WO2018186662A2 - Organic light-emitting device - Google Patents
Organic light-emitting device Download PDFInfo
- Publication number
- WO2018186662A2 WO2018186662A2 PCT/KR2018/003926 KR2018003926W WO2018186662A2 WO 2018186662 A2 WO2018186662 A2 WO 2018186662A2 KR 2018003926 W KR2018003926 W KR 2018003926W WO 2018186662 A2 WO2018186662 A2 WO 2018186662A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- carbon atoms
- substituted
- independently
- light emitting
- Prior art date
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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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-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
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 241000207961 Sesamum Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 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
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
- HUOFUOCSQCYFPW-UHFFFAOYSA-N [4-(trifluoromethoxy)phenyl]boronic acid Chemical compound OB(O)C1=CC=C(OC(F)(F)F)C=C1 HUOFUOCSQCYFPW-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 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
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003609 aryl vinyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- GQVWHWAWLPCBHB-UHFFFAOYSA-L beryllium;benzo[h]quinolin-10-olate Chemical compound [Be+2].C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21.C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21 GQVWHWAWLPCBHB-UHFFFAOYSA-L 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 150000001638 boron Chemical class 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
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- XOYLJNJLGBYDTH-UHFFFAOYSA-M chlorogallium Chemical compound [Ga]Cl XOYLJNJLGBYDTH-UHFFFAOYSA-M 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 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
- 239000000539 dimer Substances 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000004090 dissolution Methods 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
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 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
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Inorganic materials Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 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
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 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
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- XNUVVHVFAAQPQY-UHFFFAOYSA-L manganese(2+) quinolin-8-olate Chemical compound N1=CC=CC2=CC=CC(=C12)[O-].[Mn+2].N1=CC=CC2=CC=CC(=C12)[O-] XNUVVHVFAAQPQY-UHFFFAOYSA-L 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000005358 mercaptoalkyl group Chemical group 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical class OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl 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
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000005353 silylalkyl group Chemical group 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- 150000003852 triazoles Chemical class 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
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- 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
-
- 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
Definitions
- the present invention relates to an organic light emitting device.
- organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
- the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent luminance, driving voltage and response speed characteristics, many studies have been conducted.
- the organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode.
- the organic material layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
- Patent Document 0001 Korean Patent Publication No. 10-2013-073537 [Contents of the Invention]
- the present invention provides an organic light emitting device.
- the present invention is an anode; A cathode provided to face the anode; And at least one organic material layer provided between the anode and the cathode, wherein the organic material layer includes a hole injection layer adjacent to the anode, a hole transport layer provided on the hole injection layer, and the hole transport layer.
- the hole injection layer comprises a compound selected from the group consisting of compounds represented by the formula 1-1 to 1-2
- the hole transport layer is an organic light emitting device comprising a compound represented by the formula (2) To provide.
- R 1 to R 5 are each independently a cyano group, a substituted or unsubstituted carbon number
- Aryl group of 6 to 60, black is a heteroaryl group having 2 to 60 carbon atoms containing at least one of substituted or unsubstituted 0, N, Si and S,
- R 15 to R 18 each independently represent a hydrogen, a halogen, a cyano group, an alkyl group having 1 to 40 carbon atoms, a haloalkyl group having 1 to 40 carbon atoms, a haloalkoxy group having 1 to 40 carbon atoms, a substituted or unsubstituted carbon group having 6 to 60 carbon atoms
- Y 3 and Y 4 are each independently CR 19 or N,
- Each R 19 independently represents a cyano group, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, including one or more of 0, N, Si, and S; ego,
- Ar 1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 or 60 carbon atoms containing at least one of 0, N, Si, and S,
- X 1 is an unbonded, single bond, an alkylene group having 1 to 3 carbon atoms, 0 or S, and L 1 and L 2 are each independently a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted group. It is a C2-C60 hetero arylene group containing 1 or more of 0, N, Si, and S,
- Ar 2 and Ar 3 are each independently selected from the group consisting of the following substituents
- Ar 4 to Ar 6 are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms including at least one of 0, N, Si, and S. ego,
- X 2 and X 3 are each independently a single bond, 0 or S.
- FIG. 1 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
- the compound selected from the group consisting of the compounds represented by the above formulas (1-1) to 1-2 is used as a material of the hole injection layer, the compound represented by the above formula (2) is used as a material of the hole transport layer is low Driving voltage and / or life characteristics can be improved. [Specific contents to carry out invention]
- the present invention provides an organic light emitting device in which the hole injection layer includes a compound selected from the group consisting of compounds represented by Formulas 1 to 1 to 1-2, and the hole transport layer includes a compound represented by Formula 2.
- the non-bond means a case where there is no chemical bond in the moiety represented by X 1 .
- a single bond means the case where no separate atom exists in the part represented by X ⁇ 1> -X ⁇ 3> .
- X ⁇ 1> of general formula (2) is a single bond, it is represented as follows.
- R a is heavy hydrogen, a halogen, a cyano group, a nitro group, an amino group, an alkyl group having 1 to 40 carbon atoms, 1 to 40 haloalkyl group, substituted or unsubstituted 0, N, Si and S containing at least one heteroalkyl group containing 1 to 40 carbon atoms, substituted or unsubstituted 0, N, Si and S at least one It may be a heterohaloalkyl group having 1 to 40 carbon atoms, or an alkenyl group having 2 to 40 carbon atoms.
- Halogen herein may be fluorine, chlorine, bromine or iodine.
- the alkyl group having 1 to 40 carbon atoms may be a straight chain, branched chain or cyclic alkyl group.
- the alkyl group having 1 to 40 carbon atoms is a straight chain alkyl group having 1 to 40 carbon atoms; Linear alkyl groups having 1 to 20 carbon atoms; Linear alkyl groups having 1 to 10 carbon atoms; Branched or cyclic alkyl groups having 3 to 40 carbon atoms; Branched or cyclic alkyl groups having 3 to 20 carbon atoms; Or a branched or cyclic alkyl group having 3 to 10 carbon atoms.
- the alkyl group having 1 to 40 carbon atoms is methyl group, ethyl group, n-propyl group, i so-propyl group, n-butyl group, i so-butyl group, t-butyl group, n-pentyl group, i so- Pentyl group, neo-pentyl group or cyclonuclear group.
- the present invention is not limited thereto.
- the heteroalkyl group having 1 to 40 carbon atoms may be one in which at least one carbon of the alkyl group is independently substituted with 0, N, Si, or S.
- the heteroalkyl group in which carbon number 1 of the n-butyl group is substituted with 0 is n-propoxy group
- the heteroalkyl group substituted with N is n-propylamino group
- the heteroalkyl group substituted with Si is n- It is a propylsilyl group
- the heteroalkyl group substituted by S is n-propylthio group.
- examples of the branched alkyl group a heteroalkyl group in which the carbon number 1 of the neo-pentyl group is substituted with 0 is a t-subgroup, a heteroalkyl group substituted with N is a t-butylamino group, and a heteroalkyl group substituted with Si is t A butylsilyl group, wherein the heteroalkyl group substituted by S is a t-butylthio group.
- annular As an example of the alkyl group, the heteroalkyl group in which the carbon number 2 of the cyclonuclear group is substituted with 0 is 2-tetrahydropyranyl group, and the heteroalkyl group substituted with N is substituted with 2-piperidinyl group
- the heteroalkyl group is a 1-sil a-cyc lohexyl group
- the heteroalkyl group substituted with S is a 2-tetrahydrothiopyranyl group.
- the heteroalkyl group having 1 to 40 carbon atoms may be a straight, branched or cyclic hydroxyalkyl group having 1 to 40 carbon atoms; Linear, branched or cyclic alkoxy groups having 1 to 40 carbon atoms; Linear, branched or cyclic alkoxyalkyl groups having 2 to 40 carbon atoms; Linear, branched or cyclic aminoalkyl groups having 1 to 40 carbon atoms; Linear, branched or cyclic alkylamino groups having 1 to 40 carbon atoms; Linear, branched or cyclic alkylaminoalkyl groups having 1 to 40 carbon atoms; Linear, branched or cyclic silylalkyl (oxy) groups having 1 to 40 carbon atoms; Linear, branched or cyclic alkyl (oxy) silyl groups having 1 to 40 carbon atoms; Linear, branched or cyclic alkyl (oxy) silyl groups having 1 to 40 carbon atoms
- the heteroalkyl group having 1 to 40 carbon atoms has a hydroxymethyl group, a meso group, an ethoxy group, an n-propoxy group, i so-propoxy group, a t-subspecial group, a cyclonucleooxy group, a hydroxymethyl group, i so -Propoxymethyl group, cyclonuclear methyl group 2-tetrahydropyranyl group, aminomethyl group, methylamino group, n-propylamino group, t-butylamino group, methylaminopropyl group, 2-piperidinyl group, n Propylsilyl group, trimethylsilyl group, dimethylmethoxysilyl group, t-butylsilyl group, 1-si la-cyc lohexyl group, n—propylthio group, t-butylthio group or 2-tetrahydrothiopyranyl (2—tetrahydrothio
- an alkenyl group having 2 to 40 carbon atoms may be a straight chain, branched chain or cyclic alkenyl group.
- the alkenyl group having 2 to 40 carbon atoms has a straight chain alkenyl group having 2 to 40 carbon atoms; Linear alkenyl groups having 2 to 20 carbon atoms; C2-C10 and linear alkenyl group; Branched alkenyl groups having 3 to 40 carbon atoms; Branched alkenyl groups having 3 to 20 carbon atoms; Branched alkenyl groups having 3 to 10 carbon atoms; Cyclic alkenyl groups having 5 to 40 carbon atoms; Cyclic alkenyl groups having 5 to 20 carbon atoms; Or a cyclic alkenyl group having 5 to 10 carbon atoms.
- the alkenyl group having 2 to 40 carbon atoms may be an ethenyl group, propenyl group, butenyl group, pentenyl group, cyclonucleenyl group, or the like.
- the aryl group having 6 to 60 carbon atoms may be a monocyclic aryl group or a polycyclic aryl group.
- an aryl group having 6 to 60 carbon atoms has a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
- the aryl group having 6 to 60 carbon atoms may be a phenyl group, a biphenyl group or a terphenyl group as a monocyclic aryl group, and as a polycyclic aryl group, a naphthyl group, anthracenyl group, phenanthryl group, triphenylenyl group, pyre Or a phenyl group, a perrylenyl group, a chrysenyl group, or a fluorenyl group.
