KR102673121B1 - Organic compound and organic electroluminescent device using the same - Google Patents
Organic compound and organic electroluminescent device using the same Download PDFInfo
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- KR102673121B1 KR102673121B1 KR1020160133400A KR20160133400A KR102673121B1 KR 102673121 B1 KR102673121 B1 KR 102673121B1 KR 1020160133400 A KR1020160133400 A KR 1020160133400A KR 20160133400 A KR20160133400 A KR 20160133400A KR 102673121 B1 KR102673121 B1 KR 102673121B1
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- 150000002894 organic compounds Chemical class 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 447
- 239000011368 organic material Substances 0.000 claims abstract description 21
- 239000010410 layer Substances 0.000 claims description 85
- 125000003118 aryl group Chemical group 0.000 claims description 70
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 125000004429 atom Chemical group 0.000 claims description 45
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 44
- 125000001072 heteroaryl group Chemical group 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 31
- 125000003342 alkenyl group Chemical group 0.000 claims description 29
- 125000000304 alkynyl group Chemical group 0.000 claims description 28
- 125000005264 aryl amine group Chemical group 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 125000004104 aryloxy group Chemical group 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 27
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 26
- 125000005104 aryl silyl group Chemical group 0.000 claims description 26
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- 229910052805 deuterium Inorganic materials 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 238000002347 injection Methods 0.000 claims description 15
- 239000007924 injection Substances 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 125000000732 arylene group Chemical group 0.000 claims description 10
- 239000012044 organic layer Substances 0.000 claims description 9
- 230000005525 hole transport Effects 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000005549 heteroarylene group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 3
- 238000004020 luminiscence type Methods 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 description 461
- 238000003786 synthesis reaction Methods 0.000 description 461
- 238000000034 method Methods 0.000 description 161
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 133
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 127
- 239000000463 material Substances 0.000 description 48
- 238000002360 preparation method Methods 0.000 description 33
- 238000005160 1H NMR spectroscopy Methods 0.000 description 24
- 230000000052 comparative effect Effects 0.000 description 24
- MVDYXUKNMGWCKS-UHFFFAOYSA-N 2-chloro-4-phenyl-1,3,5-triazine Chemical compound ClC1=NC=NC(C=2C=CC=CC=2)=N1 MVDYXUKNMGWCKS-UHFFFAOYSA-N 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- KDAMIIXNZSDBSF-UHFFFAOYSA-N 2-(3-bromophenyl)-4-phenyl-1,3,5-triazine Chemical compound BrC=1C=C(C=CC=1)C1=NC(=NC=N1)C1=CC=CC=C1 KDAMIIXNZSDBSF-UHFFFAOYSA-N 0.000 description 12
- OXTGJLAJVNZAKW-UHFFFAOYSA-N 2-(3-bromophenyl)-4-phenylquinazoline Chemical compound BrC1=CC=CC(C=2N=C3C=CC=CC3=C(C=3C=CC=CC=3)N=2)=C1 OXTGJLAJVNZAKW-UHFFFAOYSA-N 0.000 description 12
- FARAOARIVJZINN-UHFFFAOYSA-N 2-(4-bromophenyl)-4-phenylquinazoline Chemical compound C1=CC(Br)=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 FARAOARIVJZINN-UHFFFAOYSA-N 0.000 description 12
- YTTFZSLFNVFHAQ-UHFFFAOYSA-N 2-chloro-4-(4-naphthalen-1-ylphenyl)quinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(C=3C=CC(=CC=3)C=3C4=CC=CC=C4C=CC=3)=C21 YTTFZSLFNVFHAQ-UHFFFAOYSA-N 0.000 description 12
- HGPVPXXVBLDHPA-UHFFFAOYSA-N 2-chloro-4-phenylbenzo[h]quinazoline Chemical compound C1(=NC(C2=CC=CC=C2)=C2C=CC3=CC=CC=C3C2=N1)Cl HGPVPXXVBLDHPA-UHFFFAOYSA-N 0.000 description 12
- SFKMVPQJJGJCMI-UHFFFAOYSA-N 2-chloro-4-phenylquinazoline Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1C1=CC=CC=C1 SFKMVPQJJGJCMI-UHFFFAOYSA-N 0.000 description 12
- -1 metal complex compounds Chemical class 0.000 description 12
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- 239000002019 doping agent Substances 0.000 description 8
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- MJDDVTZXYXHTRY-UHFFFAOYSA-N 4-chloro-2,6-diphenylpyrimidine Chemical compound N=1C(Cl)=CC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 MJDDVTZXYXHTRY-UHFFFAOYSA-N 0.000 description 7
- AYLPNKHVFZUMJF-UHFFFAOYSA-N (9,9-dimethyl-10-phenylacridin-2-yl)boronic acid Chemical compound C12=CC=C(B(O)O)C=C2C(C)(C)C2=CC=CC=C2N1C1=CC=CC=C1 AYLPNKHVFZUMJF-UHFFFAOYSA-N 0.000 description 6
- QNGVEVOZKYHNGL-UHFFFAOYSA-N 2-chloro-4,6-diphenylpyrimidine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 QNGVEVOZKYHNGL-UHFFFAOYSA-N 0.000 description 6
- RDLQLVAVVVLVEW-UHFFFAOYSA-N 4-chloro-2-phenylpyrimidine Chemical compound ClC1=CC=NC(C=2C=CC=CC=2)=N1 RDLQLVAVVVLVEW-UHFFFAOYSA-N 0.000 description 6
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- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 6
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 5
- YHAHNQXQOZYZLP-UHFFFAOYSA-N 10-bromo-7h-benzo[c]carbazole Chemical compound C1=CC=CC2=C(C=3C(=CC=C(C=3)Br)N3)C3=CC=C21 YHAHNQXQOZYZLP-UHFFFAOYSA-N 0.000 description 5
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- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical compound C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 3
- QXOGPTXQGKQSJT-UHFFFAOYSA-N 1-amino-4-[4-(3,4-dimethylphenyl)sulfanylanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound Cc1ccc(Sc2ccc(Nc3cc(c(N)c4C(=O)c5ccccc5C(=O)c34)S(O)(=O)=O)cc2)cc1C QXOGPTXQGKQSJT-UHFFFAOYSA-N 0.000 description 3
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- 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
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 230000000903 blocking effect Effects 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
- 125000005566 carbazolylene group Chemical group 0.000 description 1
- 239000006229 carbon black 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
- 239000003086 colorant Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 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
- 238000003618 dip coating 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
- 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
- 125000004435 hydrogen atom Chemical group [H]* 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
- 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
- 239000002346 layers by function Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000005564 oxazolylene group Chemical group 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
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 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
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 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
- 125000005551 pyridylene 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
- 125000005576 pyrimidinylene group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000011160 research Methods 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
- 229910052711 selenium Inorganic materials 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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000000126 substance Substances 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
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000005559 triazolylene group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation 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
- 235000012431 wafers Nutrition 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
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- C07D209/56—Ring systems containing three or more rings
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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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- H10K50/14—Carrier transporting layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/17—Carrier injection 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
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- 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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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
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Abstract
본 발명은 신규한 유기 화합물 및 이를 이용한 유기 전계 발광 소자에 관한 것으로, 보다 상세하게는 발광능이 우수한 신규 화합물 및 이를 하나 이상의 유기물층에 포함함으로써, 높은 발광효율, 낮은 구동전압, 긴 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic compound and an organic electroluminescent device using the same. More specifically, a novel compound with excellent luminescence performance and its inclusion in one or more organic material layers provide characteristics such as high luminous efficiency, low driving voltage, and long lifespan. It relates to improved organic electroluminescent devices.
Description
본 발명은 신규한 유기 화합물 및 이를 이용한 유기 전계 발광 소자에 관한 것으로, 보다 상세하게는 발광능이 우수한 화합물 및 이를 하나 이상의 유기물층에 포함함으로써, 발광효율, 구동전압, 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more specifically, to a compound with excellent luminescence performance and its inclusion in one or more organic material layers, thereby improving organic electroluminescence properties such as luminous efficiency, driving voltage, and lifespan. It's about elements.
1950년대 Bernanose의 유기 박막 발광 관측을 시점으로 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계 발광(electroluminescent) 소자에 대한 연구는 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층구조의 유기 전계 발광 소자가 제시되었다. 이후, 고효율, 고수명의 유기 전계 발광 소자를 만들기 위하여, 소자 내 각각의 특징적인 유기물층을 도입하는 형태로 발전하여 왔으며, 이에 사용되는 특화된 물질의 개발로 이어졌다.Beginning with Bernanose's observation of organic thin film luminescence in the 1950s, research on organic electroluminescent devices, which led to blue electroluminescence using anthracene single crystals in 1965, was divided into a functional layer of a hole layer and a light emitting layer by Tang in 1987. An organic electroluminescent device with a layered structure was presented. Since then, in order to create high-efficiency, long-life organic electroluminescent devices, there has been development in the form of introducing each characteristic organic material layer within the device, leading to the development of specialized materials used for this.
유기 전계 발광 소자에서는 두 전극 사이에 전압을 걸어 주면 양극에서는 정공이 주입되고, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 이때 유기물층으로 사용되는 물질은 그 기능에 따라, 발광 물질, 정공 주입 물질, 정공 수송 물질, 전자 수송 물질, 전자 주입 물질 등으로 분류될 수 있다.In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected from the anode and electrons are injected from the cathode into the organic material layer. When the injected hole and electron meet, an exciton is formed, and when this exciton falls to the ground state, light is emitted. At this time, the material used as the organic material layer can be classified into light-emitting material, hole injection material, hole transport material, electron transport material, electron injection material, etc., depending on its function.
유기 전계 발광 소자의 발광층 형성재료는 발광색에 따라 청색, 녹색, 적색 발광 재료로 구분될 수 있다. 그밖에, 보다 나은 천연색을 구현하기 위한 발광재료로 노란색 및 주황색 발광재료도 사용된다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 재료로서 호스트/도펀트 계를 사용할 수 있다.Materials for forming the light-emitting layer of an organic electroluminescent device can be classified into blue, green, and red light-emitting materials depending on the color of the light. In addition, yellow and orange luminescent materials are also used as luminescent materials to realize better natural colors. Additionally, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system can be used as a luminescent material.
도판트 물질은 유기 물질을 사용하는 형광 도판트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도판트로 나눌 수 있다. 이러한 인광 재료의 개발은 이론적으로 형광에 비해 4배까지의 발광 효율을 향상시킬 수 있어 인광 도판트 뿐만 아니라 인광 호스트 재료들에 대해 관심이 집중되고 있다.Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. The development of these phosphorescent materials can theoretically improve luminous efficiency by up to 4 times compared to fluorescence, so interest is focused on not only phosphorescent dopants but also phosphorescent host materials.
현재까지 정공 주입층, 정공 수송층. 정공 차단층, 전자 수송층으로 사용되는 물질은, 하기 화학식으로 표현된 NPB, BCP, Alq3 등이 널리 알려져 있고, 발광 물질로는 안트라센 유도체들이 형광 도판트/호스트 재료로서 보고되고 있다. 특히 발광재료 중 효율 향상 측면에서 큰 장점을 가지고 있는 인광 도펀트 재료로서는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 청색, 녹색, 적색 도판트 재료로 사용되고 있다. 현재까지는 CBP가 인광 호스트 재료로 우수한 특성을 나타내고 있다.So far, hole injection layer and hole transport layer. Materials used as hole blocking layers and electron transport layers are widely known, such as NPB, BCP, and Alq 3 expressed by the following chemical formula, and as light-emitting materials, anthracene derivatives have been reported as fluorescent dopant/host materials. In particular, among light emitting materials, phosphorescent dopant materials that have great advantages in terms of efficiency improvement include metal complex compounds containing Ir such as Firpic, Ir(ppy) 3 , (acac)Ir(btp) 2 , etc., which produce blue, green, and red dopants. It is used as a material. To date, CBP has shown excellent properties as a phosphorescent host material.
그러나, 종래 발광 물질들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮고 열적 안정성이 매우 좋지 않기 때문에, 유기 전계 발광 소자에서의 수명 측면에서 만족할만한 수준이 되지 못하고 있다. 따라서, 우수한 성능을 가지는 발광 물질의 개발이 요구되고 있다.However, although conventional light-emitting materials have advantages in terms of light-emitting properties, their glass transition temperature is low and thermal stability is very poor, so they are not at a satisfactory level in terms of lifespan in organic electroluminescent devices. Therefore, there is a demand for the development of light-emitting materials with excellent performance.
상기한 문제점을 해결하기 위해, 본 발명은 유기 전계 발광 소자에 적용할 수 있으며, 발광능이 우수한 신규 유기 화합물을 제공하는 것을 목적으로 한다.In order to solve the above problems, the present invention aims to provide a new organic compound that can be applied to organic electroluminescent devices and has excellent luminescent performance.
또한, 본 발명은 상기 신규 유기 화합물을 포함하여 낮은 구동전압과 높은 발광효율을 나타내며 수명이 향상되는 유기 전계 발광 소자를 제공하는 것을 또 다른 목적으로 한다.Another object of the present invention is to provide an organic electroluminescent device containing the novel organic compound, which exhibits low driving voltage and high luminous efficiency and has improved lifespan.
상기 목적을 달성하기 위하여, 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다.In order to achieve the above object, the present invention provides a compound represented by the following formula (1).
[화학식 1][Formula 1]
상기 화학식 1에서,In Formula 1,
L1 및 L2는 서로 동일하거나 상이하며, 각각 독립적으로 단일결합이거나, 혹은 C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되고,L 1 and L 2 are the same or different from each other, and are each independently a single bond or selected from the group consisting of an arylene group of C 6 to C 18 and a heteroarylene group of 5 to 18 nuclear atoms,
복수의 R1은 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기 및 C2~C40의 알키닐기로 이루어진 군에서 선택되거나, 혹은 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며, 다만 적어도 하나 이상의 축합 고리를 형성하고,A plurality of R 1 is the same or different from each other, and each independently represents hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, and C 2 ~ C It may be selected from the group consisting of 40 alkynyl groups, or may be combined with adjacent groups to form a condensed ring, provided that at least one condensed ring is formed,
B는 하기 화학식 2로 표시되는 치환체이고,B is a substituent represented by the following formula (2),
[화학식 2][Formula 2]
상기 화학식 2에서,In Formula 2,
*은 상기 화학식 1에 결합되는 부분을 의미하고,* refers to the portion bonded to Formula 1 above,
X는 C(R3)(R4), O 및 S로 이루어진 군으로부터 선택되고,X is selected from the group consisting of C(R 3 )(R 4 ), O and S,
Ar1 및 Ar2는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고,Ar 1 and Ar 2 are the same or different from each other, and are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group, and C 6 ~ C 60 arylamine group,
m은 0 내지 3의 정수이고,m is an integer from 0 to 3,
R2 내지 R4는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 혹은 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, R 2 to R 4 are the same or different from each other, and each independently represents hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C Selected from the group consisting of an aryl boron group of 60 , an arylphosphine group of C 6 ~ C 60 , an arylphosphine oxide group of C 6 ~ C 60 , and an arylamine group of C 6 ~ C 60 , or condensed by combining with an adjacent group can form a ring,
상기 L1 및 L2의 아릴렌기 및 헤테로아릴렌기와, 상기 Ar1 및 Ar2, R1 내지 R4의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.The arylene group and heteroarylene group of L 1 and L 2 , the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group of Ar 1 and Ar 2 , R 1 to R 4 , Alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group, and aryl amine group are each independently deuterium (D), halogen, cyano group, Nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group and arylamine groups of C 6 to C 60 . In this case, when the substituents are plural, they 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 포함하고, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 것인 유기 전계 발광 소자를 제공한다. 여기서, 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자 수송층 및 전자 주입층으로 이루어진 군에서 선택될 수 있다. 이때, 상기 화학식 1로 표시되는 화합물은 발광층의 인광 호스트로 사용될 수 있다.In addition, the present invention provides an organic material comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers includes the compound represented by Formula 1 above. An electroluminescent device is provided. Here, the organic material layer containing the compound represented by Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, an auxiliary light emitting layer, a light emitting layer, an electron transport layer, and an electron injection layer. At this time, the compound represented by Formula 1 may be used as a phosphorescent host of the light-emitting layer.
본 발명의 화학식 1로 표시되는 화합물은 열적 안정성 및 발광 특성이 우수하기 때문에 유기 전계 발광 소자의 유기물층의 재료로 사용될 수 있다.The compound represented by Formula 1 of the present invention has excellent thermal stability and luminescence properties, so it can be used as a material for the organic layer of an organic electroluminescent device.
특히, 본 발명의 화학식 1로 표시되는 화합물을 인광 호스트 재료로 사용할 경우, 종래의 호스트 재료에 비해 낮은 구동전압, 높은 효율 및 긴 수명을 갖는 유기 전계 발광 소자를 제조할 수 있고, 나아가 성능 및 수명이 향상된 풀 칼라 디스플레이 패널도 제조할 수 있다.In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host material, an organic electroluminescent device with low driving voltage, high efficiency, and long lifespan can be manufactured compared to conventional host materials, and further improves performance and lifespan. This improved full-color display panel can also be manufactured.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
1. 신규 유기 화합물1. Novel organic compounds
본 발명에 따른 신규 유기 화합물은 '벤조카바졸(benzocarbazole)'에 '아크리딘(acridine), 페녹사진(phenoxazine) 또는 페녹시아진(phenothiazine)'이 직접 결합되거나 링커(예컨대, 아릴렌기 또는 헤테로아릴렌기)를 통해 결합된 형태를 기본 골격으로 하며, 이러한 기본 골격에 다양한 치환체가 도입되어 상기 화학식 1로 표시되는 것을 특징으로 한다. The new organic compound according to the present invention is 'benzocarbazole' with 'acridine, phenoxazine or phenothiazine' directly bonded to it or with a linker (for example, an arylene group or hetero The basic skeleton is a form bonded through an arylene group, and various substituents are introduced into this basic skeleton, which is represented by the above formula (1).
구체적으로, 상기 화학식 1의 화합물은 승화성 및 우수한 열적 안정성을 갖는 아크리딘, 페녹사진 또는 페녹시아진을 포함한다. 이러한 화학식 1의 화합물을 유기 전계 발광 소자에 사용할 경우에는 소자의 수명이 연장되어 장기간 사용될 수 있다.Specifically, the compound of Formula 1 includes acridine, phenoxazine, or phenoxyazine, which has sublimation properties and excellent thermal stability. When the compound of Formula 1 is used in an organic electroluminescent device, the lifespan of the device is extended and it can be used for a long period of time.
