WO2019107932A1 - Compound and organic light emitting device comprising same - Google Patents
Compound and organic light emitting device comprising same Download PDFInfo
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- WO2019107932A1 WO2019107932A1 PCT/KR2018/014859 KR2018014859W WO2019107932A1 WO 2019107932 A1 WO2019107932 A1 WO 2019107932A1 KR 2018014859 W KR2018014859 W KR 2018014859W WO 2019107932 A1 WO2019107932 A1 WO 2019107932A1
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- substituted
- compound
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- light emitting
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- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
Definitions
- the present invention relates to a compound and an organic light emitting device including the same.
- thermally activated delayed fluorescence is a phenomenon in which the inverse energy transfer from the excited triplet state to the excited singlet state is caused by thermal activation, leading to fluorescence emission.
- thermally activated delayed fluorescence is a phenomenon in which the inverse energy transfer from the excited triplet state to the excited singlet state is caused by thermal activation, leading to fluorescence emission.
- the lifetime It is called delayed fluorescence in that long luminescence occurs. Since the retardation fluorescent material can use both fluorescence emission and phosphorescence emission, the problem of the cost of the phosphorescent material can be solved in that the problem of the external quantum efficiency of the conventional fluorescent material can be solved and the metal complex is not required.
- the present invention provides a compound and an organic light emitting device comprising the same.
- A1 to A5 are the same or different from each other, and each independently hydrogen; A halogen group; Cyano; Haloalkyl; An alkyl group; An alkenyl group; A haloalkoxy group; An aryl group substituted or unsubstituted with a halogen group, a cyano group, a haloalkyl group, an alkyl group, or a haloalkoxy group; Or a heteroaryl group, or adjacent groups are bonded to each other to form an aromatic ring,
- R1 to R8 and R11 to R18 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubsti
- n 1 or 2
- n 2
- the structures in the plurality of parentheses are equal to or different from each other
- n is 1, and any one of A1 to A5 is a heteroaryl group, the remainder is hydrogen.
- a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound described above.
- the organic light emitting device including the compound represented by Chemical Formula 1 according to one embodiment of the present invention can improve the efficiency, improve the driving voltage and / or the lifetime characteristics.
- FIG 1 shows an organic light emitting device according to an embodiment of the present invention.
- the compound represented by the formula (1) combines two cyano groups at the para position with a benzene core as a center, so that the organic light emitting device emitting light in a specific wavelength range, .
- the charge balance injected into the light emitting layer is controlled, and the organic light emitting device including the benzene core has low driving voltage, The life can be improved.
- substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.
- substituted or unsubstituted A halogen group; Cyano; A nitro group; Imide; Amide group; Carbonyl group; An ester group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or
- a substituent to which at least two substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.
- the halogen group may be fluorine, chlorine, bromine or iodine.
- the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
- the amide group may be substituted with nitrogen of the amide group by hydrogen, a straight chain, branched chain or cyclic alkyl group of 1 to 30 carbon atoms or an aryl group of 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
- the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
- the ester group may be substituted with an ester group oxygen in a straight chain, branched chain or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms.
- it may be a compound of the following structural formula, but is not limited thereto.
- the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
- Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methyl
- the cycloalkyl group is not particularly limited, but is preferably a group having 3 to 30 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, isobutyl, sec-butyl, It is not.
- the alkoxy group may be linear, branched or cyclic.
- the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n Butyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like. But is not limited thereto.
- the amine group is -NH 2 ; An alkylamine group; N-alkylarylamine groups; An arylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
- amine group examples include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, Phenylnaphthylenediamine group, N-phenylphenylenediamine group, N-phenyltriphenylamine group, N-phenylphenanthrenylamine group, N-phenylphenanthrenylamine group, Group, an N-phenanthrenylfluorenylamine group, and an N-biphenylfluorenylamine group, but the present invention is not limited thereto.
- the N-alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group.
- the N-arylheteroarylamine group means an amine group in which N in the amine group is substituted with an aryl group and a heteroaryl group.
- the N-alkylheteroarylamine group means an amine group in which N in the amine group is substituted with an alkyl group and a heteroaryl group.
- the alkyl group in the alkylamine group, the N-arylalkylamine group, the alkylthio group, the alkylsulfoxy group and the N-alkylheteroarylamine group is the same as the alkyl group described above.
- Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group.
- Examples of the alkylsulfoxy group include a methylsulfoxy group, an ethylsulfoxy group, a propylsulfoxy group, And the like, but the present invention is not limited thereto.
- the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30.
- Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.
- the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group,
- the present invention is not limited thereto.
- the boron group may be -BR 100 R 101 , wherein R 100 and R 101 are the same or different and each independently hydrogen; heavy hydrogen; halogen; Cyano; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
- the phosphine oxide group specifically includes a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, and the like, but is not limited thereto.
- the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
- the aryl group is a monocyclic aryl group
- the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms.
- Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.
- the aryl group is a polycyclic aryl group
- the number of carbon atoms is not particularly limited. And preferably 10 to 30 carbon atoms.
- Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, triphenyl, pyrenyl, phenalenyl, perylenyl, , But is not limited thereto.
- the fluorenyl group may be substituted, and adjacent groups may combine with each other to form a ring.
- adjacent means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom .
- two substituents substituted in the benzene ring to the ortho position and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.
- the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the N-arylalkylamine group, the N-arylheteroarylamine group and the arylphosphine group is the same as the aforementioned aryl group.
- aryloxy group examples include a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6- trimethylphenoxy group, a p- Naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group and 9-phenanthryloxy group and the arylthioxy group includes phenylthio group, 2- Methylphenylthio group, 4-tert-butylphenylthio group and the like, and examples of the arylsulfoxy group include a benzene sulfoxide group and a p-toluenesulfoxy group.
- the present invention is not limited thereto.
- examples of the arylamine group include a substituted or unsubstituted monoarylamine group, or a substituted or unsubstituted diarylamine group.
- the aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group.
- the arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.
- the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
- the heteroaryl group includes at least one non-carbon atom and at least one hetero atom.
- the hetero atom may include one or more atoms selected from the group consisting of O, N, Se and S, and the like.
- the number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic.
- heterocyclic group examples include a thiophene group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic
- examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group.
- the heteroarylamine group having two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time.
- the heteroaryl group in the heteroarylamine group may be selected from the examples of the above-mentioned heteroaryl group.
- heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the above-mentioned heteroaryl group.
- the "ring” means a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.
- the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from the examples of the cycloalkyl group or the aryl group except the univalent hydrocarbon ring.
- the aromatic ring may be monocyclic or polycyclic and may be selected from the examples of the aryl group except that it is not monovalent.
- the hetero ring includes one or more non-carbon atoms and hetero atoms.
- the hetero atom may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like.
- the heterocyclic ring may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and examples thereof may be selected from the heteroaryl group or the heterocyclic group except that the monocyclic group is not monovalent.
- the formula (1) is represented by the following formula (1-1) or (1-2).
- A11 to A15 are the same or different and each independently hydrogen; A halogen group; Cyano; Haloalkyl; An alkyl group; An alkenyl group; A haloalkoxy group; An aryl group substituted or unsubstituted with a halogen group, a cyano group, a haloalkyl group, an alkyl group, or a haloalkoxy group; Or a heteroaryl group, or adjacent groups are bonded to each other to form an aromatic ring.
- R 1 to R 8 and R 11 to R 18 are the same or different and each independently hydrogen; Or a substituted or unsubstituted alkyl group.
- R 1 to R 8 and R 11 to R 18 are the same or different and each independently hydrogen; Or an alkyl group.
- R 1 to R 8 and R 11 to R 18 are the same or different and each independently hydrogen; Or a methyl group.
- adjacent groups among R1 to R8 and R11 to R18 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.
- adjacent groups among R1 to R8 and R11 to R18 in the formula (1) are bonded to each other to form a hydrocarbon ring substituted with at least one alkyl group.
- adjacent groups among R1 to R8 and R11 to R18 in the formula (1) are bonded to each other to form an aromatic ring substituted with at least one alkyl group.
- adjacent groups among R1 to R8 and R11 to R18 are bonded to each other to form an indene ring substituted with at least one alkyl group.
- adjacent groups among R1 to R8 and R11 to R18 in the general formula (1) are bonded to each other to form an indene ring substituted with at least one methyl group.
- R 2 and R 3 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.
- R 2 and R 3 are bonded to each other to form a hydrocarbon ring substituted with at least one alkyl group.
- R 2 and R 3 are bonded to each other to form an aromatic ring substituted with at least one alkyl group.
- R 2 and R 3 are bonded to each other to form an indene ring substituted with at least one alkyl group.
- R 2 and R 3 are bonded to each other to form an indene ring substituted with at least one methyl group.
- any one of R 2 and R 3 in the general formula (1) is a substituted or unsubstituted aryl group, and the other is a substituted or unsubstituted alkyl group; To form an unsubstituted hydrocarbon ring.
- any one of R 2 and R 3 in the general formula (1) is a substituted or unsubstituted phenyl group, and the other is a substituted or unsubstituted alkyl group; To form a ring-opened hydrocarbon ring.
- R 3 is a substituted or unsubstituted phenyl group
- R 2 is a substituted or unsubstituted alkyl group
- R 2 and R 3 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring .
- R 3 is a phenyl group
- R 2 is an isopropyl group
- R 2 and R 3 are bonded to each other to form an indene ring substituted with two methyl groups.
- R 6 and R 7 combine with each other to form a substituted or unsubstituted hydrocarbon ring.
- R 6 and R 7 are bonded to each other to form a hydrocarbon ring substituted with at least one alkyl group.
- R 6 and R 7 combine with each other to form an aromatic ring substituted with at least one alkyl group.
- R 6 and R 7 combine with each other to form an indene ring substituted with at least one alkyl group.
- R 6 and R 7 combine with each other to form an indene ring substituted with at least one methyl group.
- any one of R6 and R7 is a substituted or unsubstituted aryl group and the remaining is a substituted or unsubstituted alkyl group, and R6 and R7 are bonded to each other to form a substituted or unsubstituted To form an unsubstituted hydrocarbon ring.
- any one of R6 and R7 is a substituted or unsubstituted phenyl group and the remaining is a substituted or unsubstituted alkyl group, and R6 and R7 are bonded to each other to form a substituted or unsubstituted To form a ring-opened hydrocarbon ring.
- R6 is a substituted or unsubstituted phenyl group
- R7 is a substituted or unsubstituted alkyl group
- R6 and R7 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring .
- R6 is a phenyl group
- R7 is an isopropyl group
- R6 and R7 are bonded to each other to form an indene ring substituted with two methyl groups.
- R 12 and R 13 combine with each other to form a substituted or unsubstituted hydrocarbon ring.
- R12 and R13 in the formula (1) are bonded to each other to form a hydrocarbon ring substituted with at least one alkyl group.
- R 12 and R 13 combine with each other to form an aromatic ring substituted with at least one alkyl group.
- R12 and R13 are bonded to each other to form an indene ring substituted with at least one alkyl group.
- R 12 and R 13 combine with each other to form an indene ring substituted with at least one methyl group.
- any one of R12 and R13 is a substituted or unsubstituted aryl group and the remaining is a substituted or unsubstituted alkyl group, and R12 and R13 are bonded to each other to form a substituted or unsubstituted To form an unsubstituted hydrocarbon ring.
- any one of R12 and R13 is a substituted or unsubstituted phenyl group and the remaining is a substituted or unsubstituted alkyl group, and R12 and R13 are bonded to each other to be substituted or to be substituted To form a ring-opened hydrocarbon ring.
- R13 is a substituted or unsubstituted phenyl group
- R12 is a substituted or unsubstituted alkyl group
- R12 and R13 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring .
- R13 is a phenyl group
- R12 is an isopropyl group
- R12 and R13 are bonded to each other to form an indene ring substituted with two methyl groups.
- R16 and R17 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.
- R16 and R17 are bonded to each other to form a hydrocarbon ring substituted with at least one alkyl group.
- R16 and R17 are bonded to each other to form an aromatic ring substituted with at least one alkyl group.
- R16 and R17 are bonded to each other to form an indene ring substituted with at least one alkyl group.
- R16 and R17 are bonded to each other to form an indene ring substituted with at least one methyl group.
- any one of R16 and R17 is a substituted or unsubstituted aryl group and the remaining is a substituted or unsubstituted alkyl group, and R16 and R17 are bonded to each other to form a substituted or unsubstituted To form an unsubstituted hydrocarbon ring.
- any one of R16 and R17 is a substituted or unsubstituted phenyl group and the remaining is a substituted or unsubstituted alkyl group, and R16 and R17 are bonded to each other to be substituted or to be substituted To form a ring-opened hydrocarbon ring.
- R16 is a substituted or unsubstituted phenyl group
- R17 is a substituted or unsubstituted alkyl group
- R16 and R17 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring .
- R16 is a phenyl group
- R17 is an isopropyl group
- R16 and R17 are bonded to each other to form an indene ring substituted with two methyl groups.
- A1 to A5 and A11 to A15 are the same or different from each other, and each independently hydrogen; A halogen group; Cyano; Haloalkyl; An alkyl group; An alkenyl group; A haloalkoxy group; An aryl group substituted or unsubstituted with a halogen group, a cyano group, a haloalkyl group, an alkyl group, or a haloalkoxy group; Or a heteroaryl group.
- A1 to A5 and A11 to A15 are the same or different from each other, and each independently hydrogen; Fluorine; Cyano; A trifluoromethyl group; Methyl group; Isopropyl group; t-butyl group; A trifluoromethoxy group; An aryl group which is substituted or unsubstituted with a fluorine atom, a cyano group, a trifluoromethyl group, a methyl group, or a trifluoromethoxy group; Or a polycyclic heteroaryl group.
- A1 to A5 and A11 to A15 are the same or different from each other, and each independently hydrogen; Fluorine; Cyano; A trifluoromethyl group; Methyl group; Isopropyl group; t-butyl group; A trifluoromethoxy group; A phenyl group substituted or unsubstituted by fluorine, a cyano group, a trifluoromethyl group, a methyl group, or a trifluoromethoxy group; Or a carbazolyl group.
- adjacent groups of A1 to A5 are bonded to each other to form an aromatic ring.
- adjacent groups of A1 to A5 combine with each other to form a benzene ring.
- adjacent groups among A11 to A15 are bonded to each other to form an aromatic ring.
- adjacent groups among A11 to A15 are bonded to each other to form a benzene ring.
- a 1 and A 5 combine with each other to form an aromatic ring.
- a 1 and A 5 combine with each other to form a benzene ring.
- A1 and A5 are each a substituted or unsubstituted alkenyl group, and combine with each other to form a substituted or unsubstituted benzene ring.
- A1 and A5 are each ethenyl and combine with each other to form a benzene ring.
- A2 and A3 combine with each other to form an aromatic ring.
- A2 and A3 combine with each other to form a benzene ring.
- A2 and A3 are each a substituted or unsubstituted alkenyl group, and combine with each other to form a substituted or unsubstituted benzene ring.
- A2 and A3 are each an ethenyl and combine with each other to form a benzene ring.
- A3 and A4 are bonded to each other to form an aromatic ring.
- A3 and A4 are bonded to each other to form a benzene ring.
- A3 and A4 are each a substituted or unsubstituted alkenyl group and are bonded to each other to form a substituted or unsubstituted benzene ring.
- A3 and A4 are each an ethenyl and combine with each other to form a benzene ring.
- A4 and A5 combine with each other to form an aromatic ring.
- A4 and A5 combine with each other to form a benzene ring.
- A4 and A5 are each a substituted or unsubstituted alkenyl group and are bonded to each other to form a substituted or unsubstituted benzene ring.
- A4 and A5 are each ethenyl and combine with each other to form a benzene ring.
- A11 and A12 combine with each other to form an aromatic ring.
