Compositions comprising organic and organometallic compounds, and their applications in organic electroluminescence, light emission, display, and illumination devices
View Patent ↗An object of the present invention is to provide an organic electroluminescence device having excellent light emission efficiency and durability, in particular, durability when driving at a high temperature. Provided is an organic electroluminescence device including on a substrate a pair of electrodes, and at least one layer of an organic layer including a light emitting layer containing a light emitting material disposed between the electrodes, wherein the light emitting layer includes at least each one of specific indolocarbazole derivatives and specific condensed ring metal complexes.
1. An organic electroluminescence device, comprising on a substrate: a pair of electrodes; at least one layer of an organic layer including a light emitting layer containing a light emitting material disposed between the electrodes, wherein the light emitting layer contains at least each one of a compound represented by the following Formula (3) and a compound represented by the following Formula (D-5):
Z 3 —(Y 3 ) n 3 (3)
wherein Z 3 represents benzene, or biphenyl and may be further substituted by at least one group selected from the group consisting of an alkyl group, an aryl group, a silyl group, a cyano group, a fluorine atom and a combination thereof; Y 3 represents a group represented by the following Formula (15a); and n 3 represents an integer of 2:
wherein R 155 represents a hydrogen atom; each of R 154 and R 156 independently represents a hydrogen atom, an alkyl group, a silyl group, a fluorine atom, a cyano group or a trifluoromethyl group, and these groups may be further substituted with at least one of an alkyl group having 1 to 6 carbon atoms and a phenyl group; R 157 represents a benzene ring, a naphthalene ring, a pyridine ring, a triazine ring or a pyrimidine ring, and these rings may be further substituted with at least one group selected from a methyl group, an isobutyl group, a t-butyl group, a neopentyl group, a phenyl group, a naphthyl group, a cyano group and a fluorine atom; and * represents a bond for linking to Z 3 :
wherein each of R 3 to R 10 independently represents a hydrogen atom, an alkyl group or an aryl group; each of R 3 ′ to R 6 ′ represents a hydrogen atom, an alkyl group or an aryl group; and each of R y independently represents a hydrogen atom, an alkyl group, a perfluoroalkyl group, a halogen atom or an aryl group;
wherein the compound of formula (D-5) is selected from the group consisting of:
2. The organic electroluminescence device according to claim 1 , wherein the compound represented by Formula (3) is represented by the following Formula (5):
wherein each of R 51 to R 56 independently represents a hydrogen atom, a methyl group, an isobutyl group, a t-butyl group, a neopentyl group, a phenyl group, a naphthyl group, a cyano group, a fluorine atom or a group represented by the following Formula (10):
wherein R 102 represents a hydrogen atom; each of R 101 and R 103 independently represents a hydrogen atom, an alkyl group, a silyl group, a fluorine atom, a cyano group or a trifluoromethyl group, and these groups may be further substituted by at least one of an alkyl group having 1 to 6carbon atoms and a phenyl group; and R 104 represents a benzene ring, a naphthalene ring, a pyridine ring, a triazine ring or a pyrimidine ring, and these rings may be further substituted by at least one group selected from the group consisting of a methyl group, an isobutyl group, a t-butyl group, a neopentyl group, a phenyl group, a naphthyl group, a cyano group and a fluorine atom.
3. The organic electroluminescence device according to claim 1 , wherein the compound represented by Formula (3) is represented by the following Formula (6):
wherein each of R 61 to R 610 independently represents a hydrogen atom, a methyl group, an isobutyl group, a t-butyl group, a neopentyl group, a phenyl group, a naphthyl group, a cyano group, a fluorine atom or a group represented by the following Formula (10), provided that each of at least two of R 61 to R 610 is independently a group represented by the following Formula (10):
wherein R 102 represents a hydrogen atom; each of R 101 and R 103 independently represents a hydrogen atom, an alkyl group, a silyl group, a fluorine atom, a cyano group or a trifluoromethyl group, and these groups may be further substituted by at least one of an alkyl group having 1 to 6carbon atoms and a phenyl group; and R 104 represents a benzene ring, a naphthalene ring, a pyridine ring, a triazine ring or a pyrimidine ring, and these rings may be further substituted by at least one group selected from the group consisting of a methyl group, an isobutyl group, a t-butyl group, a neopentyl group, a phenyl group, a naphthyl group, a cyano group and a fluorine atom.
4. The organic electroluminescence device according to claim 3 , wherein the compound represented by Formula (6) is represented by the following Formula (7):
wherein each of R 71 to R 78 independently represents a hydrogen atom, a methyl group, an isobutyl group, a t-butyl group, a neopentyl group, a phenyl group, a naphthyl group, a cyano group, or a fluorine atom; and
each of Y 71 and Y 72 is independently a group represented by the following Formula (10):
wherein R 102 represents a hydrogen atom; each of R 101 and R 103 independently represents a hydrogen atom, an alkyl group, a silyl group, a fluorine atom, a cyano group or a trifluoromethyl group, and these groups may be further substituted by at least one of an alkyl group having 1 to 6carbon atoms and a phenyl group; and R 104 represents a benzene ring, a naphthalene ring, a pyridine ring, a triazine ring or a pyrimidine ring, and these rings may be further substituted by at least one group selected from the group consisting of a methyl group, an isobutyl group, a t-butyl group, a neopentyl group, a phenyl group, a naphthyl group, a cyano group and a fluorine atom.
