KR101603390B1 - Organic compounds and organic electro luminescence device comprising the same - Google Patents
Organic compounds and organic electro luminescence device comprising the same Download PDFInfo
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- KR101603390B1 KR101603390B1 KR1020130165005A KR20130165005A KR101603390B1 KR 101603390 B1 KR101603390 B1 KR 101603390B1 KR 1020130165005 A KR1020130165005 A KR 1020130165005A KR 20130165005 A KR20130165005 A KR 20130165005A KR 101603390 B1 KR101603390 B1 KR 101603390B1
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 11
- 238000005401 electroluminescence Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 79
- 125000003118 aryl group Chemical group 0.000 claims description 44
- 239000010410 layer Substances 0.000 claims description 43
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 29
- 125000004429 atom Chemical group 0.000 claims description 15
- 239000012044 organic layer Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000005264 aryl amine group Chemical group 0.000 claims description 10
- 125000005104 aryl silyl group Chemical group 0.000 claims description 10
- 239000011368 organic material Substances 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 2
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- 238000003786 synthesis reaction Methods 0.000 description 76
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- 125000001424 substituent group Chemical group 0.000 description 18
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- 239000002904 solvent Substances 0.000 description 4
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- ACMBKPGNTZECCN-UHFFFAOYSA-N 13-nitro-8-thia-2,3-diazatetracyclo[10.4.0.02,6.07,11]hexadeca-1(12),3,5,7(11),9,13,15-heptaene Chemical compound [N+](=O)([O-])C1=C2C3=C(C=4N(C2=CC=C1)N=CC=4)SC=C3 ACMBKPGNTZECCN-UHFFFAOYSA-N 0.000 description 2
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- PURXICPWFRCCQS-UHFFFAOYSA-N 8-nitro-3-phenylpyrrolo[1,2-f]phenanthridine Chemical compound [N+](=O)([O-])C1=CC=CC=2N3C(C=4C=CC=CC=4C1=2)=CC=C3C1=CC=CC=C1 PURXICPWFRCCQS-UHFFFAOYSA-N 0.000 description 2
- SCMNLAQPNCYUHE-UHFFFAOYSA-N 8-nitroimidazo[1,2-f]phenanthridine Chemical compound [N+](=O)([O-])C1=CC=CC=2N3C(C=4C=CC=CC=4C1=2)=NC=C3 SCMNLAQPNCYUHE-UHFFFAOYSA-N 0.000 description 2
- HUVBCZVCVZJQLA-UHFFFAOYSA-N 8-nitropyrazolo[1,5-f]phenanthridine Chemical compound [N+](=O)([O-])C1=CC=CC=2N3C(C4=CC=CC=C4C1=2)=CC=N3 HUVBCZVCVZJQLA-UHFFFAOYSA-N 0.000 description 2
- DFFWEIOAJQFKCA-UHFFFAOYSA-N 9-nitro-14,21-diazapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(21),2,4,6,8(13),9,11,15,17,19-decaene Chemical compound [N+](=O)([O-])C1=CC=CC=2N3C(C=4C=CC=CC=4C1=2)=NC1=C3C=CC=C1 DFFWEIOAJQFKCA-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
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- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- XLIQPEZVRBALDD-UHFFFAOYSA-N pyrrolo[1,2-a]quinoline Chemical group C1=CC2=CC=CC=C2N2C1=CC=C2 XLIQPEZVRBALDD-UHFFFAOYSA-N 0.000 description 2
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
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- UDZSLJULKCKKPX-UHFFFAOYSA-N (4-bromophenyl)-triphenylsilane Chemical compound C1=CC(Br)=CC=C1[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 UDZSLJULKCKKPX-UHFFFAOYSA-N 0.000 description 1
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- QZFBYWYSPPBBTR-UHFFFAOYSA-N 14-nitro-2,3,16-triazatetracyclo[11.4.0.02,6.07,12]heptadeca-1(17),3,5,7,9,11,13,15-octaene Chemical compound [N+](=O)([O-])C1=C2C3=C(C=4N(C2=CN=C1)N=CC=4)C=CC=C3 QZFBYWYSPPBBTR-UHFFFAOYSA-N 0.000 description 1
- UJOBAGMOOBYCLZ-UHFFFAOYSA-N 14-nitro-2,3,9-triazatetracyclo[11.4.0.02,6.07,12]heptadeca-1(13),3,5,7(12),8,10,14,16-octaene Chemical compound [N+](=O)([O-])C1=CC=CC=2N3C(C=4C=NC=CC=4C=21)=CC=N3 UJOBAGMOOBYCLZ-UHFFFAOYSA-N 0.000 description 1
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- YOTNZYAIAMJNSQ-UHFFFAOYSA-N C1=CC=C2C(=C1)C3=C(C=CC=C3[N+](=O)[O-])N4C2=NC(=C4)Br Chemical compound C1=CC=C2C(=C1)C3=C(C=CC=C3[N+](=O)[O-])N4C2=NC(=C4)Br YOTNZYAIAMJNSQ-UHFFFAOYSA-N 0.000 description 1
- UPIREIZWOMWENS-UHFFFAOYSA-N C1=CC=C2C(=C1)C3=C(C=NC=C3)C4=CC(=NN24)[N+](=O)[O-] Chemical compound C1=CC=C2C(=C1)C3=C(C=NC=C3)C4=CC(=NN24)[N+](=O)[O-] UPIREIZWOMWENS-UHFFFAOYSA-N 0.000 description 1
- FJAIUQBQCUAQRY-UHFFFAOYSA-N C1=CC=C2C(=C1)C3=C(C=NC=C3)N4C2=CC(=N4)[N+](=O)[O-] Chemical compound C1=CC=C2C(=C1)C3=C(C=NC=C3)N4C2=CC(=N4)[N+](=O)[O-] FJAIUQBQCUAQRY-UHFFFAOYSA-N 0.000 description 1
- VBYOCGMACDPIHC-UHFFFAOYSA-N C1=CC=C2C(=C1)C3=CC=CC=C3N4C2=CC(=N4)[N+](=O)[O-] Chemical compound C1=CC=C2C(=C1)C3=CC=CC=C3N4C2=CC(=N4)[N+](=O)[O-] VBYOCGMACDPIHC-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
- 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- UQFQONCQIQEYPJ-UHFFFAOYSA-N N-methylpyrazole Chemical compound CN1C=CC=N1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
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- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- 229910001573 adamantine Inorganic materials 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- URAZVWXGWMBUGJ-UHFFFAOYSA-N di(propan-2-yl)azanium;chloride Chemical compound [Cl-].CC(C)[NH2+]C(C)C URAZVWXGWMBUGJ-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 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
- 230000005283 ground state Effects 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 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
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000007774 positive electrode material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 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
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 description 1
- SCHZCUMIENIQMY-UHFFFAOYSA-N tris(trimethylsilyl)silicon Chemical compound C[Si](C)(C)[Si]([Si](C)(C)C)[Si](C)(C)C SCHZCUMIENIQMY-UHFFFAOYSA-N 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
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/16—Peri-condensed systems
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5325—Aromatic phosphine oxides or thioxides (P-C aromatic linkage)
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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Abstract
본 발명은 유기 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로서, 본 발명에 따른 화합물은 유기 전계 발광 소자의 유기물층, 바람직하게는 발광층에 사용됨에 따라 유기 전계 발광 소자의 발광효율, 구동 전압, 수명 등을 향상시킬 수 있다.BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic compound and an organic electroluminescent device including the organic compound, wherein the compound according to the present invention is used in an organic compound layer of an organic electroluminescent device, And the like can be improved.
Description
본 발명은 신규한 유기 화합물 및 상기 화합물을 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic compound and an organic electroluminescent device comprising the compound.
유기 전계 발광 소자는 두 전극 사이에 전압을 걸어 주면 양극에서는 정공이 유기물층으로 주입되고, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 상기 유기물층에 포함되는 물질은 그 기능에 따라, 발광 물질, 정공 주입 물질, 정공 수송 물질, 전자 수송 물질, 전자 주입 물질 등으로 분류될 수 있다.In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic layer in the anode, and electrons are injected into the organic layer in the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. The material contained in the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material, or the like depending on its function.
상기 발광 물질은 발광색에 따라 청색, 녹색, 적색의 발광 물질과, 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색의 발광 물질로 구분될 수 있다. 또한 색순도의 증가와 에너지 전이를 통해 발광 효율을 증가시키기 위하여 발광 물질로서 호스트/도판트 계를 사용할 수 있다.The luminescent material may be classified into blue, green, and red luminescent materials according to luminescent colors, and yellow and orange luminescent materials necessary to realize better natural colors. A host / dopant system can be used as a luminescent material to increase the luminous efficiency through increase of color purity and energy transfer.
도판트 물질은 유기 물질을 사용하는 형광 도판트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도판트로 나눌 수 있다. 이때 인광 도판트는 이론적으로 형광 도판트에 비해 최대 4배의 발광 효율을 향상시킬 수 있기 때문에 인광 도판트 뿐만 아니라 인광 호스트에 대한 연구가 많이 진행되고 있다.The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. Since the phosphorescent dopant can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescent dopant, studies on the phosphorescent dopant as well as the phosphorescent host have been conducted.
현재 발광층에 사용되는 형광 도판트/호스트 물질로는 안트라센 유도체들이 알려져 있다. 또한 발광층에 사용되는 인광 도판트 물질로는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등의 Ir을 포함하는 금속 착체 화합물이 알려져 있고, 인광 호스트 물질로는 4,4-dicarbazolybiphenyl(CBP)가 알려져 있다.Currently, anthracene derivatives are known as fluorescent dopant / host materials used in the light emitting layer. As phosphorescent dopant materials used for the light emitting layer, metal complex compounds including Ir such as Firpic, Ir (ppy) 3 , (acac) Ir (btp) 2 and the like are known. As phosphorescent host materials, 4,4-dicarbazolybiphenyl (CBP) is known.
