KR101477703B1 - 풀러렌 및 그의 유도체를 포함하는 유기 광기전력 소자 - Google Patents
풀러렌 및 그의 유도체를 포함하는 유기 광기전력 소자 Download PDFInfo
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- KR101477703B1 KR101477703B1 KR1020097000567A KR20097000567A KR101477703B1 KR 101477703 B1 KR101477703 B1 KR 101477703B1 KR 1020097000567 A KR1020097000567 A KR 1020097000567A KR 20097000567 A KR20097000567 A KR 20097000567A KR 101477703 B1 KR101477703 B1 KR 101477703B1
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- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 title claims abstract description 128
- 229910003472 fullerene Inorganic materials 0.000 title claims abstract description 91
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- 238000010521 absorption reaction Methods 0.000 description 3
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Abstract
Description
Claims (87)
- (i) 하나 이상의 p형 물질, 및(ii) 하기 화학식으로 나타내어지는 풀러렌 유도체 및 그의 용매화물, 염 및 혼합물을 포함하는 하나 이상의 n형 물질을 포함하는 혼합물을 포함하는 조성물.F* - (R)n(여기서, n은 1 이상의 정수이고; F*는 6원 및 5원 고리를 포함하는 표면을 갖는 풀러렌을 포함하고; R은 하나 이상의 임의 치환된, 불포화 또는 포화된, 카르보시클릭 또는 헤테로시클릭 제 1 고리를 포함하는 치환체이고, 제 1 고리는 풀러렌에 직접 결합됨).
- 하기 화학식으로 나타내어지는 풀러렌 유도체 및 그의 용매화물, 염 및 혼합물을 포함하는 하나 이상의 n형 물질을 포함하는 조성물.F* - (R)n(여기서, n은 1 이상의 정수이고; F*는 6원 및 5원 고리를 포함하는 표면을 갖는 풀러렌을 포함하고; R은 하나 이상의 임의 치환된, 불포화 또는 포화된, 카르보시클릭 또는 헤테로시클릭 제 1 고리를 포함하는 치환체이고, 제 1 고리는 풀러렌에 직접 결합됨).
- 제 1 항 또는 제 2 항에 있어서, 제 1 고리가 치환된 조성물.
- 제 1 항 또는 제 2 항에 있어서, 제 1 고리가 치환되지 않은 조성물.
- 제 1 항 또는 제 2 항에 있어서, 제 1 고리가 불포화 고리인 조성물.
- 제 1 항 또는 제 2 항에 있어서, 제 1 고리가 포화 고리인 조성물.
- 제 1 항 또는 제 2 항에 있어서, 제 1 고리가 카르보시클릭 고리인 조성물.
- 제 1 항 또는 제 2 항에 있어서, 제 1 고리가 헤테로시클릭 고리인 조성물.
- 제 1 항 또는 제 2 항에 있어서, 제 1 고리가 임의 치환된 4원, 5원 또는 6원 고리인 조성물.
- 제 1 항 또는 제 2 항에 있어서, 고리가 임의 치환된 5원 고리인 조성물.
- 제 1 항 또는 제 2 항에 있어서, R이 제 1 고리에 결합되거나 또는 융합된 제 2 고리를 더 포함하는 조성물.
- 제 1 항 또는 제 2 항에 있어서, R이 제 1 고리에 융합된 임의 치환된 제 2 고리를 더 포함하는 조성물.
- 제 1 항 또는 제 2 항에 있어서, R이 제 1 고리에 융합된 아릴기인 임의 치환된 제 2 고리를 더 포함하는 조성물.
- 제 1 항 또는 제 2 항에 있어서, R이 임의 치환된 인덴, 임의 치환된 나프틸, 임의 치환된 페닐, 임의 치환된 피리디닐, 임의 치환된 퀴놀리닐, 임의 치환된 시클로헥실, 또는 임의 치환된 시클로펜틸인 조성물.
