KR20240087115A - Organic compound and electroluminescent device comprising the same - Google Patents
Organic compound and electroluminescent device comprising the same Download PDFInfo
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- KR20240087115A KR20240087115A KR1020220172490A KR20220172490A KR20240087115A KR 20240087115 A KR20240087115 A KR 20240087115A KR 1020220172490 A KR1020220172490 A KR 1020220172490A KR 20220172490 A KR20220172490 A KR 20220172490A KR 20240087115 A KR20240087115 A KR 20240087115A
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- 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- JZIRXBHGSUKMLQ-UHFFFAOYSA-N N-(2-phenylphenyl)dibenzofuran-3-amine Chemical compound C1(=C(C=CC=C1)NC=1C=CC2=C(OC3=C2C=CC=C3)C=1)C1=CC=CC=C1 JZIRXBHGSUKMLQ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 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
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 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
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical group C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- GHQCIALFYKYZGS-UHFFFAOYSA-N dibenzofuran-3-amine Chemical compound C1=CC=C2C3=CC=C(N)C=C3OC2=C1 GHQCIALFYKYZGS-UHFFFAOYSA-N 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical group C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000005921 isopentoxy group Chemical group 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006610 n-decyloxy group Chemical group 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000006609 n-nonyloxy group Chemical group 0.000 description 1
- 125000006608 n-octyloxy group Chemical group 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005484 neopentoxy group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 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
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005580 triphenylene group Chemical group 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
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- 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
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
본 발명은 하기 [화학식 Ⅰ]로 표시되는 유기 화합물로서, 청색, 녹색, 적색 각 파장대에서의 굴절률 값이 종래의 정공수송 재료에 비하여 낮은 굴절률을 가져서 이를 정공수송층에 채용하여 소자를 구성하는 경우 유기발광소자의 효율 최적화를 기대할 수 있으며, 이에 따라 본 발명에 따른 화합물을 소자 내의 정공수송층 등에 채용하는 경우, 발광 효율, 양자 효율 등 발광 특성이 매우 우수한 유기발광소자의 구현이 가능하다.
[화학식 Ⅰ]
The present invention is an organic compound represented by the following [Chemical Formula I], which has a lower refractive index value in each of the blue, green, and red wavelength bands compared to conventional hole transport materials, so when it is used in the hole transport layer to construct a device, the organic compound Optimization of the efficiency of the light-emitting device can be expected, and accordingly, when the compound according to the present invention is employed in the hole transport layer within the device, it is possible to implement an organic light-emitting device with excellent light-emitting properties such as luminous efficiency and quantum efficiency.
[Formula Ⅰ]
Description
본 발명은 유기 화합물에 관한 것으로서, 보다 구체적으로는 유기발광소자 내의 정공수송층 등의 유기층에 채용되는 유기 화합물 및 이를 채용하여 저전압 구동, 장수명, 발광 효율 등의 소자 특성이 현저히 향상된 유기발광소자에 관한 것이다.The present invention relates to organic compounds, and more specifically, to organic compounds employed in organic layers such as hole transport layers in organic light-emitting devices, and to organic light-emitting devices whose device characteristics, such as low-voltage operation, long life, and luminous efficiency, are significantly improved by employing the same. will be.
유기발광소자는 투명 기판 위에도 소자를 형성할 수 있을 뿐 아니라, 플라즈마 디스플레이 패널 (Plasma Display Panel)이나 무기전계발광 (EL) 디스플레이에 비해 10 V 이하의 저전압 구동이 가능하고, 전력 소모가 비교적 적으며, 색감이 뛰어나다는 장점이 있고, 녹색, 청색, 적색의 3가지 색을 나타낼 수가 있어 최근에 차세대 디스플레이 소자로 많은 관심의 대상이 되고 있다.Organic light emitting devices not only can be formed on transparent substrates, but also can be driven at low voltages of 10 V or less compared to plasma display panels or inorganic electroluminescence (EL) displays, and consume relatively little power. , It has the advantage of excellent color and can display three colors of green, blue, and red, so it has recently been the subject of much attention as a next-generation display device.
다만, 이러한 유기발광소자가 상기와 같은 특징으로 발휘하기 위해서는 소자 내 유기층을 이루는 물질인 정공주입 물질, 정공수송 물질, 정공저지 물질, 발광 물질, 전자수송 물질, 전자주입 물질, 전자저지 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 하나, 아직까지는 안정하고 효율적인 유기발광소자용 유기층 재료의 개발이 충분히 이루어지지 않은 상태이다.However, in order for this organic light-emitting device to exhibit the above characteristics, the materials that make up the organic layer within the device, such as hole injection material, hole transport material, hole blocking material, light emitting material, electron transport material, electron injection material, and electron blocking material, are required. Support by stable and efficient materials should be a priority, but the development of stable and efficient organic layer materials for organic light-emitting devices has not yet been sufficiently developed.
따라서, 재료의 광학적 특성과 발광 특성을 개선할 수 있는 새로운 재료의 개발과 소자 내 유기층 구조에 대한 개발이 계속 요구되고 있는 실정이다.Therefore, there is a continued need for the development of new materials that can improve the optical and luminous properties of materials and the development of organic layer structures within devices.
따라서, 본 발명은 유기발광소자 내의 정공수송층 등의 유기층 재료로 채용되어 저전압 구동 특성과, 장수명, 발광 효율 등의 소자 특성을 현저히 향상시킬 수 있는 유기 화합물 및 이를 포함하는 유기발광소자를 제공하고자 한다.Therefore, the present invention seeks to provide an organic compound that can be used as an organic layer material such as a hole transport layer in an organic light-emitting device to significantly improve device characteristics such as low-voltage driving characteristics, long life, and luminous efficiency, and an organic light-emitting device containing the same. .
본 발명은 상기 과제를 해결하기 위하여, 하기 [화학식 Ⅰ]로 표시되는 유기 화합물 및 이를 정공수송층 등의 유기층에 포함하는 유기발광소자를 제공한다.In order to solve the above problems, the present invention provides an organic compound represented by the following [Chemical Formula I] and an organic light-emitting device containing the same in an organic layer such as a hole transport layer.
[화학식 Ⅰ][Formula Ⅰ]
상기 [화학식 Ⅰ]의 구체적인 구조와 이에 의하여 구현되는 구체적인 화합물, 그리고 R1 및 Ar1 내지 Ar3의 정의에 대해서는 후술한다.The specific structure of [Chemical Formula I], the specific compounds implemented thereby, and the definitions of R 1 and Ar 1 to Ar 3 will be described later.
본 발명에 따른 유기 화합물을 정공수송층 등의 유기층에 채용한 유기발광소자는 종래 소자에 비하여 저전압 구동, 장수명 특성, 발광 효율 등의 소자 특성이 현저히 우수하여 다양한 조명 소자 및 디스플레이 소자 등에 유용하게 사용될 수 있다.The organic light-emitting device employing the organic compound according to the present invention in an organic layer such as a hole transport layer is significantly superior to conventional devices in device characteristics such as low-voltage operation, long lifespan, and luminous efficiency, and can be usefully used in various lighting devices and display devices. there is.
이하, 본 발명을 더욱 상세하게 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명은 하기 [화학식 Ⅰ]로 표시되는 유기 화합물에 관한 것으로서, 유기발광소자 내의 다양한 유기층에, 바람직하게는 정공수송층 등에 채용하는 경우에 저전압 구동, 장수명, 발광 효율 등의 소자 특성이 현저히 향상된 유기발광소자의 구현이 가능하다.The present invention relates to an organic compound represented by the following [Chemical Formula I], which has significantly improved device characteristics such as low-voltage driving, long life, and luminous efficiency when employed in various organic layers in an organic light-emitting device, preferably in a hole transport layer. It is possible to implement a light emitting device.
또한, 본 발명에 따른 하기 [화학식 Ⅰ]로 표시되는 유기 화합물은 청색, 녹색, 적색 각 파장대 (450, 520, 630 nm)에서의 굴절률 값이 종래의 정공수송 재료에 비하여 낮은 굴절률을 가져서 이를 정공수송층에 채용하여 소자를 구성하는 경우 유기발광소자의 효율 최적화를 기대할 수 있다.In addition, the organic compound represented by the following [Chemical Formula I] according to the present invention has a lower refractive index value in each of the blue, green, and red wavelength bands (450, 520, and 630 nm) compared to conventional hole transport materials, and thus When used in the transport layer to form a device, optimization of the efficiency of the organic light emitting device can be expected.
[화학식 Ⅰ][Formula Ⅰ]
상기 [화학식 Ⅰ]에서,In the above [Chemical Formula I],
R1은 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 치환 또는 비치환된 탄소수 1 내지 20의 할로겐화된 알킬기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬실릴기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬저마늄기 및 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기 중에서 선택되며, n은 1 내지 4의 정수이고, 상기 n이 2 이상인 경우 복수 개의 R1은 서로 동일하거나 상이하다.R 1 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. It is selected from an alkyl germanium group having to 20 carbon atoms and a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, n is an integer of 1 to 4, and when n is 2 or more, a plurality of R 1 is the same or different from each other.
Ar1은 치환 또는 비치환된 탄소수 6 내지 30의 아릴기인 것을 특징으로 한다.Ar 1 is characterized in that it is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
본 발명의 일 실시예에 의하면, 상기 Ar1은 할로겐기, 알킬기 및 시클로알킬기 중에서 선택된 1종 이상을 치환기로 갖는 치환된 탄소수 6 내지 30의 아릴기일 수 있다.According to one embodiment of the present invention, Ar 1 may be a substituted aryl group having 6 to 30 carbon atoms having at least one selected from a halogen group, an alkyl group, and a cycloalkyl group as a substituent.
본 발명의 일 실시예에 의하면, 상기 Ar1은 할로겐기; 및 알킬기와 시클로알킬기 중에서 선택된 어느 하나;를 각각 반드시 치환기로 더 포함하는 치환된 탄소수 6 내지 30의 아릴기일 수 있다.According to one embodiment of the present invention, Ar 1 is a halogen group; and any one selected from an alkyl group and a cycloalkyl group; each may be a substituted aryl group having 6 to 30 carbon atoms, which further includes a substituent.
Ar2 내지 Ar3은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴기 및 상기 [구조식 1] 중에서 선택된다.Ar 2 to Ar 3 are the same or different from each other, and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and the above [Structural Formula 1] .
본 발명에 있어서 상기 Ar2 내지 Ar3에서 정의된 아릴기는 플루오레닐기를 제외한 아릴기인 것을 특징으로 하고, Ar2 내지 Ar3 정의에서 제외된 치환 또는 비치환된 플루오레닐기는 하기 [구조식 1]로 별도로 명확하게 정의한다.In the present invention, the aryl group defined by Ar 2 to Ar 3 is characterized in that it is an aryl group excluding a fluorenyl group, and the substituted or unsubstituted fluorenyl group excluded from the definition of Ar 2 to Ar 3 is represented by the following [structural formula 1] It is clearly defined separately.