그러나 기존의 재료들은 유리전이온도가 낮고 열적 안정성이 좋지 않아 유기 전계 발광 소자에서의 수명 측면에서 만족할만한 수준이 되지 못하고 있으며, 발광 특성 측면에서도 여전히 개선이 필요하다.However, since the conventional materials have low glass transition temperature and poor thermal stability, they are not satisfactory in terms of lifetime in organic electroluminescent devices, and still need improvement in terms of luminescent properties.
상기한 문제점을 해결하기 위해 본 발명은 유리 전이온도가 높으며 열적 안정성이 우수하고, 발광 특성이 개선된 신규 유기 화합물을 제공하는 것을 목적으로 한다.In order to solve the above problems, it is an object of the present invention to provide a novel organic compound having a high glass transition temperature, excellent thermal stability, and improved luminescence properties.
또 본 발명은 상기 유기 화합물을 포함하는 유기 전계 발광 소자를 제공하는 것을 목적으로 한다.Another object of the present invention is to provide an organic electroluminescent device comprising the organic compound.
상기한 목적을 달성하기 위해 본 발명은 하기 화학식 1 로 표시되는 화합물을 제공한다.In order to accomplish the above object, the present invention provides a compound represented by the following general formula (1).
[화학식 1][Chemical Formula 1]
상기 화학식 1에서,In Formula 1,
X1 내지 X6은 각각 독립적으로 N 또는 CR1이고,X 1 to X 6 are each independently N or CR 1 ,
Cy1은 5원 방향족 고리, 5원 헤테로방향족 고리, 6원 방향족 고리 또는 6원 헤테로방향족 고리이고,Cy1 is a 5-membered aromatic ring, a 5-membered heteroaromatic ring, a 6-membered aromatic ring or a 6-membered heteroaromatic ring,
Ar1은 C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고,Ar 1 represents a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, C C 6 to C 40 aryloxy groups, C 1 to C 40 alkyloxy groups, C 6 to C 40 arylamine groups, C 3 to C 40 cycloalkyl groups, heterocyclic cycloalkyl groups having 3 to 40 nuclear atoms, C 1 ~ C 40 alkyl silyl group, a alkyl boronic of C 1 ~ C 40, C 6 ~ C 40 aryl boron group, C 6 ~ C 40 aryl phosphine group, C 6 ~ aryl phosphine oxide of the C 40 group And an arylsilyl group of C 6 to C 40 ,
상기 R1은 수소, 중수소, 할로겐, 시아노, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되며, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고,Wherein R 1 is selected from the group consisting of hydrogen, deuterium, halogen, cyano, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 2 to C 40 alkynyl, C 6 to C 40 aryl, from 5 to 40 heteroaryl group, C 6 ~ C 40 of the aryloxy group, C 1 ~ C 40 of the alkyloxy group, C 6 ~ C 40 aryl amine group, C 3 ~ C 40 cycloalkyl group, a nuclear atom 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, the C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 40 group of the arylboronic, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ is selected from the group consisting of aryl silyl group of C 40, by combining groups of adjacent, it may form a condensed ring,
상기 R1 및 Ar1의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 아릴아민기, 시클로알킬기, 헤테로시클로알킬기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되는 1종 이상의 치환기로 치환 또는 비치환될 수 있다. 이때, R1 및 Ar1이 복수개의 치환기로 치환될 경우, 복수개의 치환기는 서로 동일하거나 상이할 수 있다.Wherein R 1 and an alkyl group of Ar 1, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, a cycloalkyl group, a heterocycloalkyl group, alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an aryl silyl group each independently selected from deuterium, halogen, a cyano, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 of the alkynyl A C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C 6 to C 40 aryloxy group, a C 1 to C 40 alkyloxy group, a C 6 to C 40 arylamine group, an aryl boronic of C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 40 group, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ C 40 aryl or silyl group substituted with one or more substituents selected from the group consisting of It can be unsubstituted. When R 1 and Ar 1 are substituted with a plurality of substituents, the plurality of substituents may be the same or different from each other.
또한 본 발명은 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중에서 적어도 하나는 상기 화학식 1의 화합물을 포함하는 유기 전계 발광 소자를 제공한다.Also, the present invention is an organic electroluminescent device comprising a cathode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes an organic An electroluminescent device is provided.
여기서 상기 화합물을 포함하는 유기물층은 발광층인 것이 바람직하다.Here, the organic compound layer containing the compound is preferably a light emitting layer.
본 발명의 화합물은 열적 안정성, 전자 및 정공 수송능, 발광능 등이 우수하기 때문에 유기 전계 발광 소자의 유기물층 재료로 유용하게 적용될 수 있다.Since the compound of the present invention is excellent in thermal stability, electron transporting ability, hole transporting ability, and light emitting ability, the compound of the present invention can be effectively applied as an organic layer material of an organic electroluminescent device.
또한 본 발명의 화합물을 유기물층에 포함하는 유기 전계 발광 소자는 발광성능, 구동전압, 수명, 효율 등의 측면이 크게 향상되어 풀 칼라 디스플레이 패널 등에 효과적으로 적용될 수 있다.In addition, the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full color display panel, etc. in terms of light emitting performance, driving voltage, lifetime and efficiency.
이하, 본 발명을 설명한다.
Hereinafter, the present invention will be described.
1. 신규 유기 화합물1. New organic compounds
본 발명의 신규 화합물은 피롤로퀴나졸린 모이어티(pyrrolo[1,2-a]quinoline moiety)에 5원 헤테로방향족 고리 또는 6원 헤테로방향족 고리가 융합되어 기본 골격을 이루며, 상기 기본 골격에 다양한 치환체가 결합된 구조로서, 상기 화학식 1로 표시되는 것을 특징으로 한다.The novel compounds of the present invention are prepared by fusing a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring to a pyrrolo [1,2-a] quinoline moiety to form a basic skeleton, And is characterized by being represented by the above formula (1).
상기 피롤로퀴나졸린 모이어티(pyrrolo[1,2-a]quinoline moiety)에 5원 헤테로방향족 고리 또는 6원 헤테로방향족 고리가 결합된 기본 골격은 전자 흡수성이 큰 전자끌게기(EWG)와 전자 공여성이 큰 전자주게기(EDG)를 모두 가지기 때문에 양극성(bipolar) 화합물의 특성을 가질 수 있다. 또한 기본 골격에 결합된 다양한 치환체로 인해 넓은 밴드갭을 가지며, 정공과 전자의 결합력을 높일 수 있다. 또 다양한 치환체로 인해 화합물의 분자량이 유의적으로 증대되어 유리전이온도가 높으며, 이로 인해 종래의 유기물층 재료(예를 들어, CBP(4,4-dicarbazolybiphenyl))보다 높은 열적 안정성을 가질 수 있다. 아울러, 본 발명의 화합물은 유기물층의 결정화 억제에도 효과적이다.The basic skeleton in which a pyrrolo [1,2-a] quinoline moiety is bonded to a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring is an electron withdrawing group (EWG) Women can have the property of bipolar compounds because they have all of the large electron donors (EDG). In addition, due to various substituents bonded to the basic skeleton, they have a wide bandgap and can enhance the bonding force between holes and electrons. In addition, due to the various substituents, the molecular weight of the compound is significantly increased to have a high glass transition temperature, which can have higher thermal stability than conventional organic layer materials (for example, CBP (4,4-dicarbazolylbiphenyl)). In addition, the compound of the present invention is also effective for inhibiting crystallization of the organic material layer.
따라서 본 발명의 화학식 1로 표시되는 화합물을 유기 전계 발광 소자에 적용할 경우(구체적으로 유기 전계 발광 소자의 정공 주입층, 정공 수송층, 전자 수송층 또는 발광층에 적용) 성능 및 수명이 향상된 유기 전계 발광 소자를 제공할 수 있다. 또한 이와 같이 성능이 향상된 유기 전계 발광 소자는 풀 칼라 유기 발광 패널에서의 성능 극대화를 가져올 수 있다.Therefore, when the compound represented by Formula 1 of the present invention is applied to an organic electroluminescent device (specifically, a hole injecting layer, a hole transporting layer, an electron transporting layer, or a light emitting layer of an organic electroluminescent device) Can be provided. Also, the organic electroluminescent device having such improved performance can maximize the performance of the full-color organic light emitting panel.
본 발명의 화학식 1로 표시되는 화합물에서, Cy1은 5원 방향족 고리, 5원 헤테로방향족 고리, 6원 방향족 고리 또는 6원 헤테로방향족 고리이다. 상기 5원 방향족 고리의 예로는 시클로펜타디엔을 들 수 있고, 상기 5원 헤테로방향족 고리의 예로는 피롤, 퓨란, 싸이오펜을 들 수 있으며, 상기 6원 방향족 고리의 예로는 벤젠을 들 수 있고, 상기 6원 헤테로방향족 고리의 예로는 피리딘, 피리미딘, 트리아진을 들 수 있다. 여기서, 유기 전계 발광 소자의 특성을 고려할 때, 상기 Cy1은 벤젠 고리 또는 피리딘 고리인 것이 바람직하다.In the compound represented by formula (1) of the present invention, Cy1 is a 5-membered aromatic ring, a 5-membered heteroaromatic ring, a 6-membered aromatic ring or a 6-membered heteroaromatic ring. Examples of the 5-membered aromatic ring include cyclopentadiene, and examples of the 5-membered heteroaromatic ring include pyrrole, furan and thiophene. Examples of the 6-membered aromatic ring include benzene, Examples of the 6-membered heteroaromatic ring include pyridine, pyrimidine and triazine. Here, in consideration of the characteristics of the organic electroluminescent device, it is preferable that Cy1 is a benzene ring or a pyridine ring.
