KR20100119077A - New compounds and organic electronic device using the same - Google Patents
New compounds and organic electronic device using the same Download PDFInfo
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- KR20100119077A KR20100119077A KR1020090038001A KR20090038001A KR20100119077A KR 20100119077 A KR20100119077 A KR 20100119077A KR 1020090038001 A KR1020090038001 A KR 1020090038001A KR 20090038001 A KR20090038001 A KR 20090038001A KR 20100119077 A KR20100119077 A KR 20100119077A
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- South Korea
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 141
- 239000011368 organic material Substances 0.000 claims abstract description 37
- 239000000126 substance Substances 0.000 claims abstract description 31
- 125000003118 aryl group Chemical group 0.000 claims abstract description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
- 125000001769 aryl amino group Chemical group 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 239000010410 layer Substances 0.000 claims description 121
- 238000002347 injection Methods 0.000 claims description 38
- 239000007924 injection Substances 0.000 claims description 38
- -1 phosphoryl group Chemical group 0.000 claims description 30
- 230000005525 hole transport Effects 0.000 claims description 23
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000005264 aryl amine group Chemical group 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 125000004431 deuterium atom Chemical group 0.000 claims description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000005377 alkyl thioxy group Chemical group 0.000 claims description 3
- 125000005165 aryl thioxy group Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000012044 organic layer Substances 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims 1
- 150000001543 aryl boronic acids Chemical class 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 125000002560 nitrile group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 61
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical group [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 39
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 18
- 238000002474 experimental method Methods 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-UHFFFAOYSA-N 0.000 description 13
- 239000002019 doping agent Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000000151 deposition Methods 0.000 description 10
- 239000012153 distilled water Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- RDZVTJIEJKNVDG-UHFFFAOYSA-N C1=CC=C2C(=C1)C=C3C=CC=CC3=C2C4=CC=C(C5=CC=CC=C54)F Chemical compound C1=CC=C2C(=C1)C=C3C=CC=CC3=C2C4=CC=C(C5=CC=CC=C54)F RDZVTJIEJKNVDG-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
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- 230000008021 deposition Effects 0.000 description 5
- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 230000021615 conjugation Effects 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- XEKTVXADUPBFOA-UHFFFAOYSA-N 1-bromo-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(Br)C(F)=C1F XEKTVXADUPBFOA-UHFFFAOYSA-N 0.000 description 2
- SAODOTSIOILVSO-UHFFFAOYSA-N 2-(4-bromophenyl)naphthalene Chemical compound C1=CC(Br)=CC=C1C1=CC=C(C=CC=C2)C2=C1 SAODOTSIOILVSO-UHFFFAOYSA-N 0.000 description 2
- SYACRXBYRNYMLN-UHFFFAOYSA-N 9-bromo-10-naphthalen-1-ylanthracene Chemical compound C12=CC=CC=C2C(Br)=C(C=CC=C2)C2=C1C1=CC=CC2=CC=CC=C12 SYACRXBYRNYMLN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 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 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- BQHVXFQXTOIMQM-UHFFFAOYSA-N (4-naphthalen-1-ylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC2=CC=CC=C12 BQHVXFQXTOIMQM-UHFFFAOYSA-N 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 1
- YRPIGRRBBMFFBE-UHFFFAOYSA-N 1-(4-bromophenyl)naphthalene Chemical compound C1=CC(Br)=CC=C1C1=CC=CC2=CC=CC=C12 YRPIGRRBBMFFBE-UHFFFAOYSA-N 0.000 description 1
- UPFTWKGGLHJPJX-UHFFFAOYSA-N 1-N,2,4-triphenylbenzene-1,3-diamine Chemical group C1(=CC=CC=C1)NC1=C(C(=C(C=C1)C1=CC=CC=C1)N)C1=CC=CC=C1 UPFTWKGGLHJPJX-UHFFFAOYSA-N 0.000 description 1
- FMOZIATXSMLFJS-UHFFFAOYSA-N 1-[2-cyclohexyloxy-4-ethoxy-5-(2-methoxyphenoxy)-3-phenoxy-6-propan-2-yloxyphenoxy]naphthalene Chemical group COC1=C(C=CC=C1)OC1=C(C(=C(C(=C1OCC)OC1=CC=CC=C1)OC1CCCCC1)OC1=CC=CC2=CC=CC=C12)OC(C)C FMOZIATXSMLFJS-UHFFFAOYSA-N 0.000 description 1
- VAUJZKBFENPOCH-UHFFFAOYSA-N 1-bromo-4-fluoronaphthalene Chemical compound C1=CC=C2C(F)=CC=C(Br)C2=C1 VAUJZKBFENPOCH-UHFFFAOYSA-N 0.000 description 1
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 1
- NTYDMFCZXBCEJY-UHFFFAOYSA-N 1-methyl-2-phenylcyclohexa-2,4-dien-1-amine Chemical group CC1(N)CC=CC=C1C1=CC=CC=C1 NTYDMFCZXBCEJY-UHFFFAOYSA-N 0.000 description 1
- DSQMLISBVUTWJB-UHFFFAOYSA-N 2,6-diphenylaniline Chemical group NC1=C(C=2C=CC=CC=2)C=CC=C1C1=CC=CC=C1 DSQMLISBVUTWJB-UHFFFAOYSA-N 0.000 description 1
- WONYVCKUEUULQN-UHFFFAOYSA-N 2-methyl-n-(2-methylphenyl)aniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1C WONYVCKUEUULQN-UHFFFAOYSA-N 0.000 description 1
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical group CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
- MQFYUZCANYLWEI-UHFFFAOYSA-N 4-methylnaphthalen-1-amine Chemical group C1=CC=C2C(C)=CC=C(N)C2=C1 MQFYUZCANYLWEI-UHFFFAOYSA-N 0.000 description 1
- GYCNHFWRPJXTSB-UHFFFAOYSA-N 5-bromo-2-fluorobenzonitrile Chemical compound FC1=CC=C(Br)C=C1C#N GYCNHFWRPJXTSB-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- QXDWMAODKPOTKK-UHFFFAOYSA-N 9-methylanthracen-1-amine Chemical group C1=CC(N)=C2C(C)=C(C=CC=C3)C3=CC2=C1 QXDWMAODKPOTKK-UHFFFAOYSA-N 0.000 description 1
- NUIZJYUSWRJASQ-UHFFFAOYSA-N BrC1=C2C=CC=CC2=C(C2=CC=CC=C12)C1=C(C2=CC=CC=C2C=C1)F Chemical compound BrC1=C2C=CC=CC2=C(C2=CC=CC=C12)C1=C(C2=CC=CC=C2C=C1)F NUIZJYUSWRJASQ-UHFFFAOYSA-N 0.000 description 1
- OHKPCBXHHQBZPI-UHFFFAOYSA-N BrC1=CC=C(C=C1)C1=CC=C(C2=CC=CC=C12)F Chemical compound BrC1=CC=C(C=C1)C1=CC=C(C2=CC=CC=C12)F OHKPCBXHHQBZPI-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 1
- YFLBOAWYEYTIIL-UHFFFAOYSA-N CC(CC1)C(C)C(CC2)C12c(c-1cc2c(cc3)-c4c(cccc5)c5c(-c(cc5)ccc5-c5cc6ccccc6cc5)c5c4cc-1c(C)c5)cc2c3F Chemical compound CC(CC1)C(C)C(CC2)C12c(c-1cc2c(cc3)-c4c(cccc5)c5c(-c(cc5)ccc5-c5cc6ccccc6cc5)c5c4cc-1c(C)c5)cc2c3F YFLBOAWYEYTIIL-UHFFFAOYSA-N 0.000 description 1
- HZQKFYYOTDCEBK-UHFFFAOYSA-N COB(c(c1ccccc11)c(cccc2)c2c1-c(c1c2cccc1)ccc2F)O Chemical compound COB(c(c1ccccc11)c(cccc2)c2c1-c(c1c2cccc1)ccc2F)O HZQKFYYOTDCEBK-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
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- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical group C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
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- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
- C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed rings
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Abstract
Description
본 발명은 신규한 화합물 및 이를 이용한 유기 전자 소자에 관한 것이다.The present invention relates to a novel compound and an organic electronic device using the same.
본 명세서에서, 유기 전자 소자란 유기 반도체 물질을 이용한 전자 소자로서, 이러한 유기 전자 소자는 전극과 유기 반도체 물질 사이에서의 정공 및/또는 전자의 교류를 필요로 한다.In the present specification, an organic electronic device is an electronic device using an organic semiconductor material, which requires an exchange of holes and / or electrons between the electrode and the organic semiconductor material.
유기 전자 소자는 동작 원리에 따라 하기와 같이 크게 두 가지로 나눌 수 있다. 첫째는 외부의 광원으로부터 소자로 유입된 광자에 의하여 유기물층에서 엑시톤(exiton)이 형성되고, 이 엑시톤이 전자와 정공으로 분리되고, 이 전자와 정공이 각각 다른 전극으로 전달되어 전류원(전압원)으로 사용되는 형태의 전자 소자이다. 둘째는 2개 이상의 전극에 전압 또는 전류를 가하여 전극과 계면을 이루는 유기 반도체 물질층에 정공 및/또는 전자를 주입하고, 주입된 전자와 정공에 의하여 작동하는 형태의 전자소자이다.The organic electronic device can be divided into two types according to the operating principle. First, an exciton is formed in the organic layer by photons introduced into the device from an external light source, and the exciton is separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is an electronic device of the form. The second type is an electronic device in which holes and / or electrons are injected into the organic semiconductor material layer that interfaces with the electrodes by applying voltage or current to two or more electrodes, and is operated by the injected electrons and holes.
