Organic electroluminescent materials and devices

• US 9,166,175 B2
• Filed: 11/27/2012
• Issued: 10/20/2015
• Est. Priority Date: 11/27/2012
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Xia, Chuanjun, Lin, Chun
• Primary Examiner(s): CLARK, GREGORY D
• Application Number:
  US13/686,763
• Publication Number:
  US 20140145151A1
• Time in Patent Office: 1,057 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 71/00 Manufacture or treatment specially adapted for the organic devices covered by this subclass
• CPC Class Codes: H10K 85/654 comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/656 comprising two or more different heteroatoms per ring H10K85/652 takes precedence
• CPC Class Codes: H10K 85/657 Polycyclic condensed heteroaromatic hydrocarbons

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

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;

G¹-Z, 

 

Formula I;

wherein G¹ is an electron acceptor group; and

wherein Z is an electron donor group;

wherein Z has the formula;

2. The first device of claim 1, wherein G¹ comprises at least one chemical group selected from the group consisting of:

3. The first device of claim 1, wherein G¹ comprises at least one chemical group selected from the group consisting of:

4. The first device of claim 1, wherein R³ 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:

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 G¹ comprises at least one chemical group selected from the group consisting of:

8. The first device of claim 1, wherein G¹ comprises at least one chemical group selected from the group consisting of:

9. The first device of claim 1, wherein G¹ 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;

G¹-Z, 

 

Formula I;

wherein G¹ is an electron acceptor group; and

wherein Z is an electron donor group;

wherein Z has the formula;

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