Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-11716902-B2
Application number	US-202017089278-A
Country	US
Kind code	B2
Filing date	Nov 4, 2020
Priority date	Dec 7, 2012
Publication date	Aug 1, 2023
Grant date	Aug 1, 2023

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. An organic light emitting device (OLED), 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 s 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 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 at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is

 which can be further substituted;
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 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;
wherein at least one of Z 1 , Z 2 , Z 3 , Z 4 and Z 5 is CR 9 , wherein R 9 is aryl, which can be further substituted;
wherein the emissive layer further comprises a first phosphorescent emitting material; and
wherein at least one of the following is true:
(i) at least one of the at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 that is

 comprises an electron donor group independently selected from the group consisting of:

wherein X and Y are selected from the group consisting of O, S, NR 14 , m is an integer from 1 to 20, n 2 is an integer from 1 to 20, and wherein R 14 is selected from the group consisting of aryl and heteroaryl;
(ii) L 1 is selected from the group consisting of

 and combinations thereof; and
(iii) Z 1 , Z 3 , and Z 5 are N.

2. The OLED of claim 1 , wherein condition (iii) is met.

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

wherein R 91 and R 92 are aryl, which can be further substituted.

4. The OLED 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

is which is not further substituted.

5. The OLED of claim 1 , wherein R 3 is

which is not further substituted, and R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , and R 8 are H.

6. The OLED of claim 1 , wherein the compound is

7. The OLED of claim 1 , wherein the first phosphorescent emitting material is an Ir(III) organometallic complex.

8. The OLED of claim 7 , wherein the Ir(III) organometallic complex comprises a phenylpyridine ligand.

9. The OLED of claim 1 , wherein the first phosphorescent emitting material is a Pt(II) organometallic complex.

10. The OLED of claim 9 , wherein the Pt(II) organometallic complex is a Pt tetradentate complex.

11. The OLED of claim 10 , wherein the Pt tetradentate complex comprises at least one metal-carbene bond.

12. The OLED of claim 1 , wherein the emissive layer further comprises a host material.

13. The OLED of claim 1 , wherein the host material comprises a group selected from the group consisting of aromatic fused rings, arylcarbazoles, aryltriphenylene, poly-fused heteroaryl, donor acceptor type molecules, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, spirofluorene, spirofluorene-carbazole, indolocabazoles, 5-member ring electron deficient heterocycles, tetraphenylene, dibenzothiophene-carbazole, dibenzofuran-carbazole, silicon aryl, germanium aryl, aryl benzoyl ester, and carbazole linked by non-conjugated groups.

14. An emissive region in an organic light emitting device, the emissive region comprising 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 s 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 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 at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is

 which can be further substituted;
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 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;
wherein at least one of Z 1 , Z 2 , Z 3 , Z 4 and Z 5 is CR 9 , wherein R 9 is aryl, which can be further substituted;
wherein the emissive layer further comprises a first phosphorescent emitting material; and
wherein at least one of the following is true:
(i) at least one of the at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 that is

Assignees

• Universal Display Corp

Inventors

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

Classifications

• H10K85/654 Primary

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title

• C07D403/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D403/14

  containing three or more hetero rings · CPC title

• C07D405/14

  containing three or more hetero rings · CPC title

• C07D409/14

  containing three or more hetero rings · CPC title