AMINE DERIVATIVE, ORGANIC LUMINESCENT MATERIAL AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE AMINE DERIVATIVE OR THE ORGANIC LUMINESCENT MATERIAL

• US 20150270502A1
• Filed: 06/04/2015
• Published: 09/24/2015
• Est. Priority Date: 12/05/2012
• Status: Active Grant

• Current Assignee: Samsung Display Company Limited (Samsung Electronics Co. Ltd.)
• Original Assignee: Samsung Display Company Limited (Samsung Electronics Co. Ltd.)
• Inventors: FUCHIWAKI, Junta, MIYATA, Yasuo, SAKAMOTO, Naoya, UENO, Masatsugu, TAKADA, Ichinori, OYAMA, Hiromi
• Granted Patent: US 9,780,317 B2
• Time in Patent Office: Days
• US Class Current: 1/1
• CPC Class Codes: C07F 7/081 comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
• 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: C07F 7/0816 said ring comprising Si as a ring atom
• CPC Class Codes: C07F 9/65685 the ring phosphorus atom being part of a phosphine oxide or thioxide
• 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 2211/1025 characterised by ligands
• 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 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/1092 containing sulfur as the only heteroatom
• 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 50/81 Anodes
• CPC Class Codes: H10K 85/40 Organosilicon compounds, e.g. TIPS pentacene
• CPC Class Codes: H10K 85/615 Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/631 : Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
• CPC Class Codes: H10K 85/633 : comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/636 : comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/654 : comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/655 : comprising only sulfur as heteroatom
• CPC Class Codes: H10K 85/6572 : comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: H10K 85/6574 : comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
• CPC Class Codes: H10K 85/6576 : comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Abstract

An amine derivative represented by the following General Formula (1) is provided.

In the above General Formula (1), Ar¹, Ar² and Ar³ are independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, at least one of Ar¹, Ar² and Ar³ is substituted with a substituted or unsubstituted silyl group, and L is a single bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

Claims

1. An amine derivative represented by the following General Formula (1):

2. The amine derivative as claimed in claim 1, wherein at least one of Ar¹, Ar² and Ar³ is the substituted or unsubstituted heteroaryl group.

3. The amine derivative as claimed in claim 1, wherein Ar¹ and Ar² are independently the substituted or unsubstituted aryl group.

4. The amine derivative as claimed in claim 2, wherein Ar¹ and Ar² are independently a substituted or unsubstituted aryl group having 6 to 18 carbon atoms for forming a ring, and Ar³ is a substituted or unsubstituted dibenzoheterole group.

5. The amine derivative as claimed in claim 1, wherein the silyl group is:

a triarylsilyl group where an aryl substituent at the silyl group has 6 to 18 carbon atoms for forming a ring, or

a trialkylsilyl group where an alkyl substituent at the silyl group has 1 to 6 carbon atoms.

6. The amine derivative as claimed in claim 1, wherein each of Ar¹ and Ar² is substituted with a silyl group.

7. The amine derivative as claimed in claim 1, wherein each of Ar¹, Ar² and Ar³ is substituted with a silyl group.

8. The amine derivative having a silyl group as claimed in claim 1, wherein L is a single bond or an arylene group having 6 to 14 carbon atoms for forming a ring.

9. The amine derivative as claimed in claim 4, wherein Ar³ is a substituted or unsubstituted dibenzofuryl group.

10. The amine derivative as claimed in claim 9, wherein L is not the single bond.

11. The amine derivative as claimed in claim 10, wherein L is a phenylene group, and the dibenzofuryl group is combined with L at position 3 of the dibenzofuryl group.

12. The amine derivative as claimed in claim 11, wherein the amine derivative represented by General Formula (1) is a compound represented by the following General Formula (2):

13. The amine derivative as claimed in claim 1, wherein Ar¹ and Ar² are independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, at least one of Ar¹ and Ar² being substituted with a substituted or unsubstituted silyl group, Ar³ is a substituted or unsubstituted dibenzofuryl group, and L is a single bond.

14. The amine derivative as claimed in claim 13, wherein the dibenzofuryl group is combined with L at position 3 of the dibenzofuryl group.

15. The amine derivative as claimed in claim 1, wherein Ar¹ and Ar² are independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, at least one of Ar¹ and Ar² is substituted with a substituted or unsubstituted silyl group, Ar³ is a substituted or unsubstituted carbazolyl group, and L is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.

16. The amine derivative as claimed in claim 1, wherein Ar³ is a substituted or unsubstituted fluorenyl group, and L is a single bond, and the amine derivative is represented by the following General Formula (3):

17. The amine derivative as claimed in claim 16, wherein the substituent of the fluorenyl group is independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

18. The amine derivative as claimed in claim 16, wherein the fluorenyl group is combined with L at position 2 of the fluorenyl group.

19. The amine derivative as claimed in claim 16, wherein Ar¹ and Ar² are independently a substituted or unsubstituted aryl group.

20. The amine derivative as claimed in claim 16, wherein Ar¹ is a substituted or unsubstituted aryl group and Ar² is a substituted or unsubstituted dibenzoheterole group.

