WO2019146938A1 - 화합물, 조성물, 유기 광전자 소자 및 표시 장치 - Google Patents
화합물, 조성물, 유기 광전자 소자 및 표시 장치 Download PDFInfo
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- WO2019146938A1 WO2019146938A1 PCT/KR2019/000402 KR2019000402W WO2019146938A1 WO 2019146938 A1 WO2019146938 A1 WO 2019146938A1 KR 2019000402 W KR2019000402 W KR 2019000402W WO 2019146938 A1 WO2019146938 A1 WO 2019146938A1
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- 239000007818 Grignard reagent Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- 229910052775 Thulium Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000005104 aryl silyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 239000004305 biphenyl Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KMBXDHUVRTWCJP-UHFFFAOYSA-N c(cc1)cc(c2ccccc22)c1[n]2-c1cccc(-c2nc(-[n]3c4ccccc4c4c3cccc4)nc(-c3cc(-c4cc5c(cccc6)c6c(cccc6)c6c5cc4)ccc3)n2)c1 Chemical compound c(cc1)cc(c2ccccc22)c1[n]2-c1cccc(-c2nc(-[n]3c4ccccc4c4c3cccc4)nc(-c3cc(-c4cc5c(cccc6)c6c(cccc6)c6c5cc4)ccc3)n2)c1 KMBXDHUVRTWCJP-UHFFFAOYSA-N 0.000 description 1
- ZAYDYNVXBIQORO-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-[n]1c(ccc(-c(cc2c3c4cccc3)ccc2[n]4-c2cccc(-c3ccccc3)c2)c2)c2c2c1cccc2 Chemical compound c(cc1)ccc1-c(cc1)ccc1-[n]1c(ccc(-c(cc2c3c4cccc3)ccc2[n]4-c2cccc(-c3ccccc3)c2)c2)c2c2c1cccc2 ZAYDYNVXBIQORO-UHFFFAOYSA-N 0.000 description 1
- 210000004899 c-terminal region Anatomy 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
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 150000002979 perylenes Chemical group 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 206010036067 polydipsia Diseases 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000003378 silver Chemical group 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 description 1
- 150000003643 triphenylenes Chemical class 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000004832 voltammetry Methods 0.000 description 1
- 238000003260 vortexing Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- RUDFQVOCFDJEEF-UHFFFAOYSA-N yttrium(III) oxide Inorganic materials [O-2].[O-2].[O-2].[Y+3].[Y+3] RUDFQVOCFDJEEF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/30—Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/90—Multiple hosts in the emissive layer
-
- 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
-
- 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
- Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
- Y02T90/00—Enabling technologies or technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02T90/10—Technologies relating to charging of electric vehicles
- Y02T90/16—Information or communication technologies improving the operation of electric vehicles
- Y02T90/167—Systems integrating technologies related to power network operation and communication or information technologies for supporting the interoperability of electric or hybrid vehicles, i.e. smartgrids as interface for battery charging of electric vehicles [EV] or hybrid vehicles [HEV]
Definitions
- Organic optoelectronic diodes are devices that can convert between electrical and optical energy.
- Organic optoelectronic devices can be roughly classified into two types according to the operating principle.
- One is an optoelectronic device in which an exciton formed by light energy is separated into an electron and a hole, and electrons and holes are transmitted to different electrodes to generate electrical energy, and the other is a voltage / Emitting device.
- organic optoelectronic devices examples include organic optoelectronic devices, organic light emitting devices, organic solar cells, and organic photo conductor drums.
- OLEDs organic light emitting diodes
- OLEDs organic light emitting diodes
- One embodiment provides a compound for an organic optoelectronic device capable of implementing a high-efficiency and long-lived organic optoelectronic device.
- Another embodiment provides a composition for an organic optoelectronic device including the above compound.
- Yet another embodiment provides an organic optoelectronic device comprising the compound or composition.
- Another embodiment provides a display device comprising the organic opto-electronic device.
- II 1 to II 14 each independently represent hydrogen, deuterium, a substituted or unsubstituted 01 to 020 alkyl group, a substituted or unsubstituted 06 to 012 aryl group, a cyano group or a combination thereof,
- ⁇ And II 4 are each independently present or connected to each other to form a ring
- I is a valence bond, a substituted or unsubstituted 6 to O30 arylene group, or a substituted or unsubstituted 02 to 030 heteroarylene group,
- 111 and 113 are each independently an integer of 0 or 1
- 112 is an integer of 1.
- composition comprising a first compound represented by Formula 1 and a second compound represented by Formula 2 below. 2019/146938 1 »(: 1 ⁇ ⁇ 2019/000402
- And ⁇ are each independently a single bond, a substituted or unsubstituted C6 to O30 arylene group, or a substituted or unsubstituted C2 to O30 heteroarylene group,
- II 15 to O are each independently hydrogen, deuterium, substituted or unsubstituted 01 to 010 alkyl group, substituted or unsubstituted 06 to 030 aryl group, substituted or unsubstituted 02 to 030 heterocyclic group, cyano group, or A combination thereof,
- 111 is one of the integers from 0 to 2;
- an organic optoelectronic device including an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, wherein the organic layer includes the compound or the composition.
- a display device including the organic opto-electronic device.
- FIG 1 and 2 are sectional views showing an organic light emitting device according to an embodiment, respectively.
- substituted means that at least one hydrogen in the substituent or compound is replaced by a substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted 01 to O30 amine group, Or an unsubstituted or substituted unsubstituted or substituted silyl group having from 1 to 30 carbon atoms, or a substituted or unsubstituted aryloxy group having from 1 to 30 carbon atoms, To 030 heteroaryl group (its 1 to 020 alkoxy group, (1 to 010 thereof, trifluoroalkyl group, cyano group, or a combination thereof).
- substituted means that at least one of the substituents or the hydrogen in the compound is deuterium, To 010 alkylsilyl groups, from 06 to 030
- An arylsilyl group a C3 to C30 cycloalkyl group, a C3 to O30 heterocycloalkyl group, a C6 to O30 aryl group, a C2 to O30 heteroaryl group, or a cyano group.
- " substituted means that at least one hydrogen in the substituent or the compound is substituted with deuterium, (: 1 to 020 alkyl group, 06 to 030 aryl group, or cyano group)
- substitution means that at least one hydrogen in the substituent or the compound is replaced by deuterium, (1) 05 alkyl group, (6) 018 aryl group or cyano group
- substituted " means that at least one hydrogen in the substituent or the compound is substituted with deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl or naphthyl .
- aryl group " is intended to encompass groups having one or more hydrocarbon aromatic moieties, in which all the elements of the hydrocarbon aromatic moiety have a p-orbital and the p-orbital is conjugated A form including a phenyl group, a naphthyl group, and the like, in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, for example, a biphenyl group, a terphenyl group, a quarter phenyl group, Non-aromatic fused rings fused directly or indirectly, such as fluorenyl groups, and the like.
- the aryl group may be monocyclic, polycyclic or fused ring polycyclic (i. E.
- heterocyclic group " is a superordinate concept including a heteroaryl group, and includes N, O, or S in the cyclic compound such as an aryl group, a cycloalkyl group, a fused ring thereof, S, P, and Si.
- the heterocyclic group may contain one or more heteroatoms in whole or in each ring. have.
- heteroaryl group " means that at least one heteroatom selected from the group consisting of N, O, S, P and Si is contained in the aryl group.
- the heteroaryl group includes two or more rings, two or more rings may be fused to each other.
- each ring may contain 1 to 3 of the above heteroatoms.
- the substituted or unsubstituted C6 to C30 aryl group may be substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthrenyl group, A substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o- A substituted or unsubstituted phenyl group,
- the substituted or unsubstituted C2 to C30 heterocyclic group may be substituted or unsubstituted Or a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrazolyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substitute
- the hole property refers to a property that electrons can be donated to form a hole when an electric field (11 11) is applied.
- the hole property has a conduction characteristic along the ⁇ 01 ⁇ 40 level, Quot; means a property that facilitates the movement of holes formed in the light emitting layer to the anode and the movement of the holes in the light emitting layer.
- the electron characteristic refers to a characteristic that electrons can be received when an electric field is applied.
- the electron characteristic has a conduction characteristic along the LUM ⁇ level to inject electrons formed in the cathode into the light emitting layer, move electrons formed in the light emitting layer to the cathode, It is a characteristic that facilitates children.
- " means that adjacent groups are connected to each other to form a substituted or unsubstituted aromatic ring
- the adjacent groups are connected to each other to form a substituted or unsubstituted phenyl group or the like.
- the compounds for organic optoelectronic devices according to embodiments will be described below.
- the compound for organic optoelectronic devices according to one embodiment is represented by the following formula (1). [Chemical Formula 1]
- II 1 to II 14 each independently represent hydrogen, deuterium, a substituted or unsubstituted 01 to 020 alkyl group, a substituted or unsubstituted 06 to 012 aryl group, a cyano group or a combination thereof,
- II < 1 > and R < 3 > are independently present or linked together to form a ring, II < 3 > and R < 4 > each independently exist or are connected to each other to form a ring, Or a substituted or unsubstituted 02 to 030 heteroarylene group,
- 111 and s are each independently an integer of 0 or 1
- the compound represented by the general formula (1) is a compound in which carbazole, triphenylene, and phenyl groups are connected to triazine, and at least one 111 k-phenylen group is interposed between carbazole and triazine, and triphenylenes and triazines Are directly connected without a linker and have a stereogenic and asymmetric molecular structure.
- At least one < RTI ID 0.0 > Relatively ⁇ 1 0 hanmyo 01 is given a value of 0, the glass in the hole injection and migration, and triphenylene and yttria Gene directly to the connector without being relatively (6 by including a phenylene linker! ) 1 ⁇ 1 ⁇ 10 Energy level, which is advantageous for electron injection and transport.
- the device including the compound represented by the formula (1), hole / electron injection and migration are advantageous, and therefore, the device can have favorable life characteristics.
- the bipolar characteristic is enhanced and the 71-bond through the C-N bond is broken by replacing the carbazole in the N-direction
- the electron cloud between HOMO-LUMO can be localized and the lifetime improvement effect can be maximized.
- the HOMO energy level for the compound represented by Formula 1 may be -6.0 eV to -5.0 eV, for example, -5.8 eV to -5.2 eV, more specifically -5.8 eV to -5.5 eV And most specifically from -5.8 eV to -5.7 eV.
