Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-11780829-B2
Application number	US-202016744728-A
Country	US
Kind code	B2
Filing date	Jan 16, 2020
Priority date	Jan 30, 2019
Publication date	Oct 10, 2023
Grant date	Oct 10, 2023

Abstract

A compound of Formula X

wherein
ring A is absent, or present and selected from a 5-membered or 6-membered, carbocyclic or heterocyclic ring, which is optionally substituted; ring B is absent, or present and selected from a 5-membered or 6-membered, carbocyclic or heterocyclic ring, which is optionally substituted; and at least one of ring A or ring B is present, and the hash line represents ring A fused to ring N—W 1 —W 3 and ring B fused to ring N—W 4 —W 6 ;
W 1 , W 2 , W 3 , W 4 , W 5 , and W 6 are independently selected from CR 1 or N;
Z is selected from CR Z or N; and Y is selected from a group consisting of C(R 2 ) 2 , B(R 2 ) 2 , Al(R 2 ) 2 , Si(R 2 ) 2 , and Ge(R 2 ) 2 .

An optoelectronic device selected from the group consisting of a photovoltaic device, a photodetector device, a photosensitive device, and an OLED, the optoelectronic device including an organic layer that comprises a compound of Formula X. A consumer product that includes the optoelectronic device.

First claim

We claim:

1. An optoelectronic device selected from the group consisting of a photovoltaic device, a photodetector device, a photosensitive device, and an OLED, the optoelectronic device including an organic layer that comprises a compound of Formula X; wherein the compound of Formula X is a fluorescent acceptor; and wherein the optoelectronic device further comprises a phosphorescent sensitizer compound;

wherein
ring A is absent, or present and selected from a 5-membered or 6-membered, carbocyclic or heterocyclic ring, which is optionally substituted;
ring B is absent, or present and selected from a 5-membered or 6-membered, carbocyclic or heterocyclic ring, which is optionally substituted;
wherein at least one of ring A or ring B is present, and the hash line represents ring A fused to ring N—W 1 —W 3 and ring B fused to ring N—W 4 —W 6 ;
wherein at least one of ring A or ring B is a 6-membered heteroaryl ring;
W 1 , W 2 , W 3 , W 4 , W 5 , and W 6 are independently selected from CR 1 or N;
Z is selected from CR Z or N;
Y is selected from a group consisting of C(R 2 ) 2 , B(R 2 ) 2 , Al(R 2 ) 2 , Si(R 2 ) 2 , and Ge(R 2 ) 2 ; wherein
R Z and each R 1 and R 2 are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, or optionally, two R 2 join to form a cycloalkyl or heterocyclic ring;
wherein optionally, R 1 can join with R 2 to form a five-membered or six-membered, carbocyclic or heterocyclic ring, which is optionally substituted.

2. The OLED of claim 1 , wherein the organic layer is disposed between an anode and a cathode.

3. The OLED of claim 1 , wherein the phosphorescent sensitizer compound forms an exciplex.

4. The OLED of claim 1 , wherein the phosphorescent sensitizer compound and the compound of Formula X are in the same layer.

5. The OLED of claim 1 , wherein the phosphorescent sensitizer compound and the compound of Formula X are in different layers.

6. The OLED of claim 1 , wherein the compound of Formula X has a concentration of from about 0.001% to about 100% by weight percentage or volume percentage.

7. The OLED of claim 1 , wherein the organic layer further comprises a host material, wherein the host material comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

8. The OLED of claim 1 , wherein the organic layer further comprises a host material selected from the group consisting of

and combinations thereof.

9. The OLED of claim 1 , wherein the organic layer further comprises a phosphorescent emissive dopant with a formula of M(L A ) x (L B ) y (L C ) z wherein L A , L B and L C are each a ligand; and wherein x is 1, 2, or 3; y is 0, 1, or 2; z is 0, 1, or 2; and x+y+z is the oxidation state of a metal M selected from the group consisting of Os, Ir, Cu, Pt, and Pd;
wherein L A , L B and L C are each independently selected from the group consisting of

wherein
each Y 1 to Y 13 are independently selected from the group consisting of C and N;
Y′ is selected from the group consisting of B R e , N R e , P R e , O, S, Se, C═O, S═O, SO 2 , CR e R f , SiR e R f , and GeR e R f ,
R a , R b , R c , and R d may independently represent from mono substitution to the maximum possible number of substitution, or no substitution;
each R a , R b , R c , R d , R e and R f is independently hydeogen or a substituent selected from the group consisting of deuterium, halide, 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; or optionally, any two adjacent substituents of R a , R b , R c , or R d join to form a ring or form a multidentate ligand.

10. The OLED of claim 9 , wherein the metal is selected from Cu, Pt, or Pd, and x is 1, y is 1, and z is 0, wherein ligand L A and ligand L B can be the same or different, and the ligands L A and L B connect to form a tetradentate ligand.

11. The OLED of claim 1 , wherein the phosphorescent sensitizer and the fluorescent acceptor are in different layers.

12. A consumer product comprising an optoelectronic device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound of Formula X; wherein the compound of Formula X is a fluorescent acceptor; and wherein the optoelectronic device further comprises one or more phosphorescent sensitizer compounds;

wherein
ring A is absent, or present and selected from a 5-membered or 6-membered, carbocyclic or heterocyclic ring, which is optionally substituted;
ring B is absent, or present and selected from a 5-membered or 6-membered, carbocyclic or heterocyclic ring, which is optionally substituted;
wherein at least one of ring A or ring B is present, and the hash line represents ring A fused to ring N—W 1 —W 3 and ring B fused to ring N—W 4 —W 6 ;
wherein at least one of ring A or ring B is a 6-membered heteroaryl ring;
W 1 , W 2 , W 3 , W 4 , W 5 , and W 6 are independently selected from CR 1 or N;
Z is selected from CR Z or N;
Y is selected from a group consisting of C(R 2 ) 2 , B(R 2 ) 2 , Al(R 2 ) 2 , Si(R 2 ) 2 , and Ge(R 2 ) 2 ; wherein
R Z and each R 1 and R 2 are independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; or optionally, two R 2 join to form a cycloalkyl or heterocyclic ring;
wherein optionally, R 1 can join with R Z to form a five-membered or six-membered, carbocyclic or heterocyclic ring, which is optionally substituted;
wherein the consumer product is selected from the group consisting of a flat panel display, a computer monitor, a medical monitor, a television, a billboard, a li

Assignees

• Univ Southern California

Inventors

• Thompson Mark E
• Tadle Abegail
• El Roz Karim
• Djurovich Peter Ivan
• Muthiah Ravinson Daniel Sylvinson
• Golden Jessica H
• Sawyer Stuart W

Classifications

• H10K85/322

  comprising boron · CPC title

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• C07D405/14 Primary

  containing three or more hetero rings · CPC title

• C07F5/02

  Boron compounds · CPC title

• C07F5/022 Primary

  without C-boron linkages · CPC title