KR20110066763A - Compound containing indoloacridine and organic electronic element using the same, terminal thereof - Google Patents
Compound containing indoloacridine and organic electronic element using the same, terminal thereof Download PDFInfo
- Publication number
- KR20110066763A KR20110066763A KR1020090123541A KR20090123541A KR20110066763A KR 20110066763 A KR20110066763 A KR 20110066763A KR 1020090123541 A KR1020090123541 A KR 1020090123541A KR 20090123541 A KR20090123541 A KR 20090123541A KR 20110066763 A KR20110066763 A KR 20110066763A
- Authority
- KR
- South Korea
- Prior art keywords
- substituted
- carbon atoms
- unsubstituted
- group
- phosphorus
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 78
- PWGAMUODYKBQLG-UHFFFAOYSA-N N1C2=CC=C[CH]C2=CC2=C1C=CC1=NC3=CC=CC=C3[C]21 Chemical compound N1C2=CC=C[CH]C2=CC2=C1C=CC1=NC3=CC=CC=C3[C]21 PWGAMUODYKBQLG-UHFFFAOYSA-N 0.000 title abstract description 21
- 239000010410 layer Substances 0.000 claims abstract description 120
- 239000000463 material Substances 0.000 claims abstract description 83
- 239000011368 organic material Substances 0.000 claims abstract description 24
- 239000012044 organic layer Substances 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 134
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 94
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 50
- 229910052710 silicon Inorganic materials 0.000 claims description 50
- 239000010703 silicon Substances 0.000 claims description 50
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 48
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 48
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 48
- 229910052757 nitrogen Inorganic materials 0.000 claims description 48
- 229910052760 oxygen Inorganic materials 0.000 claims description 48
- 239000001301 oxygen Substances 0.000 claims description 48
- 229910052698 phosphorus Inorganic materials 0.000 claims description 48
- 239000011574 phosphorus Substances 0.000 claims description 48
- 229910052717 sulfur Inorganic materials 0.000 claims description 48
- 239000011593 sulfur Substances 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000000732 arylene group Chemical group 0.000 claims description 16
- 125000004104 aryloxy group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 150000001721 carbon Chemical class 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000010977 jade Substances 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 238000002347 injection Methods 0.000 abstract description 40
- 239000007924 injection Substances 0.000 abstract description 40
- 230000005525 hole transport Effects 0.000 abstract description 26
- 239000000126 substance Substances 0.000 abstract description 11
- 238000005401 electroluminescence Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- 230000015572 biosynthetic process Effects 0.000 description 29
- 238000003786 synthesis reaction Methods 0.000 description 29
- 238000004440 column chromatography Methods 0.000 description 24
- 230000032258 transport Effects 0.000 description 24
- 239000003960 organic solvent Substances 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- -1 silicon germanium oxide Compound Chemical class 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- 239000000376 reactant Substances 0.000 description 10
- 238000001914 filtration Methods 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 239000002019 doping agent Substances 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-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
- 229940126179 compound 72 Drugs 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- RBCUIRIGTNHLPS-UHFFFAOYSA-N methyl 2,5-dibromobenzoate Chemical compound COC(=O)C1=CC(Br)=CC=C1Br RBCUIRIGTNHLPS-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical compound C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 2
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- BXXLTVBTDZXPTN-UHFFFAOYSA-N methyl 2-iodobenzoate Chemical compound COC(=O)C1=CC=CC=C1I BXXLTVBTDZXPTN-UHFFFAOYSA-N 0.000 description 2
- 229960003540 oxyquinoline Drugs 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- IATRAKWUXMZMIY-UHFFFAOYSA-N strontium oxide Chemical compound [O-2].[Sr+2] IATRAKWUXMZMIY-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 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 2
- 239000011787 zinc oxide Substances 0.000 description 2
- NHEKBOACSUDJKR-UHFFFAOYSA-N 1,2-bis(2,4,4-triphenylbuta-1,3-dienyl)benzene Chemical class C1(=CC=CC=C1)C(=CC(=CC1=C(C=CC=C1)C=C(C=C(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 NHEKBOACSUDJKR-UHFFFAOYSA-N 0.000 description 1
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- PJRGCJBBXGNEGD-UHFFFAOYSA-N 2-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC=C(Br)C=C3NC2=C1 PJRGCJBBXGNEGD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- ADIHXLXYPFKAMB-UHFFFAOYSA-N 3-bromo-9H-carbazole Chemical compound BrC=1C=CC=2NC3=CC=CC=C3C2C1.BrC=1C=CC=2NC3=CC=CC=C3C2C1 ADIHXLXYPFKAMB-UHFFFAOYSA-N 0.000 description 1
- LTBWKAYPXIIVPC-UHFFFAOYSA-N 3-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC(Br)=CC=C3NC2=C1 LTBWKAYPXIIVPC-UHFFFAOYSA-N 0.000 description 1
- HXWWMGJBPGRWRS-CMDGGOBGSA-N 4- -2-tert-butyl-6- -4h-pyran Chemical compound O1C(C(C)(C)C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(C(CCN2CCC3(C)C)(C)C)=C2C3=C1 HXWWMGJBPGRWRS-CMDGGOBGSA-N 0.000 description 1
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 1
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 1
- PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 description 1
- ITHJVESPIWLLBQ-UHFFFAOYSA-N C1(=CC=CC=C1)C(=CC1=C(C=CC=C1)C=1C2=CC=CC=C2C(=C2C=CC=CC=12)C1=C(C=CC=C1)C=C(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C(=CC1=C(C=CC=C1)C=1C2=CC=CC=C2C(=C2C=CC=CC=12)C1=C(C=CC=C1)C=C(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 ITHJVESPIWLLBQ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-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
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- BEBLXYZXQGRFKD-UHFFFAOYSA-N [4-(4-phenyl-n-(4-phenylphenyl)anilino)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=C(C=2C=CC=CC=2)C=C1 BEBLXYZXQGRFKD-UHFFFAOYSA-N 0.000 description 1
- JNSBSKVWZPRJJZ-UHFFFAOYSA-N [4-(n-(9,9-dimethylfluoren-2-yl)-4-phenylanilino)phenyl]boronic acid Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1N(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=C(B(O)O)C=C1 JNSBSKVWZPRJJZ-UHFFFAOYSA-N 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- PPYIVKOTTQCYIV-UHFFFAOYSA-L beryllium;selenate Chemical compound [Be+2].[O-][Se]([O-])(=O)=O PPYIVKOTTQCYIV-UHFFFAOYSA-L 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 1
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- 239000011777 magnesium Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
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- 238000010295 mobile communication Methods 0.000 description 1
- YGNUPJXMDOFFDO-UHFFFAOYSA-N n,4-diphenylaniline Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 YGNUPJXMDOFFDO-UHFFFAOYSA-N 0.000 description 1
- LCSMGMWMTSWXDD-UHFFFAOYSA-N n-(9,9-dimethylfluoren-2-yl)-9,9-dimethylfluoren-2-amine Chemical compound C1=CC=C2C(C)(C)C3=CC(NC4=CC=C5C6=CC=CC=C6C(C5=C4)(C)C)=CC=C3C2=C1 LCSMGMWMTSWXDD-UHFFFAOYSA-N 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
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- 229920000123 polythiophene Polymers 0.000 description 1
- 239000007774 positive electrode material Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
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- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052725 zinc 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
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Abstract
Description
본 발명은 인돌로아크리딘을 포함하는 화합물 및 이를 이용한 유기전기소자, 그 단말에 관한 것이다. The present invention relates to a compound containing indolo acridine, an organic electric device using the same, and a terminal thereof.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기전기소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기전기소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층 등으로 이루어질 수 있다.In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic electric device using an organic light emitting phenomenon generally has a structure including an anode, an anode, and an organic material layer therebetween. In this case, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
유기전기소자에서 유기물층으로 사용되는 재료는 기능에 따라, 발광 재료와 전하 수송 재료, 예컨대 정공주입 재료, 정공수송 재료, 전자수송 재료, 전자주입 재료 등으로 분류될 수 있다. 그리고, 상기 발광 재료는 분자량에 따라 고분자형과 저분자형으로 분류될 수 있고, 발광 메커니즘에 따라 전자의 일중항 여기상태로부 터 유래되는 형광 재료와 전자의 삼중항 여기상태로부터 유래되는 인광 재료로 분류될 수 있다. 또한, 발광 재료는 발광색에 따라 청색, 녹색, 적색 발광 재료와 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료로 구분될 수 있다.Materials used as the organic material layer in the organic electric element 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 light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. Can be classified. In addition, the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.
한편, 발광 재료로서 하나의 물질만 사용하는 경우 분자간 상호 작용에 의하여 최대 발광 파장이 장파장으로 이동하고 색순도가 떨어지거나 발광 감쇄 효과로 소자의 효율이 감소되는 문제가 발생하므로, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여 발광 재료로서 호스트/도판트 계를 사용할 수 있다. 그 원리는 발광층을 형성하는 호스트 보다 에너지 대역 간극이 작은 도판트를 발광층에 소량 혼합하면, 발광층에서 발생한 엑시톤이 도판트로 수송되어 효율이 높은 빛을 내는 것이다. 이 때 호스트의 파장이 도판트의 파장대로 이동하므로, 이용하는 도판트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다.On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system may be used as the light emitting material in order to increase the light emitting efficiency through the light emitting layer. The principle is that when a small amount of dopant having an energy band gap smaller than that of a host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant, thereby producing high-efficiency light. At this time, since the wavelength of the host shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
전술한 유기전기소자가 갖는 우수한 특징들을 충분히 발휘하기 위해서는 소자내 유기물층을 이루는 물질, 예컨대 정공주입 물질, 정공수송 물질, 발광 물질, 전자수송 물질, 전자주입 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 하나, 아직까지 안정하고 효율적인 유기전기소자용 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 electroluminescent 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 electric element has not yet been made sufficiently, and therefore, the development of new materials is continuously required.