본 발명의 화학식 1로 표시되는 화합물에서, X1 내지 X6은 각각 독립적으로 N 또는 CR1인데. 모두 CR1이거나 N을 한 개 포함하는 것이 바람직하다. 한편 복수개의 CR1은 서로 동일하거나 상이할 수 있다(즉, R1이 서로 동일하거나 상이할 수 있음).In the compounds represented by the formula (1) of the present invention, each of X 1 to X 6 is independently N or CR 1 . It is preferable that all of CR 1 and N are included. The plural CR 1 s may be the same or different from each other (that is, R 1 may be the same or different from each other).
이러한 본 발명의 화학식 1로 표시되는 화합물은 유기 전계 발광 소자의 특성을 고려할 때, 하기 화학식 2 내지 5로 표시되는 화합물로 이루어진 군에서 선택되는 것이 바람직하다.The compound represented by the formula (1) of the present invention is preferably selected from the group consisting of compounds represented by the following formulas (2) to (5) in view of the characteristics of the organic electroluminescent device.
[화학식 2](2)
[화학식 3](3)
[화학식 4][Chemical Formula 4]
[화학식 5][Chemical Formula 5]
상기 화학식 2 내지 5 에서,In the above formulas 2 to 5,
X1 내지 X6 및 Ar1은 상기에서 정의된 바와 같으며, X7 내지 X9은 각각 독립적으로, N 또는 CR2이고,X 1 to X 6 and Ar 1 are as defined above and X 7 to X 9 are each independently N or CR 2 ,
Y1은 O, S, Se, N(R3) 및 C(R4)(R5)로 이루어진 군에서 선택되며,Y 1 is selected from the group consisting of O, S, Se, N (R 3 ) and C (R 4 ) (R 5 )
상기 R2 내지 R5는 각각 독립적으로, 수소, 중수소, 할로겐, 시아노, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되며, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고,Wherein R 2 to R 5 are each independently, hydrogen, deuterium, halogen, cyano, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C of 40 of the aryl group, the number of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group of, C 6 ~ C 40 aryl amine group, a C 3 ~ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group 1 ~ C 40 alkyl silyl group, the group alkyl boronic of C 1 ~ C 40, an aryl boronic a C 6 ~ C 40, C 6 ~ C A C 6 to C 40 arylphosphine oxide group, and a C 6 to C 40 arylsilyl group, which may be bonded to adjacent groups to form a condensed ring,
상기 R2 내지 R5의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 아릴아민기, 시클로알킬기, 헤테로시클로알킬기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되는 1종 이상의 치환기로 치환 또는 비치환될 수 있다. 여기서 R2 내지 R5가 복수개의 치환기로 치환될 경우, 복수개의 치환기는 서로 동일하거나 상이할 수 있다.Alkyl group of the R 2 to R 5, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, a cycloalkyl group, a heterocycloalkyl group, alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an aryl silyl group each independently selected from deuterium, halogen, a cyano, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 of the alkynyl A C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C 6 to C 40 aryloxy group, a C 1 to C 40 alkyloxy group, a C 6 to C 40 arylamine group, an aryl boronic of C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 40 group, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ substituted with a substituent at least one selected from the group consisting of C 40 again arylsilyl Beach can be ring. When R 2 to R 5 are substituted with a plurality of substituents, the plurality of substituents may be the same or different from each other.
또한 본 발명의 화학식 1로 표시되는 화합물은 유기 전계 발광 소자의 특성을 고려할 때, Ar1이 C6~C40의 아릴기 또는 핵원자수 5 내지 40의 헤테로아릴기인 것이 바람직하다.In addition, the compound represented by the general formula (I) of the present invention is preferably given the characteristics of the organic light emitting device, Ar 1 is C 6 ~ C 40 heteroaryl group of the aryl group or 5 to 40 nuclear atoms.
구체적으로 본 발명의 화학식 1로 표시되는 화합물에서, R1 내지 R5 및 Ar1은 각각 독립적으로, 수소 또는 하기 S1 내지 S204로 표시되는 구조(치환체)로 이루어진 군에서 선택되는 것이 바람직하다.Specifically, in the compound represented by the formula (1) of the present invention, R 1 to R 5 and Ar 1 are each independently selected from the group consisting of hydrogen or a structure (substituent) shown by the following S1 to S204.
이러한 본 발명의 화학식 1로 표시되는 화합물은 하기 화합물들로 구체화될 수 있으나, 이들에 한정되는 것은 아니다.The compound represented by the formula (1) of the present invention can be exemplified by the following compounds, but is not limited thereto.
본 발명의 화학식 1로 표시되는 화합물은 하기 합성예를 참조하여 다양하게 합성할 수 있다.The compounds represented by formula (1) of the present invention can be synthesized in various ways with reference to the following Synthesis Examples.
본 발명에서 알킬은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, alkyl means a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl.
본 발명에서 알케닐(alkenyl)은 탄소-탄소 이중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, alkenyl means a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
본 발명에서 알키닐(alkynyl)은 탄소-탄소 삼중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, alkynyl means a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
본 발명에서 아릴은 단독 고리 또는 2이상의 고리가 조합된 탄소수 6 내지 40의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있다. 이러한 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, aryl means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms in which a single ring or two or more rings are combined. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
본 발명에서 헤테로아릴은 핵원자수 5 내지 40의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로원자로 치환된다. 또한 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있고, 나아가 아릴기와의 축합된 형태도 포함될 수 있다. 이러한 헤테로아릴의 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6-원 모노사이클릭 고리, 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리 및 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, heteroaryl means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. It is also possible to include a form in which two or more rings are pendant or condensed with each other, and further, a condensed form with an aryl group may be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, and heterocyclic rings such as 2-furanyl, N-imidazolyl, 2- , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
본 발명에서 아릴옥시는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 6 내지 40의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, aryloxy is a monovalent substituent represented by RO-, and R represents aryl having 6 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
본 발명에서 알킬옥시는 R'O-로 표시되는 1가의 치환기로, 상기 R'는 탄소수 1 내지 40의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함할 수 있다. 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, alkyloxy is a monovalent substituent group represented by R'O-, wherein R 'represents alkyl having 1 to 40 carbon atoms, and includes a linear, branched or cyclic structure can do. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy and pentoxy.
본 발명에서 아릴아민은 탄소수 6 내지 40의 아릴로 치환된 아민을 의미한다.In the present invention, arylamine refers to an amine substituted with aryl having 6 to 40 carbon atoms.
본 발명에서 시클로알킬은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 노르보닐(norbornyl), 아다만틴(adamantine) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, cycloalkyl means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
본 발명에서 헤테로시클로알킬은 핵원자수 3 내지 40의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로 원자로 치환된다. 이러한 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, heterocycloalkyl means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon atom, preferably 1 to 3 carbons, of the ring is N, O, S or Se Lt; / RTI > Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
본 발명에서 알킬실릴은 탄소수 1 내지 40의 알킬로 치환된 실릴이고, 아릴실릴은 탄소수 6 내지 40의 아릴로 치환된 실릴을 의미한다.In the present invention, alkylsilyl is silyl substituted with alkyl having 1 to 40 carbon atoms, and arylsilyl means silyl substituted with aryl having 6 to 40 carbon atoms.
본 발명에서 축합고리는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.
In the present invention, the condensed rings refer to condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.
2. 유기 전계 발광 소자2. Organic electroluminescent device
본 발명은 양극(anode), 음극(cathode) 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다. 이때, 상기 화합물은 단독으로 사용되거나, 또는 2 이상이 혼합되어 사용될 수 있다.The present invention relates to an organic electroluminescent device comprising at least an anode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes a compound represented by Formula 1 An organic electroluminescent device is provided. At this time, the compounds may be used alone or in combination of two or more.
상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 발광층, 전자 수송층 및 전자 주입층 중 어느 하나 이상일 수 있다. 여기서 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 발광층인 것이 바람직하다.The one or more organic material layers may be at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. Here, the organic compound layer including the compound represented by Formula 1 is preferably a light emitting layer.
본 발명의 유기 전계 발광 소자의 발광층은 호스트 재료를 포함할 수 있는데, 이때 호스트 재료로 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 상기 화학식 1로 표시되는 화합물을 유기 전계 발광 소자의 발광층 재료, 바람직하게는 청색, 녹색, 적색의 인광 호스트 재료로 포함할 경우, 발광층에서 정공과 전자의 결합력이 높아지기 때문에, 유기 전계 발광 소자의 효율(발광효율 및 전력효율), 수명, 휘도 및 구동전압 등을 향상시킬 수 있다. 구체적으로 상기 화학식 1로 표시되는 화합물은 녹색 및/또는 적색의 인광 호스트, 형광 호스트, 또는 도펀트 재료로서 유기 전계 발광 소자에 포함되는 것이 바람직하다.The light emitting layer of the organic electroluminescent device of the present invention may include a host material, wherein the host material may include a compound represented by the above formula (1). When the compound represented by Formula 1 is contained as a light emitting layer material of an organic electroluminescent device, preferably a blue, green, or red phosphorescent host material, the bonding strength between holes and electrons in the light emitting layer is increased. (Luminous efficiency and power efficiency), lifetime, luminance, driving voltage and the like can be improved. Specifically, the compound represented by Formula 1 is preferably included in the organic electroluminescent device as a green and / or red phosphorescent host, a fluorescent host, or a dopant material.
본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 기판, 양극, 정공 주입층, 정공 수송층, 발광층, 전자 수송층 및 음극이 순차적으로 적층된 구조일 수 있다. 상기 전자 수송층 위에는 전자 주입층이 추가로 적층될 수 있다.The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially laminated. An electron injection layer may be further stacked on the electron transport layer.