- the LUMO energy level can be calculated, for example, from -2.2 eV to -2.9 eV, more specifically from -2.3 eV to -2.8 eV, and more specifically from -2.4 eV to -2.75 eV.
- the HOMO energy level and the LUMO energy level can be measured by cyclic voltammetry (CV, cyclic voltammogram) consisting of EC-Epsilon of BAS (bioanalytical systems Inc. USA) and c-3 cell stand
- the potential of the ferrocene was set to -4.8 eV compared to the energy level of the vacuum
- the HOMO energy level and the LUMO energy level were calculated.
- the HOMO energy level and the LUMO energy level of the green dopant are formed between -5.5 eV and -5.0 eV and -2.9 eV and -2.5 eV, respectively.
- it may be 0 £ 111 + 113 £ 1.
- 112 is 1, and 111 and 0 are both 0s.
- ⁇ is 1, 111 is 1, and 113 is 0.
- 112 is 1, 111 is 0, and 113 is 1.
- the formula (1) may be represented by one of the following formulas (1-1) to (1-6).
- the compound represented by Formula 1 may be represented by Formula 1-1 or Formula 1-
- the grains 1 to < RTI ID 0.0 & gt ; 14 & lt ; / RTI & 010 alkyl group, a 06 to 012 aryl group, or a cyano group.
- each of II 1 to 4 may independently be hydrogen, a methyl group, an ethyl group, a phenyl group, a biphenyl group, a naphthyl group or a cyano group.
- II 1 to II 4 each independently may be hydrogen or a 6 to 12-aryl group.
- ⁇ and # may be independently present or may be connected to each other to form a substituted or unsubstituted aromatic ring.
- each of Formula (I) to ( IV) may be independently present, and may be, for example, hydrogen or a phenyl group, but is not limited thereto.
- ⁇ and 0 are each independently hydrogen, deuterium, a substituted or unsubstituted 01 to 020 alkyl group, a substituted or unsubstituted C6 to O12 aryl group, a cyano group, or combinations thereof.
- ⁇ and 0 may be hydrogen, but are not limited thereto.
- each of II 5 to I 9 may independently be hydrogen, ⁇ 31 to 05 alkyl group, 06 to 12 aryl group or cyano group.
- each of the above groups may independently be hydrogen, a methyl group, an ethyl group, a phenyl group or a cyano group, but is not limited thereto.
- 11 1) and 1 are each independently selected from the group consisting of hydrogen, 2019/146938 12 1 (2019/000402-12) aryl groups or cyano groups.
- For example II is hydrogen, (the alkyl group of 1 to 05, 06 to 012 days aryl group, or a cyano group independently.
- each of the above-mentioned 2 to 4 may independently be hydrogen, a methyl group, an ethyl group, a phenyl group or a cyano group, but is not limited thereto.
- the above-mentioned silver atom-containing bond or a substituted or unsubstituted 06 to 020 arylene group.
- substituted or unsubstituted phenylenes substituted or unsubstituted phenylenes, substituted or unsubstituted 0-phenylene groups, substituted or unsubstituted 111-phenylene groups,
- a biphenylene group a substituted or unsubstituted 111-terphenylene group, a substituted or unsubstituted I) -terphenylene group, or a substituted or unsubstituted 0 -terphenylene group.
- the compound represented by Formula 1 may be selected from the compounds listed in Group 1 below, but is not limited thereto.
- composition for an organic optoelectronic device includes the aforementioned compound (hereinafter referred to as "first compound") and a second compound represented by the following formula (2).
- And ⁇ are each independently a single bond, a substituted or unsubstituted C6 to O30 arylene group, or a substituted or unsubstituted C2 to O30 heteroarylene group,
- Mo 15 to 11 2 are each independently hydrogen, deuterium, substituted or unsubstituted 01 to 010 alkyl group, a substituted or unsubstituted 06 to 030 an aryl group, a substituted or unsubstituted 02 to 030 a heterocyclic group, a cyano group, or A combination thereof,
- III is one of the integers from 0 to 2;
- the second compound may be used in the light emitting layer together with the first compound to improve charge transportability and stability, thereby improving light emitting efficiency and lifetime characteristics.
- 2019/146938 15 (1/10) 019/000402 As an example, the formula (2) may include one of the structures listed in the following group II.
- formula (2) can be represented by the following formula (2-1) or (2-2).
- each of ⁇ and I may be independently a single bond or a substituted or unsubstituted 06 to 020 arylene group.
- each of the rings 2 and 3 may independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, or a substituted or unsubstituted naphthylene group.
- I 111 and third, respectively a single bond, independently, substituted or unsubstituted - A substituted or unsubstituted phenylene group, a substituted or unsubstituted 0 -phenylpentene group, a substituted or unsubstituted 111 -biphenylene group, a substituted or unsubstituted phenylene group, A substituted or unsubstituted naphthylene group, a substituted biphenylen group, a substituted or unsubstituted 0 -biphenylene group, a substituted or unsubstituted 111 -terphenylene group, a substituted or unsubstituted terphenylene group or a substituted or unsubstituted 0 -terphenylene group .
- the substitution may be, for example, but not limited to, at least one hydrogen is deuterium, the 1-202 alkyl group, the
- the above and may each independently be a substituted or unsubstituted 06-membered 030 aryl group.
- * -1 and * 3 * may independently be substituents listed in Group III below, but are not limited thereto.
- the compound represented by the formula (2) may be selected from the compounds listed in the following group 2, but is not limited thereto. f-2]
- the composition may include a first compound represented by one of the above formulas (1-1) to (1-3) and a second compound represented by the above formula (2-1).
- the first compound problem 2 compound may be included in a weight ratio of, for example, 1:99 to 99: 1.
- the electron transport ability of the first compound can be adjusted to a proper weight ratio using the hole transporting ability of the compound 2, Implementation can improve efficiency and lifetime.
- a weight ratio of about 10:90 to 90:10 about 20:80 to 80:20, such as about 20:80, about 70:30, about 20:80 to about 60:40, And in a weight ratio of about 20:80 to about 50:50.
- a weight ratio of 20:80 to 40:60 and can be included in a specific ratio, for example, 20:80, 30:70, or 40:60 by weight.
- the aforementioned compound or composition may be a host.
- the above-mentioned compounds may further include one or more compounds.
- composition may contain, in addition to the above-mentioned first compound and second compound,
- the above-described compounds or compositions may further comprise a dopant.
- the dopant may be, for example, a phosphorescent dopant, for example a red, green or blue phosphorescent dopant, for example a red or green phosphorescent dopant.
- the dopant is a water-gauge that is mixed with a small amount of light to cause luminescence, and a metal that emits light by multiple excitation,
- a metal complex may be used.
- the dopant may be, for example, an inorganic, an organic, or an organic compound, and may include one or two or more species.
- Examples of the dopant include a phosphorescent dopant.
- Examples of the phosphorescent dopant include Ir, Pt,
- Examples of the phosphorescent dopant include, but are not limited to, compounds represented by the following formulas: ???????? 2019/146938 20 1 ????? (201)
- M is a gold ligand, and are the same or different from each other and are ligands which form a complex with M. .
- M is, for example,
- 1 / and X may be, for example, bidentate ligands.
- the compound or composition can be formed by a dry film forming method such as chemical vapor deposition.
- organic optoelectronic device to which the above-described compound or composition is applied will be described.
- the organic optoelectronic device is not particularly limited as long as it is capable of converting electric energy and light energy into each other, and examples thereof include organic optoelectronic devices, organic light emitting devices, organic solar cells, and organic photoconductor drums.
- the organic light emitting device 100 is an organic layer (10 5) located between the positive electrode 120, excessive drinking electrode 110, and anode 120, binge pole 110 which face each other, .
- the anode 120 may be made, for example, of a high work function conductive body to facilitate hole injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer.
- the anode 120 may be made of a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or an alloy thereof; zinc oxide, indium oxide, indium tin oxide (110)
- Metal oxides such as indium zinc oxide (Mo 0); 23 ⁇ 4 ⁇ wasin 3 ⁇ 40 or a combination of a metal and an oxide, such as 2 and;? Poly (3-methyl thiophene), poly (3, 4- (ethylene-1,2-dioxy) thiophene) (1 01 ⁇ 16 116 ( 3 ⁇ 40 ⁇ 11101)] 1 to £ 1) 1 '), it includes a conductive polypyrrole and aniline sound, but is not limited to this.
- the cathode 110 may be made of a conductive material having a low work function for facilitating electron injection, and may be made of a metal, a metal oxide, and / or a conductive polymer .
- the cathode 110 is made of a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lyrium, gadolinium, aluminum, silver, tin, lead, cesium, barium or the like or an alloy thereof; Layer structure materials such as LiF / Al, LiO 2 / Al, LiF / Ca, LiF / Al and BaF 2 / Ca.
- the organic layer 105 includes a light emitting layer 130 comprising the above-described compound or composition.
- Emissum 130 can be, for example, encapsulated in the aforementioned compound or composition.
- composition comprising the compound represented by the above-mentioned formula (1) or the compound represented by the formula (1) and the compound represented by the formula (2)
- the organic light emitting device 200 further includes a hole-assist layer H0 in addition to the light-emitting layer 130.
- the hole assist layer 140 can further enhance hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.
- the hole-assist layer 140 may be, for example, a hole transport layer, a hole injection layer, and / or an electron blocking layer, and may include at least one layer.
- the organic layer 105 may further include an electron transport layer, an electron injection layer, a hole injection layer, and the like, as shown in FIG. 1 or 2.
- the organic light emitting devices 100 and 200 may be formed by forming an anode or a cathode on a substrate,
- a dry film forming method such as vacuum evaporation, sputtering, plasma plating and ion plating, and then forming a cathode or anode thereon.
- the organic light emitting device described above can be applied to an organic light emitting display.
- a more specific example of the compound of the present invention is synthesized through the following steps.
- HostIO Compound HostlO was synthesized by reference to the synthetic method of patent WO2017-069258.
- Compound No. 0-1 was synthesized by referring to the synthesis method of Patent No. 101-2014-0042630.
- the cyclic voltammetry consisting of EC-Epsilon (BAS) (bioanalytical systems Inc. USA) and c-3 cell stand was used to measure HOMO and LUMO of each compound By way of Respectively.
