IP Library › Granted Patent US 10,700,284
Granted Patent B2
US 10,700,284 · App. 15/189,812 · Granted Jun 30, 2020

Photoactive composition

Inventors: Norman Herron (Newark, DE); Weiying Gao (Landenberg, PA); Mark A Guidry (Wilmington, DE)
Assignee: LG Chem, Ltd.
H01L51/006C07C211/61C07D213/74C07D307/91C09K11/025C09K11/06H01L51/002H01L51/0052H01L51/0054H01L51/0058H01L51/0073C07C2603/40C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1088C09K2211/1092H01L51/5012
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Quick Facts
Patent No.
US 10,700,284
App. No.
15/189,812
Granted
Jun 30, 2020
Kind
B2
Abstract

There is disclosed a photoactive composition; and there is also disclosed an organic electronic device comprising a first electrical contact, a second electrical contact and a photoactive layer therebetween, the photoactive layer comprising the photoactive composition.

Claims (44)

1. A photoactive composition comprising:

(a) a dopant material having Formula I

wherein:

Ar 1 and Ar 2 are the same or different and are selected from the group consisting of hydrocarbon aryl and deuterated hydrocarbon aryl;

R 1 -R 4 are the same or different at each occurrence and are selected from the group consisting of D, F, CN, alkyl, fluoroalkyl, aromatic hydrocarbon having one point of attachment, fluorinated aromatic hydrocarbon having one point of attachment, N-heteroaromatic hydrocarbon having one point of attachment, amino, silyl, germyl, alkoxy, RO— where R is an aromatic hydrocarbon having one point of attachment, fluoroalkoxy, siloxane, siloxy, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated aromatic hydrocarbon having one point of attachment, deuterated partially-fluorinated aromatic hydrocarbon having one point of attachment, deuterated N-heteroaromatic hydrocarbon having one point of attachment, deuterated amino, deuterated silyl, deuterated germyl, deuterated alkoxy, deuterated RO— where R is an aromatic hydrocarbon having one point of attachment, deuterated fluoroalkoxy, deuterated siloxane, and deuterated siloxy;

a and b are the same or different and are 0 or 1;

x, x1, y, and y1 are the same or different and are an integer from 0-5; and

BzF has formula BzF-1

where

R 5 and R 6 are the same or different at each occurrence and are selected from the group consisting of alkyl, fluoroalkyl, aromatic hydrocarbon having one point of attachment, fluorinated aromatic hydrocarbon having one point of attachment, deuterated alkyl, deuterated fluoroalkyl, deuterated aromatic hydrocarbon having one point of attachment, and deuterated fluorinated aromatic hydrocarbon having one point of attachment, where two R 5 and R 6 alkyl groups can be joined together to make a cycloalkyl ring, and where two R 5 and R 6 phenyl groups can be joined to form a fluorene group;

R 7 and R 8 are the same or different at each occurrence and are selected from the group consisting of D, F, CN, alkyl, fluoroalkyl, aromatic hydrocarbon having one point of attachment, fluorinated aromatic hydrocarbon having one point of attachment, N-heteroaromatic hydrocarbon having one point of attachment, amino, silyl, germyl, alkoxy, RO— where R is an aromatic hydrocarbon having one point of attachment, fluoroalkoxy, siloxane, siloxy, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated aromatic hydrocarbon having one point of attachment, deuterated partially-fluorinated aromatic hydrocarbon having one point of attachment, deuterated N-heteroaromatic hydrocarbon having one point of attachment, deuterated amino, deuterated silyl, deuterated germyl, deuterated alkoxy, deuterated RO— where R is an aromatic hydrocarbon having one point of attachment, deuterated fluoroalkoxy, deuterated siloxane, and deuterated siloxy;

x2 is an integer from 0-5;

z is an integer from 0-3; and

indicates a point of attachment; and

(b) a host material having Formula II

wherein:

Q is selected from the group consisting of aromatic hydrocarbon having one point of attachment, aromatic hydrocarbon having at least one heteroatom in the ring structure and one point of attachment, deuterated aromatic hydrocarbon having one point of attachment, and deuterated aromatic hydrocarbon having at least one heteroatom in the ring structure and one point of attachment;

