Organic semiconductor element, organic semiconductor composition, method of manufacturing organic semiconductor film, organic semiconductor film, and compound and polymer using the same

Patent metadata

Field	Value
Publication number	US-2020028092-A1
Application number	US-201916588574-A
Country	US
Kind code	A1
Filing date	Sep 30, 2019
Priority date	Mar 31, 2017
Publication date	Jan 23, 2020
Grant date	—

Abstract

in which X1 represents a nitrogen atom or CRa, and rings A to B each represent a specific nitrogen-containing ring; Y1 represents an oxygen atom, a sulfur atom, CRb2, or NRc; V1 represents NRd, an oxygen atom, a sulfur atom, or a selenium atom; Ra to Rd each represent a hydrogen atom or a substituent; R1 represents a specific substituent, and p is an integer of 0 to 2; n represents 1 or 2; and * represents a bonding site.

First claim

What is claimed is:

1 . An organic semiconductor element, comprising:
an organic semiconductor layer containing a compound represented by Formula (1), a compound represented by Formula (2), and/or a compound represented by Formula (3), or containing a polymer having at least one structural unit represented by any one of Formulae (8) to (10),

in each formula, X 1 represents a nitrogen atom or CR a , rings A and B each are a 5-membered or 6-membered aromatic heterocyclic ring having a nitrogen atom as a ring-constituting atom or a fused ring including a 5-membered or 6-membered aromatic heterocyclic ring having a nitrogen atom as a ring-constituting atom,
Y 1 represents an oxygen atom, a sulfur atom, CR b 2 , or NR c ,
V 1 represents NR d , an oxygen atom, a sulfur atom, or a selenium atom,
R a , R b , R c , and R d each represent a hydrogen atom or a substituent,
R 1 represents a halogen atom or a group represented by Formula (W), and p is an integer of 0 to 2,
n represents 1 or 2,
* represents a bonding site,
*-L-T  Formula (W)

in Formula (W), L is a single bond, or a divalent group represented by any one of Formulae (L-1) to (L-25), or a divalent group formed by bonding two or more divalent groups represented by any of (L-1) to (L-25),
T represents a hydrogen atom, a halogen atom, or a cyano group,
* represents a bonding site,

in Formulae (L-1) to (L-25), the wavy line portion represents a bonding site to a ring structure represented by Formula (1) to (3), and (8) to (10), or a bonding site to * of a divalent group represented by any one of Formulae (L-1) to (L-25),
* represents a bonding site to T, or a bonding site to a wavy line portion of a divalent group represented by any one of Formulae (L-1) to (L-25),
in Formulae (L-1), (L-2), (L-6), and (L-13) to (L-24), R A represents a hydrogen atom or a substituent,
in Formula (L-13), m is an integer of 1 to 4, m in Formulae (L-14) and (L-15) is an integer of 1 to 3, and m in Formulae (L-16) to (L-20) is 1 or 2, and m in Formula (L-22) is an integer of 1 to 6,
in Formulae (L-20) and (L-24), R N represents a hydrogen atom or a substituent, and
in Formula (L-25), R si represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group.

2 . The organic semiconductor element according to claim 1 ,
wherein in Formulae (1) to (3), and (8) to (10), Y 1 represents an oxygen atom or a sulfur atom.

3 . The organic semiconductor element according to claim 1 ,
wherein rings A and B each are a fused ring structure represented by Formula (4) or (5),

in each formula, rings C and D each represent a 5-membered aromatic ring or a 6-membered aromatic ring, or a fused ring including a 5-membered aromatic ring or a 6-membered aromatic ring,
R 2 represents a hydrogen atom, a halogen atom, or a group represented by Formula (W), and
* represents a bonding site,
here, in the fused ring structure represented by Formula (4) or (5) in Formulae (8) the (10), the rings C and D each have one bonding site for being incorporated into a polymer chain.

4 . The organic semiconductor element according to claim 3 ,
wherein the fused ring structure represented by Formula (4) is a fused ring structure represented by Formula (6) or (7),

in each formula, R 3 and R 4 each represent a halogen atom or a group represented by Formula (W),
q is an integer of 0 to 4, and r is an integer of 0 to 2, and
W 1 represents a chalcogen atom,
here, in the fused ring structure represented by Formula (6) or (7) in Formulae (8) to (10), one of the ring-constituting atoms of a ring which may have R 3 or R 4 has a bonding site to be incorporated into a polymer chain.

5 . The organic semiconductor element according to claim 4 ,
wherein the rings A and B each are a fused ring structure represented by Formula (7), here, in the fused ring structure represented by Formula (7) in Formulae (8) to (10), one of the ring-constituting atoms of the ring which may have R 4 has one bonding site for being incorporated into a polymer chain.

6 . The organic semiconductor element according to claim 1 ,
wherein, in Formula (W), L is a divalent group selected from Formulae (L-1), (L-2), (L-3), (L-4), (L-13), (L-17), and (L-18), or a group obtained by bonding two or more divalent groups selected from Formulae (L-1), (L-2), (L-3), (L-4), (L-13), (L-17), and (L-18).

7 . The organic semiconductor element according to claim 1 ,
wherein the polymer has a structure represented by Formula (G),
*—Ar 1 -(Vr) p3 -Ar 2 —*  Formula (G)

in Formula (G), Ar 1 and Ar 2 each represent a single bond, or is a vinylene group, an ethynylene group, an arylene group, or a heteroarylene group, or is a divalent group formed by linking two or more groups selected from the vinylene group, the ethynylene group, the arylene group, and the heteroarylene group, and Vr represents a divalent conjugated group having 2 to 40 carbon atoms, and p3 is an integer of 1 to 6.

8 . The organic semiconductor element according to claim 7 ,
wherein the polymers alternately have a structural unit represented by any one of Formulae (8) to (10) and a structure represented by Formula (G).

9 . The organic semiconductor element according to claim 7 ,
wherein, in Formula (G), Vr is a structure selected from Formulae (V D -1) to (V D -16) and (V A -1) to (V A -11),

in each formula, R and Z each represent a hydrogen atom, a halogen atom, or an alkyl group,
R G represents an alkyl group,
R J represents a hydrogen atom, an alkyl group, a cyano group, or a halogen atom, and
* represents a bonding site.

10 . The organic semiconductor element according to claim 7 ,
wherein p3 in Formula (G) is 1.

11 . The organic semiconductor element according to claim 7 ,
wherein Ar 1 and Ar 2 each represent a single bond or a divalent group represented by Formula (Ar-1) or (Ar-2),

in each formula, R W represents an alkyl group, and p1 is an integer of 0 to 2,
L W represents a chalcogen atom,
R W2 represents an alkyl group, and p2 is an integer of 0 to 4,
q1 and q2 each are an integer of 1 to 4, and
* represents a bonding site.

12 . The organic semiconductor element according to claim 7 ,
wherein Vr in Formula (G) represents a divalen

Assignees

• Fujifilm Corp
• Univ Tokyo

Inventors

• Shirokane Kenji
• Fukuzaki Eiji
• Tani Yukio
• TAMAKUNI Fumiko
• Usami Yoshihisa
• Watanabe Tetsuya
• Okamoto Toshihiro
• Takeya Junichi

Classifications

• C07D495/22

  in which the condensed system contains four or more hetero rings · CPC title

• C07D495/16

  Peri-condensed systems · CPC title

• C08G2261/1412

  Saturated aliphatic units · CPC title

• C08G2261/312

  Non-condensed aromatic systems, e.g. benzene · CPC title

• C08G2261/3243

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