- the potential of ferrocene was set to -4.8 eV compared to the energy level of vacuum, and then a solution of tetrabutylammonium tetrafluoroborate dissolved in dichloromethane solvent at a concentration of 0.1 M was used as the electrolyte using the reference electrode Ag / Ag +.
- the HOMO and LUMO energy levels were calculated using the following equations.
- Redox is the potential potential and Ei / ⁇ Ferrocene) is the half-wave potential of ferrocene.
- the HOMO energy values of Compound 1, Compound 2, Compound 4, Compound 11, Compound 15, Compound 20 and Compound 22 were -5.80 Or more, and the primary 0 energy 2019/146938 39 1 ((1/10) Since the value of 019/000402 is -2.40 eV or less, it can be predicted that hole / electron injection and migration are more desirable than Host 1 to Host 10.
- the glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500A was washed with distilled water ultrasonic wave. After washing with distilled water, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, and methanol, dried and transferred to a plasma cleaner Next, the substrate was cleaned using oxygen plasma for 10 minutes, and then the substrate was transferred to a co-evaporation apparatus. Then, compound A was vacuum deposited on the ITO substrate using the prepared ITO transparent electrode as an anode to form a hole injection layer having a thickness of 700 A Compound B was deposited to a thickness of 50 A on the injection layer, and Compound C was deposited to a thickness of 1020 A to form a hole transport layer.
- ITO Indium tin oxide
- the organic light emitting device has a structure having five organic thin film layers. Specifically, the organic light emitting device has the following structure.
- EXAMPLES 1 TO 18 The driving voltage, the luminous efficiency and the lifespan characteristics of the organic luminescent device according to Comparative Examples 1 to 21 were evaluated.
- the current flowing through the unit device was measured using a current-voltmeter (Fig. 11 72400) while increasing the voltage from 10 V to 10 V, dividing the measured current by the area, .
- a voltage The luminance was measured using a luminance meter (Minolta Cs-1000A) while the luminance was increased to 10 ⁇ .
- Brightness / 1 ⁇ 2 2 was maintained at 6000 0 (1/111 2 , and the time at which the current efficiency / time decreased to 97% was measured to obtain the results.
- the organic light emitting devices according to Examples 1 to 18 have remarkably improved driving voltage, luminous efficiency, and lifetime characteristics as compared with the organic light emitting devices according to Comparative Examples 1 to 21. This is because Exemplary Compounds Compared to the Compounds of the Examples
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Abstract
화학식 1로 표현되는 화합물, 이를 포함하는 조성물, 유기 광전자 소자 표시 장치에 관한 것이다. 상기 화학식 1의 정의는 명세서에서 정의한 바와 같다.
Description
【명세서】
【발명의 명칭】
화합물,조성물,유기 광전자소자및 표시 장치
【기술분야】
화합물,조성물,유기 광전자소자및 표시 장치에 관한것이다.
【배경기술】
유기 광전자소자 (organic optoelectronic diode)는전기 에너지와광에너지를 상호전환할수 있는소자이다.
유기 광전자소자는동작원리에 따라크게 두가지로나눌수 있다. 하나는 광에너지에 의해 형성된 엑시톤 (exciton)이 전자와정공으로분리되고전자와 정공이 각각다른전극으로전달되면서 전기 에너지를발생하는광전소자이고, 다른하나는전극에 전압또는전류를공급하여 전기 에너지로부터 광에너지를 발생하는발광소자이다.
유기 광전자소자의 예로는유기 광전소자,유기 발광소자,유기 태양전지 및유기 감광체 드럼 (organic photo conductor drum)등을들수있다.
이 중,유기 발광소자 (organic light emitting diode, OLED)는근래 평판표시 장치 (flat panel display device)의 수요증가에 따라크게주목받고 있다.유기 발광 소자는전기 에너지를빛으로전환시키는소자로서,유기 발광소자의 성능은전극 사이에 위치하는유기 재료에 의해 많은영향을받는다.
【발명의 상세한설명】
【기술적 과제】
일구현예는고효율및 장수명 유기 광전자소자를구현할수 있는유기 광전자소자용화합물을제공한다.
다른구현예는상기 화합물을포함하는유기 광전자소자용조성물을 제공한다.
또다른구현예는상기 화합물또는조성물을포함하는유기 광전자소자를 제공한다.
또다른구현예는상기 유기 광전자소자를포함하는표시 장치를제공한다. 【기술적 해결방법】
일구현예에 따르면,하기 화학식 1로표현되는제 1화합물을제공한다.
2019/146938 1»(:1/10公019/000402
[화학식 1]
상기 화학식 1에서,
II1내지 II14는각각독립적으로수소,중수소,치환또는비치환된 01 내지 020알킬기 ,치환또는비치환된 06내지 012아릴기,시아노기 또는이들의 조합이고,
II1및 II2는각각독립적으로존재하거나서로연결되어 고리를형성하고,
^및 II4는각각독립적으로존재하거나서로연결되어 고리를형성하고,
I;은단일결합,치환또는비치환된 6내지 030아릴렌기,또는치환또는 비치환된 02내지 030헤테로아릴렌기이고,
111 및 113은각각독립적으로 0또는 1의 정수이고,
112는 1의 정수이다.
다른구현예에 따르면,상기 화학식 1로표현되는제 1 화합물,및 하기 화학식 2로표현되는제 2화합물을포함하는조성물을제공한다.
2019/146938 1»(:1^1{2019/000402
[화학식 2]
상기 화학식 2에서,
\}및 I?은각각독립적으로단일결합,치환또는비치환된 06내지 030 아릴렌기,또는치환또는비치환된 02내지 030헤테로아릴렌기이고,
및 는각각독립적으로치환또는비치환된 06내지 030아릴기 또는 치환또는비치환된 02내지 030헤테로고리기이고,
II15내지 0은각각독립적으로수소,중수소,치환또는비치환된 01 내지 010알킬기,치환또는비치환된 06내지 030아릴기,치환또는비치환된 02내지 030헤테로고리기이고,시아노기,또는이들의 조합이고,
111은 0내지 2의 정수중하나이다.
또다른구현예에 따르면,서로마주하는양극과음극,상기 양극과상기 음극사이에 위치하는적어도 1층의 유기층을포함하고,상기 유기층은상기 화합물 또는조성물을포함하는유기 광전자소자를제공한다.
또다른구현예에 따르면,상기 유기 광전자소자를포함하는표시 장치를 제공한다.
【발명의 효과】
고효율장수명 유기 광전자소자를구현할수 있다.
【도면의 간단한설명】
도 1 및도 2는각각일구현예에 따른유기 발광소자를도시한단면도이다.
<부호의 설명>
100, 200:유기 발광소자
105:유기증
2019/146938 1»(:1^1{2019/000402
110:음극
120:양극
130:발광층
140:정공보조층
【발명의 실시를위한최선의 형태】
이하,본발명의 구현예를상세히 설명하기로한다. 다만,이는예시로서 제시되는것으로,이에 의해 본발명이 제한되지는않으며 본발명은후술할 청구범위의 범주에 의해 정의될뿐이다.
본명세서에서 "치환”이란별도의 정의가없는한,치환기 또는화합물중의 적어도하나의 수소가중수소,할로겐기,히드록실기,아미노기,치환또는비치환된 01 내지 030아민기,니트로기,치환또는비치환된 01 내지 040실릴기,(:1 내지 030알킬기, 내지 010알킬실릴기, 06내지 030아릴실릴기, 03내지 030 시클로알킬기, 03내지 030헤테로시클로알킬기, 06내지 030아릴기, 02내지 030 헤테로아릴기,(그1내지 020알콕시기,(그1 내지 010트리플루오로알킬기,시아노기, 또는이들의 조합으로치환된 것을의미한다.
아릴실릴기, 03내지 030시클로알킬기, 03내지 030헤테로시클로알킬기, 06내지 030아릴기, 02내지 030헤테로아릴기,또는시아노기로치환된 것을의미한다. 또한,본발명의 구체적인 일 예에서,”치환”은치환기 또는화합물중의 적어도 하나의 수소가중수소,(:1 내지 020알킬기, 06내지 030아릴기,또는시아노기로 치환된것을의미한다.또한,본발명의 구체적인 일 예에서,”치환’'은치환기 또는 화합물중의 적어도하나의 수소가중수소,(그1 내지 05알킬기, 06내지 018아릴기, 시아노기로치환된 것을의미한다.또한,본발명의 구체적인 일 예에서,"치환”은 치환기 또는화합물중의 적어도하나의 수소가중수소,시아노기,메틸기,에틸기, 프로필기,부틸기,페닐기,바이페닐기,터페닐기 또는나프틸기로치환된것을 의미한다.
본명세서에서 "헤테로”란별도의 정의가없는한,하나의 작용기 내에凡0, !5및와로이루어진군에서 선택되는헤테로원자를 1 내지 3개 함유하고, 나머지는탄소인 것을의미한다.
본명세서에서 ’’아릴 (aryl)기”는탄화수소방향족모이어티를하나이상갖는 그룹을총괄하는개념으로서,탄화수소방향족모이어티의 모든원소가 p-오비탈을 가지면서,이들 p_오비탈이 공액 (conjugation)을형성하고 있는형태,예컨대 페닐기, 나프틸기 등을포함하고 , 2이상의 탄화수소방향족모이어티들이 시그마결합을 통하여 연결된형태,예컨대 바이페닐기,터페닐기,쿼터페닐기 등을포함하며 , 2 이상의 탄화수소방향족모이어티들이 직접 또는간접적으로융합된 비방향족융합 고리,예컨대 플루오레닐기 등을포함할수있다.
아릴기는모노시클릭,폴리시클릭 또는융합고리 폴리시클릭 (즉,
탄소원자들의 인접한쌍들을나눠 가지는고리)작용기를포함한다. '
본명세서에서 "헤테로고리기 (heterocyclic group)”는헤테로아릴기를포함하는 상위 개념으로서,아릴기,시클로알킬기,이들의 융합고리 또는이들의 조합과같은 고리 화합물내에 탄소 (C)대신 N, O, S, P및 Si로이루어진군에서 선택되는 헤테로원자를적어도한개를함유하는것을의미한다.상기 헤테로고리기가 융합고리인 경우,상기 헤테로고리기 전체 또는각각의 고리마다헤테로원자를한 개 이상포함할수있다.
