Composition for forming organic semiconductor film, organic semiconductor element, and method for manufacturing organic semiconductor element

Patent metadata

Field	Value
Publication number	US-10355215-B2
Application number	US-201615367185-A
Country	US
Kind code	B2
Filing date	Dec 2, 2016
Priority date	Jul 18, 2014
Publication date	Jul 16, 2019
Grant date	Jul 16, 2019

Abstract

The composition for forming an organic semiconductor film of the present invention contains an organic semiconductor as a component A and a polymer chemically modified some or all of the ethylenically unsaturated double bonds of a ethylenically unsaturated double bond-containing polymer, as a component B. It is preferable that the ethylenically unsaturated double bond-containing polymer is at least one kind of polymer selected from the group consisting of natural rubber, an acrylonitrile-butadiene copolymer, polyisoprene, a styrene-butadiene copolymer, polybutadiene, polychloroprene, an ethylene-propylene-diene copolymer, a styrene-butadiene-styrene block copolymer, and a styrene-isoprene-styrene block copolymer.

First claim

What is claimed is:

1. A composition for forming an organic semiconductor film comprising:
an organic semiconductor as a component A; and
a polymer chemically modified some or all of the ethylenically unsaturated double bonds of an ethylenically unsaturated double bond-containing polymer, as a component B.

2. The composition for forming an organic semiconductor film according to claim 1 ,
wherein the ethylenically unsaturated double bond-containing polymer is at least one kind of polymer selected from the group consisting of natural rubber, an acrylonitrile-butadiene copolymer, polyisoprene, a styrene-butadiene copolymer, polybutadiene, polychloroprene, an ethylene-propylene-diene copolymer, a styrene-butadiene-styrene block copolymer, and a styrene-isoprene-styrene block copolymer.

3. The composition for forming an organic semiconductor film according to claim 1 ,
wherein the ethylenically unsaturated double bond-containing polymer is at least one kind of polymer selected from the group consisting of polybutadiene and an ethylene-propylene-diene copolymer.

4. The composition for forming an organic semiconductor film according to claim 1 ,
wherein the ethylenically unsaturated double bond-containing polymer contains an ethylene-propylene-diene copolymer.

5. The composition for forming an organic semiconductor film according to claim 1 ,
wherein the component A is a condensed polycyclic aromatic compound having 3 to 7 rings.

6. The composition for forming an organic semiconductor film according to claim 1 ,
wherein in the component B, a modification rate of the ethylenically unsaturated double bonds in the ethylenically unsaturated double bond-containing polymer is 5% to 50%.

7. The composition for forming an organic semiconductor film according to claim 1 ,
wherein the component A has a condensed polycyclic aromatic group,
the number of rings in the condensed polycyclic aromatic group is equal to or greater than 4,
at least two rings in the condensed polycyclic aromatic group contains at least 1 atom selected from the group consisting of a sulfur atom, a nitrogen atom, a selenium atom, and an oxygen atom, and
the condensed polycyclic aromatic group has, as a partial structure, at least one structure selected from the group consisting of a benzene ring, a naphthalene ring, and a phenanthrene ring.

8. The composition for forming an organic semiconductor film according to claim 7 ,
wherein the number of rings in the condensed polycyclic aromatic group is 5 or 6.

9. The composition for forming an organic semiconductor film according to claim 7 ,
wherein the condensed polycyclic aromatic group contains at least two heterocyclic rings, and
the heterocyclic rings each contain one heteroatom.

