Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10403826-B2
Application number	US-201615145961-A
Country	US
Kind code	B2
Filing date	May 4, 2016
Priority date	May 7, 2015
Publication date	Sep 3, 2019
Grant date	Sep 3, 2019

Abstract

The present invention includes organic compounds with two substituted triazine, pyridine, pyrimidine or pyrazine rings attached to an aromatic or heteroaromatic ring system. The compounds are expected to improve OLED performance.

First claim

We claim:

1. A compound having Formula I:
A-(L 1 ) n -Z-(L 2 ) m -B,  Formula I;

wherein A and B are each independently

wherein R 1 and R 2 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 L 1 and L 2 are each independently selected from the group consisting of heteroaryl, alkyl, cycloalkyl, non-aromatic heterocycle, silyl, oxygen, and combination thereof;
wherein L 1 and L 2 may be optionally substituted with one or more substituents selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein n and m are each 0;
wherein Z is selected from the group consisting of:

and
wherein Z can be optionally substituted by one or more substituents selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

2. The compound of claim 1 , wherein R 1 and R 2 are each independently selected from the group consisting of phenyl, biphenyl, naphthalene, terphenyl, naphthalene, triphenylene, phenanthrene, anthracene, pyrene, chrysene, fluoranthene, dibenzofuran, dibenzothiophene, benzofuran, benzothiophene, dibenzoselenophene, benzoselenophene, carbazole, indolocarbazole, indolodibenzofuran, indolodibenzothiophene, indolofluorene, pyridine, pyrimidine, phenylpyridine, quinolone, quinazoline, quinoxaline, benzoquinoline, phenanthridine, phenanthroline, acridine, azatriphenylene, azadibenzofuran, azadibenzothiophene, azadibenzoselenophene and azacarbazole.

3. The compound of claim 1 , wherein A and B are each independently selected from the group consisting of:

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

5. A compound selected from the group consisting of:

6. 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 selected from the group consisting of compounds 33-41 and a compound of Formula I:

wherein in Formula I:
A-(L 1 ) n -Z-(L 2 ) m -B  (Formula I);

wherein A and B are each independently

wherein R 1 and R 2 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 L 1 and L 2 are each independently selected from the group consisting of heteroaryl, alkyl, cycloalkyl, non-aromatic heterocycle, silyl, oxygen, and combination thereof;
wherein L 1 and L 2 may be optionally substituted with one or more substituents selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein n and m are each 0;
wherein Z is selected from the group consisting of:

and
wherein Z can be optionally substituted by one or more substituents selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

7. The OLED of claim 6 , wherein the organic layer is an emissive layer and the compound is a host.

8. The OLED of claim 6 , wherein the organic layer further comprises a phosphorescent emissive dopant; wherein the emissive dopant is a transition metal complex having at least one ligand or part of the ligand if the ligand is more than bidentate selected from the group consisting of:

wherein each X

Assignees

• Universal Display Corp

Inventors

• Dyatkin Alexey Borisovich
• Yeager Walter
• Zeng Lichang
• Xia Chuanjun

Classifications

• H05B33/20 Primary

  characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded · CPC title

• C07D403/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D409/14

  containing three or more hetero rings · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title