[구조식 1][Structural Formula 1]
상기 [구조식 1]에서,In [Structural Formula 1] above,
R2 및 R3은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소, 시아노기, 할로겐기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기 중에서 선택된다.R 2 and R 3 are the same or different from each other, and are each independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, It is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
m 및 o는 각각 0 내지 4의 정수이고, 상기 m 및 o가 각각 2 이상인 경우 복수 개의 R2 및 R3은 각각 서로 동일하거나 상이하다.m and o are each integers from 0 to 4, and when m and o are each 2 or more, a plurality of R 2 and R 3 are the same or different from each other.
R4 및 R5는 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기, 치환 또는 비치환된 탄소수 2 내지 20의 헤테로시클로알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기 중에서 선택된다.R 4 and R 5 are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 20 carbon atoms, or a substituted or unsubstituted group. It is selected from an aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
또한, 상기 R4 및 R5는 서로 연결되어 지환족 또는 방향족의 단일환 또는 다환 고리를 추가 형성할 수 있다.In addition, R 4 and R 5 may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.
본 발명의 일 실시예에 의하면, 상기 R4 및 R5는 각각 독립적으로 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기 및 치환 또는 비치환된 탄소수 6 내지 30의 아릴기 중에서 선택되는 어느 하나일 수 있다.According to one embodiment of the present invention, R 4 and R 5 are each independently selected from a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. You can.
또한, 본 발명의 일 실시에에 의하면, 상기 Ar2 내지 Ar3 중 적어도 하나 이상은 시클로알킬기를 치환기로 갖는 구조체일 수 있다.Additionally, according to one embodiment of the present invention, at least one of Ar 2 to Ar 3 may be a structure having a cycloalkyl group as a substituent.
한편, 상기 R1 및 Ar1 내지 Ar3의 정의에서, 치환 또는 비치환이란 상기 R1 및 Ar1 내지 Ar3가 각각 중수소, 시아노기, 할로겐기, 알킬기, 알콕시기, 할로겐화된 알콕시기, 할로겐화된 알킬기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 실릴기 및 아민기 중에서 선택된 1 또는 2 이상의 치환기로 치환되거나, 상기 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다.Meanwhile, in the definition of R 1 and Ar 1 to Ar 3 , substituted or unsubstituted means that R 1 and Ar 1 to Ar 3 are respectively deuterium, cyano group, halogen group, alkyl group, alkoxy group, halogenated alkoxy group, and halogenated group. is substituted with one or two or more substituents selected from an alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, silyl group and amine group, or is substituted with a substituent in which two or more of the substituents are connected, or any substituent. It means not having it.
구체적인 예를 들면, 치환된 아릴기라 함은, 페닐기, 비페닐기, 나프탈렌기, 플루오레닐기, 파이레닐기, 페난트레닐기, 페릴렌기, 테트라세닐기, 안트라센닐기 등이 중수소 등의 다른 치환기로 치환된 것을 의미하고, 치환된 헤테로아릴기라 함은, 피리딜기, 티오페닐기, 트리아진기, 퀴놀린기, 페난트롤린기, 이미다졸기, 티아졸기, 옥사졸기, 카바졸기 및 이들의 축합헤테로고리기, 예컨대 벤즈퀴놀린기, 벤즈이미다졸기, 벤즈옥사졸기, 벤즈티아졸기, 벤즈카바졸기, 디벤조티오페닐기, 디벤조퓨란기 등이 역시 중수소 등의 다른 치환기로 치환된 것을 의미한다.For specific examples, a substituted aryl group refers to a phenyl group, biphenyl group, naphthalene group, fluorenyl group, pyrenyl group, phenanthrenyl group, perylene group, tetracenyl group, anthracenyl group, etc. substituted with another substituent such as deuterium. means, and substituted heteroaryl group refers to pyridyl group, thiophenyl group, triazine group, quinoline group, phenanthroline group, imidazole group, thiazole group, oxazole group, carbazole group and condensed heterocyclic groups thereof, such as This means that benzquinoline group, benzimidazole group, benzoxazole group, benzthiazole group, benzcarbazole group, dibenzothiophenyl group, dibenzofuran group, etc. are also substituted with other substituents such as deuterium.
본 발명에 있어서, 상기 치환기들의 예시들에 대해서 아래에서 구체적으로 설명하나, 이에 한정되는 것은 아니다.In the present invention, examples of the above substituents will be described in detail below, but are not limited thereto.
본 발명에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 20인 것이 바람직하다. 구체적인 예로는 메틸기, 에틸기, 프로필기, n-프로필기, 이소프로필기, 부틸기, n-부틸기, 이소부틸기, tert-부틸기, sec-부틸기, 1-메틸-부틸기, 1-에틸-부틸기, 펜틸기, n-펜틸기, 이소펜틸기, 네오펜틸기, tert-펜틸기, 헥실기, n-헥실기, 1-메틸펜틸기, 2-메틸펜틸기, 4-메틸-2-펜틸기, 3,3-디메틸부틸기, 2-에틸부틸기, 헵틸기, n-헵틸기, 1-메틸헥실기, 시클로펜틸메틸기, 시클로헥틸메틸기, 옥틸기, n-옥틸기, tert-옥틸기, 1-메틸헵틸기, 2-에틸헥실기, 2-프로필펜틸기, n-노닐기, 2,2-디메틸헵틸기, 1-에틸-프로필기, 1,1-디메틸-프로필기, 이소헥실기, 2-메틸펜틸기, 4-메틸헥실기, 5-메틸헥실기 등이 있으나, 이들에 한정되지 않는다.In the present invention, the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert -Octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, etc., but is not limited to these.
본 발명에 있어서, 알콕시기는 직쇄 또는 분지쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 입체적 방해를 주지 않는 범위인 1 내지 20개인 것이 바람직하다. 구체적으로, 메톡시기, 에톡시기, n-프로폭시기, 이소프로폭시기, i-프로필옥시기, n-부톡시기, 이소부톡시기, tert-부톡시기, sec-부톡시기, n-펜틸옥시기, 네오펜틸옥시기, 이소펜틸옥시기, n-헥실옥시기, 3,3-디메틸부틸옥시기, 2-에틸부틸옥시기, n-옥틸옥시기, n-노닐옥시기, n-데실옥시기, 벤질옥시기, p-메틸벤질옥시기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present invention, the alkoxy group may be straight chain or branched chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20, which is a range that does not cause steric interference. Specifically, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, i-propyloxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentyloxy group. , neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group , benzyloxy group, p-methylbenzyloxy group, etc., but is not limited thereto.
본 발명에 있어서, 상기 알킬기 내지 알콕시기는 중수소화된 알킬기 또는 알콕시기, 할로겐화된 알킬기 또는 알콕시기일 수 있으며, 이는 상기 알킬기 또는 알콕시기가 중수소 또는 할로겐기로 치환된 알킬기 또는 알콕시기를 의미한다.In the present invention, the alkyl group or alkoxy group may be a deuterated alkyl group or alkoxy group, a halogenated alkyl group, or an alkoxy group, which means an alkyl group or alkoxy group in which the alkyl group or alkoxy group is substituted with a deuterium or halogen group.
본 발명에 있어서, 아릴기는 단환식 또는 다환식일 수 있고, 탄소수는 특별히 한정되지 않으나 6 내지 30인 것이 바람직하며, 또한 시클로알킬 등이 융합된 다환식 아릴기 구조를 포함하고, 단환식 아릴기의 예로는 페닐기, 비페닐기, 터페닐기, 스틸벤기 등이 있고, 다환식 아릴기의 예로는 나프틸기, 안트라세닐기, 페난트레닐기, 파이레닐기, 페릴레닐기, 테트라세닐기, 크라이세닐기, 플루오레닐기, 아세나프타센닐기, 트리페닐렌기, 플루오안트렌기 (fluoranthrene) 등이 있으나, 본 발명의 범위가 이들 예로만 한정되는 것은 아니다.In the present invention, the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 30. It also includes a polycyclic aryl group structure fused with cycloalkyl, etc., and the monocyclic aryl group Examples of phenyl group, biphenyl group, terphenyl group, stilbene group, etc. Examples of polycyclic aryl groups include naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, tetracenyl group, and chrysenyl group. , fluorenyl group, acenaphthacenyl group, triphenylene group, fluoranthrene group, etc., but the scope of the present invention is not limited to these examples.
다만, 본 발명의 Ar2 내지 Ar3 정의에서의 아릴기는 플루오레닐기를 제외하고, 제외된 플루오레닐기에 대해서는 상기에서와 같이 별도로 정의한다.However, the aryl group in the definition of Ar 2 to Ar 3 of the present invention excludes the fluorenyl group, and the excluded fluorenyl group is separately defined as above.
본 발명에 있어서, 헤테로아릴기는 이종원자로 O, N 또는 S를 포함하는 헤테로고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 2 내지 30인 것이 바람직하며, 시클로알킬 또는 헤테로시클로알킬 등이 융합된 다환식 헤테로아릴기 구조를 포함하며, 본 발명에서 이의 구체적인 예를 들면, 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 트리아졸기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤조옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 디벤조퓨라닐기, 페난트롤린기, 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 벤조티아졸릴기, 페노티아지닐기, 페녹사진기, 페노티아진기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present invention, the heteroaryl group is a heterocyclic group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and is a polycyclic group fused with cycloalkyl or heterocycloalkyl, etc. It contains a heteroaryl group structure, and specific examples thereof in the present invention include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, and bipyridyl group. , pyrimidyl group, triazine group, triazole group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzooxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, Dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, phenoxazine group, phenothiazine group, etc., but only these It is not limited.
본 발명에 있어서, 실릴기는 비치환된 실릴기 또는 알킬기, 아릴기 등으로 치환된 실릴기로서, 이러한 실릴기의 구체적인 예로는 트리메틸실릴, 트리에틸실릴, 트리페닐실릴, 트리메톡시실릴, 디메톡시페닐실릴, 디페닐메틸실릴, 디페닐비닐실릴, 메틸사이클로뷰틸실릴, 디메틸퓨릴실릴 등을 들 수 있으며, 이에 한정되는 것은 아니다.In the present invention, the silyl group is an unsubstituted silyl group or a silyl group substituted with an alkyl group, an aryl group, etc., and specific examples of such silyl groups include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, and dimethoxysilyl. Examples include phenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, etc., but are not limited thereto.
본 발명에서 사용되는 할로겐기의 구체적인 예로는 플루오르(F), 클로린(Cl), 브롬(Br) 등을 들 수 있다.Specific examples of halogen groups used in the present invention include fluorine (F), chlorine (Cl), and bromine (Br).
본 발명에 있어서, 시클로알킬기는 단환, 다환 및 스피로 알킬 라디칼을 지칭하고, 이를 포함하며, 바람직하게는 탄소수 3 내지 20의 고리 탄소 원자를 함유하는 것으로서, 시클로프로필, 시클로펜틸, 시클로헥실, 비시클로헵틸, 스피로데실, 스피로운데실, 아다만틸 등을 포함하며, 시클로알킬기는 임의로 치환될 수 있다.In the present invention, cycloalkyl groups refer to and include monocyclic, polycyclic and spiro alkyl radicals, and preferably contain ring carbon atoms having 3 to 20 carbon atoms, such as cyclopropyl, cyclopentyl, cyclohexyl, and bicyclo. Includes heptyl, spirodecyl, spiroundecyl, adamantyl, etc., and the cycloalkyl group may be optionally substituted.
