CARBAZOLE-CONTAINING MATERIALS IN PHOSPHORESCENT LIGHT EMITTING DIODES

• US 20090134784A1
• Filed: 11/21/2008
• Published: 05/28/2009
• Est. Priority Date: 12/28/2007
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Dyatkin, Alexey, Lin, Chun, Elshenawy, Zeinab
• Granted Patent: US 8,221,905 B2
• Time in Patent Office: Days
• US Class Current: 313/504
• CPC Class Codes: C07D 209/88 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
• CPC Class Codes: C07D 401/14 containing three or more hetero 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 491/14 Ortho-condensed systems
• CPC Class Codes: C07D 495/04 Ortho-condensed systems
• CPC Class Codes: C07D 495/14 Ortho-condensed systems
• CPC Class Codes: C07D 513/04 Ortho-condensed systems
• CPC Class Codes: C07D 513/14 Ortho-condensed systems
• CPC Class Codes: C09B 57/00 Other synthetic dyes of known constitution
• CPC Class Codes: C09B 67/0033 Blends of pigments; Mixtured crystals; Solid solutions
• CPC Class Codes: C09B 69/109 containing other specific dyes
• 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 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1416 Condensed systems
• CPC Class Codes: C09K 2211/145 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/1458 : containing sulfur as the only heteroatom
• CPC Class Codes: C09K 2211/1466 : containing nitrogen as the only heteroatom
• 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 85/324 : comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/342 : comprising iridium
• CPC Class Codes: H10K 85/6572 : comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: Y10S 428/917 : Electroluminescent

Abstract

Carbazole-containing compounds are provided. In particular, the compounds are oligocarbazole-containing compounds having an unsymmetrical structure. The compounds may be useful in organic light emitting devices, in particular as hosts in the emissive layer of such devices.

Claims

1. A carbazole-containing compound comprising:

wherein a is 1 to 20;

wherein b is 0 to 20;

wherein m is 0 to 2;

wherein n is 0 to 2;

wherein m+n is at least 1;

wherein X is selected from the group consisting of biphenyl, terphenyl, naphthalene, triphenylene, phenanthrene, fluorene, chrysene, dibenzothiophene, dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, and thienodipyridine; and

wherein X is substituted by R, where R is selected from the group consisting of hydrogen, alkyl, heteroalkyl, benzene, biphenyl, terphenyl, naphthalene, phenalene, phenanthrene, fluorene, chrysene, dibenzothiophene, dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, and thienodipyridine.

2. The compound of claim 1, wherein a is 1 to 20 and n is 0.

3. The compound of claim 1, wherein a is 1 or 2 and n is 0.

4. The compound of claim 1, wherein a is 1, b is 1, and n is 1.

5. The compound of claim 1, wherein X is selected from biphenyl, terphenyl, triphenylene, phenanthrene, fluorene, dibenzothiophene, dibenzofuran, pyridine, pyridazine, pyrimidine, pyrazine, triazine, benzimidazole, benzothiazole, quinoline, isoquinoline, benzofuropyridine, furodipyridine, benzothienopyridine, and thienodipyridine.

6. The compound of claim 1, wherein X is selected from the group consisting of dibenzothiophene, dibenzofuran, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, and triphenylene.

7. The compound of claim 1, wherein R is selected from the group consisting of hydrogen, alkyl, benzene, biphenyl, terphenyl, triphenylene, phenanthrene, fluorene, dibenzothiophene, dibenzofuran, pyridine, pyridazine, pyrimidine, pyrazine, triazine, benzimidazole, benzothiazole, quinoline, isoquinoline, benzofuropyridine, furodipyridine, benzothienopyridine, and thienodipyridine.

8. The compound of claim 1 wherein R is selected from the group consisting of hydrogen, alkyl, benzene, biphenyl, terphenyl, dibenzothiophene, dibenzofuran.

9. The compound of claim 5, wherein R is selected from the group consisting of hydrogen, alkyl, benzene, biphenyl, terphenyl, triphenylene, phenanthrene, fluorene, dibenzothiophene, dibenzofuran, pyridine, pyridazine, pyrimidine, pyrazine, triazine, benzimidazole, benzothiazole, quinoline, isoquinoline, benzofuropyridine, furodipyridine, benzothienopyridine, and thienodipyridine.

10. The compound of claim 6, wherein R is selected from the group consisting of hydrogen, alkyl, benzene, biphenyl, terphenyl, dibenzothiophene, dibenzofuran.

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

12. The compound of claim 11, wherein the compound is selected from the group consisting of:

13. The compound of claim 11, wherein the compound is selected from the group consisting of:

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

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

16. The compound of claim 11, wherein the compound is selected from the group consisting of:

17. The compound of claim 11, wherein the compound is selected from the group consisting of:

18. An organic light emitting device, comprising:

an anode;

a cathode; and

a first organic layer disposed between the anode and the cathode, wherein the organic layer comprises a carbazole-containing compound, comprising

wherein a is 1 to 20;

wherein b is 0 to 20;

wherein m is 0 to 2;

wherein n is 0 to 2;

wherein m+n is at least 1;

wherein X is selected from the group consisting of biphenyl, terphenyl, naphthalene, triphenylene, phenanthrene, fluorene, chrysene, dibenzothiophene, dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, and thienodipyridine; and

wherein X is substituted by R, where R is selected from the group consisting of hydrogen, alkyl, heteroalkyl, benzene, biphenyl, terphenyl, naphthalene, phenalene, phenanthrene, fluorene, chrysene, dibenzothiophene, dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, and thienodipyridine.