본 발명자들은 신규한 구조를 갖는 인돌로아크리딘을 포함하는 화합물을 밝혀내었으며, 또한 이 화합물을 유기전기소자에 적용시 소자의 발광효율, 안정성 및 수명을 크게 향상시킬 수 있다는 사실을 밝혀내었다.The inventors have found a compound containing indoloacridin having a novel structure, and it has also been found that when the compound is applied to an organic electric device, the luminous efficiency, stability and lifetime of the device can be greatly improved.
이에 본 발명은 신규한 인돌로아크리딘을 포함하는 화합물 및 이를 이용한 유기전기소자, 그 단말을 제공하는 것을 목적으로 한다.Accordingly, an object of the present invention is to provide a compound containing a novel indolo acridine, an organic electric device using the same, and a terminal thereof.
일측면에서, 본 발명은 아래 화학식의 화합물을 제공한다.In one aspect, the present invention provides a compound of the formula
본 발명은 인돌로아크리딘을 포함하는 화합물에 따라서 적색, 녹색, 청색, 흰색 등의 모든 칼라의 형광과 인광소자에 적합한 정공주입 재료, 정공수송 재료, 발광 재료 및/또는 전자수송 재료로 유용하다.The present invention is useful as a hole injection material, a hole transport material, a light emitting material and / or an electron transport material suitable for fluorescence and phosphorescent devices of all colors such as red, green, blue, white, etc., depending on the compound containing indoloacridin. .
또한, 본 발명은 상기의 화학식을 가지는 화합물을 이용한 유기 전자 소자 및 이 유기 전자 소자를 포함하는 단말을 제공한다.The present invention also provides an organic electronic device using the compound having the above formula and a terminal including the organic electronic device.
인돌로아크리딘을 포함하는 화합물은 유기전기소자 및 단말에서 다양한 역할을 할 수 있으며, 적색, 녹색, 청색, 흰색 등의 모든 칼라의 형광과 인광소자에 적합한 정공주입 재료, 정공수송 재료, 발광 재료 및/또는 전자수송 재료로 유용하다.Compounds containing indoloacridin can play a variety of roles in organic electronic devices and terminals, and are suitable for hole injection materials, hole transport materials, and luminescent materials for fluorescent and phosphorescent devices of all colors such as red, green, blue, and white. And / or as electron transport materials.
이하, 본 발명의 일부 실시예들을 예시적인 도면을 통해 상세하게 설명한다. 각 도면의 구성요소들에 참조부호를 부가함에 있어서, 동일한 구성요소들에 대해서는 비록 다른 도면상에 표시되더라도 가능한 한 동일한 부호를 가지도록 하고 있음에 유의해야 한다. 또한, 본 발명을 설명함에 있어, 관련된 공지 구성 또는 기능에 대한 구체적인 설명이 본 발명의 요지를 흐릴 수 있다고 판단되는 경우에는 그 상세한 설명은 생략한다.Hereinafter, some embodiments of the present invention will be described in detail through exemplary drawings. In adding reference numerals to the components of each drawing, it should be noted that the same reference numerals are assigned to the same components as much as possible even though they are shown in different drawings. In the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.
또한, 본 발명의 구성 요소를 설명하는 데 있어서, 제 1, 제 2, A, B, (a), (b) 등의 용어를 사용할 수 있다. 이러한 용어는 그 구성 요소를 다른 구성 요소와 구별하기 위한 것일 뿐, 그 용어에 의해 해당 구성 요소의 본질이나 차례 또는 순서 등이 한정되지 않는다. 어떤 구성 요소가 다른 구성요소에 "연결", "결합" 또는 "접속"된다고 기재된 경우, 그 구성 요소는 그 다른 구성요소에 직접적으로 연결되거나 또는 접속될 수 있지만, 각 구성 요소 사이에 또 다른 구성 요소가 "연결", "결합" 또는 "접속"될 수도 있다고 이해되어야 할 것이다.In addition, in describing the component of this invention, terms, such as 1st, 2nd, A, B, (a), (b), can be used. These terms are only for distinguishing the components from other components, and the nature, order or order of the components are not limited by the terms. If a component is described as being "connected", "coupled" or "connected" to another component, that component may be directly connected to or connected to that other component, but there may be another configuration between each component. It is to be understood that the elements may be "connected", "coupled" or "connected".
일측면에서, 본 발명은 아래 화학식 1의 화합물을 제공한다. In one aspect, the present invention provides a compound of Formula 1 below.
위 화학식 1에 있어서, In Chemical Formula 1,
(1) R1 및 R2는 각각 독립적으로 수소원자, 치환 또는 비치환된 탄소수 1 내지 50의 알킬기, 치환 또는 비치환된 탄소수 1 내지 50의 알콕시기, 치환 또는 비치환의 탄소수 1 내지 50의 알케닐기, 치환 또는 비치환의 탄소수 5 내지 60의 아릴렌기, 치환 또는 비치환된 탄소수 5 내지 60의 아릴기, 치환 또는 비치환된 탄소수 5 내지 60의 아릴옥시기, 황(S), 질소(N), 산소(O), 인(P) 및 규소(Si)를 적어도 하나 이상 포함하는 치환 또는 비치환된 탄소수 1 내지 50의 알킬기 또는 황(S), 질소(N), 산소(O), 인(P) 및 규소(Si)를 적어도 하나 이상 포함하는 치환 또는 비치환된 탄소수 5 내지 60의 헤테로아릴기 또는 황(S), 질소(N), 산소(O), 인(P) 및 규소(Si)를 적어도 하나 이상 포함하는 치환 또는 비치환된 탄소수 5 내지 60의 헤테로아릴옥시기이다. (1) R 1 and R 2 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alken having 1 to 50 carbon atoms A substituted or unsubstituted arylene group having 5 to 60 carbon atoms, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, sulfur (S), nitrogen (N) , A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or at least one of oxygen (O), phosphorus (P) and silicon (Si) or sulfur (S), nitrogen (N), oxygen (O), phosphorus ( A substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms or at least one of P) and silicon (Si) or sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) Substituted or unsubstituted heteroaryloxy group having 5 to 60 carbon atoms containing at least one.
(2) R3, R4 및 R5는 각각 서로 독립적으로 수소 원자, 할로겐 원자, 시아노기, 알콕시기, 티올기, 치환 또는 비치환된 탄소수 1 내지 50의 알킬기, 치환 또는 비치환된 탄소수 1 내지 50의 알콕시기, 치환 또는 비치환의 탄소수 1 내지 50의 알케닐기, 치환 또는 비치환의 탄소수 5 내지 60의 아릴렌기, 치환 또는 비치환된 탄소수 5 내지 60의 아릴기, 치환 또는 비치환된 탄소수 5 내지 60의 아릴옥시기, 황(S), 질소(N), 산소(O), 인(P) 및 규소(Si)를 적어도 하나 이상 포함하는 치환 또는 비치환된 탄소수 1 내지 50의 알킬기 또는 황(S), 질소(N), 산소(O), 인(P) 및 규소(Si)를 적어도 하나 이상 포함하는 치환 또는 비치환된 탄소수 5 내지 60의 헤테로아릴기 또는 황(S), 질소(N), 산소(O), 인(P) 및 규소(Si)를 적어도 하나 이상 포함하는 치환 또는 비치환된 탄소수 5 내지 60의 헤테로아릴옥시기이다.(2) R 3 , R 4 and R 5 are each independently a hydrogen atom, a halogen atom, a cyano group, an alkoxy group, a thiol group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted carbon number 1 An alkoxy group of 50 to 50, a substituted or unsubstituted alkenyl group of 1 to 50 carbon atoms, a substituted or unsubstituted arylene group of 5 to 60 carbon atoms, a substituted or unsubstituted aryl group of 5 to 60 carbon atoms, a substituted or unsubstituted carbon number 5 Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or sulfur containing at least one aryloxy group, sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) of 60 to 60 A substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms or at least one sulfur (S), nitrogen (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si); N), oxygen (O), phosphorus (P) and silicon (Si) substituted or unsubstituted carbon having 5 to 60 carbon atoms containing at least one Roatan is rilok time.
(3) n1 및 n2는 0에서 4의 정수이며, n3은 0에서 3의 정수를 가진다.(3) n 1 and n 2 are integers of 0 to 4, and n 3 has an integer of 0 to 3.
(4) 상기 구조식을 가지는 화합물은 용액 공정(soluble process)에 사용될 수 있다.(4) The compound having the above structural formula can be used in a soluble process.
다른 측면에서, 본 발명은 아래 화학식 2의 화합물을 제공한다. In another aspect, the present invention provides a compound of Formula 2 below.
또다른 측면에서, 본 발명은 아래 화학식 3의 화합물을 제공한다. In another aspect, the present invention provides a compound of formula 3 below.