본 발명에 있어서, 헤테로시클로알킬기는 하나 이상의 헤테로 원자를 함유하는 방향족 및 비방향족 시클릭 라디칼을 지칭하고, 이를 포함하며, 하나 이상의 헤테로원자는 O, S, N, P, B, Si, 및 Se, 바람직하게는 O, N 또는 S로부터 선택되며, 구체적으로 N을 포함하는 경우 아지리딘, 피롤리딘, 피페리딘, 아제판, 아조칸 등일 수 있다.In the present invention, heterocycloalkyl groups refer to and include aromatic and non-aromatic cyclic radicals containing one or more heteroatoms, wherein one or more heteroatoms are O, S, N, P, B, Si, and Se. , preferably selected from O, N or S, and specifically, when it contains N, it may be aziridine, pyrrolidine, piperidine, azepane, azocan, etc.
본 발명에 있어서, 아민기는 -NH2, 알킬아민기, 아릴아민기, 아릴헤테로아릴아민기 등일 수 있고, 아릴아민기는 아릴로 치환된 아민을 의미하고, 알킬아민기는 알킬로 치환된 아민을 의미하는 것이며, 아릴헤테로아릴아민기는 아릴 및 헤테로아릴기로 치환된 아민을 의미하는 것으로서, 아릴아민기의 예로는 치환 또는 비치환된 모노아릴아민기, 치환 또는 비치환된 디아릴아민기, 또는 치환 또는 비치환된 트리아릴아민기가 있고, 상기 아릴아민기 및 아릴헤테로아릴아민기 중의 아릴기 및 헤테로아릴기는 단환식 아릴기, 단환식 헤테로아릴기일 수 있고, 다환식 아릴기, 다환식 헤테로아릴기일 수 있으며, 상기 아릴기, 헤테로아릴기를 2 이상을 포함하는 아릴아민기, 아릴헤테로아릴아민기는 단환식 아릴기(헤테로아릴기), 다환식 아릴기(헤테로아릴기), 또는 단환식 아릴기(헤테로아릴기)와 다환식 아릴기(헤테로아릴기)를 동시에 포함할 수 있다. 또한, 상기 아릴아민기 및 아릴헤테로아릴아민기 중의 아릴기, 헤테로아릴기는 전술한 아릴기, 헤테로아릴기의 예시 중에서 선택될 수 있다.In the present invention, the amine group may be -NH 2 , an alkylamine group, an arylamine group, an arylheteroarylamine group, etc., an arylamine group refers to an amine substituted with aryl, and an alkylamine group refers to an amine substituted with alkyl. The arylheteroarylamine group refers to an amine substituted with aryl and heteroaryl groups. Examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or There is an unsubstituted triarylamine group, and the aryl group and heteroaryl group in the arylamine group and arylheteroarylamine group may be a monocyclic aryl group, a monocyclic heteroaryl group, or a polycyclic aryl group or a polycyclic heteroaryl group. and the aryl group, the arylamine group containing two or more heteroaryl groups, and the arylheteroarylamine group include a monocyclic aryl group (heteroaryl group), a polycyclic aryl group (heteroaryl group), or a monocyclic aryl group (heteroaryl group). It may contain both an aryl group) and a polycyclic aryl group (heteroaryl group). In addition, the aryl group and heteroaryl group of the arylamine group and arylheteroarylamine group may be selected from examples of the above-mentioned aryl group and heteroaryl group.
또한, 본 발명에 따른 치환기의 다양한 구체적인 예는 하기 기재된 구체적인 화합물에서 명확하게 확인할 수 있다.Additionally, various specific examples of substituents according to the present invention can be clearly identified in the specific compounds described below.
상기 [화학식 Ⅰ]로 표시되는 본 발명에 따른 유기 화합물은 상술한 바와 같이 그 구조적 특이성으로 인하여 유기발광소자의 유기층으로 사용될 수 있고, 보다 구체적으로는 도입되는 다양한 치환기의 특성에 따라 유기층의 정공수송층 등의 재료로 사용될 수 있다.The organic compound according to the present invention represented by [Formula I] can be used as an organic layer of an organic light-emitting device due to its structural specificity as described above, and more specifically, depending on the characteristics of the various substituents introduced, it can be used as a hole transport layer of the organic layer. It can be used as a material such as
본 발명에 따른 [화학식 Ⅰ]로 표시되는 화합물의 바람직한 구체예로는 하기 화합물들이 있으나, 이들에만 한정되는 것은 아니다.Preferred specific examples of the compound represented by [Chemical Formula I] according to the present invention include the following compounds, but are not limited to these.
상기와 같은 특징적 골격 구조 및 치환기를 통하여 골격 구조 및 치환기의 고유 특성을 갖는 유기 화합물을 합성할 수 있으며, 예컨대, 유기발광소자의 제조시 정공수송층 등의 각 유기층에서 요구하는 조건들을 충족시키는 유기발광 화합물 물질을 제조할 수 있으며, 특히, 본 발명에 따른 [화학식 Ⅰ]의 화합물을 정공수송층 등에 채용한 경우 소자의 발광 효율 등의 소자 특성을 더욱 향상시킬 수 있다.Through the above-mentioned characteristic skeletal structure and substituents, organic compounds with unique properties of the skeletal structure and substituents can be synthesized, and, for example, organic light emitting devices meet the conditions required for each organic layer, such as a hole transport layer, when manufacturing an organic light-emitting device. Compound materials can be manufactured, and in particular, when the compound of [Chemical Formula I] according to the present invention is used in the hole transport layer, etc., device characteristics such as luminous efficiency of the device can be further improved.
본 발명에 따른 유기발광 화합물을 이용하여 통상의 제조방법에 따라 유기발광소자에 적용할 수 있다.The organic light-emitting compound according to the present invention can be applied to an organic light-emitting device according to a conventional manufacturing method.
본 발명의 일 실시예에 따른 유기발광소자는 제1 전극과 제2 전극 및 이 사이에 배치된 유기층을 포함하는 구조로 이루어질 수 있으며, 본 발명에 따른 유기 화합물을 소자의 유기층에 사용한다는 것을 제외하고는 통상의 소자의 제조 방법 및 재료를 사용하여 제조될 수 있다.The organic light emitting device according to an embodiment of the present invention may have a structure including a first electrode, a second electrode, and an organic layer disposed between them, except that the organic compound according to the present invention is used in the organic layer of the device. It can be manufactured using conventional device manufacturing methods and materials.
본 발명에 따른 유기발광소자의 유기층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층, 전자저지층 등을 포함하는 구조를 가질 수 있다. 그러나, 이에 한정되지 않고 더 적은 수 또는 더 많은 수의 유기층을 포함할 수도 있다.The organic layer of the organic light emitting device according to the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, etc. However, it is not limited to this and may include fewer or more organic layers.
따라서, 본 발명에 따른 유기발광소자에서, 상기 유기층은 정공수송층 또는 전자저지층을 포함할 수 있고, 상기 층들 중 1층 이상이 상기 [화학식 Ⅰ]로 표시되는 유기 화합물을 포함할 수 있다.Therefore, in the organic light emitting device according to the present invention, the organic layer may include a hole transport layer or an electron blocking layer, and one or more of the layers may include the organic compound represented by [Chemical Formula I].
또한, 본 발명에 따른 유기발광소자는 스퍼터링 (sputtering)이나 전자빔 증발 (e-beam evaporation)과 같은 PVD (physical vapor deposition) 방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공주입층, 정공수송층, 정공저지층, 발광층, 전자저지층, 전자수송층, 전자저지층 등을 포함하는 유기층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다.In addition, the organic light emitting device according to the present invention deposits a metal, a conductive metal oxide, or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation. is deposited to form an anode, and an organic layer including a hole injection layer, a hole transport layer, a hole blocking layer, a light-emitting layer, an electron blocking layer, an electron transport layer, an electron blocking layer, etc. is formed thereon, and then an organic layer that can be used as a cathode is formed thereon. It can be manufactured by depositing the material.
이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기층, 양극 물질을 차례로 증착시켜 유기발광소자를 만들 수도 있다. 상기 유기층은 정공주입층, 정공수송층, 정공저지층, 발광층, 전자저지층, 전자수송층, 전자저지층 등을 포함하는 다층 구조일 수도 있으나, 이에 한정되지 않고 단층 구조일 수 있다. 또한, 상기 유기층은 다양한 고분자 소재를 사용하여 증착법이 아닌 솔벤트 프로세스(solvent process), 예컨대 스핀 코팅, 딥 코팅, 닥터 블레이딩, 스크린 프린팅, 잉크젯 프린팅 또는 열 전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다.In addition to this method, an organic light-emitting device can also be made by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate. The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron blocking layer, an electron transport layer, an electron blocking layer, etc., but is not limited to this and may have a single layer structure. In addition, the organic layer uses a variety of polymer materials to form a smaller number of layers by a solvent process, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than deposition. It can be manufactured in layers.
양극 물질로는 통상 유기층으로 정공주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 본 발명에서 사용될 수 있는 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금, 아연 산화물, 인듐 산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물, ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.As an anode material, a material with a large work function is generally preferred to ensure smooth hole injection into the organic layer. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO). Metal oxides, combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT) , conductive polymers such as polypyrrole and polyaniline, but are not limited to these.
음극 물질로는 통상 유기층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금, LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다.The cathode material is generally preferably a material with a small work function to facilitate electron injection into the organic layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof, multilayers such as LiF/Al or LiO 2 /Al. Structural materials, etc., but are not limited to these.
정공주입 물질로는 낮은 전압에서 양극으로부터 정공을 잘 주입받을 수 있는 물질로서, 정공주입 물질의 HOMO (highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기층의 HOMO 사이인 것이 바람직하다. 정공주입 물질의 구체적인 예로는 금속 포피린 (porphyrine), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴 헥사아자트리페닐렌, 퀴나크리돈 (quinacridone) 계열의 유기물, 페릴렌 (perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.The hole injection material is a material that can easily inject holes from the anode at a low voltage. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene, quinacridone-based organic substances, perylene-based organic substances, Examples include anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited to these.
정공수송 물질로는 양극이나 정공주입층으로부터 정공을 수송 받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. 또한, 본 발명에 따른 [화학식 Ⅰ]로 표시되는 화합물을 이용할 수 있다.The hole transport material is a material that can transport holes from the anode or hole injection layer and transfer them to the light emitting layer, and a material with high mobility for holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these. Additionally, the compound represented by [Chemical Formula I] according to the present invention can be used.
