KR20210056219A - Novel compound and organic light emitting device comprising the same - Google Patents
Novel compound and organic light emitting device comprising the same Download PDFInfo
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- KR20210056219A KR20210056219A KR1020200118540A KR20200118540A KR20210056219A KR 20210056219 A KR20210056219 A KR 20210056219A KR 1020200118540 A KR1020200118540 A KR 1020200118540A KR 20200118540 A KR20200118540 A KR 20200118540A KR 20210056219 A KR20210056219 A KR 20210056219A
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- South Korea
- Prior art keywords
- group
- compound
- emitting device
- organic light
- alkyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 86
- 238000000034 method Methods 0.000 claims abstract description 31
- 239000011368 organic material Substances 0.000 claims abstract description 25
- -1 biphenylyl Chemical group 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 229920001187 thermosetting polymer Polymers 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 27
- 239000000126 substance Substances 0.000 abstract description 8
- 239000010410 layer Substances 0.000 description 85
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 238000002347 injection Methods 0.000 description 36
- 239000007924 injection Substances 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 125000004432 carbon atom Chemical group C* 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 18
- 239000008199 coating composition Substances 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000758 substrate Substances 0.000 description 13
- 230000032258 transport Effects 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 230000005525 hole transport Effects 0.000 description 12
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 10
- 229940125904 compound 1 Drugs 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000000151 deposition Methods 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 229940126214 compound 3 Drugs 0.000 description 4
- 229940125898 compound 5 Drugs 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 239000010406 cathode material Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- NPFYZDNDJHZQKY-UHFFFAOYSA-N 4-Hydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 NPFYZDNDJHZQKY-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- PFYHAAAQPNMZHO-UHFFFAOYSA-N Methyl 2-methoxybenzoate Chemical compound COC(=O)C1=CC=CC=C1OC PFYHAAAQPNMZHO-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000005137 deposition process Methods 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005241 heteroarylamino group Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 125000005462 imide group Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 229940015975 1,2-hexanediol Drugs 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- HSKPJQYAHCKJQC-UHFFFAOYSA-N 1-ethylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2CC HSKPJQYAHCKJQC-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical compound CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-UHFFFAOYSA-N 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- UXCIJKOCUAQMKD-UHFFFAOYSA-N 2,4-dichlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC(Cl)=C3SC2=C1 UXCIJKOCUAQMKD-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- LZHUBCULTHIFNO-UHFFFAOYSA-N 2,4-dihydroxy-1,5-bis[4-(2-hydroxyethoxy)phenyl]-2,4-dimethylpentan-3-one Chemical compound C=1C=C(OCCO)C=CC=1CC(C)(O)C(=O)C(O)(C)CC1=CC=C(OCCO)C=C1 LZHUBCULTHIFNO-UHFFFAOYSA-N 0.000 description 1
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- CGMMPMYKMDITEA-UHFFFAOYSA-N 2-ethylbenzoic acid Chemical compound CCC1=CC=CC=C1C(O)=O CGMMPMYKMDITEA-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SJNXJRVDSTZUFB-UHFFFAOYSA-N naphthalen-2-yl(phenyl)methanone Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)C1=CC=CC=C1 SJNXJRVDSTZUFB-UHFFFAOYSA-N 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
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 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
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- 238000000746 purification Methods 0.000 description 1
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- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
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- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl 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
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- 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
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning 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
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 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
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- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- H10K50/00—Organic light-emitting devices
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- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H—ELECTRICITY
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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Abstract
Description
본 발명은 신규한 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. The present invention relates to a novel compound and an organic light emitting device comprising the same.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 넓은 시야각, 우수한 콘트라스트, 빠른 응답 시간을 가지며, 휘도, 구동 전압 및 응답 속도 특성이 우수하여 많은 연구가 진행되고 있다. In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using an organic material. An organic light-emitting device using the organic light-emitting phenomenon has a wide viewing angle, excellent contrast, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.
유기 발광 소자는 일반적으로 양극과 음극 및 상기 양극과 음극 사이에 유기물층을 포함하는 구조를 가진다. 상기 유기물층은 유기 발광 소자의 효율과 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 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. An 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 multilayer structure made of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. When it falls back to the ground, it glows.
상기와 같은 유기 발광 소자에 사용되는 유기물에 대하여 새로운 재료의 개발이 지속적으로 요구되고 있다.Development of new materials for organic materials used in organic light emitting devices as described above is continuously required.
한편, 최근에는 공정 비용 절감을 위하여 기존의 증착 공정 대신 용액 공정, 특히 잉크젯 공정을 이용한 유기 발광 소자가 개발되고 있다. 초창기에는 모든 유기 발광 소자 층을 용액 공정으로 코팅하여 유기 발광 소자를 개발하려 하였으나 현재 기술로는 한계가 있어, 정구조 형태에서 HIL, HTL, EML만을 용액 공정으로 진행하고 추후 공정은 기존의 증착 공정을 활용하는 하이브리드(hybrid) 공정이 연구 중이다. On the other hand, in recent years, in order to reduce process cost, an organic light emitting device using a solution process, in particular an inkjet process, instead of a conventional deposition process has been developed. In the early days, an attempt was made to develop an organic light-emitting device by coating all organic light-emitting device layers by a solution process, but the current technology has limitations, so only HIL, HTL, and EML in the form of a regular structure are carried out as a solution process, and the later process is the existing deposition process. A hybrid process that utilizes is being studied.
이에 본 발명에서는 유기 발광 소자에 사용될 수 있으면서 동시에 용액 공정에 사용 가능한 신규한 유기 발광 소자의 소재를 제공한다.Accordingly, in the present invention, a material for a novel organic light-emitting device that can be used in an organic light-emitting device and at the same time can be used in a solution process is provided.
본 발명은 신규한 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. The present invention relates to a novel compound and an organic light emitting device comprising the same.
본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다: The present invention provides a compound represented by the following formula (1):
[화학식 1] [Formula 1]
상기 화학식 1에서,In Formula 1,
R1은 각각 독립적으로, C3-10 알킬이고, Each R 1 is independently C 3-10 alkyl,
R2는 각각 독립적으로, 수소, 또는 C1-10 알킬이고, Each R 2 is independently hydrogen or C 1-10 alkyl,
Ar1은 광경화성기; 또는 열경화성기이고, Ar 1 is a photocurable group; Or a thermosetting group,
Ar2는 각각 독립적으로, 1개 내지 3개의 C3-10 알킬로 치환된 C6-60 아릴이고,Ar 2 are each independently C 6-60 aryl substituted with 1 to 3 C 3-10 alkyl,
Ar3은 각각 독립적으로, 비치환되거나 또는 C3-10 알킬로 치환된 C6-60 아릴이다. Each Ar 3 is independently C 6-60 aryl unsubstituted or substituted with C 3-10 alkyl.
또한, 본 발명은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물의 경화물을 포함하는 것인, 유기 발광 소자를 제공한다.In addition, the present invention is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a cured product of the compound represented by Formula 1 It provides a light emitting device.
상술한 화학식 1로 표시되는 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있으며, 또한 용액 공정에 사용이 가능하며, 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는 수명 특성을 향상시킬 수 있다. The compound represented by Formula 1 above can be used as a material for an organic material layer of an organic light-emitting device, and can also be used in a solution process, and can improve efficiency, low driving voltage, and/or life characteristics in an organic light-emitting device. have.
도 1은 기판(1), 양극(2), 발광층(3), 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.