- A11 and A12 combine with each other to form a benzene ring.
- A11 and A12 are each a substituted or unsubstituted alkenyl group and are bonded to each other to form a substituted or unsubstituted benzene ring.
- A11 and A12 are each ethenyl and combine with each other to form a benzene ring.
- A12 and A13 are bonded to each other to form an aromatic ring.
- A12 and A13 combine with each other to form a benzene ring.
- A12 and A13 are each a substituted or unsubstituted alkenyl group, and combine with each other to form a substituted or unsubstituted benzene ring.
- A12 and A13 are each ethenyl and combine with each other to form a benzene ring.
- A13 and A14 combine with each other to form an aromatic ring.
- A13 and A14 combine with each other to form a benzene ring.
- A13 and A14 are each a substituted or unsubstituted alkenyl group, and combine with each other to form a substituted or unsubstituted benzene ring.
- A13 and A14 are each an ethenyl group and combine with each other to form a benzene ring.
- A14 and A15 combine with each other to form an aromatic ring.
- A14 and A15 combine with each other to form a benzene ring.
- A14 and A15 are each a substituted or unsubstituted alkenyl group and are bonded to each other to form a substituted or unsubstituted benzene ring.
- A14 and A15 are each ethenyl and combine with each other to form a benzene ring.
- n is 1 and either one of A1 to A5 is a polycyclic heteroaryl group in the general formula (1), the remainder is hydrogen.
- n is 1 and one of A 1 to A 5 is a carbazolyl group in the general formula (1), the other is hydrogen.
- Formula 1 is selected from the following compounds.
- the compound represented by Formula 1 is a retardation fluorescent compound.
- the number of excitons generated in the singlet and triplet is generated at a ratio of 25:75 (monomodal: triplet), and depending on the type of emission due to exciton migration, fluorescence emission, It can be divided into luminescence.
- the phosphorescent light emission it means that the exciton of the excited state moves to the ground state and emits light.
- the fluorescent emission the exciton of the excited state is in the ground state ground state, and the light is emitted.
- the thermal activation delay fluorescent light emission is induced in the excited state from the excited state to the excited state, and the singlet excited state Means that the exciton moves to the ground state to cause fluorescent light emission.
- the thermal activation delayed fluorescence emission is distinguished from fluorescence emission in that the peak position of the emission spectrum is the same as that of fluorescence but the decay time is long. The decay time is long, but the peak position of the emission spectrum differs from the phosphorescence spectrum and S 1 -T 1 < / RTI > energy difference.
- S 1 is a singlet energy level
- T 1 is a triplet energy level.
- a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound described above.
- the organic material layer of the organic light emitting device may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
- the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, and an electron injecting layer as an organic material layer.
- the structure of the organic light emitting device is not limited thereto and may include fewer or more organic layers.
- the structure of the organic light emitting device of the present invention may have a structure as shown in FIG. 1, but is not limited thereto.
- 1 illustrates a structure of an organic light emitting diode 10 in which a first electrode 30, a light emitting layer 40, and a second electrode 50 are sequentially stacked on a substrate 20.
- 1 is an exemplary structure of an organic light emitting diode according to an embodiment of the present invention, and may further include another organic layer.
- the organic layer includes a light emitting layer, and the light emitting layer includes the compound.
- the organic layer includes a light emitting layer, and the light emitting layer includes the compound as a dopant of the light emitting layer.
- the maximum emission wavelength of the dopant is 480 nm to 570 nm.
- the dopant is a green dopant.
- the light emitting material of the light emitting layer is a material capable of emitting light in a visible light region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, At least one of the excited singlet energy and the excitation triplet energy has a higher value than the light emitting material of the compound and has a hole transporting ability and an electron transporting ability and also prevents a long wavelength of light emission, And may include an organic compound having a high glass transition temperature as a host.
- the organic layer includes a light emitting layer, and the light emitting layer includes a host.
- the organic layer includes a light emitting layer, and the light emitting layer includes at least one selected from a condensed aromatic ring derivative and a heterocyclic compound as a host of the light emitting layer.
- the condensed aromatic ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a fluorene derivative, a phenanthrene compound, a fluoranthene compound, Include, but are not limited to, carbazole derivatives, dibenzofuran derivatives, ladder furan compounds, and pyrimidine derivatives.
- the host may include any one or more selected from the following compounds, but is not limited thereto.
- the organic material layer includes a light emitting layer, and the light emitting layer contains the compound represented by Formula 1 as a dopant of the light emitting layer, and at least one selected from a condensed aromatic ring derivative and a heterocyclic compound As a host of the light emitting layer.
- the light emitting layer contains the dopant and the host in a weight ratio of 1:99 to 50:50.
- the organic material layer includes a light emitting layer
- the light emitting layer may include at least one selected from the group consisting of the dopant including the compound represented by the above-mentioned formula (1), the condensed aromatic ring derivative, and the heterocyclic compound Containing host at a weight ratio of 1:99 to 50:50.
- the organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that the dopant of the light emitting layer contains the compound of the present specification, that is, the compound represented by the above formula (1).
- the organic layers may be formed of the same material or different materials.
- the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate.
- a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate by a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation Forming a first electrode, forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer on the first electrode, and depositing a material usable as a second electrode thereon.
- PVD physical vapor deposition
- an organic light emitting device can be formed by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate.
- the heterocyclic compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device.
- the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.
- the first electrode is an anode and the second electrode is a cathode.
- the first electrode is a cathode and the second electrode is a cathode.
- the cathode material a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer.
- the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.
- the negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
- Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al, LiO 2 / Al, and Mg / Ag, but are not limited thereto.
- the hole injecting layer is a layer for injecting holes from an electrode.
- the hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material.
- a compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer.
- HOMO highest occupied molecular orbital
- the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.
- the hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer.
- the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer.
- the material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
- the electron transporting layer is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer.
- the electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Do. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
- the electron transporting layer can be used with any desired cathode material as used according to the prior art.
- suitable cathode materials are conventional materials with a low work function followed by an aluminum or silver layer, specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum or silver layer.
- the electron injection layer is a layer for injecting electrons from the electrode.
- the electron injection layer has the ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material.
- a compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable.
- Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.
- Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.
- the organic light emitting device according to the present invention may be of a top emission type, a back emission type, or a both-side emission type, depending on the material used.
- the toluene layer was separated, dried over magnesium sulfate, filtered and the filtrate was distilled under reduced pressure.
- a glass substrate with a 40 mm x 40 mm x 0.5 mm thick ITO electrode was ultrasonically cleaned with isopropyl alcohol, acetone and DI water for 5 minutes, and then dried in an oven at 100 ° C. After the substrate was cleaned, it was subjected to an O 2 plasma treatment in a vacuum for 2 minutes and transferred to a deposition chamber for deposition of other layers on the top.
- An organic layer was deposited on the ITO of the glass substrate by evaporation from a heated boat under a vacuum of about 10 -7 Torr in the following order. At this time, the deposition rate of the organic material was set at 10 nm / s.
- Hole injection layer HAT-CN, thickness 10 nm
- HTL Hole transport layer
- Electron barrier layer (EBL) mCBP, thickness 15 nm
- Emissive material layer TH1 90 wt%, Compound 1 10 wt%, thickness 35 nm
- Hole blocking layer (HBL) B3PYMPM, thickness 10 nm
- Electron transport layer (ETL) TPBi, thickness 25 nm
- Electron Injection Layer LiF, thickness 80 nm
- a capping layer (CPL) was formed and encapsulated with glass. After deposition of these layers, the film was transferred from the deposition chamber into a dry box for subsequent film formation and subsequently encapsulated using a UV cured epoxy and a getter.
- An organic light emitting device was prepared using Compound 2 instead of Compound 1 as a dopant in the light emitting layer.
- An organic light emitting device was prepared using Compound 3 instead of Compound 1 as a dopant in the light emitting layer.
- An organic light emitting device was prepared using Compound 4 instead of Compound 1 as a dopant of the light emitting layer.
- An organic light emitting device was prepared using Compound 5 instead of Compound 1 as a dopant in the light emitting layer.
- An organic light emitting device was prepared by using Compound 6 instead of Compound 1 as a dopant in the light emitting layer.
- An organic light emitting device was prepared using Compound 8 instead of Compound 1 as a dopant in the light emitting layer.
- An organic light emitting device was prepared using Compound 9 instead of Compound 1 as a dopant in the light emitting layer.
- An organic light emitting device was prepared by using Compound 10 instead of Compound 1 as a dopant in the light emitting layer.
- An organic light emitting device was prepared using Compound 13 instead of Compound 1 as a dopant in the light emitting layer.
- An organic light emitting device was prepared by using Compound 14 instead of Compound 1 as a dopant of the light emitting layer.
- An organic luminescent device was prepared using the following Compound D1 instead of Compound 1 as a dopant in the light emitting layer.
- An organic luminescent device was prepared using the following compound D2 instead of compound 1 as a dopant in the light emitting layer.
- An organic light emitting device was prepared using the following compound D3 instead of Compound 1 as a dopant of the light emitting layer.
- An organic luminescent device was prepared using the following compound D4 instead of compound 1 as a dopant in the light emitting layer.
- An organic light emitting device was prepared using the following compound D5 instead of compound 1 as a dopant of the light emitting layer.
- An organic luminescent device was prepared using the following compound D6 instead of compound 1 as a dopant in the light emitting layer.
- the devices of Examples 1 to 11 using the heterocyclic compound of the present invention had lower driving voltage, higher current efficiency, higher power efficiency, higher luminance, and higher lifetime characteristics than the devices of Comparative Examples 1 to 6 .
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Abstract
The specification relates to a compound of chemical formula 1 and an organic light emitting device comprising the same.
Description
본 출원은 2017년 11월 28일에 한국특허청에 제출된 한국 특허 출원 제 10-2017-0160620호 및 2018년 11월 26일에 한국특허청에 제출된 한국 특허 출원 제 10-2018-0147707호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This application claims priority to Korean Patent Application No. 10-2017-0160620 filed on November 28, 2017 and Korean Patent Application No. 10-2018-0147707 filed on November 26, 2018 The contents of which are incorporated herein by reference.
본 명세서는 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound and an organic light emitting device including the same.
유기 발광 소자가 상용화되기 위해서는 발광재료의 효율 향상이 필요하고, 이를 위해 인광 및 지연 형광 재료에 대한 연구가 활발히 진행되고 있다. 하지만, 상기 인광 재료의 경우, 높은 효율을 달성할 수 있음에도 불구하고 인광을 구현하기 위해 필요한 금속착화물의 가격이 높고 수명이 짧은 문제가 있다.In order to commercialize an organic light emitting device, it is necessary to improve the efficiency of a light emitting material. For this purpose, studies on phosphorescent and retarding fluorescent materials have been actively conducted. However, in the case of the above-mentioned phosphorescent material, there is a problem that the cost of the metal complex required to realize phosphorescence is high and the lifetime is short, although high efficiency can be achieved.
지연 형광 재료의 경우, 최근 열활성화지연형광(TADF: Thermally Activated Delayed Fluorescence)의 개념을 도입하여 형광재료이면서도 외부양자효율이 높은 고효율 녹색 형광 재료를 발표하였다. 열활성화지연형광(TADF) 개념은 여기 삼중항 상태로부터 여기 단일항 상태로의 역 에너지 이동을 열 활성화에 의해서 생기게 하여 형광 발광에 이르는 현상을 나타내고, 삼중항 경유로 발광이 생기기 때문에 일반적으로 수명이 긴 발광이 생기는 점에서 지연 형광으로 부른다. 지연 형광 재료는 형광발광과 인광발광을 모두 사용할 수 있으므로, 기존의 형광재료가 가지는 외부양자효율의 문제점을 해결할 수 있고 금속 착화물을 포함하지 않아도 된다는 점에서 인광 재료의 가격 문제를 해결할 수 있다.Recently, the introduction of the concept of thermally activated delayed fluorescence (TADF) in the case of the retarded fluorescent material has revealed a highly efficient green fluorescent material having a high external quantum efficiency as well as a fluorescent material. The concept of thermally activated delayed fluorescence (TADF) is a phenomenon in which the inverse energy transfer from the excited triplet state to the excited singlet state is caused by thermal activation, leading to fluorescence emission. Generally, the lifetime It is called delayed fluorescence in that long luminescence occurs. Since the retardation fluorescent material can use both fluorescence emission and phosphorescence emission, the problem of the cost of the phosphorescent material can be solved in that the problem of the external quantum efficiency of the conventional fluorescent material can be solved and the metal complex is not required.
본 명세서는 화합물 및 이를 포함하는 유기 발광 소자를 제공한다.The present invention provides a compound and an organic light emitting device comprising the same.
본 명세서의 일 실시상태에 따르면, 하기 화학식 1로 표시되는 화합물을 제공한다.According to one embodiment of the present invention, there is provided a compound represented by the following formula (1).
[화학식 1][Chemical Formula 1]
상기 화학식 1에 있어서,In Formula 1,
A1 내지 A5는 서로 같거나 상이하고, 각각 독립적으로 수소; 할로겐기; 시아노기; 할로알킬기; 알킬기; 알케닐기; 할로알콕시기; 할로겐기, 시아노기, 할로알킬기, 알킬기, 또는 할로알콕시기로 치환 또는 비치환된 아릴기; 또는 헤테로아릴기이거나, 인접한 기는 서로 결합하여 방향족 고리를 형성하며,A1 to A5 are the same or different from each other, and each independently hydrogen; A halogen group; Cyano; Haloalkyl; An alkyl group; An alkenyl group; A haloalkoxy group; An aryl group substituted or unsubstituted with a halogen group, a cyano group, a haloalkyl group, an alkyl group, or a haloalkoxy group; Or a heteroaryl group, or adjacent groups are bonded to each other to form an aromatic ring,
R1 내지 R8 및 R11 내지 R18은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 니트로기; 히드록시기; 카르보닐기; 에스테르기; 이미드기; 아미드기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기는 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R1 to R8 and R11 to R18 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups may be bonded to each other to form a substituted or unsubstituted ring,
n은 1 또는 2이며,n is 1 or 2,
n이 2인 경우, 복수 개의 괄호 내의 구조는 서로 같거나 상이하고,When n is 2, the structures in the plurality of parentheses are equal to or different from each other,
n이 1이고, 상기 A1 내지 A5 중 어느 하나가 헤테로아릴기인 경우, 나머지는 수소이다.When n is 1, and any one of A1 to A5 is a heteroaryl group, the remainder is hydrogen.
또한, 본 명세서의 일 실시상태에 따르면, 제1 전극; 상기 제1 전극에 대향하여 구비된 제2 전극; 및 상기 제1 전극과 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1 층 이상은 전술한 화합물을 포함하는 것인 유기 발광 소자를 제공한다.According to an embodiment of the present invention, there is also provided a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound described above.
본 명세서의 일 실시상태에 따른 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자는 효율의 향상, 낮은 구동전압 및/또는 수명 특성의 향상이 가능하다.The organic light emitting device including the compound represented by Chemical Formula 1 according to one embodiment of the present invention can improve the efficiency, improve the driving voltage and / or the lifetime characteristics.
도 1은 본 명세서의 일 실시상태에 따르는 유기 발광 소자를 도시한 것이다.1 shows an organic light emitting device according to an embodiment of the present invention.
<부호의 설명><Description of Symbols>
10: 유기 발광 소자10: Organic light emitting device
20: 기판20: substrate
30: 제1 전극30: first electrode
40: 발광층40: light emitting layer
50: 제2 전극50: second electrode
이하, 본 명세서에 대하여 더욱 상세하게 설명한다.Hereinafter, the present invention will be described in more detail.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1로 표시되는 화합물을 제공한다.According to one embodiment of the present invention, there is provided a compound represented by the above formula (1).
본 명세서의 일 실시상태에 따른 화학식 1로 표시되는 화합물은 벤젠코어를 중심으로 2개의 시아노기가 파라(para)위치로 결합하므로, 특정 파장 영역의 빛을 발광하며 이를 포함하는 유기 발광 소자는 고효율의 특성이 있다.According to one embodiment of the present invention, the compound represented by the formula (1) combines two cyano groups at the para position with a benzene core as a center, so that the organic light emitting device emitting light in a specific wavelength range, .
또한, 본원 화학식 1의 벤젠 코어를 중심으로 2개의 카바졸 유도체 및 1개 또는 2개의 아릴기가 결합되므로, 발광층에 주입되는 전하 밸런스가 조절되어, 이를 포함하는 유기 발광 소자는 낮은 구동 전압, 효율 및 수명의 향상이 가능하다.Since the two carbazole derivatives and one or two aryl groups are bonded around the benzene core of Formula 1, the charge balance injected into the light emitting layer is controlled, and the organic light emitting device including the benzene core has low driving voltage, The life can be improved.
본 명세서에 있어서, 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다.In this specification, when a part is referred to as "including " an element, it is to be understood that it may include other elements as well, without departing from the other elements unless specifically stated otherwise.
본 명세서에 있어서 치환기의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다.Examples of substituents in the present specification are described below, but are not limited thereto.
상기 "치환"이라는 용어는 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미하며, 치환되는 위치는 수소 원자가 치환되는 위치 즉, 치환기가 치환 가능한 위치라면 한정하지 않으며, 2 이상 치환되는 경우, 2 이상의 치환기는 서로 동일하거나 상이할 수 있다.The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 시아노기; 니트로기; 이미드기; 아미드기; 카르보닐기; 에스테르기; 히드록시기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 바이페닐기일 수 있다. 즉, 바이페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다.As used herein, the term " substituted or unsubstituted " A halogen group; Cyano; A nitro group; Imide; Amide group; Carbonyl group; An ester group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or that at least two of the substituents exemplified above are substituted with a substituent to which they are linked, or have no substituent. For example, "a substituent to which at least two substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.
본 명세서에 있어서, 할로겐기는 불소, 염소, 브롬 또는 요오드가 될 수 있다.In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 30인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
본 명세서에 있어서, 아미드기는 아미드기의 질소가 수소, 탄소수 1 내지 30의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 30의 아릴기로 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the amide group may be substituted with nitrogen of the amide group by hydrogen, a straight chain, branched chain or cyclic alkyl group of 1 to 30 carbon atoms or an aryl group of 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
본 명세서에서 카르보닐기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 30인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
본 명세서에 있어서, 에스테르기는 에스테르기의 산소가 탄소수 1 내지 25의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 30의 아릴기로 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the ester group may be substituted with an ester group oxygen in a straight chain, branched chain or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 30인 것이 바람직하다. 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 시클로펜틸메틸, 시클로헥실메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸펜틸, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 30인 것이 바람직하며, 구체적으로 시클로프로필, 시클로부틸, 시클로펜틸, 3-메틸시클로펜틸, 2,3-디메틸시클로펜틸, 시클로헥실, 3-메틸시클로헥실, 4-메틸시클로헥실, 2,3-디메틸시클로헥실, 3,4,5-트리메틸시클로헥실, 4-tert-부틸시클로헥실, 시클로헵틸, 시클로옥틸 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the cycloalkyl group is not particularly limited, but is preferably a group having 3 to 30 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, isobutyl, sec-butyl, It is not.
본 명세서에 있어서, 상기 알콕시기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 30인 것이 바람직하다. 구체적으로, 메톡시, 에톡시, n-프로폭시, 이소프로폭시, n-부톡시, 이소부톡시, tert-부톡시, sec-부톡시, n-펜틸옥시, 네오펜틸옥시, 이소펜틸옥시, n-헥실옥시, 3,3-디메틸부틸옥시, 2-에틸부틸옥시, n-옥틸옥시, n-노닐옥시, n-데실옥시, 벤질옥시, p-메틸벤질옥시 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n Butyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like. But is not limited thereto.
본 명세서에 있어서, 아민기는 -NH2; 알킬아민기; N-알킬아릴아민기; 아릴아민기; N-아릴헤테로아릴아민기; N-알킬헤테로아릴아민기 및 헤테로아릴아민기로 이루어진 군으로부터 선택될 수 있으며, 탄소수는 특별히 한정되지 않으나, 1 내지 30인 것이 바람직하다. 아민기의 구체적인 예로는 메틸아민기, 디메틸아민기, 에틸아민기, 디에틸아민기, 페닐아민기, 나프틸아민기, 바이페닐아민기, 안트라세닐아민기, 9-메틸-안트라세닐아민기, 디페닐아민기, N-페닐나프틸아민기, 디톨릴아민기, N-페닐톨릴아민기, 트리페닐아민기, N-페닐바이페닐아민기, N-페닐나프틸아민기, N-바이페닐나프틸아민기, N-나프틸플루오레닐아민기, N-페닐페난트레닐아민기, N-바이페닐페난트레닐아민기, N-페닐플루오레닐아민기, N-페닐터페닐아민기, N-페난트레닐플루오레닐아민기, N-바이페닐플루오레닐아민기 등이 있으나, 이에 한정되는 것은 아니다.In this specification, the amine group is -NH 2 ; An alkylamine group; N-alkylarylamine groups; An arylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, Phenylnaphthylenediamine group, N-phenylphenylenediamine group, N-phenyltriphenylamine group, N-phenylphenanthrenylamine group, N-phenylphenanthrenylamine group, Group, an N-phenanthrenylfluorenylamine group, and an N-biphenylfluorenylamine group, but the present invention is not limited thereto.
본 명세서에 있어서, N-알킬아릴아민기는 아민기의 N에 알킬기 및 아릴기가 치환된 아민기를 의미한다.In the present specification, the N-alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group.
본 명세서에 있어서, N-아릴헤테로아릴아민기는 아민기의 N에 아릴기 및 헤테로아릴기가 치환된 아민기를 의미한다.In the present specification, the N-arylheteroarylamine group means an amine group in which N in the amine group is substituted with an aryl group and a heteroaryl group.
본 명세서에 있어서, N-알킬헤테로아릴아민기는 아민기의 N에 알킬기 및 헤테로아릴기가 치환된 아민기를 의미한다.In the present specification, the N-alkylheteroarylamine group means an amine group in which N in the amine group is substituted with an alkyl group and a heteroaryl group.
본 명세서에 있어서, 알킬아민기, N-아릴알킬아민기, 알킬티옥시기, 알킬술폭시기, N-알킬헤테로아릴아민기 중의 알킬기는 전술한 알킬기의 예시와 같다. 구체적으로 알킬티옥시기로는 메틸티옥시기, 에틸티옥시기, tert-부틸티옥시기, 헥실티옥시기, 옥틸티옥시기 등이 있고, 알킬술폭시기로는 메틸술폭시기, 에틸술폭시기, 프로필술폭시기, 부틸술폭시기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkyl group in the alkylamine group, the N-arylalkylamine group, the alkylthio group, the alkylsulfoxy group and the N-alkylheteroarylamine group is the same as the alkyl group described above. Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group. Examples of the alkylsulfoxy group include a methylsulfoxy group, an ethylsulfoxy group, a propylsulfoxy group, And the like, but the present invention is not limited thereto.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 30인 것이 바람직하다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 알릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.
본 명세서에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, However, the present invention is not limited thereto.
본 명세서에 있어서, 붕소기는 -BR100R101일 수 있으며, 상기 R100 및 R101은 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐; 시아노기; 치환 또는 비치환된 탄소수 3 내지 30의 단환 또는 다환의 시클로알킬기; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 및 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기로 이루어진 군으로부터 선택될 수 있다.In the present specification, the boron group may be -BR 100 R 101 , wherein R 100 and R 101 are the same or different and each independently hydrogen; heavy hydrogen; halogen; Cyano; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
본 명세서에 있어서, 포스핀옥사이드기는 구체적으로 디페닐포스핀옥사이드기, 디나프틸포스핀옥사이드기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the phosphine oxide group specifically includes a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, and the like, but is not limited thereto.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나, 탄소수 6 내지 30인 것이 바람직하며, 상기 아릴기는 단환식 또는 다환식일 수 있다.In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
상기 아릴기가 단환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나, 탄소수 6 내지 30인 것이 바람직하다. 구체적으로 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.
상기 아릴기가 다환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나. 탄소수 10 내지 30인 것이 바람직하다. 구체적으로 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 트리페닐기, 파이레닐기, 페날레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기, 플루오란테닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably 10 to 30 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, triphenyl, pyrenyl, phenalenyl, perylenyl, , But is not limited thereto.
본 명세서에 있어서, 상기 플루오레닐기는 치환될 수 있으며, 인접한 기들이 서로 결합하여 고리를 형성할 수 있다. In the present specification, the fluorenyl group may be substituted, and adjacent groups may combine with each other to form a ring.
상기 플루오레닐기가 치환되는 경우, 등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted, And the like. However, the present invention is not limited thereto.
본 명세서에 있어서, "인접한" 기는 해당 치환기가 치환된 원자와 직접 연결된 원자에 치환된 치환기, 해당 치환기와 입체구조적으로 가장 가깝게 위치한 치환기, 또는 해당 치환기가 치환된 원자에 치환된 다른 치환기를 의미할 수 있다. 예컨대, 벤젠고리에서 오르토(ortho)위치로 치환된 2개의 치환기 및 지방족 고리에서 동일 탄소에 치환된 2개의 치환기는 서로 "인접한" 기로 해석될 수 있다.As used herein, the term " adjacent " means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom . For example, two substituents substituted in the benzene ring to the ortho position and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.
본 명세서에 있어서, 아릴옥시기, 아릴티옥시기, 아릴술폭시기, N-아릴알킬아민기, N-아릴헤테로아릴아민기 및 아릴포스핀기 중의 아릴기는 전술한 아릴기의 예시와 같다. 구체적으로 아릴옥시기로는 페녹시기, p-토릴옥시기, m-토릴옥시기, 3,5-디메틸-페녹시기, 2,4,6-트리메틸페녹시기, p-tert-부틸페녹시기, 3-바이페닐옥시기, 4-바이페닐옥시기, 1-나프틸옥시기, 2-나프틸옥시기, 4-메틸-1-나프틸옥시기, 5-메틸-2-나프틸옥시기, 1-안트릴옥시기, 2-안트릴옥시기, 9-안트릴옥시기, 1-페난트릴옥시기, 3-페난트릴옥시기, 9-페난트릴옥시기 등이 있고, 아릴티옥시기로는 페닐티옥시기, 2-메틸페닐티옥시기, 4-tert-부틸페닐티옥시기 등이 있으며, 아릴술폭시기로는 벤젠술폭시기, p-톨루엔술폭시기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the N-arylalkylamine group, the N-arylheteroarylamine group and the arylphosphine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6- trimethylphenoxy group, a p- Naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group and 9-phenanthryloxy group and the arylthioxy group includes phenylthio group, 2- Methylphenylthio group, 4-tert-butylphenylthio group and the like, and examples of the arylsulfoxy group include a benzene sulfoxide group and a p-toluenesulfoxy group. However, the present invention is not limited thereto.
본 명세서에 있어서, 아릴아민기의 예로는 치환 또는 비치환된 모노아릴아민기, 또는 치환 또는 비치환된 디아릴아민기가 있다. 상기 아릴아민기 중의 아릴기는 단환식 아릴기일 수 있고, 다환식 아릴기일 수 있다. 상기 아릴기가 2 이상을 포함하는 아릴아민기는 단환식 아릴기, 다환식 아릴기, 또는 단환식 아릴기와 다환식 아릴기를 동시에 포함할 수 있다. 예컨대, 상기 아릴아민기 중의 아릴기는 전술한 아릴기의 예시 중에서 선택될 수 있다.In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, or a substituted or unsubstituted diarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
본 명세서에 있어서, 헤테로아릴기는 탄소가 아닌 원자, 이종원자를 1 이상 포함하는 것으로서, 구체적으로 상기 이종 원자는 O, N, Se 및 S 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 30인 것이 바람직하며, 상기 헤테로아릴기는 단환식 또는 다환식일 수 있다. 헤테로고리기의 예로는 티오펜기, 퓨라닐기, 피롤기, 이미다졸릴기, 티아졸릴기, 옥사졸릴기, 옥사디아졸릴기, 피리딜기, 바이피리딜기, 피리미딜기, 트리아지닐기, 트리아졸릴기, 아크리딜기, 피리다지닐기, 피라지닐기, 퀴놀릴기, 퀴나졸릴기, 퀴녹살릴기, 프탈라지닐기, 피리도 피리미딜기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀릴기, 인돌릴기, 카바졸릴기, 벤즈옥사졸릴기, 벤즈이미다졸릴기, 벤조티아졸릴기, 벤조카바졸릴기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 페난쓰롤리닐기(phenanthroline), 이소옥사졸릴기, 티아디아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the heteroaryl group includes at least one non-carbon atom and at least one hetero atom. Specifically, the hetero atom may include one or more atoms selected from the group consisting of O, N, Se and S, and the like. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include a thiophene group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, , An isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, Phenanthroline, isoxazolyl group, thiadiazolyl group, phenothiazinyl group, and dibenzofuranyl group, but the present invention is not limited thereto.
본 명세서에 있어서, 헤테로아릴아민기의 예로는 치환 또는 비치환된 모노헤테로아릴아민기, 또는 치환 또는 비치환된 디헤테로아릴아민기가 있다. 상기 헤테로아릴기가 2 이상을 포함하는 헤테로아릴아민기는 단환식 헤테로아릴기, 다환식 헤테로아릴기, 또는 단환식 헤테로아릴기와 다환식 헤테로아릴기를 동시에 포함할 수 있다. 예컨대, 상기 헤테로아릴아민기 중의 헤테로아릴기는 전술한 헤테로아릴기의 예시 중에서 선택될 수 있다.In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group. The heteroarylamine group having two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the above-mentioned heteroaryl group.
본 명세서에 있어서, N-아릴헤테로아릴아민기 및 N-알킬헤테로아릴아민기 중의 헤테로아릴기의 예시는 전술한 헤테로아릴기의 예시와 같다.In the present specification, examples of the heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the above-mentioned heteroaryl group.
본 명세서에 있어서, 인접한 기가 서로 결합하여 형성되는 치환 또는 비치환된 고리에서, "고리"는 치환 또는 비치환된 탄화수소고리; 또는 치환 또는 비치환된 헤테로고리를 의미한다.In the present specification, in the substituted or unsubstituted ring formed by bonding adjacent groups to each other, the "ring" means a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.
명세서에 있어서, 탄화수소고리는 방향족, 지방족 또는 방향족과 지방족의 축합고리일 수 있으며, 상기 1가가 아닌 것을 제외하고 상기 시클로알킬기 또는 아릴기의 예시 중에서 선택될 수 있다.In the specification, the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from the examples of the cycloalkyl group or the aryl group except the univalent hydrocarbon ring.
본 명세서에 있어서, 방향족고리는 단환 또는 다환일 수 있으며, 1가가 아닌 것을 제외하고 상기 아릴기의 예시 중에서 선택될 수 있다.In this specification, the aromatic ring may be monocyclic or polycyclic and may be selected from the examples of the aryl group except that it is not monovalent.
본 명세서에 있어서, 헤테로고리는 탄소가 아닌 원자, 이종원자를 1 이상 포함하는 것으로서, 구체적으로 상기 이종 원자는 O, N, Se 및 S 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 상기 헤테로고리는 단환 또는 다환일 수 있으며, 방향족, 지방족 또는 방향족과 지방족의 축합고리일 수 있으며, 1가가 아닌 것을 제외하고 상기 헤테로아릴기 또는 헤테로고리기의 예시 중에서 선택될 수 있다.In the present specification, the hetero ring includes one or more non-carbon atoms and hetero atoms. Specifically, the hetero atom may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. The heterocyclic ring may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and examples thereof may be selected from the heteroaryl group or the heterocyclic group except that the monocyclic group is not monovalent.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 1-1 또는 1-2로 표시된다.According to one embodiment of the present invention, the formula (1) is represented by the following formula (1-1) or (1-2).
[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
상기 화학식 1-1 및 1-2에 있어서,In the above formulas 1-1 and 1-2,
A1 내지 A5, R1 내지 R8 및 R11 내지 R18의 정의는 상기 화학식 1에서 정의한 바와 동일하고, The definitions of A 1 to A 5, R 1 to R 8 and R 11 to R 18 are as defined in the above formula (1)
A11 내지 A15는 서로 같거나 상이하고, 각각 독립적으로 수소; 할로겐기; 시아노기; 할로알킬기; 알킬기; 알케닐기; 할로알콕시기; 할로겐기, 시아노기, 할로알킬기, 알킬기, 또는 할로알콕시기로 치환 또는 비치환된 아릴기; 또는 헤테로아릴기이거나, 인접한 기는 서로 결합하여 방향족 고리를 형성한다.A11 to A15 are the same or different and each independently hydrogen; A halogen group; Cyano; Haloalkyl; An alkyl group; An alkenyl group; A haloalkoxy group; An aryl group substituted or unsubstituted with a halogen group, a cyano group, a haloalkyl group, an alkyl group, or a haloalkoxy group; Or a heteroaryl group, or adjacent groups are bonded to each other to form an aromatic ring.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R1 내지 R8 및 R11 내지 R18는 서로 같거나 상이하고, 각각 독립적으로 수소; 또는 치환 또는 비치환된 알킬기이다.According to one embodiment of the present invention, in the general formula (1), R 1 to R 8 and R 11 to R 18 are the same or different and each independently hydrogen; Or a substituted or unsubstituted alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R1 내지 R8 및 R11 내지 R18는 서로 같거나 상이하고, 각각 독립적으로 수소; 또는 알킬기이다.According to one embodiment of the present invention, in the general formula (1), R 1 to R 8 and R 11 to R 18 are the same or different and each independently hydrogen; Or an alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R1 내지 R8 및 R11 내지 R18는 서로 같거나 상이하고, 각각 독립적으로 수소; 또는 메틸기이다.According to one embodiment of the present invention, in the general formula (1), R 1 to R 8 and R 11 to R 18 are the same or different and each independently hydrogen; Or a methyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R1 내지 R8 및 R11 내지 R18 중 인접한 기는 서로 결합하여, 치환 또는 비치환된 탄화수소고리를 형성한다.According to one embodiment of the present invention, in the general formula (1), adjacent groups among R1 to R8 and R11 to R18 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R1 내지 R8 및 R11 내지 R18 중 인접한 기는 서로 결합하여, 1 이상의 알킬기로 치환된 탄화수소고리를 형성한다.According to one embodiment of the present invention, adjacent groups among R1 to R8 and R11 to R18 in the formula (1) are bonded to each other to form a hydrocarbon ring substituted with at least one alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R1 내지 R8 및 R11 내지 R18 중 인접한 기는 서로 결합하여, 1 이상의 알킬기로 치환된 방향족 고리를 형성한다.According to one embodiment of the present invention, adjacent groups among R1 to R8 and R11 to R18 in the formula (1) are bonded to each other to form an aromatic ring substituted with at least one alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R1 내지 R8 및 R11 내지 R18 중 인접한 기는 서로 결합하여, 1 이상의 알킬기로 치환된 인덴고리를 형성한다.According to one embodiment of the present invention, in the above formula (1), adjacent groups among R1 to R8 and R11 to R18 are bonded to each other to form an indene ring substituted with at least one alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R1 내지 R8 및 R11 내지 R18 중 인접한 기는 서로 결합하여, 1 이상의 메틸기로 치환된 인덴고리를 형성한다.According to one embodiment of the present invention, adjacent groups among R1 to R8 and R11 to R18 in the general formula (1) are bonded to each other to form an indene ring substituted with at least one methyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R2 및 R3은 서로 결합하여, 치환 또는 비치환된 탄화수소고리를 형성한다.According to one embodiment of the present invention, in the general formula (1), R 2 and R 3 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R2 및 R3은 서로 결합하여, 1 이상의 알킬기로 치환된 탄화수소고리를 형성한다.According to one embodiment of the present invention, in Formula 1, R 2 and R 3 are bonded to each other to form a hydrocarbon ring substituted with at least one alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R2 및 R3은 서로 결합하여, 1 이상의 알킬기로 치환된 방향족 고리를 형성한다.According to one embodiment of the present invention, in Formula 1, R 2 and R 3 are bonded to each other to form an aromatic ring substituted with at least one alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R2 및 R3은 서로 결합하여, 1 이상의 알킬기로 치환된 인덴고리를 형성한다.According to one embodiment of the present invention, in the general formula (1), R 2 and R 3 are bonded to each other to form an indene ring substituted with at least one alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R2 및 R3은 서로 결합하여, 1 이상의 메틸기로 치환된 인덴고리를 형성한다.According to one embodiment of the present invention, in the general formula (1), R 2 and R 3 are bonded to each other to form an indene ring substituted with at least one methyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R2 및 R3 중 어느 하나가 치환 또는 비치환된 아릴기이고, 나머지는 치환 또는 비치환된 알킬기이며, R2 및 R3이 서로 결합하여 치환 또는 비치환된 탄화수소고리를 형성한다.According to one embodiment of the present invention, any one of R 2 and R 3 in the general formula (1) is a substituted or unsubstituted aryl group, and the other is a substituted or unsubstituted alkyl group; To form an unsubstituted hydrocarbon ring.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R2 및 R3 중 어느 하나가 치환 또는 비치환된 페닐기이고, 나머지는 치환 또는 비치환된 알킬기이며, R2 및 R3이 서로 결합하여 치환 또는 비치환된 탄화수소고리를 형성한다.According to one embodiment of the present invention, any one of R 2 and R 3 in the general formula (1) is a substituted or unsubstituted phenyl group, and the other is a substituted or unsubstituted alkyl group; To form a ring-opened hydrocarbon ring.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R3은 치환 또는 비치환된 페닐기이고, R2는 치환 또는 비치환된 알킬기이며, R2 및 R3이 서로 결합하여 치환 또는 비치환된 탄화수소고리를 형성한다.According to one embodiment of the present invention, in Formula 1, R 3 is a substituted or unsubstituted phenyl group, R 2 is a substituted or unsubstituted alkyl group, and R 2 and R 3 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring .
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R3은 페닐기이고, R2는 이소프로필기이며, R2 및 R3이 서로 결합하여 2개의 메틸기로 치환된 인덴고리를 형성한다.According to one embodiment of the present invention, in the general formula (1), R 3 is a phenyl group, R 2 is an isopropyl group, and R 2 and R 3 are bonded to each other to form an indene ring substituted with two methyl groups.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R6 및 R7은 서로 결합하여, 치환 또는 비치환된 탄화수소고리를 형성한다.According to one embodiment of the present invention, in the general formula (1), R 6 and R 7 combine with each other to form a substituted or unsubstituted hydrocarbon ring.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R6 및 R7은 서로 결합하여, 1 이상의 알킬기로 치환된 탄화수소고리를 형성한다.According to one embodiment of the present invention, in Formula 1, R 6 and R 7 are bonded to each other to form a hydrocarbon ring substituted with at least one alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R6 및 R7은 서로 결합하여, 1 이상의 알킬기로 치환된 방향족 고리를 형성한다.According to one embodiment of the present invention, in the above formula (1), R 6 and R 7 combine with each other to form an aromatic ring substituted with at least one alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R6 및 R7은 서로 결합하여, 1 이상의 알킬기로 치환된 인덴고리를 형성한다.According to one embodiment of the present invention, in the general formula (1), R 6 and R 7 combine with each other to form an indene ring substituted with at least one alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R6 및 R7은 서로 결합하여, 1 이상의 메틸기로 치환된 인덴고리를 형성한다.According to one embodiment of the present invention, in the above formula (1), R 6 and R 7 combine with each other to form an indene ring substituted with at least one methyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R6 및 R7 중 어느 하나가 치환 또는 비치환된 아릴기이고, 나머지는 치환 또는 비치환된 알킬기이며, R6 및 R7이 서로 결합하여 치환 또는 비치환된 탄화수소고리를 형성한다.According to one embodiment of the present invention, any one of R6 and R7 is a substituted or unsubstituted aryl group and the remaining is a substituted or unsubstituted alkyl group, and R6 and R7 are bonded to each other to form a substituted or unsubstituted To form an unsubstituted hydrocarbon ring.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R6 및 R7 중 어느 하나가 치환 또는 비치환된 페닐기이고, 나머지는 치환 또는 비치환된 알킬기이며, R6 및 R7이 서로 결합하여 치환 또는 비치환된 탄화수소고리를 형성한다.According to one embodiment of the present invention, any one of R6 and R7 is a substituted or unsubstituted phenyl group and the remaining is a substituted or unsubstituted alkyl group, and R6 and R7 are bonded to each other to form a substituted or unsubstituted To form a ring-opened hydrocarbon ring.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R6은 치환 또는 비치환된 페닐기이고, R7은 치환 또는 비치환된 알킬기이며, R6 및 R7이 서로 결합하여 치환 또는 비치환된 탄화수소고리를 형성한다.According to one embodiment of the present invention, R6 is a substituted or unsubstituted phenyl group, R7 is a substituted or unsubstituted alkyl group, and R6 and R7 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring .
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R6은 페닐기이고, R7은 이소프로필기이며, R6 및 R7이 서로 결합하여 2개의 메틸기로 치환된 인덴고리를 형성한다.According to one embodiment of the present invention, R6 is a phenyl group, R7 is an isopropyl group, and R6 and R7 are bonded to each other to form an indene ring substituted with two methyl groups.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R12 및 R13은 서로 결합하여, 치환 또는 비치환된 탄화수소고리를 형성한다.According to one embodiment of the present invention, in the general formula (1), R 12 and R 13 combine with each other to form a substituted or unsubstituted hydrocarbon ring.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R12 및 R13은 서로 결합하여, 1 이상의 알킬기로 치환된 탄화수소고리를 형성한다.According to one embodiment of the present invention, R12 and R13 in the formula (1) are bonded to each other to form a hydrocarbon ring substituted with at least one alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R12 및 R13은 서로 결합하여, 1 이상의 알킬기로 치환된 방향족 고리를 형성한다.According to one embodiment of the present invention, in the above formula (1), R 12 and R 13 combine with each other to form an aromatic ring substituted with at least one alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R12 및 R13은 서로 결합하여, 1 이상의 알킬기로 치환된 인덴고리를 형성한다.According to one embodiment of the present invention, in the general formula (1), R12 and R13 are bonded to each other to form an indene ring substituted with at least one alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R12 및 R13은 서로 결합하여, 1 이상의 메틸기로 치환된 인덴고리를 형성한다.According to one embodiment of the present invention, in the general formula (1), R 12 and R 13 combine with each other to form an indene ring substituted with at least one methyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R12 및 R13 중 어느 하나가 치환 또는 비치환된 아릴기이고, 나머지는 치환 또는 비치환된 알킬기이며, R12 및 R13이 서로 결합하여 치환 또는 비치환된 탄화수소고리를 형성한다.According to one embodiment of the present invention, any one of R12 and R13 is a substituted or unsubstituted aryl group and the remaining is a substituted or unsubstituted alkyl group, and R12 and R13 are bonded to each other to form a substituted or unsubstituted To form an unsubstituted hydrocarbon ring.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R12 및 R13 중 어느 하나가 치환 또는 비치환된 페닐기이고, 나머지는 치환 또는 비치환된 알킬기이며, R12 및 R13이 서로 결합하여 치환 또는 비치환된 탄화수소고리를 형성한다.According to an embodiment of the present invention, any one of R12 and R13 is a substituted or unsubstituted phenyl group and the remaining is a substituted or unsubstituted alkyl group, and R12 and R13 are bonded to each other to be substituted or to be substituted To form a ring-opened hydrocarbon ring.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R13은 치환 또는 비치환된 페닐기이고, R12는 치환 또는 비치환된 알킬기이며, R12 및 R13이 서로 결합하여 치환 또는 비치환된 탄화수소고리를 형성한다.According to an embodiment of the present invention, R13 is a substituted or unsubstituted phenyl group, R12 is a substituted or unsubstituted alkyl group, and R12 and R13 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring .
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R13은 페닐기이고, R12는 이소프로필기이며, R12 및 R13이 서로 결합하여 2개의 메틸기로 치환된 인덴고리를 형성한다.According to one embodiment of the present invention, R13 is a phenyl group, R12 is an isopropyl group, and R12 and R13 are bonded to each other to form an indene ring substituted with two methyl groups.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R16 및 R17은 서로 결합하여, 치환 또는 비치환된 탄화수소고리를 형성한다.According to one embodiment of the present invention, in the above formula (1), R16 and R17 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R16 및 R17은 서로 결합하여, 1 이상의 알킬기로 치환된 탄화수소고리를 형성한다.According to one embodiment of the present invention, R16 and R17 are bonded to each other to form a hydrocarbon ring substituted with at least one alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R16 및 R17은 서로 결합하여, 1 이상의 알킬기로 치환된 방향족 고리를 형성한다.According to one embodiment of the present invention, in the above Formula 1, R16 and R17 are bonded to each other to form an aromatic ring substituted with at least one alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R16 및 R17은 서로 결합하여, 1 이상의 알킬기로 치환된 인덴고리를 형성한다.According to one embodiment of the present invention, in the general formula (1), R16 and R17 are bonded to each other to form an indene ring substituted with at least one alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R16 및 R17은 서로 결합하여, 1 이상의 메틸기로 치환된 인덴고리를 형성한다.According to one embodiment of the present invention, in the general formula (1), R16 and R17 are bonded to each other to form an indene ring substituted with at least one methyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R16 및 R17 중 어느 하나가 치환 또는 비치환된 아릴기이고, 나머지는 치환 또는 비치환된 알킬기이며, R16 및 R17이 서로 결합하여 치환 또는 비치환된 탄화수소고리를 형성한다.According to one embodiment of the present invention, any one of R16 and R17 is a substituted or unsubstituted aryl group and the remaining is a substituted or unsubstituted alkyl group, and R16 and R17 are bonded to each other to form a substituted or unsubstituted To form an unsubstituted hydrocarbon ring.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R16 및 R17 중 어느 하나가 치환 또는 비치환된 페닐기이고, 나머지는 치환 또는 비치환된 알킬기이며, R16 및 R17이 서로 결합하여 치환 또는 비치환된 탄화수소고리를 형성한다.According to one embodiment of the present invention, any one of R16 and R17 is a substituted or unsubstituted phenyl group and the remaining is a substituted or unsubstituted alkyl group, and R16 and R17 are bonded to each other to be substituted or to be substituted To form a ring-opened hydrocarbon ring.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R16은 치환 또는 비치환된 페닐기이고, R17은 치환 또는 비치환된 알킬기이며, R16 및 R17이 서로 결합하여 치환 또는 비치환된 탄화수소고리를 형성한다.According to one embodiment of the present invention, R16 is a substituted or unsubstituted phenyl group, R17 is a substituted or unsubstituted alkyl group, and R16 and R17 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring .
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, R16은 페닐기이고, R17은 이소프로필기이며, R16 및 R17이 서로 결합하여 2개의 메틸기로 치환된 인덴고리를 형성한다.According to one embodiment of the present invention, R16 is a phenyl group, R17 is an isopropyl group, and R16 and R17 are bonded to each other to form an indene ring substituted with two methyl groups.