10. The composition for forming an organic semiconductor film according to claim 1 ,
wherein the component A contains at least one kind of compound represented by any one of Formulae 1 to 16,

in Formula 1, A 1a and A 1b each independently represent a S atom, an O atom, or a Se atom, R 1a to R 1f each independently represent a hydrogen atom or a substituent, and at least one of R 1a , R 1b , R 1c , R 1d , R 1e , or R 1f is a group represented by the following Formula W,
-L W -R W   (W)

in Formula W, L W represents a divalent linking group which is represented by any one of the following Formula L-1 to L-25 or a divalent linking group in which two or more divalent linking groups represented by any one of the following Formulae L-1 to L-25 are bonded to each other, and R W represents an alkyl group, a cyano group, a vinyl group, an ethynyl group, an oxyethylene group, an oligo-oxyethylene group in which a repetition number v of an oxyethylene unit is equal to or greater than 2, a siloxane group, an oligosiloxane group having two or more silicon atoms, or a trialkylsilyl group,

in Formulae L-1 to L-25, * represents a bonding position for R W , the portion of a wavy line represents the other bonding position, R′ in Formulae L-1, L-2, L-6, and L-13 to L-24 each independently represent a hydrogen atom or a substituent, R N in Formulae L-20 and L-24 represents a hydrogen atom or a substituent, and R si in Formula L-25 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group,
in Formula 2, X 2a and X 2b each independently represent NR 2i , an O atom, or a S atom, A 2a represents CR 2g or a N atom, A 2b represents CR 2h or a N atom, R 2i represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, or an acyl group, R 2a to R 2h each independently represent a hydrogen atom or a substituent, and at least one of R 2a , R 2b , R 2c , R 2d , R 2e , R 2f , R 2g , or R 2h is a group represented by Formula W,
in Formula 3, X 3a and X 3b each independently represent a S atom, an O atom, or NR 3g , A 3a and A 3b each independently represent CR 3h or a N atom, R 3a to R 3h each independently represent a hydrogen atom or a substituent, and at least one of R 3a , R 3b , R 3c , R 3d , R 3e , R 3f , R 3g , or R 3h is a group represented by Formula W,
in Formula 4, X 4a and X 4b each independently represent an O atom, a S atom, or a Se atom, 4p and 4q each independently represent an integer of 0 to 2, R 4a to R 4j , R 4k , and R 4m each independently represent a hydrogen atom, a halogen atom, or a group represented by Formula W, at least one of R 4a , R 4b , R 4c , R 4d , R 4e , R 4f , R 4g , R 4h , R 4i , R 4j , R 4k , or R 4m is a group represented by Formula W, and in a case where at least one of R 4e or R 4f is a group represented by Formula W, L W in Formula W represented by R 4e and R 4f is a divalent linking group represented by Formula L-2 or L-3,
in Formula 5, X 5a and X 5b each independently represent NR 5i , an O atom, or a S atom, A 5a represents CR 5g or a N atom, A 5b represents CR 5h or a N atom, R 5i represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an acyl group, an aryl group, or a heteroaryl group, R 5a to R 5h each independently represent a hydrogen atom or a substituent, and at least one of R 5a , R 5b , R 5c , R 5d , R 5e , R 5f , R 5g , or R 5h is a group represented by Formula W,
in Formula 6, X 6a to X 6d each independently represent NR 6g , an O atom, or a S atom, R 6g represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an acyl group, an aryl group, or a heteroaryl group, R 6a to R 6f each independently represent a hydrogen atom or a substituent, and at least one of R 6a , R 6b , R 6c , R 6d , R 6e , or R 6f is a group represented by Formula W,
in Formula 7, X 7a and X 7c each independently represent a S atom, an O atom, a Se atom, or NR 7i , X 7b and X 7d each independently represent a S atom, an O atom, or a Se atom, R 7a to R 7i each independently represent a hydrogen atom or a substituent, and at least one of R 7a , R 7b , R 7c , R 7d , R 7e , R 7f , R 7g , R 7h , or R 7i is a group represented by Formula W,
in Formula 8, X 8a and X 8c each independently represent a S atom, an O atom, a Se atom, or NR

Assignees

• Fujifilm Corp

Inventors

• Nakayama Takafumi
• Kikuchi Wataru
• Masui Kensuke

Classifications

• H01L51/0074

  Electricity · mapped topic

• C09D5/24 Primary

  Electrically-conducting paints {(conductive materials H01B1/00)} · CPC title

• H01L51/0558

  Electricity · mapped topic

• C08F236/20

  unconjugated · CPC title

• H01L51/0068

  Electricity · mapped topic