Photovoltaic cell containing novel photoactive polymer

Patent metadata

Field	Value
Publication number	US-8969508-B2
Application number	US-201313777183-A
Country	US
Kind code	B2
Filing date	Feb 26, 2013
Priority date	Sep 2, 2010
Publication date	Mar 3, 2015
Grant date	Mar 3, 2015

Abstract

Photoactive polymers are provided, as well as related photovoltaic cells, articles, systems, and methods comprising these photoactive polymers.

First claim

What is claimed is:

1. An article, comprising:
a first electrode,
a second electrode, and
a photoactive material disposed between the first and second electrodes, the photoactive material comprising a polymer including first and second comonomer repeat units,
wherein the first comonomer repeat unit comprises a phenyl moiety substituted with 2-4 halo groups or 2-4 C 1 -C 4 trihaloalkyl groups;
the second comonomer repeat unit comprises a cyclopentadithiazole moiety, a benzothiadiazole moiety, a thiadiazoloquinoxaline moiety, a benzoisothiazole moiety, a benzothiazole moiety, a dibenzosilole moiety, a thienothiophene moiety, a carbazole moiety, a dithienothiophene moiety, a tetrahydroisoindole moiety, a silole moiety, a cyclopentadithiophene moiety, a thiazole moiety, a thiazolothiazole moiety, a naphthothiadiazole moiety, a thienopyrazine moiety, a silacyclopentadithiophene moiety, an oxazole moiety, an imidazole moiety, a pyrimidine moiety, a benzoxazole moiety, a benzimidazole moiety, a pyridopyrazine moiety, a pyrazinopyridazine moiety, a pyrazinoquinoxaline moiety, a thiadiazolopyridine moiety, a thiadiazolopyridazine moiety, a benzooxadiazole moiety, an oxadiazolopyridine moiety, an oxadiazolopyridazine moiety, a benzoselenadiazole moiety, a benzobisoxazole moiety, a thienothiadiazole moiety, a thienopyrroledione moiety, a tetrazine moiety, a pyrrolopyrroledione moiety, or a benzotriazole moiety; and
the article is configured as a photovoltaic cell.

2. The article of claim 1 , wherein the first comonomer repeat unit comprises a phenyl moiety of formula (1):

in which each of R 1 , R 2 , R 3 , and R 4 , independently, is H, halo, or C 1 -C 4 trihaloalkyl, provided that at least two of R 1 , R 2 , R 3 , and R 4 is halo or C 1 -C 4 trihaloalkyl.

3. The article of claim 2 , wherein each of R 1 , R 2 , R 3 , and R 4 , independently, is halo.

4. The article of claim 2 , wherein each of R 1 , R 2 , R 3 , and R 4 is fluoro.

5. The article of claim 1 , wherein the second comonomer repeat unit comprises a cyclopentadithiazole moiety of formula (4), a benzothiadiazole moiety of formula (5), a thiadiazoloquinoxaline moiety of formula (6), a benzoisothiazole moiety of formula (7), a benzothiazole moiety of formula (8), a dibenzosilole moiety of formula (9), a thienothiophene moiety of formula (10), a thienothiophene moiety of formula (11), a carbazole moiety of formula (12), a dithienothiophene moiety of formula (13), a tetrahydroisoindole moiety of formula (14), a silole moiety of formula (16), a cyclopentadithiophene moiety of formula (17), a thiazole moiety of formula (18), a thiazolothiazole moiety of formula (19), a naphthothiadiazole moiety of formula (20), a thienopyrazine moiety of formula (21), a silacyclopentadithiophene moiety of formula (22), an oxazole moiety of formula (23), an imidazole moiety of formula (24), a pyrimidine moiety of formula (25), a benzoxazole moiety of formula (26), a benzimidazole moiety of formula (27), a pyridopyrazine moiety of formula (28), a pyrazinopyridazine moiety of formula (29), a pyrazinoquinoxaline moiety of formula (30), a thiadiazolopyridine moiety of formula (31), a thiadiazolopyridazine moiety of formula (32), a benzooxadiazole moiety of formula (33), an oxadiazolopyridine moiety of formula (34), an oxadiazolopyridazine moiety of formula (35), a benzoselenadiazole moiety of formula (36), a benzobisoxazole moiety of formula (37), a benzobisoxazole moiety of formula (38), a thienothiadiazole moiety of formula (39), a thienopyrroledione moiety of formula (40), a tetrazine moiety of formula (41), a pyrrolopyrroledione moiety of formula (42), or a benzotriazole moiety of formula (47):

