Organic semiconductor element, manufacturing method thereof, organic semiconductor composition, organic semiconductor film, compound, and oligomer or polymer

Patent metadata

Field	Value
Publication number	US-9954172-B2
Application number	US-201715593337-A
Country	US
Kind code	B2
Filing date	May 12, 2017
Priority date	Nov 25, 2014
Publication date	Apr 24, 2018
Grant date	Apr 24, 2018

Abstract

An object is to provide an organic semiconductor element having excellent carrier mobility and heat resistance of a semiconductor active layer, an organic semiconductor composition for obtaining this element, an organic semiconductor film, and a method of manufacturing an organic semiconductor element in which the composition is used, and another object is to provide a compound and an oligomer or a polymer that are suitably used in the organic semiconductor element, the organic semiconductor composition, the organic semiconductor film, and the method of manufacturing an organic semiconductor element.
The organic semiconductor element of the present invention includes a compound represented by Formula 1 below in a semiconductor active layer. In Formula 1, X represents a chalcogen atom, p and q each independently represent an integer of 0 to 2, and R 1 and R 2 each independently represent a halogen atom or a group represented by Formula W below.

First claim

What is claimed is:

1. A compound represented by Formula 1, or an oligomer or a polymer, the oligomer or the polymer comprising a constitutional repeating unit including a structure represented by Formula 3:

wherein, in Formula 1, X represents a chalcogen atom, p and q each independently represent an integer of 0 to 2, and R 1 and R 2 each independently represent a halogen atom or a group represented by Formula W below,
—S-L-T  (W)

wherein, in Formula W, S represents a single bond or —(C(R s ) 2 ) n —, each R s independently represents a hydrogen atom or a halogen atom, n represents an integer of 1 to 17, L represents a single bond, a divalent linking group represented by any one of Formulae L-1 to L-15 below, or a divalent linking group obtained by bonding two or more divalent linking groups represented by any one of Formulae L-1 to L-15 below, and T represents an alkyl group, a haloalkyl group, a cyano group, a vinyl group, an ethynyl group, an aryl group, a heteroaryl group, an oxyethylene group, an oligooxyethylene group in which a repetition number of oxyethylene units is 2 or greater, a siloxane group, an oligosiloxane group having two or more silicon atoms, or a trialkylsilyl group, and

wherein, in Formulae L-1 to L-15, a wavy line portion represents a bonding position to S or another divalent linking group represented by any one of Formulae L-1 to L-15, * represents a bonding position to T or another divalent linking group represented by any one of Formulae L-1 to L-15, m in Formula L-13 represents an integer of 0 to 4, m in Formulae L-14 and L-15 represents an integer of 0 to 2, each R′ in Formulae L-1 and L-2 independently represents a hydrogen atom, a halogen atom or an alkyl group and each R″ in Formulae L-13, L-14, and L-15 independently represents a halogen atom, an alkyl group, an alkynyl group, an alkenyl group, an alkoxy group, an alkylthiogroup or an aryl group; and

wherein, in Formula 3,each X 3 independently represents a chalcogen atom, R 31 and R 32 each independently represent a hydrogen atom, a halogen atom, a substituent represented by Formula W below, and * represents a bonding position,
—S-L-T  (W)

wherein, in Formula W, S represents a single bond or —(C(R s ) 2 ) n —, each R s independently represents a hydrogen atom or a halogen atom, n represents an integer of 1 to 17, L represents a single bond, a divalent linking group represented by any one of Formulae L-1 to L-15 below, or a divalent linking group obtained by bonding two or more divalent linking groups represented by any one of Formulae L-1 to L-15 below, and T represents an alkyl group, a haloalkyl group, a cyano group, a vinyl group, an ethynyl group, an aryl group, a heteroaryl group, an oxyethylene group, an oligooxyethylene group in which a repetition number of oxyethylene units is 2 or greater, a siloxane group, an oligosiloxane group having two or more silicon atoms, or a trialkylsilyl group, and