위 화학식 3에서, In Chemical Formula 3,
(5) R6 및 R7은 각각 독립적으로 수소원자, 치환 또는 비치환된 탄소수 1 내지 50의 알킬기, 치환 또는 비치환된 탄소수 1 내지 50의 알콕시기, 치환 또는 비치환의 탄소수 1 내지 50의 알케닐기, 치환 또는 비치환의 탄소수 5 내지 60의 아릴렌기, 치환 또는 비치환된 탄소수 5 내지 60의 아릴기, 치환 또는 비치환된 탄소수 5 내지 60의 아릴옥시기, 황(S), 질소(N), 산소(O), 인(P) 및 규소(Si)를 적어도 하나 이상 포함하는 치환 또는 비치환된 탄소수 1 내지 50의 알킬기 또는 황(S), 질소(N), 산소(O), 인(P) 및 규소(Si)를 적어도 하나 이상 포함하는 치환 또는 비치환된 탄소수 5 내지 60의 헤테로아릴기 또는 황(S), 질소(N), 산소(O), 인(P) 및 규소(Si)를 적어도 하나 이상 포함하는 치환 또는 비치환된 탄소수 5 내지 60의 헤테로아릴옥시기이다.(5) R 6 and R 7 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alken having 1 to 50 carbon atoms A substituted or unsubstituted arylene group having 5 to 60 carbon atoms, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, sulfur (S), nitrogen (N) , A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or at least one of oxygen (O), phosphorus (P) and silicon (Si) or sulfur (S), nitrogen (N), oxygen (O), phosphorus ( A substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms or at least one of P) and silicon (Si) or sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon (Si) Substituted or unsubstituted heteroaryloxy group having 5 to 60 carbon atoms containing at least one.
또다른 측면에서, 본 발명은 아래 화학식 4의 화합물을 제공한다. In another aspect, the present invention provides a compound of formula (4) below.
또다른 측면에서, 본 발명은 아래 화학식 5의 화합물을 제공한다. In another aspect, the present invention provides a compound of formula 5 below.
위 화학식 4 및 5에 있어서, In the above formulas 4 and 5,
(6) R8 및 R9는 각각 독립적으로 수소원자, 치환 또는 비치환된 탄소수 1 내지 50의 알킬기, 치환 또는 비치환된 탄소수 1 내지 50의 알콕시기, 치환 또는 비치환의 탄소수 1 내지 50의 알케닐기, 치환 또는 비치환의 탄소수 5 내지 60의 아릴렌기, 치환 또는 비치환된 탄소수 5 내지 60의 아릴기, 치환 또는 비치환된 탄소수 5 내지 60의 아릴옥시기, 황(S), 질소(N), 산소(O), 인(P) 및 규소(Si)를 적어 도 하나 이상 포함하는 치환 또는 비치환된 탄소수 1 내지 50의 알킬기 또는 황(S), 질소(N), 산소(O), 인(P) 및 규소(Si)를 적어도 하나 이상 포함하는 치환 또는 비치환된 탄소수 5 내지 60의 헤테로아릴기 또는 황(S), 질소(N), 산소(O), 인(P) 및 규소(Si)를 적어도 하나 이상 포함하는 치환 또는 비치환된 탄소수 5 내지 60의 헤테로아릴옥시기이다.(6) R 8 and R 9 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alken having 1 to 50 carbon atoms A substituted or unsubstituted arylene group having 5 to 60 carbon atoms, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, sulfur (S), nitrogen (N) , A substituted or unsubstituted C1-50 alkyl group containing at least one or more oxygen (O), phosphorus (P) and silicon (Si) or sulfur (S), nitrogen (N), oxygen (O), phosphorus A substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms or at least one of (P) and silicon (Si) or sulfur (S), nitrogen (N), oxygen (O), phosphorus (P) and silicon ( Substituted or unsubstituted heteroaryloxy group having 5 to 60 carbon atoms containing at least one Si).
이때 화학식 2 내지 5로 표시되는 화합물들은 용액 공정(soluble process)에 사용될 수 있다.In this case, the compounds represented by Formulas 2 to 5 may be used in a solution process.
본 발명의 일실시예에 따른 인돌로아크리딘을 포함하는 화합물인 화학식 1 내지 5에 속하는 화합물의 구체적 예로서 아래 화학식 6의 화합물들이 있으나, 본 발명이 이들에만 한정되는 것은 아니다.Specific examples of the compounds belonging to Formulas 1 to 5, which are compounds containing indoloacridin according to one embodiment of the present invention, include the compounds of Formula 6 below, but the present invention is not limited thereto.
화학식 1 내지 6을 참조하여 설명한 인돌로아크리딘을 포함하는 화합물들이 유기물층으로 사용되는 다양한 유기전기소자들이 존재한다. 화학식 1 내지 6을 참조하여 설명한 인돌로아크리딘을 포함하는 화합물들이 사용될 수 있는 유기전기소자는 예를 들어, 유기전계발광소자(OLED), 유기태양전지, 유기감광체(OPC) 드럼, 유기트랜지스트(유기 TFT), 포토다이오드(photodiode), 유기레이저(organic laser), 레이저 다이오드(laser diode) 등이 있다.Various organic electric devices exist in which compounds including indoloacridin described with reference to Chemical Formulas 1 to 6 are used as the organic material layer. Examples of organic electroluminescent devices in which compounds including indoloacridin described with reference to Chemical Formulas 1 to 6 may be used include organic electroluminescent devices (OLEDs), organic solar cells, organic photoconductor (OPC) drums, and organic transistors. (Organic TFT), photodiode, organic laser, laser diode and the like.
화학식 1 내지 6을 참조하여 설명한 인돌로아크리딘을 포함하는 화합물들이 적용될 수 있는 유기전기소자 중 일예로 유기전계발광소자(OLED)에 대하여 아래 설명하나, 본 발명은 이에 제한되지 않고 다양한 유기전기소자에 위에서 설명한 인돌로아크리딘을 포함하는 화합물이 적용될 수 있다.As an example of the organic electroluminescent device (OLED) to which the compounds including the indolo acridine described with reference to Chemical Formulas 1 to 6 can be applied, the present invention is not limited thereto. To the compound containing indolo acridine described above can be applied.
본 발명의 다른 실시예는 제1 전극, 제2 전극 및 이들 전극 사이에 배치된 유기물층을 포함하는 유기전기소자에 있어서, 상기 유기물층 중 1층 이상이 상기 화학식 1 내지 6의 화합물들을 포함하는 유기전계발광소자를 제공한다.Another embodiment of the present invention is an organic electric device comprising a first electrode, a second electrode and an organic material layer disposed between the electrodes, wherein at least one of the organic material layer of the organic electric field comprising the compounds of Formula 1 to 6 Provided is a light emitting device.
도 1 내지 도 6은 본 발명의 화합물을 적용할 수 있는 유기전계발광소자의 예를 도시한 것이다.1 to 6 show examples of the organic light emitting display device to which the compound of the present invention can be applied.
본 발명의 다른 실시예에 따른 유기전계발광소자는, 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층을 포함하는 유기물층 중 1층 이상을 상기 화학식 1 내지 6의 화합물들을 포함하도록 형성하는 것을 제외하고는, 당 기술 분야에 통상의 제조 방법 및 재료를 이용하여 당 기술 분야에 알려져 있는 구조로 제 조될 수 있다.The organic light emitting device according to another embodiment of the present invention, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer And a structure known in the art using conventional manufacturing methods and materials in the art, except that at least one layer of the organic material layer including the electron injection layer is formed to include the compounds of Formulas 1 to 6. Can be manufactured.
본 발명에 다른 실시예에 따른 유기전계발광소자의 구조는 도 1 내지 6에 예시되어 있으나, 이들 구조에만 한정된 것은 아니다. 이때, 도면번호 101은 기판, 102는 양극, 103는 정공주입층(HIL), 104는 정공수송층(HTL), 105는 발광층(EML), 106은 전자주입층(EIL), 107은 전자수송층(ETL), 108은 음극을 나타낸다. 미도시하였지만, 이러한 유기전계발광소자는 정공의 이동을 저지하는 정공저지층(HBL), 전자의 이동을 저지하는 전자저지층(EBL) 및 보호층이 더 위치할 수도 있다. 보호층의 경우 최상위층에서 유기물층을 보호하거나 음극을 보호하도록 형성될 수 있다.The structure of the organic light emitting display device according to another embodiment of the present invention is illustrated in FIGS. 1 to 6, but is not limited thereto. In this case, reference numeral 101 denotes a substrate, 102 an anode, 103 a hole injection layer (HIL), 104 a hole transport layer (HTL), 105 a light emitting layer (EML), 106 an electron injection layer (EIL), 107 an electron transport layer ( ETL), 108 represents a negative electrode. Although not shown, the organic light emitting diode may further include a hole blocking layer (HBL) for blocking the movement of holes, an electron blocking layer (EBL) for preventing the movement of electrons, and a protective layer. The protective layer may be formed to protect the organic material layer or the cathode at the uppermost layer.
이때, 화학식 1 내지 12를 참조하여 설명한 인돌로아크리딘을 포함하는 화합물은 정공주입층, 정공수송층, 발광층 및 전자수송층을 포함하는 유기물층 중 하나 이상에 포함될 수 있다. 구체적으로, 화학식 1 내지 12를 참조하여 설명한 인돌로아크리딘을 포함하는 화합물은 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층, 정공저지층, 전자저지층, 보호층 중 하나 이상을 대신하여 사용되거나 이들과 함께 층을 형성하여 사용될 수도 있다. 물론 유기물층 중 한층에만 사용되는 것이 아니라 두층 이상에 사용될 수 있다.In this case, the compound including the indolo acridine described with reference to Chemical Formulas 1 to 12 may be included in one or more of an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer. Specifically, the compound including the indolo acridine described with reference to Chemical Formulas 1 to 12 may include at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, and a protective layer. It may be used instead or in combination with them. Of course, the organic layer may be used not only in one layer but also in two or more layers.
