WO2015163584A1 - Novel compound and light emitting element comprising same - Google Patents
Novel compound and light emitting element comprising same Download PDFInfo
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- WO2015163584A1 WO2015163584A1 PCT/KR2015/002781 KR2015002781W WO2015163584A1 WO 2015163584 A1 WO2015163584 A1 WO 2015163584A1 KR 2015002781 W KR2015002781 W KR 2015002781W WO 2015163584 A1 WO2015163584 A1 WO 2015163584A1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 179
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- 238000000034 method Methods 0.000 claims description 25
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- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000006059 cover glass Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Images
Classifications
-
- 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
- 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
Definitions
- the present invention relates to a novel compound and a light emitting device comprising the same.
- Organic Light-Emitting Diode is basically a structure in which an organic thin film including an organic light emitting layer is sandwiched between two electrodes, at least one of the two electrodes being transparent, and a suitable voltage between the two electrodes.
- the organic light emitting diode is a kind of organic electronic device utilizing light emitted from the visible light region from the organic light emitting layer.
- Such a light emitting device is basically a very thin device having a thickness of several micrometers or less, and is a self-light emitting device that emits light directly from the device itself. Therefore, the response speed is high and the viewing angle is wide as a display device.
- the manufacturing process is simple, the flexible device using the organic thin film can be realized, and in addition to the vacuum process, in some cases, the device can be realized through the printing process from the solution state. Is getting.
- the light emitting device has been applied as a component to be applied to a low current / low output mobile products, but in recent years, its application range has been gradually extended to the high current / high output field, high brightness / high reliability is required accordingly.
- various methods for improving the luminous efficiency of light emitting devices have been studied.
- Patent Document 1 relates to a light emitting device comprising PEDOT / PSS as a hole transporting material, wherein the composition comprising PEDOT / PSS has a medium ionization potential slightly higher than 4.8 eV (between the ionization potential of the anode and the ionization potential of the light emitter). Median of This occurs as the composition induces holes injected from the anode to reach the HOMO level of the organic light emitting material or hole transport material.
- Patent Document 2 relates to a composition containing PEDOT / PSS, the composition has the advantage that can be a solution process such as inkjet printing can be manufactured more easily.
- the composition uses an excessive amount of PSS (i.e., an amount exceeding the amount required to stabilize the charge on the PEDOT), which not only prolongs the life of the light emitting device but also prevents the precipitation of the PSS from the PEDOT solution. have.
- the composition used in the light emitting device has a strong acidity by including an excess of PSS, such a strong acid is etched indium tin oxide (ITO) to remove indium, tin and oxygen components Problems such as release into the PEDOT, degradation of the light emitting polymer, and the like.
- ITO indium tin oxide
- Patent Document 1 European Patent No. 0,686,662;
- Patent Document 2 US Patent No. 6,605,823.
- An object of the present invention is to provide a compound capable of improving the luminous efficiency and lifespan of the light emitting device.
- Another object of the present invention is to provide a light emitting device including the compound, the luminous efficiency is increased, and the light emitting life is improved.
- Still another object of the present invention is to provide an electronic device including the light emitting device.
- R 1 and R 2 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms;
- L a and L b are each independently a single bond or an arylene group having 6 to 30 carbon atoms
- Ar 1 , Ar 2 and Ar 3 are each independently hydrogen or an aryl group having 6 to 30 carbon atoms.
- a light emitting layer disposed between the first electrode and the second electrode
- a hole transport layer disposed between the first electrode and the light emitting layer
- a light emitting device is disposed between a hole transporting layer and a light emitting layer, and includes a blocking layer including a compound represented by Formula 1 below:
- R 1 , R 2 , L a , L b , Ar 1 , Ar 2 and Ar 3 are as defined above.
- the present invention provides an electronic device including the light emitting device.
- the light emitting device includes a blocking layer containing the compound represented by Formula 1, and thus has excellent luminous efficiency and light emitting life as compared to a conventional light emitting device having no blocking layer, and thus displays using a light emitting device. It can be used easily for electronic devices, such as an apparatus and a lighting apparatus.
- FIG. 1 is an image showing the structure of a light emitting device manufactured in one embodiment according to the present invention.
- FIG. 2 is an image showing the structure of a light emitting device manufactured in another embodiment according to the present invention.
- the terms "comprises” or “having” are intended to indicate that there is a feature, number, step, operation, component, part, or combination thereof described in the specification, and one or more other features. It is to be understood that the present invention does not exclude the possibility of the presence or the addition of numbers, steps, operations, components, components, or a combination thereof.
- alkyl group means a functional group derived from a saturated hydrocarbon in a linear or branched form.
- alkyl group for example, methyl group (ethyl group), ethyl group (ethyl group), n-propyl group (n-propyl group), isopropyl group (iso-propyl group), n-butyl group (n -butyl group, sec-butyl group, t-butyl group, tert-butyl group, n-pentyl group, 1,1-dimethylpropyl group (1,1- dimethylpropyl group), 1,2-dimethylpropyl group (1,2-dimethylpropyl group), 2,2-dimethylpropyl group (2,2-dimethylpropyl group), 1-ethylpropyl group (1-ethylpropyl group), 2- 2-ethylpropyl group, n-hexyl group, 1-methyl-2-ethylpropyl group, 1-ethyl-2-methylpropyl group (1-ethyl-2-methylpropyl group (1-ethyl
- alkyl group may have 1 to 20 carbon atoms, for example, 1 to 12 carbon atoms, 1 to 6 carbon atoms, or 1 to 4 carbon atoms.
- aryl group means a monovalent substituent derived from an aromatic hydrocarbon.
- the "aryl group” for example, a phenyl group (phenyl group), naphthyl group (naphthyl group), anthracenyl group (anthracenyl group), phenanthryl group (phenanthryl group) naphthacenyl group (naphthacenyl group), tolyl group (tolyl group), biphenyl group, terphenyl group, terphenyl group, chrycenyl group, spirobifluorenyl group, fluoranthenyl group, fluorenyl group ( fluorenyl group, perylenyl group, indenyl group, indenyl group, azulenyl group, heptarenyl group, heparenyl group, phenalenyl group, phenanthrenyl group Etc.
- a phenyl group phenyl group
- naphthyl group naphthyl group
- the "aryl group” may have 6 to 30 carbon atoms, for example, 6 to 20 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms.
- heteroaryl group means “aromatic heterocycle” or “heterocyclic” derived from a monocyclic or condensed ring.
- the “heteroaryl group” is a hetero atom, at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se) and silicon (Si), for example, one, two Dogs, three or four.
- the "heteroaryl group” for example, pyrrolyl group (pyrrolyl group), pyridyl group (pyridyl group), pyridazinyl group (pyridazinyl group), pyrimidinyl group, pyrazinyl group (pyrazinyl group) ), Triazolyl group, tetrazolyl group, benzotriazolyl group, benzotriazolyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group ( benzimidazolyl group, indolyl group, isoindolyl group, indodolyl group, indolinzinyl group, purinyl group, purinyl group, indazolyl group, quinolyl group ), Isoquinolinyl group (isoquinolinyl group), quinolizinyl group (quinolizinyl group), phthalazinyl group (phthalazine)
- thiazolyl group (thiazolyl group), isothiazolyl group (isothiazolyl group), benzothiazolyl group (benzothiazolyl group), benzothiadiazolyl group (benzothiadiazolyl group), phenothia Phenothiazinyl group, isoxazolyl group, furazanyl group, furazanyl group, phenoxazinyl group, oxazolyl group, oxazolyl group, benzoxazolyl group, Oxadiazolyl group, pyrazoloxazolyl group, imidazothiazolyl group, thienofuranyl group, furopyrrolyl group, pyridoxazinyl group and compounds containing at least two or more heteroatoms such as (pyridoxazinyl group).
- heteroaryl group may have 2 to 20 carbon atoms, for example, 3 to 19 carbon atoms, 4 to 15 carbon atoms, or 5 to 11 carbon atoms.
- the heteroaryl group may have a ring member of 5 to 21.
- cycloalkyl group means a substituent derived from a monocyclic saturated hydrocarbon.
- cycloalkyl group examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloheptyl group, Cyclooctyl group etc. are mentioned.
- cycloalkyl group may have 3 to 20 carbon atoms, for example, 3 to 12 carbon atoms, or 3 to 6 carbon atoms.
- arylene group may mean a divalent substituent derived from the aryl group described above.
- heteroarylene group may refer to a divalent substituent derived from the heteroaryl group described above.
- the present invention provides a compound which can improve the luminous efficiency of the light emitting device and improve the light emitting life and a light emitting device comprising the same.
- the light emitting devices developed to date have low power efficiency and short lifespan.
- various compounds have been developed as materials of the light emitting device, but there are limitations in manufacturing a light emitting device that satisfies both the light emitting efficiency and the light emitting lifetime.
- the present invention proposes a light emitting device having a structure including a blocking layer including a compound represented by Chemical Formula 1, which can improve light emission efficiency and light emission life, and an electronic device including the same.
- the light emitting device according to the present invention is provided with a blocking layer containing the compound represented by the formula (1), it is excellent in luminous efficiency and light emitting life compared to the conventional general light emitting device without a blocking layer. Therefore, the light emitting device according to the present invention can be easily used in an electronic device such as a display device and a lighting device using the light emitting device.
- R 1 and R 2 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms;
- L a and L b are each independently a single bond or an arylene group having 6 to 30 carbon atoms
- Ar 1 , Ar 2 and Ar 3 are each independently hydrogen or an aryl group having 6 to 30 carbon atoms.
- R 1 and R 2 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms;
- L a and L b are each independently a single bond or an arylene group having 6 to 14 carbon atoms;
- Ar 1 is hydrogen
- Ar 2 and Ar 3 may be independently hydrogen or an aryl group having 6 to 20 carbon atoms.
- the compound represented by Formula 1 may be selected from compounds having the structures of Formulas a-1 to a-27:
- R 1 and R 2 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms;
- L a and L b are each independently a single bond or an arylene group having 6 to 14 carbon atoms;
- Ar 1 is an aryl group having 6 to 30 carbon atoms
- Ar 2 and Ar 3 may be independently hydrogen or an aryl group having 6 to 20 carbon atoms.
- Ar 1 may be a phenyl group or a biphenyl group.
- the compound represented by Formula 1 may be selected from compounds having the structures of Formulas b-1 to b-54:
- Ar 1 may be a naphthyl group or a phenanthrene group.
- the compound represented by Formula 1 may be selected from compounds having the structures of Formulas c-1 to c-54:
- a light emitting layer disposed between the first electrode and the second electrode
- a hole transport layer disposed between the first electrode and the light emitting layer
- a light emitting device is disposed between a hole transporting layer and a light emitting layer, and includes a blocking layer including a compound represented by Formula 1 below:
- R 1 , R 2 , L a , L b , Ar 1 , Ar 2 and Ar 3 are as defined above.
- the light emitting device As the application range of the light emitting device is expanded to the high current / high power field, it is required to increase the light emitting efficiency and the light emitting lifetime of the light emitting device. In this case, the light emission efficiency and light emission life can be improved only when the hole and the electron in the light emitting layer are smoothly combined.
- the electron mobility of the organic material is generally larger than the hole mobility, electrons injected from the second electrode may overflow the light emitting layer to the hole transporting layer, thereby causing holes and electrons in the light emitting layer.
- the coupling efficiency of can be reduced. Therefore, in order to efficiently combine holes and electrons in the light emitting layer, the electrons injected from the second electrode must be prevented from leaving the light emitting layer, and the excitons formed in the light emitting layer must be prevented from being diffused or separated.
- the light emitting device may have a structure in which a blocking layer including a compound represented by Formula 1 is introduced between the hole transporting layer and the light emitting layer.
- the blocking layer according to the present invention comprises a compound represented by the formula (1), the electrons injected from the second electrode flows into the hole transport layer via the light emitting layer, or the excitons formed in the light emitting layer is diffused in the direction of the first electrode and the ratio Light emission can be prevented from disappearing.
- the excitons formed in the light emitting layer may be prevented from disappearing by non-light emission through an 'exciton dissociation' process at the interface between the light emitting layer and the hole transporting layer.
- the blocking layer blocks electrons and excitons from leaving the light emitting layer to balance charges in the light emitting layer, thereby maximizing the generation efficiency and excitation of excitons in the light emitting layer. Therefore, the light emitting device having a blocking layer including the compound represented by Chemical Formula 1 according to the present invention may increase luminous efficiency and decrease driving voltage, thereby improving luminous lifetime.
- FIG 1 and 2 are images showing a schematic structural cross-sectional view of a light emitting device according to the present invention.
- the light emitting devices 100 and 100A may include a first electrode 102, a hole transporting layer 103, a blocking layer 104, and the like formed on the base substrate 101.
- the light emitting layer 105 and the second electrode 106 may be included.
- the light emitting devices 100 and 100A may be organic light emitting diodes (OLEDs).
- OLEDs organic light emitting diodes
- the first electrode 102 is a conductive material and is formed on the base substrate 101 to form an anode of the light emitting devices 100 and 100A. Play a role.
- the first electrode 102 may be a transparent electrode or an opaque (reflective) electrode.
- the first electrode 102 may include indium tin oxide (ITO), tin oxide (SnO 2 ), or the like.
- the first electrode 102 may include an ITO / silver (Ag) / ITO structure.
- a hole transporting layer 103 is formed on the first electrode 102, and is formed between the first electrode 102 and the blocking layer 104. Will be located.
- the hole transport layer 103 may include a hole transport layer and / or a hole injection layer.
- the hole transport layer for example, 4,4-bis [N- (1-naphthyl) -N-phenyl-amine] biphenyl (? -NPD), N, N-diphenyl-N, N-bis (3-methylphenyl) -1,1-biphenyl-4,4-diamine (TPD), poly- (N-vinylcarbazole) (PVCz) and the like may be included alone or in combination of two or more thereof, Two or more layers may be laminated as a layer, but is not limited thereto.
- the hole injection layer may be stacked between the anode and the hole transport layer, and may include, for example, copper phthalocyanine (CuPc), but is not limited thereto.
- the hole transport layer 103 may include a compound represented by the following formula (3) as a hole transport compound:
- R 3 and R 4 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms;
- L c is -L 1 -L 2 -L 3 -L 4- ,
- L 1 , L 2 , L 3, and L 4 are each independently a single bond, —O—, —S—, an arylene group having 6 to 30 carbon atoms, a heteroarylene group having 2 to 20 carbon atoms, or 3 to 20 carbon atoms. Having cycloalkylene groups, except where L 1 , L 2 , L 3 and L 4 are all single bonds;
- Ar 4 and Ar 5 are each independently an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, or a substituent represented by the following general formula (4),
- X is O, S or C (R 7 ) (R 8 ),
- R 5 , R 6 , R 7 and R 8 are each independently an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms,
- p is an integer from 0 to 3
- q is an integer of 0-4.
- the hole transporting compound represented by Formula 3 according to the present invention may be a compound represented by the following Formula 5:
- R 3 is an aryl group having 6 to 30 carbon atoms
- R 4 is hydrogen
- L c is an arylene group having 6 to 20 carbon atoms
- Ar 4 is an aryl group having 6 to 30 carbon atoms or a substituent represented by the following formula (4),
- X is O, S or C (R 7 ) (R 8 ),
- R 5 , R 6 , R 7 and R 8 are each independently an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 30 carbon atoms,
- p is an integer from 0 to 2
- q is an integer of 0-2.
- R 3 is a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group;
- R 4 is hydrogen
- L c is a phenylene group, a biphenylene group, a terphenylene group or a naphthalene group
- Ar 4 may be a phenyl group, biphenyl group, terphenyl group, naphthyl group, dibenzothienyl group, dibenzofuranyl group, fluorenyl group, dimethylfluorenyl group or diphenylfluorenyl group.
- a first hole transport layer 103a which may include a P-type dopant
- the second hole transport layer 103b including the compound represented by Chemical Formula 3 may be included.
- the hole transport layer 103 includes a first hole transport layer 103a in contact with the first electrode 102; And a second hole transport layer 103b positioned between the first hole transport layer 103a and the blocking layer 104. That is, the hole transport layer 103 may have a two-layer structure. In addition, the hole transport layer 103 may have a multilayer structure of two or more layers including the first and second hole transport layers 103a and 103b.
- the first and second hole transport layers 103a and 103b according to the present invention may include the same kind of hole transport compound.
- the emission layer may be reduced by reducing physicochemical defects that may occur at an interface between different materials. This can facilitate the hole injection.
- the same type of host material is used for the first hole transporting layer 103a and the second hole transporting layer 103b
- the first hole transporting layer 103a and the second hole transporting layer 103b are formed in one chamber. Since it is formed continuously within, there is an advantage that the manufacturing process is simplified and the production time can be shortened.
- the physical properties such as the glass transition temperature T g are similar in the region where the first hole transporting layer 103a and the second hole transporting layer 103b are adjacent to each other, the durability of the device may be improved.
- the first hole transporting layer 103a may include a hole transporting compound represented by Chemical Formula 3 and a P-type dopant as a hole transporting compound.
- the second hole transporting layer 103b is a hole transporting compound, and includes a hole transporting compound represented by Chemical Formula 3, but the hole transporting compound included in the second hole transporting layer 103b may be a first hole transporting layer ( 103a) and the structure may be the same or different.
- the hole transport compounds constituting the first and second hole transport layers (103a, 103b) is a hole transport compound represented by the formula (3), R 3 , R 4 , L c , Ar 4 And Ar Any one or more of 5 may be different from each other independently.
- the compound constituting each of the first and second hole transport layers 103a and 103b may be selected to have a HOMO value for efficiently transferring holes to the light emitting layer 105.
- the P-type dopant according to the present invention constituting the first hole transporting layer 103a may include at least one P-type organic dopant or a P-type inorganic dopant, and at least one P-type organic dopant and at least one P-type. It may include the form inorganic dopant at the same time.
- hexadecafluorophthalocyanine represented by the following Chemical Formulas 6 to 10, 11,11,12,12-tetracyanonaphtho-2,6-quinodi Methane (11,11,12,12-tetracyanonaphtho-2,6-quinodimethane, TNAP), 3,6-difluoro-2,5,7,7,8,8-hexacyano-quinomimethane (3 , 6-difluoro-2,5,7,7,8,8-hexacyano-quinodimethane, F2-HCNQ), Tetracyanoquinodimethane (TCNQ), and the like:
- R is a cyano group, sulfone group, sulfoxide group, sulfonamide group, sulfonate group, nitro group or trifluoromethyl group,
- n and n are independently of each other an integer from 1 to 5;
- Y 1 and Y 2 are each independently an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms;
- Hydrogen of the aryl and heteroaryl group is unsubstituted independently from each other; Or an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a haloalkoxy group having 1 to 5 carbon atoms, a hydroxyl group or a halogen group.
- the compound represented by Formula 10 may include a compound represented by Formula 10a or Formula 10b.
- a metal oxide, a metal halide, etc. are mentioned, for example.
- the content of the P-type dopant may be about 0.5 parts by weight to about 15 parts by weight, or about 0.5 parts by weight to about 5 parts by weight based on 100 parts by weight of the hole transporting compound. Or about 1 part by weight to 10 parts by weight based on 100 parts by weight of the hole transporting compound; 1 part by weight to 5 parts by weight; 1.5 parts by weight to 6 parts by weight; Or 2 parts by weight to 5 parts by weight.
- the P-type dopant When the content of the P-type dopant is about 0.5 part by weight to about 20 parts by weight with respect to 100 parts by weight of the hole transporting compound, the P-type dopant may generate excessive leakage current without reducing the physical properties of the hole-transporting compound. It can prevent. In addition, the energy barrier at the interface with each of the upper and lower layers in contact with the hole transport layer 103 may be reduced by the P-type dopant.
- the blocking layer 104 may include a compound represented by Formula 1 below, and is located between the hole transport layer 103 and the light emitting layer 105.
- R 1 , R 2 , L a , L b , Ar 1 , Ar 2 and Ar 3 are as defined above.
- the luminous efficiency and the light emitting life of the light emitting devices (100 and 100A) including the compound represented by Formula 1 in the blocking layer 104 according to the present invention was evaluated.
- the light emitting device according to the present invention showed that the luminous efficiency is increased by about 1.17 to 1.54 times and the light emission lifetime is about 1.23 times to 1.66 times compared to the light emitting device that does not include the blocking layer 104.
- the luminous efficiency was increased by about 1.13 times to 1.48 times, and the light emission lifetime was improved by about 1.13 times to 1.52 times as compared with the light emitting device having the blocking layer not containing the compound represented by Formula 1.
- the light emitting devices 100 and 100A according to the present invention have excellent blocking efficiency and light emitting lifetime by providing the blocking layer 104 including the compound represented by Chemical Formula 1.
- the blocking layer 104 has a single layer structure including at least one compound represented by Chemical Formula 1, or as shown in FIG. 2, the blocking 1 layer 104a and the blocking 2 layer. It may be a two-layer structure including 104b.
- both the blocking 1 layer 104a and the blocking 2 layer 104b constituting the double layer structure may include at least one compound represented by Formula 1, wherein each individual layer Compounds represented by Formula 1 included in may have a different structure.
- the blocking layer 104 is any one of the first blocking layer 104a and the second blocking layer 104b constituting a two-layer structure includes at least one compound represented by the formula (1), the other layer is the following formula It may have a structure comprising a compound represented by 2:
- R a , R b , R c and R d are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 14 carbon atoms.
- the blocking layer 104 can increase the luminous efficiency by adjusting the thickness according to the resonance length of the light emitting device (100 and 100A), the exciton self-interface between the light emitting layer 105 and the other layer
- the thickness thereof is not particularly limited.
- the barrier layer when the structure of the barrier layer is a single layer, it may have a thickness in the range of 20 kPa to 400 kPa, and in the case of a two-layer structure, each individual layer may have a thickness in the range of 10 kPa to 200 kPa.
- the light emitting layer 105 is located between the blocking layer 104 and the second electrode 106, and the wavelength of the light emitted by the light emitting layer 105.
- the silver may be different depending on the kind of the compound forming the light emitting layer 105.
- the compound forming the light emitting layer 105 is not particularly limited as long as it is generally used in the art, and may be obtained commercially or manufactured and used.
- the second electrode 106 is a conductive material and is disposed on the light emitting layer 105 to cathode the light emitting devices 100 and 100A. Play a role.
- the second electrode 106 may include a metal such as nickel, magnesium, calcium, silver, aluminum, indium, or an alloy including two or more metals thereof, and more specifically, may include aluminum. .
- the second electrode 106 may include a single layer structure or a multilayer structure of two or more layers.
- the first electrode 102 is an opaque electrode
- the second electrode 106 may be a transparent or translucent electrode, and in this case, the second electrode 106 may use an alloy including magnesium and silver. , 100 ⁇ s to 150 ⁇ m in thickness.
- the light emitting device 100 and 100A is an electron transporting layer between the light emitting layer 105 and the second electrode 106, an electron transporting layer (ETL) and / or electron injection layer (electron injecting) layer, EIL) (not shown) may be further included.
- ETL electron transporting layer
- EIL electron injection layer
- the material for forming the electron transport layer or the electron injection layer is not particularly limited as long as it is generally used in the art, it may be obtained commercially or manufactured and used.
- the light emitting devices 100 and 100A When a current flows between the first and second electrodes 102 and 106 of the light emitting devices 100 and 100A, holes and holes injected from the first electrode 102 to the light emitting layer 105 are formed. Electrons injected from the second electrode 106 into the light emitting layer 105 combine to form excitons. In this case, the excitons may be singlet excitons, and may also be triplet excitons. Then, in the process of transition of the excitons to the ground state, light having a wavelength of a specific region is generated. Accordingly, the light emitting devices 100 and 100A may provide light to the outside.