도 2는 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(7), 전자주입 및 수송층(8) 및 음극(4)로 이루어진 유기 발광 소자의 예를 도시한 것이다.
도 3 및 도 4는, 본 발명의 실험예 4의 결과를 나타낸 것이다. 1 shows an example of an organic light-emitting device comprising a
2 is an example of an organic light-emitting device comprising a
3 and 4 show the results of Experimental Example 4 of the present invention.
이하, 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다.Hereinafter, it will be described in more detail to aid in understanding the present invention.
(용어의 정의)(Definition of Terms)
본 명세서에서, 
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 시아노기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 사이클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로아릴로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환 또는 비치환된 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 비페닐기일 수 있다. 즉, 비페닐이기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수도 있다.In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Cyano group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Arylsulfoxy group; Silyl group; Boron group; Alkyl group; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or it means substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl containing one or more of N, O, and S atoms, or substituted or unsubstituted with two or more substituents connected among the above exemplified substituents. . For example, "a substituent to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent to which two phenyl groups are connected.
본 명세서에서 카보닐기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 40인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
본 명세서에 있어서, 에스테르기는 에스테르기의 산소가 탄소수 1 내지 25의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 25의 아릴기로 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the ester group may be substituted with a C1-C25 linear, branched or cyclic alkyl group or an aryl group having 6 to 25 carbon atoms in the oxygen of the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
본 명세서에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.
본 명세서에 있어서, 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, but is not limited thereto.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 6이다. 알킬기의 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 사이클로펜틸메틸, 사이클로헥틸메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸펜틸, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이들에 한정되지 않는다.In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cycloheptylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 6이다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 알릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나 이들에 한정되지 않는다.In the present specification, the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
본 명세서에 있어서, 사이클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 사이클로프로필, 사이클로부틸, 사이클로펜틸, 3-메틸사이클로펜틸, 2,3-디메틸사이클로펜틸, 사이클로헥실, 3-메틸사이클로헥실, 4-메틸사이클로헥실, 2,3-디메틸사이클로헥실, 3,4,5-트리메틸사이클로헥실, 4-tert-부틸사이클로헥실, 사이클로헵틸, 사이클로옥틸 등이 있으나, 이에 한정되지 않는다.In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 비페닐이기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난쓰레닐기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. 상기 플루오레닐기가 치환되는 경우, 
본 명세서에 있어서, 헤테로아릴은 이종 원소로 O, N, Si 및 S 중 1개 이상을 포함하는 헤테로아릴로서, 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로아릴의 예로는 잔텐(xanthene), 티오잔텐(thioxanthen), 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤즈옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 페난쓰롤린기(phenanthroline), 이소옥사졸릴기, 티아디아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, heteroaryl is a heteroaryl containing at least one of O, N, Si, and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but it is preferably 2 to 60 carbon atoms. Examples of heteroaryl include xanthene, thioxanthen, thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, Pyrimidyl group, triazine group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino Pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group ( phenanthroline), isoxazolyl group, thiadiazolyl group, phenothiazinyl group, and dibenzofuranyl group, but are not limited thereto.
본 명세서에 있어서, 아르알킬기, 아르알케닐기, 알킬아릴기, 아릴아민기, 아릴실릴기 중의 아릴기는 전술한 아릴기의 예시와 같다. 본 명세서에 있어서, 아르알킬기, 알킬아릴기, 알킬아민기 중 알킬기는 전술한 알킬기의 예시와 같다. 본 명세서에 있어서, 헤테로아릴아민 중 헤테로아릴은 전술한 헤테로아릴에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 아르알케닐기 중 알케닐기는 전술한 알케닐기의 예시와 같다. 본 명세서에 있어서, 아릴렌은 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로아릴렌은 2가기인 것을 제외하고는 전술한 헤테로아릴에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 탄화수소 고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 아릴기 또는 사이클로알킬기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 헤테로아릴에 관한 설명이 적용될 수 있다.In the present specification, the aryl group among the aralkyl group, aralkenyl group, alkylaryl group, arylamine group, and arylsilyl group is the same as the example of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group and the alkylamine group is the same as the example of the aforementioned alkyl group. In the present specification, the heteroaryl among the heteroarylamines may be described above for heteroaryl. In the present specification, the alkenyl group of the aralkenyl group is the same as the example of the alkenyl group described above. In the present specification, the description of the aryl group described above may be applied except that the arylene is a divalent group. In the present specification, the description of the above-described heteroaryl may be applied except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aryl group or cycloalkyl group described above may be applied except that the hydrocarbon ring is formed by bonding of two substituents. In the present specification, the heterocycle is not a monovalent group, and the description of the above-described heteroaryl may be applied except that the heterocycle is formed by bonding of two substituents.
(화합물)(compound)
본 발명은 상기 화학식 1로 표시되는 화합물을 제공한다. The present invention provides a compound represented by
바람직하게는, Ar1은 -L"-R"이고, L"는 단일 결합, -O-, -S-, -CH2-, -CH2O-, -OCH2-, 또는 -CH2OCH2-이고, R"는 하기로 구성되는 군으로부터 선택되는 어느 하나이다:Preferably, Ar 1 is -L"-R" and L" is a single bond, -O-, -S-, -CH 2 -, -CH 2 O-, -OCH 2 -, or -CH 2 OCH 2 -and R" is any one selected from the group consisting of:
보다 바람직하게는, Ar1은 하기 중 어느 하나이다:More preferably, Ar 1 is any one of:
바람직하게는, R1은 각각 독립적으로, 직쇄 C3-10 알킬이고, 보다 바람직하게는 직쇄 C3-6 알킬이다. 바람직하게는, R1은 각각 독립적으로, 프로필, 부틸, 펜틸, 또는 헥실이다. Preferably, each R 1 is independently, straight-chain C 3-10 alkyl, more preferably straight-chain C 3-6 alkyl. Preferably, each R 1 is independently propyl, butyl, pentyl, or hexyl.
바람직하게는, R2는 각각 독립적으로, 수소, 또는 C1-4 알킬이다. 바람직하게는, R2는 각각 독립적으로, 수소, 메틸, 에틸, 또는 프로필이다. Preferably, each R 2 is independently hydrogen or C 1-4 alkyl. Preferably, each R 2 is independently hydrogen, methyl, ethyl, or propyl.
바람직하게는, Ar2는 페닐이고, 상기 페닐은 1개 또는 2개의 C1-5 알킬로 치환된다. 바람직하게는, Ar2는 페닐이고, 상기 페닐은 메틸, 에틸, 프로필, 부틸, 이소부틸 및 터트부틸로 구성되는 군으로부터 선택되는 1개 또는 2개의 치환기로 치환된다.Preferably, Ar 2 is phenyl and the phenyl is substituted with 1 or 2 C 1-5 alkyl. Preferably, Ar 2 is phenyl, and the phenyl is substituted with one or two substituents selected from the group consisting of methyl, ethyl, propyl, butyl, isobutyl and tertbutyl.
바람직하게는, Ar3은 C6-12 아릴이고, 상기 C6-12 아릴은 비치환되거나, 또는 C1-5 알킬로 치환된다. 바람직하게는, Ar3은 페닐 또는 비페닐릴이고; 상기 페닐 또는 비페닐릴은 비치환되거나, 또는 메틸, 에틸, 또는 프로필로 치환된다. Preferably, Ar 3 is C 6-12 aryl, and the C 6-12 aryl is unsubstituted or substituted with C 1-5 alkyl. Preferably, Ar 3 is phenyl or biphenylyl; The phenyl or biphenylyl is unsubstituted or substituted with methyl, ethyl, or propyl.
