Compound, Light-emitting Lifetime Lengthening Agent, Use of N-type Compound, Film and Light-emitting Device

• US 20200136056A1
• Filed: 05/23/2018
• Published: 04/30/2020
• Est. Priority Date: 05/23/2017
• Status: Active Grant

• Current Assignee: Kyushu University
• Original Assignee: Kyushu University
• Inventors: CUI, Linsong, NAKANOTANI, Hajime, ADACHI, Chihaya
• Granted Patent: US 11,482,679 B2
• Time in Patent Office: Days
• CPC Class Codes: C07D 251/24 to three ring carbon atoms
• CPC Class Codes: C09K 11/025 non-luminescent particle coatings or suspension media
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 2101/20 Delayed fluorescence emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/121 for assisting energy transfer, e.g. sensitization
• CPC Class Codes: H10K 71/18 using non-liquid printing techniques, e.g. thermal transfer printing from a donor sheet
• CPC Class Codes: H10K 85/615 Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/654 comprising only nitrogen as heteroatom H10K85/652 takes precedence

Abstract

A light-emitting device having a light-emitting layer containing a delayed fluorescence emitter and an n-type compound has an extended lifetime and high performance. A compound having a triazine ring substituted by a spiro aromatic group can be used as the n-type compound.

Claims

1-33. -33. (canceled)

34. A light-emitting device emitting a delayed fluorescent light, which contains a compound represented by the following formula (1):

35. The light-emitting device according to claim 34, wherein Ar¹ and Ar² are each independently a substituted or unsubstituted phenyl group.

36. The light-emitting device according to claim 34, wherein R¹ to R⁴ are each independently an alkyl group having 1-20 carbon atoms, an aryl group having 6-40 carbon atoms, a heteroaryl group having 3-40 carbon atoms, an alkoxy group having 1-20 carbon atoms, an aryloxy group having 6-40 carbon atoms, or a heteroaryloxy group having 3-40 carbon atoms.

37. A light-emitting device containing a delayed fluorescence emitter and a host for the delayed fluorescence emitter in a light-emitting layer wherein the host is a compound represented by the following formula (1):

38. The light-emitting device according to claim 37, wherein Ar¹ and Ar² are each independently a substituted or unsubstituted phenyl group.

39. The light-emitting device according to claim 37, wherein R¹ to R⁴ are each independently an alkyl group having 1-20 carbon atoms, an aryl group having 6-40 carbon atoms, a heteroaryl group having 3-40 carbon atoms, an alkoxy group having 1-20 carbon atoms, an aryloxy group having 6-40 carbon atoms, or a heteroaryloxy group having 3-40 carbon atoms.

40. The light-emitting device according to claim 37, wherein the compound represented by the formula (1) is also contained in a layer which is in contact with the light-emitting layer.

41. The light-emitting device according to claim 37, which is an organic electroluminescence device.

42. A film containing a delayed fluorescence emitter and a compound represented by the following formula (1):

43. The film according to claim 42, wherein Ar¹ and Ar² are each independently a substituted or unsubstituted phenyl group.

44. The film according to claim 42, wherein R¹ to R⁴ are each independently an alkyl group having 1-20 carbon atoms, an aryl group having 6-40 carbon atoms, a heteroaryl group having 3-40 carbon atoms, an alkoxy group having 1-20 carbon atoms, an aryloxy group having 6-40 carbon atoms, or a heteroaryloxy group having 3-40 carbon atoms.

45. The film according to claim 42, further containing an emitter.

46. The film according to claim 42, wherein the delayed fluorescence emitter has a benzene ring substituted with at least one cyano group and at least one electron-donating group.

47. The film according to claim 42, wherein the delayed fluorescence emitter has a benzene ring substituted with at least one cyano group and at least one diarylamino group.

48. The film according to claim 47, wherein the two aryl groups of the diarylamino group are bonded to each other to form a ring.

49. The film according to claim 42, which can emit a light by injection of holes and electrons from opposing surfaces of the film.

50. The film according to claim 42, which can emit a light by irradiation of an excitation light.

51. The film according to claim 42 as a light-emitting layer.

52. The film according to claim 42, which emits a delayed fluorescent light.