Organic semiconductor composition and method for manufacturing organic semiconductor element

Patent metadata

Field	Value
Publication number	US-10074813-B2
Application number	US-201715648463-A
Country	US
Kind code	B2
Filing date	Jul 13, 2017
Priority date	Mar 17, 2015
Publication date	Sep 11, 2018
Grant date	Sep 11, 2018

Abstract

An object of the present invention is to provide an organic semiconductor composition, which makes it possible to obtain an organic semiconductor film having high mobility and being excellent in film uniformity and heat resistance, and a method for manufacturing an organic semiconductor element.
The organic semiconductor composition of the present invention contains an organic semiconductor as Component A and an organic solvent, which is represented by Formula B-1 and has a melting point of equal to or lower than 25° C. and a boiling point of equal to or higher than 150° C. and equal to or lower than 280° C., as Component B, in which an ionization potential of Component A is equal to or higher than 5.1 eV. In the formula, X represents O, S, S═O, O═S═O, or NR, Y 1 to Y 4 each independently represent NR 1 or CR 10 R 11 , R, R 1 , R 10 , and R 11 each independently represent a hydrogen atom or a substituent, and n represents 1 or 2.

First claim

What is claimed is:

1. An organic semiconductor composition comprising:
an organic semiconductor as Component A; and
an organic solvent, which is represented by Formula B-1 and has a melting point of equal to or lower than 25° C. and a boiling point of equal to or higher than 150° C. and equal to or lower than 280° C., as Component B,
wherein an ionization potential of Component A is equal to or higher than 5.1 eV,

in Formula B-1, X represents O, S, S═O, O═S═O, or NR; Y 1 to Y 4 each independently represent NR 1 or CR 10 R 11 ; R, R 1 , R 10 , and R 11 each independently represent a hydrogen atom or a substituent; n represents 1 or 2; in a case where n is 2, two Y 4 's may be the same as or different from each other; in a case where X is NR, a substituent on Y 1 or Y 4 and the substituent R on N may form a ring or may form a double bond in a 5-membered or 6-membered ring containing X by being bonded to each other; substituents of Y 1 to Y 4 adjacent to each other may form a ring or may form a double bond in a 5-membered or 6-membered ring containing X by being bonded to each other; and in a case where X is O, a substituent of Y 1 and a substituent of Y 2 do not form a double bond by being bonded to each other.

2. The organic semiconductor composition according to claim 1 ,
wherein Component B is an organic solvent which is represented by the following Formula B-2 and has a melting point of equal to or lower than 25° C. and a boiling point of equal to or higher than 150° C. and equal to or lower than 280° C.,

in Formula B-2, X represents O, S, S═O, O═S═O, or NR; n represents 1 or 2; R and R 20 to R 27 each independently represent a hydrogen atom or a substituent; in a case where n is 2, two R 26 's and two R 27 's may be the same as or different from each other; two out of R and R 20 to R 27 may form a ring by being bonded to each other; R and R 20 , R 20 and R 2 , R 2 and R 24 , and R 24 and R 26 may form a double bond in a 5-membered or 6-membered ring containing X by being bonded to each other; and in a case where X is O, R 20 and R 22 do not form a double bond by being bonded to each other.

3. The organic semiconductor composition according to claim 1 ,
wherein Component B is an organic solvent which is represented by any one of the following Formulae B-3 to B-6 and has a melting point of equal to or lower than 25° C. and a boiling point of equal to or higher than 150° C. and equal to or lower than 280° C.,

in Formulae B-3 to B-6, X represents an oxygen atom or a sulfur atom; n represents 1 or 2; R 30 to R 33 , R 40 to R 43 , R 50 to R 55 , and R to R 64 each independently represent a hydrogen atom or a substituent; at least one of R 40 , R 41 , R 42 , or R 43 represents a halogen atom; and R 60 and R 61 and R 61 and R 62 may form a ring by being linked to each other.

4. The organic semiconductor composition according to claim 1 ,
wherein 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 one ring in the condensed polycyclic aromatic group is a heterocyclic ring, and
at least one structure selected from the group consisting of a benzene ring, a naphthalene ring, and a phenanthrene ring is contained as a partial structure in the condensed polycyclic aromatic group.

5. The organic semiconductor composition according to claim 4 ,
wherein the number of rings in the condensed polycyclic aromatic group is 5 or 6.

6. The organic semiconductor composition according to claim 1 ,
wherein Component A contains at least one kind of compound represented by any one of Formulae 1 to 16,

in Formula 1, Ala 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 represented by any one of the following Formulae L-1 to L-25 or a divalent linking group in which 2 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 2 or more silicon atoms, or a trialkylsilyl group,

in Formulae L-1 to L-25, * represents a bonding position with respect to R W , the portion of a wavy line represents a bonding position on the other side, R′ in Formulae L-1, L-2, L-6, and L-13 to L-24 each independently represents 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 represents 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 , and A 3a and A 3b each independently represent CR 3h or a N atom, R 3a to R 3b 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, and 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 , 5 5f , R 5g , or R 5h is a group represented by

Assignees

• Fujifilm Corp

Inventors

• Yamamoto Yosuke
• HONGO Yushi
• Masui Kensuke

Classifications

• H01L51/05

  Electricity · mapped topic

• C09D11/36

  based on non-aqueous solvents · CPC title

• H01L51/0072

  Electricity · mapped topic

• H01L51/0094

  Electricity · mapped topic

• H01L51/0071

  Electricity · mapped topic