WO2021177616A1 - Organic electronic device comprising capping layer, and electronic apparatus comprising same - Google Patents
Organic electronic device comprising capping layer, and electronic apparatus comprising same Download PDFInfo
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- WO2021177616A1 WO2021177616A1 PCT/KR2021/001707 KR2021001707W WO2021177616A1 WO 2021177616 A1 WO2021177616 A1 WO 2021177616A1 KR 2021001707 W KR2021001707 W KR 2021001707W WO 2021177616 A1 WO2021177616 A1 WO 2021177616A1
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- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 239000010410 layer Substances 0.000 claims description 171
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 239000012044 organic layer Substances 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 27
- 229910052698 phosphorus Inorganic materials 0.000 claims description 26
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 24
- 239000011368 organic material Substances 0.000 claims description 23
- 125000001931 aliphatic group Chemical group 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- 230000005525 hole transport Effects 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000000732 arylene group Chemical group 0.000 claims description 16
- 229910052710 silicon Inorganic materials 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000005567 fluorenylene group Chemical group 0.000 claims description 14
- 125000004104 aryloxy group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 5
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052805 deuterium Inorganic materials 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims description 2
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 2
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 239000002096 quantum dot Substances 0.000 claims description 2
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims description 2
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 description 43
- 238000003786 synthesis reaction Methods 0.000 description 42
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- 238000006243 chemical reaction Methods 0.000 description 27
- 239000000047 product Substances 0.000 description 26
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 239000012141 concentrate Substances 0.000 description 22
- 239000000741 silica gel Substances 0.000 description 22
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- 239000000203 mixture Substances 0.000 description 19
- 238000002347 injection Methods 0.000 description 17
- 239000007924 injection Substances 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 15
- 239000000463 material Substances 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 239000002019 doping agent Substances 0.000 description 8
- 230000006872 improvement Effects 0.000 description 8
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229940126062 Compound A Drugs 0.000 description 6
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000005401 electroluminescence Methods 0.000 description 6
- -1 silol Chemical compound 0.000 description 6
- 239000000470 constituent Substances 0.000 description 5
- 238000000434 field desorption mass spectrometry Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 150000003413 spiro compounds Chemical class 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- XZYQBYQGHHGXBC-UHFFFAOYSA-N 4-(1,3-benzoxazol-2-yl)aniline Chemical compound C1=CC(N)=CC=C1C1=NC2=CC=CC=C2O1 XZYQBYQGHHGXBC-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- YUFRAQHYKKPYLH-UHFFFAOYSA-N benzo[f]quinoxaline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=N1 YUFRAQHYKKPYLH-UHFFFAOYSA-N 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
- 125000003003 spiro group Chemical group 0.000 description 3
- 101150075118 sub1 gene Proteins 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- 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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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- FBVBNCGJVKIEHH-UHFFFAOYSA-N [1]benzofuro[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3OC2=C1 FBVBNCGJVKIEHH-UHFFFAOYSA-N 0.000 description 2
- ITOKSWHFPQBNSE-UHFFFAOYSA-N [1]benzofuro[3,2-d]pyrimidine Chemical compound N1=CN=C2C3=CC=CC=C3OC2=C1 ITOKSWHFPQBNSE-UHFFFAOYSA-N 0.000 description 2
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- 125000003277 amino group Chemical group 0.000 description 2
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- PQIUGRLKNKSKTC-UHFFFAOYSA-N benzo[h]quinazoline Chemical compound N1=CN=C2C3=CC=CC=C3C=CC2=C1 PQIUGRLKNKSKTC-UHFFFAOYSA-N 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
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- 230000000903 blocking effect Effects 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
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- 230000003287 optical effect Effects 0.000 description 2
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- RIXZZVOJMJBWSQ-UHFFFAOYSA-N (2-chloro-6-methylsulfanylphenyl)boronic acid Chemical compound ClC1=C(C(=CC=C1)SC)B(O)O RIXZZVOJMJBWSQ-UHFFFAOYSA-N 0.000 description 1
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- YFHQVYMBFLUUDD-UHFFFAOYSA-N 1-bromo-2-(iodomethyl)benzene Chemical compound BrC1=CC=CC=C1CI YFHQVYMBFLUUDD-UHFFFAOYSA-N 0.000 description 1
- FFMJAFCTEHLDQG-UHFFFAOYSA-N 1-phenyl-11H-benzo[a]carbazole Chemical compound C1(=CC=CC=C1)C1=CC=CC=2C1=C1NC3=CC=CC=C3C1=CC2 FFMJAFCTEHLDQG-UHFFFAOYSA-N 0.000 description 1
- FBTOLQFRGURPJH-UHFFFAOYSA-N 1-phenyl-9h-carbazole Chemical compound C1=CC=CC=C1C1=CC=CC2=C1NC1=CC=CC=C12 FBTOLQFRGURPJH-UHFFFAOYSA-N 0.000 description 1
- LAVLDGSVWFEKJG-UHFFFAOYSA-N 10-phenylphenoxazine Chemical compound C12=CC=CC=C2OC2=CC=CC=C2N1C1=CC=CC=C1 LAVLDGSVWFEKJG-UHFFFAOYSA-N 0.000 description 1
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- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- AELZBFQHFNMGJS-UHFFFAOYSA-N 1h-1-benzosilole Chemical compound C1=CC=C2[SiH2]C=CC2=C1 AELZBFQHFNMGJS-UHFFFAOYSA-N 0.000 description 1
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- RBVHJNZMSBQFDK-UHFFFAOYSA-N 2-(4-bromophenyl)-1,3-benzoxazole Chemical compound C1=CC(Br)=CC=C1C1=NC2=CC=CC=C2O1 RBVHJNZMSBQFDK-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/10—OLED displays
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/80—Constructional details
- H10K30/865—Intermediate layers comprising a mixture of materials of the adjoining active layers
-
- 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]
- H10K50/14—Carrier transporting layers
-
- 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
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Definitions
- the present invention relates to an organic electric device including a light efficiency improving layer and an electronic device including the same.
- the organic light emitting device is a self-luminous device, and has a wide viewing angle and excellent contrast, as well as a fast response time, excellent luminance, driving voltage and response speed characteristics, and multicolorization is possible.
- Such an organic light emitting device has a structure in which a first electrode (anode), a hole transport region, a light emitting layer, an electron transport region, and a second electrode (cathode) are sequentially formed on a substrate. Holes injected from the first electrode move to the emission layer via the hole transport region, and electrons injected from the second electrode move to the emission layer via the electron transport region. Carriers such as holes and electrons recombine in the emission layer region to generate excitons, and light is generated as the excitons change from an excited state to a ground state.
- the luminous efficiency of the organic light emitting diode can be generally divided into internal luminescent efficiency and external liminescent efficiency.
- the internal luminous efficiency is related to how efficiently excitons are generated and light conversion is performed in the organic layer interposed between the first and second electrodes (that is, between the anode and the cathode), such as a hole transport layer, a light emitting layer, and an electron transport layer, etc.
- External luminous efficiency refers to the efficiency at which light generated in the organic layer is extracted to the outside of the organic light emitting device, and even if high light conversion efficiency is achieved in the organic layer (that is, , even if the internal luminous efficiency is high), if the external luminous efficiency is low, the overall luminous efficiency of the organic light emitting diode is inevitably reduced.
- the top device structure has a large optical energy loss due to surface plasmon polariton (SPP) because the formed light is reflected by the anode, which is a reflective film, and emitted toward the cathode.
- SPP surface plasmon polariton
- one of the important methods for improving the shape and efficiency of the EL spectrum is a method of applying a capping layer to a top cathode type.
- metals such as Al, Pt, Ag, and Au are mainly used as cathode electrodes, and SSP is generated on the surface of these metal electrodes.
- SSP is generated on the surface of these metal electrodes.
- the cathode is used as Ag
- the light emitted by the Ag of the cathode is quenched by the SPP (light energy loss due to Ag) and the efficiency is reduced.
- an object of the present invention is to provide an organic electric device having significantly improved luminous efficiency and color purity by forming a light efficiency improving layer with a specific compound, and an electronic device including the same.
- the present invention provides an organic electric device comprising a compound represented by the following formula in a light efficiency improving layer and an electronic device thereof.
- the compound according to the present invention as a material for the light efficiency improvement layer, the luminous efficiency and color purity of the organic electric device can be improved.
- 1 to 3 are exemplary views of an organic electroluminescent device according to the present invention.
- organic electric device 110 first electrode
- first hole transport layer 340 first light emitting layer
- second charge generation layer 420 second hole injection layer
- aryl group and arylene group used in the present invention have 6 to 60 carbon atoms, respectively, unless otherwise specified, but are not limited thereto.
- the aryl group or the arylene group may include a monocyclic type, a ring aggregate, a fused multiple ring system, a spiro compound, and the like.
- the aryl group may include a fluorenyl group and the arylene group may include a fluorenylene group.
- fluorenyl group refers to a substituted or unsubstituted fluorenyl group
- fluorenylene group refers to a substituted or unsubstituted fluorenyl group
- the fluorenyl group or The fluorenylene group includes a case in which R and R' are bonded to each other in the following structure to form a spiro compound together with the carbon to which they are bonded.
- Substituted fluorenyl group means that at least one of R, R', R" in the following structure is a substituent other than hydrogen, and in the present specification, regardless of the valence, a fluorenyl group , a fluorenylene group, a fluorentriyl group, etc. may all be called a fluorene group.
- the term "spiro compound" has a 'spiro linkage', and the spiro linkage means a linkage formed by sharing only one atom between two rings. At this time, the atoms shared by the two rings are called 'spiro atoms', and they are respectively 'monospiro-', 'dispiro-', 'trispiro-', depending on the number of spiro atoms in a compound. ' It's called a compound.
- heterocyclic group used in the present invention includes not only aromatic rings such as “heteroaryl group” or “heteroarylene group” but also non-aromatic rings, and unless otherwise specified, the number of carbon atoms each containing at least one heteroatom It means a ring of 2 to 60, but is not limited thereto.
- heteroatom refers to N, O, S, P or Si, unless otherwise specified, and the heterocyclic group is a monocyclic group including a heteroatom, a ring aggregate, a fused multiple ring system, a spy means a compound or the like.
- aliphatic ring group used in the present invention refers to a cyclic hydrocarbon other than an aromatic hydrocarbon, and includes a monocyclic type, a ring aggregate, a fused multiple ring system, a spiro compound, etc., unless otherwise specified, the number of carbon atoms It means a ring of 3 to 60, but is not limited thereto. For example, even when benzene, which is an aromatic ring, and cyclohexane, which is a non-aromatic ring, are fused, it corresponds to an aliphatic ring.
- the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc. exemplified as examples of each symbol and its substituents may be described as 'the name of the group reflecting the valence', but is described as 'name of the parent compound' You may.
- the monovalent 'group' is 'phenanthryl' and the divalent group is 'phenanthrylene'. Regardless, it can also be described as the name of the parent compound, 'phenanthrene'.
- pyrimidine regardless of the valence, it can be described as 'pyrimidine', or in the case of monovalent, as a pyrimidinyl group, in the case of divalent, as the 'name of the group' of the corresponding valence, such as pyrimidinylene. have.
- the substituent R 1 means that it does not exist, that is, when a is 0, it means that all hydrogens are bonded to the carbons forming the benzene ring, and in this case, the indication of hydrogen bonded to carbon is shown. It can be omitted and the chemical formula or compound can be described.
- R 1 when a is an integer of 1, one substituent R 1 is bonded to any one of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it may be bonded as follows, for example, a is 4 to 6 Even if it is an integer of , it is bonded to the carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R 1 may be the same as or different from each other.
- the number in 'number-condensed ring' indicates the number of rings to be condensed.
- a form in which three rings are condensed with each other, such as anthracene, phenanthrene, benzoquinazoline, etc. may be expressed as a 3-condensed ring.
- a ring when expressed in the form of a 'numeric atom' such as a 5-membered ring, a 6-membered ring, etc., the number in 'number-atom' indicates the number of elements forming the ring.
- thiophene or furan may correspond to a 5-membered ring
- benzene or pyridine may correspond to a 6-membered ring.
- the ring formed by bonding adjacent groups to each other is a C 6 ⁇ C 60 aromatic ring group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; And C 3 ⁇ C 60
- An aliphatic ring group may be selected from the group consisting of.
- 'neighboring groups' refers to each other when describing the following chemical formula as an example, R 1 and R 2 each other , R 2 and R 3 each other , R 3 and R 4 each other , Not only R 5 and R 6 but also R 7 and R 8 sharing one carbon are included, and not immediately adjacent, such as R 1 and R 7 , R 1 and R 8 , or R 4 and R 5 , etc. Substituents bonded to ring constituents (such as carbon or nitrogen) may also be included.
- substituents on a ring constituent element such as carbon or nitrogen immediately adjacent to it, they may be a neighboring group, but if no substituent is bonded to a ring constituent element at the immediately adjacent position, it is bonded to the next ring constituent element It can be a group adjacent to the substituent group, and also the substituents bonded to the same ring constituent carbon can be said to be adjacent groups.
- the expression 'neighboring groups may combine with each other to form a ring' is used in the same meaning as 'neighboring groups combine with each other to selectively form a ring', and at least one pair of It means a case where adjacent groups are bonded to each other to form a ring.
- 1 to 3 are exemplary views of an organic electric device according to an embodiment of the present invention.
- an organic electric device 100 includes a first electrode 110 , a second electrode 170 , and a first electrode 110 formed on a substrate (not shown). and an organic material layer formed between the second electrode 170 and the light efficiency improving layer 180 formed on the first electrode 170 .
- the first electrode 110 may be an anode (anode)
- the second electrode 170 may be a cathode (cathode)
- the first electrode may be a cathode and the second electrode may be an anode.
- the organic material layer may include a hole injection layer 120 , a hole transport layer 130 , a light emitting layer 140 , an electron transport layer 150 , and an electron injection layer 160 .
- the hole injection layer 120 , the hole transport layer 130 , the light emitting layer 140 , the electron transport layer 150 , and the electron injection layer 160 may be sequentially formed on the first electrode 110 .
- the light efficiency improving layer 180 is formed on one side of the second electrode 170 that is not in contact with the organic material layer.
- the thickness of the light efficiency improving layer may be 30 ⁇ 120nm.
- the lower limit of the thickness of the light efficiency improving layer may be, for example, 40 nm or more, 50 nm or more, or 55 nm or more.
- the upper limit of the thickness of the light efficiency improving layer may be, for example, 100 nm or less, 80 nm or less, or 65 nm or less.
- the light efficiency improving layer may have a refractive index of 1.85 or more for light having a wavelength of 450 to 750 nm.
- the upper limit of the refractive index of the light efficiency improving layer is not particularly limited, but may be, for example, 3.0 or less or 2.5 or less.
- the light efficiency improving layer 180 is formed on the second electrode 170 in the top emission method, the light efficiency improving layer is also on one side of both surfaces of the first electrode 110 that is not in contact with the organic material layer. can be formed.
- a buffer layer 210 or a light emitting auxiliary layer 220 may be further formed between the hole transport layer 130 and the light emitting layer 140 , which will be described with reference to FIG. 2 .
- the organic electric device 200 includes a hole injection layer 120 , a hole transport layer 130 , a buffer layer 210 sequentially formed on the first electrode 110 , It may include a light emitting auxiliary layer 220 , a light emitting layer 140 , an electron transport layer 150 , an electron injection layer 160 , and a second electrode 170 , and a light efficiency improving layer 180 is formed on the second electrode.
- a light emitting auxiliary layer 220 a light emitting layer 140 , an electron transport layer 150 , an electron injection layer 160 , and a second electrode 170 , and a light efficiency improving layer 180 is formed on the second electrode.
- an electron transport auxiliary layer may be further formed between the light emitting layer 140 and the electron transport layer 150 .
- the organic material layer may have a form in which a plurality of stacks including a hole transport layer, a light emitting layer, and an electron transport layer are formed. This will be described with reference to FIG. 3 .
- an organic electric device 300 includes two stacks ST1 and ST2 of an organic material layer formed of a multilayer between the first electrode 110 and the second electrode 170 . More than one set may be formed, and a charge generating layer (CGL) may be formed between stacks of organic material layers.
- CGL charge generating layer
- the organic electric device includes a first electrode 110 , a first stack ST1 , a charge generation layer (CGL), a second stack ST2, and a second electrode. 170 and the light efficiency improving layer 180 may be included.
- the first stack ST1 is an organic material layer formed on the first electrode 110 , which is a first hole injection layer 320 , a first hole transport layer 330 , a first emission layer 340 , and a first electron transport layer 350 .
- the second stack ST2 may include a second hole injection layer 420 , a second hole transport layer 430 , a second emission layer 440 , and a second electron transport layer 450 .
- the first stack and the second stack may be organic material layers having the same stacked structure or organic material layers having different stacked structures.
- a charge generation layer CGL may be formed between the first stack ST1 and the second stack ST2 .
- the charge generation layer CGL may include a first charge generation layer 360 and a second charge generation layer 361 .
- the charge generating layer CGL is formed between the first light emitting layer 340 and the second light emitting layer 440 to increase the efficiency of current generated in each light emitting layer and smoothly distribute charges.
- the first light-emitting layer 340 may include a light-emitting material including a blue fluorescent dopant in a blue host, and the second light-emitting layer 440 includes a material in which a green host is doped with a greenish yellow dopant and a red dopant. may be included, but is not limited thereto.
- n may be an integer of 1 to 5.
- the charge generation layer CGL and the third stack may be additionally stacked on the second stack ST2 .
