WO2018105775A1 - Composé d'indazole et dispositif électroluminescent organique le contenant - Google Patents
Composé d'indazole et dispositif électroluminescent organique le contenant Download PDFInfo
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- WO2018105775A1 WO2018105775A1 PCT/KR2016/014305 KR2016014305W WO2018105775A1 WO 2018105775 A1 WO2018105775 A1 WO 2018105775A1 KR 2016014305 W KR2016014305 W KR 2016014305W WO 2018105775 A1 WO2018105775 A1 WO 2018105775A1
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- light emitting
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- electrode
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- organic light
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- -1 Indazole compound Chemical class 0.000 title claims abstract description 53
- 239000012044 organic layer Substances 0.000 claims abstract description 6
- 239000010410 layer Substances 0.000 claims description 82
- 150000001875 compounds Chemical class 0.000 claims description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 10
- 239000011368 organic material Substances 0.000 claims description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 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 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
- 125000006383 alkylpyridyl group Chemical group 0.000 claims description 3
- 125000005264 aryl amine group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 125000004623 carbolinyl group Chemical group 0.000 claims description 3
- 125000004802 cyanophenyl group Chemical group 0.000 claims description 3
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 125000006485 halo alkoxy phenyl group Chemical group 0.000 claims description 3
- 125000005059 halophenyl group Chemical group 0.000 claims description 3
- 125000006377 halopyridyl group Chemical group 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- 150000001340 alkali metals Chemical class 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 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
- RVPCPPWNSMAZKR-UHFFFAOYSA-N (10-phenylanthracen-9-yl)boronic acid Chemical compound C12=CC=CC=C2C(B(O)O)=C2C=CC=CC2=C1C1=CC=CC=C1 RVPCPPWNSMAZKR-UHFFFAOYSA-N 0.000 description 1
- SFUIGUOONHIVLG-UHFFFAOYSA-N (2-nitrophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1[N+]([O-])=O SFUIGUOONHIVLG-UHFFFAOYSA-N 0.000 description 1
- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 1
- RUJTWTUYVOEEFW-UHFFFAOYSA-N 1-(6-bromopyridin-2-yl)ethanone Chemical compound CC(=O)C1=CC=CC(Br)=N1 RUJTWTUYVOEEFW-UHFFFAOYSA-N 0.000 description 1
- HWZJQLSBBQLPAJ-UHFFFAOYSA-N 1h-pyrazolo[3,4-f]quinoline Chemical compound C1=CC2=NC=CC=C2C2=C1C=NN2 HWZJQLSBBQLPAJ-UHFFFAOYSA-N 0.000 description 1
- BVKRPQCDGACLPX-UHFFFAOYSA-N 2-[4-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyindol-1-yl]-N-methyl-N-phenylacetamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC1=C2C=CN(C2=CC=C1)CC(=O)N(C1=CC=CC=C1)C BVKRPQCDGACLPX-UHFFFAOYSA-N 0.000 description 1
- ZZVUOSVSPAPBEJ-UHFFFAOYSA-N 2-amino-4-bromobenzaldehyde Chemical compound NC1=CC(Br)=CC=C1C=O ZZVUOSVSPAPBEJ-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- DVLLMPLACXRDOE-UHFFFAOYSA-N 5-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyrimidine Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(C=2C=NC=NC=2)C=C1 DVLLMPLACXRDOE-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002473 indoazoles Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
-
- 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
- H10K50/16—Electron transporting layers
Definitions
- the present invention relates to an indazole compound and an organic light emitting device comprising the same.
- the organic light emitting device is a device for converting electrical energy into light energy using an organic material, and includes a structure in which a light emitting organic material layer is formed between an anode and a cathode.
- the organic light emitting device may be formed in various structures, among which a tandem organic light emitting device in which a plurality of light emitting parts are stacked is studied.
- a tandem organic light emitting device a plurality of light emitting parts including a light emitting layer are stacked between an anode and a cathode.
- a charge generation layer for generating and moving charges is positioned between adjacent light emitting units.
- the charge generation layer requires low driving voltage and high efficiency.
- Another object of the present invention is to minimize the energy level difference between the n-type charge generation layer and the p-type charge generation layer in the tandem organic light emitting device to improve the amount of electron injection in the light emitting portion and the organic light emitting comprising the same It is to provide an element.
- Still another object of the present invention is to provide an indazole compound capable of minimizing the diffusion of alkali metal into the p-type charge generation layer even when the n-type charge generation layer is doped with an alkali metal, and an organic light emitting device including the same. It is.
- R 1 and R 2 are hydrogen or unsubstituted or unsubstituted 5 to 60 containing one or more heteroatoms selected from aryl groups having 3 to 60 carbon atoms, nitrogen, oxygen and sulfur.
- a membered heteroaryl group, an arylamine group, or a secondary amine group, X 1 and X 2 are selected from nitrogen or carbon, and at least one of X 1 and X 2 is nitrogen.
- the indazole compound may be represented by the following formula (2).