- a fluorenyl group may be substituted, and two substituents may be
- the heteroaryl group having 2 to 60 carbon atoms may be one or more carbons of the aryl group are each independently substituted with 0, N, Si or S.
- the heteroaryl group substituted with 0 carbon of the fluorenyl group with 0 is a dibenzofuranyl group
- the heteroaryl group substituted with N is a carbazolyl group
- the heteroaryl group substituted with Si is a 9-sila-fluoroenyl group
- the heteroaryl group substituted with S is a dibenzothiophenyl group.
- a heteroaryl group having 2 to 60 carbon atoms is a heteroaryl group having 2 to 30 carbon atoms; Or a heteroaryl group having 2 to 20 carbon atoms. More specifically, the heteroaryl group having 2 to 60 carbon atoms may be a thiophene group, Furan group, Pyl group, imidazole group, Thiazole group, Oxazole group, Oxadiazole group, Triazole group, Pyridyl group, Bipyridyl group, Pyrimidyl group, Triazine group, Triazole group, Acridyl group, Pyridazine group, Pyrazin group Genyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxa
- the arylene group means a divalent organic group in which any one hydrogen radical of the aryl group has been removed
- the heteroarylene group means a divalent organic group in which any one hydrogen radical of the aforementioned heteroaryl group has been removed.
- one of R 2 and R 3 and one of R 4 and R 5 are cyano groups, R 1 ; The other of R 2 and R 3 ; And each other of R 4 and R 5 is independently a cyano group;
- R 2 and R 4 may be a cyano group
- R 1 , R 3 and R 5 may each independently be a phenyl group substituted with at least one member selected from the group consisting of halogen and cyano groups.
- the compound represented by Formula 1-1 may be the following compound.
- one of R 15 and R 16 and one of R 17 and R 18 may be each independently halogen, cyano group, alkyl group of 1 to 5 carbon atoms, haloalkyl group of 1 to 5 carbon atoms, and 1 to 5 carbon atoms.
- Y 3 and Y 4 are CR 19 , and R 19 is each independently a cyano group; Aryl group "of the group having 6 to 20 carbon atoms substituted with one or more selected from the group consisting of halogen and cyano; Or a heteroaryl group having 2 to 20 carbon atoms including one or more of 0, N, Si, and S substituted with one or more substituents selected from the group consisting of halogen and cyano groups.
- the compound represented by Chemical Formula 1-2 may be selected from the group consisting of the following compounds.
- the compound represented by Chemical Formula 1-2 may be prepared by a preparation method such as the following formula A.
- the manufacturing method may be more specific in the production examples to be described later.
- R 15 , R 16 , R 17 and R 18 are as described above, and further substituents may be further included.
- Ar 1 in Formula 2 is benzene, naphthalene, biphenyl, terphenyl, triphenylene, phenylnaphthalene, 9, 9-dimethyl fluorene, 9, 9-diphenyl fluorene and spiro [fluorene— 9, 9 ' -Fluorene] may be a monovalent residue from an arene selected from the group consisting of.
- L 1 and L 2 may each independently be a divalent residue derived from arene selected from the group consisting of benzene, naphthalene, biphenyl, and terphenyl.
- Ar 4 and Ar 5 may each independently be a monovalent residue derived from arene selected from the group consisting of benzene, naphthalene, biphenyl, and terphenyl.
- the compound represented by Chemical Formula 2 may be a compound represented by Chemical Formula 2-1.
- Ar 1 to Ar 3 and X 1 is the same as in Chemical Formula 2,
- L 3 to L 6 each independently represent a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted 0, N, Si, and S having at least one of 2 to 50 carbon atoms Heteroarylene group.
- the compound represented by Formula 2 may be selected from the group consisting of the following compounds.
- the compound represented by Chemical Formula 2 may be prepared by a preparation method such as the following reaction formula B.
- the manufacturing method may be more specific in the production examples to be described later.
- the reaction is carried out in the presence of a palladium catalyst and a base as a Suzuki coupling reaction.
- the kind of the reaction group and the catalyst used in the reaction system can be appropriately changed.
- the manufacturing method may be more specific in the production examples to be described later.
- the organic light emitting device of the present invention includes a cathode provided with both the anode; And at least one raised layer provided between the anode and the cathode.
- the organic material layer is composed of a multilayered structure of three or more organic material layers. Specifically, the organic material layer includes a hole main pressure layer adjacent to the anode, a hole transport layer provided on the hole injection layer, and a light emitting layer provided on the hole transport layer.
- the hole injection layer refers to a layer in which holes are injected from an anode and transferred to another organic material layer as an organic material layer contacting the anode of the organic light emitting device. Accordingly, the hole injection layer may also be referred to as a charge generating layer.
- the hole transport layer is an organic material layer provided on the hole injection layer of the organic light emitting diode, and refers to a layer that transfers holes transferred from the hole injection layer to the light emitting layer and suppresses electrons transferred from the light emitting layer from being transferred to the hole injection layer. Accordingly, the hole transport layer may also be referred to as an electron suppression layer.
- the organic light emitting device may include an electron transport layer, an electron injection layer, and the like between the light emitting layer and the cathode.
- the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers.
- the organic light emitting device according to the present invention may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
- the organic light emitting device according to the present invention may be an organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
- FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
- the compound selected from the group consisting of compounds represented by Formulas 1-1 to 1 ′ 2 is included in the hole injection layer 5, and the compound represented by Formula 2 is a hole transport layer 6. It can be included to improve the low driving voltage and / or life characteristics.
- the organic light emitting device includes a compound selected from the group consisting of compounds represented by Formulas 1-1 to 1-2 in the hole injection layer, and includes a compound represented by Formula 2 in the hole transport layer. It can be prepared by materials and methods known in the art, except that In addition, the plurality of organic material layers may be formed of the same material or different materials.
- the organic light emitting device according to the present invention may be manufactured by sequentially stacking an electrode of any one of an anode and a cathode, an organic material layer, and another electrode of the anode and the cathode on a substrate.
- PVD physical vapor deposition
- An oxide or an alloy thereof may be deposited to form an anode, and an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer may be formed thereon, and then a material that may be used as a cathode may be deposited thereon.
- an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (W0 2003/012890).
- the manufacturing method is not limited thereto.
- the compounds represented by Formulas 1-1 to 1-2 and the compound represented by Formula 2 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
- the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating and the like, but is not limited thereto.
- the anode material a material having a large work function is generally preferred to facilitate hole injection into the organic material layer.
- the positive electrode material include metals such as vanadium, crumb, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (IT0), indium zinc oxide (IZ0); ⁇ : A1 or SN0 2 : Combination of metal and oxide, such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4— (ethylene-1,2-dioxy) thiophene] (? £ 0 1), polypyrrole and polyaniline, but only It is not limited. It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
- the negative electrode material include metals such as magnesium, kaleum, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or Li0 2 / Al, and the like, but are not limited thereto.
- the hole injection layer is a layer for injecting holes from the electrode, the material forming the hole injection layer represented by the formula (1-1) to 1-2 Compounds selected from the group consisting of compounds are used. Since the compounds represented by Chemical Formulas 1-1 to 1-2 have been described above in detail, detailed descriptions thereof will be omitted.
- the compounds represented by Formulas 1-1 to 1-2 have the ability to transport holes, have a hole injection effect at the anode, an excellent hole injection effect to the light emitting layer or the light emitting material, an electron injection layer of excitons generated in the light emitting layer Alternatively, movement of the electron injection material can be prevented.
- the compounds of Formulas 1—1 to 1-2 have excellent thin film formation ability.
- the hole injection layer may further include a hole injection material known in the art to which the present invention pertains, in addition to the compound of Formulas 1-1 to 1-2.
- HOMO highest occupied molecul ar orbi tal is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
- hole-injecting materials include metal porphyr, oligothiophene, arylamine-based organic matter, nucleonitrile-nucleated azatriphenylene-based organic material, quinacridone-based organic material, and perylene ( perylene) organic materials, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
- the hole transport layer is a layer for receiving holes from the hole injection layer and transporting holes to the light emitting layer, and the compound represented by Chemical Formula 2 is used as a material for forming the hole transport layer. Since the compound represented by Chemical Formula 2 has been described in detail above, a detailed description thereof will be omitted.
- the compound represented by Chemical Formula 2 is suitable for transporting holes from the anode or the hole injection layer to the light emitting layer because of high mobility to the holes.
- the hole transport layer may further include a hole transport material known in the art. Specific examples of such hole transport materials include, but are not limited to, arylamine-based organics, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.
- the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and preferably a material having a high quantum efficiency with respect to fluorescence or phosphorescence.
- the light emitting layer may include a host material and a dopant material.
- the host material is a condensed aromatic ring derivative or a heterocyclic containing compound.
- the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
- the heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
- Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like.
- the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and the styrylamine compound may be substituted or unsubstituted.
- At least one arylvinyl group is substituted with the substituted arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
- the electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer.
- the electron transporting material is a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer. Suitable.
- the electron transport layer can be used with any desired cathode material as used in accordance with the prior art.
- suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically, they are sesame, barium, calcium, ytterbium and samarium, each followed by an aluminum layer or a silver layer.
- the electron injection layer is a layer for injecting electrons from an electrode, has a capability of transporting electrons, has an electron injection effect from the cathode, excellent electron injection effect to the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer
- the compound which prevents migration to a worm and is excellent in thin film formation ability is preferable.
- fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and their derivatives, Metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
- metal complex compound 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc,.
- the organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type according to the material used.
- the compound represented by Chemical Formulas 1-1 to 1-2 and the compound represented by Chemical Formula 2 And manufacturing of the organic light emitting device including the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto. Sejoye
- 1,4—Dibromo-2,5—Diiodobenzene 18.5 g (0.038 mol) to (4-trifluoromethoxy) phenylboronic acid 16.Og (0.078mol), tetrakis (triphenylphosphine) palladium ( 0) It was mixed with 2.2 g, 114 ml of 2M potassium carbonate, and 360 ml of tetrahydrofuran, and reflux stirring was performed for 8 hours on nitrogen conditions.