발광 물질로는 정공수송층과 전자수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자효율이 좋은 물질이 바람직하다. 구체적인 예로는 8-히드록시-퀴놀린 알루미늄 착물 (Alq3), 카르바졸 계열 화합물, 이량체화 스티릴 (dimerized styryl) 화합물, BAlq, 10-히드록시벤조 퀴놀린-금속 화합물, 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물, 폴리(p-페닐렌비닐렌) (PPV) 계열의 고분자, 스피로 (spiro) 화합물, 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다.The light-emitting material is a material that can emit light in the visible light range by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining them, and a material with good quantum efficiency for fluorescence or phosphorescence is preferred. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ), carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzthiazole, and Examples include benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, and rubrene, but are not limited to these.
전자수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al 착물, Alq3를 포함한 착물, 유기 라디칼 화합물, 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다.The electron transport material is a material that can easily inject electrons from the cathode and transfer them to the light-emitting layer, and a material with high mobility for electrons is suitable. Specific examples include, but are not limited to, an Al complex of 8-hydroxyquinoline, a complex containing Alq 3 , an organic radical compound, and a hydroxyflavone-metal complex.
본 발명에 따른 유기발광소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present invention may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.
또한, 본 발명에 따른 유기발광 화합물은 유기 태양 전지, 유기 감광체, 유기 트랜지스터 등을 비롯한 유기전자소자에서도 유기발광소자에 적용되는 것과 유사한 원리로 작용할 수 있다.In addition, the organic light-emitting compound according to the present invention can function in organic electronic devices, including organic solar cells, organic photoreceptors, and organic transistors, on a principle similar to that applied to organic light-emitting devices.
이하, 본 발명의 이해를 돕기 위하여 바람직한 화합물의 합성예 및 소자 실시예를 제시한다. 그러나, 하기의 실시예는 본 발명을 예시하기 위한 것이며, 이에 의하여 본 발명의 범위가 한정되는 것은 아니다.Hereinafter, synthesis examples of preferred compounds and device examples are presented to aid understanding of the present invention. However, the following examples are intended to illustrate the present invention and are not intended to limit the scope of the present invention.
합성예Synthesis example 1 : 화합물 7의 합성 1: Synthesis of Compound 7
(1) (One) 제조예Manufacturing example 1 : 중간체 7-1의 합성 1: Synthesis of intermediate 7-1
2-Bromo-1-chloro-4-fluorobenzene (10.0 g, 0.048 mol), (3,5-di-tert-butylphenyl)boronic acid (13.4 g, 0.057 mol), K2CO3 (19.8 g, 0.143 mol), Pd(PPh3)4 (1.1 g, 0.001 mol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 7-1>을 8.6 g (수율 56.5%) 수득하였다.2-Bromo-1-chloro-4-fluorobenzene (10.0 g, 0.048 mol), (3,5-di-tert-butylphenyl)boronic acid (13.4 g, 0.057 mol), K 2 CO 3 (19.8 g, 0.143 mol) ), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added to Pd(PPh 3 ) 4 (1.1 g, 0.001 mol) and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 8.6 g (yield 56.5%) of <Intermediate 7-1>.
(2) (2) 제조예Manufacturing example 2 : 중간체 7-2의 합성 2: Synthesis of intermediate 7-2
중간체 7-1 (10.0 g, 0.031 mol), Bis(pinacolato)diborane (9.6 g, 0.038 mol), CH3COOK (9.2 g, 0.094 mol), Pd(dppf)Cl2 (1.2 g, 1.6 mmol), XPhos (1.4 g, 2.8 mmol)에 dioxane 넣고 100 ℃에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 7-2>를 9.3 g (수율 72.3%) 수득하였다.Intermediate 7-1 (10.0 g, 0.031 mol), Bis(pinacolato)diborane (9.6 g, 0.038 mol), CH 3 COOK (9.2 g, 0.094 mol), Pd(dppf)Cl 2 (1.2 g, 1.6 mmol), Dioxane was added to XPhos (1.4 g, 2.8 mmol) and stirred at 100°C for 12 hours to react. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 9.3 g (yield 72.3%) of <Intermediate 7-2>.
(3) (3) 제조예Manufacturing example 3 : 중간체 7-3의 합성 3: Synthesis of intermediate 7-3
3-Bromo-5-chloro-tert-butylbenzene (10.0 g, 0.040 mol), 중간체 7-2 (19.9 g, 0.049 mol), K2CO3 (16.8 g, 0.121 mol), Pd(PPh3)4 (0.9 g, 0.8 mmol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 7-3>을 11.4 g (수율 62.6%) 수득하였다.3-Bromo-5-chloro-tert-butylbenzene (10.0 g, 0.040 mol), intermediate 7-2 (19.9 g, 0.049 mol), K 2 CO 3 (16.8 g, 0.121 mol), Pd(PPh 3 ) 4 ( 0.9 g, 0.8 mmol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 11.4 g of <Intermediate 7-3> (yield 62.6%).
(4) (4) 제조예Manufacturing example 4 : 중간체 7-4의 합성 4: Synthesis of intermediate 7-4
2-Aminobiphenyl (10.0 g, 0.059 mol), 1-Bromo-4-cyclohexylbenzene (21.2 g, 0.089 mol), NaOtBu (17.0 g, 0.177 mol), Pd(dba)2 (1.4 g, 2.4 mmol), t-Bu3P (1.0 g, 4.7 mmol)에 Xylene 150 mL를 넣고 4시간 동안 70 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 7-4>를 12.4 g (수율 64.1%) 수득하였다.2-Aminobiphenyl (10.0 g, 0.059 mol), 1-Bromo-4-cyclohexylbenzene (21.2 g, 0.089 mol), NaOtBu (17.0 g, 0.177 mol), Pd(dba) 2 (1.4 g, 2.4 mmol), t- 150 mL of Xylene was added to Bu 3 P (1.0 g, 4.7 mmol) and stirred at 70°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and recrystallized using a column to obtain 12.4 g of <Intermediate 7-4> (yield 64.1%).
(5) (5) 제조예Manufacturing example 5 : 화합물 7의 합성 5: Synthesis of Compound 7
중간체 7-3 (10.0 g, 0.022 mol), 중간체 7-4 (10.9 g, 0.033 mol), NaOtBu (6.4 g, 0.067 mol), Pd(dba)2 (0.5 g, 0.9 mmol), t-Bu3P (0.4 g, 1.8 mmol)에 Xylene 150 mL를 넣고 4시간 동안 120 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 7>을 11.7 g (수율 71.1%) 수득하였다.Intermediate 7-3 (10.0 g, 0.022 mol), Intermediate 7-4 (10.9 g, 0.033 mol), NaOtBu (6.4 g, 0.067 mol), Pd(dba) 2 (0.5 g, 0.9 mmol), t-Bu 3 150 mL of Xylene was added to P (0.4 g, 1.8 mmol) and stirred at 120°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 11.7 g of <Compound 7> (yield 71.1%).
LC/MS: m/z=741[(M)+]LC/MS: m/z=741[(M) + ]
합성예Synthesis example 2 : 화합물 18의 합성 2: Synthesis of Compound 18
(1) (One) 제조예Manufacturing example 1 : 중간체 18-1의 합성 1: Synthesis of intermediate 18-1
1-Bromo-3-cyclohexyl-2-fluorobenzene (10.0 g, 0.039 mol), Bis(pinacolato)diboron (11.9 g, 0.047 mol), CH3COOK (11.5 g, 0.117 mol), Pd(dppf)Cl2 (1.4 g, 1.9 mmol)에 dioxane 200 mL 넣고 100 ℃에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 18-1>을 8.2 g (수율 69.3%) 수득하였다.1-Bromo-3-cyclohexyl-2-fluorobenzene (10.0 g, 0.039 mol), Bis(pinacolato)diboron (11.9 g, 0.047 mol), CH 3 COOK (11.5 g, 0.117 mol), Pd(dppf)Cl 2 ( 1.4 g, 1.9 mmol) was added to 200 mL of dioxane and stirred at 100°C for 12 hours to react. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 8.2 g (yield 69.3%) of <Intermediate 18-1>.
(2) (2) 제조예Manufacturing example 2 : 중간체 18-2의 합성 2: Synthesis of intermediate 18-2
3-Bromo-5-chloro-tert-butylbenzene (10.0 g, 0.040 mol), 중간체 18-1 (14.8 g, 0.049 mol), K2CO3 (16.8 g, 0.121 mol), Pd(PPh3)4 (0.9 g, 0.8 mmol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 18-2>를 9.3 g (수율 66.8%) 수득하였다.3-Bromo-5-chloro-tert-butylbenzene (10.0 g, 0.040 mol), intermediate 18-1 (14.8 g, 0.049 mol), K 2 CO 3 (16.8 g, 0.121 mol), Pd(PPh 3 ) 4 ( 0.9 g, 0.8 mmol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 9.3 g (yield 66.8%) of <Intermediate 18-2>.
(3) (3) 제조예Manufacturing example 3 : 중간체 18-3의 합성 3: Synthesis of intermediate 18-3
9,9-diphenyl-9H-fluoren-2-amine (10.0 g, 0.030 mol), 1-Bromo-4-cyclohexylbenzene (10.8 g, 0.045 mol), NaOtBu (8.7 g, 0.09 mol), Pd(dba)2 (0.7 g, 1.2 mmol), t-Bu3P (0.5 g, 2.4 mmol)에 Xylene 150 mL를 넣고 4시간 동안 70 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 18-3>을 9.4 g (수율 63.7%) 수득하였다.9,9-diphenyl-9H-fluoren-2-amine (10.0 g, 0.030 mol), 1-Bromo-4-cyclohexylbenzene (10.8 g, 0.045 mol), NaOtBu (8.7 g, 0.09 mol), Pd(dba) 2 (0.7 g, 1.2 mmol) and t-Bu 3 P (0.5 g, 2.4 mmol) were added with 150 mL of Xylene and stirred at 70°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 9.4 g of <Intermediate 18-3> (yield 63.7%).
(4) (4) 제조예Manufacturing example 4 : 화합물 18의 합성 4: Synthesis of Compound 18
중간체 18-2 (10.0 g, 0.029 mol), 중간체 18-3 (21.4 g, 0.044 mol), NaOtBu (8.4 g, 0.087 mol), Pd(dba)2 (0.7 g, 1.2 mmol), t-Bu3P (0.5 g, 2.3 mmol)에 Xylene 150 mL를 넣고 4시간 동안 120 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 18>을 15.9 g (수율 68.5%) 수득하였다.Intermediate 18-2 (10.0 g, 0.029 mol), Intermediate 18-3 (21.4 g, 0.044 mol), NaOtBu (8.4 g, 0.087 mol), Pd(dba) 2 (0.7 g, 1.2 mmol), t-Bu 3 150 mL of Xylene was added to P (0.5 g, 2.3 mmol) and stirred at 120°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 15.9 g of <Compound 18> (yield 68.5%).