- X 3 may be selected from nitrogen or carbon.
- R 1 and R 2 are each independently hydrogen, substituted or unsubstituted phenyl, alkylphenyl, biphenyl, alkylbiphenyl, halophenyl, alkoxyphenyl, haloalkoxyphenyl, cyanophenyl, silylphenyl, naphthyl, alkyl Naphthyl, halonaphthyl, cyanonaphthyl, silylnaphthyl, pyridyl, alkylpyridyl, halopyridyl, cyanopyridyl, alkoxypyridyl, silylpyridyl, pyrimidyl, halopyrimidyl, cyanopyri Midyl, alkoxypyrimidyl, quinolinyl, isoquinolinyl, quinoxalinyl, pyrazinyl, quinazolinyl, naphthy
- the object of the present invention is a first electrode; Second electrode; And an organic material layer disposed between the first electrode and the second electrode and emitting light, wherein the organic material layer is formed of a plurality of layers, and at least one layer is achieved by an organic light emitting device including the indazole compound. do.
- the at least one layer may include a charge generation layer (CGL).
- CGL charge generation layer
- the charge generation layer CGL may be n-type.
- the at least one layer may include an electron transport layer.
- the object of the present invention is a first electrode; Second electrode; And a first light emitting part disposed between the first electrode and the second electrode and including a first light emitting layer.
- a second light emitting part disposed between the second electrode and the first light emitting part and including a second light emitting layer; And a charge generating layer positioned between the first light emitting portion and the second light emitting portion, wherein the charge generating layer is achieved by an organic light emitting device including the indazole compound.
- an indazole compound of a novel structure is provided.
- an indazole compound capable of improving the driving voltage and efficiency by improving the electron injection amount in the light emitting part by minimizing the energy level difference between the n-type charge generation layer and the p-type charge generation layer and an organic light emitting device comprising the same Is provided.
- the alkali metal is tightly coordinated with an indazole compound which is a host material to minimize diffusion of the alkali metal into the p-type charge generation layer.
- an indazole compound capable of improving lifespan and an organic light emitting device comprising the same.
- FIG. 1 is a cross-sectional view of an organic light emitting diode according to an embodiment of the present invention.
- the indazole compound according to the present invention is represented by the formula (1) or (2).
- Formula (I) and R 1 and R 2 are hydrogen, a substituted or non-substituted C 3 -C 60 aryl group, to 5 won unsubstituted or substituted, which contain one or more heteroatoms selected from nitrogen, oxygen and sulfur in the general formula (2)
- a 60-membered heteroaryl group, an arylamine group, or a secondary amine group is represented.
- X 1, X 2 and X 3 are selected from nitrogen or carbon, and at least one of X 1 and X 2 is nitrogen.
- R 1 and R 2 are each independently hydrogen, substituted or unsubstituted phenyl, alkylphenyl, biphenyl, alkylbiphenyl, halophenyl, alkoxyphenyl, haloalkoxyphenyl, cyanophenyl, silylphenyl, naphthyl, alkyl Naphthyl, halonaphthyl, cyanonaphthyl, silylnaphthyl, pyridyl, alkylpyridyl, halopyridyl, cyanopyridyl, alkoxypyridyl, silylpyridyl, pyrimidyl, halopyrimidyl, cyanopyri Midyl, alkoxypyrimidyl, quinolinyl, isoquinolinyl, quinoxalinyl, pyrazinyl, quinazolinyl, naphthy
- the indazole compound according to the present invention may be a compound shown below.
- the organic light emitting diode 1 is a cross-sectional view of an organic light emitting diode according to an embodiment of the present invention.
- the organic light emitting diode 1 has a tandem type structure, and includes a first electrode (anode 110), a second electrode (cathode 120), a first light emitter 210, and a second light emitter 220. And a charge generation layer 230.
- the first light emitting unit 210, the second light emitting unit 220, and the charge generation layer 230 are positioned between the first electrode 110 and the second electrode 120 as an organic layer, and the charge generation layer 230 is Located between the first light emitting unit 210 and the second light emitting unit 220.
- the first light emitting part 210 includes a hole injection layer 211, a first hole transporting layer 212, a first light emitting layer 213, and a first electron transporting layer 214, and the second light emitting part 220 is formed of a first light emitting part 220.
- the charge generation layer 230 includes an n-type charge generation layer 231 and a p-type charge generation layer 232.
- the n-type charge generation layer 231 may be doped with an alkali metal.
- the indazole compound according to the present invention may be used in the first electron transport layer 212, the second electron transport layer 223, and the charge generation layer 230, and in particular, may be used in the n-type charge generation layer 231. .
- the organic light emitting device 1 described above can be variously modified. Some organic layers may be omitted or added, may not be tandem, or may be tandem having three or more light emitting layers.
- substrate After patterning the ITO board
- HAT-CN compound was vacuum deposited to form a 5 nm thick. This compound acts as a hole transport layer.
