KR20090044975A - Anthracene-based compound and organic light emitting device employing the same - Google Patents
Anthracene-based compound and organic light emitting device employing the same Download PDFInfo
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- KR20090044975A KR20090044975A KR1020080039348A KR20080039348A KR20090044975A KR 20090044975 A KR20090044975 A KR 20090044975A KR 1020080039348 A KR1020080039348 A KR 1020080039348A KR 20080039348 A KR20080039348 A KR 20080039348A KR 20090044975 A KR20090044975 A KR 20090044975A
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- South Korea
- Prior art keywords
- formula
- substituted
- group
- unsubstituted
- anthracene
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 100
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 title claims abstract description 43
- 125000003118 aryl group Chemical group 0.000 claims abstract description 26
- 125000001424 substituent group Chemical group 0.000 claims abstract description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical group 0.000 claims abstract description 11
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000000732 arylene group Chemical group 0.000 claims abstract description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 6
- 125000005647 linker group Chemical group 0.000 claims abstract description 6
- 238000002347 injection Methods 0.000 claims description 48
- 239000007924 injection Substances 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 41
- -1 anthracene compound Chemical class 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 18
- 230000005525 hole transport Effects 0.000 claims description 15
- 230000000903 blocking effect Effects 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 7
- 125000002524 organometallic group Chemical group 0.000 claims description 5
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 102
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000463 material Substances 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 19
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 239000010408 film Substances 0.000 description 15
- 238000000065 atmospheric pressure chemical ionisation Methods 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 13
- 238000004528 spin coating Methods 0.000 description 13
- 238000001771 vacuum deposition Methods 0.000 description 13
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- 125000001246 bromo group Chemical group Br* 0.000 description 8
- 125000001309 chloro group Chemical group Cl* 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 238000000113 differential scanning calorimetry Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- KDPGIUXKYMCDIE-UHFFFAOYSA-N 3-[5-(4-bromophenyl)pyridin-2-yl]quinoline Chemical compound C1=CC(Br)=CC=C1C1=CC=C(C=2C=C3C=CC=CC3=NC=2)N=C1 KDPGIUXKYMCDIE-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 3
- YQZGQXPHGLAEHA-UHFFFAOYSA-N 2-pyridin-2-ylquinoline Chemical compound N1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 YQZGQXPHGLAEHA-UHFFFAOYSA-N 0.000 description 3
- SOSPMXMEOFGPIM-UHFFFAOYSA-N 3,5-dibromopyridine Chemical compound BrC1=CN=CC(Br)=C1 SOSPMXMEOFGPIM-UHFFFAOYSA-N 0.000 description 3
- KGTJBUVGZASOLT-UHFFFAOYSA-N 3-(5-bromopyridin-2-yl)quinoline Chemical compound N1=CC(Br)=CC=C1C1=CN=C(C=CC=C2)C2=C1 KGTJBUVGZASOLT-UHFFFAOYSA-N 0.000 description 3
- XBANMTDPADPEMI-UHFFFAOYSA-N 3-(5-bromopyridin-3-yl)quinoline Chemical compound BrC1=CN=CC(C=2C=C3C=CC=CC3=NC=2)=C1 XBANMTDPADPEMI-UHFFFAOYSA-N 0.000 description 3
- PAWSGKQRXZYKPA-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-(10-naphthalen-2-ylanthracen-9-yl)-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 PAWSGKQRXZYKPA-UHFFFAOYSA-N 0.000 description 3
- JTYRNQDDKWKZLP-UHFFFAOYSA-N 4-(5-bromopyridin-2-yl)isoquinoline Chemical compound N1=CC(Br)=CC=C1C1=CN=CC2=CC=CC=C12 JTYRNQDDKWKZLP-UHFFFAOYSA-N 0.000 description 3
- FSZSVKKLLDHRLI-UHFFFAOYSA-N 4-(6-bromopyridin-2-yl)isoquinoline Chemical compound BrC1=CC=CC(C=2C3=CC=CC=C3C=NC=2)=N1 FSZSVKKLLDHRLI-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910021645 metal ion Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 150000002910 rare earth metals Chemical class 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- 125000001425 triazolyl group Chemical group 0.000 description 3
- CJEZLXXESOYJHS-UHFFFAOYSA-N 1-pyridin-2-ylisoquinoline Chemical compound N1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CJEZLXXESOYJHS-UHFFFAOYSA-N 0.000 description 2
- ZHXUWDPHUQHFOV-UHFFFAOYSA-N 2,5-dibromopyridine Chemical compound BrC1=CC=C(Br)N=C1 ZHXUWDPHUQHFOV-UHFFFAOYSA-N 0.000 description 2
- FEYDZHNIIMENOB-UHFFFAOYSA-N 2,6-dibromopyridine Chemical compound BrC1=CC=CC(Br)=N1 FEYDZHNIIMENOB-UHFFFAOYSA-N 0.000 description 2
- IVTVQFFPFMLDJJ-UHFFFAOYSA-N 3-(6-bromopyridin-2-yl)quinoline Chemical compound BrC1=CC=CC(C=2C=C3C=CC=CC3=NC=2)=N1 IVTVQFFPFMLDJJ-UHFFFAOYSA-N 0.000 description 2
- LOMKRPABAXIQJL-UHFFFAOYSA-N 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinoline Chemical compound O1C(C)(C)C(C)(C)OB1C1=CN=CC2=CC=CC=C12 LOMKRPABAXIQJL-UHFFFAOYSA-N 0.000 description 2
- MZANSVCFKCGDGW-UHFFFAOYSA-N BrC=1C=C(C=NC1)C=1C=NC2=CC=CC=C2C1.BrC=1C=C(C=NC1)C=1C=NC2=CC=CC=C2C1 Chemical compound BrC=1C=C(C=NC1)C=1C=NC2=CC=CC=C2C1.BrC=1C=C(C=NC1)C=1C=NC2=CC=CC=C2C1 MZANSVCFKCGDGW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910052693 Europium Inorganic materials 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 229960002796 polystyrene sulfonate Drugs 0.000 description 2
- 239000011970 polystyrene sulfonate Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 1
- QBLFZIBJXUQVRF-UHFFFAOYSA-N (4-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Br)C=C1 QBLFZIBJXUQVRF-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- OGNSDRMLWYNUED-UHFFFAOYSA-N 1-cyclohexyl-4-[4-[4-(4-cyclohexylcyclohexyl)cyclohexyl]cyclohexyl]cyclohexane Chemical group C1CCCCC1C1CCC(C2CCC(CC2)C2CCC(CC2)C2CCC(CC2)C2CCCCC2)CC1 OGNSDRMLWYNUED-UHFFFAOYSA-N 0.000 description 1
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- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 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
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229910052727 yttrium Inorganic materials 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
- 229910052726 zirconium Inorganic materials 0.000 description 1
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Abstract
하기 화학식 1 또는 화학식 2로 표시되는 치환기를 갖는 안트라센계 화합물 및 이를 이용한 유기 전계 발광 소자가 제공된다.An anthracene-based compound having a substituent represented by Formula 1 or Formula 2 and an organic electroluminescent device using the same are provided.
[화학식 1][Formula 1]
[화학식 2][Formula 2]
상기 화학식 1 또는 화학식 2에서, R은 수소, 할로겐, 시아노기, 히드록실기, 치환 또는 비치환된 C1~ C20의 알킬기, 치환 또는 비치환된 C3 ~ C20의 사이클로알킬기, 치환 또는 비치환된 C5 -C30 헤테로사이클로알킬기, 치환 또는 비치환된 C1~ C20의 알콕시기, 치환 또는 비치환된 C6 ~ C30의 아릴기, 치환 또는 비치환된 C6 ~ C30의 아랄킬기, 치환 또는 비치환된 C2 ~ C30의 헤테로아릴기이고, L 은 2가의 연결기로서, 치환 또는 비치환된 C6 ~ C30의 아릴렌 또는 치환 또는 비치환된 C2 ~ C30의 헤테로아릴렌이고, l은 0 내지 3의 정수이다.In Formula 1 or Formula 2, R is hydrogen, halogen, cyano group, hydroxyl group, substituted or unsubstituted C1 ~ C20 alkyl group, substituted or unsubstituted C3 ~ C20 cycloalkyl group, substituted or unsubstituted C5 -C30 heterocycloalkyl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C6-C30 aralkyl group, substituted or unsubstituted C2-C30 Is a heteroaryl group, L is a divalent linking group, substituted or unsubstituted C6 to C30 arylene or substituted or unsubstituted C2 to C30 heteroarylene, l is an integer of 0 to 3.
Description
본 발명은 안트라센계계 화합물 및 이를 이용한 유기 전계 발광 소자에 관한 것으로서, 보다 상세하기로는 피리디닐퀴놀린(pyridinylquinoline)계 또는 피리디닐이소퀴놀린(pyridinylisoquinoline)계 치환기가 도입된 안트라센계 화합물과, 이를 이용하여 형성된 유기막을 구비하고 있는 유기 전계 발광 소자에 관한 것이다.The present invention relates to an anthracene-based compound and an organic electroluminescent device using the same, and more particularly, an anthracene-based compound having a pyridinylquinoline-based or pyridinylisoquinoline-based substituent introduced therein, and formed using the same. An organic electroluminescent element provided with an organic film.
유기 전계 발광 소자는 형광성 또는 인광성 유기 화합물 박막(이하, 유기막이라고 함)에 전류를 흘려주면, 전자와 홀이 유기막에서 결합하면서 빛이 발생하는 현상을 이용한 능동 발광형 표시 소자로서, 경량화가 가능하고, 부품이 간소하여 제작공정이 간단하며, 고화질에 광시야각을 확보하고 있다는 장점을 갖는다. 또한 동영상을 완벽하게 구현할 수 있고, 고색순도 구현이 가능하며, 저소비 전력과 저전압 구동이 가능하여 휴대용 전자기기에 적합한 전기적 특성을 갖고 있다.The organic electroluminescent device is an active light emitting display device using a phenomenon in which light is generated while electrons and holes are combined in an organic film when a current flows through a thin film of fluorescent or phosphorescent organic compound (hereinafter referred to as an organic film). It is possible, and the parts are simple, the manufacturing process is simple, and has the advantage of ensuring a wide viewing angle in high quality. In addition, video can be fully realized, high color purity can be realized, and low power consumption and low voltage can be driven to have electrical characteristics suitable for portable electronic devices.
이스트만 코닥사(Eastman Kodak Co.)에서는 알루미늄 퀴놀리놀 착화합물층(Aluminum Quinolinol Complex Layer)과 트리페닐아민 유도체층(Triphenylamine Derivative Layer)을 이용한 다층 구조의 유기 전계 발광 소자를 개발하였고 (미국 특허 US 4,885,211), 유기 발광층 형성시 저분자가 이용됨에 따라 자외선에서 적외선 영역에 이르기까지의 다양한 발광이 가능해졌다. (미국 특허 US 5,151,629). Eastman Kodak Co. has developed a multi-layered organic electroluminescent device using an aluminum quinolinol complex layer and a triphenylamine derivative layer (US Pat. No. 4,885,211). As the low molecular weight is used in forming the organic light emitting layer, various light emission from the ultraviolet ray to the infrared ray region is possible. (US Pat. No. 5,151,629).
발광 소자(light emitting device)는 자발광형 소자로 시야각이 넓으며 콘트 라스트가 우수할 뿐만 아니라 응답시간이 빠르다는 장점을 가지고 있다. 상기 발광 소자에는 발광층(emitting layer)에 무기 화합물을 사용하는 무기 발광 소자와 유기 화합물을 사용하는 유기 발광 소자(Organic Light Emitting Deveice : OLED)가 있는데, 유기 발광 소자는 무기 발광 소자에 비하여 휘도, 구동전압 및 응답속도 특성이 우수하고 다색화가 가능하다는 점에서 많은 연구가 이루어지고 있다.The light emitting device is a self-luminous device and has a wide viewing angle, excellent contrast, and fast response time. The light emitting device includes an inorganic light emitting device using an inorganic compound and an organic light emitting device using an organic compound (OLED) in the light emitting layer, and the organic light emitting device has higher luminance and driving than the inorganic light emitting device. Much research has been conducted in that the voltage and response speed characteristics are excellent and multicoloring is possible.
유기 발광 소자는 일반적으로 애노드/유기 발광층/캐소드의 적층구조를 가지며, 애노드/정공주입층/정공수송층/발광층/전자수송층/전자주입층/캐소드 또는 애노드/정공주입층/정공수송층/발광층/정공저지층/전자수송층/전자주입층/캐소드 등과 같은 다양한 구조도 가질 수 있다.The organic light emitting device generally has a stacked structure of anode / organic light emitting layer / cathode, and includes anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode or anode / hole injection layer / hole transport layer / light emitting layer / hole It may also have various structures such as a blocking layer / electron transport layer / electron injection layer / cathode.
유기 발광 소자에 사용하는 물질은 유기막의 제조 방법에 따라 진공증착성 물질과 용액도포성 물질로 나눌 수 있다. 진공 증착성 물질은 500℃이하에서 10-6 torr 이상의 증기압을 가질 수 있어야 하며, 주로 분자량 1200 이하의 저분자 물질이 바람직하다. 용액 도포성 물질로는 용제에 대한 용해성이 높아서 용액으로 제조 가능하여야 하며 주로 방향족 또는 복소환을 포함한다.The material used for the organic light emitting device may be classified into a vacuum deposition material and a solution coating material according to the method of manufacturing an organic film. The vacuum evaporable material should have a vapor pressure of 10 −6 torr or more under 500 ° C., and preferably a low molecular weight material having a molecular weight of 1200 or less. The solution coatable material is highly soluble in a solvent and must be able to be prepared as a solution, and mainly includes an aromatic or heterocyclic ring.