유기 전자 소자의 예로는 유기 발광 소자, 유기 태양 전지, 유기 감광체(OPC) 드럼, 유기 트랜지스터 등이 있으며, 이들은 모두 소자의 구동을 위하여 전자/정공 주입 물질, 전자/정공 추출 물질, 전자/정공 수송 물질 또는 발광 물질을 필요로 한다. 이하에서는 주로 유기 발광 소자에 대하여 구체적으로 설명하지만, 상기 유기 전자 소자들에서는 전자/정공 주입 물질, 전자/정공 추출 물질, 전자/정공 수송 물질 또는 발광 물질이 모두 유사한 원리로 작용한다.Examples of organic electronic devices include organic light emitting devices, organic solar cells, organic photoconductor (OPC) drums, and organic transistors, all of which are electron / hole injection materials, electron / hole extraction materials, and electron / hole transport materials for driving the devices. Materials or luminescent materials are required. Hereinafter, the organic light emitting device will be described in detail. However, in the organic electronic devices, an electron / hole injection material, an electron / hole extraction material, an electron / hole transport material, or a light emitting material may all operate on a similar principle.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기 에너지를 빛 에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 통상 양극과 음극 및 이들 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 주입층 등을 포함할 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층으로 주입되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 이러한 유기 발광 소자는 자발광, 고휘도, 고효율, 낮은 구동 전압, 넓은 시야각, 높은 콘트라스트, 고속 응답성 등의 특성을 갖는 것으로 알려져 있다.In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode and an organic material layer therebetween. In this case, the organic material layer is often formed of a multilayer structure composed of different materials to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet, and the excitons are at the bottom. When it falls to the state, it becomes light. Such organic light emitting devices are known to have characteristics such as self-luminous, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.
유기 발광 소자에서 유기물층으로 사용되는 재료는 기능에 따라, 발광 재료와 전하 수송 재료, 예컨대 정공 주입 재료, 정공 수송 재료, 전자 수송 재료, 전자 주입 재료 등으로 분류될 수 있다. 발광 재료는 발광색에 따라 청색, 녹색, 적색 발광 재료와 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료가 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 재료로서 호스트/도판트 계를 사용할 수 있다. 그 원리는 발광층을 주로 구성하는 호스트보다 에너지 대역 간극이 작고 발광 효율이 우수한 도판트를 발광층에 소량 혼합하면, 호스트에서 발생한 엑시톤이 도판트로 수송되어 효율이 높은 빛을 내는 것이다. 이때 호스트의 파장이 도판트의 파장대로 이동하므로, 이용하는 도판트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다.Materials used as the organic material layer in the organic light emitting device may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on their functions. The luminescent material includes blue, green, and red luminescent materials and yellow and orange luminescent materials necessary to realize better natural colors depending on the emission color. In addition, in order to increase luminous efficiency through increase in color purity and energy transfer, a host / dopant system may be used as the light emitting material. The principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to produce high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the desired wavelength light can be obtained depending on the type of the dopant used.
전술한 유기 발광 소자가 갖는 우수한 특징들을 충분히 발휘하기 위해서는 소자 내 유기물층을 이루는 물질, 예컨대 정공 주입 물질, 정공 수송 물질, 발광 물질, 전자 수송 물질, 전자 주입 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 하나, 아직까지 안정하고 효율적인 유기 발광 소자용 유기물층 재료의 개발이 충분히 이루어지지 않은 상태이며, 따라서 새로운 재료의 개발이 계속 요구되고 있다.In order to fully exhibit the excellent characteristics of the above-described organic light emitting device, a material forming the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material. Although this should be preceded, the development of a stable and efficient organic material layer for an organic light emitting device has not been sufficiently achieved, and therefore, the development of new materials is continuously required.
본 발명은 상기와 같은 종래 기술의 문제점을 해결하기 위한 것으로, 본 발명의 목적은 유기 전자 소자의 유기물층을 형성하는 경우 소자의 효율 상승, 구동 전압 하강 및 안정성 상승 등의 효과를 나타낼 수 있는 신규한 화합물을 제공하는 것이다.The present invention is to solve the problems of the prior art as described above, an object of the present invention when forming an organic material layer of an organic electronic device is a novel that can exhibit the effects of the efficiency of the device, the driving voltage drop and the stability increase To provide a compound.
본 발명의 또 다른 목적은 상기 화합물을 이용한 유기 전자 소자를 제공하는 것이다.Still another object of the present invention is to provide an organic electronic device using the compound.
상기 목적을 달성하기 위한 본 발명의 일 측면은 하기 화학식 1로 표시되는 화합물을 제공한다.One aspect of the present invention for achieving the above object provides a compound represented by the following formula (1).
[화학식 1][Formula 1]
상기 화학식 1에서,In Chemical Formula 1,
R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소 원자, 중수소 원자, 치환 또는 비치환된 C1~C30의 알킬기, 치환 또는 비치환된 C2~C12의 알케닐기, 치환 또는 비치환된 C3~C30의 시클로알킬기, 치환 또는 비치환된 C5~C20의 시클로알케닐 기, 치환 또는 비치환된 C6~C30의 아릴아미노기, 치환 또는 비치환된 C6~C30의 아릴기, 치환 또는 비치환되고 이종 원자로 O, N 또는 S를 갖는 C3~C30의 헤테로아릴기이고,R1 and R2 are the same as or different from each other, and each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 2 to C 12 alkenyl group, a substituted or unsubstituted A substituted C 3 to C 30 cycloalkyl group, a substituted or unsubstituted C 5 to C 20 cycloalkenyl group, a substituted or unsubstituted C 6 to C 30 arylamino group, a substituted or unsubstituted C 6 to C 30 Is an aryl group, a substituted or unsubstituted C 3 to C 30 heteroaryl group having O, N or S as a hetero atom,
Ar1 내지 Ar6는 서로 같거나 상이하고, 이중 하나 이상은 하기 화학식 2 또는 화학식 3으로 표시되는 치환기이며, 그 나머지는 각각 독립적으로 수소원자, 중수소 원자, 치환 또는 비치환된 C1~C30의 알킬기, 치환 또는 비치환된 C2~C12의 알케닐기, 치환 또는 비치환된 C3~C30의 시클로알킬기, 치환 또는 비치환된 C5~C20의 시클로알케닐기, 치환 또는 비치환된 C6~C30의 아릴아미노기, 치환 또는 비치환된 C6~C30의 아릴기 및 치환 또는 비치환되고 이종 원자로 O, N 또는 S를 갖는 C3~C30의 헤테로아릴기로 이루어진 군에서 선택되는 치환기이고,Ar 1 to Ar 6 are the same as or different from each other, at least one of them is a substituent represented by the following formula (2) or (3), the rest are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 ~ C 30 An alkyl group, a substituted or unsubstituted C 2 to C 12 alkenyl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, a substituted or unsubstituted C 5 to C 20 cycloalkenyl group, a substituted or unsubstituted C 6 ~ C 30 arylamino group, substituted or unsubstituted C 6 ~ C 30 aryl group and substituted or unsubstituted and C 3 ~ C 30 heteroaryl group having O, N or S in the heteroaryl group Is a substituent selected,
[화학식 2] [화학식 3] [Formula 2] [Formula 3]
상기 화학식 2 및 3에서,In Chemical Formulas 2 and 3,
n, p, 및 m은 0 내지 4의 정수이며, n과 p가 동시에 0은 아니고,n, p, and m are integers from 0 to 4, n and p are not 0 at the same time,
R3는 수소 원자, 중수소 원자, 치환 또는 비치환된 C1~C20의 알킬기, 치환 또 는 비치환된 C2~C20의 알케닐기, 치환 또는 비치환된 C3~C20의 시클로알킬기, 치환 또는 비치환된 C5~C30의 시클로알케닐기, 치환 또는 비치환된 C1~C30의 알콕시기, 치환 또는 비치환된 C6~C20의 아릴옥시기, 치환 또는 비치환된 C1~C30의 알킬티옥시기, 치환 또는 비치환된 C5~C20의 아릴티옥시기, 치환 또는 비치환된 C1~C30의 알킬아민기, 치환 또는 비치환된 C5~C30의 아릴아민기, 치환 또는 비치환된 C6~C30의 아릴기, 치환 또는 비치환되고 이종 원자로 O, N 또는 S를 갖는 C3~C30의 헤테로아릴기, 치환 또는 비치환된 붕소기, 치환 또는 비치환된 실란기, 카르보닐기, 포스포릴기, 아미노기, 니트릴기, 니트로기, 히드록시기, 할로겐기, 아미드기 및 에스테르기로 이루어진 군에서 선택되고, 상기 m이 2 이상의 정수인 경우에 상기 2 이상의 R3는 서로 동일하거나 상이할 수 있으며, 서로 인접하는 기와 지방족, 방향족, 지방족헤테로 또는 방향족헤테로의 축합 고리를 형성하거나 스피로 결합을 이룰 수 있다.R 3 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 3 -C 20 cycloalkyl group , Substituted or unsubstituted C 5 ~ C 30 cycloalkenyl group, substituted or unsubstituted C 1 ~ C 30 alkoxy group, substituted or unsubstituted C 6 ~ C 20 aryloxy group, substituted or unsubstituted C 1 ~ C 30 Alkylthioxy group, substituted or unsubstituted C 5 ~ C 20 Arylthioxy group, substituted or unsubstituted C 1 ~ C 30 Alkylamine group, substituted or unsubstituted C 5 ~ C 30 Arylamine group, substituted or unsubstituted C 6 ~ C 30 aryl group, substituted or unsubstituted C 3 ~ C 30 heteroaryl group having O, N or S as a hetero atom, substituted or unsubstituted boron group Substituted or unsubstituted silane, carbonyl, phosphoryl, amino, nitrile, nitro, hydroxy, halogen, amide and ester groups And when m is an integer of 2 or more, the two or more R 3 may be the same or different from each other, and may form a condensed ring of an aliphatic, aromatic, aliphatic hetero or aromatic hetero group with adjacent groups, or form a spiro bond. Can be achieved.
상기 목적을 달성하기 위한 본 발명의 두 번째 측면은 상기 화합물을 제조하는 방법을 제공한다.A second aspect of the present invention for achieving the above object provides a method for preparing the compound.