상기 화학식 1로 표시되는 화합물의 대표적인 예는 하기와 같다:Representative examples of the compound represented by
또한, 본 발명은 일례로 하기 반응식 1과 같은 상기 화학식 1로 표시되는 화합물의 제조방법을 제공한다:In addition, the present invention provides a method for preparing a compound represented by
[반응식 1][Scheme 1]
상기 반응식 1에서, X를 제외한 나머지 정의는 앞서 정의한 바와 같으며, X는 할로겐이고, 바람직하게는 클로로, 또는 브로모이다. 상기 반응은 아민 치환 반응으로서, 팔라듐 촉매와 염기 존재하에 수행하는 것이 바람직하며, 아민 치환 반응을 위한 반응기는 당업계에 알려진 바에 따라 변경이 가능하다. 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다. In
(코팅 조성물)(Coating composition)
한편, 본 발명에 따른 화합물은 용액 공정으로 유기 발광 소자의 유기물 층, 특히 정공주입층 또는 정공수송층을 형성할 수 있다. 이를 위하여, 본 발명은 상술한 본 발명에 따른 화합물 및 용매를 포함하는 코팅 조성물을 제공한다. Meanwhile, the compound according to the present invention may form an organic material layer, particularly a hole injection layer or a hole transport layer, of an organic light-emitting device by a solution process. To this end, the present invention provides a coating composition comprising the compound and a solvent according to the present invention described above.
상기 용매는 본 발명에 따른 화합물을 용해 또는 분산시킬 수 있는 용매이면 특별히 제한되지 않으며, 일례로 클로로포름, 염화메틸렌, 1,2-디클로로에탄, 1,1,2-트리클로로에탄, 클로로벤젠, o-디클로로벤젠 등의 염소계 용매; 테트라하이드로퓨란, 디옥산 등의 에테르계 용매; 톨루엔, 크실렌, 트리메틸벤젠, 메시틸렌 등의 방향족 탄화수소계 용매; 시클로헥산, 메틸시클로헥산, n-펜탄, n-헥산, n-헵탄, n-옥탄, n-노난, n-데칸 등의 지방족 탄화수소계 용매; 아세톤, 메틸에틸케톤, 시클로헥사논 등의 케톤계 용매; 아세트산에틸, 아세트산부틸, 에틸셀로솔브아세테이트 등의 에스테르계 용매; 에틸렌글리콜, 에틸렌글리콜모노부틸에테르, 에틸렌글리콜모노에틸에테르, 에틸렌글리콜모노메틸에테르, 디메톡시에탄, 프로필렌글리콜, 디에톡시메탄, 트리에틸렌글리콜모노에틸에테르, 글리세린, 1,2-헥산디올 등의 다가 알코올 및 그의 유도체; 메탄올, 에탄올, 프로판올, 이소프로판올, 시클로헥산올 등의 알코올계 용매; 디메틸술폭사이드 등의 술폭사이드계 용매; 및 N-메틸-2-피롤리돈, N,N-디메틸포름아미드 등의 아미드계 용매; 부틸벤조에이트, 메틸-2-메톡시벤조에이트 등의 벤조에이트계 용매; 테트랄린; 3-phenoxy-toluene 등의 용매를 들 수 있다. 또한, 상술한 용매를 1종 단독으로 사용하거나 2종 이상의 용매를 혼합하여 사용할 수 있다. The solvent is not particularly limited as long as it is a solvent capable of dissolving or dispersing the compound according to the present invention, and examples include chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o -Chlorine solvents such as dichlorobenzene; Ether solvents such as tetrahydrofuran and dioxane; Aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; Aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; Ketone solvents such as acetone, methyl ethyl ketone, and cyclohexanone; Ester solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; Polyvalents such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol, etc. Alcohol and its derivatives; Alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; Sulfoxide solvents such as dimethyl sulfoxide; And amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; Benzoate solvents such as butyl benzoate and methyl-2-methoxybenzoate; Tetralin; Solvents, such as 3-phenoxy-toluene, are mentioned. In addition, the above-described solvent may be used alone or in combination of two or more solvents.
또한, 상기 코팅 조성물의 점도는 1 cP 내지 10 cP가 바람직하며, 상기의 범위에서 코팅이 용이하다. 또한, 상기 코팅 조성물 내 본 발명에 따른 화합물의 농도는 0.1 wt/v% 내지 20 wt/v%인 것이 바람직하다. In addition, the viscosity of the coating composition is preferably 1 cP to 10 cP, and coating is easy within the above range. In addition, it is preferable that the concentration of the compound according to the present invention in the coating composition is 0.1 wt/v% to 20 wt/v%.
또한, 상기 코팅 조성물은 열중합 개시제 및 광중합 개시제로 이루어진 군에서 선택되는 1종 또는 2종 이상의 첨가제를 추가로 포함할 수 있다.In addition, the coating composition may further include one or two or more additives selected from the group consisting of a thermal polymerization initiator and a photopolymerization initiator.
상기 열중합 개시제로, 메틸 에틸 케톤퍼옥사이드, 메틸 이소부틸 케톤퍼옥사이드, 아세틸아세톤퍼옥사이드, 메틸사이클로헥사논 퍼옥사이드, 시클로헥사논 퍼옥사이드, 이소부티릴 퍼옥사이드, 2,4-디클로로벤조일 퍼옥사이드, 비스-3,5,5-트리메틸 헥사노일 퍼옥사이드, 라우릴 퍼옥사이드, 벤조일 퍼옥사이드 등의 과산화물, 또는 아조비스 이소부틸니트릴, 아조비스디메틸발레로니트릴, 및 아조비스 시클로헥실 니트릴 등의 아조계가 있으나, 이에 한정되지 않는다. As the thermal polymerization initiator, methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, acetylacetone peroxide, methyl cyclohexanone peroxide, cyclohexanone peroxide, isobutyryl peroxide, 2,4-dichlorobenzoyl peroxide Peroxides such as oxide, bis-3,5,5-trimethyl hexanoyl peroxide, lauryl peroxide, benzoyl peroxide, or azobis isobutylnitrile, azobisdimethylvaleronitrile, and azobis cyclohexyl nitrile. There is an azo system, but it is not limited thereto.