- 1,4-dibromo-2, 5-difluoro-3, 6-Taiyo Goto benzene (Compound b-2) 19.9g (0.038mol) of (2-fluoro-4 'trifluoromethoxy ) 17.5 g (0.078 mol) of phenyl boronic acids, 2.2 g of tetrakis (triphenylphosphine) palladium (0), 11M1 of 2M potassium carbonate, and 360 ml of tetrahydrofuran were mixed, and reflux stirring was performed for 12 hours on nitrogen conditions.
- a glass substrate coated with a thin film having an indium tin oxide (IT0) thickness of 1,000 A was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
- IT0 indium tin oxide
- Fischer Co. product was used as a detergent
- distilled water filtered secondly as a filter of Mi 11 ipore Co. was used as distilled water.
- the ultrasonic cleaning was performed twice with distilled water for 10 minutes.
- ultrasonic cleaning with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
- the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
- a hole transport layer was formed by vacuum depositing the following compound [HT1] (1150A), which is a material for transporting holes on the hole injection layer. Subsequently, the following compound [EB1] was vacuum deposited on the hole transport layer with a film thickness of 50 A to form an electron blocking layer.
- the following compound [BH] and compound [BD] were vacuum-deposited at a weight ratio of 50: 1 on the electron blocking layer at 200 A to form a light emitting layer.
- the compound [HB 1] was vacuum deposited on the hole transport layer to a film thickness of 50 A to form a hole blocking layer.
- Compound [ET1] and Compound [LiQ] were vacuum-deposited at a weight ratio of 1: 1 on the hole blocking layer to form a layer for simultaneously injecting and transporting electrons at a thickness of 310A.
- Lithium fluoride (LiF) and aluminum at a thickness of 2,000A were sequentially deposited on the electron injection and transport layer to form a cathode.
- the deposition rate of the organic material was maintained at 0.4-0.7 A / sec
- the lithium fluoride of the cathode was maintained at 0.3 A / sec
- the aluminum was maintained at the deposition rate of 2 A / sec.
- the organic light emitting device was manufactured by maintaining 7 to 5 ⁇ 10 ⁇ 6 torr.
- Comparative Example 1-1 an organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except for using the compounds shown in Table 1 below as components for the hole injection layer and the hole transport layer.
- the device structure used shows the characteristics of basic P-doping devices.
- the blue organic light emitting device of Comparative Examples 1-5 to 1-16 uses a compound of 1-2-1 to 1-2-3 as the hole injection layer and a compound of compounds ⁇ to HT4 as the hole transport layer. The characteristics of the type element are shown.
- Example 1-1 and 1-2 when the compound of 2-1 and 2-2 is used as the hole transport layer instead of the compounds of HT-1 to HT-4 in the basic p ⁇ doping device, the luminous efficiency and driving of the organic light emitting device It can be seen that the voltage and lifetime can be improved.
- Example 1—3 to 1-8 are 2-1 and 2- instead of the compounds of HT-1 to HT-4 in a layer type device using a compound of 1-2-1 magnetic 1-2-3 as a hole injection layer.
- the compound of 2 is used as the hole transport layer, it can be seen that the luminous efficiency, driving voltage and lifetime of the organic light emitting device can be improved.
- HT4 has a structure connected by met a and has a relatively low efficiency.
- the compound of Chemical Formula 1-2 (Tetracyanoquinodimethane: TCNQ core and its derivatives as a core) according to one embodiment of the present specification is used as a layer type hole injection layer material, or the compound of Chemical Formula 1-1
- the driving voltage, luminous efficiency and lifetime characteristics of the blue organic light emitting device formed by combining the compound of Formula 2 as the hole transport layer can be improved.
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Abstract
Description
【발명의 명칭】 [Name of invention]
유기 발광 소자 Organic light emitting device
【기술분야】 Technical Field
관련 출원 (들)과의 상호 인용 Cross Citation with Related Application (s)
본 출원은 2017 년 4 월 7 일자 한국 특허 출원 제 10—2017-0045389 호 및 2018 년 4 월 2 일자 한국 특허 출원 제 10-2018-0038119 호에 기초한 우선권의 이익을 주장하며， 해당 한국 특허 출원들의 문헌에 개시된 모든 내용은 본 명세서의 일부로서 포함된다. This application claims the benefit of priority based on Korean Patent Application No. 10—2017-0045389 dated April 7, 2017 and Korean Patent Application No. 10-2018-0038119 dated April 2, 2018. All content disclosed in the literature is included as part of this specification.
본 발명은 유기 발광 소자에 관한 것이다. The present invention relates to an organic light emitting device.
【발명의 배경이 되는 기술】 [Technique to become background of invention]
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 넓은 시야각， 우수한 콘트라스트， 빠른 웅답 시간을 가지며， 휘도， 구동 전압 및 웅답 속도 특성이 우수하여 많은 연구가 진행되고 있다. 유기 발광 소자는 일반적으로 양극과 음극 및 상기 양극과 음극 사이에 유기물층을 포함하는 구조를 가진다. 상기 유기물층은 유기 발광 소자의 효을과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며， 예컨대 정공주입층， 정공수송층， 발광층， 전자수송층， 전자주입층 등으로 이루어질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이， 음극에서는 전자가 유기물층에 주입되게 되고， 주입된 정공과 전자가 만났을 때 액시톤 (exci ton)이 형성되며， 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent luminance, driving voltage and response speed characteristics, many studies have been conducted. The organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode. The organic material layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. It will glow when the excitons fall back to the ground.
상기와 같은 유기 발광 소자에 사용되는 유기물에 대하여 새로운 재료의 개발이 지속적으로 요구되고 있다. 【선행기술문헌】 There is a continuous demand for the development of new materials for organic materials used in such organic light emitting devices. Prior Art Documents
【특허문헌】 [Patent literature]
(특허문헌 0001) 한국특허 공개번호 제 10-2013-073537호 【발명의 내용】 (Patent Document 0001) Korean Patent Publication No. 10-2013-073537 [Contents of the Invention]
【해결하고자 하는 과제】 Problem to be solved
본 발명은 유기 발광 소자를 제공한다. The present invention provides an organic light emitting device.
【과제의 해결 수단】 [Measures of problem]
본 발명은 양극; 상기 양극과 대향하여 구비된 음극; 및 상기 양극과 음극 사이에 구비된 1 층 이상의 유기물층을 포함하는 유기 발광 소자로서 , 상기 유기물층은 양극에 인접하는 정공 주입층， 상기 정공 주입층 상에 구비된 정공 수송층 및 상기 정공 수송층 상에 구비된 발광층을 포함하고， 상기 정공 주입층은 하기 화학식 1-1 내지 1-2로 표시되는 화합물로 구성된 군에서 선택된 화합물을 포함하고， 상기 정공 수송층은 하기 화학식 2로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다. The present invention is an anode; A cathode provided to face the anode; And at least one organic material layer provided between the anode and the cathode, wherein the organic material layer includes a hole injection layer adjacent to the anode, a hole transport layer provided on the hole injection layer, and the hole transport layer. Including an emission layer, The hole injection layer comprises a compound selected from the group consisting of compounds represented by the formula 1-1 to 1-2, The hole transport layer is an organic light emitting device comprising a compound represented by the formula (2) To provide.
상기 화학식 1ᅳ 1에서, In Chemical Formula 1-1,
R1 내지 R5는 각각 독립적으로 시아노기， 치환 또는 비치환된 탄소수R 1 to R 5 are each independently a cyano group, a substituted or unsubstituted carbon number
6 내지 60의 아릴기 , 흑은 치환 또는 비치환된 0， N , Si 및 S 중 1개 이상을 포함하는 탄소수 2 내지 60의 헤테로아릴기이고， Aryl group of 6 to 60, black is a heteroaryl group having 2 to 60 carbon atoms containing at least one of substituted or unsubstituted 0, N, Si and S,
상가화학식 1-2에서， In the formula 1-2,
R15 내지 R18은 각각 독립적으로 수소， 할로겐, 시아노기， 탄소수 1 내지 40의 알킬기， 탄소수 1 내지 40의 할로알킬기， 탄소수 1 내지 40의 할로알콕시기， 치환 또는 비차환된 탄소수 6 내지 60의 아릴기， 흑은 치환 또는 비치환된 0， N , Si 및 S 중 1개 이상을 포함하는 탄소수 2 내지 60의 헤테로아릴기이고， R 15 to R 18 each independently represent a hydrogen, a halogen, a cyano group, an alkyl group having 1 to 40 carbon atoms, a haloalkyl group having 1 to 40 carbon atoms, a haloalkoxy group having 1 to 40 carbon atoms, a substituted or unsubstituted carbon group having 6 to 60 carbon atoms An aryl group, black having 2 to 60 carbon atoms, including one or more of substituted, unsubstituted 0, N, Si, and S; Heteroaryl group,
Y3 및 Y4는 각각 독립적으로 C-R19 또는 N이고， Y 3 and Y 4 are each independently CR 19 or N,
R19는 각각 독립적으로 시아노기， 치환 또는 비치환된 탄소수 6 내지 60의 아릴기， 혹은 치환 또는 비치환된 0， N , Si 및 S 중 1개 이상을 포함하는 탄소수 2 내지 60의 헤테로아릴기이고， Each R 19 independently represents a cyano group, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, including one or more of 0, N, Si, and S; ego,
상기 화학식 2에서， In Chemical Formula 2,
Ar1은 치환 또는 비치환된 탄소수 6 내지 60의 아릴기， 혹은 치환 또는 비치환된 0, N , Si 및 S 중 1개 이상을 포함하는 탄소수 2 내지 60의 헤테로아릴렌기이고, Ar 1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 or 60 carbon atoms containing at least one of 0, N, Si, and S,
X1은 비결합， 단일결합， 탄소수 1 내지 3의 알킬렌기， 0또는 S이고, L1 및 L2는 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 60의 아릴렌기， 혹은 치환 또는 비치환된 0， N , Si 및 S 중 1개 이상을 포함하는 탄소수 2 내지 60의 헤테로아릴렌기이고， X 1 is an unbonded, single bond, an alkylene group having 1 to 3 carbon atoms, 0 or S, and L 1 and L 2 are each independently a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted group. It is a C2-C60 hetero arylene group containing 1 or more of 0, N, Si, and S,
Ar2 및 Ar3는 각각 독립적으로 하기 치환기로 구성된 군으로부터 선택된 Ar 2 and Ar 3 are each independently selected from the group consisting of the following substituents
Ar4 내지 Ar6는 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기， 혹은 치환 또는 비치환된 0, N, Si 및 S 중 1개 이상을 포함하는 탄소수 2 내지 60의 헤테로아릴기이고， Ar 4 to Ar 6 are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms including at least one of 0, N, Si, and S. ego,
X2 및 X3는 각각 독립적으로 단일결합， 0 또는 S이다. X 2 and X 3 are each independently a single bond, 0 or S.