또한 본 발명의 유기 전계 발광 소자의 구조는 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층될 뿐만 아니라, 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조일 수 있다.Further, the structure of the organic electroluminescent device of the present invention may be a structure in which an anode, one or more organic material layers and a cathode are sequentially laminated, and an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic material layer.
본 발명의 유기 전계 발광 소자는 상기 유기물층 중 1층 이상 (예컨대, 발광층)이 상기 화학식 1로 표시되는 화합물을 포함하도록 형성하는 것을 제외하고는, 당업계에 공지된 재료 및 방법을 이용하여 다른 유기물층 및 전극을 형성하여 제조될 수 있다.The organic electroluminescent device of the present invention may be formed by using materials and methods known in the art, except that at least one of the organic layers (for example, the light emitting layer) includes the compound represented by the above formula (1) And electrodes.
상기 유기물층은 진공 증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이들에 한정되지 않는다.The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
본 발명의 유기 전계 발광 소자에 포함되는 기판으로는 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등이 사용될 수 있다.As the substrate included in the organic electroluminescent device of the present invention, a silicon wafer, quartz, a glass plate, a metal plate, a plastic film and a sheet can be used.
또 양극 물질로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 또는 폴리아닐린과 같은 전도성 고분자; 및 카본블랙 등이 사용될 수 있다.Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black may be used.
또한 음극 물질로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금 및 LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 사용될 수 있다.The negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or an alloy thereof and a multilayer such as LiF / Al or LiO 2 / Structural materials and the like can be used.
또 정공 주입층, 정공 수송층, 전자 주입층 및 전자 수송층은 특별히 한정되는 것은 아니며, 당 업계에 알려진 통상의 물질이 사용될 수 있다.
The hole injecting layer, the hole transporting layer, the electron injecting layer and the electron transporting layer are not particularly limited, and ordinary materials known in the art can be used.
이하 본 발명을 실시예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐, 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.
Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are illustrative of the present invention, and the present invention is not limited by the following examples.
[준비예 1] 화합물 IC-1의 합성[Preparation Example 1] Synthesis of Compound IC-1
<단계 1> 1-(2-bromo-3-nitrophenyl)-5-phenyl-1H-pyrazole의 합성<Step 1> Synthesis of 1- (2-bromo-3-nitrophenyl) -5-phenyl-1H-pyrazole
질소 기류 하에서 5-phenyl-1H-pyrazole (6.65 g, 46.17 mmol), 2-bromo-1-iodo-3-nitrobenzene (15.13 g, 46.17 mmol), Cu powder (0.29 g, 4.62 mmol), K2CO3 (6.38 g, 46.17 mmol), nitrobenzene (200 ml)를 혼합한 다음, 190℃에서 12시간 동안 교반하였다. 반응 종결 후 nitrobenzene을 제거한 다음, 메틸렌클로라이드로 유기층을 분리하여 MgSO4를 사용하여 물을 제거하였다. 물이 제거된 유기층에서 용매를 제거한 후 컬럼크로마토그래피 (Hexane:MC = 3:1 (v/v))로 정제하여 1-(2-bromo-3-nitrophenyl)-5-phenyl-1H-pyrazole (12.39 g, 수율: 78%)을 얻었다.2-bromo-1-iodo-3-nitrobenzene (15.13 g, 46.17 mmol), Cu powder (0.29 g, 4.62 mmol), K 2 CO 3 (6.38 g, 46.17 mmol) and nitrobenzene (200 ml) were mixed and then stirred at 190 ° C for 12 hours. After completion of the reaction, nitrobenzene was removed, and the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . After removal of the solvent from the organic layer from which water had been removed, the residue was purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to give 1- (2-bromo-3-nitrophenyl) 12.39 g, yield: 78%).
1H-NMR: δ 6.74 (d, 1H), 7.09 (m, 2H), 7.48 (m, 4H), 7.66 (t, 1H), 7.90 (d, 1H), 8.18 (d, 1H) 1 H-NMR: δ 6.74 ( d, 1H), 7.09 (m, 2H), 7.48 (m, 4H), 7.66 (t, 1H), 7.90 (d, 1H), 8.18 (d, 1H)
<단계 2> 8-nitropyrazolo[1,5-f]phenanthridine의 합성<Step 2> Synthesis of 8-nitropyrazolo [1,5-f] phenanthridine
tris(trimethylsilyl)silane (0.49g, 2 mmol), azobisisobutyronitrile (0.82g, 5 mmol)를 dry degassed toluene (45 mL)에 녹인 후, 같은 용매 (60 mL)에 상기 준비예 1의 <단계 1>에서 얻은 1-(2-bromo-3-nitrophenyl)-5-phenyl-1H-pyrazole (1.72g, 5 mmol)를 한 방울씩 첨가하였다. 이 혼합물을 110℃에서 7시간 동안 교반한 후 상온에서 식혔다. 반응이 종결된 후, 감압 증류하여 유기 용매를 제거하고 컬럼크로마토그래피(Hexane:EA)로 정제하여 8-nitropyrazolo[1,5-f]phenanthridine (0.85 g, 수율 65%)을 얻었다.After dissolving tris (trimethylsilyl) silane (0.49 g, 2 mmol) and azobisisobutyronitrile (0.82 g, 5 mmol) in dry degassed toluene (45 mL), the same solvent (60 mL) The resulting 1- (2-bromo-3-nitrophenyl) -5-phenyl-1H-pyrazole (1.72 g, 5 mmol) was added dropwise. The mixture was stirred at 110 DEG C for 7 hours and then cooled at room temperature. After the reaction was completed, the organic solvent was removed by distillation under reduced pressure and the residue was purified by column chromatography (Hexane: EA) to obtain 8-nitropyrazolo [1,5-f] phenanthridine (0.85 g, yield 65%).
1H-NMR: δ 6.39 (d, 1H), 7.45 (m, 2H), 7.78 (m, 2H), 7.91 (m, 2H), 8.15 (m, 2H) 1 H-NMR: δ 6.39 ( d, 1H), 7.45 (m, 2H), 7.78 (m, 2H), 7.91 (m, 2H), 8.15 (m, 2H)
<단계 3> IC-1의 합성<Step 3> Synthesis of IC-1
질소 기류 하에서 상기 준비예 1의 <단계 2>에서 얻은 8-nitropyrazolo[1,5-f]phenanthridine (4.19 g, 15.91 mmol), triphenylphosphine (10.43 g, 39.77 mmol) 및 1,2-dichlorobenzene (50 ml)를 혼합한 다음, 12시간 동안 교반하였다. 반응 종료 후 1,2-dichlorobenzene를 제거하고 디클로로메탄으로 추출하였다. 얻어진 유기층에 대해 MgSO4로 물을 제거하고, 컬럼크로마토그래피 (Hexane:MC=3:1 (v/v))로 정제하여 화합물 IC-1 (1.91 g, 수율: 52%)를 얻었다.Nitropyrazolo [1,5-f] phenanthridine (4.19 g, 15.91 mmol), triphenylphosphine (10.43 g, 39.77 mmol) obtained in Step 2 of Preparation Example 1 and 1,2-dichlorobenzene ) Were mixed and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed and extracted with dichloromethane. Water was removed from the obtained organic layer with MgSO 4 and purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain Compound IC-1 (1.91 g, yield: 52%).
1H-NMR: δ 6.39 (d, 1H), 7.40 (m, 2H), 7.58 (d, 1H), 7.79 (m, 2H), 7.95 (m, 2H), 10.42 (s, 1H)
1 H-NMR: δ 6.39 ( d, 1H), 7.40 (m, 2H), 7.58 (d, 1H), 7.79 (m, 2H), 7.95 (m, 2H), 10.42 (s, 1H)
[준비예 2] 화합물 IC-2의 합성[Preparation Example 2] Synthesis of compound IC-2
<단계 1> 3-(1-(2-bromo-3-nitrophenyl)-1H-pyrazol-5-yl)pyridine의 합성<Step 1> Synthesis of 3- (1- (2-bromo-3-nitrophenyl) -1H-pyrazol-5-yl) pyridine
5-phenyl-1H-pyrazole 대신 3-(1H-pyrazol-5-yl)pyridine (6.70 g, 46.17 mmol)를 사용하는 것을 제외하고는, 상기 준비예 1의 <단계 1>과 동일한 과정을 수행하여 3-(1-(2-bromo-3-nitrophenyl)-1H-pyrazol-5-yl)pyridine을 얻었다.(1H-pyrazol-5-yl) pyridine (6.70 g, 46.17 mmol) instead of 5-phenyl- (2-bromo-3-nitrophenyl) -1H-pyrazol-5-yl) pyridine was obtained by following the procedure of <Step 1> of Preparation Example 1,
1H-NMR: δ 6.77 (d, 1H), 7.60 (m, 3H), 7.91 (d, 1H), 8.16 (d, 1H), 8.42 (d, 1H), 8.70 (d, 1H), 9.25 (s, 1H) 1 H-NMR:? 6.77 (d, 1 H), 7.60 (m, 3H), 7.91 (d, s, 1 H)
<단계 2> 8-nitrobenzo[c]pyrazolo[5,1-a][2,7]naphthyridine의 합성<Step 2> Synthesis of 8-nitrobenzo [c] pyrazolo [5,1-a] [2,7] naphthyridine
1-(2-bromo-3-nitrophenyl)-5-phenyl-1H-pyrazole 대신 상기 준비예 2의 <단계 1>에서 얻은 3-(1-(2-bromo-3-nitrophenyl)-1H-pyrazol-5-yl)pyridine (1.72 g, 5 mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 2>와 동일한 과정을 수행하여 8-nitrobenzo[c]pyrazolo[5,1-a][2,7]naphthyridine를 얻었다.(1- (2-bromo-3-nitrophenyl) -1H-pyrazol-3-yl] -pyrrolidine obtained in Step 1 of Preparation Example 2 was used instead of 1- (2-bromo- Pyrazolo [5,1-a] [2, 5-a] pyridine (1.72 g, 5 mmol) was used in the same manner as Step 2 of Preparation Example 1, , 7] naphthyridine.
