Organic Electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10529931-B2
Application number	US-201615075622-A
Country	US
Kind code	B2
Filing date	Mar 21, 2016
Priority date	Mar 24, 2015
Publication date	Jan 7, 2020
Grant date	Jan 7, 2020

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, cycloalkyl, 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 triphenylene, aza-triphenylene, and the formula

wherein the triphenylene or aza-triphenylene 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;
wherein Z 1 to Z 8 are each independently selected from the group consisting of CR 1 and N;
wherein X 1 is selected from the group consisting of O, S, Se, NR 2 , CR 3 R 4 ;
wherein each R 1 is independently selected from the group consisting of a direct bond, 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;
wherein 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;
wherein L 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;
wherein each member in group A can be used no more than twice; and
wherein when any G 1 , G 2 , and G 3 is of the formula

then one of Z 1 to Z 4 and one of Z 5 to Z 8 is CR 1 and R 1 is a direct bond.

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. 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, cycloalkyl, 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:

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 each R 1 is independently selected from the group consisting of a direct bond, 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;
wherein 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,
wherein any two adjacent substituents can optionally join or fuse into a ring;
wherein L 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;
wherein each member in group A can be used no more than twice; and
two Z groups are each CR 1 and R 1 is a direct bond.

7. The compound of claim 6 , wherein R 2 is selected from the group consisting of,

8. A compound selected from the group consisting of:

Assignees

• Universal Display Corp

Inventors

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

Classifications

• C07D495/22

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

• C07D495/08

  Bridged systems · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• C07D495/18

  Bridged systems · CPC title