Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12295262-B2
Application number	US-202117186440-A
Country	US
Kind code	B2
Filing date	Feb 26, 2021
Priority date	Apr 6, 2015
Publication date	May 6, 2025
Grant date	May 6, 2025

Abstract

The present invention relates in part to compounds containing indolocarbazole and terphenyl building blocks. These compounds are useful for application in organic electroluminescent devices wherein the combination of indolocarbazoles with terphenyl groups leads to novel compounds that demonstrate superior device performance.

First claim

We claim:

1. A compound of Formula I:

wherein R is selected from the group consisting of:

wherein R 4 is

wherein R 1 , R 2 and R 3 each independently represents mono to maximum allowable substitutions, or no substitution;
wherein R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen, deuterium, alkyl, alkene, alkyne, alkoxy, halogen, silane, nitrile, nitro, aryl, heteroaryl and combinations thereof;
wherein R 4 , R 1 , R 2 , and R 3 are each independently, optionally, further substituted with one or more substituents selected from the group consisting of hydrogen, deuterium, alkyl, alkene, alkyne, alkoxy, halogen, silane, nitrile, nitro, aryl, heteroaryl, and combinations thereof;
wherein any two adjacent substituents are optionally joined or fused into a ring;
provided that no two adjacent substituents R 1 , R 2 , or R 3 are joined or fused to form an aromatic ring; and
wherein any hydrogen in the compound is optionally replaced with deuterium.

2. The compound of claim 1 , wherein R 1 , R 2 and R 3 are each a hydrogen.

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

4. An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound of Formula I

wherein R is selected from the group consisting of:

wherein R 4 is

wherein R 1 , R 2 and R 3 each independently represents mono to maximum allowable substitutions, or no substitution;
wherein R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen, deuterium, alkyl, alkene, alkyne, alkoxy, halogen, silane, nitrile, nitro, aryl, heteroaryl and combinations thereof;
wherein any two adjacent substituents are optionally joined or fused into a ring;
provided that no two adjacent substituents R 1 , R 2 , or R 3 are joined or fused to form an aromatic ring;
wherein R 4 , R 1 , R 2 , and R 3 are each independently, optionally, further substituted with one or more substituents selected from the group consisting of hydrogen, deuterium, alkyl, alkene, alkyne, alkoxy, halogen, silane, nitrile, nitro, aryl, heteroaryl, and combinations thereof; and
wherein any hydrogen in the compound is optionally replaced with deuterium.

5. The OLED of claim 4 , wherein the organic layer is an emissive layer and the compound of Formula I is a host.

6. The OLED of claim 4 , wherein the organic layer further comprises a phosphorescent emissive dopant; wherein the emissive dopant is a transition metal complex having at least one ligand or part of the ligand if the ligand is more than bidentate selected from the group consisting of:

wherein each X 1 to X 13 are independently selected from the group consisting of carbon and nitrogen;
wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO 2 , CR′R″, SiR′R″, and GeR′R″;
wherein R′ and R″ are optionally fused or joined to form a ring;
wherein each R a , R b , R c , and R d may represent from mono substitution to the possible maximum number of substitution, or no substitution;
wherein R′, R″, R a , R b , R c , and R d 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; and
wherein any two adjacent substituents of R a , R b , R c , and R d are optionally fused or joined to form a ring or form a multidentate ligand.

7. The OLED of claim 4 , wherein the organic layer is a blocking layer and the compound of Formula I is a blocking material in the organic layer.

8. The OLED of claim 4 , wherein the organic layer is a transporting layer and the compound of Formula I is a transporting material in the organic layer.

9. The OLED of claim 4 , wherein the OLED is incorporated into a device selected from the group consisting of a consumer product, an electronic component module, and a lighting panel.

10. A formulation comprising a compound of Formula I

wherein R is selected from the group consisting of:

wherein R 4 is

wherein R 1 , R 2 and R 3 each independently represents mono to maximum allowable substitutions, or no substitution;
wherein R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen, deuterium, alkyl, alkene, alkyne, alkoxy, halogen, silane, nitrile, nitro, aryl, heteroaryl and combinations thereof;
wherein R 4 , R 1 , R 2 , and R 3 are each independently, optionally, further substituted with one or more substituents selected from the group consisting of hydrogen, deuterium, alkyl, alkene, alkyne, alkoxy, halogen, silane, nitrile, nitro, aryl, heteroaryl, and combinations thereof;
wherein any two adjacent substituents are optionally joined or fused into a ring;
provided that no two adjacent substituents R 1 , R 2 , or R 3 are joined or fused to form an aromatic ring; and
wherein any hydrogen in the compound is optionally replaced with deuterium.

Assignees

• Universal Display Corp

Inventors

• Zeng Lichang
• Ji Zhiqiang
• Yeager Walter
• Dyatkin Alexey Borisovich
• Xia Chuanjun

Classifications

• C07D405/14

  containing three or more hetero rings · CPC title

• H10K2101/90

  Multiple hosts in the emissive layer · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K85/342

  comprising iridium · CPC title

• H10K50/16

  Electron transporting layers · CPC title