1H-NMR: δ 6.40 (d, 1H), 7.38 (d, 1H), 7.80 (d, 1H), 7.93 (t, 1H), 8.14 (m, 2H), 8.43 (d, 1H), 9.38 (s, 1H) 1 H-NMR: δ 6.40 ( d, 1H), 7.38 (d, 1H), 7.80 (d, 1H), 7.93 (t, 1H), 8.14 (m, 2H), 8.43 (d, 1H), 9.38 ( s, 1 H)
<단계 3> IC-2의 합성<Step 3> Synthesis of IC-2
8-nitropyrazolo[1,5-f]phenanthridine 대신 상기 준비예 2의 <단계 2>에서 얻은 8-nitrobenzo[c]pyrazolo[5,1-a][2,7]naphthyridine (4.20 g, 15.91 mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 3>와 동일한 과정을 수행하여 화합물 IC-2를 얻었다.Nitrobenzo [c] pyrazolo [5,1-a] [2,7] naphthyridine (4.20 g, 15.91 mmol) obtained in Step 2 of Preparation Example 2 was used instead of 8-nitropyrazolo [ Was used to obtain Compound IC-2 by the same procedure as < Step 3 > of Preparation Example 1 above.
1H-NMR: δ 6.39 (d, 1H), 7.36 (d, 1H), 7.79 (m, 2H), 7.99 (d, 1H), 8.87 (s, 1H), 9.34 (s, 1H), 11.10 (s, 1H)
1 H-NMR: δ 6.39 ( d, 1H), 7.36 (d, 1H), 7.79 (m, 2H), 7.99 (d, 1H), 8.87 (s, 1H), 9.34 (s, 1H), 11.10 ( s, 1 H)
[준비예 3] 화합물 IC-3의 합성[Preparation Example 3] Synthesis of Compound IC-3
<단계 1> 1-(2-bromo-3-nitrophenyl)-5-(thiophen-2-yl)-1H-pyrazole의 합성<Step 1> Synthesis of 1- (2-bromo-3-nitrophenyl) -5- (thiophen-2-yl) -1H-pyrazole
5-phenyl-1H-pyrazole 대신 5-(thiophen-2-yl)-1H-pyrazole (6.93 g, 46.17 mmol)를 사용하는 것을 제외하고는, 상기 준비예 1의 <단계 1>과 동일한 과정을 수행하여 1-(2-bromo-3-nitrophenyl)-5-(thiophen-2-yl)-1H-pyrazole을 얻었다.5- (thiophen-2-yl) -1H-pyrazole (6.93 g, 46.17 mmol) instead of 5-phenyl- (2-bromo-3-nitrophenyl) -5- (thiophen-2-yl) -1H-pyrazole was obtained by following the procedure of <Step 1> of Preparation Example 1,
1H-NMR: δ 6.79 (d, 1H), 7.17 (t, 1H), 7.50 (d, 1H), 7.67 (m, 2H), 7.90 (d, 1H), 8.19 (m, 2H) 1 H-NMR: δ 6.79 ( d, 1H), 7.17 (t, 1H), 7.50 (d, 1H), 7.67 (m, 2H), 7.90 (d, 1H), 8.19 (m, 2H)
<단계 2> 7-nitropyrazolo[1,5-a]thieno[2,3-c]quinoline의 합성<Step 2> Synthesis of 7-nitropyrazolo [1,5-a] thieno [2,3-c] quinoline
1-(2-bromo-3-nitrophenyl)-5-phenyl-1H-pyrazole 대신 상기 준비예 3의 <단계 1>에서 얻은 1-(2-bromo-3-nitrophenyl)-5-(thiophen-2-yl)-1H-pyrazole (1.75 g, 5 mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 2>와 동일한 과정을 수행하여 7-nitropyrazolo[1,5-a]thieno[2,3-c]quinoline를 얻었다.(2-bromo-3-nitrophenyl) -5- (thiophen-2-yl) pyrazole obtained in Step 1 of Preparation Example 3 was used instead of 1- (2-bromo- The same procedure as in <Step 2> of Preparation Example 1 was carried out except that 1-methyl-1H-pyrazole (1.75 g, 5 mmol) was used instead of 7-nitropyrazolo [ -c] quinoline.
1H-NMR: δ 6.39 (d, 1H), 6.96 (d, 1H), 7.20 (d, 1H), 7.80 (d, 1H), 7.92 (t, 1H), 8.12 (m, 2H) 1 H-NMR: δ 6.39 ( d, 1H), 6.96 (d, 1H), 7.20 (d, 1H), 7.80 (d, 1H), 7.92 (t, 1H), 8.12 (m, 2H)
<단계 3> IC-3의 합성<Step 3> Synthesis of IC-3
8-nitropyrazolo[1,5-f]phenanthridine 대신 상기 준비예 3의 <단계 2>에서 얻은 7-nitropyrazolo[1,5-a]thieno[2,3-c]quinoline (4.28 g, 15.91 mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 3>와 동일한 과정을 수행하여 화합물 IC-3를 얻었다.7-nitropyrazolo [1,5-a] thieno [2,3-c] quinoline (4.28 g, 15.91 mmol) obtained in Step 2 of Preparation Example 3 was used instead of 8-nitropyrazolo [ The compound IC-3 was obtained in the same manner as in < Step 3 >
1H-NMR: δ 6.32 (d, 1H), 7.22 (s, 1H), 7.38 (d, 1H), 7.80 (m, 2H), 7.98 (d, 1H), 10.23 (s, 1H)
1 H-NMR:? 6.32 (d, IH), 7.22 (s, IH), 7.38 (d, IH), 7.80
[준비예 4] 화합물 IC-4의 합성[Preparation Example 4] Synthesis of Compound IC-4
<단계 1> 1-(2-bromo-3-nitrophenyl)-2-phenyl-1H-imidazole의 합성<Step 1> Synthesis of 1- (2-bromo-3-nitrophenyl) -2-phenyl-1H-imidazole
5-phenyl-1H-pyrazole 대신 2-phenyl-1H-imidazole (6.65 g, 46.17 mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 1>과 동일한 과정을 수행하여 1-(2-bromo-3-nitrophenyl)-2-phenyl-1H-imidazole을 얻었다.2-phenyl-1H-imidazole (6.65 g, 46.17 mmol) instead of 5-phenyl-1H- (2-bromo-3-nitrophenyl) -2-phenyl-1H-imidazole was obtained by following the procedure of <Step 1> of Preparation Example 1,
1H-NMR: δ 7.16 (d, 1H), 7.60 (m, 5H), 7.95 (d, 1H), 8.16 (d, 1H), 8.28 (m, 2H) 1 H-NMR: δ 7.16 ( d, 1H), 7.60 (m, 5H), 7.95 (d, 1H), 8.16 (d, 1H), 8.28 (m, 2H)
<단계 2> 8-nitroimidazo[1,2-f]phenanthridine의 합성<Step 2> Synthesis of 8-nitroimidazo [1,2-f] phenanthridine
1-(2-bromo-3-nitrophenyl)-5-phenyl-1H-pyrazole 대신 상기 준비예 4의 <단계 1>에서 얻은 1-(2-bromo-3-nitrophenyl)-2-phenyl-1H-imidazole (1.72 g, 5 mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 2>와 동일한 과정을 수행하여 8-nitroimidazo[1,2-f]phenanthridine를 얻었다.2-bromo-3-nitrophenyl) -2-phenyl-1H-imidazole obtained in Step 1 of Preparation Example 4 was used instead of 1- (2-bromo- 8-nitroimidazo [1,2-f] phenanthridine was obtained by following the procedure of <Step 2> of Preparation Example 1, except that the compound (1.72 g, 5 mmol) was used.
1H-NMR: δ 7.48 (m, 4H), 7.77 (d, 1H), 7.94 (m, 2H), 8.11 (d, 1H), 8.88 (d, 1H) 1 H-NMR: δ 7.48 ( m, 4H), 7.77 (d, 1H), 7.94 (m, 2H), 8.11 (d, 1H), 8.88 (d, 1H)
<단계 3> IC-4의 합성<Step 3> Synthesis of IC-4
8-nitropyrazolo[1,5-f]phenanthridine 대신 상기 준비예 4의 <단계 2>에서 얻은 8-nitroimidazo[1,2-f]phenanthridine (4.18 g, 15.91 mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 3>와 동일한 과정을 수행하여 화합물 IC-4를 얻었다.Except that 8-nitroimidazo [1,2-f] phenanthridine (4.18 g, 15.91 mmol) obtained in Step 2 of Preparation Example 4 was used in place of 8-nitropyrazolo [1,5- The same procedure as in <Step 3> of Example 1 was conducted to obtain compound IC-4.
