CN110709387B - Novel cyclic compound and organic light-emitting device using same - Google Patents
Novel cyclic compound and organic light-emitting device using same Download PDFInfo
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- CN110709387B CN110709387B CN201880033346.8A CN201880033346A CN110709387B CN 110709387 B CN110709387 B CN 110709387B CN 201880033346 A CN201880033346 A CN 201880033346A CN 110709387 B CN110709387 B CN 110709387B
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- 150000001923 cyclic compounds Chemical class 0.000 title abstract description 7
- 239000012044 organic layer Substances 0.000 claims abstract description 34
- 239000000126 substance Substances 0.000 claims description 81
- 150000001875 compounds Chemical class 0.000 claims description 78
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000000463 material Substances 0.000 abstract description 19
- 239000010410 layer Substances 0.000 description 123
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 42
- -1 hole transport Substances 0.000 description 37
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- 125000003118 aryl group Chemical group 0.000 description 28
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 15
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 14
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- 125000001424 substituent group Chemical group 0.000 description 11
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- 229910052736 halogen Inorganic materials 0.000 description 6
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- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
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- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
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- 125000001769 aryl amino group Chemical group 0.000 description 3
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
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- 125000005549 heteroarylene group Chemical group 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 3
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- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
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- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
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- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- ZVFJWYZMQAEBMO-UHFFFAOYSA-N 1h-benzo[h]quinolin-10-one Chemical compound C1=CNC2=C3C(=O)C=CC=C3C=CC2=C1 ZVFJWYZMQAEBMO-UHFFFAOYSA-N 0.000 description 1
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- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 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
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- YDBLFISDFDCYCC-UHFFFAOYSA-N spiro[9h-anthracene-10,9'-fluorene] Chemical compound C12=CC=CC=C2CC2=CC=CC=C2C11C2=CC=CC=C2C2=CC=CC=C21 YDBLFISDFDCYCC-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The present invention relates to a novel cyclic compound and an organic light-emitting element including the same. The cyclic compound can be used as a material for an organic layer of an organic electroluminescent element, and can improve efficiency, a low driving voltage, and/or life characteristics in the organic electroluminescent element.
Description
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2017-0137662, 10-23 of 2017, the entire contents of the disclosure of the document of which are incorporated as part of the present specification.
The present invention relates to a novel cyclic compound and an organic electroluminescent element including the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic electroluminescent element utilizing an organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
The organic electroluminescent element generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. In order to improve efficiency and stability of the organic electroluminescent element, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like.
With the structure of such an organic electroluminescent element, if a voltage is applied between both electrodes, holes are injected from the anode to the organic layer, electrons are injected from the cathode to the organic layer, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons re-transition to the ground state.
For the organic material used for the organic electroluminescent element as described above, development of new materials is continuously demanded.
Prior art literature
Patent literature
(patent document 0001) Korean patent laid-open No. 10-2000-0051826 (2000.08.16)
Disclosure of Invention
Problems to be solved
The present invention is useful for providing novel cyclic compounds as organic electroluminescent compounds.
The present invention also provides an organic electroluminescent element comprising the above cyclic compound.
Solution to the problem
According to the present invention, there is provided a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the above-mentioned chemical formula 1,
R 1 each independently is hydrogen, C 1-30 Alkyl or C of (2) 6-30 Is a group consisting of an aryl group,
L 1 is a direct bond; by deuterium, halogen, amino, nitrile, nitro, C 1-30 Alkyl, C of (2) 2-30 Alkenyl, C 2-30 Alkynyl, C 1-30 Alkoxy, C 6-30 Aryloxy group of (C) 6-30 Aryl substituted or unsubstituted C 6-50 Arylene of (a); or comprises a heteroatom selected from any one or more of N, O and S and is C 6-30 Aryl substituted or unsubstituted C 2-60 Is a heteroarylene group of (a),
X 1 、X 2 and X 3 Each independently is N or C (R a ) The above X 1 、X 2 And X 3 At least one of which is N,
R a is hydrogen or C 1-30 Is a group comprising an alkyl group,
Ar 1 and Ar is a group 2 Each independently is deuterium, halogen, amino, nitrile, nitro, C 1-30 Alkyl, C of (2) 2-30 Alkenyl, C 2-30 Alkynyl, C 1-30 Alkoxy, C 6-30 Aryloxy group of (C) 6-30 Aryl substituted or unsubstituted C 6-50 Aryl of (a); or comprises a heteroatom selected from any one or more of N, O and S and is C 6-30 Aryl substituted or unsubstituted C 2-60 Heteroaryl of (a).
Further, according to the present invention, there is provided an organic electroluminescent element comprising: a first electrode, a second electrode disposed opposite to the first electrode, and at least one organic layer disposed between the first electrode and the second electrode,
one of the organic layers contains a compound represented by the above chemical formula 1.
Effects of the invention
The compound represented by the above chemical formula 1 can be used as a material for an organic layer of an organic electroluminescent element, and can improve efficiency, a low driving voltage, and/or life characteristics in the organic electroluminescent element. In particular, the compound represented by the above chemical formula 1 may be used as a material for hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection.