상기 광중합 개시제로, 디에톡시 아세토페논, 2,2-디메톡시-1,2-디페닐 에탄-1-온, 1-하이드록시-사이클로헥실-페닐-케톤, 4-(2-히드록시에톡시)페닐-(2-하이드록시-2-프로필) 케톤, 2-벤질-2-디메틸아미노-1-(4-모르폴리노페닐) 부타논-1,2-하이드록시-2-메틸-1-페닐 프로판-1-온, 2-메틸-2-모르폴리노(4-메틸 티오 페닐) 프로판-1-온, 1-페닐-1,2-프로판디온-2-(o-에톡시카르보닐) 옥심 등의 아세토페논계 또는 케탈계 광중합 개시제; 벤조인, 벤조인 메틸 에테르, 벤조인 에틸 에테르 등의 벤조인에테르계 광중합 개시제; 벤조페논, 4-하이드록시벤조페논, 2-벤조일나프탈렌, 4-벤조일비페닐, 4-벤조일 페닐 에테르, 등의 벤조페논계 광중합 개시제; 2-이소프로필티옥산톤, 2-클로로티옥산톤, 2,4-디메틸 티옥산톤, 2,4-디에틸티옥산톤, 2,4-디클로로티옥산톤 등의 티옥산톤계 광중합 개시제; 및 에틸 안트라퀴논, 2,4,6-트리메틸벤조일 디페닐 포스핀옥사이드, 2,4,6-트리메틸벤조일 페닐 에톡시 포스핀옥사이드, 비스(2,4,6-트리메틸벤조일) 페닐 포스핀옥사이드, 비스(2,4-디메톡시 벤조일)-2,4,4-트리메틸 펜틸포스핀 옥사이드 등의 기타 광중합 개시제가 있으나, 이에 한정되지 않는다. As the photoinitiator, diethoxy acetophenone, 2,2-dimethoxy-1,2-diphenyl ethan-1-one, 1-hydroxy-cyclohexyl-phenyl-ketone, 4-(2-hydroxyethoxy ) Phenyl-(2-hydroxy-2-propyl) ketone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl) butanone-1,2-hydroxy-2-methyl-1- Phenyl propan-1-one, 2-methyl-2-morpholino (4-methyl thiophenyl) propan-1-one, 1-phenyl-1,2-propanedione-2-(o-ethoxycarbonyl) Acetophenone-based or ketal-based photopolymerization initiators such as oxime; Benzoin ether photopolymerization initiators such as benzoin, benzoin methyl ether, and benzoin ethyl ether; Benzophenone photopolymerization initiators such as benzophenone, 4-hydroxybenzophenone, 2-benzoylnaphthalene, 4-benzoylbiphenyl, and 4-benzoylphenyl ether; Thioxanthone photopolymerization initiators, such as 2-isopropyl thioxanthone, 2-chloro thioxanthone, 2,4-dimethyl thioxanthone, 2,4-diethyl thioxanthone, and 2,4-dichloro thioxanthone; And ethyl anthraquinone, 2,4,6-trimethylbenzoyl diphenyl phosphine oxide, 2,4,6-trimethylbenzoyl phenyl ethoxy phosphine oxide, bis(2,4,6-trimethylbenzoyl) phenyl phosphine oxide, Other photoinitiators such as bis(2,4-dimethoxy benzoyl)-2,4,4-trimethyl pentylphosphine oxide, but are not limited thereto.
또한, 광중합 촉진 효과를 가지는 것을 단독 또는 상기 광 중합개시제와 병용해 이용할 수도 있다. 예를 들면, 트리에탄올아민, 메틸디에탄올아민, 4-디메틸아미노안식향산 에틸, 4-디메틸아미노 안식향산 이소아밀, 안식향산(2-디메틸아미노) 에틸, 4,4'-디메틸아미노벤조페논 등이 있으나, 이에 한정되지 않는다. Moreover, what has a photopolymerization accelerating effect can also be used individually or in combination with the said photoinitiator. For example, triethanolamine, methyldiethanolamine, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, ethyl benzoic acid (2-dimethylamino), 4,4'-dimethylaminobenzophenone, etc. Not limited.
또한, 본 발명은 상술한 코팅 조성물을 사용하여 유기물층, 일례로 정공주입층 또는 정공수송층을 형성하는 방법을 제공한다. 구체적으로, 양극(또는 정공주입층) 상에, 상술한 코팅 조성물을 용액 공정으로 코팅하는 단계; 및 상기 코팅된 코팅 조성물을 열처리 또는 광처리하는 단계를 포함한다. In addition, the present invention provides a method of forming an organic material layer, for example, a hole injection layer or a hole transport layer by using the above-described coating composition. Specifically, coating the above-described coating composition on the anode (or hole injection layer) by a solution process; And heat-treating or light-treating the coated coating composition.
상기 용액 공정은 상술한 본 발명에 따른 코팅 조성물을 사용하는 것으로, 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.The solution process is to use the coating composition according to the present invention described above, and means spin coating, dip coating, doctor blading, ink jet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
상기 열처리 단계에서 열처리 온도는 150 내지 230℃가 바람직하다. 또한, 상기 열처리 시간은 1분 내지 3시간이고, 보다 바람직하게는 10분 내지 1시간이다. 또한, 상기 열처리는 아르곤, 질소 등의 불활성 기체 분위기에서 수행하는 것이 바람직하다. 또한, 상기 코팅 단계와 상기 열처리 또는 광처리 단계 사이에 용매를 증발시키는 단계를 추가로 포함할 수 있다. In the heat treatment step, the heat treatment temperature is preferably 150 to 230°C. In addition, the heat treatment time is 1 minute to 3 hours, more preferably 10 minutes to 1 hour. In addition, the heat treatment is preferably performed in an inert gas atmosphere such as argon or nitrogen. In addition, it may further include evaporating the solvent between the coating step and the heat treatment or light treatment step.
(유기 발광 소자)(Organic Light-Emitting Element)
또한, 본 발명은 상기 화학식 1로 표시되는 화합물의 경화물을 포함하는 유기 발광 소자를 제공한다. 일례로, 본 발명은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물의 경화물을 포함하는 것인, 유기 발광 소자를 제공한다.In addition, the present invention provides an organic light-emitting device including a cured product of the compound represented by
또한, 본 발명에 따른 유기 발광 소자는, 기판 상에 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층된 구조(normal type)의 유기 발광 소자일 수 있다. 또한, 본 발명에 따른 유기 발광 소자는 기판 상에 음극, 1층 이상의 유기물층 및 양극이 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다. 예컨대, 본 발명의 일실시예에 따른 유기 발광 소자의 구조는 도 1 및 2에 예시되어 있다.In addition, the organic light-emitting device according to the present invention may be a normal type organic light-emitting device 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 inverted type organic light-emitting device 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 device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
도 1은 기판(1), 양극(2), 발광층(3), 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 발광층에 포함될 수 있다. 1 shows an example of an organic light-emitting device comprising a
도 2는 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(7), 전자 주입 및 수송층(8) 및 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 정공주입층, 정공수송층, 또는 발광층에 포함될 수 있다.2 is an example of an organic light-emitting device comprising a
본 발명에 따른 유기 발광 소자는, 상술한 방법과 같이 제조되는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조할 수 있다.The organic light-emitting device according to the present invention can be manufactured by materials and methods known in the art, except that it is manufactured in the manner described above.
예컨대, 본 발명에 따른 유기 발광 소자는 기판 상에 양극, 유기물층 및 음극을 순차적으로 적층시켜 제조할 수 있다. 이때, 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(physical Vapor Deposition) 방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물 층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시켜 제조할 수 있다. For example, the organic light emitting device according to the present invention may be manufactured by sequentially laminating an anode, an organic material layer, and a cathode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or a conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. And, after forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, it can be prepared by depositing a material that can be used as a cathode thereon.
이와 같은 방법 외에도, 기판 상에 음극 물질로부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 제조할 수 있다(WO 2003/012890). 다만, 제조 방법이 이에 한정되는 것은 아니다. In addition to such a method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
일례로, 상기 제1 전극은 양극이고, 상기 제2 전극은 음극이거나, 또는 상기 제1 전극은 음극이고, 상기 제2 전극은 양극이다.For example, the first electrode is an anode, the second electrode is a cathode, or the first electrode is a cathode, and the second electrode is an anode.
