WO2020071721A1 - Compound for organic electric element, organic electric element using same, and electronic device thereof - Google Patents
Compound for organic electric element, organic electric element using same, and electronic device thereofInfo
- Publication number
- WO2020071721A1 WO2020071721A1 PCT/KR2019/012796 KR2019012796W WO2020071721A1 WO 2020071721 A1 WO2020071721 A1 WO 2020071721A1 KR 2019012796 W KR2019012796 W KR 2019012796W WO 2020071721 A1 WO2020071721 A1 WO 2020071721A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- group
- sub
- ring
- mmol
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 156
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 239000011368 organic material Substances 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000001931 aliphatic group Chemical group 0.000 claims description 14
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 13
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- -1 fused ring group Chemical group 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 229910052710 silicon Inorganic materials 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 4
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000005567 fluorenylene group Chemical group 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 22
- 230000015572 biosynthetic process Effects 0.000 description 115
- 238000003786 synthesis reaction Methods 0.000 description 115
- 239000010410 layer Substances 0.000 description 91
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 81
- 239000000047 product Substances 0.000 description 78
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- 238000001308 synthesis method Methods 0.000 description 50
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 41
- 230000000052 comparative effect Effects 0.000 description 35
- 239000000463 material Substances 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 125000004432 carbon atom Chemical group C* 0.000 description 22
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 20
- 239000000126 substance Substances 0.000 description 20
- 238000000434 field desorption mass spectrometry Methods 0.000 description 19
- 239000012044 organic layer Substances 0.000 description 16
- 238000002474 experimental method Methods 0.000 description 14
- 238000002347 injection Methods 0.000 description 14
- 239000007924 injection Substances 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000000460 chlorine Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 230000005525 hole transport Effects 0.000 description 11
- 239000012467 final product Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
- 239000012153 distilled water Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 229960001866 silicon dioxide Drugs 0.000 description 7
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 5
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 5
- 101150003085 Pdcl gene Proteins 0.000 description 5
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- SFUIGUOONHIVLG-UHFFFAOYSA-N (2-nitrophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1[N+]([O-])=O SFUIGUOONHIVLG-UHFFFAOYSA-N 0.000 description 3
- NXYICUMSYKIABQ-UHFFFAOYSA-N 1-iodo-4-phenylbenzene Chemical group C1=CC(I)=CC=C1C1=CC=CC=C1 NXYICUMSYKIABQ-UHFFFAOYSA-N 0.000 description 3
- UWIWGZCNYRBVJL-UHFFFAOYSA-N 2-chloronaphthalen-1-amine Chemical compound C1=CC=C2C(N)=C(Cl)C=CC2=C1 UWIWGZCNYRBVJL-UHFFFAOYSA-N 0.000 description 3
- 0 CC(*)(C=C1)C=CC2=C1C1=CC(C)(*)C=CC=C1N2Ic1nc([Al]*)nc(*[Al])n1 Chemical compound CC(*)(C=C1)C=CC2=C1C1=CC(C)(*)C=CC=C1N2Ic1nc([Al]*)nc(*[Al])n1 0.000 description 3
- 125000005129 aryl carbonyl group Chemical group 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 238000000691 measurement method Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 2
- SDXVREWXCAWCNV-UHFFFAOYSA-N 10-bromo-12-thiapentacyclo[11.8.0.02,11.03,8.014,19]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaene Chemical compound BrC1=CC2=C(C=CC=C2)C2=C1SC1=C3C=CC=CC3=CC=C21 SDXVREWXCAWCNV-UHFFFAOYSA-N 0.000 description 2
- PNKYJFALBICZKX-UHFFFAOYSA-N 2,4-dibromodibenzothiophene Chemical compound C1=CC=C2C3=CC(Br)=CC(Br)=C3SC2=C1 PNKYJFALBICZKX-UHFFFAOYSA-N 0.000 description 2
- KRQFZBUWIOZDMP-UHFFFAOYSA-N 2-bromo-3-nitronaphthalene Chemical compound C1=CC=C2C=C(Br)C([N+](=O)[O-])=CC2=C1 KRQFZBUWIOZDMP-UHFFFAOYSA-N 0.000 description 2
- APSMUYYLXZULMS-UHFFFAOYSA-N 2-bromonaphthalene Chemical compound C1=CC=CC2=CC(Br)=CC=C21 APSMUYYLXZULMS-UHFFFAOYSA-N 0.000 description 2
- VECLPBKDHAALGQ-UHFFFAOYSA-N 3-bromo-9,9-dimethylfluorene Chemical compound BrC1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 VECLPBKDHAALGQ-UHFFFAOYSA-N 0.000 description 2
- XIYLVRAXCQDLSE-UHFFFAOYSA-N 6-bromonaphtho[1,2-b][1]benzothiole Chemical compound S1C2=CC=CC=C2C2=C1C1=CC=CC=C1C=C2Br XIYLVRAXCQDLSE-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- KADWHAUZQLIELL-UHFFFAOYSA-N c(cc1)cc2c1[nH]c1c3[s]c(c4ccccc4cc4)c4c3c(cccc3)c3c21 Chemical compound c(cc1)cc2c1[nH]c1c3[s]c(c4ccccc4cc4)c4c3c(cccc3)c3c21 KADWHAUZQLIELL-UHFFFAOYSA-N 0.000 description 2
- BAGCJCDOQQNPGN-UHFFFAOYSA-N c(cc1)ccc1-[n]1c(c2c(c(-c(cc3)cc4c3[s]c3ccccc43)c3)[s]c4ccccc24)c3c2c1cccc2 Chemical compound c(cc1)ccc1-[n]1c(c2c(c(-c(cc3)cc4c3[s]c3ccccc43)c3)[s]c4ccccc24)c3c2c1cccc2 BAGCJCDOQQNPGN-UHFFFAOYSA-N 0.000 description 2
- UQNQQFBLWNGJKC-UHFFFAOYSA-N c(cc1)ccc1-[n]1c(ccc(-c(c2c3c4ccccc4[o]2)cc(c2cc(-c(cc4)cc(-c5c6ccc(-c(c7c8c9ccccc9[s]7)cc(c7ccccc77)c8[n]7-c7ccccc7)c5)c4[Si+]6(c4ccccc4)c4ccccc4)ccc22)c3[n]2-c2ccccc2)c2)c2c2c1cccc2 Chemical compound c(cc1)ccc1-[n]1c(ccc(-c(c2c3c4ccccc4[o]2)cc(c2cc(-c(cc4)cc(-c5c6ccc(-c(c7c8c9ccccc9[s]7)cc(c7ccccc77)c8[n]7-c7ccccc7)c5)c4[Si+]6(c4ccccc4)c4ccccc4)ccc22)c3[n]2-c2ccccc2)c2)c2c2c1cccc2 UQNQQFBLWNGJKC-UHFFFAOYSA-N 0.000 description 2
- LMXWDTNOCCDYPE-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-[n](c(cccc1)c1c1c2)c1ccc2-c(c1c2c3ccccc3[o]1)cc(c1ccccc11)c2[n]1-c1ccccc1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-[n](c(cccc1)c1c1c2)c1ccc2-c(c1c2c3ccccc3[o]1)cc(c1ccccc11)c2[n]1-c1ccccc1 LMXWDTNOCCDYPE-UHFFFAOYSA-N 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000004404 heteroalkyl group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical group C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 description 1
