IP Library › Granted Patent US 9,876,173

Granted Patent B2

US 9,876,173 · App. 14/100,767 · Granted Jan 23, 2018

Organic electroluminescent materials and devices

Inventors: Lichang Zeng (Lawrenceville, NJ); Walter Yeager (Yardley, PA); Suman Layek (Lawrenceville, NJ); Bin Ma (Plainsboro, NJ); Kwang-Ohk Cheon (Holland, PA); Chuanjun Xia (Lawrenceville, NJ)

Assignee: Universal Display Corporation

H01L51/0054 H01L51/0072 H01L51/0081 H01L51/0085 H01L51/5016

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Quick Facts

Patent No.: US 9,876,173
App. No.: 14/100,767
Granted: Jan 23, 2018
Kind: B2

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Abstract

Novel oligocarbazole compounds containing a triphenylene and an oligocarbazole are provided. The compounds are useful in devices including organic light emitting devices (OLEDs).

Claims (531)

1. A compound having the formula:

A-L-C (I);

wherein A has the formula:

wherein C has the formula:

wherein L has the formula:

wherein R 1 , R 2 , R 4 , R 5 , R 8 and R 9 each independently represent mono, di, tri, tetra substitutions, or no substitution;

wherein R 3 , R 6 and R 7 each independently represent mono, di, tri substitutions, or no substitution;

wherein m is 0;

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, 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 Z 1 , Z 2 , Z 3 and Z 4 are each independently selected from the group consisting of N, CH and CD.

2. The compound of claim 1 , 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, aryl, heteroaryl, and combinations thereof.

3. The compound of claim 1 , 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, phenyl, and combinations thereof.

4. The compound of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are hydrogen.

5. The compound of claim 1 , wherein L is selected from the group consisting of phenyl and pyridine.

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

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

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

wherein L is selected from the group consisting of:

and

wherein C is selected from the group consisting of:

9. The compound of claim 8 , wherein the compound is selected from the group consisting of Compound 1 to Compound 5, Compound 10 to Compound 15, Compound 20 to Compound 25, Compound 30 to Compound 35, Compound 40 to Compound 45, Compound 50 to Compound 55, Compound 60 to Compound 65, Compound 70 to Compound 75, Compound 80 to Compound 85, Compound 90 to Compound 95, Compound 100 to Compound 105, Compound 110 to Compound 115, Compound 120 to Compound 125, Compound 130 to Compound 135, Compound 140 to Compound 145, Compound 150 to Compound 155, Compound 160 to Compound 165, Compound 170 to Compound 175, Compound 180 to Compound 185, Compound 190 to Compound 195, and Compound 200 listed below:

Comp #

Comp 1

Comp 2

Comp 3

Comp 4

Comp 5

Comp 10

A10

Comp 11

Comp 12

Comp 13

Comp 14

Comp 15

Comp 20

A10

Comp 21

Comp 22

Comp 23

Comp 24

Comp 25

Comp 30

A10

Comp 31

Comp 32

Comp 33

Comp 34

Comp 35

Comp 40

A10

Comp 41

Comp 42

Comp 43

Comp 44

Comp 45

Comp 50

A10

Comp 51

Comp 52

Comp 53

Comp 54

Comp 55

Comp 60

A10

Comp 61

Comp 62

Comp 63

Comp 64

Comp 65

Comp 70

A10

Comp 71

Comp 72

Comp 73

Comp 74

Comp 75

Comp 80

A10

Comp 81

Comp 82

Comp 83

Comp 84

Comp 85

Comp 90

A10

Comp 91

Comp 92

Comp 93

Comp 94

Comp 95

Comp 100

A10

Comp 101

Comp 102

Comp 103

Comp 104

Comp 105

Comp 110

A10

Comp 111

Comp 112

Comp 113

Comp 114

Comp 115

Comp 120

A10

Comp 121

Comp 122

Comp 123

Comp 124

Comp 125

Comp 130

A10

Comp 131

Comp 132

Comp 133

Comp 134

Comp 135

Comp 140

A10

Comp 141

Comp 142

Comp 143

Comp 144

Comp 145

Comp 150

A10

Comp 151

Comp 152

Comp 153

Comp 154

Comp 155

Comp 160

A10

Comp 161

Comp 162

Comp 163

Comp 164

Comp 165

Comp 170

A10

Comp 171

Comp 172

Comp 173

Comp 174

Comp 175

Comp 180

Comp 181

Comp 182

Comp 183

Comp 184

Comp 185

Comp 190

A10

Comp 191

Comp 192

Comp 193

Comp 194

Comp 195

Comp 200

A10

C4.

10. The compound of claim 1 , wherein the compound has the formula:

11. A first device comprising a first organic light emitting device, the first organic light emitting device comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound having the formula:

A-L-C (I);

wherein A has the formula:

wherein C has the formula:

wherein L has the formula:

wherein R 1 , R 2 , R 4 , R 5 , R 8 and R 9 each independently represent mono, di, tri, tetra substitutions, or no substitution;

wherein R 3 , R 6 and R 7 each independently represent mono, di, tri substitutions, or no substitution;

wherein m is 0;

wherein Z 1 , Z 2 , Z 3 and Z 4 are each independently selected from the group consisting of N, CH and CD.

12. The first device of claim 11 , wherein the organic layer is an emissive layer and the compound of the formula I is a host.

13. The first device of claim 11 , wherein the organic layer further comprises a phosphorescent emissive dopant.

14. The first device of claim 13 , wherein the phosphorescent 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 R a , R b , R c , and R d may represent mono, di, tri, or tetra substitution, or no substitution;

wherein R a , R b , R c , and R d are 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 two adjacent substituents of R a , R b , R c , and R d are optionally joined to form a fused ring or form a multidentate ligand.

15. The first device of claim 11 , wherein the organic layer is a blocking layer and the compound of formula I is a blocking material in the organic layer.

16. The first device of claim 11 , wherein the first device is a consumer product.

17. The first device of claim 11 , wherein the first device is an organic light-emitting device.

18. The first device of claim 11 , wherein the first device comprises a lighting panel.

19. The first device of claim 11 , wherein the compound of formula I is:

20. A formulation comprising the compound of claim 1 .

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 4, 2014

From: ZENG, LICHANG; YEAGER, WALTER; LAYEK, SUMAN; MA, BIN; CHEON, KWANG-OHK; XIA, CHUANJUN

To: UNIVERSAL DISPLAY CORPORATION

Reel/Frame 034378/0411 →

Continuity (1)

Related Publication 20150162538A1 · Jun 11, 2015