화학식 1 내지 6을 참조하여 설명한 인돌로아크리딘을 포함하는 화합물은 유기전기소자 및 단말에서 다양한 역할을 할 수 있으며, 적색, 녹색, 청색, 흰색 등의 모든 칼라의 형광과 인광소자에 적합한 정공주입 재료, 정공수송 재료, 발광 재료 및/또는 전자수송 재료로 유용하다. Compounds containing indoloacridin described with reference to Chemical Formulas 1 to 6 may play various roles in the organic electric device and the terminal, and may be hole injection suitable for fluorescent and phosphorescent devices of all colors such as red, green, blue, and white. It is useful as a material, a hole transport material, a light emitting material and / or an electron transport material.
예컨대, 본 발명의 다른 실시예에 따른 유기전계발광소자는 스퍼터 링(sputtering)이나 전자빔 증발(e-beam evaporation)과 같은 PVD(physical vapor deposition) 방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층을 포함하는 유기물층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다.For example, an organic light emitting display device according to another embodiment of the present invention has a metal or conductivity on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. A metal oxide or an alloy thereof is deposited to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer is formed thereon, and then a material that can be used as a cathode is deposited thereon. Can be prepared by
이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기전기소자를 만들 수도 있다. 상기 유기물층은 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층 등을 포함하는 다층 구조일 수도 있으나, 이에 한정되지 않고 단층 구조일 수 있다. 또한, 상기 유기물층은 다양한 고분자 소재를 사용하여 증착법이 아닌 솔벤트 프로세스(solvent process), 예컨대 스핀 코팅, 딥 코팅, 닥터 블레이딩, 스크린 프린팅, 잉크젯 프린팅 또는 열 전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다.In addition to the above method, an organic electronic device may be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, but is not limited thereto and may have a single layer structure. In addition, the organic material layer may be formed using a variety of polymer materials by a solvent process such as a spin coating process, a dip coating process, a doctor blading process, a screen printing process, an inkjet printing process or a thermal transfer process, Layer.
본 발명의 다른 실시예에 따른 유기전계발광소자는 위에서 설명한 인돌로아크리딘을 포함하는 화합물을 용액 공정(soluble process)에 의해 유기물층, 예를 들어 발광층이나 정송수송층을 형성할 수도 있다. The organic electroluminescent device according to another embodiment of the present invention may form an organic material layer, for example, a light emitting layer or a transport layer by a soluble process of the compound including the indolo-acridine described above.
기판은 유기전계발광소자의 지지체이며, 실리콘 웨이퍼, 석영 또는 유리판, 금속판, 플라스틱 필름이나 시트 등이 사용될 수 있다.The substrate is a support of the organic light emitting device, and a silicon wafer, quartz or glass plate, metal plate, plastic film or sheet, or the like can be used.
기판 위에는 양극이 위치된다. 이러한 양극은 그 위에 위치되는 정공주입층으로 정공을 주입한다. 양극 물질로는 통상 유기물층으로 정공주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 본 발명에서 사용될 수 있는 양극 물질의 구 체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐주석 산화물(ITO), 인듐아연산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. An anode is positioned over the substrate. This anode injects holes into the hole injection layer located thereon. 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, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline.
양극 위에는 정공주입층이 위치된다. 이러한 정공주입층의 물질로 요구되는 조건은 양극으로부터의 정공주입 효율이 높으며, 주입된 정공을 효율적으로 수송할 수 있어야 한다. 이를 위해서는 이온화 포텐셜이 작고 가시광선에 대한 투명성이 높으며, 정공에 대한 안정성이 우수해야 한다.The hole injection layer is located on the anode. The conditions required for the material of the hole injection layer are high hole injection efficiency from the anode, it should be able to transport the injected holes efficiently. This requires a small ionization potential, high transparency to visible light, and excellent hole stability.
정공주입 물질로는 낮은 전압에서 양극으로부터 정공을 잘 주입받을 수 있는 물질로서, 정공주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 정공주입 물질의 구체적인 예로는 금속 포피린(porphyrine), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴 헥사아자트리페닐렌, 퀴나크리돈(quinacridone) 계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene, quinacridone-based organics, perylene-based organics, Anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
상기 정공주입층 위에는 정공수송층이 위치된다. 이러한 정공수송층은 정공주입층으로부터 정공을 전달받아 그 위에 위치되는 유기발광층으로 수송하는 역할을 하며, 높은 정공 이동도와 정공에 대한 안정성 및 전자를 막아주는 역할를 한 다. 이러한 일반적 요구 이외에 차체 표시용으로 응용할 경우 소자에 대한 내열성이 요구되며, 유리 전이 온도(Tg)가 70 ℃ 이상의 값을 갖는 재료가 바람직하다. 이와 같은 조건을 만족하는 물질들로는 NPD(혹은 NPB라 함), 스피로-아릴아민계화합물, 페릴렌-아릴아민계화합물, 아자시클로헵타트리엔화합물, 비스(디페닐비닐페닐)안트라센, 실리콘게르마늄옥사이드화합물, 실리콘계아릴아민화합물 등이 될 수 있다.The hole transport layer is positioned on the hole injection layer. The hole transport layer receives the holes from the hole injection layer and transports them to the organic light emitting layer positioned thereon, and serves to prevent high hole mobility, hole stability, and electrons. In addition to these general requirements, when applied for vehicle body display, heat resistance to the device is required, and a material having a glass transition temperature (Tg) of 70 ° C. or higher is preferable. Materials satisfying these conditions include NPD (or NPB), spiro-arylamine compounds, perylene-arylamine compounds, azacycloheptatriene compounds, bis (diphenylvinylphenyl) anthracene, silicon germanium oxide Compound, a silicon-based arylamine compound, and the like.
정공수송층 위에는 유기발광층이 위치된다. 이러한 유기발광층는 양극과 음극으로부터 각각 주입된 정공과 전자가 재결합하여 발광을 하는 층이며, 양자효율이 높은 물질로 이루어져 있다. 발광 물질로는 정공수송층과 전자수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자효율이 좋은 물질이 바람직하다. The organic light emitting layer is positioned on the hole transport layer. The organic light emitting layer is a layer for emitting light by recombination of holes and electrons injected from the anode and the cathode, respectively, and is made of a material having high quantum efficiency. 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.
이와 같은 조건을 만족하는 물질 또는 화합물로는 녹색의 경우 Alq3가, 청색의 경우 Balq(8-hydroxyquinoline beryllium salt), DPVBi(4,4'-bis(2,2-diphenylethenyl)-1,1'-biphenyl) 계열, 스피로(Spiro) 물질, 스피로-DPVBi(Spiro-4,4'-bis(2,2-diphenylethenyl)-1,1'-biphenyl), LiPBO(2-(2-benzoxazoyl)-phenol lithium salt), 비스(디페닐비닐페닐비닐)벤젠, 알루미늄-퀴놀린 금속착체, 이미다졸, 티아졸 및 옥사졸의 금속착체 등이 있으며, 청색 발광 효율을 높이기 위해 페릴렌, 및 BczVBi(3,3'[(1,1'-biphenyl)-4,4'-diyldi-2,1-ethenediyl]bis(9-ethyl)-9H-carbazole; DSA(distrylamine)류)를 소량 도핑하여 사용할 수 있다. 적색의 경우는 녹색 발광 물질에 DCJTB([2-(1,1-dimethylethyl)-6-[2-(2,3,6,7-tetrahydro- 1,1,7,7-tetramethyl-1H,5H-benzo(ij)quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene]-propanedinitrile)와 같은 물질을 소량 도핑하여 사용할 수 있다. 잉크젯프린팅, 롤코팅, 스핀코팅 등의 공정을 사용하여 발광층을 형성할 경우에, 폴리페닐렌비닐렌(PPV) 계통의 고분자나 폴리 플로렌(poly 플루오렌(fluorene)) 등의 고분자를 유기발광층에 사용할 수 있다.Substances or compounds that satisfy these conditions include Alq3 for green, Balq (8-hydroxyquinoline beryllium salt) for blue, DPVBi (4,4'-bis (2,2-diphenylethenyl) -1,1'- biphenyl) series, Spiro material, Spiro-DPVBi (Spiro-4,4'-bis (2,2-diphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzoxazoyl) -phenol lithium salt), bis (diphenylvinylphenylvinyl) benzene, aluminum-quinoline metal complex, metal complexes of imidazole, thiazole and oxazole, and the like, perylene, and BczVBi (3,3 ') to increase blue light emission efficiency. [(1,1'-biphenyl) -4,4'-diyldi-2,1-ethenediyl] bis (9-ethyl) -9H-carbazole; DSA (distrylamine) can be used by doping in small amounts. In the red case, DCJTB ([2- (1,1-dimethylethyl) -6- [2- (2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H, 5H Small amounts of doping such as -benzo (ij) quinolizin-9-yl) ethenyl] -4H-pyran-4-ylidene] -propanedinitrile) can be used. When the light emitting layer is formed using a process such as inkjet printing, roll coating, or spin coating, an organic light emitting layer is formed of a polymer of polyphenylene vinylene (PPV) or a polymer such as poly fluorene. Can be used for
유기발광층 위에는 전자수송층이 위치된다. 이러한 전자수송층은 그 위에 위치되는 음극으로부터 전자주입 효율이 높고 주입된 전자를 효율적으로 수송할 수 있는 물질이 필요하다. 이를 위해서는 전자 친화력과 전자 이동속도가 크고 전자에 대한 안정성이 우수한 물질로 이루어져야 한다. 이와 같은 조건을 충족시키는 전자수송 물질로는 구체적인 예로 8-히드록시퀴놀린의 Al 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다.The electron transport layer is positioned on the organic light emitting layer. The electron transport layer needs a material having high electron injection efficiency from the cathode positioned thereon and capable of efficiently transporting the injected electrons. To this end, it must be made of a material having high electron affinity and electron transfer speed and excellent stability to electrons. Examples of the electron transport material that satisfies such conditions include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
전자수송층 위에는 전자주입층이 적층된다. 전자주입층은 Balq, Alq3, Be(bq)2, Zn(BTZ)2, Zn(phq)2, PBD, spiro-PBD, TPBI, Tf-6P 등과 같은 금속착제 화합물, imidazole ring 을 갖는 aromatic화합물이나 boron화합물 등을 포함하는 저분자 물질을 이용하여 제작할 수 있다. 이때, 전자주입층은 100Å ~ 300Å의 두께 범위에서 형성될 수 있다.The electron injection layer is stacked on the electron transport layer. The electron injection layer is a metal complex compound such as Balq, Alq3, Be (bq) 2, Zn (BTZ) 2, Zn (phq) 2, PBD, spiro-PBD, TPBI, Tf-6P, aromatic compound with imidazole ring, It can be produced using a low molecular weight material containing boron compounds and the like. At this time, the electron injection layer may be formed in a thickness range of 100 ~ 300Å.
