IP Library › Granted Patent US 12,193,319
Granted Patent B2
US 12,193,319 · App. 18/353,347 · Granted Jan 7, 2025

Organic electroluminescent materials and devices

Inventors: Tyler Fleetham (Newtown, PA); Nicholas J. Thompson (New Hope, PA)
Assignee: UNIVERSAL DISPLAY CORPORATION
H10K85/346H10K85/40H10K85/654H10K85/6572H10K85/6574H10K85/6576H10K50/15H10K50/16H10K2101/30
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Quick Facts
Patent No.
US 12,193,319
App. No.
18/353,347
Granted
Jan 7, 2025
Kind
B2
Abstract

Provided are organometallic compounds. Also provided are formulations comprising these organometallic compounds. Further provided are OLEDs and related consumer products that utilize both a disclosed compound and a Pt complex compound.

Claims (39)

1. A compound having the formula:

wherein X 5 -X 20 are each independently C or N;

each of R 6 , R 7 , R 8 , R 9 and R 10 is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

wherein R 10 is a substituted biphenyl;

wherein the substituted biphenyl is substituted with at least one carbazole.

2. The compound of claim 1 , wherein the substituted biphenyl R 10 is substituted with at least two carbazole moieties.

3. The compound of claim 1 , wherein the substituted biphenyl R 10 is substituted with an unsubstituted carbazole.

4. The compound of claim 1 , wherein the substituted biphenyl R 10 is a dicarbazole biphenyl.

5. The compound of claim 1 , wherein each phenyl of the substituted biphenyl R 10 is substituted with at least one carbazole.

6. The compound of claim 1 , wherein at least one phenyl of the substituted biphenyl R 10 is substituted with at least two carbazole moieties.

7. The compound of claim 1 , wherein the substituted biphenyl R 10 is [1,1′-biphenyl]-4-yl that is substituted with at least one carbazole.

8. The compound of claim 1 , wherein at least one carbazole is substituted ortho to the biphenyl bond.

9. The compound of claim 1 , wherein at least two carbazoles are substituted ortho to the biphenyl bond.

10. The compound of claim 1 , wherein the compound comprises a 3,9 biscarbazole.

11. The compound of claim 1 , wherein the compound comprises at least four carbazole moieties.

12. The compound of claim 1 , wherein the compound is partially or fully deuterated.

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

14. An organic light emitting device (OLED) comprising:

an anode;

a cathode; and

an emissive layer disposed between the anode and the cathode, the emissive layer comprising a host compound,

wherein the host compound has the formula of

wherein X 5 -X 20 are each independently C or N;

each of R 6 , R 7 , R 8 , R 9 and R 10 is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

wherein R 10 is a substituted biphenyl;

wherein the substituted biphenyl is substituted with at least one carbazole.

15. The OLED of claim 14 , wherein the host compound is selected from the group consisting of

16. The OLED of claim 14 , wherein the emissive layer comprises an additional compound, and the additional compound is also a co-host which comprises a chemical moiety selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, pyridine, pyrimidine, triazine, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene).

17. A consumer product comprising an organic light emitting device (OLED) comprising:

an anode;

a cathode; and

an emissive layer disposed between the anode and the cathode, the emissive layer comprising a host compound, wherein the host compound has the formula of

wherein X 5 -X 20 are each independently C or N;

each of R 6 , R 7 , R 8 , R 9 and R 10 is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

wherein R 10 is a substituted biphenyl;

wherein the substituted biphenyl is substituted with at least one carbazole.

18. The consumer product of claim 17 , wherein the host compound is selected from the group consisting of

19. The consumer product of claim 17 , wherein the consumer product is selected from the group consisting of a flat panel display, a computer monitor, a medical monitor, a television, a billboard, a light for interior or exterior illumination and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cell phone, tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display, a 3-D display, a virtual reality or augmented reality display, a vehicle, a large area wall, a theater or stadium screen, and a sign.

20. The consumer product of claim 17 , wherein the emissive layer of the OLED comprises an additional compound, and the additional compound is also a co-host which comprises a chemical moiety selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, pyridine, pyrimidine, triazine, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene).

Assignments (1)
NUNC PRO TUNC ASSIGNMENT Recorded Jul 18, 2023
From: FLEETHAM, TYLER; THOMPSON, NICHOLAS J.
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 064291/0056 →
Continuity (6)
Continuation 17201222 · Mar 15, 2021
Continuation In Part 16841182 · Apr 6, 2020
Continuation In Part 16683507 · Nov 14, 2019
Provisional Application 63036764 · Jun 9, 2020
Provisional Application 62772403 · Nov 28, 2018
Related Publication 20230363254A1 · Nov 9, 2023
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