LC/MS: m/z=799[(M)+]LC/MS: m/z=799[(M) + ]
합성예Synthesis example 3 : 화합물 28의 합성 3: Synthesis of Compound 28
(1) (One) 제조예Manufacturing example 1 : 중간체 28-1의 합성 1: Synthesis of intermediate 28-1
3-Bromo-5-chloro-tert-butylbenzene (10.0 g, 0.040 mol), (3,5-dimethylphenyl)boronic acid (7.3 g, 0.049 mol), K2CO3 (16.8 g, 0.121 mol), Pd(PPh3)4 (0.9 g, 0.8 mmol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 28-1>을 6.8 g (수율 61.7%) 수득하였다.3-Bromo-5-chloro-tert-butylbenzene (10.0 g, 0.040 mol), (3,5-dimethylphenyl)boronic acid (7.3 g, 0.049 mol), K 2 CO 3 (16.8 g, 0.121 mol), Pd ( To PPh 3 ) 4 (0.9 g, 0.8 mmol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 6.8 g (yield 61.7%) of <Intermediate 28-1>.
(2) (2) 제조예Manufacturing example 2 : 중간체 28-2의 합성 2: Synthesis of intermediate 28-2
3-dibenzofuranamine (10.0 g, 0.055 mol), 1-Bromo-4-cyclohexylbenzene (19.6 g, 0.082 mol), NaOtBu (15.7 g, 0.164 mol), Pd(dba)2 (1.3 g, 2.2 mmol), t-Bu3P (0.9 g, 4.4 mmol)에 Xylene 150 mL를 넣고 4시간 동안 70 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 28-2>를 12.4 g (수율 66.5%) 수득하였다.3-dibenzofuranamine (10.0 g, 0.055 mol), 1-Bromo-4-cyclohexylbenzene (19.6 g, 0.082 mol), NaOtBu (15.7 g, 0.164 mol), Pd(dba) 2 (1.3 g, 2.2 mmol), t- 150 mL of xylene was added to Bu 3 P (0.9 g, 4.4 mmol) and stirred at 70°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 12.4 g of <Intermediate 28-2> (yield 66.5%).
(3) (3) 제조예Manufacturing example 3 : 화합물 28의 합성 3: Synthesis of Compound 28
중간체 28-1 (10.0 g, 0.037 mol), 중간체 28-2 (18.8 g, 0.055 mol), NaOtBu (10.6 g, 0.110 mol), Pd(dba)2 (0.8 g, 1.5 mmol), t-Bu3P (0.6 g, 2.9 mmol)에 Xylene 150 mL를 넣고 4시간 동안 120 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 28>을 14.7 g (수율 69.4%) 수득하였다.Intermediate 28-1 (10.0 g, 0.037 mol), Intermediate 28-2 (18.8 g, 0.055 mol), NaOtBu (10.6 g, 0.110 mol), Pd(dba) 2 (0.8 g, 1.5 mmol), t-Bu 3 150 mL of Xylene was added to P (0.6 g, 2.9 mmol) and stirred at 120°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and recrystallized with a column to obtain 14.7 g of <Compound 28> (yield 69.4%).
LC/MS: m/z=577[(M)+]LC/MS: m/z=577[(M) + ]
합성예Synthesis example 4 : 화합물 44의 합성 4: Synthesis of Compound 44
(1) (One) 제조예Manufacturing example 1 : 중간체 44-1의 합성 1: Synthesis of intermediate 44-1
3-Bromo-5-chloro-tert-butylbenzene (10.0 g, 0.040 mol), (3,5-di-tert-butylphenyl)boronic acid (11.4 g, 0.049 mol), K2CO3 (16.8 g, 0.121 mol), Pd(PPh3)4 (0.9 g, 0.8 mmol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 44-1>을 9.1 g (수율 63.1%) 수득하였다.3-Bromo-5-chloro-tert-butylbenzene (10.0 g, 0.040 mol), (3,5-di-tert-butylphenyl)boronic acid (11.4 g, 0.049 mol), K 2 CO 3 (16.8 g, 0.121 mol) ), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added to Pd(PPh 3 ) 4 (0.9 g, 0.8 mmol) and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and recrystallized using a column to obtain 9.1 g of <Intermediate 44-1> (yield 63.1%).
(2) (2) 제조예Manufacturing example 2 : 화합물 44의 합성 2: Synthesis of Compound 44
중간체 44-1 (10.0 g, 0.028 mol), 중간체 18-3 (20.7 g, 0.042 mol), NaOtBu (8.1 g, 0.084 mol), Pd(dba)2 (0.6 g, 1.1 mmol), t-Bu3P (0.5 g, 2.2 mmol)에 Xylene 150 mL를 넣고 4시간 동안 120 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 44>를 16.2 g (수율 71.2%) 수득하였다.Intermediate 44-1 (10.0 g, 0.028 mol), Intermediate 18-3 (20.7 g, 0.042 mol), NaOtBu (8.1 g, 0.084 mol), Pd(dba) 2 (0.6 g, 1.1 mmol), t-Bu 3 150 mL of Xylene was added to P (0.5 g, 2.2 mmol) and stirred at 120°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and recrystallized using a column to obtain 16.2 g of <Compound 44> (yield 71.2%).
LC/MS: m/z=812[(M)+]LC/MS: m/z=812[(M) + ]
합성예Synthesis example 5 : 화합물 58의 합성 5: Synthesis of Compound 58
(1) (One) 제조예Manufacturing example 1 : 화합물 58의 합성 1: Synthesis of Compound 58
3-bromo-5-tert-butyl-1,1'-biphenyl (10.0 g, 0.035 mol), N-([1,1'-biphenyl]-2-yl)-9,9-diphenyl-9H-fluoren-2-amine (25.2 g, 0.052 mol), NaOtBu (10.0 g, 0.104 mol), Pd(dba)2 (0.8 g, 1.4 mmol), t-Bu3P (0.6 g, 2.8 mmol)에 Xylene 150 mL를 넣고 4시간 동안 70 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 58>을 17.5 g (수율 72.9%) 수득하였다.3-bromo-5-tert-butyl-1,1'-biphenyl (10.0 g, 0.035 mol), N-([1,1'-biphenyl]-2-yl)-9,9-diphenyl-9H-fluoren -2-amine (25.2 g, 0.052 mol), NaOtBu (10.0 g, 0.104 mol), Pd(dba) 2 (0.8 g, 1.4 mmol), t-Bu 3 P (0.6 g, 2.8 mmol) in 150 mL of Xylene was added and stirred at 70°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 17.5 g of <Compound 58> (yield 72.9%).
LC/MS: m/z=693[(M)+]LC/MS: m/z=693[(M) + ]
합성예Synthesis example 6 : 화합물 72의 합성 6: Synthesis of Compound 72
(1) (One) 제조예Manufacturing example 1 : 중간체 72-1의 합성 1: Synthesis of intermediate 72-1
(4-Fluoro-3,5-dimethylphenyl)boronic acid (10.0 g, 0.040 mol), 3-Bromo-5-chloro-tert-butylbenzene (8.1 g, 0.058 mol), K2CO3 (16.8 g, 0.121 mol), Pd(PPh3)4 (0.9 g, 0.8 mmol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 72-1>을 7.1 g (수율 60.4%) 수득하였다.(4-Fluoro-3,5-dimethylphenyl)boronic acid (10.0 g, 0.040 mol), 3-Bromo-5-chloro-tert-butylbenzene (8.1 g, 0.058 mol), K 2 CO 3 (16.8 g, 0.121 mol) ), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added to Pd(PPh 3 ) 4 (0.9 g, 0.8 mmol) and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 7.1 g of <Intermediate 72-1> (yield 60.4%).
(2) (2) 제조예Manufacturing example 2 : 화합물 72의 합성 2: Synthesis of Compound 72
중간체 72-1 (10.0 g, 0.034 mol), 중간체 7-4 (16.9 g, 0.052 mol), NaOtBu (9.9 g, 0.103 mol), Pd(dba)2 (0.8 g, 1.4 mmol), t-Bu3P (0.6 g, 2.8 mmol)에 Xylene 150 mL를 넣고 4시간 동안 120 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 72>를 13.0 g (수율 65.0%) 수득하였다.Intermediate 72-1 (10.0 g, 0.034 mol), Intermediate 7-4 (16.9 g, 0.052 mol), NaOtBu (9.9 g, 0.103 mol), Pd(dba) 2 (0.8 g, 1.4 mmol), t-Bu 3 150 mL of Xylene was added to P (0.6 g, 2.8 mmol) and stirred at 120°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 13.0 g of <Compound 72> (yield 65.0%).
LC/MS: m/z=581[(M)+]LC/MS: m/z=581[(M) + ]
합성예Synthesis example 7 : 화합물 97의 합성 7: Synthesis of Compound 97
(1) (One) 제조예Manufacturing example 1 : 중간체 97-1의 합성 1: Synthesis of intermediate 97-1
1-Bromo-2-chloro-4,5-dimethylbenzene (10.0 g, 0.046 mol), (3,5-di-tert-butylphenyl)boronic acid (12.8 g, 0.055 mol), K2CO3 (18.9 g, 0.137 mol), Pd(PPh3)4 (1.1 g, 0.9 mmol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 97-1>을 9.5 g (수율 63.4%) 수득하였다.1-Bromo-2-chloro-4,5-dimethylbenzene (10.0 g, 0.046 mol), (3,5-di-tert-butylphenyl)boronic acid (12.8 g, 0.055 mol), K 2 CO 3 (18.9 g, 0.137 mol), Pd(PPh 3 ) 4 (1.1 g, 0.9 mmol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 9.5 g of <Intermediate 97-1> (yield 63.4%).
(2) (2) 제조예Manufacturing example 2 : 중간체 97-2의 합성 2: Synthesis of intermediate 97-2
중간체 97-1 (10.0 g, 0.030 mol), Bis(pinacolato)diborane (9.3 g, 0.037 mol), CH3COOK (9.0 g, 0.091 mol), Pd(dppf)Cl2 (1.1 g, 1.5 mmol), XPhos (1.3 g, 2.7 mmol)에 dioxane 넣고 100 ℃에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 97-2>를 9.4 g (수율 73.5%) 수득하였다.Intermediate 97-1 (10.0 g, 0.030 mol), Bis(pinacolato)diborane (9.3 g, 0.037 mol), CH 3 COOK (9.0 g, 0.091 mol), Pd(dppf)Cl 2 (1.1 g, 1.5 mmol), Dioxane was added to XPhos (1.3 g, 2.7 mmol) and stirred at 100°C for 12 hours to react. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 9.4 g (yield 73.5%) of <Intermediate 97-2>.
(3) (3) 제조예Manufacturing example 3 : 중간체 97-3의 합성 3: Synthesis of intermediate 97-3
3-Bromo-5-chloro-tert-butylbenzene (10.0 g, 0.040 mol), 중간체 97-2 (20.4 g, 0.049 mol), K2CO3 (16.8 g, 0.121 mol), Pd(PPh3)4 (0.9 g, 0.8 mmol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 97-3>을 10.8 g (수율 58.0%) 수득하였다.3-Bromo-5-chloro-tert-butylbenzene (10.0 g, 0.040 mol), intermediate 97-2 (20.4 g, 0.049 mol), K 2 CO 3 (16.8 g, 0.121 mol), Pd(PPh 3 ) 4 ( 0.9 g, 0.8 mmol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added and stirred at 80°C for 6 hours to react. After completion of the reaction, it was extracted, concentrated, and recrystallized with a column to obtain 10.8 g of <Intermediate 97-3> (yield 58.0%).