- an organic electroluminescent device that emits white light by the mixing effect of light emitted from each light emitting layer can be manufactured as well as light of various colors. It is also possible to manufacture an organic electroluminescent device that emits light.
- the compound represented by Formula 1 of the present invention as a material for the light efficiency improving layer 180, it is possible to significantly improve the luminous efficiency and color purity while improving the lifespan of the organic electric device.
- the organic electroluminescent device may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD, for example, by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form the anode 110, and the hole injection layer 120 thereon , after forming an organic material layer including the hole transport layer 130 , the light emitting layer 140 , the electron transport layer 150 and the electron injection layer 160 , a material that can be used as the cathode 170 is deposited on the organic material layer, and then It may be manufactured by forming the light efficiency improving layer 180 on the cathode 170 .
- a deposition method such as PVD or CVD, for example, by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form the anode 110, and the hole injection layer 120 thereon , after forming an organic material layer including the hole transport layer 130 , the light emitting layer 140 , the electron transport layer 150 and the electron injection layer 160
- an auxiliary light emitting layer 220 may be formed between the hole transport layer 130 and the light emitting layer 140 , and an electron transport auxiliary layer (not shown) may be further formed between the light emitting layer 140 and the electron transport layer 150 . It can also be formed in a stack structure as shown.
- the organic layer is a solution process or a solvent process rather than a deposition method using various polymer materials, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, Dr. Blay It can be manufactured with a smaller number of layers by a method such as a printing process, a screen printing process, or a thermal transfer method. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the formation method.
- the organic electric device may be a top emission type, a back emission type, or a double-sided emission type depending on the material used.
- the organic electric device may be selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a device for monochromatic lighting, and a device for a quantum dot display.
- Another embodiment of the present invention may include a display device including the organic electric device of the present invention described above, and an electronic device including a control unit for controlling the display device.
- the electronic device may be a current or future wired/wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote control, a navigation system, a game machine, various TVs, and various computers.
- An organic electric device includes a first electrode; a second electrode; at least one organic material layer formed between the first electrode and the second electrode; and a light efficiency improving layer formed on one surface of both surfaces of the first electrode not in contact with the organic material layer or on one surface of both surfaces of the second electrode not in contact with the organic material layer, wherein the light efficiency improving layer is represented by the following formula (1) compounds.
- X and Z independently of one another are O or S, and Y is N(R), C(R')(R"), O or S.
- Ar 1 To Ar 4 are each independently a C 6 ⁇ C 60 Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; C 3 ⁇ C 60 aliphatic group; -L'-N(R a )(R b ); and Formula 1-1, and at least one of Ar 1 to Ar 4 is represented by Formula 1-1.
- L 1 To L 7 are each independently a single bond; C 6 ⁇ C 60 Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; And C 3 ⁇ C 60 It is selected from the group consisting of an aliphatic cyclic group.
- R 1 to R 3 are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; C 6 ⁇ C 60 Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; C 3 ⁇ C 60 aliphatic group; C 1 ⁇ C 30 Alkyl group; C 2 ⁇ C 30 Alkenyl group; C 2 ⁇ C 30 Alkynyl group; C 1 ⁇ C 30 An alkoxyl group; C 6 ⁇ C 30 Aryloxy group; and -L′-N(R a )(R b ), and adjacent groups may be bonded to each other to form a ring.
- n and p are each an integer of 0-4, m is an integer of 0-2, and when each of these is an integer of 2 or more, each of R 1 , each of R 2 , and each of R 3 are the same as or different from each other.
- o is an integer of 0 to 2, and when o is 2, each of L 1 , each of L 2 , each of L 3 , each of Ar 1 , and each of Ar 2 are the same as or different from each other.
- the L' is a single bond; C 6 ⁇ C 60 Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; And C 3 ⁇ C 60 It is selected from the group consisting of an aliphatic cyclic group.
- the R, R a and R b are each independently a C 6 ⁇ C 60 aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; And C 3 ⁇ C 60 It is selected from the group consisting of an aliphatic cyclic group.
- R' and R" are each independently hydrogen; deuterium; halogen; cyano group; nitro group; C 6 ⁇ C 60 aryl group; fluorenyl group; O, N, S, at least one heteroatom of S, Si and P Containing C 2 ⁇ C 60 Heterocyclic group; C 3 ⁇ C 60 Aliphatic ring group; C 1 ⁇ C 30 Alkyl group; C 2 ⁇ C 30 Alkenyl group; C 2 ⁇ C 30 Alkynyl group; C 1 ⁇ C 30 An alkoxyl group; And C 6 ⁇ C 30 It is selected from the group consisting of an aryloxy group, R' and R" may be bonded to each other to form a ring. When R' and R" combine with each other to form a ring, a spiro compound may be formed.
- the aryl group is, for example, C 6 to C 30 , C 6 to C 25 , C 6 ⁇ C 20 , C 6 ⁇ C 18 , C 6 ⁇ C 16 , C 6 ⁇ C 14 , C 6 ⁇ C 12 , C 6 ⁇ C 10 , C 6 , C 10 , C 12 , C 13 , C 14 , C 16 , may be an aryl group such as C 18 , and specifically, phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, and the like.
- the arylene group is, for example, C 6 to C 30 , C 6 to C 25 , C 6 to C 20 , C 6 to C 18 , C 6 ⁇ C 16 , C 6 ⁇ C 14 , C 6 ⁇ C 12 , C 6 ⁇ C 10 , C 6 , C 10 , C 12 , C 13 , C 14 , C 16 , C 18 may be an arylene group, Specifically, it may be phenylene, biphenyl, naphthylene, terphenyl, and the like.
- the heterocyclic group is, for example, C 2 ⁇ C 30 , C 2 ⁇ C 24 , C 2 ⁇ C 20 , C 2 ⁇ C 18 , C 2 ⁇ C 16 , C 2 ⁇ C 12 , C 2 ⁇ C 8 , C 3 , C 4 , C 5 , C 7 , C 8 , C 12 , C 13 , C 16 , may be a heterocyclic group such as C 18 , and specifically, pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, pyrrole, silol, indene, Indole, phenyl-indole, benzoindole, phenyl-benzoindole, pyrazinoindole
- the alkyl group is, for example, C 1 to C 20 , C 1 to C 10 , C 1 to C 4 , C 1 , C 2 , C 3 , may be an alkyl group such as C 4 , specifically methyl, ethyl, propyl, t-butyl, and the like.
- the aryl group is, for example, C 6 -C 20 , C 6 -C 18 , C 6 -C 16 , C 6 -C 14 , C 6 -C 12 , C 6 -C 10 , C It may be an aryl group such as 6 , C 10 , C 12 , C 13 , C 14 , C 16 , C 18 .
- the heterocyclic group is, for example, C 2 ⁇ C 20 , C 2 ⁇ C 18 , C 2 ⁇ C 16 , C 2 ⁇ C 12 , C 2 ⁇ C 8 , C 3 , C 4 , C 5 , C 7 , C 8 , C 12 , C 13 , C 16 , C 18 may be a heterocyclic group.
- the alkyl group may be, for example, an alkyl group such as C 1 to C 20 , C 1 to C 10 , C 1 to C 4 , C 1 , C 2 , C 3 , C 4 .
- Formula 1 may be represented by Formula 2 or Formula 3 below.
- Formula 1 may be represented by one of Formulas 4 to 7 below.
- the Chemical Formula 1-1 may be represented by the following Chemical Formula 1-1A.
- the compound represented by Formula 1 may be one of the following compounds, but is not limited thereto.
- the compound represented by Formula 1 according to the present invention (final product) may be prepared by reacting Core 1 and Sub1 as shown in Scheme 1 below, but is not limited thereto.
- Hal 1 and Hal 2 are each I, Br or Cl, L′ is L 2 or L 5 , L′′ is L 3 or L 6 , Ar′ is Ar 1 or Ar 3 , Ar′′ is Ar 2 or Ar 4 Lim)
- Core 1 of Scheme 1 may be synthesized by the reaction routes of Schemes 2 to 5, but is not limited thereto.
- Hal 3 is halogen.
- the compound belonging to Core1 may be a compound as follows, but is not limited thereto, and Table 1 shows FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.
- Sub1 of Scheme 1 may be synthesized by the reaction route of Scheme 6 below, but is not limited thereto.
- the compound belonging to Sub1 may be a compound as follows, but is not limited thereto, and Table 2 shows FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.
- Core1-1 (20 g, 50.65 mmol) to Sub1-1 (20.43 g, 50.65 mmol), Pd 2 (dba) 3 (0.75 g, 0.82 mmol), 50% P( t- Bu) 3 (0.75 g, 0.82) mmol), NaO t -Bu (7.87 g, 81.87 mmol), and toluene (169 ml) were added and stirred at 130°C. Upon completion of the reaction , the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 22.90 g (yield: 86%) of the product.
- N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4 on the ITO layer (anode) formed on the glass substrate -diamine (hereinafter abbreviated as '2-TNATA') film was vacuum deposited to form a 60 nm thick hole injection layer, and then N,N'-bis(1-naphthalenyl)-N,N'-bis-phenyl- A (1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as 'NPB') film was vacuum-deposited to a thickness of 60 nm to form a hole transport layer.
- 9,10-di(naphthalen-2-yl)anthracene as a host and BD-052X (Idemitsu kosan) as a dopant were used on the hole transport layer, but doped with dopants so that these weight ratios were 93:7 A light emitting layer was formed.
- 'BAlq' (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum
- Alq 3 tris(8-quinolinol)aluminum
- LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer
- Al was deposited on the electron injection layer to a thickness of 150 nm to form a cathode
- the compound P-1 of the present invention was A film was formed to a thickness of 60 nm to form a light efficiency improving layer.
- An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention described in Table 4 was used instead of the compound P-1 of the present invention as a material for the light efficiency improvement layer.
- An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the light efficiency improving layer was not formed.
- An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the following comparative compound A was used instead of the compound P-1 of the present invention as a material for the light efficiency improvement layer.
- CBP 4,4'-N,N'-dicarbazole-biphenyl
- Ir(ppy) 3 tris(2-phenylpyridine)-iridium
- An organic electroluminescent device was manufactured in the same manner as in Example 17, except that the light efficiency improving layer was not formed.
- An organic electroluminescent device was manufactured in the same manner as in Example 17, except that Comparative Compound A was used as a material for the light efficiency improving layer.
- An organic electroluminescent device was manufactured in the same manner as in Example 33, except that the light efficiency improving layer was not formed.
- An organic electroluminescent device was manufactured in the same manner as in Example 33, except that Comparative Compound A was used as a material for the light efficiency improving layer.
- SPPs Surface plasmon polaritons
- TE transverse electric
- TM transverse magnetic
- the compound of the present invention has a tetracyclic core in which oxazole and thiazole moieties having a high refractive index in the visible wavelength band (range of 430 nm to 780 nm) are fused, and at least one amino group is bonded to this core, It has a structure in which a substituent such as benzoxazole and benzothiazole, which can increase the refractive index, is also bonded to the amino group.
- the compound of the present invention has a higher refractive index than the comparative compound A due to synergy due to the combination of the core and the substituent, and as a result, the light generated in the organic layer is extracted to the outside of the organic light emitting device by the principle of constructive interference. As this increases, the overall light efficiency of the organic light emitting diode is improved.
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Abstract
The present invention relates to an organic electronic device comprising a capping layer, and an electronic apparatus comprising same, and the capping layer is formed with a compound represented by chemical formula 1, of the present invention, and thus the efficiency and color purity of an organic electronic device can be improved.
Description
본 발명은 광효율 개선층을 포함하는 유기전기소자 및 이를 포함하는 전자 장치에 관한 것이다.The present invention relates to an organic electric device including a light efficiency improving layer and an electronic device including the same.
유기발광소자는 자발광형 소자로서 시야각이 넓고 콘트라스트가 우수할 뿐만 아니라, 응답시간이 빠르며, 휘도, 구동전압 및 응답속도 특성이 우수하고 다색화가 가능하다는 장점을 가지고 있다.The organic light emitting device is a self-luminous device, and has a wide viewing angle and excellent contrast, as well as a fast response time, excellent luminance, driving voltage and response speed characteristics, and multicolorization is possible.
이러한 유기 발광 소자는 기판 상에 제1전극(애노드), 정공수송 영역, 발광층, 전자수송 영역 및 제2전극(캐소드)이 순차적으로 형성된 구조를 가진다. 제1전극으로부터 주입된 정공은 정공수송 영역을 경유하여 발광층으로 이동하고, 제2전극으로부터 주입된 전자는 전자수송 영역을 경유하여 발광층으로 이동한다. 정공 및 전자와 같은 캐리어들은 발광층 영역에서 재결합하여 엑시톤(exciton)을 생성하는데, 엑시톤이 여기 상태에서 기저상태로 변하면서 광이 생성된다.Such an organic light emitting device has a structure in which a first electrode (anode), a hole transport region, a light emitting layer, an electron transport region, and a second electrode (cathode) are sequentially formed on a substrate. Holes injected from the first electrode move to the emission layer via the hole transport region, and electrons injected from the second electrode move to the emission layer via the electron transport region. Carriers such as holes and electrons recombine in the emission layer region to generate excitons, and light is generated as the excitons change from an excited state to a ground state.
유기 발광 소자의 광효율은 통상적으로 내부 발광 효율(internal liminescnet efficiency)과 외부 발광 효율(external liminescent efficiency)로 나눌 수 있다.The luminous efficiency of the organic light emitting diode can be generally divided into internal luminescent efficiency and external liminescent efficiency.
내부 발광 효율은 정공 수송층, 발광층 및 전자 수송층 등과 같이 제1전극과 제2전극 사이(즉, 애노드와 캐소드 사이)에 개재된 유기층에서 얼마나 효율적으로 엑시톤이 생성되어 광변환이 이루어지는가와 관련이 있고, 외부 발광 효율(이하, "광취출율"(light coupling efficiency)이라고도 함)이란, 유기층에서 생성된 광이 유기 발광 소자 외부로 취출되는 효율을 가리키는 것으로서, 유기층에서 높은 광변환 효율을 달성하더라도(즉, 내부 발광 효율이 높더라도), 외부 발광 효율이 낮다면, 유기 발광 소자의 전체적인 광효율은 저하될 수 밖에 없다.The internal luminous efficiency is related to how efficiently excitons are generated and light conversion is performed in the organic layer interposed between the first and second electrodes (that is, between the anode and the cathode), such as a hole transport layer, a light emitting layer, and an electron transport layer, etc. External luminous efficiency (hereinafter also referred to as “light coupling efficiency”) refers to the efficiency at which light generated in the organic layer is extracted to the outside of the organic light emitting device, and even if high light conversion efficiency is achieved in the organic layer (that is, , even if the internal luminous efficiency is high), if the external luminous efficiency is low, the overall luminous efficiency of the organic light emitting diode is inevitably reduced.
최근에는 각 재료의 성능에 변화를 주어 소자 특성을 향상시키는 연구뿐만 아니라, 공진 구조의 Top 소자에서는 애노드(anode)와 캐소드(cathode) 사이에 최적화된 광학 두께에 의한 색순도 향상 및 효율 증대기술이 소자 성능을 향상시키는데 중요한 요소 중의 하나이다. 비공진 구조의 바텀(Bottom) 소자구조와 비교해보면 탑(Top) 소자구조는 형성된 빛이 반사막인 애노드에 반사되어 캐소드쪽으로 빛이 나오므로 SPP(surface plasmon polariton)에 의한 광학 에너지 손실이 크다.Recently, in addition to research on improving device characteristics by changing the performance of each material, technology for improving color purity and increasing efficiency by optimized optical thickness between an anode and a cathode in a top device with a resonance structure has been developed. It is one of the important factors to improve performance. Compared with the bottom device structure of the non-resonant structure, the top device structure has a large optical energy loss due to surface plasmon polariton (SPP) because the formed light is reflected by the anode, which is a reflective film, and emitted toward the cathode.
따라서, EL 스펙트럼의 모양과 효율향상을 위한 중요한 방법 중의 하나는 탑 캐소드(Top cathode) 타입에 광효율 개선층 (Capping layer)을 적용하는 방법이 있다. Accordingly, one of the important methods for improving the shape and efficiency of the EL spectrum is a method of applying a capping layer to a top cathode type.
일반적으로 캐소드 전극으로 Al, Pt, Ag, Au 등의 금속이 주로 사용되며 SSP는 이들 금속 전극 표면에서 발생한다. 예를 들어 음극을 Ag로 사용할 경우 음극의 Ag로 인해 방출되는 빛이 SPP에 의해 Quenching(Ag로 인한 빛에너지 손실)되어 효율이 감소된다.In general, metals such as Al, Pt, Ag, and Au are mainly used as cathode electrodes, and SSP is generated on the surface of these metal electrodes. For example, when the cathode is used as Ag, the light emitted by the Ag of the cathode is quenched by the SPP (light energy loss due to Ag) and the efficiency is reduced.
하지만, 광효율 개선층을 사용할 경우에는 MgAg 전극과 고굴절의 유기재료 경계면에서 SPP가 발생하며 그 중 TE(transverse electric) 편광된 빛은 소산파(evanescent wave)에 의해 수직 방향으로 광효율 개선층면에서 소멸되며, 음극과 캐핑층을 따라 이동하는 TM(transverse magnetic) 편광된 빛은 표면 플라즈마 공진(surface plasma resonance)에 의해 파장의 증폭현상이 일어난다. 그 결과, 피크(peak)의 세기(intensity)가 증가하여 결국 높은 효율과 효과적인 색순도 조절이 가능하게 된다.However, when the light efficiency improvement layer is used, SPP occurs at the interface between the MgAg electrode and the high refractive organic material, and among them, transverse electric (TE) polarized light is annihilated in the vertical direction by the evanescent wave. , TM (transverse magnetic) polarized light traveling along the cathode and the capping layer has a wavelength amplification phenomenon due to surface plasma resonance. As a result, the intensity of the peak increases, so that high efficiency and effective color purity control are possible.
