Organic semiconductor element, compound, organic semiconductor composition, and method of manufacturing organic semiconductor film

Patent metadata

Field	Value
Publication number	US-2018145259-A1
Application number	US-201715857746-A
Country	US
Kind code	A1
Filing date	Dec 29, 2017
Priority date	Jul 7, 2015
Publication date	May 24, 2018
Grant date	—

Abstract

An object of the present invention is to provide an organic semiconductor element (in particular, an organic thin film transistor) that exhibits high carrier mobility and can stably maintain carrier mobility even after long-term storage under high temperature and high humidity, a compound, an organic semiconductor composition, and a method of manufacturing an organic semiconductor film. The organic semiconductor element of the present invention contains a compound having a molecular weight of 2,000 or greater and a repeating unit represented by Formula (1). In Formula (1), A represents an electron acceptor unit, D is an electron donor unit, and at least one of D or A has at least one monovalent group represented by Formula (1-1). In Formula (1-1), Ar represents an aromatic heterocyclic group or an aromatic hydrocarbon group having 5 to 18 carbon atoms. C a represents CR 1 R 2 . L a represents an alkylene group having 1 to 20 carbon atoms. L b represents an alkyl group having 9 or more carbon atoms. l represents an integer of 1 to 5. * represents a bonding site to another structure.
D-A(1)*-C a -L a -ArL b ) l   (1-1)

First claim

What is claimed is:

1 . An organic semiconductor element comprising:
a compound having a molecular weight of 2,000 or greater and having a repeating unit represented by Formula (1),
D-A  (1)

in Formula (1), A represents an electron acceptor unit including a partial structure having at least one of a sp2 nitrogen atom, a carbonyl group, or a thiocarbonyl group in a ring structure, D represents an electron donor unit including a divalent aromatic heterocyclic group having at least one of a N atom, an O atom, a S atom, or a Se atom in a ring structure or a divalent aromatic hydrocarbon group consisting of a fused ring structure having two or more rings, as a partial structure, and at least one of D or A has at least one monovalent group represented by Formula (1-1),
*-C a -L a -ArL b ) l   (1-1)

in Formula (1-1), Ar represents an aromatic heterocyclic group or an aromatic hydrocarbon group having 5 to 18 carbon atoms, C a represents CR 1 R 2 , L a represents an alkylene group having 1 to 20 carbon atoms that may contain at least one of —O—, —S—, or —NR 3 —, L b represents an alkyl group having 9 or more carbon atoms that may contain at least one of —O—, —S—, or —NR 4 —, R 1 to R 4 each independently represent a hydrogen atom or a substituent, l represents an integer of 1 to 5, in a case where l is 2 or greater, a plurality of L b 's may be identical to as or different from each other, and * represents a bonding site to another structure.

2 . The organic semiconductor element according to claim 1 ,
wherein, in -(L b ) l in Formula (1-1), the number of carbon atoms of at least one L b is 20 to 100.

3 . The organic semiconductor element according to claim 1 ,
wherein A in Formula (1) has at least one structure selected from the group consisting of structures represented by Formulae (A-1) to (A-12), as a partial structure,

in Formulae (A-1) to (A-12), X's each independently represent an O atom, a S atom, a Se atom, or NR A1 ,
Y's each independently represent an O atom or a S atom,
Z a 's each independently represent CR A2 or a N atom,
W's each independently represent C(R A2 ) 2 , NR A1 , a N atom, CR A2 , an O atom, a S atom, or a Se atom,
R A1 's each independently represent an alkyl group that may contain at least one of —O—, —S—, or —NR A3 —, the monovalent group represented by Formula (1-1), or a bonding site to another structure,
R A2 's each independently represent a hydrogen atom, a halogen atom, an alkyl group that may contain at least one of —O—, —S—, or —NR A3 —, or a bonding site to another structure,
R A3 's each independently represent a hydrogen atom or a substituent, and
*'s each independently represent a bonding site to another structure.

