Organic semiconducting polymers

• US 8,664,339 B2
• Filed: 11/06/2009
• Issued: 03/04/2014
• Est. Priority Date: 11/07/2008
• Status: Active Grant

• Current Assignee: BASF SE, Flexterra, Inc.
• Original Assignee: BASF SE, Polyera Corporation
• Inventors: Facchetti, Antonio
• Primary Examiner(s): Truong, Duc
• Application Number:
  US13/128,214
• Publication Number:
  US 20110213117A1
• Time in Patent Office: 1,579 Days
• Field of Search: 525/282, 525/279, 525/242, 528/322, 528/310, 257/40
• US Class Current: 525/282
• CPC Class Codes: C08G 2261/3241 containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
• CPC Class Codes: C08G 2261/3243 containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene
• CPC Class Codes: C08G 2261/3246 containing nitrogen and sulfur as heteroatoms
• CPC Class Codes: C08G 2261/344 containing heteroatoms
• CPC Class Codes: C08G 61/12 Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
• CPC Class Codes: C08G 61/122 derived from five- or six-membered heterocyclic compounds, other than imides
• CPC Class Codes: C08G 61/123 derived from five-membered heterocyclic compounds
• CPC Class Codes: C08G 61/124 with a five-membered ring containing one nitrogen atom in the ring
• CPC Class Codes: C08G 61/126 with a five-membered ring containing one sulfur atom in the ring
• CPC Class Codes: C09B 69/109 containing other specific dyes
• CPC Class Codes: H10K 10/466 Lateral bottom-gate IGFETs comprising only a single gate
• CPC Class Codes: H10K 30/00 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 Class Codes: H10K 30/50 Photovoltaic [PV] devices
• CPC Class Codes: H10K 85/111 comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
• CPC Class Codes: H10K 85/113 Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
• CPC Class Codes: H10K 85/621 Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
• CPC Class Codes: Y02E 10/549 Organic PV cells
• CPC Class Codes: Y02P 70/50 Manufacturing or production processes characterised by the final manufactured product

Abstract

Disclosed are new organic semiconducting polymers. The polymers disclosed herein can exhibit high carrier mobility and/or efficient light absorption/emission characteristics, and can possess certain processing advantages such as solution-processability and/or good stability at ambient conditions.

Claims

1. A homopolymer or copolymer comprising a repeating unit M₁ selected from:

2. A copolymer according to claim 1 having the formula:

3. The homopolymer or copolymer of claim 1, wherein M₁ is

4. The hompolymer or copolymer of claim 1, wherein M₁ is selected from:

5. A copolymer according to claim 2, wherein Z is selected from:

6. A copolymer according to claim 2, wherein π

-2 is an optionally substituted C_8-22 aryl group or 8-22 membered heteroaryl group selected from;

7. A copolymer according to claim 2, wherein Ar, at each occurrence, is independently selected from:

8. A copolymer according to claim 1, wherein (Ar)_m, (Ar)_m′

, and (Ar)_m″

are selected from;

9. A copolymer according to claim 2, wherein π

-2 is selected from;

10. A copolymer according to claim 2, wherein M₂ is selected from:

11. A copolymer according to claim 2, wherein M₂ is selected from:

12. A copolymer according to claim 2, wherein M₂ is selected from:

13. A homopolymer or copolymer according to claim 1, wherein R¹, at each occurrence, is independently selected from:

14. A homopolymer or copolymer according to claim 1, wherein R¹ is independently selected from a branched C_3-40 alkyl group or a branched C_3-40 alkenyl group.

15. A homopolymer or copolymer according to claim 1, wherein R¹ is independently selected from an n-hexyl group, a 1-methylhexyl group, a 2-ethylhexyl group, and a 2-octyldodecyl group.

16. A homopolymer or copolymer according to claim 1, wherein R¹ is a -L-C_3-14 cycloalkyl group optionally substituted with 1-4 C_1-6 alkyl groups, wherein L is as defined in claim 1.

17. A homopolymer or copolymer according to claim 1, wherein n is an integer between 4 and 1,000.

18. An article of manufacture comprising a thin film semiconductor comprising one or more homopolymers or copolymers of claim 1.

19. The article of manufacture of claim 18, wherein the article of manufacture is an electronic device, an optical device, or an optoelectronic device.

20. The article of manufacture of claim 18, wherein the article of manufacture is selected from an organic field effect transistor device, an organic photovoltaic device, and an organic light emitting device.