전자주입층 위에는 음극이 위치된다. 이러한 음극은 전자를 주입하는 역할을 한다. 음극으로 사용하는 재료는 양극에 사용된 재료를 이용하는 것이 가능하며, 효율적인 전자주입을 위해서는 일 함수가 낮은 금속이 보다 바람직하다. 특히 주석, 마그네슘, 인듐, 칼슘, 나트륨, 리튬, 알루미늄, 은 등의 적당한 금속, 또는 그들의 적절한 합금이 사용될 수 있다. 또한 100 ㎛ 이하 두께의 리튬플루오라이드와 알루미늄, 산화리튬과 알루미늄, 스트론튬산화물과 알루미늄 등의 2 층 구조의 전극도 사용될 수 있다.The cathode is positioned on the electron injection layer. This cathode serves to inject electrons. As the material used as the cathode, it is possible to use the material used for the anode, and a metal having a low work function is more preferable for efficient electron injection. In particular, a suitable metal such as tin, magnesium, indium, calcium, sodium, lithium, aluminum, silver, or a suitable alloy thereof can be used. In addition, an electrode having a two-layer structure such as lithium fluoride and aluminum, lithium oxide and aluminum, strontium oxide and aluminum having a thickness of 100 μm or less may also be used.
전술하였듯이, 화학식 1 내지 12을 참조하여 설명한 인돌로아크리딘을 포함하는 화합물에 따라서 적색, 녹색, 청색, 흰색 등의 모든 칼라의 형광과 인광소자에 적합한 정공주입 재료, 정공수송 재료, 발광 재료, 전자수송 재료 및 전자주입 재료로 사용할 수 있으며, 다양한 색의 인광 도판트의 호스트 물질로 사용될 수 있다.As described above, a hole injection material, a hole transport material, a light emitting material, suitable for fluorescence and phosphorescent devices of all colors, such as red, green, blue, and white, according to the compound containing indoloacridin described with reference to Chemical Formulas 1 to 12, It can be used as an electron transport material and an electron injection material, and can be used as a host material for phosphorescent dopants of various colors.
본 발명에 따른 유기전계발광소자는 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 according to the material used.
한편 본 발명은, 위에서 설명한 유기전기소자를 포함하는 디스플레이장치와, 이 디스플레이장치를 구동하는 제어부를 포함하는 단말을 포함한다. 이 단말은 현재 또는 장래의 유무선 통신단말을 의미한다. 이상에서 전술한 본 발명에 따른 단말은 휴대폰 등의 이동 통신 단말기일 수 있으며, PDA, 전자사전, PMP, 리모콘, 네비게이션, 게임기, 각종 TV, 각종 컴퓨터 등 모든 단말을 포함한다.Meanwhile, the present invention includes a display device including the organic electric element described above, and a terminal including a control unit for driving the display device. This terminal means a current or future wired or wireless communication terminal. The terminal according to the present invention described above may be a mobile communication terminal such as a mobile phone, and includes all terminals such as a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, various computers, and the like.
실시예Example
이하, 제조예 및 실험예를 통하여 본 발명을 보다 상세하게 설명한다.그러 나, 이하의 제조예 및 실험예는 본 발명을 예시하기 위한 것이며, 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail with reference to Preparation Examples and Experimental Examples. However, the following Preparation Examples and Experimental Examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.
제조예Manufacturing example
이하, 화학식 6에 속하는 인돌로아크리딘을 포함하는 화합물들에 대한 제조예 또는 합성예를 설명한다. 다만, 화학식 6에 속하는 인돌로아크리딘을 포함하는 화합물들의 수가 많기 때문에 화학식 6에 속하는 인돌로아크리딘을 포함하는 화합물들 중 하나 또는 둘을 예시적으로 설명한다. 본 발명이 속하는 기술분야의 통상의 지식을 가진 자, 즉 당업자라면 아래에서 설명한 제조예들을 통해, 예시하지 않은 본 발명에 속하는 인돌로아크리딘을 포함하는 화합물을 제조할 수 있다.Hereinafter, preparation or synthesis examples of the compounds containing indoloacridine belonging to formula (6) will be described. However, since the number of compounds containing indolo-acridine belonging to the formula (6) is large, one or two of the compounds containing indolo-acridine belonging to the formula (6) will be described as an example. Those skilled in the art, that is, those skilled in the art can prepare a compound comprising indoloacridine belonging to the present invention not illustrated through the preparation examples described below.
중간체 합성방법Intermediate synthesis method
단계1)중간체 A의 합성Step 1) Synthesis of Intermediate A
카바졸(Carbazole)과 2,5-Dibromobenzoic acid methyl ester, Pd2(dba)3, P(tBu)3 그리고 NaOtBu를 톨루엔(Toluene) 용매에 녹인 후, 110 ℃에서 12시간동안 교반시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식힘 다음 CH2Cl2로 추출하고 물로 닦아주었다. 무수 MgSO4로 소량의 물을 제거하고 감압여과 후, 유기 용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 원하는 중간체 A를 얻어내었다 (수율: 48%).Carbazole, 2,5-Dibromobenzoic acid methyl ester, Pd 2 (dba) 3 , P ( t Bu) 3 and NaO t Bu were dissolved in toluene solvent and stirred at 110 ° C. for 12 hours. . After the reaction was completed, the reaction was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removal of a small amount of water with anhydrous MgSO 4 and filtration under reduced pressure, the organic solvent was concentrated to give the desired product A by column chromatography (yield: 48%).
단계2)중간체 B의 합성 Step 2) Synthesis of Intermediate B
상기 단계에서 얻은 중간체 A를 무수 THF에 녹이고, 반응물의 온도를 -78 ℃로 낮추고, 메틸리튬(Methyllithium)(1.6 M in Diethyl ether)을 천천히 적가하고 난 후, 상온에서 12시간동안 교반시켰다. 반응이 종결되면 1N-HCl 수용액을 넣고, 30분간 교반시킨 후, CH2Cl2로 추출하였다. 무수 MgSO4로 반응물 내의 물을 제거하고 감압 여과 후, 유기용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 분리하여 원하는 중간체 B를 얻었다 (수율: 82%).The intermediate A obtained in the above step was dissolved in anhydrous THF, the reaction temperature was lowered to -78 ° C, methyllithium (1.6 M in Diethyl ether) was slowly added dropwise, and the mixture was stirred at room temperature for 12 hours. After the reaction was completed, 1N-HCl aqueous solution was added thereto, stirred for 30 minutes, and extracted with CH 2 Cl 2 . After removing the water in the reaction with anhydrous MgSO 4 and filtered under reduced pressure, the organic solvent was concentrated and the resulting product was separated by column chromatography to give the desired intermediate B (yield: 82%).
단계3)중간체 C의 합성Step 3) Synthesis of Intermediate C
상기 단계에서 얻은 중간체 B를 아세트산(Acetic acid)에 녹이고 HCl 수용액을 천천히 적가한 후, 12시간 동안 환류시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, 반응물을 얼음물에 넣었다. 생성된 침전물을 에탄올(Ethanol)로 닦은 후, 컬럼크로마토그래피를 이용하여 분리하여 원하는 중간체 C를 얻었다 (수율: 57%). The intermediate B obtained in the above step was dissolved in acetic acid and slowly added dropwise an aqueous HCl solution, followed by reflux for 12 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, and the reactant was placed in ice water. The resulting precipitate was washed with ethanol and then separated using column chromatography to obtain the desired intermediate C (yield: 57%).
단계4)중간체 D의 합성Step 4) Synthesis of Intermediate D
2-브로모카바졸(2-Bromocarbazole)과 1-페닐보론산(1-Phenylboronic acid), Pd(PPh3)4, K2CO3를 무수 THF와 소량의 물에 녹인 후, 24시간동안 환류시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식힌 후, CH2Cl2로 추출하고 물로 닦아주었다. 무수 MgSO4로 소량의 물을 제거하고 감압여과 후, 유기용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 원하는 중간체 D를 얻어내었다 (수율: 88%).2-Bromocarbazole, 1-Phenylboronic acid, Pd (PPh 3 ) 4 and K 2 CO 3 were dissolved in anhydrous THF and a small amount of water, and then refluxed for 24 hours. . After the reaction was completed, the reaction mixture was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removal of a small amount of water with anhydrous MgSO 4 and filtration under reduced pressure, the organic solvent was concentrated and the resulting product was purified by column chromatography to give the desired intermediate D (yield: 88%).