상기 목적을 달성하기 위한 본 발명의 세 번째 측면은 상기 화합물을 포함하는 유기전자소자를 제공한다.The third aspect of the present invention for achieving the above object provides an organic electronic device comprising the compound.
본 발명에 따른 신규한 화합물은 다양한 알킬기, 아릴기, 헤테로아릴기, 아릴아민기, 아릴카르보닐기, 아릴포스포릴기 등을 도입하여, 유기 발광 소자를 비롯 한 유기 전자 소자의 유기물층 재료로서 사용될 수 있다. 상기 본 발명에 따른 화합물을 유기물층의 재료로서 이용한 유기 발광 소자를 비롯한 유기 전자 소자는 효율, 구동전압, 수명 등에서 우수한 특성을 나타낸다.The novel compounds according to the present invention can be used as organic material layers of organic electronic devices including organic light emitting devices by introducing various alkyl groups, aryl groups, heteroaryl groups, arylamine groups, arylcarbonyl groups, arylphosphoryl groups, and the like. . The organic electronic device including the organic light emitting device using the compound according to the present invention as a material of the organic material layer exhibits excellent characteristics in efficiency, driving voltage, lifetime, and the like.
이하, 본 발명을 더욱 구체적으로 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명의 일 측면은, 상기 화학식 1로 표시되는 화합물에 관한 것이다.One aspect of the present invention relates to a compound represented by Chemical Formula 1.
본 발명에 따른 화합물에 있어서, 상기 화학식 1의 치환기들을 보다 구체적으로 설명하면 하기와 같다.In the compound according to the present invention, the substituents of Chemical Formula 1 will be described in more detail.
상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 12인 것이 바람직하다. 구체적인 예로는 메틸기, 에틸기, 프로필기, 이소프로필기, 부틸기, t-부틸기, 펜틸기, 헥실기, 헵틸기 등이 있으나, 이에만 한정되는 것은 아니다.The alkyl group may be straight or branched chain, carbon number is not particularly limited, but is preferably 1 to 12. Specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl, heptyl, and the like.
상기 알케닐기는 직쇄 또는 분지쇄일 수 있으며, 탄소수는 특별히 한정되지 않으나 2 내지 12인 것이 바람직하다. 구체적인 예로는 스틸베닐기(stylbenyl), 스티레닐기(styrenyl) 등의 아릴기가 연결된 알케닐기가 있으나, 이에만 한정되는 것은 아니다.The alkenyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 2 to 12. Specific examples thereof include alkenyl groups in which aryl groups such as stylbenyl and styrenyl are connected, but are not limited thereto.
상기 시클로알킬기는 탄소수 3 내지 12의 입체적 방해를 주지 않는 것이 바람직하다. 구체적인 예로는 시클로펜틸기, 시클로헥실기 등이 있으나, 이에만 한정되는 것은 아니다.It is preferable that the cycloalkyl group does not give a steric hindrance of 3 to 12 carbon atoms. Specific examples include a cyclopentyl group and a cyclohexyl group, but are not limited thereto.
상기 시클로알케닐기는 탄소수 3 내지 12인 것이 바람직하고, 보다 구체적으 로는 오각형 또는 육각형 고리 내에 에테닐렌을 갖는 고리 화합물 등을 들 수 있으나, 이에만 한정되는 것은 아니다.The cycloalkenyl group preferably has 3 to 12 carbon atoms, and more particularly, a cyclic compound having ethenylene in a pentagonal or hexagonal ring, and the like, but is not limited thereto.
상기 알콕시기는 탄소수 1 내지 12인 것이 바람직하고, 보다 구체적으로 메톡시, 에톡시, 페닐옥시, 시클로헥실옥시, 나프틸옥시, 이소프로필옥시, 디페닐옥시 등을 들 수 있으나, 이에만 한정되는 것은 아니다.The alkoxy group preferably has 1 to 12 carbon atoms, more specifically methoxy, ethoxy, phenyloxy, cyclohexyloxy, naphthyloxy, isopropyloxy, diphenyloxy, and the like, but is not limited thereto. It is not.
상기 치환 또는 비치환된 C5~C30의 아민기라 함은 독립적으로 -N(Z1)(Z2)의 형태로 Z1 및 Z2는 치환 비치환된 C1-C50알킬기, 치환 비치환된 C2-C50알케닐기, 치환 비치환된 C5-C50사이클로알킬기, 치환 비치환된 C5-C50사이클로알케닐기, 치환 비치환된 C5-C50 헤테로사이클로알킬기, 치환 비치환 C6-C50아릴기, 치환 비치환 C2-C50 헤테로아릴기 등이다.The substituted or unsubstituted C 5 ~ C 30 amine group is independently in the form of -N (Z 1) (Z 2) Z 1 and Z 2 is a substituted unsubstituted C 1 -C 50 alkyl group, substituted unsubstituted C 2 -C 50 alkenyl group, substituted unsubstituted C 5 -C 50 cycloalkyl group, substituted unsubstituted C 5 -C 50 cycloalkenyl group, substituted unsubstituted C 5 -C 50 heterocycloalkyl group, substituted unsubstituted C 6- C 50 aryl group, substituted unsubstituted C 2 -C 50 Heteroaryl group;
상기 아릴아민기에 있어서, 아릴기라 함은 탄소수 5 내지 30인 것이 바람직하고, 보다 구체적으로 디페닐아민기, 페닐나프틸아민기, 페닐비페닐아민기, 나프틸비페닐아민기, 디나프틸아민기, 디비페닐아민기, 디안트라세닐아민기, 3-메틸-페닐아민기, 4-메틸-나프틸아민기, 2-메틸-비페닐아민기, 9-메틸-안트라세닐아민기, 디톨릴 아민기, 페닐 톨릴 아민기, 트리페닐아미노페닐 아민기, 페닐 비페닐아미노 페닐 아민기, 나프틸 페닐아미노페닐 비페닐아민기 등을 들 수 있으나, 이에만 한정되는 것은 아니다.In the arylamine group, the aryl group preferably has 5 to 30 carbon atoms, and more specifically, a diphenylamine group, a phenylnaphthylamine group, a phenylbiphenylamine group, a naphthylbiphenylamine group, and a dinaphthylamine group. , Dibiphenylamine group, dianthracenylamine group, 3-methyl-phenylamine group, 4-methyl-naphthylamine group, 2-methyl-biphenylamine group, 9-methyl-anthracenylamine group, ditolyl amine Group, a phenyl tolyl amine group, a triphenylaminophenyl amine group, a phenyl biphenylamino phenyl amine group, a naphthyl phenylaminophenyl biphenylamine group, etc. are mentioned, but it is not limited to this.
상기 아릴기는 단환식 또는 다환식일 수 있고, 탄소수는 특별히 한정되지 않으나 6 내지 30인 것이 바람직하다. 단환식 아릴기의 예로는 페닐기, 바이페닐기, 터페닐기, 스틸벤 등을 들 수 있고, 다환식 아릴기의 예로는 나프틸기, 안트라세닐기, 페나트렌기, 파이레닐기, 페릴레닐기, 크라이세닐기 등을 들 수 있으나, 이에만 한정되는 것은 아니다.The aryl group may be monocyclic or polycyclic, and the carbon number is not particularly limited, but is preferably 6 to 30. Examples of the monocyclic aryl group include phenyl group, biphenyl group, terphenyl group, stilbene, and the like. Examples of the polycyclic aryl group include naphthyl group, anthracenyl group, phenanthrene group, pyrenyl group, perrylenyl group, and cryo. But may be exemplified, but is not limited thereto.
상기 헤테로아릴기는 이종 원자로 O, N 또는 S를 포함하는 고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 3 내지 30인 것이 바람직하다. 헤테로고리기의 예로는 카바졸기, 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 피라다진기, 퀴놀리닐기, 이소퀴놀린기, 아크리딜기 등을 들 수 있으나, 이에만 한정되는 것은 아니다.The heteroaryl group is a ring group containing O, N or S as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 3 to 30 carbon atoms. Examples of the heterocyclic group include a carbazole group, a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a pyridazine group, a quinolinyl group, an isoquinoline group , Acridil group and the like, but is not limited thereto.
상기 할로겐기로는 불소, 염소, 브롬, 요오드 등을 들 수 있으나, 이에만 한정되는 것은 아니다.Examples of the halogen group include fluorine, chlorine, bromine and iodine, but are not limited thereto.
상기 화학식 1의 Ar1 내지 Ar6, R1 및 R2에 치환될 수 있는 치환기로는 중수소, 할로겐 원자, 카르보닐기, 에스테르기, 포스포릴기, 이미드기, 아미노기, 니트로기, 시아노기, 히드록시기, 알킬기, 알콕시기, 아릴티옥시기, 알킬티옥시기, 알킬아민기, 아랄킬아민기, 아릴아민기, 알케닐기, 시클로알킬기, 시클로알케닐기, 실란기, 붕소기, C6~C30의 아릴기, C3~C30의 헤테로아릴기 등을 들 수 있으나, 이에만 한정되는 것은 아니다.Substituents which may be substituted with Ar 1 to Ar 6 , R 1 and R 2 of Formula 1 may include deuterium, a halogen atom, a carbonyl group, an ester group, a phosphoryl group, an imide group, an amino group, a nitro group, a cyano group, a hydroxy group, an alkyl group, Alkoxy group, arylthioxy group, alkylthioxy group, alkylamine group, aralkylamine group, arylamine group, alkenyl group, cycloalkyl group, cycloalkenyl group, silane group, boron group, C 6 ~ C 30 aryl group, C And a heteroaryl group of 3 to C 30 , but are not limited thereto.
본 발명에 따른 화합물에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 화학식 4 내지 화학식 7 중 하나로 표시될 수 있다.In the compound according to the present invention, the compound represented by Chemical Formula 1 may be represented by one of the following Chemical Formulas 4 to 7.
