Fused polycyclic heteroaromatic compound, organic thin film including compound and electronic device including organic thin film

Patent metadata

Field	Value
Publication number	US-10559764-B2
Application number	US-201615008976-A
Country	US
Kind code	B2
Filing date	Jan 28, 2016
Priority date	Jan 29, 2015
Publication date	Feb 11, 2020
Grant date	Feb 11, 2020

Abstract

A fused polycyclic heteroaromatic compound represented by Chemical Formula 1A or 1B that has a compact planar structure in which eight or more rings are fused together.

First claim

What is claimed is:

1. A fused polycyclic heteroaromatic compound represented by Chemical Formula 1A

wherein, in Chemical Formula 1A,
each of X 1 to X 4 are independently O, S, Se, Te, N—R a , or —NC(═O)OR f ,
wherein each R a is independently hydrogen, a substituted or unsubstituted linear or branched C 1 to C 30 alkyl group, a substituted or unsubstituted C 2 to C 30 alkenyl group, a substituted or unsubstituted C 2 to C 30 alkynyl group, a substituted or unsubstituted C 7 to C 30 arylalkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, or a substituted or unsubstituted C 1 to C 30 alkoxy group, and
wherein R f is a substituted or unsubstituted C 1 to C 30 alkyl group,
each of R 1 to R 12 are independently hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a substituted or unsubstituted C 2 to C 30 alkenyl group, a substituted or unsubstituted C 2 to C 30 alkynyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 2 to C 30 heteroaryl group, a substituted or unsubstituted C 7 to C 30 arylalkyl group, a substituted or unsubstituted C 2 to C 30 heteroarylalkyl group, a substituted or unsubstituted C 2 to C 30 alkylheteroaryl group, a substituted or unsubstituted C 5 to C 30 cycloalkyl group, or a substituted or unsubstituted C 2 to C 30 heterocycloalkyl group,
each of n1 and n2 are independently 1, 2, or 3.

2. The fused polycyclic heteroaromatic compound of claim 1 , wherein each of the R 1 and R 7 groups are independently a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 2 to C 30 heteroaryl group, a substituted or unsubstituted C 7 to C 30 arylalkyl group, a substituted or unsubstituted C 2 to C 30 heteroarylalkyl group, a substituted or unsubstituted C 2 to C 30 alkylheteroaryl group, a substituted or unsubstituted C 5 to C 30 cycloalkyl group, or a substituted or unsubstituted C 2 to C 30 heterocycloalkyl group.

3. The fused polycyclic heteroaromatic compound of claim 1 , wherein each of the R 1 and R 7 groups are independently a fluoro-substituted C 1 to C 30 alkyl group.

4. The fused polycyclic heteroaromatic compound of claim 1 , wherein Ra is a substituted or unsubstituted C 10 to C 30 alkyl group, or a substituted or unsubstituted C 10 to C 30 alkoxy group, a substituted or unsubstituted C 10 to C 30 alkenyl group, or a substituted or unsubstituted C 10 to C 30 alkynyl group.

5. The fused polycyclic heteroaromatic compound of claim 1 , wherein the R a is a fluoro-substituted C 1 to C 30 alkyl group.

6. The fused polycyclic heteroaromatic compound of claim 1 , wherein the fused polycyclic heteroaromatic compound has an average molecular weight of about 350 to about 3,000.

7. The fused polycyclic heteroaromatic compound of claim 1 , wherein n1 and n2 are each 1.

8. The fused polycyclic heteroaromatic compound of claim 1 , wherein n1 and n2 are independently 2 or 3.

9. The fused polycyclic heteroaromatic compound of claim 1 , wherein X 1 and X 2 are S.

10. The fused polycyclic heteroaromatic compound of claim 1 , wherein X 1 and X 2 are O.

11. The fused polycyclic heteroaromatic compound of claim 1 , wherein X 1 and X 2 are Te.

12. The fused polycyclic heteroaromatic compound of claim 1 , wherein each of X 1 to X 2 are N—R a .

13. The fused polycyclic heteroaromatic compound of claim 1 , wherein n1 and n2 are 1.

14. The fused polycylic heteroaromatic compound of claim 13 , wherein X 1 to X 4 are S.

15. The fused polycyclic heteroaromatic compound of claim 1 , wherein the compound is at least one of compounds (1), (1a), (3), (5), (7), (9), (11), (13), (15), (17), (19), (21), (23), and (25):

wherein:
a hydrogen of each benzene ring, each thiophene ring, each selenophene ring or each pyrrole ring is optionally replaced by a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a substituted or unsubstituted C 2 to C 30 alkenyl group, a substituted or unsubstituted C 2 to C 30 alkynyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 2 to C 30 heteroaryl group, a substituted or unsubstituted C 7 to C 30 arylalkyl group, a substituted or unsubstituted C 2 to C 30 heteroarylalkyl group, a substituted or unsubstituted C 2 to C 30 alkylheteroaryl group, a substituted or unsubstituted C 5 to C 30 cycloalkyl group, or a substituted or unsubstituted C 2 to C 30 heterocycloalkyl group; and
in R a1 , R a2 , R a5 , R a6 , R a9 , R a10 , R a13 , R a14 , R a17 , R a18 , R a21 , R a22 , R a25 , Ra 26 , R a29 , and R a30 of the compounds (11), (13), (15), (17), (19), (21), (23), and (25) are independently the same as R a of Chemical Formulae 1A.

16. The fused polycyclic heteroaromatic compound of claim 15 , wherein R a1 , R a2 , R a5 , R a6 , R a9 , R a10 , R a13 , R a14 , R a17 , R a18 , R a21 , R a22 , R a25 , R a26 , R a29 , and R a30 of the compounds (11), (13), (15), (17), (19), (21), (23), and (25), respectively, are independently hydrogen, a substituted or unsubstituted linear or branched C 1 to C 30 alkyl group, or a substituted or unsubstituted C 6 to C 30 aryl group.

17. An organic thin film comprising the fused polycyclic heteroaromatic compound of claim 1 .

18. An electronic device comprising the fused polycyclic heteroaromatic compound of claim 1 .

19. The electronic device of claim 18 , wherein the electronic device is a transistor, an organic light emitting diode (OLED), a photovoltaic device, a solar cell, a laser device, a memory device, or a sensor.

20. The electronic device of claim 18 , wherein
the electronic device includes at least one charge transport layer; and
the charge transport layer includes the fused polycyclic heteroaromatic compound.

Assignees

• Samsung Electronics Co Ltd

Inventors

• Park Jeong Il
• Miyazaki Eigo
• Lee Eun Kyung
• Choi Ajeong

Classifications

• C07D495/22 Primary

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

• C07D487/22

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

• C07D517/22 Primary

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

• H01L51/0074 Primary

  Electricity · mapped topic

• H01L51/0558

  Electricity · mapped topic