상기 양극 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 상기 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 화합물 등이 있으나, 이들에만 한정되는 것은 아니다. As the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the cathode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; Conductive compounds such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 상기 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다. 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, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multilayered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
상기 정공주입층은 전극으로부터 정공을 주입하는 층으로, 정공 주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입효과, 발광층 또는 발광재료에 대하여 우수한 정공 주입 효과를 갖고, 발광층에서 생성된 여기자의 전자주입층 또는 전자주입재료에의 이동을 방지하며, 또한, 박막 형성 능력이 우수한 화합물이 바람직하다. 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물 층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrin), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone)계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 화합물 등이 있으나, 이들에만 한정 되는 것은 아니다. The hole injection layer is a layer that injects holes from the electrode, and has the ability to transport holes as a hole injection material, so that it has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and is generated from the light emitting layer. A compound that prevents the movement of excitons to the electron injection layer or the electron injection material and has excellent ability to form a thin film is preferable. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive compounds, but are not limited thereto.
상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 화합물, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer.The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the emission layer, and has high mobility for holes. The material is suitable. Specific examples include an arylamine-based organic material, a conductive compound, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 도펀트 재료로는 상술한 화학식 1로 표시되는 화합물이 사용될 수 있다. 또한, 호스트 재료로는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등을 사용할 수 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. The emission layer may include a host material and a dopant material. As the dopant material, the compound represented by
상기 전자 주입 및 수송층은 전극으로부터 전자를 주입하고, 수취된 전자를 발광층까지 수송하는 전자수송층 및 전자주입층의 역할을 동시에 수행하는 층으로, 상기 발광층 또는 상기 전자조절층 상에 형성된다. 이러한 전자 주입 및 수송물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 전자 주입 및 수송물질의 예로는 8-히드록시퀴놀린의 Al 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물; 트리아진 유도체 등이 있으나, 이들에만 한정되는 것은 아니다. 또는 LiF, NaF, NaCl, CsF, Li2O, BaO, 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물, 또는 질소 함유 5원환 유도체 등을 사용할 수도 있으나, 이에 한정되는 것은 아니다. The electron injection and transport layer is a layer that simultaneously serves as an electron transport layer and an electron injection layer for injecting electrons from an electrode and transporting received electrons to the emission layer, and is formed on the emission layer or the electron control layer. As the electron injection and transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high mobility for electrons is suitable. Examples of specific electron injection and transport materials include Al complex of 8-hydroxyquinoline; Complexes containing Alq 3; Organic radical compounds; Hydroxyflavone-metal complex; Triazine derivatives, etc., but are not limited thereto. Or LiF, NaF, NaCl, CsF, Li 2 O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, pre Orenylidene methane, anthrone, and the like, derivatives thereof, metal complex compounds, or nitrogen-containing 5-membered ring derivatives may be used, but are not limited thereto.
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)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되지 않는다.Examples of the metal complex compound include 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)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.
본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light-emitting device according to the present invention may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
또한, 본 발명에 따른 화합물은 유기 발광 소자 외에도 유기 태양 전지 또는 유기 트랜지스터에 포함될 수 있다.In addition, the compound according to the present invention may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
상기 화학식 1로 표시되는 화합물 및 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.The preparation of the compound represented by
[실시예][Example]
실시예 1: 화합물 1의 제조Example 1: Preparation of
단계 1) 화합물 1-3의 제조Step 1) Preparation of compound 1-3
250 mL 둥근 바닥 플라스크에 화합물 1-1(5.0 g, 11.43 mmol), 화합물 1-2(5.8 g, 34.30 mmol), 비스(트리-터트-부틸포스핀)팔라듐(0)(292 mg, 0.57 mmol), NaOt-Bu(3.30 g, 34.30 mmol), 및 톨루엔(38 mL)을 넣고 100℃에서 12시간 동안 교반하였다. 상온에서 반응 용액을 차가운 물에 가하였다. 에틸 아세테이트로 추출하고 MgSO4로 잔여 수분을 제거한 후, 헥산:메틸렌클로라이드(3:1(v:v))로 실리카 컬럼 정제하여 화합물 1-3(5 g)을 제조하였다. In a 250 mL round bottom flask, compound 1-1 (5.0 g, 11.43 mmol), compound 1-2 (5.8 g, 34.30 mmol), bis (tri-tert-butylphosphine) palladium (0) (292 mg, 0.57 mmol) ), NaOt-Bu (3.30 g, 34.30 mmol), and toluene (38 mL) were added and stirred at 100° C. for 12 hours. At room temperature, the reaction solution was added to cold water. After extraction with ethyl acetate and removal of residual moisture with MgSO 4 , it was purified by silica column with hexane:methylene chloride (3:1 (v:v)) to prepare compound 1-3 (5 g).
단계 2) 화합물 1의 제조Step 2) Preparation of
100 mL 둥근 바닥 플라스크에 화합물 1-3(4.16 g, 7.91 mmol), 화합물 1-4(2.0 g, 3.59 mmol), 비스(트리-터트-부틸포스핀)팔라듐(0)(92 mg, 0.18 mmol), NaOt-Bu(1.38 g, 14.38 mmol), 및 톨루엔(12 mL)을 넣고 120℃에서 12시간 동안 교반하였다. 상온에서 반응 용액을 차가운 물에 가하였다. 에틸 아세테이트로 추출하고 MgSO4로 잔여 수분을 잔여 수분을 제거한 후, 헥산:메틸렌클로라이드(2:1(v:v))로 실리카 컬럼 정제하여 화합물 1(3 g)을 제조하였다. In a 100 mL round bottom flask, compound 1-3 (4.16 g, 7.91 mmol), compound 1-4 (2.0 g, 3.59 mmol), bis (tri-tert-butylphosphine) palladium (0) (92 mg, 0.18 mmol) ), NaOt-Bu (1.38 g, 14.38 mmol), and toluene (12 mL) were added and stirred at 120° C. for 12 hours. At room temperature, the reaction solution was added to cold water. After extraction with ethyl acetate and removal of residual moisture with MgSO 4 , compound 1 (3 g) was prepared by purifying a silica column with hexane:methylene chloride (2:1 (v:v)).
MS: [M+H]+= 1473MS: [M+H] + = 1473
실시예 2: 화합물 2의 제조Example 2: Preparation of
단계 1) 화합물 2-3의 제조Step 1) Preparation of compound 2-3
250 mL 둥근 바닥 플라스크에 화합물 2-1(10.0 g, 22.15 mmol), 화합물 2-2(12.38 g, 133.92 mmol), 비스(트리-터트-부틸포스핀)팔라듐(0)(1.01 g, 1.11 mmol), NaOt-Bu(6.39 g, 66.46 mmol), 및 톨루엔(74 mL)을 넣고 100℃에서 12시간 동안 교반하였다. 상온에서 반응 용액을 차가운 물에 가하였다. 에틸 아세테이트로 추출하고 MgSO4로 잔여 수분을 제거한 후, 헥산:메틸렌클로라이드(3:1(v:v))로 실리카 컬럼 정제하여 화합물 2-3(10 g)을 제조하였다. In a 250 mL round bottom flask, compound 2-1 (10.0 g, 22.15 mmol), compound 2-2 (12.38 g, 133.92 mmol), bis (tri-tert-butylphosphine) palladium (0) (1.01 g, 1.11 mmol) ), NaOt-Bu (6.39 g, 66.46 mmol), and toluene (74 mL) were added and stirred at 100° C. for 12 hours. At room temperature, the reaction solution was added to cold water. After extraction with ethyl acetate and removal of residual moisture with MgSO 4 , it was purified by silica column with hexane:methylene chloride (3:1 (v:v)) to prepare compound 2-3 (10 g).