Drawings
Fig. 1 illustrates an example of an organic electroluminescent element constituted by a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic electroluminescent element constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4.
Detailed Description
In the following, a compound according to an embodiment of the present invention and an organic electroluminescent element including the same will be described in detail to help understanding the present invention.
Unless explicitly stated otherwise, the technical terms are used for describing specific embodiments only and are not intended to limit the present invention.
As used in this specification, the singular form also includes the plural form unless the sentence indicates a meaning clearly contrary to the meaning.
The use of "including" in this specification means that a particular feature, field, integer, stage, action, element and/or component is specified, but does not preclude the presence or addition of other features, fields, integers, stages, actions, elements, components and/or groups thereof.
In the present description of the invention,or- -the label represents the moiety of the group that is linked to the other group.
In the present specification, the term "substituted or unsubstituted" means that it is selected from deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio group [ ]Alkylthio) is described; arylthio (/ -> Arylthioxy); alkylsulfonyl (+)>Alkylsulfoxy); arylsulfonyl (+)>Aryl sulfoxy); a silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl phosphino; or a substituent comprising N, O and 1 or more substituents in a heterocyclic group comprising 1 or more of S atoms, or a substituent which is bonded to 2 or more substituents in the above-exemplified substituents. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 carbon atoms. According to another embodiment, the above alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.
In the present specification, the alkenyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples of the alkenyl group include vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-methyl-1-butenyl group, 1, 3-butadienyl group, allyl group, 1-phenylen-1-yl group, 2-diphenylethylene-1-yl group, 2-phenyl-2- (naphthalen-1-yl) ethylene-1-yl group, 2-bis (diphenyl-1-yl) ethylene-1-yl group, stilbene group, styryl group and the like, but are not limited thereto.
In the present specification, an alkynyl group is a 1-valent group in a form in which one hydrogen atom is removed from an alkyne having 2 to 30 carbon atoms or a derivative thereof.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as phenyl, biphenyl, and terphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, and the like,A group, a fluorenyl group, etc., but is not limited thereto.
In this specification, a fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. In the case where the above fluorenyl group is substituted, it may beEtc. However, the present invention is not limited thereto.
In the present specification, the heterocyclic group is a ring group containing 1 or more heteroatoms in O, N, si and S, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl, (-) -and (II) radicals>Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo->Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline (phenanthrinyl), iso>Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In this specification, the arylene group is not a 2-valent group, and the above description of the aryl group can be applied. In addition to the heteroarylene group being a 2-valent group, the above description of the heterocyclic group may be applied.
In one embodiment of the present invention, a compound represented by the following chemical formula 1 is provided.
[ chemical formula 1]
As a result of the continuous studies by the present inventors, the compound represented by the above chemical formula 1 was represented by 10H-spiro [ anthracene-9, 9' -fluorene](10H-spiro[anthracene-9，9′-fluorene]) The derivative being nuclear and containing L 1 、X 1 、X 2 、X 3 、Ar 1 And Ar is a group 2 The substituent form of the compound having the above structural characteristics can be applied to an organic electroluminescent element to improve the efficiency and lifetime characteristics of the element.
Preferably, the compound of the above chemical formula 1 may be a compound represented by any one of the following chemical formulas 2-a to 2-c depending on the binding site:
[ chemical formula 2-a ]
[ chemical formula 2-b ]
[ chemical formula 2-c ]
In the above chemical formulas 2-a to 2-c,
R 1 、L 1 、X 1 、X 2 、X 3 、Ar 1 and Ar is a group 2 Respectively, are as defined in the above chemical formula 1.
In the above chemical formula 1, R 1 Each independently is hydrogen, C 1-30 Alkyl or C of (2) 6-30 Aryl groups of (a). Preferably, R 1 May each independently be methyl or phenyl.
In the above chemical formula 1, L 1 Is a direct bond; by deuterium, halogen, amino, nitrile, nitro, C 1-30 Alkyl, C of (2) 2-30 Alkenyl, C 2-30 Alkynyl, C 1-30 Alkoxy, C 6-30 Aryloxy group of (C) 6-30 Aryl substituted or unsubstituted C 6-50 Arylene of (a); or comprises a heteroatom selected from any one or more of N, O and S and is C 6-30 Aryl substituted or unsubstituted C 2-60 Is a heteroarylene group.
Preferably L 1 Is directly bonded or any one of the following groups:
in the above chemical formula 1, X 1 、X 2 And X 3 Each independently is N or C (R a ) The above X 1 、X 2 And X 3 At least one of which is N.
Here, R is a Is hydrogen or C 1-30 Preferably hydrogen.
For example, in the above chemical formula 1, X is contained 1 、X 2 And X 3 The group of (a) may be any one selected from the group represented by the following chemical formulas 3-a to 3-f:
[ chemical formula 3-a ]
[ chemical formula 3-b ]
[ chemical formula 3-c ]
[ chemical formula 3-d ]
[ chemical formula 3-e ]
[ chemical formula 3-f ]
In the above chemical formulas 3-a to 3-f,
L 1 、Ar 1 and Ar is a group 2 Respectively, are as defined in the above chemical formula 1.
