IP Library Granted Patent US 9,680,111
Granted Patent B2
US 9,680,111 · App. 15/015,469 · Granted Jun 13, 2017

Compositions for electronic applications

Inventors: Jerald Feldman (Wilmington, DE); Norman Herron (Newark, DE); Michael Henry Howard, Jr. (Montchanin, DE); Nora Sabina Radu (Landenberg, PA); Vsevolod Rostovtsev (Swarthmore, PA); Kerwin D Dobbs (Wilmington, DE); Adam Fennimore (Wilmington, DE); Weiying Gao (Landenberg, PA); Weishi Wu (Landenberg, PA); Ying Wang (Wilmington, DE); Charles D McLaren (Landenberg, PA)
Assignee: E I DU PONT DE NEMOURS AND COMPANY
H01L51/0072C09K11/025C09K11/06H01L51/0061H01L51/0067H01L51/0074H01L51/0085H01L51/0087H05B33/14C09K2211/1003C09K2211/1029C09K2211/1059C09K2211/185H01L51/0558H01L51/5016H01L2251/5384
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,680,111
App. No.
15/015,469
Granted
Jun 13, 2017
Kind
B2
Abstract

This invention relates to a composition including (a) a dopant, (b) a first host having at least one unit of Formula I, and (c) a second host compound. Formula I has the structure where Q is a fused ring linkage having the formula In Formula I: R 1 is the same or different at each occurrence and is D, alkyl, aryl, silyl, alkoxy, aryloxy, cyano, vinyl, or allyl; R 2 is the same or different at each occurrence and is H, D, alkyl, or aryl, or both R 2 are an N-heterocycle; R 3 is the same or different at each occurrence and is H, D, cyano, alkyl or aryl; and a is the same or different at each occurrence and is an integer from 0-4.

Claims (43)

1. A composition comprising (a) a dopant capable of electroluminescence having an emission maximum between 380 and 750 nm, (b) a host compound having at least one unit of Formula II(a)

wherein:

R 1 is the same or different at each occurrence and is D, alkyl, aryl, silyl, alkoxy, aryloxy, cyano, styryl, vinyl, or allyl;

R 3 is the same or different at each occurrence and is H, D, alkyl, aryl, silyl, alkoxy, aryloxy, cyano, styryl, vinyl, or allyl;

R 4 is the same or different at each occurrence and is an O-heterocycle, an S-heterocycle, or a deuterated analog thereof;

a is the same or different at each occurrence and is an integer from 0-4;

b is the same or different at each occurrence and is an integer from 1-5; and

(c) a second host compound which is an indolocarbazole or a deuterated analog thereof.

2. The composition of claim 1 , wherein the first host compound is at least 10% deuterated.

3. The composition of claim 1 , wherein R 3 is H or D.

4. The composition of claim 1 , wherein the second host is an indolocarbazole having an N-heterocycle substituent, or a deuterated analog thereof.

5. The composition of claim 1 , wherein the second host material has Formula V

wherein:

Q is a fused ring linkage having the formula

R 1 is the same or different at each occurrence and is D, alkyl, aryl, silyl, alkoxy, aryloxy, cyano, vinyl, or allyl;

R 3 is the same or different at each occurrence and is H, D, cyano, alkyl, or aryl;

R 4 is the same or different at each occurrence and is D, aryl, silyl, alkoxy, aryloxy, cyano, vinyl, allyl, dialkylamino, diarylamine, carbazole, pyridine, pyrimidine, triazine, dibenzothiophene, dibenzopyran, or a deuterated analog thereof;

R 8 is the same or different at each occurrence and is H, D, alkyl, or aryl, or R 8 may form a fused 5- or 6-membered ring;

X is the same or different at each occurrence and is CH or N, with the proviso that at least one X is N;

a is the same or different at each occurrence and is an integer from 0-4; and

b is the same or different at each occurrence and is an integer from 0-5.

6. An organic electronic device comprising a first electrical contact layer, a second electrical contact layer, and a photoactive layer therebetween, wherein the photoactive layer comprises (a) a dopant capable of electroluminescence having an emission maximum between 380 and 750 nm, (b) a first host compound having at least one unit of Formula II(a)

wherein:

R 1 is the same or different at each occurrence and is D, alkyl, aryl, silyl, alkoxy, aryloxy, cyano, styryl, vinyl, or allyl;

R 3 is the same or different at each occurrence and is H, D, alkyl, aryl, silyl, alkoxy, aryloxy, cyano, styryl, vinyl, or allyl;

R 4 is the same or different at each occurrence and is an O-heterocycle, an S-heterocycle, or a deuterated analog thereof;

a is the same or different at each occurrence and is an integer from 0-4;

b is the same or different at each occurrence and is an integer from 1-5; and

(c) a second host compound which is an indolocarbazole or a deuterated analog thereof.

7. The device of claim 6 , wherein the dopant is a luminescent organometallic complex.

8. The device of claim 7 , wherein the organometallic complex is a cyclometalated compex of iridium or platinum.

9. The device of claim 6 , wherein the second host is an indolocarbazole having an N-heterocycle substituent, or a deuterated analog thereof.

10. The device of claim 6 , wherein the second host material has Formula V

wherein:

Q is a fused ring linkage having the formula

R 1 is the same or different at each occurrence and is D, alkyl, aryl, silyl, alkoxy, aryloxy, cyano, vinyl, or allyl;

R 3 is the same or different at each occurrence and is H, D, cyano, alkyl, or aryl;

R 4 is the same or different at each occurrence and is D, aryl, silyl, alkoxy, aryloxy, cyano, vinyl, allyl, dialkylamino, diarylamine, carbazole, pyridine, pyrimidine, triazine, dibenzothiophene, dibenzopyran, or a deuterated analog thereof;

R 8 is the same or different at each occurrence and is H, D, alkyl, or aryl, or R 8 may form a fused 5- or 6-membered ring;

X is the same or different at each occurrence and is CH or N, with the proviso that at least one X is N;

a is the same or different at each occurrence and is an integer from 0-4; and

b is the same or different at each occurrence and is an integer from 0-5.

11. The device of claim 6 , wherein the photoactive layer consists essentially of (a) a dopant capable of electroluminescence having an emission maximum between 380 and 750 nm and (b) a first host compound having at least one unit of Formula II(a), and (c) a second host compound which is an indolocarbazole or a deuterated analog thereof.

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 Feb 28, 2019
From: FELDMAN, JERALD; WANG, YING; MCLAREN, CHARLES D.; HERRON, NORMAN; HOWARD, MICHAEL HENRY, JR.; RADU, NORA SABINA; ROSTOVTSEV, VSEVOLOD; DOBBS, KERWIN D.; FENNIMORE, ADAM; GAO, WEIYING; WU, WEISHI
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 048462/0411 →
Continuity (3)
Continuation 13990832
Provisional Application 61424955 · Dec 20, 2010
Related Publication 20160164005A1 · Jun 9, 2016