진공 증착 방법을 사용하여 유기 전계 발광 소자를 제조할 경우 진공 시스템의 사용으로 제조 비용이 증가하며 천연색 디스플레이용 픽셀을 제조하기 위해 쉐 도우 마스크를 사용할 경우 고해상도의 픽셀을 제조하기 어렵다. 이에 반해 잉크젯 프린팅, 스크린 프린팅, 스핀 코팅과 같은 용액 도포법의 경우에는 제조가 용이하고 제조 비용이 저렴하며 쉐도우 마스크를 사용할 경우보다 상대적으로 우수한 해상도를 얻을 수 있다.In the case of manufacturing the organic EL device using the vacuum deposition method, the manufacturing cost increases due to the use of a vacuum system, and when the shadow mask is used to manufacture the pixels for the color display, it is difficult to manufacture the high resolution pixels. On the other hand, solution coating methods such as inkjet printing, screen printing, and spin coating are easy to manufacture, inexpensive to manufacture, and have a relatively higher resolution than shadow masks.
한편, 종래의 유기 전계 발광 소자는 고온환경하에서 유기 발광 소자를 구동시키거나 보관하면 발광색의 변화, 발광효율의 저하, 구동전압의 상승, 짧은 발광수명등의 문제점이 생긴다. 이러한 문제점들을 해결하기 위해서는 높은 유리전이온도와 더불어 구동전압을 낮출 수 있는 새로운 전자수송재료의 개발이 필요하다. On the other hand, when the organic light emitting device is driven or stored in a high temperature environment, there are problems such as a change in emission color, a decrease in luminous efficiency, an increase in driving voltage, and a short emission life. To solve these problems, it is necessary to develop a new electron transport material capable of lowering the driving voltage with a high glass transition temperature.
전자수송재료는 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, 알루미늄 착물(aluminum complex) 등이 널리 사용되고 있으며, 특히 최근 들어서는 펜안트롤린 또는 비피리딘계 화합물을 이용한 전자수송재료의 연구가 활발히 진행되고 있다.As the electron transporting material, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, etc. are widely used, and in recent years, active researches on electron transporting materials using phenanthroline or bipyridine compounds have been actively conducted. It's going on.
WO2007/026847에서는 치환된 피리디닐기와 연결된 트리아졸 고리 구조를 갖는 화합물을 개시하고, 일본 특개평 15-123983에는 1,10-펜안트롤린계 화합물을 개시하여서, 상기 화합물들이 기존의 재료에 비해 높은 전자수송특성을 갖는다는 점을 이용하여, 저전압구동이 가능하고 비교적 고효율의 특성을 얻을 수 있는 유기 전계 발광 소자에 적용하고자 하였다.WO2007 / 026847 discloses a compound having a triazole ring structure linked to a substituted pyridinyl group, and Japanese Patent Laid-Open No. 15-123983 discloses a 1,10-phenanthroline-based compound, in which the compounds have higher electrons than conventional materials. It is intended to be applied to an organic electroluminescent device capable of low voltage drive and obtain a relatively high efficiency characteristics by using the transport characteristics.
하기 화학식 1 또는 화학식 2로 표시되는 치환기를 갖는 안트라센계 화합물이 제공된다:An anthracene-based compound having a substituent represented by Formula 1 or Formula 2 is provided:
[화학식 1][Formula 1]
[화학식 2][Formula 2]
상기 화학식 1 또는 화학식 2에서 In Chemical Formula 1 or Chemical Formula 2
R은 수소, 할로겐, 시아노기, 히드록실기, 치환 또는 비치환된 C1~ C20의 알킬기, 치환 또는 비치환된 C3 ~ C20의 사이클로알킬기, 치환 또는 비치환된 C5 -C30 헤테로사이클로알킬기, 치환 또는 비치환된 C1~ C20의 알콕시기, 치환 또는 비치환된 C6 ~ C30의 아릴기, 치환 또는 비치환된 C6 ~ C30의 아랄킬기, 치환 또는 비치환된 C2 ~ C30의 헤테로아릴기이고, R is hydrogen, halogen, cyano group, hydroxyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C5-C30 heterocycloalkyl group, substituted or Unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C6-C30 aralkyl group, substituted or unsubstituted C2-C30 heteroaryl group,
L 은 2가의 연결기로서, 치환 또는 비치환된 C6 ~ C30의 아릴렌 또는 치환 또는 비치환된 C2 ~ C30의 헤테로아릴렌이고, L is a divalent linking group, which is substituted or unsubstituted C6 to C30 arylene or substituted or unsubstituted C2 to C30 heteroarylene,
l은 0, 1, 2 또는 3이다.l is 0, 1, 2 or 3.
제1전극; 제2전극; 및 상기 제1전극과 상기 제2전극 사이에 적어도 한 층의 유기막을 포함하는 유기 전계 발광 소자로서, 상기 유기막이 전술한 바와 같은 안트라센계 화합물을 포함하는 유기 전계 발광 소자가 제공된다.A first electrode; Second electrode; And an organic electroluminescent device comprising at least one organic film between the first electrode and the second electrode, wherein the organic film includes an anthracene-based compound as described above.
본 발명의 일 실시예에 따르는 화합물은 하기 화학식 1 또는 화학식 2로 표시되는 치환기, 즉 피리디닐퀴놀린(pyridinylquinoline)계 또는 피리디닐이소퀴놀린(pyridinylisoquinoline)계 치환기가 도입된 안트라센계 화합물이다.The compound according to an embodiment of the present invention is an anthracene-based compound into which a substituent represented by Formula 1 or Formula 2 below, that is, a pyridinylquinoline-based or pyridinylisoquinoline-based substituent is introduced.
[화학식 1][Formula 1]
[화학식 2][Formula 2]
상기 화학식 1 또는 화학식 2에서 In Chemical Formula 1 or Chemical Formula 2
R은 수소, 할로겐, 시아노기, 히드록실기, 치환 또는 비치환된 C1~ C20의 알킬기, 치환 또는 비치환된 C3 ~ C20의 사이클로알킬기, 치환 또는 비치환된 C5 -C30 헤테로사이클로알킬기, 치환 또는 비치환된 C1~ C20의 알콕시기, 치환 또는 비치환된 C6 ~ C30의 아릴기, 치환 또는 비치환된 C6 ~ C30의 아랄킬기, 치환 또는 비치환된 C2 ~ C30의 헤테로아릴기이고, R is hydrogen, halogen, cyano group, hydroxyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C5-C30 heterocycloalkyl group, substituted or Unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C6-C30 aralkyl group, substituted or unsubstituted C2-C30 heteroaryl group,
L 은 2가의 연결기로서, 치환 또는 비치환된 C6 ~ C30의 아릴렌 또는 치환 또는 비치환된 C2 ~ C30의 헤테로아릴렌이고, L is a divalent linking group, which is substituted or unsubstituted C6 to C30 arylene or substituted or unsubstituted C2 to C30 heteroarylene,
l은 0, 1, 2, 또는 3이다.l is 0, 1, 2, or 3.
이때, 안트라센의 탄소 위치의 번호를 정하는 방식은 하기와 같이 나타낼 수 있다. At this time, the method of determining the number of carbon positions of anthracene can be expressed as follows.
본 발명의 일 실시예에 따른 안트란센계 화함물은 상기 화학식 1 또는 화학식 2로 표시되는 치환기가 안트라센의 2, 3, 6, 7, 9, 및 10 중 하나의 위치에 치환될 수 있다. In the anthracene-based compound according to an embodiment of the present invention, the substituent represented by Formula 1 or Formula 2 may be substituted at one of 2, 3, 6, 7, 9, and 10 of anthracene.
본 발명의 일 실시예에 따른 안트라센계 화합물은 하기 화학식 3 내지 화학식 6으로 표시될 수 있다:Anthracene-based compound according to an embodiment of the present invention may be represented by the following formula (3):
[화학식 3][Formula 3]
[화학식 4][Formula 4]
[화학식 5][Formula 5]
[화학식 6][Formula 6]
상기 화학식 3 내지 화학식 6에서, In
R1 내지 R17 은 서로 동일 또는 상이하며 각각 수소, 할로겐, 시아노기, 히드록실기, 치환 또는 비치환된 C1~ C20의 알킬기, 치환 또는 비치환된 C3 ~ C20의 사이클로알킬기, 치환 또는 비치환된 C5 -C30 헤테로사이클로알킬기, 치환 또는 비치환된 C1~ C20의 알콕시기, 치환 또는 비치환된 C6 ~ C30의 아릴기, 치환 또는 비치환된 C6 ~ C30의 아랄킬기, 치환 또는 비치환된 C2 ~ C30의 헤테로아릴기이고, R 1 to R 17 are the same as or different from each other, and each hydrogen, halogen, cyano group, hydroxyl group, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C3 to C20 cycloalkyl group, substituted or unsubstituted C5-C30 heterocycloalkyl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C6-C30 aralkyl group, substituted or unsubstituted C2 C30 is a heteroaryl group,
Ar1, Ar2 및 Ar3은 동일하거나 상이하게 각각 치환 또는 비치환된 C6 ~ C30의 아릴기이고 Ar 1 , Ar 2, and Ar 3 are the same or differently substituted or unsubstituted C6 to C30 aryl groups, respectively.
L'및 L"은 2가의 연결기로서, 치환 또는 비치환된 C6 ~ C30의 아릴렌 또는 치환 또는 비치환된 C2 ~ C30의 헤테로아릴렌이고 L 'and L "are divalent linking groups, which may be substituted or unsubstituted C6 to C30 arylene or substituted or unsubstituted C2 to C30 heteroarylene.
m 및 n은 0, 1, 2, 또는 3이다.m and n are 0, 1, 2, or 3.
이때, 상기 화학식 1 내지 화학식 6에서, L, L'및 L"가 서로 동일 또는 상이하며, 하기의 구조식 중 어느 하나로 표시될 수 있다. At this time, in Formula 1 to Formula 6, L, L 'and L "are the same or different from each other, it may be represented by any one of the following structural formula.
상기 구조식에서, R`는 서로 동일 또는 상이하며 각각 수소, 할로겐, 시아노기, 히드록실기, 치환 또는 비치환된 C1~ C20의 알킬기, 치환 또는 비치환된 C3 ~ C20의 사이클로알킬기, 치환 또는 비치환된 C5 ~ C30 헤테로사이클로알킬기, 치환 또는 비치환된 C1~ C20의 알콕시기, 치환 또는 비치환된 C6 ~ C30의 아릴기, 치환 또는 비치환된 C 6 ~ C 30의 아랄킬기, 치환 또는 비치환된 C2 ~ C 30의 헤테로아릴기이다.In the above structural formula, R` is the same or different from each other and each hydrogen, halogen, cyano group, hydroxyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted A substituted C5 to C30 heterocycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aralkyl group, a substituted or unsubstituted It is a substituted C2 ~
또한, 상기 화학식 3 내지 화학식 6에서, Ar1, Ar2 및 Ar3이 서로 동일 또는 상이하며, 하기의 구조식 중 어느 하나로 표시될 수 있다. In addition, in
상기 구조식에서, R`는 서로 동일 또는 상이하며 각각 수소, 할로겐, 시아노기, 히드록실기, 치환 또는 비치환된 C1~ C20의 알킬기, 치환 또는 비치환된 C3 ~ C20의 사이클로알킬기, 치환 또는 비치환된 C5 -C30 헤테로사이클로알킬기, 치환 또는 비치환된 C1~ C20의 알콕시기, 치환 또는 비치환된 C6 ~ C30의 아릴기, 치환 또는 비치환된 C6 ~ C30의 아랄킬기, 치환 또는 비치환된 C2 ~ C30의 헤테로아릴기이다.In the above structural formula, R` is the same or different from each other and each hydrogen, halogen, cyano group, hydroxyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted A substituted C5-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group, a substituted or unsubstituted C2-C30 heteroaryl group.
본 발명에 사용된 치환기의 용어 중, 알킬기는 탄소수 1 내지 20의 직쇄형 또는 분지형 알킬기가 바람직하고, 탄소수 1 내지 12의 직쇄형 또는 분지형 알킬기가 더욱 바람직하고, 탄소수 1 내지 6의 직쇄형 또는 분지형 알킬기가 가장 바람직하다. 이와 같은 비치환된 알킬기의 예로는 메틸, 에틸, n-프로필, 이소프로필, n-부틸, 이소부틸, sec-부틸, t-부틸, 펜틸, 이소아밀, 헥실 등을 들 수 있다. Among the terms of the substituent used in the present invention, the alkyl group is preferably a straight or branched alkyl group having 1 to 20 carbon atoms, more preferably a straight or branched alkyl group having 1 to 12 carbon atoms, and a straight chain having 1 to 6 carbon atoms. Or branched alkyl groups are most preferred. Examples of such unsubstituted alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, pentyl, isoamyl, hexyl and the like.
본 발명에서 사용되는 사이클로알킬기는 탄소원자수 3 내지 20, 바람직하게는 3 내지 10개, 보다 바람직하게는 3 내지 6개의 1가 모노사이클릭 시스템을 의미한다. By cycloalkyl group used in the present invention is meant a monovalent monocyclic system having 3 to 20 carbon atoms, preferably 3 to 10 carbon atoms, more preferably 3 to 6 carbon atoms.
본 발명에서 사용되는 헤테로사이클로알킬기는 N, O, P 또는 S 중에서 선택된 1, 2 또는 3개의 헤테로원자를 포함하고, 나머지 고리원자가 C인 고리원자수 3 내지 20, 바람직하게는 3 내지 10개, 보다 바람직하게는 3 내지 6개의 1가 모노사이클릭 시스템을 의미한다. The heterocycloalkyl group used in the present invention includes 1, 2 or 3 heteroatoms selected from N, O, P or S, and has 3 to 20, preferably 3 to 10 ring atoms having the remaining ring atoms of C, More preferably 3 to 6 monovalent monocyclic systems.
