JP6126937B2 - 有機ヘテロ高分子及びそれを用いた半導体デバイス - Google Patents
有機ヘテロ高分子及びそれを用いた半導体デバイス Download PDFInfo
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- JP6126937B2 JP6126937B2 JP2013165967A JP2013165967A JP6126937B2 JP 6126937 B2 JP6126937 B2 JP 6126937B2 JP 2013165967 A JP2013165967 A JP 2013165967A JP 2013165967 A JP2013165967 A JP 2013165967A JP 6126937 B2 JP6126937 B2 JP 6126937B2
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- 239000004065 semiconductor Substances 0.000 title claims description 60
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- 125000005842 heteroatom Chemical group 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 229910052717 sulfur Inorganic materials 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
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- 125000004429 atom Chemical group 0.000 claims description 23
- 229910052751 metal Inorganic materials 0.000 claims description 23
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
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- 238000006243 chemical reaction Methods 0.000 claims description 17
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
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- 150000004791 alkyl magnesium halides Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000002390 heteroarenes Chemical group 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
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- 229910052709 silver Inorganic materials 0.000 description 3
- 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 3
- 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 description 2
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- ISXUHJXWYNONDI-UHFFFAOYSA-L dichloro(diphenyl)stannane Chemical compound C=1C=CC=CC=1[Sn](Cl)(Cl)C1=CC=CC=C1 ISXUHJXWYNONDI-UHFFFAOYSA-L 0.000 description 1
- YFWKSZYIADVCEP-UHFFFAOYSA-N dichloro(octyl)phosphane Chemical compound CCCCCCCCP(Cl)Cl YFWKSZYIADVCEP-UHFFFAOYSA-N 0.000 description 1
- IMDXZWRLUZPMDH-UHFFFAOYSA-N dichlorophenylphosphine Chemical compound ClP(Cl)C1=CC=CC=C1 IMDXZWRLUZPMDH-UHFFFAOYSA-N 0.000 description 1
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- FDWREHZXQUYJFJ-UHFFFAOYSA-M gold monochloride Chemical compound [Cl-].[Au+] FDWREHZXQUYJFJ-UHFFFAOYSA-M 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
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- 150000002576 ketones Chemical class 0.000 description 1