In the above chemical formula 1, ar 1 And Ar is a group 2 Each independently is deuterium, halogen, amino, nitrile, nitro, C 1-30 Alkyl, C of (2) 2-30 Alkenyl, C 2-30 Alkynyl, C 1-30 Alkoxy, C 6-30 Aryloxy group of (C) 6-30 Aryl substituted or unsubstituted C 6-50 Aryl of (a); or comprises a heteroatom selected from any one or more of N, O and S and is C 6-30 Aryl substituted or unsubstituted C 2-60 Heteroaryl groups.
Specifically, ar 1 And Ar is a group 2 Each independently may be any one selected from the group consisting of:
preferably, the compound represented by the above chemical formula 1 may be any one selected from the following compounds.
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The compound represented by the above chemical formula 1 can be produced by the following reaction formula 1.
[ reaction type 1]
In the above-mentioned reaction scheme 1,
Z 1 is a halogen, and is preferably a halogen,
L 1 、X 1 、X 2 、X 3 、Ar 1 and Ar is a group 2 Respectively, are as defined in the above chemical formula 1.
As a non-limiting example, an intermediate used in the method for producing the compound represented by the above chemical formula 1 may be produced by the following method.
[ reaction formula I-A ]
[ reaction formula I-B ]
[ reaction formula I-C ]
[ reaction formula I-D ]
[ reaction formulae I-E ]
[ reaction formula I-F ]
[ formulas I-A' to I-F ]
The above-described production method may be further embodied in a production example which will be described later.
In one embodiment of the present invention, an organic electroluminescent device is provided that includes the compound represented by chemical formula 1.
As an example, there is provided an organic electroluminescent element according to the present invention, comprising: a first electrode, a second electrode provided opposite to the first electrode, and at least 1 organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers contains a compound represented by chemical formula 1 of the first term.
The organic layer of the organic electroluminescent element of the present invention may be formed of a single-layer structure, or may be formed of a multilayer structure in which two or more organic layers are stacked.
For example, the organic electroluminescent element of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as the organic layer. However, the structure of the organic electroluminescent element is not limited thereto, and may include a smaller number of organic layers.
The organic layer may include a hole injection layer, a hole transport layer, or a layer that performs hole injection and transport simultaneously, and the hole injection layer, the hole transport layer, or the layer that performs hole injection and transport simultaneously may include a compound represented by chemical formula 1.
The organic layer may include a light-emitting layer including a compound represented by chemical formula 1.
The organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include a compound represented by chemical formula 1.
The electron transport layer, the electron injection layer, or the layer in which both electron transport and electron injection are performed contains the compound represented by the chemical formula 1.
The organic layer may include a light-emitting layer and an electron-transporting layer, and the electron-transporting layer may include a compound represented by chemical formula 1.
The organic electroluminescent element according to the present invention may have a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate.
The organic electroluminescent element according to the present invention may have a reverse structure (inverted type) in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate.
For example, a structure of an organic electroluminescent element according to an embodiment of the present invention is illustrated in fig. 1 and 2.
Fig. 1 illustrates an example of an organic electroluminescent element comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In the structure as in fig. 1, the compound represented by the above chemical formula 1 may be contained in the above light emitting layer.
Fig. 2 illustrates an example of an organic electroluminescent element constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4. In the structure as in fig. 2, the compound represented by the above chemical formula 1 may be contained in 1 or more layers among the above hole injection layer, hole transport layer, and electron transport layer, and preferably may be contained in the above hole transport layer.
In one aspect, the organic electroluminescent element according to the present invention may be manufactured using materials and methods well known in the art, except that 1 or more of the organic layers contains the compound represented by chemical formula 1.
In addition, in the case where the organic electroluminescent element includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
For example, the organic electroluminescent element according to the present invention may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate.
This can be manufactured as follows: PVD (physical Vapor Deposition) such as sputtering (sputtering) or electron beam evaporation (physical vapor deposition) is used to deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is deposited on the organic layer.
In addition to this method, an organic electroluminescent element may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
The compound represented by the above chemical formula 1 may be used not only in the vacuum deposition method but also in the solution coating method to form an organic layer in the production of an organic electroluminescent element. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
In addition to the above method, an organic electroluminescent element can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003/012890).
As an example, the first electrode may be an anode, the second electrode may be a cathode, or the first electrode may be a cathode, and the second electrode may be an anode.
As the anode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected into the organic layer.
Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); a combination of a metal such as ZnO, al or SNO2, sb and an oxide; conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ] (PEDOT), polypyrrole and polyaniline, etc., but are not limited thereto.
As the cathode material, a material having a small work function is generally preferred in order to facilitate injection of electrons into the organic layer.
Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; liF/Al or LiO 2 And/or Al, but is not limited thereto.