본 발명에 사용된 치환기의 용어 중, 알콕시기는 탄소수 1 내지 20의 알킬 부분을 각각 갖는 산소-함유 직쇄형 또는 분지형 알콕시기가 바람직하다. 1 내지 6개의 탄소 원자를 갖는 알콕시기가 더욱 바람직하고 1 내지 3개의 탄소 원자를 갖는 알콕시기가 가장 바람직하다. 이러한 알콕시기의 예로는 메톡시, 에톡시, 프로폭시, 부톡시, 및 t-부톡시를 들 수 있다. 상기 알콕시기는 플루오로, 클로로 또 는 브로모와 같은 하나 이상의 할로 원자로 더 치환되어 할로알콕시기를 제공할 수도 있다. 이와 같은 예로는 플루오로메톡시, 클로로메톡시, 트리플루오로메톡시, 트리플루오로에톡시, 플로오로에톡시 및 플루오로프로폭시 등을 들 수 있다. Among the terms of the substituents used in the present invention, an alkoxy group is preferably an oxygen-containing straight or branched alkoxy group each having an alkyl moiety of 1 to 20 carbon atoms. More preferred are alkoxy groups having 1 to 6 carbon atoms and most preferred are alkoxy groups having 1 to 3 carbon atoms. Examples of such alkoxy groups include methoxy, ethoxy, propoxy, butoxy, and t-butoxy. The alkoxy group may be further substituted with one or more halo atoms such as fluoro, chloro or bromo to provide a haloalkoxy group. Examples thereof include fluoromethoxy, chloromethoxy, trifluoromethoxy, trifluoroethoxy, fluoroethoxy, fluoropropoxy and the like.
본 발명에 사용된 치환기의 용어 중, 헤테로알킬기는 상기 알킬기에서 탄소원자수 1 내지 20, 바람직하게는 1 내지 12, 더욱 바람직하게는 1 내지 6의 주쇄 내에 헤테로원자, 예를 들어 N, O, P, S 등을 포함하는 것을 의미한다. In the terminology of a substituent used in the present invention, a heteroalkyl group is a heteroatom in the main chain of 1 to 20, preferably 1 to 12, more preferably 1 to 6 carbon atoms in the alkyl group, for example N, O, P , S and the like.
본 발명에 사용된 치환기의 용어 중, 아릴기는 단독 또는 조합하여 사용되어 하나 이상의 고리를 포함하는 탄소수 6 내지 30의 카보사이클 방향족 시스템을 의미하며 상기 고리들은 펜던트 방법으로 함께 부착되거나 융합될 수 있다. 아릴이라는 용어는 페닐, 나프틸, 테트라히드로나프틸, 인단 및 비페닐과 같은 방향족 라디칼을 포함한다. 더욱 바람직하게는 페닐이다. Among the terms of the substituents used in the present invention, an aryl group is used alone or in combination to mean a carbocycle aromatic system having 6 to 30 carbon atoms containing one or more rings, which rings may be attached or fused together in a pendant manner. The term aryl includes aromatic radicals such as phenyl, naphthyl, tetrahydronaphthyl, indane and biphenyl. More preferably phenyl.
본 발명에 사용된 치환기의 용어 중, 아릴알킬기는 상기 알킬기의 하나 이상의 수소원자가 상기 아릴기로 치환되어 있는 것을 의미한다.In the term of the substituent used in the present invention, an arylalkyl group means that one or more hydrogen atoms of the alkyl group are substituted with the aryl group.
본 발명에 사용된 치환기의 용어 중, 헤테로아릴기는 N, O, 또는 S 중에서 선택된 1, 2 또는 3개의 헤테로 원자를 포함하고, 나머지 고리 원자가 C인 고리 원자수 5 내지 30의 1가 모노사이클릭 또는 비사이클릭 방향족 라디칼을 의미한다. 또한 상기 용어는 고리내 헤테로 원자가 산화되거나 사원화되어 예를 들어 N-옥사이드 또는 4차 염을 형성하는 1가 모노사이클릭 또는 비사이클릭 방향족 라디칼을 의미한다. 대표적인 예로는 티에닐, 벤조티에닐, 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 퀴놀리닐, 퀴녹살리닐, 이미다졸릴, 푸라닐, 벤조푸라닐, 티아졸릴, 이속사졸린, 벤즈이속사졸린, 벤즈이미다졸릴, 트리아졸릴, 피라졸릴, 피롤릴, 인돌릴, 2-피리도닐, N-알킬-2-피리도닐, 피라지노닐, 피리다지노닐, 피리미디노닐, 옥사졸로닐 및 이들의 상응하는 N-옥사이드(예를 들어 피리딜 N-옥사이드, 퀴놀리닐 N-옥사이드), 이들의 4차 염 등을 포함하지만 이에 한정되지 않는다. In the term of the substituent used in the present invention, the heteroaryl group contains 1, 2 or 3 heteroatoms selected from N, O, or S, and the remaining ring atoms are C to monovalent monocyclic monocyclic having 5 to 30 ring atoms. Or acyclic aromatic radicals. The term also refers to monovalent monocyclic or bicyclic aromatic radicals in which heteroatoms in the ring are oxidized or quaternized to form, for example, N-oxides or quaternary salts. Representative examples include thienyl, benzothienyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, quinoxalinyl, imidazolyl, furanyl, benzofuranyl, thiazolyl, isoxazolin, Benzisoxazolin, benzimidazolyl, triazolyl, pyrazolyl, pyrrolyl, indolyl, 2-pyridonyl, N-alkyl-2-pyridonyl, pyrazinyl, pyridazininyl, pyrimidinyl , Oxazoloyl and their corresponding N-oxides (eg pyridyl N-oxides, quinolinyl N-oxides), quaternary salts thereof, and the like.
상기 화학식들에서 알킬기, 알콕시기, 아릴기, 헤테로아릴기, 사이클로알킬기 및 헤테로사이클로알킬기가 치환될 경우, 이들의 치환기는, -F; -Cl; -Br; -CN; -NO2; -OH; 비치환 또는 -F, -Cl, -Br, -CN, -NO2 또는 -OH로 치환된 C1 ~ C20 알킬기; 비치환 또는 -F, -Cl, -Br, -CN, -NO2 또는 -OH로 치환된 C1 ~ C20 알콕시기; 비치환 또는 C1 ~ C20 알킬기, C1 ~ C20 알콕시기, -F, -Cl, -Br, -CN, -NO2 또는 -OH로 치환된 C6 ~ C30 아릴기; 비치환 또는 C1 ~ C20 알킬기, C1 ~ C20 알콕시기, -F, -Cl, -Br, -CN, -NO2 또는 -OH로 치환된 C2 ~ C30 헤테로아릴기; 비치환 또는 C1 ~ C20 알킬기, C1 ~ C20 알콕시기, -F, -Cl, -Br, -CN, -NO2 또는 -OH로 치환된 C5 ~ C20 사이클로알킬기; 비치환 또는 C1 ~ C20 알킬기, C1 ~ 20 알콕시기, -F, -Cl, -Br, -CN, -NO2 또는 -OH로 치환된 C5 ~ C30 헤테로사이클로알킬기 및 -N(G6)(G7)으로 표시되는 기로 이루어진 군으로부터 선택된 하나 이상일 수 있다. 이 때, 상기 G6 및 G7 은 서로 독립적으로 각각 수소; C1 ~ C10 알킬기; 또는 C1 ~ C10 알킬기로 치환된 C6 ~ C30 아릴기일 수 있다.In the above formulas, when an alkyl group, an alkoxy group, an aryl group, a heteroaryl group, a cycloalkyl group and a heterocycloalkyl group are substituted, their substituents are -F; -Cl; -Br; -CN; -NO 2 ; -OH; C1 to C20 alkyl group unsubstituted or substituted with -F, -Cl, -Br, -CN, -NO 2 or -OH; C1-C20 alkoxy group unsubstituted or substituted with -F, -Cl, -Br, -CN, -NO 2 or -OH; C6 to C30 aryl group which is unsubstituted or substituted with C1 to C20 alkyl group, C1 to C20 alkoxy group, -F, -Cl, -Br, -CN, -NO 2 or -OH; A C2 to C30 heteroaryl group unsubstituted or substituted with a C1 to C20 alkyl group, a C1 to C20 alkoxy group, -F, -Cl, -Br, -CN, -NO 2 or -OH; A C5 to C20 cycloalkyl group unsubstituted or substituted with a C1 to C20 alkyl group, a C1 to C20 alkoxy group, -F, -Cl, -Br, -CN, -NO 2 or -OH; Unsubstituted or substituted C1 to C20 alkyl group, C1 to 20 alkoxy group, C5 to C30 heterocycloalkyl group substituted with -F, -Cl, -Br, -CN, -NO 2 or -OH and -N (G6) (G7) It may be one or more selected from the group consisting of a group represented by. In this case, G6 and G7 are each independently hydrogen; C1-C10 alkyl group; Or a C6 to C30 aryl group substituted with a C1 to C10 alkyl group.
보다 구체적으로, R1 내지 R17 은 서로 독립적으로, 수소, 할로겐, 시아노기, 히드록실기, C1 ~ C10 알킬기, C1 ~ C10 알콕시기이고, 치환 또는 비치환된 다음과 같은 유도체로 이루어진 군으로부터 선택될 수 있다: 페닐기, 비페닐기, 펜타레닐기, 인데닐기, 나프틸기, 비페닐레닐기, 안트라세닐기, 아즈레닐기, 헵타레닐기, 아세나프틸레닐기, 페나레닐기, 플루오레닐기, 메틸안트릴기, 페난트레닐기, 트리페닐레닐기, 피레닐기, 크리세닐기, 에틸-크리세닐기, 피세닐기, 페릴레닐기, 클로로페릴레닐기, 펜타페닐기, 펜타세닐기, 테트라페닐레닐기, 헥사페닐기, 헥사세닐기, 루비세닐기, 코로네닐기, 트리나프틸레닐기, 헵타페닐기, 헵타세닐기, 플루오레닐기, 피란트레닐기, 오바레닐기, 카르바졸릴기, 티오페닐기, 인돌일기, 푸리닐기, 벤즈이미다졸일기, 퀴놀리닐기, 벤조티오페닐기, 파라티아지닐기, 피롤일기, 피라졸릴기, 이미다졸릴기, 이미다졸리닐기, 옥사졸릴기, 티아졸릴기, 트리아졸릴기, 테트라졸일기, 옥사디아졸릴기, 피리디닐기, 피리다지닐기, 피리미디닐기, 피라지닐기, 티안트레닐기(thianthrenyl), 사이클로펜틸기, 사이클로헥실기, 옥시라닐기, 피롤리디닐기, 피라졸리디닐기, 이미다졸리디닐기, 피페리디닐기, 피페라지닐기, 모르폴리닐기, 디(C6 ~ C30 아릴)아미노기, 트리(C6 ~ C30 아릴)실릴기 및 이들의 유도체.More specifically, R 1 to R 17 are independently from each other, hydrogen, halogen, cyano group, hydroxyl group, C1 to C10 alkyl group, C1 to C10 alkoxy group, and from the group consisting of substituted or unsubstituted derivatives as follows: Can be selected: phenyl group, biphenyl group, pentarenyl group, indenyl group, naphthyl group, biphenylenyl group, anthracenyl group, azurenyl group, heptarenyl group, acenaphthylenyl group, phenenyl group, fluorenyl group, Methyl anthryl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, ethyl- chrysenyl group, pisenyl group, peryllenyl group, chloroperylenyl group, pentaphenyl group, pentacenyl group, tetraphenylle Neyl group, hexaphenyl group, hexasenyl group, rubisenyl group, coronyl group, trinaphthylenyl group, heptaphenyl group, heptasenyl group, fluorenyl group, pyrantrenyl group, ovarenyl group, carbazolyl group, thiophenyl group, indole Diary, Furinyl, Benzimidazolyl, Quinol Nyl group, benzothiophenyl group, parathiazinyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, imidazolinyl group, oxazolyl group, thiazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, pyri Dinyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, thianthrenyl group, thianthrenyl group, cyclopentyl group, cyclohexyl group, oxiranyl group, pyrrolidinyl group, pyrazolidinyl group, imidazolidinyl group , Piperidinyl group, piperazinyl group, morpholinyl group, di (C6 to C30 aryl) amino group, tri (C6 to C30 aryl) silyl group and derivatives thereof.
본 명세서에 있어서, 상기 "유도체"란 용어는 상기 나열한 기들 중 하나 이상의 수소가 전술한 바와 같은 치환기로 치환된 기를 가리키는 것이다.As used herein, the term "derivative" refers to a group in which one or more hydrogens of the groups listed above are substituted with a substituent as described above.
본 발명의 일 실시예에 따른 안트라센계 화합물은 유기막 형성시 용매에 대한 용해도가 크고, 비편재화된 전자분포 및 강직한 구조로 인해 유리전이온도가 높아 열안정성이 우수하며, 특히 피리디닐퀴놀린계 치환기가 도입되어 개선된 우수 한 전자주입성 및 전자수송성을 보이여, 유기 전계 발광 소자에 적용시 저전압 구동이 가능하고, 고효율의 특성을 얻을 수 있다. The anthracene-based compound according to an embodiment of the present invention has high thermal stability due to high solubility in a solvent when forming an organic layer, high glass transition temperature due to unlocalized electron distribution and rigid structure, and particularly pyridinylquinoline Substituents are introduced to show excellent electron injection and electron transportability, and thus, when applied to an organic EL device, low voltage driving is possible and high efficiency characteristics can be obtained.