- QTPLEVOKSWEYAC-UHFFFAOYSA-N 1,2-diphenyl-9h-fluorene Chemical group C=1C=CC=CC=1C1=C2CC3=CC=CC=C3C2=CC=C1C1=CC=CC=C1 QTPLEVOKSWEYAC-UHFFFAOYSA-N 0.000 description 1
- SWSGBRBPLKJIFT-UHFFFAOYSA-N 1,4-dibromo-9,9-dimethylfluorene Chemical compound BrC1=CC=C(C=2C3=CC=CC=C3C(C1=2)(C)C)Br SWSGBRBPLKJIFT-UHFFFAOYSA-N 0.000 description 1
- SJPWYOJYEGIRLP-UHFFFAOYSA-N 1,4-dibromodibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1C(Br)=CC=C2Br SJPWYOJYEGIRLP-UHFFFAOYSA-N 0.000 description 1
- UZDTVDFSVGJREW-UHFFFAOYSA-N 1,4-dibromodibenzothiophene Chemical compound BrC1=CC=C(C=2SC3=C(C21)C=CC=C3)Br UZDTVDFSVGJREW-UHFFFAOYSA-N 0.000 description 1
- XAOMFUPJQYNDEG-LBPRGKRZSA-N 1-[(3S)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxypiperidin-1-yl]-2-methylpropan-1-one Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@@H]1CN(CCC1)C(C(C)C)=O XAOMFUPJQYNDEG-LBPRGKRZSA-N 0.000 description 1
- LEHBLKHJWCNXKQ-UHFFFAOYSA-N 1-bromo-2-nitronaphthalene Chemical compound C1=CC=CC2=C(Br)C([N+](=O)[O-])=CC=C21 LEHBLKHJWCNXKQ-UHFFFAOYSA-N 0.000 description 1
- USYQKCQEVBFJRP-UHFFFAOYSA-N 1-bromo-3-phenylbenzene Chemical group BrC1=CC=CC(C=2C=CC=CC=2)=C1 USYQKCQEVBFJRP-UHFFFAOYSA-N 0.000 description 1
- WUYYVOWEBMOELQ-UHFFFAOYSA-N 1-bromodibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2Br WUYYVOWEBMOELQ-UHFFFAOYSA-N 0.000 description 1
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 1
- ZTSYGXLLTYTXCS-UHFFFAOYSA-N 1-chloronaphthalen-2-amine Chemical compound C1=CC=CC2=C(Cl)C(N)=CC=C21 ZTSYGXLLTYTXCS-UHFFFAOYSA-N 0.000 description 1
- CRJISNQTZDMKQD-UHFFFAOYSA-N 2-bromodibenzofuran Chemical compound C1=CC=C2C3=CC(Br)=CC=C3OC2=C1 CRJISNQTZDMKQD-UHFFFAOYSA-N 0.000 description 1
- IJICRIUYZZESMW-UHFFFAOYSA-N 2-bromodibenzothiophene Chemical compound C1=CC=C2C3=CC(Br)=CC=C3SC2=C1 IJICRIUYZZESMW-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- SONNQRNOTIAJDS-GFCCVEGCSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[(2R)-2,3-dihydroxypropyl]benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC[C@H](CO)O)C=CC=1 SONNQRNOTIAJDS-GFCCVEGCSA-N 0.000 description 1
- ZMCQQCBOZIGNRV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[2-(1,2,4-triazol-1-yl)ethyl]benzamide Chemical compound NCC1=CC(OC2=CC=CC(=C2)C(=O)NCCN2C=NC=N2)=NC(=C1)C(F)(F)F ZMCQQCBOZIGNRV-UHFFFAOYSA-N 0.000 description 1
- HAEQAUJYNHQVHV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 HAEQAUJYNHQVHV-UHFFFAOYSA-N 0.000 description 1
- NYRAFWUKMMOGNZ-UHFFFAOYSA-N 3-bromo-5,5-dimethylbenzo[b][1]benzosilole Chemical compound C1=C(Br)C=C2[Si](C)(C)C3=CC=CC=C3C2=C1 NYRAFWUKMMOGNZ-UHFFFAOYSA-N 0.000 description 1
- DYTYBRPMNQQFFL-UHFFFAOYSA-N 4-bromodibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1C(Br)=CC=C2 DYTYBRPMNQQFFL-UHFFFAOYSA-N 0.000 description 1
- AZFHXIBNMPIGOD-UHFFFAOYSA-N 4-hydroxypent-3-en-2-one iridium Chemical compound [Ir].CC(O)=CC(C)=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O AZFHXIBNMPIGOD-UHFFFAOYSA-N 0.000 description 1
- ZFYXJIYPIORSQE-UHFFFAOYSA-N 5-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(2-methylsulfonylethyl)pyridine-3-carboxamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=NC=C(C(=O)NCCS(=O)(=O)C)C=1 ZFYXJIYPIORSQE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NRLQBVLOUUPAMI-UHFFFAOYSA-N 8-[3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxybenzoyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)N2CCC3(CNC(O3)=O)CC2)C=CC=1 NRLQBVLOUUPAMI-UHFFFAOYSA-N 0.000 description 1
- ZTWLQKKXJILNLO-UHFFFAOYSA-N 8-bromonaphtho[2,1-b][1]benzoselenole Chemical compound BrC1=CC=CC2=C1[Se]C1=C2C=2C=CC=CC=2C=C1 ZTWLQKKXJILNLO-UHFFFAOYSA-N 0.000 description 1
- JPTTZALREWAVON-UHFFFAOYSA-N Brc(c1c2[s]c3c1cccc3)cc(c1c3c4ccccc4cc1)c2[n]3-c1ccccc1 Chemical compound Brc(c1c2[s]c3c1cccc3)cc(c1c3c4ccccc4cc1)c2[n]3-c1ccccc1 JPTTZALREWAVON-UHFFFAOYSA-N 0.000 description 1
- SUIABOJBGAMRNE-UHFFFAOYSA-N Brc(c1c2c3ccccc3[s]1)cc(c1c3cccc1)c2[n]3-c1nc(-c2ccccc2)cc(-c2ccccc2)n1 Chemical compound Brc(c1c2c3ccccc3[s]1)cc(c1c3cccc1)c2[n]3-c1nc(-c2ccccc2)cc(-c2ccccc2)n1 SUIABOJBGAMRNE-UHFFFAOYSA-N 0.000 description 1
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- XBGODLMCJCUXMY-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c(cc2)cc3c2c(cccc2)c2[o]3)nc(-[n](c2c3cccc2)c2c3c3ccccc3c3c2c2ccccc2[o]3)n1 Chemical compound c(cc1)ccc1-c1nc(-c(cc2)cc3c2c(cccc2)c2[o]3)nc(-[n](c2c3cccc2)c2c3c3ccccc3c3c2c2ccccc2[o]3)n1 XBGODLMCJCUXMY-UHFFFAOYSA-N 0.000 description 1
- LMJUOXWBHGJHEM-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2cc(-[n](c(cccc3)c3c3c4)c3ccc4-c(cc3c4ccccc44)c(c(cccc5)c5[s]5)c5c3[n]4-c3ccccc3)ccc2)nc2c1[s]c1ccccc21 Chemical compound c(cc1)ccc1-c1nc(-c2cc(-[n](c(cccc3)c3c3c4)c3ccc4-c(cc3c4ccccc44)c(c(cccc5)c5[s]5)c5c3[n]4-c3ccccc3)ccc2)nc2c1[s]c1ccccc21 LMJUOXWBHGJHEM-UHFFFAOYSA-N 0.000 description 1
- KLNXXCQWBOECCC-UHFFFAOYSA-N c1ccc2[nH]c3ccc4[o]c5cc(cccc6)c6cc5c4c3c2c1 Chemical compound c1ccc2[nH]c3ccc4[o]c5cc(cccc6)c6cc5c4c3c2c1 KLNXXCQWBOECCC-UHFFFAOYSA-N 0.000 description 1
- FHQMDJVUANCJJQ-UHFFFAOYSA-N c1ccc2[nH]c3ccc4[s]c5cc(cccc6)c6cc5c4c3c2c1 Chemical compound c1ccc2[nH]c3ccc4[s]c5cc(cccc6)c6cc5c4c3c2c1 FHQMDJVUANCJJQ-UHFFFAOYSA-N 0.000 description 1
- TXGTXSPQIOKENN-UHFFFAOYSA-N c1ccc2[o]c(cc3[nH]c4ccc(cccc5)c5c4c3c3)c3c2c1 Chemical compound c1ccc2[o]c(cc3[nH]c4ccc(cccc5)c5c4c3c3)c3c2c1 TXGTXSPQIOKENN-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001690 polydopamine Polymers 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
Images
Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D403/02—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 two hetero rings
- C07D403/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D517/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D517/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms in which the condensed system contains two hetero rings
- C07D517/04—Ortho-condensed systems
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
Definitions
- the present invention relates to a compound for an organic electric element, an organic electric element using the same, and an electronic device thereof.