- the light emitting devices 100 and 100A further include a second blocking layer (not shown) positioned between the light emitting layer 105 and the second electrode 106. It may include.
- the second blocking layer is positioned between the light emitting layer 105 and the second electrode 106, specifically, the light emitting layer 105 and the electron transporting layer, so that holes are formed by electrons from the first electrode 102 via the light emitting layer 105. It may be a hole blocking layer (HBL) to prevent the flow into the transport layer (HBL). In addition, the second blocking layer may be an exciton blocking layer that prevents excitons formed in the emission layer 105 from diffusing in the direction of the second electrode 106 to prevent the excitons from extinction.
- HBL hole blocking layer
- the second blocking layer may be an exciton blocking layer that prevents excitons formed in the emission layer 105 from diffusing in the direction of the second electrode 106 to prevent the excitons from extinction.
- the second blocking layer may increase the luminous efficiency by adjusting the thickness according to the resonance lengths of the light emitting devices 100 and 100A, and the excitons are not the interface between the light emitting layer 105 and the other layer.
- 105 may be formed at the center portion.
- the light emitting devices 100 and 100A according to the present invention typically include the first electrode 102, the hole transport layer 103, the blocking layer 104, the light emitting layer 105, the second electrode 106, and the like described above. Although it may be prepared using a deposition method, any method commonly used in the art other than the deposition method may be applied without limitation.
- the present invention provides an electronic device including the light emitting device described above.
- the electronic device according to the present invention may be a display device or a lighting device, but is not limited thereto.
- the electronic device includes a light emitting device having an improved luminous efficiency and an improved luminous lifetime by introducing a blocking layer containing the compound represented by Chemical Formula 1, so that the electronic device may also be used in high current / high power fields requiring high brightness / high reliability. Can be used.
- the cooled reaction mixture was dissolved in tetrahydrofuran (THF, 50 mL) and added to a 1 L reaction vessel containing methanol (300 mL). Thereafter, the mixture was stirred for 20 minutes, and the resulting precipitate was filtered and collected to obtain a target compound (Formula 1a, 18.0 g, 96%) as a light gray solid.
- THF tetrahydrofuran
- the cooled reaction mixture was dissolved in tetrahydrofuran (THF, 100 mL) and added to a 1 L reaction vessel containing methanol (300 mL). Thereafter, the mixture was stirred for 40 minutes, and the resulting precipitate was filtered and collected to obtain a target compound (Formula 1b, 17.0 g, 92%) as a light gray solid.
- THF tetrahydrofuran
- the cooled reaction mixture was dissolved in tetrahydrofuran (THF, 70 mL) and added to a 1 L reaction vessel containing methanol (300 mL). Thereafter, the mixture was stirred for 20 minutes, and the resulting precipitate was filtered and collected to obtain a target compound (Formula 1c, 11.5 g, 94%) as a light gray solid.
- THF tetrahydrofuran
- the cooled reaction mixture was dissolved in tetrahydrofuran (THF, 100 mL) and added to a 1 L reaction vessel containing methanol (300 mL). Thereafter, the mixture was stirred for 50 minutes, and the resulting precipitate was filtered and collected to obtain a target compound (Formula 1d, 11.0 g, 86%) as a light gray solid.
- THF tetrahydrofuran
- the cooled reaction mixture was dissolved in tetrahydrofuran (THF, 100 mL) and added to a 1 L reaction vessel containing methanol (300 mL). Thereafter, the mixture was stirred for 30 minutes, and the resulting precipitate was filtered and collected to obtain a target compound (Formula 1e, 13.5 g, 91%) as a light gray solid.
- THF tetrahydrofuran
- the cooled reaction mixture was dissolved in tetrahydrofuran (THF, 70 mL) and added to a 1 L reaction vessel containing methanol (300 mL). Thereafter, the mixture was stirred for 40 minutes, and the resulting precipitate was filtered and collected to obtain a target compound (Formula 1f, 12.5 g, 90%) as a light gray solid.
- THF tetrahydrofuran
- the cooled reaction mixture was dissolved in tetrahydrofuran (THF, 80 mL) and added to a 1 L reaction vessel containing methanol (300 mL). Thereafter, the mixture was stirred for 30 minutes, and the resulting precipitate was filtered and collected to obtain a target compound (Formula 1g, 14.9 g, 91%) as a light gray solid.
- THF tetrahydrofuran
- Example 8-14 Fabrication of Light-Emitting Device comprising a Blocking Layer with a Single Layer Structure
- a compound represented by the following formula (11) as a host material was deposited at a rate of 1 ⁇ / sec and simultaneously a P-type dopant represented by the following formula (HAT-CN) ) was co-evaporated at a ratio of 3 parts by weight to 100 parts by weight of the host material to form a first hole transport layer having a thickness of 100 mm 3.
- the compound represented by Formula 11 was deposited on the first hole transporting layer to a thickness of 300 GPa to form a second hole transporting layer.
- the compounds prepared in Examples 1 to 7 were respectively deposited to a thickness of 100 GPa to form a blocking layer.
- a compound represented by the following Chemical Formula 13 and a compound represented by Chemical Formula 14 were co-deposited on the blocking layer at a weight ratio of 100: 5 to form a light emitting layer having a thickness of 200 kHz.
- the compound represented by the following Formula 15 and the compound represented by the following Formula 16 were co-deposited in a 50:50 weight ratio on the emission layer to form an electron transport layer having a thickness of 360 kHz. Subsequently, an electron injection layer having a thickness of 5 kHz was formed on the electron transport layer by using the compound represented by the following formula (16).
- a second electrode was formed of an aluminum thin film having a thickness of 1,000 ⁇ on the electron injection layer to manufacture a light emitting device including a blocking layer having a single layer structure.
- Example 8 Compound of Formula 1a prepared in Example 1
- Example 9 Compound of Formula 1b prepared in Example 2
- Example 10 Compound of Formula 1c prepared in Example 3
- Example 11 Compound of Formula 1d, prepared in Example 4
- Example 12 Compound of Formula 1e prepared in Example 5
- Example 13 Compound of Formula 1f prepared in Example 6
- Example 14 Compound of Formula 1g prepared in Example 7
- a compound represented by the above formula (11) is deposited as a host material at a rate of 1 ⁇ / sec and simultaneously a P-type dopant represented by the above formula (HAT-CN) ) Was co-evaporated at a ratio of 3 parts by weight to 100 parts by weight of the host material to form a first hole transport layer having a thickness of 100 mm 3.
- the compound represented by Formula 11 was deposited on the first hole transporting layer to a thickness of 300 GPa to form a second hole transporting layer.
- a compound represented by the following Chemical Formula 17 was deposited to form a blocking layer 1, and then the compounds prepared in Examples 1 to 7 were formed on the blocking layer 1, respectively.
- Deposition formed a barrier 2 layer. At this time, the thickness of the blocking layer 1 and the blocking layer 2 is 50 kPa each.
- the compound represented by Chemical Formula 13 and the compound represented by Chemical Formula 14 were co-deposited at a weight ratio of 100: 5 on the blocking 2 layer to form a light emitting layer having a thickness of 200 kHz.
- the compound represented by Chemical Formula 15 and the compound represented by Chemical Formula 16 were co-deposited in a 50:50 weight ratio on the emission layer to form an electron transport layer having a thickness of 360 kHz. Subsequently, an electron injection layer having a thickness of 5 mV was formed on the electron transport layer by using the compound represented by Chemical Formula 16.
- a second electrode was formed of an aluminum thin film having a thickness of 1,000 ⁇ on the electron injection layer to manufacture a light emitting device including a blocking layer having a two-layer structure.
- a compound represented by the above formula (11) is deposited as a host material at a rate of 1 ⁇ / sec and simultaneously a P-type dopant represented by the above formula (HAT-CN) ) Was co-evaporated at a ratio of 3 parts by weight to 100 parts by weight of the host material to form a first hole transport layer having a thickness of 100 mm 3.
- the compound represented by Formula 11 was deposited on the first hole transporting layer to a thickness of 300 GPa to form a second hole transporting layer.
- Example 4 As shown in Table 3 below, on the second hole transporting layer, the compound prepared in Example 4 (Formula 1d) was deposited to form a blocking layer 1, and then on the blocking layer 1, Examples 1-3 and The compounds prepared in Examples 5-7 (Chemical Formulas 1a-1c and 1e-1g) were respectively deposited to form a barrier 2 layer. At this time, the thickness of the blocking layer 1 and the blocking layer 2 is 50 kPa each.
- the compound represented by Chemical Formula 13 and the compound represented by Chemical Formula 14 were co-deposited at a weight ratio of 100: 5 on the blocking 2 layer to form a light emitting layer having a thickness of 200 kHz.
- the compound represented by Chemical Formula 15 and the compound represented by Chemical Formula 16 were co-deposited in a 50:50 weight ratio on the emission layer to form an electron transport layer having a thickness of 360 kHz. Subsequently, an electron injection layer having a thickness of 5 mV was formed on the electron transport layer by using the compound represented by Chemical Formula 16.
- a second electrode was formed of an aluminum thin film having a thickness of 1,000 ⁇ on the electron injection layer to manufacture a light emitting device including a blocking layer having a two-layer structure.
- Example 8 except that the blocking layer is not formed on the second hole transport layer, except that the light emitting layer is formed in the same manner as in Example 8 to prepare a light emitting device containing no blocking layer.
- Example 8 except that the blocking layer is formed using the compound represented by Formula 17 instead of forming the blocking layer using the compound (Formula 1a) prepared in Example 1 and the Example 8 A light emitting device including a blocking layer having a single layer structure was prepared by the same method.
- the following experiment was performed to evaluate the luminous efficiency and luminous lifetime of the light emitting device including the compound represented by Chemical Formula 1 in the blocking layer.
- the bonded light emitting device was irradiated with UV light and cured, and the luminous efficiency of the cured light emitting device was measured.
- the luminous efficiency was measured based on the value when the luminance is 1,000 cd / m 2 , and the unit of the measured value is lm / W.
- T 50 means a time taken until the luminance of the light emitting device becomes 50% of the initial luminance.
- the value for lifetime can be converted to the expected lifetime when measured under different measurement conditions on the basis of conversion equations known to those skilled in the art.
- Table 4 shows the results of comparing the luminous efficiency and light emitting lifetime of the light emitting device according to Examples 8-14 with those of the light emitting device according to Comparative Example 1 and Comparative Example 2.
- Examples 8 to 14 are cases in which the barrier layer is composed of a single layer, but the barrier layer of the monolayer is configured to include the compound of the present invention represented by Chemical Formula 1.
- Table 5 shows the light emission efficiency and the light emitting life of the light emitting device according to Examples 15-27.
- the light emitting device according to Examples 15 to 27 is a case where the blocking layer has a two-layer structure.
- the blocking layer has a two-layer structure.
- only one layer of the blocking layer having a two-layer structure is configured to include the compound of Formula 1 according to the present invention (two-layer structure case 1)
- the light emitting device according to Examples 22 to 27 is 2
- all the dog blocking layer is configured to include the compound of formula 1 according to the present invention (two-layer structure case 2).
- the light emitting device comprising a blocking layer of a single layer structure
- the light emitting device comprising a compound represented by the formula (1) according to the invention in the blocking layer has a light emission efficiency of 6.8 to 8.6lm / W
- Luminescence lifetime was found to be 207 to 289 hours.
- the light emitting efficiency is 5.2 lm / W
- the light emitting lifetime is 154 hours
- the light emitting efficiency and the light emitting lifetime are significantly lower than those of the light emitting device according to the present invention. It was confirmed.
- the light emitting device of Comparative Example 2 in which the blocking layer includes a compound other than the compound represented by Chemical Formula 1 even though the blocking layer is included the light emitting efficiency and the light emitting lifetime are 5.4 lm / W and 168 hours, respectively. And it is confirmed that the degree of improvement in the light emitting life is low compared to the light emitting device according to the present invention.
- the light emitting device having a single-layer blocking layer including the compound represented by Chemical Formula 1 according to the present invention has a light emission efficiency of about 1.30 to 1.65 times that of the light emitting device that does not include the blocking layer, and has a light emitting lifetime. It can be seen that about 1.34 to 1.88 fold improvement.
- the light emitting device having a single layer structure blocking layer including the compound represented by Formula 1 according to the present invention is compared with the light emitting device having a single layer structure blocking layer comprising a compound other than the compound represented by Formula 1
- the luminous efficiency is increased by about 1.26 to 1.59 times, and the light emitting life is improved by 1.23 to 1.72 times.
- a light emitting device including a blocking layer having a two-layer structure one layer of the blocking layer of a two-layer structure includes a light emitting device comprising a compound represented by the formula (1) according to the present invention (two-layer structure case 1)
- the luminous efficiency was found to be 6.1 to 8.0 lm / W, and the light emitting lifetime was 189 to 255 hours.
- the light-emitting device (two-layer structure case 2) containing all of the two-layer blocking layer compound represented by the formula (1) according to the present invention is that the luminous efficiency is 6.5 to 8.3 m / W, the emission life is 198 to 274 hours appear.
- the luminous efficiency is increased by about 1.17 to 1.54 times and the luminous lifetime is about 1.23 to 1.66 times as compared with the light emitting device that does not include the blocking layer. It can be seen that the luminous efficiency is increased by about 1.13 to 1.48 times, and the light emission life is improved by 1.13 to 1.52 times even when compared with a light emitting device having a single-layer blocking layer including a compound other than the compound.
- the light emission efficiency is increased by about 1.25 to 1.60 times, and the light emission life is improved by about 1.29 to 1.78 times as compared to the light emitting device that does not include the blocking layer. It can be seen that the luminous efficiency is increased by about 1.20 to 1.54 times and the luminous lifetime is 1.18 to 1.63 times compared to the light emitting device having a single layer blocking layer including a compound other than the compound.
- both the case 1 and case 2 of the two-layer structure does not include a blocking layer, or the luminous efficiency and the light-emitting lifetime are greatly improved as compared with the case of forming a blocking layer of a single layer structure with a compound other than the compound represented by Formula 1 according to the present invention. It can be seen that.
- the case of the barrier layer composed of a single layer structure comprising the compound of the formula (1) according to the present invention than the case of the two-layer structure case 1 and case 2 is more advantageous in terms of luminous efficiency and light emitting life.
- the compound having the same luminous efficiency and lifespan of Example 8-14 in which the barrier layer is formed in a single layer structure is used for the barrier layer 2. It turns out that it is superior to the case of Examples 15-21.
- Examples 8 to 14 in which the barrier layer was formed in the single layer structure were blocked with the compound of Example 4 while forming the barrier layer 2 with the same compound. It can be seen that the luminous efficiency and the light emitting lifetime are superior to those in the case of forming one layer.
- the blocking layer may include a compound other than the compound of Formula 1 in the blocking layer even if it does not include the blocking layer or includes the blocking layer. In contrast, it can be seen that the luminous efficiency and the light emitting lifetime are remarkably improved.
- the light emitting device according to the present invention has an excellent light emitting device and a light emitting life by providing a blocking layer including the compound represented by Chemical Formula 1, and thus is useful for electronic devices in high current / high power fields requiring high brightness / high reliability. Can be used.
Abstract
A light emitting element according to the present invention comprises a shielding layer containing a compound represented by chemical formula 1, and thus has excellent light emitting efficiency and light emission lifespan compared with a conventional general light emitting element without a shielding layer. Therefore, the light emitting element according to the present invention can be easily used for an electronic apparatus using a light emitting element, such as a display apparatus or an illumination apparatus.
Description
본 발명은 신규한 화합물 및 이를 포함하는 발광소자에 관한 것이다.The present invention relates to a novel compound and a light emitting device comprising the same.
발광소자(Organic Light-Emitting Diode; OLED)는 기본적으로 두 개의 전극 사이에 유기 발광층을 포함하는 유기 박막이 샌드위치 되어 있는 구조로서, 두 전극 중 최소 하나의 전극은 투명하고, 두 전극 사이에 적당한 전압, 일반적으로 직류 5 내지 10 V 사이의 전압이 인가되면 유기 발광층에서 가시광선 영역의 빛이 나오는 것을 활용한 일종의 유기 전자 소자이다.Organic Light-Emitting Diode (OLED) is basically a structure in which an organic thin film including an organic light emitting layer is sandwiched between two electrodes, at least one of the two electrodes being transparent, and a suitable voltage between the two electrodes. In general, when a voltage of 5 to 10 V DC is applied, the organic light emitting diode is a kind of organic electronic device utilizing light emitted from the visible light region from the organic light emitting layer.
이와 같은 발광소자는 기본적으로 전극을 포함한 실제 소자의 두께가 수 마이크로미터 이하로 매우 얇고, 소자 자체에서 직접 빛이 나오는 자발광소자이므로, 이에 따른 응답 속도가 빠르며, 표시 소자로서 시야각이 넓다. 또한, 제조 공정이 간단하고, 유기 박막을 이용한 유연한 소자의 구현이 가능하며, 진공 공정뿐만 아니라 경우에 따라서는 용액 상태로부터 인쇄 공정을 통한 소자의 구현이 가능하므로 차세대 표시소자 및 조명 측면에서 많은 주목을 받고 있다.Such a light emitting device is basically a very thin device having a thickness of several micrometers or less, and is a self-light emitting device that emits light directly from the device itself. Therefore, the response speed is high and the viewing angle is wide as a display device. In addition, since the manufacturing process is simple, the flexible device using the organic thin film can be realized, and in addition to the vacuum process, in some cases, the device can be realized through the printing process from the solution state. Is getting.
종래, 발광소자는 저전류/저출력의 모바일 제품에 적용되는 부품으로 적용되었으나, 최근 들어 점차 그 활용범위가 고전류/고출력 분야로 확대되고 있으며, 이에 따른 고휘도/고신뢰성이 요구되고 있다. 이러한 추세에 따라 발광소자의 발광효율을 향상시키기 위한 다양한 방법이 연구되고 있다.Conventionally, the light emitting device has been applied as a component to be applied to a low current / low output mobile products, but in recent years, its application range has been gradually extended to the high current / high output field, high brightness / high reliability is required accordingly. In accordance with this trend, various methods for improving the luminous efficiency of light emitting devices have been studied.
현재까지 진행된 연구결과들을 살펴보면, 다음과 같다:The results of the research so far are as follows:
먼저, 특허문헌 1은 PEDOT/PSS를 정공 수송 물질로서 포함하는 발광소자에 관한 것으로, 상기 PEDOT/PSS를 포함하는 조성물은 4.8eV보다 약간 높은 중간 이온화 전위(애노드의 이온화 전위와 발광체의 이온화 전위 사이의 중간값)를 제공한다. 이는 상기 조성물이 애노드로부터 주입된 정공을 유기발광물질 또는 정공 수송물질의 HOMO 준위에 도달하도록 유도함에 따라 발생된다.First, Patent Document 1 relates to a light emitting device comprising PEDOT / PSS as a hole transporting material, wherein the composition comprising PEDOT / PSS has a medium ionization potential slightly higher than 4.8 eV (between the ionization potential of the anode and the ionization potential of the light emitter). Median of This occurs as the composition induces holes injected from the anode to reach the HOMO level of the organic light emitting material or hole transport material.
다음으로, 특허문헌 2는 PEDOT/PSS를 포함하는 조성물에 관한 것으로, 상기 조성물은 잉크젯 프린팅 등의 용액공정이 가능하여 디바이스를 보다 쉽게 제조할 수 있는 이점이 있다. 더불어, 상기 조성물은 과량의 PSS(즉, PEDOT 상의 전하를 안정화하는데 요구되는 양보다 과도한 양)를 사용하므로, 발광소자의 수명을 연장시킬 수 있을 뿐만 아니라 PEDOT 용액으로부터 PSS가 석출되는 것을 방지할 수 있다.Next, Patent Document 2 relates to a composition containing PEDOT / PSS, the composition has the advantage that can be a solution process such as inkjet printing can be manufactured more easily. In addition, the composition uses an excessive amount of PSS (i.e., an amount exceeding the amount required to stabilize the charge on the PEDOT), which not only prolongs the life of the light emitting device but also prevents the precipitation of the PSS from the PEDOT solution. have.
그러나, 상기 특허문헌의 1에 따른 발광소자의 경우, 발광층 물질로 사용되는 유기물의 LUMO 에너지 준위에 비하여 PEDOT/PSS의 LUMO 에너지 준위가 낮기 때문에 고효율 장수명의 발광소자 제조에 어려움이 있다. 또한, 특허문헌 2의 경우, 발광소자에 사용되는 조성물은 과량의 PSS를 포함함으로써 강한 산성을 띄게 되는데, 이러한 강산은 인듐 틴 옥사이드(indium tin oxide, ITO)를 식각시켜 인듐, 주석 및 산소 성분을 PEDOT 내로 방출시키거나, 발광 중합체를 열화시키는 등의 문제를 야기할 수 있다.However, in the light emitting device according to Patent Document 1, since the LUMO energy level of PEDOT / PSS is lower than the LUMO energy level of the organic material used as the light emitting layer material, it is difficult to manufacture a high efficiency long life light emitting device. In addition, in the case of Patent Document 2, the composition used in the light emitting device has a strong acidity by including an excess of PSS, such a strong acid is etched indium tin oxide (ITO) to remove indium, tin and oxygen components Problems such as release into the PEDOT, degradation of the light emitting polymer, and the like.
상술한 바와 같이, 종래 발광소자의 발광효율 및 발광수명을 개선하기 위한 연구는 지속적으로 이루어져 왔다. 그러나, 현재까지 개발된 발광소자 및 발광소자에 사용되는 화합물은 고전류/고출력 분야에서 사용하기에는 그 효과가 미미하므로, 이를 해결할 수 있는 대안이 절실히 요구되고 있다.As described above, studies to improve the luminous efficiency and the light emitting life of the conventional light emitting device have been continuously made. However, the light emitting device and the compound used in the light emitting device developed to date have a minimal effect for use in the field of high current / high power, there is an urgent need for an alternative to solve this problem.
[특허문헌][Patent Documents]
(특허문헌 1) 유럽특허 제0,686,662호;(Patent Document 1) European Patent No. 0,686,662;
(특허문헌 2) 미국특허 제6,605,823호.(Patent Document 2) US Patent No. 6,605,823.
본 발명의 목적은 발광소자의 발광효율 향상 및 발광수명 개선이 가능한 화합물을 제공하는데 있다.An object of the present invention is to provide a compound capable of improving the luminous efficiency and lifespan of the light emitting device.
본 발명의 다른 목적은 상기 화합물을 포함하여 발광효율이 증대되고, 발광수명이 개선된 발광소자를 제공하는데 있다.Another object of the present invention is to provide a light emitting device including the compound, the luminous efficiency is increased, and the light emitting life is improved.
본 발명의 또 다른 목적은 상기 발광소자를 포함하는 전자 장치를 제공하는데 있다.Still another object of the present invention is to provide an electronic device including the light emitting device.
