Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10468609-B2
Application number	US-201715583429-A
Country	US
Kind code	B2
Filing date	May 1, 2017
Priority date	Jun 2, 2016
Publication date	Nov 5, 2019
Grant date	Nov 5, 2019

Abstract

New organic materials having polyaromatic structure containing boron and high triplet energy are disclosed. The high triplet energy materials are useful as host materials in PHOLEDs and improve device quantum efficiency and stability.

First claim

We claim:

1. A compound having a structure or partial structure of Formula I:

wherein R A , R B , and R C are each independently 5 or 6 membered aryl or heteroaryl rings;
wherein R 1 , R 2 , and R 3 each independently represent no substitutions or up to the maximum available substitutions;
wherein R 1 , R 2 , and R 3 are 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, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphine, and combinations thereof;
wherein any adjacent R 1 , R 2 , and R 3 are optionally joined or fused to form a ring;
wherein X 1 and X 7 are C or N;
wherein X 2 to X 6 are independently C;
wherein Y is N or P;
wherein Z is CRR′, O, PR, P(O)R, or S;
wherein Y 1 and Y 2 are each independently selected from the group consisting of carbon and nitrogen;
wherein R and R′ are 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, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphine, and combinations thereof;
wherein R and/or R′ are optionally joined or fused with R 1 or R 3 to form a ring;
wherein the dashed lines represent a metal M optionally coordinated to R B and R C ; and
wherein when M is coordinated to R B and R C , M replaces R 2 and R 3 on Y 1 and Y 2 and bonds to Y 1 and Y 2 .

2. The compound of claim 1 , wherein the compound has the formula:

3. The compound of claim 1 , wherein the compound is a dimer comprising two structures or partial structures of Formula I.

4. The compound of claim 1 , wherein at least one of R 1 , R 2 , and R 3 substituents are joined or fused to form a 5- or 6-membered ring, which can be further substituted.

5. The compound of claim 1 , wherein X 1 -X 6 are C, and X 7 is C or N.

6. The compound of claim 1 , wherein R and R′ are independently aryl or heteroaryl.

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

8. The compound of claim 1 , wherein X 1 is C or N, R A is aryl or heteroaryl and R A is connected to X 1 to form a fused ring.

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

10. The compound of claim 1 , wherein (a) at least one R 1 , R 2 , or R 3 comprises a substituent selected from the group consisting of carbazole, azacarbazole, dibenzofuran, azadibenzofuran, dibenzothiophene, azadibenzothiophene, dibenzoselenophene, azadibenzoselenophene, triphenylene, azatriphenylene, diphenylsilyl, triphenylsilyl, and tetraphenylsilyl;
(b) two adjacent substituents of R 1 , R 2 , or R 3 form a fused benzo substituent on R A , R B , or R C , respectively; or
(c) both (a) and (b) are true.

11. The compound of claim 1 , wherein M is coordinated to Y 1 and Y 2 , and the compound has the formula:

12. The compound of claim 11 , wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

13. The compound of claim 11 , wherein one of Y 1 and Y 2 is nitrogen and the other one of Y 1 and Y 2 is carbon; or one of Y 1 and Y 2 is neutral carbene carbon and the other one of Y 1 and Y 2 is anionic carbon.

14. The compound of claim 11 , wherein the compound is selected from the group consisting of:

Assignees

• Universal Display Corp

Inventors

• Lee Chi Hang
• Lam Siu Tung
• Kwong Raymond

Classifications

• C09K2211/10

  Non-macromolecular compounds · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C09K2211/18

  Metal complexes · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• H01L51/5056

  Electricity · mapped topic