본 발명의 일 실시예에 따른 화합물은 하기 화학식 7 내지 화학식 50으로 표시되는 화합물일 수 있으나, 이에 한정되는 것은 아니다:The compound according to an embodiment of the present invention may be a compound represented by the following
[화학식 7][Formula 7]
[화학식 8][Formula 8]
[화학식 9][Formula 9]
[화학식 10][Formula 10]
[화학식 11][Formula 11]
[화학식 12][Formula 12]
[화학식 13][Formula 13]
[화학식 14][Formula 14]
[화학식 15][Formula 15]
[화학식 16][Formula 16]
[화학식 17] [Formula 17]
[화학식 18][Formula 18]
[화학식 19][Formula 19]
[화학식 20][Formula 20]
[화학식 21][Formula 21]
[화학식 22][Formula 22]
[화학식 23][Formula 23]
[화학식 24][Formula 24]
[화학식 25][Formula 25]
[화학식 26] [Formula 26]
[화학식 27][Formula 27]
[화학식 28][Formula 28]
[화학식 29][Formula 29]
[화학식 30][Formula 30]
[화학식 31][Formula 31]
[화학식 32][Formula 32]
[화학식 33][Formula 33]
[화학식 34][Formula 34]
[화학식 35][Formula 35]
[화학식 36][Formula 36]
[화학식 37][Formula 37]
[화학식 38][Formula 38]
[화학식 39][Formula 39]
[화학식 40][Formula 40]
[화학식 41][Formula 41]
[화학식 42][Formula 42]
[화학식 43][Formula 43]
[화학식 44][Formula 44]
[화학식 45][Formula 45]
[화학식 46][Formula 46]
[화학식 47][Formula 47]
[화학식 48][Formula 48]
[화학식 49][Formula 49]
[화학식 50][Formula 50]
본 발명의 일 실시예에 따른 화합물은 통상의 합성 방법을 이용하여 합성될 수 있으며, 상기 화합물의 보다 상세한 합성 경로는 하기 합성예의 반응식을 참조한다.Compounds according to one embodiment of the present invention can be synthesized using conventional synthetic methods, for a more detailed synthetic route of the compounds refer to the scheme of the following synthesis examples.
본 발명의 유기 전계 발광 소자는, The organic electroluminescent device of the present invention,
제1전극;A first electrode;
제2전극; 및Second electrode; And
상기 제1전극과 상기 제2전극 사이에 개재된 유기막을 포함하는 유기 전계 발광 소자로서, 상기 유기막이 상기 화학식 1 또는 화학식 2로 표시되는 치환기를 갖는 안트라센계 화합물 하나 이상 포함하는 것을 특징으로 한다.An organic electroluminescent device comprising an organic film interposed between the first electrode and the second electrode, characterized in that the organic film includes at least one anthracene-based compound having a substituent represented by the formula (1) or (2).
본 발명의 일 실시예 따른 안트라센계 화합물은 유기 전계 발광 소자의 유기막, 특히 발광층, 전자주입층, 전자수송층 또는 정공저지층에 사용되기 적합하다. 본 발명에 다른 유기 전계 발광 소자의 발광층은 적색, 녹색, 청색 또는 백색을 포함하는 인광 또는 형광 도펀트를 포함할 수 있다. 이 중, 상기 인광 도펀트는 Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb 및 Tm으로 이루어진 군으로부터 선택된 하나 이상의 원소를 포함하는 유기금속화합물일 수 있다.The anthracene-based compound according to an embodiment of the present invention is suitable for use in an organic film, particularly a light emitting layer, an electron injection layer, an electron transport layer or a hole blocking layer of an organic EL device. The light emitting layer of the organic electroluminescent device according to the present invention may include a phosphorescent or fluorescent dopant including red, green, blue or white. Among these, the phosphorescent dopant may be an organometallic compound including at least one element selected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, and Tm.
본 발명의 일 실시예에 따른 유기 전계 발광 소자는, 용액 도포법으로 제조할 경우 유기막의 안정성이 떨어지는 종래의 유기 전계 발광 소자의 경우와 달리, 우수한 용해성과 열 안정성을 가지면서도 안정한 유기막의 형성이 가능한 화합물을 포함하여, 우수한 구동 전압 및 색순도 등의 향상된 발광 특성을 제공할 수 있다.According to the organic electroluminescent device according to an embodiment of the present invention, unlike the conventional organic electroluminescent device in which the stability of the organic film is poor when manufactured by the solution coating method, formation of a stable organic film with excellent solubility and thermal stability Possible compounds can be included to provide improved luminescent properties such as excellent drive voltage and color purity.
본 발명의 일 실시예에 따른 유기 전계 발광 소자의 구조는 매우 다양할 수 있다. 즉, 상기 제1전극과 제2전극 사이에 정공주입층, 정공수송층, 정공저지층, 전자저지층, 전자수송층 및 전자주입층으로 이루어진 군으로부터 선택된 하나 이상의 층을 더 포함할 수 있다.The structure of the organic electroluminescent device according to an embodiment of the present invention can be very diverse. That is, one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole blocking layer, an electron blocking layer, an electron transport layer and an electron injection layer may be further included between the first electrode and the second electrode.
보다 구체적으로, 본 발명의 일 실시예에 따른 유기 전계 발광 소자의 구체적인 예는 도 1a, 1b 및 1c를 참조한다. 도 1a의 유기 전계 발광 소자는 제1전극/정공주입층/정공수송층/발광층/전자수송층/전자주입층/제2전극으로 이루어진 구조를 갖고, 도 1b의 유기 전계 발광 소자는 제1전극/정공주입층/발광층/전자수송층/전자주입층/제2전극으로 이루어진 구조를 갖는다. More specifically, for specific examples of the organic electroluminescent device according to an embodiment of the present invention refer to Figures 1a, 1b and 1c. The organic electroluminescent device of FIG. 1A has a structure consisting of a first electrode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / second electrode, and the organic electroluminescent device of FIG. 1B includes a first electrode / hole It has a structure consisting of an injection layer / light emitting layer / electron transport layer / electron injection layer / second electrode.
본 발명의 일 실시예에 따른 유기 전계 발광 소자의 유기막은 유기 금속 착체를 더 포함할 수 있다.The organic film of the organic electroluminescent device according to an embodiment of the present invention may further include an organometallic complex.
상기 유기 금속 착체라 함은, 유기배위자를 가지며, 금속과의 결합이 배위결합만으로 이루어진 화합물을 말한다. The organometallic complex refers to a compound having an organic ligand and composed of only coordinating bonds with the metal.
이때, 상기 금속으로는 Li, Na, K, Rb, Cs 등의 알카리금속(Ⅰ); Mg, Ca, Sr, Ba 등의 알카리토금속(Ⅱ); Y, La, Ce, Pr, Nd, Sm, Eu, Er, Yb 등의 희토류금속(Ⅲ) 등이다.At this time, the metal is an alkali metal (I) such as Li, Na, K, Rb, Cs; Alkaline earth metal (II) such as Mg, Ca, Sr, and Ba; Rare earth metals (III) such as Y, La, Ce, Pr, Nd, Sm, Eu, Er, and Yb.
상기 유기 금속 착체에 있어서, 이들의 금속에 배위하는 배위자로는 β-디케톤류(예를 들어, 아세틸아세톤, 1,3-디페닐-1,3-프로판디온, 2,2,6,6-테트라메틸-3,5-헵탄디온, 1,1,1,2,2,3,3,-헵타플루오로-7,7-디메틸-4,6-옥탄디온, 1-페닐-1,3-부탄디온 등), 살리틸알데히드류(예를 들어, 살리틸알데히드, 디에틸아미노살리티알데히드 등), 안트라센, 나프탈렌, 페난트렌, 피렌, 테트라센, 코로넨, 크리 센, 플루오레세인, 페릴렌, 프탈로페릴렌, 나프탈로페릴렌, 페리논, 프탈로페리논, 나프탈로페리논, 디페닐부타디엔, 테트라페닐부타디엔, 쿠마린, 옥사디아졸, 알다진, 비스벤즈옥사졸린, 비스스티릴, 피라진, 사이클로펜타디엔, 퀴놀린, 아미노퀴놀린, 벤조퀴놀린의 등을 들 수 있다.In the organometallic complex, as ligands coordinated with these metals, β-diketones (eg, acetylacetone, 1,3-diphenyl-1,3-propanedione, 2,2,6,6- Tetramethyl-3,5-heptanedione, 1,1,1,2,2,3,3, -heptafluoro-7,7-dimethyl-4,6-octanedione, 1-phenyl-1,3- Butanedione, etc.), salicylaldehydes (e.g., salylaldehyde, diethylaminosaltyaldehyde, etc.), anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, ferric Reylene, Phthaloferylene, Naphthaloperylene, Perinone, Phthaloperinone, Naphthalopelinone, Diphenylbutadiene, Tetraphenylbutadiene, Coumarin, Oxadiazole, Aldazine, Bisbenzoxazolin, Bisstyryl And pyrazine, cyclopentadiene, quinoline, aminoquinoline, benzoquinoline, and the like.
상기 유기 금속 착체의 함량은 유기막을 형성하는 고형분 100 중량부에 대하여 0.01 내지 90 중량부, 바람직하게는 0.1 내지 60 중량부이고, 이때, 상기 함량이 0.01 중량부 미만이면 발광 효율의 향상 및 전자주입 효과가 불충분하고, 90 중량부 초과이면 전자수송특성의 저하로 인해 바람직하지 않다. The content of the organometallic complex is 0.01 to 90 parts by weight, preferably 0.1 to 60 parts by weight, based on 100 parts by weight of solids forming the organic film. In this case, when the content is less than 0.01 parts by weight, the emission efficiency is improved and electron injection is performed. If the effect is insufficient and more than 90 parts by weight, it is not preferable due to the deterioration of the electron transport characteristics.
또한, 본 발명의 일 실시예에 따른 유기 전계 발광 소자의 유기막은 이온성 염, 즉, 무기 이온염, 유기 이온염 또는 금속 이온염을 더 포함할 수 있다. In addition, the organic layer of the organic EL device according to an embodiment of the present invention may further include an ionic salt, that is, an inorganic ion salt, an organic ion salt or a metal ion salt.
본 발명의 일 실시예에 따라 상기 유기막에 포함되는 이온성 염으로는 대표적으로 LiClO4, LiPF6, LiBF4, LiN(CF3SO2)2, 리튬트리플로로메탄 트리설포네이트(lithium trifluoromethane sulfonate) 등의 Li 양이온 함유 무기 이온염(inorganic salts) 및 TEA-BF4 (tetraethylammonium tetrafluoroborate), Bu4N-BF4 (tetra-n-butylammonium tetrafluoroborate), 테트라 알킬, 아릴(aryl) 또는 헤테로아릴 쿼터너리 암모늄염 [예: tetra-n-alkylammonium toluenesulfonate, tetra-n-alkylammonium tetrafluoroborate, tetra-n-alkyl ammonium tetraphenylborate, tetra-n-alkyl ammonium toluenesulfonate, tetraalkylammonium tetrafluoro borate, tetra-n-alkyl ammonium tetraphenylborate] 등의 유기 이온염, 폴리스티렌설포네이트 (Polystyrenesulfonate: PSS) 등의 고분자 이온염 (polymeric salt) 등이 사용될 수 있다. In accordance with an embodiment of the present invention, the ionic salts included in the organic membrane are typically LiClO 4 , LiPF 6 , LiBF 4 , LiN (CF 3 SO 2 ) 2 , and lithium trifluoromethane trisulfonate. Inorganic salts containing Li cations such as sulfonate) and tetraethylammonium tetrafluoroborate (TEA-BF 4 ), tetra-n-butylammonium tetrafluoroborate (Bu 4 N-BF 4 ), tetraalkyl, aryl or heteroaryl quarters Organic ammonium salts such as tetra-n-alkylammonium toluenesulfonate, tetra-n-alkylammonium tetrafluoroborate, tetra-n-alkyl ammonium tetraphenylborate, tetra-n-alkyl ammonium toluenesulfonate, tetraalkylammonium tetrafluoro borate, tetra-n-alkyl ammonium tetraphenylborate Polymeric salts such as ionic salts and polystyrenesulfonate (PSS) may be used.
또한, 금속 이온염은 Al(Ⅲ), Mn(Ⅱ), Zr(Ⅳ), Ti(Ⅱ), Hf(Ⅳ), Ta(Ⅴ), Nb(Ⅲ), V(Ⅱ) 등의 금속을 포함하고, 무기 금속 이온염으로는 무기산의 수소를 금속으로 치환한 것이며, 예를 들어 할로겐화물(구체적으로는, 염화물, 플루오르화물, 브롬화물, 요오드화물 등)을 들 수 있으며, 유기 금속 이온염으로는 유기산, 알코올, 디알킬아미드의 수소를 금속으로 치환한 것이며, 구체적으로는 카르본산, 페놀 등의 유기산 염, 알콜시드, 디아킬아미드 염 등을 들 수 있다.In addition, the metal ion salt includes metals such as Al (III), Mn (II), Zr (IV), Ti (II), Hf (IV), Ta (V), Nb (III) and V (II). As the inorganic metal ion salt, hydrogen of the inorganic acid is substituted with a metal, and for example, halides (specifically, chloride, fluoride, bromide, iodide, etc.) are mentioned. Hydrogens of organic acids, alcohols and dialkylamides are substituted with metals, and specific examples include organic acid salts such as carboxylic acid and phenol, alcohol seeds and dialkylamide salts.