wherein
each of X and Y, independently, is CH 2 , O, or S;
each of R 5 , R 6 , R 7 , and R 8 , independently, is H, halo, C 1 -C 24 alkyl, C 1 -C 24 alkoxy, aryl, heteroaryl, C 3 -C 24 cycloalkyl, C 3 -C 24 heterocycloalkyl, CN, OR, COR, COOR, or CON(RR′), in which each of R and R′, independently, is H, C 1 -C 24 alkyl, aryl, heteroaryl, C 3 -C 24 cycloalkyl, or C 3 -C 24 heterocycloalkyl; and
each of R 9 and R 10 , independently, is H, C 1 -C 24 alkyl, aryl, heteroaryl, C 3 -C 24 cycloalkyl, or C 3 -C 24 heterocycloalkyl.

6. The article of claim 5 , wherein the second comonomer repeat unit comprises t the silacyclopentadithiophene moiety of formula (22), in which each of R 5 , R 6 , R 7 , and R 8 , independently, is H, C 1 -C 24 alkyl, or COOR.

7. The article of claim 6 , wherein the second comonomer repeat unit comprises silacyclopentadithiophene moiety of formula (22), in which each of R 5 , R 6 , R 7 , and R 8 , independently, is H, C 8 H 17 alkyl, or COOC 12 H 25 .

8. A polymer, comprising first and second comonomer repeat units,
wherein the first comonomer repeat unit comprises a phenyl moiety substituted with 2-4 halo groups or 2-4 C 1 -C 4 trihaloalkyl groups; and
the second comonomer repeat unit comprises a cyclopentadithiazole moiety, a benzothiadiazole moiety, a thiadiazoloquinoxaline moiety, a benzoisothiazole moiety, a benzothiazole moiety, a dibenzosilole moiety, a thienothiophene moiety, a carbazole moiety, a dithienothiophene moiety, a tetrahydroisoindole moiety, a silole moiety, a cyclopentadithiophene moiety, a thiazole moiety, a thiazolothiazole moiety, a naphthothiadiazole moiety, a thienopyrazine moiety, a silacyclopentadithiophene moiety, an oxazole moiety, an imidazole moiety, a pyrimidine moiety, a benzoxazole moiety, a benzimidazole moiety, a pyridopyrazine moiety, a pyrazinopyridazine moiety, a pyrazinoquinoxaline moiety, a thiadiazolopyridine moiety, a thiadiazolopyridazine moiety, a benzooxadiazole moiety, an oxadiazolopyridine moiety, an oxadiazolopyridazine moiety, a benzoselenadiazole moiety, a benzobisoxazole moiety, a thienothiadiazole moiety, a thienopyrroledione moiety, a tetrazine moiety, a pyrrolopyrroledione moiety, or a benzotriazole moiety.

9. The polymer of claim 8 , wherein the first comonomer repeat unit comprises a phenyl moiety of formula (1):

in which each of R 1 , R 2 , R 3 , and R 4 , independently, is H, halo, or C 1 -C 4 trihaloalkyl, provided that at least two of R 1 , R 2 , R 3 , and R 4 is halo or C 1 -C 4 trihaloalkyl.

10. The polymer of claim 9 , wherein each of R 1 , R 2 , R 3 , and R 4 , independently, is halo.

11. The polymer of claim 9 , wherein each of R 1 , R 2 , R 3 , and R 4 is fluoro.

12. The polymer of claim 8 , wherein the second comonomer repeat unit comprises a cyclopentadithiazole moiety of formula (4), a benzothiadiazole moiety of formula (5), a thiadiazoloquinoxaline moiety of formula (6), a benzoisothiazole moiety of formula (7), a benzothiazole moiety of formula (8), a dibenzosilole moiety of formula (9), a thienothiophene moiety of formula (10), a thienothiophene moiety of formula (11), a carbazole moiety of formula (12), a dithienothiophene moiety of formula (13), a tetrahydroisoindole moiety of formula (14

Assignees

• Merck Patent Gmbh

Inventors

• Wen Li
• Waller David P
• Byrne Paul
• Drolet Nicolas
• Dennler Gilles Herve Regis
• Cheon Kap-Soo

Classifications

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• H10K30/20

  comprising organic-organic junctions, e.g. donor-acceptor junctions · CPC title

• H10K85/113

  Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene · CPC title

• H10F99/00

  Subject matter not provided for in other groups of this subclass · CPC title

• H10K30/00 Primary

  Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation (integrated devices or assemblies of multiple devices H10K39/00, H10K65/00; electrolytic light-sensitive devices H01G9/20) · CPC title