Electroactive materials

Patent metadata

Field	Value
Publication number	US-10193070-B2
Application number	US-201515518854-A
Country	US
Kind code	B2
Filing date	Oct 20, 2015
Priority date	Oct 31, 2014
Publication date	Jan 29, 2019
Grant date	Jan 29, 2019

Abstract

There is disclosed a compound having Formula I, Formula II, Formula III, Formula VIII, Formula IX, or Formula X

The variables are described in detail in the application.

First claim

What is claimed is:

1. A compound having Formula I

wherein:
R 1 and R 2 are the same or different at each occurrence and are selected from the group consisting of alkyl, silyl, germyl, hydrocarbon aryl, N-heteroaryl, O-heteroaryl, S-heteroaryl, N,O-heteroaryl, and deuterated analogs thereof;
R 3 and R 4 are the same or different at each occurrence and are selected from the group consisting of alkoxy, siloxy, siloxane, alkenylaryl, aryloxy, deuterated alkoxy, deuterated siloxy, deuterated siloxane, deuterated alkenylaryl, and deuterated aryloxy;
a is an integer from 1-4; and
b is an integer from 0-4;
wherein the N-heteroaryl is derived from a compound selected from the group consisting of pyrrole, pyridine, pyrimidine, carbazole, imidazole, benzimidazole, imidazolobenzimidazole, triazole, benzotriazole, triazolopyridine, indole, indolocarbazole, phenanthroline, quinoline, isoquinoline, quinoxaline, substituted derivatives thereof, and deuterated analogs thereof;
wherein the O-heteroaryl is derived from a compound selected from the group consisting of furan, benzofuran, dibenzofuran, substituted derivatives thereof, and deuterated analogs thereof;
wherein the S-heteroaryl is derived from a compound selected form the group consisting of thiophene, benzothiophene, dibenzothiophene, substituted derivatives thereof, and deuterated analogs thereof; and
wherein the N,O-heteroaryl is derived from a compound selected from the group consisting of oxazole, benzoxazole, phenoxazine, substituted derivatives thereof, and deuterated analogs thereof;
wherein the substituted derivatives have substituents selected from the group consisting of D, alkyl, silyl, germyl, aryl, deuterated alkyl, deuterated silyl, deuterated germyl, and deuterated aryl.

2. The compound of claim 1 , wherein R 1 is an alkyl group or deuterated alkyl group having 1-30 carbons.

3. The compound of claim 1 , wherein a>0 and at least one R 3 is alkenylaryl or deuterated alkenylaryl.

4. The compound of claim 3 , wherein b>0 and at least one R 4 is alkenylaryl or deuterated alkenylaryl.

5. The compound of claim 1 , wherein a>0 and b>0.

6. An organic electronic device comprising an anode, a cathode, and at least one organic active layer therebetween, wherein the organic active layer is a photoactive layer which comprises a compound having Formula I as a photoactive material and further comprises a host material

wherein:
R 1 and R 2 are the same or different at each occurrence and are selected from the group consisting of alkyl, silyl, germyl, hydrocarbon aryl, N-heteroaryl, O-heteroaryl, S-heteroaryl, N,O-heteroaryl, and deuterated analogs thereof;
R 3 and R 4 are the same or different at each occurrence and are selected from the group consisting of D, alkyl, alkoxy, silyl, siloxy, siloxane, germyl, aryl, alkenylaryl, aryloxy, heteroaryl, diarylamino, deuterated alkyl, deuterated alkoxy, deuterated silyl, deuterated siloxy, deuterated siloxane, deuterated germyl, deuterated aryl, deuterated alkenylaryl, deuterated aryloxy, deuterated heteroaryl, and deuterated diarylamino;
a and b are the same or different and are an integer from 0-4; and
wherein the N-heteroaryl is derived from a compound selected from the group consisting of pyrrole, pyridine, pyrimidine, carbazole, imidazole, benzimidazole, imidazolobenzimidazole, triazole, benzotriazole, triazolopyridine, indole, indolocarbazole, phenanthroline, quinoline, isoquinoline, quinoxaline, substituted derivatives thereof, and deuterated analogs thereof;
wherein the O-heteroaryl is derived from a compound selected from the group consisting of furan, benzofuran, dibenzofuran, substituted derivatives thereof, and deuterated analogs thereof;
wherein the S-heteroaryl is derived from a compound selected form the group consisting of thiophene, benzothiophene, dibenzothiophene, substituted derivatives thereof, and deuterated analogs thereof; and
wherein the N,O-heteroaryl is derived from a compound selected from the group consisting of oxazole, benzoxazole, phenoxazine, substituted derivatives thereof, and deuterated analogs thereof;
wherein the substituted derivatives have substituents selected from the group consisting of D, alkyl, silyl, germyl, aryl, deuterated alkyl, deuterated silyl, deuterated germyl, and deuterated aryl.

7. The device of claim 6 , wherein the compound having Formula I is selected from the group consisting of Compound I-1 through Compound I-32

8. The device of claim 6 , wherein a>0 and b>0.

9. The device of claim 6 , wherein R 1 has Formula a

where:
R 5 is the same or different at each occurrence and is selected from the group consisting of D, alkyl, alkoxy, siloxane, silyl, germyl, deuterated alkyl, deuterated alkoxy, deuterated siloxane, deuterated silyl, and deuterated germyl, where adjacent R 5 groups can be joined together to form an fused aromatic ring or a deuterated fused aromatic ring;
p is the same or different at each occurrence and is an integer from 0-4;
q is an integer from 0-5;
r is an integer from 1 to 5; and
** represents a point of attachment to N.

10. The device of claim 9 , wherein R 2 has Formula a.

11. The device of claim 6 , wherein a>0 and at least one R 3 is selected from the group consisting of styryl, stilbenyl, phenyl, naphthyl, Formula a1, substituted derivatives thereof, and deuterated analogs thereof, where Formula a1 is

where:
R 5 is the same or different at each occurrence and is selected from the group consisting of D, alkyl, alkoxy, siloxane, silyl, germyl, deuterated alkyl, deuterated alkoxy, deuterated siloxane, deuterated silyl, and deuterated germyl, where adjacent R 5 groups can be joined together to form an fused aromatic ring or a deuterated fused aromatic ring;
p is the same or different at each occurrence and is an integer from 0-4;
q is an integer from 0-5;
r is an integer from 1 to 5; and
# indicates a point of attachment;

wherein the substituted derivatives have substituents selected from the group consisting of D, CN, alkyl, silyl, germyl, diarylamino, aryl, heteroaryl, deuterated alkyl, deuterated silyl, deuterated germyl, deuterated diarylamino, deuterated aryl, and deuterated heteroaryl.

12. The device of claim 6 , wherein a>0 and at least one R 3 is an N-heteroaryl group.

13. The compound of claim 6 , wherein a=1 and R 3 is a diarylamino group or deuterated diarylamino group.

14. The device

Assignees

• Du Pont

Inventors

• Gao Weiying
• Howard Jr Michael Henry
• Diev Viacheslav V
• Wu Weishi
• Meng Hong

Classifications

• C07D517/06

  Peri-condensed systems · CPC title

• H01L51/5206

  Electricity · mapped topic

• H01L2251/308

  Electricity · mapped topic

• H01L51/0058

  Electricity · mapped topic

• H01L51/0052

  Electricity · mapped topic