이러한 상기 화학식 1의 화합물은 아크리딘, 페녹사진 또는 페녹시아진이 '벤조카바졸'과 결합되어, '카바졸'과 결합된 경우에 비해 컨쥬게이션(conjugation) 길이가 증가하여 밴드갭(band gap)이 감소할 수 있다. 또한, 상기 화학식 1의 화합물은 벤조카바졸이 '아크리딘, 페녹사진 또는 페녹시아진'과 결합되어, '카바졸'과 결합된 경우에 비해 컨쥬게이션(conjugation) 길이가 증가하여 밴드갭(band gap)이 감소할 수 있다(하기 표 1 참조). 이와 같은 화학식 1의 화합물은 유기 전계 발광 소자의 유기물층 재료에 사용될 수 있으며, 이때 발광층 재료로 사용될 경우, 장파장을 나타내어 적색의 인광 호스트 재료로 사용될 수 있다.In the compound of Formula 1, acridine, phenoxazine or phenoxyazine is combined with 'benzocarbazole', and the conjugation length increases compared to the case where it is combined with 'carbazole', resulting in a band gap. ) may decrease. In addition, in the compound of Formula 1, benzocarbazole is combined with 'acridine, phenoxazine or phenoxyazine', and the conjugation length increases compared to the case where benzocarbazole is combined with 'carbazole', resulting in a band gap ( band gap) may decrease (see Table 1 below). The compound of Formula 1 can be used as an organic layer material of an organic electroluminescent device. When used as a light-emitting layer material, it exhibits a long wavelength and can be used as a red phosphorescent host material.
또한, 상기 화학식 1의 화합물은 상기 기본 골격에 도입되는 다양한 치환기의 종류에 따라 HOMO 및 LUMO 에너지 레벨을 조절할 수 있으며, 넓은 밴드갭 뿐만 아니라 높은 캐리어 수송성을 가질 수 있다. 이러한 화학식 1의 화합물은 상기 기본 골격에 질소-함유 헤테로환(예컨대, 피리딘기, 피리미딘기, 퀴나졸린기, 트리아진기 등)과 같이 전자 흡수성이 큰 전자 끌개기(EWG)가 결합될 경우, 분자 전체가 바이폴라(bipolar) 특성을 갖기 때문에 정공과 전자의 결합력을 높일 수 있다. 이러한 화학식 1의 화합물은 유기 전계 발광 소자의 유기물층 재료, 특히 발광층 재료로 사용될 수 있다.In addition, the compound of Formula 1 can control HOMO and LUMO energy levels depending on the types of various substituents introduced into the basic skeleton, and can have a wide band gap as well as high carrier transport properties. In the compound of Formula 1, when an electron withdrawing group (EWG) with high electron absorption, such as a nitrogen-containing heterocycle (e.g., pyridine group, pyrimidine group, quinazoline group, triazine group, etc.) is bonded to the basic skeleton, Because the entire molecule has bipolar characteristics, the bonding force between holes and electrons can be increased. The compound of Formula 1 can be used as an organic layer material, especially a light-emitting layer material, in an organic electroluminescent device.
이와 같은 화학식 1로 표시되는 화합물은 종래 유기 전계 발광 소자용 재료[예: 4,4-dicarbazolybiphenyl (이하, ‘CBP’라 함)]보다 높은 분자량을 갖기 때문에, 유리전이온도가 높아 열적 안정성이 우수할 뿐만 아니라 발광능이 우수하다. 따라서, 상기 화학식 1의 화합물을 유기 전계 발광 소자의 유기물층에 적용할 경우에는 소자의 구동전압, 효율, 수명 등이 향상될 수 있다. 이러한 화학식 1의 화합물은 유기 전계 발광 소자의 유기물층 재료로 사용될 수 있으며, 바람직하게는 발광층 재료(청색, 녹색 및/또는 적색의 인광 호스트 재료)로 사용될 수 있다.The compound represented by Formula 1 has a higher molecular weight than conventional materials for organic electroluminescent devices (e.g., 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')), and therefore has a high glass transition temperature and excellent thermal stability. Not only that, it has excellent luminous ability. Therefore, when the compound of Formula 1 is applied to the organic material layer of an organic electroluminescent device, the driving voltage, efficiency, lifespan, etc. of the device can be improved. The compound of Formula 1 can be used as an organic layer material of an organic electroluminescent device, and preferably as a light-emitting layer material (blue, green, and/or red phosphorescent host material).
따라서, 본 발명에 따른 화학식 1의 화합물을 포함하는 유기 전계 발광 소자는 성능 및 수명 특성이 크게 향상될 수 있고, 이러한 유기 전계 발광 소자가 적용된 풀 칼라 유기 발광 패널도 성능이 극대화될 수 있다.Therefore, the performance and lifespan characteristics of the organic electroluminescent device containing the compound of Formula 1 according to the present invention can be greatly improved, and the performance of a full-color organic light emitting panel to which such an organic electroluminescent device is applied can also be maximized.
본 발명에 따른 신규 화합물은 벤조카바졸에 아크리딘, 페녹사진 또는 페녹시아진이 직접 결합되거나 링커를 통해 결합되면서 다양한 치환체가 도입되는 것으로, 상기 화학식 1로 표시된다.The new compound according to the present invention is one in which various substituents are introduced by linking acridine, phenoxazine, or phenoxyazine directly or through a linker to benzocarbazole, and is represented by the above formula (1).
구체적으로, 상기 화학식 1로 표시되는 화합물에서, L1 및 L2는 서로 동일하거나 상이하며, 각각 독립적으로 단일결합이거나, 혹은 2가의 연결기일 수 있다. 이때, 상기 2가의 연결기는 C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택된다. 상기 아릴렌기 및 헤테로아릴렌기의 비제한적인 예로는 페닐렌기, 비페닐렌기, 나프틸렌기, 안트라세닐렌기, 인데닐렌기, 피란트레닐렌기, 카르바졸릴렌기, 티오페닐렌기, 인돌일렌기, 푸리닐렌기, 퀴놀리닐렌기, 피롤일렌기, 이미다졸릴렌기, 옥사졸릴렌기, 티아졸릴렌기, 트리아졸릴렌기, 피리디닐렌기, 피리미디닐렌기 등이 있다.Specifically, in the compound represented by Formula 1, L 1 and L 2 are the same as or different from each other, and may each independently be a single bond or a divalent linking group. At this time, the divalent linking group is selected from the group consisting of an arylene group having C 6 to C 18 and a heteroarylene group having 5 to 18 nuclear atoms. Non-limiting examples of the arylene group and heteroarylene group include phenylene group, biphenylene group, naphthylene group, anthracenylene group, indenylene group, pyrantrenylene group, carbazolylene group, thiophenylene group, indolylene group, There are purinylene group, quinolinylene group, pyrrolylene group, imidazolylene group, oxazolylene group, thiazolilene group, triazolylene group, pyridinylene group, pyrimidinylene group, etc.
바람직하게는, 상기 L1 및 L2는 서로 동일하거나 상이하며, 각각 독립적으로 단일결합 또는 C6~C18의 아릴렌기일 수 있다.Preferably, L 1 and L 2 are the same as or different from each other, and may each independently be a single bond or a C 6 to C 18 arylene group.
복수의 R1은 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기 및 C2~C40의 알키닐기로 이루어진 군에서 선택되거나, 혹은 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며, 다만 적어도 하나 이상 축합 고리를 형성한다.A plurality of R 1 is the same or different from each other, and each independently represents hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, and C 2 ~ C It may be selected from the group consisting of 40 alkynyl groups, or may be combined with adjacent groups to form a condensed ring, provided that at least one condensed ring is formed.
바람직하게는, 상기 복수의 R1은 하나의 R1과 다른 하나의 R1이 결합하여 하나의 축합 고리를 형성하며, 나머지 R1은 수소일 수 있다. 이러한 화학식 1의 화합물은 하기 화학식 3 내지 8로 표시되는 화합물로 구체화할 수 있다.Preferably, the plurality of R 1 forms one condensed ring by combining one R 1 and the other R 1 , and the remaining R 1 may be hydrogen. These compounds of Formula 1 can be specified as compounds represented by the following Formulas 3 to 8.
X는 C(R1)(R2), O 및 S로 이루어진 군에서 선택된다.X is selected from the group consisting of C(R 1 )(R 2 ), O and S.
Ar1 및 Ar2는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된다.Ar 1 and Ar 2 are the same or different from each other, and are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C It is selected from the group consisting of 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group, and C 6 ~ C 60 arylamine group.
바람직하게는, 상기 Ar1 및 Ar2는 서로 동일하거나 상이하며, 각각 독립적으로 C1~C40의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택될 수 있다. 더욱 바람직하게는, 상기 Ar1은 C6~C60의 아릴기 또는 핵원자수 5 내지 60의 헤테로아릴기일 수 있고, 상기 Ar2는 C6~C60의 아릴기일 수 있다. 이때, 상기 Ar1이 헤테로아릴기이고, Ar2가 아릴기일 경우에는 'Ar1이 아릴기이고, Ar2가 헤테로아릴기인 경우' 또는 'Ar1 및 Ar2 모두 C6~C60의 헤테로아릴기인 경우'에 비해 밴드갭이 더 감소할 수 있다. 이러한 화합물은 유기 전계 발광 소자의 발광층 재료로 사용될 수 있으며, 바람직하게는, 적색의 인광 호스트 재료로 사용될 수 있다.Preferably, Ar 1 and Ar 2 are the same as or different from each other, and are each independently an alkyl group of C 1 to C 40 , an aryl group of C 6 to C 60 , a heteroaryl group of 5 to 60 nuclear atoms, and a C 6 It may be selected from the group consisting of ~C 60 arylamine groups. More preferably, Ar 1 may be an aryl group having C 6 to C 60 or a heteroaryl group having 5 to 60 nuclear atoms, and Ar 2 may be an aryl group having C 6 to C 60 . At this time, when Ar 1 is a heteroaryl group and Ar 2 is an aryl group, ‘if Ar 1 is an aryl group and Ar 2 is a heteroaryl group’ or ‘both Ar 1 and Ar 2 are C 6 ~ C 60 heteroaryl The band gap may be further reduced compared to the 'gigi case'. These compounds can be used as a light-emitting layer material for an organic electroluminescent device, and preferably as a red phosphorescent host material.
m은 0 내지 3의 정수이다. 이때, m이 0일 경우에는 수소가 치환기 R2로 치환되지 않은 것을 의미한다. m이 1 내지 3의 정수일 경우에는 수소가 치환기 R2로 치환된 것을 의미하며, R2는 서로 동일하거나 상이하며, 각각 독립적으로 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된다.m is an integer from 0 to 3. At this time, when m is 0, it means that hydrogen is not substituted with substituent R 2 . When m is an integer of 1 to 3, it means that hydrogen is substituted with a substituent R 2 , and R 2 are the same or different from each other, and each independently represents deuterium (D), halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group , heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl. group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphine group, C 6 to C 60 arylphosphine oxide group and C 6 to C 60 It is selected from the group consisting of an arylamine group.
R3 및 R4는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 혹은 인접하는 기와 결합하여 축합 고리를 형성할 수 있다.R 3 and R 4 are the same or different from each other, and are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C Selected from the group consisting of an aryl boron group of 60 , an arylphosphine group of C 6 ~ C 60 , an arylphosphine oxide group of C 6 ~ C 60 , and an arylamine group of C 6 ~ C 60 , or condensed by combining with an adjacent group A ring can be formed.
바람직하게는, 상기 R3 및 R4는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 혹은 인접하는 기와 결합하여 축합 고리를 형성할 수 있다. Preferably, R 3 and R 4 are the same or different from each other, and are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 6 ~ C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and an arylamine group having C 6 to C 60 , or may be combined with an adjacent group to form a condensed ring.
상기 L1 및 L2의 아릴렌기 및 헤테로아릴렌기와, 상기 Ar1 및 Ar2, R1 내지 R4의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.The arylene group and heteroarylene group of L 1 and L 2 , the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group of Ar 1 and Ar 2 , R 1 to R 4 , Alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group, and aryl amine group are each independently deuterium (D), halogen, cyano group, Nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group and arylamine groups of C 6 to C 60 . In this case, when the substituents are plural, they may be the same or different from each other.
이러한 화학식 1로 표시되는 화합물은 하기 화학식 3 내지 5 중에서 적어도 어느 하나로 구체화될 수 있다. 그러나, 이에 특별히 한정되지 않는다.The compound represented by Formula 1 may be embodied in at least one of the following Formulas 3 to 5. However, it is not particularly limited thereto.
[화학식 3][Formula 3]
[화학식 4][Formula 4]
[화학식 5][Formula 5]
상기 화학식 3 내지 5에서, L1, L2, Ar1, Ar2, m, R2는 각각 상기 화학식 1에서 정의한 바와 같다.In Formulas 3 to 5, L 1 , L 2 , Ar 1 , Ar 2 , m, and R 2 are each as defined in Formula 1 above.
또한, 이러한 화학식 1로 표시되는 화합물은 하기 화학식 6 내지 8 중에서 적어도 어느 하나로 보다 구체화될 수 있다. 그러나, 이에 특별히 한정되지 않는다.Additionally, the compound represented by Formula 1 may be further specified as at least one of the following Formulas 6 to 8. However, it is not particularly limited thereto.
[화학식 6][Formula 6]
[화학식 7][Formula 7]
[화학식 8][Formula 8]
상기 화학식 6 내지 8에서, L1, L2, Ar1, Ar2, m, R2는 각각 상기 화학식 1에서 정의한 바와 같다.In Formulas 6 to 8, L 1 , L 2 , Ar 1 , Ar 2 , m, and R 2 are each as defined in Formula 1 above.
본 발명의 바람직한 일례에 따르면, 상기 Ar1은 하기 화학식 9로 표시되는 치환체일 수 있다. According to a preferred example of the present invention, Ar 1 may be a substituent represented by the following formula (9).
[화학식 9][Formula 9]
상기 화학식 9에서, *는 상기 화학식 1에 결합되는 부분을 의미한다.In Formula 9, * means a portion bonded to Formula 1.
Z1 내지 Z5는 서로 동일하거나 상이하며, 각각 독립적으로 N 또는 C(R5)이고, 이때 상기 R5이 복수인 경우, 이들은 서로 동일하거나 상이하다.Z 1 to Z 5 are the same or different from each other and are each independently N or C(R 5 ). In this case, when R 5 is plural, they are the same or different from each other.
R5는 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 혹은 인접하는 기와 결합하여 축합 고리를 형성할 수 있다.R 5 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 Cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 Aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 It may be selected from the group consisting of an arylphosphine group, a C 6 -C 60 arylphosphine oxide group, and a C 6 -C 60 arylamine group, or may be combined with an adjacent group to form a condensed ring.
상기 R5의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, Arylphosphine group, arylphosphine oxide group, and arylamine group each independently contain deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 Alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 may be substituted with one or more substituents selected from the group consisting of aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group, and C 6 ~ C 60 arylamine group, At this time, when the substituents are plural, they may be the same or different from each other.
상기 화학식 9로 표시되는 치환체는 하기 A-1 내지 A-15 중 어느 하나로 보다 구체화될 수 있다. 그러나, 이에 특별히 한정되지 않는다.The substituent represented by Formula 9 may be further specified as any one of A-1 to A-15 below. However, it is not particularly limited thereto.
상기 A-1 내지 A-15 에서, R5는 상기 화학식 9에서 정의한 바와 같다.In A-1 to A-15, R 5 is as defined in Formula 9 above.
p는 0 내지 4의 정수이다. 상기 p가 0일 경우, 수소가 치환기 R6으로 치환되지 않은 것을 의미한다. 상기 p가 1 내지 4의 정수일 경우, R6은 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 혹은 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며, 상기 R6이 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.p is an integer from 0 to 4. When p is 0, it means that hydrogen is not substituted with a substituent R 6 . When p is an integer of 1 to 4, R 6 is deuterium (D), halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkyl group. Nyl group, C 3 to C 40 cycloalkyl group, C 3 to C 40 heterocycloalkyl group, C 6 to C 60 aryl group, 5 to 60 nuclear atoms heteroaryl group, C 1 to C 40 alkyl group. Period, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group, and C 6 ~ C 60 arylamine group, or combined with an adjacent group to form a condensed ring. When R 6 is plural, they may be the same or different from each other.
상기 R6의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, Arylphosphine group, arylphosphine oxide group, and arylamine group each independently contain deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 Alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 may be substituted with one or more substituents selected from the group consisting of aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group, and C 6 ~ C 60 arylamine group, At this time, when the substituents are plural, they may be the same or different from each other.
이상에서 설명한 본 발명의 화학식 1로 표시되는 화합물은 하기 예시되는 화합물 1 내지 576 중 어느 하나로 표시되는 화합물로 보다 구체화될 수 있다. 그러나, 본 발명의 화학식 1로 표시되는 화합물이 하기 예시된 것들에 의해 한정되는 것은 아니다.The compound represented by Formula 1 of the present invention described above may be further specified as a compound represented by any one of compounds 1 to 576 exemplified below. However, the compound represented by Formula 1 of the present invention is not limited to those exemplified below.
본 발명에서 “알킬”은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이러한 알킬의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, “alkyl” refers to a monovalent substituent derived from a straight-chain or branched-chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples of such alkyl 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 가진탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이러한 알케닐의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, “alkenyl” refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon double bonds. Examples of such alkenyl include vinyl, allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.
본 발명에서“알키닐(alkynyl)”은 탄소-탄소 삼중 결합을 1개 이상 가진탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이러한 알키닐의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, “alkynyl” refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples of such alkynyl include ethynyl, 2-propynyl, etc., but are not limited thereto.
본 발명에서 “아릴”은 단독 고리 또는 2 이상의 고리가 조합된 탄소수 6 내지 60의 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” refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, either a single ring or a combination of two or more rings. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may also be included. Examples of such aryl include phenyl, naphthyl, phenanthryl, anthryl, etc., but are not limited thereto.
본 발명에서 “헤테로아릴”은 핵원자수 5 내지 60의 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” refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon, preferably 1 to 3 carbons, of the ring is replaced with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply pendant or condensed with each other may be included, and a condensed form with an aryl group may also be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, phenoxathienyl, indolizinyl, and indolyl ( Polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, etc., but are not limited thereto.
본 발명에서 “아릴옥시”는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 6 내지 60의 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-, where R refers to aryl having 6 to 60 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, etc., but are not limited thereto.
본 발명에서 “알킬옥시”는 R’O-로 표시되는 1가의 치환기로, 상기 R’는 탄소수 1 내지 40의 알킬을 의미한다. 이러한 알킬옥시는 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함할 수 있다. 이러한 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 represented by R’O-, where R’ refers to alkyl having 1 to 40 carbon atoms. These alkyloxy may include linear, branched, or cyclic structures. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.
본 발명에서 “아릴아민”은 탄소수 6 내지 60의 아릴로 치환된 아민을 의미한다.In the present invention, “arylamine” refers to an amine substituted with aryl having 6 to 60 carbon atoms.
본 발명에서 “시클로알킬”은 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” refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.
본 발명에서 “헤테로시클로알킬”은 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” refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S Or it is substituted with a hetero atom such as Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.
본 발명에서 “알킬실릴”은 탄소수 1 내지 40의 알킬로 치환된 실릴이고, “아릴실릴”은 탄소수 6 내지 60의 아릴로 치환된 실릴을 의미한다.In the present invention, “alkylsilyl” refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” refers to silyl substituted with aryl having 6 to 60 carbon atoms.
본 발명에서 “알킬보론”은 탄소수 1 내지 40의 알킬로 치환된 보론이고, “아릴보론”은 탄소수 6 내지 60의 아릴로 치환된 보론을 의미한다.In the present invention, “alkylboron” refers to boron substituted with alkyl having 1 to 40 carbon atoms, and “arylboron” refers to boron substituted with aryl having 6 to 60 carbon atoms.
본 발명에서 "아릴포스핀"은 탄소수 6 내지 60의 아릴로 치환된 포스핀을 의미하고, "아릴포스핀옥사이드기"는 탄소수 6 내지 60의 아릴로 치환된 포스핀이 O를 포함하는 것을 의미한다.In the present invention, “arylphosphine” refers to phosphine substituted with aryl having 6 to 60 carbon atoms, and “arylphosphine oxide group” refers to phosphine substituted with aryl having 6 to 60 carbon atoms containing O. do.
본 발명에서 “축합고리”는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.In the present invention, “condensed ring” means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
이와 같은 본 발명의 화학식 1로 표시되는 화합물은 하기 실시예의 합성과정을 참고하여 다양하게 합성할 수 있다.The compound represented by Formula 1 of the present invention can be synthesized in various ways by referring to the synthesis process in the examples below.
2. 유기 2. Organic 전계electric field 발광 소자 light emitting element
본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.The present invention provides an organic electroluminescent device containing the compound represented by Formula 1 above.
보다 구체적으로, 본 발명에 따른 유기 전계 발광 소자는 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 포함한다. 이때, 상기 화합물은 단독으로 사용되거나, 또는 2 이상이 혼합되어 사용될 수 있다.More specifically, the organic electroluminescent device according to the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers includes a compound represented by Formula 1 above. At this time, the above compounds may be used alone, or two or more may be used in combination.
상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자 수송층 및 전자 주입층 중 어느 하나 이상일 수 있고, 이 중에서 적어도 하나의 유기물층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 구체적으로, 상기 화학식 1의 화합물을 포함하는 유기물층은 발광층인 것이 바람직하다.The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, and an electron injection layer, and among these, at least one organic material layer may include a compound represented by Formula 1. there is. Specifically, it is preferable that the organic material layer containing the compound of Formula 1 is a light-emitting layer.
본 발명의 유기 전계 발광 소자의 발광층은 호스트 재료(바람직하게는, 인광 호스트 재료)를 포함할 수 있다. 또한, 본 발명의 유기 전계 발광 소자의 발광층은 상기 화학식 1의 화합물 이외의 화합물을 호스트로 포함할 수 있다.The light-emitting layer of the organic electroluminescent device of the present invention may include a host material (preferably, a phosphorescent host material). Additionally, the light-emitting layer of the organic electroluminescent device of the present invention may include a compound other than the compound of Formula 1 above as a host.
이러한 본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 비제한적인 예로 기판, 양극, 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자 수송층 및 음극이 순차적으로 적층된 구조일 수 있다. 이때, 상기 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자 수송층 및 전자 주입층 중 하나 이상은 상기 화학식 1로 표시되는 화합물을 포함할 수 있고, 바람직하게는 발광층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 여기서, 상기 전자 수송층 위에는 전자 주입층이 추가로 적층될 수 있다. 또한, 본 발명의 유기 전계 발광 소자의 구조는 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조일 수 있다.The structure of the organic electroluminescent device of the present invention is not particularly limited, but as a non-limiting example, it may have a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, an auxiliary light emitting layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. . At this time, one or more of the hole injection layer, hole transport layer, light emitting auxiliary layer, light emitting layer, electron transport layer, and electron injection layer may include a compound represented by Formula 1, and preferably the light emitting layer is represented by Formula 1. It may contain compounds. Here, an electron injection layer may be additionally stacked on the electron transport layer. Additionally, the structure of the organic electroluminescent device of the present invention may be one in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer.
한편, 본 발명의 유기 전계 발광 소자는 상기 유기물층 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는, 당업계에 공지된 재료 및 방법으로 유기물층 및 전극을 형성하여 제조할 수 있다.Meanwhile, the organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode using materials and methods known in the art, except that at least one layer of the organic material layer contains the compound represented by Formula 1. there is.
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, 이에 한정되지는 않는다.The organic material layer may be formed by vacuum deposition or solution application. Examples of the solution application method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
본 발명의 유기 전계 발광 소자 제조시 사용되는 기판은 특별히 한정되지 않으나, 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등을 사용할 수 있다.The substrate used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, but silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, etc. can be used.
또한, 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 등을 들 수 있으나, 이에 한정되지는 않는다.Additionally, the anode material includes metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO2:Sb; Conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black, but are not limited thereto.
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 등을 들 수 있으나, 이에 한정되지는 않는다.Additionally, the cathode material may include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multilayer structure materials such as LiF/Al or LiO2/Al, etc., but are not limited thereto.
또한, 정공 주입층, 정공 수송층, 전자 주입층 및 전자 수송층은 특별히 한정되는 것은 아니며, 당 업계에 알려진 통상의 물질을 사용할 수 있다.Additionally, the hole injection layer, hole transport layer, electron injection layer, and electron transport layer are not particularly limited, and common 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 through examples. However, the following examples are merely illustrative of the present invention, and the present invention is not limited by the following examples.
[[ 준비예Preparation example 1] Core1] Core 1 의1 of 합성 synthesis
질소 기류 하에서 10-bromo-7H-benzo[c]carbazole (50 g, 168.82 mmol), (9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl)boronic acid (55.58 g, 168.82 mmol), Pd(PPh3)4 (9.76 g, 5 mol%), NaOH (20.26 g, 506.47 mmol)을 THF/H2O (400 ml/100 ml)에 넣고 80에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 Core 1 (72.7 g, 수율 86 %)을 획득하였다. 10-bromo-7H-benzo[c]carbazole (50 g, 168.82 mmol), (9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl)boronic acid (55.58 g, 168.82) under nitrogen flow. mmol), Pd(PPh 3 ) 4 (9.76 g, 5 mol%) and NaOH (20.26 g, 506.47 mmol) were added to THF/H 2 O (400 ml/100 ml) and stirred at 80° C. for 12 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO 4 was added and filtered. After removing the solvent in the filtered organic layer, the target compound Core 1 (72.7 g, yield 86%) was obtained using column chromatography.
1H-NMR: δ 1.68 (s, 6H), 7.14 (m, 9H), 7.33 (d, 1H), 7.69 (m, 5H), 7.74 (m, 2H), 7.86 (s, 1H), 7.95 (d, 2H), 8.52 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 1.68 (s, 6H), 7.14 (m, 9H), 7.33 (d, 1H), 7.69 (m, 5H), 7.74 (m, 2H), 7.86 (s, 1H), 7.95 ( d, 2H), 8.52 (d, 1H), 11.63 (s, 1H)
[[ 준비예Preparation example 2] Core2] Core 2 의2 of 합성 synthesis
(9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl)boronic acid 대신 (9,9-dimethyl-10-phenyl-9,10-dihydroacridin-3-yl)boronic acid (55.58 g, 168.82 mmol)을 사용하는 것을 제외하고는 준비예 1과 동일한 과정을 수행하여 Core 2 (69.3 g, 수율 82 %)을 얻었다.(9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl)boronic acid (55.58 g) Core 2 (69.3 g, yield 82%) was obtained by performing the same process as Preparation Example 1 except for using , 168.82 mmol).
1H-NMR: δ 1.68 (s, 6H), 7.11 (m, 12H), 7.62 (m, 4H), 7.74 (d, 1H), 7.85 (s, 1H), 7.97 (d, 2H), 8.56 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 1.68 (s, 6H), 7.11 (m, 12H), 7.62 (m, 4H), 7.74 (d, 1H), 7.85 (s, 1H), 7.97 (d, 2H), 8.56 ( d, 1H), 11.63 (s, 1H)
[[ 준비예Preparation example 3] Core3] Core 3 의3 of 합성 synthesis
(9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl)boronic acid 대신 (10-phenyl-10H-phenoxazin-3-yl)boronic acid (51.2 g, 168.8 mmol)을 사용하는 것을 제외하고는 준비예 1과 동일한 과정을 수행하여 Core 3 (67.3 g, 수율 84 %)을 얻었다.Using (10-phenyl-10H-phenoxazin-3-yl)boronic acid (51.2 g, 168.8 mmol) instead of (9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl)boronic acid Core 3 (67.3 g, yield 84%) was obtained by performing the same process as Preparation Example 1 except.
1H-NMR: δ 7.19 (m, 12H), 7.58 (m, 4H), 7.76 (d, 1H), 7.85 (s, 1H), 8.01 (d, 2H), 8.56 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 7.19 (m, 12H), 7.58 (m, 4H), 7.76 (d, 1H), 7.85 (s, 1H), 8.01 (d, 2H), 8.56 (d, 1H), 11.63 ( s, 1H)
[[ 준비예Preparation example 4] Core4] Core 4 의4 of 합성 synthesis
(9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl)boronic acid 대신 (10-phenyl-10H-phenoxazin-2-yl)boronic acid (51.2 g, 168.8 mmol)을 사용하는 것을 제외하고는 준비예 1과 동일한 과정을 수행하여 Core 4 (63.3 g, 수율 79 %)을 얻었다.Using (10-phenyl-10H-phenoxazin-2-yl)boronic acid (51.2 g, 168.8 mmol) instead of (9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl)boronic acid Core 4 (63.3 g, yield 79%) was obtained by performing the same process as Preparation Example 1 except.
1H-NMR: δ 7.17 (m, 12H), 7.57 (m, 4H), 7.74 (d, 1H), 7.86 (s, 1H), 8.01 (d, 2H), 8.55 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 7.17 (m, 12H), 7.57 (m, 4H), 7.74 (d, 1H), 7.86 (s, 1H), 8.01 (d, 2H), 8.55 (d, 1H), 11.63 ( s, 1H)
[[ 준비예Preparation example 5] Core5] Core 5 의5 of 합성 synthesis
(9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl)boronic acid 대신 (10-phenyl-10H-phenothiazin-3-yl)boronic acid (53.9 g, 168.8 mmol)을 사용하는 것을 제외하고는 준비예 1과 동일한 과정을 수행하여 Core 5 (68.7 g, 수율 83 %)을 얻었다.Using (10-phenyl-10H-phenothiazin-3-yl)boronic acid (53.9 g, 168.8 mmol) instead of (9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl)boronic acid Core 5 (68.7 g, yield 83%) was obtained by performing the same process as Preparation Example 1 except.
1H-NMR: δ 7.18 (m, 12H), 7.58 (m, 4H), 7.75 (d, 1H), 7.98 (d, 2H), 8.53 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 7.18 (m, 12H), 7.58 (m, 4H), 7.75 (d, 1H), 7.98 (d, 2H), 8.53 (d, 1H), 11.63 (s, 1H)
[[ 준비예Preparation example 6] Core6] Core 6 의6 of 합성 synthesis
(9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl)boronic acid 대신 (10-phenyl-10H-phenothiazin-2-yl)boronic acid (53.9 g, 168.8 mmol)을 사용하는 것을 제외하고는 준비예 1과 동일한 과정을 수행하여 Core 6 (67.1 g, 수율 81 %)을 얻었다.Using (10-phenyl-10H-phenothiazin-2-yl)boronic acid (53.9 g, 168.8 mmol) instead of (9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl)boronic acid Core 6 (67.1 g, yield 81%) was obtained by performing the same process as Preparation Example 1 except.
1H-NMR: δ 7.13 (m, 11H), 7.34 (d, 1H), 7.57 (m, 4H), 7.78 (d, 1H), 7.85 (s, 1H), 7.97 (d, 2H), 8.52 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 7.13 (m, 11H), 7.34 (d, 1H), 7.57 (m, 4H), 7.78 (d, 1H), 7.85 (s, 1H), 7.97 (d, 2H), 8.52 ( d, 1H), 11.63 (s, 1H)
[[ 준비예Preparation example 7] Core7] Core 7 의7 of 합성 synthesis
10-bromo-7H-benzo[c]carbazole 대신 9-bromo-7H-benzo[c]carbazole (55.58 g, 168.82mmol)을 사용하는 것을 제외하고는 준비예 1과 동일한 과정을 수행하여 Core 7 (69.3 g, 수율 82 %)을 얻었다.Core 7 (69.3 g, yield 82%) was obtained.
1H-NMR: δ 1.68 (s, 6H), 7.17 (m, 9H), 7.35 (d, 1H), 7.57 (m, 5H), 7.75 (s, 2H), 7.95 (d, 2H), 8.34 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 1.68 (s, 6H), 7.17 (m, 9H), 7.35 (d, 1H), 7.57 (m, 5H), 7.75 (s, 2H), 7.95 (d, 2H), 8.34 ( d, 1H), 11.63 (s, 1H)
[[ 준비예Preparation example 8] Core8] Core 8 의8 of 합성 synthesis
10-bromo-7H-benzo[c]carbazole 대신 9-bromo-7H-benzo[c]carbazole (55.58 g, 168.82 mmol)을 사용하는 것을 제외하고는 준비예 2와 동일한 과정을 수행하여 Core 8 (65.9 g, 수율 78 %)을 얻었다.Core 8 (65.9 g, yield 78%) was obtained.
1H-NMR: δ 1.68 (s, 6H), 7.18 (m, 12H), 7.57 (m, 4H), 7.72 (s, 1H), 7.99 (d, 2H), 8.30 (d, 1H), 8.55 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 1.68 (s, 6H), 7.18 (m, 12H), 7.57 (m, 4H), 7.72 (s, 1H), 7.99 (d, 2H), 8.30 (d, 1H), 8.55 ( d, 1H), 11.63 (s, 1H)
[[ 준비예Preparation example 9] Core9] Core 9 의9 of 합성 synthesis
10-bromo-7H-benzo[c]carbazole 대신 9-bromo-7H-benzo[c]carbazole (51.2 g, 168.8 mmol)을 사용하는 것을 제외하고는 준비예 3과 동일한 과정을 수행하여 Core 9 (64.1 g, 수율 80 %)을 얻었다.Core 9 (64.1 g, yield 80%) was obtained.
1H-NMR: δ 7.19 (m, 12H), 7.55 (m, 4H), 7.96 (d, 2H), 8.29 (d, 1H), 8.57 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 7.19 (m, 12H), 7.55 (m, 4H), 7.96 (d, 2H), 8.29 (d, 1H), 8.57 (d, 1H), 11.63 (s, 1H)
[[ 준비예Preparation example 10] Core10] Core 10 의10 of 합성 synthesis
10-bromo-7H-benzo[c]carbazole 대신 9-bromo-7H-benzo[c]carbazole (51.2 g, 168.8 mmol)을 사용하는 것을 제외하고는 준비예 4과 동일한 과정을 수행하여 Core 10 (60.9 g, 수율 76 %)을 얻었다.Core 10 (60.9 mmol) was prepared in the same manner as in Preparation Example 4, except that 9-bromo-7H-benzo[c]carbazole (51.2 g, 168.8 mmol) was used instead of 10-bromo-7H-benzo[c]carbazole. g, yield 76%) was obtained.
1H-NMR: δ 7.21 (m, 12H), 7.57 (m, 4H), 7.72 (s, 1H), 7.96 (d, 2H), 8.30 (d, 1H), 8.55 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 7.21 (m, 12H), 7.57 (m, 4H), 7.72 (s, 1H), 7.96 (d, 2H), 8.30 (d, 1H), 8.55 (d, 1H), 11.63 ( s, 1H)
[[ 준비예Preparation example 11] Core11] Core 11 의11 of 합성 synthesis
10-bromo-7H-benzo[c]carbazole 대신 9-bromo-7H-benzo[c]carbazole (53.9 g, 168.8 mmol)을 사용하는 것을 제외하고는 준비예 5와 동일한 과정을 수행하여 Core 11 (67.1 g, 수율 81 %)을 얻었다.Core 11 (67.1 g, yield 81%) was obtained.
1H-NMR: δ 7.29 (m, 12H), 7.57 (m, 4H), 7.72 (s, 1H), 7.94 (d, 2H), 8.29 (d, 1H), 8.55 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 7.29 (m, 12H), 7.57 (m, 4H), 7.72 (s, 1H), 7.94 (d, 2H), 8.29 (d, 1H), 8.55 (d, 1H), 11.63 ( s, 1H)
[[ 준비예Preparation example 12] Core12] Core 12 의12 of 합성 synthesis
10-bromo-7H-benzo[c]carbazole 대신 9-bromo-7H-benzo[c]carbazole (53.9 g, 168.8 mmol)을 사용하는 것을 제외하고는 준비예 6과 동일한 과정을 수행하여 Core 12 (63.8 g, 수율 77 %)을 얻었다.Core 12 (63.8 g, yield 77%) was obtained.
