IP Library Granted Patent US 9,876,174
Granted Patent B2
US 9,876,174 · App. 15/472,680 · Granted Jan 23, 2018

Electronic device including a fluoranthene derivative

Inventors: Weishi Wu (Landenberg, PA); Weiying Gao (Landenberg, PA)
Assignee: E I DU PONT DE NEMOURS AND COMPANY
H01L51/0054C07C13/66C07D235/08C07D235/14C07D239/26C07D307/91C07D403/14C09K11/025C09K11/06H01L51/0058H01L51/0067H01L51/5036H05B33/14C07C2103/18C07C2103/40C07C2603/18C07C2603/40C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1088C09K2211/1092H01L51/5012H01L51/5016H01L51/5072H01L2251/5384
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Quick Facts
Patent No.
US 9,876,174
App. No.
15/472,680
Granted
Jan 23, 2018
Kind
B2
Abstract

There is provided a compound having Formula I. In Formula I: R 3 -R 16 are the same or different and are H, D, alkyl, silyl, aryl, deuterated alkyl, deuterated silyl, or deuterated aryl, where no more than two R 1 -R 16 are biphenyl and where at least two of R 1 -R 16 have Formula II. In Formula II: Ar is phenyl, naphthyl, heteroaryl, spirofluorenyl, or a deuterated analog thereof; R 11 is the same or different at each occurrence and is D, alkyl, silyl, aryl, deuterated alkyl, deuterated silyl, or deuterated aryl, where adjacent R 11 groups can join to form a fused aromatic ring or fused deuterated aromatic ring; m is an integer form 0-4; n is an integer from 1-5; and the asterisk represents a point of attachment.

Claims (46)

1. An electroactive material having Formula I

wherein:

R 1 -R 10 are the same or different and are selected from the group consisting of H, D, alkyl, silyl, aryl, deuterated alkyl, deuterated silyl, and deuterated aryl;

with the proviso that no more than one of R 1 -R 10 is biphenyl and at least one of R 1 -R 6 and at least one of R 7 -R 10 have Formula II

wherein:

Ar is selected from the group consisting of S-heteroaryl, N,O-heteroaryl, N,S-heteroaryl, spirofluorenyl, and deuterated analogs thereof;

R 11 is the same or different at each occurrence and is selected from the group consisting of D, alkyl, silyl, aryl, deuterated alkyl, deuterated silyl, and deuterated aryl, wherein adjacent R 11 groups can join to form a fused aromatic ring or fused deuterated aromatic ring;

m is an integer from 0-4; and

n is an integer from 1-5.

2. The electroactive material of claim 1 , wherein at least two of R 7 -R 10 have Formula II.

3. The electroactive material of claim 1 , wherein Ar is an N,O-heteroaryl selected from the group consisting of oxazole, benzoxazole, and deuterated analogs thereof.

4. The electroactive material of claim 1 , wherein Ar is an N,S-heteroaryl selected from the group consisting of thiazole, benzothiazole, and deuterated analogs thereof.

5. An electronic device comprising at least one electroactive layer positioned between two electrical contact layers, wherein the at least one electroactive layer comprises the electroactive material having Formula I according to claim 1 .

6. The device of claim 5 , comprising an anode, a hole transport layer, a photoactive layer, an electron transport layer, and a cathode, wherein at least one of the photoactive layer and the electron transport layer comprises the electroactive material having Formula I.

7. The device of claim 5 , wherein the photoactive layer comprises (a) a host material which is the electroactive material having Formula I and (b) an organometallic electroluminescent dopant.

8. The device of claim 5 , wherein the electron transport layer comprises the electroactive material having Formula I.

9. An electroactive material having Formula I

wherein:

R 1 -R 10 are the same or different and are selected from the group consisting of H, D, alkyl, silyl, aryl, deuterated alkyl, deuterated silyl, and deuterated aryl;

with the proviso that no more than one of R 1 -R 10 is biphenyl and at least two of R 1 -R 10 have Formula II

wherein:

Ar is an S-heteroaryl selected from the group consisting of thiophene, (di)benzothiophene, thienothiophene, and deuterated analogs thereof;

R 11 is the same or different at each occurrence and is selected from the group consisting of D, alkyl, silyl, aryl, deuterated alkyl, deuterated silyl, and deuterated aryl, wherein adjacent R 11 groups can join to form a fused aromatic ring or fused deuterated aromatic ring;

m is an integer from 0-4; and

n is an integer from 1-5.

10. An electronic device comprising at least one electroactive layer positioned between two electrical contact layers, wherein the at least one electroactive layer comprises the electroactive material having Formula I according to claim 9 .

11. The device of claim 10 , comprising an anode, a hole transport layer, a photoactive layer, an electron transport layer, and a cathode, wherein at least one of the photoactive layer and the electron transport layer comprises the electroactive material having Formula I.

12. The device of claim 10 , wherein the photoactive layer comprises (a) a host material which is the electroactive material having Formula I and (b) an organometallic electroluminescent dopant.

13. The device of claim 10 , wherein the electron transport layer comprises the electroactive material having Formula I.

14. An electroactive material having Formula I

wherein:

R 1 -R 10 are the same or different and are selected from the group consisting of H, D, alkyl, silyl, aryl, deuterated alkyl, deuterated silyl, and deuterated aryl;

with the proviso that no more than one of R 1 -R 10 is biphenyl and at least two of R 1 -R 10 have Formula II

wherein:

Ar is selected from the group consisting of spirofluorenyl and a deuterated analog thereof;

R 11 is the same or different at each occurrence and is selected from the group consisting of D, alkyl, silyl, aryl, deuterated alkyl, deuterated silyl, and deuterated aryl, wherein adjacent R 11 groups can join to form a fused aromatic ring or fused deuterated aromatic ring;

m is an integer from 0-4; and

n is an integer from 1-5.

15. The electroactive material of claim 14 , wherein Ar is selected from the group consisting of

where:

R″ is the same or different at each occurrence and is selected from the group consisting of H, D, C 1-12 alkyl, and deuterated C 1-12 alkyl, and positions available for H can be H or D, and

* indicates a point of attachment.

16. An electronic device comprising at least one electroactive layer positioned between two electrical contact layers, wherein the at least one electroactive layer comprises the electroactive material having Formula I according to claim 14 .

17. The device of claim 16 , comprising an anode, a hole transport layer, a photoactive layer, an electron transport layer, and a cathode, wherein at least one of the photoactive layer and the electron transport layer comprises the electroactive material having Formula I.

18. The device of claim 16 , wherein the photoactive layer comprises (a) a host material which is the electroactive material having Formula I and (b) an organometallic electroluminescent dopant.

19. The device of claim 16 , wherein the electron transport layer comprises the electroactive material having Formula I.

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 Apr 5, 2017
From: WU, WEISHI; GAO, WEIYING
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 041855/0409 →
Continuity (3)
Continuation 15031031
Provisional Application 61895497 · Oct 25, 2013
Related Publication 20170200900A1 · Jul 13, 2017