상기 목적을 달성하기 위하여,In order to achieve the above object,
본 발명은 하나의 실시예에서,The invention in one embodiment,
하기 화학식 1로 나타내는 화합물을 제공한다:There is provided a compound represented by the formula:
[화학식 1][Formula 1]
상기 화학식 1에서,In Chemical Formula 1,
R1 및 R2는 서로 독립적으로 수소, 탄소수 1 내지 4를 갖는 알킬기 또는 탄소수 6 내지 10을 갖는 아릴기이고;R 1 and R 2 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms;
La 및 Lb는 서로 독립적으로 단일결합 또는 탄소수 6 내지 30을 갖는 아릴렌기이며; 및L a and L b are each independently a single bond or an arylene group having 6 to 30 carbon atoms; And
Ar1, Ar2 및 Ar3은 서로 독립적으로 수소 또는 탄소수 6 내지 30을 갖는 아릴기이다.Ar 1 , Ar 2 and Ar 3 are each independently hydrogen or an aryl group having 6 to 30 carbon atoms.
또한, 본 발명은 하나의 실시예에서,In addition, the present invention in one embodiment,
제1 전극;A first electrode;
제2 전극;Second electrode;
제1 전극과 제2 전극 사이에 배치된 발광층; A light emitting layer disposed between the first electrode and the second electrode;
제1 전극과 발광층 사이에 배치되는 정공 수송성층; 및A hole transport layer disposed between the first electrode and the light emitting layer; And
정공 수송성층과 발광층 사이에 배치되고, 하기 화학식 1로 나타내는 화합물을 포함하는 차단층을 포함하는 발광소자를 제공한다:A light emitting device is disposed between a hole transporting layer and a light emitting layer, and includes a blocking layer including a compound represented by Formula 1 below:
[화학식 1][Formula 1]
상기 화학식 1에서, R1, R2, La, Lb, Ar1, Ar2 및 Ar3은 상기에서 정의한 바와 같다.In Formula 1, R 1 , R 2 , L a , L b , Ar 1 , Ar 2 and Ar 3 are as defined above.
나아가, 본 발명은 하나의 실시예에서, 상기 발광소자를 포함하는 전자 장치를 제공한다.Furthermore, in one embodiment, the present invention provides an electronic device including the light emitting device.
본 발명에 따른 발광소자는 화학식 1로 나타내는 화합물을 포함하는 차단층을 구비함으로써, 차단층을 구비하지 않은 종래 일반적인 발광소자와 대비하여 우수한 발광효율 및 발광수명을 가지므로, 발광소자를 사용하는 디스플레이 장치, 조명 장치 등의 전자 장치에 용이하게 사용할 수 있다.The light emitting device according to the present invention includes a blocking layer containing the compound represented by Formula 1, and thus has excellent luminous efficiency and light emitting life as compared to a conventional light emitting device having no blocking layer, and thus displays using a light emitting device. It can be used easily for electronic devices, such as an apparatus and a lighting apparatus.
도 1은 본 발명에 따른 하나의 실시예에서 제조되는 발광소자의 구조를 도시한 이미지이다;1 is an image showing the structure of a light emitting device manufactured in one embodiment according to the present invention;
도 2는 본 발명에 따른 다른 실시예에서 제조되는 발광소자의 구조를 도시한 이미지이다.2 is an image showing the structure of a light emitting device manufactured in another embodiment according to the present invention.
본 발명은 다양한 변경을 가할 수 있고 여러 가지 실시예를 가질 수 있는 바, 특정 실시예들을 도면에 예시하고 상세한 설명에 상세하게 설명하고자 한다.As the invention allows for various changes and numerous embodiments, particular embodiments will be illustrated in the drawings and described in detail in the written description.
그러나, 이는 본 발명을 특정한 실시 형태에 대해 한정하려는 것이 아니며, 본 발명의 사상 및 기술 범위에 포함되는 모든 변경, 균등물 내지 대체물을 포함하는 것으로 이해되어야 한다.However, this is not intended to limit the present invention to specific embodiments, it should be understood to include all modifications, equivalents, and substitutes included in the spirit and scope of the present invention.
본 발명에서, "포함한다" 또는 "가지다" 등의 용어는 명세서상에 기재된 특징, 숫자, 단계, 동작, 구성요소, 부품 또는 이들을 조합한 것이 존재함을 지정하려는 것이지, 하나 또는 그 이상의 다른 특징들이나 숫자, 단계, 동작, 구성요소, 부품 또는 이들을 조합한 것들의 존재 또는 부가 가능성을 미리 배제하지 않는 것으로 이해되어야 한다.In the present invention, the terms "comprises" or "having" are intended to indicate that there is a feature, number, step, operation, component, part, or combination thereof described in the specification, and one or more other features. It is to be understood that the present invention does not exclude the possibility of the presence or the addition of numbers, steps, operations, components, components, or a combination thereof.
또한, 본 발명에서 첨부된 도면은 설명의 편의를 위하여 확대 또는 축소하여 도시된 것으로 이해되어야 한다.In addition, it is to be understood that the accompanying drawings in the present invention are shown enlarged or reduced for convenience of description.
이하, 본 발명에 대하여 도면을 참고하여 상세하게 설명하고, 도면 부호에 관계없이 동일하거나 대응하는 구성 요소는 동일한 참조 번호를 부여하고 이에 대한 중복되는 설명은 생략하기로 한다.Hereinafter, the present invention will be described in detail with reference to the accompanying drawings, and the same or corresponding components will be given the same reference numerals regardless of the reference numerals, and redundant description thereof will be omitted.
본 발명에서, "알킬기"란 직쇄(linear) 또는 분지(branched) 형태의 포화 탄화수소로부터 유도된 작용기를 의미한다.In the present invention, "alkyl group" means a functional group derived from a saturated hydrocarbon in a linear or branched form.
이때, 상기 "알킬기"로는 예를 들면, 메틸기(methyl group), 에틸기(ethyl group), n-프로필기(n-propyl group), 이소프로필기(iso-propyl group), n-부틸기(n-butyl group), sec-부틸기(sec-butyl group), t-부틸기(tert-butyl group), n-펜틸기(n-pentyl group), 1,1-디메틸프로필기(1,1-dimethylpropyl group), 1,2-디메틸프로필기(1,2-dimethylpropyl group), 2,2-디메틸프로필기(2,2-dimethylpropyl group), 1-에틸프로필기(1-ethylpropyl group), 2-에틸프로필기(2-ethylpropyl group), n-헥실기(n-hexyl group), 1-메틸-2-에틸프로필기(1-methyl-2-ethylpropyl group), 1-에틸-2-메틸프로필기(1-ethyl-2-methylpropyl group), 1,1,2-트리메틸프로필기(1,1,2-trimethylpropyl group), 1-프로필프로필기(1-propylpropyl group), 1-메틸부틸기(1-methylbutyl group), 2-메틸부틸기(2-methylbutyl group), 1,1-디메틸부틸기(1,1-dimethylbutyl group), 1,2-디메틸부틸기(1,2-dimethylbutyl group), 2,2-디메틸부틸기(2,2-dimethylbutyl group), 1,3-디메틸부틸기(1,3-dimethylbutyl group), 2,3-디메틸부틸기(2,3-dimethylbutyl group), 2-에틸부틸기(2-ethylbutyl group), 2-메틸펜틸기(2-methylpentyl group), 3-메틸펜틸기(3-methylpentyl group) 등을 들 수 있다.At this time, as the "alkyl group", for example, methyl group (ethyl group), ethyl group (ethyl group), n-propyl group (n-propyl group), isopropyl group (iso-propyl group), n-butyl group (n -butyl group, sec-butyl group, t-butyl group, tert-butyl group, n-pentyl group, 1,1-dimethylpropyl group (1,1- dimethylpropyl group), 1,2-dimethylpropyl group (1,2-dimethylpropyl group), 2,2-dimethylpropyl group (2,2-dimethylpropyl group), 1-ethylpropyl group (1-ethylpropyl group), 2- 2-ethylpropyl group, n-hexyl group, 1-methyl-2-ethylpropyl group, 1-ethyl-2-methylpropyl group (1-ethyl-2-methylpropyl group), 1,1,2-trimethylpropyl group, 1-propylpropyl group, 1-methylbutyl group (1 -methylbutyl group), 2-methylbutyl group, 1,1-dimethylbutyl group (1,1-dimethylbutyl group), 1,2-dimethylbutyl group (1,2-dimethylbutyl group), 2 , 2-dimethylbutyl group (2,2-dimet hylbutyl group), 1,3-dimethylbutyl group (1,3-dimethylbutyl group), 2,3-dimethylbutyl group (2,3-dimethylbutyl group), 2-ethylbutyl group (2-ethylbutyl group), 2- Methyl pentyl group (2-methylpentyl group), 3-methylpentyl group, etc. are mentioned.
또한, 상기 “알킬기”는 1 내지 20의 탄소수, 예를 들어 1 내지 12의 탄소수, 1 내지 6의 탄소수, 또는 1 내지 4의 탄소수를 가질 수 있다.In addition, the "alkyl group" may have 1 to 20 carbon atoms, for example, 1 to 12 carbon atoms, 1 to 6 carbon atoms, or 1 to 4 carbon atoms.
본 발명에서, "아릴기"란 방향족 탄화수소로부터 유도된 1가의 치환기를 의미한다.In the present invention, "aryl group" means a monovalent substituent derived from an aromatic hydrocarbon.
이때, 상기 "아릴기"로는 예를 들면, 페닐기(phenyl group), 나프틸기(naphthyl group), 안트라세닐기(anthracenyl group), 페난트릴기(phenanthryl group) 나프타세닐기(naphthacenyl group), 톨릴기(tolyl group), 바이페닐기(biphenyl group), 터페닐기(terphenyl group), 크리세닐기(chrycenyl group), 스피로바이플루오레닐기(spirobifluorenyl group), 플루오란테닐기(fluoranthenyl group), 플루오레닐기(fluorenyl group), 페릴레닐기(perylenyl group), 인데닐기(indenyl group), 아줄레닐기(azulenyl group), 헵타레닐기(heptalenyl group), 페날레닐기(phenalenyl group), 페난트레닐기(phenanthrenyl group) 등을 들 수 있다.At this time, the "aryl group", for example, a phenyl group (phenyl group), naphthyl group (naphthyl group), anthracenyl group (anthracenyl group), phenanthryl group (phenanthryl group) naphthacenyl group (naphthacenyl group), tolyl group (tolyl group), biphenyl group, terphenyl group, terphenyl group, chrycenyl group, spirobifluorenyl group, fluoranthenyl group, fluorenyl group ( fluorenyl group, perylenyl group, indenyl group, indenyl group, azulenyl group, heptarenyl group, heparenyl group, phenalenyl group, phenanthrenyl group Etc. can be mentioned.
또한, 상기 "아릴기"는 6 내지 30의 탄소수, 예를 들어, 6 내지 20의 탄소수, 6 내지 18의 탄소수, 또는 6 내지 12의 탄소수를 가질 수 있다.In addition, the "aryl group" may have 6 to 30 carbon atoms, for example, 6 to 20 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms.
본 발명에서, "헤테로아릴기"란 단환 또는 축합환으로부터 유도된 "방향족 복소환"또는 "헤테로사이클릭"을 의미한다. 상기 "헤테로아릴기"는 헤테로원자로서 질소(N), 황(S), 산소(O), 인(P), 셀레늄(Se) 및 규소(Si) 중에서 적어도 하나, 예를 들어 1개, 2개, 3개 또는 4개를 포함할 수 있다.In the present invention, "heteroaryl group" means "aromatic heterocycle" or "heterocyclic" derived from a monocyclic or condensed ring. The "heteroaryl group" is a hetero atom, at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se) and silicon (Si), for example, one, two Dogs, three or four.
이때, 상기 "헤테로아릴기"로는 예를 들면, 피롤릴기(pyrrolyl group), 피리딜기(pyridyl group), 피리다지닐기(pyridazinyl group), 피리미디닐기(pyrimidinyl group), 피라지닐기(pyrazinyl group), 트리아졸릴기(triazolyl group), 테트라졸릴기(tetrazolyl group), 벤조트리아졸릴기(benzotriazolyl group), 피라졸릴기(pyrazolyl group), 이미다졸릴기(imidazolyl group), 벤즈이미다졸릴기(benzimidazolyl group), 인돌릴기(indolyl group), 이소인돌릴기(isoindolyl group), 인돌리지닐기(indolizinyl group), 푸리닐기(purinyl group), 인다졸릴기(indazolyl group), 퀴놀릴기(quinolyl group), 이소퀴놀리닐기(isoquinolinyl group), 퀴놀리지닐기(quinolizinyl group), 프탈라지닐기(phthalazinyl group), 나프틸리디닐기(naphthylidinyl group), 퀴녹살리닐기(quinoxalinyl group), 퀴나졸리닐기(quinazolinyl group), 신놀리닐기(cinnolinyl group), 프테리디닐기(pteridinyl group), 이미다조트리아지닐기(imidazotriazinyl group), 아크리디닐기(acridinyl group), 페난트리디닐기(phenanthridinyl group), 카바졸릴기(carbazolyl group), 카바졸리닐기(carbazolinyl group), 피리미디닐기(pyrimidinyl group), 페난트롤리닐기(phenanthrolinyl group), 페나지닐기(phenazinyl group), 이미다조피리디닐기(imidazopyridinyl group), 이미다조피리미디닐기(imidazopyrimidinyl group), 피라졸로피리디닐기(pyrazolopyridinyl group) 등을 포함하는 함질소 헤테로아릴기; 티에닐기(thienyl group), 벤조티에닐기(benzothienyl group), 디벤조티에닐기(dibenzothienyl group) 등을 포함하는 황 함유 헤테로아릴기; 퓨릴기(furyl group), 피라닐기(pyranyl group), 사이클로펜타피라닐기(cyclopentapyranyl group), 벤조퓨라닐기(benzofuranyl group), 이소벤조퓨라닐기(isobenzofuranyl group), 디벤조퓨라닐기(dibenzofuranyl group) 등을 포함하는 함산소 헤테로아릴기 등을 들 수 있다.In this case, the "heteroaryl group", for example, pyrrolyl group (pyrrolyl group), pyridyl group (pyridyl group), pyridazinyl group (pyridazinyl group), pyrimidinyl group, pyrazinyl group (pyrazinyl group) ), Triazolyl group, tetrazolyl group, benzotriazolyl group, benzotriazolyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group ( benzimidazolyl group, indolyl group, isoindolyl group, indodolyl group, indolinzinyl group, purinyl group, purinyl group, indazolyl group, quinolyl group ), Isoquinolinyl group (isoquinolinyl group), quinolizinyl group (quinolizinyl group), phthalazinyl group (phthalazinyl group), naphthylidinyl group, quinoxalinyl group (quinoxalinyl group), quinazolinyl group ( quinazolinyl group, cinnolinyl group, pteridinyl group, already Zotriazinyl group (imidazotriazinyl group), acridinyl group (acridinyl group), phenanthridinyl group (phenanthridinyl group), carbazolyl group, carbazolinyl group (carbazolinyl group), pyrimidinyl group, Phenanthrolinyl group (phenanthrolinyl group), phenazinyl group (phenazinyl group), imidazopyridinyl group (imidazopyridinyl group), imidazopyrimidinyl group, pyrazolopyridinyl group (pyrazolopyridinyl group) Nitrogen heteroaryl groups; Sulfur-containing heteroaryl groups including thienyl group, benzothienyl group, dibenzothienyl group and the like; Furyl group, pyranyl group, cyclopentapyranyl group, cyclopentapyranyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group and dibenzofuranyl group An oxygen-containing heteroaryl group etc. which are included are mentioned.
또한, 상기 "헤테로아릴기"의 구체적인 예로서는, 티아졸릴기(thiazolyl group), 이소티아졸릴기(isothiazolyl group), 벤조티아졸릴기(benzothiazolyl group), 벤조티아디아졸릴기(benzothiadiazolyl group), 페노티아지닐기(phenothiazinyl group), 이소옥사졸릴기(isoxazolyl group), 퓨라자닐기(furazanyl group), 페녹사지닐기(phenoxazinyl group), 옥사졸릴기(oxazolyl group), 벤조옥사졸릴기(benzoxazolyl group), 옥사다이아졸릴기(oxadiazolyl group), 피라졸로옥사졸릴기(pyrazoloxazolyl group), 이미다조티아졸릴기(imidazothiazolyl group), 티에노퓨라닐기(thienofuranyl group), 퓨로피롤릴기(furopyrrolyl group), 피리독사지닐기(pyridoxazinyl group) 등의 적어도 2개 이상의 헤테로원자를 포함하는 화합물들을 들 수 있다.In addition, as a specific example of the "heteroaryl group", thiazolyl group (thiazolyl group), isothiazolyl group (isothiazolyl group), benzothiazolyl group (benzothiazolyl group), benzothiadiazolyl group (benzothiadiazolyl group), phenothia Phenothiazinyl group, isoxazolyl group, furazanyl group, furazanyl group, phenoxazinyl group, oxazolyl group, oxazolyl group, benzoxazolyl group, Oxadiazolyl group, pyrazoloxazolyl group, imidazothiazolyl group, thienofuranyl group, furopyrrolyl group, pyridoxazinyl group and compounds containing at least two or more heteroatoms such as (pyridoxazinyl group).
또한, 상기 "헤테로아릴기"는 2 내지 20의 탄소수, 예를 들어 3 내지 19의 탄소수, 4 내지 15의 탄소수 또는 5 내지 11의 탄소수를 가질 수 있다. 예를 들어, 헤테로원자를 포함하면, 헤테로아릴기는 5 내지 21의 환원(ring member)을 가질 수 있다.In addition, the "heteroaryl group" may have 2 to 20 carbon atoms, for example, 3 to 19 carbon atoms, 4 to 15 carbon atoms, or 5 to 11 carbon atoms. For example, when including a heteroatom, the heteroaryl group may have a ring member of 5 to 21.
본 발명에서, "사이클로알킬기"란 단일고리(monocyclic)의 포화 탄화수소로부터 유도된 치환기를 의미한다.In the present invention, "cycloalkyl group" means a substituent derived from a monocyclic saturated hydrocarbon.
상기 "사이클로알킬기"로는 예를 들면, 사이클로프로필기(cyclopropyl group), 사이클로부틸기(cyclobutyl group), 사이클로펜틸기(cyclopentyl group), 사이클로헥실기(cyclohexyl group), 사이클로헵틸기(cycloheptyl group), 사이클로옥틸기(cyclooctyl group) 등을 들 수 있다.Examples of the "cycloalkyl group" include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloheptyl group, Cyclooctyl group etc. are mentioned.
또한, 상기 "사이클로알킬기"는 3 내지 20의 탄소수, 예를 들어 3 내지 12의 탄소수, 또는 3 내지 6의 탄소수를 가질 수 있다.In addition, the "cycloalkyl group" may have 3 to 20 carbon atoms, for example, 3 to 12 carbon atoms, or 3 to 6 carbon atoms.
본 발명에서, "아릴렌기"란 상기에서 설명한 아릴기로부터 유도된 2가의 치환기를 의미할 수 있다.In the present invention, "arylene group" may mean a divalent substituent derived from the aryl group described above.
또한, 본 발명에서, "헤테로아릴렌기"란 상기에서 설명한 헤테로아릴기로부터 유도된 2가의 치환기를 의미할 수 있다.In addition, in the present invention, "heteroarylene group" may refer to a divalent substituent derived from the heteroaryl group described above.
본 발명은 발광소자의 발광효율을 향상시키고 발광수명을 개선시킬 수 있는 화합물 및 이를 포함하는 발광소자를 제공한다.The present invention provides a compound which can improve the luminous efficiency of the light emitting device and improve the light emitting life and a light emitting device comprising the same.
현재까지 개발된 발광소자는 전력 효율이 낮고, 발광수명이 짧은 문제점이 있다. 이와 같은 문제점들을 해결하기 위해서, 발광소자의 재료로서 다양한 화합물들이 개발되고 있지만 발광효율 및 발광수명을 모두 만족시키는 발광소자를 제조하는데 한계가 있다.The light emitting devices developed to date have low power efficiency and short lifespan. In order to solve these problems, various compounds have been developed as materials of the light emitting device, but there are limitations in manufacturing a light emitting device that satisfies both the light emitting efficiency and the light emitting lifetime.
이에, 본 발명은 발광효율을 향상시키고 발광수명을 개선할 수 있는 화학식 1로 나타내는 화합물을 포함하는 차단층이 구비된 구조의 발광소자 및 이를 포함하는 전자 장치를 제안한다. 본 발명에 따른 발광소자는 화학식 1로 나타내는 화합물을 포함하는 차단층을 구비함으로써, 차단층을 구비하지 않은 종래 일반적인 발광소자와 대비하여 발광효율 및 발광수명이 우수하다. 따라서, 본 발명에 따른 발광소자는 발광소자를 사용하는 디스플레이 장치, 조명 장치 등의 전자 장치에 용이하게 사용할 수 있다.Accordingly, the present invention proposes a light emitting device having a structure including a blocking layer including a compound represented by Chemical Formula 1, which can improve light emission efficiency and light emission life, and an electronic device including the same. The light emitting device according to the present invention is provided with a blocking layer containing the compound represented by the formula (1), it is excellent in luminous efficiency and light emitting life compared to the conventional general light emitting device without a blocking layer. Therefore, the light emitting device according to the present invention can be easily used in an electronic device such as a display device and a lighting device using the light emitting device.
이하, 본 발명을 보다 상세히 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명은 하나의 실시예에서,The invention in one embodiment,
하기 화학식 1로 나타내는 화합물을 제공한다:There is provided a compound represented by the formula:
화학식 1 
Formula 1
상기 화학식 1에서,In Chemical Formula 1,
R1 및 R2는 서로 독립적으로 수소, 탄소수 1 내지 4를 갖는 알킬기 또는 탄소수 6 내지 10을 갖는 아릴기이고;R 1 and R 2 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms;
La 및 Lb는 서로 독립적으로 단일결합 또는 탄소수 6 내지 30을 갖는 아릴렌기이며; 및L a and L b are each independently a single bond or an arylene group having 6 to 30 carbon atoms; And
Ar1, Ar2 및 Ar3은 서로 독립적으로 수소 또는 탄소수 6 내지 30을 갖는 아릴기이다.Ar 1 , Ar 2 and Ar 3 are each independently hydrogen or an aryl group having 6 to 30 carbon atoms.
이때, 본 발명에 따른 화학식 1로 나타내는 화합물에 있어서,At this time, in the compound represented by the formula (1) according to the present invention,
상기 R1 및 R2는 서로 독립적으로 수소, 탄소수 1 내지 4를 갖는 알킬기 또는 탄소수 6 내지 10을 갖는 아릴기이고;R 1 and R 2 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms;
La 및 Lb는 서로 독립적으로 단일결합 또는 탄소수 6 내지 14를 갖는 아릴렌기이며;L a and L b are each independently a single bond or an arylene group having 6 to 14 carbon atoms;
Ar1은 수소이고; 및Ar 1 is hydrogen; And
Ar2 및 Ar3은 서로 독립적으로 수소 또는 탄소수 6 내지 20을 갖는 아릴기일 수 있다.Ar 2 and Ar 3 may be independently hydrogen or an aryl group having 6 to 20 carbon atoms.
구체적으로, 상기 화학식 1로 나타내는 화합물은 하기 화학식 a-1 내지 a-27의 구조를 갖는 화합물로부터 선택될 수 있다:Specifically, the compound represented by Formula 1 may be selected from compounds having the structures of Formulas a-1 to a-27:
<화학식 a-1> <Formula a-1>
<화학식 a-2> <Formula a-2>
<화학식 a-3> <Formula a-3>
<화학식 a-4> <Formula a-4>
<화학식 a-5> <Formula a-5>
<화학식 a-6> <Formula a-6>
<화학식 a-7> <Formula a-7>
<화학식 a-8> <Formula a-8>
<화학식 a-9> <Formula a-9>
<화학식 a-10> <Formula a-10>
<화학식 a-11> <Formula a-11>
<화학식 a-12> <Formula a-12>
<화학식 a-13> <Formula a-13>
<화학식 a-14> <Formula a-14>
<화학식 a-15> <Formula a-15>
<화학식 a-16> <Formula a-16>
<화학식 a-17> <Formula a-17>
<화학식 a-18> <Formula a-18>
<화학식 a-19> <Formula a-19>
<화학식 a-20> <Formula a-20>
<화학식 a-21> <Formula a-21>
<화학식 a-22> <Formula a-22>
<화학식 a-23> <Formula a-23>
<화학식 a-24> <Formula a-24>
<화학식 a-25> <Formula a-25>
<화학식 a-26> <Formula a-26>
<화학식 a-27> <Formula a-27>
또한, 본 발명에 따른 화학식 1로 나타내는 화합물에 있어서,In addition, in the compound represented by Formula 1 according to the present invention,
상기 R1 및 R2는 서로 독립적으로 수소, 탄소수 1 내지 4를 갖는 알킬기 또는 탄소수 6 내지 10을 갖는 아릴기이고;R 1 and R 2 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms;
La 및 Lb는 서로 독립적으로 단일결합 또는 탄소수 6 내지 14를 갖는 아릴렌기이며;L a and L b are each independently a single bond or an arylene group having 6 to 14 carbon atoms;
Ar1은 탄소수 6 내지 30을 갖는 아릴기이고; 및Ar 1 is an aryl group having 6 to 30 carbon atoms; And
Ar2 및 Ar3은 서로 독립적으로 수소 또는 탄소수 6 내지 20을 갖는 아릴기일 수 있다.Ar 2 and Ar 3 may be independently hydrogen or an aryl group having 6 to 20 carbon atoms.
구체적으로, 본 발명에 따른 화학식 1로 나타내는 화합물에 있어서,Specifically, in the compound represented by Formula 1 according to the present invention,
상기 Ar1은 페닐기 또는 바이페닐기일 수 있다.Ar 1 may be a phenyl group or a biphenyl group.
보다 구체적으로, 상기 화학식 1로 나타내는 화합물은 하기 화학식 b-1 내지 b-54의 구조를 갖는 화합물로부터 선택될 수 있다:More specifically, the compound represented by Formula 1 may be selected from compounds having the structures of Formulas b-1 to b-54:
<화학식 b-1> <Formula b-1>
<화학식 b-2> <Formula b-2>
<화학식 b-3> <Formula b-3>
<화학식 b-4> <Formula b-4>
<화학식 b-5> <Formula b-5>
<화학식 b-6> <Formula b-6>
<화학식 b-7> <Formula b-7>
<화학식 b-8> <Formula b-8>
<화학식 b-9> <Formula b-9>
<화학식 b-10> <Formula b-10>
<화학식 b-11> <Formula b-11>
<화학식 b-12> <Formula b-12>
<화학식 b-13> <Formula b-13>
<화학식 b-14> <Formula b-14>
<화학식 b-15> <Formula b-15>
<화학식 b-16> <Formula b-16>
<화학식 b-17> <Formula b-17>
<화학식 b-18> <Formula b-18>
<화학식 b-19> <Formula b-19>
<화학식 b-20> <Formula b-20>
<화학식 b-21> <Formula b-21>
<화학식 b-22> <Formula b-22>
<화학식 b-23> <Formula b-23>
<화학식 b-24> <Formula b-24>
<화학식 b-25> <Formula b-25>
<화학식 b-26> <Formula b-26>
<화학식 b-27> <Formula b-27>
<화학식 b-28> <Formula b-28>
<화학식 b-29> <Formula b-29>
<화학식 b-30> <Formula b-30>
<화학식 b-31> <Formula b-31>
<화학식 b-32> <Formula b-32>
<화학식 b-33> <Formula b-33>
<화학식 b-34> <Formula b-34>
<화학식 b-35> <Formula b-35>
<화학식 b-36> <Formula b-36>
<화학식 b-37> <Formula b-37>
<화학식 b-38> <Formula b-38>
<화학식 b-39> <Formula b-39>
<화학식 b-40> <Formula b-40>
<화학식 b-41> <Formula b-41>
<화학식 b-42> <Formula b-42>
<화학식 b-43> <Formula b-43>
<화학식 b-44> <Formula b-44>
<화학식 b-45> <Formula b-45>
<화학식 b-46> <Formula b-46>
<화학식 b-47> <Formula b-47>
<화학식 b-48> <Formula b-48>
<화학식 b-49> <Formula b-49>
<화학식 b-50> <Formula b-50>
<화학식 b-51> <Formula b-51>
<화학식 b-52> <Formula b-52>
<화학식 b-53> <Formula b-53>
<화학식 b-54> <Formula b-54>
나아가, 본 발명에 따른 화학식 1로 나타내는 화합물에 있어서,Furthermore, in the compound represented by the formula (1) according to the present invention,
상기 Ar1은 나프틸기 또는 페난트렌기일 수 있다.Ar 1 may be a naphthyl group or a phenanthrene group.
구체적으로, 상기 화학식 1로 나타내는 화합물은 하기 화학식 c-1 내지 c-54의 구조를 갖는 화합물로부터 선택될 수 있다:Specifically, the compound represented by Formula 1 may be selected from compounds having the structures of Formulas c-1 to c-54:
<화학식 c-1> <Formula c-1>
<화학식 c-2> <Formula c-2>
<화학식 c-3> <Formula c-3>
<화학식 c-4> <Formula c-4>
<화학식 c-5> <Formula c-5>
<화학식 c-6> <Formula c-6>
<화학식 c-7> <Formula c-7>
<화학식 c-8> <Formula c-8>
<화학식 c-9> <Formula c-9>
<화학식 c-10> <Formula c-10>
<화학식 c-11> <Formula c-11>
<화학식 c-12> <Formula c-12>
<화학식 c-13> <Formula c-13>
<화학식 c-14> <Formula c-14>
<화학식 c-15> <Formula c-15>
<화학식 c-16> <Formula c-16>
<화학식 c-17> <Formula c-17>
<화학식 c-18> <Formula c-18>
<화학식 c-19> <Formula c-19>
<화학식 c-20> <Formula c-20>
<화학식 c-21> <Formula c-21>
<화학식 c-22> <Formula c-22>
<화학식 c-23> <Formula c-23>
<화학식 c-24> <Formula c-24>
<화학식 c-25> <Formula c-25>
<화학식 c-26> <Formula c-26>
<화학식 c-27> <Formula c-27>
<화학식 c-28> <Formula c-28>
<화학식 c-29> <Formula c-29>
<화학식 c-30> <Formula c-30>
<화학식 c-31> <Formula c-31>
<화학식 c-32> <Formula c-32>
<화학식 c-33> <Formula c-33>
<화학식 c-34> <Formula c-34>
<화학식 c-35> <Formula c-35>
<화학식 c-36> <Formula c-36>
<화학식 c-37> <Formula c-37>
<화학식 c-38> <Formula c-38>
<화학식 c-39> <Formula c-39>
<화학식 c-40> <Formula c-40>
<화학식 c-41> <Formula c-41>
<화학식 c-42> <Formula c-42>
<화학식 c-43> <Formula c-43>
<화학식 c-44> <Formula c-44>
<화학식 c-45> <Formula c-45>
<화학식 c-46> <Formula c-46>
<화학식 c-47> <Formula c-47>
<화학식 c-48> <Formula c-48>
<화학식 c-49> <Formula c-49>
<화학식 c-50> <Formula c-50>
<화학식 c-51> <Formula c-51>
<화학식 c-52> <Formula c-52>
<화학식 c-53> <Formula c-53>
<화학식 c-54><Formula c-54>
또한, 본 발명은 하나의 실시예에서,In addition, the present invention in one embodiment,
제1 전극;A first electrode;
제2 전극;Second electrode;
제1 전극과 제2 전극 사이에 배치된 발광층; A light emitting layer disposed between the first electrode and the second electrode;
제1 전극과 발광층 사이에 배치되는 정공 수송성층; 및A hole transport layer disposed between the first electrode and the light emitting layer; And
정공 수송성층과 발광층 사이에 배치되고, 하기 화학식 1로 나타내는 화합물을 포함하는 차단층을 포함하는 발광소자를 제공한다:A light emitting device is disposed between a hole transporting layer and a light emitting layer, and includes a blocking layer including a compound represented by Formula 1 below:
[화학식 1][Formula 1]
상기 화학식 1에서, R1, R2, La, Lb, Ar1, Ar2 및 Ar3은 상기에서 정의한 바와 같다.In Formula 1, R 1 , R 2 , L a , L b , Ar 1 , Ar 2 and Ar 3 are as defined above.
최근 발광소자의 적용 범위가 고전류/고출력 분야로 확대되면서, 발광소자에 대한 발광효율의 증대 및 발광수명의 개선이 요구되고 있다. 이때, 상기 발광효율 및 발광수명은 발광층 내에서의 정공과 전자의 결합이 원활히 이루어져야 개선될 수 있다. 그러나, 일반적으로 유기물의 전자 이동도는 정공 이동도에 비해 크므로, 제2 전극으로부터 주입되는 전자가 발광층을 지나 정공 수송성층으로 오버플로우(overflow) 될 수 있으며, 이로 인하여 발광층에서의 정공 및 전자의 결합 효율이 감소될 수 있다. 따라서, 발광층 내의 정공과 전자의 결합이 효율적으로 이루어지기 위해서는, 제2 전극에서 주입된 전자가 발광층을 벗어나지 못하도록 차단하는 한편, 발광층에서 형성된 여기자가 확산되거나 분리되는 것을 방지할 수 있어야 한다.Recently, as the application range of the light emitting device is expanded to the high current / high power field, it is required to increase the light emitting efficiency and the light emitting lifetime of the light emitting device. In this case, the light emission efficiency and light emission life can be improved only when the hole and the electron in the light emitting layer are smoothly combined. However, since the electron mobility of the organic material is generally larger than the hole mobility, electrons injected from the second electrode may overflow the light emitting layer to the hole transporting layer, thereby causing holes and electrons in the light emitting layer. The coupling efficiency of can be reduced. Therefore, in order to efficiently combine holes and electrons in the light emitting layer, the electrons injected from the second electrode must be prevented from leaving the light emitting layer, and the excitons formed in the light emitting layer must be prevented from being diffused or separated.
이러한 문제를 극복하기 위하여, 본 발명에 따른 상기 발광소자는 정공 수송성층과 발광층 사이에, 화학식 1로 나타내는 화합물을 포함하는 차단층이 도입된 구조를 가질 수 있다. 본 발명에 따른 상기 차단층은 화학식 1로 나타내는 화합물을 포함함으로써, 제2 전극에서 주입된 전자가 발광층을 경유하여 정공 수송성층으로 유입되거나, 발광층에서 형성된 여기자가 제1 전극의 방향으로 확산되어 비발광 소멸되는 것을 방지할 수 있다. 또한, 발광층에서 형성된 여기자가 발광층과 정공 수송성층 사이의 계면에서 '여기자 분리(exciton dissociation)' 과정을 거쳐 비발광 소멸하는 것을 방지할 수 있다. 즉, 상기 차단층은 전자 및 여기자가 발광층을 벗어나지 못하도록 차단하여 발광층 내의 전하 균형을 맞춤으로써 발광층에서의 여기자의 생성효율 및 발광소멸을 극대화할 수 있다. 따라서, 본 발명에 따른 화학식 1로 나타내는 화합물을 포함하는 차단층이 구비된 발광소자는 발광효율이 증대되고, 구동전압이 저하되어 발광수명이 개선될 수 있다. In order to overcome this problem, the light emitting device according to the present invention may have a structure in which a blocking layer including a compound represented by Formula 1 is introduced between the hole transporting layer and the light emitting layer. The blocking layer according to the present invention comprises a compound represented by the formula (1), the electrons injected from the second electrode flows into the hole transport layer via the light emitting layer, or the excitons formed in the light emitting layer is diffused in the direction of the first electrode and the ratio Light emission can be prevented from disappearing. In addition, the excitons formed in the light emitting layer may be prevented from disappearing by non-light emission through an 'exciton dissociation' process at the interface between the light emitting layer and the hole transporting layer. That is, the blocking layer blocks electrons and excitons from leaving the light emitting layer to balance charges in the light emitting layer, thereby maximizing the generation efficiency and excitation of excitons in the light emitting layer. Therefore, the light emitting device having a blocking layer including the compound represented by Chemical Formula 1 according to the present invention may increase luminous efficiency and decrease driving voltage, thereby improving luminous lifetime.
도 1 및 도 2는 본 발명에 따른 발광소자의 개략적인 구조 단면도를 도시한 이미지이다.1 and 2 are images showing a schematic structural cross-sectional view of a light emitting device according to the present invention.
도 1 및 도 2에 나타낸 바와 같이, 본 발명에 따른 발광소자(100 및 100A)는 베이스 기판(101) 상에 형성된 제1 전극(102), 정공 수송성층(103), 차단층(104), 발광층(105) 및 제2 전극(106)을 포함할 수 있다. 이때, 상기 발광소자(100 및 100A)는 유기 발광 다이오드(organic light emitting diode, OLED)일 수 있다. 이하, 본 발명에 따른 상기 발광소자의 각 구성요소를 도 1 및 도 2를 참고하여 상세히 설명한다.1 and 2, the light emitting devices 100 and 100A according to the present invention may include a first electrode 102, a hole transporting layer 103, a blocking layer 104, and the like formed on the base substrate 101. The light emitting layer 105 and the second electrode 106 may be included. In this case, the light emitting devices 100 and 100A may be organic light emitting diodes (OLEDs). Hereinafter, each component of the light emitting device according to the present invention will be described in detail with reference to FIGS. 1 and 2.
먼저, 본 발명에 따른 발광소자(100 및 100A)에 있어서, 상기 제1 전극(102)은 도전성 물질로서, 상기 베이스 기판(101) 상에 형성되어 발광소자(100 및 100A)의 양극(anode) 역할을 수행한다.First, in the light emitting devices 100 and 100A according to the present invention, the first electrode 102 is a conductive material and is formed on the base substrate 101 to form an anode of the light emitting devices 100 and 100A. Play a role.
이때, 상기 제1 전극(102)은 투명 전극 또는 불투명(반사) 전극일 수 있다. 상기 제1 전극(102)이 투명 전극인 경우, 제1 전극(102)은 인듐 틴 옥사이드 (indium tin oxide, ITO), 산화주석(SnO2) 등을 포함할 수 있다. 또한, 불투명(반사) 전극인 경우, 제1 전극(102)은 ITO/은(Ag)/ITO 구조를 포함할 수 있다.In this case, the first electrode 102 may be a transparent electrode or an opaque (reflective) electrode. When the first electrode 102 is a transparent electrode, the first electrode 102 may include indium tin oxide (ITO), tin oxide (SnO 2 ), or the like. In addition, in the case of an opaque (reflective) electrode, the first electrode 102 may include an ITO / silver (Ag) / ITO structure.
다음으로, 본 발명에 따른 발광소자(100 및 100A)에 있어서, 정공 수송성층(103)은 상기 제1 전극(102) 상에 형성되어, 제1 전극(102)과 차단층(104) 사이에 위치하게 된다.Next, in the light emitting devices 100 and 100A according to the present invention, a hole transporting layer 103 is formed on the first electrode 102, and is formed between the first electrode 102 and the blocking layer 104. Will be located.
이때, 상기 정공 수송성층(103)은 정공 수송층 및/또는 정공 주입층을 포함할 수 있다. 상기 정공 수송층으로는 예를 들면, 4,4-비스[N-(1-나프틸)-N-페닐-아민]바이페닐(α-NPD), N,N-디페닐-N,N-비스(3-메틸페닐)-1,1-바이페닐-4,4-디아민(TPD), 폴리-(N-비닐카바졸)(PVCz) 등을 단독 또는 2종 이상 혼합하여 포함할 수 있고, 별개의 층으로 하여 2층 이상 적층될 수 있으나, 이에 제한되는 것은 아니다. 또한, 상기 정공 주입층은 양극과 정공 수송층의 사이에 적층되며, 예를 들면, 구리 프탈로시아닌(copper phthalocyanine, CuPc) 등을 포함할 수 있으나, 이에 제한되는 것은 아니다In this case, the hole transport layer 103 may include a hole transport layer and / or a hole injection layer. As the hole transport layer, for example, 4,4-bis [N- (1-naphthyl) -N-phenyl-amine] biphenyl (? -NPD), N, N-diphenyl-N, N-bis (3-methylphenyl) -1,1-biphenyl-4,4-diamine (TPD), poly- (N-vinylcarbazole) (PVCz) and the like may be included alone or in combination of two or more thereof, Two or more layers may be laminated as a layer, but is not limited thereto. In addition, the hole injection layer may be stacked between the anode and the hole transport layer, and may include, for example, copper phthalocyanine (CuPc), but is not limited thereto.
또한, 본 발명에 따른 상기 정공 수송성층(103)은 하기 화학식 3으로 나타내는 화합물을 정공 수송성 화합물로 포함할 수 있다:In addition, the hole transport layer 103 according to the present invention may include a compound represented by the following formula (3) as a hole transport compound:
[화학식 3][Formula 3]
상기 화학식 3에서,In Chemical Formula 3,
R3 및 R4는 서로 독립적으로 수소, 탄소수 1 내지 6을 갖는 알킬기, 탄소수 6 내지 30을 갖는 아릴기 또는 탄소수 2 내지 20을 갖는 헤테로아릴기이고;R 3 and R 4 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms;
Lc는 -L1-L2-L3-L4-이며,L c is -L 1 -L 2 -L 3 -L 4- ,
L1, L2, L3 및 L4는 서로 독립적으로 단일결합, -O-, -S-, 탄소수 6 내지 30을 갖는 아릴렌기, 탄소수 2 내지 20을 갖는 헤테로아릴렌기 또는 탄소수 3 내지 20을 갖는 사이클로알킬렌기이되, L1, L2, L3 및 L4가 모두 단일결합인 경우는 제외되고;L 1 , L 2 , L 3, and L 4 are each independently a single bond, —O—, —S—, an arylene group having 6 to 30 carbon atoms, a heteroarylene group having 2 to 20 carbon atoms, or 3 to 20 carbon atoms. Having cycloalkylene groups, except where L 1 , L 2 , L 3 and L 4 are all single bonds;
Ar4 및 Ar5는 서로 독립적으로 탄소수 6 내지 30을 갖는 아릴기, 탄소수 2 내지 20을 갖는 헤테로아릴기 또는 하기 화학식 4로 나타내는 치환기이며,Ar 4 and Ar 5 are each independently an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, or a substituent represented by the following general formula (4),
[화학식 4][Formula 4]
상기 화학식 4에서,In Chemical Formula 4,
X는 O, S 또는 C(R7)(R8)이고,X is O, S or C (R 7 ) (R 8 ),
R5, R6, R7 및 R8은 서로 독립적으로 탄소수 1 내지 6을 갖는 알킬기, 탄소수 6 내지 30을 갖는 아릴기 또는 탄소수 2 내지 20을 갖는 헤테로아릴기이며,R 5 , R 6 , R 7 and R 8 are each independently an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms,
p는 0 내지 3의 정수이고,p is an integer from 0 to 3,
q는 0 내지 4의 정수이다.q is an integer of 0-4.
구체적으로, 본 발명에 따른 상기 화학식 3으로 나타내는 정공 수송성 화합물은 하기 화학식 5로 나타내는 화합물일 수 있다:Specifically, the hole transporting compound represented by Formula 3 according to the present invention may be a compound represented by the following Formula 5:
[화학식 5][Formula 5]
상기 화학식 5에서,In Chemical Formula 5,
R3은 탄소수 6 내지 30을 갖는 아릴기이고;R 3 is an aryl group having 6 to 30 carbon atoms;
R4는 수소이며;R 4 is hydrogen;
Lc는 탄소수 6 내지 20을 갖는 아릴렌기이고;L c is an arylene group having 6 to 20 carbon atoms;
Ar4는 탄소수 6 내지 30을 갖는 아릴기 또는 하기 화학식 4로 나타내는 치환기이며,Ar 4 is an aryl group having 6 to 30 carbon atoms or a substituent represented by the following formula (4),
[화학식 4][Formula 4]
상기 화학식 4에서,In Chemical Formula 4,
X는 O, S 또는 C(R7)(R8)이고,X is O, S or C (R 7 ) (R 8 ),
R5, R6, R7 및 R8은 서로 독립적으로 탄소수 1 내지 6을 갖는 알킬기 또는 탄소수 6 내지 30을 갖는 아릴기이며,R 5 , R 6 , R 7 and R 8 are each independently an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 30 carbon atoms,
p는 0 내지 2의 정수이고,p is an integer from 0 to 2,
q는 0 내지 2의 정수이다.q is an integer of 0-2.
보다 구체적으로, 본 발명에 따른 화학식 5로 나타내는 화합물에 있어서,More specifically, in the compound represented by Formula 5 according to the present invention,
상기 R3은 페닐기, 바이페닐기, 터페닐기 또는 나프틸기이고;R 3 is a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group;
R4는 수소이며;R 4 is hydrogen;
Lc는 페닐렌기, 바이페닐렌기, 터페닐렌기 또는 나프탈렌기이고; 및L c is a phenylene group, a biphenylene group, a terphenylene group or a naphthalene group; And
Ar4는 페닐기, 바이페닐기, 터페닐기, 나프틸기, 디벤조티에닐기, 디벤조퓨라닐기, 플루오레닐기, 디메틸플루오레닐기 또는 디페닐플루오레닐기일 수 있다.Ar 4 may be a phenyl group, biphenyl group, terphenyl group, naphthyl group, dibenzothienyl group, dibenzofuranyl group, fluorenyl group, dimethylfluorenyl group or diphenylfluorenyl group.
나아가, 본 발명에 따른 상기 정공 수송성층(103)은,Furthermore, the hole transport layer 103 according to the present invention,
P형 도펀트를 포함할 수 있는 제1 정공 수송성층(103a); 및A first hole transport layer 103a, which may include a P-type dopant; And
상기 화학식 3으로 나타내는 화합물을 포함하는 제2 정공 수송성층(103b)을 포함할 수 있다.The second hole transport layer 103b including the compound represented by Chemical Formula 3 may be included.
도 2에 나타낸 바와 같이, 본 발명에 따른 상기 정공 수송성층(103)은 상기 제1 전극(102)과 접촉하는 제1 정공 수송성층(103a); 및 상기 제1 정공 수송성층(103a)과 상기 차단층(104) 사이에 위치하는 제2 정공 수송성층(103b)을 포함할 수 있다. 즉, 상기 정공 수송성층(103)은 이층 구조를 가질 수 있다. 또한, 상기 정공 수송성층(103)은 상기 제1 및 제2 정공 수송성층(103a, 103b)을 포함하는 2층 이상의 다층 구조를 가질 수 있다.As shown in FIG. 2, the hole transport layer 103 according to the present invention includes a first hole transport layer 103a in contact with the first electrode 102; And a second hole transport layer 103b positioned between the first hole transport layer 103a and the blocking layer 104. That is, the hole transport layer 103 may have a two-layer structure. In addition, the hole transport layer 103 may have a multilayer structure of two or more layers including the first and second hole transport layers 103a and 103b.
본 발명에 따른 상기 제1 및 제2 정공 수송성층(103a, 103b)은 서로 동일한 종류의 정공 수송성 화합물을 포함할 수 있다. 상기 제1 정공 수송성층(103a)과 상기 제2 정공 수송성층(103b)에 포함되는 정공 수송성 화합물의 성분을 동일하게 사용하는 경우, 이종 물질간의 계면에서 발생될 수 있는 물리화학적 결함을 감소시켜 발광층으로 정공 주입을 용이하게 할 수 있다. 또한, 제1 정공 수송성층(103a)과 제2 정공 수송성층(103b)에 동일한 종류의 호스트 물질을 사용할 경우, 제1 정공 수송성층(103a)과 제2 정공 수송성층(103b)을 하나의 챔버 내에서 연속적으로 형성하므로, 제작 공정이 단순해지고 제작 시간을 단축시킬 수 있는 이점이 있다. 나아가, 제1 정공 수송성층(103a)과 제2 정공 수송성층(103b)이 인접하는 영역은 유리전이온도(Tg) 등의 물성이 유사하게 되므로, 소자의 내구성을 향상시킬 수 있는 이점도 있다.The first and second hole transport layers 103a and 103b according to the present invention may include the same kind of hole transport compound. When the same components of the hole transporting compound included in the first hole transporting layer 103a and the second hole transporting layer 103b are used in the same manner, the emission layer may be reduced by reducing physicochemical defects that may occur at an interface between different materials. This can facilitate the hole injection. In addition, when the same type of host material is used for the first hole transporting layer 103a and the second hole transporting layer 103b, the first hole transporting layer 103a and the second hole transporting layer 103b are formed in one chamber. Since it is formed continuously within, there is an advantage that the manufacturing process is simplified and the production time can be shortened. Furthermore, since the physical properties such as the glass transition temperature T g are similar in the region where the first hole transporting layer 103a and the second hole transporting layer 103b are adjacent to each other, the durability of the device may be improved.
또한, 본 발명에 따른 상기 제1 정공 수송성층(103a)은 정공 수송성 화합물로서, 상기 화학식 3으로 나타내는 정공 수송성 화합물과 P형 도펀트를 포함할 수 있다. 아울러, 상기 제2 정공 수송성층(103b)은 정공 수송성 화합물로서, 상기 화학식 3으로 나타내는 정공 수송성 화합물을 포함하되, 제2 정공 수송성층(103b)에 포함된 정공 수송성 화합물은 제1 정공 수송성층(103a)과 그 구조가 동일하거나 또는 상이할 수 있다. 보다 구체적으로, 상기 제1 및 제2 정공 수송성층(103a, 103b)을 구성하는 상기 정공 수송성 화합물은 상기 화학식 3으로 나타내는 정공 수송성 화합물이되, R3, R4, Lc, Ar4 및 Ar5 중 어느 하나 이상은 서로 독립적으로 상이할 수 있다. 이때, 상기 제1 및 제2 정공 수송성층(103a, 103b) 각각을 구성하는 화합물은 정공을 상기 발광층(105)으로 효율적으로 전달하기 위한 HOMO값을 갖도록 선택될 수 있다.In addition, the first hole transporting layer 103a according to the present invention may include a hole transporting compound represented by Chemical Formula 3 and a P-type dopant as a hole transporting compound. In addition, the second hole transporting layer 103b is a hole transporting compound, and includes a hole transporting compound represented by Chemical Formula 3, but the hole transporting compound included in the second hole transporting layer 103b may be a first hole transporting layer ( 103a) and the structure may be the same or different. More specifically, the hole transport compounds constituting the first and second hole transport layers (103a, 103b) is a hole transport compound represented by the formula (3), R 3 , R 4 , L c , Ar 4 And Ar Any one or more of 5 may be different from each other independently. In this case, the compound constituting each of the first and second hole transport layers 103a and 103b may be selected to have a HOMO value for efficiently transferring holes to the light emitting layer 105.
나아가, 상기 제1 정공 수송성층(103a)을 구성하는 본 발명에 따른 상기 P형 도펀트는 1 이상의 P형 유기물 도펀트 또는 P형 무기물 도펀트를 포함할 수 있고, 1 이상의 P형 유기물 도펀트 및 1 이상의 P형 무기물 도펀트를 동시에 포함할 수 있다.Furthermore, the P-type dopant according to the present invention constituting the first hole transporting layer 103a may include at least one P-type organic dopant or a P-type inorganic dopant, and at least one P-type organic dopant and at least one P-type. It may include the form inorganic dopant at the same time.
이때, 상기 P형 유기물 도펀트로는 예를 들면, 하기 화학식 6 내지 10으로 나타내는 헥사데카플루오로프탈로시아닌 (Hexadecafluorophthalocyanine, F16CuPc), 11,11,12,12-테트라시아노나프토-2,6-퀴노디메탄 (11,11,12,12-tetracyanonaphtho-2,6-quinodimethane, TNAP), 3,6-디플루오로-2,5,7,7,8,8-헥사시아노-퀴노디메탄 (3,6-difluoro-2,5,7,7,8,8-hexacyano-quinodimethane, F2-HCNQ), 테트라시아노퀴노디메탄(Tetracyanoquinodimethane, TCNQ) 등을 포함할 수 있다:In this case, as the P-type organic dopant, for example, hexadecafluorophthalocyanine (F16CuPc) represented by the following Chemical Formulas 6 to 10, 11,11,12,12-tetracyanonaphtho-2,6-quinodi Methane (11,11,12,12-tetracyanonaphtho-2,6-quinodimethane, TNAP), 3,6-difluoro-2,5,7,7,8,8-hexacyano-quinomimethane (3 , 6-difluoro-2,5,7,7,8,8-hexacyano-quinodimethane, F2-HCNQ), Tetracyanoquinodimethane (TCNQ), and the like:
[화학식 6][Formula 6]
상기 화학식 6에서,In Chemical Formula 6,
R은 시아노기, 설폰기, 설폭사이드기, 설폰아마이드기, 설포네이트기, 나이트로기 또는 트리플루오로메틸기이고,R is a cyano group, sulfone group, sulfoxide group, sulfonamide group, sulfonate group, nitro group or trifluoromethyl group,
[화학식 7][Formula 7]
[화학식 8][Formula 8]
[화학식 9][Formula 9]
[화학식 10][Formula 10]
상기 화학식 7 내지 10에서,In Chemical Formulas 7 to 10,
m 및 n은 서로 독립적으로 1 내지 5의 정수이고;m and n are independently of each other an integer from 1 to 5;
Y1 및 Y2는 서로 독립적으로 탄소수 6 내지 30을 갖는 아릴기 또는 탄소수 2 내지 20을 갖는 헤테로아릴기이며; 및Y 1 and Y 2 are each independently an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms; And
상기 아릴 및 헤테로아릴기의 수소는 서로 독립적으로 비치환; 또는 탄소수 1 내지 5를 갖는 알킬기, 탄소수 1 내지 5를 갖는 알콕시기, 탄소수 1 내지 5를 갖는 할로알콕시기, 하이드록시기 또는 할로겐기로 치환될 수 있다.Hydrogen of the aryl and heteroaryl group is unsubstituted independently from each other; Or an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a haloalkoxy group having 1 to 5 carbon atoms, a hydroxyl group or a halogen group.
또한, 상기 화학식 10으로 나타내는 화합물은 하기 화학식 10a 또는 하기 화학식 10b로 나타내는 화합물을 포함할 수 있다.In addition, the compound represented by Formula 10 may include a compound represented by Formula 10a or Formula 10b.
[화학식 10a][Formula 10a]
[화학식 10b][Formula 10b]
나아가, 상기 P형 무기물 도펀트로는 예를 들면, 금속 산화물, 금속 할라이드 등을 들 수 있다. 구체적으로는, MoO3, V2O5, WO3, SnO2, ZnO, MnO2, CoO2, ReO3, TiO2, FeCl3, SbCl5, MgF2 등을 들 수 있으며, 이들은 각각 단독으로 또는 2종 이상 혼합되어 사용될 수 있다.Furthermore, as said P-type inorganic dopant, a metal oxide, a metal halide, etc. are mentioned, for example. Specifically, MoO 3 , V 2 O 5 , WO 3 , SnO 2 , ZnO, MnO 2 , CoO 2 , ReO 3 , TiO 2, FeCl 3 , SbCl 5 , MgF 2 , and the like, each of which may be used alone. Or two or more kinds can be mixed and used.
또한, 상기 P형 도펀트의 함량은 상기 정공 수송성 화합물 100 중량부에 대하여, 약 0.5 중량부 내지 약 15 중량부이거나, 약 0.5 중량부 내지 약 5 중량부일 수 있다. 또는, 상기 정공 수송성 화합물 100 중량부에 대해서, 약 1 중량부 내지 10 중량부; 1 중량부 내지 5 중량부; 1.5 중량부 내지 6 중량부; 또는 2 중량부 내지 5 중량부일 수 있다.In addition, the content of the P-type dopant may be about 0.5 parts by weight to about 15 parts by weight, or about 0.5 parts by weight to about 5 parts by weight based on 100 parts by weight of the hole transporting compound. Or about 1 part by weight to 10 parts by weight based on 100 parts by weight of the hole transporting compound; 1 part by weight to 5 parts by weight; 1.5 parts by weight to 6 parts by weight; Or 2 parts by weight to 5 parts by weight.
상기 P형 도펀트의 함량이 상기 정공 수송성 화합물 100 중량부에 대해서, 약 0.5 중량부 내지 약 20 중량부인 경우, 상기 P형 도펀트가 상기 정공 수송성 화합물의 물성을 저하시키지 않으면서도 과도한 누설 전류의 발생을 방지할 수 있다. 또한, 상기 P형 도펀트에 의해서 상기 정공 수송성층(103)과 접촉하는 상, 하부층들 각각과의 계면에서의 에너지 장벽을 감소시킬 수 있다.When the content of the P-type dopant is about 0.5 part by weight to about 20 parts by weight with respect to 100 parts by weight of the hole transporting compound, the P-type dopant may generate excessive leakage current without reducing the physical properties of the hole-transporting compound. It can prevent. In addition, the energy barrier at the interface with each of the upper and lower layers in contact with the hole transport layer 103 may be reduced by the P-type dopant.
다음으로, 본 발명에 따른 발광소자(100 및 100A)에 있어서, 상기 차단층(104)은 하기 화학식 1로 나타내는 화합물을 포함할 수 있으며, 정공 수송성층(103)과 발광층(105) 사이에 위치하여, 전자 차단층(electron blocking layer, EBL); 여기자 차단층; 또는 여기자 분리 차단층(exciton dissociation blocking layer, EDBL)의 역할을 수행한다:Next, in the light emitting devices 100 and 100A according to the present invention, the blocking layer 104 may include a compound represented by Formula 1 below, and is located between the hole transport layer 103 and the light emitting layer 105. An electron blocking layer (EBL); Exciton blocking layer; Or serves as an exciton dissociation blocking layer (EDBL):
[화학식 1][Formula 1]
상기 화학식 1에서, R1, R2, La, Lb, Ar1, Ar2 및 Ar3은 상기에서 정의한 바와 같다.In Formula 1, R 1 , R 2 , L a , L b , Ar 1 , Ar 2 and Ar 3 are as defined above.
보다 구체적으로, 하나의 실시예에서, 본 발명에 따른 상기 화학식 1로 나타내는 화합물을 차단층(104)에 포함하는 발광소자(100 및 100A)에 대한 발광효율 및 발광수명을 평가하였다.More specifically, in one embodiment, the luminous efficiency and the light emitting life of the light emitting devices (100 and 100A) including the compound represented by Formula 1 in the blocking layer 104 according to the present invention was evaluated.
그 결과, 본 발명에 따른 발광소자는 차단층(104)을 포함하지 않는 발광소자에 비하여 발광효율은 약 1.17배 내지 1.54배 증대되고 발광수명은 약 1.23배 내지 1.66배 향상되는 것으로 나타났다. 또한, 화학식 1로 나타내는 화합물을 포함하지 않는 차단층이 구비된 발광소자와 대비하여 발광효율은 약 1.13배 내지 1.48배 증대되고, 발광수명은 약 1.13배 내지 1.52배 향상된 것으로 확인되었다.As a result, the light emitting device according to the present invention showed that the luminous efficiency is increased by about 1.17 to 1.54 times and the light emission lifetime is about 1.23 times to 1.66 times compared to the light emitting device that does not include the blocking layer 104. In addition, the luminous efficiency was increased by about 1.13 times to 1.48 times, and the light emission lifetime was improved by about 1.13 times to 1.52 times as compared with the light emitting device having the blocking layer not containing the compound represented by Formula 1.
이로부터, 본 발명에 따른 발광소자(100 및 100A)는 상기 화학식 1로 나타내는 화합물을 포함하는 차단층(104)을 구비함으로써, 우수한 발광효율 및 발광수명을 갖는 것을 알 수 있다.From this, it can be seen that the light emitting devices 100 and 100A according to the present invention have excellent blocking efficiency and light emitting lifetime by providing the blocking layer 104 including the compound represented by Chemical Formula 1.
본 발명에 따른 상기 차단층(104)은 도 1에 나타낸 바와 같이, 화학식 1로 나타내는 화합물을 1종 이상 포함하는 단층 구조이거나, 도 2에 나타낸 바와 같이, 차단1층(104a) 및 차단2층(104b)을 포함하는 이층 구조일 수 있다.As shown in FIG. 1, the blocking layer 104 according to the present invention has a single layer structure including at least one compound represented by Chemical Formula 1, or as shown in FIG. 2, the blocking 1 layer 104a and the blocking 2 layer. It may be a two-layer structure including 104b.
상기 차단층(104)이 이층 구조일 경우, 이층 구조를 구성하는 차단1층(104a) 및 차단2층(104b) 모두 화학식 1로 나타내는 화합물을 1종 이상 포함할 수 있으며, 이때, 각 개별층에 포함되는 화학식 1로 나타내는 화합물은 서로 다른 구조를 가질 수 있다. 또한, 상기 차단층(104)은 이층 구조를 구성하는 차단1층(104a) 및 차단2층(104b) 중 어느 한 층은 화학식 1로 나타내는 화합물을 1종 이상 포함하고, 다른 한 층은 하기 화학식 2로 나타내는 화합물을 포함하는 구조를 가질 수 있다:When the blocking layer 104 is a two-layer structure, both the blocking 1 layer 104a and the blocking 2 layer 104b constituting the double layer structure may include at least one compound represented by Formula 1, wherein each individual layer Compounds represented by Formula 1 included in may have a different structure. In addition, the blocking layer 104 is any one of the first blocking layer 104a and the second blocking layer 104b constituting a two-layer structure includes at least one compound represented by the formula (1), the other layer is the following formula It may have a structure comprising a compound represented by 2:
[화학식 2][Formula 2]
상기 화학식 2에서,In Chemical Formula 2,
Ra, Rb, Rc 및 Rd는 서로 독립적으로, 수소, 탄소수 1 내지 4를 갖는 알킬기 또는 탄소수 6 내지 14를 갖는 아릴기이다.R a , R b , R c and R d are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 14 carbon atoms.
또한, 본 발명에 따른 상기 차단층(104)은 발광소자(100 및 100A)의 공진 길이에 따라 두께를 조절함으로써 발광효율을 증가시킬 수 있고, 여기자가 발광층(105)과 다른 층 사이의 계면이 아닌, 상기 발광층(105)의 중앙부에서 형성될 수 있으므로, 그 두께를 특별히 제한되지는 않는다.In addition, the blocking layer 104 according to the present invention can increase the luminous efficiency by adjusting the thickness according to the resonance length of the light emitting device (100 and 100A), the exciton self-interface between the light emitting layer 105 and the other layer Instead, since the light emitting layer 105 may be formed at the center portion thereof, the thickness thereof is not particularly limited.
구체적으로, 상기 차단층의 구조가 단층인 경우, 20 Å 내지 400 Å 범위의 두께를 가질 수 있으며, 이층 구조인 경우에는 각 개별층이 10 Å 내지 200 Å 범위의 두께를 가질 수 있다.Specifically, when the structure of the barrier layer is a single layer, it may have a thickness in the range of 20 kPa to 400 kPa, and in the case of a two-layer structure, each individual layer may have a thickness in the range of 10 kPa to 200 kPa.
다음으로, 본 발명에 따른 발광소자(100 및 100A)에 있어서, 상기 발광층(105)은 차단층(104)과 제2 전극(106) 사이에 위치하며, 상기 발광층(105)이 방출하는 광의 파장은 발광층(105)을 형성하는 화합물의 종류에 따라 상이할 수 있다. 이때, 상기 발광층(105)을 형성하는 화합물로는 당업계에서 일반적으로 사용되는 것이라면 특별히 제한되지 않으며, 이를 상업적으로 입수하거나 또는 제조하여 사용할 수 있다.Next, in the light emitting devices 100 and 100A according to the present invention, the light emitting layer 105 is located between the blocking layer 104 and the second electrode 106, and the wavelength of the light emitted by the light emitting layer 105. The silver may be different depending on the kind of the compound forming the light emitting layer 105. In this case, the compound forming the light emitting layer 105 is not particularly limited as long as it is generally used in the art, and may be obtained commercially or manufactured and used.
다음으로, 본 발명에 따른 발광소자(100 및 100A)에 있어서, 상기 제2 전극(106)은 전도성 물질로서, 상기 발광층(105) 상에 위치하여 발광소자(100 및 100A)의 음극(cathode) 역할을 수행한다.Next, in the light emitting devices 100 and 100A according to the present invention, the second electrode 106 is a conductive material and is disposed on the light emitting layer 105 to cathode the light emitting devices 100 and 100A. Play a role.
이때, 상기 제2 전극(106)은 니켈, 마그네슘, 칼슘, 은, 알루미늄, 인듐 등의 금속 또는 이들 중 2 이상의 금속을 포함하는 합금을 포함할 수 있으며, 보다 구체적으로는 알루미늄을 포함할 수 있다. 또한, 상기 제2 전극(106)은 상기 금속이 단층 구조 또는 2층 이상의 다층 구조를 포함할 수 있다. 아울러, 상기 제1 전극(102)이 불투명 전극인 경우, 제2 전극(106)은 투명 또는 반투명 전극일 수 있으며, 이때, 제2 전극(106)은 마그네슘 및 은을 포함하는 합금을 사용할 수 있으며, 100Å 내지 150Å의 두께를 가질 수 있다.In this case, the second electrode 106 may include a metal such as nickel, magnesium, calcium, silver, aluminum, indium, or an alloy including two or more metals thereof, and more specifically, may include aluminum. . The second electrode 106 may include a single layer structure or a multilayer structure of two or more layers. In addition, when the first electrode 102 is an opaque electrode, the second electrode 106 may be a transparent or translucent electrode, and in this case, the second electrode 106 may use an alloy including magnesium and silver. , 100 μs to 150 μm in thickness.
한편, 본 발명에 따른 발광소자(100 및 100A)는 발광층(105)과 제2 전극(106) 사이에 전자 수송성층으로서, 전자 수송층(electron transporting layer, ETL) 및/또는 전자 주입층(electron injecting layer, EIL)(미도시)을 더 포함할 수 있다. 이때, 상기 전자 수송층 또는 상기 전자 주입층을 형성하는 물질로는 당업계에서 일반적으로 사용되는 것이라면 특별히 제한되지 않으며, 이를 상업적으로 입수하거나 또는 제조하여 사용할 수 있다.On the other hand, the light emitting device 100 and 100A according to the present invention is an electron transporting layer between the light emitting layer 105 and the second electrode 106, an electron transporting layer (ETL) and / or electron injection layer (electron injecting) layer, EIL) (not shown) may be further included. In this case, the material for forming the electron transport layer or the electron injection layer is not particularly limited as long as it is generally used in the art, it may be obtained commercially or manufactured and used.
상기 발광소자(100 및 100A)의 상기 제1 전극 및 제2 전극(102, 106) 사이에 전류를 흘려주는 경우, 제1 전극(102)으로부터 발광층(105)으로 주입된 정공(hole)과 제2 전극(106)으로부터 발광층(105)으로 주입된 전자(electron)가 결합하여 여기자(exciton)를 형성한다. 이때, 상기 여기자는 일중항(singlet) 여기자일 수 있으며, 또한 삼중항(triplet) 여기자일 수 있다. 이후, 상기 여기자가 기저 상태로 전이되는 과정에서, 특정 영역대의 파장을 갖는 광이 생성된다. 이에 따라, 상기 발광소자(100 및 100A)가 외부로 광을 제공할 수 있다.When a current flows between the first and second electrodes 102 and 106 of the light emitting devices 100 and 100A, holes and holes injected from the first electrode 102 to the light emitting layer 105 are formed. Electrons injected from the second electrode 106 into the light emitting layer 105 combine to form excitons. In this case, the excitons may be singlet excitons, and may also be triplet excitons. Then, in the process of transition of the excitons to the ground state, light having a wavelength of a specific region is generated. Accordingly, the light emitting devices 100 and 100A may provide light to the outside.
또한, 본 발명에 따른 발광소자(100 및 100A)에 있어서, 상기 발광소자(100 및 100A)는 발광층(105)과 제2 전극(106) 사이에 위치하는 제2 차단층(미도시)을 더 포함할 수 있다.In addition, in the light emitting devices 100 and 100A according to the present invention, the light emitting devices 100 and 100A further include a second blocking layer (not shown) positioned between the light emitting layer 105 and the second electrode 106. It may include.
상기 제2 차단층은 발광층(105)과 제2 전극(106), 구체적으로는 발광층(105)과 전자 수송층 사이에 위치하여, 정공이 제1 전극(102)에서부터 발광층(105)을 경유하여 전자 수송층으로 유입되는 것을 방지하는 정공 차단층(hole blocking layer, HBL)일 수 있다. 또한, 상기 제2 차단층은 상기 발광층(105)에서 형성된 여기자가 제2 전극(106)의 방향으로 확산되어 상기 여기자가 비발광 소멸하는 것을 방지하는 여기자 차단층(exciton blocking layer)일 수 있다.The second blocking layer is positioned between the light emitting layer 105 and the second electrode 106, specifically, the light emitting layer 105 and the electron transporting layer, so that holes are formed by electrons from the first electrode 102 via the light emitting layer 105. It may be a hole blocking layer (HBL) to prevent the flow into the transport layer (HBL). In addition, the second blocking layer may be an exciton blocking layer that prevents excitons formed in the emission layer 105 from diffusing in the direction of the second electrode 106 to prevent the excitons from extinction.
이때, 상기 제2 차단층은 발광소자(100 및 100A)의 공진 길이에 따라 두께를 조절함으로써 발광효율을 증가시킬 수 있고, 여기자가 발광층(105)과 다른 층 사이의 계면이 아닌, 상기 발광층(105)의 중앙부에서 형성되도록 할 수 있다.In this case, the second blocking layer may increase the luminous efficiency by adjusting the thickness according to the resonance lengths of the light emitting devices 100 and 100A, and the excitons are not the interface between the light emitting layer 105 and the other layer. 105 may be formed at the center portion.
본 발명에 따른 발광소자(100 및 100A)는 상기에서 설명한 제1 전극(102), 정공 수송성층(103), 차단층(104), 발광층(105), 제2 전극(106) 등을 통상적인 증착 방법을 이용하여 제조할 수 있으나, 증착 방법 외에 당업계에서 통상적으로 사용하는 방법이라면 제한없이 적용될 수 있다.The light emitting devices 100 and 100A according to the present invention typically include the first electrode 102, the hole transport layer 103, the blocking layer 104, the light emitting layer 105, the second electrode 106, and the like described above. Although it may be prepared using a deposition method, any method commonly used in the art other than the deposition method may be applied without limitation.
나아가, 본 발명은 하나의 실시예에서, 상기에서 설명된 발광소자를 포함하는 전자 장치를 제공한다. 이때, 본 발명에 따른 상기 전자 장치는 디스플레이 장치 또는 조명 장치일 수 있으나, 이에 제한되는 것은 아니다.Furthermore, in one embodiment, the present invention provides an electronic device including the light emitting device described above. In this case, the electronic device according to the present invention may be a display device or a lighting device, but is not limited thereto.
본 발명에 따른 전자 장치는 화학식 1로 나타내는 화합물을 포함하는 차단층을 도입함으로써, 발광효율이 증대되고, 발광수명이 개선된 발광소자를 포함하므로, 고휘도/고신뢰성이 요구되는 고전류/고출력 분야에서도 사용할 수 있다.The electronic device according to the present invention includes a light emitting device having an improved luminous efficiency and an improved luminous lifetime by introducing a blocking layer containing the compound represented by Chemical Formula 1, so that the electronic device may also be used in high current / high power fields requiring high brightness / high reliability. Can be used.
이하, 본 발명을 실시예 및 실험예에 의해 보다 상세히 설명한다.Hereinafter, the present invention will be described in more detail with reference to Examples and Experimental Examples.
단, 하기 실시예 및 실험예는 본 발명을 예시하는 것일 뿐, 본 발명의 내용이 하기 실시예 및 실험예에 한정되는 것은 아니다.However, the following Examples and Experimental Examples are only illustrative of the present invention, and the content of the present invention is not limited to the following Examples and Experimental Examples.
실시예 1.Example 1.
500 mL의 3구 둥근 바닥 플라스크에 질소를 충전한 후, 테트라히드로퓨란(THF, 150 mL)을 주입하였다. 상기 플라스크에 화학식 A(15.0 g, 25.27 mmol) 및 화학식 B(11.0 g, 55.61 mmol)를 용해시키고, 30분 동안 교반하였다. 그 후, 탄산나트륨(21.4 g, 202.22 mmol)을 증류수(100 mL)에 용해시켜 상기 혼합물에 첨가하고, 테트라키스(트리페닐포스핀)팔라듐(2.4 g, 2.03 mmol)을 첨가하였다. 그 후, 빛을 차단하고, 24시간 동안 환류한 다음, 반응 혼합물을 상온으로 냉각시켰다. 냉각된 반응 혼합물을 테트라히드로퓨란(THF, 50 mL)에 용해시키고, 메탄올(300 mL)이 담긴 1L 반응 용기에 첨가하였다. 그 후, 20분 동안 교반하고, 생성된 침전물을 여과 및 수집하여 연회색 고체의 목적화합물(화학식 1a, 18.0 g, 96%)을 얻었다.500 mL three-necked round bottom flask was charged with nitrogen, followed by injection of tetrahydrofuran (THF, 150 mL). To the flask was dissolved Formula A (15.0 g, 25.27 mmol) and Formula B (11.0 g, 55.61 mmol) and stirred for 30 minutes. Sodium carbonate (21.4 g, 202.22 mmol) was then dissolved in distilled water (100 mL) and added to the mixture and tetrakis (triphenylphosphine) palladium (2.4 g, 2.03 mmol) was added. Thereafter, the light was blocked, refluxed for 24 hours, and then the reaction mixture was cooled to room temperature. The cooled reaction mixture was dissolved in tetrahydrofuran (THF, 50 mL) and added to a 1 L reaction vessel containing methanol (300 mL). Thereafter, the mixture was stirred for 20 minutes, and the resulting precipitate was filtered and collected to obtain a target compound (Formula 1a, 18.0 g, 96%) as a light gray solid.
MALDI-TOF : m/z = 739.3245 (C57H41N = 739.3).MALDI-TOF: m / z = 739.3245 (C 57 H 41 N = 739.3).
실시예 2.Example 2.
500 mL의 3구 둥근 바닥 플라스크에 질소를 충전한 후, 테트라히드로퓨란(THF, 150 mL)을 주입하였다. 상기 플라스크에 화학식 C(15.0 g, 23.31 mmol) 및 화학식 B(10.16 g, 51.29 mmol)를 용해시키고, 30분 동안 교반하였다. 그 후, 탄산나트륨(19.77 g, 186.50 mmol)을 증류수(150 mL)에 용해시켜 상기 혼합물에 첨가하고, 테트라키스(트리페닐포스핀)팔라듐(2.2 g, 1.87 mmol)을 첨가하였다. 그 후, 빛을 차단하고, 10시간 동안 환류한 다음, 반응 혼합물을 상온으로 냉각시켰다. 냉각된 반응 혼합물을 테트라히드로퓨란(THF, 100 mL)에 용해시키고, 메탄올(300 mL)이 담긴 1L 반응 용기에 첨가하였다. 그 후, 40분 동안 교반하고, 생성된 침전물을 여과 및 수집하여 연회색 고체의 목적화합물(화학식 1b, 17.0 g, 92%)을 얻었다.500 mL three-necked round bottom flask was charged with nitrogen, followed by injection of tetrahydrofuran (THF, 150 mL). To the flask was dissolved Formula C (15.0 g, 23.31 mmol) and Formula B (10.16 g, 51.29 mmol) and stirred for 30 minutes. Sodium carbonate (19.77 g, 186.50 mmol) was then dissolved in distilled water (150 mL) and added to the mixture and tetrakis (triphenylphosphine) palladium (2.2 g, 1.87 mmol) was added. Thereafter, the light was blocked, refluxed for 10 hours, and then the reaction mixture was cooled to room temperature. The cooled reaction mixture was dissolved in tetrahydrofuran (THF, 100 mL) and added to a 1 L reaction vessel containing methanol (300 mL). Thereafter, the mixture was stirred for 40 minutes, and the resulting precipitate was filtered and collected to obtain a target compound (Formula 1b, 17.0 g, 92%) as a light gray solid.
MALDI-TOF : m/z = 789.2985 (C61H43N = 789.3).MALDI-TOF: m / z = 789.2985 (C 61 H 43 N = 789.3).
실시예 3.Example 3.
500 mL의 3구 둥근 바닥 플라스크에 질소를 충전한 후, 테트라히드로퓨란(THF, 100 mL)을 주입하였다. 상기 플라스크에 화학식 D(10.0 g, 15.59 mmol) 및 화학식 B(6.8 g, 34.30 mmol)를 용해시키고, 30분 동안 교반하였다. 그 후, 탄산나트륨(13.22 g, 124.72 mmol)을 증류수(120 mL)에 용해시켜 상기 혼합물에 첨가하고, 테트라키스(트리페닐포스핀)팔라듐(1.44 g, 1.25 mmol)을 첨가하였다. 그 후, 빛을 차단하고, 12시간 동안 환류한 다음, 반응 혼합물을 상온으로 냉각시켰다. 냉각된 반응 혼합물을 테트라히드로퓨란(THF, 70 mL)에 용해시키고, 메탄올(300 mL)이 담긴 1L 반응 용기에 첨가하였다. 그 후, 20분 동안 교반하고, 생성된 침전물을 여과 및 수집하여 연회색 고체의 목적화합물(화학식 1c, 11.5 g, 94%)을 얻었다.500 mL three-necked round bottom flask was charged with nitrogen and then tetrahydrofuran (THF, 100 mL) was injected. To the flask was dissolved Formula D (10.0 g, 15.59 mmol) and Formula B (6.8 g, 34.30 mmol) and stirred for 30 minutes. Sodium carbonate (13.22 g, 124.72 mmol) was then dissolved in distilled water (120 mL) and added to the mixture and tetrakis (triphenylphosphine) palladium (1.44 g, 1.25 mmol) was added. Thereafter, the light was blocked, refluxed for 12 hours, and the reaction mixture was cooled to room temperature. The cooled reaction mixture was dissolved in tetrahydrofuran (THF, 70 mL) and added to a 1 L reaction vessel containing methanol (300 mL). Thereafter, the mixture was stirred for 20 minutes, and the resulting precipitate was filtered and collected to obtain a target compound (Formula 1c, 11.5 g, 94%) as a light gray solid.
MALDI-TOF : m/z = 787.4510 (C61H41N = 787.3).MALDI-TOF: m / z = 787.4510 (C 61 H 41 N = 787.3).
실시예 4.Example 4.
500 mL의 3구 둥근 바닥 플라스크에 질소를 충전한 후, 테트라히드로퓨란(THF, 100 mL)을 주입하였다. 상기 플라스크에 화학식 E(10.0 g, 19.33 mmol) 및 화학식 B(8.42 g, 42.52 mmol)를 용해시키고, 30분 동안 교반하였다. 그 후, 탄산나트륨(21.37 g, 154.6 mmol)을 증류수(100 mL)에 용해시켜 상기 혼합물에 첨가하고, 테트라키스(트리페닐포스핀)팔라듐(1.79 g, 1.55 mmol)을 첨가하였다. 그 후, 빛을 차단하고, 18시간 동안 환류한 다음, 반응 혼합물을 상온으로 냉각시켰다. 냉각된 반응 혼합물을 테트라히드로퓨란(THF, 100 mL)에 용해시키고, 메탄올(300 mL)이 담긴 1L 반응 용기에 첨가하였다. 그 후, 50분 동안 교반하고, 생성된 침전물을 여과 및 수집하여 연회색 고체의 목적화합물(화학식 1d, 11.0 g, 86%)을 얻었다.500 mL three-necked round bottom flask was charged with nitrogen and then tetrahydrofuran (THF, 100 mL) was injected. To the flask was dissolved Formula E (10.0 g, 19.33 mmol) and Formula B (8.42 g, 42.52 mmol) and stirred for 30 minutes. Sodium carbonate (21.37 g, 154.6 mmol) was then dissolved in distilled water (100 mL) and added to the mixture and tetrakis (triphenylphosphine) palladium (1.79 g, 1.55 mmol) was added. Thereafter, the light was blocked, refluxed for 18 hours, and then the reaction mixture was cooled to room temperature. The cooled reaction mixture was dissolved in tetrahydrofuran (THF, 100 mL) and added to a 1 L reaction vessel containing methanol (300 mL). Thereafter, the mixture was stirred for 50 minutes, and the resulting precipitate was filtered and collected to obtain a target compound (Formula 1d, 11.0 g, 86%) as a light gray solid.
MALDI-TOF : m/z = 663.3101 (C51H37N = 663.3).MALDI-TOF: m / z = 663.3101 (C 51 H 37 N = 663.3).
실시예 5.Example 5.
500 mL의 3구 둥근 바닥 플라스크에 질소를 충전한 후, 테트라히드로퓨란(THF, 150 mL)을 주입하였다. 상기 플라스크에 화학식 A(15.0 g, 25.28 mmol) 및 화학식 F(6.78 g, 55.61 mmol)를 용해시키고, 30분 동안 교반하였다. 그 후, 탄산나트륨(21.43 g, 202.22 mmol)을 증류수(150 mL)에 용해시켜 상기 혼합물에 첨가하고, 테트라키스(트리페닐포스핀)팔라듐(2.34 g, 2.02 mmol)을 첨가하였다. 그 후, 빛을 차단하고, 20시간 동안 환류한 다음, 반응 혼합물을 상온으로 냉각시켰다. 냉각된 반응 혼합물을 테트라히드로퓨란(THF, 100 mL)에 용해시키고, 메탄올(300 mL)이 담긴 1L 반응 용기에 첨가하였다. 그 후, 30분 동안 교반하고, 생성된 침전물을 여과 및 수집하여 연회색 고체의 목적화합물(화학식 1e, 13.5 g, 91%)을 얻었다.500 mL three-necked round bottom flask was charged with nitrogen, followed by injection of tetrahydrofuran (THF, 150 mL). To the flask was dissolved Formula A (15.0 g, 25.28 mmol) and Formula F (6.78 g, 55.61 mmol) and stirred for 30 minutes. Sodium carbonate (21.43 g, 202.22 mmol) was then dissolved in distilled water (150 mL) and added to the mixture and tetrakis (triphenylphosphine) palladium (2.34 g, 2.02 mmol) was added. Thereafter, the light was blocked, refluxed for 20 hours, and then the reaction mixture was cooled to room temperature. The cooled reaction mixture was dissolved in tetrahydrofuran (THF, 100 mL) and added to a 1 L reaction vessel containing methanol (300 mL). Thereafter, the mixture was stirred for 30 minutes, and the resulting precipitate was filtered and collected to obtain a target compound (Formula 1e, 13.5 g, 91%) as a light gray solid.
MALDI-TOF : m/z = 587.3365 (C45H33N = 587.3).MALDI-TOF: m / z = 587.3365 (C 45 H 33 N = 587.3).
실시예 6.Example 6.
500 mL의 3구 둥근 바닥 플라스크에 질소를 충전한 후, 테트라히드로퓨란(THF, 100 mL)을 주입하였다. 상기 플라스크에 화학식 G(7.86 g, 13.02 mmol) 및 화학식 H(7.86 g, 28.66 mmol)를 용해시키고, 30분 동안 교반하였다. 그 후, 탄산나트륨(11.05 g, 104.23 mmol)을 증류수(100 mL)에 용해시켜 상기 혼합물에 첨가하고, 테트라키스(트리페닐포스핀)팔라듐(1.20 g, 1.04 mmol)을 첨가하였다. 그 후, 빛을 차단하고, 22시간 동안 환류한 다음, 반응 혼합물을 상온으로 냉각시켰다. 냉각된 반응 혼합물을 테트라히드로퓨란(THF, 70 mL)에 용해시키고, 메탄올(300 mL)이 담긴 1L 반응 용기에 첨가하였다. 그 후, 40분 동안 교반하고, 생성된 침전물을 여과 및 수집하여 연회색 고체의 목적화합물(화학식 1f, 12.5 g, 90%)을 얻었다.500 mL three-necked round bottom flask was charged with nitrogen and then tetrahydrofuran (THF, 100 mL) was injected. In the flask, Formula G (7.86 g, 13.02 mmol) and Formula H (7.86 g, 28.66 mmol) were dissolved and stirred for 30 minutes. Sodium carbonate (11.05 g, 104.23 mmol) was then dissolved in distilled water (100 mL) and added to the mixture and tetrakis (triphenylphosphine) palladium (1.20 g, 1.04 mmol) was added. Thereafter, the light was blocked, refluxed for 22 hours, and then the reaction mixture was cooled to room temperature. The cooled reaction mixture was dissolved in tetrahydrofuran (THF, 70 mL) and added to a 1 L reaction vessel containing methanol (300 mL). Thereafter, the mixture was stirred for 40 minutes, and the resulting precipitate was filtered and collected to obtain a target compound (Formula 1f, 12.5 g, 90%) as a light gray solid.
MALDI-TOF : m/z = 1065.4598 (C83H55N = 1065.4).MALDI-TOF: m / z = 1065.4598 (C 83 H 55 N = 1065.4).
실시예 7.Example 7.
500 mL의 3구 둥근 바닥 플라스크에 질소를 충전한 후, 테트라히드로퓨란(THF, 100 mL)을 주입하였다. 상기 플라스크에 화학식 I(12.0 g, 14.67 mmol) 및 화학식 H(8.85 g, 32.29 mmol)를 용해시키고, 30분 동안 교반하였다. 그 후, 탄산나트륨(12.45 g, 117.41 mmol)을 증류수(100 mL)에 용해시켜 상기 혼합물에 첨가하고, 테트라키스(트리페닐포스핀)팔라듐(1.36 g, 1.174 mmol)을 첨가하였다. 그 후, 빛을 차단하고, 9시간 동안 환류한 다음, 반응 혼합물을 상온으로 냉각시켰다. 냉각된 반응 혼합물을 테트라히드로퓨란(THF, 80 mL)에 용해시키고, 메탄올(300 mL)이 담긴 1L 반응 용기에 첨가하였다. 그 후, 30분 동안 교반하고, 생성된 침전물을 여과 및 수집하여 연회색 고체의 목적화합물(화학식 1g, 14.9 g, 91%)을 얻었다.500 mL three-necked round bottom flask was charged with nitrogen and then tetrahydrofuran (THF, 100 mL) was injected. To the flask was dissolved Formula I (12.0 g, 14.67 mmol) and Formula H (8.85 g, 32.29 mmol) and stirred for 30 minutes. Sodium carbonate (12.45 g, 117.41 mmol) was then dissolved in distilled water (100 mL) and added to the mixture and tetrakis (triphenylphosphine) palladium (1.36 g, 1.174 mmol) was added. Thereafter, the light was blocked and refluxed for 9 hours, and then the reaction mixture was cooled to room temperature. The cooled reaction mixture was dissolved in tetrahydrofuran (THF, 80 mL) and added to a 1 L reaction vessel containing methanol (300 mL). Thereafter, the mixture was stirred for 30 minutes, and the resulting precipitate was filtered and collected to obtain a target compound (Formula 1g, 14.9 g, 91%) as a light gray solid.
MALDI-TOF : m/z = 1115.4534 (C87H57N = 1115.5).MALDI-TOF: m / z = 1115.4534 (C 87 H 57 N = 1115.5).
실시예 8 - 14. 단층 구조의 차단층을 포함하는 발광소자의 제조Example 8-14. Fabrication of Light-Emitting Device comprising a Blocking Layer with a Single Layer Structure
인듐 틴 옥사이드(indium tin oxide, ITO)로 형성된 제1 전극 상에, 호스트 물질로서 하기 화학식 11로 나타내는 화합물을 1 Å/sec의 속도로 증착하고 동시에 하기 화학식 12로 나타내는 P형 도펀트(HAT-CN)를 상기 호스트 물질 100 중량부에 대해 3 중량부의 비율로 공증착(Co-evaporation)하여 100 Å 두께의 ㅈ제1 정공 수송성층을 형성하였다. 상기 제1 정공 수송성층 상에 화학식 11로 나타내는 화합물을 300 Å의 두께로 증착하여 제2 정공 수송성층을 형성하였다.On the first electrode formed of indium tin oxide (ITO), a compound represented by the following formula (11) as a host material was deposited at a rate of 1 Å / sec and simultaneously a P-type dopant represented by the following formula (HAT-CN) ) Was co-evaporated at a ratio of 3 parts by weight to 100 parts by weight of the host material to form a first hole transport layer having a thickness of 100 mm 3. The compound represented by Formula 11 was deposited on the first hole transporting layer to a thickness of 300 GPa to form a second hole transporting layer.
상기 제2 정공 수송성층 상에 하기 표 1에 나타낸 바와 같이, 실시예 1 - 7에서 제조된 화합물을 100 Å의 두께로 각각 증착하여 차단층을 형성하였다.As shown in Table 1 below, on the second hole transporting layer, the compounds prepared in Examples 1 to 7 were respectively deposited to a thickness of 100 GPa to form a blocking layer.
상기 차단층 상에 하기 화학식 13으로 나타내는 화합물과 화학식 14로 나타내는 화합물을 100:5 중량비로 공증착하여 200 Å 두께의 발광층을 형성하였다.A compound represented by the following Chemical Formula 13 and a compound represented by Chemical Formula 14 were co-deposited on the blocking layer at a weight ratio of 100: 5 to form a light emitting layer having a thickness of 200 kHz.
그런 다음, 상기 발광층 상에 하기 화학식 15로 나타내는 화합물과 하기 화학식 16으로 나타내는 화합물을 50:50 중량비로 공증착하여 360 Å 두께의 전자 수송층을 형성하였다. 이어서, 상기 전자 수송층 상에 하기 화학식 16으로 나타내는 화합물을 이용하여 5 Å 두께의 전자 주입층을 형성하였다.Thereafter, the compound represented by the following Formula 15 and the compound represented by the following Formula 16 were co-deposited in a 50:50 weight ratio on the emission layer to form an electron transport layer having a thickness of 360 kHz. Subsequently, an electron injection layer having a thickness of 5 kHz was formed on the electron transport layer by using the compound represented by the following formula (16).
마지막으로, 상기 전자 주입층 상에 1,000 Å 두께의 알루미늄 박막으로 제2 전극을 형성하여 단층 구조의 차단층을 포함하는 발광소자를 제조하였다.Finally, a second electrode was formed of an aluminum thin film having a thickness of 1,000 Å on the electron injection layer to manufacture a light emitting device including a blocking layer having a single layer structure.
표 1
Table 1
| 단층 구조의 차단층 | |
| 실시예 8 | 실시예 1에서 제조된 화학식 1a의 화합물 |
| 실시예 9 | 실시예 2에서 제조된 화학식 1b의 화합물 |
| 실시예 10 | 실시예 3에서 제조된 화학식 1c의 화합물 |
| 실시예 11 | 실시예 4에서 제조된 화학식 1d의 화합물 |
| 실시예 12 | 실시예 5에서 제조된 화학식 1e의 화합물 |
| 실시예 13 | 실시예 6에서 제조된 화학식 1f의 화합물 |
| 실시예 14 | 실시예 7에서 제조된 화학식 1g의 화합물 |
| Monolayer barrier layer | |
| Example 8 | Compound of Formula 1a prepared in Example 1 |
| Example 9 | Compound of Formula 1b prepared in Example 2 |
| Example 10 | Compound of Formula 1c prepared in Example 3 |
| Example 11 | Compound of Formula 1d, prepared in Example 4 |
| Example 12 | Compound of Formula 1e prepared in Example 5 |
| Example 13 | Compound of Formula 1f prepared in Example 6 |
| Example 14 | Compound of Formula 1g prepared in Example 7 |
[화학식 11][Formula 11]
[화학식 12][Formula 12]
[화학식 13][Formula 13]
[화학식 14][Formula 14]
[화학식 15][Formula 15]
[화학식 16][Formula 16]
실시예 15 - 21 (이층 구조 case 1). 이층 구조의 차단층을 포함하는 발광소자의 제조 Examples 15-21 (two-layer structure case 1). Fabrication of Light Emitting Diodes Including Blocking Layers of Two-layer Structure
인듐 틴 옥사이드(indium tin oxide, ITO)로 형성된 제1 전극 상에, 호스트 물질로서 상기 화학식 11로 나타내는 화합물을 1 Å/sec의 속도로 증착하고 동시에 상기 화학식 12로 나타내는 P형 도펀트(HAT-CN)를 상기 호스트 물질 100 중량부에 대해 3 중량부의 비율로 공증착(Co-evaporation)하여 100 Å 두께의 제1 정공 수송성층을 형성하였다. 상기 제1 정공 수송성층 상에 화학식 11로 나타내는 화합물을 300 Å의 두께로 증착하여 제2 정공 수송성층을 형성하였다.On the first electrode formed of indium tin oxide (ITO), a compound represented by the above formula (11) is deposited as a host material at a rate of 1 동시에 / sec and simultaneously a P-type dopant represented by the above formula (HAT-CN) ) Was co-evaporated at a ratio of 3 parts by weight to 100 parts by weight of the host material to form a first hole transport layer having a thickness of 100 mm 3. The compound represented by Formula 11 was deposited on the first hole transporting layer to a thickness of 300 GPa to form a second hole transporting layer.
상기 제2 정공 수송성층 상에 하기 표 2에 나타낸 바와 같이, 하기 화학식 17로 나타내는 화합물을 증착하여 차단1층을 형성한 다음, 상기 차단1층 상에 실시예 1 - 7에서 제조된 화합물을 각각 증착하여 차단2층을 형성하였다. 이때, 상기 차단1층 및 차단2층의 두께는 각각 50 Å이다.As shown in Table 2 below, on the second hole transporting layer, a compound represented by the following Chemical Formula 17 was deposited to form a blocking layer 1, and then the compounds prepared in Examples 1 to 7 were formed on the blocking layer 1, respectively. Deposition formed a barrier 2 layer. At this time, the thickness of the blocking layer 1 and the blocking layer 2 is 50 kPa each.