- 제 1 항 또는 제 2 항에 있어서, R이 인덴, 나프틸, 페닐, 피리디닐, 퀴놀리닐, 시클로헥실 또는 시클로펜틸인 조성물.
- 제 1 항 또는 제 2 항에 있어서, R이 임의 치환된 인덴인 조성물.
- 제 1 항 또는 제 2 항에 있어서, R이 인덴인 조성물.
- 제 1 항 또는 제 2 항에 있어서, n이 1 내지 6인 조성물.
- 제 1 항 또는 제 2 항에 있어서, n이 1 내지 3인 조성물.
- 제 1 항 또는 제 2 항에 있어서, R이 인덴이고, n이 1인 조성물.
- 제 1 항 또는 제 2 항에 있어서, R이 인덴이고, n이 2인 조성물.
- 제 1 항 또는 제 2 항에 있어서, R이 인덴이고, n이 3인 조성물.
- 제 1 항 또는 제 2 항에 있어서, R이 인덴이고, n이 1 내지 20인 조성물.
- 제 1 항 또는 제 2 항에 있어서, R이 인덴이고, n이 1 내지 10인 조성물.
- 제 1 항 또는 제 2 항에 있어서, 제 1 고리가 히드록시, 아실, 아실아미노, 아실옥시, 알킬, 치환된 알킬, 알콕시, 치환된 알콕시, 알케닐, 치환된 알케닐, 알키닐, 치환된 알키닐, 아미노, 치환된 아미노, 아미노아실, 아릴, 치환된 아릴, 아릴옥시, 치환된 아릴옥시, 시클로알콕시, 치환된 시클로알콕시, 카르복실, 카르복실 에스테르, 시아노, 티올, 티오알킬, 치환된 티오알킬, 티오아릴, 치환된 티오아릴, 티오헤테로아릴, 치환된 티오헤테로아릴, 티오시클로알킬, 치환된 티오시클로알킬, 티오헤테로시클릭, 치환된 티오헤테로시클릭, 시클로알킬, 치환된 시클로알킬, 할로, 니트로, 헤테로아릴, 치환된 헤테로아릴, 헤테로시클릭, 치환된 헤테로시클릭, 헤테로아릴옥시, 치환된 헤테로아릴옥시, 헤테로시클릴옥시, 치환된 헤테로시클릴옥시 및 이들의 조합으로 이루어지는 군으로부터 선택되는 하나 이상의 치환체로 임의로 치환된 조성물.
- 제 1 항 또는 제 2 항에 있어서, R이 [4+2] 고리화 첨가에 의해 풀러렌에 공유 결합된 조성물.
- 제 1 항 또는 제 2 항에 있어서, R이 1 개 또는 2 개의 공유 결합에 의해 풀러렌에 공유 결합된 조성물.
- 제 1 항 또는 제 2 항에 있어서, R이 2 개의 결합에 의해 풀러렌에 공유 결합된 조성물.
- 제 1 항 또는 제 2 항에 있어서, R이 2 개의 탄소-탄소 결합에 의해 풀러렌에 공유 결합된 조성물.
- 제 1 항 또는 제 2 항에 있어서, R이 풀러렌[6,6] 위치에서 2 개의 탄소-탄소 결합에 의해 풀러렌에 공유 결합된 조성물.
- 제 1 항 또는 제 2 항에 있어서, 풀러렌이 C60, C70 또는 C84 풀러렌 또는 이들의 조합을 포함하는 조성물.
- 제 1 항 또는 제 2 항에 있어서, 풀러렌이 탄소만을 포함하는 조성물.
- 제 1 항 또는 제 2 항에 있어서, 풀러렌이 R 이외에 풀러렌에 결합된 하나 이상의 유도체기를 포함하는 조성물.
- 제 1 항에 있어서, p형 물질이 공액 중합체를 포함하는 조성물.
- 제 1 항에 있어서, p형 물질이 유기 용매 또는 물에 용해될 수 있거나 또는 분산될 수 있는 공액 중합체를 포함하는 조성물.