The hole injection substance is a layer that injects holes from the electrode, and the following compounds are preferable as the hole injection substance: the light-emitting device has a hole transporting capability, a hole injecting effect from an anode, an excellent hole injecting effect for a light-emitting layer or a light-emitting material, prevention of migration of excitons generated in the light-emitting layer to the electron injecting layer or the electron injecting material, and an excellent thin film forming capability.
The HOMO (highest occupied molecular orbital ) of the hole-injecting substance is preferably between the work function of the anode substance and the HOMO of the surrounding organic layer.
Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophenes, arylamine-based organic substances, hexanitrile hexaazabenzophenanthrene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.
The hole-transporting layer is a layer that receives holes from the hole-injecting layer and transports the holes to the light-emitting layer, and as a hole-transporting substance, a substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer, a substance having a large mobility to the holes is preferable.
Specific examples of the hole transporting material include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and unconjugated portions.
The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and preferably has high quantum efficiency for fluorescence or phosphorescence.
As a specific example of the above-mentioned luminescent material, there is 8-hydroxy-quinolAluminum-in-line complex (Alq 3); carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material includes aromatic condensed ring derivatives, heterocyclic compounds, and the like.
Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds Pyrimidine derivatives, etc., but are not limited thereto.
Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene having an arylamino group,Bisindenopyrene (Periflant hene) and the like, which is a styrylamine compound in which at least one aryl vinyl group is substituted on a substituted or unsubstituted aryl amine, are substituted or unsubstituted with 1 or 2 or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl and arylamino groups. Specifically, there are styrylamine, styrylenediamine, styryltriamineAnd styrenetetramine, but is not limited thereto. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like.
The electron mediator is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer, and as the electron mediator, a substance that can satisfactorily receive electrons from the cathode and transfer the electrons to the light-emitting layer is suitable for a substance having high electron mobility.
Specific examples of the electron-transporting substance include, but are not limited to, al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, hydroxyflavone-metal complexes, and the like.
The electron transport layer may be used with any desired cathode material as used in the art. In particular, examples of suitable cathode materials are the usual materials having a low work function accompanied by an aluminum layer or a silver layer. In particular cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum layer or a silver layer.
The electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound as follows: has an electron transporting ability, an electron injecting effect from a cathode, an excellent electron injecting effect to a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from migrating to a hole injecting layer, and has an excellent thin film forming ability.
Specific examples of the electron injection layer include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and,Azole,/->Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The organic electroluminescent element according to the present invention may be of a top emission type, a bottom emission type or a bi-directional emission type, depending on the materials used.
The compound represented by the above chemical formula 1 can be applied to an organic solar cell or an organic transistor in addition to an organic electroluminescent element.
In the following, preferred embodiments are presented to aid in understanding the invention. However, the following examples are merely for illustration of the invention, and the invention is not limited thereto.
Production example 1
After the above compound A (7.46 g,17.11 mmol) and (4- (4, 6-diphenyl-1,3, 5-triazin-2-yl) phenyl) boronic acid ((4- (4, 6-diphen-yl-1, 3, 5-triazin-2-yl) phenyl) acrylic acid) (6.95 g,19.68 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask, a 2M aqueous potassium carbonate solution (120 ml) was added, and tetrakis (triphenylphosphine) palladium (0.59 g,0.51 mmol) was added thereto and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 180ml of tetrahydrofuran, whereby the above-mentioned compound 1 (8.89 g, yield 78%) was obtained.
MS[M+H] + ＝666
Production example 2
After the above compound A (6.75 g,15.48 mmol) and (3- (4, 6-diphenyl-1,3, 5-triazin-2-yl) phenyl) boronic acid ((3- (4, 6-diphen-yl-1, 3, 5-triazin-2-yl) phenyl) acrylic acid) (6.28 g,17.80 mmol) were completely dissolved in 220ml of tetrahydrofuran in a 500ml round bottom flask, a 2M aqueous potassium carbonate solution (110 ml) was added, and tetrakis (triphenylphosphine) palladium (0.54 g,0.46 mmol) was added thereto and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 260ml of ethyl acetate, whereby the above-mentioned compound 2 (7.39 g, yield 72%) was obtained.
MS[M+H] + ＝666
Production example 3
After the above compound A (7.13 g,16.35 mmol) and (3- (2, 6-diphenylpyrimidin-4-yl) phenyl) boronic acid ((3- (2, 6-diphenylpyrimidin-4-yl) phenyl) acrylic acid) (6.62 g,18.81 mmol) were completely dissolved in 190ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (95 ml) was added, and tetrakis (triphenylphosphine) palladium (0.57 g,0.49 mmol) was added thereto and then heated and stirred for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 240ml of ethyl acetate, whereby the above-mentioned compound 3 (6.38 g, yield 59%) was obtained.
MS[M+H] + ＝665
Production example 4
After the above compound A (5.46 g,12.52 mmol) and (3- (4- (dibenzo [ b, d ] furan-4-yl) -6-phenyl-1,3, 5-triazin-2-yl) phenyl) boronic acid ((3- (4- (dibenzo [ b, d ] furan-4-yl) -6-phenyl-1,3, 5-triazin-2-yl) phenyl) carboxylic acid) (6.38 g,14.40 mmol) were completely dissolved in 180ml of tetrahydrofuran in a 500ml round bottom flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (90 ml) was added, and after adding tetrakis (triphenylphosphine) palladium (0.43 g,0.38 mmol), the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 230ml of ethyl acetate, whereby the above-mentioned compound 4 (6.29 g, yield 66%) was obtained.
MS[M+H] + ＝756
Production example 5
In a 500ml round bottom flask, the above compound B (5.92 g,13.58 mmol) and (3 '- (4, 6-diphenyl-1,3, 5-triazin-2-yl) - [1,1' -biphenyl ] -3-yl) boronic acid ((3 '- (4, 6-diphenyl-1,3, 5-triazin-2-yl) - [1,1' -biphen-yl ] -3-yl) carboxylic acid) (6.70 g,15.61 mmol) were completely dissolved in 200ml of tetrahydrofuran under nitrogen atmosphere, and then a 2M aqueous solution of potassium carbonate (100M 1) was added thereto, followed by addition of tetrakis (triphenylphosphine) palladium (0.47 g,0.41 mmol) and then heated and stirred for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 210ml of tetrahydrofuran, whereby the above-mentioned compound 5 (5.76 g, yield 57%) was obtained.
MS[M+H] + ＝742
Production example 6
After the above compound B (5.26 g,12.06 mmol) and (7- (4, 6-diphenyl-1,3, 5-triazin-2-yl) -9, 9-dimethyl-9H-fluoren-2-yl) boronic acid ((7- (4, 6-diphenyl-1,3, 5-triazin-2-yl) -9, 9-dimethyl-9H-fluoren-2-yl) carboxylic acid) (6.51 g,13.87 mmol) were completely dissolved in 280ml of tetrahydrofuran in a 500ml round bottom flask, a 2M aqueous solution of potassium carbonate (140 ml) was added thereto, and after adding tetrakis (triphenylphosphine) palladium (0.42 g,0.36 mmol), the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 250ml of tetrahydrofuran, whereby the above-mentioned compound 6 (5.18 g, yield 76%) was obtained.
MS[M+H] + ＝782
PREPARATION EXAMPLE 7
After the above compound B (6.12 g,14.04 mmol) and (3- (2, 6-diphenylpyrimidin-4-yl) phenyl) boronic acid ((3- (2, 6-diphenylpyrimidin-4-yl) phenyl) acrylic acid) (5.68 g,16.14 mmol) were completely dissolved in 210ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (105 ml) was added, and tetrakis (triphenylphosphine) palladium (0.49 g,0.42 mmol) was added, followed by stirring with heating for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 240ml of ethyl acetate, whereby the above-mentioned compound 7 (6.34 g, yield 68%) was obtained.
MS[M+H] + ＝665
Production example 8
After the above compound C (5.55 g,12.73 mmol), ((4- (4, 6-diphenyl-1,3, 5-triazin-2-yl) phenyl) boronic acid ((4- (4, 6-diphenyl-1,3, 5-triazin-2-yl) carbonyl) acid) (5.17 g,14.64 mmol) was completely dissolved in 200ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (100 ml) was added, tetrakis (triphenylphosphine) palladium (0.44 g,0.38 mmol) was added, and then heated and stirred for 5 hours, the temperature was lowered to normal temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, it was concentrated under reduced pressure and recrystallized from 190ml of tetrahydrofuran to give the above compound 8 (6.62 g, yield 78%).
MS[M+H] + ＝666
Production example 9
After the above compound C (4.92 g,11.28 mmol) and (3- (4, 6-diphenyl-1,3, 5-triazin-2-yl) phenyl) boronic acid ((3- (4, 6-diphen-yl-1, 3, 5-triazin-2-yl) phenyl) acrylic acid) (4.58 g,12.98 mmol) were completely dissolved in 160ml of tetrahydrofuran in a 500ml round bottom flask, a 2M aqueous potassium carbonate solution (80 ml) was added, and tetrakis (triphenylphosphine) palladium (0.39 g,0.34 mmol) was added thereto and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 210ml of tetrahydrofuran, whereby the above-mentioned compound 9 (5.16 g, yield 69%) was obtained.
MS[M+H] + ＝666
Production example 10
After the above compound A (5.36 g,12.29 mmol) and (3- (4, 6-diphenyl-1,3, 5-triazin-2-yl) phenyl) boronic acid ((3- (4, 6-diphen-yl-1, 3, 5-triazin-2-yl) phenyl) acrylic acid) (6.07 g,14.14 mmol) were completely dissolved in 260ml of tetrahydrofuran in a 500ml round bottom flask, a 2M aqueous potassium carbonate solution (130 ml) was added, and tetrakis (triphenylphosphine) palladium (0.43 g,0.37 mmol) was added thereto and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 210ml of ethyl acetate, whereby the above-mentioned compound 10 (6.12 g, yield 67%) was obtained.