【도면의 간단한 설명】 도 1 은 기판 ( 1)， 양극 (2)， 정공주입층 (5)， 정공수송층 (6)， 발광층 (7)， 전자수송층 (8) 및 음극 (4)로 이루어진 유기 발광 소자의 예를 도시한 것이다. [Brief Description of Drawings] FIG. 1 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
【발명의 효과] 【Effects of the Invention]
상술한 화학식 1-1 내지 1-2 으로 표시되는 화합물로 구성된 군에서 선택된 화합물은 정공 주입층의 재료로 사용되고, 상술한 화학식 2 로 표시되는 화합물은 정공 수송층의 재료로 사용되어 유기 발광 소자의 낮은 구동전압 및 /또는 수명 특성을 향상시킬 수 있다. 【발명을 실시하기 위한 구체적인 내용】 The compound selected from the group consisting of the compounds represented by the above formulas (1-1) to 1-2 is used as a material of the hole injection layer, the compound represented by the above formula (2) is used as a material of the hole transport layer is low Driving voltage and / or life characteristics can be improved. [Specific contents to carry out invention]
이하, 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다. 이하， 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다. 본 발명은 정공 주입층이 상기 화학식 1—1 내지 1-2 로 표시되는 화합물로 구성된 군에서 선택된 화합물을 포함하고， 정공 수송층이 상기 화학식 2로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다 . 본 명세서에서， 비결합은 X1으로 표시되는 부분에 화학적 결합이 없는 경우를 의미한다. 예컨대， 화학식 2 에서 X1 이 비결합이면 하기와 같이 '표시된다.
또한， 단일 결합은 X1 내지 X3 로 표시되는 부분에 별도의 원자가 존재하지 않은 경우를 의미한다. 예컨대, 화학식 2 의 X1 이 단일 결합이면 하기와 같이 표시된다 .
등이 될 수 있다. 다만， 이에 한정되는 것은 아니다. 본 명세서에서 탄소수 2 내지 60 의 헤테로아릴기는 아릴기의 1 개 이상의 탄소가 각각 독립적으로 0, N , Si 또는 S 로 치환된 것일 수 있다. 예컨대， 플루오레닐기의 9 번 탄소가 0 로 치환된 해테로아릴기는 디벤조퓨라닐기이고， N 으로 치환된 헤테로아릴기는 카바졸리기이며， Si 로 치환된 헤테로아릴기는 9-실라-플로오레닐기이고， S로 치환된 해테로아릴기는 디벤조티오페닐기이다. 구체적으로， 탄소수 2 내지 60 의 헤테로아릴기는 탄소수 2 내지 30 의 헤테로아릴기 ; 또는 탄소수 2 내지 20의 헤테로아릴기일 수 있다. 보다 구체적으로，ᅳ탄소수 2 내지 60 의 헤테로아릴기는 티오펜기， 퓨란기， 피를기， 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, 페난쓰를린기 (phenanthrol ine) , 티아졸릴기， 이소옥사졸릴기， 옥사디아졸릴기， 티아디아졸릴기， 벤조티아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나， 이들에만 한정되는 것은 아니다. 본 명세서에서 아릴렌기는 상술한 아릴기의 어느 하나의 수소 라디칼이 제거된 2 가의 유기기를 의미하고， 헤테로아릴렌기는 상술한 헤테로아릴기의 어느 하나의 수소 라디칼이 제거된 2가의 유기기를 의미한다. 상기 화학식 1-1 에서 R2 및 R3 중 하나와 R4 및 R5 중 하나는 시아노기이고， R1 ; R2 및 R3 중 다른 하나; 그리고 R4 및 R5 중 다른 하나는 각각 독립적으로 시아노기 ; 할로겐 및 시아노기로 구성된 군에서 선택된 1 종 이상으로 치환된 탄소수 6 내지 20 의 아릴기； 혹은 할로겐 및 시아노기로 구성된 군에서 선택된 1 개 이상의 치환기로 치환된 0， N, Si 및 S 중 1 개 이상을 포함하는 탄소수 2 내지 20의 헤테로아릴기일 수 있다. 구체적으로， 상기 화학식 1—1 에서 R2 및 R4는 시아노기이고, R1 , R3 및 R5 는 각각 독립적으로 할로겐 및 시아노기로 구성된 군에서 선택된 1 종 이상으로 치환된 페닐기일 수 있다. 보다 구체적으로， 상기 화학식 1-1 로 표시되는 화합물은 하기 화합물일 수 있다. And so on. However, the present invention is not limited thereto. In the present specification, the heteroaryl group having 2 to 60 carbon atoms may be one or more carbons of the aryl group are each independently substituted with 0, N, Si or S. For example, the heteroaryl group substituted with 0 carbon of the fluorenyl group with 0 is a dibenzofuranyl group, the heteroaryl group substituted with N is a carbazolyl group, and the heteroaryl group substituted with Si is a 9-sila-fluoroenyl group And the heteroaryl group substituted with S is a dibenzothiophenyl group. Specifically, a heteroaryl group having 2 to 60 carbon atoms is a heteroaryl group having 2 to 30 carbon atoms; Or a heteroaryl group having 2 to 20 carbon atoms. More specifically, the heteroaryl group having 2 to 60 carbon atoms may be a thiophene group, Furan group, Pyl group, imidazole group, Thiazole group, Oxazole group, Oxadiazole group, Triazole group, Pyridyl group, Bipyridyl group, Pyrimidyl group, Triazine group, Triazole group, Acridyl group, Pyridazine group, Pyrazin group Genyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxa Drowsiness, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthrol group (phenanthrol ine), thiazolyl group, isoxazolyl group, oxadia There may be a sleepy group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, a dibenzofuranyl group, and the like, but is not limited thereto. In the present specification, the arylene group means a divalent organic group in which any one hydrogen radical of the aryl group has been removed, and the heteroarylene group means a divalent organic group in which any one hydrogen radical of the aforementioned heteroaryl group has been removed. . In Formula 1-1, one of R 2 and R 3 and one of R 4 and R 5 are cyano groups, R 1 ; The other of R 2 and R 3 ; And each other of R 4 and R 5 is independently a cyano group; An aryl group having 6 to 20 carbon atoms substituted with one or more selected from the group consisting of halogen and cyano groups; or one of 0, N, Si, and S substituted with one or more substituents selected from the group consisting of halogen and cyano groups It may be a C2-C20 heteroaryl group containing the above. Specifically, in Formula 1-1, R 2 and R 4 may be a cyano group, and R 1 , R 3 and R 5 may each independently be a phenyl group substituted with at least one member selected from the group consisting of halogen and cyano groups. . More specifically, the compound represented by Formula 1-1 may be the following compound.
11 11
[반웅식 A] [Bungungsik A]
상기 반응은 말로노니트릴 (malononi tr i le)을 도입하는 반웅으로서， 팔라듐 촉매와 염기 존재하에 수행하는 것이 바람직하다. 또한， 상기 반웅식에 사용된 반웅기 및 촉매의 종류는 적절하게 변경 가능하다. 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다. 상기 화학식 2 에서 Ar1 은 벤젠， 나프탈렌， 바이페닐， 터페닐， 트리페닐렌， 페닐나프탈렌， 9 , 9-디메틸플루오렌， 9 , 9-디페닐플루오렌 및 스피로 [플루오렌— 9，9 ' -플루오렌]으로 구성된 군에서 선택된 아렌 유래의 1 가 잔기일 수 있다. 상기 화학식 2 에서 L1 및 L2 는 각각 독립적으로, 벤젠， 나프탈렌, 바이페닐 및 터페닐로 구성된 군에서 선택된 아렌 유래의 2가 잔기일 수 있다. The reaction is carried out in the presence of a palladium catalyst and a base as a reaction for introducing malononitrile. In addition, the kind of the reaction group and the catalyst used in the reaction system can be appropriately changed. The manufacturing method may be more specific in the production examples to be described later. Ar 1 in Formula 2 is benzene, naphthalene, biphenyl, terphenyl, triphenylene, phenylnaphthalene, 9, 9-dimethyl fluorene, 9, 9-diphenyl fluorene and spiro [fluorene— 9, 9 ' -Fluorene] may be a monovalent residue from an arene selected from the group consisting of. In Formula 2, L 1 and L 2 may each independently be a divalent residue derived from arene selected from the group consisting of benzene, naphthalene, biphenyl, and terphenyl.
Ar4 Ar 4
, / , /
상기 화학식 2 에서 Ar2 및 /또는 Ar3가 Ar5일 때， Ar4 및 Ar5는 각각 독립적으로 벤젠， 나프탈렌， 바이페닐 및 터페닐로 구성된 군에서 선택된 아렌 유래의 1가 잔기일 수 있다. When Ar 2 and / or Ar 3 in Ar 2 are Ar 5 , Ar 4 and Ar 5 may each independently be a monovalent residue derived from arene selected from the group consisting of benzene, naphthalene, biphenyl, and terphenyl.
상기 화학식 2 에서 Ar2 및 /또는 Ar3가
페닐일 수 있다. 상기 화학식 2 로 표시되는 화합물은 하기 화학식 2-1 로 표시되는 화합물일 수 있다. Phenyl. The compound represented by Chemical Formula 2 may be a compound represented by Chemical Formula 2-1.