(4) (4) 제조예Manufacturing example 4 : 화합물 97의 합성 4: Synthesis of Compound 97
중간체 97-3 (10.0 g, 0.022 mol), N-([1,1'-biphenyl]-2-yl)-9,9-diphenyl-9H-fluoren-2-amine (15.8 g, 0.033 mol), NaOtBu (6.3 g, 0.065 mol), Pd(dba)2 (0.5 g, 0.9 mmol), t-Bu3P (0.4 g, 1.7 mmol)에 Xylene 150 mL를 넣고 4시간 동안 120 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 97>을 13.8 g (수율 69.9%) 수득하였다.Intermediate 97-3 (10.0 g, 0.022 mol), N-([1,1'-biphenyl]-2-yl)-9,9-diphenyl-9H-fluoren-2-amine (15.8 g, 0.033 mol), Add 150 mL of . After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 13.8 g of <Compound 97> (yield 69.9%).
LC/MS: m/z=910[(M)+]LC/MS: m/z=910[(M) + ]
합성예Synthesis example 8 : 화합물 159의 합성 8: Synthesis of Compound 159
(1) (One) 제조예Manufacturing example 1 : 화합물 159의 합성 1: Synthesis of Compound 159
3-bromo-5-tert-butyl-1,1'-biphenyl (10.0 g, 0.035 mol), N-(biphenyl-2-yl)dibenzo[b,d]furan-3-amine (17.4 g, 0.052 mol), NaOtBu (10.0 g, 0.104 mol), Pd(dba)2 (0.8 g, 1.4 mmol), t-Bu3P (0.6 g, 2.8 mmol)에 Xylene 150 mL를 넣고 4시간 동안 120 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 159>를 13.7 g (수율 72.9%) 수득하였다.3-bromo-5-tert-butyl-1,1'-biphenyl (10.0 g, 0.035 mol), N-(biphenyl-2-yl)dibenzo[b,d]furan-3-amine (17.4 g, 0.052 mol) ), NaOtBu (10.0 g, 0.104 mol), Pd(dba) 2 (0.8 g, 1.4 mmol), and t-Bu 3 P (0.6 g, 2.8 mmol) were mixed with 150 mL of Xylene and stirred at 120°C for 4 hours. reacted. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 13.7 g of <Compound 159> (yield 72.9%).
LC/MS: m/z=543[(M)+]LC/MS: m/z=543[(M) + ]
합성예Synthesis example 9 : 화합물 168의 합성 9: Synthesis of Compound 168
(1) (One) 제조예Manufacturing example 1 : 중간체 168-1의 합성 1: Synthesis of intermediate 168-1
1,3-dibromo-5-chlorobenzene (10.0 g, 0.037 mol), (3,5-di-tert-butylphenyl)boronic acid (20.8 g, 0.089 mol), K2CO3 (30.7 g, 0.222 mol), Pd(PPh3)4 (0.9 g, 0.7 mmol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼하여 <중간체 168-1>을 13.4 g (수율 74.0%) 수득하였다.1,3-dibromo-5-chlorobenzene (10.0 g, 0.037 mol), (3,5-di-tert-butylphenyl)boronic acid (20.8 g, 0.089 mol), K 2 CO 3 (30.7 g, 0.222 mol), To Pd(PPh 3 ) 4 (0.9 g, 0.7 mmol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 13.4 g (yield 74.0%) of <Intermediate 168-1>.
(2) (2) 제조예Manufacturing example 2 : 중간체 168-2의 합성 2: Synthesis of intermediate 168-2
중간체 168-1 (10.0 g, 0.020 mol), Bis(pinacolato)diborane (6.2 g, 0.025 mol), CH3COOK (6.0 g, 0.061 mol), Pd(dppf)Cl2 (0.8 g, 1.0 mmol), XPhos (0.9 g, 1.8 mmol)에 dioxane 넣고 100 ℃에서 12시간 동안 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼하여 <중간체 168-2>를 8.9 g (수율 75.0%) 수득하였다.Intermediate 168-1 (10.0 g, 0.020 mol), Bis(pinacolato)diborane (6.2 g, 0.025 mol), CH 3 COOK (6.0 g, 0.061 mol), Pd(dppf)Cl 2 (0.8 g, 1.0 mmol), Dioxane was added to XPhos (0.9 g, 1.8 mmol) and stirred at 100°C for 12 hours to react. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 8.9 g (yield 75.0%) of <Intermediate 168-2>.
(3) (3) 제조예Manufacturing example 3 : 중간체 168-3의 합성 3: Synthesis of intermediate 168-3
3-Bromo-5-chloro-tert-butylbenzene (10.0 g, 0.040 mol), 중간체 168-2 (28.2 g, 0.049 mol), K2CO3 (16.8 g, 0.121 mol), Pd(PPh3)4 (0.9 g, 0.8 mmol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 168-3>을 14.8 g (수율 59.0%) 수득하였다.3-Bromo-5-chloro-tert-butylbenzene (10.0 g, 0.040 mol), intermediate 168-2 (28.2 g, 0.049 mol), K 2 CO 3 (16.8 g, 0.121 mol), Pd(PPh 3 ) 4 ( 0.9 g, 0.8 mmol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 14.8 g of <Intermediate 168-3> (yield 59.0%).
(4) (4) 제조예Manufacturing example 4 : 화합물 168의 합성 4: Synthesis of Compound 168
중간체 168-3 (10.0 g, 0.016 mol), 중간체 18-3 (11.9 g, 0.024 mol), NaOtBu (4.6 g, 0.048 mol), Pd(dba)2 (0.4 g, 0.6 mmol), t-Bu3P (0.3 g, 1.3 mmol)에 Xylene 150 mL를 넣고 4시간 동안 120 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 168>을 10.7 g (수율 61.8%) 수득하였다.Intermediate 168-3 (10.0 g, 0.016 mol), Intermediate 18-3 (11.9 g, 0.024 mol), NaOtBu (4.6 g, 0.048 mol), Pd(dba) 2 (0.4 g, 0.6 mmol), t-Bu 3 150 mL of Xylene was added to P (0.3 g, 1.3 mmol) and stirred at 120°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 10.7 g of <Compound 168> (yield 61.8%).
LC/MS: m/z=1076[(M)+]LC/MS: m/z=1076[(M) + ]
합성예Synthesis example 10 : 화합물 203의 합성 10: Synthesis of compound 203
(1) (One) 제조예Manufacturing example 1 : 화합물 203의 합성 1: Synthesis of Compound 203
중간체 7-3 (10.0 g, 0.022 mol), Bis-biphenyl-4-yl-amine (10.7 g, 0.033 mol), NaOtBu (6.4 g, 0.067 mol), Pd(dba)2 (0.5 g, 0.9 mmol), t-Bu3P (0.4 g, 1.8 mmol)에 Xylene 150 mL를 넣고 4시간 동안 120 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 203>을 11.6 g (수율 71.1%) 수득하였다.Intermediate 7-3 (10.0 g, 0.022 mol), Bis-biphenyl-4-yl-amine (10.7 g, 0.033 mol), NaOtBu (6.4 g, 0.067 mol), Pd(dba) 2 (0.5 g, 0.9 mmol) , 150 mL of Xylene was added to t-Bu 3 P (0.4 g, 1.8 mmol) and stirred at 120°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 11.6 g of <Compound 203> (yield 71.1%).
LC/MS: m/z=735[(M)+]LC/MS: m/z=735[(M) + ]
합성예Synthesis example 11 : 화합물 215의 합성 11: Synthesis of compound 215
(1) (One) 제조예Manufacturing example 1 : 중간체 215-1의 합성 1: Synthesis of intermediate 215-1
1-Bromo-3-chloro-5-cyclohexylbenzene (10.0 g, 0.037 mol), (3,5-di-tert-butylphenyl)boronic acid (10.3 g, 0.044 mol), K2CO3 (15.2 g, 0.110 mol), Pd(PPh3)4 (0.8 g, 0.7 mmol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 215-1>을 8.5 g (수율 60.7%) 수득하였다.1-Bromo-3-chloro-5-cyclohexylbenzene (10.0 g, 0.037 mol), (3,5-di-tert-butylphenyl)boronic acid (10.3 g, 0.044 mol), K 2 CO 3 (15.2 g, 0.110 mol) ), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added to Pd(PPh 3 ) 4 (0.8 g, 0.7 mmol) and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 8.5 g of <Intermediate 215-1> (yield 60.7%).
(2) (2) 제조예Manufacturing example 2 : 중간체 215-2의 합성 2: Synthesis of intermediate 215-2
9,9-diphenyl-9H-fluoren-2-amine (10.0 g, 0.030 mol), 1-Bromo-2,4-diphenyl-benzene (13.9 g, 0.045 mol), NaOtBu (8.7 g, 0.09 mol), Pd(dba)2 (0.7 g, 1.2 mmol), t-Bu3P (0.5 g, 2.4 mmol)에 Xylene 150 mL를 넣고 4시간 동안 70 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 215-2>를 11.4 g (수율 67.7%) 수득하였다.9,9-diphenyl-9H-fluoren-2-amine (10.0 g, 0.030 mol), 1-Bromo-2,4-diphenyl-benzene (13.9 g, 0.045 mol), NaOtBu (8.7 g, 0.09 mol), Pd (dba) 2 (0.7 g, 1.2 mmol) and t-Bu 3 P (0.5 g, 2.4 mmol) were mixed with 150 mL of xylene and stirred at 70°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 11.4 g of <Intermediate 215-2> (yield 67.7%).
(3) (3) 제조예Manufacturing example 3 : 화합물 215의 합성 3: Synthesis of Compound 215
중간체 215-1 (10.0 g, 0.026 mol), 중간체 215-2 (22.0 g, 0.039 mol), NaOtBu (7.5 g, 0.078 mol), Pd(dba)2 (0.6 g, 1.0 mmol), t-Bu3P (0.4 g, 2.1 mmol)에 Xylene 150 mL를 넣고 4시간 동안 120 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 215>를 17.9 g (수율 75.5%) 수득하였다.Intermediate 215-1 (10.0 g, 0.026 mol), Intermediate 215-2 (22.0 g, 0.039 mol), NaOtBu (7.5 g, 0.078 mol), Pd(dba) 2 (0.6 g, 1.0 mmol), t-Bu 3 150 mL of Xylene was added to P (0.4 g, 2.1 mmol) and stirred at 120°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 17.9 g of <Compound 215> (yield 75.5%).