따라서, 유기전기소자의 전체적인 효율을 향상시키면서 색순도를 향상시킬 수 있는 광효율 개선층의 재료에 대한 연구개발이 필요하다.Therefore, there is a need for research and development on the material of the light efficiency improving layer capable of improving the color purity while improving the overall efficiency of the organic electric device.
따라서, 본 발명은 특정 화합물로 광효율 개선층을 형성함으로써 발광효율과 색순도가 현저히 향상된 유기전기소자 및 이를 포함하는 전자장치를 제공하는 것을 목적으로 한다.Accordingly, an object of the present invention is to provide an organic electric device having significantly improved luminous efficiency and color purity by forming a light efficiency improving layer with a specific compound, and an electronic device including the same.
일 측면에서, 본 발명은 하기 화학식으로 표시되는 화합물을 광효율 개선층에 포함하는 유기전기소자 및 그 전자장치를 제공한다.In one aspect, the present invention provides an organic electric device comprising a compound represented by the following formula in a light efficiency improving layer and an electronic device thereof.
본 발명에 따른 화합물을 광효율 개선층 재료로 사용함으로써 유기전기소자의 발광효율 및 색순도를 향상시킬 수 있다.By using the compound according to the present invention as a material for the light efficiency improvement layer, the luminous efficiency and color purity of the organic electric device can be improved.
도 1 내지 도 3은 본 발명에 따른 유기전기발광소자의 예시도이다.1 to 3 are exemplary views of an organic electroluminescent device according to the present invention.
[부호의 설명][Explanation of code]
100, 200, 300: 유기전기소자 110: 제1 전극100, 200, 300: organic electric device 110: first electrode
120: 정공주입층 130: 정공수송층120: hole injection layer 130: hole transport layer
140: 발광층 150: 전자수송층140: light emitting layer 150: electron transport layer
160: 전자주입층 170: 제2 전극160: electron injection layer 170: second electrode
180: 광효율 개선층 210: 버퍼층180: light efficiency improvement layer 210: buffer layer
220: 발광보조층 320: 제1 정공주입층220: light emitting auxiliary layer 320: first hole injection layer
330: 제1 정공수송층 340: 제1 발광층330: first hole transport layer 340: first light emitting layer
350: 제1 전자수송 층 360: 제1 전하생성층350: first electron transport layer 360: first charge generation layer
361: 제2 전하생성층 420: 제2 정공주입층361: second charge generation layer 420: second hole injection layer
430: 제2 정공수송층 440: 제2 발광층430: second hole transport layer 440: second light emitting layer
450: 제2 전자수송층 CGL: 전하생성층450: second electron transport layer CGL: charge generation layer
ST1: 제1 스택 ST2: 제2 스택ST1: first stack ST2: second stack
본 발명에서 사용된 용어 "아릴기" 및 "아릴렌기"는 다른 설명이 없는 한 각각 6 내지 60의 탄소수를 가지며, 이에 제한되는 것은 아니다. 본 발명에서 아릴기 또는 아릴렌기는 단일고리형, 고리집합체, 접합된 여러 고리계, 스파이로 화합물 등을 포함할 수 있다. 또한, 본 명세서에서 다른 설명이 없는 한 아릴기에는 플루오렌일기가 포함될 수 있고 아릴렌기에는 플루오렌일렌기가 포함될 수 있다.The terms "aryl group" and "arylene group" used in the present invention have 6 to 60 carbon atoms, respectively, unless otherwise specified, but are not limited thereto. In the present invention, the aryl group or the arylene group may include a monocyclic type, a ring aggregate, a fused multiple ring system, a spiro compound, and the like. In addition, unless otherwise specified in the present specification, the aryl group may include a fluorenyl group and the arylene group may include a fluorenylene group.
본 발명에서 사용된 용어 "플루오렌일기"는 치환 또는 비치환된 플루오렌일기를, "플루오렌일렌기"는 치환 또는 비치환된 플루오렌일기를 의미하며, 본 발명에서 사용된 플루오렌일기 또는 플루오렌일렌기는 하기 구조에서 R과 R'이 서로 결합되어 이들이 결합된 탄소와 함께 스파이로 화합물을 형성한 경우를 포함한다.As used herein, the term "fluorenyl group" refers to a substituted or unsubstituted fluorenyl group, "fluorenylene group" refers to a substituted or unsubstituted fluorenyl group, and as used in the present invention, the fluorenyl group or The fluorenylene group includes a case in which R and R' are bonded to each other in the following structure to form a spiro compound together with the carbon to which they are bonded.
"치환된 플루오렌일기", "치환된 플루오렌일렌기"는 하기 구조에서 R, R', R" 중 적어도 하나가 수소 이외의 치환기인 것을 의미하며, 본 명세서에서는 가수와 상관없이 플루오렌일기, 플루오렌일렌기, 플루오렌트리일기 등을 모두 플루오렌기라고 명명할 수도 있다."Substituted fluorenyl group", "substituted fluorenylene group" means that at least one of R, R', R" in the following structure is a substituent other than hydrogen, and in the present specification, regardless of the valence, a fluorenyl group , a fluorenylene group, a fluorentriyl group, etc. may all be called a fluorene group.
본 발명에서 사용된 용어 "스파이로 화합물"은 '스파이로 연결'을 가지며, 스파이로 연결은 2개의 고리가 오로지 1개의 원자를 공유함으로써 이루어지는 연결을 의미한다. 이때, 두 고리에 공유된 원자를 '스파이로 원자'라 하며, 한 화합물에 들어 있는 스파이로 원자의 수에 따라 이들을 각각 '모노스파이로-', '다이스파이로-', '트라이스파이로-' 화합물이라 한다.As used herein, the term "spiro compound" has a 'spiro linkage', and the spiro linkage means a linkage formed by sharing only one atom between two rings. At this time, the atoms shared by the two rings are called 'spiro atoms', and they are respectively 'monospiro-', 'dispiro-', 'trispiro-', depending on the number of spiro atoms in a compound. ' It's called a compound.
본 발명에 사용된 용어 "헤테로고리기"는 "헤테로아릴기" 또는 "헤테로아릴렌기"와 같은 방향족 고리뿐만 아니라 비방향족 고리도 포함하며, 다른 설명이 없는 한 각각 하나 이상의 헤테로원자를 포함하는 탄소수 2 내지 60의 고리를 의미하나 여기에 제한되는 것은 아니다. 본 명세서에서 사용된 용어 "헤테로원자"는 다른 설명이 없는 한 N, O, S, P 또는 Si를 나타내며, 헤테로고리기는 헤테로원자를 포함하는 단일고리형, 고리집합체, 접합된 여러 고리계, 스파이로 화합물 등을 의미한다. 또한, 고리를 형성하는 탄소 대신 하기 화합물과 같이 SO2, P=O 등과 같은 헤테로원자단을 포함하는 화합물도 헤테로고리기에 포함될 수 있다.The term "heterocyclic group" used in the present invention includes not only aromatic rings such as "heteroaryl group" or "heteroarylene group" but also non-aromatic rings, and unless otherwise specified, the number of carbon atoms each containing at least one heteroatom It means a ring of 2 to 60, but is not limited thereto. As used herein, the term "heteroatom" refers to N, O, S, P or Si, unless otherwise specified, and the heterocyclic group is a monocyclic group including a heteroatom, a ring aggregate, a fused multiple ring system, a spy means a compound or the like. In addition, a compound including a heteroatom group such as SO 2 , P=O, etc. may be included in the heterocyclic group, such as the following compounds instead of carbon forming a ring.
본 발명에 사용된 용어 "지방족고리기"는 방향족탄화수소를 제외한 고리형 탄화수소를의미하며, 단일고리형, 고리집합체, 접합된 여러 고리계, 스파이로 화합물 등을 포함하며, 다른 설명이 없는 한 탄소수 3 내지 60의 고리를의미하나 여기에 제한되는 것은 아니다. 예컨대, 방향족고리인 벤젠과 비방향족고리인 사이클로헥산이 융합된 경우에도 지방족고리에 해당한다.The term "aliphatic ring group" used in the present invention refers to a cyclic hydrocarbon other than an aromatic hydrocarbon, and includes a monocyclic type, a ring aggregate, a fused multiple ring system, a spiro compound, etc., unless otherwise specified, the number of carbon atoms It means a ring of 3 to 60, but is not limited thereto. For example, even when benzene, which is an aromatic ring, and cyclohexane, which is a non-aromatic ring, are fused, it corresponds to an aliphatic ring.
본 명세서에서 각 기호 및 그 치환기의 예로 예시되는 아릴기, 아릴렌기, 헤테로고리기 등에 해당하는 '기 이름'은 '가수를 반영한 기의 이름'을 기재할 수도 있지만, '모체화합물 명칭'으로 기재할 수도 있다. 예컨대, 아릴기의 일종인 '페난트렌'의 경우, 1가의 '기'는 '페난트릴'로 2가의 기는 '페난트릴렌' 등과 같이 가수를 구분하여 기의 이름을 기재할 수도 있지만, 가수와 상관없이 모체 화합물 명칭인 '페난트렌'으로 기재할 수도 있다. 유사하게, 피리미딘의 경우에도, 가수와 상관없이 '피리미딘'으로 기재하거나, 1가인 경우에는 피리미딘일기, 2가의 경우에는 피리미딘일렌 등과 같이 해당 가수의 '기의 이름'으로 기재할 수도 있다. In the present specification, the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc. exemplified as examples of each symbol and its substituents may be described as 'the name of the group reflecting the valence', but is described as 'name of the parent compound' You may. For example, in the case of 'phenanthrene', which is a type of aryl group, the monovalent 'group' is 'phenanthryl' and the divalent group is 'phenanthrylene'. Regardless, it can also be described as the name of the parent compound, 'phenanthrene'. Similarly, in the case of pyrimidine, regardless of the valence, it can be described as 'pyrimidine', or in the case of monovalent, as a pyrimidinyl group, in the case of divalent, as the 'name of the group' of the corresponding valence, such as pyrimidinylene. have.
또한, 본 명세서에서는 화합물 명칭이나 치환기 명칭을 기재함에 있어 위치를 표시하는 숫자나 알파벳 등은 생략할 수도 있다. 예컨대, 피리도[4,3-d]피리미딘을 피리도피리미딘으로, 벤조퓨로[2,3-d]피리미딘을 벤조퓨로피리미딘으로, 9,9-다이메틸-9H-플루오렌을 다이메틸플루오렌 등과 같이 기재할 수 있다. 따라서, 벤조[g]퀴녹살린이나 벤조[f]퀴녹살린을 모두 벤조퀴녹살린이라고 기재할 수 있다.In addition, in the present specification, in describing the compound name or the substituent name, numbers or alphabets indicating positions may be omitted. For example, pyrido[4,3-d]pyrimidine to pyridopyrimidine, benzofuro[2,3-d]pyrimidine to benzofuropyrimidine, 9,9-dimethyl-9H-flu Orene can be described as dimethylfluorene and the like. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.
또한, 명시적인 설명이 없는 한, 본 발명에서 사용되는 화학식은 하기 화학식의 지수 정의에 의한 치환기 정의와 동일하게 적용된다.In addition, unless there is an explicit explanation, the formula used in the present invention is the same as the definition of the substituent by the exponential definition of the following formula.
여기서, a가 0의 정수인 경우 치환기 R1은 부존재하는 것을 의미하는데, 즉 a가 0인 경우는 벤젠고리를 형성하는 탄소에 모두 수소가 결합된 것을 의미하며, 이때 탄소에 결합된 수소의 표시를 생략하고 화학식이나 화합물을 기재할 수 있다. 또한, a가 1의 정수인 경우 하나의 치환기 R1은 벤젠 고리를 형성하는 탄소 중 어느 하나의 탄소에 결합하며, a가 2 또는 3의 정수인 경우 예컨대 아래와 같이 결합할 수 있고, a가 4 내지 6의 정수인 경우에도 이와 유사한 방식으로 벤젠 고리의 탄소에 결합하며, a가 2 이상의 정수인 경우 R1은 서로 같거나 상이할 수 있다.Here, when a is an integer of 0, the substituent R 1 means that it does not exist, that is, when a is 0, it means that all hydrogens are bonded to the carbons forming the benzene ring, and in this case, the indication of hydrogen bonded to carbon is shown. It can be omitted and the chemical formula or compound can be described. In addition, when a is an integer of 1, one substituent R 1 is bonded to any one of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it may be bonded as follows, for example, a is 4 to 6 Even if it is an integer of , it is bonded to the carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R 1 may be the same as or different from each other.
또한, 본 명세서에서 다른 설명이 없는 한, 축합환을 표시할 때 '숫자-축합환'에서 숫자는 축합되는 고리의 개수를 나타낸다. 예컨대, 안트라센, 페난트렌, 벤조퀴나졸린 등과 같이 3개의 고리가 서로 축합한 형태는 3-축합환으로 표기할 수 있다.In addition, unless otherwise specified in the present specification, when representing a condensed ring, the number in 'number-condensed ring' indicates the number of rings to be condensed. For example, a form in which three rings are condensed with each other, such as anthracene, phenanthrene, benzoquinazoline, etc., may be expressed as a 3-condensed ring.
또한, 본 명세서에서 다른 설명이 없는 한, 5원자 고리, 6원자 고리 등과 같이 '숫자원자' 형식으로 고리를 표현한 경우, '숫자-원자'에서 숫자는 고리를 형성하는 원소의 개수를 나타낸다. 예컨대, 싸이오펜이나 퓨란 등은 5원자 고리에 해당할 수 있고, 벤젠이나 피리딘은 6원자 고리에 해당할 수 있다.In addition, unless otherwise specified in the present specification, when a ring is expressed in the form of a 'numeric atom' such as a 5-membered ring, a 6-membered ring, etc., the number in 'number-atom' indicates the number of elements forming the ring. For example, thiophene or furan may correspond to a 5-membered ring, and benzene or pyridine may correspond to a 6-membered ring.
또한, 본 명세서에서 다른 설명이 없는 한, 이웃한 기끼리 서로 결합하여 형성한 고리는 C6~C60의 방향족고리기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 C3~C60의 지방족고리기;로 이루어진 군에서 선택될 수 있다. In addition, unless otherwise stated in the present specification, the ring formed by bonding adjacent groups to each other is a C 6 ~ C 60 aromatic ring group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; And C 3 ~ C 60 An aliphatic ring group; may be selected from the group consisting of.
이때, 본 명세서에서 다른 설명이 없는 한, '이웃한 기끼리'라 함은, 하기 화학식을 예로 들어 설명하면, R1과 R2끼리, R2와 R3끼리, R3과 R4끼리, R5와 R6끼리 뿐만 아니라, 하나의 탄소를 공유하는 R7과 R8끼리도 포함되고, R1과 R7끼리, R1과 R8끼리 또는 R4와 R5끼리 등과 같이 바로 인접하지 않은 고리 구성 원소(탄소나 질소 등)에 결합된 치환기도 포함될 수 있다. 즉, 바로 인접한 탄소나 질소 등과 같은 고리 구성 원소에 치환기가 있을 경우에는 이들이 이웃한 기가 될 수 있지만, 바로 인접한 위치의 고리 구성 원소에 그 어떤 치환기도 결합되지 않은 경우에는 그 다음 고리 구성 원소에 결합된 치환기와 이웃한 기가 될 수 있고, 또한 동일 고리 구성 탄소에 결합된 치환기끼리도 이웃한 기라고 할 수 있다. At this time, unless otherwise specified in the present specification, 'neighboring groups' refers to each other when describing the following chemical formula as an example, R 1 and R 2 each other , R 2 and R 3 each other , R 3 and R 4 each other , Not only R 5 and R 6 but also R 7 and R 8 sharing one carbon are included, and not immediately adjacent, such as R 1 and R 7 , R 1 and R 8 , or R 4 and R 5 , etc. Substituents bonded to ring constituents (such as carbon or nitrogen) may also be included. That is, if there is a substituent on a ring constituent element such as carbon or nitrogen immediately adjacent to it, they may be a neighboring group, but if no substituent is bonded to a ring constituent element at the immediately adjacent position, it is bonded to the next ring constituent element It can be a group adjacent to the substituent group, and also the substituents bonded to the same ring constituent carbon can be said to be adjacent groups.
하기 화학식에서 R7과 R8처럼 동일 탄소에 결합된 치환기가 서로 결합하여 고리를 형성할 경우에는 스파이로 모이어티가 포함된 화합물이 형성될 수 있다. When substituents bonded to the same carbon as R 7 and R 8 in the following formula combine with each other to form a ring, a compound including a spiro moiety may be formed.
또한, 본 명세서에서 '이웃한 기끼리 서로 결합하여 고리를 형성할 수 있다'라는 표현은 '이웃한 기끼리 서로 결합하여 선택적으로 고리를 형성한다'라는 것과 동일한 의미로 사용되며, 적어도 한 쌍의 이웃한 기끼리 서로 결합하여 고리를 형성하는 경우를 의미한다. In addition, in the present specification, the expression 'neighboring groups may combine with each other to form a ring' is used in the same meaning as 'neighboring groups combine with each other to selectively form a ring', and at least one pair of It means a case where adjacent groups are bonded to each other to form a ring.