상기 화학식 4 내지 화학식 7에 있어서 R1, R2, Ar1, Ar2, Ar4, Ar5 및 Ar6은 상기 화학식 1에 대한 설명과 같다.In Formulas 4 to 7, R 1, R 2 , Ar 1 , Ar 2 , Ar 4 , Ar 5, and Ar 6 are the same as the descriptions of Formula 1 above.
상기 화학식 1로 표시되는 화합물이 상기 화학식 6으로 표시되는 경우에 있어서, 상기 Ar6은 상기 화학식 2 또는 상기 화학식 3으로 표시되는 경우, 상기 Ar4 는 치환 또는 비치환된 C1 ~ C20의 알킬기, 치환 또는 비치환된 C5 ~ C30의 아릴아미노기, 치환 또는 비치환된 C3 ~ C50의 헤테로아릴기, 치환 또는 비치환된 페닐기, 치환 또는 비치환된 F 내지 CN으로 치환된 C10~C50의 아릴기이다.When the compound represented by Formula 1 is represented by Formula 6, Ar 6 is represented by Formula 2 or Formula 3, Ar 4 Is a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 5 to C 30 arylamino group, a substituted or unsubstituted C 3 to C 50 heteroaryl group, a substituted or unsubstituted phenyl group, Or a C 10 to C 50 aryl group substituted with substituted or unsubstituted F to CN.
상기 화학식 4 내지 7에 있어서, Ar1, Ar2 및 Ar4는 각각 독립적으로 치환 또 는 비치환된 C1~C20의 알킬기, 치환 또는 비치환된 C2~C20의 알케닐기, 치환 또는 비치환된 C5~C30의 아릴아민기, 치환 또는 비치환된 C6~C30의 아릴기, 치환 또는 비치환되고 이종 원자로 O, N 또는 S를 갖는 C3~C30의 헤테로아릴기, 치환 또는 비치환된 붕소기, 치환 또는 비치환된 실란기 등인 것이 바람직하다.In Formulas 4 to 7, Ar 1 , Ar 2 and Ar 4 are each independently a substituted or unsubstituted C 1 ~ C 20 Alkyl group, a substituted or unsubstituted C 2 ~ C 20 Alkenyl group, a substituted or Unsubstituted C 5 to C 30 arylamine group, substituted or unsubstituted C 6 to C 30 aryl group, substituted or unsubstituted C 3 to C 30 heteroaryl group having O, N or S as a hetero atom , A substituted or unsubstituted boron group, a substituted or unsubstituted silane group, and the like.
상기 화학식 1로 표시되는 화합물의 바람직한 구체적인 예로는 하기 화합물들이 있으나, 이들에만 한정되는 것은 아니다.Preferred specific examples of the compound represented by Formula 1 include the following compounds, but are not limited thereto.
본 발명의 두 번째 측면은 상기 화학식 1로 표시되는 화합물의 제조방법에 관한 것이다.The second aspect of the present invention relates to a method for preparing the compound represented by Chemical Formula 1.
상기 화학식 1로 표시되는 화합물의 제조방법은 아릴보론산계 또는 아릴보로네이트계 화합물을 팔라듐(Pd) 촉매하에서 할로겐화 아릴 화합물과 스즈키 커플링(Suzuki coupling) 하여 상기 화학식 1을 제조하는 단계를 포함하는 것을 특징으로 한다.The method for preparing a compound represented by Chemical Formula 1 includes preparing an Chemical Formula 1 by suzuki coupling an arylboronic acid compound or an arylboronate compound with a halogenated aryl compound under a palladium (Pd) catalyst. It is characterized by.
University of Southern California의 Thomson은 사각평면구조를 갖는 Pt(II) 착물들의 흡수, 인광발광성 등을 조사하였다. 특히 짧은 파장의 인광 도펀트를 만들기 위해서 아릴기에 Fluoro 원자를 도입하여 청색도펀트를 얻었다.Thomson of the University of Southern California investigated the absorption and phosphorescence of Pt (II) complexes with rectangular planar structure. In particular, in order to make a phosphorescent dopant having a short wavelength, Fluoro atoms were introduced into an aryl group to obtain a blue dopant.
상기 ppy의 최대발광파장은 477 nm, 6Fppy의 최대발광파장은 468 nm, 46dfppy의 최대발광파장은 458 nm로 F원자의 도입으로 발광파장대가 단파장의 영역으로 이동(blue-shift)한다. 이에 본 발명은 F 원자의 영향으로 화합물의 밴드갭이 증가하는 성질을 이용하여 단파장의 청색 발광물질을 개발하고자 한 것이다. 그 결과, 상기 화학식 2와 상기 화학식 3으로 표시되는 화합물을 치환체로 갖는 상기 화학식 1로 표시되는 화합물들은 Fluoro 원자를 포함하지 않는 상기 화학식 1로 표시되는 화합물보다 단파장의 청색발광영역을 나타낼 수 있다.The maximum emission wavelength of ppy is 477 nm, the maximum emission wavelength of 6Fppy is 468 nm, and the maximum emission wavelength of 46 dfppy is 458 nm. The emission wavelength is shifted to the short wavelength region by introduction of F atoms (blue-shift). Accordingly, the present invention is to develop a short wavelength blue light emitting material by using the property of increasing the band gap of the compound under the influence of F atoms. As a result, the compounds represented by Chemical Formula 1 having the compounds represented by Chemical Formula 2 and Chemical Formula 3 as substituents may exhibit a shorter wavelength blue light emitting region than the compound represented by Chemical Formula 1 not containing a Fluoro atom.
상기 화학식 1로 표시되는 화합물은 상기 화학식 1에 표시된 코어 구조에 다양한 치환체를 도입함으로써 유기 발광 소자에서 사용되는 유기물층으로 사용되기에 적합한 특성을 가질 수 있다. 상기 화학식 1로 표시되는 화합물은 유기 발광 소자의 어느 층에 사용해도 특성을 나타낼 수 있으나, 특히 다음과 같은 특성을 나타낼 수 있다.The compound represented by Chemical Formula 1 may have properties suitable for use as an organic material layer used in an organic light emitting device by introducing various substituents into the core structure represented by Chemical Formula 1. The compound represented by Chemical Formula 1 may exhibit properties in any layer of the organic light emitting device, but may exhibit the following properties in particular.
치환 또는 비치환된 아릴아민기가 도입된 화합물들은 발광층, 정공 주입 및 정공 수송층 물질로 적합하며, N을 포함하는 헤테로 고리환 치환체가 도입된 경우 전자 주입, 전자 전달층 및 홀 저지층 물질로 적합하다.Compounds in which substituted or unsubstituted arylamine groups are introduced are suitable as light emitting layer, hole injection and hole transport layer materials, and when heterocyclic ring substituents containing N are introduced, they are suitable as electron injection, electron transport layer and hole blocking layer materials. .
화합물의 컨쥬게이션 길이와 에너지 밴드갭은 밀접한 관계가 있다. 구체적으로, 화합물의 컨쥬게이션 길이가 길수록 에너지 밴드갭이 작아진다. 전술한 바와 같이, 상기 화학식 1로 표시되는 화합물의 코어는 제한된 컨쥬게이션을 포함하고 있으므로, 이는 에너지 밴드갭이 작은 성질에서부터 큰 성질을 갖는다.The conjugation length of the compound and the energy bandgap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy bandgap. As described above, since the core of the compound represented by Chemical Formula 1 includes limited conjugation, it has a property from small to large energy bandgap.
또한, 상기와 같은 구조의 코어 구조에 다양한 치환기를 도입함으로써 도입된 치환기의 고유 특성을 갖는 화합물을 합성할 수 있다. 예컨대, 유기 발광 소자 제조시 사용되는 정공 주입층 물질, 정공 수송층 물질들은 HOMO(highest occupied molecular orbital)를 따라 정공을 전달해 줄 수 있을 만큼의 에너지 준위를 갖게 하며, 발광층으로부터 LUMO(lowest unoccupied molecular orbital)를 따라 넘어오는 전자를 막아 줄 정도의 에너지 준위를 가질 수 있는 화합물이 될 수 있다. 특히, 본 화합물의 코어 구조는 전자에 안정적인 특성을 보여 소자의 수명 향상에 기여할 수 있다. 발광층 및 전자 수송층 물질에 사용되도록 치환체들을 도입하여 이루어진 유도체들은 다양한 아릴아민계 도펀트, 아릴계 도펀트, 금속을 함유한 도펀트 등에 적당한 에너지 밴드갭을 갖도록 제조가 가능하다.Moreover, the compound which has the intrinsic property of the introduced substituent can be synthesize | combined by introducing various substituents into the core structure of the above structure. For example, the hole injection layer material and the hole transport layer material used in manufacturing the organic light emitting device have an energy level sufficient to transfer holes along the highest occupied molecular orbital (HOMO), and the low unoccupied molecular orbital (LUMO) from the light emitting layer. It can be a compound that can have an energy level enough to block the electrons coming along. In particular, the core structure of the compound exhibits stable properties to the electrons and may contribute to improving the life of the device. Derivatives made by introducing substituents to be used in the light emitting layer and the electron transport layer material may be manufactured to have an appropriate energy band gap in various arylamine dopants, aryl dopants, metal dopants, and the like.
또한, 상기 코어 구조에 다양한 치환기를 도입함으로써 에너지 밴드갭을 미세하게 조절이 가능하게 하며, 한편으로 유기물 사이에서의 계면에서의 특성을 향상되게 하며 물질의 용도를 다양하게 할 수 있다.In addition, by introducing a variety of substituents in the core structure it is possible to finely control the energy band gap, on the other hand to improve the properties at the interface between the organic material and to vary the use of the material.
한편, 상기 화학식 1로 표시되는 화합물은 유리 전이 온도(Tg)가 높아 열적 안정성이 우수하다. 이러한 열적 안정성의 증가는 소자에 구동 안정성을 제공하는 중요한 요인이 된다.On the other hand, the compound represented by Formula 1 has a high glass transition temperature (Tg) is excellent in thermal stability. This increase in thermal stability is an important factor in providing drive stability to the device.
