Organic Electroluminescent Materials and Devices

Patent metadata

Field	Value
Publication number	US-2016285009-A1
Application number	US-201615075622-A
Country	US
Kind code	A1
Filing date	Mar 21, 2016
Priority date	Mar 24, 2015
Publication date	Sep 29, 2016
Grant date	—

Abstract

Organic macrocyclic compounds with a ring including functional groups, such as carbazole units and several aromatic or heteroaromatic units, are disclosed in this application. The compounds are expected to improve OLED performance.

First claim

We claim:

1 . A compound having Formula I:

wherein m is an integer from 0 to 10, n is an integer from 1 to 10;
wherein when m or n is larger than 1, each L and G 3 can be the same or different;
wherein when m is 0, G 3 is not present;
wherein L is a linker selected from the group consisting of a direct bond, alkyl, cycloalkyl, amino, silyl, oxygen, non-fused aryl, non-fused heteroaryl, and combinations thereof;
wherein G 1 , G 2 , and G 3 are each independently selected from the group A consisting of carbazole, dibenzofuran, dibenzothiophene, dibenzoselenphene, triphenylene, fluorene, aza-carbazole, aza-dibenzofuran, aza-dibenzothiophene, aza-dibenzoselenphene, aza-triphenylene, and aza-fluorene;
wherein L, G 1 , G 2 , and G 3 each can be further substituted by one or more substituents 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 substituents can optionally join or fuse into a ring; and
wherein each member in group A can be used no more than twice.

2 . The compound of claim 1 , wherein m is an integer from 0 to 5, and n is an integer from 1 to 5.

3 . The compound of claim 1 , wherein m is an integer from 0 to 3, and n is an integer from 1 to 3.

4 . The compound of claim 1 , wherein each member in group A can be used only once.

5 . The compound of claim 1 , wherein L is selected from the group consisting of:
direct bond,

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

7 . The compound of claim 1 , wherein G 1 , G 2 , and G 3 are each independently selected from the group consisting of:

wherein Z 1 to Z 13 are each independently selected from the group consisting of CR 1 and N;
wherein X 1 and X 2 are selected from the group consisting of O, S, Se, NR 2 , CR 3 R 4 ;
wherein R 1 , R 2 , R 3 , and R 4 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, and
wherein any two adjacent substituents can optionally join or fuse into a ring.

8 . The compound of claim 7 , wherein R 2 is selected from the group consisting of,

9 . The compound of claim 1 , 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, comprising a compound having Formula I:

wherein m is an integer from 0 to 10, n is an integer from 1 to 10;
wherein when m or n is larger than 1, each L and G 3 can be the same or different;
wherein when m is 0, G 3 is not present;
wherein L is a linker selected from the group consisting of a direct bond, alkyl, cycloalkyl, amino, silyl, oxygen, non-fused aryl, non-fused heteroaryl, and combinations thereof;
wherein G 1 , G 2 , and G 3 are each independently selected from the group A consisting of carbazole, dibenzofuran, dibenzothiophene, dibenzoselenphene, triphenylene, fluorene, aza-carbazole, aza-dibenzofuran, aza-dibenzothiophene, aza-dibenzoselenphene, aza-triphenylene, and aza-fluorene;
wherein L, G 1 , G 2 , and G 3 each can be further substituted by one or more substituents 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 substituents can optionally join or fuse into a ring; and
wherein each member in group A can be used no more than twice.

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

12 . The OLED of claim 10 , 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 e

Assignees

• Universal Display Corp

Inventors

• Dyatkin Alexey Borisovich
• Xia Chuanjun
• Zeng Lichang
• Lin Chun

Classifications

• C07D495/18

  Bridged systems · CPC title

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C07D495/22

  in which the condensed system contains four or more hetero rings · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title