[화학식 2-1]
상기 화학식 2-1에서， In Chemical Formula 2-1,
Ar1 내지 Ar3 및 X1은 상기 화학식 2와 동일하며， Ar 1 to Ar 3 and X 1 is the same as in Chemical Formula 2,
L3 내지 L6은 각각 독립적으로 단일 결합， 치환 또는 비치환된 탄소수 6 내지 50 의 아릴렌기， 혹은 치환 또는 비치환된 0， N , Si 및 S 중 1 개 이상을 포함하는 탄소수 2 내지 50의 헤테로아릴렌기이다. . 상기 화학식 2 로 표시되는 화합물은 하기 화합물로 구성되는 군으로부터 선택될 수 있다. L 3 to L 6 each independently represent a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted 0, N, Si, and S having at least one of 2 to 50 carbon atoms Heteroarylene group. . The compound represented by Formula 2 may be selected from the group consisting of the following compounds.
oz oz
9Z6C00/8T0ZaM/X3d Ζ9998Ϊ/8Ϊ0Ζ OAV 9Z6C00 / 8T0ZaM / X3d Ζ9998Ϊ / 8Ϊ0Ζ OAV
Z Z
[반응식 B]
상기 반웅은 스즈키 커플링 반웅으로서， 팔라듐 촉매와 염기 존재하에 수행하는 것이 바람직하다. 또한， 상기 반웅식에 사용된 반웅기 및 촉매의 종류는 적절하게 변경 가능하다. 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다. 본 발명의 유기 발광 소자는 양 상기 양극과 대 구비된 음극; 및 상기 양극과 음극 사이에 구비된 1 이상의 융기물층을 포함한다. 상기 유기물층은 3 층 이상의 유기물층。 적층된 다층 구조로 이루어진다. 구체적으로, 상기 유기물층은 양극에 인접하는 정공 주압층， 상기 정공 주입층 상에 구비된 정공 수송층 및 상기 정공 수송층 상에 구비된 발광층을 포함한다. 본 명세서에서， 정공 주입층은 유기 발광 소자의 양극에 접하는 유기물층으로 양극으로부터 정공을 주입 받아 다른 유기물층에 전달하는 층을 의미한다. 이에 따라， 상기 정공 주입층은 전하 발생층으로도 호칭될 수 있다. 정공 수송층은 유기 발광 소자의 정공 주입층 상에 구비된 유기물층으로 정공 주입층에서 전달된 정공을 발광층에 전달하고， 발광층에서 전달된 전자가 정공 주입층에 전달되지 못하도록 억제하는 층을 의미한다. 이에 따라， 상기 정공 수송층은 전자 억제층으로도 호칭될 수 있다. 이외， 상기 유기 발광 소자는 상기 발광층과 음극 사이에 전자 수송층 및 전자 주입층 등을 포함할 수 있다. 그러나， 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기물층을 포함할 수 있다. 본 발명에 따른 유기 발광 소자는， 기판 상에 양극， 1 층 이상의 유기물 층 및 음극이 순차적으로 적층된 구조 (normal type)의 유기 발광 소자일 수 있다. 또한， 본 발명에 따른 유기 발광 소자는 기판 상에 음극， 1 층 이상의 유기물 층 및 양극이 순차적으로 적층된 역방향 구조 ( inverted type)의 유기 발광 소자일 수 있다. 예컨대， 본 발명의 일 실시예에 따른 유기 발광 소자의 구조는 도 1에 예시되어 있다. 도 1 은 기판 ( 1)， 양극 (2)， 정공 주입층 (5)， 정공 수송층 (6) , 발광층 (7)， 전자 수송층 (8) 및 음극 (4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1-1 내지 1ᅳ 2 로 표시되는 화합물로 구성된 군에서 선택된 화합물은 상기 정공 주입층 (5)에 포함되고, 상기 화학식 2 로 표시되는 화합물은 정공 수송층 (6)에 포함되어 낮은 구동전압 및 /또는 수명 특성을 향상시킬 수 있다. 본 발명에 따른 유기 발광 소자는, 상기 정공 주입층에 상기 화학식 1- 1 내지 1-2 로 표시되는 화합물로 구성된 군에서 선택된 화합물을 포함하고， 상기 정공 수송층에 상기 화학식 2 로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. 또한， 상기 복수개의 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다. 예컨대， 본 발명에 따른 유기 발광 소자는 기판 상에 양극 및 음극 중 어느 하나의 전극， 유기물층 및 상기 양극 및 음극 중 다른 하나의 전극을 순차적으로 적층시켜 제조할 수 있다. 이때， 스퍼터링법 (sputter ing)이나 전자범 증발법 (e-beam evaporat ion)과 같은 PVD (phys i cal Vapor Depos i t ion)방법을 이용하여, 기판 상에 금속 또는 도전성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고， 그 위에 정공 주입층， 정공 수송층， 발광층 및 전자 수송층을 포함하는 유기물 층을 형성한 후， 그 위에 음극으로 사용할 수 있는 물질을 증착시켜 제조할 수 있다. 이와 같은 방법 외에도， 기판 상에 음극 물질부터 유기물 층， 양극 물질을 차례로 증착시켜 유기 발광 소자를 제조할 수 있다 (W0 2003/012890) . 다만， 제조 방법이 이에 한정되는 것은 아니다. 또한, 상기 화학식 1-1 내지 1-2 로 표시되는 화합물과， 상기 화학식 2 로 표시되는 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서， 용액 도포법이라 함은 스핀 코팅， 딥코팅， 닥터 불레이딩， 잉크젯 프린팅 , 스크린 프린팅， 스프레이법， 롤 코팅 등을 의미하지만， 이들만으로 한정되는 것은 아니다. 상기 양극 물질로는 통상 유기물 층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 상기 양극 물질의 구체적인 예로는 바나듐， 크름， 구리， 아연， 금과 같은 금속 또는 이들의 합금; 아연 산화물， 인듐 산화물， 인듐주석 산화물 ( IT0) , 인듐아연 산화물 ( IZ0)과 같은 금속 산화물; ΖηΟ :Α1 또는 SN02 : Sb 와 같은 금속과 산화물의 조합; 폴리 (3-메틸티오펜) , 폴리 [3 , 4—(에틸렌-1，2-디옥시)티오펜] (?£0 1)， 폴리피를 및 폴리아닐린과 같은 전도성 고분자 등이 있으나， 이들에만 한정되는 것은 아니다. 상기 음극 물질로는 통상 유기물 층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 상기 음극 물질의 구체적인 예로는 마그네슘， 칼슴， 나트륨， 칼륨， 티타늄， 인듐， 이트륨， 리튬， 가돌리늄， 알루미늄， 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 Li02/Al 과 같은 다층 구조 물질 등이 있으나， 이들에만 한정되는 것은 아니다. 상기 정공 주입층은 전극으로부터 정공을 주입하는 층으로， 이러한 정공 주입층을 형성하는 재료로 상기 화학식 1-1 내지 1-2 으로 표시되는 화합물로 구성된 군에서 선택된 화합물이 사용된다. 상기 화학식 1-1 내지 1- 2으로 표시되는 화합물에 대해서는 앞서 구체적으로 설명하였으므로 여기서는 자세한 설명을 생략한다. The reaction is carried out in the presence of a palladium catalyst and a base as a Suzuki coupling reaction. In addition, the kind of the reaction group and the catalyst used in the reaction system can be appropriately changed. The manufacturing method may be more specific in the production examples to be described later. The organic light emitting device of the present invention includes a cathode provided with both the anode; And at least one raised layer provided between the anode and the cathode. The organic material layer is composed of a multilayered structure of three or more organic material layers. Specifically, the organic material layer includes a hole main pressure layer adjacent to the anode, a hole transport layer provided on the hole injection layer, and a light emitting layer provided on the hole transport layer. In the present specification, the hole injection layer refers to a layer in which holes are injected from an anode and transferred to another organic material layer as an organic material layer contacting the anode of the organic light emitting device. Accordingly, the hole injection layer may also be referred to as a charge generating layer. The hole transport layer is an organic material layer provided on the hole injection layer of the organic light emitting diode, and refers to a layer that transfers holes transferred from the hole injection layer to the light emitting layer and suppresses electrons transferred from the light emitting layer from being transferred to the hole injection layer. Accordingly, the hole transport layer may also be referred to as an electron suppression layer. In addition, the organic light emitting device may include an electron transport layer, an electron injection layer, and the like between the light emitting layer and the cathode. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers. The organic light emitting device according to the present invention may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting device according to the present invention may be an organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting diode according to an embodiment of the present invention is illustrated in FIG. 1. FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is. In such a structure, the compound selected from the group consisting of compounds represented by Formulas 1-1 to 1 ′ 2 is included in the hole injection layer 5, and the compound represented by Formula 2 is a hole transport layer 6. It can be included to improve the low driving voltage and / or life characteristics. The organic light emitting device according to the present invention includes a compound selected from the group consisting of compounds represented by Formulas 1-1 to 1-2 in the hole injection layer, and includes a compound represented by Formula 2 in the hole transport layer. It can be prepared by materials and methods known in the art, except that In addition, the plurality of organic material layers may be formed of the same material or different materials. For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking an electrode of any one of an anode and a cathode, an organic material layer, and another electrode of the anode and the cathode on a substrate. At this time, the metal or the metal having conductivity on the substrate using a method of physical vapor deposition (PVD), such as sputtering or e-beam evaporat ion An oxide or an alloy thereof may be deposited to form an anode, and an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer may be formed thereon, and then a material that may be used as a cathode may be deposited thereon. have. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (W0 2003/012890). However, the manufacturing method is not limited thereto. In addition, the compounds represented by Formulas 1-1 to 1-2 and the compound represented by Formula 2 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating and the like, but is not limited thereto. As the anode material, a material having a large work function is generally preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material include metals such as vanadium, crumb, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (IT0), indium zinc oxide (IZ0); ΖηΟ: A1 or SN0 2 : Combination of metal and oxide, such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4— (ethylene-1,2-dioxy) thiophene] (? £ 0 1), polypyrrole and polyaniline, but only It is not limited. It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, kaleum, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or Li0 2 / Al, and the like, but are not limited thereto. The hole injection layer is a layer for injecting holes from the electrode, the material forming the hole injection layer represented by the formula (1-1) to 1-2 Compounds selected from the group consisting of compounds are used. Since the compounds represented by Chemical Formulas 1-1 to 1-2 have been described above in detail, detailed descriptions thereof will be omitted.
