Semiconductor materials prepared from dithienylvinylene copolymers

• US 9,650,461 B2
• Filed: 11/19/2015
• Issued: 05/16/2017
• Est. Priority Date: 12/18/2008
• Status: Active Grant

• Current Assignee: Flexterra, Inc.
• Original Assignee: BASF SE, Flexterra, Inc.
• Inventors: Kastler, Marcel, Mishra, Ashok Kumar, Doetz, Florian, Koehler, Silke, Noguchi, Hiroyoshi, Vaidyanathan, Subramanian
• Primary Examiner(s): Fang, Shane
• Application Number:
  US14/946,190
• Publication Number:
  US 20160075808A1
• Time in Patent Office: 544 Days
• CPC Class Codes: C08F 228/06 by a heterocyclic ring containing sulfur
• CPC Class Codes: C08G 2261/124 alternating
• CPC Class Codes: C08G 2261/18 conjugated
• CPC Class Codes: C08G 2261/3223 containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
• CPC Class Codes: C08G 2261/3327 alkene-based
• CPC Class Codes: C08G 2261/344 containing heteroatoms
• CPC Class Codes: C08G 2261/364 containing hetero atoms
• CPC Class Codes: C08G 2261/414 Stille reactions
• CPC Class Codes: C08G 2261/512 Hole transport
• CPC Class Codes: C08G 2261/5222 electrofluorescent
• CPC Class Codes: C08G 2261/91 Photovoltaic applications
• CPC Class Codes: C08G 2261/92 TFT applications
• CPC Class Codes: C08G 61/126 with a five-membered ring containing one sulfur atom in the ring
• CPC Class Codes: C08K 3/01 characterized by their specific function
• CPC Class Codes: C08K 5/0008 Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1416 Condensed systems
• CPC Class Codes: C09K 2211/1425 Non-condensed systems
• CPC Class Codes: C09K 2211/1458 containing sulfur as the only heteroatom
• CPC Class Codes: C09K 2211/1491 containing other combinations of heteroatoms
• CPC Class Codes: H10K 10/466 : Lateral bottom-gate IGFETs comprising only a single gate
• CPC Class Codes: H10K 10/484 : characterised by the channel regions
• 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 85/113 : Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
• CPC Class Codes: H10K 85/151 : Copolymers
• 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 herein are new semiconductor materials prepared from dithienylvinylene copolymers with aromatic or heteroaromatic π-conjugated systems. Such copolymers, with little or no post-deposition heat treatment, can exhibit high charge carrier mobility and/or good current modulation characteristics. In addition, the polymers of the present disclosure can possess certain processing advantages such as improved solution-processability and low annealing temperature.

Claims

1. A polymer, comprising a repeat unit is selected from the group consisting of the formula Ia and Ia′

;

2. The polymer of claim 1, wherein the repeat unit is selected from the group consisting of:

3. The polymer according to claim 1, wherein the repeat unit is the formula:

4. The polymer according to claim 1, wherein n is an integer between 2 and 5000.

5. A composition, comprising one or more polymers of claim 1 dissolved or dispersed in a liquid medium.

6. The composition of claim 5, wherein the liquid medium comprises water or an organic solvent.

7. The composition of claim 5, further comprising one or more additives.

8. The composition of claim 7, wherein the additives are independently selected from the group consisting of viscosity modulators, detergents, dispersants, binding agents, compatiblizing agents, curing agents, initiators, humectants, antifoaming agents, wetting agents, pH modifiers, biocides, and bactereriostats.

9. A thin film semiconductor, comprising one or more polymers of claim 1.

10. A field effect transistor device, comprising the thin film semiconductor of claim 9.

11. The field effect transistor device of claim 10, wherein the field effect transistor has a structure selected from top-gate bottom-contact structure, bottom-gate top-contact structure, top-gate top-contact structure, and bottom-gate bottom-contact structure.

12. A photovoltaic device, comprising the thin film semiconductor of claim 9.

13. An organic light emitting device, comprising the thin film semiconductor of claim 9.

14. The polymer according to claim 1, wherein when the repeat unit is a structure of formula Ia, m″

is 2, 3, 4, 5, 6, 7, 8, 9 or 10, and when the repeat unit is a structure of formula Ia′

, m″

is 3, 4, 5, 6, 7, 8, 9 or 10.