Organic electroluminescent materials and devices

• US 9,419,225 B2
• Filed: 03/14/2013
• Issued: 08/16/2016
• Est. Priority Date: 03/14/2013
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Xia, Chuanjun, Adamovich, Vadim, Wu, Yonggang, Zeng, Lichang
• Primary Examiner(s): Zhang, Ruiyun
• Application Number:
  US13/803,044
• Publication Number:
  US 20140264292A1
• Time in Patent Office: 1,251 Days
• Field of Search: 428/690, 428/917, 257/40, 313/504, 313/505, 313/506, 546/276.7, 546/80, 546/89, 548/440, 548/445
• US Class Current: 1/1
• CPC Class Codes: C07D 209/86 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 403/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C09B 57/00 Other synthetic dyes of known constitution
• CPC Class Codes: C09B 57/008 Triarylamine dyes containing no other chromophores
• CPC Class Codes: C09B 57/10 Metal complexes of organic compounds not being dyes in uncomplexed form
• CPC Class Codes: C09K 11/025 non-luminescent particle coatings or suspension media
• 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 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 2101/30 Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/15 Hole transporting layers
• CPC Class Codes: H10K 50/16 Electron transporting layers
• CPC Class Codes: H10K 50/17 Carrier injection layers
• CPC Class Codes: H10K 50/171 Electron injection layers
• CPC Class Codes: H10K 50/18 : Carrier blocking layers
• CPC Class Codes: H10K 50/822 : characterised by their shape
• CPC Class Codes: H10K 85/324 : comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/342 : comprising iridium
• CPC Class Codes: H10K 85/622 : containing four rings, e.g. pyrene
• 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

Abstract

A compound according to a formula I, devices incorporating the same, and formulations including the same are described. The compound according to the formula I can have the structure

wherein R¹, R², R³, R⁴, R⁵ and R⁶ each represent mono, di, tri, tetra substitutions, or no substitution, R⁹ represents mono, di, tri substitutions, or no substitution, R¹, R², R³, R⁴, R⁵, R⁶ and R⁹ are each 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 acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof. A¹, A², A³, A⁴, A⁵, and A⁶ are each independently selected from N or C and n is an integer from 1 to 20.

Claims

1. A compound having a structure selected from the group consisting of formula II, III, IV, and V:

2. The compound of claim 1, wherein the compound has a structure of formula IV:

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

4. The compound of claim 1, wherein R¹, R², R³, R⁴, R⁵, R⁶ and R⁹ are each independently selected from the group consisting of hydrogen, deuterium, silyl, aryl, and heteroaryl.

5. The compound of claim 1, wherein n is an integer from 1 to 5.

6. The compound of claim 1, wherein

n is an integer from 1 to 3;

and

R¹, R², R³, R⁴, R⁵, R⁶ and R⁹ are each independently selected from the group consisting of hydrogen and phenyl.

7. The compound of claim 6, wherein n is 1;

and R¹, R², R³, R⁴, R⁵, R⁶ and R⁹ are hydrogen.

8. The compound of claim 1, wherein n is 2.

19. A composition comprising a compound of claim 1.

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

9. A first device comprising an organic light-emitting device, further comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound having a structure selected from the group consisting of formula II, III, IV, and V;

10. The first device of claim 9, wherein R¹, R², R³, R⁴, R⁵, R⁶ and R⁹ are each independently selected from the group consisting of hydrogen, deuterium, silyl, aryl, and heteroaryl.

11. The first device of claim 9, wherein the organic layer is an emissive layer and the compound of the formula I is a host.

12. The first device of claim 11, wherein the organic layer further comprises an emissive dopant.

13. The first device of claim 12, wherein the emissive dopant is a transition metal complex having at least one ligand selected from the group consisting of:

14. The first device of claim 9, wherein the organic layer is a blocking layer and the compound having the formula I is a blocking material in the organic layer.

15. The first device of claim 9, wherein the organic layer is an electron transporting and the compound having formula I is an electron transporting material in the organic layer.

16. The first device of claim 9, wherein the first device is a consumer product.

17. The first device of claim 9, wherein the first device is an organic light-emitting device.

18. The first device of claim 9, wherein the first device comprises a lighting panel.

20. The first device of claim 9, wherein the compound of the formula I is selected from the group consisting of: