Phenanthrocarbazole compound, and organic electroluminescent device using same
View Patent ↗The present invention relates to a material for an organic electroluminescent device, including a phenanthrocarbazole-based compound having a specific structure, and an organic electroluminescent device including the same. More specifically, the phenanthrocarbazole-based compound is applied as a material for a phosphorescent and fluorescent organic electroluminescent device, thereby providing an organic light emitting device with improved light emitting efficiency, luminance, thermal stability, driving voltage, lifetime and the like.
1. A material for an organic electroluminescent device represented by the following Chemical Formula 1:
wherein,
Ar is an aromatic hydrocarbon ring group or an aromatic amine ring group, and selected from the group consisting of benzene, naphthalene, biphenyl, anthracene, phenanthrene, pyrene, perylene, triphenylene, and triphenyl amine,
R 1 to R 14 are each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, an alkyl group having 1 to 40 carbon atoms, a hetero-ring group having 3 to 40 nucleus atoms, an alkoxy group having 1 to 40 carbon atoms, an aromatic hydrocarbon group having 6 to 40 nucleus carbon atoms, an aryloxy group having 6 to 40 carbon atoms, an arylalkyl group having 7 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an alkylamino group having 1 to 40 carbon atoms, an arylamino group having 6 to 40 carbon atoms, an arylalkylamino group having 7 to 40 carbon atoms, an alkylsilyl group having 3 to 20 carbon atoms, an arylsilyl group having 8 to 40 carbon atoms, a ketoaryl group having 7 to 40 carbon atoms, a halogenated alkyl group having 1 to 40 carbon atoms, and a cyano group,
R 1 to R 14 may each independently bind with adjacent substituents, or the substituents introduced to Ar may each independently bind with adjacent substituents to form a saturated or unsaturated ring structure.
2. A material for an organic electroluminescent device represented by the following Chemical Formula 2:
wherein,
Ar 1 and Ar 2 may be the same as or different from each other, and are each independently selected from the group consisting of benzene, naphthalene, biphenyl, anthracene, phenanthrene, pyrene, perylene, and triphenylene, and in Ar 1 and Ar 2 , the adjacent substituents may be bonded to each other to form a saturated or unsaturated ring structure,
R 1 to R 14 are each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, an alkyl group having 1 to 40 carbon atoms, a hetero-ring group having 3 to 40 nucleus atoms, an alkoxy group having 1 to 40 carbon atoms, an aromatic hydrocarbon group having 6 to 40 nucleus carbon atoms, an aryloxy group having 6 to 40 carbon atoms, an arylalkyl group having 7 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an alkylamino group having 1 to 40 carbon atoms, an arylamino group having 6 to 40 carbon atoms, an arylalkylamino group having 7 to 40 carbon atoms, an alkylsilyl group having 3 to 20 carbon atoms, an arylsilyl group having 8 to 40 carbon atoms, a ketoaryl group having 7 to 40 carbon atoms, a halogenated alkyl group having 1 to 40 carbon atoms, and a cyano group, and
R 1 to R 4 , R 5 to R 8 , R 9 to R 12 , and R 13 to R 14 may each independently bind with adjacent substituents, or R 12 and R 13 may be bonded to each other to form a saturated or unsaturated ring structure.
3. A material for an organic electroluminescent device represented by the following Chemical Formula 3:
wherein,
R 1 to R19 are each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, an alkyl group having 1 to 40 carbon atoms, a hetero-ring group having 3 to 40 nucleus atoms, an alkoxy group having 1 to 40 carbon atoms, an aromatic hydrocarbon group having 6 to 40 nucleus carbon atoms, an aryloxy group having 6 to 40 carbon atoms, an arylalkyl group having 7 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an alkylamino group having 1 to 40 carbon atoms, an arylamino group having 6 to 40 carbon atoms, an arylalkylamino group having 7 to 40 carbon atoms, an alkylsilyl group having 3 to 20 carbon atoms, an arylsilyl group having 8 to 40 carbon atoms, a ketoaryl group having 7 to 40 carbon atoms, a halogenated alkyl group having 1 to 40 carbon atoms, and a cyano group, and
R 7 to R 8 , R 8 to R 13 , and R 8 to R 12 may each independently bind with adjacent substituents to form a saturated or unsaturated ring structure.
