Organic electronic device comprising an organic semiconductor layer and a device

Patent metadata

Field	Value
Publication number	US-11795186-B2
Application number	US-201816615224-A
Country	US
Kind code	B2
Filing date	May 18, 2018
Priority date	May 23, 2017
Publication date	Oct 24, 2023
Grant date	Oct 24, 2023

Abstract

The present invention relates to a compound of formula 1 and an organic electronic device comprising an organic semiconductor layer, wherein at least one organic semiconductor layer comprises a compound of formula (1), wherein X is selected from O, S or Se; Ar1 is selected from unsubstituted or substituted C2 to C60 heteroarylene, and wherein the substituted C2 to C60 heteroarylene comprises at least about one to about six substituents, wherein the substituent of the substituted C2 to C60 heteroarylene are independently selected from C1 to C12 alkyl, C1 to C12 alkoxy, CN, OH, halogen, C6 to C36 arylene, or C2 to C25 heteroarylene; n is 1 or 2; L1 is selected from a single bond, C1 to C4 alkyl, substituted or unsubstituted C6 to C36 arylene, wherein the substituent of substituted C6 to C36 arylene is selected from C1 to C12 alkyl, C6 to C18 arylene; L2 is selected from a single bond or C1 to C6 alkyl; R1, R2 are independently selected from substituted or unsubstituted C1 to C16 alkyl, wherein the substituent of substituted C1 to C16 alkyl is selected from C6 to C18 arylene or C2 to C12 heteroarylene; wherein the compound of formula 1 comprises at least about 4 of C6-arylene rings and a molecular mass of at least about 400 g/mol to about 1800 g/mol.

First claim

The invention claimed is:

1. Organic electronic device comprising at least one organic semiconductor layer, wherein the at least one organic semiconductor layer comprises a compound of formula 1:

wherein
X is selected from O, S or Se;
Ar 1 is selected from unsubstituted or substituted C 2 to C 60 heteroarylene, and wherein the substituted C 2 to C 60 heteroarylene comprises at least about one to about six substituents,
wherein the substituent of the substituted C 2 to C 60 heteroarylene are independently selected from C 1 to C 12 alkyl, C 1 to C 12 alkoxy, CN, OH, halogen, C 6 to C 36 arylene, or C 2 to C 25 heteroarylene;

n is 1 or 2;
L 1 is selected from a single bond, C 1 to C 4 alkyl, substituted or unsubstituted C 6 to C 36 arylene,
wherein the substituent of substituted C 6 to C 36 arylene is selected from C 1 to C 12 alkyl, C 6 to C 18 arylene;

L 2 is selected from a single bond or C 1 to C 6 alkyl,
R 1 , R 2 are independently selected from substituted or unsubstituted C 1 to C 16 alkyl, wherein the substituent of substituted C 1 to C 16 alkyl is selected from C 6 to C 18 arylene or C 2 to C 12 heteroarylene,
wherein the compound of formula 1 comprises:
at least about 4 of C 6 -arylene rings,
a molecular mass of at least about 400 g/mol to about 1800 g/mol;
wherein Ar 1 comprises at least one N-heteroaryl group selected from the group comprising a triazine, quinazoline, quinoline, benzimidazole, benzothiazole, benzo[4,5]thieno[3,2-d]pyrimidine, pyrimidine and pyridine.

2. The organic electronic device according to claim 1 , wherein the compound of formula 1 comprises at least about 4 to about 12 C 6 -arylene rings, or at least about 4 to about 12 condensed C 6 -arylene rings.

3. The organic electronic device according to claim 1 , wherein L 1 bonds via a single bond directly on a heteroarylene group of Ar 1 .

4. The organic electronic device according to claim 1 , wherein in formula 1:
X is selected from 0 or S;
Ar 1 is selected from unsubstituted or substituted C 3 to C 51 heteroarylene, and
wherein the substituted C 3 to C 51 heteroarylene comprises at least one to three substituents,
wherein the substituent of the substituted C 3 to C 51 heteroarylene are independently selected from C 1 to C 12 alkyl, CN, C 6 to C 36 arylene or C 2 to C 25 heteroarylene;

n is 1 or 2;
L 1 is selected from unsubstituted C 6 to C 36 arylene, wherein L 1 comprises at least one to six aromatic-6-member rings;
L 2 is selected from a single bond or C 1 to C 6 alkyl,
R 1 , R 2 are independently selected from unsubstituted C 1 to C 4 alkyl.