단계 2) 화합물 2의 제조Step 2) Preparation of
100 mL 둥근 바닥 플라스크에 화합물 2-3(1.8 g, 3.91 mmol), 화합물 1-4(817 mg, 1.78 mmol), 비스(트리-터트-부틸포스핀)팔라듐(0)(34 mg, 0.09 mmol), NaOt-Bu(683 mg, 7.11 mmol), 및 톨루엔(6 mL)을 넣고 120℃에서 12시간 동안 교반하였다. 상온에서 반응 용액을 차가운 물에 가하였다. 에틸 아세테이트로 추출하고 MgSO4로 잔여 수분을 잔여 수분을 제거한 후, 헥산:메틸렌클로라이드(2:1(v:v))로 실리카 컬럼 정제하여 화합물 2(287 mg)을 제조하였다. In a 100 mL round bottom flask, compound 2-3 (1.8 g, 3.91 mmol), compound 1-4 (817 mg, 1.78 mmol), bis (tri-tert-butylphosphine) palladium (0) (34 mg, 0.09 mmol) ), NaOt-Bu (683 mg, 7.11 mmol), and toluene (6 mL) were added and stirred at 120° C. for 12 hours. At room temperature, the reaction solution was added to cold water. After extraction with ethyl acetate and removal of residual moisture with MgSO 4 , compound 2 (287 mg) was prepared by purifying a silica column with hexane:methylene chloride (2:1 (v:v)).
MS: [M+H]+= 1348MS: [M+H] + = 1348
실시예 3: 화합물 3의 제조Example 3: Preparation of
단계 1) 화합물 3-3의 제조Step 1) Preparation of compound 3-3
250 mL 둥근 바닥 플라스크에 화합물 3-1(5.0 g, 11.43 mmol), 화합물 3-2(7.2 g, 34.30 mmol), 비스(트리-터트-부틸포스핀)팔라듐(0)(292 mg, 0.57 mmol), NaOt-Bu(3.30 g, 34.30 mmol), 및 톨루엔(38 mL)을 넣고 100℃에서 12시간 동안 교반하였다. 상온에서 반응 용액을 차가운 물에 가하였다. 에틸 아세테이트로 추출하고 MgSO4로 잔여 수분을 제거한 후, 헥산:메틸렌클로라이드(3:1(v:v))로 실리카 컬럼 정제하여 화합물 3-3(4.6 g)을 제조하였다. In a 250 mL round bottom flask, compound 3-1 (5.0 g, 11.43 mmol), compound 3-2 (7.2 g, 34.30 mmol), bis (tri-tert-butylphosphine) palladium (0) (292 mg, 0.57 mmol) ), NaOt-Bu (3.30 g, 34.30 mmol), and toluene (38 mL) were added and stirred at 100° C. for 12 hours. At room temperature, the reaction solution was added to cold water. After extraction with ethyl acetate and removal of residual moisture with MgSO 4 , compound 3-3 (4.6 g) was prepared by silica column purification with hexane:methylene chloride (3:1 (v:v)).
단계 2) 화합물 3의 제조Step 2) Preparation of
100 mL 둥근 바닥 플라스크에 화합물 1-3(4.5 g, 7.91 mmol), 화합물 1-4(2.0 g, 3.59 mmol), 비스(트리-터트-부틸포스핀)팔라듐(0)(92 mg, 0.18 mmol), NaOt-Bu(1.38 g, 14.38 mmol), 및 톨루엔(12 mL)을 넣고 120℃에서 12시간 동안 교반하였다. 상온에서 반응 용액을 차가운 물에 가하였다. 에틸 아세테이트로 추출하고 MgSO4로 잔여 수분을 잔여 수분을 제거한 후, 헥산:메틸렌클로라이드(2:1(v:v))로 실리카 컬럼 정제하여 화합물 3(2 g)을 제조하였다. In a 100 mL round bottom flask, compound 1-3 (4.5 g, 7.91 mmol), compound 1-4 (2.0 g, 3.59 mmol), bis (tri-tert-butylphosphine) palladium (0) (92 mg, 0.18 mmol) ), NaOt-Bu (1.38 g, 14.38 mmol), and toluene (12 mL) were added and stirred at 120° C. for 12 hours. At room temperature, the reaction solution was added to cold water. After extraction with ethyl acetate and removal of residual moisture with MgSO 4 , compound 3 (2 g) was prepared by purifying a silica column with hexane:methylene chloride (2:1 (v:v)).
MS: [M+H]+= 1530MS: [M+H] + = 1530
실시예 4: 화합물 4의 제조Example 4: Preparation of
단계 1) 화합물 4-3의 제조Step 1) Preparation of compound 4-3
250 mL 둥근 바닥 플라스크에 화합물 4-1(2.0 g, 5.00 mmol), 화합물 4-2(4.4 g, 12.5 mmol), 비스(트리-터트-부틸포스핀)팔라듐(0)(256 mg, 0.5 mmol), 및 세슘 카보네이트(8.15 g, 25 mmol)를 넣고 질소 치환하였다. 테트라하이드로퓨란(30 mL), 및 증류수(10 mL)를 넣고 80℃에서 밤새 교반하였다. 상온으로 냉각한 후 증류수(40 mL)를 투입하여 반응을 종결하였다. 디클로로메탄(20 mL)으로 3회 유기층을 추출하고, MgSO4로 잔여 수분을 제거한 후, 헥산:메틸렌클로라이드(3:1(v:v))로 실리카 컬럼 정제하여 화합물 4-3(2.5 g)을 제조하였다. In a 250 mL round bottom flask, compound 4-1 (2.0 g, 5.00 mmol), compound 4-2 (4.4 g, 12.5 mmol), bis (tri-tert-butylphosphine) palladium (0) (256 mg, 0.5 mmol) ), and cesium carbonate (8.15 g, 25 mmol) were added, followed by nitrogen substitution. Tetrahydrofuran (30 mL), and distilled water (10 mL) were added and stirred at 80°C overnight. After cooling to room temperature, distilled water (40 mL) was added to terminate the reaction. The organic layer was extracted three times with dichloromethane (20 mL), residual moisture was removed with MgSO 4 , and then purified on a silica column with hexane:methylene chloride (3:1 (v:v)), and compound 4-3 (2.5 g) Was prepared.
단계 2) 화합물 4의 제조Step 2) Preparation of
50 mL 둥근 바닥 플라스크에 화합물 4-3(1.0 g, 1.36 mmol), 화합물 4-4(1.26 g, 2.3 mmol), 비스(트리-터트-부틸포스핀)팔라듐(0)(93 mg), NaOt-Bu(0.392 g, 4.08 mmol)을 넣고 질소 치환하였다. 톨루엔(10 mL)을 넣고 60℃에서 2시간 동안 교반하였다. 상온으로 냉각한 후 증류수(10 mL)를 투입하여 반응을 종결하였다. 디클로로메탄(10 mL)으로 3회 유기층을 추출하고, MgSO4로 잔여 수분을 잔여 수분을 제거한 후, 헥산:메틸렌클로라이드(3:1(v:v))로 실리카 컬럼 정제하여 화합물 4(1.4 g)을 제조하였다. In a 50 mL round bottom flask, compound 4-3 (1.0 g, 1.36 mmol), compound 4-4 (1.26 g, 2.3 mmol), bis (tri-tert-butylphosphine) palladium (0) (93 mg), NaOt -Bu (0.392 g, 4.08 mmol) was added and nitrogen was substituted. Toluene (10 mL) was added and stirred at 60°C for 2 hours. After cooling to room temperature, distilled water (10 mL) was added to terminate the reaction. The organic layer was extracted three times with dichloromethane (10 mL), and the residual moisture was removed with MgSO 4 , and then purified on a silica column with hexane: methylene chloride (3:1 (v:v)) to obtain compound 4 (1.4 g). ) Was prepared.
