IP Library Granted Patent US 7,425,723
Granted Patent B2
US 7,425,723 · App. 11/314,687 · Granted Sep 16, 2008

Organic thin-film transistors

Assignee: Xerox Corporation
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Quick Facts
Patent No.
US 7,425,723
App. No.
11/314,687
Granted
Sep 16, 2008
Kind
B2
Abstract

An organic thin-film transistor has a p-type semiconducting layer, wherein the semiconducting layer comprises a crystalline conjugated polyarylamine of the chemical structure: wherein R 1 through R 5 are independently selected from hydrogen, alkyl having from about 1 to about 30 carbon atoms, aryl having from about 6 to about 40 carbon atoms, heteroaryl having from about 3 to about 40 atoms, alkoxy having from about 1 to about 30 carbon atoms, aryloxy having from about 6 to about 40 carbon atoms, and substituted derivatives thereof; wherein A and B are the same or different independently selected from arylenes having from about 6 to about 20 carbon atoms or heteroarylenes having from about 3 to about 20 carbon atoms; and wherein n is the degree of polymerization; and wherein the polyarylamine has a mobility (μ 0 ) of 10 −4 cm 2 /V·sec or greater.

Claims (37)

1. An organic thin-film transistor having a p-type semiconducting layer, wherein the semiconducting layer comprises a crystalline conjugated polyarylamine having the chemical structure of Formula (I):

wherein R 1 through R 5 are independently selected from hydrogen, alkyl having from about 1 to about 30 carbon atoms, aryl having from about 6 to about 40 carbon atoms, heteroaryl having from about 3 to about 40 atoms, alkoxy having from about 1 to about 30 carbon atoms, aryloxy having from about 6 to about 40 carbon atoms, and substituted derivatives thereof; wherein A and B are the same or different independently selected from arylenes having from about 6 to about 20 carbon atoms or heteroarylenes having from about 3 to about 20 carbon atoms; and wherein n is the degree of polymerization;

and wherein the polyarylamine has a mobility (μ 0 ) of 10 −4 cm 2 /V·sec or greater.

2. The organic thin-film transistor of claim 1 , wherein the polyarylamine has the chemical structure of Formula (II):

wherein R 6 is independently selected from hydrogen, alkyl having from about 1 to about 30 carbon atoms, aryl having from about 6 to about 40 carbon atoms, heteroaryl having from about 3 to about 40 atoms, alkoxy having from about 1 to about 30 carbon atoms, aryloxy having from about 6 to about 40 carbon atoms, and substituted derivatives thereof; wherein A and B are the same or different independently selected from arylenes having from about 6 to about 20 carbon atoms or heteroarylenes having from about 3 to about 20 carbon atoms; and wherein n is the degree of polymerization.

3. The organic thin-film transistor of claim 2 , wherein R 6 is alkyl.

4. The organic thin-film transistor of claim 2 , wherein A and B are phenylene.

5. The organic thin-film transistor of claim 4 , wherein A and B are phenylene and R 6 is alkyl.

6. The organic thin-film transistor of claim 2 , wherein R 6 is a fluorine-substituted alkyl or aryl.

7. The organic thin-film transistor of claim 2 , wherein n is from about 2 to about 5000.

8. The organic thin-film transistor of claim 1 , wherein n is from about 2 to about 5000.

9. The organic thin-film transistor of claim 1 , wherein A and B are phenylene.

10. The organic thin-film transistor of claim 1 , wherein at least one of R 1 through R 5 is a fluorine-substituted alkyl or aryl.

11. The organic thin-film transistor of claim 1 , wherein A and B are phenylene; R 1 , R 2 , R 4 , and R 5 are hydrogen; and R 3 is alkyl.

12. The organic thin-film transistor of claim 1 , wherein the semiconducting layer is from about 5 nm to about 1000 nm thick.

13. The organic thin-film transistor of claim 1 , further comprising a dielectric layer comprising an organic polymer film.

14. The organic thin-film transistor of claim 1 , further comprising at least one electrode made from a material selected from the group consisting of aluminum, gold, chromium, indium tin oxide, nickel, and platinum.

