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US 8,895,693 B2Granted
Electron-donating polymers and organic solar cells including the same
AssigneeSamsung Electronics Co., Ltd.
InventorsYeong Suk Choi, Soo-Ghang Ihn, Bulliard Xavier, Sung Young Yun, Youn Hee Lim, In Sun Park, Yeon Ji Chung
Life of this patent
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Abstract
An electron-donating polymer including a repeating unit A with a repeating unit represented by Chemical Formula 1 and at least one of repeating units represented by Chemical Formulae 2-4.
Claims25
An electron-donating polymer, comprising:
- a repeating unit A including a repeating unit according to Chemical Formula 1 and at least one repeating unit according to one of Chemical Formulae 2-4,
- wherein, in Chemical Formula 1, X1 and X2 are one of same and different, and each of X1 and X2 are independently one of
- hydrogen, a halogen, a substituted C1-C20 aliphatic organic group, an unsubstituted C1-C20 aliphatic organic group, a hydroxy group, a substituted C1-C20 alkoxy group, an unsubstituted C1-C20 alkoxy group, a substituted C1-C20 ester group, an unsubstituted C1-C20 ester group, a thiol group, and SR100,
- where R100 is one of a substituted C1-C20 aliphatic organic group, an unsubstituted C1-C20 aliphatic organic group, a substituted C2-C30 aromatic organic group, an unsubstituted C2-C30 aromatic organic group, a substituted C2-C30 heterocycloalkyl group, an unsubstituted C2-C30 heterocycloalkyl group, and
- R1 and R2 are one of same and different, and
- R1 and R2 are each independently one of
- hydrogen, a substituted C1-C20 linear alkyl group, a substituted C1-C20 branched alkyl group, an unsubstituted C1-20 linear alkyl group, and an unsubstituted C1-C20 branched alkyl group, a substituted C3-C20 cycloakyl group, an unsubstituted C3-C20 cycloalkyl group, a substituted C1-C20 alkoxy group, an unsubstituted C1-C20 alkoxy group, a substituted C6-C30 aryl group, and an unsubstituted C6-C30 aryl group, a substituted C2-C30 heteroaryl group, and an and unsubstituted C2-C30 heteroaryl group, and
- at least one CH2 group included in R1 and R2 is substituted with one of —O—, —S—, —SO2—, —CO—, —OCO—, —COO—, —CH═CH—, —C≡C—, and —SiR101R102, where R101 and R102 are one of same and different, and R101 and R102 are each independently one of
- hydrogen, a substituted C1-C20 linear alkyl group, a;
- substituted C1-C20 branched alkyl group, an unsubstituted C1-C20 linear alkyl group and an unsubstituted C1-C20 branched alkyl group, a substituted C3-C20 cycloalkyl group, an unsubstituted C3-C20 cycloalkyl group, a substituted C1-C20 alkoxy group, an unsubstituted C1-C20 alkoxy group, a substituted C6-C30 aryl group, an unsubstituted C6-C30 aryl group, a substituted C2-C30 heteroaryl group, and an unsubstituted C2-C30 heteroaryl group;
- and
- wherein, in Chemical Formulae 2-4, Z1-Z6 are one of same and different, and are each independently one of hydrogen and an electron withdrawing group,
- n1 is an integer ranging from 1 to 5, inclusive,
- n2 is an integer ranging from 0 to 3, inclusive,
- n3 is an integer ranging from 0 to 4, inclusive,
- n2+n3 is an integer ranging from 1 to 5, inclusive,
- n4 is an integer ranging from 0 to 3, inclusive,
- n5 is an integer ranging from 0 to 2, inclusive,
- n6 is an integer ranging from 0 to 4, inclusive,
- n4+n5+n6 is an integer ranging from 1 to 5, inclusive,
- R4, R6, R7, and R9-R11 are one of same and different, and
- R4, R6, R7, and R9-R11 are each independently one of
- hydrogen, a substituted C1-C20 linear alkyl group, a substituted C1-C20 branched alkyl group, an unsubstituted C1-C20 linear alkyl group, an unsubstituted C1-C20 branched alkyl group, a substituted C3-C20 cycloalkyl group, an unsubstituted C3-C20 cycloalkyl group, substituted C1-C20 alkoxy group, an unsubstituted C1-C20 alkoxy group, a substituted C6-C30 aryl group, an unsubstituted C6-C30 aryl group, a substituted C2-C30 heteroaryl group, and an unsubstituted C2-C30 heteroaryl group, and
- at least one CH2 group included in the R4, R6, R7, and R9-R11 is substituted with one of —O—, —S—, —SO2—, —CO—, —OCO—, —COO—, —CH═CH—, —C≡C—, and —SiR103R104, where R103 and R104 are one of same and different, and R103 and R104 are each independently one of