MS[M+H] + ＝742
Production example 11
After the above compound A-1 (13.40 g,27.69 mmol) and 2-chloro-4, 6-phenyl-1,3,5-triazine (2-chloro-4, 6-dipheno-1, 3, 5-triazine) (6.43 g,24.08 mmol) were completely dissolved in 200ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (100 rl) was added, tetrakis (triphenylphosphine) palladium (0.83 g,0.72 mmol) was added, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure, and recrystallized from 290ml of acetonitrile to obtain the above-mentioned compound 11 (10.67 g, yield 75%).
MS[M+H] + ＝590
Production example 12
After the above compound A-1 (8.03 g,16.60 mmol) and 2- ([ 1,1'-biphenyl ] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine (2- ([ 1,1' -biphen-yl ] -4-yl) -4-chloro-6-phenyl-1,3, 5-triazine) (4.95 g,14.43 mmol) were completely dissolved in 160M1 of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (80 ml) was added, and tetrakis (triphenylphosphine) palladium (0.50 g,0.43 mmol) was added thereto and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 230ml of acetonitrile, whereby the above-mentioned compound 12 (7.65 g, yield 80%) was obtained.
MS[M+H] + ＝590
PREPARATION EXAMPLE 13
After the above compound A-1 (11.24 g,23.22 mmol) and 4-chloro-2,6-diphenylpyrimidine (4-chloro-2, 6-diphenylpyrimide) (5.37 g,20.19 mmol) were completely dissolved in 220ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (110 ml) was added, tetrakis (triphenylphosphine) palladium (0.70 g,0.61 mmol) was added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure, and recrystallized from 220ml of acetonitrile to obtain the above-mentioned compound 13 (8.52 g, yield 72%).
MS[M+H] + ＝589
PREPARATION EXAMPLE 14
After the above compound B-1 (7.93 g,16.38 mmol), 2- ([ 1,1'-biphenyl ] -4-yl) -4-chloro-6-phenylpyrimidine (2- ([ 1,1' -biphen yl ]. 4-yl) -4-chloro-6-phenyl pyrimide) (4.87 g,14.24 mmol) was completely dissolved in 180ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (90 ml) was added, and tetrakis (triphenylphosphine) palladium (0.49 g,0.43 mmol) was added, and the mixture was heated and stirred for 2 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 260ml of ethyl acetate, whereby the above-mentioned compound 14 (6.28 g, yield 6%) was obtained.
MS[M+H] + ＝665
Production example 15
After the above compound B-1 (12.31 g,25.43 mmol) and 2-chloro-4,6-diphenylpyridine (2-chloro-4, 6-diphenylpyridine) (5.86 g,22.11 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 ml) was added, tetrakis (triphenylphosphine) palladium (0.77 g,0.66 mmol) was added, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 180ml of ethanol, whereby the above-mentioned compound 15 (7.76 g, yield 60%) was obtained.
MS[M+H] + ＝588
PREPARATION EXAMPLE 16
After the above compound A-1 (7.20 g,14.88 mmol) and 4'- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) - [1,1' -biphenyl ] -3-carbonitrile (4 '- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) - [1,1' -biphen ] -3-carbo-trie) (4.76 g,12.93 mmol) were completely dissolved in 140ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (70 ml) was added and tetrakis (triphenylphosphine) palladium (0.45 g,0.39 mmol) was added and heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 250ml of ethyl acetate to give the above-mentioned compound 16 (6.30 g, yield 70%).
MS[M+H] + ＝691
Production example 17
After the above compound C-1 (7.70 g,15.92 mmol), 2-chloro-4, 6-bis (naphthalen-1-yl) -1,3,5-triazine (2-chloro-4, 6-di (naphthalen-1-yl) -1,3, 5-triazine) (5.08 g,13.84 mmol) was completely dissolved in 220ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (110 ml) was added, and tetrakis (triphenylphosphine) palladium (0.48 g,0.42 mmol) was added thereto and then heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 260ml of ethyl acetate, whereby the above-mentioned compound 17 (7.26 g, yield 76%) was obtained.
MS[M+H] + ＝690
PREPARATION EXAMPLE 18
After the above compound B-1 (8.74 g,18.05 mmoI), 2-chloro-4, 6-bis (naphthalen-2-yl) -1,3,5-triazine (2-chloro-4, 6-di (naphthalen-2-yl) -1,3, 5-triazine) (5.76 g,15.69 mmol) was completely dissolved in 260ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (130 ml) was added, and tetrakis (triphenylphosphine) palladium (0.54 g,0.47 mmol) was added thereto, followed by stirring with heating for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 220ml of ethyl acetate, whereby the above-mentioned compound 18 (6.27 g, yield 58%) was obtained.
MS[M+H] + ＝690
Production example 19
After the above compound A-1 (8.66 g,17.90 mmol) and 2-chloro-4- (9, 9-dimethyl-9H-fluoren-2-yl) -6-phenyl-1,3,5-triazine (2-chloro-4- (9, 9-dimethyl-9H-fluoren-2-y 1) -6-phenyl-1,3, 5-triazine) (5.96 g,15.56 mmol) were completely dissolved in 180ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, a 2M aqueous potassium carbonate solution (90 ml) was added, and tetrakis (triphenylphosphine) palladium (0.54 g,0.47 mmol) was added, followed by stirring with heating for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 260ml of ethyl acetate, whereby the above-mentioned compound 19 (5.29 g, yield 48%) was obtained.
MS[M+H] + ＝706
Production example 20
After the above compound A-1 (9.15 g,18.90 mmol) and 2-chloro-4- (dibenzo [ b, d ] thiophen-4-yl) -6-phenyl-1,3,5-triazine (2-chloro-4- (dibenzo [ b, d ] thiophen-4-yl) -6-phenyl-1,3, 5-triazine) (6.13 g,16.43 mmol) were completely dissolved in 220ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, a 2M aqueous potassium carbonate solution (110M 1) was added, and tetrakis (triphenylphosphine) palladium (0.57 g,0.49 mmol) was added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 260ml of ethyl acetate, whereby the above-mentioned compound 20 (5.29 g, yield 48%) was obtained.
MS[M+H] + ＝696
Production example 21
After the above compound C-1 (6.83 g,14.10 mmol) and 2-chloro-4- (phenanthren-9-yl) -6- (triphenylen-2-yl) -1,3,5-triazine (2-chloro-4- (triphenylen-9-yl) -6- (triphenylen-2-y 1) -1,3, 5-triazine) (6.34 g,12.26 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (120 ml) was added, and tetrakis (triphenylphosphine) palladium (0.43 g,0.37 mmol) was added thereto and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 260ml of ethyl acetate, whereby the above-mentioned compound 21 (7.26 g, yield 76%) was obtained.
MS[M+H] + ＝840
Comparative example 1-1
To ITO (indium tin oxide)The glass substrate coated to a thin film is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode thus prepared, hexanitrile Hexaazatriphenylene (HAT) of the following chemical formula was preparedAnd performing thermal vacuum evaporation to form a hole injection layer.
On the hole injection layer, the following compound HT1 (4, 4'- (9-phenyl-9H-carbazole-3, 6-diyl) bis (N, N-diphenylaniline), 4' - (9-phenyl-9H-carbazol-3, 6-diyl) bis (N, N-diphenyaniline)), as a hole transporting substance, was usedVacuum deposition is performed to form a hole transport layer.
Then, the hole transport layer is formed with a film thicknessThe following compound EB1 was vacuum-deposited to form an electron blocking layer. />
Then, on the electron blocking layer, the film thickness is set to beThe following compound BH and compound BD were vacuum-evaporated at a weight ratio of 25:1 to form a light-emitting layer.
The light-emitting layer and the hole-transporting layer are formed on the substrate at a film thicknessThe following compound HB1 was vacuum-deposited to form a hole blocking layer.
Next, on the hole blocking layer, the following compound ET1 and the following compound LiQ (8-hydroxyquinoline lithium, lithium Quinolate) were vacuum-evaporated at a weight ratio of 1:1 to give a film having a composition of 3Form an electron injection and transport layer. />
On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added toIs made of aluminum +.>The thickness was evaporated to form a cathode.
In the process, the evaporation rate of the organic matters is maintained to be 0.4 toLithium fluoride maintenance of cathodeIs kept at>Is to maintain a vacuum degree of 2X 10 during vapor deposition -7 To 5X 10 -6 A support, thereby manufacturing an organic hairAn optical element.
Examples 1-1 to 1-11
An organic light-emitting device was manufactured in the same manner as in comparative example 1-1 except that the compound described in table 1 below was used instead of the compound HB1 in comparative example 1-1.
Comparative examples 1-2 to 1-4
An organic light-emitting device was manufactured in the same manner as in comparative example 1-1 except that the compound described in table 1 below was used instead of the compound HB1 in comparative example 1-1. The compounds HB2, HB3 and HB4 in Table 1 below are shown below.
Test example 1
When electric current was applied to the organic light emitting elements manufactured in examples 1-1 to 1-11 and comparative examples 1-1 to 1-4 described above, voltage, efficiency, color coordinates and lifetime were measured, and the results thereof are shown in table 1 below. T95 represents the time required for the luminance to decrease from the initial luminance (1300 nit) to 95%.
[ Table 1]
As shown in table 1 above, in the case of an organic light-emitting element manufactured using the compound of the present invention as a hole blocking layer, excellent characteristics were exhibited in terms of efficiency, driving voltage, and/or stability of the organic light-emitting element.
The organic light-emitting element exhibits characteristics of low voltage, high efficiency, and long lifetime, compared with an organic light-emitting element produced by using fluorene (HB 2 to HB 4) as a hole blocking layer.
The core of the present invention has a relatively high electron content compared to Spirobifluorene (Spirobifluorene), 9, 10-diphenylfluorene (9, 10-diphen ylfluorene) and 9, 10-dimethylfluorene (9, 10-dimethylfluorene) cores, and when used as a hole blocking layer, results in a greatly improved lifetime while exhibiting advantages in voltage and efficiency.
As shown in the results of table 1 above, it was confirmed that the compound according to the present invention was excellent in hole blocking ability and applicable to an organic light emitting element.
