IP Library Granted Patent US 10,897,016
Granted Patent B2
US 10,897,016 · App. 15/789,096 · Granted Jan 19, 2021

Organic electroluminescent materials and devices

Inventors: Bin Ma (Piainsboro, NJ); Alan Deangelis (Pennington, NJ)
Assignee: UNIVERSAL DISPLAY CORPORATION
H01L51/0074C07D333/76C09K11/025C09K11/06H01L51/0054C09K2211/1029C09K2211/185H01L51/0085H01L51/5004H01L51/5016H01L51/5024H01L51/5056H01L51/5072H01L51/5088H01L51/5096H01L2251/308
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Quick Facts
Patent No.
US 10,897,016
App. No.
15/789,096
Granted
Jan 19, 2021
Kind
B2
Abstract

A compound useful as a host material in an OLED is provided. The compound includes at least one chemical group selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, aza-triphenylene, azacarbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene; wherein the compound is substituted by at least one R selected from the group consisting of alkyl, cycloalkyl, spiroalkyl, partially or fully deuterated variants thereof, partially or fully fluorinated variants thereof, and combination thereof.

Claims (34)

1. A compound, wherein the compound has a structure selected from

wherein R 1 to R 5 each independently represents mono to the possible maximum number of substitution, or no substitution;

wherein R 1 to R 6 each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein L is an organic linker or a direct bond;

wherein at least one of R 1 , R 2 , R 3 , R 4 , and R 5 is an R;

wherein R is selected from the group consisting of partially or fully deuterated alkyl, partially or fully fluorinated alkyl, cycloalkyl, partially or fully deuterated cycloalkyl, partially or fully fluorinated cycloalkyl, spiroalkyl, partially or fully deuterated spiroalkyl, partially or fully fluorinated spiroalkyl, and combination thereof; and

X 1 is S, O, or Se.

2. The compound of claim 1 , wherein the compound has the structure

and X 1 is S.

3. The compound of claim 1 , wherein the compound has the structure

and X 1 is O.

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

and X 1 is Se.

5. The compound of claim 1 , wherein the compound has the structure

and at least one R 1 is R.

6. The compound of claim 1 , wherein the compound has the structure

and at least one R 2 is R.

7. The compound of claim 1 , wherein the compound has the structure

and at least one R 3 is R.

8. The compound of claim 1 , wherein the compound has the structure

and at least one R 4 is R.

9. The compound of claim 1 , wherein the compound has the structure

and at least one R 5 is R.

10. The compound of claim 1 , wherein the compound has the structure

11. The compound of claim 1 , wherein the at least one R contains at least two carbon atoms.

12. The compound of claim 1 , wherein the at least one R contains at least three carbon atoms.

13. The compound of claim 1 , wherein the at least one R contains at least four carbon atoms.

14. The compound of claim 1 , wherein the at least one R contains at least six carbon atoms.

15. The compound of claim 1 , wherein the at least one R comprises at least one cycloalkyl or spiroalkyl.

16. The compound of claim 1 , wherein the at least one R is CD 3 .

17. The compound of claim 1 , wherein R comprises a moiety selected from the group consisting of partially or fully deuterated alkyl, partially or fully fluorinated alkyl, and combinations thereof.

18. The compound of claim 1 , wherein R comprises a moiety selected from the group consisting of cycloalkyl, partially or fully deuterated cycloalkyl, partially or fully fluorinated cycloalkyl, and combinations thereof.

19. The compound of claim 1 , wherein R comprises a moiety selected from the group consisting of spiroalkyl, partially or fully deuterated spiroalkyl, partially or fully fluorinated spiroalkyl, and combination thereof.

20. The compound of claim 1 , wherein the compound is selected from the group consisting of:

Assignments (1)
NUNC PRO TUNC ASSIGNMENT Recorded Oct 20, 2017
From: MA, BIN; DEANGELIS, ALAN
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 043911/0731 →
Continuity (2)
Provisional Application 62421412 · Nov 14, 2016
Related Publication 20180138425A1 · May 17, 2018
Cited By (1)
US 12,501,829