5. The organic electroluminescence device according to claim 3 , wherein the compound represented by Formula (6) is represented by the following Formula (8):
wherein each of R 81 to R 88 independently represents a hydrogen atom, a methyl group, an isobutyl group, a t-butyl group, a neopentyl group, a phenyl group, a naphthyl group, a cyano group, or a fluorine atom; and each of Y 81 and Y 82 is independently a group represented by the following Formula (10):
wherein R 102 represents a hydrogen atom; each of R 101 and R 103 independently represents a hydrogen atom, an alkyl group, a silyl group, a fluorine atom, a cyano group or a trifluoromethyl group, and these groups may be further substituted by at least one of an alkyl group having 1 to 6carbon atoms and a phenyl group; and R 104 represents a benzene ring, a naphthalene ring, a pyridine ring, a triazine ring or a pyrimidine ring, and these rings may be further substituted by at least one group selected from the group consisting of a methyl group, an isobutyl group, a t-butyl group, a neopentyl group, a phenyl group, a naphthyl group, a cyano group and a fluorine atom.
6. The organic electroluminescence device according to claim 1 , wherein the light emitting layer containing at least each one of the compound represented by Formula (3) and the compound represented by Formula (D-5) is formed by a wet process.
7. A light emission apparatus including the organic electroluminescence device according to claim 1 .
8. A display apparatus including the organic electroluminescence device according to claim 1 .
9. An illumination apparatus including the organic electroluminescence device according to claim 1 .
10. The organic electroluminescence device of claim 1 , wherein the compound of Formula (15a) is selected from the group consisting of:
11. A composition, comprising: at least each one of a compound represented by the following Formula (3) and a compound represented by the following Formula (D-5):
Z 3 —(Y 3 ) n 3 (3)
wherein Z 3 represents benzene, or biphenyl, and may be further substituted by at least one group selected from the group consisting of an alkyl group, an aryl group, a silyl group, a cyano group, a fluorine atom and a combination thereof; Y 3 represents a group represented by the following Formula (15a); and n 3 represents an integer of 2:
wherein R 155 represents a hydrogen atom; each of R 154 and R 156 independently represents a hydrogen atom, an alkyl group, a silyl group, a fluorine atom, a cyano group or a trifluoromethyl group, and these groups may be further substituted with at least one of an alkyl group having 1 to 6 carbon atoms and a phenyl group; R 157 represents a benzene ring, a naphthalene ring, a pyridine ring, a triazine ring or a pyrimidine ring, and these rings may be further substituted with at least one group selected from a methyl group, an isobutyl group, a t-butyl group, a neopentyl group, a phenyl group, a naphthyl group, a cyano group and a fluorine atom; and * represents a bond for linking to Z 3 :
wherein each of R 3 to R 10 independently represents a hydrogen atom, an alkyl group or an aryl group; each of R 3 ′ to R 6 ′ represents a hydrogen atom, an alkyl group or an aryl group; wherein each of R y independently represents a hydrogen atom, an alkyl group, a perfluoroalkyl group, a halogen atom or an aryl group;
wherein the compound of formula (D-5) is selected from the group consisting of:
12. A light emitting layer, comprising: at least each one of a compound represented by the following Formula (3) and a compound represented by the following Formula (D-5):
Z 3 —(Y 3 ) n 3 (3)
wherein Z 3 represents benzene, or biphenyl and may be further substituted by at least one group selected from the group consisting of an alkyl group, an aryl group, a silyl group, a cyano group, a fluorine atom and a combination thereof; Y 3 represents a group represented by the following Formula (15a); and n 3 represents an integer of 2:
wherein R 155 represents a hydrogen atom; each of R 154 and R 156 independently represents a hydrogen atom, an alkyl group, a silyl group, a fluorine atom, a cyano group or a trifluoromethyl group, and these groups may be further substituted with at least one of an alkyl group having 1 to 6 carbon atoms and a phenyl group; R 157 represents a benzene ring, a naphthalene ring, a pyridine ring, a triazine ring or a pyrimidine ring, and these rings may be further substituted with at least one group selected from a methyl group, an isobutyl group, a t-butyl group, a neopentyl group, a phenyl group, a naphthyl group, a cyano group and a fluorine atom; and represents a bond for linking to Z 3 :
wherein each of R 3 to R 10 independently represents a hydrogen atom, an alkyl group or an aryl group; R 3 ′ to R 6 ′ represents a hydrogen atom, an alkyl group or an aryl group; wherein each of R y independently represents a hydrogen atom, an alkyl group, a perfluoroalkyl group, a halogen atom or an aryl group
wherein the compound of formula (D-5) is selected from the group consisting of: