエノピロールジオン系共重合体、イソインジゴ系共重合体、ジケトピロロピロール系共重合体、ポリ−p−フェニレンビニレン系重合体、ポリ−p−フェニレン系重合体、ポリフルオレン系重合体、ポリピロール系重合体、ポリアニリン系重合体、ポリアセチレン系重合体、ポリチエニレンビニレン系重合体などの共役系重合体、H2フタロシアニン(H2Pc)、銅フタロシアニン(CuPc)、亜鉛フタロシアニン(ZnPc)等のフタロシアニン誘導体、ポルフィリン誘導体、N,N’−ジフェニル−N,N’−ジ(3−メチルフェニル)−4,4’−ジフェニル−1,1’−ジアミン(TPD)、N,N’−ジナフチル−N,N’−ジフェニル−4,4’−ジフェニル−1,1’−ジアミン(NPD)等のトリアリールアミン誘導体、4,4’−ジ(カルバゾール−9−イル)ビフェニル(CBP)等のカルバゾール誘導体、オリゴチオフェン誘導体(ターチオフェン、クウォーターチオフェン、セキシチオフェン、オクチチオフェンなど)等の低分子有機化合物などが挙げられる。これらを2種以上用いてもよい。
(上記一般式(5)中、R5はアルコキシカルボニル基またはアルカノイル基を表す。Yは水素原子またはハロゲンを表す。)
(上記一般式(6)中、R6はアルキル基、置換されていてもよいヘテロアリール基または置換されていてもよいアリール基を示す。)
上記の骨格構造を有する共役系重合体の中でも、広い光吸収波長領域と深いHOMO準位を有することから高い光起電力特性が得られる下記一般式(7)で表される共役系重合体が本発明の組成物の電子供与性有機半導体としてより好ましい。
〔電子受容性有機半導体〕
電子受容性有機半導体とは、n型半導体特性を示すか、または電子輸送性を有する有機化合物であり、これらの特性を有する化合物であれば特に限定されない。n型半導体特性を示すか、または電子輸送性を有する有機物としては、例えば、1,4,5,8−ナフタレンテトラカルボキシリックジアンハイドライド、N,N'−ジオクチル−3,4,9,10−ナフチルテトラカルボキシジイミド、ペリレン誘導体(3,4,9,10−ペリレンテトラカルボキシリックジアンハイドライド、ペリレンジイミド誘導体、ペリレンジイミド2量体、ペリレンジイミド重合体など)、オキサゾール誘導体(2−(4−ビフェニリル)−5−(4−t−ブチルフェニル)−1,3,4−オキサジアゾール、2,5−ジ(1−ナフチル)−1,3,4−オキサジアゾール等)、トリアゾール誘導体(3−(4−ビフェニリル)−4−フェニル−5−(4−t−ブチルフェニル)−1,2,4−トリアゾール等)、フェナントロリン誘導体、フラーレン誘導体、カーボンナノチューブ、ポリ−p−フェニレンビニレン系重合体にシアノ基を導入した誘導体(CN−PPV)などが挙げられる。これらを2種以上用いてもよい。中でも、安定でキャリア移動度の高いn型半導体であることから、フラーレン誘導体が好ましく用いられる。
溶媒とは、電子供与性有機半導体と電子受容性有機半導体を溶解または分散させて均一な溶液を与えるものであれば特に限定されない。したがって、電子供与性有機半導体と電子受容性有機半導体の溶解性によって適当な溶媒は異なってくるが、例えば、水、ヘキサン、ヘプタン、オクタン、イソオクタン、ノナン、デカン、シクロヘキサン、デカリン、ビシクロヘキシルなどの脂肪族炭化水素類、メタノール、エタノール、ブタノール、プロパノール、エチレングリコール、グリセリンなどのアルコール類、アセトン、メチルエチルケトン、シクロペンタノン、シクロヘキサノン、イソホロンなどのケトン類、酢酸エチル、酢酸ブチル、乳酸メチル、γ−ブチロラクトン、ジエチレングリコールモノブチルエーテルアセテート、ジメチルカーボネートなどのエステル類、エチルエーテル、メチルターシャリーブチルエーテル、テトラヒドロフラン、1,4−ジオキサン、テトラヒドロピラン、3,4−ジヒドロ−2H−ピラン、イソクロマン、エチレングリコールモノメチルエーテル、ジグリムなどのエーテル類、アンモニア、エタノールアミンなどのアミン類、N,N−ジメチルホルムアミド、ジメチルアセトアミド、N−メチル−2−ピロリドンなどのアミド類、スルホランなどのスルホン類、ジメチルスルホキシドなどのスルホキシド類、二硫化炭素、1,8−オクタンジチオールなどのチオール類、アセトニトリル、アクリロニトリルなどのニトリル類、酢酸、乳酸などの脂肪酸類、フラン、チオフェン、ピロール、ピリジンなどの複素環式化合物類、ベンゼン、トルエン、キシレン、エチルベンゼン、クメン、n−ブチルベンゼン、sec−ブチルベンゼン、tert−ブチルベンゼン、スチレン、メシチレン、1,2,4−トリメチルベンゼン、p−シメン、シクロヘキシルベンゼン、ジエチルベンゼン、ペンチルベンゼン、ジペンチルベンゼン、ドデシルベンゼン、エチニルベンゼン、テトラリン、アニソール、フェネトール、ブチルフェニルエーテル、ペンチルフェニルエーテル、1,2−ジメトキシベンゼン、1,3−ジメトキシベンゼン、1,2,4−トリメトキシベンゼン、2−メトキシトルエン、2,5−ジメチルアニソール、o−クロロフェノール、クロロベンゼン、ジクロロベンゼン、トリクロロベンゼン、1−クロロナフタレン、1−ブロモナフタレン、1−メチルナフタレン、o−ジヨードベンゼン、アセトフェノン、2,3−ベンゾフラン、2,3−ジヒドロベンゾフラン、1,4−ベンゾジオキサン、酢酸フェニル、安息香酸メチル、クレゾール、アニリン、ニトロベンゼンなどの芳香族炭化水素類、ジクロロメタン、1,2−ジクロロエチレン、トリクロロエチレン、テトラクロロエチレン、クロロホルム、四塩化炭素、ジクロロエタン、トリクロロエタン、1,3−ジクロロプロパン、1,1,1,2―テトラクロロエタン、1,1,1,3−テトラクロロプロパン、1,2,2,3−テトラクロロプロパン、1,1,2,3−テトラクロロプロパン、ペンタクロロプロパン、ヘキサクロロプロパン、ヘプタクロロプロパン、1−ブロモプロパン、1,2−ジブロモプロパン、2,2−ジブロモプロパン、1,3−ジブロモプロパン、1,2,3−トリブロモプロパン、1,4−ジブロモブタン、1,5−ジブロモペンタン、1,6−ジブロモヘキサン、1,7−ジブロモヘプタン、1,8−ジブロモオクタン、1−ヨードプロパン、1,3−ジヨードプロパン、1,4−ジヨードブタン、1,5−ジヨードペンタン、1,6−ジヨードヘキサン、1,7−ジヨードヘプタン、1,8−ジヨードオクタンなどのハロゲン炭化水素類などが挙げられる。
本発明の有機半導体組成物に含まれる添加剤は、下記一般式(1)〜(3)のいずれかで表される化合物からなる群より選択される1または2以上の化合物である。
(上記一般式(2)中、Bは任意の二環芳香族炭化水素基または二環ヘテロ芳香族基を示す。nは1以上の自然数である。R2は、Bに任意の位置で結合しているn個の置換基であり、それぞれ同じでも異なっていてもよく、アルキル基、アルコキシ基、アルカノイル基またはチオアルキル基を示す。また、R2の内、少なくとも、1つはアルコキシ基、アルカノイル基またはチオアルキル基のいずれかである。また、複数のR2が結合して環を形成していてもよい。)
(上記一般式(3)中、Cは任意の一環芳香族炭化水素基または一環ヘテロ芳香族基を示す。nは1以上の自然数である。R3は、Cに任意の位置で結合しているn個の置換基であり、それぞれ同じでも異なっていてもよく、アルキル基、アルコキシ基、アルカノイル基またはチオアルキル基を示す。また、R3の内、少なくとも1つはチオアルキル基である。また、複数のR3が結合して環を形成していてもよい。)
一般式(1)中、Aは任意の一環芳香族炭化水素基または一環ヘテロ芳香族基であり、これらの例としては、ベンゼン環、チオフェン環、ピリジン環、ピリミジン環、ピリダシン環、ピラジン環、トリアジン環、フラン環、ピロール環、イミダゾール環、ピラゾール環、オキサゾール環、イソオキサゾール環、チアゾール環、イソチアゾール環などが挙げられる。Aが一環芳香族炭化水素基または一環ヘテロ芳香族基であることにより、共役系材料であることが多い電子受容性有機半導体との親和性が高まる。これらの環構造の中でも、安定性の観点や、汎用的で扱いやすい点などから、Aとしてはベンゼン環が好ましい。
次に、本発明の光起電力素子について説明する。
次に本発明の有機半導体組成物および光起電力素子の製造方法について例を挙げて説明する。
Isc:短絡電流密度
Voc:開放電圧
FF:フィルファクター
η:光電変換効率
ITO:インジウム錫酸化物
[70]PCBM:フェニル C71 ブチリックアシッドメチルエステル
各実施例・比較例における光電変換効率は、次式により求めた。
η(%)=Isc(mA/cm2)×Voc(V)×FF/照射光強度(mW/cm2)×100
FF=JVmax/(Isc(mA/cm2)×Voc(V))