이때, 카르본산으로는 지방족이거나 방향족일 수도 있다. 지방족카르본산으로는 총탄소수 1∼24인 것이 바람직하며, 포화지방족카르본산이거나 불포화지방산카르본산일 수도 있으며, 카르복실기를 2개이상 갖는 것일 수도 있다. 또 아릴기 등의 치환기를 가질 수도 있다. 구체적으로는, 아세트산, 프로피온산, 옥틸신, 이소옥틸산, 데칸산, 라우릴산 등의 지방족카르본산; 올레인산, 리시놀산(리시노렌 등)등의 불포화지방족카르본산, 구연산, 사과산, 수산 등의 디 및 트리 등의 다가의 카르본산 등을 들 수가 있다. 방향족카르본산으로는 총탄소수 7∼24의 것이 바람직하며, 치환기(탄소기 1∼8의 알킬기, 히드록시기)를 가질 수도 있으며, 구체적으로는 안식향산, o-(t-부틸)안식향산, m-(t-부틸)안식향산, 살리틸산, m-(히드록시)안식향산, p-(히드록시)안식향산)등을 들 수가 있다. 페놀로는 총탄소수 6∼46의 것이 바람직하며, 치환기(탄소수 1∼8의 직쇄상 또는 분지상 알킬기나, 페닐기 등의 아릴기 등)나 축합고리(치환고리를 가질 수도 있는 벤젠고리 등의 방향고리 등)를 가질 수도 있으며, 1가의 페놀이거나, 2가 이상인 다가의 페놀일 수도 있다. 구체적으로는 페놀, 나프톨, 4-페닐페놀, 2,2-비스(p-히드록시페닐)프로판(비스페놀A) 등을 들 수 있다. 알콕시이드를 형성하는 알코올으로는, 총탄소수 1∼10인 것이 바람직하며, 에틸알코올, n-프로필알코올, n-부틸알코올 등의 제1급 알코올; 이소프로필알코올, s-부틸알코올 등의 제2급 알코올; t-부틸알코올 등의 제3급 알코올 등을 들 수 있다. 또 2가 이상의 다가 알코올일 수도 있으며, 예를 들어 에틸렌글리콜 등을 들 수 있다.At this time, the carboxylic acid may be aliphatic or aromatic. The aliphatic carboxylic acid preferably has 1 to 24 carbon atoms, and may be saturated aliphatic carboxylic acid or unsaturated fatty acid carboxylic acid, or may have two or more carboxyl groups. Moreover, you may have substituents, such as an aryl group. Specific examples include aliphatic carboxylic acids such as acetic acid, propionic acid, octylcin, isooctyl acid, decanoic acid and lauryl acid; And polyvalent carboxylic acids such as di and tri, such as unsaturated aliphatic carboxylic acids such as oleic acid and ricinolic acid (such as licinorene), citric acid, malic acid, and oxalic acid. As aromatic carboxylic acid, the thing of 7-24 total carbons is preferable, It may have a substituent (alkyl group of 1-8 carbon atoms, a hydroxyl group), Specifically, benzoic acid, o- (t-butyl) benzoic acid, m- (t -Butyl) benzoic acid, salicylic acid, m- (hydroxy) benzoic acid, p- (hydroxy) benzoic acid), and the like. As the phenol, those having 6 to 46 carbon atoms in total are preferable, and a substituent (such as a linear or branched alkyl group having 1 to 8 carbon atoms or an aryl group such as a phenyl group) or a condensed ring (benzene ring which may have a substituted ring) Ring), or a monovalent phenol or a divalent or higher polyhydric phenol. Specifically, phenol, naphthol, 4-phenylphenol, 2, 2-bis (p-hydroxyphenyl) propane (bisphenol A), etc. are mentioned. As an alcohol which forms an alkoxide, it is preferable that it is C1-C10, A primary alcohol, such as ethyl alcohol, n-propyl alcohol, n-butyl alcohol; Secondary alcohols such as isopropyl alcohol and s-butyl alcohol; tertiary alcohols such as t-butyl alcohol; and the like. Moreover, a bivalent or more polyhydric alcohol may be sufficient, for example, ethylene glycol etc. are mentioned.
디아킬아미드로는, 치환기를 가질 수도 있으며, 총탄소수는 2∼24인 것이 바람직하다. 구체적으로는 디메틸아미드, 디에틸아미드, N-메틸-N-에틸아미드 등을 들 수 있다.As dialkylamide, you may have a substituent and it is preferable that total carbon number is 2-24. Specifically, dimethylamide, diethylamide, N-methyl-N-ethylamide, etc. are mentioned.
그러나, 상기 염들은 단지 본 발명의 이온성 염으로 사용될 수 있는 예에 불과하고, 양이온과 음이온으로 구성되는 다양한 염들이 본 발명에 사용될 수 있다. However, the salts are merely examples that can be used as the ionic salt of the present invention, and various salts composed of cations and anions can be used in the present invention.
상기 이온성 염의 함량은 제조하는 EL층의 용도, 성분, 두께 등에 따라 달라질 수 있으나, 상기 유기막의 고형분 100중량부에 대하여 0.01 내지 50 중량부, 바람직하게는 1 내지 30 중량부이고, 이때, 상기 이온성 염의 함량이 0.01 중량부 미만일 경우에는 유기 전계 발광 소자의 발광 효율 향상 및 동작 개시전압 감소 효과가 불충분하며, 50 중량부를 초과하면 과도한 이온의 농도로 인해 소자의 작동이 불량해질 수 있어 바람직하지 않다.The content of the ionic salt may vary depending on the use, component, thickness, etc. of the EL layer to be manufactured, but is 0.01 to 50 parts by weight, preferably 1 to 30 parts by weight, based on 100 parts by weight of the solid content of the organic film. If the content of the ionic salt is less than 0.01 parts by weight, the effect of improving the luminous efficiency and reducing the operation start voltage of the organic electroluminescent device is insufficient, and if it exceeds 50 parts by weight, the operation of the device may be poor due to the excessive concentration of ions. not.
이하, 본 발명의 일 실시예에 따른 유기 전계 발광 소자의 제조 방법을 도 1a에 도시된 유기 전계 발광 소자를 참조하여, 살펴보기로 한다.Hereinafter, a method of manufacturing an organic EL device according to an embodiment of the present invention will be described with reference to the organic EL device shown in FIG. 1A.
먼저 기판 상부에 높은 일함수를 갖는 제1전극용 물질을 증착법 또는 스퍼터링법 등에 의해 형성하여 제1전극을 형성한다. 상기 제1전극은 애노드(Anode)일 수 있다. 여기에서 기판으로는 통상적인 유기 전계 발광 소자에서 사용되는 기판을 사용하는데 기계적 강도, 열적 안정성, 투명성, 표면 평활성, 취급용이성 및 방수성이 우수한 유리 기판 또는 투명 플라스틱 기판이 바람직하다. 제1전극용 물질로는 투명하고 전도성이 우수한 산화인듐주석(ITO), 산화인듐아연(IZO), 산화주석(SnO2), 산화아연(ZnO) 등을 사용한다.First, a first electrode material having a high work function on the substrate is formed by a deposition method or a sputtering method to form a first electrode. The first electrode may be an anode. Herein, a substrate used in a conventional organic electroluminescent device is used, and a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness is preferable. Indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, are used as the material for the first electrode.
다음으로, 상기 제1전극 상부에 진공증착법, 스핀코팅법, 캐스트법, LB법 등과 같은 다양한 방법을 이용하여 정공주입층(HIL)을 형성할 수 있다.Next, a hole injection layer HIL may be formed on the first electrode by using various methods such as vacuum deposition, spin coating, casting, and LB.
진공증착법에 의하여 정공주입층을 형성하는 경우, 그 증착 조건은 정공주입층의 재료로서 사용하는 화합물, 목적으로 하는 정공주입층의 구조 및 열적 특성 등에 따라 다르지만, 일반적으로 증착온도 100 내지 500℃, 진공도 10-8 내지 10-3 torr, 증착속도 0.01 내지 100Å/sec, 막 두께는 통상 10Å 내지 5㎛ 범위에서 적절히 선택하는 것이 바람직하다.In the case of forming the hole injection layer by vacuum deposition, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the hole injection layer, and the like. It is preferable that a vacuum degree of 10 -8 to 10 -3 torr, a deposition rate of 0.01 to 100 mW / sec, and a film thickness are usually appropriately selected in the range of 10 mV to 5 m.
스핀코팅법에 의하여 정공주입층을 형성하는 경우, 그 코팅 조건은 정공주입층의 재료로서 사용하는 화합물, 목적하는 하는 정공주입층의 구조 및 열적 특성에 따라 상이하지만, 약 2000rpm 내지 5000rpm의 코팅 속도, 코팅 후 용매 제거를 위한 열처리 온도는 약 80℃ 내지 200℃의 온도 범위에서 적절히 선택하는 것이 바람 직하다.In the case of forming the hole injection layer by spin coating, the coating conditions vary depending on the compound used as the material of the hole injection layer, the structure and the thermal properties of the desired hole injection layer, but the coating speed is about 2000 rpm to 5000 rpm. The heat treatment temperature for removing the solvent after coating is preferably selected in a temperature range of about 80 ° C to 200 ° C.
상기 정공주입층 두께는 약 100Å 내지 10000Å, 바람직하게는 100Å 내지 1000Å일 수 있다. 상기 정공주입층의 두께가 100Å 미만인 경우, 정공주입 특성이 저하될 수 있으며, 상기 정공주입층의 두께가 10000Å를 초과하는 경우, 구동전압이 상승할 수 있기 때문이다.The hole injection layer thickness may be about 100 kPa to 10000 kPa, preferably 100 kPa to 1000 kPa. This is because when the thickness of the hole injection layer is less than 100 kV, the hole injection characteristic may be lowered, and when the thickness of the hole injection layer exceeds 10000 kV, the driving voltage may increase.
다음으로 상기 정공주입층 상부에 진공증착법, 스핀코팅법, 캐스트법, LB법 등과 같은 다양한 방법을 이용하여 정공수송층(HTL)을 형성할 수 있다. 진공증착법 및 스핀코팅법에 의하여 정공수송층을 형성하는 경우, 그 증착조건 및 코팅조건은 사용하는 화합물에 따라 다르지만, 일반적으로 정공주입층의 형성과 거의 동일한 조건범위 중에서 선택된다.Next, a hole transport layer (HTL) may be formed on the hole injection layer by using various methods such as vacuum deposition, spin coating, cast, and LB. When the hole transport layer is formed by vacuum deposition or spin coating, the deposition conditions and coating conditions vary depending on the compound used, and are generally selected from the ranges of conditions substantially the same as those of forming the hole injection layer.
상기 정공수송층 두께는 약 50Å 내지 1000Å, 바람직하게는 100Å 내지 600Å일 수 있다. 상기 정공수송층의 두께가 50Å 미만인 경우, 정공수송 특성이 저하될 수 있으며, 상기 정공수송층의 두께가 1000Å를 초과하는 경우, 구동전압이 상승할 수 있기 때문이다.The hole transport layer thickness may be about 50 kPa to 1000 kPa, preferably 100 kPa to 600 kPa. This is because when the thickness of the hole transport layer is less than 50 kV, hole transport characteristics may be degraded, and when the thickness of the hole transport layer exceeds 1000 kW, the driving voltage may increase.
다음으로 상기 정공수송층 상부에 진공증착법, 스핀코팅법, 캐스트법, LB법 등과 같은 방법을 이용하여 발광층(EML)을 형성할 수 있다. 진공증착법 및 스핀코팅법에 의해 발광층을 형성하는 경우, 그 증착조건은 사용하는 화합물에 따라 다르지만, 일반적으로 정공주입층의 형성과 거의 동일한 조건범위 중에서 선택된다. Next, the light emitting layer EML may be formed on the hole transport layer by using a vacuum deposition method, a spin coating method, a cast method, an LB method, or the like. When the light emitting layer is formed by the vacuum deposition method or the spin coating method, the deposition conditions vary depending on the compound used, but are generally selected from the ranges of conditions substantially the same as those of forming the hole injection layer.
상기 발광층의 두께는 약 100Å 내지 1000Å, 바람직하게는 200Å 내지 600Å일 수 있다. 상기 발광층의 두께가 100Å 미만인 경우, 발광 특성이 저하될 수 있으며, 상기 발광층의 두께가 1000Å를 초과하는 경우, 구동전압이 상승할 수 있기 때문이다The thickness of the light emitting layer may be about 100 kPa to 1000 kPa, preferably 200 kPa to 600 kPa. This is because when the thickness of the light emitting layer is less than 100 kV, the light emission characteristic may be reduced, and when the thickness of the light emitting layer exceeds 1000 kW, the driving voltage may increase.
발광층에 인광 도펀트와 함께 사용할 경우에는 삼중항 여기자 또는 정공이 전자수송층으로 확산되는 현상을 방지하기 위하여, 상기 정공수송층 상부에 진공증 착법, 스핀코팅법, 캐스트법, LB법 등과 같은 방법을 이용하여 정공저지층(HBL)을 형성할 수 있다. 진공증착법 및 스핀코팅법에 의해 정공저지층을 형성하는 경우, 그 조건은 사용하는 화합물에 따라 다르지만, 일반적으로 정공주입층의 형성과 거의 동일한 조건범위 중에서 선택된다. 상기 정공저지층 물질은 전술한 바와 같은 상기 화학식 3 내지 화학식 6을 갖는 화합물일 수 있고, 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, BCP, 알루미늄 착물(aluminum complex) 등일 수도 있다.In the case of using the phosphorescent dopant in the light emitting layer, in order to prevent the triplet excitons or holes from diffusing into the electron transport layer, a method such as vacuum deposition, spin coating, cast method, LB method, etc. is used on the hole transport layer. The hole blocking layer HBL may be formed. In the case of forming the hole blocking layer by vacuum deposition or spin coating, the conditions vary depending on the compound used, but are generally selected from the ranges of conditions almost the same as that of forming the hole injection layer. The hole blocking layer material may be a compound having the
페난트롤린 함유 유기 화합물 이미다졸 함유 유기 화합물Phenanthroline-containing organic compounds Imidazole-containing organic compounds
트리아졸 함유 유기 화합물Triazole-containing organic compound
옥사디아졸 함유 화합물 Oxadiazole-containing compound
BAlq BAlq
상기 정공저지층의 두께는 약 50Å 내지 1000Å, 바람직하게는 100Å 내지 300Å일 수 있다. 상기 정공저지층의 두께가 50Å 미만인 경우, 정공저지 특성이 저하될 수 있으며, 상기 정공저지층의 두께가 1000Å를 초과하는 경우, 구동전압이 상승할 수 있기 때문이다.The hole blocking layer may have a thickness of about 50 kPa to 1000 kPa, preferably 100 kPa to 300 kPa. This is because when the thickness of the hole blocking layer is less than 50 kV, the hole blocking property may be deteriorated. When the thickness of the hole blocking layer is more than 1000 kV, the driving voltage may increase.