4. A material for an organic electroluminescent device represented by the following Chemical Formula 4:
wherein,
R 1 to R 15 are each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, an alkyl group having 1 to 40 carbon atoms, a hetero-ring group having 3 to 40 nucleus atoms, an alkoxy group having 1 to 40 carbon atoms, an aromatic hydrocarbon group having 6 to 40 nucleus carbon atoms, an aryloxy group having 6 to 40 carbon atoms, an arylalkyl group having 7 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an alkylamino group having 1 to 40 carbon atoms, an arylamino group having 6 to 40 carbon atoms, an arylalkylamino group having 7 to 40 carbon atoms, an alkylsilyl group having 3 to 20 carbon atoms, an arylsilyl group having 8 to 40 carbon atoms, a ketoaryl group having 7 to 40 carbon atoms, a halogenated alkyl group having 1 to 40 carbon atoms, and a cyano group, and
a plurality of Zs are each independent and may be the same as or different from each other even though the plurality of Zs are identically represented, and at least one of the plurality of Zs is a nitrogen atom and others are a carbon atom.
5. An organic light emitting device comprising:
an anode;
a cathode; and
one or more organic layers interposed between the anode and the cathode,
wherein at least one of the organic layers comprises one or more compounds selected from the group consisting of a compound represented by the following Chemical Formula 1, a compound represented by the following Chemical Formula 2, a compound represented by the following Chemical Formula 3, and a compound represented by the following Chemical Formula 4:
wherein,
Ar is an aromatic hydrocarbon ring group or an aromatic amine ring group, and selected from the group consisting of benzene, naphthalene, biphenyl, anthracene, phenanthrene, pyrene, perylene, triphenylene, and triphenyl amine;
R 1 to R 14 are each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, an alkyl group having 1 to 40 carbon atoms, a hetero-ring group having 3 to 40 nucleus atoms, an alkoxy group having 1 to 40 carbon atoms, an aromatic hydrocarbon group having 6 to 40 nucleus carbon atoms, an aryloxy group having 6 to 40 carbon atoms, an arylalkyl group having 7 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an alkylamino group having 1 to 40 carbon atoms, an arylamino group having 6 to 40 carbon atoms, an arylalkylamino group having 7 to 40 carbon atoms, an alkylsilyl group having 3 to 20 carbon atoms, an arylsilyl group having 8 to 40 carbon atoms, a ketoaryl group having 7 to 40 carbon atoms, a halogenated alkyl group having 1 to 40 carbon atoms, and a cyano group, and
R 1 to R 14 may each independently bind with adjacent substituents, or the substituents introduced to Ar may each independently bind with adjacent substituents to form a saturated or unsaturated ring structure;
wherein,
Ar 1 and Ar 2 may be the same as or different from each other, and are each independently selected from the group consisting of benzene, naphthalene, biphenyl, anthracene, phenanthrene, pyrene, perylene, and triphenylene, and Ar 1 and Ar 2 may each independently bind with the adjacent substituents to form a saturated or unsaturated ring structure,
R 1 to R 14 are the same as definitions of Chemical Formula 1;
R 1 to R 4 , R 5 to R 8 , R 9 to R 12 , and R 13 to R 14 may each independently bind with adjacent substituents, or R 12 and R 13 may be bonded to each other to form a saturated or unsaturated ring structure;
wherein,
R 1 to R 19 are the same as definitions of R 1 to R 14 of Chemical Formula 1;
R 7 to R 8 , R 8 to R 13 , and R 8 to R 12 may each independently bind with adjacent substituents to form a saturated or unsaturated ring structure;
wherein,
R 1 to R 15 are the same as definitions of R 1 to R 14 of Chemical Formula 1; and
a plurality of Zs are each independent and may be the same as or different from each other even though the plurality of Zs are identically represented, and at least one of the plurality of Zs is a nitrogen atom and others are a carbon atom.
6. The organic light emitting device of claim 5 , wherein the compound is included in one or more organic layers selected from the group consisting of a light emitting layer, a hole injection layer, and a hole transport layer.