IP Library Granted Patent US 9,324,949
Granted Patent B2
US 9,324,949 · App. 13/942,879 · Granted Apr 26, 2016

Organic electroluminescent materials and devices

Inventors: Raymond Kwong (Fo Tan, HK); Chuanjun Xia (Lawrenceville, NJ); Scott Joseph (Ewing, NJ); Siu Tung Lam (Apleichau, HK); Chi Hang Lee (Chaiwan, HK)
Assignee: Universal Display Corporation
H01L51/0061C09K11/06H01L51/0071H01L51/0072H01L51/0073H01L51/0074H01L51/5016
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Quick Facts
Patent No.
US 9,324,949
App. No.
13/942,879
Granted
Apr 26, 2016
Kind
B2
Abstract

Luminescent materials including donor-acceptor compounds with a high triplet energy heteropolyaromatic system, namely, dibenzofuran, dibenzothiophene and dibenzoselenophene with one or multiple nitrogens in the ring as the electron acceptor for use as emitters in organic light emitting diodes is disclosed.

Claims (55)

1. A compound having the formula:

wherein each of Y 1 to Y 8 is C—R or N;

wherein at least two of Y 1 to Y 8 is N;

wherein at least one of Y 1 to Y 8 is C—R;

X is O, S, or Se;

each R is 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;

wherein at least one of the R is selected from the group consisting of

wherein S 1 to S 7 represent mono, di, tri, tetra or penta substitutions with 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 compound of claim 1 , wherein the compound is selected from the group consisting of

wherein at least one of R 1 -R 8 is selected from the group consisting of D1 to D140.

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

wherein D10, D31, D54, D55, D56, D57, D58, D59, D60, D70 and D61 are

wherein S 1 to S 6 represent mono, di, tri, tetra or penta substitutions with 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, sulfonyl, phosphino, and combinations thereof.

4. The compound of claim 3 , wherein S 1 to S 6 are H.

5. A first device comprising a first organic light emitting device, the 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 and a first emitting compound having the formula:

wherein each of Y 1 to Y 8 is C—R or N;

wherein at least one of Y 1 to Y 8 is N;

wherein at least one of Y 1 to Y 8 is C—R;

X is O, S, or Se;

each R is 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 at least one of the R comprises a donor group with at least one electron-donating nitrogen.

6. The first device of claim 5 , wherein at least two of Y 1 to Y 8 are N.

7. The first device of claim 5 , wherein the first emitting compound is selected from the group consisting of

wherein R 1 -R 8 is independently hydrogen, deuterium, halide, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfonyl, phosphino, and combinations thereof;

at least one of R 1 to R 8 is (L m Donor) n ;

wherein L is a linker,

in is 1 or 0,

n≧1; and

wherein Donor is an electron donating group containing at least one electron-donating nitrogen and Donors can be different when n>1.

8. The first device of claim 7 , wherein the linker L is selected from the group consisting of

wherein A 1 to A 2 represent mono, di, tri or tetra substitutions with hydrogen, deuterium, halide, cycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

9. The first device of claim 7 , wherein the Donor is selected from the group consisting of:

wherein S 1 to S 7 represent mono, di, tri, tetra or penta substitutions with 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.

10. The first device of claim 5 , wherein the first emitting compound is selected from the group consisting of:

wherein D7, D10, D31, D54, D55, D56, D57, D58, D59, D60, D61, D70 and D144 are

wherein S 1 to S 6 represent mono, di, tri, tetra or penta substitutions with 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.

11. The first device of claim 10 , wherein S 1 to S 6 are H.

12. The first device of claim 5 , wherein the first device emits a luminescent radiation at room temperature when a voltage is applied across the organic light emitting device;

wherein the luminescent radiation comprises a delayed fluorescence process.

13. The first device of claim 5 , wherein the emissive layer further comprises a first phosphorescent emitting material.

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

15. The first device of claim 5 , wherein the emissive layer further comprises a host material.

16. The first device of claim 13 , wherein the first device emits a white light at room temperature when a voltage is applied across the organic light emitting device.

17. The first device of claim 16 , wherein the first emitting compound emits a blue light with a peak wavelength of about 400 nm to about 500 nm.

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

19. The first device of claim 5 , 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.

20. The first device of claim 5 , wherein the first device is a consumer product.

21. The first device of claim 5 , wherein the first device is an organic light-emitting device.

22. The first device of claim 5 , wherein the first device is a lighting panel.

23. The first device of claim 5 , wherein at least one of the R comprises a donor group with at least two electron-donating nitrogens.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 17, 2013
From: KWONG, RAYMOND; XIA, CHUANJUN; JOSEPH, SCOTT; LAM, SIU TUNG; LEE, CHI HANG
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 030816/0421 →
Continuity (1)
Related Publication 20150021555A1 · Jan 22, 2015