본 발명의 세 번째 측면은 상기 화학식 1로 표시되는 화합물을 포함하는 유기전자소자에 관한 것이다.A third aspect of the present invention relates to an organic electronic device comprising the compound represented by the formula (1).
본 발명에 따른 유기 전자 소자는 제1 전극, 제2 전극, 및 상기 제1 전극과 제2 전극 사이에 배치된 1층 이상의 유기물층을 포함하는 유기 전자 소자로서, 상기 유기물층 중 1 층 이상은 상기 화학식 1의 화합물을 포함하는 것을 특징으로 한다.The organic electronic device according to the present invention is an organic electronic device including a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers is the chemical formula It is characterized by including the compound of 1.
본 발명의 유기 전자 소자는 전술한 화합물들을 이용하여 한 층 이상의 유기 물층을 형성하는 것을 제외하고는, 통상의 유기 전자 소자의 제조방법 및 재료에 의하여 제조될 수 있다.The organic electronic device of the present invention may be manufactured by a conventional method and material for manufacturing an organic electronic device, except that at least one organic water layer is formed using the above-described compounds.
상기 화학식 1의 화합물은 유기 전자 소자의 제조시 진공 증착법뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥 코팅, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.The compound of Chemical Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in manufacturing an organic electronic device. Here, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, roll coating and the like, but is not limited thereto.
본 발명의 유기 전자 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 전자 소자는 유기물층으로서 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 주입층 등을 포함하는 구조를 가질 수 있다. 그러나, 유기 전자 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기물층을 포함할 수 있다.The organic material layer of the organic electronic device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic electronic device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer. However, the structure of the organic electronic device is not limited thereto and may include a smaller number of organic material layers.
따라서, 본 발명의 유기 전자 소자에서, 상기 유기물층은 정공 주입층 및 정공 수송층을 포함할 수 있고, 이 정공 주입층 및 정공 수송층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.Therefore, in the organic electronic device of the present invention, the organic material layer may include a hole injection layer and a hole transport layer, the hole injection layer and the hole transport layer may include a compound represented by the formula (1).
또한, 상기 유기물층은 발광층을 포함할 수 있고, 이 발광층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.In addition, the organic material layer may include a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1.
이와 같은 다층 구조의 유기물층에서 상기 화학식 1의 화합물은 발광층, 정공 주입/정공 수송과 발광을 동시에 하는 층, 정공 수송과 발광을 동시에 하는 층, 또는 전자 수송과 발광을 동시에 하는 층 등에 포함될 수 있다.In the organic layer of the multilayer structure, the compound of Formula 1 may be included in a light emitting layer, a layer for simultaneously injecting / holes transporting and emitting light, a layer for simultaneously transporting holes and emitting light, or a layer for simultaneously transporting electrons and emitting light.
예컨대, 본 발명의 유기 발광 소자의 구조는 도 1 내지 도 4에 나타낸 것과 같은 구조를 가질 수 있으나, 이들에만 한정되는 것은 아니다.For example, the structure of the organic light emitting device of the present invention may have a structure as shown in Figs. 1 to 4, but is not limited thereto.
도 1에는 기판(101) 위에 양극(102), 발광층(105) 및 음극(107)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1의 화합물은 상기 발광층(105)에 포함될 수 있다.1 illustrates a structure of an organic light emitting device in which an anode 102, a light emitting layer 105, and a cathode 107 are sequentially stacked on a substrate 101. In such a structure, the compound of Formula 1 may be included in the light emitting layer 105.
도 2에는 기판(101) 위에 양극(102), 정공 주입/정공 수송 및 발광층(105), 전자 수송층(106) 및 음극(107)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1의 화합물은 정공 주입/정공 수송 및 발광층(105)에 포함될 수 있다.2 illustrates a structure of an organic light emitting device in which an anode 102, a hole injection / hole transport and light emitting layer 105, an electron transport layer 106, and a cathode 107 are sequentially stacked on a substrate 101. In such a structure, the compound of Formula 1 may be included in the hole injection / hole transport and the light emitting layer 105.
도 3에는 기판(101), 양극(102), 정공 주입층(103), 정공 수송 및 발광층(105), 전자 수송층(106) 및 음극(107)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1의 화합물은 정공 주입/정공 수송 및 발광층(105)에 포함될 수 있다.3 illustrates a structure of an organic light emitting device in which a substrate 101, an anode 102, a hole injection layer 103, a hole transport and emission layer 105, an electron transport layer 106, and a cathode 107 are sequentially stacked. It is. In such a structure, the compound of Formula 1 may be included in the hole injection / hole transport and the light emitting layer 105.
도 4에는 기판(101), 양극(102), 정공 주입층(103), 정공 수송층(104), 전자 수송 및 발광층(105) 및 음극(107)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1의 화합물은 전자 수송 및 발광층(105)에 포함될 수 있다.4 illustrates a structure of an organic light emitting device in which a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron transport and light emitting layer 105, and a cathode 107 are sequentially stacked. It is. In such a structure, the compound of Formula 1 may be included in the electron transport and emission layer 105.
예컨대, 본 발명에 따른 유기 발광 소자는 스퍼터링(sputtering)이나 전자빔 증발(e-beam evaporation)과 같은 PVD(physical vapor deposition) 방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수도 있다.For example, the organic light emitting device according to the present invention uses a metal vapor deposition (PVD) method such as sputtering or e-beam evaporation, and has a metal oxide or a metal oxide or an alloy thereof on a substrate. It can be prepared by depositing an anode to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
상기 유기물층은 정공 주입층, 정공 수송층, 발광층 및 전자 수송층 등을 포함하는 다층 구조일 수도 있으나, 이에 한정되지 않고 단층 구조일 수 있다. 또한, 상기 유기물층은 다양한 고분자 소재를 사용하여 증착법이 아닌 용매 공정(solvent process), 예컨대 스핀 코팅, 딥 코팅, 닥터 블레이딩, 스크린 프린팅, 잉크젯 프린팅 또는 열 전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다.The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic material layer may be formed by using a variety of polymer materials, and by using a method such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method, rather than a deposition method. It can be prepared in layers.
상기 양극 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 본 발명에서 사용될 수 있는 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO : Al 또는 SnO2 : Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸화합물의), 폴리[3,4-(에틸렌-1,2-디옥시)화합물의](PEDT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.As the anode material, a material having a large work function is usually preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methyl compound), poly [3,4- (ethylene-1,2-dioxy) compound] (PEDT), polypyrrole and polyaniline, and the like, but are not limited thereto.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으 나, 이들에만 한정되는 것은 아니다.It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
상기 정공 주입 물질로는 낮은 전압에서 양극으로부터 정공을 잘 주입받을 수 있는 물질로서, 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrine), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone) 계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리화합물의 계열의 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.The hole injection material is a material capable of well injecting holes from the anode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene-based organics, quinacridone-based organics, and perylene-based Organic compounds, anthraquinones and polyaniline and poly-compounds of conductive polymers, and the like, but are not limited thereto.
상기 정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다.As the hole transporting material, a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
상기 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 구체적인 예로는 8-히드록시-퀴놀린 알루미늄 착물(Alq3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다.The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
상기 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다.The electron transporting material is a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer. A material having high mobility to electrons is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
본 발명에 따른 화합물은 유기 태양 전지, 유기 감광체, 유기 트랜지스터 등을 비롯한 유기 전자 소자에서도 유기 발광 소자에 적용되는 것과 유사한 원리로 작용할 수 있다.The compound according to the present invention may also operate on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic solar cells, organic photoconductors, organic transistors, and the like.
따라서, 상기 유기 전자 소자는 유기 발광 소자, 유기 인광 소자, 유기 태양 전지, 유기 감광체(OPC) 및 유기 트랜지스터로 이루어진 군에서 선택될 수 있다.Therefore, the organic electronic device may be selected from the group consisting of an organic light emitting device, an organic phosphorescent device, an organic solar cell, an organic photoconductor (OPC), and an organic transistor.
이하, 실시예를 통하여 본 발명의 화학식 1로 표시되는 화합물들의 제조방법 및 이들을 이용한 유기 전자 소자의 제조방법 및 성능에 대하여 구체적으로 설명한다. 그러나, 하기 실시예는 설명을 위한 것이며, 본 발명의 범위가 하기 실시예에 의하여 한정되는 것은 아니다.Hereinafter, the method of preparing the compounds represented by Chemical Formula 1 of the present invention and the method and performance of the organic electronic device using the same will be described in detail through Examples. However, the following examples are for illustrative purposes, and the scope of the present invention is not limited by the following examples.
실시예에 있어서 평가 방법은 하기와 같다.In the Example, the evaluation method is as follows.
1. 구동전압: Kethley 236(source measure unit)을 사용하여 측정Drive voltage: measured using Kethley 236 (source measure unit)
2. 전류효율: SpectraScan Pr-650을 사용하여 측정2. Current efficiency: measured using SpectraScan Pr-650
3. 색좌표: SpectraScan Pr-650을 사용하여 측정3. Color coordinates: measured using SpectraScan Pr-650
본 발명에 따른 화학식 1로 표시되는 화합물은 일반적으로 다단계 화학 반응으로 제조될 수 있다. 즉, 일부 중간체 화합물이 먼저 제조되고, 그 중간체 화합물들로부터 화학식 1의 화합물이 제조된다. 예증적인 중간체 화합물들은 하기 합성예에 나타낸 화합물 1A, 1B, 1C, 2B, 2C, 3A, 3B, 3C, 4A, 4B와 같은 화합물들이다.The compound represented by Formula 1 according to the present invention may generally be prepared by a multistage chemical reaction. That is, some intermediate compounds are prepared first, and compounds of formula 1 are prepared from the intermediate compounds. Exemplary intermediate compounds are compounds such as compounds 1A, 1B, 1C, 2B, 2C, 3A, 3B, 3C, 4A, 4B shown in the following synthesis examples.