LC/MS: m/z=908[(M)+]LC/MS: m/z=908[(M) + ]
합성예Synthesis example 12 : 화합물 227의 합성 12: Synthesis of compound 227
(1) (One) 제조예Manufacturing example 1 : 중간체 227-1의 합성 1: Synthesis of intermediate 227-1
3-Bromo-5-chloro-tert-butylbenzene (10.0 g, 0.040 mol), 3,5-dicyclohexylphenylboronic Acid (13.9 g, 0.049 mol), K2CO3 (16.8 g, 0.121 mol), Pd(PPh3)4 (0.9 g, 0.8 mmol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 227-1>을 9.7 g (수율 58.7%) 수득하였다.3-Bromo-5-chloro-tert-butylbenzene (10.0 g, 0.040 mol), 3,5-dicyclohexylphenylboronic Acid (13.9 g, 0.049 mol), K 2 CO 3 (16.8 g, 0.121 mol), Pd(PPh 3 ) To 4 (0.9 g, 0.8 mmol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 9.7 g of <Intermediate 227-1> (yield 58.7%).
(2) (2) 제조예Manufacturing example 2 : 화합물 227의 합성 2: Synthesis of Compound 227
중간체 227-1 (10.0 g, 0.024 mol), N-([1,1'-biphenyl]-2-yl)-9,9-diphenyl-9H-fluoren-2-amine (17.9 g, 0.024 mol), NaOtBu (4.6 g, 0.048 mol), Pd(dba)2 (0.4 g, 0.6 mmol), t-Bu3P (0.3 g, 1.3 mmol)에 Xylene 150 mL를 넣고 4시간 동안 120 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 227>을 13.8 g (수율 65.8%) 수득하였다.Intermediate 227-1 (10.0 g, 0.024 mol), N-([1,1'-biphenyl]-2-yl)-9,9-diphenyl-9H-fluoren-2-amine (17.9 g, 0.024 mol), Add 150 mL of . After completion of the reaction, the extract was extracted and concentrated, followed by column and recrystallization to obtain 13.8 g of <Compound 227> (yield 65.8%).
LC/MS: m/z=858[(M)+]LC/MS: m/z=858[(M) + ]
합성예Synthesis example 13 : 화합물 248의 합성 13: Synthesis of compound 248
(1) (One) 제조예Manufacturing example 1 : 중간체 248-1의 합성 1: Synthesis of intermediate 248-1
2-Bromo-4-chloro-1,3,5-trimethylbenzene (10.0 g, 0.043 mol), (3,5-di-tert-butylphenyl) boronic acid (12.0 g, 0.051 mol), K2CO3 (17.8 g, 0.129 mol), Pd(PPh3)4 (1.0 g, 0.9 mmol)에 toluene 200 mL, ethanol 50 mL, H2O 50 mL를 넣고 6시간 동안 80 ℃에서 교반하여 반응시켰다. 반응 종료 후 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 248-1>을 9.1 g (수율 62.0%) 수득하였다.2-Bromo-4-chloro-1,3,5-trimethylbenzene (10.0 g, 0.043 mol), (3,5-di-tert-butylphenyl) boronic acid (12.0 g, 0.051 mol), K 2 CO 3 (17.8 g, 0.129 mol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H 2 O were added to Pd(PPh 3 ) 4 (1.0 g, 0.9 mmol) and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 9.1 g of <Intermediate 248-1> (yield 62.0%).
(2) (2) 제조예Manufacturing example 2 : 중간체 248-2의 합성 2: Synthesis of intermediate 248-2
9,9-diphenyl-9H-fluoren-2-amine (10.0 g, 0.030 mol), 1-Bromo-2-cyclohexylbenzene (10.8 g, 0.045 mol), NaOtBu (8.7 g, 0.09 mol), Pd(dba)2 (0.7 g, 1.2 mmol), t-Bu3P (0.5 g, 2.4 mmol)에 Xylene 150 mL를 넣고 4시간 동안 70 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <중간체 248-2>를 9.4 g (수율 63.8%) 수득하였다.9,9-diphenyl-9H-fluoren-2-amine (10.0 g, 0.030 mol), 1-Bromo-2-cyclohexylbenzene (10.8 g, 0.045 mol), NaOtBu (8.7 g, 0.09 mol), Pd(dba) 2 (0.7 g, 1.2 mmol) and t-Bu 3 P (0.5 g, 2.4 mmol) were added with 150 mL of Xylene and stirred at 70°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 9.4 g of <Intermediate 248-2> (yield 63.8%).
(3) (3) 제조예Manufacturing example 3 : 화합물 248의 합성 3: Synthesis of Compound 248
중간체 248-1 (10.0 g, 0.029mol), 중간체 248-2 (21.5 g, 0.044 mol), NaOtBu (8.4 g, 0.088 mol), Pd(dba)2 (0.7 g, 1.2 mmol), t-Bu3P (0.5 g, 2.3 mmol)에 Xylene 150 mL를 넣고 4시간 동안 120 ℃에서 교반하여 반응시켰다. 반응 종료 후, 추출하여 농축한 후 컬럼 및 재결정하여 <화합물 248>을 16.0 g (수율 68.8%) 수득하였다.Intermediate 248-1 (10.0 g, 0.029 mol), Intermediate 248-2 (21.5 g, 0.044 mol), NaOtBu (8.4 g, 0.088 mol), Pd(dba) 2 (0.7 g, 1.2 mmol), t-Bu 3 150 mL of Xylene was added to P (0.5 g, 2.3 mmol) and stirred at 120°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 16.0 g of <Compound 248> (yield 68.8%).
LC/MS: m/z=798[(M)+]LC/MS: m/z=798[(M) + ]
실험예Experiment example 1 : 본 발명에 따른 화합물의 광학 특성 1: Optical properties of the compound according to the present invention
본 발명에 따른 화합물의 광학 특성 실험을 위하여, 25 mm × 25 mm 크기를 갖는 Quartz glass를 세정한 후에, 진공 챔버에 장착하여 베이스 압력이 1 × 10-6 torr 이상 되면 유리 기판 위에 하기 [표 1]에 기재된 본 발명에 따른 실시예 1 내지 13 화합물 및 비교예 1 화합물을 각각 증착하여 광학 특성을 측정하였다.In order to test the optical properties of the compound according to the present invention, quartz glass having a size of 25 mm × 25 mm is cleaned, mounted in a vacuum chamber, and when the base pressure is greater than 1 × 10-6 torr, the glass substrate is placed on the glass substrate as shown below [Table 1 The optical properties were measured by depositing the compounds of Examples 1 to 13 and the compound of Comparative Example 1 according to the present invention described in ], respectively.
실시예Example 1 내지 13 1 to 13
본 발명에 따른 유기발광소자를 구현하는 실시예 화합물 1 내지 13을 유리 기판 위에 각각 100 nm 증착하여 굴절률을 측정하였다.Examples of implementing an organic light emitting device according to the present invention Compounds 1 to 13 were each deposited at 100 nm on a glass substrate, and the refractive index was measured.
Quartz glass / 유기물 (100 nm)Quartz glass / organic matter (100 nm)
비교예Comparative example 1 One
비교예 1을 위한 기판은 본 발명에 따른 실시예 화합물 1 내지 13 대신에 하기 α-NPB를 사용한 것을 제외하고 동일하게 제작하여 광학 특성을 측정하였다.The substrate for Comparative Example 1 was manufactured in the same manner, except that the following α-NPB was used instead of Example Compounds 1 to 13 according to the present invention, and optical properties were measured.
실험예Experiment example 1 : One : 실시예Example 화합물 1 내지 13의 광학 특성 Optical properties of compounds 1 to 13
상기 실시예에 따라 제작된 기판은 Ellipsometry (Elli-SE)를 이용하여 굴절률을 측정하였다. 청색 (450 nm), 녹색 (520 nm), 적색 (630 nm)의 각 파장 영역에서 굴절률을 측정하였으며 그 결과를 하기 [표 1]에 나타내었다.The refractive index of the substrate manufactured according to the above example was measured using Ellipsometry (Elli-SE). The refractive index was measured in each wavelength range of blue (450 nm), green (520 nm), and red (630 nm), and the results are shown in [Table 1] below.
상기 [표 1]을 살펴보면, 본 발명에 따른 화합물은 청색, 녹색, 적색 각 파장대 (450, 520, 630 nm)에서의 굴절률 값이 종래의 정공수송 재료인 비교예 1 화합물 (α-NPB) 대비 현저히 낮음을 확인할 수 있으며, 이에 따라 낮은 굴절률 값을 갖는 본 발명에 따른 화합물을 소자 내의 정공수송층에 채용할 경우 유기발광소자의 효율 최적화를 기대할 수 있다.Looking at [Table 1], the refractive index values of the compound according to the present invention in each of the blue, green, and red wavelength bands (450, 520, 630 nm) are compared to the compound of Comparative Example 1 (α-NPB), which is a conventional hole transport material. It can be confirmed that it is significantly low, and accordingly, when the compound according to the present invention having a low refractive index value is employed in the hole transport layer in the device, optimization of the efficiency of the organic light-emitting device can be expected.
[α-NPB][α-NPB]
소자 device 실시예Example ( ( HTLHTL ))
본 발명에 따른 실시예에서, 양극은 25 mm × 25 mm × 0.7 mm의 Ag를 포함하는 ITO 유리 기판을 이용하여, 발광 면적이 2 mm × 2 mm 크기가 되도록 패터닝한 후 세정하였다. 패터닝된 ITO 기판을 진공 챔버에 장착한 후, 1 × 10-6 torr 이상의 공정 압력에서 기판 위에 하기 구조로 유기물과 금속을 증착하였다.In an example according to the present invention, the anode was patterned to have a light emitting area of 2 mm × 2 mm using an ITO glass substrate containing Ag of 25 mm × 25 mm × 0.7 mm and then cleaned. After the patterned ITO substrate was mounted in a vacuum chamber, organic materials and metals were deposited on the substrate in the structure below at a process pressure of 1 × 10 -6 torr or more.
소자 device 실시예Example 14 내지 37 14 to 37
본 발명에 따라 구현되는 화합물을 정공수송층에 채용하여, 하기와 같은 소자 구조를 갖는 유기발광소자를 제작한 후에, 본 발명에 따라 구현되는 화합물 및 이를 정공수송층에 채용한 소자가 갖는 발광 및 구동 특성을 측정하였다.After manufacturing an organic light-emitting device having the following device structure by employing the compound implemented according to the present invention in the hole transport layer, the light emission and driving characteristics of the compound implemented according to the present invention and the device employing the same in the hole transport layer was measured.
