Organic electroluminescent materials and devices

• US 9,670,185 B2
• Filed: 10/23/2015
• Issued: 06/06/2017
• Est. Priority Date: 12/07/2012
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Lin, Chun, Kwong, Raymond, Joseph, Scott, Xia, Chuanjun, Esler, James
• Primary Examiner(s): CLARK, GREGORY D
• Application Number:
  US14/921,446
• Publication Number:
  US 20160060251A1
• Time in Patent Office: 592 Days
• Field of Search: None
• 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 compound having the formula:

2. The compound of claim 1, wherein at least one of R¹, R², R³, R⁴, R⁵, R⁶, R⁷, and R⁸ comprises the electron donor group selected from the group consisting of:

3. The compound of claim 1, wherein the compound has the formula:

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

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

6. The compound of claim 1, wherein at least one of R¹, R², R³, R⁴, R⁵, R⁶, R⁷, and R⁸ comprises at least one electron donor group having the structure

7. The compound of claim 1, wherein at least one of R¹, R², R³, R⁴, R⁵, R⁶, R⁷, and R⁸ comprises at least one electron donor group having the structure

8. The compound of claim 1, wherein at least one of R¹, R², R³, R⁴, R⁵, R⁶, R⁷, and R⁸ comprises at least one electron donor group having the structure

9. The compound of claim 1, wherein at least one of R¹, R², R³, R⁴, R⁵, R⁶, R⁷, and R⁸ comprises at least one electron donor group having the structure

10. The compound of claim 1, wherein at least one of R¹, R², R³, R⁴, R⁵, R⁶, R⁷, and R⁸ comprises at least one electron donor group having the structure

11. The compound of claim 1, wherein at least one of R¹, R², R³, R⁴, R⁵, R⁶, R⁷, and R⁸ comprises at least one electron donor group having the structure

12. The compound of claim 1, wherein at least one of R¹, R², R³, R⁴, R⁵, R⁶, R⁷, and R⁸ comprises at least one electron donor group having the structure

13. The compound of claim 1, wherein at least one of R¹, R², R³, R⁴, R⁵, R⁶, R⁷, and R⁸ comprises at least one electron donor group having the structure

14. The compound of claim 1, wherein at least one of R¹, R², R³, R⁴, R⁵, R⁶, R⁷, and R⁸ comprises at least one electron donor group having the structure

15. The compound of claim 1, wherein L¹ is

16. The compound of claim 1, wherein L¹ is

17. The compound of claim 1, wherein L¹ is

18. The compound of claim 1, wherein L¹ is

19. The compound of claim 1, wherein L¹ is

20. The compound of claim 1, wherein L¹ is