1H-NMR: δ 7.17 (m, 11H), 7.37 (d, 1H), 7.57 (m, 4H), 7.79 (s, 1H), 8.01 (d, 2H), 8.34 (d, 1H), 8.57 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 7.17 (m, 11H), 7.37 (d, 1H), 7.57 (m, 4H), 7.79 (s, 1H), 8.01 (d, 2H), 8.34 (d, 1H), 8.57 ( d, 1H), 11.63 (s, 1H)
[[ 준비예Preparation example 13] Core13] Core 13 의13 of 합성 synthesis
10-bromo-7H-benzo[c]carbazole 대신 8-bromo-7H-benzo[c]carbazole (55.58 g, 168.82 mmol)을 사용하는 것을 제외하고는 준비예 1과 동일한 과정을 수행하여 Core 13 (60.6 g, 수율 72 %)을 얻었다.Core 13 (60.6 g, yield 72%) was obtained.
1H-NMR: δ 1.68 (s, 6H), 7.13 (m, 9H), 7.34 (d, 1H), 7.52 (m, 6H), 7.79 (s, 1H), 8.01 (d, 2H), 8.27 (d, 1H), 8.53 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 1.68 (s, 6H), 7.13 (m, 9H), 7.34 (d, 1H), 7.52 (m, 6H), 7.79 (s, 1H), 8.01 (d, 2H), 8.27 ( d, 1H), 8.53 (d, 1H), 11.63 (s, 1H)
[[ 준비예Preparation example 14] Core14] Core 14 의14 of 합성 synthesis
10-bromo-7H-benzo[c]carbazole 대신 8-bromo-7H-benzo[c]carbazole (55.58 g, 168.82 mmol)을 사용하는 것을 제외하고는 준비예 2와 동일한 과정을 수행하여 Core 14 (57.5 g, 수율 68 %)을 얻었다.Core 14 (57.5) was prepared in the same manner as in Preparation Example 2, except that 8-bromo-7H-benzo[c]carbazole (55.58 g, 168.82 mmol) was used instead of 10-bromo-7H-benzo[c]carbazole. g, yield 68%) was obtained.
1H-NMR: δ 7.17 (m, 12H), 7.56 (m, 5H), 8.03 (d, 2H), 8.27 (d, 1H), 8.53 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 7.17 (m, 12H), 7.56 (m, 5H), 8.03 (d, 2H), 8.27 (d, 1H), 8.53 (d, 1H), 11.63 (s, 1H)
[[ 준비예Preparation example 15] Core15] Core 15 의15 of 합성 synthesis
10-bromo-7H-benzo[c]carbazole 대신 8-bromo-7H-benzo[c]carbazole (51.2 g, 168.8 mmol)을 사용하는 것을 제외하고는 준비예 3과 동일한 과정을 수행하여 Core 15 (56.1 g, 수율 70 %)을 얻었다.Core 15 (56.1 g, yield 70%) was obtained.
1H-NMR: δ 7.17 (m, 12H), 7.57 (m, 5H), 8.02 (d, 2H), 8.28 (d, 1H), 8.53 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 7.17 (m, 12H), 7.57 (m, 5H), 8.02 (d, 2H), 8.28 (d, 1H), 8.53 (d, 1H), 11.63 (s, 1H)
[[ 준비예Preparation example 16] Core16] Core 16 의16 of 합성 synthesis
10-bromo-7H-benzo[c]carbazole 대신 8-bromo-7H-benzo[c]carbazole (51.2 g, 168.8 mmol)을 사용하는 것을 제외하고는 준비예 4와 동일한 과정을 수행하여 Core 16 (52.8 g, 수율 66 %)을 얻었다.Core 16 (52.8 g, yield 66%) was obtained.
1H-NMR: δ 7.18 (m, 12H), 7.54 (m, 5H), 8.02 (d, 2H), 8.28 (d, 1H), 8.53 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 7.18 (m, 12H), 7.54 (m, 5H), 8.02 (d, 2H), 8.28 (d, 1H), 8.53 (d, 1H), 11.63 (s, 1H)
[[ 준비예Preparation example 17] Core17] Core 17 의17 of 합성 synthesis
10-bromo-7H-benzo[c]carbazole 대신 8-bromo-7H-benzo[c]carbazole (53.9 g, 168.8 mmol)을 사용하는 것을 제외하고는 준비예 5와 동일한 과정을 수행하여 Core 17 (57.2 g, 수율 69 %)을 얻었다.Core 17 (57.2 g, yield 69%) was obtained.
1H-NMR: δ 7.43 (m, 17H), 8.07 (d, 2H), 8.27 (d, 1H), 8.59 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 7.43 (m, 17H), 8.07 (d, 2H), 8.27 (d, 1H), 8.59 (d, 1H), 11.63 (s, 1H)
[[ 준비예Preparation example 18] Core18] Core 18 의18 of 합성 synthesis
10-bromo-7H-benzo[c]carbazole 대신 8-bromo-7H-benzo[c]carbazole (53.9 g, 168.8 mmol)을 사용하는 것을 제외하고는 준비예 6과 동일한 과정을 수행하여 Core 18 (52.2 g, 수율 63 %)을 얻었다.Core 18 (52.2 g, yield 63%) was obtained.
1H-NMR: δ 7.21 (m, 11H), 7.37 (d, 1H), 7.52 (m, 5H), 8.03 (d, 2H), 8.23 (d, 1H), 8.55 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 7.21 (m, 11H), 7.37 (d, 1H), 7.52 (m, 5H), 8.03 (d, 2H), 8.23 (d, 1H), 8.55 (d, 1H), 11.63 ( s, 1H)
[[ 준비예Preparation example 19] Core19] Core 19 의19 of 합성 synthesis
10-bromo-7H-benzo[c]carbazole 대신 11-bromo-7H-benzo[c]carbazole (55.58 g, 168.82 mmol)을 사용하는 것을 제외하고는 준비예 1과 동일한 과정을 수행하여 Core 19 (62.6 g, 수율 74 %)을 얻었다.Core 19 (62.6 g, yield 74%) was obtained.
1H-NMR: δ 1.68 (s, 6H), 7.11 (m, 9H), 7.37 (d, 1H), 7.52 (m, 8H), 7.94 (d, 2H), 8.32 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 1.68 (s, 6H), 7.11 (m, 9H), 7.37 (d, 1H), 7.52 (m, 8H), 7.94 (d, 2H), 8.32 (d, 1H), 11.63 ( s, 1H)
[[ 준비예Preparation example 20] Core20] Core 20 의20 of 합성 synthesis
10-bromo-7H-benzo[c]carbazole 대신 11-bromo-7H-benzo[c]carbazole (55.58 g, 168.82 mmol)을 사용하는 것을 제외하고는 준비예 2와 동일한 과정을 수행하여 Core 20 (58.3 g, 수율 69 %)을 얻었다.Core 20 (58.3 g, yield 69%) was obtained.
1H-NMR: δ 1.68 (s, 6H), 7.11 (m, 9H), 7.36 (d, 1H), 7.58 (m, 8H), 7.94 (d, 2H), 8.52 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 1.68 (s, 6H), 7.11 (m, 9H), 7.36 (d, 1H), 7.58 (m, 8H), 7.94 (d, 2H), 8.52 (d, 1H), 11.63 ( s, 1H)
[[ 준비예Preparation example 21] Core21] Core 21 의21 of 합성 synthesis
10-bromo-7H-benzo[c]carbazole 대신 11-bromo-7H-benzo[c]carbazole (51.2 g, 168.8 mmol)을 사용하는 것을 제외하고는 준비예 3과 동일한 과정을 수행하여 Core 21 (57.7 g, 수율 72 %)을 얻었다.Core 21 (57.7 mmol) was prepared in the same manner as in Preparation Example 3, except that 11-bromo-7H-benzo[c]carbazole (51.2 g, 168.8 mmol) was used instead of 10-bromo-7H-benzo[c]carbazole. g, yield 72%) was obtained.
1H-NMR: δ 7.16 (m, 12H), 7.67 (m, 5H), 7.92 (d, 2H), 8.52 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 7.16 (m, 12H), 7.67 (m, 5H), 7.92 (d, 2H), 8.52 (d, 1H), 11.63 (s, 1H)
[[ 준비예Preparation example 22] Core22] Core 22 의22 of 합성 synthesis
10-bromo-7H-benzo[c]carbazole 대신 11-bromo-7H-benzo[c]carbazole (51.2 g, 168.8 mmol)을 사용하는 것을 제외하고는 준비예 4와 동일한 과정을 수행하여 Core 22 (52.9 g, 수율 66 %)을 얻었다.Core 22 (52.9 g, yield 66%) was obtained.
1H-NMR: δ 7.11 (m, 12H), 7.67 (m, 6H), 7.97 (d, 2H), 8.59 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 7.11 (m, 12H), 7.67 (m, 6H), 7.97 (d, 2H), 8.59 (d, 1H), 11.63 (s, 1H)
[[ 준비예Preparation example 23] Core23] Core 23 의23 of 합성 synthesis
10-bromo-7H-benzo[c]carbazole 대신 11-bromo-7H-benzo[c]carbazole (53.9 g, 168.8 mmol)을 사용하는 것을 제외하고는 준비예 5와 동일한 과정을 수행하여 Core 23 (57.9 g, 수율 70 %)을 얻었다.Core 23 (57.9 mmol) was prepared in the same manner as in Preparation Example 5, except that 11-bromo-7H-benzo[c]carbazole (53.9 g, 168.8 mmol) was used instead of 10-bromo-7H-benzo[c]carbazole. g, yield 70%) was obtained.
1H-NMR: δ 7.21 (m, 12H), 7.57 (m, 6H), 7.92 (d, 2H), 8.59 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 7.21 (m, 12H), 7.57 (m, 6H), 7.92 (d, 2H), 8.59 (d, 1H), 11.63 (s, 1H)
[[ 준비예Preparation example 24] Core24] Core 24 의24 합성 synthesis
10-bromo-7H-benzo[c]carbazole 대신 11-bromo-7H-benzo[c]carbazole (53.9 g, 168.8 mmol)을 사용하는 것을 제외하고는 준비예 6과 동일한 과정을 수행하여 Core 24 (53.1 g, 수율 64 %)을 얻었다.Core 24 (53.1 g, yield 64%) was obtained.
1H-NMR: δ 7.11 (m, 11H), 7.37 (d, 1H), 7.62 (m, 6H), 7.92 (d, 2H), 8.31 (d, 1H), 11.63 (s, 1H) 1 H-NMR: δ 7.11 (m, 11H), 7.37 (d, 1H), 7.62 (m, 6H), 7.92 (d, 2H), 8.31 (d, 1H), 11.63 (s, 1H)
[[ 합성예Synthesis example 1] 화합물 1] Compound 1 의1 of 합성 synthesis
질소 기류 하에서 Core 1 (5.00 g, 10.0 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10.0 mmol), Pd2(dba)3 (0.27 g, 0.3 mmol), (t-Bu)3P (0.4 g, 2.0 mmol), sodium tert-butoxide (NaOBu-t) (1.92 g, 20.0 mmol)을 toluene (PhMe) 100 ml에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물 (6.21 g, 수율 85 %)을 얻었다. Core 1 (5.00 g, 10.0 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10.0 mmol), Pd 2 (dba) 3 (0.27 g, 0.3 mmol) under nitrogen flow. ), (t-Bu) 3 P (0.4 g, 2.0 mmol), sodium tert-butoxide (NaOBu-t) (1.92 g, 20.0 mmol) were added to 100 ml of toluene (PhMe) and stirred at 110°C for 12 hours. . After completion of the reaction, it was extracted with methylene chloride, MgSO 4 was added, and filtered. After removing the solvent in the filtered organic layer, the target compound (6.21 g, yield 85%) was obtained using column chromatography.
Mass : [(M+H)+] : 732Mass : [(M+H) + ] : 732
[[ 합성예Synthesis example 2] 화합물 2] Compound 6 의6 of 합성 synthesis
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (3.42 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (6.61 g, 수율 82%)을 얻었다.Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, use 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (3.42 g, 10.00 mmol) The target compound (6.61 g, yield 82%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 808Mass : [(M+H) + ] : 808
[[ 합성예Synthesis example 3] 화합물 3] Compound 9 의9 of 합성 synthesis
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.88 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (6.46 g, 수율 80%)을 얻었다.Use 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.88 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. Except that the same process as Synthesis Example 1 was performed to obtain the target compound (6.46 g, yield 80%).
Mass : [(M+H)+] : 809Mass : [(M+H) + ] : 809
[[ 합성예Synthesis example 4] 화합물 4] Compound 13 의13 of 합성 synthesis
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.49 g, 수율 78%)을 얻었다.The target compound was obtained by carrying out the same process as Synthesis Example 1 except that 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. (5.49 g, yield 78%) was obtained.
Mass : [(M+H)+] : 705Mass : [(M+H) + ] : 705
[[ 합성예Synthesis example 5] 화합물 5] Compound 17 의17 of 합성 synthesis
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-(3-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (6.48 g, 수율 83%)을 얻었다.The same process as Synthesis Example 1 was performed except that 2-(3-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. This was performed to obtain the target compound (6.48 g, yield 83%).
Mass : [(M+H)+] : 781Mass : [(M+H) + ] : 781
[[ 합성예Synthesis example 6] 화합물 6] Compound 15 의15 of 합성 synthesis
2-chloro-4,6-diphenyl-1,3,5-triazine 대신 4-([1,1'-biphenyl]-4-yl)-2-chloroquinazoline (3.16 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (6.32 g, 수율 81%)을 얻었다.Except for using 4-([1,1'-biphenyl]-4-yl)-2-chloroquinazoline (3.16 g, 10.00 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine. Then, the same process as Synthesis Example 1 was performed to obtain the target compound (6.32 g, yield 81%).
Mass : [(M+H)+] : 781Mass : [(M+H) + ] : 781
[[ 합성예Synthesis example 7] 화합물 7] Compound 74 의74 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 2 (5.00 g, 10.00 mmol)와 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.77 g, 수율 79%)을 얻었다.Using Core 2 (5.00 g, 10.00 mmol) and 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. Except for this, the same process as Synthesis Example 1 was performed to obtain the target compound (5.77 g, yield 79%).
Mass : [(M+H)+] : 731Mass : [(M+H) + ] : 731
[[ 합성예Synthesis example 8] 화합물 8] Compound 77 의77 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 2 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.81 g, 수율 72%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 2 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The target compound (5.81 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol).
Mass : [(M+H)+] : 809Mass : [(M+H) + ] : 809
[[ 합성예Synthesis example 9] 화합물 9] Compound 83 의83 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 2 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (6.54 g, 수율 74%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 2 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The same process as Synthesis Example 1 was performed except for using (3-bromophenyl)-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol) to obtain the target compound (6.54 g, yield 74%). got it
Mass : [(M+H)+] : 885Mass : [(M+H) + ] : 885
[[ 합성예Synthesis example 10] 화합물 10] Compound 86 의86 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 2 (5.00 g, 10.00 mmol)와 2-chloro-4-phenylbenzo[h]quinazoline (2.90 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.35 g, 수율 71%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 2 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylbenzo[h]quinazoline (2.90 g, 10.00 mmol) were used. The target compound (5.35 g, yield 71%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 11] 화합물 11] Compound 93 의93 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 2 (5.00 g, 10.00 mmol)와 2-(4-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (6.09 g, 수율 78%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 2 (5.00 g, 10.00 mmol) and 2-(4-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol) were used. The target compound (6.09 g, yield 78%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : Mass : [(M+H) + ] :
[[ 합성예Synthesis example 12] 화합물 12] Compound 94 의94 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 2 (5.00 g, 10.00 mmol)와 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline (3.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (6.39 g, 수율 77%)을 얻었다.Core 2 (5.00 g, 10.00 mmol) and 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine The target compound (6.39 g, yield 77%) was obtained by performing the same procedure as in Synthesis Example 1 except for using (3.66 g, 10.00 mmol).
Mass : [(M+H)+] : 832Mass : [(M+H) + ] : 832
[[ 합성예Synthesis example 13] 화합물 13] Compound 25 의25 of 합성 synthesis
Core 1 대신 Core 3 (5.00 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (6.21 g, 수율 88%)을 얻었다.The target compound (6.21 g, yield 88%) was obtained by performing the same process as Synthesis Example 1, except that Core 3 (5.00 g, 10.00 mmol) was used instead of Core 1.
Mass : [(M+H)+] : 706Mass : [(M+H) + ] : 706
[[ 합성예Synthesis example 14] 화합물 14] Compound 32 의32 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 3 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.42 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (6.63 g, 수율 85%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 3 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The target compound (6.63 g, yield 85%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloro-6-phenyl-1,3,5-triazine (3.42 g, 10.00 mmol).
Mass : [(M+H)+] : 781Mass : [(M+H) + ] : 781
[[ 합성예Synthesis example 15] 화합물 15] Compound 33 의33 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 3 (5.00 g, 10.00 mmol)와 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.88 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (6.48 g, 수율 83%)을 얻었다.Core 3 (5.00 g, 10.00 mmol) and 2-(3-bromophenyl)-4,6-diphenyl-1,3,5 instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. The target compound (6.48 g, yield 83%) was obtained by performing the same procedure as in Synthesis Example 1 except for using -triazine (3.88 g, 10.00 mmol).
Mass : [(M+H)+] : 782Mass : [(M+H) + ] : 782
[[ 합성예Synthesis example 16] 화합물 16] Compound 37 의37 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 3 (5.00 g, 10.00 mmol)와 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.56 g, 수율 82%)을 얻었다.Except using Core 3 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. Then, the same process as Synthesis Example 1 was performed to obtain the target compound (5.56 g, yield 82%).
Mass : [(M+H)+] : 679Mass : [(M+H) + ] : 679
[[ 합성예Synthesis example 17] 화합물 17] Compound 41 의41 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 3 (5.00 g, 10.00 mmol)와 2-(3-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (6.71 g, 수율 89%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 3 (5.00 g, 10.00 mmol) and 2-(3-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol) were used. The target compound (6.71 g, yield 89%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 18] 화합물 18] Compound 39 의39 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 3 (5.00 g, 10.00 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloroquinazoline (3.16 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (6.33 g, 수율 84%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 3 (5.00 g, 10.00 mmol) and 4-([1,1'-biphenyl]-4-yl)-2- The target compound (6.33 g, yield 84%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloroquinazoline (3.16 g, 10.00 mmol).