상기 차단2층 상에 상기 화학식 13으로 나타내는 화합물과 화학식 14로 나타내는 화합물을 100:5 중량비로 공증착하여 200 Å 두께의 발광층을 형성하였다.The compound represented by Chemical Formula 13 and the compound represented by Chemical Formula 14 were co-deposited at a weight ratio of 100: 5 on the blocking 2 layer to form a light emitting layer having a thickness of 200 kHz.
그런 다음, 상기 발광층 상에 상기 화학식 15로 나타내는 화합물과 상기 화학식 16으로 나타내는 화합물을 50:50 중량비로 공증착하여 360 Å 두께의 전자 수송층을 형성하였다. 이어서, 상기 전자 수송층 상에 상기 화학식 16으로 나타내는 화합물을 이용하여 5 Å 두께의 전자 주입층을 형성하였다.Thereafter, the compound represented by Chemical Formula 15 and the compound represented by Chemical Formula 16 were co-deposited in a 50:50 weight ratio on the emission layer to form an electron transport layer having a thickness of 360 kHz. Subsequently, an electron injection layer having a thickness of 5 mV was formed on the electron transport layer by using the compound represented by Chemical Formula 16.
마지막으로, 상기 전자 주입층 상에 1,000 Å 두께의 알루미늄 박막으로 제2 전극을 형성하여 이층 구조의 차단층을 포함하는 발광소자를 제조하였다.Finally, a second electrode was formed of an aluminum thin film having a thickness of 1,000 Å on the electron injection layer to manufacture a light emitting device including a blocking layer having a two-layer structure.
표 2
TABLE 2
| 차단1층 | 차단2층 | |
| 실시예 15 | 화학식 17의 화합물 | 실시예 1의 화합물 |
| 실시예 16 | 화학식 17의 화합물 | 실시예 2의 화합물 |
| 실시예 17 | 화학식 17의 화합물 | 실시예 3의 화합물 |
| 실시예 18 | 화학식 17의 화합물 | 실시예 4의 화합물 |
| 실시예 19 | 화학식 17의 화합물 | 실시예 5의 화합물 |
| 실시예 20 | 화학식 17의 화합물 | 실시예 6의 화합물 |
| 실시예 21 | 화학식 17의 화합물 | 실시예 7의 화합물 |
| 1st floor | 2nd floor | |
| Example 15 | Compound of formula 17 | Compound of Example 1 |
| Example 16 | Compound of formula 17 | Compound of Example 2 |
| Example 17 | Compound of formula 17 | Compound of Example 3 |
| Example 18 | Compound of formula 17 | Compound of Example 4 |
| Example 19 | Compound of formula 17 | Compound of Example 5 |
| Example 20 | Compound of formula 17 | Compound of Example 6 |
| Example 21 | Compound of formula 17 | Compound of Example 7 |
[화학식 17][Formula 17]
실시예 22 - 27 (이층 구조 case 2). 이층 구조의 차단층을 포함하는 발광소자의 제조 Examples 22-27 (two-layer structure case 2). Fabrication of Light Emitting Diodes Including Blocking Layers of Two-layer Structure
인듐 틴 옥사이드(indium tin oxide, ITO)로 형성된 제1 전극 상에, 호스트 물질로서 상기 화학식 11로 나타내는 화합물을 1 Å/sec의 속도로 증착하고 동시에 상기 화학식 12로 나타내는 P형 도펀트(HAT-CN)를 상기 호스트 물질 100 중량부에 대해 3 중량부의 비율로 공증착(Co-evaporation)하여 100 Å 두께의 제1 정공 수송성층을 형성하였다. 상기 제1 정공 수송성층 상에 화학식 11로 나타내는 화합물을 300 Å의 두께로 증착하여 제2 정공 수송성층을 형성하였다.On the first electrode formed of indium tin oxide (ITO), a compound represented by the above formula (11) is deposited as a host material at a rate of 1 동시에 / sec and simultaneously a P-type dopant represented by the above formula (HAT-CN) ) Was co-evaporated at a ratio of 3 parts by weight to 100 parts by weight of the host material to form a first hole transport layer having a thickness of 100 mm 3. The compound represented by Formula 11 was deposited on the first hole transporting layer to a thickness of 300 GPa to form a second hole transporting layer.
상기 제2 정공 수송성층 상에 하기 표 3에 나타낸 바와 같이, 실시예 4에서 제조된 화합물(화학식 1d)을 증착하여 차단1층을 형성한 다음, 상기 차단1층 상에 실시예 1 - 3 및 실시예5 - 7에서 제조된 화합물(화학식 1a - 1c 및 화학식 1e - 1g)을 각각 증착하여 차단2층을 형성하였다. 이때, 상기 차단1층 및 차단2층의 두께는 각각 50 Å이다.As shown in Table 3 below, on the second hole transporting layer, the compound prepared in Example 4 (Formula 1d) was deposited to form a blocking layer 1, and then on the blocking layer 1, Examples 1-3 and The compounds prepared in Examples 5-7 (Chemical Formulas 1a-1c and 1e-1g) were respectively deposited to form a barrier 2 layer. At this time, the thickness of the blocking layer 1 and the blocking layer 2 is 50 kPa each.
상기 차단2층 상에 상기 화학식 13으로 나타내는 화합물과 화학식 14로 나타내는 화합물을 100:5 중량비로 공증착하여 200 Å 두께의 발광층을 형성하였다.The compound represented by Chemical Formula 13 and the compound represented by Chemical Formula 14 were co-deposited at a weight ratio of 100: 5 on the blocking 2 layer to form a light emitting layer having a thickness of 200 kHz.
그런 다음, 상기 발광층 상에 상기 화학식 15로 나타내는 화합물과 상기 화학식 16으로 나타내는 화합물을 50:50 중량비로 공증착하여 360 Å 두께의 전자 수송층을 형성하였다. 이어서, 상기 전자 수송층 상에 상기 화학식 16으로 나타내는 화합물을 이용하여 5 Å 두께의 전자 주입층을 형성하였다.Thereafter, the compound represented by Chemical Formula 15 and the compound represented by Chemical Formula 16 were co-deposited in a 50:50 weight ratio on the emission layer to form an electron transport layer having a thickness of 360 kHz. Subsequently, an electron injection layer having a thickness of 5 mV was formed on the electron transport layer by using the compound represented by Chemical Formula 16.
마지막으로, 상기 전자 주입층 상에 1,000 Å 두께의 알루미늄 박막으로 제2 전극을 형성하여 이층 구조의 차단층을 포함하는 발광소자를 제조하였다.Finally, a second electrode was formed of an aluminum thin film having a thickness of 1,000 Å on the electron injection layer to manufacture a light emitting device including a blocking layer having a two-layer structure.
표 3
TABLE 3
| 차단1층 | 차단2층 | |
| 실시예 22 | 실시예 4의 화합물 | 실시예 1의 화합물 |
| 실시예 23 | 실시예 4의 화합물 | 실시예 2의 화합물 |
| 실시예 24 | 실시예 4의 화합물 | 실시예 3의 화합물 |
| 실시예 25 | 실시예 4의 화합물 | 실시예 5의 화합물 |
| 실시예 26 | 실시예 4의 화합물 | 실시예 6의 화합물 |
| 실시예 27 | 실시예 4의 화합물 | 실시예 7의 화합물 |
| 1st floor | 2nd floor | |
| Example 22 | Compound of Example 4 | Compound of Example 1 |
| Example 23 | Compound of Example 4 | Compound of Example 2 |
| Example 24 | Compound of Example 4 | Compound of Example 3 |
| Example 25 | Compound of Example 4 | Compound of Example 5 |
| Example 26 | Compound of Example 4 | Compound of Example 6 |
| Example 27 | Compound of Example 4 | Compound of Example 7 |
비교예 1. 차단층을 포함하지 않는 발광소자의 제조Comparative Example 1. Fabrication of Light-Emitting Device without Blocking Layer
상기 실시예 8에서, 제2 정공 수송성층 상에 차단층을 형성하지 않고, 발광층을 형성하는 것을 제외하고는 상기 실시예 8과 동일한 방법으로 수행하여 차단층을 포함하지 않는 발광소자를 제조하였다.In Example 8, except that the blocking layer is not formed on the second hole transport layer, except that the light emitting layer is formed in the same manner as in Example 8 to prepare a light emitting device containing no blocking layer.
비교예 2. 단층 구조의 차단층을 포함하는 발광소자의 제조Comparative Example 2. Fabrication of Light-Emitting Device Comprising Single Layer Blocking Layer
상기 실시예 8에서, 실시예 1에서 제조된 화합물(화학식 1a)을 사용하여 차단층을 형성하는 대신에 상기 화학식 17로 나타내는 화합물을 사용하여 차단층을 형성하는 것을 제외하고는 상기 실시예 8과 동일한 방법으로 수행하여 단층 구조의 차단층을 포함하는 발광소자를 제조하였다.In Example 8, except that the blocking layer is formed using the compound represented by Formula 17 instead of forming the blocking layer using the compound (Formula 1a) prepared in Example 1 and the Example 8 A light emitting device including a blocking layer having a single layer structure was prepared by the same method.
실험예 1. 발광소자의 발광효율 및 발광수명 평가Experimental Example 1. Evaluation of Luminous Efficiency and Luminous Life of Light Emitting Diode
본 발명에 따라 화학식 1로 나타내는 화합물을 차단층에 포함하는 발광소자의 발광효율 및 발광수명을 평가하기 위하여 하기와 같은 실험을 수행하였다.According to the present invention, the following experiment was performed to evaluate the luminous efficiency and luminous lifetime of the light emitting device including the compound represented by Chemical Formula 1 in the blocking layer.
먼저, 질소 분위기의 글로브 박스 안에서 흡습제(Getter)가 부착된 커버 글래스의 가장자리에 UV 경화용 실런트를 디스펜싱한 후, 상기 실시예 8 - 27 및 비교예 1 및 2에서 제조된 발광소자 각각과 커버 글래스를 합착하였다. 그 후, 합착된 발광소자에 UV 광을 조사하여 경화시키고, 경화된 발광소자의 발광효율을 측정하였다. 이때, 발광효율은 휘도가 1,000 cd/m2일 때의 값을 기준으로 하여 측정하였으며, 측정값의 단위는 lm/W이다.First, after dispensing the UV curing sealant at the edge of the cover glass with a moisture absorbent (Getter) in the glove box of nitrogen atmosphere, and then each of the light emitting device and the cover manufactured in Examples 8-27 and Comparative Examples 1 and 2 The glass was bonded. Thereafter, the bonded light emitting device was irradiated with UV light and cured, and the luminous efficiency of the cured light emitting device was measured. In this case, the luminous efficiency was measured based on the value when the luminance is 1,000 cd / m 2 , and the unit of the measured value is lm / W.
다음으로, 25℃의 온도로 일정하게 유지되고 있는 측정용 오븐 내에 설치된 수명 측정기를 이용하여 상기 실시예 8 - 27, 및 비교예 1 및 2에서 제조된 발광소자 각각의 발광수명을 측정하였다. 이때, T50은 발광소자의 초기 휘도가 5,000 cd/m2인 경우, 발광소자의 휘도가 초기 휘도 대비 50%가 되기까지 걸린 시간을 의미한다. 수명에 대한 값은 당업자에게 공지된 전환식을 기초로 하여 다른 측정 조건에서 측정한 경우에 예상되는 수명으로 전환될 수 있다.Next, the light emission life of each of the light emitting devices manufactured in Examples 8 to 27 and Comparative Examples 1 and 2 was measured using a life meter installed in a measuring oven maintained at a constant temperature of 25 ° C. In this case, when the initial luminance of the light emitting device is 5,000 cd / m 2 , T 50 means a time taken until the luminance of the light emitting device becomes 50% of the initial luminance. The value for lifetime can be converted to the expected lifetime when measured under different measurement conditions on the basis of conversion equations known to those skilled in the art.
하기 표 4는 실시예 8 - 14에 따른 발광소자의 발광효율 및 발광수명을 비교예 1 및 비교예 2에 따른 발광소자의 경우와 대비한 결과이다. 상기에서 설명한 바와 같이, 실시예 8 - 14는 차단층을 단층으로 구성하되 단층의 차단층이 상기 화학식 1로 나타내는 본 발명의 화합물을 포함하도록 구성한 경우이다.Table 4 shows the results of comparing the luminous efficiency and light emitting lifetime of the light emitting device according to Examples 8-14 with those of the light emitting device according to Comparative Example 1 and Comparative Example 2. As described above, Examples 8 to 14 are cases in which the barrier layer is composed of a single layer, but the barrier layer of the monolayer is configured to include the compound of the present invention represented by Chemical Formula 1.
표 4
Table 4
| 단층 구조의 차단층 | ||
| 발광효율[lm/W] | 발광수명(T50[hr]) | |
| 실시예 8 | 8.6 | 289 |
| 실시예 9 | 8.1 | 277 |
| 실시예 10 | 7.9 | 259 |
| 실시예 11 | 7.8 | 244 |
| 실시예 12 | 7.5 | 239 |
| 실시예 13 | 7.2 | 214 |
| 실시예 14 | 6.8 | 207 |
| 비교예 1 | 5.2 | 154 |
| 비교예 2 | 5.4 | 168 |
| Monolayer barrier layer | ||
| Luminous Efficiency [lm / W] | Light emitting life (T 50 [hr]) | |
| Example 8 | 8.6 | 289 |
| Example 9 | 8.1 | 277 |
| Example 10 | 7.9 | 259 |
| Example 11 | 7.8 | 244 |
| Example 12 | 7.5 | 239 |
| Example 13 | 7.2 | 214 |
| Example 14 | 6.8 | 207 |
| Comparative Example 1 | 5.2 | 154 |
| Comparative Example 2 | 5.4 | 168 |
또한, 하기 표 5는 실시예15 - 27에 따른 발광소자의 발광효율 및 발광수명을 나타낸 것이다. 상기에서 설명한 바와 같이 실시예 15 - 27에 따른 발광소자는 차단층을 이층 구조로 구성한 경우이다. 다만, 실시예 15 - 21은 이층 구조의 차단층 중 1개 층만이 본 발명에 따른 화학식 1의 화합물을 포함하도록 구성한 경우(이층 구조 case 1)이고, 실시예 22 - 27에 따른 발광소자는 2개 차단층이 모두 본 발명에 따른 화학식 1의 화합물을 포함하도록 구성한 경우(이층 구조 case 2) 이다.In addition, Table 5 shows the light emission efficiency and the light emitting life of the light emitting device according to Examples 15-27. As described above, the light emitting device according to Examples 15 to 27 is a case where the blocking layer has a two-layer structure. However, in Examples 15 to 21, only one layer of the blocking layer having a two-layer structure is configured to include the compound of Formula 1 according to the present invention (two-layer structure case 1), and the light emitting device according to Examples 22 to 27 is 2 It is the case that all the dog blocking layer is configured to include the compound of formula 1 according to the present invention (two-layer structure case 2).
표 5
Table 5
| 이층 구조의 차단층(이층 구조 case 1) | 이층 구조의 차단층(이층 구조 case 2) | ||||
| 발광효율[lm/W] | 발광수명(T50[hr]) | 발광효율[lm/W] | 발광수명(T50[hr]) | ||
| 실시예 15 | 8.0 | 255 | 실시예 22 | 8.3 | 274 |
| 실시예 16 | 7.8 | 241 | 실시예 23 | 7.9 | 255 |
| 실시예 17 | 7.3 | 235 | 실시예 24 | 7.7 | 239 |
| 실시예 18 | 7.1 | 231 | - | - | - |
| 실시예 19 | 6.5 | 207 | 실시예 25 | 6.8 | 224 |
| 실시예 20 | 6.3 | 198 | 실시예 26 | 6.7 | 205 |
| 실시예 21 | 6.1 | 189 | 실시예 27 | 6.5 | 198 |
| Two-layered barrier layer (two-layer case 1) | Two-layered barrier layer (two-layer case 2) | ||||
| Luminous Efficiency [lm / W] | Light emitting life (T 50 [hr]) | Luminous Efficiency [lm / W] | Light emitting life (T 50 [hr]) | ||
| Example 15 | 8.0 | 255 | Example 22 | 8.3 | 274 |
| Example 16 | 7.8 | 241 | Example 23 | 7.9 | 255 |
| Example 17 | 7.3 | 235 | Example 24 | 7.7 | 239 |
| Example 18 | 7.1 | 231 | - | - | - |
| Example 19 | 6.5 | 207 | Example 25 | 6.8 | 224 |
| Example 20 | 6.3 | 198 | Example 26 | 6.7 | 205 |
| Example 21 | 6.1 | 189 | Example 27 | 6.5 | 198 |
상기 표 4 및 표 5에 나타난 바와 같이, 본 발명에 따른 발광소자는 발광효율 및 발광수명이 비교예 1 및 비교예 2의 경우보다 우수한 것을 알 수 있다.As shown in Table 4 and Table 5, it can be seen that the light emitting device according to the present invention is superior in the luminous efficiency and light emitting life than that of Comparative Example 1 and Comparative Example 2.
구체적으로, 표 4를 참조하여 단층 구조의 차단층을 포함하는 발광소자를 살펴보면, 본 발명에 따른 화학식 1로 나타내는 화합물을 차단층에 포함하는 발광소자는 발광효율이 6.8 내지 8.6l m/W이고, 발광수명은 207 내지 289시간인 것으로 나타났다.Specifically, referring to Table 4, the light emitting device comprising a blocking layer of a single layer structure, the light emitting device comprising a compound represented by the formula (1) according to the invention in the blocking layer has a light emission efficiency of 6.8 to 8.6lm / W, Luminescence lifetime was found to be 207 to 289 hours.
반면, 차단층을 포함하지 않는 비교예 1의 발광소자의 경우, 발광효율은 5.2 lm/W이고, 발광수명은 154시간으로, 본 발명에 따른 발광소자와 대비하여 발광효율 및 발광수명이 현저히 낮은 것으로 확인되었다. 또한, 차단층을 포함하더라도 그 차단층이 화학식 1로 나타내는 화합물이 아닌 다른 화합물을 포함하는 비교예 2의 발광소자의 경우, 발광효율 및 발광수명은 각각 5.4 lm/W, 168시간으로, 발광효율 및 발광수명이 개선되는 정도가 본 발명에 따른 발광소자와 대비하여 낮은 것으로 확인되었다.On the other hand, in the light emitting device of Comparative Example 1 that does not include a blocking layer, the light emitting efficiency is 5.2 lm / W, the light emitting lifetime is 154 hours, and the light emitting efficiency and the light emitting lifetime are significantly lower than those of the light emitting device according to the present invention. It was confirmed. In addition, in the light emitting device of Comparative Example 2 in which the blocking layer includes a compound other than the compound represented by Chemical Formula 1 even though the blocking layer is included, the light emitting efficiency and the light emitting lifetime are 5.4 lm / W and 168 hours, respectively. And it is confirmed that the degree of improvement in the light emitting life is low compared to the light emitting device according to the present invention.
즉, 본 발명에 따른 화학식 1로 나타내는 화합물을 포함하는 단층 구조의 차단층을 구비한 발광소자는 차단층을 포함하지 않은 발광소자와 대비하여 발광효율은 약 1.30 내지 1.65배 증대되고, 발광수명은 약 1.34 내지 1.88배 향상된 것을 알 수 있다. 또한, 본 발명에 따른 화학식 1로 나타내는 화합물을 포함하는 단층 구조의 차단층을 구비한 발광소자는 화학식 1로 나타내는 화합물이 아닌 다른 화합물을 포함하는 단층 구조의 차단층을 구비한 발광소자와 대비해서도 발광효율이 약 1.26 내지 1.59배 증대되고, 발광수명은 1.23 내지 1.72배 향상된 것을 알 수 있다. That is, the light emitting device having a single-layer blocking layer including the compound represented by Chemical Formula 1 according to the present invention has a light emission efficiency of about 1.30 to 1.65 times that of the light emitting device that does not include the blocking layer, and has a light emitting lifetime. It can be seen that about 1.34 to 1.88 fold improvement. In addition, the light emitting device having a single layer structure blocking layer including the compound represented by Formula 1 according to the present invention is compared with the light emitting device having a single layer structure blocking layer comprising a compound other than the compound represented by Formula 1 In addition, it can be seen that the luminous efficiency is increased by about 1.26 to 1.59 times, and the light emitting life is improved by 1.23 to 1.72 times.
나아가, 표 5를 참조하여 이층 구조의 차단층을 포함하는 발광소자를 살펴보면, 이층 구조의 차단층 중 1개 층이 본 발명에 따른 화학식 1로 나타내는 화합물을 포함하는 발광소자(이층 구조 case 1)는 발광효율이 6.1 내지 8.0l m/W이고, 발광수명은 189 내지 255시간인 것으로 나타났다. 아울러, 이층 구조의 차단층이 모두 본 발명에 따른 화학식 1로 나타내는 화합물을 포함하는 발광소자(이층 구조 case 2)는 발광효율이 6.5 내지 8.3 m/W이고, 발광수명은 198 내지 274시간인 것으로 나타났다.Furthermore, referring to Table 5, a light emitting device including a blocking layer having a two-layer structure, one layer of the blocking layer of a two-layer structure includes a light emitting device comprising a compound represented by the formula (1) according to the present invention (two-layer structure case 1) The luminous efficiency was found to be 6.1 to 8.0 lm / W, and the light emitting lifetime was 189 to 255 hours. In addition, the light-emitting device (two-layer structure case 2) containing all of the two-layer blocking layer compound represented by the formula (1) according to the present invention is that the luminous efficiency is 6.5 to 8.3 m / W, the emission life is 198 to 274 hours appear.
즉, 상기 이층 구조 case 1의 경우에는 차단층을 포함하지 않는 발광소자와 대비하여 발광효율은 약 1.17 내지 1.54배 증대되고, 발광수명은 약 1.23 내지 1.66배 향상된 것을 알 수 있으며, 화학식 1로 나타내는 화합물이 아닌 다른 화합물을 포함하는 단층 구조의 차단층을 구비한 발광소자와 대비해도 발광효율이 약 1.13 내지 1.48배 증대되고, 발광수명은 1.13 내지 1.52배 향상된 것을 알 수 있다.That is, in the case of the two-layer structure case 1, the luminous efficiency is increased by about 1.17 to 1.54 times and the luminous lifetime is about 1.23 to 1.66 times as compared with the light emitting device that does not include the blocking layer. It can be seen that the luminous efficiency is increased by about 1.13 to 1.48 times, and the light emission life is improved by 1.13 to 1.52 times even when compared with a light emitting device having a single-layer blocking layer including a compound other than the compound.
아울러, 상기 이층 구조 case 2의 경우에는 차단층을 포함하지 않는 발광소자와 대비하여 발광효율은 약 1.25 내지 1.60배 증대되고, 발광수명은 약 1.29 내지 1.78배 향상된 것을 알 수 있으며, 화학식 1로 나타내는 화합물이 아닌 다른 화합물을 포함하는 단층의 차단층을 구비한 발광소자에 비해서도 발광효율이 약 1.20 내지 1.54배 증대되고, 발광수명은 1.18 내지 1.63배 향상된 것을 알 수 있다.In addition, in the case of the two-layer structure case 2, the light emission efficiency is increased by about 1.25 to 1.60 times, and the light emission life is improved by about 1.29 to 1.78 times as compared to the light emitting device that does not include the blocking layer. It can be seen that the luminous efficiency is increased by about 1.20 to 1.54 times and the luminous lifetime is 1.18 to 1.63 times compared to the light emitting device having a single layer blocking layer including a compound other than the compound.
