IP Library Granted Patent US 8,643,001
Granted Patent B2
US 8,643,001 · App. 12/977,464 · Granted Feb 4, 2014

Semiconductor composition

Inventors: Yiliang Wu (Oakville, CA); Anthony James Wigglesworth (Oakville, CA); Ping Liu (Mississauga, CA); Nan-Xing Hu (Oakville, CA)
Assignee: Samsung Electronics Co. Ltd.
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Quick Facts
Patent No.
US 8,643,001
App. No.
12/977,464
Granted
Feb 4, 2014
Kind
B2
Abstract

An electronic device, such as a thin-film transistor, includes a semiconducting layer formed from a semiconductor composition. The semiconductor composition comprises a polymer binder and a small molecule semiconductor of Formula (I): wherein R 1 , m, n, a, b, c, and X are as described herein. Devices formed from the composition exhibit high mobility and excellent stability.

Claims (42)

1. A semiconductor composition comprising:

a polymer binder; and

a small molecule semiconductor 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, ketonyl, cyano, and halogen; m and n are the number of R1 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;

wherein the semiconductor composition is capable of forming a layer having a field-effect mobility greater than 0.10 cm 2 /V·sec.

2. The semiconductor composition of claim 1 , wherein the small molecule semiconductor has the structure of Formula (II):

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

3. The semiconductor composition of claim 2 , wherein the polymer binder is a styrene-based polymer or an arylamine-based polymer.

4. The semiconductor composition of claim 3 , wherein the polymer binder is polystyrene, poly(α-methyl styrene), poly(4-methyl styrene), poly(alpha-methyl styreneco-vinyl toluene), poly(styrene-block-butadiene-block-styrene), poly(styrene-block-isopene-block-styrene), poly (vinyl toluene), a terpene resin, poly(styrene-co-2,4-dimethylstyrene), poly(chlorostyrene), poly(styrene-co-α-methyl styrene), poly(styreneco-butadiene), polycarbazole, a polytriarylamine, or poly(N-vinylcarbazole).

5. The semiconductor composition of claim 2 , wherein the polymer binder is a styrene-based polymer having a weight average molecular weight of from about 40,000 to about 2,000,000.

6. The semiconductor composition of claim 1 , wherein the polymer binder has a dielectric constant less than 3.5.

7. The semiconductor composition of claim 1 , wherein the small molecule semiconductor has the structure of Formula (II):

wherein R 2 , and R 3 are independently alkyl or substituted alkyl; and wherein the polymer binder is a styrene-based polymer or an arylamine-based polymer.

8. The semiconductor composition of claim 7 , wherein the polymer binder is polystyrene, poly(α-methyl styrene), poly(4-methyl styrene), poly(alpha-methyl styreneco-vinyl toluene), poly(styrene-block-butadiene-block-styrene), poly(styrene-block-isopene-block-styrene), poly (vinyl toluene), a terpene resin, poly(styrene-co-2,4-dimethylstyrene), poly(chlorostyrene), poly(styrene-co-α-methyl styrene), poly(styreneco-butadiene), polycarbazole, a polytriarylamine, or poly(N-vinylcarbazole).

9. The semiconductor composition of claim 8 , wherein the polymer binder is a styrene-based polymer having a weight average molecular weight of from about 100,000 to about 1,000,000.

10. The semiconductor composition of claim 1 , wherein the small molecule semiconductor has the structure of Formula (III):

wherein R 8 , and R 9 are independently alkyl or substituted alkyl; and each Ar is independently an arylene or heteroarylene group.

11. The semiconductor composition of claim 1 , wherein the small molecule semiconductor is selected from Formulas (1) through (50):

wherein each R′ is independently alkyl or substituted alkyl containing from about 4 to about 20 carbon atoms.

12. The semiconductor composition of claim 1 , wherein the small molecule semiconductor has the structure of Formula (IV):

wherein 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, ketonyl, cyano, and halogen; and j

and k are independently an integer from 0 to 6.

13. The semiconductor composition of claim 12 , wherein R 4 and R 5 are

independently alkyl, j is 1, and k is 1.

14. The semiconductor composition of claim 12 , wherein the polymer binder is a styrene-based polymer or an arylamine-based polymer.

15. The semiconductor composition of claim 1 , wherein the weight ratio of the small molecule semiconductor of Formula (I) to the polymer binder is from about 5:1 to about 2:3, and the total amount of the small molecule semiconductor and the polymer binder is from about 0.1 to about 10 weight percent of the semiconductor composition.

16. The semiconductor composition of claim 1 , wherein the small molecule semiconductor has the structure of Formula (V):

wherein 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, ketonyl, cyano, and halogen; and p and q are independently an integer from 0 to 4.

17. The semiconductor composition of claim 1 , wherein the small molecule semiconductor has the structure of Formula (VI):

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, ketonyl, cyano, and halogen; and a, b, and c are independently 0 or 1.

18. A process for making a semiconducting layer of an electronic device, comprising:

depositing upon a surface a composition comprising a polymer binder and a small molecule semiconductor 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, ketonyl, cyano, and halogen; m and n are the number of R1 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; and

drying the composition at a temperature below the melting point of the small molecular semiconductor; and

optionally annealing the composition at a temperature below the melting point of the small molecular semiconductor to form the semiconducting layer;

wherein the semiconducting layer has a mobility of at least 0.10 cm 2 /V·sec.

19. An electronic device comprising a semiconducting layer, wherein the semiconductor layer comprises a polymer binder and a small molecule semiconductor 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, ketonyl, cyano, and halogen; m and n are the number of R1 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, Se; and a, b and care independently 0 or 1; and

wherein the semiconducting layer has a field-effect mobility of at least 0.10 cm 2 /V·sec.

20. The electronic device of claim 19 , wherein the electronic device further comprises a dielectric layer having a modified surface in contact with the semiconductor layer which has been modified with a polystyrene, a polysiloxane, a polysilsesquioxane, or an organosilane agent of Formula (A):

R m —S—(R″) 4-m   Formula (A)

wherein R is hydrocarbon or fluorocarbon containing from 1 to about 20 carbon atoms, R″ is halogen or alkoxy; and m is an integer from 1 to 4.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 3, 2013
From: XEROX CORPORATION
To: SAMSUNG ELECTRONICS CO. LTD.
Reel/Frame 030733/0970 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 25, 2013
From: XEROX CORPORATION
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 030682/0757 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 23, 2010
From: WU, YILIANG; WIGGLESWORTH, ANTHONY JAMES; LIU, PING; HU, NAN-XING
To: XEROX CORPORATION
Reel/Frame 025567/0713 →
Continuity (1)
Related Publication 20120161110A1 · Jun 28, 2012