본 명세서의 일 실시상태에 따르면, A1 내지 A5 및 A11 내지 A15는 서로 같거나 상이하고, 각각 독립적으로 수소; 할로겐기; 시아노기; 할로알킬기; 알킬기; 알케닐기; 할로알콕시기; 할로겐기, 시아노기, 할로알킬기, 알킬기, 또는 할로알콕시기로 치환 또는 비치환된 아릴기; 또는 헤테로아릴기이다.According to one embodiment of the present disclosure, A1 to A5 and A11 to A15 are the same or different from each other, and each independently hydrogen; A halogen group; Cyano; Haloalkyl; An alkyl group; An alkenyl group; A haloalkoxy group; An aryl group substituted or unsubstituted with a halogen group, a cyano group, a haloalkyl group, an alkyl group, or a haloalkoxy group; Or a heteroaryl group.
본 명세서의 일 실시상태에 따르면, A1 내지 A5 및 A11 내지 A15는 서로 같거나 상이하고, 각각 독립적으로 수소; 불소; 시아노기; 트리플루오로메틸기; 메틸기; 이소프로필기; t-부틸기; 트리플루오로메톡시기; 불소, 시아노기, 트리플루오로메틸기, 메틸기, 또는 트리플루오로메톡시기로 치환 또는 비치환된 아릴기; 또는 다환의 헤테로아릴기이다.According to one embodiment of the present disclosure, A1 to A5 and A11 to A15 are the same or different from each other, and each independently hydrogen; Fluorine; Cyano; A trifluoromethyl group; Methyl group; Isopropyl group; t-butyl group; A trifluoromethoxy group; An aryl group which is substituted or unsubstituted with a fluorine atom, a cyano group, a trifluoromethyl group, a methyl group, or a trifluoromethoxy group; Or a polycyclic heteroaryl group.
본 명세서의 일 실시상태에 따르면, A1 내지 A5 및 A11 내지 A15는 서로 같거나 상이하고, 각각 독립적으로 수소; 불소; 시아노기; 트리플루오로메틸기; 메틸기; 이소프로필기; t-부틸기; 트리플루오로메톡시기; 불소, 시아노기, 트리플루오로메틸기, 메틸기, 또는 트리플루오로메톡시기로 치환 또는 비치환된 페닐기; 또는 카바졸릴기이다.According to one embodiment of the present disclosure, A1 to A5 and A11 to A15 are the same or different from each other, and each independently hydrogen; Fluorine; Cyano; A trifluoromethyl group; Methyl group; Isopropyl group; t-butyl group; A trifluoromethoxy group; A phenyl group substituted or unsubstituted by fluorine, a cyano group, a trifluoromethyl group, a methyl group, or a trifluoromethoxy group; Or a carbazolyl group.
본 명세서의 일 실시상태에 따르면, A1 내지 A5 중 인접한 기는 서로 결합하여, 방향족 고리를 형성한다.According to one embodiment of the present specification, adjacent groups of A1 to A5 are bonded to each other to form an aromatic ring.
본 명세서의 일 실시상태에 따르면, A1 내지 A5 중 인접한 기는 서로 결합하여, 벤젠 고리를 형성한다.According to one embodiment of the present disclosure, adjacent groups of A1 to A5 combine with each other to form a benzene ring.
본 명세서의 일 실시상태에 따르면, A11 내지 A15 중 인접한 기는 서로 결합하여, 방향족 고리를 형성한다.According to one embodiment of the present specification, adjacent groups among A11 to A15 are bonded to each other to form an aromatic ring.
본 명세서의 일 실시상태에 따르면, A11 내지 A15 중 인접한 기는 서로 결합하여, 벤젠 고리를 형성한다.According to one embodiment of the present specification, adjacent groups among A11 to A15 are bonded to each other to form a benzene ring.
본 명세서의 일 실시상태에 따르면, A1 및 A5는 서로 결합하여, 방향족 고리를 형성한다.According to one embodiment of the present disclosure, A 1 and A 5 combine with each other to form an aromatic ring.
본 명세서의 일 실시상태에 따르면, A1 및 A5는 서로 결합하여, 벤젠 고리를 형성한다.According to one embodiment of the present disclosure, A 1 and A 5 combine with each other to form a benzene ring.
본 명세서의 일 실시상태에 따르면, A1 및 A5는 각각 치환 또는 비치환된 알케닐기이고, 서로 결합하여, 치환 또는 비치환된 벤젠 고리를 형성한다.According to one embodiment of the present invention, A1 and A5 are each a substituted or unsubstituted alkenyl group, and combine with each other to form a substituted or unsubstituted benzene ring.
본 명세서의 일 실시상태에 따르면, A1 및 A5는 각각 에테닐기(ethenyl)이고, 서로 결합하여, 벤젠 고리를 형성한다.According to one embodiment of the present disclosure, A1 and A5 are each ethenyl and combine with each other to form a benzene ring.
본 명세서의 일 실시상태에 따르면, A2 및 A3는 서로 결합하여, 방향족 고리를 형성한다.According to one embodiment of the present disclosure, A2 and A3 combine with each other to form an aromatic ring.
본 명세서의 일 실시상태에 따르면, A2 및 A3는 서로 결합하여, 벤젠 고리를 형성한다.According to one embodiment of the present disclosure, A2 and A3 combine with each other to form a benzene ring.
본 명세서의 일 실시상태에 따르면, A2 및 A3은 각각 치환 또는 비치환된 알케닐기이고, 서로 결합하여, 치환 또는 비치환된 벤젠 고리를 형성한다.According to one embodiment of the present invention, A2 and A3 are each a substituted or unsubstituted alkenyl group, and combine with each other to form a substituted or unsubstituted benzene ring.
본 명세서의 일 실시상태에 따르면, A2 및 A3은 각각 에테닐기(ethenyl)이고, 서로 결합하여, 벤젠 고리를 형성한다.According to one embodiment of the present disclosure, A2 and A3 are each an ethenyl and combine with each other to form a benzene ring.
본 명세서의 일 실시상태에 따르면, A3 및 A4는 서로 결합하여, 방향족 고리를 형성한다.According to one embodiment of the present disclosure, A3 and A4 are bonded to each other to form an aromatic ring.
본 명세서의 일 실시상태에 따르면, A3 및 A4는 서로 결합하여, 벤젠 고리를 형성한다.According to one embodiment of the present disclosure, A3 and A4 are bonded to each other to form a benzene ring.
본 명세서의 일 실시상태에 따르면, A3 및 A4는 각각 치환 또는 비치환된 알케닐기이고, 서로 결합하여, 치환 또는 비치환된 벤젠 고리를 형성한다.According to one embodiment of the present invention, A3 and A4 are each a substituted or unsubstituted alkenyl group and are bonded to each other to form a substituted or unsubstituted benzene ring.
본 명세서의 일 실시상태에 따르면, A3 및 A4는 각각 에테닐기(ethenyl)이고, 서로 결합하여, 벤젠 고리를 형성한다.According to one embodiment of the present disclosure, A3 and A4 are each an ethenyl and combine with each other to form a benzene ring.
본 명세서의 일 실시상태에 따르면, A4 및 A5는 서로 결합하여, 방향족 고리를 형성한다.According to one embodiment of the present disclosure, A4 and A5 combine with each other to form an aromatic ring.
본 명세서의 일 실시상태에 따르면, A4 및 A5는 서로 결합하여, 벤젠 고리를 형성한다.According to one embodiment of the present disclosure, A4 and A5 combine with each other to form a benzene ring.
본 명세서의 일 실시상태에 따르면, A4 및 A5는 각각 치환 또는 비치환된 알케닐기이고, 서로 결합하여, 치환 또는 비치환된 벤젠 고리를 형성한다.According to one embodiment of the present invention, A4 and A5 are each a substituted or unsubstituted alkenyl group and are bonded to each other to form a substituted or unsubstituted benzene ring.
본 명세서의 일 실시상태에 따르면, A4 및 A5는 각각 에테닐기(ethenyl)이고, 서로 결합하여, 벤젠 고리를 형성한다.According to one embodiment of the present disclosure, A4 and A5 are each ethenyl and combine with each other to form a benzene ring.
본 명세서의 일 실시상태에 따르면, A11 및 A12는 서로 결합하여, 방향족 고리를 형성한다.According to one embodiment of the present disclosure, A11 and A12 combine with each other to form an aromatic ring.
본 명세서의 일 실시상태에 따르면, A11 및 A12는 서로 결합하여, 벤젠 고리를 형성한다.According to one embodiment of the present disclosure, A11 and A12 combine with each other to form a benzene ring.
본 명세서의 일 실시상태에 따르면, A11 및 A12는 각각 치환 또는 비치환된 알케닐기이고, 서로 결합하여, 치환 또는 비치환된 벤젠 고리를 형성한다.According to one embodiment of the present invention, A11 and A12 are each a substituted or unsubstituted alkenyl group and are bonded to each other to form a substituted or unsubstituted benzene ring.
본 명세서의 일 실시상태에 따르면, A11 및 A12는 각각 에테닐기(ethenyl)이고, 서로 결합하여, 벤젠 고리를 형성한다.According to one embodiment of the present disclosure, A11 and A12 are each ethenyl and combine with each other to form a benzene ring.
본 명세서의 일 실시상태에 따르면, A12 및 A13는 서로 결합하여, 방향족 고리를 형성한다.According to one embodiment of the present disclosure, A12 and A13 are bonded to each other to form an aromatic ring.
본 명세서의 일 실시상태에 따르면, A12 및 A13는 서로 결합하여, 벤젠 고리를 형성한다.According to one embodiment of the present disclosure, A12 and A13 combine with each other to form a benzene ring.
본 명세서의 일 실시상태에 따르면, A12 및 A13은 각각 치환 또는 비치환된 알케닐기이고, 서로 결합하여, 치환 또는 비치환된 벤젠 고리를 형성한다.According to one embodiment of the present invention, A12 and A13 are each a substituted or unsubstituted alkenyl group, and combine with each other to form a substituted or unsubstituted benzene ring.
본 명세서의 일 실시상태에 따르면, A12 및 A13은 각각 에테닐기(ethenyl)이고, 서로 결합하여, 벤젠 고리를 형성한다.According to one embodiment of the present disclosure, A12 and A13 are each ethenyl and combine with each other to form a benzene ring.
본 명세서의 일 실시상태에 따르면, A13 및 A14는 서로 결합하여, 방향족 고리를 형성한다.According to one embodiment of the present disclosure, A13 and A14 combine with each other to form an aromatic ring.
본 명세서의 일 실시상태에 따르면, A13 및 A14는 서로 결합하여, 벤젠 고리를 형성한다.According to one embodiment of the present disclosure, A13 and A14 combine with each other to form a benzene ring.
본 명세서의 일 실시상태에 따르면, A13 및 A14는 각각 치환 또는 비치환된 알케닐기이고, 서로 결합하여, 치환 또는 비치환된 벤젠 고리를 형성한다.According to one embodiment of the present disclosure, A13 and A14 are each a substituted or unsubstituted alkenyl group, and combine with each other to form a substituted or unsubstituted benzene ring.
본 명세서의 일 실시상태에 따르면, A13 및 A14는 각각 에테닐기(ethenyl)이고, 서로 결합하여, 벤젠 고리를 형성한다.According to one embodiment of the present disclosure, A13 and A14 are each an ethenyl group and combine with each other to form a benzene ring.
본 명세서의 일 실시상태에 따르면, A14 및 A15는 서로 결합하여, 방향족 고리를 형성한다.According to one embodiment of the present disclosure, A14 and A15 combine with each other to form an aromatic ring.
본 명세서의 일 실시상태에 따르면, A14 및 A15는 서로 결합하여, 벤젠 고리를 형성한다.According to one embodiment of the present disclosure, A14 and A15 combine with each other to form a benzene ring.
본 명세서의 일 실시상태에 따르면, A14 및 A15는 각각 치환 또는 비치환된 알케닐기이고, 서로 결합하여, 치환 또는 비치환된 벤젠 고리를 형성한다.According to one embodiment of the present disclosure, A14 and A15 are each a substituted or unsubstituted alkenyl group and are bonded to each other to form a substituted or unsubstituted benzene ring.
본 명세서의 일 실시상태에 따르면, A14 및 A15는 각각 에테닐기(ethenyl)이고, 서로 결합하여, 벤젠 고리를 형성한다.According to one embodiment of the present disclosure, A14 and A15 are each ethenyl and combine with each other to form a benzene ring.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, n이 1이고, A1 내지 A5 중 어느 하나가 다환의 헤테로아릴기인 경우, 나머지는 수소이다.According to one embodiment of the present invention, when n is 1 and either one of A1 to A5 is a polycyclic heteroaryl group in the general formula (1), the remainder is hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1에 있어서, n이 1이고, A1 내지 A5 중 어느 하나가 카바졸릴기인 경우, 나머지는 수소이다.According to one embodiment of the present invention, when n is 1 and one of A 1 to A 5 is a carbazolyl group in the general formula (1), the other is hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화합물 중에서 선택된다.According to one embodiment of the present disclosure, Formula 1 is selected from the following compounds.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1로 표시되는 화합물은 지연 형광 화합물이다.According to one embodiment of the present invention, the compound represented by Formula 1 is a retardation fluorescent compound.
일반적인 유기발광소자에서 일중항과 삼중항에서 생성되는 엑시톤의 수가 25:75(일중항: 삼중항)의 비율로 생성되며, 엑시톤 이동에 따른 발광 형태에 따라 형광 발광, 인광 발광 및 열활성화 지연형광 발광으로 나눌 수 있다. 상기 인광 발광의 경우 삼중항 여기 상태(excited state)의 엑시톤이 바닥 상태(ground state)로 이동하여 발광하는 것을 의미하고, 상기 형광 발광의 경우 일중항 여기 상태(excited state)의 엑시톤이 바닥 상태(ground state)로 이동하여 발광하게 되는 것을 의미하며, 상기 열활성화 지연형광 발광은 삼중항 여기 상태(excited state)로부터 일중항 여기 상태(excited state)로 역계간전이가 유도되고, 일중항 여기 상태의 엑시톤이 바닥 상태(Ground State)로 이동하여 형광 발광을 일으키는 것을 의미한다.In the general organic light emitting device, the number of excitons generated in the singlet and triplet is generated at a ratio of 25:75 (monomodal: triplet), and depending on the type of emission due to exciton migration, fluorescence emission, It can be divided into luminescence. In the case of the phosphorescent light emission, it means that the exciton of the excited state moves to the ground state and emits light. In the case of the fluorescent emission, the exciton of the excited state is in the ground state ground state, and the light is emitted. The thermal activation delay fluorescent light emission is induced in the excited state from the excited state to the excited state, and the singlet excited state Means that the exciton moves to the ground state to cause fluorescent light emission.
상기 열활성화 지연형광 발광은 발광스펙트럼의 피크 위치가 형광과 같지만 감쇠시간(decay time)이 길다는 점에서 형광 발광과 구분되며, 감쇠시간은 길지만 발광스펙트럼의 피크 위치가 인광 스펙트럼과 S1-T1 에너지의 차이만큼 다르다는 점에서 인광과 구별된다. 이때, S1은 일중항(singlet) 에너지 준위이며, T1는 삼중항(triplet) 에너지 준위이다.The thermal activation delayed fluorescence emission is distinguished from fluorescence emission in that the peak position of the emission spectrum is the same as that of fluorescence but the decay time is long. The decay time is long, but the peak position of the emission spectrum differs from the phosphorescence spectrum and S 1 -T 1 < / RTI > energy difference. Here, S 1 is a singlet energy level, and T 1 is a triplet energy level.
본 명세서의 일 실시상태에 따르면, 제1 전극; 상기 제1 전극에 대향하여 구비된 제2 전극; 및 상기 제1 전극과 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1 층 이상은 전술한 화합물을 포함하는 것인 유기 발광 소자를 제공한다.According to one embodiment of the present disclosure, there is provided a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound described above.