이하, 본 발명의 이해를 돕기 위하여 바람직한 실시예를 제시한다. 그러나, 하기의 실시예는 본 발명을 예시하기 위한 것이며, 이에 의하여 본 발명의 범위가 한정되는 것은 아니다.Hereinafter, preferred embodiments of the present invention will be described in order to facilitate understanding of the present invention. However, the following examples are intended to illustrate the invention, whereby the scope of the invention is not limited.
<< 제조예Production Example >>
<< 제조예Production Example 1> 화합물 1-1-1의 제조 1> Preparation of Compound 1-1-1
9-(naphthalen-5-yl)anthracen-10-yl-10-boronic acid(7.0 g, 20.0 mmol), 1-bromo-4-fluorobenzene(3.4 g, 20.0 mmol) 및 탄산나트륨(5.0 g, 35.9 mmol)을 테트라히드로퓨란(300 mL) 및 물(100 mL)의 혼합물 내 현탁시켰다. 테트라키스(트리페닐포스핀)팔라듐(0.4 g, 0.36 mmol)을 상기 현탁액에 가하였다. 혼합물을 환류에서 약 6시간 동안 교반한 다음 실온으로 냉각하였다. 생성된 용액을 추출하여 무수 황산마그네슘으로 건조한 후 용매를 증류하여 형성된 고체를 여과한 CH2Cl2/EtOH 로 정제하여 화합물 1-1-1(6.8 g, 수율 86%)을 제조하였다. MS : [M+H]+ = 3999- (naphthalen-5-yl) anthracen-10-yl-10-boronic acid (7.0 g, 20.0 mmol), 1-bromo-4-fluorobenzene (3.4 g, 20.0 mmol) and sodium carbonate (5.0 g, 35.9 mmol) Was suspended in a mixture of tetrahydrofuran (300 mL) and water (100 mL). Tetrakis (triphenylphosphine) palladium (0.4 g, 0.36 mmol) was added to the suspension. The mixture was stirred at reflux for about 6 hours and then cooled to room temperature. The resulting solution was extracted, dried over anhydrous magnesium sulfate, the solvent was distilled off and the solid formed was purified by filtered CH 2 Cl 2 / EtOH to prepare compound 1-1-1 (6.8 g, yield 86%). MS: [M + H] + = 399
<< 제조예Production Example 2> 화합물 1-1-5의 제조 2> Preparation of Compound 1-1-5
상기 제조예 1의 화합물 1-1-1의 제조예에 있어서, 1-bromo-4-fluorobenzene 대신에, 1-bromo-2,3,4,5,6-pentafluorobenzene(4.9 g, 20.0 mmol)을 사용한 것을 제외하고 동일한 방법으로 반응시켜 화합물 1-1-5(6.3 g, 수율 67%)을 제조하였다. MS : [M+H]+ =471In Preparation Example of Compound 1-1-1 of Preparation Example 1, instead of 1-bromo-4-fluorobenzene, 1-bromo-2,3,4,5,6-pentafluorobenzene (4.9 g, 20.0 mmol) was added. Compound 1-1-5 (6.3 g, yield 67%) was prepared by reacting in the same manner except using. MS: [M + H] + = 471
<< 제조예Production Example 3> 화합물 1-2-31의 제조 3> Preparation of Compound 1-2-31
상기 제조예 1의 화합물 1-1-1의 제조예에 있어서, 9-(naphthalen-5-yl)anthracen-10-yl-10-boronic acid 대신에 9-(1-fluoronaphthalen-4-yl)anthracen-10-yl-10-boronic acid(7.3 g, 20.0 mmol)을 사용하고, 1-bromo-4-fluorobenzene 대신에 1-bromo-2,3,4,5,6-pentafluorobenzene(4.9 g, 20.0 mmol)을 사용한 것을 제외하고 동일한 방법으로 반응시켜 화합물 1-2-31(8.0 g, 수율 82%)을 제조하였다. MS : [M+H]+ =489In the preparation of Compound 1-1-1 of Preparation Example 1, 9- (1-fluoronaphthalen-4-yl) anthracen instead of 9- (naphthalen-5-yl) anthracen-10-yl-10-boronic acid -10-yl-10-boronic acid (7.3 g, 20.0 mmol) was used, and 1-bromo-2,3,4,5,6-pentafluorobenzene (4.9 g, 20.0 mmol) instead of 1-bromo-4-fluorobenzene Reaction was carried out in the same manner except using) to prepare compound 1-2-31 (8.0 g, 82% yield). MS: [M + H] + = 489
<제조예 4> 화합물 1-2-9의 제조 Preparation Example 4 Preparation of Compound 1-2-9
상기 제조예 1의 화합물 1-1-1의 제조예에 있어서, 9-(naphthalen-5-yl)anthracen-10-yl-10-boronic acid 대신에 9-(1-fluoronaphthalen-4-yl)anthracen-10-yl-10-boronic acid(7.3g, 20.0 mmol)을 사용하고, 1-bromo-4-fluorobenzene 대신에 1-(4-bromophenyl)naphthalene(5.7 g, 20.0 mmol)을 사용한 것을 제외하고 동일한 방법으로 반응시켜 화합물 1-2-9(6.9 g, 수율 66%)을 제조하였다. MS : [M+H]+ =525In the preparation of Compound 1-1-1 of Preparation Example 1, 9- (1-fluoronaphthalen-4-yl) anthracen instead of 9- (naphthalen-5-yl) anthracen-10-yl-10-boronic acid -10-yl-10-boronic acid (7.3 g, 20.0 mmol) was used and the same except 1- (4-bromophenyl) naphthalene (5.7 g, 20.0 mmol) was used instead of 1-bromo-4-fluorobenzene. Reaction was carried out to prepare a compound 1-2-9 (6.9 g, yield 66%). MS: [M + H] + = 525
<< 제조예Production Example 5> 화합물 1-2-11의 제조 5> Preparation of Compound 1-2-11
상기 제조예 1의 화합물 1-1-1의 제조예에 있어서, 9-(naphthalen-5-yl)anthracen-10-yl-10-boronic acid 대신에 9-(1-fluoronaphthalen-4- yl)anthracen-10-yl-10-boronic acid(7.3 g, 20.0 mmol)를 사용하고, 1-bromo-4-fluorobenzene 대신에 2-(4-bromophenyl)naphthalene(5.7 g, 20.0 mmol)을 사용한 것을 제외하고 동일한 방법으로 반응시켜 화합물 1-2-11(6.9 g, 수율 66%)를 제조하였다. MS : [M+H]+ =525In Preparation Example 1-1 of the compound of Preparation Example 1, 9- (1-fluoronaphthalen-4-yl) anthracen instead of 9- (naphthalen-5-yl) anthracen-10-yl-10-boronic acid -10-yl-10-boronic acid (7.3 g, 20.0 mmol) was used and the same except that 2- (4-bromophenyl) naphthalene (5.7 g, 20.0 mmol) was used instead of 1-bromo-4-fluorobenzene. Reaction was carried out to prepare compound 1-2-11 (6.9 g, 66% yield). MS: [M + H] + = 525
<< 제조예Production Example 6> 화합물 1-2-43의 제조 6> Preparation of Compound 1-2-43
상기 제조예 1의 화합물 1-1-1의 제조예에 있어서, 9-(naphthalen-5-yl)anthracen-10-yl-10-boronic acid 대신에 9-(1-fluoronaphthalen-4-yl)anthracen-10-yl-10-boronic acid(7.3 g, 20.0 mmol)를 사용하고, 1-bromo-4-fluorobenzene 대신에 1-(4-bromophenyl)-4-fluoronaphthalene(6.0 g, 20.0 mmol)을 사용한 것을 제외하고 동일한 방법으로 반응시켜 화합물 1-2-43(8.5 g, 수율 78%)를 제조하였다. MS : [M+H]+ =543In the preparation of Compound 1-1-1 of Preparation Example 1, 9- (1-fluoronaphthalen-4-yl) anthracen instead of 9- (naphthalen-5-yl) anthracen-10-yl-10-boronic acid -10-yl-10-boronic acid (7.3 g, 20.0 mmol) was used, and 1- (4-bromophenyl) -4-fluoronaphthalene (6.0 g, 20.0 mmol) was used instead of 1-bromo-4-fluorobenzene. Except for the reaction in the same manner to give the compound 1-2-43 (8.5 g, yield 78%). MS: [M + H] + = 543
<< 제조예Production Example 7> 화합물 1-2-49의 제조 7> Preparation of Compound 1-2-49
상기 제조예 1의 화합물 1-1-1의 제조예에 있어서, 9-(naphthalen-5-yl)anthracen-10-yl-10-boronic acid 대신에 9-(1-fluoronaphthalen-4-yl)anthracen-10-yl-10-boronic acid(17.7 g, 44.0 mmol)를 사용하고, 1-bromo-4-fluorobenzene 대신에 4,4,5,5-tetramethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,2-dioxaborolane(6.6 g, 20.0 mmol)을 사용한 것을 제외하고 동일한 방법으로 반응시켜 화합물 1-2-49(8.5 g, 수율 78%)를 제조하였다. MS : [M+H]+ =543In the preparation of Compound 1-1-1 of Preparation Example 1, 9- (1-fluoronaphthalen-4-yl) anthracen instead of 9- (naphthalen-5-yl) anthracen-10-yl-10-boronic acid -10-yl-10-boronic acid (17.7 g, 44.0 mmol) was used, and 4,4,5,5-tetramethyl-2- (4- (4,4,5) instead of 1-bromo-4-fluorobenzene , 5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,2-dioxaborolane (6.6 g, 20.0 mmol) was reacted in the same manner except using the compound 1-2-49 (8.5 g, yield 78%) was prepared. MS: [M + H] + = 543
<< 제조예Production Example 8> 화합물 1-3-11의 제조 8> Preparation of Compound 1-3-11
