Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-2020239456-A1
Application number	US-202016744728-A
Country	US
Kind code	A1
Filing date	Jan 16, 2020
Priority date	Jan 30, 2019
Publication date	Jul 30, 2020
Grant date	—

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 . 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;
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 ;
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.

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 3 , 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 Y is C(R 2 ) 2 .

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

9 . The compound of claim 1 selected from the group consisting of

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.

10 . The compound of claim 9 , wherein Z is N, and Y is selected from B(R 2 ) 2 or C(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.

11 . The compound of claim 9 , wherein at least one of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 is N, and each distinct six-membered ring has no more than two nitrogen ring atoms.

12 . The compound of claim 9 , wherein one X 1 , X 2 , X 3 , or X 4 is N, and one of X 5 , X 6 , X 7 , or X 8 is N.

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

wherein
R 6 , R 7 , and R 8 are 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.

14 . 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 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 ;
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.

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

16 . The OLED of claim 15 , wherein the OLED further comprises one or more sensitizer compounds while the compound of Formula X is a fluorescent acceptor.

17 . The OLED of claim 16 , wherein the one or more sensitizer compounds are selected from the group consisting of a phosphorescent compound, a delayed fluorescent compound, an exciplex, and their combinations.

18 . The OLED of claim 16 , wherein the one or more sensitizer compounds and the compound of Formula X are in the same layer.

19 . The OLED of claim 16 , wherein the one or more sensitizer compounds and the compound of Formula X are in different layers.

20 . The OLED of claim 15 , wherein the compound of Formula X has a concentration of from about 0.001% to about 100% by weight percentage or volume percentage.

21 . The OLED of claim 15 , 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, dibenzothiphene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

22 . The OLED of claim 15 , wherein the organic layer further comprises a host material selected from the

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