- hydrogen, a substituted C1-C20 linear alkyl group, a substituted C1-C20 branched alkyl group, an unsubstituted C1-C20 linear alkyl group, an unsubstituted C1-C20 branched alkyl group, a substituted C3-C20 cycloalkyl group, an unsubstituted C3-C20 cycloalkyl group, a substituted C1-C20 alkoxy group, an unsubstituted C1-C20 alkoxy group, a substituted C6-C30 aryl group, an unsubstituted C6-C30 aryl group, a substituted C2-C30 heteroaryl group, and an unsubstituted C2-C30 heteroaryl group,
- R3, R5, and R8 are one of same and different, and are each independently one of
- hydrogen, a halogen, a substituted C1-C20 aliphatic organic group, an unsubstituted C1-C20 aliphatic organic group, a hydroxy group, a substituted C1-C20 alkoxy group, an unsubstituted C1-C20 alkoxy group, a substituted C1-C20 ester group, an unsubstituted C1-C20 ester group, a thiol group, and —SR105, where R105 is one of
- a substituted C1-C20 aliphatic organic group, an unsubstituted C1-C20 aliphatic organic group, a substituted C2-C20 aromatic organic group, an unsubstituted C2-C30 aromatic organic group, a substituted C2-C30 heterocycloalkyl group, and an unsubstituted C2-C30 heterocycloalkyl group,
- m4 is one of same and different in each of the repeating unit according to Chemical Formula 2, and each m4 is independently an integer ranging from 0 to 5, inclusive,
- m6 and m9 are each independently an integer ranging from 0 to 3, inclusive,
- m7 and m11 are each independently an integer ranging from 0 to 4, inclusive, and
- m10 is one of same and different in each of the repeating unit according to Chemical Formula 4, and each m10 is independently an integer ranging from 0 to 2, inclusive.
29 more elements
An electron-donating polymer, comprising:
- a repeating unit A including a repeating unit according to Chemical Formula 1 and at least one repeating unit according to one of Chemical Formulae 2-4;
- and
- a repeating unit B including a repeating unit according to Chemical Formula 1 and a repeating unit according to Chemical Formula 9,
- wherein, in Chemical Formula 1, X1 and X2 are one of same and different, and are each independently one of
- hydrogen, a halogen, a substituted C1-C20 aliphatic organic group, an unsubstituted C1-C20 aliphatic organic group, a hydroxy group, a substituted C1-C20 alkoxy group, an unsubstituted C1-C20 alkoxy group, a substituted C1-C20 ester group, an unsubstituted C1-C20 ester group, a thiol group, and SR100, where R100 is one of
- a substituted C1-C20 aliphatic organic group, an unsubstituted C1-C20 aliphatic organic group, a substituted C2-C30 aromatic organic group, an unsubstituted C2-C30 aromatic organic group, a substituted C2-C30 heterocycloalkyl group, and an unsubstituted C2-C30 heterocycloalkyl group,
- R1 and R2 are one of same and different, and
- R1 and R2 are each independently one of
- hydrogen, a substituted C1-C20 linear alkyl group, a substituted C1-C20 branched alkyl group, an unsubstituted C1-C20 linear alkyl group, an unsubstituted C1-C20 branched alkyl group, a substituted C3-C20 cycloalkyl group, an unsubstituted C3-C20 cycloalkyl group, a substituted C1-C20 alkoxy group, an unsubstituted C1-C20 alkoxy group, a substituted C6-C30 aryl group, an unsubstituted C6-C30 aryl group, a substituted C2-C30 heteroaryl group, and an unsubstituted C2-C30 heteroaryl group, and
- at least one CH2 group included in the R1 and R2 is substituted with one of —O—, —S—, —SO2—, —CO—, —OCO—, —COO—, —CH═CH—, —C≡C—, and —SiR101R102, where R101 and R102 are one of same and different, and R101 and R102 are each independently one of
- hydrogen, a substituted C1-C20 linear alkyl group, a substituted C1-C20 branched alkyl group, an unsubstituted C1-C20 linear alkyl group, an unsubstituted C1-C20 branched alkyl group, a substituted C3-C20 cycloalkyl group, an unsubstituted C3-C20 cycloalkyl group, a substituted C1-C20 alkoxy group, an unsubstituted C1-C20 alkoxy group, a substituted C6-C30 aryl group, an unsubstituted C6-C30 aryl group, a substituted C2-C30 heteroaryl group, and an unsubstituted C2-C30 heteroaryl group,
