Organic film transistor, organic semiconductor film, organic semiconductor material and application of these

Patent metadata

Field	Value
Publication number	US-9653686-B2
Application number	US-201614993371-A
Country	US
Kind code	B2
Filing date	Jan 12, 2016
Priority date	Jul 19, 2013
Publication date	May 16, 2017
Grant date	May 16, 2017

Abstract

An organic film transistor containing a compound, which is composed of n repeating units represented by Formula (1-1), (1-2), or (101), in a semiconductor active layer is an organic film transistor using a compound that results in high carrier mobility when being used in the semiconductor active layer of the organic film transistor and exhibits high solubility in an organic solvent;

(Each of R 1 R 2 represents a hydrogen atom or a substituent; each of Ar 1 and Ar 2 independently represents a heteroarylene group or an arylene group; V 1 represents a divalent linking group; m represents an integer of 0 to 6; cy represents a naphthalene ring or an anthracene ring; each of R 3 and R 4 represents a hydrogen atom or a substituent; each of Ar 3 and Ar 4 represents a heterocyclic aromatic ring or an aromatic ring; V 2 represents a divalent linking group; p represents an integer of 0 to 6; n represents an integer of equal to or greater than 2; A is a divalent linking group represented by Formula (101′); each of R A1 to R A6 represents a hydrogen atom, a substituent, or a direct bond with Ar 101 or Ar 102 in Formula (101); and among the groups represented by R A1 to R A6 , two different groups are direct bonds with Ar 101 and Ar 102 in Formula (101) respectively.)

First claim

What is claimed is:

1. An organic film transistor comprising a compound, which is composed of n repeating units represented by the following Formula (1-1), (1-2), or (101), in a semiconductor active layer;

in Formula (1-1), each of R 1 and R 2 independently represents a hydrogen atom or a substituent; each of Ar 1 and R 2 independently represents a heteroarylene group or an arylene group; V 1 represents a divalent linking group; m represents an integer of 0 to 6; when m is equal to or greater than 2, two or more groups represented by V 1 may be the same as or different from each other; and n represents an integer of equal to or greater than 2;

in Formula (1-2), cy represents a naphthalene ring or an anthracene ring; each of R 3 and R 4 independently represents a hydrogen atom or a substituent; each of Ar 3 and Ar 4 independently represents a heteroarylene group or an arylene group; V 2 represents a divalent linking group; p represents an integer of 0 to 6; when p is equal to or greater than 2, two or more groups represented by V 2 may be the same as or different from each other; and n represents an integer of equal to or greater than 2;

in Formula (101), each of Ar 101 and Ar 102 independently represents a heteroarylene group or an arylene group; V 101 represents a divalent linking group; m 101 represents an integer of 1 to 6; when m 101 is equal to or greater than 2, two or more groups represented by V 101 may be the same as or different from each other; n represents an integer of equal to or greater than 2; and A represents a divalent linking group represented by the following Formula (101′); and

in Formula (101′), each of R A1 to R A6 independently represents a hydrogen atom, a substituent, or a direct bond with Ar 101 or Ar 102 in Formula (101); and among the groups represented by R A1 to R A6 , two different groups represent direct bonds with Ar 101 and Ar 102 in Formula (101) respectively,
the transistor further comprising a compound, which is composed of n repeating units represented by Formula (101), in the semiconductor active layer;
in Formula (101), each of Ar 101 and Ar 102 independently represents a heteroarylene group or an arylene group; V 101 represents a divalent linking group; m 101 represents an integer of 1 to 6; when m 101 is equal to or greater than 2, two or more groups represented by V 101 may be the same as or different from each other; n represents an integer of equal to or greater than 2; and A represents a divalent linking group represented by Formula (101′); and
in Formula (101′), each of R A1 to R A6 independently represents a hydrogen atom, a substituent, or a direct bond with Ar 101 or Ar 102 in Formula (101); and among the groups represented by R A1 to R A6 , two different groups represent direct bonds with Ar 101 and Ar 102 in Formula (101) respectively, wherein
the compound composed of n repeating units represented by Formula (101) is a compound composed of n repeating units represented by any of the following Formulae (101-1) to (101-3);