상기 화학식 1-1 내지 1-2 로 표시되는 화합물은 정공을 수송하는 능력을 가져 양극에서의 정공 주입 효과， 발광층 또는 발광 재료에 대하여 우수한 정공 주입 효과를 갖고， 발광층에서 생성된 여기자의 전자 주입층 또는 전자 주입 재료의 이동을 방지할 수 있다. 또한， 상기 화학식 1—1 내지 1-2의 화합물은 박막 형성 능력이 우수하다. 한편， 상기 정공 주입층에는 상기 화학식 1-1 내지 1-2 의 화합물 외에도 본 발명이 속한 기술분야에 알려진 정공 주입 물질이 추가로 포함될 수 있다. 이러한 정공 주입 물질로는 HOMO highest occupi ed molecul ar orbi tal )가 양극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 이러한 정공 주입 물질의 구체적인 예로는 금속 포피린 (porphyr in) , 올리고티오펜， 아릴아민 계열의 유기물， 핵사니트릴핵사아자트리페닐렌 계열의 유기물， 퀴나크리돈 (quinacr idone)계열의 유기물, 페릴렌 (perylene) 계열의 유기물， 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나， 이들에만 한정 되는 것은 아니다. 상기 정공 수송층은 정공 주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로， 이러한 정공 수송층을 형성하는 재료로는 상기 화학식 2 로 표시되는 화합물이 사용된다. 상기 화학식 2 로 표시되는 화합물에 대해서는 앞서 구체적으로 설명하였으므로 여기서는 자세한 설명을 생략한다. The compounds represented by Formulas 1-1 to 1-2 have the ability to transport holes, have a hole injection effect at the anode, an excellent hole injection effect to the light emitting layer or the light emitting material, an electron injection layer of excitons generated in the light emitting layer Alternatively, movement of the electron injection material can be prevented. In addition, the compounds of Formulas 1—1 to 1-2 have excellent thin film formation ability. Meanwhile, the hole injection layer may further include a hole injection material known in the art to which the present invention pertains, in addition to the compound of Formulas 1-1 to 1-2. As the hole injection material, HOMO highest occupied molecul ar orbi tal) is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of such hole-injecting materials include metal porphyr, oligothiophene, arylamine-based organic matter, nucleonitrile-nucleated azatriphenylene-based organic material, quinacridone-based organic material, and perylene ( perylene) organic materials, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto. The hole transport layer is a layer for receiving holes from the hole injection layer and transporting holes to the light emitting layer, and the compound represented by Chemical Formula 2 is used as a material for forming the hole transport layer. Since the compound represented by Chemical Formula 2 has been described in detail above, a detailed description thereof will be omitted.
상기 화학식 2 로 표시되는 화합물은 정공에 대한 이동성이 크기 때문에 양극이나 정공 주입층으로부터 정공을 수송 받아 발광층으로 옮겨주기에 적합하다. 한편， 상기 정공 수송층에는 상기 화학식 2 로 표시되는 화합물 외에도 본 발명이 속한 기술분야에 알려진 정공 수송 물질이 추가로 포함될 수 있다. 이러한 정공 수송 물질의 구체적인 예로는 아릴아민 계열의 유기물， 전도성 고분자， 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나， 이들에만 한정되는 것은 아니다. 상기 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송 받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서， 형광이나 인광에 대한 양자 효율이 #은 물질이 바람직하다. 구체적인 예로 8—히드록시ᅳ퀴놀린 알루미늄 착물 (Alq3) ; 카르바졸 계열 화합물; 이량체화 스티릴 (dimer i zed styryl ) 화합물; BAl q ; 10-히드록시벤조 퀴놀린 -금속 화합물 ; 벤족사졸 벤즈티아졸 및 벤즈이미다졸 계열의 화합물 ; 폴리 (P- 페닐렌비닐렌 KPPV) 계열의 고분자; 스피로 ( sp i ro) 화합물; 폴리플루오렌， 루브렌 등이 있으나， 이들에만 한정되는 것은 아니다. 상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체， 피렌 유도체， 나프탈렌 유도체， 펜타센 유도체 , 페난트렌 화합물， 플루오란텐 화합물 등이 있고 , 헤테로환 함유 화합물로는 카바졸 유도체， 디벤조퓨란 유도체， 래더형 퓨란 화합물， 피리미딘 유도체 등이 있으나， 이에 한정되지 않는다. 도편트 재료로는 방향족 아민 유도체， 스트릴아민 화합물， 붕소 착체, 플루오란텐 화합물， 금속 착체 등이 있다. 구체적으로 방향족 아민 유도체로는 치환 또는 비치환된 아릴아미노기를 갖는 축합 방향족환 유도체로서， 아릴아미노기를 갖는 피렌， 안트라센， 크리센, 페리플란텐 등이 있으며， 스티릴아민 화합물로는 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로， 아릴기， 실릴기， 알킬기， 시클로알킬기 및 아릴아미노기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민， 스티릴디아민， 스티릴트리아민, 스티릴테트라아민 등이 있으나， 이에 한정되지 않는다. 또한, 금속 착체로는 이리듐 착체， 백금 착체 등이 있으나， 이에 한정되지 않는다. 상기 전자 수송층은 전자 주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층으로， 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 A1 착물; Al 를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본—금속 착물 등이 있으나， 이들에만 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이 임의의 원하는 캐소드 물질과 함께 사용할 수 있다. 특히, 적절한 캐소드 물질의 예는 낮은 일함수를 가지고 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로 세슴， 바륨, 칼슘, 이테르븀 및 사마륨이고， 각 경우 .알루미늄 층 또는 실버층이 뒤따른다. 상기 전자 주입층은 전극으로부터 전자를 주입하는 층으로， 전자를 수송하는 능력을 갖고, 음극으로부터의 전자 주입 효과， 발광층 또는 발광 재료에 대하여 우수한 전자 주입 효과를 가지며， 발광층에서 생성된 여기자의 정공 주입충으로의 이동을 방지하고， 또한， 박막형성능력이 우수한 화합물이 바람직하다. 구체적으로는 플루오레논， 안트라퀴노다이메탄， 다이페노퀴논， 티오피란 다이옥사이드， 옥사졸， 옥사다이아졸， 트리아졸， 이미다졸， 페릴렌테트라카복실산， 프레오레닐리덴 메탄， 안트론 둥과 그들와 유도체， 금속 착체 화합물 및 질소 함유 5 원환 유도체 등이 있으나， 이에 한정되지 않는다. 상기 금속 착체 화합물로서는 8-하이드록시퀴놀리나토 리튬， 비스 (8- 하이드록시퀴놀리나토)아연, . 비스 (8-하이드록시퀴놀리나토)구리， 비스 (8- 하이드록시퀴놀리나토)망간， 트리스 (8-하이드록시퀴놀리나토)알루미늄， 트리스 (2-메틸 -8-하이드록시퀴놀리나토)알루미늄 트리스 (8- 하이드록시퀴놀리나토)갈륨， 비스 ( 10-하이드록시벤조 [h]퀴놀리나토)베릴륨, 비스 ( 10-하이드록시벤조 [h]퀴놀리나토)아연, 비스 (2-메틸 -8- 퀴놀리나토)클로로갈륨， 비스 (2-메틸 -8-퀴놀리나토 ) (0-크레졸라토)갈륨， 비스 (2-메틸 -8-퀴놀리나토 ) ( 1-나프를라토)알루미늄， 비스 (2ᅳ메틸 -8- 퀴놀리나토) (2-나프틀라토)갈륨 등이 있으나， 이에 한정되지 않는다. 본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형， 후면 발광형 또는 양면 발광형일 수 있다.. 상술한 화학식 1-1 내지 1-2으로 표시되는 화합물 및 상기 화학식 2로 표시되는 화합물 그리고 이를 포함하는 유기 발광 소자의 제조는 이하 실시예에서 구체적으로 설명한다. 그러나 하기 실시예는 본 발명을 예시하기 위한 것이며， 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다. 쎄조예 The compound represented by Chemical Formula 2 is suitable for transporting holes from the anode or the hole injection layer to the light emitting layer because of high mobility to the holes. Meanwhile, in addition to the compound represented by Formula 2, the hole transport layer may further include a hole transport material known in the art. Specific examples of such hole transport materials include, but are not limited to, arylamine-based organics, conductive polymers, and block copolymers having both conjugated and non-conjugated portions. The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and preferably a material having a high quantum efficiency with respect to fluorescence or phosphorescence. Specific examples thereof include 8—hydroxy ᅳ quinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimer i zed styryl compounds; BAl q; 10-hydroxybenzoquinoline-metal compound; Benzoxazole benzthiazole and benzimidazole-based compounds; Poly (P-phenylenevinylene KPPV) series polymer; Spi ro compounds; Polyfluorene, rubrene and the like, but are not limited thereto. The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic containing compound. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and the heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto. Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and the styrylamine compound may be substituted or unsubstituted. At least one arylvinyl group is substituted with the substituted arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted. Specifically, styrylamine ， styryldiamine ， Styryl triamine, styryl tetraamine and the like, but is not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto. The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer. The electron transporting material is a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer. Suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Al; Organic radical compounds; Hydroxyflavones—metal complexes and the like, but are not limited to these. The electron transport layer can be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically, they are sesame, barium, calcium, ytterbium and samarium, each followed by an aluminum layer or a silver layer. The electron injection layer is a layer for injecting electrons from an electrode, has a capability of transporting electrons, has an electron injection effect from the cathode, excellent electron injection effect to the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer The compound which prevents migration to a worm and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and their derivatives, Metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto. As said metal complex compound, 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc,. Bis (8-hydroxyquinolinato) copper, Bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, Tris (2-methyl-8-hydroxyquinolinato) Aluminum tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl -8- Quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( 0 -cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphlato) aluminum, bis ( 2 ᅳ methyl-8-quinolinato) (2-naphthlato) gallium and the like, but is not limited thereto. The organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type according to the material used. The compound represented by Chemical Formulas 1-1 to 1-2 and the compound represented by Chemical Formula 2 And manufacturing of the organic light emitting device including the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto. Sejoye
제조예 1 : 화합물 1-2-1의 합성 Preparation Example 1 Synthesis of Compound 1-2-1
( 1) 중간체 A의 합성 (1) Synthesis of Intermediate A
[반웅식 1-1] [Bungungsik 1-1]
화합물 a 중간체 A Compound a Intermediate A
1， 4—다이브로모 -2， 5—다이요오도벤젠 18.5g (0.038mol )을 (4- 트리플루오로메록시)페닐보론산 16. Og (0.078mol ) , 테트라키스 (트라이페닐포스핀)팔라듐 (0) 2.2g, 2M 탄산 칼륨 114ml , 테트라하이드로퓨란 360ml 와 흔합하고， 질소 조건에서 8 시간 환류 교반을 행하였다. 넁각 후， 물과 디클로로메탄으로 추출하고， 추가로 실리카겔 컬럼 (전개 용매: 에틸아세테이트 /핵산 = 10/1)으로 분리하여， 백색 고체 (화합물 a)를 8.0g (38.0%) 얻었다. 다음으로， 이 백색 고체 (화합물 a) 8.5g (15.3mmol), 니켈 파우더 9.0g (76.6mmol), 포타슘아이오다이드 5.0g (30.½mol), 아이오딘 0.19g (0.77醒 ol)을 디메틸포름알데히드 20tnl 와 흔합하고， 아르곤 조건에서 24 시간 환류 교반을 행하였다. 반웅 종료후， 100ml 의 3% 묽은 염산과 40ml 의 디에틸 에테르을 투입하였다. 니켈 고형물을 제거하고， 물과 디에틸 에테르로 추출하고, 실리카겔 컬럼 (전개 용매 : 에틸아세테이트 /핵산 = 10/1)으로 분리하여， 백색 고체 (중간체 A)를 5.4g (54.0%) 얻었다. 1,4—Dibromo-2,5—Diiodobenzene 18.5 g (0.038 mol) to (4-trifluoromethoxy) phenylboronic acid 16.Og (0.078mol), tetrakis (triphenylphosphine) palladium ( 0) It was mixed with 2.2 g, 114 ml of 2M potassium carbonate, and 360 ml of tetrahydrofuran, and reflux stirring was performed for 8 hours on nitrogen conditions. After the extraction, the mixture was extracted with water and dichloromethane, and further separated by a silica gel column (developing solvent: ethyl acetate / nucleic acid = 10/1) to obtain 8.0 g (38.0%) of a white solid (Compound a ). Next, this white solid (compound a) 8.5g (15.3mmol), nickel powder 9.0g (76.6mmol), potassium iodide 5.0g (30.½mol) and 0.19g (0.77 醒 ol) iodine are mixed with 20tnl of dimethylformaldehyde, Time reflux agitation was performed. After completion of reaction, 100 ml of 3% dilute hydrochloric acid and 40 ml of diethyl ether were added thereto. The nickel solid was removed, extracted with water and diethyl ether, and separated by a silica gel column (developing solvent: ethyl acetate / nucleic acid = 10/1) to obtain 5.4 g (54.0%) of a white solid (intermediate A).