4 . The organic semiconductor element according to claim 1 ,
wherein D in Formula (1) is a structure represented by Formula (D-1),

in Formula (D-1), X″s each independently represent O, S, Se, or NR D1 , R D1 's each independently represent a monovalent organic group that may be the monovalent group represented by Formula (1-1),
Z d 's each independently represent N or CR D2 , R D2 's each independently represent a hydrogen atom or a monovalent organic group that may be the monovalent group represented by Formula (1-1),
M represents a single bond, a divalent aromatic heterocyclic group, a divalent aromatic hydrocarbon group, an alkenylene group, an alkynylene group, or a divalent group obtained by combining these, M may be substituted with an alkyl group that may contain at least one of —O—, —S—, or —NR D3 — or the monovalent group represented by Formula (1-1), R D3 's each independently represent a hydrogen atom or a substituent,
p and q each independently represent an integer of 0 to 4, and
*'s each independently represent a bonding site to another structure.

5 . The organic semiconductor element according to claim 1 ,
wherein the repeating unit represented by Formula (1) is a repeating unit represented by any one of Formulae (2) to (5),

in Formulae (2) to (5), X's each independently represent an O atom, a S atom, a Se atom, or NR A1 ,
R A1 's each independently represent an alkyl group that may contain at least one of —O—, —S—, or —NR A3 —, the monovalent group represented by Formula (1-1), or a bonding site to another structure,
Y's each independently represent an O atom or a S atom,
Z a 's each independently represent CR A2 or a N atom, R A2 's each independently represent a hydrogen atom, a halogen atom, an alkyl group that may contain at least one of —O—, —S—, or —NR A3 —, or a bonding site to another structure,
R A3 's each independently represent a hydrogen atom or a substituent,
X″s each independently represent O, S, Se, or NR D1 , R D1 's each independently represent a monovalent organic group that may be the monovalent group represented by Formula (1-1),
Z d 's each independently represent N or CR D2 , R D2 's each independently represent a hydrogen atom or a monovalent organic group that may be the monovalent group represented by Formula (1-1),
M represents a single bond, a divalent aromatic heterocyclic group, a divalent aromatic hydrocarbon group, an alkenylene group, an alkynylene group, or a divalent group obtained by combining these, M may be substituted with an alkyl group that may contain at least one of —O—, —S—, or —NR D3 — or the monovalent group represented by Formula (1-1), R D3 's each independently represent a hydrogen atom or a substituent, and
p and q each independently represent an integer of 0 to 4.

6 . The organic semiconductor element according to claim 3 ,
wherein Formulae (A-1) to (A-12) each have at least one of R A1 or R A2 , and wherein at least one of R A1 or R A2 in each formula is the monovalent group represented by Formula (1-1).

7 . The organic semiconductor element according to claim 5 ,
wherein Formulae (2) to (5) each have at least one of R A1 or R A2 , and wherein at least one of R A1 or R A2 in each formula is the monovalent group represented by Formula (1-1).

8 . A compound having a molecular weight of 2,000 or greater and having a repeating unit represented by Formula (1),
wherein A in Formula (1) has at least one structure selected from the group consisting of structures represented by Formulae (A-1) to (A-12), as a partial structure,
D-A  (1)

in Formula (1), A represents an electron acceptor unit including a partial structure having at least one of a sp2 nitrogen atom, a carbonyl group, or a thiocarbonyl group in a ring structure, D represents an electron donor unit including a divalent aromatic heterocyclic group having at least one of a N atom, an O atom, a S atom, or a Se atom in a ring structure or a divalent aromatic hydrocarbon group consisting of a fused ring structure having two or more rings, as a partial structure, and at least one of D or A has at least one monovalent group represented by Formula (1-1),
*-C a -L a -ArL b ) l   (1-1)

in Formula (1-1), Ar represents an aromatic heterocyclic group or an aromatic hydrocarbon group having 5 to 18 carbon atoms, C a represents CR 1 R 2 , L a represents an alkylene group having 1 to 20 carbon atoms that may contain at

Assignees

• Fujifilm Corp

Inventors

• Yamamoto Yosuke
• Shigenoi Yuta

Classifications

• C08G2261/344

  containing heteroatoms · CPC title

• C08G2261/92

  TFT applications · CPC title

• C08G2261/3243

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

• C08G2261/514

  Electron transport · CPC title

• C08G2261/149

  Side-chains having heteroaromatic units · CPC title