IP Library Patent Application 15063990
Patent Application
App. No. 15/063,990

Organic Electroluminescent Materials and Devices

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Patent No.
US None
App. No.
15/063,990
Abstract

Novel organic compounds containing indolocarbazole and fluorene moieties were disclosed in this application. These compounds are suitable for application in organic electroluminescent devices.

Claims (44)

1 . A compound having a formula selected from the group consisting of:

wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 and Ar 6 are each independently selected from the group consisting of benzene, biphenyl, terphenyl, triphenylene, fluorene, benzofuran, benzothiophene, benzoselenophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof;

wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 and Ar 6 are each independently optionally further substituted with hydrogen, deuterium, halogen, alkyl, aryl, heteromyl, cycloalkyl, silyl and combinations thereof;

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 each independently represent mono to the possible maximum number of substitutions, or no substitution;

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl,silyl, benzene, biphenyl, terphenyl, triphenylene, fluorene, benzofuran, benzothiophene, benzoselenophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, carbazole, and combinations thereof;

wherein L 1 , L 2 , L 3 , L 4 , L 5 and L 6 are each independently selected from the group consisting of direct bond, alkyl, benzene, biphenyl, terphenyl, and combinations thereof; and

wherein at least one of Ar 1 and Ar 2 is 9,9-disubstituted fluorene, at least one of Ar 3 and Ar 4 is 9,9-disubstituted fluorene, and at least one of Ar 5 and Ar 6 is 9,9-disubstituted fluorene.

2 . The compound of claim 1 , wherein the compound is a compound of Formula I.

3 . The compound of claim 1 , wherein the compound is a compound of Formula II.

4 . The compound of claim 1 , wherein the compound is a compound of Formula III.

5 . The compound of claim 1 , wherein R 1 to R 9 are each a hydrogen.

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

wherein R A and R B are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, benzene, biphenyl, and combinations thereof, and

wherein R A and R B are optionally joined to form a ring.

7 . The compound of claim 1 , wherein L 1 , L 2 , L 3 , L 4 , L 5 and L 6 are each a direct bond.

8 . The compound of claim 1 , wherein the compound is 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 having a formula selected from the group consisting of:

wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 and Ar 6 are each independently selected from the group consisting of benzene, biphenyl, terphenyl, triphenylene, fluorene, benzofuran, benzothiophene, benzoselenophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof;

wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 and Ar 6 are each independently optionally further substituted with hydrogen, deuterium, halogen, alkyl, aryl, heteroatyl, cycloalkyl, silyl and combinations thereof;

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 each independently represent mono to the possible maximum number of substitutions, or no substitution;

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl,silyl, benzene, biphenyl, terphenyl, triphenylene, fluorene, benzofuran, benzothiophene, benzoselenophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, carbazole, and combinations thereof;

wherein L 1 , L 2 , L 3 , L 4 , L 5 and L 6 are each independently selected from the group consisting of direct bond, alkyl, benzene, biphenyl, terphenyl, and combinations thereof; and

wherein at least one of Ar 1 and Ar 2 is 9,9-disubstituted fluorene, at least one of Ar 3 and Ar 4 is 9,9-disubstituted fluorene, and at least one of Ar 5 and Ar 6 is 9,9-disubstituted fluorene.

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

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, heteroatyl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

wherein any two adjacent substitutents 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, II, or III is a blocking material in the organic layer.

13 . The OLED of claim 9 , wherein the organic layer is a transporting layer and the compound of Formula I, II, or III is a transporting material in the organic layer.

14 . 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.

15 . A formulation comprising a compound having a formula selected from the group consisting of:

wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 and Ar 6 are each independently selected from the group consisting of benzene, biphenyl, terphenyl, triphenylene, fluorene, benzofuran, benzothiophene, benzoselenophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof;

wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 and Ar 6 are each independently optionally further substituted with hydrogen, deuterium, halogen, alkyl, aryl, heterowyl, cycloalkyl, silyl and combinations thereof;

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 each independently represent mono to the possible maximum number of substitutions, or no substitution;

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl,silyl, benzene, biphenyl, terphenyl, triphenylene, fluorene, benzofuran, benzothiophene, benzoselenophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, carbazole, and combinations thereof;

wherein L 1 , L 2 , L 3 , L 4 , L 5 and L 6 are each independently selected from the group consisting of direct bond, alkyl, benzene, biphenyl, terphenyl, and combinations thereof; and

wherein at least one of Ar 1 and Ar 2 is 9,9-disubstituted fluorene, at least one of Ar 3 and Ar 4 is 9,9-disubstituted fluorene, and at least one of Ar 5 and Ar 6 is 9,9-disubstituted fluorene.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 8, 2016
From: ZENG, LICHANG; DYATKIN, ALEXEY BORISOVICH; JI, ZHIQIANG; YEAGER, WALTER; XIA, CHUANJUN
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 037922/0672 →