5. The organic electronic device according to claim 1 , wherein Ar 1 has the chemical structure B1 to B12:

wherein
Ar 1 is bonded at “*” to L 1 via a single bond; and

wherein
W, Y, Z are independently selected from N, S, O, CH or CR 3 , wherein at least one of W, Y, Z is selected from N, S or O, or at least W and Y are N;
E 1 is selected from N—Ar 2 , O or S;
R 3 and R 4 are independently selected from H, C 1 to C 16 alkyl, or Ar 2 ;
Ar 2 is independently selected from substituted or unsubstituted C 6 to C 36 arylene, C 2 to C 25 heteroarylene, wherein
in structure B3 and structure B5 at least two ring atoms of the arylene or heteroarylene of Ar 2 forms with E 1 at least a five member ring, and wherein the substituent of the substituted C 6 to C 36 arylene and of the substituted C 2 to C 25 heteroarylene are selected from C 1 to C 12 alkyl and C 1 to C 12 alkoxy.

6. The organic electronic device according to claim 1 , wherein for n=2 the compound has the chemical formula 2:

7. The organic electronic device according to claim 1 , wherein
Ar 1 is selected from at least one of the following:
at least about 1 to about 5 heteroarylenes selected from 5 or 6 member rings, or about 1 to about 3 heteroarylenes selected from 5 or 6 member rings, or one 6 member heteroarylene ring;
at least about 1 to 12 arylenes selected from 5 or 6 member rings, or at least about 2 to 10 arylenes selected from 5 or 6 member rings, or at least about 2 to 8 arylenes selected from 6 member rings or about 3 to about 6 arylenes selected from 6 member rings;
at least 1 to 6 condensed 5 or 6 member rings of arylenes or heteroarylenes, or about 2 to about 4 condensed 5 or 6 member rings of arylenes or heteroarylenes, or 2 to about 4 condensed 5 or 6 member arylenes and one 5 or 6 member heteroarylene.

8. The organic electronic device according to claim 1 , wherein
Ar 1 comprise at least about one group, or about one to about 4 groups, selected from phenyl, biphenyl, terpyhenyl, quarterphenyl, naphthyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, or a group selected from chemical structures D1 to D7:

wherein
Ar 1 is bonded at“*” to Li, so that between Ar 1 and L 1 a single bond is formed; and wherein

R 5 and R 6 are independently selected from C 1 to C 16 alkyl, or Ar 2 ; and
Ar 4 and Ar 5 are independently selected from C 1 to C 16 alkyl or substituted or unsubstituted C 6 to C 36 arylene, C 2 to C 25 heteroarylene, wherein
the substituent of the substituted C 6 to C 36 arylene, C 2 to C 25 heteroarylene is selected from C 1 to C 12 alkyl, C 1 to C 12 alkoxy; and

Ar 6 is selected from H or phenyl.

9. The organic electronic device according to claim 1 , wherein
Ar 1 is selected from the chemical structures F1 to F31, and is connected with L 1 at “*” via a single bond:

10. The organic electronic device according to claim 1 , wherein for the comp according to chemical formula 1:

wherein
L 1 is selected from the group of structures G1 to G13, wherein
L 1 is connected via a single bond to L 2 at “ *1 ”, and L 1 is connected via a single bond to Ar 1 at “ *2 ”:
a) for n=1

 or
b) for n=2

Assignees

• Novaled Gmbh

Inventors

• Luschtinetz Regina
• Schulze Benjamin

Classifications

• C07F9/6521 Primary

  Six-membered rings · CPC title

• C07F9/5728 Primary

  condensed with carbocyclic rings or carbocyclic ring systems · CPC title

• C07F9/6561

  containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings · CPC title

• C07F9/65128

  condensed with carbocyclic rings or carbocyclic ring systems · CPC title

• C07F9/65583

  each of the hetero rings containing nitrogen as ring hetero atom · CPC title