상기 제조예 1의 화합물 1-1-1의 제조예에 있어서, 9-(naphthalen-5-yl)anthracen-10-yl-10-boronic acid 대신에 4-(naphthalen-1-yl)phenylboronic acid(5.0 g, 20.0 mmol)를 사용하고, 1-bromo-4-fluorobenzene 대신에 10-bromo-9-(1-fluoronaphthalen-2-yl)anthracene(8.0 g, 20.0 mmol)을 사용한 것을 제외하고 동일한 방법으로 반응시켜 화합물 1-3-11(5.1 g, 수율 49%)를 제조하였다. MS : [M+H]+ =525In Preparation Example of Compound 1-1-1 of Preparation Example 1, instead of 9- (naphthalen-5-yl) anthracen-10-yl-10-boronic acid, 4- (naphthalen-1-yl) phenylboronic acid ( 5.0 g, 20.0 mmol) and 10-bromo-9- (1-fluoronaphthalen-2-yl) anthracene (8.0 g, 20.0 mmol) instead of 1-bromo-4-fluorobenzene The reaction was conducted to prepare compound 1-3-11 (5.1 g, 49% yield). MS: [M + H] + = 525
<< 제조예Production Example 9> 화합물 1-2-3의 제조 9> Preparation of Compound 1-2-3
상기 제조예 1의 화합물 1-1-1의 제조예에 있어서, 9-(naphthalen-5-yl)anthracen-10-yl-10-boronic acid 대신에 9-(phenanthren-10-yl)anthracen-10-yl-10-boronic acid(8.0 g, 20.0 mmol)를 사용하고, 1-bromo-4-fluorobenzene 대신에 1-bromo-4-fluoronaphthalene(4.5 g, 20.0 mmol)을 사용한 것을 제외하고 동일한 방법으로 반응시켜 화합물 1-2-3(8.3 g, 수율 91%)를 제조하였다. MS : [M+H]+ =499In Preparation Example of Compound 1-1-1 of Preparation Example 1, 9- (phenanthren-10-yl) anthracen-10 instead of 9- (naphthalen-5-yl) anthracen-10-yl-10-boronic acid Reaction was carried out in the same manner except that -yl-10-boronic acid (8.0 g, 20.0 mmol) was used and 1-bromo-4-fluoronaphthalene (4.5 g, 20.0 mmol) was used instead of 1-bromo-4-fluorobenzene. Compound 1-2-3 (8.3 g, yield 91%) was prepared. MS: [M + H] + = 499
<< 제조예Production Example 10> 화합물 1-5-25의 제조 10> Preparation of Compound 1-5-25
상기 제조예 1의 화합물 1-1-1의 제조예에 있어서, 9-(naphthalen-5-yl)anthracen-10-yl-10-boronic acid 대신에 1-(phenanthren-9-yl)anthracen-10-yl-10-boronic acid(7.9 g, 20.0 mmol)를 사용하고, 1-bromo-4-fluorobenzene 대신에 5-bromo-2-fluorobenzonitrile(4.0 g, 20.0 mmol)을 사용한 것을 제외하고 동일한 방법으로 반응시켜 화합물 1-5-25(5.6 g, 수율 59%)를 제조하였다. MS : [M+H]+ =474In the preparation of Compound 1-1-1 of Preparation Example 1, 1- (phenanthren-9-yl) anthracen-10 instead of 9- (naphthalen-5-yl) anthracen-10-yl-10-boronic acid Reaction was carried out in the same manner except that -yl-10-boronic acid (7.9 g, 20.0 mmol) was used and 5-bromo-2-fluorobenzonitrile (4.0 g, 20.0 mmol) was used instead of 1-bromo-4-fluorobenzene. Compound 1-5-25 (5.6 g, 59% yield) was prepared. MS: [M + H] + = 474
<< 제조예Production Example 11> 화합물 1-1-162의 제조 11> Preparation of Compound 1-1-162
상기 제조예 1의 화합물 1-1-1의 제조예에 있어서, 9-(naphthalen-5-yl)anthracen-10-yl-10-boronic acid 대신에 4-(9-(naphthalene-5-yl)anthracen-10-yl)-2-fluorophenyl-1-pinacole boronic acid(10.5 g, 20.0 mmol)를 사용하고, 1-bromo-4-fluorobenzene 대신에 1-bromonaphthalene(4.1 g, 20.0 mmol)을 사용한 것을 제외하고 동일한 방법으로 반응시켜 화합물 1-1-162(6.3 g, 수율 59%)를 제조하였다. MS : [M+H]+ =525In Preparation Example of Compound 1-1-1 of Preparation Example 1, 4- (9- (naphthalene-5-yl) instead of 9- (naphthalen-5-yl) anthracen-10-yl-10-boronic acid except that anthracen-10-yl) -2-fluorophenyl-1-pinacole boronic acid (10.5 g, 20.0 mmol) was used and 1-bromonaphthalene (4.1 g, 20.0 mmol) was used instead of 1-bromo-4-fluorobenzene. And reacted in the same manner to give compound 1-1-162 (6.3 g, 59% yield). MS: [M + H] + = 525
<< 제조예Production Example 12> 화합물 1-1-173의 제조 12> Preparation of Compound 1-1-173
상기 제조예 1의 화합물 1-1-1의 제조예에 있어서, 9-(naphthalen-5-yl)anthracen-10-yl-10-boronic acid 대신에 4-(naphthalene-5-yl)-fluorophenyl-1-pinacole boronic acid(7.0 g, 20.0 mmol)를 사용하고, 1-bromo-4-fluorobenzene 대신에 9-(naphthalene-5-yl)-10-bromoanthracene(7.7 g, 20.0 mmol)을 사용한 것을 제외하고 동일한 방법으로 반응시켜 화합물 1-1-173(6.8 g, 수율 65%)를 제조하였다. MS : [M+H]+ =525 In Preparation Example of Compound 1-1-1 of Preparation Example 1, 4- (naphthalene-5-yl) -fluorophenyl- instead of 9- (naphthalen-5-yl) anthracen-10-yl-10-boronic acid Except for using 1-pinacole boronic acid (7.0 g, 20.0 mmol) and 9- (naphthalene-5-yl) -10-bromoanthracene (7.7 g, 20.0 mmol) instead of 1-bromo-4-fluorobenzene Reaction was carried out in the same manner to obtain Compound 1-1-173 (6.8 g, 65% yield). MS: [M + H] + = 525
<< 제조예Production Example 13> 화합물 1-1-177의 제조 13> Preparation of Compound 1-1-177
상기 제조예 1의 화합물 1-1-1의 제조예에 있어서, 9-(naphthalen-5-yl)anthracen-10-yl-10-boronic acid 대신에 4-(5-methylthiophen-2-yl)-2-fluorophenyl-1-pinacole boronic acid(6.4 g, 20.0 mmol)를 사용하고, 1-bromo-4-fluorobenzene 대신에 9-(naphthalene-5-yl)-10-bromoanthracene(7.7 g, 20.0 mmol)을 사용한 것을 제외하고 동일한 방법으로 반응시켜 화합물 1-1-177(6.7 g, 수율 68%)를 제조하였다. MS : [M+H]+ =495In Preparation Example 1-1 of the compound of Preparation Example 1, 4- (5-methylthiophen-2-yl)-instead of 9- (naphthalen-5-yl) anthracen-10-yl-10-boronic acid 2-fluorophenyl-1-pinacole boronic acid (6.4 g, 20.0 mmol) was used, and 9- (naphthalene-5-yl) -10-bromoanthracene (7.7 g, 20.0 mmol) was used instead of 1-bromo-4-fluorobenzene. Compound 1-1-177 (6.7 g, yield 68%) was prepared by reacting in the same manner except using. MS: [M + H] + = 495
<< 비교예Comparative example 1-1> 1-1>
ITO(indium tin oxide)가 1,500 Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이때, 세제로는 피셔(Fischer Co.) 사의 제품을 사용하였으며, 증류수로는 밀리포어(Millipore Co.) 사 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다.The glass substrate coated with ITO (indium tin oxide) at a thickness of 1,500 kPa was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, a product of Fischer Co. was used as a detergent, and distilled water filtered secondly as a filter of Millipore Co. was used as distilled water. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. The substrate was cleaned for 5 minutes using an oxygen plasma and then transferred to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에 헥사니트릴 헥사아자트리페닐렌(hexanitrile hexaazatriphenylene)를 500 Å의 두께로 열 진공 증착하여 정공 주입층을 형성하였다. 그 위에 정공을 수송하는 물질인 NPB(400 Å)를 진공증착한 후 발광층으로 호스트 H1과 도판트 D1 화합물을 300 Å의 두께로 진공 증착하였다.Hexanitrile hexaazatriphenylene was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a hole injection layer. NPB (400 kPa), which is a material for transporting holes, was vacuum deposited thereon, and the host H1 and the dopant D1 compound were vacuum deposited to a thickness of 300 kPa as a light emitting layer.
[헥사니트릴 헥사아자트리페닐렌] [NPB][Hexanitrile hexaazatriphenylene] [NPB]
상기 발광층 위에 화합물 E1를 200 Å 두께로 진공증착하여 전자 주입 및 수송층을 형성하였다. 상기 전자 주입 및 수송층 위에 순차적으로 12 Å 두께의 리튬 플루라이드(LiF)와 2,000 Å 두께의 알루미늄을 증착하여 음극을 형성하였다. 상기의 과정에서 유기물의 증착속도는 1 Å/sec를 유지하였고, 리튬플루라이드는 0.2 Å/sec, 알루미늄은 3 ~ 7 Å/sec의 증착속도를 유지하였다.Compound E1 was vacuum deposited to a thickness of 200 kPa on the light emitting layer to form an electron injection and transport layer. A cathode was formed by sequentially depositing 12 라이드 thick lithium fluoride (LiF) and 2,000 Å thick aluminum on the electron injection and transport layer. In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, the lithium fluoride was 0.2 Å / sec, and the aluminum was maintained at a deposition rate of 3 to 7 Å / sec.