19. The device of claim 18, wherein the carbazole-containing compound is selected from the group consisting of:

20. The device of claim 19, wherein the first organic layer is an emissive layer and the carbazole-containing compound is a host in the first organic layer.

21. The device of claim 20, wherein the emissive layer further comprises a phosphorescent emitter.

22. The device of claim 21, wherein the phosphorescent emitter is an iridium complex having the formula:

wherein n=1, 2 or 3;

wherein R^1a, R^1b, R^1c, R^1d, R^1e, R^1f, R^1g, R^1h, and R¹ⁱ are each, independently, H, hydrocarbyl, heteroatom substituted hydrocarbyl, cyano, fluoro, OR^2a, SR^2a, NR^2aR^2b, BR^2aR^2b, or SiR^2aR^2bR^2c, wherein R^2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and wherein any two of R^1a-i and R^2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring; and

wherein X-Y is an ancillary ligand.

23. The device of claim 21, wherein the phosphorescent emitter is a compound comprising a phosphorescent metal complex comprising a monoanionic, bidentate ligand having the formula:

wherein E^1a-q are selected from the group consisting of C and N and collectively comprise an 18 pi-electron system;

provided that E^1a and E^1p are different;

wherein R^1a-i are each, independently, H, hydrocarbyl, heteroatom substituted hydrocarbyl, cyano, fluoro, OR^2a, SR^2aNR^2aR^2b, BR^2a, R^2b, or SiR^2aR^2bR^2c, where R^2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and where any two of R^1a-i and R^2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring;

provided that R^1a-i is other than H when attached to N;

wherein the metal is selected from the group consisting of the non-radioactive metals with atomic numbers greater than 40; and

wherein the bidentate ligand may be linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.

24. The device of claim 20, wherein the device further comprises a second organic layer that is a non-emissive layer.

25. The device of claim 24, wherein the first organic layer is adjacent to the second organic layer.

26. The device of claim 21, wherein the phosphorescent emitter has a triplet energy of 425 nm to 495 nm, X is selected from dibenzothiophene, dibenzofuran, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, and triphenylene, and R is selected from hydrogen, alkyl, benzene, biphenyl, terphenyl, dibenzothiophene, dibenzofuran.

27. The device of claim 26, wherein the triplet energy is 440 nm to 480 nm.

28. The device of claim 21, wherein the phosphorescent emitter has a triplet energy of 495 nm to 570 nm, X is selected from biphenyl, terphenyl, triphenylene, phenanthrene, fluorene, dibenzothiophene, dibenzofuran, pyridine, pyridazine, pyrimidine, pyrazine, triazine, benzimidazole, benzothiazole, quinoline, isoquinoline, benzofuropyridine, furodipyridine, benzothienopyridine, and thienodipyridine, and R is selected from hydrogen, alkyl, benzene, biphenyl, terphenyl, triphenylene, phenanthrene, fluorene, dibenzothiophene, dibenzofuran, pyridine, pyridazine, pyrimidine, pyrazine, triazine, benzimidazole, benzothiazole, quinoline, isoquinoline, benzofuropyridine, furodipyridine, benzothienopyridine, and thienodipyridine.

29. The device of claim 28, wherein the triplet energy is 510 nm to 530 nm.

30. The device of claim 18, wherein the oligocarbazole-containing compound has a concentration of 10-100 wt %.

31. The device of claim 30, wherein the oligocarbazole-containing compound has a concentration of 40-99.9 wt %

32. The device of claim 31, further comprising a phosphorescent emitter having a concentration of 0.1 to 30 wt %.

35. The method of claim 32, wherein the first electrode is an anode and the second electrode is a cathode.

36. The method of claim 32, wherein an organic layer is deposited after the first electrode and before the emissive layer.

33. A consumer product comprising a device, the device further comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, the organic layer further comprising a carbazole-containing compound, comprising;

wherein a is 1 to 20;

wherein b is 0 to 20;

wherein m is 0 to 2;

wherein n is 0 to 2;

wherein m+n is at least 1;

wherein X is selected from the group consisting of biphenyl, terphenyl, naphthalene, triphenylene, phenanthrene, fluorene, chrysene, dibenzothiophene, dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, and thienodipyridine; and

wherein X is substituted by R, where R is selected from the group consisting of hydrogen, alkyl, heteroalkyl, benzene, biphenyl, terphenyl, naphthalene, phenalene, phenanthrene, fluorene, chrysene, dibenzothiophene, dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, and thienodipyridine.

34. A method of fabricating an organic light emitting device, comprising:

providing a first electrode;

co-depositing a host and a phosphorescent emitter to form an emissive layer;

wherein the emissive layer comprises an oligocarbazole-containing

compound, comprising;

wherein a is 1 to 20;

wherein b is 0 to 20;

wherein m is 0 to 2;

wherein n is 0 to 2;

wherein m+n is at least 1;

wherein X is selected from the group consisting of biphenyl, terphenyl, naphthalene, triphenylene, phenanthrene, fluorene, chrysene, dibenzothiophene, dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, and thienodipyridine; and

wherein X is substituted by R, where R is selected from the group consisting of hydrogen, alkyl, heteroalkyl, benzene, biphenyl, terphenyl, naphthalene, phenalene, phenanthrene, fluorene, chrysene, dibenzothiophene, dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, and thienodipyridine; and

depositing a second electrode.

37. The method of claim 34, wherein the organic layer is a hole transport layer.