- the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material.
- An organic electric device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween.
- the organic material layer is often composed of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
- Materials used as the organic material layer in the organic electric device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on the function.
- a difference in properties according to a material structure is very large, and thus, it is applied to various layers as a material for an organic electric device.
- the band gap (HOMO, LUMO), electrical properties, chemical properties, physical properties, etc. have different characteristics depending on the number of rings, fused positions, and types and arrangement of heteroatoms. This has been going on.
- the LUMO and HOMO level of the host material are factors that greatly affect the efficiency and life of the organic electrical device, depending on whether electron and hole injection in the emitting layer can be efficiently controlled.
- the charge balance in the light emitting layer, dopant quenching (quenching) and the efficiency of the light emission at the interface of the hole transport layer can be prevented from deteriorating.
- TRTP PL lifetime
- the TRTP (Time resolved transient PL) measurement method is a method of observing the decay time of the spectrum over time after irradiating a pulsed light source to the host thin film. It is a measurement method.
- the TRTP measurement is a measurement method capable of distinguishing between fluorescence and phosphorescence, energy transfer method in mixed host material, exciplex energy transfer method, and TADF energy transfer method.
- the present invention has been proposed to solve the problems of the phosphorescent host material as described above, the charge balance in the light emitting layer by adjusting the HOMO level for the host material of the phosphorescent dopant-containing organic electroluminescent device containing a phosphorescent dopant and the efficiency, life span It is an object of the present invention to provide an organic electrical device using the compound and an electronic device thereof.
- the present invention is to reduce the energy barrier between the light emitting layer and the adjacent layer by containing a specific first host material in combination with a specific first host material as a main component in order to control efficient hole injection in the light emitting layer of the phosphorescent organic electroluminescent device. It is possible to maximize the charge balance in the light emitting layer to provide high efficiency and high lifespan of the organic electric device.
- the present invention relates to an organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, and the light emitting layer is a phosphorescent light emitting layer.
- An organic electroluminescent device comprising a first host compound represented by (1) and a second host compound represented by formula (2).
- the present invention provides an organic electric device using the compound represented by the above formulas and an electronic device thereof.
- the mixture according to the present invention as a phosphorescent host material, it is possible to achieve high luminous efficiency and low driving voltage of the organic electric device, and also significantly improve the life of the device.
- FIG. 1 is an exemplary view of an organic electroluminescent device according to the present invention.
- organic electrical element 110 substrate
- first, second, A, B, (a), and (b) may be used. These terms are only for distinguishing the component from other components, and the nature, order, or order of the component is not limited by the term.
- a component is described as being “connected”, “coupled” or “connected” to another component, that component may be directly connected to or connected to the other component, but another component between each component It should be understood that elements may be “connected”, “coupled” or “connected”.
- halo or halogen as used herein are fluorine (F), bromine (Br), chlorine (Cl) or iodine (I), unless otherwise noted.
- alkyl or "alkyl group” used in the present invention has a single bond of 1 to 60 carbon atoms, unless otherwise specified, a straight chain alkyl group, a branched chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cycle.
- radicals of saturated aliphatic functional groups including alkyl groups, cycloalkyl-substituted alkyl groups.
- haloalkyl group or "halogenalkyl group” as used in the present invention means an alkyl group substituted with halogen unless otherwise specified.
- heteroalkyl group used in the present invention means that at least one of the carbon atoms constituting the alkyl group is replaced with a heteroatom.
- alkenyl group used in the present invention have a double or triple bond of 2 to 60 carbon atoms, unless otherwise specified, and include straight or branched chain groups. , But is not limited to this.
- cycloalkyl means an alkyl forming a ring having 3 to 60 carbon atoms, unless otherwise specified, but is not limited thereto.
- alkoxyl group means an alkyl group to which an oxygen radical is attached, and has a carbon number of 1 to 60 unless otherwise specified, and is limited thereto. It is not.
- alkenoxyl group means an alkenyl group to which an oxygen radical is attached, and 2 to 60 unless otherwise specified. It has a carbon number, and is not limited thereto.
- aryloxyl group or "aryloxy group” used in the present invention means an aryl group to which an oxygen radical is attached, and has a carbon number of 6 to 60 unless otherwise specified, and is not limited thereto.
- aryl group and arylene group used in the present invention have 6 to 60 carbon atoms, respectively, and are not limited thereto unless otherwise specified.
- an aryl group or an arylene group means a single ring or multi-ring aromatic, and includes an aromatic ring formed by adjacent substituents participating in a bond or reaction.
- the aryl group may be a phenyl group, biphenyl group, fluorene group, dimethylfluorene group, diphenylfluorene group, or spirofluorene group.
- aryl or "ar” means a radical substituted with an aryl group.
- an arylalkyl group is an alkyl group substituted with an aryl group
- an arylalkenyl group is an alkenyl group substituted with an aryl group
- a radical substituted with an aryl group has a carbon number described herein.
- arylalkoxy group it means an alkoxy group substituted with an aryl group
- alkoxycarbonyl group it means a carbonyl group substituted with an alkoxyl group
- arylcarbonyl alkenyl group it means an alkenyl group substituted with an arylcarbonyl group.
- the arylcarbonyl group is a carbonyl group substituted with an aryl group.
- heteroalkyl means alkyl containing one or more heteroatoms, unless otherwise specified.
- heteroaryl group or “heteroarylene group” means an aryl group or an arylene group having 2 to 60 carbon atoms each containing at least one heteroatom, unless otherwise specified, and is not limited thereto. No, it includes at least one of a single ring and multiple rings, and may be formed by combining adjacent functional devices.
- heterocyclic group used in the present invention includes at least one heteroatom, has 2 to 60 carbon atoms, includes at least one of a single ring and multiple rings, heteroaliphatic ring and hetero, unless otherwise specified. Aromatic rings. Adjacent functional groups may also be formed by bonding.
- heteroatom refers to N, O, S, P or Si, unless otherwise stated.
- heterocyclic group may include a ring containing SO 2 instead of carbon forming a ring.
- heterocyclic group includes the following compounds.
- aliphatic refers to an aliphatic hydrocarbon having 1 to 60 carbon atoms
- aliphatic ring means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.
- ring used in the present invention refers to an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocyclic ring having 2 to 60 carbon atoms or a combination thereof, and It contains a saturated or unsaturated ring.
- hetero compounds or hetero radicals other than the above-described hetero compounds include one or more hetero atoms, but are not limited thereto.
- carbonyl used in the present invention is represented by -COR ', where R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, 3 to 30 carbon atoms. Is a cycloalkyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.
- ether used in the present invention is represented by -RO-R ', wherein R or R' are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, or 6 to 30 carbon atoms. It is an aryl group, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.
- substituted in the term “substituted or unsubstituted” used in the present invention is deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 20 alkyl group, C 1 ⁇ C 20 alkoxyl group, C 1 ⁇ C 20 alkylamine group, C 1 ⁇ C 20 alkylthiophene group, C 6 ⁇ C 20 arylthiophene group, C 2 ⁇ C 20 alkenyl group, C 2 ⁇ C 20 alkynyl group, C 3 ⁇ C 20 cycloalkyl group, C 6 ⁇ C 20 aryl group, substituted with deuterium C 6 ⁇ C 20 aryl group, C 8 ⁇ C 20 aryl alkenyl group, silane group, boron Means a group, a germanium group, and one or more substituents selected from the group consisting of C 2 to C 20 heterocyclic groups, and is not limited
- the substituent R 1 means non-existent, that is, when a is 0, it means that hydrogen is bonded to all of the carbons forming the benzene ring.
- the formula or compound may be omitted.
- a is an integer of 1
- one substituent R 1 is bound to any one of carbons forming a benzene ring, and when a is an integer of 2 or 3, each of them is bonded as follows, where R 1 may be the same or different from each other.
- a is an integer of 4 to 6 it binds to the carbon of the benzene ring in a similar manner, while the indication of hydrogen bound to the carbon forming the benzene ring is omitted.
- the present invention relates to an organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, and the light emitting layer is a phosphorescent light emitting layer. It provides an organic electric device comprising a first host represented by (1) and a second host represented by the formula (2).
- W, X and Y are each independently O, S, CR'R ", SiR'R” or Se,
- a and b are each independently 0 or 1, provided that a + b is 1 or more,
- R 'and R are each independently hydrogen; an alkyl group of C 1 to C 50 ; an aryl group of C 6 to C 60 ; and a heteroaryl group of C 2 to C 60 ; or R' And R "form a ring with each other to form a spiro ring,
- L 1 , L 2 and L ' are each independently a single bond; C 6 ⁇ C 60 Arylene group; Or a C 2 ⁇ C 60 heteroarylene group; and
- Ar 1 , Ar 2 and Ar 3 are each independently hydrogen; heavy hydrogen; C 6 ⁇ C 60 Aryl group; Fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C 3 ⁇ C 60 aliphatic ring and C 6 ⁇ C 60 aromatic ring fused ring group; C 1 ⁇ C 50 alkyl group; C 2 ⁇ C 20 alkenyl group; C 2 ⁇ C 20 alkynyl group; C 1 ⁇ C 30 Alkoxy group; C 6 ⁇ C 30 Aryloxy group; And -L'-NR'R ";
- Z is NR ', O, S, CR'R ", SiR'R", or Se,
- R 1 to R 5 are each independently hydrogen; heavy hydrogen; halogen; C 6 ⁇ C 60 Aryl group; Fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C 3 ⁇ C 60 aliphatic ring and C 6 ⁇ C 60 aromatic ring fused ring group; C 1 ⁇ C 50 alkyl group; C 2 ⁇ C 20 alkenyl group; C 2 ⁇ C 20 alkynyl group; C 1 ⁇ C 30 Alkoxy group; C 6 ⁇ C 30 Aryloxy group; And -L'-N (R a ) (R b ); is selected from the group consisting of,
- R a and R b are independently of each other C 6 ⁇ C 60 aryl group; Fluorenyl group; C 3 ⁇ C 60 aliphatic ring and C 6 ⁇ C 60 aromatic ring fused ring group; And O, N, S, Si, and C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom; is selected from the group consisting of,
- R 12 , R 13 and R 14 are each independently hydrogen; heavy hydrogen; halogen; C 6 ⁇ C 60 Aryl group; Fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C 3 ⁇ C 60 aliphatic ring and C 6 ⁇ C 60 aromatic ring fused ring group; C 1 ⁇ C 50 alkyl group; C 2 ⁇ C 20 alkenyl group; C 2 ⁇ C 20 alkynyl group; C 1 ⁇ C 30 Alkoxy group; C 6 ⁇ C 30 Aryloxy group; And -L'-N (R a ) (R b ); is selected from the group consisting of,
- a plurality of each of the same or different and adjacent to each other, a plurality of adjacent R 12 , a plurality of R 13 , and a plurality of R 14 may combine with each other to form an aromatic and heteroaromatic ring, At least one pair of contiguous R 12 , contiguous R 13 , and contiguous R 14 forms a ring,
- g and i are integers from 0 to 4, h is an integer from 0 to 2, n, l and p are integers from 0 to 4, m is 0 or 1 , o is an integer from 0 to 3,
- the compound represented by the formula (1) in the present invention provides an organic electric device comprising a compound represented by the following formula (3) or (4).
- the present invention provides an organic electric device in which the compound represented by the formula (1) includes a compound represented by any one of the following formulas (5) to (12).
- the present invention provides an organic electric device including a compound in which all of l, m, n, o and p are 0 in the formula (1).
- any one of the R 1 , R 2 , R 3 , R 4 and R 5 is an organic electric device comprising a compound in which a pair of neighboring pairs to each other to form a ring
- X and Y provides an organic electric device comprising a compound of S or O.
- the formula (1) in the present invention includes the following compound.
- the present invention provides an organic electric device in which the compound represented by the formula (2) includes a compound represented by any one of the following formulas (13) to (17).
- R 12 ' , R 13' and R 14 ' are as defined in R 12 , R 13 and R 14 above .
- the present invention includes a compound represented by any one of the following formulas (18) to (57).
- Ar 2 , Ar 3 , L 2 , R 12 ' , R 13' , R 14 ' , W, g, h and i are as defined above,
- R 12 ' , R 13' and R 14 ' are as defined in R 12 , R 13 and R 14 above ,
- t is an integer from 0 to 4, and s and u are each independently an integer from 0 to 6.
- the formula (2) in the present invention includes the following compound.
- the organic electric device 100 includes a first electrode 120, a second electrode 180 and a first electrode 120 and a second electrode formed on the substrate 110. Between (180) it is provided with an organic layer containing the compound represented by the formula (1) and (2).
- the first electrode 120 may be an anode (anode)
- the second electrode 180 may be a cathode (cathode)
- the first electrode may be a cathode and the second electrode may be an anode.