다음으로 전자수송층(ETL)을 진공증착법, 또는 스핀코팅법, 캐스트법 등의 다양한 방법을 이용하여 형성한다. 진공증착법 및 스핀코팅법에 의해 전자수송층을 형성하는 경우, 그 조건은 사용하는 화합물에 따라 다르지만, 일반적으로 정공주입층의 형성과 거의 동일한 조건범위 중에서 선택된다. 상기 전자수송층 재료는 전자주입전극(Cathode)로부터 주입된 전자를 안정하게 수송하는 기능을 하는 것으로서 전술한 바와 같은 상기 화학식 3 내지 화학식 6을 갖는 화합물일 수 있고, 옥사졸계 화합물, 이소옥사졸계 화합물, 트리아졸계 화합물, 이소티아졸(isothiazole)계 화합물, 옥사디아졸계 화합물, 티아다아졸(thiadiazole)계 화합물, 페릴렌(perylene)계 화합물, 알루미늄 착물(예: Alq3(트리스(8-퀴놀리놀라토)-알루미늄(tris(8-quinolinolato)-aluminium) BAlq, SAlq, Almq3, 갈륨 착물(예: Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2))등과 같은 공지의 재료를 사용할 수도 있다.Next, the electron transport layer (ETL) is formed using various methods such as vacuum deposition, spin coating, and casting. When the electron transport layer is formed by the vacuum deposition method or the spin coating method, the conditions vary depending on the compound used, but are generally selected from the ranges of conditions almost the same as that of the formation of the hole injection layer. The electron transport layer material may be a compound having the above formulas (3) to (6) as described above as a function of stably transporting the electrons injected from the electron injection electrode (Cathode), an oxazole-based compound, isoxazole compound, Triazole-based compound, isothiazole-based compound, oxadiazole-based compound, thiadiazole-based compound, perylene-based compound, aluminum complex (e.g. Alq3 (tris (8-quinolinolato) Known materials such as tris (8-quinolinolato) -aluminum BAlq, SAlq, Almq3, gallium complexes (e.g. Gaq'2OPiv, Gaq'2OAc, 2 (Gaq'2)) and the like can also be used.
페릴렌계 화합물 Perylene-Based Compound
Alq3 BAlq Alq3 BAlq
SAlq Almq3 SAlq Almq3
Gaq'2OPiv Gaq'2Oac Gaq'2OPiv Gaq'2Oac
2(Gaq'2) 2 (Gaq'2)
상기 전자수송층의 두께는 약 100Å 내지 1000Å, 바람직하게는 200Å 내지 500Å일 수 있다. 상기 전자수송층의 두께가 100Å 미만인 경우, 전자수송 특성이 저하될 수 있으며, 상기 전자수송층의 두께가 1000Å를 초과하는 경우, 구동전압이 상승할 수 있기 때문이다.The electron transport layer may have a thickness of about 100 kPa to 1000 kPa, preferably 200 kPa to 500 kPa. This is because when the thickness of the electron transport layer is less than 100 kV, the electron transport characteristic may be degraded, and when the thickness of the electron transport layer exceeds 1000 kW, the driving voltage may increase.
또한 전자수송층 상부에 음극으로부터 전자의 주입을 용이하게 하는 기능을 가지는 물질인 전자주입층(EIL)이 적층될 수 있으며 이는 특별히 재료가 제한되지 않는다.In addition, an electron injection layer (EIL), which is a material having a function of facilitating injection of electrons from the cathode, may be stacked on the electron transport layer, and the material is not particularly limited.
전자 주입층으로서는 LiF, NaCl, CsF, Li2O, BaO 등과 같은 전자주입층 형성 재료로서 공지된 임의의 물질을 이용할 수 있다. 상기 전자주입층의 증착조건은 사용하는 화합물에 따라 다르지만, 일반적으로 정공주입층의 형성과 거의 동일한 조건범위 중에서 선택된다.As the electron injection layer, any material known as an electron injection layer forming material such as LiF, NaCl, CsF, Li 2 O, BaO or the like can be used. The deposition conditions of the electron injection layer vary depending on the compound used, but are generally selected from the range of conditions almost the same as the formation of the hole injection layer.
상기 전자주입층의 두께는 약 1Å 내지 100Å, 바람직하게는 5Å 내지 50Å일 수 있다. 상기 전자주입층의 두께가 1Å 미만인 경우, 전자주입 특성이 저하될 수 있으며, 상기 전자주입층의 두께가 100Å를 초과하는 경우, 구동전압이 상승할 수 있기 때문이다.The electron injection layer may have a thickness of about 1 kPa to 100 kPa, preferably 5 kPa to 50 kPa. This is because, when the thickness of the electron injection layer is less than 1 kW, the electron injection characteristic may be deteriorated, and when the thickness of the electron injection layer exceeds 100 kW, the driving voltage may increase.
마지막으로 전자주입층 상부에 진공증착법이나 스퍼터링법 등의 방법을 이용하여 제2전극을 형성할 수 있다. 상기 제2전극은 캐소드(Cathode)로 사용될 수 있다. 상기 제2전극 형성용 금속으로는 낮은 일함수를 가지는 금속, 합금, 전기전도성 화합물 및 이들의 혼합물을 사용할 수 있다. 구체적인 예로서는 리튬(Li), 마그네슘(Mg), 알루미늄(Al), 알루미늄-리튬(Al-Li), 칼슘(Ca), 마그네슘-인듐(Mg-In), 마그네슘-은(Mg-Ag)등을 들 수 있다. 또한 전면 발광소자를 얻기 위하여 ITO, IZO를 사용한 투과형 캐소드를 사용할 수도 있다.Finally, the second electrode may be formed on the electron injection layer by using a vacuum deposition method or a sputtering method. The second electrode may be used as a cathode. As the metal for forming the second electrode, a metal, an alloy, an electrically conductive compound having a low work function, and a mixture thereof may be used. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. Can be mentioned. In addition, a transmissive cathode using ITO and IZO may be used to obtain the front light emitting device.
이하, 본 발명을 하기 실시예를 통하여 본 발명을 보다 상세하게 설명하고자 하나, 하기의 실시예는 단지 설명의 목적을 위한 것으로 본 발명을 제한하기 위한 것은 아니다. Hereinafter, the present invention will be described in more detail with reference to the following examples, but the following examples are for illustrative purposes only and are not intended to limit the present invention.
실시예 1Example 1
1) 3-(5-브로모-피리딘-3-일)-퀴놀린 [3-(5-Bromo-pyridin-3-yl)-quinoline] 의 합성1) Synthesis of 3- (5-Bromo-pyridin-3-yl) -quinoline [3- (5-Bromo-pyridin-3-yl) -quinoline]
아르곤 기체 하에서 100 ml 둥근 바닥 플라스크에 3,5-디브로모-피리딘 (3,5-Dibromo-pyridine) 1.11g (4.7mmol), 3-(4,4,5,5-테트라메틸-[1,3,2]디옥사보로란-2-일)-퀴놀린 [3-(4,4,5,5-Tetramethyl-[1,3,2] dioxaborolan -2-yl)-quinoline] 1.0 g (3.92mmol), 테트라키스(트리페닐포스핀)팔라듐(0) 0.45g, 2M K2CO3 7.84 ml, 테트라부틸암모늄브로마이드 1.26g를 넣고 THF와 톨루엔을 각각 30ml와 15ml 넣고 100℃에서 16시간 동안 환류시켰다. 용액의 색이 진한 갈색으로 변하는 것을 확인한 후 물을 첨가하고 클로로포름으로 추출하였다. 그 후 추출해 낸 유기층을 무수 황산마그네슘으로 건조시켜 여과하고 용매를 제거하고, 실리카겔 컬럼으로 분리하여 3-(5-브로모-피리딘-3-일)-퀴놀린 [3-(5-Bromo-pyridin-3-yl)-quinoline] 1.1g의 백색고체를 얻었고, LCMS(SHIMADZU, LCMS-IT-TOF)를 이용하여 대기압화학이온화(Atmospheric Pressure Chemical ionization)(APCI)법으로 측청한 결과, [M+H]+=285가 주된 피크로 얻어져 목적 화합물임을 확인하였다.1.11 g (4.7 mmol), 3- (4,4,5,5-tetramethyl- [1,3,5-Dibromo-pyridine) in a 100 ml round bottom flask under argon gas , 3,2] dioxaborolan-2-yl) -quinoline [3- (4,4,5,5-Tetramethyl- [1,3,2] dioxaborolan-2-yl) -quinoline] 1.0 g ( 3.92mmol), tetrakis (triphenylphosphine) palladium (0) 0.45g, 2M K2CO3 7.84ml, tetrabutylammonium bromide 1.26g were added, and 30ml and 15ml of THF and toluene were added and refluxed at 100 ° C for 16 hours. After confirming that the color of the solution turned dark brown, water was added and extracted with chloroform. The extracted organic layer was then dried over anhydrous magnesium sulfate, filtered, solvent removed, separated by silica gel column, 3- (5-bromo-pyridin-3-yl) -quinoline [3- (5-Bromo-pyridin- 3-yl) -quinoline] 1.1 g of a white solid was obtained, and measured by Atmospheric Pressure Chemical Ionization (APCI) method using LCMS (SHIMADZU, LCMS-IT-TOF), [M + H ] + = 285 was obtained as the main peak to confirm that it was the target compound.
2) 화학식 9의 화합물의 합성2) Synthesis of Compound of Formula 9
아르곤 기체 하에서 100 ml 둥근 바닥 플라스크에 3-(5-브로모-피리딘-3-일)-퀴놀린 0.61g (2.15mmol), 2-(9,10-디-나프탈렌-2-일-안트라센-2-일)-4,4,5,5-테트라메틸-[1,3,2]디옥사보란 [2-(9,10-Di-나프탈렌-2-yl-anthracen-2-yl)-4,4,5,5-tetramethyl-[1,3,2] dioxaborolane] 1.0 g (1.8mmol), 1M K3PO4 3.6ml, 디옥산 20ml 넣고 120℃에서 36시간 동안 환류시켰다. 상기 반응이 완료된 후, 반응 혼합물을 실온까지 냉각시키고, 톨루엔 100 ml와 증류수 100ml를 첨가하여 유기층을 추출했다. 모아진 유기층을 MgSO4로 건조시킨 후 농축하여, 실리카겔 컬럼 크로마토그래피를 실시하였다. 여기에서 얻은 용출액을 농축, 건조시켜 고체상태의 1.1g의 목적 화합물을 얻었고, LCMS를 이용하여 APCI법으로 측청한 결과, [M+H]+=635가 얻어져 목적 화합물임을 확인하였다.0.61 g (2.15 mmol) of 3- (5-bromo-pyridin-3-yl) -quinoline, 2- (9,10-di-naphthalen-2-yl-anthracene-2 in a 100 ml round bottom flask under argon gas -Yl) -4,4,5,5-tetramethyl- [1,3,2] dioxaborane [2- (9,10-Di-naphthalene-2-yl-anthracen-2-yl) -4, 4,5,5-tetramethyl- [1,3,2] dioxaborolane] 1.0 g (1.8 mmol), 3.6 ml of 1M K 3 PO 4 and 20 ml of dioxane were added and refluxed at 120 ° C. for 36 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and 100 ml of toluene and 100 ml of distilled water were added to extract the organic layer. The combined organic layers were dried over MgSO 4 , concentrated, and silica gel column chromatography was performed. The eluate thus obtained was concentrated and dried to obtain 1.1 g of the target compound in the solid state. As a result of the measurement using the APCI method using LCMS, [M + H] + = 635 was obtained to confirm that the target compound was obtained.
실시예 2Example 2
1) 3-(6-브로모-피리딘-3-일)-퀴놀린 [3-(5-Bromo-pyridin-3-yl)-quinoline] 의 합성1) Synthesis of 3- (6-Bromo-pyridin-3-yl) -quinoline [3- (5-Bromo-pyridin-3-yl) -quinoline]
아르곤 기체 하에서 100 ml 둥근 바닥 플라스크에 2,6-디브로모-피리딘 1.11g (4.7mmol), 3-(4,4,5,5-테트라메틸l-[1,3,2]디옥사보로란-2-일)-퀴놀린 1.0 g (3.92mmol), 테트라키스(트리페닐포스핀)팔라듐(0) 0.45g, 2M K2CO3 7.84 ml, 테트라부틸암모늄브로마이드 1.26g를 넣고 THF와 톨루엔을 각각 30ml와 15ml 넣고 100℃에서 16시간 동안 환류시켰다. 용액의 색이 진한 갈색으로 변하는 것을 확인한 후 물을 첨가하고 클로로포름으로 추출하였다. 그 후 추출해 낸 유기층을 무수 황산마그네슘으로 건조시켜 여과하고 용매를 제거하고, 실리카겔 컬럼으로 분리하여 3-(6-브로모-피리딘-2-일)-퀴놀린 0.8g의 백색고체를 얻었고, LCMS를 이용하여 APCI법으로 측청한 결과, [M+H]+=285가 얻어져 목적 화합물임을 확인하였다.1.11 g (4.7 mmol) 2,6-dibromo-pyridine, 3- (4,4,5,5-tetramethyll- [1,3,2] dioxabo, in a 100 ml round bottom flask under argon gas 1.0 g (3.92 mmol) of loran-2-yl) -quinoline, 0.45 g of tetrakis (triphenylphosphine) palladium (0), 7.84 ml of 2M K 2 CO 3 , 1.26 g of tetrabutylammonium bromide, and THF and toluene 30ml and 15ml were added and refluxed at 100 ° C. for 16 hours. After confirming that the color of the solution turned dark brown, water was added and extracted with chloroform. The extracted organic layer was then dried over anhydrous magnesium sulfate, filtered, solvent removed, and separated by silica gel column to obtain 0.8 g of a white solid of 3- (6-bromo-pyridin-2-yl) -quinoline, LCMS. As a result of checking by APCI method, [M + H] + = 285 was obtained, confirming that it was the target compound.