MS: [M+H]+= 1472MS: [M+H] + = 1472
실시예 5: 화합물 5의 제조Example 5: Preparation of
단계 1) 화합물 5-3의 제조Step 1) Preparation of compound 5-3
250 mL 둥근 바닥 플라스크에 화합물 5-1(6.95 g, 12.5 mmol), 화합물 5-2(2.56 g, 2.51 mL, 27.5 mmol), 비스(트리-터트-부틸포스핀)팔라듐(0)(319 mg, 0.625 mmol), 및 NaOt-Bu(3.0 g, 31.25 mmol)를 넣고 질소 치환하였다. 톨루엔(40 mL)를 넣고 80℃에서 밤새 교반하였다. 상온으로 냉각한 후 증류수(40 mL)를 투입하여 반응을 종결하였다. 디클로로메탄(20 mL)으로 3회 유기층을 추출하고, MgSO4로 잔여 수분을 제거한 후, 헥산:메틸렌클로라이드(3:1(v:v))로 실리카 컬럼 정제하여 화합물 5-3(3 g)을 제조하였다. In a 250 mL round bottom flask, compound 5-1 (6.95 g, 12.5 mmol), compound 5-2 (2.56 g, 2.51 mL, 27.5 mmol), bis (tri-tert-butylphosphine) palladium (0) (319 mg) , 0.625 mmol), and NaOt-Bu (3.0 g, 31.25 mmol) were added, followed by nitrogen substitution. Toluene (40 mL) was added and stirred at 80°C overnight. After cooling to room temperature, distilled water (40 mL) was added to terminate the reaction. The organic layer was extracted three times with dichloromethane (20 mL), residual moisture was removed with MgSO 4 , and then purified by silica column with hexane:methylene chloride (3:1(v:v)), and compound 5-3 (3 g) Was prepared.
단계 2) 화합물 5의 제조Step 2) Preparation of
50 mL 둥근 바닥 플라스크에 화합물 5-3(1.0 g, 1.36 mmol), 화합물 4-4(1.26 g, 2.3 mmol), 비스(트리-터트-부틸포스핀)팔라듐(0)(93 mg), NaOt-Bu(0.392 g, 4.08 mmol)을 넣고 질소 치환하였다. 톨루엔(10 mL)을 넣고 60℃에서 2시간 동안 교반하였다. 상온으로 냉각한 후 증류수(10 mL)를 투입하여 반응을 종결하였다. 디클로로메탄(10 mL)으로 3회 유기층을 추출하고, MgSO4로 잔여 수분을 잔여 수분을 제거한 후, 헥산:메틸렌클로라이드(3:1(v:v))로 실리카 컬럼 정제하여 화합물 5(1.4 g)을 제조하였다. In a 50 mL round bottom flask, compound 5-3 (1.0 g, 1.36 mmol), compound 4-4 (1.26 g, 2.3 mmol), bis (tri-tert-butylphosphine) palladium (0) (93 mg), NaOt -Bu (0.392 g, 4.08 mmol) was added and nitrogen was substituted. Toluene (10 mL) was added and stirred at 60° C. for 2 hours. After cooling to room temperature, distilled water (10 mL) was added to terminate the reaction. The organic layer was extracted three times with dichloromethane (10 mL), and the residual moisture was removed with MgSO 4 , and then purified on a silica column with hexane:methylene chloride (3:1 (v:v)) to obtain compound 5 (1.4 g). ) Was prepared.
MS: [M+H]+= 1320MS: [M+H] + = 1320
실험예 1Experimental Example 1
단계 1) 코팅 조성물의 제조Step 1) Preparation of the coating composition
앞서 실시예에서 제조한 화합물 1, 하기 화합물 A, 및 용매로서 시클로헥사논을 2:8:490의 중량비로 혼합하여 코팅 조성물을 제조하였다.A coating composition was prepared by mixing
단계 2) 유기 발광 소자의 제조Step 2) Fabrication of an organic light-emitting device
ITO (indium tin oxide)가 1500 Å의 두께로 박막 증착된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. ITO를 30분간 세척한 후, 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 아이소프로필알콜, 아세톤의 용제로 초음파 세척을 각각 30분씩 하고 건조시킨 후, 상기 기판을 글러브박스로 수송시켰다.A glass substrate on which a thin film of ITO (indium tin oxide) was deposited to a thickness of 1500 Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol and acetone for 30 minutes each, followed by drying, and the substrate was transported to a glove box.
이렇게 준비된 ITO 투명 전극 위에, 상기 단계 1에서 제조한 코팅 조성물을 스핀 코팅하여 300 Å 두께의 정공주입층을 형성하고 N2 분위기 하에 핫플레이트에서 30분 동안 코팅 조성물을 경화시켰다. 이후, 진공증착기로 이송한 후, 상기 정공주입층 위에 하기 화합물 D를 1000 Å의 두께로 진공 증착하여 정공수송층을 형성하였다. 상기 정공수송층 위에 하기 화합물 E 및 하기 화합물 F를 92:8의 중량비로 300 Å의 두께로 진공 증착하여 발광층을 형성하였다. 상기 발광층 위에 하기 화합물 G를 200 Å의 두께로 진공 증착하여 전자 주입 및 수송층을 형성하였다. 상기 전자 주입 및 수송층 위에 순차적으로 12 Å의 두께로 LiF와 2000 Å의 두께로 알루미늄을 증착하여 캐소드를 형성하였다. On the thus prepared ITO transparent electrode, the coating composition prepared in
상기의 과정에서 유기물의 증착 속도는 0.4~0.7 Å/sec를 유지하였고, LiF는 0.3 Å/sec 알루미늄은 2 Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 2×10-7 ~ 5×10-8 torr를 유지하였다.In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7 Å/sec, the deposition rate of LiF was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec, and the vacuum degree during deposition was 2×10 -7 ~ 5× Maintained 10 -8 torr.
실험예 2 내지 5Experimental Examples 2 to 5
상기 실험예 1과 동일하되, 상기 코팅 조성물 제조시 화합물 1 대신 하기 표 1에 기재된 화합물을 사용하여, 유기 발광 소자를 제조하였다.The same as in Experimental Example 1, but using the compound shown in Table 1 instead of
비교실험예Comparative Experimental Example
상기 실험예 1과 동일하되, 상기 코팅 조성물 제조시 화합물 1 대신 하기 비교 화합물을 사용하여, 유기 발광 소자를 제조하였다.The same as in Experimental Example 1, but using the following comparative compound instead of
상기 실험예 및 비교실험예에서 제조한 유기 발광 소자에 전류를 인가하여 구동 전압, 전류 효율, 전력 효율 및 수명(T95)을 측정하고 그 결과를 하기 표 1에 나타내었다. 하기 표 1의 T95은 초기 휘도가 95%로 저하할 때까지 측정한 시간을 의미한다.The driving voltage, current efficiency, power efficiency, and lifetime (T95) were measured by applying a current to the organic light emitting device prepared in the Experimental Examples and Comparative Experimental Examples, and the results are shown in Table 1 below. T95 in Table 1 below refers to the time measured until the initial luminance decreases to 95%.
