Conjugated anthradithiophene terpolymers and photovoltaic devices containing them
US-2024188414-A1 · Jun 6, 2024 · US
US9905766B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9905766-B2 |
| Application number | US-201615075740-A |
| Country | US |
| Kind code | B2 |
| Filing date | Mar 21, 2016 |
| Priority date | Mar 24, 2015 |
| Publication date | Feb 27, 2018 |
| Grant date | Feb 27, 2018 |
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A polymer of an embodiment includes a repeating unit containing at least one bivalent group selected from the following formula (1) and the following formula (2). In the formulas (1) and (2), R is hydrogen, fluorine, an alkyl group, an aryl group, a heteroaryl group, or the like. X and Y are each an alkanoyl group, an aminocarbonyl group, an alkylsulfonyl group, or the like. Ar is an aryl group or a heteroaryl group.
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What is claimed is: 1. A polymer comprising a repeating unit containing at least one of a bivalent group represented by the following formula (1) and a bivalent group represented by the following formula (2), wherein R group is a monovalent group selected from hydrogen, fluorine, a cyano group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group, X group and Y group in formula (1) are each independently a monovalent group selected from hydrogen, fluorine, a cyano group, a substituted or unsubstituted alkanoyl group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted alkylsulfinyl group, a substituted or unsubstituted arylsulfinyl group, a substituted or unsubstituted alkylsulfonyl group, and a substituted or unsubstituted arylsulfonyl group, or are a condensed ring in which the X group and the Y group are bonded, X group and Y group in formula (2) are each independently a monovalent group selected from hydrogen, fluorine, a cyano group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted alkylsulfinyl group, a substituted or unsubstituted arylsulfinyl group, a substituted or unsubstituted alkylsulfonyl group, and a substituted or unsubstituted arylsulfonyl group, or are a condensed ring in which the X group and the Y group are bonded, and Ar group is a monovalent group selected from a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group. 2. The polymer of claim 1 , comprising at least one selected from a repeating unit of the bivalent group represented by the formula (1) and a repeating unit of the bivalent group represented by the formula (2), wherein a weight-average molecular weight of the polymer is not less than 3000 nor more than 1000000. 3. The polymer of claim 2 , wherein at least one selected from the R group, the X group, the Y group, the Ar group, and an end group of the polymer has a cross linking group. 4. The polymer of claim 1 , comprising at least one selected from a repeating unit represented by the following formula (3) and a repeating unit represented by the following formula (4), wherein R group is a monovalent group selected from hydrogen, fluorine, a cyano group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group, R′ group in formula (3) is a monovalent group selected from hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group, R′ group in the formula (4) is a monovalent group selected from a substituted or unsubstituted amino group and a substituted or unsubstituted heteroaryl group, and Ar group is a monovalent group selected from a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group, wherein a weight-average molecular weight of the polymer is not less than 3000 nor more than 1000000. 5. The polymer of claim 4 , wherein at least one selected from the R group, the R′ group, the Ar group, and an end group of the polymer has a cross linking group. 6. The polymer of claim 1 , comprising a structure represented by the following formula (5) or the following formula (6), wherein R group is a monovalent group selected from hydrogen, fluorine, a cyano group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group, X group and Y group in formula (5) are each independently a monovalent group selected from hydrogen, fluorine, a cyano group, a substituted or unsubstituted alkanoyl group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted alkylsulfinyl group, a substituted or unsubstituted arylsulfinyl group, a substituted or unsubstituted alkylsulfonyl group, and a substituted or unsubstituted arylsulfonyl group, or are a condensed ring in which the X group and the Y group are bonded, X group and Y group in the formula (6) are each independently a monovalent group selected from hydrogen, fluorine, a cyano group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted alkylsulfinyl group, a substituted or unsubstituted arylsulfinyl group, a substituted or unsubstituted alkylsulfonyl group, and a substituted or unsubstituted arylsulfonyl group, or are a condensed ring in which the X group and the Y group are bonded, Ar group is a monovalent group selected from a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group, R1 group and R2 group are each independently a monovalent group selected from an aryl group having an electron withdrawing group and an aryl group having an electron releasing group, and m is a positive number representing a polymerization degree, wherein a weight-average molecular weight of the polymer is not less than 3000 nor more than 1000000. 7. The polymer of claim 1 , comprising a structure represented by the following formula (7) or the following formula (8), wherein at least one selected from R5 group and Ar1 group has a cross-linking group, R group, R3 group, R4 group, and R5 group which does not have the cross-linking group are each independently a monovalent group selected from hydrogen, fluorine, a cyano group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group, X group and Y group in formula (7) are each independently a monovalent group selected from hydrogen, fluorine, a cyano group, a substituted or unsubstituted alkanoyl group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted alkylsulfinyl group, a substituted or unsubstituted arylsulfinyl group, a substituted or unsubstituted alkylsulfonyl group, and a substituted or unsubstituted arylsulfonyl group, or are a condensed ring in which the X group and the Y group are bonded, X group and Y group in the formula (8) are each independently a monovalent group selected from hydrogen, fluorine, a cyano group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted alkylsulfinyl group, a substituted or unsubstituted arylsulfinyl group, a substituted or unsubstituted alkylsulfonyl group, and a substituted or unsubstituted arylsulfonyl group, or are a condensed ring in which the X group and the Y group are bonded, X′ group and Y′ group in formula (7) are each independently a monovalent group selected from hydrogen, fluorine, a cyano group, a substituted or unsubstituted alkanoyl group, a substituted or unsub
Saturated aliphatic units · CPC title
alternating · CPC title
Polymers, i.e. more than 10 repeat units · CPC title
containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene · CPC title
Side-chains containing halogens · CPC title
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