Organic electroluminescent materials and devices

• US 9,741,941 B2
• Filed: 04/29/2014
• Issued: 08/22/2017
• Est. Priority Date: 04/29/2014
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Yeh, Tzu-Chin, Wong, Ken-Tsung, Kwong, Raymond, Lam, Siu Tung, Lee, Chi Hang
• Primary Examiner(s): Clark, Gregory
• Application Number:
  US14/264,787
• Publication Number:
  US 20150311449A1
• Time in Patent Office: 1,211 Days
• Field of Search: None
• CPC Class Codes: C07D 471/04 Ortho-condensed systems
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1014 bridged by heteroatoms, e.g. N, P, Si or B
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/1092 containing sulfur as the only heteroatom
• CPC Class Codes: H10K 2101/20 Delayed fluorescence emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/636 comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: H10K 85/6574 comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
• CPC Class Codes: H10K 85/6576 comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Abstract

A compound that has the structure according to Formula 1:

as well as, devices and formulations containing the compound of Formula 1 are disclosed. In the compound of Formula 1:

• • X¹, X², X³, X⁴, X⁵, and X⁶ are independently selected from the group consisting of C—R and N;
  • 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
    • at least one R comprises a donor group with at least two electron donating nitrogens.

Claims

1. A compound having a structure according to Formula 2:

2. The compound of claim 1, wherein the nitrogen bonded to Ar¹ and Ar² is a tertiary amine.

3. The compound of claim 1, wherein the nitrogen of the carbazole is connected meta to the nitrogen of Ring A.

4. The compound of claim 1, wherein the nitrogen of the carbazole is connected ortho to the nitrogen of Ring A.

5. The compound of claim 1, wherein at least one R⁴ or R⁵ substituent comprises a donor group with at least two electron donating nitrogens, and the donor group comprises a tertiary amine.

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

7. 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 host and an emissive dopant having a structure according to Formula 1;

8. The first device of claim 7, wherein the first device 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.

9. The first device of claim 7, wherein the emissive layer further comprises a first phosphorescent emitting material.

10. The first device of claim 9, wherein the emissive layer further comprises a second phosphorescent emitting material.

11. The first device of claim 9, wherein the first device emits a white light at room temperature when a voltage is applied across the organic light emitting device.

12. The first device of claim 11, wherein the compound of Formula 1 emits a blue light with a peak wavelength of about 400 nm to about 500 nm.

13. The first device of claim 11, wherein the compound of Formula 1 emits a yellow light with a peak wavelength of about 530 nm to about 580 nm.

17. The first device of claim 7, wherein the device is one or more of a consumer product, an organic light-emitting device, and a lighting panel.

14. 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 a structure according to Formula 2;

15. The first device of claim 14, wherein the nitrogen of the carbazole is connected meta to the nitrogen of Ring A.

16. The first device of claim 14, wherein the nitrogen of the carbazole is connected ortho to the nitrogen of Ring A.

18. The first device of claim 14, wherein the device is one or more of a consumer product, an organic light-emitting device, and a lighting panel.

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

20. The first device of claim 14, wherein the compound of Formula 2 is a host material.