- the organic material layer sequentially comprises a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, a light emitting auxiliary layer 151, an electron transport layer 160 and an electron injection layer 170 on the first electrode 120. It can contain. At this time, layers other than the emission layer 150 may not be formed.
- a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, an electron transport auxiliary layer, a buffer layer 141, and the like may be further included, and the electron transport layer 160, etc. may also serve as a hole blocking layer.
- the organic electric device according to the present invention may further include a protective layer formed on one surface opposite to the organic material layer among at least one surface of the first electrode and the second electrode.
- the compound containing Formula 1 of the present invention may be used as a material for the light efficiency improving layer or the protective layer.
- the band gap, electrical properties, and interfacial properties may vary depending on which substituents are attached to which positions, so the selection of the core and the combination of sub-substituents coupled thereto are also very good. It is important, especially when the energy level and T1 value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined, long life and high efficiency can be achieved simultaneously.
- the organic electroluminescent device may be manufactured using a physical vapor deposition (PVD) method.
- PVD physical vapor deposition
- a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode, and a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, and an electron transport layer 160 are formed thereon.
- After forming an organic material layer including the electron injection layer 170 it can be manufactured by depositing a material that can be used as a cathode thereon.
- the light emitting auxiliary layer 151 may be further formed between the hole transport layer 140 and the light emitting layer 150
- the electron transport auxiliary layer may be further formed between the light emitting layer 150 and the electron transport layer 160.
- the present invention provides a compound represented by the formula (1) and the formula (2) in an ratio of any one of 1: 9 to 9: 1 to provide an organic electric device included in the light emitting layer, preferably Is 1: 9 to 5: 5, more preferably mixed in a ratio of 2: 8 to 3: 7 and included in the light emitting layer.
- the present invention further comprises a light efficiency improving layer formed on at least one of one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer from one side of the first electrode in the organic electric device.
- a light efficiency improving layer formed on at least one of one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer from one side of the first electrode in the organic electric device.
- the organic material layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process and a roll-to-roll process, and the organic material layer according to the present invention can be formed by various methods Therefore, the scope of the present invention is not limited by the forming method.
- the organic electric device may be a front emission type, a back emission type, or a double-sided emission type depending on the material used.
- WOLED White Organic Light Emitting Device
- RGB Red
- Green Green
- B Blue
- the R, G, and B light emitting units are arranged in a mutually planar side-by-side manner, and the stacking method in which the R, G, and B light-emitting layers are stacked up and down.
- CCM color conversion material
- the present invention is a display device comprising the above-described organic electric device; And a control unit for driving the display device.
- the present invention provides an electronic device characterized in that the organic electroluminescent device is at least one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and a monochromatic or white lighting device.
- the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation, game machines, various TVs, and various computers.
- the compound represented by Chemical Formula (1) according to the present invention (final product 1) is prepared by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1 below.
- Sub 1 of Scheme 1 may be synthesized by the following Reaction Scheme 2, but is not limited thereto.
- the compound belonging to Sub 1 may be the following compound, but is not limited thereto, and Table 1 shows the FD-MS value of the compound belonging to Sub 1.
- Sub 2 of Scheme 1 may be synthesized by the following Reaction Scheme 3, but is not limited thereto.
- Sub 2-II-37 (23g, 89mmol), N-Bromosuccinimide (16g, 89mmol), and Methylene chloride (300mL) were synthesized using the synthesis method of Sub 2-III-1. 37 (21 g, 70%).
- Sub 2-II-144 (30g, 89mmol), N-Bromosuccinimide (18.8 g, 105.9 mmol), Methylene chloride (318 mL) was synthesized using the synthesis method of Sub 2-III-1. -III-144 (18.24 g, 53%).
- the compound belonging to Sub 2 may be the following compound, but is not limited thereto, and Table 2 shows the FD-MS value of the compound belonging to Sub 2.
- the compound belonging to Sub 3 may be the following compound, but is not limited thereto, and Table 3 shows the FD-MS value of the compound belonging to Sub 3.
- the compound represented by the formula (2) according to the present invention (final product 2) is prepared by reacting Sub 4 and Sub 5 as shown in Reaction Scheme 4.
- Sub 4 of Scheme 4 may be synthesized by the reaction route of Scheme 5 below, but is not limited thereto.
- Hal 1 is Br, Cl, I, and W
- R 12 , R 13 , R 14 , g, h, i are as defined in Chemical Formula 2.
- 6-bromodinaphtho [1,2-b: 1 ', 2'-d] thiophene (50.0 g, 138 mmol), 2-chloroaniline (17.6 g, 138 mmol), Pd 2 (dba) 3 (3.78 g, 4.13 mmol) ), P ( t -Bu) 3 (1.67 g, 8.26 mmol), NaO t -Bu (26.5 g, 275 mmol) was conducted in the same manner as in Sub 4-c-1, and the product was 88.0 g (yield: 78 %).
- 6-bromobenzo [b] naphtho [2,1-d] thiophene (50.0 g, 160 mmol), 2-chloroaniline (20.4 g, 160 mmol), Pd 2 (dba) 3 (4.39 g, 4.79 mmol), P ( t -Bu) 3 (1.94 g, 9.58 mmol) and NaO t -Bu (30.7 g, 319 mmol) were conducted in the same manner as in Sub 4-c-1, to obtain 41.4 g of product (yield: 72%).
- 6-bromobenzo [b] naphtho [2,1-d] thiophene (50.0 g, 160 mmol), bis (pinacolato) diboron (44.6 g, 176 mmol), KOAc (47.0 g, 479 mmol), PdCl 2 (dppf) (3.50 g, 4.79 mmol) was carried out in the same manner as the experimental method of Sub 4-a-39 to obtain 40.3 g of product (yield: 70%).
- Sub 4 examples are as follows, but are not limited thereto, and Table 5 shows FD-MS (Field Desorption-Mass Spectrometry) values of compounds belonging to Sub 4.
- -N 1 -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum deposited to form a thickness of 60 nm.
- NPB N, N'-Bis (1-naphthalenyl) -N, N'-bis-phenyl- (1,1'-biphenyl) -4,4'-diamine
- the hole blocking layer (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolineoleito) aluminum (hereinafter abbreviated as BAlq) is vacuum deposited to a thickness of 10 nm, and the electron transport layer Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nm.
- an organic electroluminescent device was manufactured by depositing LiF, an alkali metal halide as an electron injection layer, to a thickness of 0.2 nm, and then depositing Al to a thickness of 150 nm to use as a cathode.
- An organic electroluminescent device was manufactured in the same manner as in the above example, except that the compound represented by Chemical Formula 1 was used alone as a host.
- An organic electroluminescent device was manufactured in the same manner as in the above example, except that the compound represented by Chemical Formula 2 was used alone as a host.
- An organic electroluminescent device was manufactured in the same manner as in the above example, except that the compound represented by Chemical Formula 1 and Comparative Compound 1 were used as a mixture.
- An organic electroluminescent device was manufactured in the same manner as in the above example, except that the compound represented by Chemical Formula 2 and Comparative Compound 1 were used as a mixture.
- An organic electroluminescent device was manufactured in the same manner as in the above example, except that the compound represented by Chemical Formula 1 and Comparative Compound 3 to Comparative Compound 5 were used as a mixture.