JVmax(mW/cm2)は、印加電圧が0Vから開放電圧までの間で電流密度と印加電圧の積が最大となる点における電流密度と印加電圧の積の値である。
化合物A−1を式1に示す方法で合成した。なお、合成例1記載の化合物(1−i)はジャーナルオブザアメリカンケミカルソサエティ(Journal of the American Chemical Society)、2009年、131巻、7792−7799頁に記載されている方法を参考に、化合物(1−p)はアンゲバンテケミ インターナショナルエディション(Angewandte Chem Internatioal Edition)、2011年、50巻、9697−9702頁に記載されている方法を参考にして合成した。
1H−NMR(270MHz,CDCl3):7.71(s,1H),4.79(s,1H),4.59(s,1H),3.88(s,3H)ppm。
1H−NMR(270MHz,CDCl3):7.48(s,1H),4.19(t,J=3.0Hz,2H),4.05(t,J=3.0Hz,2H),3.87(s,3H)ppm。
1H−NMR(270MHz,DMSO−d6):7.46(s,1H),4.18(t,J=3.2Hz,2H),4.01(t,J=3.2Hz,2H)ppm。
1H−NMR(270MHz,DMSO−d6):13.31(brs,1H),4.20(t,J=3.0Hz,2H),4.03(t,J=3.0Hz,2H)ppm。
1H−NMR(270MHz,CDCl3):4.27(t,J=6.7Hz,2H),4.16(t,J=3.0Hz,2H),4.01(t,J=3.0Hz,2H),1.72(m,2H),1.5−1.3(m,12H),0.88(t,J=7.0Hz,3H)ppm。
1H−NMR(270MHz,CDCl3):7.65(d,J=2.7Hz,1H),7.28(dd,J=2.7Hz and 5.4Hz,1H),4.31(t,J=6.8Hz,2H),1.75(m,2H),1.42−1.29(m,12H),0.89(t,J=6.8Hz,3H)ppm。
1H−NMR(270MHz,CDCl3):4.32(t,J=6.5Hz,2H),1.75(m,2H),1.42−1.29(m,12H),0.89(t,J=6.8Hz,3H)ppm。
1H−NMR(270MHz,CDCl3):7.69(d,J=4.9Hz,2H),7.64(d,J=4.9Hz,2H)ppm。
1H−NMR(270MHz,CDCl3):7.11(d,4.9Hz,1H),6.92(dd,4.9Hz and 3.2Hz,1H),6.76(d,J=3.2Hz,1H),2.76(d,J=6.8Hz,2H),1.62(m,1H),1.4−1.3(m,8H),0.88(m,6H)ppm。
1H−NMR(270MHz,CDCl3):7.63(d,J=5.7Hz,1H),7.45(d,J=5.7Hz,1H),7.29(d,J=3.6Hz,1H),6.88(d,J=3.6Hz,1H),2.86(d,J=7.0Hz,2H),1.70−1.61(m,1H),1.56−1.41(m,8H),0.97−0.89(m,6H)ppm。
1H−NMR(270MHz,CDCl3):7.68(s,2H),7.31(d,J=3.2Hz,2H),6.90(d,J=3.2Hz,2H),2.87(d,J=6.2Hz,4H),1.69(m,2H),1.40−1.30(m,16H),1.0−0.9(m,12H),0.39(s,18H)ppm。
化合物E−1を以下の方法により合成した。
2,3−ジヒドロベンゾフラン(東京化成工業(株)製、添加剤に該当)を2質量%含むクロロホルム溶液(ナカライテスク(株) 製、クロロホルムは溶媒に該当)0.2mLを、A−1(電子供与性有機半導体に該当) 0.9mg、[70]PCBM(ソレーヌ社製、電子供与性有機半導体に該当)1.1mgの入ったサンプル瓶の中に加え、さらに、超音波洗浄機(井内盛栄堂(株)製US−2、出力120W)中で30分間超音波照射することにより溶液Aを得た。
2,3−ジヒドロベンゾフランを3,5−ジメチルアニソール(東京化成工業(株)製)に替えたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は7.47%であった。