이하, 본 발명의 화합물이 포함된 유기전기소자의 적층구조에 대하여 도 1 내지 도 3을 참조하여 설명한다.Hereinafter, the laminated structure of the organic electric device containing the compound of the present invention will be described with reference to FIGS. 1 to 3 .
도 1 내지 도 3은 본 발명의 실시예에 따른 유기전기소자의 예시도이다.1 to 3 are exemplary views of an organic electric device according to an embodiment of the present invention.
도 1을 참조하면, 본 발명의 일 실시예에 따른 유기전기소자(100)는 기판(미도시) 상에 형성된 제1 전극(110)과, 제2 전극(170), 제1 전극(110)과 제2 전극(170) 사이에 형성된 유기물층, 및 제1 전극(170) 상에 형성된 광효율 개선층(180)을 포함한다.Referring to FIG. 1 , an organic electric device 100 according to an embodiment of the present invention includes a first electrode 110 , a second electrode 170 , and a first electrode 110 formed on a substrate (not shown). and an organic material layer formed between the second electrode 170 and the light efficiency improving layer 180 formed on the first electrode 170 .
상기 제1 전극(110)은 애노드(양극)이고, 제2 전극(170)은 캐소드(음극)이며, 인버트형의 경우에는 제1 전극이 캐소드이고 제2 전극이 애노드일 수 있다.The first electrode 110 may be an anode (anode), the second electrode 170 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.
상기 유기물층은 정공주입층(120), 정공수송층(130), 발광층(140), 전자수송층(150) 및 전자주입층(160)을 포함할 수 있다. 구체적으로, 제1 전극(110) 상에 정공주입층(120), 정공수송층(130), 발광층(140), 전자수송층(150) 및 전자주입층(160)이 순차적으로 형성될 수 있다.The organic material layer may include a hole injection layer 120 , a hole transport layer 130 , a light emitting layer 140 , an electron transport layer 150 , and an electron injection layer 160 . Specifically, the hole injection layer 120 , the hole transport layer 130 , the light emitting layer 140 , the electron transport layer 150 , and the electron injection layer 160 may be sequentially formed on the first electrode 110 .
상기 광효율 개선층(180)은 제2 전극(170)의 양면 중에서 유기물층과 접하지 않는 일면에 형성된다. The light efficiency improving layer 180 is formed on one side of the second electrode 170 that is not in contact with the organic material layer.
광효율 개선층의 두께는 30~120nm일 수 있다. 상기 광효율 개선층의 두께의 하한은, 예를 들면, 40nm 이상, 50nm 이상 또는 55nm 이상일 수 있다. 상기 광효율 개선층의 두께의 상한은, 예를 들면, 100nm 이하, 80nm 이하 또는 65nm 이하일 수 있다. 광효율 개선층의 두께를 상술한 범위로 조절할 경우, 표면 플라즈마 공진 (surface plasmon resonance)에 의하여 높은 광효율과 색순도를 가지는 유기전기소자를 제공할수 있다.The thickness of the light efficiency improving layer may be 30 ~ 120nm. The lower limit of the thickness of the light efficiency improving layer may be, for example, 40 nm or more, 50 nm or more, or 55 nm or more. The upper limit of the thickness of the light efficiency improving layer may be, for example, 100 nm or less, 80 nm or less, or 65 nm or less. When the thickness of the light efficiency improving layer is adjusted within the above-described range, it is possible to provide an organic electric device having high light efficiency and color purity due to surface plasma resonance.
광효율 개선층은 파장이 450~750nm인 광에 대한 굴절률이 1.85 이상일 수 있다. 광효율 개선층의 굴절률의 상한은 특별히 제한되는 것은 아니나, 예를 들면, 3.0 이하 또는 2.5 이하일 수 있다. 광효율 개선층의 굴절률을 상술한 범위로 조절할 경우, 표면 플라즈마 공진 (surface plasmon resonance)에 의하여 높은 광효율과 색순도를 가지는 유기전기소자를 제공할 수 있다.The light efficiency improving layer may have a refractive index of 1.85 or more for light having a wavelength of 450 to 750 nm. The upper limit of the refractive index of the light efficiency improving layer is not particularly limited, but may be, for example, 3.0 or less or 2.5 or less. When the refractive index of the light efficiency improving layer is adjusted within the above-described range, an organic electric device having high light efficiency and color purity by surface plasma resonance can be provided.
도 1은 전면발광 방식에서, 광효율 개선층(180)이 제2 전극(170) 상에 형성된 경우를 예시하고 있지만, 광효율 개선층은 제1 전극(110)의 양면 중에서 유기물층과 접하지 않는 일면에도 형성될 수 있다.1 illustrates a case in which the light efficiency improving layer 180 is formed on the second electrode 170 in the top emission method, the light efficiency improving layer is also on one side of both surfaces of the first electrode 110 that is not in contact with the organic material layer. can be formed.
또한, 정공수송층(130)과 발광층(140) 사이에 버퍼층(210)이나 발광보조층(220)이 더 형성될 수 있는데 이에 대해 도 2를 참조하여 설명한다.In addition, a buffer layer 210 or a light emitting auxiliary layer 220 may be further formed between the hole transport layer 130 and the light emitting layer 140 , which will be described with reference to FIG. 2 .
도 2를 참조하면, 본 발명의 다른 실시예에 따른 유기전기소자(200)는 제1 전극(110) 상에 순차적으로 형성된 정공주입층(120), 정공수송층(130), 버퍼층(210), 발광보조층(220), 발광층(140), 전자수송층(150), 전자주입층(160), 제2 전극(170)을 포함할 수 있고, 제2 전극 상에 광효율개선층(180)이 형성될 수 있다.Referring to FIG. 2 , the organic electric device 200 according to another embodiment of the present invention includes a hole injection layer 120 , a hole transport layer 130 , a buffer layer 210 sequentially formed on the first electrode 110 , It may include a light emitting auxiliary layer 220 , a light emitting layer 140 , an electron transport layer 150 , an electron injection layer 160 , and a second electrode 170 , and a light efficiency improving layer 180 is formed on the second electrode. can be
도 2에 도시되지는 않았으나, 발광층(140)과 전자수송층(150) 사이에 전자수송보조층이 더 형성될 수도 있다.Although not shown in FIG. 2 , an electron transport auxiliary layer may be further formed between the light emitting layer 140 and the electron transport layer 150 .
또한, 본 발명의 다른 실시예에 따르면 유기물층은 정공수송층, 발광층 및 전자수송층을 포함하는 스택이 복수개 형성된 형태일 수도 있다. 이에 대해 도 3을 참조하여 설명한다.In addition, according to another embodiment of the present invention, the organic material layer may have a form in which a plurality of stacks including a hole transport layer, a light emitting layer, and an electron transport layer are formed. This will be described with reference to FIG. 3 .
도 3을 참조하면, 본 발명의 또 다른 실시예에 따른 유기전기소자(300)는 제1 전극(110)과 제2 전극(170) 사이에 다층으로 이루어진 유기물층의 스택(ST1, ST2)이 두 세트 이상 형성될 수 있고 유기물층의 스택 사이에 전하 생성층(CGL)이 형성될 수도 있다.Referring to FIG. 3 , an organic electric device 300 according to another embodiment of the present invention includes two stacks ST1 and ST2 of an organic material layer formed of a multilayer between the first electrode 110 and the second electrode 170 . More than one set may be formed, and a charge generating layer (CGL) may be formed between stacks of organic material layers.
구체적으로, 본 발명에 일 실시예에 따른 유기전기소자는 제1 전극(110), 제1 스택(ST1), 전하 생성층(CGL: Charge Generation Layer), 제2 스택(ST2), 제2 전극(170) 및 광효율 개선층(180)을 포함할 수 있다. Specifically, the organic electric device according to an embodiment of the present invention includes a first electrode 110 , a first stack ST1 , a charge generation layer (CGL), a second stack ST2, and a second electrode. 170 and the light efficiency improving layer 180 may be included.
제1 스택(ST1)은 제1 전극(110) 상에 형성된 유기물층으로, 이는 제1 정공주입층(320), 제1 정공수송층(330), 제1 발광층(340) 및 제1 전자수송층(350)을 포함할 수 있고, 제2 스택(ST2)은 제2 정공주입층(420), 제2 정공수송층(430), 제2 발광층(440) 및 제2 전자수송층(450)을 포함할 수 있다. 이와 같이 제1 스택과 제2 스택은 동일한 적층 구조를 갖는 유기물층일 수도 있지만 서로 다른 적층 구조의 유기물층일 수도 있다.The first stack ST1 is an organic material layer formed on the first electrode 110 , which is a first hole injection layer 320 , a first hole transport layer 330 , a first emission layer 340 , and a first electron transport layer 350 . ), and the second stack ST2 may include a second hole injection layer 420 , a second hole transport layer 430 , a second emission layer 440 , and a second electron transport layer 450 . . As such, the first stack and the second stack may be organic material layers having the same stacked structure or organic material layers having different stacked structures.
제1 스택(ST1)과 제2 스택(ST2) 사이에는 전하 생성층(CGL)이 형성될 수 있다. 전하 생성층(CGL)은 제1 전하 생성층(360)과 제2 전하 생성층(361)을 포함할 수 있다. 이러한 전하 생성층(CGL)은 제1 발광층(340)과 제2 발광층(440) 사이에 형성되어 각각의 발광층에서 발생하는 전류 효율을 증가시키고, 전하를 원활하게 분배하는 역할을 한다.A charge generation layer CGL may be formed between the first stack ST1 and the second stack ST2 . The charge generation layer CGL may include a first charge generation layer 360 and a second charge generation layer 361 . The charge generating layer CGL is formed between the first light emitting layer 340 and the second light emitting layer 440 to increase the efficiency of current generated in each light emitting layer and smoothly distribute charges.
제1 발광층(340)에는 청색 호스트에 청색 형광 도펀트를 포함하는 발광 재료가 포함될 수 있고, 제2 발광층(440)에는 녹색 호스트에 그리니쉬 옐로우(greenish yellow) 도펀트와 적색 도펀트가 함께 도핑된 재료가 포함될 수 있으나, 이에 한정되는 것은 아니다. The first light-emitting layer 340 may include a light-emitting material including a blue fluorescent dopant in a blue host, and the second light-emitting layer 440 includes a material in which a green host is doped with a greenish yellow dopant and a red dopant. may be included, but is not limited thereto.
도 3에서, n은 1~5의 정수일 수 있는데, n이 2인 경우, 제2 스택(ST2) 상에 전하 생성층(CGL)과 제3 스택이 추가적으로 더 적층될 수 있다.In FIG. 3 , n may be an integer of 1 to 5. When n is 2, the charge generation layer CGL and the third stack may be additionally stacked on the second stack ST2 .
도 3과 같이 다층의 스택 구조 방식에 의해 발광층이 복수개 형성될 경우, 각각의 발광층에서 발광된 광의 혼합 효과에 의해 백색 광이 발광되는 유기전기발광소자를 제조할 수 있을 뿐만 아니라 다양한 색상의 광을 발광하는 유기전기발광소자를 제조할 수도 있다.When a plurality of light emitting layers are formed by the multilayer stack structure method as shown in FIG. 3 , an organic electroluminescent device that emits white light by the mixing effect of light emitted from each light emitting layer can be manufactured as well as light of various colors. It is also possible to manufacture an organic electroluminescent device that emits light.
본 발명의 일 실시예에 따르면, 본 발명의 화학식 1로 표시되는 화합물을 광효율 개선층(180)의 재료로 사용함으로써, 유기전기소자의 수명을 향상시키면서도 발광효율과 색순도를 현저히 향상시킬 수 있다.According to an embodiment of the present invention, by using the compound represented by Formula 1 of the present invention as a material for the light efficiency improving layer 180, it is possible to significantly improve the luminous efficiency and color purity while improving the lifespan of the organic electric device.
본 발명의 일 실시예에 따른 유기전기발광소자는 다양한 증착법(deposition)을 이용하여 제조될 수 있을 것이다. PVD나 CVD 등의 증착 방법을 사용하여 제조될 수 있는데, 예컨대, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극(110)을 형성하고, 그 위에 정공주입층(120), 정공수송층(130), 발광층(140), 전자수송층(150) 및 전자주입층(160)을 포함하는 유기물층을 형성한 후, 유기물층 상에 음극(170)으로 사용할 수 있는 물질을 증착시키고, 이후 음극(170) 상에 광효율 개선층(180)을 형성함으로써 제조될 수 있다. The organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD, for example, by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form the anode 110, and the hole injection layer 120 thereon , after forming an organic material layer including the hole transport layer 130 , the light emitting layer 140 , the electron transport layer 150 and the electron injection layer 160 , a material that can be used as the cathode 170 is deposited on the organic material layer, and then It may be manufactured by forming the light efficiency improving layer 180 on the cathode 170 .
또한, 정공수송층(130)과 발광층(140) 사이에 발광보조층(220)을, 발광층(140)과 전자수송층(150) 사이에 전자수송보조층(미도시)을 더 형성할 수도 있고 상술한 바와 같이 스택 구조로 형성할 수도 있다.In addition, an auxiliary light emitting layer 220 may be formed between the hole transport layer 130 and the light emitting layer 140 , and an electron transport auxiliary layer (not shown) may be further formed between the light emitting layer 140 and the electron transport layer 150 . It can also be formed in a stack structure as shown.
또한, 유기물층은 다양한 고분자 소재를 사용하여 증착법이 아닌 용액 공정 또는 솔벤트 프로세스(solvent process), 예컨대 스핀코팅 공정, 노즐 프린팅 공정, 잉크젯 프린팅 공정, 슬롯코팅 공정, 딥코팅 공정, 롤투롤 공정, 닥터 블레이딩 공정, 스크린 프린팅 공정, 또는 열 전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다. 본 발명에 따른 유기물층은 다양한 방법으로 형성될 수 있으므로, 그 형성방법에 의해 본 발명의 권리범위가 제한되는 것은 아니다.In addition, the organic layer is a solution process or a solvent process rather than a deposition method using various polymer materials, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, Dr. Blay It can be manufactured with a smaller number of layers by a method such as a printing process, a screen printing process, or a thermal transfer method. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the formation method.
본 발명의 일 실시예에 따른 유기전기소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic electric device according to an embodiment of the present invention may be a top emission type, a back emission type, or a double-sided emission type depending on the material used.
또한, 본 발명의 일 실시예에 따른 유기전기소자는 유기전기발광소자, 유기태양전지, 유기감광체, 유기트랜지스터, 단색 조명용 소자 및 퀀텀닷 디스플레이용 소자로 이루어진 군에서 선택될 수 있다.In addition, the organic electric device according to an embodiment of the present invention may be selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a device for monochromatic lighting, and a device for a quantum dot display.
본 발명의 다른 실시예는 상술한 본 발명의 유기전기소자를 포함하는 디스플레이장치와, 이 디스플레이장치를 제어하는 제어부를 포함하는 전자장치를 포함할 수 있다. 이때, 전자장치는 현재 또는 장래의 유무선 통신단말일 수 있으며, 휴대폰 등의 이동 통신 단말기, PDA, 전자사전, PMP, 리모콘, 네비게이션, 게임기, 각종 TV, 각종 컴퓨터 등 모든 전자장치를 포함한다.Another embodiment of the present invention may include a display device including the organic electric device of the present invention described above, and an electronic device including a control unit for controlling the display device. In this case, the electronic device may be a current or future wired/wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote control, a navigation system, a game machine, various TVs, and various computers.
이하, 본 발명의 일 측면에 따른 유기전기소자에 대하여 설명한다.Hereinafter, an organic electric device according to an aspect of the present invention will be described.
본 발명의 일 측면에 따른 유기전기소자는 제 1전극; 제 2전극; 상기 제 1전극과 상기 제 2전극 사이에 형성된 1층 이상의 유기물층; 및 상기 제 1전극의 양면 중에서 상기 유기물층과 접하지 않는 일면 또는 상기 제 2전극의 양면 중에서 상기 유기물층과 접하지 않는 일면에 형성된 광효율 개선층을 포함하며, 상기 광효율 개선층은 하기 화학식 1로 표시되는 화합물을 포함한다.An organic electric device according to an aspect of the present invention includes a first electrode; a second electrode; at least one organic material layer formed between the first electrode and the second electrode; and a light efficiency improving layer formed on one surface of both surfaces of the first electrode not in contact with the organic material layer or on one surface of both surfaces of the second electrode not in contact with the organic material layer, wherein the light efficiency improving layer is represented by the following formula (1) compounds.
<화학식 1><Formula 1>
<화학식 1-1><Formula 1-1>
상기 화학식 1에서, 각 기호는 아래와 같이 정의될 수 있다.In Formula 1, each symbol may be defined as follows.
X 및 Z는 서로 독립적으로 O 또는 S이고, Y는 N(R), C(R')(R"), O 또는 S이다.X and Z independently of one another are O or S, and Y is N(R), C(R')(R"), O or S.
Ar1 내지 Ar4는 서로 독립적으로 C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; -L'-N(Ra)(Rb); 및 화학식 1-1로 이루어진 군에서 선택되며, Ar1 내지 Ar4 중에서 적어도 하나는 화학식 1-1로 표시된다.Ar 1 To Ar 4 Are each independently a C 6 ~ C 60 Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; C 3 ~ C 60 aliphatic group; -L'-N(R a )(R b ); and Formula 1-1, and at least one of Ar 1 to Ar 4 is represented by Formula 1-1.