본 명세서의 일 실시상태에 따르면, 본 명세서의 유기 발광 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 발광 소자는 유기물층으로서 정공주입층, 정공수송층, 전자차단층, 발광층, 정공차단층, 전자수송층, 전자주입층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적거나 많은 수의 유기층을 포함할 수 있다.According to one embodiment of the present disclosure, the organic material layer of the organic light emitting device may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, and an electron injecting layer as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include fewer or more organic layers.
예컨대, 본 명세서의 유기 발광 소자의 구조는 도 1에 나타난 것과 같은 구조를 가질 수 있으나 이에만 한정되는 것은 아니다.For example, the structure of the organic light emitting device of the present invention may have a structure as shown in FIG. 1, but is not limited thereto.
도 1에는 기판(20) 위에 제1 전극(30), 발광층(40) 및 제2 전극(50)이 순차적으로 적층된 유기 발광 소자(10)의 구조가 예시 되어 있다. 상기 도 1은 본 명세서의 일 실시상태에 따른 유기 발광 소자의 예시적인 구조이며, 다른 유기물층을 더 포함할 수 있다.1 illustrates a structure of an organic light emitting diode 10 in which a first electrode 30, a light emitting layer 40, and a second electrode 50 are sequentially stacked on a substrate 20. 1 is an exemplary structure of an organic light emitting diode according to an embodiment of the present invention, and may further include another organic layer.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화합물을 포함한다.According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the compound.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화합물을 발광층의 도펀트로서 포함한다.According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the compound as a dopant of the light emitting layer.
본 명세서의 일 실시상태에 따르면, 상기 도펀트의 최대 발광 파장은 480nm 내지 570nm이다.According to one embodiment of the present invention, the maximum emission wavelength of the dopant is 480 nm to 570 nm.
본 명세서의 일 실시상태에 따르면, 상기 도펀트는 녹색 도펀트이다.According to one embodiment of the present disclosure, the dopant is a green dopant.
본 명세서의 일 실시상태에 따르면, 상기 발광층의 발광 물질은 정공 수송층과 전자수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 상기 발광층은 전술한 화합물을 발광층의 도펀트로서 포함하고, 여기 홑겹항에너지 및 여기 삼중항 에너지의 적어도 어느 하나가 상기 화합물의 발광 재료보다 높은 값을 가지고, 정공 수송능, 전자 수송능을 가지며, 또한 발광의 장파장화를 방지하고, 높은 유리전이 온도를 가지는 유기 화합물을 호스트로서 포함할 수 있다.According to one embodiment of the present invention, the light emitting material of the light emitting layer is a material capable of emitting light in a visible light region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, At least one of the excited singlet energy and the excitation triplet energy has a higher value than the light emitting material of the compound and has a hole transporting ability and an electron transporting ability and also prevents a long wavelength of light emission, And may include an organic compound having a high glass transition temperature as a host.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 호스트를 포함한다.According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes a host.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 축합 방향족환 유도체 및 헤테로고리 함유 화합물 중에서 선택되는 어느 하나 이상을 발광층의 호스트로서 포함한다.According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes at least one selected from a condensed aromatic ring derivative and a heterocyclic compound as a host of the light emitting layer.
본 명세서의 일 실시상태에 따르면, 상기 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 플루오렌 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로고리 함유 화합물로는 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되지 않는다.According to one embodiment of the present invention, the condensed aromatic ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a fluorene derivative, a phenanthrene compound, a fluoranthene compound, Include, but are not limited to, carbazole derivatives, dibenzofuran derivatives, ladder furan compounds, and pyrimidine derivatives.
본 명세서의 일 실시상태에 따르면, 상기 호스트는 하기 화합물 중에서 선택되는 어느 하나 이상을 포함할 수 있으나, 이에 한정되지 않는다.According to one embodiment of the present invention, the host may include any one or more selected from the following compounds, but is not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 발광층의 도펀트로서 포함하고, 축합 방향족환 유도체 및 헤테로고리 함유 화합물 중에서 선택되는 어느 하나 이상을 발광층의 호스트로서 포함한다.According to one embodiment of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer contains the compound represented by Formula 1 as a dopant of the light emitting layer, and at least one selected from a condensed aromatic ring derivative and a heterocyclic compound As a host of the light emitting layer.
본 명세서의 일 실시상태에 따르면, 상기 발광층은 상기 도펀트 및 상기 호스트를 1:99 내지 50:50의 중량비로 포함한다.According to one embodiment of the present disclosure, the light emitting layer contains the dopant and the host in a weight ratio of 1:99 to 50:50.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 전술한 화학식 1로 표시되는 화합물을 포함하는 도펀트 및 상기 축합 방향족환 유도체 및 헤테로고리 함유 화합물 중에서 선택되는 어느 하나 이상을 포함하는 호스트를 1:99 내지 50:50의 중량비로 포함한다.According to one embodiment of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer may include at least one selected from the group consisting of the dopant including the compound represented by the above-mentioned formula (1), the condensed aromatic ring derivative, and the heterocyclic compound Containing host at a weight ratio of 1:99 to 50:50.
본 명세서의 유기 발광 소자는 발광층의 도펀트로 본 명세서의 상기 화합물, 즉, 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다.The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that the dopant of the light emitting layer contains the compound of the present specification, that is, the compound represented by the above formula (1).
상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다. When the organic light emitting diode includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
예컨대, 본 명세서의 유기 발광 소자는 기판 상에 제1 전극, 유기물층 및 제2 전극을 순차적으로 적층시킴으로써 제조할 수 있다. 이 때 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 물리 증착 방법(PVD: Physical Vapor Deposition)을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 제1 전극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물층을 형성한 후, 그 위에 제2 전극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 제2 전극 물질부터 유기물층, 제1 전극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수 있다. 또한, 상기 화학식 1로 표시되는 헤테로고리 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.For example, the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate by a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation Forming a first electrode, forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer on the first electrode, and depositing a material usable as a second electrode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate. The heterocyclic compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 제1 전극은 양극이고, 상기 제2 전극은 음극이다. According to one embodiment of the present invention, the first electrode is an anode and the second electrode is a cathode.
본 명세서의 또 하나의 실시상태에 따르면, 상기 제1 전극은 음극이고, 상기 제2 전극은 양극이다. According to another embodiment of the present invention, the first electrode is a cathode and the second electrode is a cathode.
상기 양극 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 본 발명에서 사용될 수 있는 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al, Mg/Ag과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다. The negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al, LiO 2 / Al, and Mg / Ag, but are not limited thereto.
상기 정공주입층은 전극으로부터 정공을 주입하는 층으로, 정공 주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입효과, 발광층 또는 발광재료에 대하여 우수한 정공 주입 효과를 갖고, 발광층에서 생성된 여기자의 전자주입층 또는 전자주입재료에의 이동을 방지하며, 또한, 박막 형성 능력이 우수한 화합물이 바람직하다. 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrin), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone)계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정 되는 것은 아니다. The hole injecting layer is a layer for injecting holes from an electrode. The hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material. A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.
상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer. The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
상기 전자수송층은 전자주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층으로 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이 임의의 원하는 캐소드 물질과 함께 사용할 수 있다. 특히, 적절한 캐소드 물질의 예는 낮은 일함수를 가지고 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이며, 구체적으로 세슘, 바륨, 칼슘, 이테르븀 및 사마륨이고, 각 경우 알루미늄 층 또는 실버층이 뒤따른다.The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Do. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials with a low work function followed by an aluminum or silver layer, specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum or silver layer.
상기 전자주입층은 전극으로부터 전자를 주입하는 층으로, 전자를 수송하는 능력을 갖고, 음극으로부터의 전자주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공 주입층에의 이동을 방지하고, 또한, 박막형성능력이 우수한 화합물이 바람직하다. 구체적으로는 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 함질소 5원환 유도체 등이 있으나, 이에 한정되지 않는다.The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has the ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.
상기 금속 착체 화합물로서는 8-하이드록시퀴놀리나토 리튬, 비스(8-하이드록시퀴놀리나토)아연, 비스(8-하이드록시퀴놀리나토)구리, 비스(8-하이드록시퀴놀리나토)망간, 트리스(8-하이드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-하이드록시퀴놀리나토)알루미늄, 트리스(8-하이드록시퀴놀리나토)갈륨, 비스(10-하이드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-하이드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되지 않는다.Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.
본 명세서에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present invention may be of a top emission type, a back emission type, or a both-side emission type, depending on the material used.
이하, 본 명세서를 구체적으로 설명하기 위해 실시예를 들어 상세하게 설명하기로 한다. 그러나, 본 명세서에 따른 실시예들은 여러 가지 다른 형태로 변형될 수 있으며, 본 명세서의 범위가 아래에서 상술하는 실시예들에 한정되는 것으로 해석되지 않는다. 본 명세서의 실시예들은 당업계에서 평균적인 지식을 가진 자에게 본 명세서를 보다 완전하게 설명하기 위해 제공되는 것이다.Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present specification is not construed as being limited to the embodiments described below. Embodiments of the present disclosure are provided to more fully describe the present disclosure to those of ordinary skill in the art.
[실시예][Example]
[제조예 1][Production Example 1]
가. 화합물 P2의 제조end. Preparation of Compound P2
질소 조건에서 1,4-디브로모-2,5-디플루오로벤젠(P1) 27.2g 및 트리메틸실릴클로라이드(TMSCl) 24g을 테트라하이드로퓨란(THF) 200ml와 혼합하고, -78℃로 냉각하였다. 다음으로, 리튬 다이아이소프로필아마이드(LDA, 2M) 220ml를 천천히 적가하고, -78℃에서 1시간 교반한 뒤 상온으로 천천히 승온하였다. 반응 종료 후, 3%의 묽은 염산과 디클로로메탄으로 추출하고, 무수황산나트륨으로 건조 및 여과하였다. 디클로로메탄을 감압증류한 후, 차가운 메탄올로 세척하여, 33.3g의 흰색 고체를 얻었다.27.2 g of 1,4-dibromo-2,5-difluorobenzene (P1) and 24 g of trimethylsilyl chloride (TMSCl) were mixed with 200 ml of tetrahydrofuran (THF) under nitrogen and cooled to -78 ° C . Next, 220 ml of lithium diisopropyl amide (LDA, 2M) was slowly added dropwise, and the mixture was stirred at -78 캜 for 1 hour and slowly heated to room temperature. After completion of the reaction, the reaction mixture was extracted with 3% diluted hydrochloric acid and dichloromethane, dried over anhydrous sodium sulfate and filtered. The dichloromethane was distilled off under reduced pressure, and then washed with cold methanol to obtain 33.3 g of a white solid.
다음으로, 상기 반응에서 얻은 화합물 33g을 클로로포름 1320ml에 혼합한 후 질소 상태 하에서 30분간 교반 시키고 반응물의 온도를 -78℃까지 냉각하였다. 1mol 아이오딘 모노클로라이드(ICl) 317ml를 천천히 적가하고 동일한 온도에서 1시간 동안 교반한 후, 실온으로 온도를 올려 2시간 동안 교반하였다. 반응 종료 후 소듐싸이오설파이트(Na2S2O3) 수용액으로 반응을 종결시키고, 추출한 뒤 무수황산나트륨으로 건조 및 여과하였다. 에탄올로 재결정을 실시하고 건조하여, 36.5g의 화합물 P2를 얻었다.Next, 33 g of the compound obtained in the above reaction was mixed with 1320 ml of chloroform, stirred under nitrogen for 30 minutes, and cooled to -78 캜. 317 ml of 1 mol of iodine monochloride (ICl) was slowly added dropwise, and the mixture was stirred at the same temperature for 1 hour, then the temperature was raised to room temperature and stirred for 2 hours. After completion of the reaction, the reaction was terminated with an aqueous solution of sodium thiosulfite (Na 2 S 2 O 3 ), followed by extraction with anhydrous sodium sulfate and filtration. Recrystallization was performed with ethanol, and the product was dried to obtain 36.5 g of compound P2.
나. 화합물 P3의 제조I. Preparation of compound P3
상기 화합물 P2(1,4-디브로모-2,5-디플루오로-3,6-디아이오도벤젠)(26.18g, 50mmol) 및 페닐 보론산(12.2g, 100mmol)를 테트라하이드로퓨란(THF) 800ml에 녹였다. 여기에 탄산나트륨(Na2CO3) 2M 용액(500mL) 및 테트라키스(트리페닐포스핀)팔라듐(Pd(PPh3)4, 4.6g, 4mmol)을 넣고 12시간 동안 환류시켰다. 반응이 끝난 후 상온으로 냉각시키고, 생성된 혼합물을 물과 톨루엔으로 3회 추출하였다. 톨루엔 층을 분리한 뒤 황산마그네슘(magnesium sulfate)으로 건조하여 여과한 여과액을 감압 증류하였다. 농축된 화합물을 헥산과 에틸아세테이트를 4:1의 부피비로 혼합한 용액으로 컬럼크로마토그래피 분리하여 20.2g의 화합물 P3를 얻었다. 진공 오븐에서 24시간 건조한 후, 얻어진 고체(P3)는 질량스펙트럼 측정으로 M/Z=422에서 피크가 확인되었다.The compound A solution of P2 (1,4-dibromo-2,5-difluoro-3,6-diiodobenzene) (26.18g, 50mmol) and phenylboronic acid (12.2g, 100mmol) in tetrahydrofuran (THF) Respectively. To this was added a 2 M solution of sodium carbonate (Na 2 CO 3 ) (500 mL) and tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 , 4.6 g, 4 mmol) and refluxed for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the resulting mixture was extracted three times with water and toluene. The toluene layer was separated, dried over magnesium sulfate, filtered and the filtrate was distilled under reduced pressure. The concentrated compound was subjected to column chromatography using a mixture of hexane and ethyl acetate in a volume ratio of 4: 1 to obtain 20.2 g of compound P3. After drying in a vacuum oven for 24 hours, the obtained solid (P3) had a peak at M / Z = 422 as measured by mass spectrometry.
다. 화합물 P4의 제조All. Preparation of compound P4
상기 화합물 P3(14.0g, 33.1mmol)을 N,N-디메틸포름아미드 600ml에 녹였다. 여기에, 시안화구리(CuCN, 6g, 67mmol)를 넣고 질소 조건에서 환류시켰다. 반응이 끝난 후 상온으로 냉각시키고, 생성된 혼합물을 물과 에틸아세테이트로 추출하였다. 에틸아세테이트층을 분리한 뒤 감압증류하여, 화합물을 농축하였다. 다음으로, 테트라하이드로퓨란으로 재결정하여, 화합물 P4 10.4g을 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=316에서 피크가 확인되었다.The compound P3 (14.0 g, 33.1 mmol) was dissolved in 600 ml of N, N-dimethylformamide. To this was added copper cyanide (CuCN, 6 g, 67 mmol) and refluxed under nitrogen. After the reaction was completed, the reaction mixture was cooled to room temperature, and the resulting mixture was extracted with water and ethyl acetate. The ethyl acetate layer was separated and then vacuum distilled to concentrate the compound. Next, recrystallization from tetrahydrofuran gave 10.4 g of compound P4. A peak was confirmed at M / Z = 316 by mass spectrum measurement of the obtained solid.
