IP Library Granted Patent US 10,193,070
Granted Patent B2
US 10,193,070 · App. 15/518,854 · Granted Jan 29, 2019

Electroactive materials

Inventors: Weiying Gao (Landenberg, PA); Michael Henry Howard, Jr. (Montchanin, DE); Viacheslav V. Diev (Wilmington, DE); Weishi Wu (Landenberg, PA); Hong Meng (Wilmington, DE)
Assignee: E I DU PONT DE NEMOURS AND COMPANY
H01L51/0035C07D487/06C07D493/06C07D495/06C07D517/06C08G73/026C09K11/025H01L51/006H01L51/0052H01L51/0058H01L51/0059H01L51/0081H01L51/5016H01L51/5024H01L51/5064H01L51/5206H01L51/5221C09K2211/1007H01L2251/308
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Quick Facts
Patent No.
US 10,193,070
App. No.
15/518,854
Granted
Jan 29, 2019
Kind
B2
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.

Claims (49)

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 of claim 13 , wherein b=1 and R 4 is a diarylamino group or deuterated diarylamino group.

15. The device of claim 6 , wherein a>0 and at least one R 3 is alkenylaryl or deuterated alkenylaryl.

16. The device of claim 15 , wherein b>0 and at least one R 4 is alkenylaryl or deuterated alkenylaryl an N-heteroaryl group.

17. A compound selected from the group consisting of Compound I-1, Compound I-11 through Compound I-16, Compound I-21, and Compound I-28 through Compound I-31

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 22, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: LG CHEM, LTD.
Reel/Frame 050150/0482 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 23, 2017
From: GAO, WEIYING; HOWARD, MICHAEL HENRY, JR; DIEV, VIACHESLAV V; WU, WEISHI; MENG, HONG
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 043922/0348 →
Continuity (5)
Provisional Application 62073424 · Oct 31, 2014
Provisional Application 62073561 · Oct 31, 2014
Provisional Application 62073543 · Oct 31, 2014
Provisional Application 62073408 · Oct 31, 2014
Related Publication 20170229654A1 · Aug 10, 2017