IP Library Granted Patent US 9,590,180
Granted Patent B2
US 9,590,180 · App. 14/491,280 · Granted Mar 7, 2017

Organic electroluminescent materials and devices

Inventors: Jason Brooks (Philadelphia, PA); Chuanjun Xia (Lawrenceville, NJ); Raymond Kwong (Plainsboro, NJ); James Fiordeliso (Morrisville, PA)
Assignee: UNIVERSAL DISPLAY CORPORATION
H01L51/0054C07C15/38C07D307/91C07D333/76C07D409/04C09B57/00C09K11/06H01L51/004H01L51/0061H01L51/0085H05B33/14C07C2103/42C09K2211/1007C09K2211/1011H01L51/0059H01L51/0081H01L51/5016H01L51/5024
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Quick Facts
Patent No.
US 9,590,180
App. No.
14/491,280
Granted
Mar 7, 2017
Kind
B2
Abstract

Disclosed is a compound having substructure F: wherein R′ 1 is a straight or branched chain of two or more non-fused aryl or non-fused heteroaryl groups substituted with R a , wherein R a is a non-fused aryl or non-fused heteroaryl, a branched or straight chain of non-fused aryl or a non-fused heteroaryl, or an alkyl substituted non-fused aryl or an alkyl substituted non-fused heteroaryl group. The compounds may be useful in phosphorescent organic light emitting devices.

Claims (24)

1. A compound comprising a triphenylene core of Formula I:

wherein each of R 1 , R 2 , and R 3 is independently a hydrogen, a non-fused aryl group or a non-fused heteroaryl six-membered ring having one or more meta-substituents;

wherein each meta-substituent is a non-fused aryl or heteroaryl six-membered ring optionally substituted with further substituents selected from the group consisting of non-fused aryl groups, non-fused heteroaryl groups, and alkyl groups; and

wherein at least one of R 1 , R 2 , and R 3 is a non-fused aryl or heteroaryl six-membered ring having at least one meta-substituent that is a non-fused aryl or heteroaryl group further substituted with one or more non-fused aryl or heteroaryl groups, wherein the at least one meta-substituent is substituted with a chain of at least two non-fused aryl or heteroaryl groups.

2. The compound of claim 1 , wherein at least two of R 1 , R 2 , and R 3 is a non-fused aryl or heteroaryl six-membered ring having at least one meta-substituent that is a non-fused aryl or heteroaryl group optionally substituted with further substituents selected from the group consisting of non-fused aryl groups, non-fused heteroaryl groups, and alkyl groups.

3. The compound of claim 1 , wherein each of R 1 , R 2 , and R 3 includes no more than three para-substituted phenyl rings.

4. The compound of claim 1 , wherein the compound has the structure:

wherein R′ 1 is a non-fused aryl group or a non-fused heteroaryl group; and

wherein R′ 1 is substituted with a chain of at least two non-fused aryl or heteroaryl groups.

5. A compound comprising the substructure F:

wherein R′ 1 is selected from the group consisting of a non-fused aryl group substituted with R a and a non-fused heteroaryl group substituted with R a , wherein R a is a non-fused aryl or heteroaryl, a branched or straight chain of non-fused aryls or heteroaryls, or an alkyl substituted non-fused aryl or an alkyl substituted non-fused heteroaryl group.

6. The compound of claim 5 , wherein R a is a branched or straight chain of non-fused aryls or heteroaryls, or an alkyl substituted non-fused aryl or an alkyl substituted non-fused heteroaryl group.

7. The compound of claim 5 ,

wherein R′ 1 is a straight or branched chain of two or more non-fused aryl groups substituted with R a or a straight or branched chain of two or more non-fused heteroaryl groups substituted with R a .

8. The compound of claim 5 , wherein the compound is any one of:

9. An organic light emitting device, comprising:

an anode;

a cathode;

an organic layer, disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising a triphenylene core of Formula I:

wherein each of R 1 , R 2 , and R 3 is independently a hydrogen, a non-fused aryl group or a non-fused heteroaryl six-membered ring having one or more meta-substituents;

wherein each meta-substituent is a non-fused aryl or heteroaryl group optionally substituted with further substituents selected from the group consisting of non-fused aryl groups, non-fused heteroaryl groups, and alkyl groups; and

wherein at least one of R 1 , R 2 , and R 3 is a non-fused aryl or heteroaryl six-membered ring having at least one meta-substituent that is a non-fused aryl or heteroaryl group further substituted with one or more non-fused aryl or heteroaryl groups, wherein the at least one meta-substituent is substituted with a chain of at least two non-fused aryl or heteroaryl groups.

10. The organic light emitting device of claim 9 , wherein at least one of R 1 , R 2 , and R 3 is a heteroaryl six-membered ring selected from the group consisting of pyridine, pyrazine and pyrimidine, wherein said heteroaryl six-membered ring has at least one meta-substituent that is a non-fused aryl or heteroaryl group further substituted with one or more non-fused aryl or heteroaryl groups, wherein the at least one meta-substituent is substituted with a chain of at least two non-fused aryl or heteroaryl groups.

11. The compound of claim 1 , wherein at least one of R 1 , R 2 , and R 3 is a heteroaryl six-membered ring selected from the group consisting of pyridine, pyrazine and pyrimidine, wherein said heteroaryl six-membered ring has at least one meta-substituent that is a non-fused aryl or heteroaryl group further substituted with one or more non-fused aryl or heteroaryl groups, wherein the at least one meta-substituent is substituted with a chain of at least two non-fused aryl or heteroaryl groups.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 19, 2014
From: BROOKS, JASON; XIA, CHUANJUN; KWONG, RAYMOND; FIORDELISIO, JAMES
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 033779/0585 →
Continuity (5)
Continuation 14135191 · Dec 19, 2013
Continuation 12865628
Provisional Application 61017506 · Dec 28, 2007
Provisional Application 60936944 · Jun 23, 2007
Related Publication 20150001524A1 · Jan 1, 2015