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- RYEXTBOQKFUPOE-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].CC[CH2-] RYEXTBOQKFUPOE-UHFFFAOYSA-M 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- REYCEEFBHWADHV-UHFFFAOYSA-N n-(3,4-dicyanophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C#N)C(C#N)=C1 REYCEEFBHWADHV-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000011574 phosphorus Chemical group 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000005412 pyrazyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- QGKLPGKXAVVPOJ-UHFFFAOYSA-N pyrrolidin-3-one Chemical compound O=C1CCNC1 QGKLPGKXAVVPOJ-UHFFFAOYSA-N 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical compound C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Landscapes
- Electroluminescent Light Sources (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Photovoltaic Devices (AREA)
Description
R1は、アルキル基、シクロアルキル基、アリール基又はヘテロアリール基を示し、
R2は、アルキル基、シクロアルキル基、アリール基、ヘテロアリール基、又は周期表16族(又は6B族)元素及び周期表11族(又は1B族)元素から選択された一価又は二価のヘテロ原子、又は配位子と錯体を形成した金属原子を示し、
m1及びm2はそれぞれ0又は1を示し、m1とm2との合計は1又は2であり、
R3及びR4はそれぞれ独立して水素原子、ハロゲン原子、又は式−Z−R5
(Zは周期表14族(又は4B族)元素、15族(又は5B族)元素又は16族(又は6B族)元素を示し、R5はアリール基又はヘテロアリール基を示す)を示し、
R6a及びR6bは、それぞれ独立して、水素原子、直鎖状又は分岐鎖状アルキル基、直鎖状又は分岐鎖状アルコキシ基、直鎖状又は分岐鎖状アルキルチオ基を示し、R6a及びR6bは互いに結合して環を形成してもよい。
有機ヘテロ高分子は有機半導体を形成するために有用であり、有機半導体用有機ヘテロ高分子(有機金属高分子)ともいうことができる。前記ヘテロ高分子の繰り返し単位は、例えば、下記式(1a)〜(1c)及び(2a)で表すこともできる。
M2は周期表14族(又は4B族)元素、15族(又は5B族)元素又は16族(又は6B族)元素を示し、
R1a、R1b及びR1cは、同一又は異なって、アルキル基、アリール基又はヘテロアリール基を示し、
R2aは周期表16族(又は6B族)元素を示し、
R2bは、アルキル基、アリール基又はヘテロアリール基、周期表11族(又は1B族)元素から選択された金属原子又は配位子と錯体を形成した金属原子を示し、
環Arはアレーン環又はヘテロアレーン環を示し、
R7はそれぞれ直鎖状又は分岐鎖状アルキル基、直鎖状又は分岐鎖状アルコキシ基、直鎖状又は分岐鎖状アルキルチオ基を示し、
Z1及びZ2は同一又は異なって周期表16族(又は6B族)元素を示し、
qは0又は1〜3の整数を示し、
R6a及びR6bは、同一又は異なって、水素原子、直鎖状又は分岐鎖状C1−16アルキル基、直鎖状又は分岐鎖状C1−16アルコキシ基、又は直鎖状又は分岐鎖状C1−16アルキルチオ基を示し、R6a及びR6bの少なくとも一方は水素原子ではなく、R6a及びR6bは、互いに結合して、シクロアルカン環、酸素原子、硫黄原子及び窒素原子から選択された少なくとも1つのヘテロ原子を有するヘテロ環を形成してもよい)
なお、R6a及びR6bは、同一又は異なって、水素原子、直鎖状又は分岐鎖状C4−16アルキル基又は直鎖状又は分岐鎖状C4−16アルコキシ基、直鎖状又は分岐鎖状C4−16アルキルチオ基を示し、R6a及びR6bの少なくとも一方は水素原子ではなく、R6a及びR6bは、互いに結合して、シクロアルカン環、酸素原子、及び硫黄原子から選択された少なくとも1つのヘテロ原子を有する5員乃至8員ヘテロ環を形成してもよい。さらに、R6a及びR6bの少なくとも一方は、直鎖状又は分岐鎖状C4−14アルキル基であるか、若しくはR6a及びR6bは互いに結合してアルキレンジオキシ基を形成してもよい。