- the electroluminescence (EL) characteristics were measured by the PR-650 of photoresearch by applying a net bias DC voltage to the organic electroluminescent elements of the Examples and Comparative Examples prepared as described above, and the measurement result showed a reference luminance of 2500 cd / m 2 In the T95 life was measured by a life measurement equipment manufactured by Max Science.
- the following table shows the results of device fabrication and evaluation.
- the present inventors determined that the substance of the substance of Formula 1 and the substance of Formula 2 has new characteristics other than the characteristics of the substance, respectively, and the substance of Formula 1 and the substance of Formula 2 , PL and PL lifetime were measured using the mixture of the present invention, respectively.
- the compounds of the present invention, Formula 1 and Formula 2 were mixed, it was confirmed that a new PL wavelength was formed unlike that of a single compound, and the decrease and extinction time of the newly formed PL wavelength was determined for each of Formula 1 and Formula 2 materials. It was confirmed that it was increased than the reduction and extinction time.
- the compound of the present invention When the compound of the present invention is used in combination, not only electrons and holes are moved through the energy level of each substance, but also electrons, hole movement or energy due to exciplex of new regions having new energy levels formed due to mixing. It is judged that the efficiency and life of the furnace are increased. As a result, when using the mixture of the present invention, it can be said that the mixed thin film is an important example of exciplex energy transfer and luminescence processes.
- the reason why the combination of the present invention is superior to Comparative Examples 7 to 11 used as a phosphorescent host in which a comparative compound is mixed is because of the polycyclic ring compound represented by Chemical Formula 2, which has characteristics such as stability to hole and high T1 as well as electron.
- the compound represented by Chemical Formula 1 having strong hole characteristics is mixed, the electron blocking ability is improved due to the high T1 and high LUMO energy values, and more holes are quickly and easily moved in the light emitting layer.
- Example 2 By mixing ratio Red Fabrication and testing of organic light emitting devices
- the mixture of the compounds of the present invention was measured by fabricating the device by ratio (2: 8, 3: 7, 4: 6).
- the present invention it is possible to manufacture an organic device having excellent device characteristics of high brightness, high light emission and high life, and thus there is industrial applicability.
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Abstract
The present invention provides: a novel mixture which can improve the luminous efficiency, stability, and service life of an element; an organic electric element using same; and an electronic device thereof.
Description
본 발명은 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치에 관한 것이다.The present invention relates to a compound for an organic electric element, an organic electric element using the same, and an electronic device thereof.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛 에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기전기소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기전기소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층 등으로 이루어질 수 있다.In general, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material. An organic electric device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material layer is often composed of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
유기전기소자에서 유기물층으로 사용되는 재료는 기능에 따라, 발광재료와 전하수송 재료, 예컨대 정공주입 재료, 정공수송 재료, 전자수송 재료, 전자주입 재료 등으로 분류될 수 있다.Materials used as the organic material layer in the organic electric device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on the function.
헤테로원자를 포함하고 있는 비스타입의 고리화합물의 경우 물질 구조에 따른 특성의 차이가 매우 커서 유기전기소자의 재료로 다양한 층에 적용되고 있다. 특히 환의 개수 및 fused 위치, 헤테로원자의 종류와 배열에 따라 밴드 갭(HOMO, LUMO), 전기적 특성, 화학적 특성, 물성 등이 상이한 특징을 갖고 있어, 이를 이용한 다양한 유기전기소자의 층에 대한 적용 개발이 진행되어 왔다.In the case of a bis-type cyclic compound containing a hetero atom, a difference in properties according to a material structure is very large, and thus, it is applied to various layers as a material for an organic electric device. In particular, the band gap (HOMO, LUMO), electrical properties, chemical properties, physical properties, etc. have different characteristics depending on the number of rings, fused positions, and types and arrangement of heteroatoms. This has been going on.
인광 발광 도펀트 재료를 이용하는 인광형 유기전기소자에 있어서 호스트 물질의 LUMO 및 HOMO level은 유기전기소자의 효율 및 수명에 매우 큰 영향을 주는 요인으로서 발광층 내 전자 및 정공 주입을 효율적으로 조절 가능하냐에 따라 발광층 내 charge balance 조절, 도펀트 퀜칭(quenching) 및 정공수송층 계면에서의 발광으로 인한 효율 저하 및 수명 저하를 방지할 수 있다.In the phosphorescent organic electrical device using a phosphorescent dopant material, the LUMO and HOMO level of the host material are factors that greatly affect the efficiency and life of the organic electrical device, depending on whether electron and hole injection in the emitting layer can be efficiently controlled. The charge balance in the light emitting layer, dopant quenching (quenching) and the efficiency of the light emission at the interface of the hole transport layer can be prevented from deteriorating.
형광 및 인광 발광용 호스트 물질의 경우 최근 들어 TADF (Thermal activated delayed fluorescent), Exciplex 등을 이용한 유기전기소자의 효율 증가 및 수명 증가 등을 연구하고 있으며, 특히 호스트 물질에서 도펀트 물질로의 에너지 전달 방법 규명에 많은 연구가 진행되고 있다.In the case of host materials for fluorescence and phosphorescence emission, recently, research has been conducted on increasing the efficiency and lifetime of organic electrical devices using TADF (Thermal activated delayed fluorescent), Exciplex, etc. There is a lot of research going on.
TADF (Thermal activated delayed fluorescent), exciplex에 대한 발광층 내 에너지 전달 규명은 여러 가지 방법들이 있지만, PL lifetime (TRTP) 측정법으로 손쉽게 확인할 수 있다.Although there are several methods for identifying energy transfer in a light emitting layer for TADF (Thermal Activated Delayed Fluorescent), exciplex, it can be easily confirmed by PL lifetime (TRTP) measurement.
TRTP (Time resolved transient PL) 측정법은 펄스 광원을 호스트 박막에 조사한 후, 시간에 따른 스펙트럼의 감소(Decay time)를 관찰하는 방식으로서 에너지 전달 및 발광 지연시간 관찰을 통해 에너지 전달 방식을 규명할 수 있는 측정방법이다. 상기 TRTP 측정은 형광과 인광의 구분 및 mixed 호스트 물질 내에서의 에너지 전달방식, exciplex 에너지 전달방식, TADF 에너지 전달 방식 등을 구분해 줄 수 있는 측정법이다.The TRTP (Time resolved transient PL) measurement method is a method of observing the decay time of the spectrum over time after irradiating a pulsed light source to the host thin film. It is a measurement method. The TRTP measurement is a measurement method capable of distinguishing between fluorescence and phosphorescence, energy transfer method in mixed host material, exciplex energy transfer method, and TADF energy transfer method.
이처럼 호스트 물질로부터 도펀트 물질로 에너지가 전달되는 방식에 따라 효율 및 수명에 영향을 주는 다양한 요인들이 존재하며, 물질에 따라 에너지 전달 방식이 상이하여, 아직까지 안정되고 효율적인 유기전기소자용 호스트 재료의 개발이 충분히 이루어지지 않은 상태이다. 따라서 새로운 재료의 개발이 계속 요구되고 있으며, 특히 발광층의 호스트 물질에 대한 개발이 절실히 요구되고 있다.As described above, there are various factors affecting efficiency and lifespan depending on the manner in which energy is transferred from the host material to the dopant material, and the energy transmission method is different according to the material, so that the development of a stable and efficient host material for an organic electric device This is not done enough. Therefore, the development of new materials continues to be required, and in particular, the development of the host material of the light emitting layer is urgently required.
