Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-11812624-B2
Application number	US-201916262460-A
Country	US
Kind code	B2
Filing date	Jan 30, 2019
Priority date	Jan 30, 2019
Publication date	Nov 7, 2023
Grant date	Nov 7, 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 2 and ring B fused to ring N—W 3 —W 4 ;
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. A compound of Formula X

wherein
ring A is a 6-membered aryl or heteroaryl ring, which is optionally substituted;
ring B is a 6-membered aryl or heteroaryl ring, which is optionally substituted;
wherein the hash lines represent ring A fused to W 3 and the carbon atom between W 3 and N and ring B fused to W 6 and the carbon atom between N and 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;
Y is selected from a group consisting of 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;
with the proviso that at least one of the following conditions (i) to (ii) is true:
(i) at least one of ring A or ring B is a 6-membered heteroaryl ring; and
(ii) the compound is represented by one of the following structures:

wherein R 7 and R 8 are each R 2 ; and
each R 6 is selected from the group consisting of C 1 -C 6 alkyl and C 1 -C 6 alkoxy; and
with the proviso that when Y is B(R 2 ) 2 and each R 2 is F, then:
ring A is not substituted with an aryl group;
ring B is not substituted with an aryl group; and
R 1 does not represent aryl.

2. The compound of claim 1 , wherein R Z and each R 1 and R 2 are independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

3. The compound of claim 1 , wherein R Z and each R 1 and R 2 is independently selected from the group consisting of H, D, F, —CN, —CF 3 , alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, aryl, aryloxy, heterocycle, and heteroaryl.

4. The compound of claim 1 , wherein each W 1 , W 2 , W 4 , W 5 , and W 6 are CR 1 .

5. The compound of claim 1 , wherein one of W 1 , W 2 , or W 3 is N, and one of W 4 , W 5 , or W 6 is N.

6. The compound of claim 1 , wherein Y is B(R 2 ) 2 .

7. The compound of claim 1 , wherein Z is N.

8. The compound of claim 1 , wherein the compound is represented by the following structure:

wherein
X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 are independently selected from CR 3 and N; wherein R 3 is 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, any two adjacent R 3 join to form a ring.

9. The compound of claim 8 , wherein Z is N, and Y is B(R 2 ) 2 , wherein R 2 is independently selected from the group consisting of H, D, F, —CN, —CF 3 , alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, aryl, aryloxy, heterocycle, and heteroaryl.

10. The compound of claim 9 , the compound selected from the group consisting of

wherein
each R 6 , R 7 , and R 8 is independently selected from the group consisting of H, D, F, —CN, —CF 3 , C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkenyl, C 5 -C 6 cycloalkyl, C 6 -C 10 aryl, C 6 -C 10 aryloxy, C 5 -C 6 heterocycle, and C 5 -C 10 heteroaryl.

11. The compound of claim 1 , wherein Z is N;
Y is BF 2 ; and
at least one of ring A or ring B is a 6-membered heteroaryl ring.

12. The compound of claim 1 , wherein the compound is represented by one of the following structures:

wherein Y is B;
wherein R 7 and R 8 are each F; and
each R 6 is selected from the group consisting of C 1 -C 3 alkyl and C 1 -C 3 alkoxy.

13. 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
ring A is a 6-membered aryl or heteroaryl ring, which is optionally substituted;
ring B is a 6-membered aryl or heteroaryl ring, which is optionally substituted;
wherein the hash lines represent ring A fused to W 3 and the carbon atom between W 3 and N and ring B fused to W 6 and the carbon atom between N and 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;
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;
with the proviso that at least one of the following conditions (i) to (ii) is true:
(i) at least one of ring A or ring B is a 6-membered heteroaryl ring; and
(ii) the compound is represented by one of the following structures:

wherein R 7 and R 8 are each R 2 ; and
each R 6 is selected from the group consisting of C 1 -C 6 alkyl and C 1 -C 6 alkoxy; and
with the proviso that when Y is B(R 2 ) 2 and each R 2 is F, then:
ring A is not substituted with an aryl group;
ring B is not substituted with an aryl group; and
R 1 does not represent aryl.

14. The optoelectronic device of claim 13 is an OLED, wherein the organic layer is disposed between an anode and a cathode.

15. The OLED of claim 14 , wherein the organic layer further comprises a host mat

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

• H10K85/654 Primary

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

• C09K11/025 Primary

  non-luminescent particle coatings or suspension media · CPC title

• C07D471/14

  Ortho-condensed systems · CPC title

• C07F5/02

  Boron compounds · CPC title

• C07F5/022

  without C-boron linkages · CPC title