前記式(1)又は(2)で表される繰り返し単位において、Mは、周期表14族(又は4B族)元素(例えば、Si、Ge、Sn、Pb)、15族(又は5B族)元素(例えば、N、P、As、Sb、Bi)、16族(又は6B族)元素(例えば、S、Se、Te)から選択された元素(ヘテロ原子)を示す。これらの元素Mのうち、周期表14族元素では、例えば、Si、Ge、Snなど、特にSnが好ましく、15族元素では、例えば、P、As、Sb、Biなどが好ましく、16族元素では、例えば、S、Se、Teなど、特にSe、Teが好ましい。特に、周期表14族元素(Ge、Sn)及び16族元素(Se、Te)が好ましい。これらの元素(ヘテロ原子)の原子価は、通常、元素(ヘテロ原子)の種類に応じて、3〜6価、好ましくは3〜5価である。周期表14族元素(例えば、Sn)は4価である場合が多く、15族元素(例えば、P)は3〜5価である場合が多く、周期表16族元素(例えば、S、Se、Te)は3〜5価である場合が多い。
このような有機ヘテロ高分子は、Synthetic Metals, 159 (2009), 949-951又は有機合成化学協会誌Vol66 No5 2008に記載の方法に準じて合成できる。すなわち、有機ヘテロ高分子は、以下の反応工程式により調製できる。
R8で表されるアルキル基としては、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、s−ブチル基、t−ブチル基などの直鎖状又は分岐鎖状C1−6アルキル基が例示できる。アルキル基R8としては、分岐アルキル基、例えば、イソプロピル基などである場合が多い。Xで表されるハロゲン原子としては、塩素原子、臭素原子などが例示できる。
有機ヘテロ高分子は、チオフェン環と、ヘテロ原子を含む5員環又はジエン単位とで共役系(π−共役系)を形成しており、極めて電子移動度が高く、半導体特性を有している。しかも、アルキル鎖などを導入した有機へテロ高分子は、有機溶媒に対して可溶であり、かつ高い半導体特性を示すという特色がある。そのため、本発明は有機へテロ高分子と有機溶媒とを含む組成物も包含し、この組成物は、有機半導体、特にコーティング(塗布)などにより有機半導体の薄膜を形成するのに有用である。
実施例のポリマーの塩化メチレン溶液(濃度:1mg/ml)を用いて、紫外−可視吸収スペクトル測定を行い、λmax及びλonsetを測定した。なお、λmaxは最大吸収波長(nm)、λonsetは長波長側の吸収端(nm)を意味する。バンドギャップ(BG,eV)は、紫外−可視吸収スペクトルのλonsetから以下の式を用いて算出した。
(式中、Eは電子ボルト(eV)、hはプランク定数(J・s)、cは光の速度(m/s)、eは素電荷(C)、λはλonset波長(nm)を示す)
Claims (9)
- 下記式(1)
R1は、アルキル基、シクロアルキル基、アリール基又はヘテロアリール基を示し、
R2は、アルキル基、シクロアルキル基、アリール基、ヘテロアリール基、又は周期表16族元素及び周期表11族元素から選択された一価又は二価のヘテロ原子又は配位子と錯体を形成した金属原子を示し、
m1及びm2はそれぞれ0又は1を示し、m1とm2との合計は1又は2であり、
R 6a及びR6bは、それぞれ独立して、水素原子、直鎖状又は分岐鎖状アルキル基、直鎖状又は分岐鎖状アルコキシ基、直鎖状又は分岐鎖状アルキルチオ基を示し、R6a及びR6bは互いに結合して環を形成してもよい。)
で表される繰り返し単位を有する有機ヘテロ高分子。 - 下記式(1c)
R 1b は、同一又は異なって、アルキル基、アリール基又はヘテロアリール基を示し、
R 2bは、アルキル基、アリール基又はヘテロアリール基、周期表11族元素から選択された金属原子又は配位子と錯体を形成した金属原子を示し、
R 6a及びR6bは、同一又は異なって、水素原子、直鎖状又は分岐鎖状C1−16アルキル基、直鎖状又は分岐鎖状C1−16アルコキシ基、又は直鎖状又は分岐鎖状C1−16アルキルチオ基を示し、R6a及びR6bの少なくとも一方は水素原子ではなく、R6a及びR6bは、互いに結合して、シクロアルカン環、酸素原子、硫黄原子及び窒素原子から選択された少なくとも1つのヘテロ原子を有するヘテロ環を形成してもよい)
で表される繰り返し単位を有する請求項1記載の有機ヘテロ高分子。 - R6a及びR6bが、同一又は異なって、水素原子、直鎖状又は分岐鎖状C4−16アルキル基又は直鎖状又は分岐鎖状C4−16アルコキシ基、直鎖状又は分岐鎖状C4−16アルキルチオ基を示し、R6a及びR6bの少なくとも一方は水素原子ではなく、R6a及びR6bは、互いに結合して、シクロアルカン環、酸素原子、及び硫黄原子から選択された少なくとも1つのヘテロ原子を有する5員乃至8員ヘテロ環を形成してもよい請求項1又は2記載の有機ヘテロ高分子。
- R6a及びR6bの少なくとも一方が、直鎖状又は分岐鎖状C4−14アルキル基であるか、若しくはR6a及びR6bは互いに結合してアルキレンジオキシ基を形成する請求項1〜3のいずれかに記載の有機ヘテロ高分子。
- 有機半導体を形成するための組成物であって、請求項1〜4のいずれかに記載の有機ヘテロ高分子と、有機溶媒とを含み、有機半導体を形成するための組成物。
- 請求項1〜4のいずれかに記載の有機ヘテロ高分子で形成された有機半導体。
- 基材の少なくとも一方の面に請求項5記載の組成物を塗布して乾燥し、有機半導体を形成する有機半導体の製造方法。
- 請求項1〜4のいずれかに記載の有機ヘテロ高分子で形成された有機半導体を含む電子デバイス。
- 光電変換素子、スイッチング素子及び整流素子から選択された一種である請求項8記載の電子デバイス。
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JP2014172969A (ja) * | 2013-03-07 | 2014-09-22 | Tokyo Institute Of Technology | 有機ヘテロ高分子 |
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