Examples 2-1 to 2-21
An organic light-emitting device was manufactured in the same manner as in comparative example 1-1 except that the compound ET1 was replaced with the compound described in table 2 below in the formation of the electron transport layer in comparative example 1-1.
Comparative examples 2-1 to 2-3
An organic light-emitting device was manufactured in the same manner as in comparative example 1-1 except that the compound ET1 was replaced with the compound described in table 2 below in the formation of the electron transport layer in comparative example 1-1. Compounds ET2, ET3 and ET4 in table 2 below are shown below.
Test example 2
When electric current was applied to the organic light emitting elements manufactured in examples 2-1 to 2-21 and comparative examples 2-1 to 2-3 described above, voltage, efficiency, color coordinates and lifetime were measured, and the results thereof are shown in table 2 below. T95 represents the time required for the luminance to decrease from the initial luminance (1300 nit) to 95%.
[ Table 2 ]
As shown in table 2 above, in the case of an organic light-emitting element manufactured using the compound of the present invention as an electron transport layer, excellent characteristics were exhibited in terms of efficiency, driving voltage, and/or stability of the organic light-emitting element.
The compound of comparative examples 4, 9, 10-diphenylfluorene (9, 10-diphenylfluorene) core and comparative examples 5 and 9, 10-dimethylfluorene (9, 10-dimethylfluorene) core, which are obtained by using the compound of comparative example 6 as an electron transport layer, exhibited characteristics of low voltage, high efficiency and long lifetime, compared to the organic light emitting element produced by using the compound of comparative examples 4, 9, 10-diphenylfluorene (9, 10-dimethylfluorene) core as an electron transport layer.
The result is obtained that the core of the present invention has a relatively high electron content compared to Spirobifluorene (Spirobifluorene), 9, 10-diphenylfluorene (9, 10-diphenylfluorene) and 9, 10-dimethylfluorene (9, 10-dimethylfluorene) cores, and when used as an electron transport layer, an increase in lifetime of 20% to 30% is shown to be advantageous in terms of voltage and efficiency.
While the preferred embodiments of the present invention have been described above, the present invention is not limited to these, and can be modified and implemented in various forms within the scope of the invention as claimed and the detailed description of the invention, and the present invention is also within the scope of the invention.
[ symbolic description ]
1: substrate 2: anode 3: light emitting layer 4: cathode 5: hole injection layer
6: hole transport layer 7: light emitting layer 8: an electron transport layer.
Claims (4)
1. A compound represented by the following chemical formula 1:
chemical formula 1
In the above-mentioned chemical formula 1,
R 1 each independently of the other is a methyl group or a phenyl group,
L 1 is directly bonded with,Or->X 1 、X 2 And X 3 Each independently is NOr C (R) a ) The X is 1 、X 2 And X 3 At least one of which is N,
R a is a hydrogen gas which is used as a hydrogen gas,
Ar 1 and Ar is a group 2 Each independently is any one selected from the group consisting of,
2. the compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 2-a to 2-c:
chemical formula 2-a
Chemical formula 2-b
Chemical formula 2-c
In the chemical formulas 2-a to 2-c,
R 1 、L 1 、X 1 、X 2 、X 3 、Ar 1 and Ar is a group 2 Respectively as defined in the chemical formula 1.
3. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the group consisting of,
/>
/>
4. an organic electroluminescent element, comprising: a first electrode, a second electrode disposed opposite to the first electrode, and at least one organic layer disposed between the first electrode and the second electrode,
at least one of the organic layers includes the compound represented by chemical formula 1 of claim 1.
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| KR20110108573A (en) * | 2010-03-29 | 2011-10-06 | 대주전자재료 주식회사 | Benzo chrysene derivatives and organic electroluminescent diode comprising the same |
| KR20130140303A (en) * | 2012-06-14 | 2013-12-24 | (주) 에프엔지리서치 | Novel compounds for organic electroluminescent device |
| KR20160100698A (en) * | 2015-02-16 | 2016-08-24 | 주식회사 엘지화학 | Double spiro structure compound and organic light emitting device comprising the same |
| CN106536485A (en) * | 2014-07-21 | 2017-03-22 | 默克专利有限公司 | Materials for electronic devices |
| TW201730159A (en) * | 2015-10-27 | 2017-09-01 | Ｌｇ化學股份有限公司 | Organic light emitting device |
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| KR20110108573A (en) * | 2010-03-29 | 2011-10-06 | 대주전자재료 주식회사 | Benzo chrysene derivatives and organic electroluminescent diode comprising the same |
| KR20130140303A (en) * | 2012-06-14 | 2013-12-24 | (주) 에프엔지리서치 | Novel compounds for organic electroluminescent device |
| CN106536485A (en) * | 2014-07-21 | 2017-03-22 | 默克专利有限公司 | Materials for electronic devices |
| KR20160100698A (en) * | 2015-02-16 | 2016-08-24 | 주식회사 엘지화학 | Double spiro structure compound and organic light emitting device comprising the same |
| TW201730159A (en) * | 2015-10-27 | 2017-09-01 | Ｌｇ化學股份有限公司 | Organic light emitting device |
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