IP Library Granted Patent US 8,425,808
Granted Patent B2
US 8,425,808 · App. 12/767,992 · Granted Apr 23, 2013

Semiconducting composition

Inventors: Yiliang Wu (Oakville, CA); Ping Liu (Mississauga, CA); Anthony James Wigglesworth (Oakville, CA); Nan-Xing Hu (Oakville, CA)
Assignee: Xerox Corporation
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Quick Facts
Patent No.
US 8,425,808
App. No.
12/767,992
Granted
Apr 23, 2013
Kind
B2
Abstract

The present application discloses, in various embodiments, semiconducting layer compositions comprising a non-amorphous semiconductor material and a molecular glass. Electronic devices, such as thin-film transistors, are also disclosed. The semiconducting layer compositions exhibit good film-forming properties and high mobility.

Claims (44)

1. A semiconducting composition comprising a non-amorphous semiconductor material and a molecular glass;

wherein the molecular glass is selected from the group consisting of:

(A) a spiro compound of Formula (1) or Formula (2):

wherein each R substituent is independently selected from the group consisting of hydrogen, alkyl comprising from about 1 to about 18 carbon atoms, aryl or substituted aryl haying from about 3 to about 18 carbon atoms, hydroxyl, protected hydroxyl, amino, protected amino, —OR′, —OCOOR′, —CNO, —NHCOOR′, hydroxyphenyl, —COOH, and epoxy, and R′ is alkyl;

(B) a structure selected from one of Formula (3) to Formula (8):

wherein each R is independently selected from the group consisting of hydrogen, alkyl comprising from about 1 to about 18 carbon atoms, aryl or substituted aryl having from about 3 to about 18 carbon atoms, hydroxyl, protected hydroxyl, amino, protected amino, —OR′, —OCOOR′, —CNO, —NHCOOR′, hydroxyphenyl, —COOH, and epoxy, and R′ is alkyl;

(C) a silane of Formula (9):

wherein each R is independently selected from the group consisting of hydrogen, alkyl comprising from about 1 to about 18 carbon atoms, aryl or substituted aryl having from about 3 to about 18 carbon atoms, hydroxyl, protected hydroxyl, amino, protected amino, —OR′, —OCOOR′, —CNO, —NHCOOR′, hydroxyphenyl, —COOH, and epoxy: R′ is alkyl; and m and n are both integers, wherein m+n=4:

(D) an adamantane derivative of Formula (10):

wherein each R is independently a substituent comprising a heteroatom;

(E) a structure selected from one of Formula (11) to Formula (13):

wherein each R substituent is independently selected from the group consisting of hydrogen, alkyl comprising from about 1 to about 18 carbon atoms, aryl or substituted aryl having from about 3 to about 18 carbon atoms, hydroxyl, protected hydroxyl, amino, protected amino, —OR′, —OCOOR′, —CNO, —NHCOOR′, hydroxyphenyl, —COOH, and epoxy; and R′ is alkyl;

(F) a calixarene derivative of Formula (14):

wherein each R substituent is independently selected from the group consisting of hydrogen, alkyl comprising from about 1 to about 18 carbon atoms, aryl or substituted aryl having from about 3 to about 18 carbon atoms, hydroxyl, protected hydroxyl, amino, protected amino, —OR′, —OCOOR′, —CNO, —NHCOOR′, hydroxyphenyl, —COOH and epoxy; R′ alkyl; and each R 1 is a phenyl group substituted with an oxygen-containing radical; and

(G) an arylamine derivative selected from one of Formula (16)-(24):

wherein each R, R 1 , and R 2 substituent is independently selected from the group consisting of hydrogen, alkyl comprising from about 1 to about 18 carbon atoms, aryl or substituted aryl having from about 3 to about 18 carbon atoms, hydroxyl, protected hydroxyl, amino, protected amino, —OR′, —OCOOR′, —CNO, —NHCOOR′, hydroxyphenyl, —COON, and epoxy; R′ is alkyl; n is an integer from 1 to 6; and Ar is independently selected from aryl, heteroaryl, substituted aryl, and substituted heteroaryl.

2. The semiconducting composition of claim 1 , wherein individual molecules of the molecular glass are crosslinked with different molecules of the molecular glass or with molecules of a different amorphous molecular material.

3. The semiconducting composition of claim 1 , wherein the non-amorphous semiconductor material is represented by Formula (Ia) or (Ib):

wherein R 1 and R 2 are independently selected from hydrogen, alkyl, aryl, alkoxy, substituted alkyl, substituted aryl, substituted alkoxy, trialkylsilyl, cyano, nitro, or a halogen; R 3 and R 4 are independently selected from alkyl, aryl, alkoxy, substituted alkyl, substituted aryl, substituted alkoxy, hydrogen, trialkylsilyl, cyano, nitro, or a halogen; R 5 and R 8 are independently selected from hydrogen, halogen, cyano, nitro, alkyl, aryl, alkoxy, substituted alkyl, substituted aryl, substituted alkoxy, or trialkylsilyl; Ar is independently selected from aryl, heteroaryl, substituted aryl, and substituted heteroaryl; Z represents —CH═CH—, sulfur, oxygen, selenium, or NR, wherein R is hydrogen or a hydrocarbon such as alkyl or aryl; x and y are independently from 0 to about 6; a and b are independently from 0 to about 3; and c and d are independently from 0 to about 4.