wherein, in Formulae L-1 to L-15, a wavy line portion represents a bonding position to S or another divalent linking group represented by any one of Formulae L-1 to L-15, * represents a bonding position to T or another divalent linking group represented by any one of Formulae L-1 to L-15, m in Formula L-13 represents an integer of 0 to 4, m in Formulae L-14 and L-15 represents an integer of 0 to 2, each R′ in Formulae L-1 and L-2 independently represents a hydrogen atom, a halogen atom or an alkyl group, and each R″ in Formulae L-13, L-14, and L-15 independently represents a halogen atom, an alkyl group, an alkynyl group, an alkenyl group, an alkoxy group, an alkylthiogroup or an aryl group.

2. An organic semiconductor element comprising any one selected from the group consisting of the compound, oligomer and polymer according to claim 1 in a semiconductor active layer.

3. The organic semiconductor element according to claim 2 ,
wherein at least one of p or q in Formula 1 represents 1 or 2.

4. The organic semiconductor element according to claim 2 ,
wherein at least one of p or q in Formula 1 represents 1 or 2, and
wherein at least one of R 1 or R 2 represents a group represented by Formula W.

5. The organic semiconductor element according to claim 2 ,
wherein p and q in Formula 1 represent 1.

6. The organic semiconductor element according to claim 2 ,
wherein the compound represented by Formula 1 is a compound represented by Formula 2-1 or 2-2 below,

wherein each X in Formula 2-1 and 2-2 independently represents a chalcogen atom, and R 1 ′ and R 2 ′ each independently represent a group represented by Formula W.

7. The organic semiconductor element according to claim 2 ,
wherein every X is an S atom.

8. The organic semiconductor element according to claim 2 ,
wherein a compound represented by Formula 1 is point symmetric about a point A below,

wherein, in the compound represented by Formula 1 that is point symmetric about point A, p and q each represent an integer of 0 to 2, and R 1 and R 2 each represent a halogen atom or a group represented by Formula W.

9. The organic semiconductor element according to claim 2 ,
wherein a sum of the numbers of carbon atoms of a group represented by Formula W is from 2 to 40.

10. The organic semiconductor element according to claim 2 ,
wherein L in Formula W represents a divalent linking group represented by any one selected from the group consisting of Formulae L-1 to L-4 and L-13 to L-15, or by a divalent linking group obtained by bonding two or more divalent linking groups represented by any one selected from the group consisting of Formulae L-1 to L-4 and L-13 to L-15.

11. The organic semiconductor element according to claim 2 ,
wherein an oligomer or a polymer having a constitutional repeating unit including a structure represented by Formula 3 is conjugated in a main chain direction.

12. The organic semiconductor element according to claim 2 ,
wherein a constitutional repeating unit including a structure represented by Formula 3 further includes a structure represented by Formula Z below,
—Ar 1 —(V) p—Ar 2 —  (Z)

wherein, in Formula Z, Ar 1 and Ar 2 each independently represent a single bond, a vinylene group, an ethynylene group, an arylene group, a heteroarylene group, or a divalent group obtained by bonding two or more of these, and
wherein V represents a single bond or a divalent conjugate group having from 2 to 40 carbon atoms, p represents 1 to 6, two or more instances of V may be identical to or different from each other when p is 2 or greater, and all of Ar 1 , Ar 2 , and V are not simultaneously single bonds.

13. The organic semiconductor element according to claim 12
wherein the oligomer or the polymer having a constitutional repeating unit including a structure represented by Formula 3 is an oligomer or a polymer obta

Assignees

• Fujifilm Corp

Inventors

• Hirai Yuki
• Masui Kensuke

Classifications

• C08G2261/92

  TFT applications · CPC title

• C08G2261/53

  liquid-crystalline · CPC title

• C08G2261/414

  Stille reactions · CPC title

• C08G2261/334

  containing heteroatoms · CPC title

• C08G2261/3243

  containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene · CPC title