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 19] 화합물 19] Compound 99 의99 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 4 (5.00 g, 10.00 mmol)와 2-chloro-4,6-diphenylpyrimidine (2.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.07 g, 수율 72%)을 얻었다.Using Core 4 (5.00 g, 10.00 mmol) and 2-chloro-4,6-diphenylpyrimidine (2.66 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. Except for this, the same process as Synthesis Example 1 was performed to obtain the target compound (5.07 g, yield 72%).
Mass : [(M+H)+] : 705Mass : [(M+H) + ] : 705
[[ 합성예Synthesis example 20] 화합물 20] Compound 101 의101 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 4 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (6.01 g, 수율 77%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 4 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The target compound (6.01 g, yield 77%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol).
Mass : [(M+H)+] : 782Mass : [(M+H) + ] : 782
[[ 합성예Synthesis example 21] 화합물 21] Compound 107 의107 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 4 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (6.34 g, 수율 74%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 4 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The same process as Synthesis Example 1 was performed except for using (3-bromophenyl)-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol) to obtain the target compound (6.34 g, yield 74%). got it
Mass : [(M+H)+] : 859Mass : [(M+H) + ] : 859
[[ 합성예Synthesis example 22] 화합물 22] Compound 110 의110 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 4 (5.00 g, 10.00 mmol)와 2-chloro-4-phenylbenzo[h]quinazoline (2.90 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.46 g, 수율 75%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 4 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylbenzo[h]quinazoline (2.90 g, 10.00 mmol) were used. The target compound (5.46 g, yield 75%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 729Mass : [(M+H) + ] : 729
[[ 합성예Synthesis example 23] 화합물 23] Compound 117 의117 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 4 (5.00 g, 10.00 mmol)와 2-(4-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.96 g, 수율 79%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 4 (5.00 g, 10.00 mmol) and 2-(4-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol) were used. The target compound (5.96 g, yield 79%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 24] 화합물 24] Compound 118 의118 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 4 (5.00 g, 10.00 mmol)와 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline (3.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.79 g, 수율 72%)을 얻었다.Core 4 (5.00 g, 10.00 mmol) and 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine The target compound (5.79 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 1 except for using (3.66 g, 10.00 mmol).
Mass : [(M+H)+] : 805Mass : [(M+H) + ] : 805
[[ 합성예Synthesis example 25] 화합물 25] Compound 49 의49 of 합성 synthesis
Core 1 대신 Core 5 (5.00 g, 10.00 mmol)를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (6.13 g, 수율 85%)을 얻었다.The target compound (6.13 g, yield 85%) was obtained by performing the same process as Synthesis Example 1, except that Core 5 (5.00 g, 10.00 mmol) was used instead of Core 1.
Mass : [(M+H)+] : 722Mass : [(M+H) + ] : 722
[[ 합성예Synthesis example 26] 화합물 26] Compound 55 의55 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 5 (5.00 g, 10.00 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (3.42 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (6.62 g, 수율 83%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 5 (5.00 g, 10.00 mmol) and 4-([1,1'-biphenyl]-4-yl)-2- The target compound (6.62 g, yield 83%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloro-6-phenylpyrimidine (3.42 g, 10.00 mmol).
Mass : [(M+H)+] : 797Mass : [(M+H) + ] : 797
[[ 합성예Synthesis example 27] 화합물 27] Compound 57 의57 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 5 (5.00 g, 10.00 mmol)와 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.88 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (6.70 g, 수율 84%)을 얻었다.Core 5 (5.00 g, 10.00 mmol) and 2-(3-bromophenyl)-4,6-diphenyl-1,3,5 instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. The target compound (6.70 g, yield 84%) was obtained by performing the same procedure as in Synthesis Example 1 except for using -triazine (3.88 g, 10.00 mmol).
Mass : [(M+H)+] : 798Mass : [(M+H) + ] : 798
[[ 합성예Synthesis example 28] 화합물 28] Compound 61 의61 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 5 (5.00 g, 10.00 mmol)와 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.69 g, 수율 82%)을 얻었다.Except using Core 5 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. Then, the same process as Synthesis Example 1 was performed to obtain the target compound (5.69 g, yield 82%).
Mass : [(M+H)+] : 695Mass : [(M+H) + ] : 695
[[ 합성예Synthesis example 29] 화합물 29] Compound 65 의65 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 5 (5.00 g, 10.00 mmol)와 2-(3-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (6.62 g, 수율 86%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 5 (5.00 g, 10.00 mmol) and 2-(3-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol) were used. The target compound (6.62 g, yield 86%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 771Mass : [(M+H) + ] : 771
[[ 합성예Synthesis example 30] 화합물 30] Compound 63 의63 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 5 (5.00 g, 10.00 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloroquinazoline (3.16 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (6.70 g, 수율 87%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 5 (5.00 g, 10.00 mmol) and 4-([1,1'-biphenyl]-4-yl)-2- The target compound (6.70 g, yield 87%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloroquinazoline (3.16 g, 10.00 mmol).
Mass : [(M+H)+] : 771Mass : [(M+H) + ] : 771
[[ 합성예Synthesis example 31] 화합물 31] Compound 123 의123 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 6 (5.00 g, 10.00 mmol)와 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.19 g, 수율 72%)을 얻었다.Using Core 6 (5.00 g, 10.00 mmol) and 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. Except for this, the same process as Synthesis Example 1 was performed to obtain the target compound (5.19 g, yield 72%).
Mass : [(M+H)+] : 721Mass : [(M+H) + ] : 721
[[ 합성예Synthesis example 32] 화합물 32] Compound 125 의125 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 6 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.98 g, 수율 75%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 6 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The target compound (5.98 g, yield 75%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol).
Mass : [(M+H)+] : 798Mass : [(M+H) + ] : 798
[[ 합성예Synthesis example 33] 화합물 33] Compound 131 의131 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 6 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (6.37 g, 수율 73%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 6 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The same process as Synthesis Example 1 was performed except for using (3-bromophenyl)-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol) to obtain the target compound (6.37 g, yield 73%). got it
Mass : [(M+H)+] : 875Mass : [(M+H) + ] : 875
[[ 합성예Synthesis example 34] 화합물 34] Compound 134 의134 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 6 (5.00 g, 10.00 mmol)와 2-chloro-4-phenylbenzo[h]quinazoline (2.90 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.51 g, 수율 74%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 6 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylbenzo[h]quinazoline (2.90 g, 10.00 mmol) were used. The target compound (5.51 g, yield 74%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 745Mass : [(M+H) + ] : 745
[[ 합성예Synthesis example 35] 화합물 35] Compound 141 의141 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 6 (5.00 g, 10.00 mmol)와 2-(4-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (6.08 g, 수율 79%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 6 (5.00 g, 10.00 mmol) and 2-(4-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol) were used. The target compound (6.08 g, yield 79%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 771Mass : [(M+H) + ] : 771
[[ 합성예Synthesis example 36] 화합물 36] Compound 142 의142 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 6 (5.00 g, 10.00 mmol)와 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline (3.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (6.32 g, 수율 77%)을 얻었다.Core 6 (5.00 g, 10.00 mmol) and 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine The target compound (6.32 g, yield 77%) was obtained by performing the same procedure as in Synthesis Example 1 except for using (3.66 g, 10.00 mmol).
Mass : [(M+H)+] : 822Mass : [(M+H) + ] : 822
[[ 합성예Synthesis example 37] 화합물 37] Compound 145 의145 of 합성 synthesis
Core 1 대신 Core 7 (5.00 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.63 g, 수율 77%)을 얻었다.The target compound (5.63 g, yield 77%) was obtained by performing the same process as Synthesis Example 1, except that Core 7 (5.00 g, 10.00 mmol) was used instead of Core 1.
Mass : [(M+H)+] : 732Mass : [(M+H) + ] : 732
[[ 합성예Synthesis example 38] 화합물 38] Compound 150 의150 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 7 (5.00 g, 10.00 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (3.42 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.97 g, 수율 74%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 7 (5.00 g, 10.00 mmol) and 4-([1,1'-biphenyl]-4-yl)-6- The target compound (5.97 g, yield 74%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloro-2-phenylpyrimidine (3.42 g, 10.00 mmol).
Mass : [(M+H)+] : 808Mass : [(M+H) + ] : 808
[[ 합성예Synthesis example 39] 화합물 39] Compound 153 의153 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 7 (5.00 g, 10.00 mmol)와 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.88 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.81 g, 수율 72%)을 얻었다.Core 7 (5.00 g, 10.00 mmol) and 2-(3-bromophenyl)-4,6-diphenyl-1,3,5 instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. The target compound (5.81 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 1 except for using -triazine (3.88 g, 10.00 mmol).
Mass : [(M+H)+] : 809Mass : [(M+H) + ] : 809
[[ 합성예Synthesis example 40] 화합물 40] Compound 157 의157 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 7 (5.00 g, 10.00 mmol)와 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.49 g, 수율 78%)을 얻었다.Except using Core 7 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. Then, the same process as Synthesis Example 1 was performed to obtain the target compound (5.49 g, yield 78%).
Mass : [(M+H)+] : 705Mass : [(M+H) + ] : 705
[[ 합성예Synthesis example 41] 화합물 41] Compound 161 의161 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 7 (5.00 g, 10.00 mmol)와 2-(3-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.62 g, 수율 72%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 7 (5.00 g, 10.00 mmol) and 2-(3-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol) were used. The target compound (5.62 g, yield 72%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 781Mass : [(M+H) + ] : 781
[[ 합성예Synthesis example 42] 화합물 42] Compound 159 의159 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 7 (5.00 g, 10.00 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloroquinazoline (3.16 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.77 g, 수율 74%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 7 (5.00 g, 10.00 mmol) and 4-([1,1'-biphenyl]-4-yl)-2- The target compound (5.77 g, yield 74%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloroquinazoline (3.16 g, 10.00 mmol).
Mass : [(M+H)+] : 781Mass : [(M+H) + ] : 781
[[ 합성예Synthesis example 43] 화합물 43] Compound 219 의219 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 8 (5.00 g, 10.00 mmol)와 2-chloro-4,6-diphenylpyrimidine (2.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.11 g, 수율 70%)을 얻었다.Using Core 8 (5.00 g, 10.00 mmol) and 2-chloro-4,6-diphenylpyrimidine (2.66 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. Except for this, the same process as Synthesis Example 1 was performed to obtain the target compound (5.11 g, yield 70%).
Mass : [(M+H)+] : 731Mass : [(M+H) + ] : 731
[[ 합성예Synthesis example 44] 화합물 44] Compound 221 의221 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 8 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.73 g, 수율 71%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 8 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The target compound (5.73 g, yield 71%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol).
Mass : [(M+H)+] : 809Mass : [(M+H) + ] : 809
[[ 합성예Synthesis example 45] 화합물 45] Compound 227 의227 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 8 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (6.09 g, 수율 69%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 8 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The same process as Synthesis Example 1 was performed except for using (3-bromophenyl)-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol) to obtain the target compound (6.09 g, yield 69%). got it
Mass : [(M+H)+] : 885Mass : [(M+H) + ] : 885
[[ 합성예Synthesis example 46] 화합물 46] Compound 230 의230 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 8 (5.00 g, 10.00 mmol)와 2-chloro-4-phenylbenzo[h]quinazoline (2.90 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.13 g, 수율 68%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 8 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylbenzo[h]quinazoline (2.90 g, 10.00 mmol) were used. The target compound (5.13 g, yield 68%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 47] 화합물 47] Compound 237 의237 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 8 (5.00 g, 10.00 mmol)와 2-(4-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.62 g, 수율 72%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 8 (5.00 g, 10.00 mmol) and 2-(4-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol) were used. The target compound (5.62 g, yield 72%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 781Mass : [(M+H) + ] : 781
[[ 합성예Synthesis example 48] 화합물 48] Compound 238 의238 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 8 (5.00 g, 10.00 mmol)와 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline (3.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.73 g, 수율 69%)을 얻었다.Core 8 (5.00 g, 10.00 mmol) and 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine The target compound (5.73 g, yield 69%) was obtained by performing the same procedure as in Synthesis Example 1 except for using (3.66 g, 10.00 mmol).
Mass : [(M+H)+] : 832Mass : [(M+H) + ] : 832
[[ 합성예Synthesis example 49] 화합물 49] Compound 169 의169 of 합성 synthesis
Core 1 대신 Core 9 (5.00 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.43 g, 수율 77%)을 얻었다.The target compound (5.43 g, yield 77%) was obtained by performing the same process as Synthesis Example 1, except that Core 9 (5.00 g, 10.00 mmol) was used instead of Core 1.
Mass : [(M+H)+] : 706Mass : [(M+H) + ] : 706
[[ 합성예Synthesis example 50] 화합물 50] Compound 176 의176 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 9 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.42 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.70 g, 수율 73%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 9 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The target compound (5.70 g, yield 73%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloro-6-phenyl-1,3,5-triazine (3.42 g, 10.00 mmol).
Mass : [(M+H)+] : 781Mass : [(M+H) + ] : 781
[[ 합성예Synthesis example 51] 화합물 51] Compound 177 의177 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 9 (5.00 g, 10.00 mmol)와 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.88 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.62 g, 수율 72%)을 얻었다.Core 9 (5.00 g, 10.00 mmol) and 2-(3-bromophenyl)-4,6-diphenyl-1,3,5 instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. The target compound (5.62 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 1 except for using -triazine (3.88 g, 10.00 mmol).
Mass : [(M+H)+] : 782Mass : [(M+H) + ] : 782
[[ 합성예Synthesis example 52] 화합물 52] Compound 181 의181 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 9 (5.00 g, 10.00 mmol)와 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.36 g, 수율 79%)을 얻었다.Except using Core 9 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. Then, the same process as Synthesis Example 1 was performed to obtain the target compound (5.36 g, yield 79%).
Mass : [(M+H)+] : 679Mass : [(M+H) + ] : 679
[[ 합성예Synthesis example 53] 화합물 53] Compound 185 의185 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 9 (5.00 g, 10.00 mmol)와 2-(3-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.28 g, 수율 70%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 9 (5.00 g, 10.00 mmol) and 2-(3-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol) were used. The target compound (5.28 g, yield 70%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 54] 화합물 54] Compound 183 의183 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 9 (5.00 g, 10.00 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloroquinazoline (3.16 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.51 g, 수율 73%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 9 (5.00 g, 10.00 mmol) and 4-([1,1'-biphenyl]-4-yl)-2- The target compound (5.51 g, yield 73%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloroquinazoline (3.16 g, 10.00 mmol).
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 55] 화합물 55] Compound 242 의242 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 10 (5.00 g, 10.00 mmol)와 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.07 g, 수율 72%)을 얻었다.Using Core 10 (5.00 g, 10.00 mmol) and 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. Except for this, the same process as Synthesis Example 1 was performed to obtain the target compound (5.07 g, yield 72%).
Mass : [(M+H)+] : 705Mass : [(M+H) + ] : 705
[[ 합성예Synthesis example 56] 화합물 56] Compound 245 의245 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 10 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.23 g, 수율 67%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 10 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The target compound (5.23 g, yield 67%) was obtained by performing the same procedure as in Synthesis Example 1, except for using chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol).
Mass : [(M+H)+] : 782Mass : [(M+H) + ] : 782
[[ 합성예Synthesis example 57] 화합물 57] Compound 251 의251 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 10 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.66 g, 수율 66%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 10 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The same process as Synthesis Example 1 was performed except for using (3-bromophenyl)-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol) to obtain the target compound (5.66 g, yield 66%). got it
Mass : [(M+H)+] : 859Mass : [(M+H) + ] : 859
[[ 합성예Synthesis example 58] 화합물 58] Compound 254 의254 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 10 (5.00 g, 10.00 mmol)와 2-chloro-4-phenylbenzo[h]quinazoline (2.90 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.02 g, 수율 69%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 10 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylbenzo[h]quinazoline (2.90 g, 10.00 mmol) were used. The target compound (5.02 g, yield 69%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 729Mass : [(M+H) + ] : 729
[[ 합성예Synthesis example 59] 화합물 59] Compound 261 의261 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 10 (5.00 g, 10.00 mmol)와 2-(4-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.68 g, 수율 62%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 10 (5.00 g, 10.00 mmol) and 2-(4-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol) were used. The target compound (4.68 g, yield 62%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 60] 화합물 60] Compound 262 의262 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 10 (5.00 g, 10.00 mmol)와 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline (3.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.07 g, 수율 63%)을 얻었다.Core 10 (5.00 g, 10.00 mmol) and 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine The target compound (5.07 g, yield 63%) was obtained by performing the same procedure as in Synthesis Example 1 except for using (3.66 g, 10.00 mmol).
Mass : [(M+H)+] : 805Mass : [(M+H) + ] : 805
[[ 합성예Synthesis example 61] 화합물 61] Compound 193 의193 of 합성 synthesis
Core 1 대신 Core 11 (5.00 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.34 g, 수율 74%)을 얻었다.The same process as Synthesis Example 1 was performed except that Core 11 (5.00 g, 10.00 mmol) was used instead of Core 1 to obtain the target compound (5.34 g, yield 74%).
Mass : [(M+H)+] : 722Mass : [(M+H) + ] : 722
[[ 합성예Synthesis example 62] 화합물 62] Compound 199 의199 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 11 (5.00 g, 10.00 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (3.42 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.89 g, 수율 74%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 11 (5.00 g, 10.00 mmol) and 4-([1,1'-biphenyl]-4-yl)-2- The target compound (5.89 g, yield 74%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloro-6-phenylpyrimidine (3.42 g, 10.00 mmol).
Mass : [(M+H)+] : 797Mass : [(M+H) + ] : 797
[[ 합성예Synthesis example 63] 화합물 63] Compound 201 의201 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 11 (5.00 g, 10.00 mmol)와 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.88 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.74 g, 수율 72%)을 얻었다.Core 11 (5.00 g, 10.00 mmol) and 2-(3-bromophenyl)-4,6-diphenyl-1,3,5 instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. The target compound (5.74 g, yield 72%) was obtained by performing the same procedure as in Synthesis Example 1 except for using -triazine (3.88 g, 10.00 mmol).
Mass : [(M+H)+] : 798Mass : [(M+H) + ] : 798
[[ 합성예Synthesis example 64] 화합물 64] Compound 205 의205 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 11 (5.00 g, 10.00 mmol)와 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.86 g, 수율 70%)을 얻었다.Except using Core 11 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. Then, the same process as Synthesis Example 1 was performed to obtain the target compound (4.86 g, yield 70%).