21. The amine derivative as claimed in claim 16, wherein one of Ar¹ and Ar² is substituted with a substituted or unsubstituted silyl group.

22. The amine derivative as claimed in claim 16, wherein the silyl group is:

a triarylsilyl group where an aryl substituent at the silyl group has 6 to 18 carbon atoms for forming a ring, or

a trialkylsilyl group where an alkyl substituent at the silyl group has 1 to 6 carbon atoms.

23. The amine derivative as claimed in claim 1, wherein Ar¹ and Ar² are independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, at least one of Ar¹ and Ar² being substituted with a substituted or unsubstituted silyl group, Ar³ is a substituted or unsubstituted carbazolyl group, and L is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.

24. The amine derivative as claimed in claim 23, wherein the substituted or unsubstituted carbazolyl group is combined with L at position 2 or position 3 of the carbazolyl group.

25. The amine derivative as claimed in claim 1, wherein Ar¹ and Ar² are independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, at least one of Ar¹ and Ar² being substituted with a substituted or unsubstituted silyl group, Ar³ is a substituted or unsubstituted carbazolyl group, and L is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group, and the amine derivative is represented by the following General Formula (4):

26. The amine derivative as claimed in claim 25, wherein two or more of R¹ to R⁸ are combined to each other to form a saturated or unsaturated ring.

27. The amine derivative as claimed in claim 26, wherein L is a phenylene group, a biphenylene group or a fluorenylene group.

28. The amine derivative as claimed in claim 27, wherein Ar¹ and Ar² are an aryl group having 6 to 12 carbon atoms for forming a ring when L is the fluorenylene group.

29. The amine derivative as claimed in claim 1, wherein Ar¹ is an aryl group substituted with a silyl group and represented by the following General Formula (5), Ar² is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, Ar³ is an aryl group represented by the following General Formula (6), and L is an arylene group represented by the following General Formula (7):

30. The amine derivative as claimed in claim 29, wherein R₁₁, R₁₂ and R₁₃ are each a phenyl group.

31. The amine derivative as claimed in claim 30, wherein o is 0 or 1.

32. The amine derivative as claimed in claim 31, wherein n is 2.

33. A material for an organic electroluminescent device, the material comprising the amine derivative represented by the following General Formula (1):

34. The material for an organic electroluminescent device as claimed in claim 33, wherein Ar³ is a substituted or unsubstituted fluorenyl group, and L is a single bond, and the amine derivative is represented by the following General Formula (3):

35. The material for an organic electroluminescent device as claimed in claim 34, wherein the material for an organic electroluminescent device is a hole transport material.

36. The material for an organic electroluminescent device as claimed in claim 33, wherein Ar¹ is an aryl group substituted with a silyl group and represented by the following General Formula (5), Ar² is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, Ar³ is an aryl group represented by the following General Formula (6), and L is an arylene group represented by the following General Formula (7):

37. An organic electroluminescent device comprising the amine derivative at least in an emission layer and in one layer of laminated layers between the emission layer and an anode,

wherein the amine derivative represented by the following General Formula (1):

38. The electroluminescent device comprising the amine derivative as claimed in claim 37, wherein Ar¹ and Ar² are independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, at least one of Ar¹ and Ar² being substituted with a substituted or unsubstituted silyl group, Ar³ is a substituted or unsubstituted dibenzofuryl group, and L is a single bond.

39. The organic electroluminescent device comprising the amine derivative as claimed in claim 37, wherein Ar¹ and Ar² are independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, at least one of Ar¹ and Ar² is substituted with a substituted or unsubstituted silyl group, Ar³ is a substituted or unsubstituted carbazolyl group, and L is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.

40. The organic electroluminescent device further comprising a hole transport layer disposed between a cathode and the anode, wherein the hole transport layer includes the amine derivative as claimed in claim 37, wherein Ar³ is a substituted or unsubstituted fluorenyl group, and L is a single bond, and the amine derivative is represented by the following General Formula (3):

41. The organic electroluminescent device comprising the amine derivative as claimed in claim 37, wherein Ar¹ and Ar² are independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, at least one of Ar¹ and Ar² being substituted with a substituted or unsubstituted silyl group, Ar³ is a substituted or unsubstituted carbazolyl group, and L is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.

42. The organic electroluminescent device comprising the amine derivative as claimed in claim 37, wherein Ar¹ and Ar² are independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, at least one of Ar¹ and Ar² being substituted with a substituted or unsubstituted silyl group, Ar³ is a substituted or unsubstituted carbazolyl group, and L is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group, and the amine derivative is represented by the following General Formula (4):

43. The organic electroluminescent device comprising the material for an organic electroluminescent device in one layer of laminated layers disposed between the emission layer and the anode, wherein Ar¹ is an aryl group substituted with a silyl group and represented by the following General Formula (5), Ar² is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, Ar³ is an aryl group represented by the following General Formula (6), and L is an arylene group represented by the following General Formula (7):