Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10109799-B2
Application number	US-201615359597-A
Country	US
Kind code	B2
Filing date	Nov 22, 2016
Priority date	May 21, 2015
Publication date	Oct 23, 2018
Grant date	Oct 23, 2018

Abstract

Novel substituted tetraphenylene compounds useful as host for phosphorescent emitters in OLEDs is disclosed.

First claim

We claim:

1. A compound having a formula:

wherein X 1 -X 16 are each independently selected from the group consisting of CR and N;
wherein each R is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, haloalkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, thioalkoxy, aryloxy, thioaryloxy, amino, arylamino, diarylamino, carbazolyl, silyl, halosilyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acids, nitrile, isonitrile, sulfanyl, phosphino, and combinations thereof;
wherein at least one of X 1 -X 16 is CR;
wherein R is

wherein Y 1 -Y 8 are independently selected from the group consisting of CR′ and N;
wherein each R′ is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, haloalkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, thioalkoxy, aryloxy, thioaryloxy, amino, arylamino, diarylamino, carbazolyl, aza-carbazolyl, silyl, halosilyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acids, nitrile, isonitrile, sulfanyl, phosphino, and combinations thereof;

wherein at least one of Y 1 to Y 8 is CR′ whose R′ is a group containing at least one carbazole or aza-carbazole.

2. The compound of claim 1 , wherein each of X 1 to X 16 is CR.

3. The compound of claim 1 , wherein at least one of X 1 to X 16 is N.

4. The compound of claim 1 , wherein each of Y 1 to Y 8 is CR′.

5. The compound of claim 1 , wherein at least one of Y 1 to Y 8 is N.

6. The compound of claim 1 , wherein at least one of Y 1 to Y 8 is CR′ whose R′ is a group containing at least one carbazole.

7. The compound of claim 1 , wherein at least one of Y 1 to Y 8 is CR′ whose R′ is a group containing at least one aza-carbazole.

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

9. A device comprising one or more organic light emitting devices, at least one of the organic light emitting devices comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having a formula:

wherein X 1 -X 16 are each independently selected from the group consisting of CR and N;
wherein each R is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, haloalkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, thioalkoxy, aryloxy, thioaryloxy, amino, arylamino, diarylamino, carbazolyl, silyl, halosilyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acids, nitrile, isonitrile, sulfanyl, phosphino, and combinations thereof;
wherein at least one of X 1 -X 16 is CR;
wherein R is

wherein Y 1 -Y 8 ;
wherein Y 1 to Y 8 are independently selected from the group consisting of CR′ and N;
wherein each R′ is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, haloalkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, thioalkoxy, aryloxy, thioaryloxy, amino, arylamino, diarylamino, carbazolyl, aza-carbazolyl, silyl, halosilyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acids, nitrile, isonitrile, sulfanyl, phosphino, and combinations thereof;
wherein at least one of Y 1 to Y 8 is CR′; and
wherein R′ is a group containing at least one carbazole or aza-carbazole.

10. The device of claim 9 , wherein each of X 1 -X 16 is CR.

11. The device of claim 9 , wherein at least one of X 1 -X 16 is N.

12. The device of claim 9 , wherein the compound of Formula 2 is selected from the group consisting of:

13. The device of claim 9 , wherein the organic layer is an emissive layer and the compound is a host.

14. The device of claim 9 , wherein the organic layer further comprises a phosphorescent emissive dopant.

15. The device of claim 9 , wherein the organic layer further comprises a phosphorescent emissive dopant, wherein the phosphorescent 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 1 to X 13 are independently selected from the group consisting of carbon and nitrogen;
wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO 2 , CR′R″, SiR′R″, and GeR′R″;
wherein R′ and R″ are optionally fused or joined to form a ring;
wherein each R a , R b , R c , and R d may represent from mono substitution to the possible maximum number of substitution, or no substitution;
wherein R′, R″, R a , R b , R c , and R d 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, nitrile, isonitrile, sulfanyl, phosphino,

Assignees

• Universal Display Corp

Inventors

• Kwong Raymond
• Lam Sze Kui

Classifications

• C07D209/86

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title

• H01L51/0072

  Electricity · mapped topic

• C07D519/00

  Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00 · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C07D471/04

  Ortho-condensed systems · CPC title