라. 화합물 1의 제조la. Preparation of Compound (1)
9H-카바졸(2.8g, 17mmol), 포타슘카보네이트(2.4g, 17mmol) 및 디메틸설폭사이드 40ml를 혼합하고 상온 및 질소 조건에서 1시간 교반하였다. 반응 혼합물에 화합물 P4(2.6g, 8.3mmol)를 첨가하고 16시간 동안 50℃에서 교반하였다. 상온으로 식히고 증류수를 적가하여 여과하였다. 증류수로 세정하고 얻어진 고체를 디클로로메탄에 녹이고 유기층을 분리한 후, 황산마그네슘(magnesium sulfate)으로 건조하고, 실리카젤로 여과한 후 농축하였다. 디클로로메탄과 에탄올로 재결정하여 2g의 화합물 1을 제조하였다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=610에서 피크가 확인되었다.9H-carbazole (2.8 g, 17 mmol), potassium carbonate (2.4 g, 17 mmol) and dimethyl sulfoxide (40 ml) were mixed and stirred at room temperature and under nitrogen for 1 hour. To the reaction mixture was added compound P4 (2.6 g, 8.3 mmol) and stirred at 50 < 0 > C for 16 h. The mixture was cooled to room temperature, distilled water was added dropwise, and the mixture was filtered. The organic layer was separated, dried over magnesium sulfate, filtered through silica gel, and concentrated. Recrystallization from dichloromethane and ethanol gave 2 g of compound 1. < 1 > A peak was confirmed at M / Z = 610 by mass spectrum measurement of the obtained solid.
[제조예 2][Production Example 2]
화합물 2의 제조Preparation of Compound 2
9H-카바졸 대신 3,6-디메틸-9H-카바졸을 3.3g, 17mmol을 사용한 것을 제외하고는, 화합물 1과 동일한 방법으로 제조하여, 1.6g의 화합물 2를 제조하였다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=666에서 피크가 확인되었다.Compound 1 was prepared in the same manner as Compound 1, except that 3.3 g, 17 mmol of 3,6-dimethyl-9H-carbazole was used instead of 9H-carbazole. A peak was confirmed at M / Z = 666 by mass spectrum measurement of the obtained solid.
[제조예 3][Production Example 3]
화합물 3의 제조Preparation of Compound 3
9H-카바졸 대신 7,7-디메틸-5,7-다이하이드로인데노[2,1-b]카바졸 4.8g, 17mmol을 사용한 것을 제외하고는, 화합물 1과 동일한 방법으로 제조하여, 1.8g의 화합물 3을 제조하였다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=842에서 피크가 확인되었다.1,7-dihydroindeno [2,1-b] carbazole was used instead of 4-tert-butyl-9H-carbazole as a starting material, 1.8 g Of Compound 3 was prepared. A peak was confirmed at M / Z = 842 by mass spectrum measurement of the obtained solid.
[제조예 4][Production Example 4]
가. 화합물 P5의 제조end. Preparation of compound P5
페닐 보론산을 대신 [1,1'-바이페닐]-2-일 보론산 (19.8g, 100mmol)을 사용한 것을 제외하고는, 화합물 P3 합성과 동일한 방법으로 제조하여 22.8g의 화합물 P5를 제조하였다. 얻어진 고체는 질량스펙트럼 측정으로 M/Z=574에서 피크가 확인되었다.22.8 g of compound P5 was prepared in the same manner as in the synthesis of compound P3 except that [1,1'-biphenyl] -2-ylboronic acid (19.8 g, 100 mmol) was used instead of phenylboronic acid . The obtained solid had a peak at M / Z = 574 as determined by mass spectrometry.
나. 화합물 P6의 제조I. Preparation of compound P6
화합물 P3 대신 화합물 P5 (19.1g, 33.1mmol)를 사용한 것을 제외하고는, 화합물 P4 합성과 동일한 방법으로 제조하여 11.8g의 화합물 P6을 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=468에서 피크가 확인되었다.Compound 11 was prepared in the same manner as in the synthesis of the compound P4 except that the compound P5 (19.1 g, 33.1 mmol) was used in place of the compound P3 to obtain 11.8 g of the compound P6. A peak was observed at M / Z = 468 by mass spectrum measurement of the obtained solid.
다. 화합물 4의 제조All. Preparation of compound 4
P4 대신 P6 (3.9g, 8.3mmol)을 사용한 것을 제외하고는, 화합물 1의 합성과 동일한 방법으로 제조하여 1.6g의 화합물 4를 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=762에서 피크가 확인되었다.Compound 4 was obtained in the same manner as in the synthesis of Compound 1, except that P6 (3.9 g, 8.3 mmol) was used instead of P4. A peak was confirmed at M / Z = 762 by mass spectrum measurement of the obtained solid.
[제조예 5][Production Example 5]
화합물 5의 제조Preparation of Compound 5
9H-카바졸 대신 3,6-디메틸-9H-카바졸을 3.3g, 17mmol을 사용한 것을 제외하고는, 화합물 4과 동일한 방법으로 제조하여, 2.2g의 화합물 5를 제조하였다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=818에서 피크가 확인되었다.2.2 g of Compound 5 was prepared, except that 3.3 g, 17 mmol of 3,6-dimethyl-9H-carbazole was used instead of 9H-carbazole. A peak was observed at M / Z = 818 by mass spectrum measurement of the obtained solid.
[제조예 6][Production Example 6]
화합물 6의 제조Preparation of Compound 6
9H-카바졸 대신 7,7-디메틸-5,7-다이하이드로인데노[2,1-b]카바졸 4.8g, 17mmol을 사용한 것을 제외하고는, 화합물 4와 동일한 방법으로 제조하여, 2.2g의 화합물 6을 제조하였다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=994에서 피크가 확인되었다.Carbazole was prepared in the same manner as in the compound 4 except for using 17.8 mmol of 7,7-dimethyl-5,7-dihydroindeno [2,1-b] carbazole instead of 9H- Of Compound 6 was prepared. A peak was confirmed at M / Z = 994 by mass spectrum measurement of the obtained solid.
[제조예 7][Production Example 7]
가. 화합물 P7의 제조end. Preparation of compound P7
페닐 보론산을 대신 (4-플루오로페닐)보론산 (14.0g, 100mmol)을 사용한 것을 제외하고는, 화합물 P3 합성과 동일한 방법으로 제조하여 20.6g의 화합물 P7을 제조하였다. 얻어진 고체는 질량스펙트럼 측정으로 M/Z=458에서 피크가 확인되었다.(4-fluorophenyl) boronic acid (14.0 g, 100 mmol) was used in place of the phenyl boronic acid, 20.6 g of the compound P7 was prepared. The obtained solid was confirmed by mass spectrometry to have a peak at M / Z = 458.
나. 화합물 P8의 제조I. Preparation of compound P8
화합물 P3 대신 화합물 P7 (15.2g, 33.1mmol)을 사용한 것을 제외하고는, 화합물 P4 합성과 동일한 방법으로 제조하여 9.6g의 화합물 P8을 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=352에서 피크가 확인되었다.9.6 g of the compound P8 was obtained in the same manner as in the synthesis of the compound P4 except that the compound P7 (15.2 g, 33.1 mmol) was used instead of the compound P3. A peak was confirmed at M / Z = 352 by mass spectrum measurement of the obtained solid.
다. 화합물 7의 제조All. Preparation of Compound 7
화합물 P4 대신 화합물 P8 (2.9g, 8.3mmol)을 사용한 것을 제외하고는, 화합물 1의 합성과 동일한 방법으로 제조하여 1.2g의 화합물 7을 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=646에서 피크가 확인되었다.Compound 2 was prepared in the same manner as in the synthesis of Compound 1, except that Compound P8 (2.9 g, 8.3 mmol) was used in place of Compound P4 to obtain 1.2 g of Compound 7. A peak was confirmed at M / Z = 646 by mass spectrum measurement of the obtained solid.
[제조예 8][Production Example 8]
화합물 8의 제조Preparation of Compound 8
9H-카바졸 대신 3,6-디메틸-9H-카바졸(3.3g, 17mmol)을 사용한 것을 제외하고는, 화합물 7과 동일한 방법으로 제조하여, 2.2g의 화합물 8을 제조하였다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=702에서 피크가 확인되었다.2.2g of Compound 8 was prepared in the same manner as Compound 7, except that 3,6-dimethyl-9H-carbazole (3.3g, 17mmol) was used instead of 9H-carbazole. A peak was confirmed at M / Z = 702 by mass spectrum measurement of the obtained solid.
[제조예 9][Production Example 9]
화합물 9의 제조Preparation of Compound 9
9H-카바졸 대신 7,7-디메틸-5,7-다이하이드로인데노[2,1-b]카바졸 4.8g, 17mmol을 사용한 것을 제외하고는, 화합물 7과 동일한 방법으로 제조하여, 2.2g의 화합물 9를 제조하였다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=878에서 피크가 확인되었다.Carbazole was prepared in the same manner as in the compound 7 except that 4.8 g of 17 mmol of 7,7-dimethyl-5,7-dihydroindeno [2,1-b] carbazole was used instead of 9H- Of Compound 9 was prepared. A peak was confirmed at M / Z = 878 by mass spectrum measurement of the obtained solid.
[제조예 10][Production Example 10]
가. 화합물 P9의 제조end. Preparation of Compound P9
페닐 보론산을 대신 (4-사이아노페닐)보론산 (14.7g, 100mmol)을 사용한 것을 제외하고는, 화합물 P3 합성과 동일한 방법으로 제조하여 20.0g의 화합물 P9을 제조하였다. 얻어진 고체는 질량스펙트럼 측정으로 M/Z=472에서 피크가 확인되었다.(4-cyanophenyl) boronic acid (14.7 g, 100 mmol) was used instead of phenylboronic acid in place of the compound P3. The obtained solid was confirmed by mass spectrometry to have a peak at M / Z = 472.
나. 화합물 P10의 제조I. Preparation of compound P10
P3 대신 P9 (15.7g, 33.1mmol)을 사용한 것을 제외하고는, 화합물 P4 합성과 동일한 방법으로 제조하여 10.2g의 화합물 P10을 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=366에서 피크가 확인되었다.Compound P10 was prepared in the same manner as in the synthesis of compound P4 except that P9 (15.7 g, 33.1 mmol) was used instead of P3. A peak was confirmed at M / Z = 366 by mass spectrum measurement of the obtained solid.
다. 화합물 10의 제조All. Preparation of Compound 10
P4 대신 P10 (3.0g, 8.3mmol)을 사용한 것을 제외하고는, 화합물 1의 합성과 동일한 방법으로 제조하여 1.4g의 화합물 8을 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=660에서 피크가 확인되었다.1.4 g of Compound 8 was obtained in the same manner as in the synthesis of Compound 1, except that P10 (3.0 g, 8.3 mmol) was used instead of P4. A peak was confirmed at M / Z = 660 by mass spectrum measurement of the obtained solid.
[제조예 11][Production Example 11]
화합물 11의 제조Preparation of Compound 11
9H-카바졸 대신 3,6-디메틸-9H-카바졸을 3.3g, 17mmol을 사용한 것을 제외하고는, 화합물 10과 동일한 방법으로 제조하여, 2.0g의 화합물 11을 제조하였다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=716에서 피크가 확인되었다.Compound 11 was prepared in the same manner as Compound 10, except that 3.3 g, 17 mmol of 3,6-dimethyl-9H-carbazole was used instead of 9H-carbazole. A peak was confirmed at M / Z = 716 by mass spectrum measurement of the obtained solid.
[제조예 12][Production Example 12]
화합물 12의 제조Preparation of Compound 12
9H-카바졸 대신 7,7-디메틸-5,7-다이하이드로인데노[2,1-b]카바졸 4.8g, 17mmol을 사용한 것을 제외하고는, 화합물 10과 동일한 방법으로 제조하여, 2.4g의 화합물 12를 제조하였다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=892에서 피크가 확인되었다.Carbazole was prepared in the same manner as in Compound 10, except that 4.8 g, 17 mmol of 7,7-dimethyl-5,7-dihydroindeno [2,1-b] Of Compound 12 was prepared. The peak of the obtained solid was confirmed by M / Z = 892 by mass spectrum measurement.
[제조예 13][Production Example 13]
가. 화합물 P11의 제조end. Preparation of Compound P11
페닐 보론산을 대신 (4-(털트-부틸)페닐)보론산 (17.8g, 100mmol)을 사용한 것을 제외하고는, 화합물 P3 합성과 동일한 방법으로 제조하여 화합물 P11 20.4g을 제조하였다. 얻어진 고체는 질량스펙트럼 측정으로 M/Z=534에서 피크가 확인되었다.(Tart-butyl) phenyl) boronic acid (17.8 g, 100 mmol) was used in place of the phenyl boronic acid in place of the compound P3. The obtained solid was confirmed by mass spectrometry to have a peak at M / Z = 534.
나. 화합물 P12의 제조I. Preparation of compound P12
P3 대신 P11 (15.7g, 33.1mmol)을 사용한 것을 제외하고는, 화합물 P4 합성과 동일한 방법으로 제조하여 10.4g의 화합물 P12를 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=428에서 피크가 확인되었다.10.4 g of the compound P12 was obtained in the same manner as in the synthesis of the compound P4 except that P11 (15.7 g, 33.1 mmol) was used instead of P3. A peak was confirmed at M / Z = 428 by mass spectrum measurement of the obtained solid.
다. 화합물 13의 제조All. Preparation of Compound 13
P4 대신 P12 (3.6g, 8.3mmol)을 사용한 것을 제외하고는, 화합물 1의 합성과 동일한 방법으로 제조하여 화합물 13 1.4g을 얻었다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=722에서 피크가 확인되었다.Except that P12 (3.6 g, 8.3 mmol) was used in place of P4, 1.4 g of Compound 13 was obtained. A peak was confirmed at M / Z = 722 by mass spectrum measurement of the obtained solid.
[제조예 14][Production Example 14]
화합물 14의 제조Preparation of Compound 14
9H-카바졸 대신 3,6-디메틸-9H-카바졸을 3.3g, 17mmol을 사용한 것을 제외하고는, 화합물 13과 동일한 방법으로 제조하여, 화합물 14 2.0g을 제조하였다. 얻어진 고체의 질량 스펙트럼 측정에 의해 M/Z=778에서 피크가 확인되었다.Carbazole was prepared in the same manner as in Compound 13, except that 3.3 g of 3, 6-dimethyl-9H-carbazole was used instead of 9-carbaldehyde, and 2.0 g of Compound 14 was prepared. A peak was observed at M / Z = 778 by mass spectrum measurement of the obtained solid.
[실시예 1] [Example 1]
유기 발광 소자 제조Organic Light Emitting Device Manufacturing
먼저 40mm × 40mm × 두께 0.5mm의 ITO 전극 부착 유리 기판을 이소프로필알코올, 아세톤 및 탈이온수(DI Water)로 5분 동안 초음파 세정을 진행한 후 100℃ 오븐에 건조하였다. 기판 세정 후 진공 상태에서 2분 동안 O2 플라즈마 처리하고 상부에 다른 층들을 증착하기 위하여 증착 챔버로 이송하였다. 약 10-7Torr 진공 하에 가열 보트로부터 증발에 의해, 유리 기판의 ITO 상에 다음과 같은 순서로 유기물층을 증착하였다. 이때, 유기물의 증착 속도는 10nm/s로 설정하였다. First, a glass substrate with a 40 mm x 40 mm x 0.5 mm thick ITO electrode was ultrasonically cleaned with isopropyl alcohol, acetone and DI water for 5 minutes, and then dried in an oven at 100 ° C. After the substrate was cleaned, it was subjected to an O 2 plasma treatment in a vacuum for 2 minutes and transferred to a deposition chamber for deposition of other layers on the top. An organic layer was deposited on the ITO of the glass substrate by evaporation from a heated boat under a vacuum of about 10 -7 Torr in the following order. At this time, the deposition rate of the organic material was set at 10 nm / s.