2) 화학식 10의 화합물의 합성2) Synthesis of Compound of
아르곤 기체 하에서 100 ml 둥근 바닥 플라스크에 3-(6-브로모-피리딘-2-일)-퀴놀린 0.6g (2.15mmol), 2-(9,10-디-나프탈렌-2-일-안트라센-2-일)-4,4,5,5-테트라메틸-[1,3,2]디옥사보로란 1.0 g (1.8mmol), 1M K3PO4 3.6ml, 디옥산 20ml 넣고 120℃에서 36시간 동안 환류시켰다. 상기 반응이 완료된 후, 반응 혼합물을 실온까지 냉각시키고, 톨루엔 100 ml와 증류수 100ml를 첨가하여 유기층을 추출했다. 모아진 유기층을 MgSO4로 건조시킨 후 농축하여, 실리카겔 컬럼 크로마토그래피를 실시하였다. 여기에서 얻은 용출액을 농축, 건조시켜 고체상태의 0.9g의 목적 화합물을 얻었고, LCMS를 이용하여 APCI법으로 측청한 결과, [M+H]+=635가 얻어져 목적 화합물임을 확인하였다.0.6 g (2.15 mmol) 3- (6-bromo-pyridin-2-yl) -quinoline, 2- (9,10-di-naphthalen-2-yl-anthracene-2 in a 100 ml round bottom flask under argon gas -Yl) -4,4,5,5-tetramethyl- [1,3,2] dioxaboloran 1.0 g (1.8mmol), 1M K 3 PO 4 3.6ml, 20ml dioxane and put at 120 ℃ 36 It was refluxed for hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and 100 ml of toluene and 100 ml of distilled water were added to extract the organic layer. The combined organic layers were dried over MgSO 4 , concentrated, and silica gel column chromatography was performed. The eluate thus obtained was concentrated and dried to obtain 0.9 g of the target compound in the solid state. The residue was measured by APCI method using LCMS. As a result, [M + H] + = 635 was obtained to confirm that the target compound was obtained.
실시예 3Example 3
1) 3-(5-브로모-피리딘-2-일)-퀴놀린의 합성1) Synthesis of 3- (5-bromo-pyridin-2-yl) -quinoline
아르곤 기체 하에서 100 ml 둥근 바닥 플라스크에 2,5-디브로모-피리딘 1.1g (4.7mmol), 3-(4,4,5,5-테트라메틸-[1,3,2]디옥사보로란-2-일)-퀴놀린 1.0 g (3.92mmol), 테트라키스(트리페닐포스핀)팔라듐(0) 0.45g, 2M K2CO3 7.84 ml, 테트라부틸암모늄브로마이드 1.26g를 넣고 THF와 톨루엔을 각각 30ml와 15ml 넣고 100 ℃에서 16시간 동안 환류시켰다. 용액의 색이 진한 갈색으로 변하는 것을 확인한 후 물을 첨가하고 클로로포름으로 추출하였다. 그 후 추출해 낸 유기층을 무수 황산마그네슘으로 건조시켜 여과하고 용매를 제거하고, 실리카겔 컬럼으로 분리하여 3-(5-브로모-피리딘-2-일)-퀴놀린 1.2g의 백색고체를 얻었고, LCMS를 이용하여 APCI법으로 측청한 결과, [M+H]+=285가 얻어져 목적 화합물임을 확인하였다. 1.1 g (4.7 mmol) 2,5-dibromo-pyridine, 3- (4,4,5,5-tetramethyl- [1,3,2] dioxaboro in a 100 ml round bottom flask under argon gas Lan-2-yl) -quinoline 1.0 g (3.92 mmol), tetrakis (triphenylphosphine) palladium (0) 0.45g, 2M K 2 CO 3 7.84 ml, tetrabutylammonium bromide 1.26g and THF and toluene 30ml and 15ml were added and refluxed at 100 ° C. for 16 hours. After confirming that the color of the solution turned dark brown, water was added and extracted with chloroform. The extracted organic layer was then dried over anhydrous magnesium sulfate, filtered, solvent removed, and separated by silica gel column to obtain 1.2 g of 3- (5-bromo-pyridin-2-yl) -quinoline white solid. As a result of checking by APCI method, [M + H] + = 285 was obtained, confirming that it was the target compound.
2) 화학식 11의 화합물의 합성2) Synthesis of Compound of Formula 11
아르곤 기체 하에서 100 ml 둥근 바닥 플라스크에 3-(5-브로모-피리딘-2-일)-퀴놀린 0.62g (2.15mmol), 2-(9,10-디-나프탈렌-2-일-안트라센-2-일)-4,4,5,5-테트라메틸-[1,3,2]디옥사보로란 1.0 g (1.8mmol), 1M K3PO4 3.6ml, 디옥산 20ml 넣고 120℃에서 36시간 동안 환류시켰다. 상기 반응이 완료된 후, 반응 혼합물을 실온까지 냉각시키고, 톨루엔 100 ml와 증류수 100ml를 첨가하여 유기층을 추출했다. 모아진 유기층을 MgSO4로 건조시킨 후 농축하여, 실리카겔 컬럼 크로마토그래피를 실시하였다. 여기에서 얻은 용출액을 농축, 건조시켜 고체상태의 1.1g의 목적 화합물을 얻었고, LCMS를 이용하여 APCI법으로 측청한 결과, [M+H]+=635가 얻어져 목적 화합물임을 확인하였고, LCMS결과를 도 2a에, 또한 TGA(thermo gravimetric anaysis) 및 DSC(differential scanning calorimetry)를 이용한 열분석(N2분위기, 온도구간 : 상온 ~ 600 ℃ (10℃ /min)-TGA, 상온에서 400℃ 까지-DSC, 팬 타입 (pan type) : Pt 팬 in 일회용 Al 팬 (TGA), 일회용 Al pan (DSC) )을 통해서 측정 한 결과, Td(℃) 및 Tg(℃)는 각각 467(℃)/163(℃)이었다. 이러한 상기 실시예 3에서 제조한 화학식 11의 화합물의 TGA(thermo gravimetric anaysis)의 특성 및 DSC(differential scanning calorimetry)의 특성을 도 2b 및 2c에 각각 나타내었다. 0.62 g (2.15 mmol) of 3- (5-bromo-pyridin-2-yl) -quinoline, 2- (9,10-di-naphthalen-2-yl-anthracene-2 in a 100 ml round bottom flask under argon gas -Yl) -4,4,5,5-tetramethyl- [1,3,2] dioxaboloran 1.0 g (1.8mmol), 1M K 3 PO 4 3.6ml, 20ml dioxane and put at 120 ℃ 36 It was refluxed for hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and 100 ml of toluene and 100 ml of distilled water were added to extract the organic layer. The combined organic layers were dried over MgSO 4 , concentrated, and silica gel column chromatography was performed. The eluate thus obtained was concentrated and dried to obtain 1.1 g of the target compound in the solid state. The residue was measured by APCI method using LCMS. As a result, [M + H] + = 635 was obtained. In FIG. 2A, thermal analysis (N 2 atmosphere, temperature range: normal temperature to 600 ° C. (10 ° C.) using TGA (thermo gravimetric anaysis) and DSC (differential scanning calorimetry) / min) -TGA, 400 ℃ at room temperature Up to -DSC, pan type: Pt pan in disposable Al pan (TGA), disposable Al pan (DSC)), Td (℃) and Tg (℃) are 467 (℃) / 163 (degree. C.). The properties of TGA (thermo gravimetric anaysis) and DSC (differential scanning calorimetry) of the compound of Formula 11 prepared in Example 3 are shown in FIGS. 2B and 2C, respectively.
실시예 4Example 4
1) 4-(5-브로모-피리딘-2-일)-이소퀴놀린의 합성1) Synthesis of 4- (5-bromo-pyridin-2-yl) -isoquinoline
실시예 1의 1)에서 3,5-디브로모-피리딘대신에 2,5-디브로모-피리딘을, 3-(4,4,5,5-테트라메틸-[1,3,2]디옥사보로란-2-일)-퀴놀린 대신에 4-(4,4,5,5-테트라메틸-[1,3,2]디옥사보로란-2-일)-이소퀴놀린을 사용하는 것을 제외하고는 동일한 방법을 사용하여 4-(5-브로모-피리딘-2-일)-이소퀴놀린을 합성하였고, LCMS를 이용하여 APCI법으로 측청한 결과, [M+H]+=285가 얻어져 목적 화합물임을 확인하였다.In Example 1 1), 2,5-dibromo-pyridine instead of 3,5-dibromo-pyridine, 3- (4,4,5,5-tetramethyl- [1,3,2] 4- (4,4,5,5-tetramethyl- [1,3,2] dioxaborolan-2-yl) -isoquinoline is used instead of dioxaborolan-2-yl) -quinoline 4- (5-Bromo-pyridin-2-yl) -isoquinoline was synthesized using the same method except for the following method, which was measured by APCI method using LCMS. [M + H] + = 285 Was obtained, confirming that it was a target compound.
2) 화학식 12의 화합물의 합성2) Synthesis of Compound of Formula 12
실시예 1의 2)에서 3-(5-브로모-피리딘-3-일)-퀴놀린 대신에 4-(5-브로모-피리딘-2-일)-이소퀴놀린을 사용하는 것을 동일한 방법을 사용하여 화학식 12의 화합물을 합성하였고, LCMS를 이용하여 APCI법으로 측청한 결과, [M+H]+=635가 얻어져 목적 화합물임을 확인하였다.In Example 1 2) using 4- (5-bromo-pyridin-2-yl) -isoquinoline instead of 3- (5-bromo-pyridin-3-yl) -quinoline using the same method The compound of Chemical Formula 12 was synthesized, and the residue was examined by APCI method using LCMS. As a result, [M + H] + = 635 was confirmed to be the target compound.
실시예 5Example 5
1) 4-(6-브로모-피리딘-2-일)-이소퀴놀린의 합성1) Synthesis of 4- (6-bromo-pyridin-2-yl) -isoquinoline
실시예 1의 1)에서 3,5-디브로모-피리딘대신에 2,6-디브로모-피리딘을, 3-(4,4,5,5-테트라메틸-[1,3,2]디옥사보로란-2-일)-퀴놀린대신에 4-(4,4,5,5-테트라 메틸-[1,3,2]디옥사보로란-2-일)-이소퀴놀린을 사용하는 것을 제외하고는 동일한 방법을 사용하여 4-(6-브로모-피리딘-2-일)-이소퀴놀린을 합성하였고, LCMS를 이용하여 APCI법으로 측청한 결과, [M+H]+=285가 얻어져 목적 화합물임을 확인하였다.2,6-dibromo-pyridine instead of 3,5-dibromo-pyridine in 1) of Example 1, 3- (4,4,5,5-tetramethyl- [1,3,2] Use of 4- (4,4,5,5-tetra methyl- [1,3,2] dioxaborolan-2-yl) -isoquinoline instead of dioxaborolan-2-yl) -quinoline 4- (6-Bromo-pyridin-2-yl) -isoquinoline was synthesized using the same method except for the following method, which was measured by APCI method using LCMS. [M + H] + = 285 Was obtained, confirming that it was a target compound.
2) 화학식 13의 화합물의 합성2) Synthesis of Compound of Formula 13
실시예 1의 2)에서 3-(5-브로모-피리딘-3-일)-퀴놀린 대신에 4-(6-브로모-피리딘-2-일)-이소퀴놀린 을 사용하는 것을 동일한 방법을 사용하여 화학식 13의 화합물을 합성하였고, LCMS를 이용하여 APCI법으로 측청한 결과, [M+H]+=635가 얻어져 목적 화합물임을 확인하였다.In Example 1 2) using 4- (6-bromo-pyridin-2-yl) -isoquinoline instead of 3- (5-bromo-pyridin-3-yl) -quinoline the same method was used The compound of Formula 13 was synthesized, and the resultant was examined by APCI method using LCMS. As a result, [M + H] + = 635 was obtained to confirm that the compound was the target compound.
실시예 6Example 6
1) 3-[5-(4-브로모-페닐)-피리딘-2-일]-퀴놀린의 합성1) Synthesis of 3- [5- (4-bromo-phenyl) -pyridin-2-yl] -quinoline
아르곤 기체 하에서 100 ml 둥근 바닥 플라스크에 3-[5-(4-브로모-페닐)-피리딘-2-일]-퀴놀린 1.0g (3.51mmol), 4-브로모페닐붕산 2.8 g (14mmol), 테트라키스(트리페닐포스핀)팔라듐(0) 0.4g, 2M K2CO3 7 ml, 테트라부틸암모늄브로마이드 1.2g를 넣고 THF와 톨루엔을 각각 30ml와 15ml 넣고 100℃에서 12시간 동안 환류시켰다. 반응 완결 후, 물을 첨가하고 클로로포름으로 추출하였다. 그 후 추출해 낸 유기층을 무수 황산마그네슘으로 건조시켜 여과하고 용매를 제거하고, 실리카겔 컬럼으로 분리하여 3-[5-(4-브로모-페닐)-피리딘-2-일]-퀴놀린 0.54g의 백색고체를 얻었다.1.0 g (3.51 mmol) of 3- [5- (4-bromo-phenyl) -pyridin-2-yl] -quinoline, 2.8 g (14 mmol) of 4-bromophenylboric acid in a 100 ml round bottom flask under argon gas, 0.4 g of tetrakis (triphenylphosphine) palladium (0), 7 ml of 2M K 2 CO 3 and 1.2 g of tetrabutylammonium bromide were added thereto, and 30 ml and 15 ml of THF and toluene were respectively added and refluxed at 100 ° C. for 12 hours. After completion of the reaction, water was added and extracted with chloroform. Then, the extracted organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed, and the residue was separated by a silica gel column to give 0.5 [4] white of 3- [5- (4-bromo-phenyl) -pyridin-2-yl] -quinoline. A solid was obtained.