L1 내지 L7은 서로 독립적으로 단일결합; C6~C60의 아릴렌기; 플루오렌일렌기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 C3~C60의 지방족고리기로 이루어진 군에서 선택된다.L 1 To L 7 Are each independently a single bond; C 6 ~ C 60 Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; And C 3 ~ C 60 It is selected from the group consisting of an aliphatic cyclic group.
R1 내지 R3은 서로 독립적으로 수소; 중수소; 할로겐; 시아노기; 니트로기; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; C1~C30의 알킬기; C2~C30의 알켄일기; C2~C30의 알킨일기; C1~C30의 알콕실기; C6~C30의 아릴옥시기; 및 -L'-N(Ra)(Rb)로 이루어진 군에서 선택되고, 이웃한 기끼리 서로 결합하여 고리를 형성할 수 있다.R 1 to R 3 are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; C 6 ~ C 60 Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; C 3 ~ C 60 aliphatic group; C 1 ~ C 30 Alkyl group; C 2 ~ C 30 Alkenyl group; C 2 ~ C 30 Alkynyl group; C 1 ~ C 30 An alkoxyl group; C 6 ~ C 30 Aryloxy group; and -L′-N(R a )(R b ), and adjacent groups may be bonded to each other to form a ring.
n 및 p는 각각 0~4의 정수이고, m은 0~2의 정수이며, 이들 각각이 2 이상의 정수인 경우 R1 각각, R2 각각, R3 각각은 서로 같거나 상이하다.n and p are each an integer of 0-4, m is an integer of 0-2, and when each of these is an integer of 2 or more, each of R 1 , each of R 2 , and each of R 3 are the same as or different from each other.
o는 0~2의 정수이고, o가 2인 경우 L1 각각, L2 각각, L3 각각, Ar1 각각, Ar2 각각은 서로 같거나 상이하다.o is an integer of 0 to 2, and when o is 2, each of L 1 , each of L 2 , each of L 3 , each of Ar 1 , and each of Ar 2 are the same as or different from each other.
상기 L'는 단일결합; C6~C60의 아릴렌기; 플루오렌일렌기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 C3~C60의 지방족고리기로 이루어진 군에서 선택된다.The L' is a single bond; C 6 ~ C 60 Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; And C 3 ~ C 60 It is selected from the group consisting of an aliphatic cyclic group.
상기 R, Ra 및 Rb는 서로 독립적으로 C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 C3~C60의 지방족고리기로 이루어진 군에서 선택된다.The R, R a and R b are each independently a C 6 ~ C 60 aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; And C 3 ~ C 60 It is selected from the group consisting of an aliphatic cyclic group.
상기 R' 및 R"은 서로 독립적으로 수소; 중수소; 할로겐; 시아노기; 니트로기; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; C1~C30의 알킬기; C2~C30의 알켄일기; C2~C30의 알킨일기; C1~C30의 알콕실기; 및 C6~C30의 아릴옥시기로 이루어진 군에서 선택되고, R'과 R"는 서로 결합하여 고리를 형성할 수 있다. R'과 R"가 서로 결합하여 고리를 형성할 경우 스파이로 화합물이 형성될 수 있다.Wherein R' and R" are each independently hydrogen; deuterium; halogen; cyano group; nitro group; C 6 ~ C 60 aryl group; fluorenyl group; O, N, S, at least one heteroatom of S, Si and P Containing C 2 ~ C 60 Heterocyclic group; C 3 ~ C 60 Aliphatic ring group; C 1 ~ C 30 Alkyl group; C 2 ~ C 30 Alkenyl group; C 2 ~ C 30 Alkynyl group; C 1 ~ C 30 An alkoxyl group; And C 6 ~ C 30 It is selected from the group consisting of an aryloxy group, R' and R" may be bonded to each other to form a ring. When R' and R" combine with each other to form a ring, a spiro compound may be formed.
상기 Ar1~Ar4, R1~R3, R, Ra, Rb, R', R" 중에서 적어도 하나가 아릴기인 경우, 상기 아릴기는 예컨대, C6~C30, C6~C25, C6~C20, C6~C18, C6~C16, C6~C14, C6~C12, C6~C10, C6, C10, C12, C13, C14, C16, C18 등의 아릴기일 수 있고, 구체적으로, 페닐, 바이페닐, 나프틸, 터페닐, 페난트렌 등일 수 있다.When at least one of Ar 1 to Ar 4 , R 1 to R 3 , R, R a , R b , R′, and R" is an aryl group, the aryl group is, for example, C 6 to C 30 , C 6 to C 25 , C 6 ~C 20 , C 6 ~C 18 , C 6 ~C 16 , C 6 ~C 14 , C 6 ~C 12 , C 6 ~C 10 , C 6 , C 10 , C 12 , C 13 , C 14 , C 16 , may be an aryl group such as C 18 , and specifically, phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, and the like.
상기 L1~L7, L' 중에서 적어도 하나가 아릴렌기인 경우, 상기 아릴렌기는 예컨대, C6~C30, C6~C25, C6~C20, C6~C18, C6~C16, C6~C14, C6~C12, C6~C10, C6, C10, C12, C13, C14, C16, C18 등의 아릴렌기일 수 있고, 구체적으로, 페닐렌, 바이페닐, 나프틸렌, 터페닐 등일 수 있다.When at least one of L 1 to L 7 and L' is an arylene group, the arylene group is, for example, C 6 to C 30 , C 6 to C 25 , C 6 to C 20 , C 6 to C 18 , C 6 ~C 16 , C 6 ~C 14 , C 6 ~ C 12 , C 6 ~C 10 , C 6 , C 10 , C 12 , C 13 , C 14 , C 16 , C 18 may be an arylene group, Specifically, it may be phenylene, biphenyl, naphthylene, terphenyl, and the like.
상기 Ar1~Ar4, R1~R3, R, Ra, Rb, R', R", L1~L7, L' 중에서 적어도 하나가 헤테로고리기인 경우, 상기 헤테로고리기는 예컨대, C2~C30, C2~C24, C2~C20, C2~C18, C2~C16, C2~C12, C2~C8, C3, C4, C5, C7, C8, C12, C13, C16, C18 등의 헤테로고리기일 수 있고, 구체적으로, 피리딘, 피리미딘, 피라진, 피리다진, 트리아진, 퓨란, 피롤, 실롤, 인덴, 인돌, 페닐-인돌, 벤조인돌, 페닐-벤조인돌, 피라지노인돌, 퀴놀린, 아이소퀴놀린, 벤조퀴놀린, 피리도퀴놀린, 퀴나졸린, 벤조퀴나졸린, 다이벤조퀴나졸린, 페난트로퀴나졸린, 퀴녹살린, 벤조퀴녹살린, 다이벤조퀴녹살린, 벤조퓨란, 나프토벤조퓨란, 다이벤조퓨란, 페난트로벤조퓨란, 다이나프토퓨란, 싸이오펜, 벤조싸이오펜, 다이벤조싸이오펜, 나프토벤조싸이이오펜, 페난트로벤조싸이오펜, 다이나프토싸이오펜, 카바졸, 페닐-카바졸, 벤조카바졸, 페닐-벤조카바졸, 나프틸-벤조카바졸, 다이벤조카바졸, 인돌로카바졸, 벤조퓨로피리딘, 벤조싸이에노피리딘, 벤조퓨로피리딘, 벤조싸이에노피리미딘, 벤조퓨로피리미딘, 벤조싸이에노피라진, 벤조퓨로피라진, 벤조이미다졸, 벤조티아졸, 벤조옥사졸, 벤조실롤, 페난트롤린, 다이하이드로-페닐페나진, 10-페닐-10H-페녹사진, 페녹사진, 페노싸이아진, 다이벤조다이옥신, 벤조다이벤조다이옥신, 싸이안트렌, 9,9-다이메틸-9H-잔쓰렌, 9,9-다이메틸-9H-싸이옥잔쓰렌, 다이하이드로다이메틸페닐아크리딘, 스파이로[플루오렌-9,9'-잔텐] 등일 수 있다.When at least one of Ar 1 to Ar 4 , R 1 to R 3 , R, R a , R b , R′, R″, L 1 to L 7 , and L′ is a heterocyclic group, the heterocyclic group is, for example, C 2 ~C 30 , C 2 ~C 24 , C 2 ~C 20 , C 2 ~C 18 , C 2 ~C 16 , C 2 ~C 12 , C 2 ~C 8 , C 3 , C 4 , C 5 , C 7 , C 8 , C 12 , C 13 , C 16 , may be a heterocyclic group such as C 18 , and specifically, pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, pyrrole, silol, indene, Indole, phenyl-indole, benzoindole, phenyl-benzoindole, pyrazinoindole, quinoline, isoquinoline, benzoquinoline, pyridoquinoline, quinazoline, benzoquinazoline, dibenzoquinazoline, phenanthroquinazoline, quinoxaline, Benzoquinoxaline, dibenzoquinoxaline, benzofuran, naphthobenzofuran, dibenzofuran, phenanthrobenzofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthobenzothiophene, phenanthro Benzothiophene, dinaphthothiophene, carbazole, phenyl-carbazole, benzocarbazole, phenyl-benzocarbazole, naphthyl-benzocarbazole, dibenzocarbazole, indolocarbazole, benzofuropyridine, benzo thienopyridine, benzofuropyridine, benzothienopyrimidine, benzofuropyrimidine, benzothienopyrazine, benzofuropyrazine, benzoimidazole, benzothiazole, benzoxazole, benzosilol, phenan Troline, dihydro-phenylphenazine, 10-phenyl-10H-phenoxazine, phenoxazine, phenothiazine, dibenzodioxin, benzodibenzodioxin, cyanthrene, 9,9-dimethyl-9H-xanthrene , 9,9-dimethyl-9H-thioxanthrene, dihydrodimethylphenylacridine, spiro[fluorene-9,9'-xanthene], and the like.
상기 R1~R3, R', R" 중에서 적어도 하나가 알킬기인 경우, 상기 알킬기는 예컨대 C1~C20, C1~C10, C1~C4, C1, C2, C3, C4 등의 알킬기일 수 있고, 구체적으로 메틸, 에틸, 프로필, t-부틸 등일 수 있다.When at least one of R 1 to R 3 , R', and R" is an alkyl group, the alkyl group is, for example, C 1 to C 20 , C 1 to C 10 , C 1 to C 4 , C 1 , C 2 , C 3 , may be an alkyl group such as C 4 , specifically methyl, ethyl, propyl, t-butyl, and the like.
상기 아릴기, 아릴렌기, 플루오렌일기, 플루오렌일렌기, 헤테로고리기, 지방족 고리기, 알킬기, 알켄일기, 알킨일기, 알콕실기, 아릴옥시기, 이웃한 기끼리 서로 결합하여 형성된 고리, 및 R'과 R"이 서로 결합하여 형성된 고리는 각각 중수소; 할로겐; C1-C20의 알킬기 또는 C6-C20의 아릴기로 치환 또는 비치환된 실란기; C1-C20의 알킬기 또는 C6-C20의 아릴기로 치환 또는 비치환된 포스핀옥사이드; 실록산기; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕실기; C6-C20의 아릴옥시기; C6-C20의 아릴싸이오기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C20의 헤테로고리기; 및 C3-C20의 지방족고리기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있다.The aryl group, an arylene group, a fluorenyl group, a fluorenylene group, a heterocyclic group, an aliphatic ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyl group, an aryloxy group, a ring formed by bonding adjacent groups to each other, and A ring formed by combining R′ and R″ is deuterium; halogen; a silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or C 6 -C 20 aryl group; C 1 -C 20 alkyl group or C 6 -C 20 Phosphine oxide unsubstituted or substituted with an aryl group; Siloxane group; Cyano group; Nitro group; C 1 -C 20 Alkylthio group; C 1 -C 20 Alkoxy group; C 6 -C 20 Aryloxy group; C 6 -C 20 Arylthio group; C 1 -C 20 Alkyl group; C 2 -C 20 Alkenyl group; C 2 -C 20 Alkynyl group; C 6 -C 20 Aryl group; Flu Orenyl group; C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C 3 -C 20 One selected from the group consisting of an aliphatic ring group It may be substituted with more than one substituent.
상기 아릴기, 플루오렌일기, 헤테로고리기, 지방족고리기, 알킬기, 알켄일기, 알킨일기, 알콕시기, 아릴옥시기, 아릴렌기, 플루오렌일렌기, 및 이웃한 기끼리 서로 결합하여 형성된 고리 중에서 적어도 하나가 아릴기로 치환될 경우, 상기 아릴기는 예컨대 C6~C20, C6~C18, C6~C16, C6~C14, C6~C12, C6~C10, C6, C10, C12, C13, C14, C16, C18 등의 아릴기일 수 있다.Among the rings formed by bonding the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups to each other When at least one is substituted with an aryl group, the aryl group is, for example, C 6 -C 20 , C 6 -C 18 , C 6 -C 16 , C 6 -C 14 , C 6 -C 12 , C 6 -C 10 , C It may be an aryl group such as 6 , C 10 , C 12 , C 13 , C 14 , C 16 , C 18 .
상기 아릴기, 플루오렌일기, 헤테로고리기, 지방족고리기, 알킬기, 알켄일기, 알킨일기, 알콕시기, 아릴옥시기, 아릴렌기, 플루오렌일렌기, 및 이웃한 기끼리 서로 결합하여 형성된 고리 중에서 적어도 하나가 헤테로고리기로 치환될 경우, 상기 헤테로고리기는 예컨대 C2~C20, C2~C18, C2~C16, C2~C12, C2~C8, C3, C4, C5, C7, C8, C12, C13, C16, C18 등의 헤테로고리기일 수 있다.Among the rings formed by bonding the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups to each other When at least one is substituted with a heterocyclic group, the heterocyclic group is, for example, C 2 ~ C 20 , C 2 ~ C 18 , C 2 ~ C 16 , C 2 ~ C 12 , C 2 ~ C 8 , C 3 , C 4 , C 5 , C 7 , C 8 , C 12 , C 13 , C 16 , C 18 may be a heterocyclic group.
상기 아릴기, 플루오렌일기, 헤테로고리기, 지방족고리기, 알킬기, 알켄일기, 알킨일기, 알콕시기, 아릴옥시기, 아릴렌기, 플루오렌일렌기, 및 이웃한 기끼리 서로 결합하여 형성된 고리 중에서 적어도 하나가 알킬기로 치환될 경우, 상기 알킬기는 예컨대 C1~C20, C1~C10, C1~C4, C1, C2, C3, C4 등의 알킬기일 수 있다.Among the rings formed by bonding the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups to each other When at least one is substituted with an alkyl group, the alkyl group may be, for example, an alkyl group such as C 1 to C 20 , C 1 to C 10 , C 1 to C 4 , C 1 , C 2 , C 3 , C 4 .
상기 화학식 1은 하기 화학식 2 또는 화학식 3으로 표시될 수 있다.Formula 1 may be represented by Formula 2 or Formula 3 below.
<화학식 2> <화학식 3><Formula 2> <Formula 3>
상기 화학식 2 및 3에서, X, Y, Ar1~Ar4, L1~L6, R1, R2, m, n은 상기 화학식 1에서 정의된 것과 같다.In Formulas 2 and 3, X, Y, Ar 1 to Ar 4 , L 1 to L 6 , R 1 , R 2 , m, and n are the same as defined in Formula 1 above.
상기 화학식 1은 하기 화학식 4 내지 화학식 7 중에서 하나로 표시될 수 있다.Formula 1 may be represented by one of Formulas 4 to 7 below.
<화학식 4> <화학식 5><Formula 4> <Formula 5>
<화학식 6> <화학식 7><Formula 6> <Formula 7>
상기 화학식 4 내지 7에서, X, Ar1~Ar4, L1~L6, R1, R2, R, R', R", m, n, o는 화학식 1에서 정의된 것과 같다.In Formulas 4 to 7, X, Ar 1 to Ar 4 , L 1 to L 6 , R 1 , R 2 , R, R′, R″, m, n, o are the same as defined in Formula 1.
상기 화학식 1-1은 하기 화학식 1-1A로 표시될 수 있다.The Chemical Formula 1-1 may be represented by the following Chemical Formula 1-1A.
<화학식 1-1A><Formula 1-1A>
상기 화학식 1-1A에서, Z, L7, R3, p는 화학식 1에서 정의된 것과 같다.In Formula 1-1A, Z, L 7 , R 3 , and p are the same as defined in Formula 1.
구체적으로, 상기 화학식 1로 표시되는 화합물은 하기 화합물 중에서 하나일 수 있으나, 이에 한정되는 것은 아니다.Specifically, the compound represented by Formula 1 may be one of the following compounds, but is not limited thereto.
이하, 본 발명에 따른 화학식 1로 표시되는 화합물의 합성예 및 유기전기소자의 제조예에 관하여 실시예를 들어 구체적으로 설명하지만, 본 발명이 하기의 실시예로 한정되는 것은 아니다.Hereinafter, a synthesis example of the compound represented by Formula 1 according to the present invention and a manufacturing example of an organic electric device will be described in detail with reference to examples, but the present invention is not limited to the following examples.
합성예Synthesis example
본 발명에 따른 화학식 1로 표시되는 화합물(Final product)은 하기 반응식 1과 같이 Core 1과 Sub1를 반응시켜 제조될 수 있으나, 이에 한정된 것은 아니다.The compound represented by Formula 1 according to the present invention (final product) may be prepared by reacting Core 1 and Sub1 as shown in Scheme 1 below, but is not limited thereto.