15. The organic thin-film transistor of claim 1 , further comprising at least one electrode made from a conductive polymer.

16. The organic thin-film transistor of claim 1 , wherein the transistor is a top-contact thin film transistor.

17. The organic thin-film transistor of claim 1 , wherein the transistor has an on/off ratio greater than about 10 3 .

18. The organic thin-film transistor of claim 17 , wherein the transistor has an on/off ratio from about 10 4 to about 10 5 .

19. An organic thin-film transistor, comprising:

a supporting substrate;

a gate electrode, a source electrode, and a drain electrode;

a dielectric layer; and

a p-type semiconducting layer;

wherein the semiconducting layer comprises a crystalline conjugated polyarylamine having the chemical structure of Formula (I):

 wherein R 1 through R 5 are independently selected from hydrogen, alkyl having from about 1 to about 30 carbon atoms, aryl having from about 6 to about 40 carbon atoms, heteroaryl having from about 3 to about 40 atoms, alkoxy having from about 1 to about 30 carbon atoms, aryloxy having from about 6 to about 40 carbon atoms, and substituted derivatives thereof; wherein A and B are the same or different independently selected from arylenes having from about 6 to about 20 carbon atoms or heteroarylenes having from about 3 to about 20 carbon atoms; and wherein n is the degree of polymerization;

and wherein the polyarylamine has a mobility (μ 0 ) of 10 −4 cm 2 /V·sec or greater.

20. An organic thin-film transistor, comprising:

a supporting substrate;

a gate electrode, a source electrode, and a drain electrode;

a dielectric layer; and

a p-type semiconducting layer;

wherein the semiconducting layer comprises a crystalline conjugated polyarylamine having the chemical structure of Formula (II):

 wherein R 6 is independently selected from hydrogen, alkyl having from about 1 to about 30 carbon atoms, aryl having from about 6 to about 40 carbon atoms, heteroaryl having from about 3 to about 40 atoms, alkoxy having from about 1 to about 30 carbon atoms, aryloxy having from about 6 to about 40 carbon atoms, and substituted derivatives thereof; wherein A and B are the same or different independently selected from arylenes having from about 6 to about 20 carbon atoms or heteroarylenes having from about 3 to about 20 carbon atoms; and wherein n is the degree of polymerization;

and wherein the polyarylamine has a mobility (μ 0 ) of 10 −4 cm 2 /V·sec or greater.

Assignments (9)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 6, 2025
From: XEROX CORPORATION
To: GENESEE VALLEY INNOVATIONS, LLC
Reel/Frame 073842/0479 →
SECOND LIEN NOTES PATENT SECURITY AGREEMENT Recorded Jul 2, 2025
From: XEROX CORPORATION
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 071785/0550 →
FIRST LIEN NOTES PATENT SECURITY AGREEMENT Recorded Apr 11, 2025
From: XEROX CORPORATION
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 070824/0001 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS RECORDED AT RF 064760/0389 Recorded Feb 13, 2024
From: CITIBANK, N.A., AS COLLATERAL AGENT
To: XEROX CORPORATION
Reel/Frame 068261/0001 →
SECURITY INTEREST Recorded Nov 20, 2023
From: XEROX CORPORATION
To: JEFFERIES FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 065628/0019 →
SECURITY INTEREST Recorded Jun 22, 2023
From: XEROX CORPORATION
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 064760/0389 →
RELEASE OF SECURITY INTEREST IN PATENTS AT R/F 062740/0214 Recorded May 18, 2023
From: CITIBANK, N.A., AS AGENT
To: XEROX CORPORATION
Reel/Frame 063694/0122 →
SECURITY INTEREST Recorded Nov 10, 2022
From: XEROX CORPORATION
To: CITIBANK, N.A., AS AGENT
Reel/Frame 062740/0214 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 21, 2005
From: ONG, BENG S.; LI, YUNING; WU, YILIANG; LIU, PING
To: XEROX CORPORATION
Reel/Frame 017408/0374 →
Continuity (1)
Related Publication 20070160847A1 · Jul 12, 2007