in Formulae (101-1), (101-2), and (101-3), each of R 101 to R 104 and R 141 to R 148 independently represents a hydrogen atom or a substituent; each of Ar 101 and Ar 102 independently represents a heteroarylene group or an arylene group; V 101 represents a divalent linking group; m 101 represents an integer of 1 to 6; when m 101 is equal to or greater than 2, two or more groups represented by V 101 may be the same as or different from each other; each of p 101 and r 101 represents an integer of 0 to 6; when each of p 101 and r 101 is equal to or greater than 2, two or more groups represented by V 101 may be the same as or different from each other; and n represents an integer of equal to or greater than 2, wherein in Formulae (101-1) to (101-3), V 101 is a divalent linking group represented by any of the following Formulae (V-101) to (V-117);

in Formulae (V-101) to (V-117), * represents a position where the divalent linking group is bonded to any of Ar 101 and Ar 102 when m 101 , p 101 , or r 101 is 1 and represents a position where the divalent linking group is bonded to an of Ar 101 ,Ar 102 , and divalent linking groups represented by Formulae (V-101) to (V-117) m 101 , p 101 , or r 101 is equal to or greater than 2; each R v in Formulae (V-101), (V-102), (V-105), (V-106), (V-109) to (V-111), (V-113) to (V-115), and (V-117) independently represents a hydrogen atom or an alkyl group; the groups adjacent to each other represented by R v may form a ring by being bonded to each other; each Z in Formulae (V-104), (V-107), (V-108), and (V-112) independently represents a hydrogen atom, an alkyl group, or an alkoxy group; the groups adjacent to each other represented by Z may form a ring by being bonded to each other; each Y in Formula (V-116) independently represents a hydrogen atom, an alkyl group, an alkoxy group, a CN group, or a F atom; and the groups adjacent to each other represented by Y may form a ring by being bonded to each other, and
in Formulae (101-1) to (101-3), V 101 represents a divalent linking group represented by any of Formulae (V-101) to (V-108) and (V-111) to (V-115).

2. The organic film transistor according to claim 1 , comprising a compound, which is composed of n repeating units represented by the following Formula (1-1) or (1-2), in the semiconductor active layer;

in Formula (1-1), each of R 1 and R 2 independently represents a hydrogen atom or a substituent; each of Ar 1 and Ar 2 independently represents a heteroarylene group or an arylene group; V 1 represents a divalent linking group; m represents an integer of 0 to 6; when m is equal to or greater than 2, two or more groups represented by V 1 may be the same as or different from each other; and n represents an integer of equal to or greater than 2; and

in Formula (1-2), cy represents a naphthalene ring or an anthracene ring; each of R 3 and R 4 independently represents a hydrogen atom or a substituent; each of Ar 3 and Ar 4 independently represents a heteroarylene group or an arylene group; V 2 represents a divalent linking group; p represents an integer of 0 to 6; when p is equal to or greater than 2, two or more groups represented by V 2 may be the same as or different from each other; and n represents an integer of equal to or greater than 2.

3. The organic film transistor according to claim 1 ,
wherein Formula (1-2) represents a compound composed of n repeating units represented by the following Formula (2-1), (2-2), (2-3), (2-4), or (2-5);

in Formulae (2-1) to (2-5), each of R 3 , R 4 , and R 10 to R 33 independently represents a hydrogen atom or a substituent; each of Ar 3 and Ar 4 independently represents a heteroarylene group or a

Assignees

• Fujifilm Corp

Inventors

• Takaku Koji
• Kaneko Akihiro
• Sugiura Hiroki
• Masui Kensuke
• Yonekuta Yasunori
• Hirai Yuki
• Koyanagi Masashi

Classifications

• C08G2261/3325

  derived from other polycyclic systems · CPC title

• C08G2261/344

  containing heteroatoms · CPC title

• C08G2261/1412

  Saturated aliphatic units · CPC title

• C08G2261/149

  Side-chains having heteroaromatic units · CPC title

• C08G2261/314

  Condensed aromatic systems, e.g. perylene, anthracene or pyrene · CPC title