일 예로 "헤테로아릴 (heteroaryl)기”는아릴기 내에 N, O, S, P및 Si로이루어진 군에서 선택되는헤테로원자를적어도한개를함유하는것을의미한다 . 2이상의 헤테로아릴기는시그마결합을통하여 직접 연결되거나,상기 헤테로아릴기가 2 이상의 고리를포함할경우, 2이상의 고리들은서로융합될수 있다. 상기
헤테로아릴기가융합고리인경우,각각의 고리마다상기 헤테로원자를 1 내지 3개 포함할수있다.
보다구체적으로,치환또는비치환된 C6내지 C30아릴기는,치환또는 비치환된페닐기 ,치환또는비치환된나프틸기 ,치환또는비치환된 안트라세닐기 , 치환또는비치환된페난트레닐기,치환또는비치환된나프타세닐기,치환또는 비치환된피레닐기,치환또는비치환된바이페닐기,치환또는비치환된 p-터페닐기, 치환또는비치환된 m-터페닐기,치환또는비치환된 o-터페닐기,치환또는
비치환된크리세닐기,치환또는비치환된트리페닐렌기,치환또는비치환된 페릴레닐기,치환또는비치환된플루오레닐기,치환또는비치환된 인데닐기 또는 이들의 조합일수있으나,이에 제한되지는않는다.
보다구체적으로,치환또는비치환된 C2내지 C30헤테로고리기는,치환
2019/146938 1»(:1^1{2019/000402 또는비치환된퓨라닐기,치환또는비치환된티오페닐기,치환또는비치환된 피롤릴기,치환또는비치환된피라졸릴기,치환또는비치환된 이미다졸일기,치환 또는비치환된트리아졸일기,치환또는비치환된옥사졸일기 ,치환또는비치환된 티아졸일기,치환또는비치환된옥사디아졸일기,치환또는비치환된
티아디아졸일기,치환또는비치환된피리딜기,치환또는비치환된피리미디닐기, 치환또는비치환된피라지닐기,치환또는비치환된트리아지닐기,치환또는 비치환된벤조퓨라닐기,치환또는비치환된 벤조티오페닐기,치환또는비치환된 벤즈이미다졸일기,치환또는비치환된 인돌일기,치환또는비치환된퀴놀리닐기, 치환또는비치환된 이소퀴놀리닐기,치환또는비치환된퀴나졸리닐기,치환또는 비치환된퀴녹살리닐기,치환또는비치환된나프티리디닐기,치환또는비치환된 벤즈옥사진일기 ,치환또는비치환된 벤즈티아진일기 ,치환또는비치환된
아크리디닐기,치환또는비치환된페나진일기,치환또는비치환된페노티아진일기, 치환또는비치환된페녹사진일기,치환또는비치환된카바졸일기,치환또는 비치환된디벤조퓨란일기 ,또는치환또는비치환된디벤조티오펜일기 ,또는이들의 조합일수있으나,이에 제한되지는않는다.
본명세서에서,정공특성이란,전기장 ;¾11)을가했을때 전자를 공여하여 정공을형성할수 있는특성을말하는것으로, 1크01\40준위를따라전도 특성을가져 양극에서 형성된정공의 발광층으로의 주입,발광층에서 형성된정공의 양극으로의 이동및 발광층에서의 이동을용이하게 하는특성을의미한다.
또한전자특성이란,전기장을가했을때 전자를받을수 있는특성을말하는 것으로, LUM◦준위를따라전도특성을가져 음극에서 형성된 전자의 발광층으로의 주입,발광층에서 형성된 전자의 음극으로의 이동및 발광층에서의 아동을용이하게 하는특성을의미한다.
본명세서에서 "서로연결되어 고리를형성’’이란인접한기끼리 서로
연결되어 치환또는비치환된방향족고리 또는치환또는비치환된헤테로방향족 고리를형성하는것을의미한다.
일 예로,”서로연결되어 고리를형성’’이란인접한기끼리서로연결되어 치환 또는비치환된방향족고리를형성하는것을의미하고,
더욱구체적으로,인접한기끼리 서로연결되어 치환또는비치환된페닐기 등을형성하는것을의미한다.
2019/146938 7 1»(:1^1{2019/000402 이하일구현예에 따른유기광전자소자용화합물을설명한다.
일구현예에 따른유기광전자소자용화합물은하기 화학식 1로표현된다. [화학식 1]
상기 화학식 1에서,
II1내지 II14는각각독립적으로수소,중수소,치환또는비치환된 01 내지 020알킬기,치환또는비치환된 06내지 012아릴기,시아노기 또는이들의 조합이고,
II1및 는각각독립적으로존재하거나서로연결되어 고리를형성하고, II3및요4는각각독립적으로존재하거나서로연결되어 고리를형성하고, 은단일결합,치환또는비치환된 06내지 030아릴텐기,또는치환또는 비치환된 02내지 030헤테로아릴렌기이고,
111 및 은각각독립적으로 0또는 1의 정수이고,
는 1의 정수이다.
화학식 1로표현되는화합물은트리아진을중심으로카바졸,트리페닐텐, 그리고페닐기가연결되고,카바졸과트리아진사이에 적어도하나의 111 크- 페닐텐기를포함하며,트리페닐텐과트리아진은연결기 없이 직접 연결되어 입체적이고비대칭인분자구조를갖는다.
카바졸과트리아진사이에 적어도하나의
페닐렌 링커를포함함으로써 상대적으로此 10 한묘01 0값을갖게 되어 정공주입 및 이동에 유리하고, 트리페닐렌과트리아진이 연결기 없이 직접 연결됨으로써 상대적으로( 6!)한 1乂1\10
에너지 준위를갖게 되어 전자주입 및 이동에 유리하다.
즉,화학식 1로표현되는화합물을포함하는소자에서는정공/전자주입 및 이동이 유리하여 수명에 유리한특성을가질수있다.
또한,트리아진코어에 카바졸을치환함으로써 바이폴라특성을강화하고, 카바졸을 N-방향으로치환하여 C-N결합을통한 71-결합이 끊어지게 되므로
HOMO-LUMO간전자구름이 지역화되어 수명 개선효과가극대화될수 있다.
상기 화학식 1로표현되는화합물에 대하여 HOMO에너지 준위를산출해 보면 예컨대 -6.0 eV내지 -5.0 eV일수있고,구체적으로 -5.8 eV내지 -5.2 eV일수 있고,더욱구체적으로 -5.8 eV내지 -5.5 eV일수 있으며,가장구체적으로 -5.8 eV 내지 -5.7 eV일수있다.
또한, LUMO에너지 준위를산출해보면 예컨대 -2.2 eV내지 -2.9 eV일수 있고,구체적으로 -2.3 eV내지 -2.8 eV일수 있고,더욱구체적으로 -2.4 eV내지 - 2.75 eV일수 있다.
상기 HOMO에너지 준위와 LUMO에너지 준위는 BAS(bioanalytical systems Inc. USA)사의 EC-Epsilon과 c-3 cell stand로구성된순환전압전류법 (CV, cyclic
voltammetry)을이용하여 즉정하였고,구체적인즉정 방법은하기와같다.
Ferrocene의 전위를진공의 에너지 준위에 비하여 -4.8 eV로정한후,
기준전극으로 Ag/Ag+¾-사용하고, tetrabutylammonium tetrafluoroborate이
dichloromethane용매에 0.1 M농도로녹아있는용액을전해질로사용하였다.
Ferrocene및각각의 화합물을 100 mV/sec속도로즉정한후,하기 계산식을
사용하여 HOMO에너지 준위 및 LUMO에너지 준위를계산하였다.
계산식
HOMO(or LUMO)(eV) = -4.8 -(Eonset-E i /2(F erro cene))
여기서 Eonset는 redox가시작되는전위이고 Ei/2(Ferrocene)은 ferrocene의
반파전위 (half-wave potential)이다.
일반적으로그린도펀트의 HOMO에너지 준위 및 LUMO에너지 준위는 각각 -5.5 eV내지 -5.0 eV및 -2.9 eV내지 -2.5 eV사이에서 형성된다.호스트의
HOMO에너지 준위와도펀트의 HOMO에너지 준위의 차이 및/또는호스트의
LUMO에너지 준위와도펀트의 LUMO에너지 준위의 차이가 O eV내지 0.2 eV일 경우 exciton을형성하기에 매우유리해 진다.만약상기한범위를벗어날경우
2019/146938 9 1»(:1^1{2019/000402 소자의 가깨질 우려가크다.
예컨대,상기 0£111+113£1일수있다.
일 예로, 112는 1이고, 111 및 은모두 0일수있다.
일 예로,쑈는 1이고, 111은 1이며, 113은 0일수 있다.
일 예로, 112는 1이고, 111은 0이며, 113은 1일수 있다.
구체적인 일 예로,상기 화학식 1은하기 화학식 1-1 내지 화학식 1-6중어느 하나로표현될수 있다.
[화학식 1-1] [화학식 1-2]
[화학식 1-5] [화학식 1-6]
상기 화학식 1-1내지 화학식 1-6에서, II1내지 II14및 의 정의는전술한 바와같다.
일 예로,상기 화학식 1로표현되는화합물은상기 화학식 1-1 내지 화학식 1-
3중어느하나로표현될수있으나,이에 한정되는것은아니다.
일 예로, II1내지 4는각각독립적으로수소,메틸기,에틸기,페닐기, 바이페닐기 ,나프틸기 또는시아노기일수 있다.
일 예로, II1내지 II4는각각독립적으로수소또는 06내지 012아릴기일수 있다.
예컨대 및 는각각독립적으로존재하거나서로연결되어 치환또는 비치환된방향족고리를형성할수 있다.
예컨대 ^및 #는각각독립적으로존재하거나서로연결되어 치환또는 비치환된방향족고리를형성할수 있다.
일 예로, 내지묘4는각각독립적으로존재할수있고,예컨대수소또는 페닐기일수있으나,이에 한정되는것은아니다.
일 예로, II1및 II2또는 II3및 II4가서로연결되어 치환또는비치환된 방향족고리를형성할수있고예컨대 하기 화학식 내지 화학식 10중어느 하나로표현될수있으나,이에 한정되는것은아니다.
2019/146938 11 1»(:1/10公019/000402
[화학식 1리 [화학식 11]
상기 화학식 내지 화학식 에서,모1내지 4, 그리고 111 내지 113의 정의는전술한바와같고,
및: 는각각독립적으로수소,중수소,치환또는비치환된 01 내지 020 알킬기,치환또는비치환된 C6내지 012아릴기,시아노기 또는이들의 조합이다. 일 예로,상기 ^및 0는모두수소일수 있으나,이에 한정되는것은아니다. 일 예로상기 II5내지묘9는각각독립적으로수소,<31 내지 05알킬기, 06 내지 012아릴기 또는시아노기일 수 있다.