- 제 1 항에 있어서, p형 물질이 폴리티오펜을 포함하는 조성물.
- 제 1 항에 있어서, p형 물질이 위치규칙적 폴리티오펜을 포함하는 조성물.
- 제 1 항에 있어서, n형 및 p형 물질이 중량 기준으로 0.1 내지 4.0 : 1 (p형 : n형)의 비로 존재하는 조성물.
- 제 1 항에 있어서, p형 물질이 폴리티오펜을 포함하고, R기가 임의 치환된 인덴이고, 조성물이 10 nm 내지 300 nm의 필름 두께를 갖는 필름 형태인 조성물.
- 제 1 항에 있어서, p형 물질이 위치규칙적 폴리티오펜을 포함하고, R기가 인덴인 조성물.
- 제 1 항에 있어서, p형 물질이 위치규칙적 폴리티오펜을 포함하고, R기가 인덴이고, 조성물이 2 종 이상의 용매를 더 포함하는 조성물.
- (i) 하나 이상의 p형 물질, 및(ii) [6,6] 결합 부위의 두 탄소 원자가 R기에 공유 결합되는 하나 이상의 [6,6]풀러렌 결합 부위를 포함하는 하나 이상의 풀러렌 유도체를 포함하는 하나 이상의 n형 물질을 포함하는 혼합물을 포함하며, R기는 하나 이상의 임의 치환된, 불포화 또는 포화된, 카르보시클릭 또는 헤테로시클릭 제 1 고리를 포함하는 것인 조성물.
- [6,6] 결합 부위의 두 탄소 원자가 R기에 공유 결합되는 하나 이상의 [6,6]풀러렌 결합 부위를 포함하는 하나 이상의 풀러렌 유도체를 포함하는 하나 이상의 n형 물질을 포함하며, R기는 하나 이상의 임의 치환된, 불포화 또는 포화된, 카르보시클릭 또는 헤테로시클릭 제 1 고리를 포함하는 것인 조성물.
- 제 42 항 또는 제 43 항에 있어서, R기가 [6,6]풀러렌 결합 부위에 직접 결합된 제 1 고리를 포함하는 조성물.
- 제 42 항 또는 제 43 항에 있어서, R기는 [6,6]풀러렌 결합 부위에 직접 결합된 제 1 고리 및 제 1 고리에 융합된 제 2 고리를 포함하는 조성물.
- 제 42 항 또는 제 43 항에 있어서, R기가 [6,6]풀러렌 결합 부위에 직접 결합된 5원 카르보시클릭 제 1 고리 및 제 1 고리에 융합된 6원 카르보시클릭 제 2 고리를 포함하는 조성물.
- 제 42 항 또는 제 43 항에 있어서, R기가 임의 치환된 인덴을 포함하는 조성물.
- 제 42 항 또는 제 43 항에 있어서, R기가 인덴을 포함하는 조성물.
- 제 42 항 또는 제 43 항에 있어서, R기가 임의 치환된 o-퀴노디메탄을 포함하는 조성물.
- 제 49 항에 있어서, R기가 치환되지 않은 o-퀴노디메탄을 포함하는 조성물.
- 제 49 항에 있어서, R기가 히드록시, 아실, 아실아미노, 아실옥시, 알킬, 치환된 알킬, 알콕시, 치환된 알콕시, 알케닐, 치환된 알케닐, 알키닐, 치환된 알키닐, 아미노, 치환된 아미노, 아미노아실, 아릴, 치환된 아릴, 아릴옥시, 치환된 아릴옥시, 시클로알콕시, 치환된 시클로알콕시, 카르복실, 카르복실 에스테르, 시아노, 티올, 티오알킬, 치환된 티오알킬, 티오아릴, 치환된 티오아릴, 티오헤테로아릴, 치환된 티오헤테로아릴, 티오시클로알킬, 치환된 티오시클로알킬, 티오헤테로시클릭, 치환된 티오헤테로시클릭, 시클로알킬, 치환된 시클로알킬, 할로, 니트로, 헤테로아릴, 치환된 헤테로아릴, 헤테로시클릭, 치환된 헤테로시클릭, 헤테로아릴옥시, 치환된 헤테로아릴옥시, 헤테로시클릴옥시, 치환된 헤테로시클릴옥시 및 이들의 조합으로 이루어지는 군으로부터 선택되는 하나 이상의 치환체로 치환된 조성물.
