Organic electroluminescent materials and devices

• US 9,209,411 B2
• Filed: 12/07/2012
• Issued: 12/08/2015
• Est. Priority Date: 12/07/2012
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Xia, Chuanjun, Lin, Chun, Kwong, Raymond, Joseph, Scott, Esler, James
• Primary Examiner(s): CLARK, GREGORY D
• Application Number:
  US13/708,189
• Publication Number:
  US 20140158992A1
• Time in Patent Office: 1,096 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: C07D 403/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 403/14 containing three or more hetero rings
• CPC Class Codes: C07D 405/14 containing three or more hetero rings
• CPC Class Codes: C07D 409/14 containing three or more hetero rings
• CPC Class Codes: C07D 491/048 the oxygen-containing ring being five-membered
• CPC Class Codes: C07D 493/04 Ortho-condensed systems
• CPC Class Codes: C07D 495/04 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 2211/1011 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 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1059 containing three nitrogen atoms as heteroatoms
• 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 2101/27 Combination of fluorescent and phosphorescent emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/636 : comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/654 : comprising only nitrogen as heteroatom H10K85/652 takes precedence
• 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

Novel carbazole-containing compounds are provided. The novel compounds also contain electron donor groups, aryl linkers, and at least one nitrogen heterocycle. These novel organic compounds are useful in OLED devices and can exhibit delayed fluorescence.

Claims

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;

2. The first device of claim 1, wherein the electron donor group comprises at least one chemical group selected from the group consisting of amino, indole, carbazole, benzothiohpene, benzofuran, benzoselenophene, dibenzothiophene, dibenzofuran, dibenzoselenophene, and combinations thereof.

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

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

5. The first device of claim 1, wherein the first emitting compound having the formula:

6. The first device of claim 1, wherein the first emitting compound has a formula selected from the group consisting of:

7. The first device of claim 1, wherein the first emitting compound has a formula selected from the group consisting of:

8. The first device of claim 1, 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.

9. The first device of claim 1, 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 first emitting compound 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 emitting compound emits a yellow light with a peak wavelength of about 530 nm to about 580 nm.

14. 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.

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

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

17. The first device of claim 1, wherein the first device is a lighting panel.