IP Library Granted Patent US 10,381,583
Granted Patent B2
US 10,381,583 · App. 14/098,330 · Granted Aug 13, 2019

Electronic device

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Quick Facts
Patent No.
US 10,381,583
App. No.
14/098,330
Granted
Aug 13, 2019
Kind
B2
Abstract

An electronic device includes a substrate, a gate electrode, a dielectric layer, a source electrode, a drain electrode, and a semiconducting layer formed from an organic semiconductor compound and a photo-responsive polymer. The resistance can be switched to a “low” state by irradiation, and can be switched to a “high” state by applying a gate bias voltage. This can be useful for a memory device.

Claims (41)

1. An electronic device, comprising:

a substrate;

a first electrode and a second electrode contacting a semiconducting layer, wherein the semiconducting layer comprises an organic semiconductor and a photo-responsive polymer, wherein the photo-responsive polymer forms a matrix within which the organic semiconductor is dispersed; and

a dielectric layer separating a third electrode from the semiconducting layer, the first electrode, and the second electrode;

wherein the photo-responsive polymer includes a monomer of Formula (G-1):

2. The electronic device of claim 1 , wherein the organic semiconductor is an organic semiconducting compound or a semiconducting polymer.

3. The electronic device of claim 1 , wherein the organic semiconductor is a compound having the structure of Formula (I):

wherein each R 1 is independently selected from alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxy, alkylthio, trialkylsilyl, aldehyde, cyano, and halogen; f and g are the number of R 1 sidechains on their respective phenyl or naphthyl ring, and are independently an integer from 0 to 6; X is selected from the group consisting of O, S, and Se; and a, b, and c are independently 0 or 1.

4. The electronic device of claim 3 , wherein the organic semiconductor has the structure of Formula (II):

wherein R 2 and R 3 are independently selected from alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxy, alkylthio, trialkylsilyl, aldehyde, cyano, and halogen.

5. The electronic device of claim 4 , wherein the organic semiconductor has the structure of Formula (II-a):

6. The electronic device of claim 3 , wherein the organic semiconductor has the structure of Formula (III):

wherein R 2 and R 3 are independently selected from alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxy, alkylthio, trialkylsilyl, aldehyde, cyano, and halogen.

7. The electronic device of claim 3 , wherein the organic semiconductor has the structure of Formula (IV):

wherein each R 4 and R 5 are independently selected from alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxy, alkylthio, trialkylsilyl, aldehyde, cyano, and halogen; and j and k are independently an integer from 0 to 6.

8. The electronic device of claim 3 , wherein the organic semiconductor has the structure of Formula (V):

wherein each R 6 and R 7 are independently selected from alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxy, alkylthio, trialkylsilyl, aldehyde, cyano, and halogen; and j and k are independently an integer from 0 to 4.

9. The electronic device of claim 3 , wherein the organic semiconductor has the structure of Formula (VI):

wherein R 8 and R 9 are independently selected from alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxy, alkylthio, trialkylsilyl, aldehyde, cyano, and halogen.

10. The electronic device of claim 1 , wherein the organic semiconductor has the structure of Formula (VII):

wherein R d through R h are independently selected from alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, trialkylsilylalkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxy, alkylthio, trialkylsilyl, aldehyde, cyano, and halogen; and Z is selected from the group consisting of O, S, Se, and —CH═CH—.

11. The electronic device of claim 10 , wherein the organic semiconductor has the structure of Formula (VIII):

wherein R 10 and R 11 are independently selected from alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxy, alkylthio, trialkylsilyl, aldehyde, cyano, and halogen; and

wherein R 12 is alkyl or substituted alkyl.

12. The electronic device of claim 11 , wherein the organic semiconductor has the structure of Formula (VIII-a) or (VIII-b):

13. The electronic device of claim 10 , wherein the organic semiconductor has the structure of Formula (IX):

wherein R 12 is alkyl or substituted alkyl.

14. The electronic device of claim 1 , wherein the photo-responsive polymer is a copolymer.

15. The electronic device of claim 14 , wherein the monomer of Formula (G-1) is from about 1 mole % to about 50 mole % of the copolymer.

16. The electronic device of claim 1 , wherein the photo-responsive polymer has the structure of Formula (a):

wherein x and y are the mole ratio for the respective monomer, and are between 0 and 1.

17. The electronic device of claim 1 , wherein the weight ratio of the organic semiconductor to the photo-responsive polymer is from about 25:75 to about 95:5.

18. The electronic device of claim 1 , wherein the organic semiconductor has a band gap of from about 1.2 to about 3.5 eV.

19. The electronic device of claim 1 , wherein the device is a memory device that further comprises a light source adapted to illuminate the semiconducting layer.

20. The memory device of claim 19 , wherein the substrate is transparent and the light source illuminates the semiconducting layer through the substrate.

21. The electronic device of claim 1 , wherein the difference between the HOMO level of the organic semiconductor and the HOMO level of the photo-responsive polymer is not greater than 0.5 eV.

22. A semiconductor composition comprising:

an organic semiconductor;

a photo-responsive polymer having the structure of Formula (a):

wherein x and y are the mole ratio for the respective monomer, and are between 0 and 1; and

a non-photo-responsive polymer.

Assignments (10)
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 →
SECURITY INTEREST Recorded Feb 13, 2024
From: XEROX CORPORATION
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 066741/0001 →
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 6, 2013
From: WU, YILIANG; SMITHSON, CHAD; ZHU, SHIPING
To: XEROX CORPORATION
Reel/Frame 031727/0808 →