<< 비교예Comparative example 1-2> 1-2>
상기 비교예 1-1에서 화합물 [H1] 대신 상기 화합물 [H2]를 사용한 것을 제외하고는 동일하게 실험하였다.The same experiment was conducted except that the compound [H2] was used instead of the compound [H1] in Comparative Example 1-1.
<< 비교예Comparative example 1-3> 1-3>
상기 비교예 1-1에서 화합물 [H1] 대신 상기 화합물 [H3]를 사용한 것을 제외하고는 동일하게 실험하였다.The same experiment was conducted except that the compound [H3] was used instead of the compound [H1] in Comparative Example 1-1.
<< 실험예Experimental Example 1-1> 1-1>
ITO(indium tin oxide)가 1,500 Å 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이때, 세제로는 피셔(Fischer Co.) 사의 제품을 사용하였으며, 증류수로는 밀리포어(Millipore Co.) 사 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다.A glass substrate coated with ITO (indium tin oxide) having a thickness of 1,500 Å was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, a product of Fischer Co. was used as a detergent, and distilled water filtered secondly as a filter of Millipore Co. was used as distilled water. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. The substrate was cleaned for 5 minutes using an oxygen plasma and then transferred to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에 헥사니트릴 헥사아자트리페닐렌(hexanitrile hexaazatriphenylene)을 500 Å 두께로 열 진공 증착하여 정공 주입층을 형성하였다. 그 위에 정공을 수송하는 물질인 NPB(400 Å)를 진공증착한 후 발광층으로 상기 제조예 1에서 제조한 화합물 1-1-1을 호스트로 화합물을 300 Å 두께로 진공 증착하고 도판트 D1을 도핑하였다. 상기 발광층 위에 상기 E1을 200 Å 두께로 진공증착하여 전자 주입 및 수송층을 형성하였다. 상기 전자 수송층 위에 순차적으로 12 Å 두께의 리튬 플루라이드(LiF)와 2,000 Å 두께의 알루미늄을 증착하여 음극을 형성하고 유기 발광 소자를 제조하였다.Hexanitrile hexaazatriphenylene was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a hole injection layer. NPB (400 kPa), which is a material for transporting holes, was vacuum-deposited, and then compound 1-1-1 prepared in Preparation Example 1 was vacuum-deposited to a light-emitting layer with a compound having a thickness of 300 kPa as a host, and doped with dopant D1. It was. The E1 was vacuum deposited to a thickness of 200 kPa on the light emitting layer to form an electron injection and transport layer. 12 Å thick lithium fluoride (LiF) and 2,000 Å thick aluminum were sequentially deposited on the electron transport layer to form a cathode, thereby manufacturing an organic light emitting device.
상기의 과정에서 유기물의 증착속도는 0.4 ~ 0.7 Å/sec를 유지하였고, 음극 의 리튬플루라이드는 0.3 Å/sec, 알루미늄은 2 Å/sec의 증착속도를 유지하였으며, 증착시 진공도는 2 × 10-7 ~ 5 × 10-8 torr를 유지하였다.In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7 Å / sec, the lithium fluoride of the cathode was maintained at 0.3 Å / sec, the aluminum was maintained at a deposition rate of 2 Å / sec, the vacuum degree during deposition was 2 × 10 −7 to 5 × 10 −8 torr was maintained.
<< 실험예Experimental Example 1-2> 1-2>
상기 실험예 1-1에서 화합물 1-1-1 대신 상기 화합물 1-1-5를 사용한 것을 제외하고는 동일하게 실험하였다.Except for using the compound 1-1-5 instead of compound 1-1-1 in Experimental Example 1-1 and was the same experiment.
<< 실험예Experimental Example 1-3> 1-3>
상기 실험예 1-1에서 화합물 1-1-1 대신 상기 화합물 1-2-31을 사용한 것을 제외하고는 동일하게 실험하였다.Except for using the compound 1-2-31 instead of compound 1-1-1 in Experimental Example 1-1 and was the same experiment.
<< 실험예Experimental Example 1-4> 1-4>
상기 실험예 1-1에서 화합물 1-1-1 대신 상기 화합물 1-2-9을 사용한 것을 제외하고는 동일하게 실험하였다.Except for using the compound 1-2-9 instead of compound 1-1-1 in Experimental Example 1-1 and was the same experiment.
<< 실험예Experimental Example 1-5> 1-5>
상기 실험예 1-1에서 화합물 1-1-1 대신 상기 화합물 1-2-11을 사용한 것을 제외하고는 동일하게 실험하였다.Except for using the compound 1-2-11 instead of compound 1-1-1 in Experimental Example 1-1 was the same experiment.
<< 실험예Experimental Example 1-6> 1-6>
상기 실험예 1-1에서 화합물 1-1-1 대신 상기 화합물 1-2-43을 사용한 것을 제외하고는 동일하게 실험하였다.Except for using the compound 1-2-43 instead of compound 1-1-1 in Experimental Example 1-1 and was the same experiment.
<< 실험예Experimental Example 1-7> 1-7>
상기 실험예 1-1에서 화합물 1-1-1 대신 상기 화합물 1-2-49을 사용한 것을 제외하고는 동일하게 실험하였다.Except for using the compound 1-2-49 instead of compound 1-1-1 in Experimental Example 1-1 and was the same experiment.
<< 실험예Experimental Example 1-8> 1-8>
상기 실험예 1-1에서 화합물 1-1-1 대신 상기 화합물 1-3-11을 사용한 것을 제외하고는 동일하게 실험하였다.Except for using the compound 1-3-11 instead of compound 1-1-1 in Experimental Example 1-1 and was the same experiment.
<< 실험예Experimental Example 1-9> 1-9>
상기 실험예 1-1에서 화합물 1-1-1 대신 상기 화합물 1-2-3을 사용한 것을 제외하고는 동일하게 실험하였다.Except for using the compound 1-2-3 instead of compound 1-1-1 in Experimental Example 1-1 and was the same experiment.
<< 실험예Experimental Example 1-10> 1-10>
상기 실험예 1-1에서 화합물 1-1-1 대신 상기 화합물 1-5-25을 사용한 것을 제외하고는 동일하게 실험하였다.Except for using the compound 1-5-25 instead of compound 1-1-1 in Experimental Example 1-1 and was the same experiment.
<< 실험예Experimental Example 1-11> 1-11>
상기 실험예 1-1에서 화합물 1-1-1 대신 상기 화합물 1-1-162을 사용한 것을 제외하고는 동일하게 실험하였다.Except for using the compound 1-1-162 instead of compound 1-1-1 in Experimental Example 1-1 and was the same experiment.
<< 실험예Experimental Example 1-12> 1-12>
상기 실험예 1-1에서 화합물 1-1-1 대신 상기 화합물 1-1-173을 사용한 것을 제외하고는 동일하게 실험하였다.Except for using the compound 1-1-173 instead of compound 1-1-1 in Experimental Example 1-1 and was the same experiment.
<< 실험예Experimental Example 1-13> 1-13>
상기 실험예 1-1에서 화합물 1-1-1 대신 상기 화합물 1-1-177을 사용한 것을 제외하고는 동일하게 실험하였다.Except for using the compound 1-1-177 instead of compound 1-1-1 in Experimental Example 1-1 and was the same experiment.
상기 실험예 1-1 내지 1-13과 같이 각각의 화합물들을 발광 층으로 사용하여 제조한 유기 발광 소자를 실험한 결과를 하기 표 1에 나타내었다.Experimental results of the organic light emitting device manufactured by using the respective compounds as light emitting layers as in Experimental Examples 1-1 to 1-13 are shown in Table 1 below.
[표 1]TABLE 1
상기 표 1에서 볼 수 있듯이 실험 예 1-1 내지 1-13은 청색발광 층으로 이용될 수 있으며, 적당한 치환체 또는 치환체의 위치에 따라, 비교예 1 내지 3보다 전압 또는 효율면에서 우수한 특성을 나타내었다.As can be seen in Table 1, Experimental Examples 1-1 to 1-13 can be used as a blue light emitting layer, and exhibits superior characteristics in terms of voltage or efficiency than Comparative Examples 1 to 3, depending on appropriate substituents or positions of substituents. It was.
도 1은 기판(101) 위에 양극(102), 발광층(105) 및 음극(107)이 순차적으로 적층된 유기 발광 소자 구조의 예시이다.1 illustrates an organic light emitting device structure in which an anode 102, a light emitting layer 105, and a cathode 107 are sequentially stacked on a substrate 101.
도 2는 기판(101) 위에 양극(102), 정공 주입/정공 수송 및 발광층(105), 전자 수송층(106) 및 음극(107)이 순차적으로 적층된 유기 발광 소자 구조의 예시이다.2 illustrates an organic light emitting device structure in which an anode 102, a hole injection / hole transport and light emitting layer 105, an electron transport layer 106, and a cathode 107 are sequentially stacked on a substrate 101.
도 3은 기판(101), 양극(102), 정공 주입층(103), 정공 수송 및 발광층(105), 전자 수송층(106) 및 음극(107)이 순차적으로 적층된 유기 발광 소자 구조의 예시이다.3 is an example of an organic light emitting device structure in which a substrate 101, an anode 102, a hole injection layer 103, a hole transport and light emitting layer 105, an electron transport layer 106 and a cathode 107 are sequentially stacked. .
도 4는 기판(101), 양극(102), 정공 주입층(103), 정공 수송층(104), 전자 수송 및 발광층(105) 및 음극(107)이 순차적으로 적층된 유기 발광 소자 구조의 예시이다.4 is an example of an organic light emitting device structure in which a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron transporting and emitting layer 105, and a cathode 107 are sequentially stacked. .
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| WO2022165731A1 (en) * | 2021-02-05 | 2022-08-11 | 京东方科技集团股份有限公司 | Electroluminescent device and display device |
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