<반응식 1> <Scheme 1>
(Hal1 및 Hal2는 각각 I, Br 또는 Cl이고, L'는 L2 또는 L5, L"는 L3 또는 L6, Ar'는 Ar1 또는 Ar3, Ar"는 Ar2 또는 Ar4임)(Hal 1 and Hal 2 are each I, Br or Cl, L′ is L 2 or L 5 , L″ is L 3 or L 6 , Ar′ is Ar 1 or Ar 3 , Ar″ is Ar 2 or Ar 4 Lim)
I. Core1의 합성예I. Synthesis example of Core1
상기 반응식 1의 Core 1은 하기 반응식 2 내지 5의 반응경로에 의해 합성될 수 있으나, 이에 한정된 것은 아니다. Hal3은 할로겐이다.Core 1 of Scheme 1 may be synthesized by the reaction routes of Schemes 2 to 5, but is not limited thereto. Hal 3 is halogen.
<반응식 2> (Y=S인 경우)<Scheme 2> (when Y=S)
<반응식 3> (Y=O인 경우)<Scheme 3> (When Y=O)
<반응식 4> (Y=NR인 경우)<Scheme 4> (when Y=NR)
<반응식 5> (Y=C(R')(R")인 경우)<Scheme 5> (When Y=C(R')(R"))
(R6은 R', R"임)(R 6 is R', R")
(1) Core1-1의 합성예(1) Synthesis example of Core1-1
Core1-1b의 합성Synthesis of Core1-1b
5-bromo-2-(4-chlorophenyl)benzo[d]oxazole(20 g, 65.82 mmol)을 THF (216 mL)로 녹인 후에, (2-nitrophenyl)boronic acid (10.82g, 64.82mmol), Pd(PPh3)4 (1.50 g, 1.30 mmol), K2CO3 (17.91 g, 129.63 mmol), 물 (44 mL)을 첨가하고 80℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 17.28 g (수율: 76%)를 얻었다.After dissolving 5-bromo-2-(4-chlorophenyl)benzo[d]oxazole (20 g, 65.82 mmol) in THF (216 mL), (2-nitrophenyl)boronic acid (10.82 g, 64.82 mmol), Pd ( PPh 3 ) 4 (1.50 g, 1.30 mmol), K 2 CO 3 (17.91 g, 129.63 mmol), water (44 mL) were added and stirred at 80° C. Upon completion of the reaction , the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 17.28 g of a product (yield: 76%).
Core1-1a의 합성Synthesis of Core1-1a
Core1-1b (17.28 g, 49.26 mmol)에 triphenylphosphine (38.76 g, 147.79 mmol)을 첨가하고 220℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 12.56 g (수율: 80%)를 얻었다.To Core1-1b (17.28 g, 49.26 mmol) was added triphenylphosphine (38.76 g, 147.79 mmol) and stirred at 220°C. Upon completion of the reaction , the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 12.56 g (yield: 80%) of the product.
Core1-1의 합성Synthesis of Core1-1
Core1-1a(12.56 g, 39.40 mmol)를 DCB(56 mL)로 녹인 후에, iodobenzene (8.84 g, 43.34 mmol), copper(0.25 g, 3.94 mmol), K2CO3 (16.34 g, 118.21 mmol), 18-crown-6 (20.83 g, 78.81 mmol)을 넣고 150℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 11.36g (수율: 73%)를 얻었다.After dissolving Core1-1a (12.56 g, 39.40 mmol) in DCB (56 mL), iodobenzene (8.84 g, 43.34 mmol), copper (0.25 g, 3.94 mmol), K 2 CO 3 (16.34 g, 118.21 mmol), 18-crown-6 (20.83 g, 78.81 mmol) was added and stirred at 150°C. Upon completion of the reaction , the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 11.36 g of a product (yield: 73%).
(2) Core1-19의 합성예(2) Synthesis example of Core1-19
Core1-19a의 합성Synthesis of Core1-19a
5-bromo-2-(4-chlorophenyl)benzo[d]thiazole (20 g, 61.61 mmol)을 DMF (88 mL)로 녹인 후에, 2-chlorophenol (7.92g, 61.61mmol), copper(0.39 g, 6.16 mmol), K2CO3 (25.54 g, 184.83 mmol), 18-crown-6 (32.57 g, 123.22 mmol)을 넣고 환류시켰다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 17.43 g (수율: 76%)를 얻었다.After dissolving 5-bromo-2-(4-chlorophenyl)benzo[d]thiazole (20 g, 61.61 mmol) in DMF (88 mL), 2-chlorophenol (7.92g, 61.61mmol), copper (0.39 g, 6.16) mmol), K 2 CO 3 (25.54 g, 184.83 mmol), and 18-crown-6 (32.57 g, 123.22 mmol) were added and refluxed. Upon completion of the reaction , the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 17.43 g of a product (yield: 76%).
Core1-19의 합성Synthesis of Core1-19
Core1-19a (17.43 g, 46.82 mmol)를 AcOH (156 mL)로 녹인 후에, Pd(OAc)2 (0.21 g, 0.94 mmol), K2CO3 (19.41 g, 140.47 mmol)을 넣고 환류시켰다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 10.22 g (수율: 65%)를 얻었다.After Core1-19a (17.43 g, 46.82 mmol) was dissolved in AcOH (156 mL), Pd(OAc) 2 (0.21 g, 0.94 mmol), K 2 CO 3 (19.41 g, 140.47 mmol) was added and refluxed. Upon completion of the reaction , the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 10.22 g (yield: 65%) of the product.
(3) Core1-24의 합성예(3) Synthesis example of Core1-24
Core1-24a의 합성Synthesis of Core1-24a
7-bromo-2-(4-chlorophenyl)-4-phenylbenzo[d]thiazole(20 g, 49.91 mmol)을 둥근바닥플라스크에 DMF(71 mL)로 녹인 후에, 3-chlorophenol (7.06g, 54.90mmol), copper(0.32 g, 4.99 mmol), K2CO3 (20.69 g, 149.73 mmol), 18-crown-6 (26.38 g, 149.32 mmol)을 넣고 환류시켰다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 14.05 g (수율: 68%)를 얻었다.After dissolving 7-bromo-2-(4-chlorophenyl)-4-phenylbenzo[d]thiazole (20 g, 49.91 mmol) in DMF (71 mL) in a round-bottom flask, 3-chlorophenol (7.06 g, 54.90 mmol) , copper (0.32 g, 4.99 mmol), K 2 CO 3 (20.69 g, 149.73 mmol), 18-crown-6 (26.38 g, 149.32 mmol) was put and refluxed. Upon completion of the reaction , the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 14.05 g of a product (yield: 68%).
Core1-24의 합성Synthesis of Core1-24
Core1-24a (14.05 g, 46.82 mmol)를 둥근바닥플라스크에 AcOH (160 mL)로 녹인 후에, Pd(OAc)2 (0.15g, 0.68mmol), K2CO3 (14.07 g, 101.83 mmol)을 넣고 환류시켰다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 8.81 g (수율: 63%)를 얻었다.After Core1-24a (14.05 g, 46.82 mmol) was dissolved in AcOH (160 mL) in a round-bottom flask, Pd(OAc) 2 (0.15 g, 0.68 mmol), K 2 CO 3 (14.07 g, 101.83 mmol) was added. refluxed. Upon completion of the reaction , the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 8.81 g (yield: 63%) of the product.
(4) Core 1-43의 합성예(4) Synthesis example of Core 1-43
Core 1-43b의 합성Synthesis of Core 1-43b
2-(4-bromophenyl)-6-iodobenzo[d]oxazole (20 g, 50.00 mmol)을 THF(167mL)로 녹인 후에 (2-chloro-6-(methylthio)phenyl)boronic acid(7.09 g, 35.00 mmol), Pd(PPh3)4 (1.16 g, 1.00 mmol), K2CO3 (13.82 g, 99.99 mmol) 넣고 85℃에서 교반하였다. 반응이 완료되면 용매를 제거한 뒤 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 16.80 g (수율: 78%)를 얻었다.After dissolving 2-(4-bromophenyl)-6-iodobenzo[d]oxazole (20 g, 50.00 mmol) in THF (167 mL), (2-chloro-6-(methylthio)phenyl)boronic acid (7.09 g, 35.00 mmol) ), Pd(PPh 3 ) 4 (1.16 g, 1.00 mmol), K 2 CO 3 (13.82 g, 99.99 mmol) were added and stirred at 85°C. When the reaction was completed, the solvent was removed, extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 16.80 g (yield: 78%) of the product.
Core 1-43a의 합성Synthesis of Core 1-43a
Core1-43b (16.80 g, 39.00 mmol)에 AcOH (130 mL), H2O2 (1.46 g, 42.90 mmol)을 넣고 실온에서 교반하였다. 반응이 완료되면 용매를 제거한 뒤, 1M NaOH로 중화한 다음 Ethyl acetate와 물로 추출하였다. 이후, 유기층을 MgSO4로 건조하고 농축한 후 재결정하여 생성물 13.24g (수율: 76%)를 얻었다. AcOH (130 mL), H 2 O 2 (1.46 g, 42.90 mmol) was added to Core1-43b (16.80 g, 39.00 mmol) and stirred at room temperature. After the reaction was completed, the solvent was removed, neutralized with 1M NaOH, and extracted with ethyl acetate and water. Then, the organic layer was dried over MgSO 4 , concentrated and recrystallized to obtain 13.24 g of a product (yield: 76%).
Core 1-43의 합성Synthesis of Core 1-43
Core1-43a(13.24 g, 29.64 mmol)를 H2SO4(99 ml)에 넣고 65℃에서 교반하였다. 반응이 완료되면 NaOH 수용액을 사용하여 중화한 후 CH2Cl2와 물로 추출하였다. 이후 유기층을 MgSO4로 건조하고 농축하고, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 8.97 g (수율: 73%)를 얻었다.Core1-43a (13.24 g, 29.64 mmol) was placed in H 2 SO 4 (99 ml) and stirred at 65°C. When the reaction was completed, the mixture was neutralized using an aqueous NaOH solution, followed by extraction with CH 2 Cl 2 and water. Thereafter, the organic layer was dried over MgSO 4 and concentrated, and the concentrate was separated by a silica gel column and recrystallized to obtain 8.97 g (yield: 73%) of the product.
(5) Core1-58의 합성예(5) Synthesis example of Core1-58
Core1-58b의 합성Synthesis of Core1-58b
2-chlorobenzo[d]thiazol-6-yl)boronic acid (20 g, 93.70 mmole)을 THF(312mL)로 녹인 후에 1-bromo-2-(iodomethyl)benzene (27.82 g, 93.70 mmol), Pd(PPh3)4 (2.17 g, 1.87 mmol), K2CO3 (25.90g, 187.41 mmol) 넣고 85℃에서 교반하였다. 반응이 완료되면 용매를 제거한 뒤 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후 농축물을 실리카겔 칼럼으로 분리하여 생성물 26.34 g (수율: 83%)를 얻었다.After dissolving 2-chlorobenzo[d]thiazol-6-yl)boronic acid (20 g, 93.70 mmole) in THF (312mL), 1-bromo-2-(iodomethyl)benzene (27.82 g, 93.70 mmol), Pd(PPh) 3 ) 4 (2.17 g, 1.87 mmol), K 2 CO 3 (25.90 g, 187.41 mmol) was added and stirred at 85 °C. When the reaction was completed, the solvent was removed, extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Then, the concentrate was separated by a silica gel column to obtain 26.34 g of a product (yield: 83%).
Core1-58a의 합성Synthesis of Core1-58a
Core1-58b (26.34 g, 77.77 mmol)를 THF(259 mL)로 녹인 후에 NH4Cl (8.32 g, 155.53 mmol), Caesium pivalate (1.09 g 4.67 mmol), Pd(OAc)2 (0.35 g, 1.56 mmol)을 넣고 90℃에서 교반하였다. 반응이 완료되면 용매를 제거한 뒤 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후 농축물을 실리카겔 칼럼으로 분리하여 생성물 14.23 g (수율: 71%)를 얻었다.After dissolving Core1-58b (26.34 g, 77.77 mmol) in THF (259 mL), NH 4 Cl (8.32 g, 155.53 mmol), Caesium pivalate (1.09 g 4.67 mmol), Pd(OAc) 2 (0.35 g, 1.56 mmol) ) and stirred at 90 °C. When the reaction was completed, the solvent was removed, extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Then, the concentrate was separated by a silica gel column to obtain 14.23 g of a product (yield: 71%).
Core1-58의 합성Synthesis of Core1-58
Core1-58a (12.39 g, 48.07 mmol)를 toluene(160 mL)으로 녹인 후에 MethylIodide (17.06 g, 120.18 mol), NaH2PO4(12.69 g, 119.98 mol), Potassium bis(trimethylsilyl)amide (31.65 g 158.64 mmol)을 넣고 130℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후 농축물을 실리카겔 칼럼으로 분리하여 생성물 8.52 g (수율: 62%)를 얻었다.After dissolving Core1-58a (12.39 g, 48.07 mmol) in toluene (160 mL), MethylIodide (17.06 g, 120.18 mol), NaH 2 PO 4 (12.69 g, 119.98 mol), Potassium bis(trimethylsilyl)amide (31.65 g 158.64) mmol) and stirred at 130 °C. Upon completion of the reaction , the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Then, the concentrate was separated by a silica gel column to obtain 8.52 g of a product (yield: 62%).
Core1에 속하는 화합물은 아래와 같은 화합물일 수 있으나, 이에 한정되는 것은 아니며, 표 1은 하기 화합물의 FD-MS(Field Desorption-Mass Spectrometry) 값을 나타낸 것이다.The compound belonging to Core1 may be a compound as follows, but is not limited thereto, and Table 1 shows FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.
[표 1][Table 1]
II. Sub 1의 합성II. Synthesis of Sub 1
상기 반응식 1의 Sub1은 하기 반응식 6의 반응경로에 의해 합성될 수 있으나, 이에 한정되는 것은 아니다.Sub1 of Scheme 1 may be synthesized by the reaction route of Scheme 6 below, but is not limited thereto.
<반응식 6><Scheme 6>
(1) Sub1-1 합성예(1) Sub1-1 synthesis example
4-(benzo[d]oxazol-2-yl)aniline (20 g, 95.13 mmol)에 2-(4-bromophenyl)benzo[d]oxazole (20.86 g, 76.10 mmol), Pd2(dba)3 (0.75 g, 0.82 mmol), 50% P(t-Bu)3 (0.75 g, 0.82 mmol), NaOt-Bu (7.87 g, 81.87 mmol), toluene (136 ml)을 첨가하고 80℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 23.73 g (수율: 62%)를 얻었다.4-(benzo[d]oxazol-2-yl)aniline (20 g, 95.13 mmol) to 2-(4-bromophenyl)benzo[d]oxazole (20.86 g, 76.10 mmol), Pd 2 (dba) 3 (0.75 g, 0.82 mmol), 50% P( t- Bu) 3 (0.75 g, 0.82 mmol), NaO t- Bu (7.87 g, 81.87 mmol), toluene (136 ml) were added and stirred at 80°C. Upon completion of the reaction , the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 23.73 g (yield: 62%) of the product.
(2) Sub1-2 합성예(2) Sub1-2 Synthesis Example
4-(benzo[d]oxazol-2-yl)aniline (20 g, 95.13 mmol)에 2-(4-bromophenyl)benzo[d]thiazole (22.08 g, 76.10 mmol), Pd2(dba)3 (0.75 g, 0.82 mmol), 50% P(t-Bu)3 (0.75 g, 0.82 mmol), NaOt-Bu (7.87 g, 81.87 mmol), toluene (136 ml)을 첨가하고 80℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 26.34 g (수율: 66%)를 얻었다.4-(benzo[d]oxazol-2-yl)aniline (20 g, 95.13 mmol) to 2-(4-bromophenyl)benzo[d]thiazole (22.08 g, 76.10 mmol), Pd 2 (dba) 3 (0.75) g, 0.82 mmol), 50% P( t- Bu) 3 (0.75 g, 0.82 mmol), NaO t- Bu (7.87 g, 81.87 mmol), toluene (136 ml) were added and stirred at 80°C. Upon completion of the reaction , the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 26.34 g (yield: 66%) of the product.
(3) Sub1-33 합성예(3) Sub1-33 synthesis example
4-(benzo[d]oxazol-2-yl)aniline (20 g, 95.13 mmol)에 2-bromobenzo[d]thiazole (16.29 g, 76.10 mmol), Pd2(dba)3 (0.75 g, 0.82 mmol), 50% P(t-Bu)3 (0.75 g, 0.82 mmol), NaOt-Bu (7.87 g, 81.87 mmol), toluene (136 ml)을 첨가하고 80℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 19.93 g (수율: 61%)를 얻었다.4-(benzo[d]oxazol-2-yl)aniline (20 g, 95.13 mmol) to 2-bromobenzo[d]thiazole (16.29 g, 76.10 mmol), Pd 2 (dba) 3 (0.75 g, 0.82 mmol) , 50% P( t -Bu) 3 (0.75 g, 0.82 mmol), NaO t -Bu (7.87 g, 81.87 mmol), toluene (136 ml) were added and stirred at 80°C. Upon completion of the reaction , the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 19.93 g (yield: 61%) of the product.
(4) Sub1-56 합성예(4) Sub1-56 synthesis example
4-(benzo[d]thiazol-2-yl)aniline (20 g, 88.38 mmol)에 2-(1-chlorodibenzo[b,d]furan-4-yl)benzo[d]oxazole (22.61 g, 70.70 mmol), Pd2(dba)3 (0.75 g, 0.82 mmol), 50% P(t-Bu)3 (0.75 g, 0.82 mmol), NaOt-Bu (7.87 g, 81.87 mmol), toluene (136 ml)을 첨가하고 130℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 26.12 g (수율: 58%)를 얻었다.4-(benzo[d]thiazol-2-yl)aniline (20 g, 88.38 mmol) to 2-(1-chlorodibenzo[b,d]furan-4-yl)benzo[d]oxazole (22.61 g, 70.70 mmol) ), Pd 2 (dba) 3 (0.75 g, 0.82 mmol), 50% P( t- Bu) 3 (0.75 g, 0.82 mmol), NaO t- Bu (7.87 g, 81.87 mmol), toluene (136 ml) was added and stirred at 130 °C. Upon completion of the reaction , the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 26.12 g (yield: 58%) of the product.
(5) Sub1-62 합성예(5) Sub1-62 synthesis example
4-(benzo[d]oxazol-2-yl)aniline (20 g, 95.13 mmol)에 2-(9-chlorodibenzo[b,d]thiophen-2-yl)benzo[d]thiazole (26.78 g, 76.10 mmol), Pd2(dba)3 (0.75 g, 0.82 mmol), 50% P(t-Bu)3 (0.75 g, 0.82 mmol), NaOt-Bu (7.87 g, 81.87 mmol), toluene (136 ml)을 첨가하고 130℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 30.00 g (수율: 60%)를 얻었다.4-(benzo[d]oxazol-2-yl)aniline (20 g, 95.13 mmol) to 2-(9-chlorodibenzo[b,d]thiophen-2-yl)benzo[d]thiazole (26.78 g, 76.10 mmol) ), Pd 2 (dba) 3 (0.75 g, 0.82 mmol), 50% P( t- Bu) 3 (0.75 g, 0.82 mmol), NaO t- Bu (7.87 g, 81.87 mmol), toluene (136 ml) was added and stirred at 130 °C. Upon completion of the reaction , the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 30.00 g of a product (yield: 60%).
Sub1에 속하는 화합물은 아래와 같은 화합물일 수 있으나, 이에 한정되는 것은 아니며, 표 2는 하기 화합물의 FD-MS(Field Desorption-Mass Spectrometry) 값을 나타낸 것이다.The compound belonging to Sub1 may be a compound as follows, but is not limited thereto, and Table 2 shows FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.
[표 2][Table 2]
III. 최종 화합물의 합성예III. Synthesis example of final compound
P-1 합성예P-1 Synthesis Example
Core1-1(20 g, 50.65 mmol)에 Sub1-1(20.43 g, 50.65 mmol), Pd2(dba)3 (0.75 g, 0.82 mmol), 50% P(t-Bu)3 (0.75 g, 0.82 mmol), NaOt-Bu (7.87 g, 81.87 mmol), toluene (169ml)을 첨가하고 130℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 22.90 g (수율: 86%)를 얻었다.Core1-1 (20 g, 50.65 mmol) to Sub1-1 (20.43 g, 50.65 mmol), Pd 2 (dba) 3 (0.75 g, 0.82 mmol), 50% P( t- Bu) 3 (0.75 g, 0.82) mmol), NaO t -Bu (7.87 g, 81.87 mmol), and toluene (169 ml) were added and stirred at 130°C. Upon completion of the reaction , the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 22.90 g (yield: 86%) of the product.
P-7 합성예P-7 Synthesis Example
Core1-8 (13 g, 38.71 mmol)에 Sub1-2 (16.24 g, 38.71 mmol), Pd2(dba)3 (0.71 g, 0.77 mol), P(t-Bu)3 (0.31 g, 1.55 mmol), NaOt-Bu (7.44 g, 77.42 mmol)을 첨가하고 상기 P-1의 합성법과 같은 방법으로 진행하여 생성물 23.63 g (수율 85%) 얻었다.Sub1-2 (16.24 g, 38.71 mmol), Pd 2 (dba) 3 (0.71 g, 0.77 mol), P(t-Bu) 3 (0.31 g, 1.55 mmol) in Core1-8 (13 g, 38.71 mmol) , NaOt-Bu (7.44 g, 77.42 mmol) was added, and the same method was followed for the synthesis of P-1 to obtain 23.63 g (yield 85%) of the product.
P-12 합성예P-12 Synthesis Example
Core1-12 (15 g, 35.22 mmol)에 Sub1-1 (14.21 g, 35.22 mmol), Pd2(dba)3 (0.65 g, 0.70 mol), P(t-Bu)3 (0.29 g, 1.41 mmol), NaOt-Bu (6.77 g, 70.44 mmol)을 첨가하고 상기 P-1의 합성법과 같은 방법으로 진행하여 생성물 20.66 g (수율 74%) 얻었다.Sub1-1 (14.21 g, 35.22 mmol), Pd 2 (dba) 3 (0.65 g, 0.70 mol), P(t-Bu) 3 (0.29 g, 1.41 mmol) in Core1-12 (15 g, 35.22 mmol) , NaOt-Bu (6.77 g, 70.44 mmol) was added, followed by the same method as in the synthesis of P-1 to obtain 20.66 g (yield 74%) of the product.
P-52 합성예P-52 Synthesis Example
Core1-29 (13 g, 31.56 mmol)에 Sub1-1 (12.73 g, 31.56 mmol), Pd2(dba)3 (0.58 g, 0.63 mol), P(t-Bu)3 (0.26 g, 1.26 mmol), NaOt-Bu (6.07 g, 63.12 mmol)을 첨가하고 상기 P-1의 합성법과 같은 방법으로 진행하여 생성물 16.72 g (수율 68%) 얻었다.Core1-29 (13 g, 31.56 mmol) to Sub1-1 (12.73 g, 31.56 mmol), Pd 2 (dba) 3 (0.58 g, 0.63 mol), P(t-Bu) 3 (0.26 g, 1.26 mmol) , NaOt-Bu (6.07 g, 63.12 mmol) was added, and the same method was followed for the synthesis of P-1 to obtain 16.72 g (yield 68%) of the product.
P-92 합성예P-92 Synthesis Example
(1) Inter-92의 합성예(1) Synthesis example of Inter-92
Core1-63(15 g, 29.02 mmol)에 Sub1-46(3.93 g, 23.22 mmol), Pd2(dba)3 (0.53 g, 0.58 mmol), 50% P(t-Bu)3 (0.23g, 1.16 mmol), NaOt-Bu (5.58 g, 58.04 mmol), toluene (97ml)을 첨가하고 65℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 13.70 g (수율: 78%)를 얻었다.Core1-63 (15 g, 29.02 mmol) in Sub1-46 (3.93 g, 23.22 mmol), Pd 2 (dba) 3 (0.53 g, 0.58 mmol), 50% P( t- Bu) 3 (0.23 g, 1.16) mmol), NaO t -Bu (5.58 g, 58.04 mmol) and toluene (97 ml) were added and stirred at 65°C. Upon completion of the reaction , the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 13.70 g of a product (yield: 78%).
(2) P-92의 합성예(2) Synthesis example of P-92
Inter-92(13.70 g, 22.64 mmol)에 Sub1-26(8.88 g, 22.64 mmol), Pd2(dba)3 (0.41 g, 0.45 mmol), 50% P(t-Bu)3 (0.18g, 0.91 mmol), NaOt-Bu (4.35 g, 45.27 mmol), toluene (75ml)을 첨가하고 130℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 18.28 g (수율: 84%)를 얻었다.Inter-92 (13.70 g, 22.64 mmol) in Sub1-26 (8.88 g, 22.64 mmol), Pd 2 (dba) 3 (0.41 g, 0.45 mmol), 50% P( t- Bu) 3 (0.18 g, 0.91) mmol), NaO t -Bu (4.35 g, 45.27 mmol) and toluene (75 ml) were added and stirred at 130°C. Upon completion of the reaction , the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 18.28 g (yield: 84%) of the product.
P-99 합성예P-99 Synthesis Example
(1) Inter-99의 합성예(1) Synthesis example of Inter-99
Core1-10(14 g, 35.12 mmol)에 Sub1-26(14.03 g, 24.58 mmol), Pd2(dba)3 (0.64 g, 0.70 mmol), 50% P(t-Bu)3 (0.28g, 1.40 mmol), NaOt-Bu (6.75 g, 70.24 mmol), toluene (117ml)을 첨가하고 65℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 19.34 g (수율: 62%)를 얻었다.Core1-10 (14 g, 35.12 mmol) in Sub1-26 (14.03 g, 24.58 mmol), Pd 2 (dba) 3 (0.64 g, 0.70 mmol), 50% P( t- Bu) 3 (0.28 g, 1.40) mmol), NaO t -Bu (6.75 g, 70.24 mmol) and toluene (117 ml) were added and stirred at 65°C. Upon completion of the reaction , the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 19.34 g of a product (yield: 62%).
(2) P-99의 합성예(2) Synthesis example of P-99
Inter-99(19.34 g, 21.77 mmol)에 Sub1-46(3.68 g, 21.77 mmol), Pd2(dba)3 (0.40 g, 0.44 mmol), 50% P(t-Bu)3 (0.18g, 0.87 mmol), NaOt-Bu (4.18 g, 43.54 mmol), toluene (73ml)을 첨가하고 130℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 16.23 g (수율: 73%)를 얻었다.Inter-99 (19.34 g, 21.77 mmol) in Sub1-46 (3.68 g, 21.77 mmol), Pd 2 (dba) 3 (0.40 g, 0.44 mmol), 50% P( t- Bu) 3 (0.18 g, 0.87) mmol), NaO t -Bu (4.18 g, 43.54 mmol), and toluene (73 ml) were added and stirred at 130°C. Upon completion of the reaction , the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 16.23 g of a product (yield: 73%).
상기와 같은 합성예에 따라 제조된 본 발명의 화합물 P-1 내지 P-124의 FD-MS 값은 하기 표 3과 같다.FD-MS values of compounds P-1 to P-124 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.
[표 3][Table 3]
유기전기소자의 제조평가Manufacturing evaluation of organic electric devices
[실시예 1] 블루유기발광소자(광효율 개선층)[Example 1] Blue organic light emitting device (light efficiency improvement layer)
유리 기판에 형성된 ITO층(양극) 상에 N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (이하 '2-TNATA'로 약기함)막을 진공증착하여 60 nm 두께의 정공주입층을 형성한 후, N,N'-bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (이하 'NPB'로 약기함) 막을 60 nm 두께로 진공증착하여 정공수송층을 형성하였다.N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4 on the ITO layer (anode) formed on the glass substrate -diamine (hereinafter abbreviated as '2-TNATA') film was vacuum deposited to form a 60 nm thick hole injection layer, and then N,N'-bis(1-naphthalenyl)-N,N'-bis-phenyl- A (1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as 'NPB') film was vacuum-deposited to a thickness of 60 nm to form a hole transport layer.
이후, 정공수송층 상에 9,10-di(naphthalen-2-yl)anthracene을 호스트로, BD-052X(Idemitsu kosan)을 도펀트로 사용하되 이들 중량비가 93:7가 되도록 도펀트를 도핑하여 30nm 두께의 발광층을 형성하였다. Thereafter, 9,10-di(naphthalen-2-yl)anthracene as a host and BD-052X (Idemitsu kosan) as a dopant were used on the hole transport layer, but doped with dopants so that these weight ratios were 93:7 A light emitting layer was formed.
다음으로, 상기 발광층 상에 (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (이하 'BAlq'로 약기함)을 10 nm 두께로 진공증착하여 정공저지층을 형성하고, 상기 정공저지층 상에 트리스(8-퀴놀리놀)알루미늄(이하 Alq3로 약칭함)을 40 nm 두께로 성막하여 전자수송층을 형성하였다. Next, (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as 'BAlq') was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer was formed, and tris(8-quinolinol)aluminum (hereinafter abbreviated as Alq 3 ) was deposited on the hole blocking layer to a thickness of 40 nm to form an electron transport layer.
이후, 전자수송층 상에 LiF를 0.2 nm 두께로 증착하여 전자주입층을 형성하고, 상기 전자주입층 상에 Al을 150 nm의 두께로 증착하여 음극을 형성한 이후, 본 발명의 화합물 P-1을 60 nm 두께로 성막하여 광효율 개선층을 형성하였다.Thereafter, LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and Al was deposited on the electron injection layer to a thickness of 150 nm to form a cathode, and then the compound P-1 of the present invention was A film was formed to a thickness of 60 nm to form a light efficiency improving layer.
[실시예 2] 내지 [실시예 16][Example 2] to [Example 16]
광효율 개선층 물질로 본 발명의 화합물 P-1 대신 하기 표 4에 기재된 본 발명의 화합물을 사용한 점을 제외하고는 실시예 1과 동일한 방법으로 유기전기 발광소자를 제작하였다. An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention described in Table 4 was used instead of the compound P-1 of the present invention as a material for the light efficiency improvement layer.
[비교예 1][Comparative Example 1]
광효율 개선층을 형성하지 점을 제외하고는 상기 실시예 1과 동일한 방법으로 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the light efficiency improving layer was not formed.
[비교예 2][Comparative Example 2]
광효율 개선층 물질로 본 발명의 화합물 P-1 대신 하기 비교화합물 A를 사용한 점을 제외하고는 실시예 1과 동일한 방법으로 유기전기 발광소자를 제작하였다. An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the following comparative compound A was used instead of the compound P-1 of the present invention as a material for the light efficiency improvement layer.
<비교화합물 A><Comparative compound A>
본 발명의 실시예 1 내지 실시예 16, 비교예 1 및 비교예 2에 의해 제조된 유기전기발광소자에 순바이어스 직류전압을 가하여 포토리서치 (photoresearch) 사의 PR-650으로 전기발광(EL) 특성을 측정하였으며, 500cd/m2 기준휘도에서 맥사이언스사의 수명측정장비를 통해 T95 수명을 측정하였다. 측정 결과는 하기 표 4와 같다.By applying a forward bias DC voltage to the organic electroluminescent devices manufactured by Examples 1 to 16, Comparative Examples 1 and 2 of the present invention, the electroluminescence (EL) characteristics were obtained with PR-650 of Photoresearch. was measured, and the T95 lifespan was measured using the life measuring equipment of McScience at 500cd/m 2 standard luminance. The measurement results are shown in Table 4 below.
[표 4][Table 4]
[실시예 17] 내지 [실시예 32] 그린유기발광소자[Example 17] to [Example 32] Green organic light emitting device
호스트로 4,4'-N,N'-dicarbazole-biphenyl(이하 CBP라 함)를, 도판트로 tris(2-phenylpyridine)-iridium(이하 Ir(ppy)3 라 함)을 사용하되 이들 중량비가 95:5가 되도록 도펀트를 도핑하고, 광효율 개선층으로 하기 표 5에 기재된 화합물을 사용한 점을 제외하고는 상기 실시예 1과 동일한 방법으로 유기전기발광소자를 제작하였다.4,4'-N,N'-dicarbazole-biphenyl (hereinafter referred to as CBP) as a host and tris(2-phenylpyridine)-iridium (hereinafter referred to as Ir(ppy) 3 ) as a dopant were used, but these weight ratios were 95 : An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the dopant was doped to a ratio of 5 and the compound shown in Table 5 was used as the light efficiency improving layer.
[비교예 3][Comparative Example 3]
광효율 개선층을 형성하지 않은 점을 제외하고는 상기 실시예 17과 동일한 방법으로 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Example 17, except that the light efficiency improving layer was not formed.
[비교예 4][Comparative Example 4]
광효율 개선층 물질로 상기 비교화합물 A를 사용한 점을 제외하고는 상기 실시예 17과 동일한 방법으로 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Example 17, except that Comparative Compound A was used as a material for the light efficiency improving layer.
본 발명의 실시예 17 내지 실시예 32, 비교예 3 및 비교예 4에 의해 제조된 유기전기발광소자에 순바이어스 직류전압을 가하여 포토리서치 (photoresearch) 사의 PR-650으로 전기발광(EL) 특성을 측정하였으며, 5000 cd/m2 기준휘도에서 맥사이언스사의 수명측정장비를 통해 T95 수명을 측정하였다. 측정 결과는 하기 표 5와 같다.By applying a forward bias DC voltage to the organic electroluminescent devices manufactured by Examples 17 to 32, Comparative Examples 3 and 4 of the present invention, the electroluminescence (EL) characteristics were measured with PR-650 of Photoresearch. was measured, and the T95 lifetime was measured using a life measuring device of McScience at 5000 cd/m 2 standard luminance. The measurement results are shown in Table 5 below.
[표 5][Table 5]
[실시예 33] 내지 [실시예 48] 레드유기발광소자[Example 33] to [Example 48] Red organic light emitting device
도판트로 bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate(이하 (piq)2Ir(acac)라 함)을 사용하고, 광효율 개선층으로 하기 표 6에 기재된 화합물을 사용한 점을 제외하고는 상기 실시예 17과 동일한 방법으로 유기전기발광소자를 제작하였다.bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter referred to as (piq) 2 Ir(acac)) as the dopant, and the compound shown in Table 6 below as the light efficiency improving layer. An organic electroluminescent device was manufactured in the same manner as in Example 17.
[비교예 5][Comparative Example 5]
광효율 개선층을 형성하지 않은 점을 제외하고는 상기 실시예 33과 동일한 방법으로 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Example 33, except that the light efficiency improving layer was not formed.
[비교예 6][Comparative Example 6]
광효율 개선층 물질로 상기 비교화합물 A를 사용한 점을 제외하고는 상기 실시예 33과 동일한 방법으로 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Example 33, except that Comparative Compound A was used as a material for the light efficiency improving layer.
