IP Library › Granted Patent US 9,166,175
Granted Patent B2
US 9,166,175 · App. 13/686,763 · Granted Oct 20, 2015

Organic electroluminescent materials and devices

Inventors: Chuanjun Xia (Lawrenceville, NJ); Chun Lin (Yardley, PA)
Assignee: Universal Display Corporation
H01L51/0069H01L51/56
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Quick Facts
Patent No.
US 9,166,175
App. No.
13/686,763
Granted
Oct 20, 2015
Kind
B2
Abstract

Novel compounds containing benzothiophene or benzofuran fused to a carbazoles moiety are disclosed. The compounds are substituted such that both an electron donor fragment and an electron acceptor fragment are present within the same molecule. The compounds are capable of exhibiting delayed fluorescence when used in the emissive layer of OLED devices.

Claims (64)

1. A first device comprising a first organic light emitting device, comprising:

an anode;

a cathode; and

an emissive layer, disposed between the anode and the cathode;

wherein the emissive layer comprises a host material doped with a first emitting compound, wherein the first emitting compound has a structure of formula I:

G 1 -Z,  Formula I;

wherein G 1 is an electron acceptor group; and

wherein Z is an electron donor group;

wherein Z has the formula:

wherein G 2 has the structure

and wherein G 2 is fused to any two adjacent carbon atoms on ring A;

wherein X is selected from the group consisting of O, S, and Se;

wherein R 1 represents mono-, di-substitution, or no substitution;

wherein R 2 , and R 3 independently represent mono-, di-, tri-, or tetra-substitution;

wherein R 1 is optionally fused to ring A, R 2 is optionally fused to ring B, and R 3 is optionally fused to ring C; and

wherein R 1 , R 2 and R 3 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.

2. The first device of claim 1 , wherein G 1 comprises at least one chemical group selected from the group consisting of:

wherein A 1 to A 6 independently comprise C or N, and at least one of A 1 to A 6 is N;

wherein J 1 to J 4 independently comprise C or N, and at least one of J 1 to J 4 is N;

wherein X 1 is O, S, or NR;

wherein R is 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.

3. The first device of claim 1 , wherein G 1 comprises at least one chemical group selected from the group consisting of:

wherein E 1 to E 8 independently comprise C or N;

wherein L 1 to L 4 independently comprise C or N;

wherein X 2 is O, S, or NR; and

wherein R is 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.

4. The first device of claim 1 , wherein R 3 is alkyl or aryl.

5. The first device of claim 1 , wherein Z comprises at least one chemical group selected from the group consisting of:

wherein R 11 , R 12 , and R 13 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.

6. The first device of claim 1 , wherein Z comprises a least one chemical group selected from the group consisting of:

7. The first device of claim 1 , wherein G 1 comprises at least one chemical group selected from the group consisting of:

wherein R 21 , R 22 , and R 23 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.

8. The first device of claim 1 , wherein G 1 comprises at least one chemical group selected from the group consisting of:

9. The first device of claim 1 , wherein G 1 comprises at least one chemical group selected from the group consisting of:

10. The first device of claim 1 , wherein the compound is selected from the group consisting of:

11. The first device of claim 1 , wherein the first device emits a luminescent radiation at room temperature when a voltage is applied across the first organic light emitting device;

wherein the luminescent radiation comprises a delayed fluorescent process.

12. The first device of claim 11 , wherein the emissive layer further comprises a first phosphorescent emitting material.

13. The first device of claim 12 , wherein the emissive layer further comprises a second phosphorescent emitting material.

14. The first device of claim 12 , wherein the first device emits a white light at room temperature when a voltage is applied across the organic light emitting device.

15. The first device of claim 14 , wherein the first emitting compound emits a blue light having a peak wavelength between about 400 nm to about 500 nm.

16. The first device of claim 14 , wherein the first emitting compound emits a yellow light having a peak wavelength between about 530 nm to about 580 nm.

17. The first device of claim 1 , wherein the first device comprises a second organic light-emitting device;

wherein the second organic light emitting device is stacked on the first organic light emitting device.

18. The first device of claim 1 , wherein the first device is a consumer product.

19. The first device of claim 1 , wherein the first device is an organic light-emitting device.

20. The first device of claim 1 , wherein the first device comprises a lighting panel.

21. A method of making a first organic light emitting device, comprising:

depositing an anode on a substrate;

depositing at least one organic layer comprising a host material doped with a first emitting compound, wherein the first emitting compound has a structure of formula I:

G 1 -Z,  Formula I;

wherein G 1 is an electron acceptor group; and

wherein Z is an electron donor group;

wherein Z has the formula:

wherein G 2 has the structure

and wherein G 2 is fused to any two adjacent carbon atoms on ring A;

wherein X is selected from the group consisting of O, S, and Se;

wherein R 1 represents mono-, di-substitution, or no substitution;

wherein R 2 , and R 3 independently represent mono-, di-, tri-, or tetra-substitution;

wherein R 1 is optionally fused to ring A, R 2 is optionally fused to ring B, and R 3 is optionally fused to ring C; and

wherein R 1 , R 2 and R 3 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, sulfanyl, sulfonyl, phosphino, and combinations thereof;

depositing a cathode;

wherein the emissive layer is deposited between the anode and cathode.

22. The method of claim 21 , wherein the at least one organic layer is deposited using a solution process.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 12, 2012
From: XIA, CHUANJUN; LIN, CHUN
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 029451/0712 →
Continuity (1)
Related Publication 20140145151A1 · May 29, 2014