구체적인 일 예로상기 ¥내지 는각각독립적으로수소,메틸기,에틸기, 페닐기 또는시아노기일수있으나,이에 한정되는것은아니다.
일 예로상기 111 )및 1은각각독립적으로수소, 내지 05알킬기, 06
2019/146938 12 1»(:1^1{2019/000402 내지 012아릴기 또는시아노기일 수 있다.
111 크-바이페닐기, 0x1:110 -바이페닐기, 크 -바이페닐기 또는시아노기일수있으나,이에 한정되는것은아니다.
일 예로상기 2내지 II14는각각독립적으로수소,(그1 내지 05알킬기, 06 내지 012아릴기 또는시아노기일수 있다.
구체적인 일 예로상기 2내지 4는각각독립적으로수소,메틸기,에틸기, 페닐기 또는시아노기일수있으나,이에 한정되는것은아니다.
일 예로상기 은단일결합,또는치환또는비치환된 06내지 020 아릴렌기일수있다.
구체적인 일 예로상기 은단일 결합,치환또는비치환된페닐텐기,치환 또는비치환된바이페닐텐기,치환또는비치환된터페닐렌기,치환또는비치환된 나프틸렌기일수있다.
예컨대,상기 은단일 결합,치환또는비치환된 111페닐렌기,치환또는 비치환된 페닐텐기,치환또는비치환된 0 -페닐렌기 ,치환또는비치환된 111
바이페닐렌기 ,치환또는비치환된 바이페닐렌기,치환또는비치환된 0
바이페닐렌기,치환또는비치환된 111-터페닐텐기,치환또는비치환된 I)-터페닐텐기 또는치환또는비치환된 0 -터페닐렌기일수 있다.
예컨대,상기 은단일결합이거나하기 그룹 I에 나열된 치환또는
비치환된 연결기 중하나일수있다.
예컨대 화학식 1로표현되는화합물은하기 그룹 1에 나열된화합물에서 선택된하나일수있으나,이에 한정되는것은아니다.
[그룹 1]
다른일구현예에 따른유기 광전자소자용조성물은전술한화합물 (이하 "제 1화합물’’),및 하기 화학식 2로표현되는제 2화합물을포함한다.
[화학식 2]
상기 화학식 2에서,
\}및 I?은각각독립적으로단일결합,치환또는비치환된 06내지 030 아릴렌기,또는치환또는비치환된 02내지 030헤테로아릴렌기이고,
및 는각각독립적으로치환또는비치환된 06내지 030아릴기 또는 치환또는비치환된 02내지 030헤테로고리기이고,
모15내지 112은각각독립적으로수소,중수소,치환또는비치환된 01 내지 010알킬기,치환또는비치환된 06내지 030아릴기,치환또는비치환된 02내지 030헤테로고리기,시아노기,또는이들의 조합이고,
III은 0내지 2의 정수중하나이다.
상기 제 2화합물은상기 제 1 화합물과함께 발광층에 사용되어 전하의 이동성을높이고안정성을높임으로써 발광효율및수명 특성을개선시킬수있다.
2019/146938 15 1»(:1/10公019/000402 일 예로,상기 화학식 2는하기 그룹 II에 나열된구조중하나를포함할수 있다.
[그룹 □]
예컨대,화학식 2는하기 화학식 2-1또는화학식 2-2로표현될수 있다.
[화학식 2-1] [화학식 2-2]
상기 화학식 2-1 및 2-2에서, I?및 1八 및 2,묘15내지 ^°,그리고 III의 정의는전술한바와같다.
일 예로,상기 \}및 I?는각각독립적으로단일 결합또는치환또는 비치환된 06내지 020아릴렌기일수 있다.
예컨대,느2및 3는각각독립적으로단일 결합,치환또는비치환된페닐렌기, 치환또는비치환된바이페닐렌기,치환또는비치환된 터페닐텐기,치환또는 비치환된나프틸렌기일수 있다.
예컨대, I?및 3는각각독립적으로단일 결합,치환또는비치환된 111-
2019/146938 16 1»(:1^1{2019/000402 페닐렌기,치환또는비치환된 페닐렌기,치환또는비치환된 0 -페닐텐기,치환 또는비치환된 111-바이페닐렌기,치환또는비치환된 바이페닐텐기,치환또는 비치환된 0 -바이페닐렌기,치환또는비치환된 111-터페닐렌기,치환또는비치환된 터페닐렌기 또는치환또는비치환된 0 -터페닐렌기일 수 있다. 여기서 치환은 예컨대 적어도하나의 수소가중수소,(그1 내지 020알킬기, 06내지 020아릴기, 할로겐,시아노기 또는이들의 조합으로치환된 것일수있으나,이에 한정되는 것은아니다.
일 예로,상기 및 은각각독립적으로치환또는비치환된 06내자 030 아릴기일수있다.
예컨대, 및 은각각독립적으로치환또는비치환된페닐기,치환또는 비치환된바이페닐기,치환또는비치환된터페닐기,치환또는비치환된나프틸기, 치환또는비치환된안트라세닐기,치환또는비치환된페난트레닐기,치환또는 비치환된트리페닐레닐기,치환또는비치환된플루오레닐기,또는이들의 조합일 수있다.
예컨대, 및 은각각독립적으로치환또는비치환된페닐기,치환또는 비치환된 111-바이페닐기,치환또는비치환된 I)-바이페닐기,치환또는비치환된 0- 바이페닐기,치환또는비치환된나프틸기,또는이들의 조합일수있다.
예컨대,상기 *-1入 및 * 3- 는각각독립적으로하기 그룹 III에 나열된 치환기 중하나일수있으나,이에 한정되는것은아니다.
[그룹 III]
예컨대 화학식 2로표현되는화합물은하기 그룹 2에 나열된화합물에서 선택된하나일수있으나,미에 한정되는것은아니다.
f- 2]
일 예로조성물은상기 화학식 1-1내지 화학식 1-3중어느하나로표현되는 제 1 화합물과상기 화학식 2-1로표현되는제 2화합물을포함할수 있다.
제 1화합물과제 2화합물은예컨대 1:99내지 99:1의 중량비로포함될수 있다.상기 범위로포함됨으로써 제 1 화합물의 전자수송능력과제 2화합물의 정공 수송능력을이용해 적절한중량비를맞추어 바이폴라특성을구현하여 효율과 수명을개선할수있다. 상기 범위 내에서 예컨대 약 10:90내지 90:10,약 20:80 내지 80:20의 중량비로포함될수있고,예컨대 약 20:80내자 약 70: 30,약 20:80 내지 약 60:40,그리고약 20:80내지 약 50:50의 중량비로포함될수 있다. 일 예로, 20:80내지 40:60의 중량비로포함될수있으며,구체적인 일 예로, 20:80, 30:70,또는 40:60의 중량비로포함될수있다.
일 예로전술한화합물또는조성물은호스트일 수있다.
전술한화합물은 1종이상의 화합물을더 포함할수있다.
전술한조성물은전술한제 1화합물및 제 2화합물외에 1종이상의
화합물을더 포함할수있다.
전술한화합물또는조성물은도펀트를더 포함할수있다.도펀트는예컨대 인광도펀트일수있고,예컨대 적색,녹색또는청색의 인광도펀트일수있고, 예컨대 적색또는녹색의 인광도펀트일수있다.
도펀트는미량혼합되어 발광을일으키는물걸로,일반적으로삼중항상태 이상으로여기시키는다중항여기 (multiple excitation)에 의해 발광하는금속
착체 (metal complex)와같은물질이 사용될수 있다.도펀트는예컨대무기,유기, 유무기 화합물일수있으며, 1종또는 2종이상포함될수 있다.
도펀트의 일 예로인광도펀트를들수있으며,인광도펀트의 예로는 Ir, Pt,
Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd또는이들의 조합을포함하는유기
2019/146938 20 1»(:1^1{2019/000402 금속화합물을들수있다.인광도펀트는예컨대 하기 화학식 로표현되는 화합물을사용할수 있으나,이에 한정되는것은아니다.
[화학식 z\ 상기 화학식 å에서, M은금속이고, 및 는서로같거나다르며 M과 착화합물을형성하는리간드이다. .
이들의 조합알수있고,상기 1/및 X는 예컨대 바이덴테이트리간드일수있다. 화합물이나조성물은화학기상증착과같은건식 성막법에 의해 형성될수 있다.
이하상술한화합물또는조성물을적용한유기 광전자소자를설명한다. 유기 광전자소자는전기 에너지와광에너지를상호전환할수있는 소자아면특별히 한정되지 않으며,예컨대 유기 광전소자,유기 발광소자,유기 태양전지 및유기 감광체드럼 등을들수 있다.
여기서는유기 광전자소자의 일 예인유기 발광소자를도면을참고하여 설명한다.
도 1 및도 2는일구현예에 따른유기 발광소자를보여주는단면도이다. 도 1을참고하면,일구현예에 따른유기 발광소자 (100)는서로마주하는 양극 (120)과음극 (110),그리고양극 (120)과음극 (110)사이에 위치하는유기층 (105)을 포함한다.
양극 (120)은예컨대 정공주입이 원활하도록일 함수가높은도전체로 만들어질수있으며,예컨대 금속,금속산화물및/또는도전성 고분자로만들어질 수있다. 양극 (120)은예컨대 니켈,백금,바나듐,크롬,구리,아연,금과같은금속 또는이들의 합금;아연산화물,인듐산화물,인듐주석산화물 (110),
인듐아연산화물 (모0)과같은금속산화물; 2¾◦와신또는 ¾02와 와같은금속과 산화물의 조합;폴리 (3 -메틸티오펜),폴리 (3, 4-(에틸렌- 1,2- 디옥시)티오펜) (1?01} 16116(¾0}11101)]1해 £1)1'),폴리피롤및 들리아닐린과같은 도전성 고분자등을들수있으나,이에 한정되는것은아니다.