참고 선행기술문헌으로는 KR101170666 B1을 이용하였다.Reference KR101170666 B1 was used as a prior art document.
본 발명은 상기와 같은 인광 호스트 물질의 문제점을 해결하기 위하여 제안된 것으로, 인광 도펀트를 포함하는 인광 발광형 유기전기소자의 호스트 물질에 대한 HOMO level 조절을 통한 발광층 내 charge balance 조절 및 효율, 수명을 향상시킬 수 있는 화합물 이를 이용한 유기전기소자 및 그 전자장치를 제공하는 것을 목적으로 한다.The present invention has been proposed to solve the problems of the phosphorescent host material as described above, the charge balance in the light emitting layer by adjusting the HOMO level for the host material of the phosphorescent dopant-containing organic electroluminescent device containing a phosphorescent dopant and the efficiency, life span It is an object of the present invention to provide an organic electrical device using the compound and an electronic device thereof.
본 발명은 인광 발광형 유기전기소자의 발광층 내 효율적인 정공 주입을 조절하기 위해 주성분으로서 특정의 제 1호스트 재료에 특정의 제 2호스트 재료를 조합하여 함유함으로써, 발광층과 인접층의 에너지 장벽을 작게 할 수 있고, 발광층 내 charge balance를 최대화시켜 유기전기소자의 고효율, 고수명을 제공하는 것이다.The present invention is to reduce the energy barrier between the light emitting layer and the adjacent layer by containing a specific first host material in combination with a specific first host material as a main component in order to control efficient hole injection in the light emitting layer of the phosphorescent organic electroluminescent device. It is possible to maximize the charge balance in the light emitting layer to provide high efficiency and high lifespan of the organic electric device.
본 발명은 제 1전극, 제 2전극, 및 상기 제 1전극과 상기 제 2전극 사이에 형성된 유기물층을 포함하는 유기전기소자에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 인광성 발광층으로서 화학식 (1)로 표시되는 제 1호스트 화합물 및 화학식 (2)로 표시되는 제 2호스트 화합물을 포함하는 것을 특징으로 하는 유기전기소자를 제공한다.The present invention relates to an organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, and the light emitting layer is a phosphorescent light emitting layer. An organic electroluminescent device comprising a first host compound represented by (1) and a second host compound represented by formula (2).
화학식 (1) 화학식 (2) 화학식 (2-1)Formula (1) Formula (2) Formula (2-1)
또한, 본 발명은 상기 화학식들로 표시되는 화합물을 이용한 유기전기소자 및 그 전자장치를 제공한다.In addition, the present invention provides an organic electric device using the compound represented by the above formulas and an electronic device thereof.
본 발명에 따른 혼합물을 인광 호스트 물질로 이용함으로써, 유기전기소자의 높은 발광효율, 낮은 구동전압을 달성할 수 있으며, 또한 소자의 수명을 크게 향상시킬 수 있다.By using the mixture according to the present invention as a phosphorescent host material, it is possible to achieve high luminous efficiency and low driving voltage of the organic electric device, and also significantly improve the life of the device.
도 1은 본 발명에 따른 유기전기발광소자의 예시도이다.1 is an exemplary view of an organic electroluminescent device according to the present invention.
100 : 유기전기소자 110 : 기판100: organic electrical element 110: substrate
120 : 제 1전극(양극) 130 : 정공주입층120: first electrode (anode) 130: hole injection layer
140 : 정공수송층 141 : 버퍼층140: hole transport layer 141: buffer layer
150 : 발광층 151 : 발광보조층150: light emitting layer 151: light emitting auxiliary layer
160 : 전자수송층 170 : 전자주입층160: electron transport layer 170: electron injection layer
180 : 제 2전극(음극)180: second electrode (cathode)
이하, 본 발명의 실시예를 참조하여 상세하게 설명한다. 본 발명을 설명함에 있어, 관련된 공지 구성 또는 기능에 대한 구체적인 설명이 본 발명의 요지를 흐릴 수 있다고 판단되는 경우에는 그 상세한 설명은 생략한다.Hereinafter, with reference to the embodiment of the present invention will be described in detail. In describing the present invention, when it is determined that detailed descriptions of related known configurations or functions may obscure the subject matter of the present invention, detailed descriptions thereof will be omitted.
또한, 본 발명의 구성 요소를 설명하는 데 있어서, 제 1, 제 2, A, B, (a), (b) 등의 용어를 사용할 수 있다. 이러한 용어는 그 구성 요소를 다른 구성요소와 구별하기 위한 것일 뿐, 그 용어에 의해 해당 구성 요소의 본질이나 차례 또는 순서 등이 한정되지 않는다. 어떤 구성 요소가 다른 구성 요소에 "연결", "결합" 또는 "접속"된다고 기재된 경우, 그 구성 요소는 그 다른 구성 요소에 직접적으로 연결되거나 또는 접속될 수 있지만, 각 구성 요소 사이에 또 다른 구성 요소가 "연결", "결합" 또는 "접속"될 수도 있다고 이해되어야 할 것이다.In addition, in describing the components of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are only for distinguishing the component from other components, and the nature, order, or order of the component is not limited by the term. When a component is described as being "connected", "coupled" or "connected" to another component, that component may be directly connected to or connected to the other component, but another component between each component It should be understood that elements may be "connected", "coupled" or "connected".
본 명세서 및 첨부된 청구의 범위에서 사용된 바와 같이, 달리 언급하지 않는 한, 하기 용어의 의미는 하기와 같다: As used in this specification and the appended claims, unless otherwise stated, the meaning of the following terms is as follows:
본 명세서에서 사용된 용어 "할로" 또는 "할로겐"은 다른 설명이 없는 한 불소(F), 브롬(Br), 염소(Cl) 또는 요오드(I)이다.The terms "halo" or "halogen" as used herein are fluorine (F), bromine (Br), chlorine (Cl) or iodine (I), unless otherwise noted.
본 발명에 사용된 용어 "알킬" 또는 "알킬기"는 다른 설명이 없는 한 1 내지 60의 탄소수의 단일결합을 가지며, 직쇄 알킬기, 분지쇄 알킬기, 사이클로알킬(지환족)기, 알킬-치환된 사이클로알킬기, 사이클로알킬-치환된 알킬기를 비롯한 포화 지방족 작용기의 라디칼을 의미한다.The term "alkyl" or "alkyl group" used in the present invention has a single bond of 1 to 60 carbon atoms, unless otherwise specified, a straight chain alkyl group, a branched chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cycle. By radicals of saturated aliphatic functional groups, including alkyl groups, cycloalkyl-substituted alkyl groups.
본 발명에 사용된 용어 "할로알킬기" 또는 "할로겐알킬기"는 다른 설명이 없는 한 할로겐으로 치환된 알킬기를 의미한다. The term "haloalkyl group" or "halogenalkyl group" as used in the present invention means an alkyl group substituted with halogen unless otherwise specified.
본 발명에 사용된 용어 "헤테로알킬기"는 알킬기를 구성하는 탄소원자 중 하나 이상이 헤테로원자로 대체된 것을 의미한다.The term "heteroalkyl group" used in the present invention means that at least one of the carbon atoms constituting the alkyl group is replaced with a heteroatom.
