Organic Electroluminescence Device
AssigneeUDC Ireland Limited
InventorEiji Fukuzaki
Life of this patent
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Abstract
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.
Claims21
An organic electroluminescence device, comprising on a substrate:
- a pair of electrodes;
- and
- at least one organic light emitting layer 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-1):
- Z3Y3)n 3 (3)
- wherein Z3 represents benzene, pyridine, triazine, pyrimidine, biphenyl, phenylpyridine, bipyridine, a silicon atom or a carbon atom, 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;
- Y3 represents a group represented by the following Formula (3a-1) or (3a-2);
- and
- n3 represents an integer of 1 to 4:
- in Formulas (3a-1) and (3a-2), the ring A represents an aromatic ring or a heterocyclic ring, represented by Formula (3b), which is condensed with an adjacent ring;
- the ring B represents a heterocyclic ring represented by Formula (3c), which is condensed with an adjacent ring;
- X3 represents C—R″ in which R″ represents a hydrogen atom or a substituent, or a nitrogen atom;
- each of R34 and R311 independently 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;
- R33 represents a hydrogen atom;
- each of R31 and R32 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 6 carbon atoms and a phenyl group;
- and
- * represents a bond for linking to Z3;
- in Formula (D-1), M represents iridium;
- each of R3 to R6 independently represents a hydrogen atom, an alkyl group or an aryl group;
- R3′ represents a hydrogen atom, an alkyl group or an aryl group;
- the ring Q represents a pyridine ring, a quinoline ring or an isoquinoline ring, which is coordinated to iridium, and may be further substituted by an alkyl group or an aryl group;
- R5 represents an aryl group or a heteroaryl group when the ring Q is a pyridine ring, and the aryl group or the heteroaryl group may be further substituted by an alkyl group;
- R3′ and R6 may be linked to each other by a linking group selected from the group consisting of —CR2—CR2—, —CR═CR—, —CR2—, —O—, —NR—, —O—CR2—, —NR—CR2— and —N═CR— to form a ring;
- each R independently represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group or a heteroaryl group, and may further have a substituent selected from the group consisting of a halogen atom, —R′, —OR′, —N(R′)2, —SR′, —C(O)R′, —C(O)OR′, —C(O)N(R′)2, —CN, —NO2, —SO2, —SOR′, —SO2R′ and —SO3R′;
- each R′ independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, an aryl group or a heteroaryl group;
- (X—Y) represents a ligand represented by any one of the following Formula (1-1), (1-4) and (1-15);
- m represents an integer of 1 to 3;
- and
- n represents an integer of 0 to 2, provided that m+n is 3:
- in Formulas (1-1), (1-4) and (1-15), each of Rx, Ry and Rz independently represents a hydrogen atom, an alkyl group, a perfluoroalkyl group, a halogen atom or an aryl group.
