Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10833276-B2
Application number	US-201715421012-A
Country	US
Kind code	B2
Filing date	Jan 31, 2017
Priority date	Nov 21, 2016
Publication date	Nov 10, 2020
Grant date	Nov 10, 2020

Abstract

This invention relates to carbazole- or indolocarbazole-containing donor acceptor type compounds with an ortho substitution on the aromatic group that is connected to carbazole. This unique substitution pattern will provide materials with superior performance for host applications. These compounds can also be used as delayed fluorescent emitters.

First claim

We claim:

1. A compound of Formula I:

wherein Ar 1 is an aryl or heteroaryl moiety;
wherein R 1 is mono substitution and ortho to G 1 or L 1 ;
wherein R 1 is selected from the group consisting of:

wherein G 1 is selected from the group consisting of:

wherein the dashed line represents the attachment point of G 1 to Ar 1 ;
wherein G 3 is selected from the group consisting of

indolocarbazole, and combinations thereof;
wherein L 1 is selected from a group consisting of a direct bond, aryl, heteroaryl, and combinations thereof;
wherein G 2 is an aromatic moiety comprising a six-member aromatic ring containing at least one nitrogen atom;
wherein R 2 and R 3 each independently represents none to maximum allowable number of substitutions, or no substitution, and any two adjacent R 2 and R 3 are optionally joined or fused into a ring;
wherein R 2 and R 3 are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, halogen, nitrile, nitro, amine, carbonyl, aryl, heteroaryl, and combinations thereof;
wherein R 4 and R 5 are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof;
wherein G 1 , R 1 , and L 1 are independently optionally further substituted with one or more substituents selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, halogen, nitrile, nitro, amine, carbonyl, aryl, heteroaryl, and combinations thereof; and
wherein when G 1 is

at least one of the following conditions apply:
(1) G 2 is selected from the group consisting of

or
(2) R 4 is selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroaryl, and combinations thereof.

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

wherein R 5 is selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

3. The compound of claim 1 , wherein G 2 is selected from the group consisting of:

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

5. The compound of claim 1 , wherein L 1 is selected from the group consisting of:
direct bond,

6. The compound of claim 1 , wherein Ar 1 is a phenyl.

7. The compound of claim 1 , wherein L 1 is a direct bond.

8. A compound selected from the group consisting of:

9. 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 Ar 1 is an aryl or heteroaryl moiety;
wherein R 1 is mono substitution and ortho to G 1 or L 1 ;
wherein R 1 is selected from the group consisting of:

wherein G 1 is selected from the group consisting of:

wherein the dashed line represents the attachment point of G 1 to Ar 1 ;
wherein G 3 is selected from the group consisting of

indolocarbazole, and combinations thereof;
wherein L 1 is selected from a group consisting of a direct bond, aryl, heteroaryl, and combinations thereof;
wherein G 2 is an aromatic moiety comprising a six-member aromatic ring containing at least one nitrogen atom;
wherein R 2 and R 3 each independently represents none to maximum allowable number of substitutions, or no substitution, and any two adjacent R 2 and R 3 are optionally joined or fused into a ring;
wherein R 2 and R 3 are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, halogen, nitrile, nitro, amine, carbonyl, aryl, heteroaryl, and combinations thereof;
wherein R 4 and R 5 are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof;
wherein G 1 , R 1 , and L 1 are independently optionally further substituted with one or more substituents selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, halogen, nitrile, nitro, amine, carbonyl, aryl, heteroaryl, and combinations thereof; and
wherein when G 1 is

at least one of the following conditions apply:
(1) G 2 is selected from the group consisting of

or
(2) R 4 is selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroaryl, and combinations thereof.

10. The OLED of claim 9 , wherein the organic layer is an emissive layer and the compound of Formula I is a host, or
wherein the organic layer is an emissive layer and the compound of Formula I is an emitter.

11. The OLED of claim 9 , 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:

Assignees

• Universal Display Corp

Inventors

• Zeng Lichang
• Ma Bin
• Xia Chuanjun

Classifications

• H10K2101/20

  Delayed fluorescence emission · CPC title

• H10K85/654

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

• C09K11/025 Primary

  non-luminescent particle coatings or suspension media · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title