4. The semiconducting composition of claim 1 , wherein the non-amorphous semiconductor material is represented by one of Formulas (25)-(41):

wherein R 7 is independently selected from the group consisting of hydrogen, halogen, alkyl, phenyl substituted with one alkyl chain, or trialkylsilyl.

5. The semiconducting composition of claim 1 , wherein the non-amorphous semiconductor material is a crystalline, semicrystalline, or liquid crystalline semiconductor.

6. The semiconducting composition of claim 1 , wherein the molecular glass has a dielectric constant less than 4.0.

7. An electronic device comprising a semiconducting layer; wherein the semiconducting layer comprises a non-amorphous semiconductor material and a molecular glass; and wherein the molecular glass is selected from the group consisting of:

(A) a spiro compound of Formula (1) or Formula (2):

wherein each R substituent is independently selected from the group consisting of hydrogen, alkyl comprising from about 1 to about 18 carbon atoms, aryl or substituted aryl having from about 3 to about 18 carbon atoms, hydroxyl, protected hydroxyl, amino, protected amino, —OR′, —OCOOR′, —CNO, —NHCOOR′, hydroxyphenyl, —COOH, and epoxy, and R′ is alkyl;

(B) a structure selected from one of Formula (3) to Formula (8):

wherein each R is independently selected from the group consisting of hydrogen, alkyl comprising from about 1 to about 18 carbon atoms, aryl or substituted aryl having from about 3 to about 18 carbon atoms, hydroxyl, protected hydroxyl, amino, protected amino, —OR′, —OCOOR′, —CNO, —NHCOOR′, hydroxyphenyl, —COOH, and epoxy, and R′ is alkyl;

(C) a silane of Formula (9):

wherein each R is independently selected from the group consisting of hydrogen, alkyl comprising from about 1 to about 18 carbon atoms, aryl or substituted aryl having from about 3 to about 18 carbon atoms, hydroxyl, protected hydroxyl, amino, protected amino, —OR′, —OCOOR′, —CNO, —NHCOOR′, hydroxyphenyl, —COON, and, epoxy; R′ is alkyl; and m and n are both integers, wherein m+n=4;

(D) an adamantane derivative of Formula (10):

wherein each R is independently a substituent comprising a heteroatom;

(E) a structure selected from one of Formula (11) to Formula (13):

wherein each R substituent is independently selected from the group consisting of hydrogen, alkyl comprising from about 1 to about 18 carbon atoms, aryl or substituted aryl having from about 3 to about 18 carbon atoms, hydroxyl, protected hydroxyl, amino, protected amino, —OR′, —OCOOR′, —CNO, —NHCOOR′, hydroxyphenyl, —COOH, and epoxy; and R′ is alkyl;

(F) a calixarene derivative of Formula (14):

wherein each R substituent is independently selected from the group consisting of hydrogen, alkyl comprising from about 1 to about 18 carbon atoms, aryl or substituted aryl having from about 3 to about 18 carbon atoms, hydroxyl, protected hydroxyl, amino, protected amino, —OR′, —OCOOR′, —CNO, —NHCOOR′, hydroxyphenyl, —COOH and epoxy; R′ is alkly; and each R 1 is a phenyl group substituted with an oxygen-containing radical; and

(G) an arylamine derivative selected from one of Formula (16)-(24):

wherein each R, R 1 , and R 2 substituent is independently selected from the group consisting of hydrogen, alkyl comprising from about 1 to about 18 carbon atoms, aryl or substituted aryl having from about 3 to about 18 carbon atoms, hydroxyl, protected hydroxyl, amino, protected amino, —OR′, —OCOOR′, —CNO, —NHCOOR′, hydroxyphenyl, —COOH, and epoxy; R′ is alkyl; n is an integer from 1 to 6; and Ar is independently selected from aryl, heteroaryl, substituted aryl, and substituted heteroaryl.

8. The electronic device of claim 7 , wherein the electronic device is a thin-film transistor.

9. An electronic device comprising a semiconducting layer; wherein the semiconducting layer comprises a non-amorphous semiconductor material and a molecular glass;

wherein the non-amorphous semiconductor material is represented by Formula (26a) or (26b):

wherein R 7 is independently selected from the group consisting of hydrogen, halogen, alkyl, phenyl substituted with one alkyl chain, or trialkylsilyl; and

wherein the molecular glass is represented by Formula (16):

wherein each R substituent is independently selected from the group consisting of hydrogen, alkyl comprising from about 1 to about 18 carbon atoms, aryl or substituted aryl having from about 3 to about 18 carbon atoms, hydroxyl, protected hydroxyl, amino, protected amino, —OR′, —OCOOR′, —CNO, —NHCOOR′, hydroxyphenyl, —COOH, and epoxy.

Assignments (2)
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 Apr 27, 2010
From: WU, YILIANG; LIU, PING; WIGGLESWORTH, ANTHONY JAMES; HU, NAN-XING
To: XEROX CORPORATION
Reel/Frame 024293/0487 →
Continuity (1)
Related Publication 20110260114A1 · Oct 27, 2011