(V@10 mA/cm2)Driving voltage
(V@10 mA/cm 2 )
(cd/A@10 mA/cm2)Current efficiency
(cd/A@10 mA/cm 2 )
(lm/W@10 mA/cm2)Power efficiency
(lm/W@10 mA/cm 2 )
(hr@10 mA/cm2)LT95
(hr@10 mA/cm 2 )
상기 표 1에 나타난 바와 같이, 본 발명의 화학식 1의 구조를 포함하는 갖는 정공주입층의 호스트는 일반적으로 사용되는 정공주입층의 호스트에 비해 유기 용매에 대한 용해도가 우수하여 용액 공정에 적합함을 확인할 수 있었다. 특히, 코팅 조성물의 제조가 용이하여, 상기 코팅 조성물을 이용하여 균일한 코팅층을 형성할 수 있으며 기존의 정공주입층의 호스트와 달리 경화기가 존재하므로 층간 유입으로 인한 수명 저하를 막아주므로 유기 발광 소자에 적용할 수 있음을 확인하였다.As shown in Table 1, the host of the hole injection layer having the structure of
실험예 4Experimental Example 4
사이클로헥사논을 사용하여, 본 발명에 따른 화합물의 용매 내성을 평가하였다. Using cyclohexanone, the solvent resistance of the compounds according to the invention was evaluated.
구체적으로, 앞서 실시예에서 제조한 화합물 1 및 상기 비교실험예에서 화합물 1 대신 사용한 화합물을 각각 2 wt%로 사이클로헥사논에 녹인 용액을 제조하였다. 상기 용액을 스핀 코팅으로 quartz 기판에 100 nm 두께로 코팅하였다. 질소 분위기에서 1시간 동안 190 내지 200℃에서 열처리한 후 UV-Vis absorption spectrum을 측정(제1 측정)하였다. 이어, 동일한 샘플을 사이클로헥사논에 10분 동안 담궈 두었다가 꺼내어, 용매가 건조된 뒤 다시 UV-Vis absorption spectrum을 측정(제2 측정)하였다. 상기 결과를 도 3 및 도 4에 나타내었으며, 검은색이 상기 제1 측정을, 붉은색이 상기 제2 측정을 나타낸다. Specifically, a solution in which the
도 3에 나타난 바와 같이 본 발명의 따른 화합물은 스펙트럼 간에 차이가 거의 없는 반면, 도 4에 나타난 바와 같이 비교화합물은 스펙트럼 간에 큰 차이를 나타내었으며, 따라서 본 발명에 따른 화합물의 용매 내성이 현저히 우수함을 확인할 수 있었다. As shown in FIG. 3, the compound according to the present invention showed little difference between the spectra, whereas the comparative compound showed a large difference between the spectra as shown in FIG. 4, and thus, the solvent resistance of the compound according to the present invention was remarkably excellent I could confirm.
1: 기판
2: 양극
3: 발광층
4: 음극
5: 정공주입층
6: 정공수송층
7: 발광층
8: 전자주입 및 수송층1: substrate 2: anode
3: light-emitting layer 4: cathode
5: hole injection layer 6: hole transport layer
7: light emitting layer 8: electron injection and transport layer
Claims (12)
[화학식 1]
상기 화학식 1에서,
R1은 각각 독립적으로, C3-10 알킬이고,
R2는 각각 독립적으로, 수소, 또는 C1-10 알킬이고,
Ar1은 광경화성기; 또는 열경화성기이고,
Ar2는 각각 독립적으로, 1개 내지 3개의 C3-10 알킬로 치환된 C6-60 아릴이고,
Ar3은 각각 독립적으로, 비치환되거나 또는 C3-10 알킬로 치환된 C6-60 아릴이다.
Compound represented by the following formula (1):
[Formula 1]
In Formula 1,
Each R 1 is independently C 3-10 alkyl,
Each R 2 is independently hydrogen or C 1-10 alkyl,
Ar 1 is a photocurable group; Or a thermosetting group,
Ar 2 are each independently C 6-60 aryl substituted with 1 to 3 C 3-10 alkyl,
Each Ar 3 is independently C 6-60 aryl unsubstituted or substituted with C 3-10 alkyl.
Ar1은 -L"-R"이고,
L"는 단일 결합, -O-, -S-, -CH2-, -CH2O-, -OCH2-, 또는 -CH2OCH2-이고,
R"는 하기로 구성되는 군으로부터 선택되는 어느 하나인,
화합물:
The method of claim 1,
Ar 1 is -L"-R",
L" is a single bond, -O-, -S-, -CH 2 -, -CH 2 O-, -OCH 2 -, or -CH 2 OCH 2 -,
R" is any one selected from the group consisting of,
compound:
R1은 각각 독립적으로, 직쇄 C3-10 알킬인,
화합물.
The method of claim 1,
Each R 1 is independently, straight-chain C 3-10 alkyl,
compound.
R1은 각각 독립적으로, 프로필, 부틸, 펜틸, 또는 헥실인,
화합물.
The method of claim 1,
Each R 1 is independently propyl, butyl, pentyl, or hexyl,
compound.
R2는 각각 독립적으로, 수소, 또는 C1-4 알킬인,
화합물.
The method of claim 1,
Each R 2 is independently hydrogen or C 1-4 alkyl,
compound.
R2는 각각 독립적으로, 수소, 메틸, 에틸, 또는 프로필인,
화합물.
The method of claim 1,
Each R 2 is independently hydrogen, methyl, ethyl, or propyl,
compound.
Ar2는 페닐이고, 상기 페닐은 1개 또는 2개의 C1-5 알킬로 치환된,
화합물.
The method of claim 1,
Ar 2 is phenyl, and the phenyl is substituted with 1 or 2 C 1-5 alkyl,
compound.
Ar2는 페닐이고, 상기 페닐은 메틸, 에틸, 프로필, 부틸, 이소부틸 및 터트부틸로 구성되는 군으로부터 선택되는 1개 또는 2개의 치환기로 치환된,
화합물.
The method of claim 1,
Ar 2 is phenyl, and the phenyl is substituted with one or two substituents selected from the group consisting of methyl, ethyl, propyl, butyl, isobutyl and tertbutyl,
compound.
Ar3은 C6-12 아릴이고, 상기 C6-12 아릴은 비치환되거나, 또는 C1-5 알킬로 치환된,
화합물.
The method of claim 1,
Ar 3 is C 6-12 aryl, the C 6-12 aryl is unsubstituted or substituted with C 1-5 alkyl,
compound.
Ar3은 페닐 또는 비페닐릴이고,
상기 페닐 또는 비페닐릴은 비치환되거나, 또는 메틸, 에틸, 또는 프로필로 치환된,
화합물.
The method of claim 1,
Ar 3 is phenyl or biphenylyl,
The phenyl or biphenylyl is unsubstituted or substituted with methyl, ethyl, or propyl,
compound.
상기 화학식 1로 표시되는 화합물은 하기 화합물로 구성되는 군으로부터 선택되는 어느 하나인,
화합물:
The method of claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of the following compounds,
compound:
A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers is formed of the compound according to any one of claims 1 to 11. The organic light-emitting device comprising a cargo.
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