Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10069081-B2
Application number	US-201715586997-A
Country	US
Kind code	B2
Filing date	May 4, 2017
Priority date	Dec 7, 2012
Publication date	Sep 4, 2018
Grant date	Sep 4, 2018

Abstract

Devices containing novel carbazole-containing compounds are provided. The novel compounds also contain electron donor groups, aryl linkers, and at least one nitrogen heterocycle. These novel organic compounds can exhibit delayed fluorescence in the devices.

First claim

The invention claimed is:

1. A first device comprising a first organic light emitting device, comprising:
an anode;
a cathode; and
an emissive layer, disposed between the anode and the cathode;
wherein the emissive layer comprises a compound having the formula:

wherein Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are each independently selected from group consisting of CR 9 and N;
wherein any adjacent R 9 are optionally joined to form a fused ring;
wherein at least one of Z 1 , Z 2 , Z 3 , Z 4 and Z 5 is N;
wherein L 1 is selected from the group consisting of:

and combinations thereof;
wherein X 1 is O, S, or CRR′;
wherein R, R′ are optionally joined to form a ring;
wherein n 1 is an integer from 1 to 20;
wherein L 1 can be further substituted by a substituent selected from the group consisting of alkyl, aryl, and heteroaryl;
wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 comprises at least one electron donor group selected from the group consisting of:

wherein X and Y is selected from the group consisting of O, S, NR 14 ; and
wherein R 11 , R 12 , R 13 and R 14 are selected from the group consisting of aryl and heteroaryl;
wherein any two adjacent R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are not joined to form a ring;
wherein m is an integer from 1 to 20;
wherein n 2 is an integer from 1 to 20;
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 do not contain an electron acceptor group;
wherein R 9 does not contain an electron donor group;
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof;
wherein R 9 , R, and R′ are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, arylalkyl, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof; and
wherein at least one of Z 1 , Z 2 , Z 3 , Z 4 and Z 5 is CR 9 wherein R 9 is selected from aryl and heteroaryl, and can be further substituted.

2. The first device of claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 comprises the electron donor group selected from the group consisting of:

3. The first device of claim 1 , wherein the compound has the formula:

and
wherein R 91 and R 92 are independently selected from aryl or heteroaryl, and can be further substituted.

4. The first device of claim 1 , wherein the electron donor group is selected from the group consisting of:

5. The first device of claim 1 , wherein the compound is selected from the group consisting of:

Assignees

• Universal Display Corp

Inventors

• Xia Chuanjun
• Lin Chun
• Kwong Raymond
• Joseph Scott
• Esler James

Classifications

• C07D409/14

  containing three or more hetero rings · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C07D403/14

  containing three or more hetero rings · CPC title

• C07D403/10

  linked by a carbon chain containing aromatic rings · CPC title