(2) 화합물 1-2-1의 합성 (2) Synthesis of Compound 1-2-1
중간체 A 화합물 1-2-1 말로노나이트릴 1.7g 을 1，2-다이메특시에탄 60ml 에 녹인 후 질소조건에서 -10 ° C 로 넁각하였다. 소듐 하이드라이드 (1.3g)을 4 회로 나누어 적하하고， 상은에서 20 분간 교반한 뒤 0 °C로 재넁각하였다. 2'，5'- 다이요오도 -4，4' '- 비스 (트라이플루오르메톡시) -1，1' :4'，1' '-터페닐 (중간체 A) 3.60g (5.54隱01)과 테트라키스 (트리페닐포스핀)팔라듐 0.64g (0.55醒 ol)을 투입하고， 환류 조건에서 8 시간 교반하였다. 그 후， 묽은 염산과 에틸아세테이트로 분리하고， 무수황산나트륨으로 건조 및 여과하였다. 에틸아세테이트를 감압증류한 후， 실리카겔 컬럼 (전개 용매 : 에틸아세테이트)으로 분리하여, 고체를 1.8g (62.0%) 얻었다. Intermediate A compound 1-2-1 malononitrile 1.7g was dissolved in 60ml of 1,2-dimethecethane and then cooled to -10 ° C under nitrogen. Sodium hydride (1.3 g) was added dropwise into four portions, stirred for 20 minutes at phase silver, and re-cooled to 0 ° C. 2 ', 5'-diiodo-4,4'-bis (trifluoromethoxy) -1,1': 4 ', 1'-terphenyl (intermediate A) 3.60 g (5.54 隱 01) and tetra 0.64 g (0.55 Pa) of kiss (triphenylphosphine) palladium was added thereto, followed by stirring at reflux for 8 hours. Thereafter, the mixture was separated with dilute hydrochloric acid and ethyl acetate, dried over anhydrous sodium sulfate, and filtered. The ethyl acetate was distilled under reduced pressure, and then separated by silica gel column (developing solvent: ethyl acetate) to obtain 1.8 g (62.0%) of a solid.
다음으로， 상기 고체 1.8g 을 아세토니트릴 3( l 에 녹인 후， 희석한 브롬수 20ml 를 투입하였다. 20 분 교반 후, 과량의 증류수를 투입하여 석출된 고체를 여과하고， 증류수로 세정하였다. 그 후， 아세토니트릴로 재결정하여 1.20g의 고체 (화합물 1-2-1)을 얻었다. 제조예 2: 화합물 1-2-2의 합성 Next, 1.8 g of the solid was dissolved in acetonitrile 3 (l, and 20 ml of diluted bromine water was added. After stirring for 20 minutes, an excess of distilled water was added thereto, and the precipitated solid was filtered and washed with distilled water. Then, recrystallized with acetonitrile to obtain 1.20 g of solid (Compound 1-2-1) Preparation Example 2: Synthesis of Compound 1-2-2
(1) 중간체 B의 합성
화합물 b-1 화합물 b-2 화합물 b-3 중간체 B Compound b-1 Compound b-2 Compound b-3 Intermediate B
2，2，6， 6—테트라메틸피페리다이드화 리튬 (100隱01)을 테트라하이드로퓨란 120ml 에 녹인 후 질소조건에서 -78 °C로 넁각하였다. 1,4-디브로모 -2, 5-디플루오르벤젠 27.2g (100醒 ol)을 테트라하이드로퓨란 60ml 에 녹여， 질소조건, -78 ° C 에서 삽관 투입하고， 상온으로 승온하였다. 그 후， 소듐 티오 설페이트 수용액으로 반웅을 종료하고， 에틸아세테이트로 분리하여， 무수황산나트륨으로 건조 및 여과하였다. 실리카겔 컬럼 (전개 용매: 에틸아세테이트 /핵산 = 10/1)으로 분리하여， 고체 (화합물 b-1) 26.3g (66.0%) 얻었다. 2,2,6, 6-tetramethylpiperidide lithium (100 隱0 1) was dissolved in 120 ml of tetrahydrofuran and then cooled to -78 ° C. under nitrogen. 27.2 g of 1,4-dibromo-2 and 5-difluorobenzene (100 μl) were dissolved in 60 ml of tetrahydrofuran, intubated at -78 ° C. under nitrogen, and the temperature was raised to room temperature. Thereafter, the reaction was terminated with an aqueous sodium thiosulfate solution, separated with ethyl acetate, dried over anhydrous sodium sulfate, and filtered. A silica gel column (developing solvent: ethyl acetate / nucleic acid = 10/1) was separated to give 26.3 g (66.0%) of a solid (compound b-1).
다음으로， 2,2， 6 ,6-테트라메틸피페리다이드화 리튬 (100隱01)을 테트라하이드로퓨란 120ml 에 녹인 후 질소조건에서 -78 °C로 넁각하였다. 1,4- 디브로모 -2，5-디플루오르 -3-요오도벤젠 (화합물 b-1) 39.8g (100隱 ol)을 테트라하이드로퓨란 60ml 에 녹여， 질소조건, —78 ° C 에서 삽관 투입하고， 상은으로 승온하였다. 그 후， 소듐 티오 설페이트 수용액으로 반웅을 종료하고， 에틸아세테이트로 분리하여， 무수황산나트륨으로 건조 및 여과하였다. 실리카겔 컬럼 (전개 용매 : 에틸아세테이트 /핵산 = 10/1)으로 분리하여， 고체 (화합물 b-2) 30.3g (58.0%) 얻었다. Next, 2,2, 6,6-tetramethylpiperidide lithium (100 隱0 1) was dissolved in 120 ml of tetrahydrofuran, and then cooled to -78 ° C under nitrogen. Dissolve 39.8 g (100 μl) of 1,4-dibromo-2,5-difluoro-3-iodobenzene (Compound b-1) in 60 ml of tetrahydrofuran, intubate at nitrogen conditions, —78 ° C. It put in and heated up to silver. Thereafter, the reaction was terminated with an aqueous sodium thiosulfate solution, separated with ethyl acetate, dried over anhydrous sodium sulfate, and filtered. A silica gel column (developing solvent: ethyl acetate / nucleic acid = 10/1) was separated to give 30.3 g (58.0%) of a solid (compound b-2).
다음으로， 1， 4-다이브로모 -2， 5-다이플루오로 -3， 6- 다이요오도벤젠 (화합물 b-2) 19.9g (0.038mol)을 (2—플루오르 -4- ' 트리플루오로메톡시)페닐보론산 17.5g (0.078mol), 테트라키스 (트라이페닐포스핀)팔라듐 (0) 2.2g, 2M 탄산 칼륨 11½1， 테트라하이드로퓨란 360ml 와 흔합하고， 질소 조건에서 12 시간 환류 교반을 행하몄다. 넁각 후， 물과 .디클로로메탄으로 추출하고， 추가로 실리카겔 컬럼 (전개 용매 : 에틸아세테이트 /핵산 = 10/1)으로 분리하여， 백색 고체 (화합물 b— 3)를 7.8g (34.7%) 얻었다. Next, 1,4-dibromo-2, 5-difluoro-3, 6-Taiyo Goto benzene (Compound b-2) 19.9g (0.038mol) of (2-fluoro-4 'trifluoromethoxy ) 17.5 g (0.078 mol) of phenyl boronic acids, 2.2 g of tetrakis (triphenylphosphine) palladium (0), 11M1 of 2M potassium carbonate, and 360 ml of tetrahydrofuran were mixed, and reflux stirring was performed for 12 hours on nitrogen conditions. After the extraction, the mixture was extracted with water and dichloromethane and further separated with a silica gel column (developing solvent: ethyl acetate / nucleic acid = 10/1) to obtain 7.8 g (34.7%) of a white solid (Compound b-3).