음극 (110)은예컨대 전자주입이 원활하도록일 함수가낮은도전체로 만들어질수있으며,예컨대금속,금속산화물및/또는도전성 고분자로만들어질
수있다. 음극 (110)은예컨대마그네슘,칼슘,나트륨,칼륨,타이타늄,인둠,이트륨, 리륨,가돌리늄,알루미늄,은,주석,납,세슘,바륨등과같은금속또는이들의 합금; LiF/Al, Li02/Al, LiF/Ca, LiF/Al및 BaF2/Ca과같은다층구조물질을들수 있으나,이에 한정되는것은아니다.
유기층 (105)은전술한화합물또는조성물을포함하는발광층 (130)을포함한다. 발광증 (130)은예컨대 전술한화합물또는조성물을포담할수있다.
예컨대,전술한화학식 1로표현되는화합물또는화학식 1로표현되는 화합물및 화학식 2로표현되는화합물을포함하는조성물은발광층내에
호스트로서 포함될수있다.
도 2를참고하면,유기 발광소자 (200)는발광층 (130)외에 정공보조층 (H0)을 더 포함한다. 정공보조층 (140)은양극 (120)과발광층 (130)사이의 정공주입 및/또는정공이동성을더욱높이고전자를차단할수있다. 정공보조층 (140)은 예컨대 정공수송층,정공주입층및/또는전자차단층일수 있으며,적어도 1층을 포함할수있다.
또한,본발명의 일구현예에서는도 1또는도 2에서 유기층 (105)으로서 추가로전자수송층,전자주입층,전공주입층등을더 포함한유기 발광소자일 수도있다.
유기 발광소자 (100, 200)는기판위에 양극또는음극을형성한후,
진공증착법 (evaporation),스퍼터링 (sputtering),플라즈마도금및 이온도금과같은 건식성막법 등으로유기층을형성한후,그위에 음극또는양극을형성하여 제조할 수있다.
상술한유기 발광소자는유기 발광표시 장치에 적용될수있다.
【발명의 실시를위한형태】
이하실시예를통하여 상술한구현예를보다상세하게 설명한다. 다만 하기의 실시예는단지 설명의 목적을위한것이며 권리범위를제한하는것은 아니다.
이하,실시예 및 합성예에서 사용된출발물질 및 반응물질은특별한언급이 없는한, Sigma- Aldrich St, TCI /¾, tokyo chemical industry또는 P&H tech에서
구입하였거나,공지된방법을통해 합성하였다.
2019/146938 22 1»(:1/10公019/000402
(유기 광전자소자용화합물의 제조)
본발명의 화합물의 보다구체적인 예로사제시된화합물을하기 단계를 통해 합성하였다.
(제 1화합물의제조)
합성예 1:중간체 1-1의합성
질소환경에서 4,4,555-tetramethyl-2-(triphenylen-2-yl)-l,3,2-dioxaborolane(50 g, 141 mmol)을 tetrahydrofiiran(THF) 0.5 L에 녹인후,여기에 2,4-dichloro-6-phenyl- 1 ,3,5- triazine(47.9 g, 212 mmol)와 tetrakis(triphenylphosphine)palladium(1.63 g, 1.41 mmol)을 넣고교반시켰다.그리고물에 포화된 potassium carbonate(48.7 g, 353 mmol)을넣고 80 °C에서 12시간동안가열하여 환류시켰다.반응완료후반응액에 물을넣고 dichloromethane(DCM)로추출한다음 magnesium sulfate anhydrous로수분을제거한투, 필터하고감압농축하였다.이렇게 얻어진 잔사를 flash column chromatography로분리 정제하여 중간체 1-1(40.1 g, 68 %)를얻었다.
HRMS (70 eV, EI+): m/z calcd for C27H16C1N3: 417.1033, found: 417.
Elemental Analysis: C, 78 %; H, 4 % 합성예 2:중간체 1-2의합성
1 - 2
질소환경에서 9H-carbazole(100 g, 598 mmol)을 toluene 1.0 L에 녹인투,여기에
1 -bromo-3-chlorobenzene(l 37 g, 718 mmol), tris(dibenzylideneacetone)dipalladium(0)(5.48 g, 5.98 mmol), tris-tert butylphosphine(0.60 g, 0.30 mmol)그리고 sodium tert-butoxide(69.0 g,
2019/146938 23 1»(:1/10公019/000402
718 mmol)을순차적으로넣고 110°C에서 18시간동안가열하여 환류시켰다.반응 완료후반응액에 물을넣고 dichloromethane(DCM)로추출한다음 magnesium sulfate anhydrous로수분을제거한후,필터하고감압농죽하였다.이렇게 얻어진잔사를 flash column chromatography로분리 정제하여 중간체 1-2(118 g, 71 %)를얻었다.
HRMS (70 eV, EI+): m/z calcd for C18H12C1N: 277.0658, found: 277.
질소환경에서 중간체 1-2(100용, 360 11111101)를 111하11 £01111크111 6 ]\417) 1.0 에 녹인투,여기에 bis(pinacolato)diboron (110 g, 432 mmol)와 (1,1’- bis(diphenylphosphine)ferrocene)dichloropalladium(II)(2.94 g, 3.60 mmol)그리고 potassium acetate(106 & 1,080 mmol)을넣고 150 °C에서 20시간동안가열하여 환류시켰다. 반응완료후반응액에 물을넣고혼합물을필터한후,진공오븐에서 건조하였다. 이렇게 얻어진잔사를 flash column chromatography로분리 정제하여 중간체 1-3(113 g, 85 %)를얻었다.
HRMS (70 eV, EI+): m/z calcd for C24H24BN02: 369.1900, found: 369.
합성예 1과동일한방법으로중간체 1-1(10 & 23.9 11111101)과중간체 1-3(8.83 &
2019/146938 24 1»(:1/10公019/000402
23.9 mmol)를사용하여 화합물 1(14.6 g, 98 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C45H28N4: 624.2314, found: 624.
합성예 1과동일한방법으로 4,4,5,5나 111 1171-2-( 1)1伯11> 11-2- 1)-1,3,2- 0ᄌ )01‘01 50 & 141ᄆ1!]101)과 2-(biphenyl-4-yl)-4?6-dichloro- 1,3, 5-10 azine(64.0 ¾ 212 11111101)를사용하여 중간체 1-4(46.0 & 66 %)를얻었다.
합성예 1과동일한방법으로중간체 1-4(10 g, 20.2 mmol)와중간체 1-3(7.48 g,
20.2 mmol)를사용하여 화합물 2(13.4 g, 95 %)를얻었다.
HRMS (70 eV, EI+): m/z calcd for C51H32N4: 700.2627, found: 700.
Elemental Analysis: C, 87 %; H, 5 % 합성예 7:중간체 1-5의합성
2019/146938 25 1»(:1/10公019/000402
합성예 1과동일한방법으로 4-chlorophenylboronic acid(100 g, 640 mmol)과 1- bromo-2-iodobenzene(199 g, 703 mmol)를사용하여 중간체 1-5(152 g, 89 %)를얻었다.
HRMS (70 eV, EI+): m/z calcd for C12H8BrCl: 265.9498, found: 266.
합성예 3과동일한방법으로중간체 1-5(150 ^ 477 1111X101)를사용하여 중간체 I - 6(135 & 90 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C18H20BC1O2: 314.1245, found: 314.
합성예 1과동일한방법으로중간체 1-6(130 & 413 _01)과 3-^000-4- 10(101넜|)11611 (163은, 455 11111101)를사용하여 중간체 1-7(161 ¾ 93 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C24H16BrCl: 418.0124, found: 418.
Elemental Analysis: C, 69 %; H, 4 %
2019/146938 26 1»(:1/10公019/000402 합성예 10:중간체 1-8의합성
질소환경에서 중간체 1-7(155 & 369 mmol)을 xylene 0.5 L에 녹인후,여기에 bis(dibenzylideneacetone)palladium(0)(6.37 g, 11.1 mmol)와 triphenylphosphine(9.67 g, 36.9 mmol)그리고 cesium carbonate(120 g, 369 mmol)을넣고 140 °C에서 27시간동안 가열하여 환류시켰다.반응완료후반응액에 물을넣고산比111이0111 11 여 [)로 주줄한다음 magnesium sulfate anhydrous로수분을제거한후,필터하고감압 농축하였다.이렇게 얻어진잔사를 flash column chromatography로분리 정제하여 중간체 1-8(87.5 g, 70 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C24H15C1: 338.0862, found: 338.
합성예 3과동일한방법으로중간체 1-8(80 ¾ 236 11111101)을사용하여 중간체 I -
9(67.0 ^ 66 %)를얻었다.
HRMS (70 eV? EI+): m/z calcd for C30H27BO2: 430.2104, found: 430.
Elemental Analysis: C? 84 %; H, 6 % 합성예 12:중간체 1-10의 합성
2019/146938 27 1»(:1/10公019/000402
합성예 1과동일한방법으로중간체 1-9(50 ¾ 116 11111101)와 2,4-(1 111이:0-6-|)11611 - 1,3,54! 39.4 & 174 1101)를사용하여 중간체 1-10(40.1 & 70 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C33H20C1N3: 493.1346, found: 493.
합성예 1과동일한방법으로중간체 1-10(10 & 20.2 11111101)과중간체 1-3(7.48 20.2 11111101)를사용하여 화합물 4(13.6 & 96 %)를얻었다.
HRMS (70 eV, EI+): m/z calcd for C51H32N4: 700.2627, found: 700.
질소환경에서 magnesium(13.3 g, 549 mmol)과 iodine(2.79 g, 11.0 mmol)을
tetrahydroftiran(THF) 0.1 L에 녹인후,30분간교반시켰다.이투, THF 0.1 L에 녹아있는 3-bromobenzonitrile(100 g, 549 mmol)을 30분간천천히 첨가하였다. 이렇게 만들어잔 grignard시약을 THF 1 L에 녹아있는 cyanuric chloride(12 g, 659 mmol)용액에 30분간
2019/146938 28 1»(:1/10公019/000402 천천히 첨가후 3시간동안교반하였다.반응완료후반응액에 물을넣고
dichloromethane(DCM)로주줄한다음 magnesium sulfate anhydrous로수분을제거한후, 필터하고감압농죽하였다.이렇게 얻어진잔사를 flash column chromatography로분리 정제하여 중간체 1-11(56.5 g, 41 %)를얻었다.
HRMS (70 eV, EI+): m/z calcd for C10H4C12N4: 249.8913, found: 250.
합성예 1과동일한방법으로 4,4,5 5-tetramethyl-2-(triphenylen-2-yl)- 1,3,2- dioxaborolane(50 g, 141 mmol)과중간체 1-11(53.1 g, 212 mmol)를사용하여 중간체 I-
12(30.0 & 48 %)를얻었다.
