Asymmetric hosts with triaryl silane side chains

• US 9,184,399 B2
• Filed: 05/04/2012
• Issued: 11/10/2015
• Est. Priority Date: 05/04/2012
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Dyatkin, Alexey, Zeng, Lichang, Xia, Chuanjun
• Primary Examiner(s): Clark, Gregory
• Application Number:
  US13/464,122
• Publication Number:
  US 20130293094A1
• Time in Patent Office: 1,285 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: C07F 7/0812 comprising a heterocyclic ring
• CPC Class Codes: C07F 7/0814 said ring is substituted at a C ring atom by Si
• CPC Class Codes: H10K 50/00 Organic light-emitting devices integrated devices or assemblies of multiple devices H10K59/00, H10K65/00; organic semiconductor lasers H01S5/36
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/40 Organosilicon compounds, e.g. TIPS pentacene
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/6574 comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes

Abstract

Novel asymmetric host compounds containing an electron-transport moiety, a hole-transport moiety, an aromatic spacer, and a triaryl silane group are provided. These compounds are useful materials that can be incorporated into OLED devices.

Claims

1. A compound having the formula:

L₁-L₂-L₃ 

 

Formula I;

wherein L₁ is selected from the group consisting of carbazole, azacarbazole, triphenylene, aza-triphenylene and combinations thereof;

wherein L₂ is selected from the group consisting of phenyl, pyridine, pyrazine, triazine and combinations thereof;

wherein L₃ is selected from the group consisting of dibenzofuran, dibenzothiophene, azadibenzofuran, azadibenzothiophene, dibenzoselenophene, azadibenzoselenophene, and combinations thereof;

wherein at least one of L₁ to L₃ is substituted by at least one SiAr₁Ar₂Ar₃ group;

wherein Ar₁ to Ar₃ are independently selected from aryl or heteroaryl groups;

wherein each of L₁ to L₃ is optionally substituted with a group 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, sulfanyl, sulfonyl, phosphino, and combinations thereof; and

wherein any optional substitution on L₁ and L₃ can be fused to L₁ and L₃ respectively; and

wherein any optional substitution on L₂ is unfused.

2. The compound of claim 1, wherein each of L₁ to L₃ is optionally substituted with a group selected from the group consisting of hydrogen, deuterium, aryl, heteroaryl, or combinations thereof.

3. The compound of claim 1, wherein each of L₁ to L₃ is substituted with hydrogen.

4. The compound of claim 1, wherein L₁ is selected from the group consisting of:

5. The compound of claim 1, wherein L₁ is selected from the group consisting of:

6. The compound of claim 1, wherein L₂ is selected from the group consisting of:

7. The compound of claim 1, wherein L₃ is selected from the group consisting of:

8. The compound of claim 1, wherein L₃ is selected from the group consisting of:

9. The compound of claim 1, wherein Ar₁ to Ar₃ are selected from the group consisting of phenyl, biphenyl, pyridyl, naphthyl, and combinations thereof.

10. The compound of claim 1, wherein Ar₁, Ar₂, and Ar₃ are phenyl.

11. The compound of claim 1, wherein L₃ contains dibenzothiophene.

12. The compound of claim 1, wherein L₃ contains dibenzofuran.

13. The compound of claim 1, wherein L₂ contains phenyl.

14. The compound of claim 1, wherein L₂ contains a biphenyl.

15. The compound of claim 1, wherein L₂ contains a terphenyl.

16. The compound of claim 1, wherein L₁ contains carbazole.

17. The compound of claim 1, wherein L₁ contains triphenylene.

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

19. 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 the formula;

L₁-L₂-L₃ 

 

Formula I;

wherein L₁ is selected from the group consisting of carbazole, azacarbazole, triphenylene, aza-triphenylene and combinations thereof;

wherein L₂ is selected from the group consisting of phenyl, pyridine, pyrazine, triazine and combinations thereof;

wherein L₃ is selected from the group consisting of dibenzofuran, dibenzothiophene, azadibenzofuran, azadibenzothiophene, dibenzoselenophene, azadibenzoselenophene, and combinations thereof;

wherein at least one of L₁ to L₃ is substituted by at least one SiAr₁Ar₂Ar₃ group;

wherein Ar₁ to Ar_a are independently selected from aryl or heteroaryl groups;

wherein each of L₁ to L₃ is optionally substituted with a group 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, sulfonyl, sulfonyl, phosphino, and combinations thereof; and

wherein any optional substitution on L₁ and L₃ can be fused to L₁ and L₃ respectively; and

wherein any optional substitution on L₂ is unfused.

20. The first device of claim 19, wherein the organic layer is an emissive layer and the compound of Formula I is a host.

21. The first device of claim 20, further comprising a first dopant material that is an emissive dopant comprising a transition metal complex having at least one ligand or part of the ligand if the ligand is more than bidentate selected from the group consisting of:

22. The first device of claim 19, wherein the organic layer is a non-emissive layer.

23. The first device of claim 19, wherein the organic layer is a first organic layer, and the device further comprises a second organic layer that is a non-emissive layer and the compound having Formula I is a material in the second organic layer.

24. The first device of claim 23, wherein the second organic layer is a blocking layer and the compound having Formula I is a blocking material in the second organic layer.

25. The first device of claim 19, wherein the first device is a consumer product.

26. The first device of claim 19, wherein the first device is an organic light-emitting device.

27. The first device of claim 19, wherein the first device comprises a lighting panel.