Organic electroluminescent materials and devices

• US 9,735,378 B2
• Filed: 09/09/2013
• Issued: 08/15/2017
• Est. Priority Date: 09/09/2013
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Xia, Chuanjun, Lin, Chun
• Primary Examiner(s): Vetere, Robert
• Application Number:
  US14/021,274
• Publication Number:
  US 20150069334A1
• Time in Patent Office: 1,436 Days
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/0086 Platinum compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• 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 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/346 comprising platinum
• CPC Class Codes: H10K 85/361 Polynuclear complexes, i.e. complexes comprising two or more metal centers

Abstract

Ir/Pt metal complexes, devices containing the Ir/Pt metal complexes, and methods of making such devices are described. The Ir/Pt metal complex includes a first Ir moiety and a first Pt moiety. The first Ir moiety can be an Ir(III) six-coordinated structure. The first Pt moiety can be a Pt(II) four-coordinated tetradentate structure. The devices can have layers that include the Ir/Pt metal complexes. The layers containing the Ir/Pt metal complexes can be made by a solution process.

Claims

1. A compound comprising the formula

2. The compound of claim 1, wherein the first Ir moiety comprises an Ir tris-bidentate structure.

3. The compound of claim 1, wherein the organic moiety comprises a chemical group selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof.

4. The compound of claim 3, wherein the organic moiety comprises a chemical group selected from the group consisting of alkyl, cycloalkyl, amino, silyl, aryl, heteroaryl and combinations thereof.

5. The compound of claim 3, wherein the organic moiety comprises a chemical group selected from the group consisting of methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, triphenylene, terphenyl, tetraphenyl, pentaphenyl, pyridine, phenyl pyridine, pyridyl phenyl, fluorene, carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, partially or fully deuterated variants thereof, and combinations thereof.

6. The compound of claim 1, wherein the compound further comprises a second Ir moiety.

7. The compound of claim 1, wherein the compound further comprises a second Pt moiety.

8. The compound of claim 1, wherein the compound has an emissive spectrum having a peak wavelength of about 400 nm to about 480 nm.

9. The compound of claim 1, wherein the compound emits yellow to orange light with a full width at half maximum between about 70 nm to about 110 nm when the light has a peak wavelength between about 530 nm to about 580 nm.

10. The compound of claim 1, wherein the total number of metal atoms is 2 to 7.

11. The compound of claim 1, wherein the compound is neutral.

12. The compound of claim 1, wherein the first Ir moiety comprises an Ir six-coordinated structure having at least one ligand or part of the ligand if the ligand is more than bidentate selected from the group consisting of:

13. The compound of claim 12, wherein the first Ir moiety comprises an Ir six-coordinated structure having at least one ligand or part of the ligand if the ligand is more than bidentate selected from the group consisting of:

14. The compound of claim 1, wherein the first Pt moiety comprises a Pt four-coordinated structure wherein part of the tetradentate ligand is selected from the group consisting of:

15. The compound of claim 14, wherein the first Pt moiety comprises a Pt four-coordinated structure, wherein part of the tetradentate ligand is selected from the group consisting of:

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

17. The compound of claim 1, wherein the first Ir moiety comprises a chemical structure selected from the group consisting of

18. The compound of claim 1, wherein the first Pt moiety comprises a chemical structure selected from the group consisting of

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

20. A first device comprising a first organic light emitting device, the first organic light emitting device comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound comprising the formula

21. The first device of claim 20, wherein the organic layer is deposited using a solution process.

22. The first device of claim 20, wherein the first device is a consumer product.

23. The first device of claim 20, wherein the first device is an organic light emitting device.

24. The first device of claim 20, wherein the first device comprises a light panel.

25. The first device of claim 20, wherein the organic layer is an emissive layer and the compound is an emissive dopant.

26. The first device of claim 20, wherein the organic layer is an emissive layer and the compound is a non-emissive dopant.

27. The first device of claim 20, wherein the organic layer further comprises a host material.

28. The first device of claim 27, wherein the host material comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;

wherein any substituent in the host material is an unfused substituent independently selected from the group consisting of C_nH_2n+1, OC_nH_2n+1, OAr₁, N(C_nH_2n+1)₂, N(Ar₁)(Ar₂), CH═

CH—

C_nH_2n+1, C≡

C—

C_nH_2n+1, Ar₁, Ar₁-Ar₂, C_nH_2n—

Ar₁, or no substitution;

wherein n is from 1 to 10; and

wherein Ar₁ and Ar₂ are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

29. The first device of claim 27, wherein the host material comprises at least one chemical group selected from the group consisting of carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

30. The first device of claim 27, wherein the host material is selected from the group consisting of:

31. The first device of claim 27, wherein the host material comprises a metal complex.

32. A method for making an organic electronic device, comprising:

providing a first electrode disposed on a substrate;

forming a first organic layer over the first electrode, wherein the first organic layer comprises a first compound; and

forming a second electrode disposed over the first organic layer, wherein the first compound comprises the formula

33. The method of claim 32, wherein forming the first organic layer comprises depositing the first compound by solution processing.

34. The method of claim 32, further comprising forming a second organic layer over the first electrode such that the second organic layer is disposed between the first organic layer and the first electrode.

35. The method of claim 34, wherein forming the second organic layer comprises depositing by solution processing.

36. The method of claim 34, wherein the second organic layer comprises a hole injection material.

37. The method of claim 35, further comprising cross-linking the second organic layer.

38. The method of claim 34, further comprising forming a third organic layer over the second organic layer such that the third organic layer is disposed between the second organic layer and the first organic layer, wherein the third organic layer comprises a hole transport material.

39. The method of claim 38, wherein forming the third organic layer comprises depositing by solution processing.

40. The method of claim 39, further comprising cross-linking the third organic layer.

41. The method of claim 38, further comprising depositing a fourth organic layer over the first organic layer such that the fourth organic layer is disposed between the first organic layer and the cathode, wherein the fourth organic layer comprises an electron transport material.

42. The method of claim 41, wherein the fourth organic layer is deposited by vacuum thermal evaporation.

43. The method of claim 41, further comprising depositing a fifth organic layer over the fourth organic layer such that the fifth organic layer is disposed between the fourth organic layer and the cathode, wherein the fifth organic layer comprises an electron transport material.