HRMS (70 eV, EI+): m/z calcd for C28H15C1N4: 442.0985, found: 442.
합성예 1과동일한방법으로중간체 1-12(10 g, 22.6 mmol)와중간체 1-3(8.34 g? 22.6 mmol)를사용하여 화합물 11(11.16 g, 76 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C46H27N5: 649.2266, found: 649.
Elemental Analysis: C, 85 %; H, 4 % 합성예 17:중간체 1-13의 합성
2019/146938 29 1»(:1/10公019/000402
1 - 13 합성예 14와동일한방법으로 3-bromotoluene(100 g, 585 mmol)과 cyanuric chloride(129 g, 702 mmol)를사용하여 중간체 1-13(92.7 g, 66 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C10H7C12N3: 239.0017, found: 239.
합성예 1과동일한방법으로 4,4,5, 5 仕 하뇨 -2-(번 해 해-2- 1)-1, 3,2- dioxaborolane(50 g, 141 mmol)과중간체 1-13(33.9 g, 212 mmol)을사용하여 중간체 I- 14(42.6 & 70 %)를얻었다.
HRMS (70 eV, EI+): m/z calcd for C28H18C1N3: 431.1189, found: 431.
합성예 1과동일한방법으로중간체 1-14(10 & 23.2 11111101)와중간체 1-3(8.55 & 23.2 11111101)를사용하여 화합물 15(13.3 & 90 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C46H30N4: 638.2470, found: 638.
1 - 3 1 - 15
합성예 1과동일한방법으로중간체 1-3(50 g, 135 mmol)와 l-bromo-3- chlorobenzene(28.5 g, 149 mmol)l-사용하여 중간체 1-15(42.5 g, 89 %)를얻었다.
HRMS (70 eV, EI+): m/z calcd for C24H16C1N: 353.0971, found: 353.
합성예 3과동일한방법으로중간체 1-15(40 & 113 11111101)을사용하여 중간체 I - 16(31.2 ^ 62 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C3QH28BN02: 445.2213, found: 445.
합성예 1과동일한방법으로중간체 1-1(10 & 23.9 _01)과중간체 1-16(10.6 & 3.9 11111101)을사용하여 화합물 20(15.9 & 95 %)을얻었다.
묘及^ (70 +): X 0511132 700.2627,꾼_ 1: 700.
2019/146938 31 1»(:1/10公019/000402
bromophenyl)carbazole(50 g, 155 mmol)와 3-chlorophenylboronic acid(26.7 g, 171 mmol)를 사용하여 중간체 1-17(50.5 g, 92 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C24H16C1N: 353.0971, found: 353.
합성예 3과동일한방법으로중간체 1-17(45 g, 127 mmol)을사용하여 중간체 I- 18(41.9 g, 74 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C30H28BNO2: 445.2213, found: 445.
합성예 1과동일한방법으로중간체 1-1(10 g, 23.9 mmol)과중간체 1-18(10.6 g, 23.9 mmol)을사용하여 화합물 22(15.4 g, 92 %)을얻었다.
2019/146938 32 1»(:1/10公019/000402
HRMS (70 eV, EI+): m/z calcd for C51H32N4: 700.2627, found: 700.
합성예 14와동일한방법으로 3-bromobiphenyl(100 g, 429 mmol)과 cyanuric chloride(94.9 g, 515 rnmol 사용하여 중간체 1-19(92.0 g, 71 %)를얻었다.
HRMS (70 eV, EI+): m/z calcd for C15H9C12N3: 301.0174, found: 301.
합성예 1과동일한방법으로 4345555-tetramethyl-2-(triphenylen-2-yl)- 1,3,2- dioxaborolane(50 g, 141 mmol)과중간체 1-19(64.1 g, 212 mmol)을사용하여 중간체 I- 20(43.9 g, 63 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C33H20C1N3: 493.1346, found: 493.
Elemental Analysis: C, 80 %; H, 4 % 비교합성예 1:화합물 110財1의 합성
- 20 Hostl
2019/146938 33 1»(:1/10公019/000402 합성예 2와동일한방법으로중간체 1-20(10 ¾ 20.2 _()1)와 0 20 (3.72 & 22.3 1111x101)을사용하여 화합물 ¾ 1(12.4 & 98 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C45H28N4: 624.2314, found: 624.
Elemental Analysis: C, 87 %; H, 5 % 비교합성예 2:중간체 1-21의 합성
합성예 1과동일한방법으로 4?4,5?5-tetramethyl-2-(3-(triphenylen-2-yl)phenyl)- l,3,2-dioxaborolane(50 g, 116 mmol)과 2,4-dichloro-6-phenyl-l,3,5-triazine(39.4 g, 174 mmol)을사용하여 충간체 1-21(37.2 & 65 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C33H20C1N3: 493.1346, found: 493.
Elemental Analysis: C, 80 %; H, 4 % 비교합성예 3:화합물 1¾0社2의 합성
22.3 1X111101)을사용하여 화합물 ¾ 2(12.0 & 95 %)을얻었다.
HRMS (70 eV, EI+): m/z calcd for C45H28N4: 624.2314, found: 624.
Host3
특허 KR 10-2012-0116282의 합성법을참고하여 화합물 Host3을합성하였다. HRMS (70 eV, EI+): m/z calcd for C33H20N4: 472.1688, found: 472.
Host4
특허 KR 10-2012-0116282의 합성법을참고하여 화합물 Host4를합성하였다. HRMS (70 eV, EI+): m/z calcd for C46H29N3: 623.2361, found: 623.
Host5
특허 KR 10-2012-0116282의 합성법을참고하여 화합물 Host5를합성하였다.
2019/146938 35 1»(:1/10公019/000402
HRMS (70 eV, EI+): m/z calcd for C57H35N5: 789.2892, found: 789.
Elemental Analysis: C, 87 %; H, 4 % 비교합성예 7:화합물 Host6의 합성
Host6
특허 KR 10-2012-0116282의 합성법을참고하여 화합물 Host6을합성하였다. HRMS (70 eV, EI+): m/z calcd for C46H29N3: 623.2361, found: 623.
Host7
특허 KR 10-2014-0113483의 합성법을참고하여 화합물 Host7을합성하였다. HRMS (70 eV, EI+): m/z calcd for C47H30N2: 622.2409, found: 623.
Host8
특허 WO2017-069258의 합성법을참고하여 화합물 Host8을합성하였다. HRMS (70 eV, EI+): m/z calcd for C40H25N3: 547.2048, found: 547.
Host9
특허 WO2017-069258의 합성법을참고하여 화합물 Host9를합성하였다. HRMS (70 eV, EI+): m/z calcd for C46H29N3: 623.2361, found: 623.
Elemental Analysis: C, 89 %; H, 5 % 비교합성예 11:화합물 1¾0 10의 합성
HostIO
2019/146938 37 1»(:1/10公019/000402 특허 WO2017-069258의 합성법을참고하여 화합물 HostlO을합성하였다. HRMS (70 eV, EI+): m/z calcd for C46H29N3: 623.2361, found: 623.
Elemental Analysis: C, 89 %; H, 5 % 합성예 28:화합물이의 합성
특허 101 10-2014-0042630의 합성법을참고하여 화합물 0-1을합성하였다.
HRMS (70 eV, EI+): m/z calcd for C36H24N2: 484.1939, found: 484.
Elemental Analysis: C, 89 %; H, 5 % 합성예 29:화합물<:-10의 합성
특허 KR 10-2014-0042630의 합성법을참고하여 화합물 C-10을합성하였다. HRMS (70 eV, EI+): m/z calcd for C48H32N2: 636.2565, found: 636.
Elemental Analysis: C, 91 %; H? 5 %
(순환전압전류법 (CV, cyclic voltammetry)을이용한에너지준위측정) BAS(bioanalytical systems Inc. USA)사의 EC-Epsilon과 c-3 cell stand로구성된 Cyclic Voltammetry을사용하여 각화합물의 HOMO및 LUMO를하기의 방법으로
측정 하였다.
우선 Ferrocene의 전위를진공의 에너지 준위에 비하여 -4.8 eV로정한후, 기준전극 Ag/Ag+를사용하고 tetrabutylammonium tetrafluoroborate이 dichloromethane 용매에 0.1 M농도로녹아있는용액을전해질로사용하였다. Ferrocene및 각각의 화합물을 100 mV/sec속도로측정한후,하기 계산식을사용하여 HOMO및 LUMO 에너지 준위를계산하였다.
<계산식 >
HOMO (이· LUMO)(eV) = -4.8-(Eonset-El/2(Ferrocene))
[표 1]
표 1을참고하면,화합물 1,화합물 2,화합물 4,화합물 11,화합물 15, 화합물 20및 화합물 22의 HOMO에너지 값은 -5.80
이상이고, 1차 0에너지
2019/146938 39 1»(:1/10公019/000402 값은 -2.40 eV이하이므로, Host 1 내지 Host 10에 비해 정공/전자주입 및 이동이 원할 할것으로예측할수있다.
(유기 발광소자의 제작)
실시예 1
ITO (Indium tin oxide)가 1500A의 두께로박막코팅된유리 기판을증류수 초음파로세척하였다.증류수세척이 끝나면 이소프로필 알코올,아세톤,메탄올 등의 용제로초음파세척을하고건조시킨후플라즈마세정기로이송시킨다음 산소플라즈마를이용하여 상기 기판을 10분간세정 한후진공증착기로기판을 이송하였다.이렇게준비된 ITO투명 전극을양극으로사용하여 ITO기판상부에 화합물 A를진공증착하여 700 A두께의 정공주입층을형성하고상기 주입층 상부에 화합물 B를 50 A의 두께로증착한후,화합물 C를 1020 A의 두께로 증착하여 정공수송층을형성하였다.정공수송층상부에 상기에서 합성예 4에서 얻은 화합물 1과합성예 29에서 얻은화합물 C-10을동시에 호스트로사용하고도판트로 트리스 (2 -페닐피리딘)이리듐 (III) [Ir(ppy)3]를 10wt%로도핑하여 진공증착으로 400 A 두께의 발광층을형성하였다. 여기서 화합물 1과화합물 C-1은 3:7비율로 사용되었다.이어서 상기 발광층상부에 화합물 D와 Liq를동시에 1:1 비율로진공 증착하여 300A두께의 전자수송층을형성하고상기 전자수송층상부에 Liq l5A과 A1 1200A을순차적으로진공증착하여 음극을형성함으로써 유기발광소자를 제작하였다.