- 제 42 항에 있어서, p형 물질이 공액 중합체를 포함하는 조성물.
- 제 42 항에 있어서, p형 물질이 폴리티오펜을 포함하는 조성물.
- 제 42 항에 있어서, p형 물질이 위치규칙적 폴리티오펜을 포함하는 조성물.
- 제 42 항에 있어서, p형 물질이 위치규칙적 폴리티오펜을 포함하고, R기가 임의 치환된 인덴인 조성물.
- (i) 하나 이상의 p형 물질, 및(ii) 하나 이상의 유도체 모이어티에 [4+2] 고리화 첨가에 의해 공유 결합된 하나 이상의 풀러렌을 포함하는 풀러렌 유도체를 포함하는 하나 이상의 n형 물질을 포함하는 혼합물을 포함하며, 유도체 모이어티가 하나 이상의 임의 치환된, 불포화 또는 포화된, 카르보시클릭 또는 헤테로시클릭 제 1 고리를 포함하는 것인 조성물.
- 하나 이상의 유도체 모이어티에 [4+2] 고리화 첨가에 의해 공유 결합된 하나 이상의 풀러렌을 포함하는 풀러렌 유도체를 포함하는 하나 이상의 n형 물질을 포함하며, 유도체 모이어티가 하나 이상의 임의 치환된, 불포화 또는 포화된, 카르보시클릭 또는 헤테로시클릭 제 1 고리를 포함하는 것인 조성물.
- 제 56 항 또는 제 57 항에 있어서, 유도체 모이어티가 풀러렌에 직접 결합된 제 1 고리를 포함하는 조성물.
- 제 56 항 또는 제 57 항, 유도체 모이어티가 풀러렌에 직접 결합된 제 1 고리 및 제 1 고리에 융합된 제 2 고리를 포함하는 조성물.
- 제 56 항 또는 제 57 항, 유도체 모이어티가 풀러렌 결합 부위에 직접 결합된 5원 카르보시클릭 제 1 고리 및 제 1 고리에 융합된 6원 카르보시클릭 제 2 고리를 포함하는 조성물.
- 제 56 항 또는 제 57 항에 있어서, 유도체 모이어티가 임의 치환된 인덴을 포함하는 조성물.
- 제 56 항 또는 제 57 항에 있어서, 유도체 모이어티가 인덴을 포함하는 조성물.
- 제 56 항 또는 제 57 항에 있어서, 유도체 모이어티가 임의 치환된 o-퀴노디메탄을 포함하는 조성물.
- 제 63 항에 있어서, 유도체 모이어티가 치환되지 않은 o-퀴노디메탄을 포함하는 조성물.
- 제 63 항에 있어서, 유도체 모이어티가 히드록시, 아실, 아실아미노, 아실옥시, 알킬, 치환된 알킬, 알콕시, 치환된 알콕시, 알케닐, 치환된 알케닐, 알키닐, 치환된 알키닐, 아미노, 치환된 아미노, 아미노아실, 아릴, 치환된 아릴, 아릴옥시, 치환된 아릴옥시, 시클로알콕시, 치환된 시클로알콕시, 카르복실, 카르복실 에스테르, 시아노, 티올, 티오알킬, 치환된 티오알킬, 티오아릴, 치환된 티오아릴, 티오헤테로아릴, 치환된 티오헤테로아릴, 티오시클로알킬, 치환된 티오시클로알킬, 티오헤테로시클릭, 치환된 티오헤테로시클릭, 시클로알킬, 치환된 시클로알킬, 할로, 니트로, 헤테로아릴, 치환된 헤테로아릴, 헤테로시클릭, 치환된 헤테로시클릭, 헤테로아릴옥시, 치환된 헤테로아릴옥시, 헤테로시클릴옥시, 치환된 헤테로시클릴옥시 및 이들의 조합으로 이루어지는 군으로부터 선택되는 하나 이상의 치환체로 치환된 것인 조성물.