다음으로， 이 백색 고체 (화합물 b-3) 9.06g (15.3瞧01)， 니켈 파우더 9.0g (76.6mmol), 포타슘아이오다이드 5.0g (30.4匪01)， 아이오딘 0.19g (0.77画 ol)을 디메틸포름알데히드 20ml 와 흔합하고， 아르곤 조건에서 24시간 환류 교반을 행하였다. 반웅 종료후， 100ml 의 3%묽은 염산과 40ml 의 디에틸 에테르을 투입하였다. 니켈 고형물을 제거하고, 물과 디에틸 에테르로 추출하고， 실리카겔 컬럼 (전개 용매 : 에틸아세테이트 /핵산 = 10/1)으로 분리하여，.백색 고체 (중간체 B)를 3.2g(30.4« 얻었다. Next, this white solid (Compound b-3) 9.06g (15.3-301), nickel powder 9.0g (76.6mmol), potassium iodide 5.0g (30.4 匪0 1), iodine 0.19g (0.77 Pa) was mixed with 20 ml of dimethylformaldehyde, and reflux stirring was performed for 24 hours under argon conditions. After completion of reaction, 100 ml of 3% diluted hydrochloric acid and 40 ml of diethyl ether were added thereto. The nickel solid was removed, extracted with water and diethyl ether, and separated by a silica gel column (developing solvent: ethyl acetate / nucleic acid = 10/1) to give 3.2 g (30.4 '' of a white solid (intermediate B).
(2) 화합물 1-2-2의 합성(2) Synthesis of Compound 1-2-2
-4] -4]
1，1' :4'，1' 'ᅳ터페닐 (중간체 B) 3.8g 으로 변경한 것 이외에는 동일하게 반웅, 정제를 행하여 고체 (화합물 1—2—2) 0.84g 을 얻었다. 얻어진 고체의 질량 스펙트럼 측정 결과， M/Z=560에서 피크가 확인되었다. 제조예 3: 화합물 1-2-3의 합성 The reaction was carried out in the same manner, except that the content was changed to 3.8 g of 1,1 ': 4' and 1''terphenyl (intermediate B), and 0.84 g of a solid (compound 1-2-2) was obtained. As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at M / Z = 560. Preparation Example 3 Synthesis of Compound 1-2-3
중간체 C 화합물 1-2-3 화합물 1—2-1 의 합성에서 2' ,5'-다이요오도ᅳ 4,4' '- 비스 (트라이플루오르메록시) -1，1' :4'，1' '-터페닐 (중간체 A) 3.60g 을 2,2 - (4，4' '-비스 (트라이폴루오로메톡시) -[1，1' :4'，1' '-터페닐] -2'，5'- 디일)비스 (2- (펜타플루오로페닐)아세토니트릴) (중간체 C) 2.2g 으로 변경한 것 이외에는 동일하게 반웅， 정제를 행하여 고체 (화합물 1-2-3) 0.8g 을 얻었다. 얻어진 고체의 질량 스펙트럼 측정 결과， M/Z=806 에서 피크가 확인되었다. 제조예 4: 화합물 2-1의 합성 Intermediate C Compound 1-2-3 2 ', 5'-Diiododo 4,4''-bis (trifluoromeroxy) -1,1': 4 ', 1''-terphenyl (Intermediate A) in the synthesis of compound 1-2 3.60 g of 2,2-(4,4 '' -bis (tripololomethoxy)-[1,1 ': 4', 1'-terphenyl] -2 ', 5'-diyl) bis ( Aside from changing to 2.2 g of 2- (pentafluorophenyl) acetonitrile) (Intermediate C), the reaction was carried out in the same manner to obtain 0.8 g of a solid (compound 1-2-3). As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at M / Z = 806. Preparation Example 4 Synthesis of Compound 2-1
MS[M+H]+= 730 제조예 5: 화합물 2-2의 합성 MS [M + H] + = 730 Preparation Example 5 Synthesis of Compound 2-2
[반웅식 2-2] [Bungungsik 2-2]
질소 분위기에서 500 mL 등근 바닥 플라스크에 화합물 3,6-dibromo-9- (naphthalen-2-yl )-9H-carbazole (5.32 g, 11.85 誦 ol), 및 화합물 al(7.46 g, 26.07 mmol)을 테트라하이드로퓨란 240 mL 에 완전히 녹인 후 2M 탄산칼륨수용액 (120 mL)을 첨가하고， 테트라키스- In a 500 mL back-bottom flask in a nitrogen atmosphere, add compound 3,6-dibromo-9- (naphthalen-2-yl) -9H-carbazole (5.32 g, 11.85 誦 ol), and compound al (7.46 g, 26.07 mmol) in tetra After completely dissolved in 240 mL of hydrofuran, 2M aqueous potassium carbonate solution (120 mL) was added thereto, followed by tetrakis-
(트리페닐포스판)팔라듐 (0.41 g, 0.36 瞧 ol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에틸아세테이트 230 mL 로 재결정하여 화합물 2- 2(5.57 g, 60%)를 제조하였다. (Triphenylphosphane) palladium (0.41 g, 0.36 dl ol) was added thereto, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 230 mL of ethyl acetate to obtain Compound 2- 2 (5.57 g, 60%).
MS[M+H]+= 780 실시예 및 비교예 MS [M + H] + = 780 Examples and Comparative Examples
(1) 비교예 1-1의 제조 (1) Preparation of Comparative Example 1-1
IT0( indium tin oxide)가 1,000A의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이 때， 세제로는 피셔사 (Fischer Co.) 제품을 사용하였으며， 증류수로는 밀러포어사 (Mi 11 ipore Co.) 제품의 필터 (Filter)로 2 차로 걸러진 증류수를 사용하였다. IT0 를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후， 이소프로필알콜， 아세톤， 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한， 산소 플라즈마를 이용하여 상기 기판을 5 분간 세정한 후 진공 증착기로 기판을 수송시켰다. A glass substrate coated with a thin film having an indium tin oxide (IT0) thickness of 1,000 A was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. product was used as a detergent, and distilled water filtered secondly as a filter of Mi 11 ipore Co. was used as distilled water. After washing IT0 for 30 minutes, the ultrasonic cleaning was performed twice with distilled water for 10 minutes. After the distilled water wash, ultrasonic cleaning with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
이렇게 준비된 양극인 ΠΌ 투명 전극 위에 하기 화합물 [HI1] 및 하기 화합물 1-1-1 의 화합물을 98:2(몰비)의 비가 되도록 100A의 두께로 열 진공 증착하여 정공주입층을 형성하였다 (p-doping matrix). Thus prepared compound [HI1] and the compound of the following compound 1-1-1 were thermally vacuum-deposited at a thickness of 100 A so as to have a ratio of 98: 2 (molar ratio) on the transparent electrode as a positive electrode thus prepared to form a hole injection layer (p- doping matrix).
상기 정공주입층 위에 정공을 수송하는 물질인 하기 화합물 [HT1] (1150A)를 진공 증착하여 정공수송층을 형성하였다. 이어서， 상기 정공수송층 위에 막 두께 50A으로 하기 화합물 [EB1]을 진공 증착하여 전자차단층을 형성하였다. A hole transport layer was formed by vacuum depositing the following compound [HT1] (1150A), which is a material for transporting holes on the hole injection layer. Subsequently, the following compound [EB1] was vacuum deposited on the hole transport layer with a film thickness of 50 A to form an electron blocking layer.
[BH] [BD] [BH] [BD]
(2) 비교예 1—2 내지 1—16 및 실시예 1-1 내지 1-8의 제조 상기 비교예 1-1 에서， 전공주입층 및 정공수송층의 성분을 하기 표 1 에 기재된 화합물을 사용한 것을 제외하고는， 비교예 1-1 과 동일한 방법으로 유기 발광 소자를 제조하였다. (2) Preparation of Comparative Examples 1 to 2 to 16 and Examples 1-1 to 1-8 In Comparative Example 1-1, an organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except for using the compounds shown in Table 1 below as components for the hole injection layer and the hole transport layer.
【표 1】 Table 1
Homo값이 5.2eV 정도인 ΗΊΊ 및 5.8eV 정도인 HT— 3은 인접한 층에 대한 barr i er 가 커서 전압이 크게 상승하는 결과를 얻었다. 카바졸의 3， 6 번위치에 직접 아민기가 연결된 HT2 의 물질을 사용한 비교예는 소자의 특성이 가장 저조하게 측정되었다. HT4 는 청구항 1 의 화학식 2 와는 달리 met a로 연결된 구조이며， 상대적으로 효율이 낮게 측정되었다. Homo values of about 5.2eV, Η— and 5.8eV, and HT–3 resulted in a large voltage increase due to large barr ier for adjacent layers. In the comparative example using the substance of HT2 having an amine group directly connected to the 3 and 6 positions of carbazole, the characteristics of the device were the lowest. Unlike Formula 2 of claim 1, HT4 has a structure connected by met a and has a relatively low efficiency.
이를 통하여 본 명세서의 일 실시상태에 따른 화학식 1- 2(Tetracyanoquinodimethane :TCNQ 코어 및 이의 유도체를 코어로 포함)의 화합물을 Layer type 정공주입층 재료로 사용하거나， 상기 화학식 1-1 의 화합물을 p-doping 정공주입층 재료로 사용한 소자구조에서 화학식 2 의 화합물을 정공수송층으로 조합하여 만들어지는 청색 유기 발광 소자의 구동전압, 발광효율 및 수명 특성을 개선할 수 있다는 것을 확인할 수 있다. Through this, the compound of Chemical Formula 1-2 (Tetracyanoquinodimethane: TCNQ core and its derivatives as a core) according to one embodiment of the present specification is used as a layer type hole injection layer material, or the compound of Chemical Formula 1-1 In the device structure used as the doping hole injection layer material, it can be seen that the driving voltage, luminous efficiency and lifetime characteristics of the blue organic light emitting device formed by combining the compound of Formula 2 as the hole transport layer can be improved.
【부호의 설명】 [Explanation of code]
1 : 기판 2 : 양극 1 substrate 2 anode
4： 음극 5： 정공 주입층 4: cathode 5: hole injection layer
6： 정공 수송층 7 : 발광층 6: hole transport layer 7: light emitting layer
8： 전자 수송층 8: electron transport layer
Claims
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| KR1020180038119A KR102088506B1 (en) | 2017-04-07 | 2018-04-02 | Organic light emitting device |
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| KR20090028943A (en) * | 2007-09-17 | 2009-03-20 | (주)루디스 | Hole injection layer / hole transport layer material and organic light emitting device comprising the same |
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