이로부터, 이층 구조 case 1 및 case 2 모두 차단층을 포함하지 않거나 본 발명에 따른 화학식 1로 나타내는 화합물이 아닌 다른 화합물로 단층 구조의 차단층을 구성한 경우와 대비하여 발광효율 및 발광수명이 크게 향상된 것을 알 수 있다.From this, both the case 1 and case 2 of the two-layer structure does not include a blocking layer, or the luminous efficiency and the light-emitting lifetime are greatly improved as compared with the case of forming a blocking layer of a single layer structure with a compound other than the compound represented by Formula 1 according to the present invention. It can be seen that.
한편, 상기 결과로부터 이층 구조 case 1 및 case 2의 경우 보다는 본 발명에 따른 화학식 1의 화합물을 포함하는 단층 구조로 차단층을 구성하는 경우가 발광효율 및 발광수명 측면에서 보다 유리한 것을 알 수 있다.On the other hand, from the above results it can be seen that the case of the barrier layer composed of a single layer structure comprising the compound of the formula (1) according to the present invention than the case of the two-layer structure case 1 and case 2 is more advantageous in terms of luminous efficiency and light emitting life.
보다 구체적으로 단층 구조로 차단층을 형성한 경우와 이층 구조 case 1을 대비해 보면, 단층 구조로 차단층을 형성한 실시예 8 - 14의 발광효율 및 발광수명이 동일한 화합물을 차단2층에 사용한 실시예 15 - 21의 경우보다 우수한 것을 알 수 있다. 단층 구조로 차단층을 형성한 경우와 이층 구조 case 2를 대비해 보면, 단층 구조로 차단층을 형성한 실시예 8 - 14의 경우가 동일한 화합물로 차단2층을 형성하면서 실시예 4의 화합물로 차단1층을 형성한 경우보다 발광효율 및 발광수명이 우수한 것을 알 수 있다.More specifically, in contrast to the case in which the barrier layer is formed of a single layer structure and the case of the two-layer structure case 1, the compound having the same luminous efficiency and lifespan of Example 8-14 in which the barrier layer is formed in a single layer structure is used for the barrier layer 2. It turns out that it is superior to the case of Examples 15-21. In contrast to the case of forming the barrier layer in the single layer structure and the case of the two-layer structure case, Examples 8 to 14 in which the barrier layer was formed in the single layer structure were blocked with the compound of Example 4 while forming the barrier layer 2 with the same compound. It can be seen that the luminous efficiency and the light emitting lifetime are superior to those in the case of forming one layer.
또한, 이층 구조 case 1과 case 2를 대비해 보면, 동일한 화합물로 차단2층을 형성하더라도 차단1층을 본 발명에 따른 화합물로 형성한 이층 구조 case 2의 발광효율 및 발광수명이 이층 구조 case 1의 경우보다 우수한 것을 알 수 있다. 즉, 이층 구조로 차단층을 형성할 경우 1개 층만 본 발명에 따른 화학식 1의 화합물을 포함하는 이층 구조 case 1 보다는 2개층 모두 본 발명에 따른 화학식 1의 화합물을 포함하는 이층 구조 case 2가 더욱 향상된 발광효율 및 발광수명을 나타낸 것을 알 수 있다.In addition, in contrast to the two-layer structure case 1 and case 2, the luminous efficiency and lifetime of the two-layer structure case 1 in which the two-layer structure case 2 is formed of the compound according to the present invention even if the two-layer blocking layer is formed of the same compound. It can be seen that it is superior to the case. That is, when the barrier layer is formed in a two-layer structure, the two-layer structure case 2 including the compound of formula 1 according to the present invention is more preferable than the two-layer structure case 1 including only one layer of the compound of formula 1 according to the present invention. It can be seen that the improved luminous efficiency and emission life.
이로부터, 발광소자가 본 발명에 따른 화학식 1로 나타내는 화합물을 포함하는 차단층을 구비할 경우, 차단층을 포함하지 않거나 차단층을 포함하더라도 화학식 1의 화합물이 아닌 다른 화합물을 차단층에 포함하는 경우와 대비하여 발광효율 및 발광수명이 현저히 향상되는 것을 알 수 있다.When the light emitting device includes a blocking layer including the compound represented by Formula 1 according to the present invention, the blocking layer may include a compound other than the compound of Formula 1 in the blocking layer even if it does not include the blocking layer or includes the blocking layer. In contrast, it can be seen that the luminous efficiency and the light emitting lifetime are remarkably improved.
따라서, 본 발명에 따른 발광소자는 화학식 1로 나타내는 화합물을 포함하는 차단층을 구비함으로써, 우수한 발광소자 및 발광수명을 가지므로, 고휘도/고신뢰성이 요구되는 고전류/고출력 분야의 전자 장치에 유용하게 사용될 수 있다.Therefore, the light emitting device according to the present invention has an excellent light emitting device and a light emitting life by providing a blocking layer including the compound represented by Chemical Formula 1, and thus is useful for electronic devices in high current / high power fields requiring high brightness / high reliability. Can be used.
Claims (20)
- 하기 화학식 1로 나타내는 화합물:Compound represented by the following formula (1):[화학식 1][Formula 1]
상기 화학식 1에서,In Chemical Formula 1,R1 및 R2는 서로 독립적으로 수소, 탄소수 1 내지 4를 갖는 알킬기 또는 탄소수 6 내지 10을 갖는 아릴기이고;R 1 and R 2 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms;La 및 Lb는 서로 독립적으로 단일결합 또는 탄소수 6 내지 30을 갖는 아릴렌기이며; 및L a and L b are each independently a single bond or an arylene group having 6 to 30 carbon atoms; AndAr1, Ar2 및 Ar3은 서로 독립적으로 수소 또는 탄소수 6 내지 30을 갖는 아릴기이다.Ar 1 , Ar 2 and Ar 3 are each independently hydrogen or an aryl group having 6 to 30 carbon atoms. - 제1항에 있어서,The method of claim 1,화학식 1에서,In Formula 1,상기 R1 및 R2는 서로 독립적으로 수소, 탄소수 1 내지 4를 갖는 알킬기 또는 탄소수 6 내지 10을 갖는 아릴기이고;R 1 and R 2 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms;La 및 Lb는 서로 독립적으로 단일결합 또는 탄소수 6 내지 14를 갖는 아릴렌기이며;L a and L b are each independently a single bond or an arylene group having 6 to 14 carbon atoms;Ar1은 수소이고; 및Ar 1 is hydrogen; AndAr2 및 Ar3은 서로 독립적으로 수소 또는 탄소수 6 내지 20을 갖는 아릴기인 화합물.Ar 2 and Ar 3 are each independently hydrogen or an aryl group having 6 to 20 carbon atoms.
- 제2항에 있어서,The method of claim 2,제2항에 따른 화합물은 하기 화학식 a-1 내지 a-27의 구조로부터 선택되는 것을 특징으로 하는 화합물:A compound according to claim 2, wherein the compound is selected from the structures of formulas a-1 to a-27:<화학식 a-1> <Formula a-1>
<화학식 a-2> <Formula a-2>
<화학식 a-3> <Formula a-3>
<화학식 a-4> <Formula a-4>
<화학식 a-5> <Formula a-5>
<화학식 a-6> <Formula a-6>
<화학식 a-7> <Formula a-7>
<화학식 a-8> <Formula a-8>
<화학식 a-9> <Formula a-9>
<화학식 a-10> <Formula a-10>
<화학식 a-11> <Formula a-11>
<화학식 a-12> <Formula a-12>
<화학식 a-13> <Formula a-13>
<화학식 a-14> <Formula a-14>
<화학식 a-15> <Formula a-15>
<화학식 a-16> <Formula a-16>
<화학식 a-17> <Formula a-17><화학식 a-18> <Formula a-18>
<화학식 a-19> <Formula a-19>
<화학식 a-20> <Formula a-20>
<화학식 a-21> <Formula a-21>
<화학식 a-22> <Formula a-22>
<화학식 a-23> <Formula a-23>
<화학식 a-24> <Formula a-24>
<화학식 a-25> <Formula a-25>
<화학식 a-26> <Formula a-26>
<화학식 a-27> <Formula a-27>.
. - 제1항에 있어서,The method of claim 1,화학식 1에서,In Formula 1,상기 R1 및 R2는 서로 독립적으로 수소, 탄소수 1 내지 4를 갖는 알킬기 또는 탄소수 6 내지 10을 갖는 아릴기이고;R 1 and R 2 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms;La 및 Lb는 서로 독립적으로 단일결합 또는 탄소수 6 내지 14를 갖는 아릴렌기이며;L a and L b are each independently a single bond or an arylene group having 6 to 14 carbon atoms;Ar1은 탄소수 6 내지 30을 갖는 아릴기이고; 및Ar 1 is an aryl group having 6 to 30 carbon atoms; AndAr2 및 Ar3은 서로 독립적으로 수소 또는 탄소수 6 내지 20을 갖는 아릴기인 화합물.Ar 2 and Ar 3 are each independently hydrogen or an aryl group having 6 to 20 carbon atoms.
- 제4항에 있어서,The method of claim 4, wherein화학식 1에서,In Formula 1,상기 Ar1은 페닐기 또는 바이페닐기인 화합물.Ar 1 is a phenyl group or a biphenyl group.
- 제5항에 있어서,The method of claim 5,제5항에 따른 화합물은 하기 화학식 b-1 내지 b-54의 구조로부터 선택되는 것을 특징으로 하는 화합물:A compound according to claim 5, wherein the compound is selected from the structures of formulas b-1 to b-54:<화학식 b-1> <Formula b-1>
<화학식 b-2> <Formula b-2>
<화학식 b-3> <Formula b-3>
<화학식 b-4> <Formula b-4>
<화학식 b-5> <Formula b-5>
<화학식 b-6> <Formula b-6>
<화학식 b-7> <Formula b-7>
<화학식 b-8> <Formula b-8>
<화학식 b-9> <Formula b-9>
<화학식 b-10> <Formula b-10>
<화학식 b-11> <Formula b-11>
<화학식 b-12> <Formula b-12>
<화학식 b-13> <Formula b-13>
<화학식 b-14> <Formula b-14>
<화학식 b-15> <Formula b-15>
<화학식 b-16> <Formula b-16>
<화학식 b-17> <Formula b-17>
<화학식 b-18> <Formula b-18>
<화학식 b-19> <Formula b-19>
<화학식 b-20> <Formula b-20>
<화학식 b-21> <Formula b-21>
<화학식 b-22> <Formula b-22>
<화학식 b-23> <Formula b-23>
<화학식 b-24> <Formula b-24>
<화학식 b-25> <Formula b-25>
<화학식 b-26> <Formula b-26>
<화학식 b-27> <Formula b-27>
<화학식 b-28> <Formula b-28>
<화학식 b-29> <Formula b-29>
<화학식 b-30> <Formula b-30>
<화학식 b-31> <Formula b-31>
<화학식 b-32> <Formula b-32>
<화학식 b-33> <Formula b-33>
<화학식 b-34> <Formula b-34>
<화학식 b-35> <Formula b-35>
<화학식 b-36> <Formula b-36>
<화학식 b-37> <Formula b-37>
<화학식 b-38> <Formula b-38>
<화학식 b-39> <Formula b-39>
<화학식 b-40> <Formula b-40>
<화학식 b-41> <Formula b-41>
<화학식 b-42> <Formula b-42>
<화학식 b-43> <Formula b-43>
<화학식 b-44> <Formula b-44>
<화학식 b-45> <Formula b-45>
<화학식 b-46> <Formula b-46>
<화학식 b-47> <Formula b-47>
<화학식 b-48> <Formula b-48>
<화학식 b-49> <Formula b-49>
<화학식 b-50> <Formula b-50>
<화학식 b-51> <Formula b-51>
<화학식 b-52> <Formula b-52>
<화학식 b-53> <Formula b-53>
<화학식 b-54> <Formula b-54>.
. - 제4항에 있어서,The method of claim 4, wherein화학식 1에서,In Formula 1,상기 Ar1은 나프틸기 또는 페난트렌기인 화합물.Ar 1 is a naphthyl group or a phenanthrene group.
- 제7항에 있어서,The method of claim 7, wherein제7항에 따른 화합물은 하기 화학식 c-1 내지 c-54의 구조로부터 선택되는 것을 특징으로 하는 화합물:The compound according to claim 7, wherein the compound is selected from the structures of formulas c-1 to c-54:<화학식 c-1> <Formula c-1>
<화학식 c-2> <Formula c-2>
<화학식 c-3> <Formula c-3>
<화학식 c-4> <Formula c-4>
<화학식 c-5> <Formula c-5>
<화학식 c-6> <Formula c-6>
<화학식 c-7> <Formula c-7>
<화학식 c-8> <Formula c-8>
<화학식 c-9> <Formula c-9>
<화학식 c-10> <Formula c-10>
<화학식 c-11> <Formula c-11>
<화학식 c-12> <Formula c-12>
<화학식 c-13> <Formula c-13>
<화학식 c-14> <Formula c-14>
<화학식 c-15> <Formula c-15>
<화학식 c-16> <Formula c-16>
<화학식 c-17> <Formula c-17>
<화학식 c-18> <Formula c-18>
<화학식 c-19> <Formula c-19>
<화학식 c-20> <Formula c-20>
<화학식 c-21> <Formula c-21>
<화학식 c-22> <Formula c-22>
<화학식 c-23> <Formula c-23>
<화학식 c-24> <Formula c-24>
<화학식 c-25> <Formula c-25>
<화학식 c-26> <Formula c-26>
<화학식 c-27> <Formula c-27>
<화학식 c-28> <Formula c-28>
<화학식 c-29> <Formula c-29>
<화학식 c-30> <Formula c-30>
<화학식 c-31> <Formula c-31>
<화학식 c-32> <Formula c-32>
<화학식 c-33> <Formula c-33>
<화학식 c-34> <Formula c-34>
<화학식 c-35> <Formula c-35>
<화학식 c-36> <Formula c-36>
<화학식 c-37> <Formula c-37>
<화학식 c-38> <Formula c-38>
<화학식 c-39> <Formula c-39>
<화학식 c-40> <Formula c-40>
<화학식 c-41> <Formula c-41>
<화학식 c-42> <Formula c-42>
<화학식 c-43> <Formula c-43>
<화학식 c-44> <Formula c-44>
<화학식 c-45> <Formula c-45>
<화학식 c-46> <Formula c-46>
<화학식 c-47> <Formula c-47>
<화학식 c-48> <Formula c-48>
<화학식 c-49> <Formula c-49>
<화학식 c-50> <Formula c-50>
<화학식 c-51> <Formula c-51>
<화학식 c-52> <Formula c-52>
<화학식 c-53> <Formula c-53>
<화학식 c-54><Formula c-54>.
. - 제1 전극;A first electrode;제2 전극;Second electrode;제1 전극과 제2 전극 사이에 배치된 발광층; A light emitting layer disposed between the first electrode and the second electrode;제1 전극과 발광층 사이에 배치되는 정공 수송성층; 및A hole transport layer disposed between the first electrode and the light emitting layer; And정공 수송성층과 발광층 사이에 배치되고, 하기 화학식 1로 나타내는 화합물을 포함하는 차단층을 포함하는 발광소자:A light emitting device comprising: a blocking layer disposed between a hole transporting layer and a light emitting layer, the blocking layer comprising a compound represented by Formula 1 below:[화학식 1][Formula 1]
상기 화학식 1에서, R1, R2, La, Lb, Ar1, Ar2 및 Ar3은 제1항에서 정의한 바와 같다.In Formula 1, R 1 , R 2 , L a , L b , Ar 1 , Ar 2 and Ar 3 are as defined in claim 1. - 제9항에 있어서,The method of claim 9,차단층은 화학식 1로 나타내는 화합물을 1종 이상 포함하는 단층 구조인 발광소자.Blocking layer is a light emitting device having a single layer structure containing at least one compound represented by the formula (1).
- 제9항에 있어서,The method of claim 9,차단층은 이층 구조이고,The barrier layer is a two-layer structure,이층 구조를 구성하는 각 개별층은 서로 독립적으로 화학식 1로 나타내는 화합물을 1종 이상 포함하되,Each individual layer constituting the bilayer structure includes at least one compound represented by Formula 1 independently of each other,각 개별층에 포함되는 화합물은 서로 다른 구조를 갖는 것을 특징으로 하는 발광소자.Compounds included in each individual layer has a different structure.
- 제9항에 있어서,The method of claim 9,차단층은 이층 구조이고,The barrier layer is a two-layer structure,이층 구조 중 어느 한 층은 화학식 1로 나타내는 화합물을 1종 이상 포함하고,Any one layer of the two-layer structure contains at least one compound represented by the formula (1),다른 한 층은 하기 화학식 2로 나타내는 화합물을 포함하는 발광소자:Another layer is a light emitting device comprising a compound represented by the formula (2):[화학식 2][Formula 2]
상기 화학식 2에서,In Chemical Formula 2,Ra, Rb, Rc 및 Rd는 서로 독립적으로, 수소, 탄소수 1 내지 4를 갖는 알킬기 또는 탄소수 6 내지 14를 갖는 아릴기이다.R a , R b , R c and R d are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 14 carbon atoms. - 제10항에 있어서,The method of claim 10,차단층의 두께는 20 Å 내지 400 Å인 발광소자.The thickness of the blocking layer is 20 kHz to 400 kHz.
- 제11항 또는 제12항에 있어서,The method according to claim 11 or 12, wherein이층 구조를 구성하는 각 개별층 두께는 10 Å 내지 200 Å인 발광소자.A light emitting element having a thickness of each individual layer constituting the two-layer structure is 10 GPa to 200 GPa.
- 제9항에 있어서,The method of claim 9,정공 수송성층은 하기 화학식 3으로 나타내는 화합물을 포함하는 발광소자:The hole transport layer is a light emitting device comprising a compound represented by the following formula (3):[화학식 3][Formula 3]
상기 화학식 3에서,In Chemical Formula 3,R3 및 R4는 서로 독립적으로 수소, 탄소수 1 내지 6을 갖는 알킬기, 탄소수 6 내지 30을 갖는 아릴기 또는 탄소수 2 내지 20을 갖는 헤테로아릴기이고;R 3 and R 4 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms;Lc는 -L1-L2-L3-L4-이며,L c is -L 1 -L 2 -L 3 -L 4- ,L1, L2, L3 및 L4는 서로 독립적으로 단일결합, -O-, -S-, 탄소수 6 내지 30을 갖는 아릴렌기, 탄소수 2 내지 20을 갖는 헤테로아릴렌기 또는 탄소수 3 내지 20을 갖는 사이클로알킬렌기이되, L1, L2, L3 및 L4가 모두 단일결합인 경우는 제외되고;L 1 , L 2 , L 3, and L 4 are each independently a single bond, —O—, —S—, an arylene group having 6 to 30 carbon atoms, a heteroarylene group having 2 to 20 carbon atoms, or 3 to 20 carbon atoms. Having cycloalkylene groups, except where L 1 , L 2 , L 3 and L 4 are all single bonds;Ar4 및 Ar5는 서로 독립적으로 탄소수 6 내지 30을 갖는 아릴기, 탄소수 2 내지 20을 갖는 헤테로아릴기 또는 하기 화학식 4로 나타내는 치환기이며,Ar 4 and Ar 5 are each independently an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, or a substituent represented by the following general formula (4),[화학식 4][Formula 4]
상기 화학식 4에서,In Chemical Formula 4,X는 O, S 또는 C(R7)(R8)이고,X is O, S or C (R 7 ) (R 8 ),R5, R6, R7 및 R8은 서로 독립적으로 탄소수 1 내지 6을 갖는 알킬기, 탄소수 6 내지 30을 갖는 아릴기 또는 탄소수 2 내지 20을 갖는 헤테로아릴기이며,R 5 , R 6 , R 7 and R 8 are each independently an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms,p는 0 내지 3의 정수이고,p is an integer from 0 to 3,q는 0 내지 4의 정수이다.q is an integer of 0-4. - 제15항에 있어서,The method of claim 15,화학식 3으로 나타내는 화합물은 하기 화학식 5로 나타내는 화합물인 발광소자:Compound represented by Formula 3 is a compound represented by the formula (5):[화학식 5][Formula 5]
상기 화학식 5에서,In Chemical Formula 5,R3은 탄소수 6 내지 30을 갖는 아릴기이고;R 3 is an aryl group having 6 to 30 carbon atoms;R4는 수소이며;R 4 is hydrogen;Lc는 탄소수 6 내지 20을 갖는 아릴렌기이고;L c is an arylene group having 6 to 20 carbon atoms;Ar4는 탄소수 6 내지 30을 갖는 아릴기 또는 하기 화학식 4로 나타내는 치환기이며,Ar 4 is an aryl group having 6 to 30 carbon atoms or a substituent represented by the following formula (4),[화학식 4][Formula 4]
상기 화학식 4에서,In Chemical Formula 4,X는 O, S 또는 C(R7)(R8)이고,X is O, S or C (R 7 ) (R 8 ),R5, R6, R7 및 R8은 서로 독립적으로 탄소수 1 내지 6을 갖는 알킬기 또는 탄소수 6 내지 30을 갖는 아릴기이며,R 5 , R 6 , R 7 and R 8 are each independently an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 30 carbon atoms,p는 0 내지 2의 정수이고,p is an integer from 0 to 2,q는 0 내지 2의 정수이다.q is an integer of 0-2. - 제16항에 있어서,The method of claim 16,화학식 5에서,In Formula 5,상기 R3은 페닐기, 바이페닐기, 터페닐기 또는 나프틸기이고;R 3 is a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group;R4는 수소이며;R 4 is hydrogen;Lc는 페닐렌기, 바이페닐렌기, 터페닐렌기 또는 나프탈렌기이고; 및L c is a phenylene group, a biphenylene group, a terphenylene group or a naphthalene group; AndAr4는 페닐기, 바이페닐기, 터페닐기, 나프틸기, 디벤조티에닐기, 디벤조퓨라닐기, 플루오레닐기, 디메틸플루오레닐기 또는 디페닐플루오레닐기인 하는 발광소자.Ar 4 is a phenyl group, biphenyl group, terphenyl group, naphthyl group, dibenzothienyl group, dibenzofuranyl group, fluorenyl group, dimethyl fluorenyl group or diphenyl fluorenyl group.
- 제9항에 있어서,The method of claim 9,정공 수송성층은,Hole transport layer,P형 도펀트를 포함할 수 있는 제1 정공 수송성층; 및A first hole transport layer, which may include a P-type dopant; And제15항의 화학식 3으로 나타내는 화합물을 포함하는 제2 정공 수송성층을 포함하는 발광소자.A light emitting device comprising a second hole transport layer comprising a compound represented by Formula 3 of claim 15.
- 제9항에 따른 발광소자를 포함하는 전자 장치.An electronic device comprising the light emitting device according to claim 9.
- 제19항에 있어서,The method of claim 19,전자 장치는 디스플레이 장치 또는 조명 장치인 것을 특징으로 하는 전자 장치.The electronic device is a display device or an illumination device.
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| KR20130078749A (en) * | 2011-12-30 | 2013-07-10 | 제일모직주식회사 | Compound for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode |
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