Host materials for electroluminescent devices

Patent metadata

Field	Value
Publication number	US-11515489-B2
Application number	US-201916683507-A
Country	US
Kind code	B2
Filing date	Nov 14, 2019
Priority date	Nov 28, 2018
Publication date	Nov 29, 2022
Grant date	Nov 29, 2022

Abstract

A compound of Formula I:wherein ring A is a 5-membered or 6-membered aromatic ring;wherein RA, RB, and RC each independently represent mono to the maximum allowable substitution, or no substitution;wherein Y1 is absent or present, and when present is selected from the group consisting of a direct bond, O, S, Se, CRR′, NR, SiRR′, and BR;wherein each X1-X3 is N or CR;wherein at least one of X1-X3 is N;wherein each A1-A5 is independently C or N;wherein the maximum number of N atoms that can connect to each other within each ring is two;wherein each R1, R2, R3, and R4 is independently selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof;wherein each R, R′, RA, RB, and RC is independently a 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; andwherein any two substituents may be joined or fused together to form a ring.

First claim

We claim:

1. A compound of Formula I:

wherein ring A is a 5-membered or 6-membered aromatic ring;
wherein R A , R B , and R C each independently represent mono to the maximum allowable substitution, or no substitution;
wherein Y 1 is absent or present, and when present is selected from the group consisting of a direct bond, O, S, Se, CRR′, NR, SiRR′, and BR;
wherein each X 1 -X 3 is N or CR;
wherein at least one of X 1 -X 3 is N;
wherein each A 1 -A 5 is independently C or N;
wherein the maximum number of N atoms that can connect to each other within each ring is two;
wherein each R 1 , R 2 , R 3 , and R 4 is independently selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof;
wherein each R, R′, R A , and R B is independently a 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; wherein each R C is independently a 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, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein any two substituents may be joined or fused together to form a ring.

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

3. The compound of claim 1 , wherein X 1 -X 3 are each N.

4. The compound of claim 1 , wherein X 1 is CR, and X 2 and X 3 are N.

5. The compound of claim 1 , wherein X 2 is CR, and X 1 and X 3 are N.

6. The compound of claim 1 , wherein X 1 is N, and X 2 and X 3 are CR.

7. The compound of claim 1 , wherein R 1 , R 2 , R 3 , and R 4 are each aryl or heteroaryl.

8. The compound of claim 1 , wherein R 1 and R 2 are joined to form a carbazole group.

9. The compound of claim 1 , wherein at least one selected from the following conditions is true: (a) R 3 and R 4 are joined to form a carbazole group; (b) R 1 and R 2 are joined to form a carbazole group and R 3 and R 4 are joined together to form a carbazole group; (c) A 5 is C, and ring A is a 6-membered aromatic ring; (d) R 3 and R 4 are joined to form a carbazole group, A 5 is C, and ring A is a 6-membered aromatic ring; and (e) R 1 and R 2 are joined to form a carbazole group, R 3 and R 4 are joined together to form a carbazole group A 5 is C, and ring A is a 6-membered aromatic ring.

10. The compound of claim 1 , wherein A 5 is N, and ring A is a 5-membered aromatic ring.

11. The compound of claim 1 , wherein A 1 -A 5 are each C.

12. The compound of claim 1 , wherein the compound is selected from the group consisting of:

wherein R D , R E , R F , R G and R H represent mono to the maximum allowable substitution, or no substitution;
wherein each Y 2 and Y 3 is independently selected from a group consisting of a direct bond, O, S, Se, CRR′, NR, SiRR′, and BR, or it is not present;
wherein A 6 to A 25 are each independently C or N;
wherein the maximum number of N atoms that can connect to each other within each ring is two;
wherein Z 1 to Z 3 are each independently selected from a group consisting of O, S, Se, CRR′, NR, SiRR′, or BR;
wherein each R D , R E , R F , R G and R H is independently a 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; and
wherein any two substituents may be joined or fused together to form a ring.

13. The compound of claim 1 , wherein the compound is selected from the group consisting of Compound H1-B1-B1-B1 to Compound H50-B60-B60-B60 based on the numbering formula Hn-Bi-Bj-Bk, wherein n is an integer from 1 to 50, wherein i, j, and k are each independently an integer from 1 to 60, wherein H1 to H50 have the following structures:

or the compound is selected from the group consisting of Compound H51-B1-B1 to Compound H70-B60-B60 based on the numbering formula Hm-Bi-Bj, wherein m is an integer from 51 to 70, wherein i and j are each independently an integer from 1 to 60, wherein H51 to H70 have the following structures:

and wherein B1 to B60 have the following structures:

Assignees

• Universal Display Corp

Inventors

• Wolohan Peter
• Fleetham Tyler
• Brooks Jason
• Hamze Rasha
• Thompson Nicholas J

Classifications

• C07D487/04

  Ortho-condensed systems · CPC title

• C07D487/14

  Ortho-condensed systems · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C07F7/0814

  said ring is substituted at a C ring atom by Si · CPC title

• C07D401/14 Primary

  containing three or more hetero rings · CPC title