IP Library › Granted Patent US 10,672,996
Granted Patent B2
US 10,672,996 · App. 15/239,961 · Granted Jun 2, 2020

Organic electroluminescent materials and devices

Inventors: Bin Ma (Plainsboro, NJ); Vadim Adamovich (Yardley, PA); Edward Barron (Hamilton, NJ); Jui-Yi Tsai (Newtown, PA); Mingjuan Su (Ewing, NJ); Lech Michalski (Pennington, NJ); Chuanjun Xia (Lawrenceville, NJ); Michael S. Weaver (Princeton, NJ); Walter Yeager (Yardley, PA); Bert Alleyne (Newtown, PA)
Assignee: UNIVERSAL DISPLAY CORPORATION
H01L51/0085C07F15/0033C09K11/025C09K11/06H01L51/0067H01L51/0074C09K2211/1029C09K2211/185H01L51/5012H01L51/5016
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Quick Facts
Patent No.
US 10,672,996
App. No.
15/239,961
Granted
Jun 2, 2020
Kind
B2
Abstract

The present invention relates to organometallic complexes for use as emitters where a molecule of the compound has an orientation factor greater than 0.67, and devices, such as organic light emitting diodes, including the same.

Claims (35)

1. A compound having a formula (L A ) m Ir(L B ) 3-m , wherein L A has a structure of Formula I

wherein m is 1 or 2;

wherein R 1 and R 2 each independently represent mono, di, tri, or tetra substitution, or no substitution;

wherein R 1 and R 2 are each independently hydrogen or a substituent selected from the group consisting of deuterium, C1 to C6 alkyl, C1 to C6 cycloalkyl, and partially or fully deuterated or fluorinated variants thereof; and

wherein L B is selected from the group consisting of:

2. The compound of claim 1 , wherein L B is selected from the group consisting of:

3. The compound of claim 1 , wherein R 6 is selected from the group consisting of partially deuterated or partially fluorinated alkyl having at least seven carbon atoms, partially deuterated or partially fluorinated cycloalkyl having at least seven carbon atoms, alkyl-cycloalkyl having at least seven carbon atoms, and partially or fully deuterated or fluorinated alkyl-cycloalkyl having at least seven carbon atoms.

4. The compound of claim 1 , wherein L A is selected from the group consisting of:

5. The compound of claim 4 , wherein the compound is Compound x having the formula Ir(L Af ) 2 (L Bk );

wherein x=227j+k−227, j is an integer from 1 to 112, 131 to 192, and 212 to 217, and k is an integer from 1 to 58, 60 to 86, 89 to 128, 132 to 138, 177, and 223;

wherein L B1 to L B58 , L B60 to L B86 , L B89 to L B128 , L B132 to L B138 , L B177 , and L B223 have the following structures:

6. The compound of claim 1 , wherein m is 2.

7. The compound of claim 1 , wherein R 1 and R 2 , are each independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, and combinations thereof.

8. A formulation comprising a compound according to claim 1 .

9. An organic light-emitting device (OLED) comprising:

an anode; a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound having a formula (L A ) m Ir(L B ) 3-m , wherein L A has a structure of Formula I

wherein m is 1 or 2;

wherein R 1 and R 2 each independently represent mono, di, tri, or tetra substitution, or no substitution;

wherein R 1 and R 2 are each independently hydrogen or a substituent selected from the group consisting of deuterium, C1 to C6 alkyl, C1 to C6 cycloalkyl, and partially or fully deuterated or fluorinated variants thereof; and

wherein L B is selected from the group consisting of:

10. A device selected from the group consisting of a consumer product, an electronic component module, and a lighting panel, said device comprising an OLED according to claim 9 .

11. The OLED of claim 9 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

12. The OLED of claim 9 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

13. The OLED of claim 9 , wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of:

and combinations thereof.

14. A consumer product comprising:

an organic light-emitting device (OLED) comprising:

an anode; a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound having a formula (L A ) m Ir(Le) 3-m , wherein L A has a structure of Formula I

wherein m is 1 or 2;

wherein R 1 and R 2 each independently represent mono, di, tri, or tetra substitution, or no substitution;

wherein R 1 and R 2 are each independently hydrogen or a substituent selected from the group consisting of deuterium, C1 to C6 alkyl, C1 to C6 cycloalkyl, and partially or fully deuterated or fluorinated variants thereof; and

wherein L B is selected from the group consisting of:

15. The consumer product of claim 14 , wherein the consumer product is selected from a flat panel display, a computer monitor, a medical monitor, a television, a billboard, lights 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, a tablet, a phablet, a personal digital assistant (PDAs), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a 3-D display, a vehicle, a wall, theater or stadium screen, or a sign.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 18, 2016
From: MA, BIN; ADAMOVICH, VADIM; BARRON, EDWARD; TSAI, JUI-YI; SU, MINGJUAN; MICHALSKI, LECH; XIA, CHUANJUN; WEAVER, MICHAEL S.; YEAGER, WALTER; ALLEYNE, BERT
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 039473/0801 →
Continuity (6)
Provisional Application 62213757 · Sep 3, 2015
Provisional Application 62232194 · Sep 24, 2015
Provisional Application 62291960 · Feb 5, 2016
Provisional Application 62322510 · Apr 14, 2016
Provisional Application 62330412 · May 2, 2016
Related Publication 20170077425A1 · Mar 16, 2017
Cited By (3)
US 12,201,011 US 12,439,813 US 12,454,542