1H-NMR: δ 7.45 (m, 5H), 7.80 (t, 1H), 7.90 (d, 1H), 8.62 (d, 1H), 10.33 (s, 1H)
1 H-NMR:? 7.45 (m, 5H), 7.80 (t, IH), 7.90
[준비예 5] 화합물 IC-5의 합성[Preparation Example 5] Synthesis of Compound IC-5
<단계 1> 1-(2-bromo-3-nitrophenyl)-2-phenyl-1H-benzo[d]imidazole의 합성<Step 1> Synthesis of 1- (2-bromo-3-nitrophenyl) -2-phenyl-1H-benzo [d] imidazole
5-phenyl-1H-pyrazole 대신 2-phenyl-1H-benzo[d]imidazole (8.96 g, 46.17 mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 1>과 동일한 과정을 수행하여 1-(2-bromo-3-nitrophenyl)-2-phenyl-1H-benzo[d]imidazole을 얻었다.2-phenyl-1H-benzo [d] imidazole (8.96 g, 46.17 mmol) instead of 5-phenyl- (2-bromo-3-nitrophenyl) -2-phenyl-1H-benzo [d] imidazole was obtained by following the procedure of <Step 1> of Preparation Example 1,
1H-NMR: δ 7.22 (m, 2H), 7.60 (m, 5H), 7.91 (d, 1H), 8.10 (d, 1H), 8.28 (m, 2H), 8.55 (d, 1H) 1 H-NMR: δ 7.22 ( m, 2H), 7.60 (m, 5H), 7.91 (d, 1H), 8.10 (d, 1H), 8.28 (m, 2H), 8.55 (d, 1H)
<단계 2> 4-nitrobenzo[4,5]imidazo[1,2-f]phenanthridine의 합성<Step 2> Synthesis of 4-nitrobenzo [4,5] imidazo [1,2-f] phenanthridine
1-(2-bromo-3-nitrophenyl)-5-phenyl-1H-pyrazole 대신 상기 준비예 5의 <단계 1>에서 얻은 1-(2-bromo-3-nitrophenyl)-2-phenyl-1H-benzo[d]imidazole (1.97 g, 5 mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 2>와 동일한 과정을 수행하여 4-nitrobenzo[4,5]imidazo[1,2-f]phenanthridine를 얻었다.(2-bromo-3-nitrophenyl) -2-phenyl-1H-benzo (2-bromo-3-nitrophenyl) -5-phenyl-1H-pyrazole obtained in Step 1 of Preparation Example 5 was used instead of 1- 4-nitrobenzo [4,5] imidazo [l, 2-f] phenanthridine was obtained by following the same procedure as in [Step 2] of Preparation Example 1 except that [d] imidazole (1.97 g, .
1H-NMR: δ 7.23 (m, 2H), 7.50 (m, 3H), 7.76 (d, 1H), 7.91 (m, 2H), 8.11 (d, 1H), 8.58 (d, 1H), 8.81 (d, 1H) 1 H-NMR: δ 7.23 ( m, 2H), 7.50 (m, 3H), 7.76 (d, 1H), 7.91 (m, 2H), 8.11 (d, 1H), 8.58 (d, 1H), 8.81 ( d, 1 H)
<단계 3> IC-5의 합성<Step 3> Synthesis of IC-5
8-nitropyrazolo[1,5-f]phenanthridine 대신 상기 준비예 5의 <단계 2>에서 얻은 4-nitrobenzo[4,5]imidazo[1,2-f]phenanthridine (4.98 g, 15.91 mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 3>와 동일한 과정을 수행하여 화합물 IC-5를 얻었다.4-nitrobenzo [4,5] imidazo [1,2-f] phenanthridine (4.98 g, 15.91 mmol) obtained in Step 2 of Preparation Example 5 was used instead of 8-nitropyrazolo [ The procedure of Step 3 of Preparation Example 1 was followed except that the compound IC-5 was obtained.
1H-NMR: δ 7.24 (m, 2H), 7.40 (m, 2H), 7.58 (m, 2H), 7.78 (t, 1H), 7.92 (d, 1H), 8.60 (d, 2H), 10.19 (s, 1H)
1 H-NMR: δ 7.24 ( m, 2H), 7.40 (m, 2H), 7.58 (m, 2H), 7.78 (t, 1H), 7.92 (d, 1H), 8.60 (d, 2H), 10.19 ( s, 1 H)
[준비예 6] 화합물 IC-6의 합성[Preparation Example 6] Synthesis of compound IC-6
<단계 1> 1-(2-bromo-3-nitrophenyl)-2,5-diphenyl-1H-pyrrole의 합성<Step 1> Synthesis of 1- (2-bromo-3-nitrophenyl) -2,5-diphenyl-1H-pyrrole
5-phenyl-1H-pyrazole 대신 2,5-diphenyl-1H-pyrrole (10.12 g, 46.17 mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 1>과 동일한 과정을 수행하여 1-(2-bromo-3-nitrophenyl)-2,5-diphenyl-1H-pyrrole을 얻었다.2,5-diphenyl-1H-pyrrole (10.12 g, 46.17 mmol) instead of 5-phenyl- (2-bromo-3-nitrophenyl) -2,5-diphenyl-1H-pyrrole was obtained by following the procedure of <Step 1> of Preparation Example 1,
1H-NMR: δ 6.58 (m, 2H), 7.45 (m, 6H), 7.65 (t, 1H), 7.79 (m, 4H), 7.91 (d, 1H), 8.17 (d, 1H) 1 H-NMR: δ 6.58 ( m, 2H), 7.45 (m, 6H), 7.65 (t, 1H), 7.79 (m, 4H), 7.91 (d, 1H), 8.17 (d, 1H)
<단계 2> 8-nitro-3-phenylpyrrolo[1,2-f]phenanthridine의 합성<Step 2> Synthesis of 8-nitro-3-phenylpyrrolo [1,2-f] phenanthridine
1-(2-bromo-3-nitrophenyl)-5-phenyl-1H-pyrazole 대신 상기 준비예 6의 <단계 1>에서 얻은 1-(2-bromo-3-nitrophenyl)-2,5-diphenyl-1H-pyrrole (2.09 g, 5 mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 2>와 동일한 과정을 수행하여 8-nitro-3-phenylpyrrolo[1,2-f]phenanthridine를 얻었다.2-bromo-3-nitrophenyl) -2,5-diphenyl-1H-pyrazole obtained in Step 1 of Preparation Example 6 was used instead of 1- (2-bromo- 2-phenylpyrrolo [l, 2-f] phenanthridine was obtained by following the procedure of <Step 2> of Preparation Example 1, except that diisopropylamine hydrochloride (2.09 g, 5 mmol)
1H-NMR: δ 6.83 (d, 1H), 7.18 (d, 1H), 7.49 (m, 5H), 7.78 (m, 3H), 7.92 (m, 2H), 8.11 (d, 1H), 8.85 (d, 1H) 1 H-NMR: δ 6.83 ( d, 1H), 7.18 (d, 1H), 7.49 (m, 5H), 7.78 (m, 3H), 7.92 (m, 2H), 8.11 (d, 1H), 8.85 ( d, 1 H)
<단계 3> IC-6의 합성<Step 3> Synthesis of IC-6
8-nitropyrazolo[1,5-f]phenanthridine 대신 상기 준비예 6의 <단계 2>에서 얻은 8-nitro-3-phenylpyrrolo[1,2-f]phenanthridine (5.38 g, 15.91 mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 3>와 동일한 과정을 수행하여 화합물 IC-6를 얻었다.Except that 8-nitro-3-phenylpyrrolo [1,2-f] phenanthridine (5.38 g, 15.91 mmol) obtained in Step 2 of Preparation Example 6 was used instead of 8-nitropyrazolo [ The compound IC-6 was obtained in the same manner as in <Step 3> of Preparation Example 1.
1H-NMR: δ 6.88 (d, 1H), 7.17 (d, 1H), 7.44 (m, 6H), 7.78 (m, 3H), 7.89 (d, 1H), 8.64 (d, 1H), 10.44 (s, 1H)
1 H-NMR: δ 6.88 ( d, 1H), 7.17 (d, 1H), 7.44 (m, 6H), 7.78 (m, 3H), 7.89 (d, 1H), 8.64 (d, 1H), 10.44 ( s, 1 H)
[준비예 7] 화합물 IC-7의 합성[Preparation Example 7] Synthesis of compound IC-7
<단계 1> 4-bromo-3-nitro-5-(5-phenyl-1H-pyrazol-1-yl)pyridine의 합성Synthesis of 4-bromo-3-nitro-5- (5-phenyl-1H-pyrazol-1-yl) pyridine
2-bromo-1-iodo-3-nitrobenzene 대신 4-bromo-3-iodo-5-nitropyridine (15.18 g, 46.17 mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 1>과 동일한 과정을 수행하여 4-bromo-3-nitro-5-(5-phenyl-1H-pyrazol-1-yl)pyridine을 얻었다.4-bromo-3-iodo-5-nitropyridine (15.18 g, 46.17 mmol) was used instead of 2-bromo-1-iodo-3- 4-bromo-3-nitro-5- (5-phenyl-1H-pyrazol-1-yl) pyridine was obtained by following the procedure of <Step 1> of Preparation Example 1,
1H-NMR: δ 6.84 (d, 1H), 7.08 (m, 2H), 7.31 (d, 1H), 7.50 (m, 3H), 8.81 (s, 1H), 9.30 (s, 1H) 1 H-NMR: δ 6.84 ( d, 1H), 7.08 (m, 2H), 7.31 (d, 1H), 7.50 (m, 3H), 8.81 (s, 1H), 9.30 (s, 1H)
<단계 2> 8-nitrobenzo[c]pyrazolo[1,5-a][1,7]naphthyridine의 합성<Step 2> Synthesis of 8-nitrobenzo [c] pyrazolo [1,5-a] [1,7] naphthyridine
1-(2-bromo-3-nitrophenyl)-5-phenyl-1H-pyrazole 대신 상기 준비예 7의 <단계 1>에서 얻은 4-bromo-3-nitro-5-(5-phenyl-1H-pyrazol-1-yl)pyridine (1.72 g, 5 mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 2>와 동일한 과정을 수행하여 8-nitrobenzo[c]pyrazolo[1,5-a][1,7]naphthyridine 를 얻었다.Bromo-3-nitro-5- (5-phenyl-1H-pyrazol-3-yl) -propionate obtained in Step 1 of Preparation Example 7 was used instead of 1- (2-bromo- 1-yl) pyridine (1.72 g, 5 mmol) was used in place of 2-nitrobenzo [c] pyrazolo [ , 7] naphthyridine.