단계5)중간체 E의 합성Step 5) Synthesis of Intermediate E
상기단계에서 얻은 중간체 D와 2,5-Dibromobenzoic acid methyl ester, Pd2(dba)3, P(tBu)3 그리고 NaOtBu를 톨루엔 용매에 녹인 후, 110 ℃에서 12시간동안 교반시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식힘 다음 CH2Cl2로 추출하고 물로 닦아주었다. 무수 MgSO4로 소량의 물을 제거하고 감압여과 후, 유기 용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 원하는 중간체 E를 얻어내었다 (수율: 51%).The intermediate D and 2,5-Dibromobenzoic acid methyl ester, Pd 2 (dba) 3 , P ( t Bu) 3 and NaO t Bu obtained in the above step were dissolved in toluene solvent and stirred at 110 ° C. for 12 hours. After the reaction was completed, the reaction was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removal of a small amount of water with anhydrous MgSO 4 and filtration under reduced pressure, the organic solvent was concentrated and the resulting product was purified by column chromatography to give the desired intermediate E (yield: 51%).
단계6)중간체 F의 합성Step 6) Synthesis of Intermediate F
상기 단계에서 얻은 중간체 E를 무수 THF에 녹이고, 반응물의 온도를 -78 ℃로 낮추고, 메틸마그네슘 요오드화물(Methylmagnesium iodide)(3.0 M in Diethyl ether)을 천천히 적가하고 난 후, 상온에서 12시간동안 교반시켰다. 반응이 종결되면 1N-HCl 수용액을 넣고, 30분간 교반시킨 후, CH2Cl2로 추출하였다. 무수 MgSO4로 반응물 내의 물을 제거하고 감압 여과 후, 유기용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 분리하여 원하는 중간체 F를 얻었다 (수율: 62%).The intermediate E obtained in the above step was dissolved in anhydrous THF, the reaction temperature was lowered to -78 ° C, methylmagnesium iodide (3.0 M in Diethyl ether) was slowly added dropwise, followed by stirring at room temperature for 12 hours. I was. After the reaction was completed, 1N-HCl aqueous solution was added thereto, stirred for 30 minutes, and extracted with CH 2 Cl 2 . After removing the water in the reaction with anhydrous MgSO 4 and filtered under reduced pressure, the organic solvent was concentrated and the resulting product was separated by column chromatography to give the desired intermediate F (yield: 62%).
단계7)중간체 G의 합성Step 7) Synthesis of Intermediate G
상기 단계에서 얻은 중간체 F를 아세트산에 녹이고 HCl 수용액을 천천히 적가한 후, 12시간 동안 환류시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, 반응물을 얼음물에 넣었다. 생성된 침전물을 에탄올로 닦은 후, 컬럼크로마토그래피를 이용하여 분리하여 원하는 중간체 G를 얻었다 (수율: 55%).The intermediate F obtained in the above step was dissolved in acetic acid and slowly added dropwise an aqueous HCl solution, followed by reflux for 12 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, and the reactant was placed in ice water. The resulting precipitate was washed with ethanol and then separated using column chromatography to give the desired intermediate G (yield: 55%).
단계8)중간체 H의 합성Step 8) Synthesis of Intermediate H
3-브로모카바졸(3-Bromocarbazole)과 1-Naphthylboronic acid, Pd(PPh3)4, K2CO3를 무수 THF와 소량의 물에 녹인 후, 24시간동안 환류시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식힌 후, CH2Cl2로 추출하고 물로 닦아주었다. 무수 MgSO4로 소량의 물을 제거하고 감압여과 후, 유기용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 원하는 중간체 H를 얻어내었다 (수율: 80%).3-Bromocarbazole, 1-Naphthylboronic acid, Pd (PPh 3 ) 4 , and K 2 CO 3 were dissolved in anhydrous THF and a small amount of water, and then refluxed for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removal of a small amount of water with anhydrous MgSO 4 and filtration under reduced pressure, the resulting organic solvent was concentrated to give the desired intermediate H using column chromatography (yield: 80%).
단계9)중간체 I의 합성Step 9) Synthesis of Intermediate I
상기단계에서 얻은 중간체 H와 2,5-Dibromobenzoic acid methyl ester, Pd2(dba)3, P(tBu)3 그리고 NaOtBu를 톨루엔 용매에 녹인 후, 110 ℃에서 12시간동안 교반시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식힘 다음 CH2Cl2로 추출하고 물로 닦아주었다. 무수 MgSO4로 소량의 물을 제거하고 감압여과 후, 유기 용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 원하는 중간체 I를 얻어내었다 (수율: 48%).The intermediate H and 2,5-Dibromobenzoic acid methyl ester, Pd 2 (dba) 3 , P ( t Bu) 3 and NaO t Bu obtained in the above step were dissolved in toluene solvent and stirred at 110 ° C. for 12 hours. After the reaction was completed, the reaction was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removal of a small amount of water with anhydrous MgSO 4 and filtration under reduced pressure, the organic solvent was concentrated to give the desired product I by column chromatography (yield: 48%).
단계10)중간체 J의 합성Step 10) Synthesis of Intermediate J
상기 단계에서 얻은 중간체 I를 무수 THF에 녹이고, 반응물의 온도를 -78 ℃로 낮추고, 메틸마그네슘 요오드화물(3.0 M in Diethyl ether)을 천천히 적가하고 난 후, 상온에서 12시간동안 교반시켰다. 반응이 종결되면 1N-HCl 수용액을 넣고, 30분간 교반시킨 후, CH2Cl2로 추출하였다. 무수 MgSO4로 반응물 내의 물을 제거하고 감압 여과 후, 유기용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 분리하여 원하는 중간체 J를 얻었다 (수율: 60%).The intermediate I obtained in the above step was dissolved in anhydrous THF, the temperature of the reaction was lowered to -78 ° C, and methyl magnesium iodide (3.0 M in Diethyl ether) was slowly added dropwise, followed by stirring at room temperature for 12 hours. After the reaction was completed, 1N-HCl aqueous solution was added thereto, stirred for 30 minutes, and extracted with CH 2 Cl 2 . After removing the water in the reaction with anhydrous MgSO 4 and filtered under reduced pressure, the organic solvent was concentrated and the resulting product was separated by column chromatography to give the desired intermediate J (yield: 60%).
단계11)중간체 K의 합성Step 11) Synthesis of Intermediate K
상기 단계에서 얻은 중간체 J를 아세트산에 녹이고 HCl 수용액을 천천히 적가한 후, 12시간 동안 환류시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, 반응물을 얼음물에 넣었다. 생성된 침전물을 에탄올로 닦은 후, 컬럼크로마토그래피를 이용하여 분리하여 원하는 중간체 K를 얻었다 (수율: 52%).The intermediate J obtained in the above step was dissolved in acetic acid and slowly added dropwise an aqueous HCl solution, followed by reflux for 12 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, and the reactant was placed in ice water. The resulting precipitate was washed with ethanol and separated using column chromatography to give the desired intermediate K (yield: 52%).
단계12)중간체 L의 합성Step 12) Synthesis of Intermediate L
3-브로모카바졸(2-Bromocarbazole)과 2-Iodobenzoic acid methyl ester, Pd2(dba)3, P(tBu)3 그리고 NaOtBu를 톨루엔 용매에 녹인 후, 110 ℃에서 12시간동안 교반시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식힘 다음 CH2Cl2로 추출하고 물로 닦아주었다. 무수 MgSO4로 소량의 물을 제거하고 감압여과 후, 유기 용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 원하는 중간체 L를 얻어내었다 (수율: 45%).3-Bromocarbazole (2-Bromocarbazole), 2-Iodobenzoic acid methyl ester, Pd 2 (dba) 3 , P ( t Bu) 3 and NaO t Bu were dissolved in toluene solvent and stirred at 110 ° C. for 12 hours. . After the reaction was completed, the reaction was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removal of a small amount of water with anhydrous MgSO 4 and filtration under reduced pressure, the organic solvent was concentrated and the resulting product was purified by column chromatography to give the desired intermediate L (yield: 45%).
단계13)중간체 M의 합성Step 13) Synthesis of Intermediate M
상기 단계에서 얻은 중간체 L를 무수 THF에 녹이고, 반응물의 온도를 ?78 ℃로 낮추고, 메틸마그네슘 요오드화물(3.0 M in Diethyl ether)을 천천히 적가하고 난 후, 상온에서 12시간동안 교반시켰다. 반응이 종결되면 1N-HCl 수용액을 넣고, 30분간 교반시킨 후, CH2Cl2로 추출하였다. 무수 MgSO4로 반응물 내의 물을 제거하고 감압 여과 후, 유기용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 분리하여 원하는 중간체 M를 얻었다 (수율: 59%).The intermediate L obtained in the above step was dissolved in anhydrous THF, the temperature of the reaction was lowered to? 78 ° C, and methyl magnesium iodide (3.0 M in Diethyl ether) was slowly added dropwise, followed by stirring at room temperature for 12 hours. After the reaction was completed, 1N-HCl aqueous solution was added thereto, stirred for 30 minutes, and extracted with CH 2 Cl 2 . After removing the water in the reaction with anhydrous MgSO 4 and filtered under reduced pressure, the organic solvent was concentrated and the resulting product was separated by column chromatography to give the desired intermediate M (yield: 59%).
단계14)중간체 N의 합성Step 14) Synthesis of Intermediate N
상기 단계에서 얻은 중간체 M를 아세트산에 녹이고 HCl 수용액을 천천히 적가한 후, 12시간 동안 환류시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, 반응물을 얼음물에 넣었다. 생성된 침전물을 에탄올로 닦은 후, 컬럼크로마토그래피를 이용하여 분리하여 원하는 중간체 N를 얻었다 (수율: 48%).The intermediate M obtained in the above step was dissolved in acetic acid and slowly added dropwise an aqueous HCl solution, followed by reflux for 12 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, and the reactant was placed in ice water. The resulting precipitate was washed with ethanol and separated using column chromatography to give the desired intermediate N (yield: 48%).
