IP Library Granted Patent US 10,833,276
Granted Patent B2
US 10,833,276 · App. 15/421,012 · Granted Nov 10, 2020

Organic electroluminescent materials and devices

Inventors: Lichang Zeng (Ewing, NJ); Bin Ma (Ewing, NJ); Chuanjun Xia (Ewing, NJ)
Assignee: UNIVERSAL DISPLAY CORPORATION
H01L51/0067C07D487/04C09K11/025C09K11/06H01L51/0072C09K2211/1007C09K2211/1059H01L51/5016H01L51/5096
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Quick Facts
Patent No.
US 10,833,276
App. No.
15/421,012
Granted
Nov 10, 2020
Kind
B2
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.

Claims (72)

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:

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 acid, 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.

12. The OLED of claim 9 , wherein the organic layer is a blocking layer and the compound of Formula I is a blocking material in the organic layer, or

wherein the organic layer is a transporting layer and the compound of Formula I is a transporting material in the organic layer.

13. The OLED of claim 9 , 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.

14. The OLED of claim 10 , wherein when the organic layer is an emissive layer and the compound of Formula I is an emitter, the OLED emits a luminescent radiation at room temperature when a voltage is applied across the organic light emitting device, and wherein the luminescent radiation comprises a delayed fluorescence process.

15. The OLED of claim 10 , wherein the emissive layer further comprises a host material, or

wherein the emissive layer further comprises a first phosphorescent emitting material.

16. A formulation comprising a compound of claim 1 .

17. 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 claim 8 .

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

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 31, 2017
From: ZENG, LICHANG; MA, BIN; XIA, CHUANJUN
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 041137/0403 →
Continuity (2)
Provisional Application 62424848 · Nov 21, 2016
Related Publication 20180145262A1 · May 24, 2018