- 제 56 항에 있어서, p형 물질이 공액 중합체를 포함하는 조성물.
- 제 56 항에 있어서, p형 물질이 폴리티오펜을 포함하는 조성물.
- 제 56 항에 있어서, p형 물질이 위치규칙적 폴리티오펜을 포함하는 조성물.
- 제 56 항에 있어서, p형 물질이 위치규칙적 폴리티오펜을 포함하고, 유도체 모이어티가 임의 치환된 인덴인 조성물.
- 하나 이상의 양극, 하나 이상의 음극, 및 하나 이상의 활성층을 포함하고, 상기 활성층이(i) 하나 이상의 p형 물질, 및(ii) 하기 화학식으로 나타내어지는 풀러렌 유도체 및 그의 용매화물, 염 및 혼합물을 포함하는 하나 이상의 n형 물질을 포함하는 혼합물을 포함하는 조성물을 포함하는 광기전력 소자.F* - (R)n(여기서, n은 1 이상의 정수이고, F*는 6원 및 5원 고리를 포함하는 표면을 갖는 풀러렌을 포함하고, R은 하나 이상의 임의 치환된, 불포화 또는 포화된, 카르보시클릭 또는 헤테로시클릭 제 1 고리를 포함하는 치환체이고, 제 1 고리는 풀러렌에 직접 결합됨).
- 제 70 항에 있어서, P3HT-PCBM 활성층을 포함하는 실질적으로 유사한 소자에 비해 5% 이상의 효율 증가를 나타내는 광기전력 소자.
- 제 70 항에 있어서, P3HT-PCBM 활성층을 포함하는 실질적으로 유사한 소자에 비해 15% 이상의 효율 증가를 나타내는 광기전력 소자.
- 제 70 항에 있어서, 하나 이상의 정공 주입층을 더 포함하는 광기전력 소자.
- 제 70 항에 있어서, 폴리티오펜을 포함하는 하나 이상의 정공 주입층을 더 포함하는 광기전력 소자.
- 제 70 항에 있어서, 위치규칙적 폴리티오펜을 포함하는 하나 이상의 정공 주입층을 더 포함하는 광기전력 소자.
- 제 70 항에 있어서, R기가 임의 치환된 인덴기를 포함하는 광기전력 소자.
- 제 70 항에 있어서, R기가 인덴기를 포함하는 광기전력 소자.
- 제 70 항에 있어서, R기가 임의 치환된 인덴기를 포함하고, p형 물질이 하나 이상의 위치규칙적 폴리티오펜을 포함하는 광기전력 소자.
- 제 70 항에 있어서, R기가 임의 치환된 인덴기를 포함하고, p형 물질이 하나 이상의 위치규칙적 폴리티오펜을 포함하고, 소자가 위치규칙적 폴리티오펜을 포함하는 정공 주입층을 더 포함하는 광기전력 소자.
- 제 70 항에 있어서, R기가 2개의 공유 결합으로 풀러렌에 결합된 임의 치환된 o-퀴노디메탄인 광기전력 소자.
- 제 80 항에 있어서, R기가 치환되지 않은 o-퀴노디메탄인 광기전력 소자.