R 12 -R 15 are the same or different at each occurrence and are selected from the group consisting of D, F, CN, alkyl, fluoroalkyl, aromatic hydrocarbon having one point of attachment, fluorinated aromatic hydrocarbon having one point of attachment, aromatic hydrocarbon having at least one heteroatom in the ring structure and one point of attachment, silyl, germyl, alkoxy, RO— where R is an aromatic hydrocarbon having one point of attachment, fluoroalkoxy, siloxane, siloxy, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated hydrooarbon aryl aromatic hydrocarbon having one point of attachment, deuterated partially-fluorinated af14 aromatic hydrocarbon having one point of attachment, deuterated heteroaryl aromatic hydrocarbon having at least one heteroatom in the ring structure and one point of attachment, deuterated silyl, deuterated germyl, deuterated alkoxy, deuterated aryloxy RO— where R is an aromatic hydrocarbon having one point of attachment, deuterated fluoroalkoxy, deuterated siloxane, and deuterated siloxy;

c is an integer from 0-7;

d is an integer from 0-8;

e is an integer from 0-6;

f is an integer from 0-4; and

n is 1.

2. The composition of claim 1 , wherein the dopant has Formula I-a

3. The composition of claim 1 , wherein the dopant has Formula I-b

with the proviso that at least one of R 1 -R 4 is not D.

4. The composition of claim 1 , wherein R 1 -R 4 have no heteroaromatic groups.

5. The composition of claim 1 , wherein x>0 and at least one R 1 is an N-heteroaryl having one point of attachment or deuterated N-heteroaryl having one point of attachment.

6. The composition of claim 5 , wherein the N-heteroaryl having one point of attachment is a carbazole or the deuterated N-heteroaryl having one point of attachment is a deuterated carbazole.

7. The composition of claim 1 , wherein x>0 and at least one R 1 is an alkyl or deuterated alkyl having 1-20 carbons.

8. The composition of claim 1 , wherein x>0 and at least one R 1 is a hydrocarbon aryl group having 6-36 ring carbons, the hydrocarbon aryl group having one point of attachment.

9. The composition of claim 1 , wherein x>0 and at least one R 1 is selected from the group consisting of phenyl, naphthyl, deuterated phenyl, deuterated naphthyl, and Formula a

where:

R 9 is the same or different at each occurrence and is selected from the group consisting of D, F, CN, alkyl, fluoroalkyl, hydrocarbon aryl, fluoroaryl, N-heteroaryl, amino, silyl, germyl, alkoxy, aryloxy, fluoroalkoxy, siloxane, siloxy, deuterated alkyl, deuterated partially-fluorinated alkyl, deuterated hydrocarbon aryl, deuterated partially-fluorinated aryl, deuterated N-heteroaryl, deuterated amino, deuterated silyl, deuterated germyl, deuterated alkoxy, deuterated aryloxy, deuterated fluoroalkoxy, deuterated siloxane, and deuterated siloxy, where adjacent R9 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 the point of attachment.

10. The composition of claim 9 , wherein x>0 and at least one R 1 has one or more substituents selected from the group consisting of D, F, CN, alkyl, silyl, germyl, hydrocarbon aryl, deuterated alkyl, deuterated silyl, deuterated germyl, and deuterated hydrocarbon aryl.

11. The composition of claim 1 , wherein Q is a hydrocarbon aryl group or deuterated aryl group having 6-36 ring carbons and has no heteroaromatic groups.

12. The composition of claim 1 , wherein Q is a heteroaryl having at least one ring atom which is selected from the group consisting of N, O, and S.

13. The composition of claim 1 , wherein the host compound having Formula II is at least 10% deuterated.

14. The composition of claim 1 , wherein at least one of x, y, x1, or y1 is non-zero.

15. The composition of claim 1 , wherein the dopant material is one of the following compounds:

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 20, 2019
From: E.I. DU PONT DE NEMOURS AND COMPANY
To: LG CHEM, LTD.
Reel/Frame 049226/0488 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 22, 2016
From: HERRON, NORMAN; GAO, WEIYING; GUIDRY, MARK A
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 039495/0785 →
Continuity (2)
Provisional Application 62194583 · Jul 20, 2015
Related Publication 20170025608A1 · Jan 26, 2017