Mass : [(M+H)+] : 695Mass : [(M+H) + ] : 695
[[ 합성예Synthesis example 65] 화합물 65] Compound 209 의209 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 11 (5.00 g, 10.00 mmol)와 2-(3-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.47 g, 수율 71%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 11 (5.00 g, 10.00 mmol) and 2-(3-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol) were used. The target compound (5.47 g, yield 71%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 771Mass : [(M+H) + ] : 771
[[ 합성예Synthesis example 66] 화합물 66] Compound 207 의207 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 11 (5.00 g, 10.00 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloroquinazoline (3.16 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.62 g, 수율 73%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 11 (5.00 g, 10.00 mmol) and 4-([1,1'-biphenyl]-4-yl)-2- The target compound (5.62 g, yield 73%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloroquinazoline (3.16 g, 10.00 mmol).
Mass : [(M+H)+] : 771Mass : [(M+H) + ] : 771
[[ 합성예Synthesis example 67] 화합물 67] Compound 267 의267 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 12 (5.00 g, 10.00 mmol)와 2-chloro-4,6-diphenylpyrimidine (2.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.97 g, 수율 69%)을 얻었다.Using Core 12 (5.00 g, 10.00 mmol) and 2-chloro-4,6-diphenylpyrimidine (2.66 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. Except for this, the same process as Synthesis Example 1 was performed to obtain the target compound (4.97 g, yield 69%).
Mass : [(M+H)+] : 721Mass : [(M+H) + ] : 721
[[ 합성예Synthesis example 68] 화합물 68] Compound 269 의269 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 12 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.26 g, 수율 66%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 12 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The target compound (5.26 g, yield 66%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol).
Mass : [(M+H)+] : 798Mass : [(M+H) + ] : 798
[[ 합성예Synthesis example 69] 화합물 69] Compound 275 의275 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 12 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.59 g, 수율 64%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 12 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The same process as Synthesis Example 1 was performed except for using (3-bromophenyl)-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol) to obtain the target compound (5.59 g, yield 64%). got it
Mass : [(M+H)+] : 875Mass : [(M+H) + ] : 875
[[ 합성예Synthesis example 70] 화합물 70] Compound 278 의278 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 12 (5.00 g, 10.00 mmol)와 2-chloro-4-phenylbenzo[h]quinazoline (2.90 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.06 g, 수율 68%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 12 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylbenzo[h]quinazoline (2.90 g, 10.00 mmol) were used. The target compound (5.06 g, yield 68%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 745Mass : [(M+H) + ] : 745
[[ 합성예Synthesis example 71] 화합물 71] Compound 285 의285 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 12 (5.00 g, 10.00 mmol)와 2-(4-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.85 g, 수율 63%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 12 (5.00 g, 10.00 mmol) and 2-(4-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol) were used. The target compound (4.85 g, yield 63%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 771Mass : [(M+H) + ] : 771
[[ 합성예Synthesis example 72] 화합물 72] Compound 286 의286 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 12 (5.00 g, 10.00 mmol)와 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline (3.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.41 g, 수율 66%)을 얻었다.Core 12 (5.00 g, 10.00 mmol) and 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine The target compound (5.41 g, yield 66%) was obtained by performing the same procedure as in Synthesis Example 1 except for using (3.66 g, 10.00 mmol).
Mass : [(M+H)+] : 822Mass : [(M+H) + ] : 822
[[ 합성예Synthesis example 73] 화합물 73] Compound 433 의433 합성 synthesis
Core 1 대신 Core 13 (5.00 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.24 g, 수율 58%)을 얻었다.The target compound (4.24 g, yield 58%) was obtained by performing the same process as Synthesis Example 1, except that Core 13 (5.00 g, 10.00 mmol) was used instead of Core 1.
Mass : [(M+H)+] : 732Mass : [(M+H) + ] : 732
[[ 합성예Synthesis example 74] 화합물 74] Compound 438 의438 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 13 (5.00 g, 10.00 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (3.42 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.76 g, 수율 59%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 13 (5.00 g, 10.00 mmol) and 4-([1,1'-biphenyl]-4-yl)-6- The target compound (4.76 g, yield 59%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloro-2-phenylpyrimidine (3.42 g, 10.00 mmol).
Mass : [(M+H)+] : 808Mass : [(M+H) + ] : 808
[[ 합성예Synthesis example 75] 화합물 75] Compound 441 의441 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 13 (5.00 g, 10.00 mmol)와 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.88 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.68 g, 수율 58%)을 얻었다.Core 13 (5.00 g, 10.00 mmol) and 2-(3-bromophenyl)-4,6-diphenyl-1,3,5 instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. The target compound (4.68 g, yield 58%) was obtained by performing the same procedure as in Synthesis Example 1 except for using -triazine (3.88 g, 10.00 mmol).
Mass : [(M+H)+] : 809Mass : [(M+H) + ] : 809
[[ 합성예Synthesis example 76] 화합물 76] Compound 445 의445 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 13 (5.00 g, 10.00 mmol)와 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (3.73 g, 수율 53%)을 얻었다.Except using Core 13 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. Then, the same process as Synthesis Example 1 was performed to obtain the target compound (3.73 g, yield 53%).
Mass : [(M+H)+] : 705Mass : [(M+H) + ] : 705
[[ 합성예Synthesis example 77] 화합물 77] Compound 449 의449 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 13 (5.00 g, 10.00 mmol)와 2-(3-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.29 g, 수율 55%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 13 (5.00 g, 10.00 mmol) and 2-(3-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol) were used. The target compound (4.29 g, yield 55%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 781Mass : [(M+H) + ] : 781
[[ 합성예Synthesis example 78] 화합물 78] Compound 447 의447 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 13 (5.00 g, 10.00 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloroquinazoline (3.16 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.45 g, 수율 57%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 13 (5.00 g, 10.00 mmol) and 4-([1,1'-biphenyl]-4-yl)-2- The target compound (4.45 g, yield 57%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloroquinazoline (3.16 g, 10.00 mmol).
Mass : [(M+H)+] : 781Mass : [(M+H) + ] : 781
[[ 합성예Synthesis example 79] 화합물 79] Compound 506 의506 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 14 (5.00 g, 10.00 mmol)와 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (3.72 g, 수율 51%)을 얻었다.Using Core 14 (5.00 g, 10.00 mmol) and 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. Except for this, the same process as Synthesis Example 1 was performed to obtain the target compound (3.72 g, yield 51%).
Mass : [(M+H)+] : 731Mass : [(M+H) + ] : 731
[[ 합성예Synthesis example 80] 화합물 80] Compound 509 의509 of 합성 synthesis
Core 14 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.28 g, 수율 53%)을 얻었다.Core 14 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol) The target compound (4.28 g, yield 53%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 809Mass : [(M+H) + ] : 809
[[ 합성예Synthesis example 81] 화합물 81] Compound 515 의515 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 14 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.77 g, 수율 54%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 14 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The same process as Synthesis Example 1 was performed except for using (3-bromophenyl)-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol) to obtain the target compound (4.77 g, yield 54%). got it
Mass : [(M+H)+] : 885Mass : [(M+H) + ] : 885
[[ 합성예Synthesis example 82] 화합물 82] Compound 518 의518 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 14 (5.00 g, 10.00 mmol)와 2-chloro-4-phenylbenzo[h]quinazoline (2.90 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.15 g, 수율 55%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 14 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylbenzo[h]quinazoline (2.90 g, 10.00 mmol) were used. The target compound (4.15 g, yield 55%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 83] 화합물 83] Compound 525 의525 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 14 (5.00 g, 10.00 mmol)와 2-(4-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.06 g, 수율 52%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 14 (5.00 g, 10.00 mmol) and 2-(4-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol) were used. The target compound (4.06 g, yield 52%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 781Mass : [(M+H) + ] : 781
[[ 합성예Synthesis example 84] 화합물 84] Compound 526 의526 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 14 (5.00 g, 10.00 mmol)와 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline (3.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.15 g, 수율 50%)을 얻었다.Core 14 (5.00 g, 10.00 mmol) and 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine The target compound (4.15 g, yield 50%) was obtained by performing the same procedure as in Synthesis Example 1 except for using (3.66 g, 10.00 mmol).
Mass : [(M+H)+] : 832Mass : [(M+H) + ] : 832
[[ 합성예Synthesis example 85] 화합물 85] Compound 457 의457 of 합성 synthesis
Core 1 대신 Core 15 (5.00 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.16 g, 수율 59%)을 얻었다.The same process as Synthesis Example 1 was performed except that Core 15 (5.00 g, 10.00 mmol) was used instead of Core 1 to obtain the target compound (4.16 g, yield 59%).
Mass : [(M+H)+] : 706Mass : [(M+H) + ] : 706
[[ 합성예Synthesis example 86] 화합물 86] Compound 464 의464 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 15 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.42 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.06 g, 수율 52%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 15 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The target compound (4.06 g, yield 52%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloro-6-phenyl-1,3,5-triazine (3.42 g, 10.00 mmol).
Mass : [(M+H)+] : 781Mass : [(M+H) + ] : 781
[[ 합성예Synthesis example 87] 화합물 87] Compound 465 의465 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 15 (5.00 g, 10.00 mmol)와 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.88 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.53 g, 수율 58%)을 얻었다.Core 15 (5.00 g, 10.00 mmol) and 2-(3-bromophenyl)-4,6-diphenyl-1,3,5 instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. The target compound (4.53 g, yield 58%) was obtained by performing the same procedure as in Synthesis Example 1 except for using -triazine (3.88 g, 10.00 mmol).
Mass : [(M+H)+] : 782Mass : [(M+H) + ] : 782
[[ 합성예Synthesis example 88] 화합물 88] Compound 469 의469 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 15 (5.00 g, 10.00 mmol)와 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (3.87 g, 수율 57%)을 얻었다.Except using Core 15 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. Then, the same process as Synthesis Example 1 was performed to obtain the target compound (3.87 g, yield 57%).
Mass : [(M+H)+] : 679Mass : [(M+H) + ] : 679
[[ 합성예Synthesis example 89] 화합물 89] Compound 473 의473 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 15 (5.00 g, 10.00 mmol)와 2-(3-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.00 g, 수율 53%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 15 (5.00 g, 10.00 mmol) and 2-(3-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol) were used. The target compound (4.00 g, yield 53%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 90] 화합물 90] Compound 471 의471 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 15 (5.00 g, 10.00 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloroquinazoline (3.16 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.15 g, 수율 55%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 15 (5.00 g, 10.00 mmol) and 4-([1,1'-biphenyl]-4-yl)-2- The target compound (4.15 g, yield 55%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloroquinazoline (3.16 g, 10.00 mmol).
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 91] 화합물 91] Compound 531 의531 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 16 (5.00 g, 10.00 mmol)와 2-chloro-4,6-diphenylpyrimidine (2.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (3.52 g, 수율 50%)을 얻었다.Using Core 16 (5.00 g, 10.00 mmol) and 2-chloro-4,6-diphenylpyrimidine (2.66 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. Except that the same process as Synthesis Example 1 was performed to obtain the target compound (3.52 g, yield 50%).
Mass : [(M+H)+] : 705Mass : [(M+H) + ] : 705
[[ 합성예Synthesis example 92] 화합물 92] Compound 533 의533 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 16 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (3.83 g, 수율 49%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 16 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The target compound (3.83 g, yield 49%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol).
Mass : [(M+H)+] : 782Mass : [(M+H) + ] : 782
[[ 합성예Synthesis example 93] 화합물 93] Compound 539 의539 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 16 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.54 g, 수율 53%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 16 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The same process as Synthesis Example 1 was performed except for using (3-bromophenyl)-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol) to obtain the target compound (4.54 g, yield 53%). got it
Mass : [(M+H)+] : 859Mass : [(M+H) + ] : 859
[[ 합성예Synthesis example 94] 화합물 94] Compound 542 의542 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 16 (5.00 g, 10.00 mmol)와 2-chloro-4-phenylbenzo[h]quinazoline (2.90 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (3.86 g, 수율 53%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 16 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylbenzo[h]quinazoline (2.90 g, 10.00 mmol) were used. The target compound (3.86 g, yield 53%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 729Mass : [(M+H) + ] : 729
[[ 합성예Synthesis example 95] 화합물 95] Compound 549 의549 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 16 (5.00 g, 10.00 mmol)와 2-(4-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (3.62 g, 수율 48%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 16 (5.00 g, 10.00 mmol) and 2-(4-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol) were used. The target compound (3.62 g, yield 48%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 96] 화합물 96] Compound 550 의550 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 16 (5.00 g, 10.00 mmol)와 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline (3.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.10 g, 수율 51%)을 얻었다.Core 16 (5.00 g, 10.00 mmol) and 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine The target compound (4.10 g, yield 51%) was obtained by performing the same procedure as in Synthesis Example 1 except for using (3.66 g, 10.00 mmol).
Mass : [(M+H)+] : 805Mass : [(M+H) + ] : 805
[[ 합성예Synthesis example 97] 화합물 97] Compound 481 의481 of 합성 synthesis
Core 1 대신 Core 17 (5.00 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.25 g, 수율 59%)을 얻었다.The target compound (4.25 g, yield 59%) was obtained by performing the same process as Synthesis Example 1, except that Core 17 (5.00 g, 10.00 mmol) was used instead of Core 1.
Mass : [(M+H)+] : 722Mass : [(M+H) + ] : 722
[[ 합성예Synthesis example 98] 화합물 98] Compound 486 의486 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 17 (5.00 g, 10.00 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (3.42 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.62 g, 수율 58%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 17 (5.00 g, 10.00 mmol) and 4-([1,1'-biphenyl]-4-yl)-6- The target compound (4.62 g, yield 58%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloro-2-phenylpyrimidine (3.42 g, 10.00 mmol).
Mass : [(M+H)+] : 797Mass : [(M+H) + ] : 797
[[ 합성예Synthesis example 99] 화합물 99] Compound 489 의489 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 17 (5.00 g, 10.00 mmol)와 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.88 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.38 g, 수율 55%)을 얻었다.Core 17 (5.00 g, 10.00 mmol) and 2-(3-bromophenyl)-4,6-diphenyl-1,3,5 instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. The target compound (4.38 g, yield 55%) was obtained by performing the same procedure as in Synthesis Example 1 except for using -triazine (3.88 g, 10.00 mmol).
Mass : [(M+H)+] : 798Mass : [(M+H) + ] : 798
[[ 합성예Synthesis example 100] 화합물 100] Compound 493 의493 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 17 (5.00 g, 10.00 mmol)와 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (3.61 g, 수율 52%)을 얻었다.Except using Core 17 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. Then, the same process as Synthesis Example 1 was performed to obtain the target compound (3.61 g, yield 52%).
Mass : [(M+H)+] : 695Mass : [(M+H) + ] : 695
[[ 합성예Synthesis example 101] 화합물 101] Compound 497 의497 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 17 (5.00 g, 10.00 mmol)와 2-(3-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.08 g, 수율 53%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 17 (5.00 g, 10.00 mmol) and 2-(3-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol) were used. The target compound (4.08 g, yield 53%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 771Mass : [(M+H) + ] : 771
[[ 합성예Synthesis example 102] 화합물 102] Compound 495 의495 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 17 (5.00 g, 10.00 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloroquinazoline (3.16 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.39 g, 수율 57%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 17 (5.00 g, 10.00 mmol) and 4-([1,1'-biphenyl]-4-yl)-2- The target compound (4.39 g, yield 57%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloroquinazoline (3.16 g, 10.00 mmol).
Mass : [(M+H)+] : 771Mass : [(M+H) + ] : 771
[[ 합성예Synthesis example 103] 화합물 103] Compound 554 의554 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 18 (5.00 g, 10.00 mmol)와 2-chloro-4,6-diphenylpyrimidine (2.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (3.53 g, 수율 49%)을 얻었다.Using Core 18 (5.00 g, 10.00 mmol) and 2-chloro-4,6-diphenylpyrimidine (2.66 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. Except that the same process as Synthesis Example 1 was performed to obtain the target compound (3.53 g, yield 49%).
Mass : [(M+H)+] : 721Mass : [(M+H) + ] : 721
[[ 합성예Synthesis example 104] 화합물 104] Compound 557 의557 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 18 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (3.75 g, 수율 47%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 18 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The target compound (3.75 g, yield 47%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol).
Mass : [(M+H)+] : 798Mass : [(M+H) + ] : 798
[[ 합성예Synthesis example 105] 화합물 105] Compound 563 의563 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 18 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (3.84 g, 수율 44%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 18 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The same process as Synthesis Example 1 was performed except for using (3-bromophenyl)-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol) to obtain the target compound (3.84 g, yield 44%). got it
Mass : [(M+H)+] : 875Mass : [(M+H) + ] : 875
[[ 합성예Synthesis example 106] 화합물 106] Compound 566 의566 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 18 (5.00 g, 10.00 mmol)와 2-chloro-4-phenylbenzo[h]quinazoline (2.90 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (3.72 g, 수율 50%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 18 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylbenzo[h]quinazoline (2.90 g, 10.00 mmol) were used. The target compound (3.72 g, yield 50%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 745Mass : [(M+H) + ] : 745
[[ 합성예Synthesis example 107] 화합물 107] Compound 573 의573 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 18 (5.00 g, 10.00 mmol)와 2-(4-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (3.23 g, 수율 42%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 18 (5.00 g, 10.00 mmol) and 2-(4-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol) were used. The target compound (3.23 g, yield 42%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 771Mass : [(M+H) + ] : 771
[[ 합성예Synthesis example 108] 화합물 108] Compound 574 의574 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 18 (5.00 g, 10.00 mmol)와 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline (3.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (3.94 g, 수율 48%)을 얻었다.Core 18 (5.00 g, 10.00 mmol) and 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine The target compound (3.94 g, yield 48%) was obtained by performing the same procedure as in Synthesis Example 1 except for using (3.66 g, 10.00 mmol).
Mass : [(M+H)+] : 822Mass : [(M+H) + ] : 822
[[ 합성예Synthesis example 109] 화합물 109] Compound 289 의289 of 합성 synthesis
Core 1 대신 Core 19 (5.00 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.05 g, 수율 69%)을 얻었다.The same process as Synthesis Example 1 was performed except that Core 19 (5.00 g, 10.00 mmol) was used instead of Core 1 to obtain the target compound (5.05 g, yield 69%).