- 제 80 항에 있어서, R기가 히드록시, 아실, 아실아미노, 아실옥시, 알킬, 치환된 알킬, 알콕시, 치환된 알콕시, 알케닐, 치환된 알케닐, 알키닐, 치환된 알키닐, 아미노, 치환된 아미노, 아미노아실, 아릴, 치환된 아릴, 아릴옥시, 치환된 아릴옥시, 시클로알콕시, 치환된 시클로알콕시, 카르복실, 카르복실 에스테르, 시아노, 티올, 티오알킬, 치환된 티오알킬, 티오아릴, 치환된 티오아릴, 티오헤테로아릴, 치환된 티오헤테로아릴, 티오시클로알킬, 치환된 티오시클로알킬, 티오헤테로시클릭, 치환된 티오헤테로시클릭, 시클로알킬, 치환된 시클로알킬, 할로, 니트로, 헤테로아릴, 치환된 헤테로아릴, 헤테로시클릭, 치환된 헤테로시클릭, 헤테로아릴옥시, 치환된 헤테로아릴옥시, 헤테로시클릴옥시, 치환된 헤테로시클릴옥시 및 이들의 조합으로 이루어지는 군으로부터 선택되는 하나 이상의 치환체로 치환된 것인 광기전력 소자.
- (i) 하나 이상의 p형 물질을 제공하고,(ii) 하기 화학식으로 나타내어지는 풀러렌 유도체 및 그의 용매화물, 염 및 혼합물을 포함하는 하나 이상의 n형 물질을 제공하고,(iii) p형 및 n형 물질을 조합하여 혼합물을 형성하는것을 포함하고, 상기 혼합물이 하나 이상의 용매를 더 포함하는 것인 혼합물을 포함하는 조성물의 제조 방법.F* - (R)n(여기서, n은 1 이상의 정수이고, F*는 6원 및 5원 고리를 포함하는 표면을 갖는 풀러렌을 포함하고, R은 하나 이상의 임의 치환된, 불포화 또는 포화된, 카르보시클릭 또는 헤테로시클릭 제 1 고리를 포함하는 치환체이고, 제 1 고리는 풀러렌에 직접 결합됨)
- 제 83 항에 있어서, 혼합물이 2 종 이상의 용매를 포함하는 방법.
- 제 83 항에 있어서, 용매를 제거하고, 혼합물을 필름으로 형성하는 것을 더 포함하는 방법.
- 제 83 항에 있어서, R이 임의 치환된 인덴을 포함하는 방법.
- 제 83 항에 있어서, R이 인덴을 포함하는 방법.
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US20060076050A1 (en) | 2004-09-24 | 2006-04-13 | Plextronics, Inc. | Heteroatomic regioregular poly(3-substitutedthiophenes) for photovoltaic cells |
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CN103227289B (zh) | 2016-08-17 |
TW200812128A (en) | 2008-03-01 |
WO2008018931A2 (en) | 2008-02-14 |
JP2009540099A (ja) | 2009-11-19 |
US20120318359A1 (en) | 2012-12-20 |
JP5519275B2 (ja) | 2014-06-11 |
JP2014169287A (ja) | 2014-09-18 |
CN103227289A (zh) | 2013-07-31 |
US8217260B2 (en) | 2012-07-10 |
WO2008018931A3 (en) | 2008-04-03 |
US20140251434A1 (en) | 2014-09-11 |
EP2038940A2 (en) | 2009-03-25 |
EP2509129B1 (en) | 2019-10-30 |
CA2655135A1 (en) | 2008-02-14 |
TW201419604A (zh) | 2014-05-16 |
HK1134374A1 (en) | 2010-04-23 |
KR20090076887A (ko) | 2009-07-13 |
EP2038940B1 (en) | 2017-03-15 |
US20080319207A1 (en) | 2008-12-25 |
CN101529610A (zh) | 2009-09-09 |
US8697988B2 (en) | 2014-04-15 |
CA2655135C (en) | 2016-06-07 |
IL195846A0 (en) | 2009-09-01 |
EP2509129A1 (en) | 2012-10-10 |
US20130298993A1 (en) | 2013-11-14 |
US20100132782A1 (en) | 2010-06-03 |
US9472765B2 (en) | 2016-10-18 |
US8894887B2 (en) | 2014-11-25 |
US8815124B2 (en) | 2014-08-26 |
TWI430493B (zh) | 2014-03-11 |
CN101529610B (zh) | 2013-01-02 |
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