- in Chemical Formulae 2-4, Z1-Z6 are one of same and different, and are each independently one of hydrogen and an electron withdrawing group,
- n1 is an integer ranging from 1 to 5, inclusive,
- n2 is an integer ranging from 0 to 3, inclusive,
- n3 is an integer ranging from 0 to 4, inclusive,
- n2+n3 is an integer ranging from 1 to 5, inclusive,
- n4 is an integer ranging from 0 to 3, inclusive,
- n5 is an integer ranging from 0 to 2, inclusive,
- n6 is an integer ranging from 0 to 4, inclusive,
- n4+n5+n6 is an integer ranging from 1 to 5, inclusive,
- R4, R6, R7, and R9-R11 are one of same and different,
- R4, R6, R7, and R9-R11 are each independently one of
- hydrogen, a substituted C1-C20 linear alkyl group, a substituted C1-C20 branched alkyl group, an unsubstituted C1-C20 linear alkyl group, an unsubstituted C1-C20 branched alkyl group, a substituted C3-C20 cycloalkyl group, an unsubstituted C3-C20 cycloalkyl group, a substituted C1-C20 alkoxy group, an unsubstituted C1-C20 alkoxy group, a substituted C6-C30 aryl group, an unsubstituted C6-C30 aryl group, a substituted C2-C30 heteroaryl group, an unsubstituted C2-C30 heteroaryl group, and
- at least one CH2 group included in the R4, R6, R7, and R9-R11 is substituted with one of —O—, —S—, —SO2—, —CO—, —OCO—, —COO—, —CH═CH—, —C≡C—, and —SiR103R104, where R103 and R104 are one of same and different, and R103 and R104 are each independently one of
- hydrogen, a substituted C1-C20 linear alkyl group, a substituted C1-C20 branched alkyl group, an unsubstituted C1-C20 linear alkyl group, an unsubstituted C1-C20 branched alkyl group, a substituted C3-C20 cycloalkyl group, an unsubstituted C3-C20 cycloalkyl group, a substituted C1-C20 alkoxy group, an unsubstituted C1-C20 alkoxy group, a substituted C6-C30 aryl group, an unsubstituted C6-C30 aryl group, a substituted C2-C30 heteroaryl group, an unsubstituted C2-C30 heteroaryl group,
- R3, R5, and R8 are one of same and different, and are each independently one of
- hydrogen, a halogen, a substituted C1-C20 aliphatic organic group, an unsubstituted C1-C20 aliphatic organic group, a hydroxy group, a substituted C1-C20 alkoxy group, an unsubstituted C1-C20 alkoxy group, a substituted C1-C20 ester group, an unsubstituted C1-C20 ester group, a thiol group, and —SR105, where R105 is one of
- a substituted C1-C20 aliphatic organic group, an unsubstituted C1-C20 aliphatic organic group, a substituted C2-C30 aromatic organic group, an unsubstituted C2-C30 aromatic organic group, a substituted C2-C30 heterocycloalkyl group, and an unsubstituted C2-C30 heterocycloalkyl group,
- m4 is one of same and different in each of the repeating unit according to Chemical Formula 2, and each m4 is independently an integer ranging from 0 to 5, inclusive,
- m6 and m9 are each independently an integer ranging from 0 to 3, inclusive,
- m7 and m11 are each independently an integer ranging from 0 to 4, inclusive, and
- m10 is one of same and different in each of the repeating unit according to Chemical Formula 4, and each m10 is independently an integer ranging from 0 to 2, inclusive, and
- in Chemical Formula 9, X3 is one of same and different in each of the repeating unit according to Chemical Formula 9, and each X3 is an electron-accepting group including two ester residual groups and a divalent aliphatic organic group linking the two ester residual groups, the divalent aliphatic organic group being one of substituted and unsubstituted, and
- X4 is one of same and different in each of the repeating unit according to Chemical Formula 9, and each X4 is independently one of
- hydrogen, a halogen, a substituted C1-C20 aliphatic organic group, an unsubstituted C1-C20 aliphatic organic group, a hydroxy group, a substituted C1-C20 alkoxy group, an unsubstituted C1-C20 alkoxy group, a substituted C1-C20 ester group, an unsubstituted C1-C20 ester group, a thiol group, and —SR107, where R107 is one of
- a substituted C1-C20 aliphatic organic group, an unsubstituted C1-C20 aliphatic organic group, a substituted C2-C30 aromatic organic group, an unsubstituted C2-C30 aromatic organic group, a substituted C2-C30 heterocycloalkyl group, and an unsubstituted C2-C30 heterocycloalkyl group.
33 more elements
Dependencies are inferred from the claim text.