Organic electroluminescent materials and devices

• US 9,397,302 B2
• Filed: 10/08/2014
• Issued: 07/19/2016
• Est. Priority Date: 10/08/2014
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Boudreault, Pierre-Luc T., Yeager, Walter, Xia, Chuanjun
• Primary Examiner(s): HENRY, CALEB E
• Application Number:
  US14/509,274
• Publication Number:
  US 20160104848A1
• Time in Patent Office: 650 Days
• Field of Search: 257/40
• US Class Current: 1/1
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1033 with oxygen
• 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 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/12 comprising dopants
• CPC Class Codes: H10K 50/81 Anodes
• CPC Class Codes: H10K 50/82 Cathodes
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

Novel ligands for metal complex compounds that are useful as a phosphorescent emitter in organic light emitting devices that incorporate fluorinated side chains in the ligands are disclosed. Such metal complex has at least one substituent R selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof, wherein R is directly bonded to an aromatic ring, In the compound, C having an F attached thereto is separated by at least one carbon atom from the aromatic ring.

Claims

1. A composition comprising a first compound;

wherein the first compound is capable of functioning as a phosphorescent emitter in an organic light emitting device at room temperature;

wherein the first compound has at least one aromatic ring and at least one substituent R;

wherein each of the at least one R is independently selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof;

wherein each of the at least one R is directly bonded to one of the aromatic rings;

wherein in each of the at least one R, C having an F attached thereto is separated by at least one carbon atom from the aromatic ring;

wherein the first compound has the formula of M(L¹)_x(L²)_y(L³)_z;

wherein L¹, L², and L³ can be the same or different;

wherein x is 1, 2, or 3;

wherein y is 0, 1, or 2;

wherein z is 0, 1, or 2;

wherein x+y+z is the oxidation state of the metal M;

wherein L¹, L², and L³ are each independently selected from the group consisting of;

2. The composition of claim 1, wherein the first compound is capable of emitting light from a triplet excited state to a ground singlet state at room temperature.

3. The composition of claim 1, wherein the metal is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

4. The composition of claim 1, wherein the metal is Ir.

5. The composition of claim 1, wherein the metal is Pt.

6. The composition of claim 1, wherein the C having an F attached thereto is separated by at least two carbon atoms from the aromatic ring.

7. The composition of claim 1, wherein the C having an F attached thereto is separated by at least three carbon atoms from the aromatic ring.

8. The composition of claim 1, wherein each of the at least one R contains at least one CF₃ group.

9. The composition of claim 1, wherein none of the at least one R contain any CF₃ groups.

10. The composition of claim 1, wherein the first compound does not have any F atoms other than in the at least one R.

11. The composition of claim 1, wherein the aromatic ring comprises LUMO electron density of the first compound.

12. The composition of claim 1, wherein the first compound has the formula of Ir(L¹)₂(L²).

13. The composition of claim 12, wherein L¹ has the formula selected from the group consisting of:

14. The composition of claim 13, wherein L² has the formula:

15. The composition of claim 12, wherein L¹ and L² are different and each independently selected from the group consisting of:

16. The composition of claim 12, wherein L¹ and L² are each independently selected from the group consisting of:

17. The composition of claim 1, wherein the first compound has the formula of Pt(L¹)₂ or Pt(L¹)(L²).

18. The composition of claim 17, wherein L¹ is connected to the other L¹ or L² to form a tetradentate ligand.

19. The composition of claim 1, wherein at least one of R_a, R_b, R_c, and R_d includes an alkyl or cycloalkyl group that includes CD, CD₂, or CD₃, wherein D is deuterium.

20. The composition of claim 1, wherein L¹, L², and L³ are each independently selected from the group consisting of:

21. The composition of claim 1, wherein the first compound has the formula of Ir(L¹)₂(L²), wherein L¹ is selected from the group consisting of

22. The compound of claim 21, wherein the first compound is selected from the group consisting of Compound 1 through Compound 5,863,

wherein each of Compound x, where x=451j+k−

451, k is an integer from 1 to 451, and j is an integer from 1 to 13, has the formula Ir(L_Ak)₂(L_Bj).

23. The composition of claim 1, wherein the first compound is selected from the group consisting of

32. A formulation comprising the composition of claim 1.

24. 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 first compound, wherein the first compound is capable of functioning as a phosphorescent emitter at room temperature;

wherein the first compound has at least one aromatic ring and at least one substituent R;

wherein each of the at least one R is independently selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof;

wherein each of the at least one R is directly bonded to one of the aromatic rings; and

wherein in each of the at least one R, C having an F attached thereto is separated by at least one carbon atom from the aromatic ring;

wherein the first compound has the formula of M(L¹)_x(L²)_y(L³)_z;

wherein L¹, L², and L³ can be the same or different;

wherein x is 1, 2, or 3;

wherein y is 0, 1, or 2;

wherein z is 0, 1, or 2;

wherein x+y+z is the oxidation state of the metal M;

wherein L¹, L², and L³ are each independently selected from the group consisting of;

25. The first device of claim 24, wherein the first compound is selected from the group consisting of

26. The first device of claim 24, wherein the first device is selected from the group consisting of a consumer product, an electronic component module, an organic light emitting device, and a lighting panel.

27. The first device of claim 24, wherein the organic layer is an emissive layer and the first compound is an emissive dopant or a non-emissive dopant.

28. The first device of claim 24, wherein the organic layer further comprises a host;

wherein the host 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 24, wherein the organic layer further comprises a host;

wherein the host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

30. The first device of claim 24, wherein the organic layer further comprises a host;

wherein the host material is selected from the group consisting of;

31. The first device of claim 24, wherein the organic layer further comprises a host;

wherein the host material comprises a metal complex.