- An NPB material was formed to a thickness of 35 nm as a hole transport layer thereon.
- a CBP material was used as a host, and an Ir compound was co-deposited at a thickness of 30 nm to form a dopant of about 10% by mass to form a yellow light emitting layer.
- the first electron transport layer was formed on the light emitting layer with a TmPyPB compound having a thickness of 25 nm. Subsequently, a second electron transport layer was formed by co-depositing a Li material on the BPhen material to a thickness of 10 nm to have a 2% mass ratio. Thereafter, Al was deposited to a thickness of 100 nm to form a cathode to fabricate an organic EL device.
- the organic light emitting device was manufactured by the same method as the comparative example described above, but replacing only the second electron transport material with 1-69 compound.
- the organic light emitting device was fabricated in the same manner as the comparative example described above, but replacing only the second electron transport material with a 1-24 compound.
- the organic light emitting device was manufactured by the same method as the comparative example described above, but replacing only the second electron transport material with a 1-38 compound.
- the organic light emitting device was fabricated in the same manner as the comparative example described above, except that only the second electron transport material was converted into a 1-64 compound.
- low-voltage high-efficiency driving is realized through electrical doping of the charge transport layer in the OLED structure.
- the P doping layer is doped with an electron-lean organic material or metal oxide in the hole transport material
- the N doping layer is doped with an alkali metal such as lithium or cesium having a low work function in the electron transport material.
- the doped layer reduces the surface resistance of the organic material during operation to facilitate charge injection from adjacent layers.
- the introduction of a buffer layer on the doped anode layer realizes low voltage by energy banding and a low voltage driving technique using a material having high charge mobility, and has obtained high efficiency by manufacturing a fluorescent and phosphorescent material in a laminated structure.
- Tandem structure is a structure in which the EL units including the doped hole transport layer and the electron transport layer are vertically stacked, and the current luminous efficiency increases in proportion to the number of stacked layers.
- the CGL (change generation layer) layer is a concept of a transparent PN junction, and can be understood as a concept in which a unit PIN OLED light emitting unit is stacked in a plurality of layers. Therefore, even a single layer PIN OLED embodiment can predict the efficiency and voltage of the stack structure.
- the driving voltage of the embodiment is lower than that of the comparative example while the current efficiency and the quantum efficiency of the example are higher than the comparative example.
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- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
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- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
La présente invention concerne un composé d'indazole et un dispositif électroluminescent organique qui présente d'excellentes caractéristiques de rendement en incluant le composé d'indazole dans une ou plusieurs couches organiques.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/KR2016/014305 WO2018105775A1 (fr) | 2016-12-07 | 2016-12-07 | Composé d'indazole et dispositif électroluminescent organique le contenant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/KR2016/014305 WO2018105775A1 (fr) | 2016-12-07 | 2016-12-07 | Composé d'indazole et dispositif électroluminescent organique le contenant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2018105775A1 true WO2018105775A1 (fr) | 2018-06-14 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2016/014305 WO2018105775A1 (fr) | 2016-12-07 | 2016-12-07 | Composé d'indazole et dispositif électroluminescent organique le contenant |
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| Country | Link |
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| WO (1) | WO2018105775A1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111100146A (zh) * | 2019-12-30 | 2020-05-05 | 陕西莱特光电材料股份有限公司 | 一种有机化合物和应用以及使用其的有机电致发光器件 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| WO2015034140A1 (fr) * | 2013-09-04 | 2015-03-12 | 희성소재(주) | Composé polycyclique contenant du pyrazole et dispositif électroluminescent organique l'utilisant |
| KR20150132019A (ko) * | 2014-05-15 | 2015-11-25 | 희성소재 (주) | 헤테로고리 화합물 및 이를 이용한 유기 발광 소자 |
| KR20160049800A (ko) * | 2014-10-28 | 2016-05-10 | 희성소재 (주) | 함질소 다환 화합물 및 이를 이용한 유기발광소자 |
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| KR20150011422A (ko) * | 2013-07-22 | 2015-02-02 | 주식회사 두산 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
| WO2015034140A1 (fr) * | 2013-09-04 | 2015-03-12 | 희성소재(주) | Composé polycyclique contenant du pyrazole et dispositif électroluminescent organique l'utilisant |
| KR20150132019A (ko) * | 2014-05-15 | 2015-11-25 | 희성소재 (주) | 헤테로고리 화합물 및 이를 이용한 유기 발광 소자 |
| KR20160049800A (ko) * | 2014-10-28 | 2016-05-10 | 희성소재 (주) | 함질소 다환 화합물 및 이를 이용한 유기발광소자 |
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| CN111100146A (zh) * | 2019-12-30 | 2020-05-05 | 陕西莱特光电材料股份有限公司 | 一种有机化合物和应用以及使用其的有机电致发光器件 |
| CN111100146B (zh) * | 2019-12-30 | 2021-01-22 | 陕西莱特光电材料股份有限公司 | 一种有机化合物和应用以及使用其的有机电致发光器件 |
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