Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10680184-B2
Application number	US-201715622372-A
Country	US
Kind code	B2
Filing date	Jun 14, 2017
Priority date	Jul 11, 2016
Publication date	Jun 9, 2020
Grant date	Jun 9, 2020

Abstract

The present application includes novel containing xanthene and spiro dixanthene ring structures and alkylated variants thereof. These compounds are useful as host materials with high triplet energies for phosphorescent electroluminescent devices.

First claim

We claim:

1. A compound of Formula I:

wherein X is selected from the group consisting of O, S, Se and NR; Y is selected from the group consisting of CR 9 R 10 , SiR 9 R 10 , O, S, Se, and NR;
wherein R and R 1 to R 10 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein any adjacent substitutents are optionally joined or fused into a ring, with the proviso that when R 9 and R 10 are both aryl, they are not joined by a single chemical bond; and
wherein at least one of the following conditions is true:
condition (1): R 1 is

wherein R 1 ′ and R 2 ′ are independently selected from the group consisting of hydrogen, deuterium, chlorine, bromine, alkyl, cycloalkyl, heteroalkyl, unfused arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, unfused aryl, unfused heteroaryl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein A is 5-membered or 6-membered carbocyclic or heterocyclic ring that is optionally further substituted;
wherein at least one of R 2 , R 1 ′ and R 2 ′ is not hydrogen or deuterium, and wherein if R 1 ′ is methyl then R 2 ′ is not hydrogen or deuterium;
condition (2): at least one of R 1 to R 10 comprises a tetraphenylene group;
condition (3): at least one pair of adjacent substituents of R 1 to R 4 and R 5 to R 8 is fused to form a tetraphenlyene group, which can be further substituted;
condition (4): X is NR, and R has a structure of Formula I;
condition (5): at least one of R 1 to R 4 and R 5 to R 8 is

wherein Z 1 and Z 2 are each independently selected from the group consisting of alkyl, aryl, and substituted aryl, L is a direct bond or an organic linker, R 11 to R 13 are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, aryl, and silyl, and at least one of R 11 to R 13 comprises a structure of Formula I;
condition (6): at least one of R 1 to R 4 and R 5 to R 8 is

wherein R 16 comprises a structure of Formula I, R 17 to R 20 are each independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, silyl, and aryl, and at least one of R 17 , R 19 , and R 20 is not hydrogen or deuterium;
condition (7): at least one of R 1 to R 4 and R 5 to R 8 is

wherein R 20 to R 28 are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, silyl, and aryl, and at least one of R 20 to R 22 comprises a structure of Formula I; and
condition (8): at least one of R 1 to R 4 and R 5 to R 8 is

wherein Z 3 and Z 4 are each independently selected from the group consisting of alkyl, aryl, and substituted aryl, and R 29 comprises a structure of Formula I, provided that (a) Z 3 and Z 4 are not both aryl or substituted aryl, or (b) neither X nor Y is NR.

2. The compound of claim 1 , wherein X is selected from the group consisting of O, S, and Se.

3. The compound of claim 1 , wherein X is NR.

4. The compound of claim 1 , wherein Y is selected from the group consisting of O, S, Se, and NR.

5. The compound of claim 1 , wherein Y is CR 9 R 10 or SiR 9 R 10 .

6. The compound of claim 1 , wherein in condition (1), R 2 is not hydrogen or deuterium, and R 1 ′ and R 2 ′ are hydrogen.

7. The compound of claim 1 , wherein in condition (1), R 2 is hydrogen, and R 1 ′ and R 2 ′ are not hydrogen or deuterium.

8. The compound of claim 1 , wherein in condition (1), A is an aromatic ring.

9. The compound of claim 1 , wherein in condition (1), A is benzene.

10. The compound of claim 1 , wherein in condition (1), at least one of R 2 , R 1 ′ and R 2 ′ is selected from the group consisting of alkyl, cycloalkyl, silyl, unfused aryl, unfused heteroaryl, and combinations thereof.

11. The compound of claim 1 , wherein in condition (1), A is further substituted by a structure of Formula I.

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

Assignees

• Universal Display Corp

Inventors

• Wolohan Peter
• Fitzgerald George
• Silverstein Daniel W
• Feldman Jerald

Classifications

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• H01L51/5016

  Electricity · mapped topic

• H01L51/0073 Primary

  Electricity · mapped topic

• H01L51/0055

  Electricity · mapped topic