1H-NMR: δ 6.39 (d, 1H), 7.45 (m, 2H), 7.79 (m, 2H), 7.94 (d, 1H), 9.53 (m, 2H) 1 H-NMR: δ 6.39 ( d, 1H), 7.45 (m, 2H), 7.79 (m, 2H), 7.94 (d, 1H), 9.53 (m, 2H)
<단계 3> IC-7의 합성<Step 3> Synthesis of IC-7
8-nitropyrazolo[1,5-f]phenanthridine 대신 상기 준비예 7의 <단계 2>에서 얻은 8-nitrobenzo[c]pyrazolo[1,5-a][1,7]naphthyridine (4.20 g, 15.91 mmol)를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 3>와 동일한 과정을 수행하여 화합물 IC-7를 얻었다.Nitrobenzo [c] pyrazolo [1,5-a] [1,7] naphthyridine (4.20 g, 15.91 mmol) obtained in Step 2 of Preparation Example 7 was used in place of 8-nitropyrazolo [ Was used to obtain Compound IC-7 by the same procedure as < Step 3 > of Preparation Example 1 above.
1H-NMR: δ 6.39 (d, 1H), 7.42 (t, 1H), 7.59 (d, 1H), 7.79 (d, 1H), 7.97 (d, 1H), 8.22 (s, 1H), 9.15 (s, 1H), 10.22 (s, 1H)
1 H-NMR: δ 6.39 ( d, 1H), 7.42 (t, 1H), 7.59 (d, 1H), 7.79 (d, 1H), 7.97 (d, 1H), 8.22 (s, 1H), 9.15 ( s, 1 H), 10.22 (s, 1 H)
[합성예 1] 화합물 C-1의 합성[Synthesis Example 1] Synthesis of Compound C-1
질소 기류 하에서 합성된 화합물 IC-1 (10.67 g, 46.17 mmol), 2-(4-bromophenyl)triphenylene (21.23 g, 55.40 mmol), Cu powder (0.29 g, 4.62 mmol), K2CO3 (6.38 g, 46.17 mmol), nitrobenzene (200 ml)를 혼합한 다음, 190℃에서 12시간 동안 교반하였다. 반응 종결 후 nitrobenzene을 제거한 다음, 메틸렌클로라이드로 유기층을 분리하여 MgSO4를 사용하여 물을 제거하였다. 물이 제거된 유기층에서 용매를 제거한 후 컬럼크로마토그래피로 정제하여 화합물 C-1 (11.33 g, 수율: 46%)을 얻었다.(10.67 g, 46.17 mmol), 2- (4-bromophenyl) triphenylene (21.23 g, 55.40 mmol), Cu powder (0.29 g, 4.62 mmol) and K 2 CO 3 , 46.17 mmol) and nitrobenzene (200 ml) were mixed and then stirred at 190 ° C for 12 hours. After completion of the reaction, nitrobenzene was removed, and the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The solvent was removed from the organic layer from which water had been removed and then purified by column chromatography to obtain Compound C-1 (11.33 g, yield: 46%).
GC-Mass (이론치: 533.62 g/mol, 측정치: 533 g/mol)
GC-Mass (calculated: 533.62 g / mol, measured: 533 g / mol)
[합성예 2] 화합물 C-2의 합성[Synthesis Example 2] Synthesis of Compound C-2
2-(4-bromophenyl)triphenylene 대신 2-bromo-4,6-diphenyl-1,3,5-triazine (17.29 g, 55.40 mmol) 을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 C-2 (15.16 g, 수율: 71%)을 얻었다.The same procedure as in Synthesis Example 1 was repeated but using 2-bromo-4,6-diphenyl-1,3,5-triazine (17.29 g, 55.40 mmol) instead of 2- (4-bromophenyl) C-2 (15.16 g, yield: 71%).
GC-Mass (이론치: 462.50 g/mol, 측정치: 462 g/mol)
GC-Mass (theory: 462.50 g / mol, measurement: 462 g / mol)
[합성예 3] 화합물 C-3의 합성[Synthesis Example 3] Synthesis of Compound C-3
2-(4-bromophenyl)triphenylene 대신 2-bromo-4,6-diphenylpyrimidine (17.24 g, 55.40 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 C-3 (14.70 g, 수율: 69%)을 얻었다.The same procedure as in Synthesis Example 1 was repeated, except that 2-bromo-4,6-diphenylpyrimidine (17.24 g, 55.40 mmol) was used instead of 2- (4-bromophenyl) triphenylene to obtain Compound C- : 69%).
GC-Mass (이론치: 461.52 g/mol, 측정치: 461 g/mol)
GC-Mass (calculated: 461.52 g / mol, measured: 461 g / mol)
[합성예 4] 화합물 C-4의 합성[Synthesis Example 4] Synthesis of Compound C-4
2-(4-bromophenyl)triphenylene 대신 2-bromo-6-phenylpyridine (12.97 g, 55.40 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 C-4 (14.02 g, 수율: 79%)을 얻었다.The same procedure as in Synthesis Example 1 was repeated, except that 2-bromo-6-phenylpyridine (12.97 g, 55.40 mmol) was used instead of 2- (4-bromophenyl) triphenylene to obtain Compound C-4 (14.02 g, yield: 79 %).
GC-Mass (이론치: 384.43 g/mol, 측정치: 384 g/mol)
GC-Mass (calculated: 384.43 g / mol, measured: 384 g / mol)
[합성예 5] 화합물 C-5의 합성[Synthesis Example 5] Synthesis of Compound C-5
2-(4-bromophenyl)triphenylene 대신 4-bromo-N,N-diphenylaniline (17.96 g, 55.40 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 C-5 (15.77 g, 수율: 72%)을 얻었다.The same procedure as in Synthesis Example 1 was carried out except that 4-bromo-N, N-diphenylaniline (17.96 g, 55.40 mmol) was used instead of 2- (4-bromophenyl) triphenylene to obtain Compound C- : 72%).
GC-Mass (이론치: 474.55 g/mol, 측정치: 474 g/mol)
GC-Mass (calculated: 474.55 g / mol, measured: 474 g / mol)
[합성예 6] 화합물 C-6의 합성[Synthesis Example 6] Synthesis of Compound C-6
2-(4-bromophenyl)triphenylene 대신 (4-bromophenyl)triphenylsilane (23.01 g, 55.40 mmol)를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 C-6 (10.44 g, 수율: 40%)을 얻었다.(10.44 g, yield: 40%) was obtained in the same manner as in Synthesis Example 1, except that (4-bromophenyl) triphenylsilane (23.01 g, 55.40 mmol) ).
GC-Mass (이론치: 565.74 g/mol, 측정치: 565 g/mol)
GC-Mass (calculated: 565.74 g / mol, measured: 565 g / mol)
[합성예 7] 화합물 C-7의 합성[Synthesis Example 7] Synthesis of Compound C-7
2-(4-bromophenyl)triphenylene 대신 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (21.50 g, 55.40 mmol)를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 C-7 (20.14 g, 수율: 81%)을 얻었다.The same procedure as in Synthesis Example 1 was carried out except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (21.50 g, 55.40 mmol) was used instead of 2- (4-bromophenyl) To obtain Compound C-7 (20.14 g, yield: 81%).
GC-Mass (이론치: 538.60 g/mol, 측정치: 538 g/mol)
GC-Mass (calculated: 538.60 g / mol, measured: 538 g / mol)
[합성예 8] 화합물 C-8의 합성[Synthesis Example 8] Synthesis of Compound C-8
2-(4-bromophenyl)triphenylene 대신 2-(4'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (25.72 g, 55.40 mmol)를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 C-8 (18.73 g, 수율: 66%)를 얻었다.2- (4'-bromo- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (25.72 g, 55.40 mmol) instead of 2- (4-bromophenyl) triphenylene ), The same procedure as in Synthesis Example 1 was conducted to obtain Compound C-8 (18.73 g, yield: 66%).
GC-Mass (이론치: 614.70 g/mol, 측정치: 614 g/mol)
GC-Mass (calculated: 614.70 g / mol, measured: 614 g / mol)
[합성예 9] 화합물 C-9의 합성[Synthesis Example 9] Synthesis of Compound C-9
2-(4-bromophenyl)triphenylene 대신 4-(4-bromophenyl)-2,6-diphenylpyrimidine (21.45 g, 55.40 mmol)를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 화합물 C-9 (18.61 g, 수율: 75%)을 얻었다.The same procedure as in Synthesis Example 1 was carried out except that 4- (4-bromophenyl) -2,6-diphenylpyrimidine (21.45 g, 55.40 mmol) was used instead of 2- (4-bromophenyl) 18.61 g, yield: 75%).
GC-Mass (이론치: 537.61 g/mol, 측정치: 537 g/mol)
GC-Mass (calculated: 537.61 g / mol, measured: 537 g / mol)
[합성예 10] 화합물 C-10의 합성[Synthesis Example 10] Synthesis of Compound C-10
IC-1 대신 IC-2 (10.72 g, 46.17 mmol)를 사용하는 것을 제외하고는 합성예 2와 동일한 과정을 수행하여 화합물 C-10 (14.33 g, 수율: 67%)을 얻었다.Compound C-10 (14.33 g, yield: 67%) was obtained in the same manner as in Synthesis Example 2, except that IC-2 (10.72 g, 46.17 mmol) was used instead of IC-1.
GC-Mass (이론치: 463.49 g/mol, 측정치: 463 g/mol)
GC-Mass (calculated: 463.49 g / mol, measured: 463 g / mol)
[합성예 11] 화합물 C-11의 합성[Synthesis Example 11] Synthesis of Compound C-11
IC-1 대신 IC-3 (10.95 g, 46.17 mmol)를 사용하는 것을 제외하고는 합성예 2와 동일한 과정을 수행하여 화합물 C-11 (11.46 g, 수율: 53%)을 얻었다.Compound C-11 (11.46 g, yield: 53%) was obtained in the same manner as in Synthesis Example 2 except that IC-3 (10.95 g, 46.17 mmol) was used instead of IC-1.