1. 정공주입층(HIL): HAT-CN, 두께 10nm1. Hole injection layer (HIL): HAT-CN, thickness 10 nm
2. 정공수송층(HTL): NPB, 두께 75nm2. Hole transport layer (HTL): NPB, thickness 75 nm
3. 전자차단층(EBL): mCBP, 두께 15nm3. Electron barrier layer (EBL): mCBP, thickness 15 nm
4. 발광물질층(EML): TH1 90중량%, 화합물 1 10중량%, 두께 35nm4. Emissive material layer (EML): TH1 90 wt%, Compound 1 10 wt%, thickness 35 nm
5. 정공차단층(HBL): B3PYMPM, 두께 10nm5. Hole blocking layer (HBL): B3PYMPM, thickness 10 nm
6. 전자수송층(ETL): TPBi, 두께 25nm6. Electron transport layer (ETL): TPBi, thickness 25 nm
7. 전자주입층(EIL): LiF, 두께 80nm7. Electron Injection Layer (EIL): LiF, thickness 80 nm
8. 음극: Al, 두께 100nm8. Cathode: Al, thickness 100 nm
CPL(capping layer)을 성막한 뒤에 유리로 인캡슐레이션하였다. 이러한 층들의 증착 후 피막 형성을 위해 증착 챔버에서 건조 박스 내로 옮기고 후속적으로 UV 경화 에폭시 및 수분 게터(getter)를 사용하여 인캡슐레이션하였다. A capping layer (CPL) was formed and encapsulated with glass. After deposition of these layers, the film was transferred from the deposition chamber into a dry box for subsequent film formation and subsequently encapsulated using a UV cured epoxy and a getter.
[실시예 2][Example 2]
발광층의 도펀트로 화합물 1 대신 화합물 2를 사용하여 유기 발광 소자를 제조하였다.An organic light emitting device was prepared using Compound 2 instead of Compound 1 as a dopant in the light emitting layer.
[실시예 3][Example 3]
발광층의 도펀트로 화합물 1 대신 화합물 3을 사용하여 유기 발광 소자를 제조하였다.An organic light emitting device was prepared using Compound 3 instead of Compound 1 as a dopant in the light emitting layer.
[실시예 4][Example 4]
발광층의 도펀트로 화합물 1 대신 화합물 4를 사용하여 유기 발광 소자를 제조하였다.An organic light emitting device was prepared using Compound 4 instead of Compound 1 as a dopant of the light emitting layer.
[실시예 5][Example 5]
발광층의 도펀트로 화합물 1 대신 화합물 5를 사용하여 유기 발광 소자를 제조하였다.An organic light emitting device was prepared using Compound 5 instead of Compound 1 as a dopant in the light emitting layer.
[실시예 6][Example 6]
발광층의 도펀트로 화합물 1 대신 화합물 6을 사용하여 유기 발광 소자를 제조하였다.An organic light emitting device was prepared by using Compound 6 instead of Compound 1 as a dopant in the light emitting layer.
[실시예 7][Example 7]
발광층의 도펀트로 화합물 1 대신 화합물 8을 사용하여 유기 발광 소자를 제조하였다.An organic light emitting device was prepared using Compound 8 instead of Compound 1 as a dopant in the light emitting layer.
[실시예 8][Example 8]
발광층의 도펀트로 화합물 1 대신 화합물 9를 사용하여 유기 발광 소자를 제조하였다.An organic light emitting device was prepared using Compound 9 instead of Compound 1 as a dopant in the light emitting layer.
[실시예 9][Example 9]
발광층의 도펀트로 화합물 1 대신 화합물 10을 사용하여 유기 발광 소자를 제조하였다.An organic light emitting device was prepared by using Compound 10 instead of Compound 1 as a dopant in the light emitting layer.
[실시예 10][Example 10]
발광층의 도펀트로 화합물 1 대신 화합물 13을 사용하여 유기 발광 소자를 제조하였다.An organic light emitting device was prepared using Compound 13 instead of Compound 1 as a dopant in the light emitting layer.
[실시예 11][Example 11]
발광층의 도펀트로 화합물 1 대신 화합물 14를 사용하여 유기 발광 소자를 제조하였다.An organic light emitting device was prepared by using Compound 14 instead of Compound 1 as a dopant of the light emitting layer.
[비교예 1][Comparative Example 1]
발광층의 도펀트로 화합물 1 대신 하기 화합물 D1을 사용하여 유기 발광 소자를 제조하였다.An organic luminescent device was prepared using the following Compound D1 instead of Compound 1 as a dopant in the light emitting layer.
[비교예 2][Comparative Example 2]
발광층의 도펀트로 화합물 1 대신 하기 화합물 D2를 사용하여 유기 발광 소자를 제조하였다.An organic luminescent device was prepared using the following compound D2 instead of compound 1 as a dopant in the light emitting layer.
[비교예 3][Comparative Example 3]
발광층의 도펀트로 화합물 1 대신 하기 화합물 D3를 사용하여 유기 발광 소자를 제조하였다.An organic light emitting device was prepared using the following compound D3 instead of Compound 1 as a dopant of the light emitting layer.
[비교예 4][Comparative Example 4]
발광층의 도펀트로 화합물 1 대신 하기 화합물 D4를 사용하여 유기 발광 소자를 제조하였다.An organic luminescent device was prepared using the following compound D4 instead of compound 1 as a dopant in the light emitting layer.
[비교예 5][Comparative Example 5]
발광층의 도펀트로 화합물 1 대신 하기 화합물 D5를 사용하여 유기 발광 소자를 제조하였다.An organic light emitting device was prepared using the following compound D5 instead of compound 1 as a dopant of the light emitting layer.
[비교예 6][Comparative Example 6]
발광층의 도펀트로 화합물 1 대신 하기 화합물 D6을 사용하여 유기 발광 소자를 제조하였다.An organic luminescent device was prepared using the following compound D6 instead of compound 1 as a dopant in the light emitting layer.
[실험예 1][Experimental Example 1]
지연 형광 도펀트가 10 중량%로 도핑된 발광층의 두께를 35nm로 하여 제조된 실시예 1 내지 실시예 11과 비교예 1 내지 6에서 각각 제조된 유기 발광 소자를 대상으로 물성을 측정하였다. 전류 공급원(KEITHLEY) 및 광도계(PR 650)를 사용하여 실온에서 소자 특성을 평가하였다. 각각의 유기 발광 소자에 대하여 10㎃/㎠의 전류밀도에서 측정한 구동 전압(V), 전류효율(cd/A), 전력효율(lm/W), 휘도(cd/m2), 3000 nit에서 밝기가 95%로 감소될 때까지의 시간(T95)을 측정하였다. 측정 결과를 하기 표 1에 나타내었다. The properties of the organic luminescent devices prepared in Examples 1 to 11 and Comparative Examples 1 to 6, respectively, in which the thickness of the light emitting layer doped with the retardation fluorescent dopant of 10 wt% was 35 nm, were measured. The device characteristics were evaluated at room temperature using a current source (KEITHLEY) and a photometer (PR 650). (Cd / A), power efficiency (lm / W), luminance (cd / m < 2 >) measured at a current density of 10 mA / cm & The time (T 95 ) until the brightness was reduced to 95% was measured. The measurement results are shown in Table 1 below.
화합물compound | 구동 전압(V)The driving voltage (V) | 전류효율(cd/A)Current efficiency (cd / A) | 전력효율(lm/W)Power Efficiency (lm / W) | 휘도(cd/m2)Brightness (cd / m 2 ) | T95 T 95 | |
실시예 1Example 1 | 1One | 44 | 60.260.2 | 47.3 47.3 | 60206020 | 420420 |
실시예 2Example 2 | 22 | 44 | 61.861.8 | 48.5 48.5 | 61806180 | 440440 |
실시예 3Example 3 | 33 | 4.54.5 | 55.355.3 | 38.6 38.6 | 55305530 | 280280 |
실시예 4Example 4 | 44 | 4.54.5 | 55.655.6 | 38.8 38.8 | 55605560 | 310310 |
실시예 5Example 5 | 55 | 4.64.6 | 5252 | 35.5 35.5 | 52005200 | 240240 |
실시예 6Example 6 | 66 | 4.54.5 | 52.852.8 | 36.9 36.9 | 52805280 | 230230 |
실시예 7Example 7 | 88 | 4.74.7 | 6060 | 40.1 40.1 | 60006000 | 230230 |
실시예 8Example 8 | 99 | 4.14.1 | 6060 | 46.0 46.0 | 60006000 | 420420 |
실시예 9Example 9 | 1010 | 4.54.5 | 56.456.4 | 39.4 39.4 | 56405640 | 360360 |
실시예 10Example 10 | 1313 | 4.64.6 | 54.854.8 | 37.4 37.4 | 54805480 | 140140 |
실시예 11Example 11 | 1414 | 4.64.6 | 53.253.2 | 36.3 36.3 | 53205320 | 160160 |
비교예 1Comparative Example 1 | D1D1 | 6.86.8 | 4646 | 21.3 21.3 | 46004600 | 110110 |
비교예 2Comparative Example 2 | D2D2 | 6.26.2 | 4040 | 20.3 20.3 | 40004000 | 120120 |
비교예 3Comparative Example 3 | D3D3 | 66 | 41.841.8 | 21.9 21.9 | 41804180 | 120120 |
비교예 4Comparative Example 4 | D4D4 | 8.08.0 | 32.232.2 | 12.612.6 | 32003200 | 8080 |
비교예 5Comparative Example 5 | D5D5 | 5.45.4 | 44.844.8 | 26.126.1 | 44804480 | 120120 |
비교예 6Comparative Example 6 | D6D6 | 5.65.6 | 45.045.0 | 25.225.2 | 45004500 | 120120 |
본 발명의 헤테로고리 화합물을 사용한 실시예 1 내지 11의 소자는 비교예 1 내지 6의 소자와 비교해서, 구동 전압이 낮고, 전류 효율이 높고, 전력 효율이 높고, 휘도가 높으며, 수명 특성이 높다.The devices of Examples 1 to 11 using the heterocyclic compound of the present invention had lower driving voltage, higher current efficiency, higher power efficiency, higher luminance, and higher lifetime characteristics than the devices of Comparative Examples 1 to 6 .
Claims (14)
- 하기 화학식 1로 표시되는 화합물:A compound represented by the following formula (1):[화학식 1][Chemical Formula 1]상기 화학식 1에 있어서,In Formula 1,A1 내지 A5는 서로 같거나 상이하고, 각각 독립적으로 수소; 할로겐기; 시아노기; 할로알킬기; 알킬기; 알케닐기; 할로알콕시기; 할로겐기, 시아노기, 할로알킬기, 알킬기, 또는 할로알콕시기로 치환 또는 비치환된 아릴기; 또는 헤테로아릴기이거나, 인접한 기는 서로 결합하여 방향족 고리를 형성하며,A1 to A5 are the same or different from each other, and each independently hydrogen; A halogen group; Cyano; Haloalkyl; An alkyl group; An alkenyl group; A haloalkoxy group; An aryl group substituted or unsubstituted with a halogen group, a cyano group, a haloalkyl group, an alkyl group, or a haloalkoxy group; Or a heteroaryl group, or adjacent groups are bonded to each other to form an aromatic ring,R1 내지 R8 및 R11 내지 R18은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 니트로기; 히드록시기; 카르보닐기; 에스테르기; 이미드기; 아미드기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기는 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R1 to R8 and R11 to R18 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups may be bonded to each other to form a substituted or unsubstituted ring,n은 1 또는 2이며,n is 1 or 2,n이 2인 경우, 복수 개의 괄호 내의 구조는 서로 같거나 상이하고,When n is 2, the structures in the plurality of parentheses are equal to or different from each other,n이 1이고, 상기 A1 내지 A5 중 어느 하나가 헤테로아릴기인 경우, 나머지는 수소이다.When n is 1, and any one of A1 to A5 is a heteroaryl group, the remainder is hydrogen.
- 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 1-1 또는 1-2로 표시되는 것인 화합물:The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 1-1 or 1-2:[화학식 1-1][Formula 1-1][화학식 1-2][Formula 1-2]상기 화학식 1-1 및 1-2에 있어서,In the above formulas 1-1 and 1-2,A1 내지 A5, R1 내지 R8 및 R11 내지 R18의 정의는 상기 화학식 1에서 정의한 바와 동일하고, The definitions of A 1 to A 5, R 1 to R 8 and R 11 to R 18 are as defined in the above formula (1)A11 내지 A15는 서로 같거나 상이하고, 각각 독립적으로 수소; 할로겐기; 시아노기; 할로알킬기; 알킬기; 알케닐기; 할로알콕시기; 할로겐기, 시아노기, 할로알킬기, 알킬기, 또는 할로알콕시기로 치환 또는 비치환된 아릴기; 또는 헤테로아릴기이거나, 인접한 기는 서로 결합하여 방향족 고리를 형성한다.A11 to A15 are the same or different and each independently hydrogen; A halogen group; Cyano; Haloalkyl; An alkyl group; An alkenyl group; A haloalkoxy group; An aryl group substituted or unsubstituted with a halogen group, a cyano group, a haloalkyl group, an alkyl group, or a haloalkoxy group; Or a heteroaryl group, or adjacent groups are bonded to each other to form an aromatic ring.
- 청구항 1에 있어서, 상기 R1 내지 R8 및 R11 내지 R18는 서로 같거나 상이하고, 각각 독립적으로 수소; 또는 알킬기인 것인 화합물.The compound according to claim 1, wherein R1 to R8 and R11 to R18 are the same or different and each independently hydrogen; Or an alkyl group.
- 청구항 1에 있어서, 상기 R1 내지 R8 및 R11 내지 R18 중 인접한 기는 서로 결합하여, 알킬기로 치환된 탄화수소고리를 형성하는 것인 화합물.The compound according to claim 1, wherein adjacent groups of R1 to R8 and R11 to R18 are bonded to each other to form a hydrocarbon ring substituted with an alkyl group.
- 청구항 1에 있어서, 상기 화학식 1로 표시되는 화합물은 지연 형광 화합물인 것인 화합물.The compound according to claim 1, wherein the compound represented by Formula 1 is a retardation fluorescent compound.
- 제1 전극; 상기 제1 전극에 대향하여 구비된 제2 전극; 및 상기 제1 전극과 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1 층 이상은 청구항 1 내지 6 중 어느 한 항의 화합물을 포함하는 것인 유기 발광 소자.A first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a compound according to any one of claims 1 to 6.
- 청구항 7에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic light emitting device according to claim 7, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound.
- 청구항 7에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화합물을 발광층의 도펀트로서 포함하는 것인 유기 발광 소자.The organic light emitting device according to claim 7, wherein the organic layer includes a light emitting layer, and the light emitting layer includes the compound as a dopant of the light emitting layer.
- 청구항 9에 있어서, 상기 도펀트의 최대 발광 파장은 480nm 내지 570nm인 것인 유기 발광 소자.The organic light emitting device according to claim 9, wherein the maximum emission wavelength of the dopant is from 480 nm to 570 nm.
- 청구항 7에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 축합 방향족환 유도체 및 헤테로고리 함유 화합물 중에서 선택되는 어느 하나 이상을 발광층의 호스트로서 포함하는 것인 유기 발광 소자.The organic light emitting device according to claim 7, wherein the organic layer includes a light emitting layer, and the light emitting layer includes at least one selected from a condensed aromatic ring derivative and a heterocyclic compound as a host of the light emitting layer.
- 청구항 7에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화합물을 발광층의 도펀트로서 포함하고, 축합 방향족환 유도체 및 헤테로고리 함유 화합물 중에서 선택되는 어느 하나 이상을 발광층의 호스트로서 포함하는 것인 유기 발광 소자.The organic electroluminescent device according to claim 7, wherein the organic material layer includes a light emitting layer, the light emitting layer contains the compound as a dopant of the light emitting layer, and includes at least one selected from a condensed aromatic ring derivative and a heterocyclic- Organic light emitting device.
- 청구항 13에 있어서, 상기 발광층은 상기 도펀트 및 상기 호스트를 1: 99 내지 50: 50의 중량비로 포함하는 것인 유기 발광 소자.14. The organic light emitting device according to claim 13, wherein the light emitting layer includes the dopant and the host in a weight ratio of 1:99 to 50:50.
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