-10. (canceled)
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):
- Z3Y3)n 3 (3)
- wherein Z3 represents benzene, pyridine, triazine, pyrimidine, biphenyl, phenylpyridine, bipyridine, a silicon atom or a carbon atom, 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;
- Y3 represents a group represented by the following Formula (3a-1) or (3a-2);
- and
- n3 represents an integer of 1 to 4:
- in Formulas (3a-1) and (3a-2), the ring A represents an aromatic ring or a heterocyclic ring, represented by Formula (3b), which is condensed with an adjacent ring;
- the ring B represents a heterocyclic ring represented by Formula (3c), which is condensed with an adjacent ring;
- X3 represents C—R″ in which R″ represents a hydrogen atom or a substituent, or a nitrogen atom;
- each of R34 and R311 independently 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;
- R33 represents a hydrogen atom;
- each of R31 and R32 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 6 carbon atoms and a phenyl group;
- and
- * represents a bond for linking to Z3
- in Formula (D-1), M represents iridium;
- each of R3 to R6 independently represents a hydrogen atom, an alkyl group or an aryl group;
- R3′ represents a hydrogen atom, an alkyl group or an aryl group;
- the ring Q represents a pyridine ring, a quinoline ring or an isoquinoline ring, which is coordinated to iridium, and may be further substituted by an alkyl group or an aryl group;
- R5 represents an aryl group or a heteroaryl group when the ring Q is a pyridine ring, and the aryl group or the heteroaryl group may be further substituted by an alkyl group;
- R3′ and R6 may be linked to each other by a linking group selected from the group consisting of —CR2—CR2—, —CR═CR—, —CR2—, —O—, —NR—, —O—CR2—, —NR—CR2— and —N═CR— to form a ring;
- each R independently represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group or a heteroaryl group, and may further have a substituent selected from the group consisting of a halogen atom, —R′, —OR′, —N(R′)2, —SR′, —C(O)R′, —C(O)OR′, —C(O)N(R′)2, —CN, —NO2, —SO2, —SOR′, —SO2R′ and —SO3R′;
- each R′ independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, an aryl group or a heteroaryl group;
- (X—Y) represents a ligand represented by any one of the following Formula (1-1), (1-4) and (1-15);
- m represents an integer of 1 to 3;
- and
- n represents an integer of 0 to 2, provided that m+n is 3:
- in Formulas (1-1), (1-4) and (1-15), each of Rx, Ry and Rz independently represents a hydrogen atom, an alkyl group, a perfluoroalkyl group, a halogen atom or an aryl group.
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):
- Z3Y3)n 3 (3)
- wherein Z3 represents benzene, pyridine, triazine, pyrimidine, biphenyl, phenylpyridine, bipyridine, a silicon atom or a carbon atom, 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;
- Y3 represents a group represented by the following Formula (3a-1) or (3a-2);
- and
- n3 represents an integer of 1 to 4:
- in Formulas (3a-1) and (3a-2), the ring A represents an aromatic ring or a heterocyclic ring, represented by Formula (3b), which is condensed with an adjacent ring;
- the ring B represents a heterocyclic ring represented by Formula (3c), which is condensed with an adjacent ring;
- X3 represents C—R″ in which R″ represents a hydrogen atom or a substituent, or a nitrogen atom;
- each of R34 and R311 independently 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;
- R33 represents a hydrogen atom;
- each of R31 and R32 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 6 carbon atoms and a phenyl group;
- and
- * represents a bond for linking to Z3
- in Formula (D-1), M represents iridium;
- each of R3 to R6 independently represents a hydrogen atom, an alkyl group or an aryl group;
- R3′ represents a hydrogen atom, an alkyl group or an aryl group;
- the ring Q represents a pyridine ring, a quinoline ring or an isoquinoline ring, which is coordinated to iridium, and may be further substituted by an alkyl group or an aryl group;
- R5 represents an aryl group or a heteroaryl group when the ring Q is a pyridine ring, and the aryl group or the heteroaryl group may be further substituted by an alkyl group;
- R3′ and R6 may be linked to each other by a linking group selected from the group consisting of —CR2—CR2—, —CR═CR—, —CR2—, —O—, —NR—, —O—CR2—, —NR—CR2— and —N═CR— to form a ring;
- each R independently represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group or a heteroaryl group, and may further have a substituent selected from the group consisting of a halogen atom, —R′, —OR′, —N(R′)2, —SR′, —C(O)R′, —C(O)OR′, —C(O)N(R′)2, —CN, —NO2, —SO2, —SOR′, —SO2R′ and —SO3R′;
- each R′ independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, an aryl group or a heteroaryl group;
- (X—Y) represents a ligand represented by any one of the following Formula (1-1), (1-4) and (1-15);
- m represents an integer of 1 to 3;
- and
- n represents an integer of 0 to 2, provided that m+n is 3:
- in Formulas (1-1), (1-4) and (1-15), each of Rx, Ry and Rz independently represents a hydrogen atom, an alkyl group, a perfluoroalkyl group, a halogen atom or an aryl group.
Dependencies are inferred from the claim text.