2,3−ジヒドロベンゾフランを1−メトキシナフタレン(東京化成工業(株)製)に替えたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は7.69%であった。
2,3−ジヒドロベンゾフランを1,3−ジメトキシベンゼン(東京化成工業(株)製)に替えたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は8.38%であった。
2,3−ジヒドロベンゾフランを1,2−ジメトキシベンゼン(東京化成工業(株)製)に替えたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は8.10%であった。
2,3−ジヒドロベンゾフランを1,4−ベンゾジオキサン(東京化成工業(株)製)に替えたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は8.47%であった。
2,3−ジヒドロベンゾフランを3,4−ジメトキシトルエン(東京化成工業(株)製)に替えたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は8.43%であった。
2,3−ジヒドロベンゾフランを2,5−ジメトキシトルエン(東京化成工業(株)製)に替えたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は8.50%であった。
2,3−ジヒドロベンゾフランを1,2,4−トリメトキシベンゼン(東京化成工業(株)製)に替えたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は8.34%であった。
2,3−ジヒドロベンゾフランを3,4,5−トリメトキシトルエン(東京化成工業(株)製、融点25℃と大気下固体である場合は溶融して使用)に替えたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は8.61%であった。
2,3−ジヒドロベンゾフランを2,4,6−トリメトキシトルエン(Alfa Aesar社製)に替えたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は8.50%であった。
2,3−ジヒドロベンゾフランをα−テトラロン(東京化成工業(株)製)に替えたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は8.10%であった。
2,3−ジヒドロベンゾフランを2質量%含むクロロホルム溶液0.2mLを、1,2,3,5−テトラメトキシベンゼン(アルドリッチ社製)を5質量%含むクロロホルム溶液0.2mLに替えたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は8.26%であった。
2,3−ジヒドロベンゾフランを2質量%含むクロロホルム溶液0.2mLを、4−(メチルチオ)トルエン(東京化成工業(株)製)を5質量%含むクロロホルム溶液0.2mLに替えたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は7.67%であった。
2,3−ジヒドロベンゾフランを2質量%含むクロロホルム溶液0.2mLを、2−メトキシチオアニソール(東京化成工業(株)製)を5質量%含むクロロホルム溶液0.2mLに替えたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は8.36%であった。
2,3−ジヒドロベンゾフランを2質量%含むクロロホルム溶液0.2mLを、チオアニソール(東京化成工業(株)製)を5質量%含むクロロホルム溶液0.2mLに替えたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は8.45%であった。
2,3−ジヒドロベンゾフランを2質量%含むクロロホルム溶液0.2mLを、エチルフェニルスルフィド(東京化成工業(株)製)を5質量%含むクロロホルム溶液0.2mLに替えたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は8.27%であった。
3,4,5−トリメトキシトルエン(東京化成工業(株)製)を5質量%含むクロロベンゼン溶液(和光純薬工業(株) 製)0.1mLを、A−1 0.9mg、[70]PCBM(ソレーヌ社製)1.1mgの入ったサンプル瓶の中に加え、さらに、超音波洗浄機(井内盛栄堂(株)製US−2、出力120W)中で30分間超音波照射することにより溶液Bを得た。溶液Aに替えて溶液Bを用いたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は8.31%であった。
3,4,5−トリメトキシトルエン(東京化成工業(株)製)を5質量%含むo−ジクロロベンゼン溶媒(和光純薬工業(株) 製)0.1mLを、A−1 1.35mg、[70]PCBM(ソレーヌ社製)1.65mgの入ったサンプル瓶の中に加え、超音波洗浄機(井内盛栄堂(株)製US−2、出力120W)中で30分間超音波照射することにより溶液Cを得た。溶液Aに替えて溶液Cを用いたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は8.30%であった。
3,4,5−トリメトキシトルエン(東京化成工業(株)製)を5質量%含むトルエン溶媒(ナカライテスク(株) 製)0.1mLを、A−1 0.9mg、[70]PCBM(ソレーヌ社製)1.1mgの入ったサンプル瓶の中に加え、超音波洗浄機(井内盛栄堂(株)製US−2、出力120W)中で30分間超音波照射することにより溶液Dを得た。溶液Aに替えて溶液Dを用いたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は8.21%であった。
3,4,5−トリメトキシトルエン(東京化成工業(株)製)を5質量%含むo−キシレン溶媒(東京化成工業(株)製)0.1mLを、A−1 0.9mg、[70]PCBM(ソレーヌ社製)1.1mgの入ったサンプル瓶の中に加え、超音波洗浄機(井内盛栄堂(株)製US−2、出力120W)中で30分間超音波照射することにより溶液Eを得た。溶液Aに替えて溶液Eを用いたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は8.03%であった。
3,4,5−トリメトキシトルエン(東京化成工業(株)製)を5質量%含む1,3,5−トリメチルベンゼン溶媒(東京化成工業(株)製)0.1mLを、A−1 1.35mg、[70]PCBM(ソレーヌ社製)1.65mgの入ったサンプル瓶の中に加え、超音波洗浄機(井内盛栄堂(株)製US−2、出力120W)中で30分間超音波照射することにより溶液Fを得た。溶液Aに替えて溶液Fを用いたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は7.80%であった。
2,3−ジヒドロベンゾフランを用いなかったほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は4.45%であった。
2,3−ジヒドロベンゾフランを1,8−ジヨードオクタン(東京化成工業(株)製)に替え、加熱乾燥を減圧乾燥に替えたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は8.31%であった。
2,3−ジヒドロベンゾフランをトルエン(東京化成工業(株)製)に替えたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は2.78%であった。
2,3−ジヒドロベンゾフランをアニソール(東京化成工業(株)製)に替えたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は2.78%であった。
2,3−ジヒドロベンゾフランを1,2,3,4−テトラヒドロナフタレン(東京化成工業(株)製)に替えたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は6.93%であった。
2,3−ジヒドロベンゾフランをインダン(東京化成工業(株)製)に替えたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は5.19%であった。
2,3−ジヒドロベンゾフランを1−メチルナフタレン(東京化成工業(株)製)に替えたほかは実施例1と全く同様にして光起電力素子を作製・測定し、光電変換効率を算出した結果、光電変換効率(η)は6.27%であった。
バソクプロイン5nmおよびフッ化リチウム層0.1nmをE−1に替え、真空蒸着装置にて抵抗加熱法によってE−1層を5nm蒸着製膜したほかは実施例10と全く同様にして作製した光起電力素子を窒素雰囲気のグローブボックス中に移し、光起電力素子側にガラス板をエポキシ樹脂で接着することによって封止した。
バソクプロイン5nmおよびフッ化リチウム層0.1nmをE−1に替え、真空蒸着装置にて抵抗加熱法によってE−1層を5nm蒸着製膜したほかは比較例2と全く同様にして作製した光起電力素子を窒素雰囲気のグローブボックス中に移し、光起電力素子側にガラス板をエポキシ樹脂で接着することによって封止した。
3,4,5−トリメトキシトルエンを5質量%含むクロロホルム溶液1.0mLを、A−1 9mg、[70]PCBM 11mgの入ったサンプル瓶の中に加え、さらに、超音波洗浄機中で30分間超音波照射することにより溶液Bを得た。
2 陽極
3 正孔取出し層
4 光電変換層
5 電子取出し極
6 陰極
Claims (12)
- 電子供与性有機半導体、電子受容性有機半導体、溶媒および該溶媒よりも沸点の高い添加剤を含み、該添加剤が、下記一般式(1)〜(3)のいずれかで表される化合物からなる群より選択される1または2以上の化合物である有機半導体組成物。
(上記一般式(2)中、Bは任意の二環芳香族炭化水素基または二環ヘテロ芳香族基を示す。nは1以上の自然数である。R2は、Bに任意の位置で結合しているn個の置換基であり、それぞれ同じでも異なっていてもよく、アルキル基、アルコキシ基、アルカノイル基またはチオアルキル基を示す。また、R2の内、少なくとも、1つはアルコキシ基、アルカノイル基またはチオアルキル基のいずれかである。また、複数のR2が結合して環を形成していてもよい。)
(上記一般式(3)中、Cは任意の一環芳香族炭化水素基または一環ヘテロ芳香族基を示す。nは1以上の自然数である。R3は、Cに任意の位置で結合しているn個の置換基であり、それぞれ同じでも異なっていてもよく、アルキル基、アルコキシ基、アルカノイル基またはチオアルキル基を示す。また、R3の内、少なくとも1つはチオアルキル基である。また、複数のR3が結合して環を形成していてもよい。) - 前記添加剤が、前記一般式(1)中Aがベンゼン環である化合物、前記一般式(2)中Bがナフタレン環である化合物または前記一般式(3)中Cがベンゼン環である化合物である、請求項1に記載の有機半導体組成物。
- 前記添加剤が、前記一般式(1)中2つ以上のR1がアルコキシ基である化合物または前記一般式(1)中少なくとも2つのR1がアルカノイル基とアルキル基であって環を形成している化合物である、請求項1または2に記載の有機半導体組成物。
- 前記添加剤が、前記一般式(1)中nが3以上であり、3つ以上のR1がアルコキシ基である化合物である、請求項3に記載の有機半導体組成物。
- 前記添加剤が、前記一般式(3)中nが1で、R3がチオアルキル基である化合物である、請求項1または2に記載の有機半導体組成物。
- 前記添加剤が、前記一般式(3)中nが2以上で、少なくとも1つ以上のR3がアルコキシ基である化合物である、請求項1または2に記載の有機半導体組成物。
- 前記電子受容性有機半導体がフラーレン化合物である、請求項1〜6のいずれかに記載の有機半導体組成物。
- 前記電子供与性有機半導体が下記一般式(4)〜(6)のいずれかで表される骨格を有する共役系重合体を含む、請求項1〜7のいずれかに記載の有機半導体組成物。
(上記一般式(5)中、R5はアルコキシカルボニル基またはアルカノイル基を表す。Yは水素原子またはハロゲンを表す。)
(上記一般式(6)中、R6はアルキル基、置換されていてもよいヘテロアリール基または置換されていてもよいアリール基を示す。) - 陽極と、陰極と、該陽極と該陰極の間に形成された、請求項1〜9のいずれかに記載の有機半導体組成物を乾燥させてなる光電変換層とを有する光起電力素子。
- 請求項10に記載の光起電力素子を用いてなる光電変換デバイス。
- 陽極と、陰極と、該陽極と該陰極の間に形成された光電変換層とを有する光起電力素子の製造方法であって、請求項1〜9のいずれかに記載の有機半導体組成物の塗布乾燥により前記光電変換層を形成することを特徴とする光起電力素子の製造方法。
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