단계15)중간체 O의 합성Step 15) Synthesis of Intermediate O
3-브로모카바졸(3-Bromocarbazole)과 2-Iodobenzoic acid methyl ester, Pd2(dba)3, P(tBu)3 그리고 NaOtBu를 톨루엔 용매에 녹인 후, 110 ℃에서 12시간동안 교반시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식힘 다음 CH2Cl2로 추출하고 물로 닦아주었다. 무수 MgSO4로 소량의 물을 제거하고 감압여과 후, 유기 용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 원하는 중간체 O를 얻어내었다 (수율: 44%).3-Bromocarbazole (3-Bromocarbazole), 2-Iodobenzoic acid methyl ester, Pd 2 (dba) 3 , P ( t Bu) 3 and NaO t Bu were dissolved in toluene solvent and stirred at 110 ° C. for 12 hours. . After the reaction was completed, the reaction was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removal of a small amount of water with anhydrous MgSO 4 and filtration under reduced pressure, the organic solvent was concentrated and the resulting product was purified by column chromatography to give the desired intermediate O (yield: 44%).
단계16)중간체 P의 합성Step 16) Synthesis of Intermediate P
상기 단계에서 얻은 중간체 O를 무수 THF에 녹이고, 반응물의 온도를 -78 ℃로 낮추고, 메틸마그네슘 요오드화물(3.0 M in Diethyl ether)을 천천히 적가하고 난 후, 상온에서 12시간동안 교반시켰다. 반응이 종결되면 1N-HCl 수용액을 넣고, 30분간 교반시킨 후, CH2Cl2로 추출하였다. 무수 MgSO4로 반응물 내의 물을 제거하고 감압 여과 후, 유기용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 분리하여 원하는 중간체 P를 얻었다 (수율: 65%).The intermediate O obtained in the above step was dissolved in anhydrous THF, the reaction temperature was lowered to -78 ° C, and methyl magnesium iodide (3.0 M in Diethyl ether) was slowly added dropwise, followed by stirring at room temperature for 12 hours. After the reaction was completed, 1N-HCl aqueous solution was added thereto, stirred for 30 minutes, and extracted with CH 2 Cl 2 . After removal of water in the reaction with anhydrous MgSO 4 and filtration under reduced pressure, the product obtained by concentrating the organic solvent was separated by column chromatography to give the desired intermediate P (yield: 65%).
단계17)중간체 Q의 합성Step 17) Synthesis of Intermediate Q
상기 단계에서 얻은 중간체 P를 아세트산에 녹이고 HCl 수용액을 천천히 적가한 후, 12시간 동안 환류시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, 반응물을 얼음물에 넣었다. 생성된 침전물을 에탄올로 닦은 후, 컬럼크로마토그래피를 이용하여 분리하여 원하는 중간체 Q를 얻었다 (수율: 51%).The intermediate P obtained in the above step was dissolved in acetic acid and slowly added dropwise an aqueous HCl solution, followed by reflux for 12 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, and the reactant was placed in ice water. The resulting precipitate was washed with ethanol and then separated using column chromatography to give the desired intermediate Q (yield: 51%).
합성예1Synthesis Example 1 : 화합물 4의 합성: Synthesis of Compound 4
상기 단계에서 합성한 중간체 C와 2-Naphthylboronic acid, Pd(PPh3)4, K2CO3를 무수 THF와 소량의 물에 녹인 후, 24시간동안 환류시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식힌 후, CH2Cl2로 추출하고 물로 닦아주었다. 무수 MgSO4로 소량의 물을 제거하고 감압여과 후, 유기용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 원하는 화합물 4를 얻어내었다 (수율: 70%).Intermediate C and 2-Naphthylboronic acid, Pd (PPh 3 ) 4 and K 2 CO 3 synthesized in the above step were dissolved in anhydrous THF and a small amount of water, and then refluxed for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removing a small amount of water with anhydrous MgSO 4 and filtered under reduced pressure, the organic solvent was concentrated to give the desired compound 4 by column chromatography (yield: 70%).
합성예Synthetic example 2: 화합물 2: compound 3030 의 합성Synthesis of
상기 단계에서 합성한 중간체 G와 1-Phenylboronic acid, Pd(PPh3)4, K2CO3를 무수 THF와 소량의 물에 녹인 후, 24시간동안 환류시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식힌 후, CH2Cl2로 추출하고 물로 닦아주었다. 무수 MgSO4로 소량의 물을 제거하고 감압여과 후, 유기용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 원하는 화합물 4를 얻어내었다 (수율: 72%).The intermediate G and 1-Phenylboronic acid, Pd (PPh 3 ) 4 and K 2 CO 3 synthesized in the above step were dissolved in anhydrous THF and a small amount of water, and then refluxed for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removing a small amount of water with anhydrous MgSO 4 and filtered under reduced pressure, the organic solvent was concentrated to give the desired compound 4 by column chromatography (yield: 72%).
합성예 3: 화합물 Synthesis Example 3: Compound 7272 의 합성Synthesis of
상기 단계에서 합성한 중간체 N과 4-(Dibiphenyl-4-ylamino)phenylboronic acid, Pd(PPh3)4, K2CO3를 무수 THF와 소량의 물에 녹인 후, 24시간동안 환류시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식힌 후, CH2Cl2로 추출하고 물로 닦아주었다. 무수 MgSO4로 소량의 물을 제거하고 감압여과 후, 유기용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 원하는 화합물 72를 얻어내었다 (수율: 62%).Intermediate N and 4- (Dibiphenyl-4-ylamino) phenylboronic acid, Pd (PPh 3 ) 4 and K 2 CO 3 synthesized in the above step were dissolved in anhydrous THF and a small amount of water, and then refluxed for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removing a small amount of water with anhydrous MgSO 4 and filtered under reduced pressure, the organic solvent was concentrated to give the desired compound 72 by column chromatography (yield: 62%).
합성예 4: 화합물 Synthesis Example 4 Compound 119119 의 합성Synthesis of
상기 단계에서 합성한 중간체 Q와 4-(Biphenyl-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl-boronic acid, Pd(PPh3)4, K2CO3를 무수 THF와 소량의 물에 녹인 후, 24시간동안 환류시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식힌 후, CH2Cl2로 추출하고 물로 닦아주었다. 무수 MgSO4로 소량의 물을 제거하고 감압여과 후, 유기용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 원하는 화합물 119를 얻어내었다 (수율: 60%).Intermediate Q and 4- (Biphenyl-4-yl (9,9-dimethyl-9 H -fluoren-2-yl) amino) phenyl-boronic acid, Pd (PPh 3 ) 4 , K 2 CO 3 Was dissolved in anhydrous THF and a small amount of water and then refluxed for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removing a small amount of water with anhydrous MgSO 4 and filtered under reduced pressure, the organic solvent was concentrated to give the desired compound 119 by column chromatography (yield: 60%).
합성예Synthetic example 5: 화합물 5: compound 125125 의 합성Synthesis of
상기 단계에서 합성한 중간체 N과 N-Phenylbiphenyl-4-amine, Pd2(dba)3, P(tBu)3 그리고 NaOtBu를 톨루엔 용매에 녹인 후, 110 ℃에서 12시간동안 교반시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식힘 다음 CH2Cl2로 추출하고 물로 닦아주었다. 무수 MgSO4로 소량의 물을 제거하고 감압여과 후, 유기 용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 원하는 화합물 125를 얻어내었다 (수율: 52%).The intermediate N and N- Phenylbiphenyl-4-amine, Pd 2 (dba) 3 , P ( t Bu) 3 and NaO t Bu synthesized in the above step were dissolved in toluene solvent and stirred at 110 ° C. for 12 hours. After the reaction was completed, the reaction was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removal of a small amount of water with anhydrous MgSO 4 and filtration under reduced pressure, the resulting organic solvent was concentrated to give the desired compound 125 by column chromatography (yield: 52%).
합성예Synthetic example 6: 화합물 6: compound 144144 의 합성Synthesis of
상기 단계에서 합성한 중간체 Q와 Bis(9,9-dimethyl-9H-fluoren-2-yl)amine, Pd2(dba)3, P(tBu)3 그리고 NaOtBu를 톨루엔 용매에 녹인 후, 110 ℃에서 12시간동안 교반시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식힘 다음 CH2Cl2로 추출하고 물로 닦아주었다. 무수 MgSO4로 소량의 물을 제거하고 감압여과 후, 유기 용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 원하는 화합물 144를 얻어내었다 (수율: 47%).Intermediate Q and Bis (9,9-dimethyl-9 H -fluoren-2-yl) amine, Pd 2 (dba) 3 , P ( t Bu) 3 and NaO t Bu synthesized in the above step were dissolved in toluene solvent. And stirred at 110 ℃ for 12 hours. After the reaction was completed, the reaction was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removing a small amount of water with anhydrous MgSO 4 and filtered under reduced pressure, the organic solvent was concentrated to give the desired compound 144 by column chromatography (yield: 47%).