GC-Mass (이론치: 468.53 g/mol, 측정치: 468 g/mol)
GC-Mass (calculated: 468.53 g / mol, measured: 468 g / mol)
[합성예 12] 화합물 C-12의 합성[Synthesis Example 12] Synthesis of Compound C-12
IC-1 대신 IC-4 (10.67 g, 46.17 mmol)를 사용하는 것을 제외하고는 합성예 2와 동일한 과정을 수행하여 화합물 C-12 (13.23 g, 수율: 62%)을 얻었다.Compound C-12 (13.23 g, yield: 62%) was obtained in the same manner as in Synthesis Example 2 except that IC-4 (10.67 g, 46.17 mmol) was used instead of IC-1.
GC-Mass (이론치: 462.50 g/mol, 측정치: 462 g/mol)
GC-Mass (theory: 462.50 g / mol, measurement: 462 g / mol)
[합성예 13] 화합물 C-13의 합성[Synthesis Example 13] Synthesis of Compound C-13
IC-1 대신 IC-5 (12.98 g, 46.17 mmol)를 사용하는 것을 제외하고는 합성예 2와 동일한 과정을 수행하여 화합물 C-13 (13.01 g, 수율: 55%)을 얻었다.Compound C-13 (13.01 g, yield: 55%) was obtained in the same manner as in Synthesis Example 2 except that IC-5 (12.98 g, 46.17 mmol) was used instead of IC-1.
GC-Mass (이론치: 512.56 g/mol, 측정치: 512 g/mol)
GC-Mass (calculated: 512.56 g / mol, measured: 512 g / mol)
[합성예 14] 화합물 C-14의 합성[Synthesis Example 14] Synthesis of Compound C-14
IC-1 대신 IC-6 (14.14 g, 46.17 mmol)를 사용하는 것을 제외하고는 합성예 2와 동일한 과정을 수행하여 화합물 C-14 (16.13 g, 수율: 65%)을 얻었다.Compound C-14 (16.13 g, yield: 65%) was obtained in the same manner as in Synthesis Example 2, except that IC-6 (14.14 g, 46.17 mmol) was used instead of IC-1.
GC-Mass (이론치: 537.61 g/mol, 측정치: 537 g/mol)
GC-Mass (calculated: 537.61 g / mol, measured: 537 g / mol)
[합성예 15] 화합물 C-15의 합성[Synthesis Example 15] Synthesis of Compound C-15
IC-1 대신 IC-7 (10.72 g, 46.17 mmol)를 사용하는 것을 제외하고는 합성예 2와 동일한 과정을 수행하여 화합물 C-15 (10.48 g, 수율: 49%)을 얻었다.Compound C-15 (10.48 g, yield: 49%) was obtained in the same manner as in Synthesis Example 2, except that IC-7 (10.72 g, 46.17 mmol) was used instead of IC-1.
GC-Mass (이론치: 463.49 g/mol, 측정치: 463 g/mol)
GC-Mass (calculated: 463.49 g / mol, measured: 463 g / mol)
[실시예 1 내지 15][Examples 1 to 15]
합성예 1 내지 15에서 합성한 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 녹색 유기 전계 발광 소자를 제조하였다.The compounds synthesized in Synthesis Examples 1 to 15 were subjected to high purity sublimation purification by a conventionally known method, and then a green organic electroluminescent device was manufactured according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수로 초음파 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was ultrasonically washed with distilled water. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.
이렇게 준비된 ITO 투명 기판(전극) 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ 90% 합성예 1 내지 15 각각의 화합물 + 10 % Ir(ppy)3 (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 소자를 제조하였다.
(60 nm) / TCTA (80 nm) / 90% compound of each of Synthesis Examples 1 to 15 + 10% Ir (ppy) 3 (30 nm) / BCP (10 nm) on an ITO transparent substrate (electrode) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) in this order.
[비교예 1][Comparative Example 1]
발광층 형성시 발광 호스트 물질로서 합성예 1의 화합물 대신 CBP를 사용하는 것을 제외하고는 실시예 1과 동일한 과정으로 녹색 유기 전계 발광 소자를 제조하였다.
A green organic electroluminescent device was prepared in the same manner as in Example 1, except that CBP was used instead of the compound of Synthesis Example 1 as a luminescent host material in forming the light emitting layer.
상기 실시예 1 내지 15 및 비교예 1에서 사용된 m-MTDATA, TCTA, Ir(ppy)3, BCP 및 CBP의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, Ir (ppy) 3 , BCP and CBP used in Examples 1 to 15 and Comparative Example 1 are as follows.
[평가예][Evaluation example]
실시예 1 내지 15 및 비교예 1에서 제조한 각각의 녹색 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 1에 나타내었다.The driving voltage, current efficiency and emission peak at the current density of 10 mA / cm 2 were measured for each of the green organic electroluminescent devices prepared in Examples 1 to 15 and Comparative Example 1, and the results are shown in the following Table 1 .
상기 표 1에 나타낸 바와 같이, 본 발명의 화합물을 녹색 유기 전계 발광 소자의 발광층에 사용한 경우(실시예 1 내지 15)가 종래 CBP를 발광층에 사용한 경우(비교예 1)보다 효율 및 구동전압이 우수한 것을 확인할 수 있었다.As shown in Table 1, when the compound of the present invention was used for the light emitting layer of the green organic electroluminescent device (Examples 1 to 15), the efficiency and the drive voltage were higher than those of the conventional CBP used for the light emitting layer .
Claims (7)
[화학식 1]
상기 화학식 1에서,
X1 내지 X6은 각각 독립적으로 N 또는 CR1이고,
Cy1은 5원 헤테로방향족 고리, 6원 방향족 고리 또는 6원 헤테로방향족 고리이고,
Ar1은 C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴아민기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고,
상기 R1은 수소 및 C6~C40의 아릴기로 이루어진 군에서 선택되며, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고,
상기 Ar1의 아릴기, 헤테로아릴기, 아릴아민기 및 아릴실릴기는 각각 독립적으로 C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴아민기 및 C6~C40의 아릴실릴기로 이루어진 군으로부터 선택되는 1종 이상으로 치환될 수 있고,
상기 5원 헤테로방향족 고리, 6원 헤테로방향족 고리 및 핵원자수 5 내지 40의 헤테로아릴기는 각각 독립적으로 N, O, S 및 Se로 이루어진 군에서 선택된 1종 이상의 헤테로원자를 포함한다.A compound represented by the following formula (1):
[Chemical Formula 1]
In Formula 1,
X 1 to X 6 are each independently N or CR 1 ,
Cy1 is a 5-membered heteroaromatic ring, a 6-membered aromatic ring or a 6-membered heteroaromatic ring,
Ar 1 is selected from the group consisting of a C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C 6 to C 40 arylamine group, and a C 6 to C 40 arylsilyl group,
Wherein R 1 is selected from the group consisting of hydrogen and a C 6 -C 40 aryl group, and may be bonded to adjacent groups to form a condensed ring,
The aryl group, heteroaryl group, arylamine group and arylsilyl group of Ar 1 are each independently a C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C 6 to C 40 arylamine group And an arylsilyl group having from 6 to 40 carbon atoms,
The 5-membered heteroaromatic ring, the 6-membered heteroaromatic ring and the heteroaryl group having 5 to 40 nuclear atoms each independently contain at least one hetero atom selected from the group consisting of N, O, S and Se.
상기 화학식 1로 표시되는 화합물이 하기 화학식 2 내지 화학식 4로 표시되는 화합물로 이루어진 군에서 선택되는 화합물:
[화학식 2]
[화학식 3]
[화학식 4]
상기 화학식 2 내지 화학식 4에서,
X1 내지 X6 및 Ar1은 제1항에서 정의한 바와 같으며,
X7 내지 X9은 각각 독립적으로, N 또는 CR2이고,
Y1은 S이고,
상기 R2는 수소이다.The method according to claim 1,
Wherein the compound represented by Formula 1 is selected from the group consisting of compounds represented by Chemical Formulas 2 to 4:
(2)
(3)
[Chemical Formula 4]
In the above Chemical Formulas 2 to 4,
X 1 to X 6 and Ar 1 are as defined in claim 1,
X 7 to X 9 are each independently N or CR 2 ,
Y 1 is S,
R 2 is hydrogen.
상기 Ar1은 하기 S1 내지 S14, S16 내지 S31, S34 내지 S69, S71 내지 S122, S124 내지 S141, S145 내지 S151, S158, S160 내지 S162, S167 내지 S169, S171 내지 S176, S178 내지 S181, S183 내지 S188, S191 내지 S196, S198 내지 S202 및 S204로 표시되는 구조로 이루어진 군에서 선택되는 화합물.
The above-mentioned Ar 1 is represented by the following S1 to S14, S16 to S31, S34 to S69, S71 to S122, S124 to S141, S145 to S151, S158, S160 to S162, S167 to S169, S171 to S176, S178 to S181, S183 to S188 , S191 to S196, S198 to S202, and S204.
상기 Cy1이 벤젠 고리 또는 피리딘 고리인 화합물.The method according to claim 1,
Wherein Cy1 is a benzene ring or a pyridine ring.
상기 유기물층 중 적어도 하나는 제1항 내지 제3항 및 제5항 중 어느 한 항에 기재된 화합물을 포함하는 유기 전계 발광 소자.A cathode, and at least one organic layer interposed between the anode and the cathode,
Wherein at least one of the organic material layers comprises the compound according to any one of claims 1 to 3.
상기 화합물을 포함하는 유기물층이 발광층인 유기 전계 발광 소자.The method according to claim 6,
Wherein the organic compound layer containing the compound is a light emitting layer.
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