Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12063853-B2
Application number	US-202016819789-A
Country	US
Kind code	B2
Filing date	Mar 16, 2020
Priority date	Oct 1, 2015
Publication date	Aug 13, 2024
Grant date	Aug 13, 2024

Abstract

This invention relates to the development of heterocyclic materials with high triplet excitation energy, which can be used as host materials in electroluminescent devices such as a PHOLED. The materials improve the performance of such devices by enhancing the lifetime and efficiency of the device when the newly developed heterocyclic materials are utilized as a host.

First claim

We claim:

1. A compound having a formula selected from the group consisting of Formula I and Formula II:

wherein each occurrence of X 1 is independently selected from the group consisting of NR, SiRR′, GeRR′, O, S, and Se; and
wherein each occurrence of X 2 is independently selected from the group consisting of NR, SiRR′, GeRR′, O, S, and Se;
wherein adjacent substituents of R and R′ are optionally fused or joined to form a ring;
wherein R, R′, and R′ to R 6 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
with the proviso that, in Formula II, R 5 and R 6 are selected from the group consisting of hydrogen and deuterium; and
wherein at least one of the following conditions is true:
(i) at least one of R 1 to R 6 and R comprises at least one chemical group selected from the group consisting of triphenylene, dibenzoselenophene, aza-triphenylene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene,

wherein X 1 is selected from the group consisting of Si, Ge, O, S, and Se, X 2 is selected from the group consisting of N, Si, Ge, O, S, and Se, and wherein no more than one of X 1 and X 2 is S; and

wherein X 2 is selected from the group consisting of Si, Ge, O, S, and Se;
(ii) at least one of R 1 to R 6 and R represents a chemical group selected from the group consisting of

wherein X 1 and X 2 are each independently selected from the group consisting of N, NPh, O, S, and Se and wherein no more than one of X 1 and X 2 is S,

wherein each X 2 is independently selected from the group consisting of N, NPh, O, S, and Se, triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-triphenylene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene, each of which is not further substituted;
wherein no more than one of X 1 and X 2 represents N;
wherein when X 1 or X 2 is N, then the N is directly bound to Formula I or Formula II; and
(iii) R 1 to R 6 and R are each independently selected from the group consisting of:
hydrogen,

wherein at least one of R 1 to R 6 and R is not hydrogen, phenyl, or pyridyl.

2. The compound of claim 1 , wherein the compound is represented by Formula I.

3. The compound of claim 1 , wherein the compound is represented by Formula II.

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

wherein R 11 and R 12 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

5. The compound of claim 1 , wherein R 1 to R 6 and R are each independently selected from the group consisting of hydrogen, aryl, substituted aryl, heteroaryl, and substituted heteroaryl.

6. The compound of claim 1 , wherein at least one of R 1 to R 6 and R comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, and dibenzoselenophene; and
wherein at least one of R 1 to R 6 and R comprises at least one chemical group selected from the group consisting of

aza-triphenylene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene;
wherein each occurrence of X 1 and X 2 is independently selected from the group consisting of N, Si, Ge, O, S, and Se.

7. A compound selected from the group consisting of:

Assignees

• Universal Display Corp

Inventors

• Wolohan Peter
• Ma Bin
• Fitzgerald George
• Silverstein Daniel W

Classifications

• H10K85/6572 Primary

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• C07F7/0812 Primary

  comprising a heterocyclic ring · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• C09K2211/1048

  with oxygen · CPC title