상기 유기발광소자는 5층의 유기 박막층을가지는구조로되어 있으며, 구체적으로다음과같다.
ITO/화합물 A(700A)/화합물 B(50A)/화합물 C(1020A)/EML [화합물 1:화합물 C- 10:Ir(ppy)3 = X:X:10%](400A)/화합물 D:Liq(300A)/Liq(15A)/Al(1200A)의 구조로 제작하였다 . (X=중량비)
화합물 A: N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazol-3-yl)biphenyl-4,4'- diamine
화합물 B: 1?4?5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN),
화합물 C:N-(biphenyl-4-yl)-9?9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)- 911-£111(江 -2 11 116
2019/146938 40 1»(:1^1{2019/000402 화합물 I): 8-(4-(4,6-di(naphthalen-2-yl)-l,3,5-triazin-2-yl)phenyl)quinolme 실시예 2내지 18
표 2에 기재된조성으로변경한것을제외하고는,상기 실시예 1과동일한 방법으로유기발광소자를제작하였다. 비교예 1내지 21
표 2에 기재된조성으로변경한것을제외하고는,상기 실시예 1과동일한 방법으로유기발광소자를제작하였다 . 평가
실시예 1 내지 18과비교예 1 내지 21에 따른유기발광소자의 구동전압, 발광효율및 수명특성을평가하였다.
구체적인측정방법은하기와같고,그결과는표 2와같다.
(1)전압변화에 따른전류밀도의 변화측정
제조된유기발광소자에 대해,전압을◦V부터 10¥까지 상승시키면서 전류- 전압계 (도 11 72400)를이용하여 단위소자에 흐르는전류값을측정하고,측정된 전류값을면적으로나누어 결과를얻었다.
(2)전압변화에 따른휘도변화측정
(3)발광효율측정
(4)수명 측정
휘도 /½ 2)를 60000(1/111 2로유지하고전류효율 /시이 97%로감소하는 시간을측정하여 결과를얻었다.
(5)구동전압측정
[표 2]
표 2를참고하면,실시예 1 내지 18에 따른유기발광소자는비교예 1내지 21에 따른유기발광소자와비교하여 구동전압,발광효율및수명특성이 현저하게 개선된 것을확인할수있다.이는비교예의 화합물이 실시예의 화합물에 비해
일어나분자에 무리를주기 때문인 것으로추측된다. 이상에서 본발명의 바람직한실시예들에 대하여 상세하게 설명하였지만본 발명의 권리범위는이에 한정되는것은아니고다음의 청구범위에서 정의하고 있는본발명의 기본개념을이용한당업자의 여러 변형 및 개량형태또한본 발명의 권리범위에 속하는것이다.
Claims
[화학식 1]
상기 화학식 1에서,
모1내지 4는각각독립적으로수소,중수소,치환또는비치환된 01내지 020알킬기,치환또는비치환된 6내지 012아릴기,시아노기 또는이들의 조합이고,
및 II2는각각독립적으로존재하거나서로연결되어 고리를형성하고,
II3및 II4는각각독립적으로존재하거나서로연결되어 고리를형성하고, 은단일결합,치환또는비치환된 C6내지 030아릴렌기,또는치환또는 비치환된 02내지 030헤테로아릴텐기이고,
111 및 3은각각독립적으로 0또는 1의 정수이고,
112는 1의 정수이다.
【청구항 2]
제 1항에 있어서,
하기 계산식에 의해산출된 HOMO에너지 준위는 -6.0 eV내지 -5.0 eV이고, LUMO에너지 준위는 -2.2 eV내지 -2.9 eV인화합물:
<계산식 >
HOMO/LUMO에너지 준위 (eV)= -4.8-(Eonset-E1/2(Ferrocene)).
(Eonset: redox가시작되는전위, Ei/2(Ferrocene): ferrocene의 반파전위 (half-wave potential))
【청구항 3】
제 1항에 있어서,
상기 0£nl+n3£l인화합물.
【청구항 4】
제 1항에 있어서,
상기 화학식 1은하기 화학식 1-1 내지 화학식 1-6중어느하나로표현되는 화합물:
[화학식 14] [화학식 1-2]
[화학식 1-5] [화학식 1-6]
상기 화학식 1-1 내지 화학식 1-6에서,
내지 4는각각독립적으로수소,중수소,치환또는비치환된(그1 내지
020알킬기,치환또는비치환된 06내지 012아릴기,시아노기 또는이들의 조합이고,
II1및 는각각독립적으로존재하거나서로연결되어 고리를형성하고,
II3및 II4는각각독립적으로존재하거나서로연결되어 고리를형성하고, 은단일결합,치환또는비치환된 06내지 030아릴렌기,또는치환또는 비치환된 02내지 030헤테로아릴렌기이다.
【청구항 5]
제 1항에 있어서,
하기 그룹 1에 나열된화합물중하나인화합물:
[그룹 1]
5 6 8
【청구항 6]
제 1항에 있어서,
도펀트를더 포함하는조성물.
【청구항 7] ·
제 6항에 있어서,
【청구항 8]
제 1화합물,및 제 2화합물을포함하고,
상기 제 1 화합물은상기 제 1항의 화학식 1로표현되고,
상기 제 2화합물은하기 화학식 2로표현되는조성물:
[화학식 2]
상기 화학식 2에서,
\}및 I?은각각독립적으로단일결합,치환또는비치환된 06내지 030 아릴렌기,또는치환또는비치환된 02내지 030헤테로아릴텐기이고,
1및 는각각독립적으로치환또는비치환된 06내지 030아릴기 또는 치환또는비치환된 02내지 030헤테로고리기이고,
2019/146938 48 1»(:1^1{2019/000402
111은 0내지 2의 정수중하나이다.
【청구항 9】
제 8항에 있어서,
상기 화학식 2는하기 화학식 2-1또는화학식 2-2로표현되는조성물:
[화학식 2-1] [화학식 2-2]
상기 화학식 2-1 및 2-2에서,
1}및 I?은각각독립적으로단일결합,치환또는비치환된 06내지 030 아릴텐기,또는치환또는비치환된 02내지 030헤테로아릴렌기이고,
V 및 는각각독립적으로치환또는비치환된 06내지 030아릴기 또는 치환또는비치환된 02내지 030헤테로고리기이고,
5내지 112은각각독립적으로수소,중수소,치환또는비치환된 01내지 010알킬기,치환또는비치환된 06내지 030아릴기,치환또는비치환된 02내지 030헤테로고리기,시아노기,또는이들의 조합이고,
111은 0내지 2의 정수중하나이다.
【청구항 10】
제 8항에 있어서,
하나인조성물:
상기 그룹 III에서, *은연결지점이다.
【청구항 11】
제 8항에 있어서,
상기 제 1화합물은하기 화학식 1-1 내지 화학식 1-3중어느하나로 표현되고,
상기 제 2화합물은하기 화학식 2-1로표현되는조성물:
[화학식 1-1] [화학식 1-2]
상기 화학식 1-1 내지 화학식 1-6에서,
내지 II14는각각독립적으로수소,중수소,
내지 020알킬기,치환또는비치환된 06내지 012아릴기,시아노기 또는이들의
2019/146938 50 1»(:1'/10{2019/000402 조합이고,
및 는각각독립적으로존재하거나서로연결되어 고리를형성하고,
II3및 II4는각각독립적으로존재하거나서로연결되어 고리를형성하고, 은단일결합,치환또는비치환된 C6내지 030아릴렌기,또는치환또는 비치환된 02내지 030헤테로아릴렌기이고;
[화학식 2-1]
상기 화학식 2-1에서,
\}및 은각각독립적으로단일결합,치환또는비치환된 06내지 030 아릴텐기,또는치환또는비치환된 02내지 030헤테로아릴렌기이고,
및 는각각독립적으로치환또는비치환된 06내지 030아릴기 또는 치환또는비치환된 02내지 030헤테로고리기이고,
II15내지 II2ᄋ은각각독립적으로수소,중수소,치환또는비치환된 01 내지 010알킬기,치환또는비치환된 06내지 030아릴기,치환또는비치환된 02내지 030헤테로고리기 ,시아노기,또는이들의 조합이고,
III은 0내지 2의 정수중하나이다.
【청구항 12】
제 8항에 있어서,
도펀트를더 포함하는조성물.
【청구항 13】
제 12항에 있어서,
상기 제 1화합물및상기 제 2화합물을포함하는호스트와상기 도펀트의 HOMO에너지 준위 차;및상기 제 1 화합물및 상기 제 2화합물을포함하는 호스트와상기 도펀트의 1^ 0에너지 준위 차중적어도하나는 0.2 인조성물.
2019/146938 51 1»(:1^1{2019/000402
【청구항 14】
서로마주하는양극과음극,
상기 양극과상기 음극사이에 위치하는적어도 1층의 유기층을포함하고, 상기 유기층은제 1항내지 제 7항중어느한항에 따른화합물,또는제 8항 내지 제 13항중어느한항에 따른조성물을포함하는유기 광전자소자.
【청구항 15】
제 14항에 있어서,
상기 유기층은발광층을포함하고,
상기 발광층은상기 화합물또는상기 조성물을포함하는유기 광전자소자. 【청구항 16】
제 14항에 따른유기 광전자소자를포함하는표시 장치.
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KR102495275B1 (ko) * | 2019-10-02 | 2023-02-01 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 화합물, 유기 광전자 소자 및 표시 장치 |
KR102503221B1 (ko) * | 2019-11-21 | 2023-02-27 | 엘티소재주식회사 | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
KR102669240B1 (ko) * | 2020-11-04 | 2024-05-24 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치 |
CN112802970B (zh) * | 2020-12-27 | 2022-07-05 | 浙江华显光电科技有限公司 | 一种组合物及包含其的有机电致发光元件 |
KR20230102741A (ko) * | 2021-12-30 | 2023-07-07 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치 |
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US11926603B2 (en) | 2024-03-12 |
CN111655679A (zh) | 2020-09-11 |
KR102524650B1 (ko) | 2023-04-21 |
KR20190090204A (ko) | 2019-08-01 |
US20210130304A1 (en) | 2021-05-06 |
CN111655679B (zh) | 2023-11-21 |
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