합성예Synthetic example 7: 화합물 7: compound 163163 의 합성Synthesis of
상기 단계에서 합성한 중간체 C와 카바졸(Carbazole), Pd2(dba)3, P(tBu)3 그리고 NaOtBu를 톨루엔(Toluene) 용매에 녹인 후, 110 ℃에서 12시간동안 교반시켰다. 반응이 종료되면 반응물의 온도를 상온으로 식힘 다음 CH2Cl2로 추출하고 물로 닦아주었다. 무수 MgSO4로 소량의 물을 제거하고 감압여과 후, 유기 용매를 농축하여 생성된 생성물을 컬럼크로마토그래피를 이용하여 원하는 화합물 163를 얻어내었다 (수율: 60%).Intermediate C and carbazole, Pd 2 (dba) 3 , P ( t Bu) 3 and NaO t Bu synthesized in the above step were dissolved in toluene and then stirred at 110 ° C. for 12 hours. After the reaction was completed, the reaction was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removing a small amount of water with anhydrous MgSO 4 and filtered under reduced pressure, the organic solvent was concentrated to give the desired compound 163 by column chromatography (yield: 60%).
유기전계발광소자의 제조 평가Manufacturing Evaluation of Organic Electroluminescent Device
합성을 통해 얻은 여러 화합물을 각각 발광층의 발광 호스트 물질이나 정공 수송층으로 사용하여 통상적인 방법에 따라 유기전계발광소자를 제작하였다. Various compounds obtained through synthesis were used as light emitting host materials or hole transport layers of the light emitting layer, respectively, to fabricate an organic light emitting display device according to a conventional method.
먼저, 유리 기판에 형성된 ITO층(양극) 위에 우선 홀 주입층으로서 구리프탈로사이아닌(이하 CuPc로 약기함)막을 진공증착하여 10 nm 두께로 형성하였다.First, a copper phthalocyanine (hereinafter abbreviated as CuPc) film was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to form a thickness of 10 nm.
인광 호스트 재료로서 측정할 시에는 이 막 상에 전공수송 화합물로서 4,4-비스[N-(1-나프틸)-N-페닐아미노]비페닐(이하 a-NPD로 약기함)을 30 nm의 두께로 진공증착하여 홀 수송층을 형성하였다. 홀 수송층을 형성한 후, 이 홀 수송층 상부에 인광 발광성의 Ir 금속 착체 도펀트로서 트리스(2-페닐피리딘)이리듐 (이하 I r(ppy)3로 약기함)을 첨가하였다. 이때 발광층 중에 있어서의 I r(ppy)3의 농도는 5중량%로 하였다. 홀 저지층으로 (1,1'-비스페닐)-4-올레이토)비스(2-메틸-8-퀴놀린올레이토)알루미늄 (이하 BAlq로 약기함)을 10 nm 의 두께로 진공증착하고, 전자주입층으로 트리스(8-퀴놀리놀)알루미늄 (이하 Alq3로 약칭함)을 40 nm의 두께로 성막하였다. 이 후, 할로젠화 알칼리 금속인 LiF를 0.2 nm의 두께로 증착하고, Al을 150 nm의 두께로 증착하여 이 Al/LiF를 음극으로 사용함으로서 유기전계 발광소자를 제조하였다.When measured as a phosphorescent host material, 30 nm of 4,4-bis [ N- (1-naphthyl) -N -phenylamino] biphenyl (abbreviated as a-NPD) as a major transport compound on this film was measured. Vacuum deposition was carried out to a thickness of to form a hole transport layer. After the hole transport layer was formed, tris (2-phenylpyridine) iridium (abbreviated as I r (ppy) 3 hereinafter) was added as a phosphorescent Ir metal complex dopant on the hole transport layer. At this time, the concentration of I r (ppy) 3 in the light emitting layer was 5% by weight. (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolineoleito) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm as a hole blocking layer, Tris (8-quinolinol) aluminum (hereinafter abbreviated to Alq 3 ) was formed into an injection layer to a thickness of 40 nm. Thereafter, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm, Al was deposited to a thickness of 150 nm, and an organic light emitting device was manufactured by using this Al / LiF as a cathode.
정공수송층 재료로서 측정할 시에는 45 nm 두께의 BD-052X (Idemitus사)가 7% 도핑된 발광층을 사용하였다. 이때, BD-052X는 청색 형광 도펀트이고, 발광 호스트 물질로는 9,10-디(나프탈렌-2-일)안트라센(ADN)을 사용하여 유기전계발광소자를 제조하였다.When measuring as the hole transport layer material, a light emitting layer doped with BD-052X (Idemitus) 7% doped with a thickness of 45 nm was used. In this case, BD-052X is a blue fluorescent dopant, and an organic light emitting diode was manufactured using 9,10-di (naphthalen-2-yl) anthracene (ADN) as a light emitting host material.
비교실험예1Comparative Example 1
합성된 화합물 중에 화합물 4, 30 또는 163 각각을 위에서 설명한 유기 전기 소자의 발광 호스트 물질로 사용해 실시예 1 내지 3의 유기전계발광소자를 제작하 였다. Among the synthesized compounds, compounds 4 , 30, or 163, respectively, were used as the light emitting host material of the organic electric device described above to prepare the organic light emitting display device of Examples 1 to 3.
비교를 위해, 본 발명의 화합물 대신에 화학식 7으로 표시되는 화합물(이하 CBP로 약기함)을 발광 호스트 물질로 사용하여 시험예와 동일한 구조의 유기전계발광소자를 제작하였다. For comparison, an organic electroluminescent device having the same structure as the test example was manufactured using a compound represented by Formula 7 (hereinafter abbreviated as CBP) as a light emitting host material instead of the compound of the present invention.
호스트 재료Emitting layer
Host material
( V )Voltage
(V)
( mA/cm2 )Current density
(mA / cm 2 )
( cd/A )Luminous efficiency
(cd / A)
( x, y )Chromaticity coordinates
(x, y)
비교실험예2Comparative Experiment 2
또한 합성된 화합물 중에 화합물 72, 119, 125 또는 144 각각을 위에서 설명한 유기 전기 소자의 정공수송층 물질로 사용해 실시예 4 내지 7의 유기 전기전계발광소자를 제작하였다. In addition, compounds 72 , 119 , 125, or 144 of the synthesized compounds were used as the hole transport layer material of the organic electric device described above, thereby fabricating the organic electroluminescent devices of Examples 4 to 7.
비교를 위해, 본 발명의 화합물 대신에 화학식8으로 표시되는 화합물(이하 a-NPD 로 약기함)을 정공수송층 물질로 사용하여 시험예와 동일한 구조의 유기전계발광소자를 제작하였다. For comparison, an organic electroluminescent device having the same structure as the test example was manufactured by using the compound represented by Formula 8 (hereinafter abbreviated as a-NPD) as a hole transport material instead of the compound of the present invention.
호스트 재료Emitting layer
Host material
( V )Voltage
(V)
( mA/cm2 )Current density
(mA / cm 2 )
( cd/A )Luminous efficiency
(cd / A)
( x, y )Chromaticity coordinates
(x, y)
표 1 및 표 2의 결과로부터 알 수 있듯이, 유기전계발광소자용 재료를 이용한 유기전계발광소자는 비교예들로 사용된 CBP 및 a-NPD에 비해고효율이면서 색순도가 향상될 뿐만 아니라 구동전압 또한 현저히 향상시킬 수 있다. 따라서 장수명인 녹색 및 청색 발광이 얻어지므로 유기전계발광소자의 녹색 인광 호스트 물질 및 정공수송층 재료로 사용되어 발광효율 및 수명을 현저히 개선시킬 수 있다.As can be seen from the results of Table 1 and Table 2, the organic light emitting device using the material for the organic light emitting device is not only improved in efficiency and color purity but also driving voltage is significantly higher than CBP and a-NPD used as comparative examples. Can be improved. Therefore, since green and blue light emission of long life is obtained, it is used as a green phosphorescent host material and a hole transport layer material of the organic light emitting device, and thus it is possible to remarkably improve the luminous efficiency and lifetime.
본 발명의 화합물들을 유기전계발광소자의 다른 유기물층들, 예를 들어 발광층의 호스트 재료 및 정공수소층 뿐만 아니라, 전자주입층, 전자수송층 및 정공주입층에 사용되더라도 동일한 효과를 얻을 수 있는 것은 자명하다.It is apparent that the same effect can be obtained even when the compounds of the present invention are used in other organic material layers of the organic light emitting device, for example, the host material and the hole hydrogen layer of the light emitting layer, as well as the electron injection layer, the electron transport layer and the hole injection layer. .
이상의 설명은 본 발명을 예시적으로 설명한 것에 불과한 것으로, 본 발명이 속하는 기술분야에서 통상의 지식을 가지는 자라면 본 발명의 본질적인 특성에서 벗어나지 않는 범위에서 다양한 변형이 가능할 것이다. 따라서, 본 명세서에 개시된 실시예들은 본 발명을 한정하기 위한 것이 아니라 설명하기 위한 것이고, 이러한 실시예에 의하여 본 발명의 사상과 범위가 한정되는 것은 아니다.While the present invention has been described with reference to exemplary embodiments, it is to be understood that the invention is not limited to the disclosed exemplary embodiments. Accordingly, the embodiments disclosed herein are intended to be illustrative rather than limiting, and the spirit and scope of the present invention are not limited by these embodiments.
본 발명의 보호범위는 아래의 청구범위에 의하여 해석되어야 하며, 그와 동등한 범위 내에 있는 모든 기술은 본 발명의 권리범위에 포함되는 것으로 해석되어야 할 것이다.The protection scope of the present invention should be interpreted by the following claims, and all the technologies within the equivalent scope should be interpreted as being included in the scope of the present invention.
도 1 내지 도 6은 본 발명의 화합물을 적용할 수 있는 유기전계발광소자의 예를 도시한 것이다.1 to 6 show examples of the organic light emitting display device to which the compound of the present invention can be applied.
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