Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10593892-B2
Application number	US-201615260753-A
Country	US
Kind code	B2
Filing date	Sep 9, 2016
Priority date	Oct 1, 2015
Publication date	Mar 17, 2020
Grant date	Mar 17, 2020

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:

R 1 to R 6 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;
wherein R 5 and R 6 optionally join to form a phenyl ring or substituted phenyl ring
wherein at least one of R 1 to R 6 comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, and dibenzoselenophene;
wherein at least one of R 1 to R 6 comprises at least one chemical group selected from the group consisting of aza-triphenylene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene,

wherein each occurrence of X 1 and X 2 is independently selected from the group consisting of NR, SiRR′, GeRR′, O, S, and Se; and
wherein each occurrence of R and R′ is 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; and adjacent substituents of R and R′ are optionally fused or joined to form a ring.

2. The compound of claim 1 , wherein the compound has triplet energy Tl of at least 3.2 eV.

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

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

5. 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.

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

7. The compound of claim 1 , wherein R 1 to R 6 are each independently selected from the group consisting of:
hydrogen,

8. A compound of Formula III or Formula IV

wherein X 1 is selected from the group consisting of NR, SiRR′, and GeRR′
X 2 is O;
R, R′, R 1 , R 2 , R 3 , R 4 , R 7 , R 8 , R 9 , and R 10 are 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; and adjacent substituents of R and R′ optionally join to form a ring; and
at least one of R 1 , R 2 , R 3 , R 4 , R 7 , R 8 , R 9 , and R 10 comprises a chemical group selected from the group consisting of silyl, non-fused five-membered heteroaromatic ring, and tetraphenylene.

9. The compound of claim 8 , wherein the compound is selected from the group consisting of:

10. An organic light-emitting device (OLED) comprising:
an anode; a cathode; and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having a formula selected from the group consisting of Formula I and Formula II:

R 1 to R 6 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;
wherein R 5 and R 6 optionally join to form a phenyl ring or substituted phenyl ring
wherein at least one of R 1 to R 6 comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, and dibenzoselenophene;
wherein at least one of R 1 to R 6 comprises at least one chemical group selected from the group consisting of aza-triphenylene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene,

wherein each occurrence of X 1 and X 2 is independently selected from the group consisting of NR, SiRR′, GeRR′, O, S, and Se;
wherein each occurrence of R and R′ is independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, hetero

Assignees

• Universal Display Corp

Inventors

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

Classifications

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C09K2211/1048

  with oxygen · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C07F7/0814

  said ring is substituted at a C ring atom by Si · CPC title

• C07D513/04

  Ortho-condensed systems · CPC title