Mass : [(M+H)+] : 732Mass : [(M+H) + ] : 732
[[ 합성예Synthesis example 110] 화합물 110] Compound 294 의294 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 19 (5.00 g, 10.00 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (3.42 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.32 g, 수율 66%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 19 (5.00 g, 10.00 mmol) and 4-([1,1'-biphenyl]-4-yl)-6- The target compound (5.32 g, yield 66%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloro-2-phenylpyrimidine (3.42 g, 10.00 mmol).
Mass : [(M+H)+] : 808Mass : [(M+H) + ] : 808
[[ 합성예Synthesis example 111] 화합물 111] Compound 297 의297 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 19 (5.00 g, 10.00 mmol)와 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.88 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.89 g, 수율 73%)을 얻었다.Core 19 (5.00 g, 10.00 mmol) and 2-(3-bromophenyl)-4,6-diphenyl-1,3,5 instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. The target compound (5.89 g, yield 73%) was obtained by performing the same procedure as in Synthesis Example 1 except for using -triazine (3.88 g, 10.00 mmol).
Mass : [(M+H)+] : 809Mass : [(M+H) + ] : 809
[[ 합성예Synthesis example 112] 화합물 112] Compound 301 의301 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 19 (5.00 g, 10.00 mmol)와 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.86 g, 수율 69%)을 얻었다.Except using Core 19 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. Then, the same process as Synthesis Example 1 was performed to obtain the target compound (4.86 g, yield 69%).
Mass : [(M+H)+] : 705Mass : [(M+H) + ] : 705
[[ 합성예Synthesis example 113] 화합물 113] Compound 305 의305 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 19 (5.00 g, 10.00 mmol)와 2-(3-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.46 g, 수율 70%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 19 (5.00 g, 10.00 mmol) and 2-(3-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol) were used. The target compound (5.46 g, yield 70%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 781Mass : [(M+H) + ] : 781
[[ 합성예Synthesis example 114] 화합물 114] Compound 303 의303 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 19 (5.00 g, 10.00 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloroquinazoline (3.16 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.31 g, 수율 68%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 19 (5.00 g, 10.00 mmol) and 4-([1,1'-biphenyl]-4-yl)-2- The target compound (5.31 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloroquinazoline (3.16 g, 10.00 mmol).
Mass : [(M+H)+] : 781Mass : [(M+H) + ] : 781
[[ 합성예Synthesis example 115] 화합물 115] Compound 362 의362 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 20 (5.00 g, 10.00 mmol)와 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.45 g, 수율 61%)을 얻었다.Using Core 20 (5.00 g, 10.00 mmol) and 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. Except for this, the same process as Synthesis Example 1 was performed to obtain the target compound (4.45 g, yield 61%).
Mass : [(M+H)+] : 731Mass : [(M+H) + ] : 731
[[ 합성예Synthesis example 116] 화합물 116] Compound 365 의365 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 20 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.84 g, 수율 60%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 20 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The target compound (4.84 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 1, except for using chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol).
Mass : [(M+H)+] : 809Mass : [(M+H) + ] : 809
[[ 합성예Synthesis example 117] 화합물 117] Compound 371 의371 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 20 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.12 g, 수율 58%)을 얻었다. Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 20 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The same process as Synthesis Example 1 was performed except for using (3-bromophenyl)-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol) to obtain the target compound (5.12 g, yield 58%). got it
Mass : [(M+H)+] : 885Mass : [(M+H) + ] : 885
[[ 합성예Synthesis example 118] 화합물 118] Compound 374 의374 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 20 (5.00 g, 10.00 mmol)와 2-chloro-4-phenylbenzo[h]quinazoline (2.90 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.68 g, 수율 62%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 20 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylbenzo[h]quinazoline (2.90 g, 10.00 mmol) were used. The target compound (4.68 g, yield 62%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 119] 화합물 119] Compound 381 의381 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 20 (5.00 g, 10.00 mmol)와 2-(4-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.15 g, 수율 66%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 20 (5.00 g, 10.00 mmol) and 2-(4-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol) were used. The target compound (5.15 g, yield 66%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 781Mass : [(M+H) + ] : 781
[[ 합성예Synthesis example 120] 화합물 120] Compound 382 의382 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 20 (5.00 g, 10.00 mmol)와 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline (3.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.23 g, 수율 63%)을 얻었다.Core 20 (5.00 g, 10.00 mmol) and 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine The target compound (5.23 g, yield 63%) was obtained by performing the same procedure as in Synthesis Example 1 except for using (3.66 g, 10.00 mmol).
Mass : [(M+H)+] : 832Mass : [(M+H) + ] : 832
[[ 합성예Synthesis example 121] 화합물 121] Compound 313 의313 합성 synthesis
Core 1 대신 Core 21 (5.00 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.79 g, 수율 68%)을 얻었다.The same process as Synthesis Example 1 was performed except that Core 21 (5.00 g, 10.00 mmol) was used instead of Core 1 to obtain the target compound (4.79 g, yield 68%).
Mass : [(M+H)+] : 706Mass : [(M+H) + ] : 706
[[ 합성예Synthesis example 122] 화합물 122] Compound 318 의318 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 21 (5.00 g, 10.00 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (3.42 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.31 g, 수율 68%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 21 (5.00 g, 10.00 mmol) and 4-([1,1'-biphenyl]-4-yl)-6- The target compound (5.31 g, yield 68%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloro-2-phenylpyrimidine (3.42 g, 10.00 mmol).
Mass : [(M+H)+] : 781Mass : [(M+H) + ] : 781
[[ 합성예Synthesis example 123] 화합물 123] Compound 321 의321 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 21 (5.00 g, 10.00 mmol)와 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.88 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.84 g, 수율 62%)을 얻었다.Core 21 (5.00 g, 10.00 mmol) and 2-(3-bromophenyl)-4,6-diphenyl-1,3,5 instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. The target compound (4.84 g, yield 62%) was obtained by performing the same procedure as in Synthesis Example 1 except for using -triazine (3.88 g, 10.00 mmol).
Mass : [(M+H)+] : 782Mass : [(M+H) + ] : 782
[[ 합성예Synthesis example 124] 화합물 124] Compound 325 의325 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 21 (5.00 g, 10.00 mmol)와 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.48 g, 수율 66%)을 얻었다.Except using Core 21 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. Then, the same process as Synthesis Example 1 was performed to obtain the target compound (4.48 g, yield 66%).
Mass : [(M+H)+] : 679Mass : [(M+H) + ] : 679
[[ 합성예Synthesis example 125] 화합물 125] Compound 329 의329 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 21 (5.00 g, 10.00 mmol)와 2-(3-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.52 g, 수율 60%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 21 (5.00 g, 10.00 mmol) and 2-(3-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol) were used. The target compound (4.52 g, yield 60%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 126] 화합물 126] Compound 327 의327 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 21 (5.00 g, 10.00 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloroquinazoline (3.16 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.20 g, 수율 69%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 21 (5.00 g, 10.00 mmol) and 4-([1,1'-biphenyl]-4-yl)-2- The target compound (5.20 g, yield 69%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloroquinazoline (3.16 g, 10.00 mmol).
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 127] 화합물 127] Compound 386 의386 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 22 (5.00 g, 10.00 mmol)와 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.30 g, 수율 61%)을 얻었다.Using Core 22 (5.00 g, 10.00 mmol) and 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. Except for this, the same process as Synthesis Example 1 was performed to obtain the target compound (4.30 g, yield 61%).
Mass : [(M+H)+] : 705Mass : [(M+H) + ] : 705
[[ 합성예Synthesis example 128] 화합물 128] Compound 389 의389 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 22 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.53 g, 수율 58%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 22 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The target compound (4.53 g, yield 58%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol).
Mass : [(M+H)+] : 782Mass : [(M+H) + ] : 782
[[ 합성예Synthesis example 129] 화합물 129] Compound 395 의395 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 22 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.97 g, 수율 58%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 22 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The target compound (4.97 g, yield 58%) was obtained by performing the same process as Synthesis Example 1 except for using (3-bromophenyl)-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol). got it
Mass : [(M+H)+] : 859Mass : [(M+H) + ] : 859
[[ 합성예Synthesis example 130] 화합물 130] Compound 398 의398 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 22 (5.00 g, 10.00 mmol)와 2-chloro-4-phenylbenzo[h]quinazoline (2.90 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.51 g, 수율 62%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 22 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylbenzo[h]quinazoline (2.90 g, 10.00 mmol) were used. The target compound (4.51 g, yield 62%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 729Mass : [(M+H) + ] : 729
[[ 합성예Synthesis example 131] 화합물 131] Compound 405 의405 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 22 (5.00 g, 10.00 mmol)와 2-(4-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.98 g, 수율 66%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 22 (5.00 g, 10.00 mmol) and 2-(4-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol) were used. The target compound (4.98 g, yield 66%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 755Mass : [(M+H) + ] : 755
[[ 합성예Synthesis example 132] 화합물 132] Compound 406 의406 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 22 (5.00 g, 10.00 mmol)와 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline (3.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.82 g, 수율 60%)을 얻었다.Core 22 (5.00 g, 10.00 mmol) and 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine The target compound (4.82 g, yield 60%) was obtained by performing the same procedure as in Synthesis Example 1 except for using (3.66 g, 10.00 mmol).
Mass : [(M+H)+] : 805Mass : [(M+H) + ] : 805
[[ 합성예Synthesis example 133] 화합물 133] Compound 337 의337 합성 synthesis
Core 1 대신 Core 23 (5.00 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.47 g, 수율 62%)을 얻었다.The target compound (4.47 g, yield 62%) was obtained by performing the same process as Synthesis Example 1, except that Core 23 (5.00 g, 10.00 mmol) was used instead of Core 1.
Mass : [(M+H)+] : 722Mass : [(M+H) + ] : 722
[[ 합성예Synthesis example 134] 화합물 134] Compound 342 의342 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 23 (5.00 g, 10.00 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (3.42 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.02 g, 수율 63%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 23 (5.00 g, 10.00 mmol) and 4-([1,1'-biphenyl]-4-yl)-6- The target compound (5.02 g, yield 63%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloro-2-phenylpyrimidine (3.42 g, 10.00 mmol).
Mass : [(M+H)+] : 797Mass : [(M+H) + ] : 797
[[ 합성예Synthesis example 135] 화합물 135] Compound 345 의345 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 23 (5.00 g, 10.00 mmol)와 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.88 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (5.26 g, 수율 63%)을 얻었다.Core 23 (5.00 g, 10.00 mmol) and 2-(3-bromophenyl)-4,6-diphenyl-1,3,5 instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. The target compound (5.26 g, yield 63%) was obtained by performing the same procedure as in Synthesis Example 1 except for using -triazine (3.88 g, 10.00 mmol).
Mass : [(M+H)+] : 798Mass : [(M+H) + ] : 798
[[ 합성예Synthesis example 136] 화합물 136] Compound 349 의349 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 23 (5.00 g, 10.00 mmol)와 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.16 g, 수율 60%)을 얻었다.Except using Core 23 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylquinazoline (2.40 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. Then, the same process as Synthesis Example 1 was performed to obtain the target compound (4.16 g, yield 60%).
Mass : [(M+H)+] : 695Mass : [(M+H) + ] : 695
[[ 합성예Synthesis example 137] 화합물 137] Compound 353 의353 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 23 (5.00 g, 10.00 mmol)와 2-(3-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.70 g, 수율 61%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 23 (5.00 g, 10.00 mmol) and 2-(3-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol) were used. The target compound (4.70 g, yield 61%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 771Mass : [(M+H) + ] : 771
[[ 합성예Synthesis example 138] 화합물 138] Compound 351 의351 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 23 (5.00 g, 10.00 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloroquinazoline (3.16 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.54 g, 수율 59%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 23 (5.00 g, 10.00 mmol) and 4-([1,1'-biphenyl]-4-yl)-2- The target compound (4.54 g, yield 59%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloroquinazoline (3.16 g, 10.00 mmol).
Mass : [(M+H)+] : 771Mass : [(M+H) + ] : 771
[[ 합성예Synthesis example 139] 화합물 139] Compound 410 의410 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 24 (5.00 g, 10.00 mmol)와 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.18 g, 수율 58%)을 얻었다.Using Core 24 (5.00 g, 10.00 mmol) and 4-chloro-2,6-diphenylpyrimidine (2.66 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. Except for this, the same process as Synthesis Example 1 was performed to obtain the target compound (4.18 g, yield 58%).
Mass : [(M+H)+] : 721Mass : [(M+H) + ] : 721
[[ 합성예Synthesis example 140] 화합물 140] Compound 413 의413 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 24 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.38 g, 수율 55%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 24 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The target compound (4.38 g, yield 55%) was obtained by performing the same procedure as in Synthesis Example 1 except for using chloro-6-phenyl-1,3,5-triazine (3.43 g, 10.00 mmol).
Mass : [(M+H)+] : 798Mass : [(M+H) + ] : 798
[[ 합성예Synthesis example 141] 화합물 141] Compound 419 의419 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 24 (5.00 g, 10.00 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.98 g, 수율 57%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 24 (5.00 g, 10.00 mmol) and 2-([1,1'-biphenyl]-4-yl)-4- The same process as Synthesis Example 1 was performed except for using (3-bromophenyl)-6-phenyl-1,3,5-triazine (4.64 g, 10.00 mmol) to obtain the target compound (4.98 g, yield 57%). got it
Mass : [(M+H)+] : 875Mass : [(M+H) + ] : 875
[[ 합성예Synthesis example 142] 화합물 142] Compound 422 의422 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 24 (5.00 g, 10.00 mmol)와 2-chloro-4-phenylbenzo[h]quinazoline (2.90 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (3.72 g, 수율 50%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 24 (5.00 g, 10.00 mmol) and 2-chloro-4-phenylbenzo[h]quinazoline (2.90 g, 10.00 mmol) were used. The target compound (3.72 g, yield 50%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 745Mass : [(M+H) + ] : 745
[[ 합성예Synthesis example 143] 화합물 143] Compound 429 의429 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 24 (5.00 g, 10.00 mmol)와 2-(4-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (3.93 g, 수율 51%)을 얻었다.Instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, Core 24 (5.00 g, 10.00 mmol) and 2-(4-bromophenyl)-4-phenylquinazoline (3.61 g, 10.00 mmol) were used. The target compound (3.93 g, yield 51%) was obtained by performing the same process as Synthesis Example 1 except for using.
Mass : [(M+H)+] : 771Mass : [(M+H) + ] : 771
[[ 합성예Synthesis example 144] 화합물 144] Compound 430 의430 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 24 (5.00 g, 10.00 mmol)와 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline (3.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.51 g, 수율 55%)을 얻었다.Core 24 (5.00 g, 10.00 mmol) and 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine The target compound (4.51 g, yield 55%) was obtained by performing the same procedure as in Synthesis Example 1 except for using (3.66 g, 10.00 mmol).
Mass : [(M+H)+] : 822Mass : [(M+H) + ] : 822
[[ 합성예Synthesis example 145] 화합물 145] Compound 27 의27 of 합성 synthesis
Core 1과 2-chloro-4,6-diphenyl-1,3,5-triazine 대신 Core 3 (5.00 g, 10.00 mmol)와 2-chloro-4,6-diphenylpyrimidine (2.66 g, 10.00 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물 (4.23 g, 수율 60%)을 얻었다.Using Core 3 (5.00 g, 10.00 mmol) and 2-chloro-4,6-diphenylpyrimidine (2.66 g, 10.00 mmol) instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5-triazine. Except for this, the same process as Synthesis Example 1 was performed to obtain the target compound (4.23 g, yield 60%).
Mass : [(M+H)+] : 705Mass : [(M+H) + ] : 705
[[ 실시예Example 1 내지 72] 적색 유기 1 to 72] red organic 전계electric field 발광 소자의 제작 Fabrication of light emitting devices
상기 합성예에서 합성한 화합물 13, 15, 17, 37, 39, 41, 61, 63, 65, 86, 93, 94, 110, 117, 118, 134, 141, 142, 157, 159, 161, 181, 183, 185, 205, 207, 209, 230, 237, 238, 254, 261, 262, 278, 285, 286, 301, 303, 305, 325, 327, 329, 349, 351, 353, 374, 381, 382, 398, 405, 406, 422, 429, 430, 445, 447, 469, 471, 473, 493, 495, 497, 518, 525, 526, 542, 549, 550, 566, 573, 574를 통상적으로 알려진 방법으로 고순도 승화정제한 후 아래의 과정에 따라 적색 유기 전계 발광 소자를 제작하였다.Compounds 13, 15, 17, 37, 39, 41, 61, 63, 65, 86, 93, 94, 110, 117, 118, 134, 141, 142, 157, 159, 161, 181 synthesized in the above synthesis example , 183, 185, 205, 207, 209, 230, 237, 238, 254, 261, 262, 278, 285, 286, 301, 303, 305, 325, 327, 329, 349, 351, 353, 374, 381 , 382, 398, 405, 406, 422, 429, 430, 445, 447, 469, 471, 473, 493, 495, 497, 518, 525, 526, 542, 549, 550, 566, 573, 574 commercial After high-purity sublimation purification using a known method, a red organic electroluminescent device was produced according to the process below.
먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 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 a thin film of ITO (indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonic waves. After cleaning with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, methanol, etc., drying, transferring to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then cleaning the substrate using UV for 5 minutes and using a vacuum evaporator. The substrate was transferred to .
이렇게 준비된 ITO 투명 전극 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ 90% 표 2의 각각의 화합물 + 10 % (piq)2Ir(acac) (300 nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다.On the ITO transparent electrode prepared in this way, m-MTDATA (60 nm)/TCTA (80 nm)/ 90% each compound in Table 2 + 10% (piq) 2 Ir(acac) (300 nm)/BCP (10 nm)/ An organic electroluminescent device was manufactured by stacking Alq 3 (30 nm)/LiF (1 nm)/Al (200 nm) in that order.
[[ 비교예Comparative example 1] 적색 유기 1] Red organic 전계electric field 발광 소자의 제작 Fabrication of light emitting devices
발광층 형성시 발광 호스트 물질로서 화합물 13 대신 CBP를 사용하는 것을 제외하고는 상기 실시예 1과 동일한 과정으로 적색 유기 전계 발광 소자를 제작하였다.A red organic electroluminescent device was manufactured in the same process as Example 1, except that CBP was used instead of Compound 13 as the light-emitting host material when forming the light-emitting layer.
