Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10777749-B2
Application number	US-201615140768-A
Country	US
Kind code	B2
Filing date	Apr 28, 2016
Priority date	May 7, 2015
Publication date	Sep 15, 2020
Grant date	Sep 15, 2020

Abstract

Novel organic compounds containing aza-dibenzofuran, aza-dibenzothiophene and aza-dibenzoselenophene are disclosed in this application. These compounds improve OLED performance.

First claim

We claim:

1. A compound of Formula I:

wherein
X is selected from the group consisting of O, S, and Se;
R 2 represents mono, di, or tri substitution;
each R 2 is independently selected from the group consisting of hydrogen, 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 any two adjacent R 2 are optionally joined to form a ring;
wherein at least one R 2 is not hydrogen;
R 1 is selected from the group consisting of

wherein R 1 may be further substituted with a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof
wherein each occurrence of R 3 and R 4 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
wherein any two adjacent R 3 and R 4 are optionally joined to form a ring;
provided that when R 1 is selected from the group consisting of

 and

 then R 2 comprises

2. The compound of claim 1 , wherein X is O.

3. The compound of claim 1 , wherein X is S.

4. The compound of claim 1 , wherein R 2 comprises

wherein R 3 and R 4 are as defined in claim 1 .

5. The compound of claim 1 , wherein at least one of R 1 and R 2 comprises at least one F atom.

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

7. The compound of claim 1 , wherein R 1 is selected from the group consisting of biphenyl, dibenzofuran, dibenzothiophene, fluorene, and triphenylene.

8. The compound of claim 1 , wherein R 1 is selected from the group consisting of

wherein R 1 may be further substituted with a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

9. 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 of Formula I:

wherein
X is selected from the group consisting of O, S, and Se;
R 2 represents mono, di, or tri substitution;
each R 2 is independently selected from the group consisting of hydrogen, 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 any two adjacent R 2 are optionally joined to form a ring;
wherein at least one R 2 is not hydrogen;
R 1 is selected from the group consisting of

wherein R 1 may be further substituted with a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof
wherein each occurrence of R 3 and R 4 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
wherein any two adjacent R 3 and R 4 are optionally joined to form a ring;
provided that when R 1 is selected from the group consisting of

 and

 then R 2 comprises

10. The OLED of claim 9 , wherein the organic layer is an emissive layer and the compound of Formula I is a host.

11. The OLED of claim 9 , 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 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

Assignees

• Universal Display Corp

Inventors

• Yeager Walter
• Zeng Lichang
• Xia Chuanjun

Classifications

• C09K11/025 Primary

  non-luminescent particle coatings or suspension media · CPC title

• C07D495/04

  Ortho-condensed systems · CPC title

• C07D517/04

  Ortho-condensed systems · CPC title

• C07D491/048

  the oxygen-containing ring being five-membered · CPC title

• 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