본 발명의 실시예 33 내지 실시예 48, 비교예 5 및 비교예 6에 의해 제조된 유기전기발광소자에 순바이어스 직류전압을 가하여 포토리서치 (photoresearch) 사의 PR-650으로 전기발광(EL) 특성을 측정하였으며, 2500 cd/m2 기준휘도에서 맥사이언스사의 수명측정장비를 통해 T95 수명을 측정하였다. 측정 결과는 하기 표 6과 같다.By applying a forward bias DC voltage to the organic electroluminescent devices manufactured by Examples 33 to 48, Comparative Examples 5 and 6 of the present invention, the electroluminescence (EL) characteristics were measured with PR-650 of Photoresearch. was measured, and the T95 lifetime was measured using a life measuring device of McScience at 2500 cd/m 2 standard luminance. The measurement results are shown in Table 6 below.
[표 6][Table 6]
상기 표 4 내지 표 6으로부터 알 수 있듯이, 본 발명의 화학식 1로 표시되는 화합물을 광효율 개선층 재료로 사용할 경우, 광효율 개선층을 형성하지 않거나 비교화합물 A를 사용한 경우에 비해 수명이 증가하면서도 효율과 색순도가 현저히 향상된다.As can be seen from Tables 4 to 6, when the compound represented by Formula 1 of the present invention is used as a material for the light efficiency improving layer, the lifespan is increased compared to the case where the light efficiency improving layer is not formed or when the comparative compound A is used, but the efficiency and Color purity is significantly improved.
광효율 개선층이 형성될 경우 Al 전극(음극)과 고굴절의 유기재료 경계면에서 SPPs (Surface plasmon polaritons)가 발생하는데, 그 중 TE (transverse electric) 편광된 빛은 소산파 (evanescent wave)에 의해 광효율 개선층에서 수직 방향으로 소멸되고, 음극과 광효율 개선층을 따라 이동하는 TM (transverse magnetic) 편광된 빛은 표면 플라즈마 공진 (surface plasmon resonance)에 의해 파장의 증폭현상이 일어난다. 그 결과 효율과 색순도가 향상된 것으로 보인다.When the light efficiency improvement layer is formed, SPPs (Surface plasmon polaritons) are generated at the interface between the Al electrode (cathode) and the high refractive organic material. Among them, TE (transverse electric) polarized light improves light efficiency by evanescent wave TM (transverse magnetic) polarized light that is dissipated in the vertical direction in the layer and moves along the cathode and the light efficiency improvement layer is amplified by surface plasma resonance. As a result, the efficiency and color purity seem to be improved.
본 발명의 화합물은 가시광선 파장대 (430 nm 내지 780 nm의 범위)에서 굴절률이 높은 옥사졸과 싸이아졸 모이어티가 융합된 4환 코어를 가지며, 이러한 코어에 적어도 하나의 아미노 그룹이 결합되면서, 이러한 아미노 그룹에도 굴절률을 높일 수 있는 벤조옥사졸, 벤조싸이아졸 등과 같은 치환기가 결합된 구조이다.The compound of the present invention has a tetracyclic core in which oxazole and thiazole moieties having a high refractive index in the visible wavelength band (range of 430 nm to 780 nm) are fused, and at least one amino group is bonded to this core, It has a structure in which a substituent such as benzoxazole and benzothiazole, which can increase the refractive index, is also bonded to the amino group.
따라서, 본 발명의 화합물은 코어와 치환기가 결합에 의한 시너지로 인해 비교화합물 A보다 더 큰 굴절률을 가지게 되고, 그 결과 유기층에서 생성된 광은 보강간섭의 원리에 의해 유기발광 소자 외부로 취출되는 효율이 증가하게 되어 유기발광소자의 전체 광효율이 향상된다.Therefore, the compound of the present invention has a higher refractive index than the comparative compound A due to synergy due to the combination of the core and the substituent, and as a result, the light generated in the organic layer is extracted to the outside of the organic light emitting device by the principle of constructive interference. As this increases, the overall light efficiency of the organic light emitting diode is improved.
이상의 설명은 본 발명을 예시적으로 설명한 것에 불과한 것으로, 본 발명에 속하는 기술분야에서 통상의 지식을 가지는 자라면 본 발명의 본질적인 특성에서 벗어나지 않는 범위에서 다양한 변형이 가능할 것이다. 따라서, 본 명세서에 개시된 실시예들은 본 발명을 한정하기 위한 것이 아니라 설명하기 위한 것이고, 이러한 실시예에 의하여 본 발명의 범위가 한정되는 것은 아니다. 본 발명의 보호범위는 아래의 청구범위에 의하여 해석되어야 하며, 그와 동등한 범위 내의 모든 기술은 본 발명의 권리범위에 포함하는 것으로 해석되어야 할 것이다.The above description is merely illustrative of the present invention, and those of ordinary skill in the art to which the present invention pertains will be able to make various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed herein are for illustrative purposes rather than limiting the present invention, and the scope of the present invention is not limited by these embodiments. The protection scope of the present invention should be construed by the following claims, and all technologies within the scope equivalent thereto should be construed as being included in the scope of the present invention.
CROSS-REFERENCE TO RELATED APPLICATIONCROSS-REFERENCE TO RELATED APPLICATION
본 특허출원은 2020년 03월 04일 한국에 출원한 특허출원번호 제10-2020-0026915호에 대해 미국 특허법 119조 내지 121조, 365조 (35 U.S.C §119조 내지 §121조, §365조)에 따라 우선권을 주장하며, 그 모든 내용은 참고문헌으로 본 특허출원에 병합된다. 아울러, 본 특허출원은 미국 이외에 국가에 대해서도 위와 동일한 이유로 우선권을 주장하면 그 모든 내용은 참고문헌으로 본 특허출원에 병합된다.This patent application is based on U.S. Patent Law Articles 119 to 121 and 365 (35 USC §119 to §121, §365 Articles) with respect to Patent Application No. 10-2020-0026915 filed in Korea on March 04, 2020. ), and all contents are incorporated into this patent application by reference. In addition, if this patent application claims priority to countries other than the United States for the same reason as above, all contents thereof are incorporated into this patent application by reference.
Claims (10)
- 제 1전극; 제 2전극; 상기 제 1전극과 상기 제 2전극 사이에 형성된 1층 이상의 유기물층; 및 상기 제 1전극의 양면 중에서 상기 유기물층과 접하지 않는 일면 또는 상기 제 2전극의 양면 중에서 상기 유기물층과 접하지 않는 일면에 형성된 광효율 개선층을 포함하는 유기전기소자에 있어서,a first electrode; a second electrode; at least one organic material layer formed between the first electrode and the second electrode; and a light efficiency improving layer formed on one surface of both surfaces of the first electrode not in contact with the organic material layer or on one surface of both surfaces of the second electrode not in contact with the organic material layer,상기 광효율 개선층은 하기 화학식 1로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기전기소자:The light efficiency improving layer is an organic electric device comprising a compound represented by the following formula (1):<화학식 1><Formula 1><화학식 1-1><Formula 1-1>상기 화학식 1에서,In Formula 1,X 및 Z는 서로 독립적으로 O 또는 S이고,X and Z are each independently O or S,Y는 N(R), C(R')(R"), O 또는 S이고,Y is N(R), C(R')(R"), O or S;Ar1 내지 Ar4는 서로 독립적으로 C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; 및 -L'-N(Ra)(Rb)로 이루어진 군에서 선택되며, Ar1 내지 Ar4 중에서 적어도 하나는 화학식 1-1로 표시되며, Ar 1 To Ar 4 Are each independently a C 6 ~ C 60 Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; C 3 ~ C 60 aliphatic group; and -L'-N(R a )(R b ), wherein at least one of Ar 1 to Ar 4 is represented by Formula 1-1,L1 내지 L7은 서로 독립적으로 단일결합; C6~C60의 아릴렌기; 플루오렌일렌기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 C3~C60의 지방족고리기로 이루어진 군에서 선택되며,L 1 To L 7 Are each independently a single bond; C 6 ~ C 60 Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; And C 3 ~ C 60 It is selected from the group consisting of an aliphatic cyclic group,R1 내지 R3은 서로 독립적으로 수소; 중수소; 할로겐; 시아노기; 니트로기; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; C1~C30의 알킬기; C2~C30의 알켄일기; C2~C30의 알킨일기; C1~C30의 알콕실기; C6~C30의 아릴옥시기; 및 -L'-N(Ra)(Rb)로 이루어진 군에서 선택되고, 이웃한 기끼리 서로 결합하여 고리를 형성할 수 있으며, R 1 to R 3 are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; C 6 ~ C 60 Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; C 3 ~ C 60 aliphatic group; C 1 ~ C 30 Alkyl group; C 2 ~ C 30 Alkenyl group; C 2 ~ C 30 Alkynyl group; C 1 ~ C 30 An alkoxyl group; C 6 ~ C 30 Aryloxy group; And -L'-N(R a ) (R b ) is selected from the group consisting of, adjacent groups may combine with each other to form a ring,n 및 p는 각각 0~4의 정수이고, m은 0~2의 정수이며, 이들 각각이 2 이상의 정수인 경우 R1 각각, R2 각각, R3 각각은 서로 같거나 상이하며,n and p are each an integer of 0-4, m is an integer of 0-2, and when each of these is an integer of 2 or more, each of R 1 , each of R 2 , and each of R 3 are the same as or different from each other,o는 0~2의 정수이고, o가 2인 경우 L1 각각, L2 각각, L3 각각, Ar1 각각, Ar2 각각은 서로 같거나 상이하며,o is an integer of 0 to 2, and when o is 2, each of L 1 , each of L 2 , each of L 3 , each of Ar 1 , each of Ar 2 are the same as or different from each other,상기 L'는 단일결합; C6~C60의 아릴렌기; 플루오렌일렌기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 C3~C60의 지방족고리기로 이루어진 군에서 선택되며,The L' is a single bond; C 6 ~ C 60 Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; And C 3 ~ C 60 It is selected from the group consisting of an aliphatic cyclic group,상기 R, Ra 및 Rb는 서로 독립적으로 C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 C3~C60의 지방족고리기로 이루어진 군에서 선택되며,The R, R a and R b are each independently a C 6 ~ C 60 aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; And C 3 ~ C 60 It is selected from the group consisting of an aliphatic cyclic group,상기 R' 및 R"은 서로 독립적으로 수소; 중수소; 할로겐; 시아노기; 니트로기; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; C1~C30의 알킬기; C2~C30의 알켄일기; C2~C30의 알킨일기; C1~C30의 알콕실기; 및 C6~C30의 아릴옥시기로 이루어진 군에서 선택되고, R'과 R"은 서로 결합하여 고리를 형성할 수 있으며,Wherein R' and R" are each independently hydrogen; deuterium; halogen; cyano group; nitro group; C 6 ~ C 60 aryl group; fluorenyl group; O, N, S, at least one heteroatom of S, Si and P Containing C 2 ~ C 60 Heterocyclic group; C 3 ~ C 60 Aliphatic ring group; C 1 ~ C 30 Alkyl group; C 2 ~ C 30 Alkenyl group; C 2 ~ C 30 Alkynyl group; C 1 ~ C 30 An alkoxyl group; And C 6 ~ C 30 selected from the group consisting of an aryloxy group, R' and R" may be bonded to each other to form a ring,상기 아릴기, 아릴렌기, 플루오렌일기, 플루오렌일렌기, 헤테로고리기, 지방족 고리기, 알킬기, 알켄일기, 알킨일기, 알콕실기, 아릴옥시기, 이웃한 기끼리 서로 결합하여 형성된 고리, 및 R'과 R"이 서로 결합하여 형성된 고리는 각각 중수소; 할로겐; C1-C20의 알킬기 또는 C6-C20의 아릴기로 치환 또는 비치환된 실란기; C1-C20의 알킬기 또는 C6-C20의 아릴기로 치환 또는 비치환된 포스핀옥사이드; 실록산기; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕실기; C6-C20의 아릴옥시기; C6-C20의 아릴싸이오기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C20의 헤테로고리기; 및 C3-C20의 지방족고리기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있다.The aryl group, an arylene group, a fluorenyl group, a fluorenylene group, a heterocyclic group, an aliphatic ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyl group, an aryloxy group, a ring formed by bonding adjacent groups to each other, and A ring formed by combining R′ and R″ is deuterium; halogen; a silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; a C 1 -C 20 alkyl group or C 6 -C 20 Phosphine oxide unsubstituted or substituted with an aryl group; Siloxane group; Cyano group; Nitro group; C 1 -C 20 Alkylthio group; C 1 -C 20 Alkoxy group; C 6 -C 20 Aryloxy group; C 6 -C 20 Arylthio group; C 1 -C 20 Alkyl group; C 2 -C 20 Alkenyl group; C 2 -C 20 Alkynyl group; C 6 -C 20 Aryl group; Flu Orenyl group; C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; And one selected from the group consisting of C 3 -C 20 aliphatic ring group It may be substituted with more than one substituent.
- 제 1항에 있어서,The method of claim 1,상기 화학식 1은 하기 화학식 2 또는 화학식 3으로 표시되는 것을 특징으로 하는 유기전기소자:Formula 1 is an organic electric device, characterized in that represented by Formula 2 or Formula 3:<화학식 2> <화학식 3><Formula 2> <Formula 3>상기 화학식 2 및 3에서, X, Y, Ar1~Ar4, L1~L6, R1, R2, m, n은 제1항에서 정의된 것과 같다.In Formulas 2 and 3, X, Y, Ar 1 to Ar 4 , L 1 to L 6 , R 1 , R 2 , m, and n are the same as defined in claim 1.
- 제 1항에 있어서,The method of claim 1,상기 화학식 1은 하기 화학식 4 내지 화학식 7 중에서 하나로 표시되는 것을 특징으로 하는 유기전기소자:Formula 1 is an organic electric device, characterized in that represented by one of the following Formulas 4 to 7:<화학식 4> <화학식 5><Formula 4> <Formula 5><화학식 6> <화학식 7><Formula 6> <Formula 7>상기 화학식 4 내지 7에서, X, Ar1~Ar4, L1~L6, R1, R2, R, R', R", m, n, o는 제1항에서 정의된 것과 같다.In Formulas 4 to 7, X, Ar 1 to Ar 4 , L 1 to L 6 , R 1 , R 2 , R, R′, R″, m, n, o are the same as defined in claim 1.
- 제 1항에 있어서,The method of claim 1,상기 화학식 1-1은 하기 화학식 1-1A로 표시되는 것을 특징으로 하는 유기전기소자:The formula 1-1 is an organic electric device, characterized in that represented by the following formula 1-1A:<화학식 1-1A><Formula 1-1A>상기 화학식 1-1A에서, Z, L7, R3, p는 제1항에서 정의된 것과 같다.In Formula 1-1A, Z, L 7 , R 3 , and p are as defined in claim 1.
- 제 1항에 있어서,The method of claim 1,상기 유기물층은 정공 수송층, 발광층 및 전자수송층을 포함하는 것을 특징으로 하는 유기전기소자.The organic material layer is an organic electric device comprising a hole transport layer, a light emitting layer and an electron transport layer.
- 제 6에 있어서,According to claim 6,상기 유기물층은 상기 정공수송층, 발광층 및 전자수송층을 포함하는 스택을 둘 이상 포함하는 것을 특징으로 하는 유기전기소자.The organic layer comprises at least two stacks including the hole transport layer, the light emitting layer and the electron transport layer.
- 제 7항에 있어서,8. The method of claim 7,상기 유기물층은 상기 둘 이상의 스택 사이에 형성된 전하생성층을 더 포함하는 것을 특징으로 하는 유기전기소자.The organic material layer is an organic electric device, characterized in that it further comprises a charge generation layer formed between the two or more stacks.
- 제1항의 유기전기소자를 포함하는 디스플레이장치; 및 A display device comprising the organic electric device of claim 1; and상기 디스플레이장치를 구동하는 제어부;를 포함하는 전자장치.An electronic device comprising a; a control unit for driving the display device.
- 제 9항에 있어서,10. The method of claim 9,상기 유기전기소자는 유기전기발광소자, 유기태양전지, 유기감광체, 유기트랜지스터, 단색 조명용 소자 및 퀀텀닷 디스플레이용 소자로 이루어진 군에서 선택되는 것을 특징으로 하는 전자장치.The organic electric device is an electronic device, characterized in that selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a device for monochromatic lighting, and a device for a quantum dot display.
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CN114436971A (en) * | 2022-02-25 | 2022-05-06 | 陕西维世诺新材料有限公司 | Di (4- (benzoxazol-2-yl) phenyl) methylamine derivative and preparation method thereof |
CN114874235A (en) * | 2022-05-23 | 2022-08-09 | 武汉天马微电子有限公司 | Heterocyclic compound and application thereof |
CN114989181A (en) * | 2022-06-30 | 2022-09-02 | 武汉天马微电子有限公司 | Heterocyclic arylamine compound, organic electroluminescent device and display panel |
WO2023241136A1 (en) * | 2022-06-13 | 2023-12-21 | 陕西莱特光电材料股份有限公司 | Heterocyclic compound, organic electroluminescent apparatus, and electronic device |
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KR102559876B1 (en) * | 2020-04-16 | 2023-07-26 | 주식회사 동진쎄미켐 | New compound for capping layer and Organic light emitting diode comprising to the same |
KR102568928B1 (en) * | 2020-12-14 | 2023-08-22 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
CN116157407A (en) * | 2020-12-17 | 2023-05-23 | 株式会社Lg化学 | Novel compound and organic light emitting device including the same |
KR20230136874A (en) * | 2022-03-18 | 2023-09-27 | 에스에프씨 주식회사 | Novel Heterocyclic compounds and Organic light emitting diode including the same |
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