[[ 비교예Comparative example 2] 적색 유기 2] Red organic 전계electric field 발광 소자의 제작 Fabrication of light emitting devices
발광층 형성시 발광 호스트 물질로서 화합물 13 대신 화합물 A를 사용하는 것을 제외하고는 상기 실시예 1과 동일한 과정으로 적색 유기 전계 발광 소자를 제작하였다.A red organic electroluminescent device was manufactured in the same process as Example 1, except that Compound A was used instead of Compound 13 as the light-emitting host material when forming the light-emitting layer.
상기 실시예 1 내지 72, 비교예 1 및 2 에서 사용된 m-MTDATA, TCTA, (piq)2Ir(acac), BCP, CBP 및 화합물 A의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, (piq) 2 Ir(acac), BCP, CBP, and Compound A used in Examples 1 to 72 and Comparative Examples 1 and 2 are as follows.
[[ 평가예Evaluation example 1] One]
실시예 1 내지 72, 비교예 1 및 2에서 제작한 각각의 적색 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압 및 전류효율을 측정하고, 그 결과를 하기 표 2에 나타내었다.The driving voltage and current efficiency were measured at a current density of 10 mA/cm2 for each red organic electroluminescent device manufactured in Examples 1 to 72 and Comparative Examples 1 and 2, and the results are shown in Table 2 below.
상기 표 2에 나타낸 바와 같이, 본 발명에 따른 화합물을 발광층에 사용한 적색 유기 전계 발광 소자(실시예 1 내지 72)는 CBP 또는 화합물 A를 발광층에 사용한 적색 유기 전계 발광 소자(비교예 1 또는 2)에 비해 전류효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있었다.As shown in Table 2, the red organic electroluminescent device using the compound according to the present invention in the emitting layer (Examples 1 to 72) is the red organic electroluminescent device using CBP or Compound A in the emitting layer (Comparative Example 1 or 2) It was found that it showed better performance in terms of current efficiency and driving voltage compared to .
또한, 실시예 1, 5, 7, 8, 10, 13, 19, 22, 25, 28, 31 및 34, 비교예 1 및 2에서 제작한 각각의 적색 유기 전계 발광 소자에 대하여 수명(T90: 초기 휘도에서 90%로 감소하는데 소요되는 시간)을 측정하고, 그 결과를 하기 표 3에 나타내었다.In addition, the lifespan (T90: initial period) for each of the red organic electroluminescent devices manufactured in Examples 1, 5, 7, 8, 10, 13, 19, 22, 25, 28, 31, and 34, and Comparative Examples 1 and 2. The time required for luminance to decrease to 90%) was measured, and the results are shown in Table 3 below.
상기 표 3에 나타낸 바와 같이, 본 발명에 따른 화합물을 발광층에 사용한 적색 유기 전계 발광 소자(실시예 1, 5, 7, 8, 10, 13, 19, 22, 25, 28, 31 및 34)는 CBP 또는 화합물 A를 발광층에 사용한 적색 유기 전계 발광 소자(비교예 1 또는 2)에 비해 긴 수명을 나타내는 것을 알 수 있었다.As shown in Table 3, the red organic electroluminescent device (Examples 1, 5, 7, 8, 10, 13, 19, 22, 25, 28, 31, and 34) using the compound according to the present invention in the emitting layer was It was found that the red organic electroluminescent device using CBP or Compound A in the emitting layer (Comparative Example 1 or 2) had a longer lifespan.
[[ 실시예Example 73 내지 145] 녹색 유기 73 to 145] green organic 전계electric field 발광 소자의 제작 Fabrication of light emitting devices
상기 합성예에서 합성한 화합물 1, 6, 9, 25, 27, 32, 33, 49, 55, 57, 74, 77, 83, 99, 101, 107, 123, 125, 131, 145, 150, 153, 169, 176, 177, 193, 199, 201, 219, 221, 227, 242, 245, 251, 267, 269, 275, 289, 294, 297, 313, 318, 321, 337, 342, 345, 362, 365, 371, 386, 389, 395, 410, 413, 419, 433, 438, 441, 457, 464, 465, 481, 486, 489, 506, 509, 515, 531, 533, 539, 554, 557, 563을 통상적으로 알려진 방법으로 고순도 승화정제한 후 아래의 과정에 따라 녹색 유기 전계 발광 소자를 제작하였다.Compounds 1, 6, 9, 25, 27, 32, 33, 49, 55, 57, 74, 77, 83, 99, 101, 107, 123, 125, 131, 145, 150, 153 synthesized in the above synthesis example , 169, 176, 177, 193, 199, 201, 219, 221, 227, 242, 245, 251, 267, 269, 275, 289, 294, 297, 313, 318, 321, 337, 342, 345, 362 , 365, 371, 386, 389, 395, 410, 413, 419, 433, 438, 441, 457, 464, 465, 481, 486, 489, 506, 509, 515, 531, 533, 539, 554, 557 , 563 was purified to high purity by sublimation using a commonly known method, and then a green organic electroluminescent device was produced according to the process below.
먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 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 a 1500 Å thin film of ITO (indium tin oxide) was washed with distilled water ultrasonic waves. After cleaning with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, methanol, etc., drying, transferring to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaning the substrate for 5 minutes using UV, and vacuum evaporation. The substrate was transferred to .
이렇게 준비된 ITO 투명 전극 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ 90% 표 4의 각각의 화합물 + 10 % Ir(ppy)3 (300 nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다. On the ITO transparent electrode prepared in this way, m-MTDATA (60 nm)/TCTA (80 nm)/90% each compound in Table 4 + 10% Ir(ppy) 3 (300 nm)/BCP (10 nm)/Alq 3 ( An organic electroluminescent device was manufactured by stacking in the following order: 30 nm)/LiF (1 nm)/Al (200 nm).
[[ 비교예Comparative example 3] 녹색 유기 3] Green Organic 전계electric field 발광 소자의 제작 Fabrication of light emitting devices
발광층 형성시 발광 호스트 물질로서 화합물 1 대신 CBP를 사용하는 것을 제외하고는 실시예 73 과 동일한 과정으로 녹색 유기 전계 발광 소자를 제작하였다.A green organic electroluminescent device was manufactured in the same process as Example 73, except that CBP was used instead of Compound 1 as the light-emitting host material when forming the light-emitting layer.
[[ 비교예Comparative example 4] 녹색 유기 4] Green Organic 전계electric field 발광 소자의 제작 Fabrication of light emitting devices
발광층 형성시 발광 호스트 물질로서 화합물 1 대신 화합물 B 를 사용하는 것을 제외하고는 실시예 73 과 동일한 과정으로 녹색 유기 전계 발광 소자를 제작하였다.A green organic electroluminescent device was manufactured in the same process as Example 73, except that Compound B was used instead of Compound 1 as the light-emitting host material when forming the light-emitting layer.
[[ 비교예Comparative example 5] 녹색 유기 5] Green Organic 전계electric field 발광 소자의 제작 Fabrication of light emitting devices
발광층 형성시 발광 호스트 물질로서 화합물 1 대신 화합물 C 를 사용하는 것을 제외하고는 실시예 73 과 동일한 과정으로 녹색 유기 전계 발광 소자를 제작하였다.A green organic electroluminescent device was manufactured in the same process as Example 73, except that Compound C was used instead of Compound 1 as the light-emitting host material when forming the light-emitting layer.
상기 Ir(ppy)3, 화합물 B 및 화합물 C의 구조는 하기와 같다.The structures of Ir(ppy) 3 , Compound B, and Compound C are as follows.
[[ 평가예Evaluation example 2] 2]
실시예 73 내지 145, 비교예 3 내지 5 에서 제작한 각각의 녹색 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 4에 나타내었다.For each green organic electroluminescent device manufactured in Examples 73 to 145 and Comparative Examples 3 to 5, the driving voltage, current efficiency, and luminescence peak were measured at a current density of 10 mA/cm2, and the results are shown in Table 4 below. indicated.
(V)driving voltage
(V)
(nm)EL peak
(nm)
(cd/A)Current efficiency
(cd/A)
상기 표4에 나타낸 바와 같이, 본 발명에 따른 화합물을 발광층에 사용한 녹색 유기 전계 발광 소자(실시예 73 내지 145)는 CBP, 화합물 B 또는 화합물 C를 발광층에 사용한 녹색 유기 전계 발광 소자(비교예 3, 4 또는 5)에 비해 전류효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있었다.As shown in Table 4, the green organic electroluminescent device using the compound according to the present invention in the emitting layer (Examples 73 to 145) is the green organic electroluminescent device using CBP, Compound B, or Compound C in the emitting layer (Comparative Example 3) , 4 or 5), it was found to exhibit better performance in terms of current efficiency and driving voltage.
또한, 실시예 73, 75, 76, 79, 85, 89, 91, 93, 94, 96, 97, 99, 비교예 3 내지 5에서 제작한 각각의 녹색 유기 전계 발광 소자에 대하여 수명(T90: 초기 휘도에서 90%로 감소하는데 소요되는 시간)을 측정하고, 그 결과를 하기 표 5에 나타내었다.In addition, for each green organic electroluminescent device manufactured in Examples 73, 75, 76, 79, 85, 89, 91, 93, 94, 96, 97, 99 and Comparative Examples 3 to 5, the lifespan (T90: initial The time required for luminance to decrease to 90%) was measured, and the results are shown in Table 5 below.
상기 표 5에 나타낸 바와 같이, 본 발명에 따른 화합물을 발광층에 사용한 녹색 유기 전계 발광 소자(실시예 73, 75, 76, 79, 85, 89, 91, 93, 94, 96, 97, 99)는 CBP, 화합물 B 또는 화합물 C를 발광층에 사용한 녹색 유기 전계 발광 소자(비교예 3, 4 또는 5)에 비해 긴 수명을 나타내는 것을 알 수 있었다. As shown in Table 5, the green organic electroluminescent device (Examples 73, 75, 76, 79, 85, 89, 91, 93, 94, 96, 97, 99) using the compound according to the present invention in the emitting layer was It was found that the green organic electroluminescent device using CBP, Compound B, or Compound C in the emitting layer had a longer lifespan compared to the green organic electroluminescent device (Comparative Examples 3, 4, or 5).
Claims (9)
[화학식 1]
상기 화학식 1에서,
L1 및 L2는 서로 동일하거나 상이하며, 각각 독립적으로 단일결합이거나, 혹은 C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되고,
X는 C(R3)(R4), O 및 S로 이루어진 군으로부터 선택되고,
Ar1는 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고,
Ar2는 C6~C60의 아릴기이고,
m은 0 내지 3의 정수이고,
R2는 수소이고,
R3 내지 R4는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 혹은 인접하는 기와 결합하여 축합 고리를 형성할 수 있고,
상기 L1 및 L2의 아릴렌기 및 헤테로아릴렌기와, 상기 Ar1 및 Ar2, R1 내지 R4의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.Compound represented by Formula 1:
[Formula 1]
In Formula 1,
L 1 and L 2 are the same or different from each other, and are each independently a single bond or selected from the group consisting of an arylene group of C 6 to C 18 and a heteroarylene group of 5 to 18 nuclear atoms,
X is selected from the group consisting of C(R 3 )(R 4 ), O and S,
Ar 1 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 Cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 Aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 Selected from the group consisting of an arylphosphine group, a C 6 to C 60 arylphosphine oxide group, and a C 6 to C 60 arylamine group,
Ar 2 is an aryl group from C 6 to C 60 ,
m is an integer from 0 to 3,
R 2 is hydrogen,
R 3 to R 4 are the same or different from each other, and each independently represents hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C Selected from the group consisting of an aryl boron group of 60 , an arylphosphine group of C 6 ~ C 60 , an arylphosphine oxide group of C 6 ~ C 60 , and an arylamine group of C 6 ~ C 60 , or condensed by combining with an adjacent group can form a ring,
The arylene group and heteroarylene group of L 1 and L 2 , the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group of Ar 1 and Ar 2 , R 1 to R 4 , Alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group, and aryl amine group are each independently deuterium (D), halogen, cyano group, Nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group and arylamine groups of C 6 to C 60 . In this case, when the substituents are plural, they may be the same or different from each other.
상기 Ar1는 C1~C40의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되는 것인 화합물.According to paragraph 1,
The Ar 1 is a compound selected from the group consisting of a C 1 ~ C 40 alkyl group, a C 6 ~ C 60 aryl group, a heteroaryl group with 5 to 60 nuclear atoms, and a C 6 ~ C 60 arylamine group.
상기 화학식 1로 표시되는 화합물은 하기 화학식 6 내지 8 중 적어도 어느 하나로 표시되는 것인 화합물.
[화학식 6]
[화학식 7]
[화학식 8]
상기 화학식 6 내지 8에서,
L1, L2, Ar1, Ar2, m, R2는 각각 제1항에서 정의한 바와 같다.According to paragraph 1,
The compound represented by Formula 1 is a compound represented by at least one of the following Formulas 6 to 8.
[Formula 6]
[Formula 7]
[Formula 8]
In Formulas 6 to 8,
L 1 , L 2 , Ar 1 , Ar 2 , m, and R 2 are each as defined in paragraph 1.
상기 Ar1은 하기 화학식 9로 표시되는 치환체인 것인 화합물.
[화학식 9]
상기 화학식 9에서,
*는 상기 화학식 1에 결합되는 부분을 의미하고,
Z1 내지 Z5는 서로 동일하거나 상이하며, 각각 독립적으로 N 또는 C(R5)이고, 이때 상기 R5이 복수인 경우, 이들은 서로 동일하거나 상이하고,
R5는 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 혹은 인접하는 기와 결합하여 축합 고리를 형성할 수 있고,
상기 R5의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.According to paragraph 1,
A compound wherein Ar 1 is a substituent represented by the following formula (9).
[Formula 9]
In Formula 9 above,
* refers to the portion bonded to Formula 1 above,
Z 1 to Z 5 are the same or different from each other and are each independently N or C(R 5 ), wherein when R 5 is plural, they are the same or different from each other,
R 5 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 Cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 Aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 It may be selected from the group consisting of an arylphosphine group, a C 6 to C 60 arylphosphine oxide group, and a C 6 to C 60 arylamine group, or may be combined with an adjacent group to form a condensed ring,
The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, Arylphosphine group, arylphosphine oxide group, and arylamine group each independently contain deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 Alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 may be substituted with one or more substituents selected from the group consisting of aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group, and C 6 ~ C 60 arylamine group, At this time, when the substituents are plural, they may be the same or different from each other.
상기 화학식 9로 표시되는 치환체는 하기 A-1 내지 A-15 중 어느 하나로 표시되는 것인 화합물.
상기 A-1 내지 A-15 에서,
R5는 제5항에서 정의한 바와 같고,
p는 0 내지 4의 정수이고,
R6은 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 혹은 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며, 상기 R6이 복수인 경우, 이들은 서로 동일하거나 상이할 수 있고,
상기 R6의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.According to clause 5,
The substituent represented by Formula 9 is a compound represented by any one of A-1 to A-15 below.
In A-1 to A-15 above,
R 5 is as defined in paragraph 5,
p is an integer from 0 to 4,
R 6 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 Cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 Aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 It may be selected from the group consisting of an arylphosphine group, a C 6 to C 60 arylphosphine oxide group, and a C 6 to C 60 arylamine group, or may be combined with an adjacent group to form a condensed ring, and R 6 is plural. In this case, they may be the same or different from each other,
The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, Arylphosphine group, arylphosphine oxide group, and arylamine group each independently contain deuterium (D), halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 6 to C 60 aryl group, heteroaryl group with 5 to 60 nuclear atoms, C 1 to C 40 Alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 may be substituted with one or more substituents selected from the group consisting of aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 arylphosphine oxide group, and C 6 ~ C 60 arylamine group, At this time, when the substituents are plural, they may be the same or different from each other.
상기 1층 이상의 유기물층 중 적어도 하나는 제1항 내지 제2항, 및 제4항 내지 제6항 중 어느 한 항에 기재된 화합물을 포함하는 것인 유기 전계 발광 소자.It includes an anode, a cathode, and one or more organic layers interposed between the anode and the cathode,
An organic electroluminescent device wherein at least one of the one or more organic layers includes the compound according to any one of claims 1 to 2 and claims 4 to 6.
상기 화합물을 포함하는 유기물층은 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자 수송층 및 전자 주입층으로 이루어진 군에서 선택되는 것인 유기 전계 발광 소자.In clause 7,
An organic electroluminescent device wherein the organic material layer containing the compound is selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, and an electron injection layer.
상기 화합물을 포함하는 유기물층은 인광 발광층인 유기 전계 발광 소자.According to clause 8,
An organic electroluminescent device in which the organic layer containing the compound is a phosphorescent layer.
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| KR1020160133400A KR102673121B1 (en) | 2016-10-14 | 2016-10-14 | Organic compound and organic electroluminescent device using the same |
| PCT/KR2017/011329 WO2018070835A1 (en) | 2016-10-14 | 2017-10-13 | Organic compound and organic electroluminescent element using same |
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| CN109988154A (en) * | 2019-01-16 | 2019-07-09 | 浙江华显光电科技有限公司 | A kind of phosphorescence host compound and its organic electroluminescence device using the compound |
| CN112390783A (en) * | 2019-08-19 | 2021-02-23 | 北京鼎材科技有限公司 | Compound, application thereof and organic electroluminescent device comprising compound |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2014204464A1 (en) * | 2013-06-20 | 2014-12-24 | Universal Display Corporation | Phosphorescent organic light emitting devices having a hole-transporting host in the emissive region |
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| JP2001160489A (en) | 1999-12-01 | 2001-06-12 | Toyota Central Res & Dev Lab Inc | Organic electroluminescent element |
| JP2014103212A (en) * | 2012-11-19 | 2014-06-05 | Samsung Display Co Ltd | Organic el material containing amine derivative having acridine moiety and carbazole moiety, and organic el element using the same |
| KR101512012B1 (en) * | 2013-02-14 | 2015-04-16 | (주)씨에스엘쏠라 | Organic light compound and organic light device using the same |
| KR102169447B1 (en) * | 2013-05-31 | 2020-10-23 | 에스에프씨 주식회사 | An organoelectro luminescent compounds and organoelectro luminescent device using the same |
| KR101778359B1 (en) * | 2014-05-29 | 2017-09-14 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
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| WO2018070835A1 (en) | 2018-04-19 |
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