2) 화학식 16의 화합물의 합성2) Synthesis of Compound of Formula 16
아르곤 기체 하에서 100 ml 둥근 바닥 플라스크에 3-[5-(4-브로모-페닐)-피리딘-2-일]-퀴놀린 0.5g (1.38mmol), 2-(9,10-디-나프탈렌-2-일-안트라센-2-일)-4,4,5,5-테트라메틸-[1,3,2]디옥사보로란 1.0 g (1.8mmol), 1M K3PO4 3.6ml, 디옥산 20ml 넣고 120℃에서 36시간 동안 환류시켰다. 상기 반응이 완료된 후, 반응 혼합물을 실온까지 냉각시키고, 톨루엔 100 ml와 증류수 100ml를 첨가하여 유기층을 추출했다. 모아진 유기층을 MgSO4로 건조시킨 후 농축하여, 실리카겔 컬럼 크로마토그래피를 실시하였다. 여기에서 얻은 용출액을 농축, 건조시켜 고체상태의 0.67g의 목적 화합물을 얻었고, LCMS를 이용하여 APCI법으로 측청한 결과, [M+H]+=710이 얻어져 목적 화합물임을 확인하였다.0.5 g (1.38 mmol), 2- (9,10-di-naphthalene-2, 3- [5- (4-bromo-phenyl) -pyridin-2-yl] -quinoline, in a 100 ml round bottom flask under argon gas -Yl-anthracene-2-yl) -4,4,5,5-tetramethyl- [1,3,2] dioxaboloran 1.0 g (1.8mmol), 1M K3PO4 3.6ml, dioxane 20ml and 120 It was refluxed at 36 ° C. for 36 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and 100 ml of toluene and 100 ml of distilled water were added to extract the organic layer. The combined organic layers were dried over MgSO 4 , concentrated, and silica gel column chromatography was performed. The eluate thus obtained was concentrated and dried to obtain 0.67 g of the target compound in the solid state. The residue was measured by APCI method using LCMS. As a result, [M + H] + = 710 was obtained to confirm that the target compound was obtained.
실시예Example
7 : 화학식 30의 화합물의 합성 7: Synthesis of Compound of
실시예 4의 2)에서 2-(9,10-디-나프탈렌-2-일-안트라센-2-일)-4,4,5,5-테트라메틸-[1,3,2]디옥사보로란 대신에 4,4,5,5-테트라메틸-2-(10-나프탈렌-2-일-안트라센-9-일)-[1,3,2]디옥사보로란 을 사용하는 것을 제외하고는 동일한 방법을 사용하여 화학식 30의 화합물을 합성하였다.2- (9,10-di-naphthalen-2-yl-anthracen-2-yl) -4,4,5,5-tetramethyl- [1,3,2] dioxabo in 2) of Example 4 Except using 4,4,5,5-tetramethyl-2- (10-naphthalen-2-yl-anthracene-9-yl)-[1,3,2] dioxaborolane instead of loran Then, the compound of
실시예Example 8 : 화학식 32의 화합물의 합성 8: Synthesis of Compound of Formula 32
실시예 3의 2)에서 2-(9,10-디-나프탈렌-2-일-안트라센-2-일)-4,4,5,5-테트라메틸-[1,3,2]디옥사보로란 대신에 4,4,5,5-테트라메틸-2-(10-나프탈렌-2-일-안트라센-9-일)-[1,3,2]디옥사보로란 을 사용하는 것을 제외하고는 동일한 방법을 사용하여 화학식 32의 화합물을 합성하였고, LCMS를 이용하여 APCI법으로 측청한 결 과, [M+H]+=509가 얻어져 목적 화합물임을 확인하였다.2- (9,10-di-naphthalen-2-yl-anthracen-2-yl) -4,4,5,5-tetramethyl- [1,3,2] dioxabolic in 2) of Example 3) Except using 4,4,5,5-tetramethyl-2- (10-naphthalen-2-yl-anthracene-9-yl)-[1,3,2] dioxaborolane instead of loran Then, the compound of Chemical Formula 32 was synthesized using the same method, and the result of having been measured by APCI method using LCMS, [M + H] + = 509 was obtained to confirm that the target compound.
실시예Example 9 : 화학식 42의 화합물의 합성 9: Synthesis of Compound of Formula 42
실시예 6의 2)에서 2-(9,10-디-나프탈렌-2-일-안트라센-2-일)-4,4,5,5-테트라메틸-[1,3,2]디옥사보로란 대신에 4,4,5,5-테트라메틸-2-(10-나프탈렌-2-일-안트라센-9-일)-[1,3,2]디옥사보로란 을 사용하는 것을 제외하고는 동일한 방법을 사용하여 화학식 42의 화합물을 합성하였고, LCMS를 이용하여 APCI법으로 측청한 결과, [M+H]+=585가 얻어져 목적 화합물임을 확인하였다.2- (9,10-di-naphthalen-2-yl-anthracen-2-yl) -4,4,5,5-tetramethyl- [1,3,2] dioxabo in 2) of Example 6 Except using 4,4,5,5-tetramethyl-2- (10-naphthalen-2-yl-anthracene-9-yl)-[1,3,2] dioxaborolane instead of loran Then, using the same method to synthesize a compound of formula 42, and by LCCI using APCI method as a result, [M + H] + = 585 was obtained to confirm that the target compound.
[화학식 51][Formula 51]
[화학식 52][Formula 52]
[화학식 53][Formula 53]
[화학식 54][Formula 54]
실시예 10: 유기 전계 발광 소자의 제조 및 평가Example 10 Fabrication and Evaluation of Organic Electroluminescent Device
실시예 1에서 제조된 화학식 9의 화합물을 전자수송층으로, 상기 화학식 51의 화합물을 정공주입층으로, 상기 화학식 52의 화합물을 정공수송층으로, 상기 화학식 53의 화합물과 화학식 54의 화합물을 각각 발광층의 호스트와 도펀트로 사용하여, 다음과 같은 구조를 갖는 유기 발광 소자를 제작하였다: ITO / 화학식 51의 화합물 (600Å)/화학식 52의 화합물 (300Å) / 화학식 53의 화합물 : 화학식 54의 화합물 (300Å) / 화학식 9의 화합물 (250Å) / LiF(6Å) / Al(1500Å).The compound of Formula 9 prepared in Example 1 is an electron transport layer, the compound of Formula 51 is a hole injection layer, the compound of Formula 52 is a hole transport layer, the compound of Formula 53 and the compound of Formula 54 are respectively Using a host and a dopant, an organic light emitting device was manufactured having the following structure: ITO / Compound 51 (600 ') / Compound 52 (300') / Compound 53: Compound 54 (300 ') / Compound of formula 9 (250 ') / LiF (6') / Al (1500 ').
애노드는 15Ω/cm2 (1000Å) ITO 유리 기판을 50mm x 50mm x 0.7mm크기로 잘라서 아세톤 이소프로필 알콜과 순수물 속에서 각 15분 동안 초음파 세정한 후, 30분 동안 UV 오존 세정하여 사용하였다. 상기 기판 상부에 상기 화학식 51의 화합물 (정공주입층), 화학식 52의 화합물 (정공수송층) 을 각각 진공증착하고, 화학식 53과 화학식 54의 화합물을 중량비 100:5의 비율로 진공증착하여 발광층을 형성하였다. 이 후, 상기 발광층 상부에 화학식 9의 화합물을 250Å의 두께로 진공증착하여 전자수송층을 형성하였다. 상기 전자수송층 상부에 LiF 6Å(전자주입층)과 Al 1500Å(캐소드)을 순차적으로 진공증착하여, 도 1a에 도시된 바와 같은 유기 발광 소자를 제조하였다. 이 소자에서 전압 6.1V에서 20 mA/cm2의 청색발광이 얻어지고, 이때의 발광효율 및 2000nit에서의 반감수명을 표 1에 나타내었다. The anode was cut into 50 mm x 50 mm x 0.7 mm sized 15 Ω / cm 2 (1000 Å) ITO glass substrate, sonicated for 15 minutes in acetone isopropyl alcohol and pure water, followed by UV ozone cleaning for 30 minutes. The compound of Formula 51 (hole injection layer) and the compound of Formula 52 (hole transport layer) were vacuum deposited on the substrate, and the compounds of Formula 53 and Formula 54 were vacuum deposited at a weight ratio of 100: 5 to form a light emitting layer. It was. Thereafter, the compound of Formula 9 was vacuum deposited to a thickness of 250 kPa on the emission layer to form an electron transport layer. LiF 6Å (electron injection layer) and Al 1500Å (cathode) were sequentially vacuum deposited on the electron transport layer to manufacture an organic light emitting device as shown in FIG. 1A. In this device, blue light emission of 20 mA / cm 2 was obtained at a voltage of 6.1 V, and the luminous efficiency at this time and the half-life of 2000 nits are shown in Table 1.
실시예 11 내지 18 : 유기 전계 발광 소자의 제조 및 평가Examples 11 to 18 Fabrication and Evaluation of Organic Electroluminescent Devices
실시예 10에서, 전자수송층으로서 실시예 1에서 제조된 화학식 9의 화합물 대신 실시예 2 내지 9에서 제조된 화합물을 각각 사용한 것을 제외하고는 상기 실시예 10과 동일한 방법으로 유기 발광 소자를 제조하였다. 이 소자에서 20mA/cm2의 정전류 구동시의 구동전압, 발광효율 및 2000nit에서의 반감수명을 표 1에 나타내었다. 특히, 본 발명의 실시예 12에서 제조된 유기 전계 발광 소자의 전류밀도-전압의 특성 및 전압-휘도의 특성을 도 3a 및 도 3b에 각각 나타내었다. In Example 10, an organic light emitting diode was manufactured according to the same method as Example 10 except for using the compounds prepared in Examples 2 to 9 instead of the compounds of formula 9 prepared in Example 1 as the electron transporting layer. Table 1 shows the driving voltage, luminous efficiency, and half-life at 2000 nits during constant current driving of 20 mA / cm 2 in this device. In particular, the characteristics of the current density-voltage and the voltage-luminance of the organic EL device manufactured in Example 12 of the present invention are shown in FIGS. 3A and 3B, respectively.
비교예 1: 유기 전계 발광 소자의 제조 및 평가Comparative Example 1: Fabrication and Evaluation of Organic Electroluminescent Device
실시예 10에서, 전자수송층으로서 실시예 1에서 제조된 화학식 9의 화합물 대신 Alq3를 사용한 것을 제외하고는 실시예 10과 동일한 방법으로 유기 발광 소자 를 제조하였다. 이 소자에서의 발광효율, 발광색, 휘도 및 수명을 표 1에 나타내었다. 이 소자에서 20 mA/cm2의 정전류구동시의 구동전압, 발광효율 및 2000nit에서의 반감수명을 표 1에 나타내었다. In Example 10, an organic light emitting device was manufactured in the same manner as in Example 10, except that Alq3 was used instead of the compound of Formula 9 prepared in Example 1 as the electron transport layer. The luminous efficiency, luminous color, luminance and lifetime in this device are shown in Table 1. Table 1 shows the driving voltage, luminous efficiency, and half life at 2000 nits when driving the constant current at 20 mA / cm 2 in this device.
이상의 실시예로부터 본 발명의 일 실시예에 따른 화합물은 낮은 구동전압과 높은 발광효율이 얻어졌으며, 이 결과로부터 비교예 1에서 전자수송층으로 사용된 화합물에 비해 전자주입과 전자이동도 특성이 훨씬 우수하다라는 것을 알 수 있었다. 또한, 본 발명의 일 실시예에 따른 화합물은 높은 유리전이온도로 인한 열적 안정성으로 인해, 이를 사용한 유기 전계 발광 소자에서 우수한 수명특성을 얻을 수 있었다.From the above examples, the compound according to the embodiment of the present invention has obtained a low driving voltage and high luminous efficiency, and from this result, the electron injection and electron mobility characteristics are much superior to the compound used as the electron transport layer in Comparative Example 1. I could see that. In addition, the compound according to an embodiment of the present invention was able to obtain excellent life characteristics in the organic electroluminescent device using the same due to the thermal stability due to the high glass transition temperature.
도 1a는 본 발명의 일 구현예에 따른 유기 전계 발광 소자의 구조를 개략적으로 나타낸 도면이다.1A is a view schematically illustrating a structure of an organic EL device according to an embodiment of the present invention.
도 1b는 본 발명의 다른 구현예에 따른 유기 전계 발광 소자의 구조를 개략적으로 나타낸 도면이다.1B is a view schematically showing a structure of an organic EL device according to another embodiment of the present invention.
도 2a는 본 발명의 실시예 3에서 제조한 화합물의 LCMS의 결과를 나타내는 그래프이다.2A is a graph showing the results of LCMS of the compound prepared in Example 3 of the present invention.
도 2b는 본 발명의 실시예 3에서 제조한 화합물의 TGA(thermo gravimetric anaysis)의 특성을 나타내는 그래프이다.Figure 2b is a graph showing the characteristics of the TGA (thermo gravimetric anaysis) of the compound prepared in Example 3 of the present invention.
도 2c는 본 발명의 실시예 3에서 제조한 화합물의 DSC(differential scanning calorimetry)의 특성을 나타내는 그래프이다.Figure 2c is a graph showing the characteristics of the differential scanning calorimetry (DSC) of the compound prepared in Example 3 of the present invention.
도 3a는 본 발명의 실시예 12에서 제조된 유기 전계 발광 소자의 전류밀도-전압의 특성을 나타내는 그래프이다.3A is a graph showing the characteristics of current density-voltage of the organic EL device manufactured in Example 12 of the present invention.
도 3b는 본 발명의 실시예 12에서 제조된 유기 전계 발광 소자의 전압-휘도의 특성을 나타내는 그래프이다3B is a graph showing characteristics of voltage-luminance of the organic EL device manufactured in Example 12 of the present invention.
Claims (11)
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WO2011037380A2 (en) * | 2009-09-22 | 2011-03-31 | 주식회사 두산 | Novel anthracene derivative and organic electroluminescent device using same |
WO2011037380A3 (en) * | 2009-09-22 | 2011-10-13 | 주식회사 두산 | Novel anthracene derivative and organic electroluminescent device using same |
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