Ag/ITO / 정공주입층 (HAT-CN, 5 nm) / 정공수송층 (60 nm) / 전자저지층 (TCTA, 10 nm) / 발광층 (20 nm) / 전자수송층 (ET1:Liq, 30 nm) / LiF (1 nm) / Mg:Ag (15nm) / 광효율 개선층 (70 nm)Ag/ITO / hole injection layer (HAT-CN, 5 nm) / hole transport layer (60 nm) / electron blocking layer (TCTA, 10 nm) / emission layer (20 nm) / electron transport layer (ET1:Liq, 30 nm) / LiF (1 nm) / Mg:Ag (15 nm) / Light efficiency improvement layer (70 nm)
유리 기판상에 Ag를 포함하는 ITO 투명 전극 상부에 [HAT-CN]을 5 nm 두께로 성막하여 정공주입층을 형성한 후에, 하기 [표 2]에 기재된 본 발명에 따른 화합물을 60 nm로 성막하여 정공수송층을 형성하였으며, [TCTA]를 10 nm 두께로 성막하여 전자저지층을 형성하였다. 이후, 호스트 화합물로 [BH1], 도펀트 화합물로 [BD1]을 사용하여 20 nm로 공증착하여 발광층을 형성하였다. 이후, 전자수송층 (하기 [ET1] 화합물 Liq 50% 도핑)을 30 nm 증착 후, LiF를 1 nm의 두께로 성막하여 전자주입층을 형성하였다. 그후, Mg:Ag를 1:9의 비율로 15 nm의 두께로 성막하여 캐소드를 형성하였다. 그리고 광효율 개선층 (capping layer) 화합물로는 Alq3 화합물을 70 nm의 두께로 성막하여 유기발광소자를 제작하였다.After forming a hole injection layer by forming a 5 nm thick film of [HAT-CN] on an ITO transparent electrode containing Ag on a glass substrate, a 60 nm thick film was formed with the compound according to the present invention shown in [Table 2] below. A hole transport layer was formed, and [TCTA] was deposited to a thickness of 10 nm to form an electron blocking layer. Afterwards, [BH1] as a host compound and [BD1] as a dopant compound were co-deposited to a thickness of 20 nm to form an emitting layer. Afterwards, an electron transport layer (50% doped with [ET1] compound Liq below) was deposited to a thickness of 30 nm, and then LiF was deposited to a thickness of 1 nm to form an electron injection layer. Afterwards, a cathode was formed by forming a film of Mg:Ag at a ratio of 1:9 to a thickness of 15 nm. And the light efficiency improvement layer (capping layer) compound is Alq 3. An organic light emitting device was manufactured by depositing the compound into a film with a thickness of 70 nm.
소자 device 비교예Comparative example 2 2
소자 비교예 2를 위한 유기발광소자는 상기 실시예 14 내지 37의 소자구조에서 정공 수송층에 본 발명에 따른 화합물 대신에 하기 [α-NPB]를 사용한 것을 제외하고 동일하게 제작하였다.The organic light emitting device for Device Comparative Example 2 was manufactured in the same manner as the device structures of Examples 14 to 37, except that the following [α-NPB] was used instead of the compound according to the present invention in the hole transport layer.
소자 device 비교예Comparative example 3 3
소자 비교예 3을 위한 유기발광소자는 상기 실시예 14 내지 37의 소자구조에서 정공 수송층에 본 발명에 따른 화합물 대신에 하기 [HT1]을 사용한 것을 제외하고 동일하게 제작하였다.The organic light emitting device for Device Comparative Example 3 was manufactured in the same manner as the device structures of Examples 14 to 37, except that [HT1] below was used in the hole transport layer instead of the compound according to the present invention.
실험예Experiment example 2 : 소자 2: element 실시예Example 14 내지 37의 발광 특성 Luminous properties of 14 to 37
상기 실시예 및 비교예에 따라 제조된 유기발광소자에 대해서 Source meter (Model 237, Keithley)와 휘도계 (PR-650, Photo Research)를 이용하여 구동 전압, 전류 효율 및 색좌표를 측정하였고, 1,000 nit 기준의 결과값은 하기 [표 2]와 같다.The driving voltage, current efficiency, and color coordinates of the organic light emitting devices manufactured according to the above examples and comparative examples were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research), and were measured at 1,000 nit. The standard result values are shown in [Table 2] below.
상기 [표 2]에 나타낸 결과를 살펴보면, 본 발명에 따른 화합물을 소자 내 정공수송층에 채용한 유기발광소자의 경우 종래 정공수송 재료로 널리 사용된 화합물을 채용한 유기발광소자 (비교예 2 내지 3)에 비하여 구동 전압이 감소하고, 전류 효율이 향상되는 것을 확인할 수 있다.Looking at the results shown in [Table 2], in the case of an organic light-emitting device employing a compound according to the present invention as a hole transport layer in the device, an organic light-emitting device employing a compound widely used as a conventional hole transport material (Comparative Examples 2 to 3 ), it can be seen that the driving voltage is reduced and the current efficiency is improved compared to ).
이는 상기 [표 1]에서 확인한 바와 같이, 본 발명에 따른 정공수송층 채용 유기 화합물의 굴절률이 비교예 화합물에 비하여 현저하게 낮아짐에 따라 발광효율이 개선됨을 명확히 확인할 수 있다.As confirmed in [Table 1] above, it can be clearly confirmed that the luminous efficiency is improved as the refractive index of the organic compound employing a hole transport layer according to the present invention is significantly lowered compared to the comparative example compound.
[HAT_CN] [α-NPB] [BH1] [BD1] [ET1][HAT_CN] [α-NPB] [BH1] [BD1] [ET1]
[TCTA] [HT1][TCTA] [HT1]
Claims (10)
[화학식 Ⅰ]
상기 [화학식 Ⅰ]에서,
R1은 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 치환 또는 비치환된 탄소수 1 내지 20의 할로겐화된 알킬기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬실릴기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬저마늄기 및 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기 중에서 선택되는 어느 하나이고,
n은 1 내지 4의 정수이며, 상기 n이 2 이상인 경우 복수 개의 R1은 서로 동일하거나 상이하고,
Ar1은 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이며,
Ar2 내지 Ar3은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기, 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴기 및 하기 [구조식 1] 중에서 선택되는 어느 하나이며,
[구조식 1]
상기 [구조식 1]에서,
R2 및 R3은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소, 시아노기, 할로겐기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기 중에서 선택되는 어느 하나이며,
m 및 o는 각각 0 내지 4의 정수이고, 상기 m 및 o가 각각 2 이상인 경우 복수 개의 R2 및 R3은 각각 서로 동일하거나 상이하며,
R4 및 R5는 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기, 치환 또는 비치환된 탄소수 2 내지 20의 헤테로시클로알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기 중에서 선택되는 어느 하나이다.
상기 R4 및 R5는 서로 연결되어 지환족 또는 방향족의 단일환 또는 다환 고를 추가 형성할 수 있다.Organic compounds represented by the following [Chemical Formula I]:
[Formula Ⅰ]
In the above [Chemical Formula I],
R 1 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. Any one selected from an alkyl germanium group having 3 to 20 carbon atoms and a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms,
n is an integer from 1 to 4, and when n is 2 or more, a plurality of R 1 are the same or different from each other,
Ar 1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Ar 2 to Ar 3 are the same or different from each other, and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and the following [Structural Formula 1] Which one,
[Structural Formula 1]
In [Structural Formula 1] above,
R 2 and R 3 are the same or different from each other, and are each independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, Any one selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,
m and o are each integers from 0 to 4, and when m and o are each 2 or more, a plurality of R 2 and R 3 are the same or different from each other,
R 4 and R 5 are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 20 carbon atoms, or a substituted or unsubstituted group. It is any one selected from an aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
R 4 and R 5 may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.
상기 Ar1은 할로겐기, 알킬기 및 시클로알킬기 중에서 선택된 1종 이상을 치환기로 갖는 치환된 탄소수 6 내지 30의 아릴기인 것을 특징으로 하는 유기 화합물.According to paragraph 1,
The organic compound wherein Ar 1 is a substituted aryl group having 6 to 30 carbon atoms having one or more substituents selected from a halogen group, an alkyl group, and a cycloalkyl group.
상기 Ar1은 할로겐기; 및 알킬기와 시클로알킬기 중에서 선택된 어느 하나;를 각각 치환기로 갖는 치환된 탄소수 6 내지 30의 아릴기인 것을 특징으로 하는 유기 화합물.According to paragraph 2,
Ar 1 is a halogen group; and any one selected from an alkyl group and a cycloalkyl group; an organic compound characterized in that it is a substituted aryl group having 6 to 30 carbon atoms, each having as a substituent.
상기 R4 및 R5는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기 및 치환 또는 비치환된 탄소수 6 내지 30의 아릴기 중에서 선택되는 어느 하나인 것을 특징으로 하는 유기 화합물.According to paragraph 1,
R 4 and R 5 are the same or different from each other, and are each independently selected from a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. organic compounds that do.
상기 Ar2 내지 Ar3 중 적어도 하나 이상은 시클로알킬기를 치환기로 갖는 구조체인 것을 특징으로 하는 유기 화합물.According to paragraph 1,
An organic compound characterized in that at least one of Ar 2 to Ar 3 is a structure having a cycloalkyl group as a substituent.
상기 R1 및 Ar1 내지 Ar3의 정의에서, 치환 또는 비치환이란 상기 R1 및 Ar1 내지 Ar3가 각각 중수소, 시아노기, 할로겐기, 알킬기, 알콕시기, 할로겐화된 알콕시기, 할로겐화된 알킬기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 실릴기 및 아민기 중에서 선택된 1 또는 2 이상의 치환기로 치환되거나, 상기 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미하는 유기 화합물.According to paragraph 1,
In the definition of R 1 and Ar 1 to Ar 3 , substituted or unsubstituted means that R 1 and Ar 1 to Ar 3 are respectively deuterium, cyano group, halogen group, alkyl group, alkoxy group, halogenated alkoxy group, and halogenated alkyl group. , is substituted with one or two or more substituents selected from cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups, silyl groups and amine groups, is substituted with substituents where two or more of the substituents are connected, or does not have any substituents. an organic compound that means
상기 [화학식 Ⅰ]은 하기 [화학식 1] 내지 [화학식 252] 중에서 선택되는 어느 하나인 것을 특징으로 하는 유기 화합물:
According to paragraph 1,
[Formula I] is an organic compound selected from the following [Formula 1] to [Formula 252]:
상기 유기층 중 1 층 이상은 제1항에 따른 [화학식 Ⅰ]로 표시되는 유기 화합물을 하나 이상 포함하는 것을 특징으로 하는 유기발광소자.An organic light-emitting device comprising a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode,
An organic light-emitting device, wherein at least one of the organic layers includes at least one organic compound represented by [Chemical Formula I] according to claim 1.
상기 유기층은 전자주입층, 전자수송층, 정공주입층, 정공수송층, 전자저지층, 정공저지층 및 발광층 중 1층 이상을 포함하고,
상기 층들 중 1층 이상이 상기 [화학식 Ⅰ]로 표시되는 유기 화합물을 포함하는 것을 특징으로 하는 유기발광소자.According to clause 8,
The organic layer includes one or more of an electron injection layer, an electron transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, and a light emitting layer,
An organic light-emitting device, wherein at least one of the layers includes an organic compound represented by [Chemical Formula I].
상기 정공수송층에 상기 [화학식 Ⅰ]로 표시되는 유기 화합물을 포함하는 것을 특징으로 하는 유기발광소자.According to clause 9,
An organic light-emitting device comprising an organic compound represented by [Chemical Formula I] in the hole transport layer.
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