IP Library Granted Patent US 9,212,254
Granted Patent B2
US 9,212,254 · App. 14/556,767 · Granted Dec 15, 2015

Copolymer, organic semiconductor material, organic electrical device, photovoltaic module

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Quick Facts
Patent No.
US 9,212,254
App. No.
14/556,767
Granted
Dec 15, 2015
Kind
B2
Abstract

A copolymer containing a repeating unit having a dioxopyrrole condensed ring skeleton and a repeating unit having a dithieno condensed ring skeleton and also having a specific substituent is provided.

Claims (37)

1. A copolymer, comprising:

a repeating unit represented by Formula (1A);

a repeating unit represented by Formula (1B); and

a repeating unit represented by Formula (1C),

where A represents an atom selected from elements of Group 16 of the periodic table,

each of Q 1 and Q 2 independently represents an atom selected from elements of Group 14 of the periodic table,

R 1 represents a hydrocarbon group optionally having a heteroatom,

R 2 represents an optionally substituted branched alkyl group,

R 4 represents an optionally substituted linear alkyl group, optionally substituted aromatic hydrocarbon group, or optionally substituted aromatic heterocyclic group,

each of R 3 and R 5 independently represents an optionally substituted branched alkyl group, optionally substituted linear alkyl group, optionally substituted cycloalkyl group, optionally substituted aromatic hydrocarbon group, optionally substituted aliphatic heterocyclic group, or optionally substituted aromatic heterocyclic group, and

at least one of a combination of R 2 and R 5 and a combination of R 3 and R 4 is a combination of groups that are different from each other, wherein a ratio of the repeating units represented by Formula (1B) and a ratio of the repeating units represented by Formula (1C) each satisfies 1 mol % or more and 98 mol % or less.

2. The copolymer according to claim 1 , wherein the copolymer comprises a repeating unit represented by Formula (2A) and a repeating unit represented by Formula (2B),

wherein each of A 1 and A 2 independently represents an atom selected from elements of group 16 of the periodic table,

each of Q 1 and Q 2 independently represents an atom selected from elements of Group 14 of the periodic table,

each of R 1 and R 6 independently represents a hydrocarbon group optionally having a heteroatom,

R 2 represents an optionally substituted branched alkyl group,

R 4 represents an optionally substituted linear alkyl group, optionally substituted aromatic hydrocarbon group, or optionally substituted aromatic heterocyclic group,

each of R 3 and R 5 independently represents an optionally substituted branched alkyl group, optionally substituted linear alkyl group, optionally substituted cycloalkyl group, optionally substituted aromatic hydrocarbon group, optionally substituted aliphatic heterocyclic group, or optionally substituted aromatic heterocyclic group, and

at least one of a combination of R 2 and R 5 and a combination of R 3 and R 4 is a combination of groups that are different from each other.

3. An organic semiconductor material, comprising the copolymer according to claim 1 .

4. An organic electronic device, comprising the organic semiconductor material according to claim 3 .

5. The organic electronic device according to claim 4 , which is a photoelectric conversion element.

6. The organic electronic device according to claim 4 , which is a photovoltaics.

7. A photovoltaic module, comprising the organic electronic device according to claim 6 .

8. An organic semiconductor material, comprising the copolymer according to claim 2 .

9. An organic electronic device comprising the organic semiconductor material according to claim 8 .

10. The organic electronic device according to claim 9 , which is a photoelectric conversion element.

11. The organic electronic device according to claim 9 , which is a photovoltaics.

12. A photovoltaic module comprising the organic electronic device according to claim 11 .

13. The copolymer according to claim 1 , wherein A represents O or S.

14. The copolymer according to claim 1 , wherein each of Q 1 and Q 2 independently represents C, Si, Ge, or Sn.

15. The copolymer according to claim 1 , wherein R 1 is selected from the group consisting of an optionally substituted alkyl group, optionally substituted alkenyl group, optionally substituted aromatic hydrocarbon group, and optionally substituted aromatic heterocyclic group.

16. The copolymer according to claim 1 , wherein R 4 is an optionally substituted linear alkyl group, and each of R 3 and R 5 is independently selected from the group consisting of an optionally substituted branched alkyl group, an optionally substituted linear alkyl group, an optionally substituted aromatic hydrocarbon group, and optionally substituted aromatic heterocyclic group.

17. The copolymer according to claim 2 , wherein each of A 1 and A 2 independently represents O or S.

18. The copolymer according to claim 2 , wherein each of Q 1 and Q 2 independently represents C, Si, Ge, or Sn.

19. The copolymer according to claim 2 , wherein each of R 1 and R 6 is independently selected from the group consisting of an optionally substituted alkyl group, optionally substituted alkenyl group, optionally substituted aromatic hydrocarbon group, and optionally substituted aromatic heterocyclic group.

20. The copolymer according to claim 2 , wherein R 4 is an optionally substituted linear alkyl group, and each of R 3 and R 5 is independently selected from the group consisting of an optionally substituted branched alkyl group, an optionally substituted linear alkyl group, and optionally substituted aromatic hydrocarbon group, and optionally substituted aromatic heterocyclic group.

Assignments (3)
CHANGE OF NAME Recorded Sep 5, 2017
From: MITSUBISHI RAYON CO., LTD.
To: MITSUBISHI CHEMICAL CORPORATION
Reel/Frame 043750/0834 →
MERGER Recorded Sep 4, 2017
From: MITSUBISHI CHEMICAL CORPORATION
To: MITSUBISHI RAYON CO., LTD.
Reel/Frame 043750/0207 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 2, 2014
From: KAWAI, JUNYA; FUJITA, RIEKO; SATO, WATARU; FURUYA, MITSUNORI; SATAKE, KENICHI; OBA, MAKI
To: MITSUBISHI CHEMICAL CORPORATION
Reel/Frame 034299/0809 →