본 발명에 사용된 용어 "알켄일기", "알케닐기" 또는 "알킨일기"는 다른 설명이 없는 한 각각 2 내지 60의 탄소수의 이중결합 또는 삼중결합을 가지며, 직쇄형 또는 측쇄형 사슬기를 포함하며, 여기에 제한되는 것은 아니다.The terms "alkenyl group", "alkenyl group" or "alkynyl group" used in the present invention have a double or triple bond of 2 to 60 carbon atoms, unless otherwise specified, and include straight or branched chain groups. , But is not limited to this.
본 발명에 사용된 용어 "시클로알킬"은 다른 설명이 없는 한 3 내지 60의 탄소수를 갖는 고리를 형성하는 알킬을 의미하며, 여기에 제한되는 것은 아니다.As used herein, the term "cycloalkyl" means an alkyl forming a ring having 3 to 60 carbon atoms, unless otherwise specified, but is not limited thereto.
본 발명에 사용된 용어 "알콕실기", "알콕시기", 또는 "알킬옥시기"는 산소 라디칼이 부착된 알킬기를 의미하며, 다른 설명이 없는 한 1 내지 60의 탄소수를 가지며, 여기에 제한되는 것은 아니다.The term "alkoxyl group", "alkoxy group", or "alkyloxy group" used in the present invention means an alkyl group to which an oxygen radical is attached, and has a carbon number of 1 to 60 unless otherwise specified, and is limited thereto. It is not.
본 발명에 사용된 용어 "알켄옥실기", "알켄옥시기", "알켄일옥실기", 또는 "알켄일옥시기"는 산소 라디칼이 부착된 알켄일기를 의미하며, 다른 설명이 없는 한 2 내지 60의 탄소수를 가지며, 여기에 제한되는 것은 아니다.As used herein, the terms "alkenoxyl group", "alkenoxy group", "alkenyloxyl group", or "alkenyloxy group" means an alkenyl group to which an oxygen radical is attached, and 2 to 60 unless otherwise specified. It has a carbon number, and is not limited thereto.
본 발명에 사용된 용어 "아릴옥실기" 또는 "아릴옥시기"는 산소 라디칼이 부착된 아릴기를 의미하며, 다른 설명이 없는 한 6 내지 60의 탄소수를 가지며, 여기에 제한되는 것은 아니다.The term "aryloxyl group" or "aryloxy group" used in the present invention means an aryl group to which an oxygen radical is attached, and has a carbon number of 6 to 60 unless otherwise specified, and is not limited thereto.
본 발명에 사용된 용어 "아릴기" 및 "아릴렌기"는 다른 설명이 없는 한 각각 6 내지 60의 탄소수를 가지며, 이에 제한되는 것은 아니다. 본 발명에서 아릴기 또는 아릴렌기는 단일 고리 또는 다중 고리의 방향족을 의미하며, 이웃한 치환기가 결합 또는 반응에 참여하여 형성된 방향족 고리를 포함한다. 예컨대, 아릴기는 페닐기, 비페닐기, 플루오렌기, 디메틸플루오렌기, 디페닐플루오렌기, 스파이로플루오렌기일 수 있다.The terms "aryl group" and "arylene group" used in the present invention have 6 to 60 carbon atoms, respectively, and are not limited thereto unless otherwise specified. In the present invention, an aryl group or an arylene group means a single ring or multi-ring aromatic, and includes an aromatic ring formed by adjacent substituents participating in a bond or reaction. For example, the aryl group may be a phenyl group, biphenyl group, fluorene group, dimethylfluorene group, diphenylfluorene group, or spirofluorene group.
접두사 "아릴" 또는 "아르"는 아릴기로 치환된 라디칼을 의미한다. 예를 들어 아릴알킬기는 아릴기로 치환된 알킬기이며, 아릴알켄일기는 아릴기로 치환된 알켄일기이며, 아릴기로 치환된 라디칼은 본 명세서에서 설명한 탄소수를 가진다. The prefix "aryl" or "ar" means a radical substituted with an aryl group. For example, an arylalkyl group is an alkyl group substituted with an aryl group, an arylalkenyl group is an alkenyl group substituted with an aryl group, and a radical substituted with an aryl group has a carbon number described herein.
또한 접두사가 연속으로 명명되는 경우 먼저 기재된 순서대로 치환기가 나열되는 것을 의미한다. 예를 들어, 아릴알콕시기의 경우 아릴기로 치환된 알콕시기를 의미하며, 알콕실카르보닐기의 경우 알콕실기로 치환된 카르보닐기를 의미하며, 또한 아릴카르보닐알켄일기의 경우 아릴카르보닐기로 치환된 알켄일기를 의미하며 여기서 아릴카르보닐기는 아릴기로 치환된 카르보닐기이다.Also, when the prefix is named in succession, it means that the substituents are listed in the order described first. For example, in the case of an arylalkoxy group, it means an alkoxy group substituted with an aryl group, in the case of an alkoxycarbonyl group, it means a carbonyl group substituted with an alkoxyl group, and in the case of an arylcarbonyl alkenyl group, it means an alkenyl group substituted with an arylcarbonyl group. Wherein the arylcarbonyl group is a carbonyl group substituted with an aryl group.
본 명세서에서 사용된 용어 "헤테로알킬"은 다른 설명이 없는 한 하나 이상의 헤테로원자를 포함하는 알킬을 의미한다. 본 발명에 사용된 용어 "헤테로아릴기" 또는 "헤테로아릴렌기"는 다른 설명이 없는 한 각각 하나 이상의 헤테로원자를 포함하는 탄소수 2 내지 60의 아릴기 또는 아릴렌기를 의미하며, 여기에 제한되는 것은 아니며, 단일 고리 및 다중 고리 중 적어도 하나를 포함하며, 이웃한 작용기기가 결합하여 형성될 수도 있다.As used herein, the term "heteroalkyl" means alkyl containing one or more heteroatoms, unless otherwise specified. As used herein, the term "heteroaryl group" or "heteroarylene group" means an aryl group or an arylene group having 2 to 60 carbon atoms each containing at least one heteroatom, unless otherwise specified, and is not limited thereto. No, it includes at least one of a single ring and multiple rings, and may be formed by combining adjacent functional devices.
본 발명에 사용된 용어 "헤테로고리기"는 다른 설명이 없는 한 하나 이상의 헤테로원자를 포함하고, 2 내지 60의 탄소수를 가지며, 단일 고리 및 다중 고리 중 적어도 하나를 포함하며, 헤테로지방족 고리 및 헤테로방향족 고리를 포함한다. 이웃한 작용기가 결합하여 형성될 수도 있다.The term "heterocyclic group" used in the present invention includes at least one heteroatom, has 2 to 60 carbon atoms, includes at least one of a single ring and multiple rings, heteroaliphatic ring and hetero, unless otherwise specified. Aromatic rings. Adjacent functional groups may also be formed by bonding.
본 명세서에서 사용된 용어 "헤테로원자"는 다른 설명이 없는 한 N, O, S, P 또는 Si를 나타낸다.The term “heteroatom” as used herein refers to N, O, S, P or Si, unless otherwise stated.
또한 "헤테로고리기"는 고리를 형성하는 탄소 대신 SO2를 포함하는 고리도 포함할 수 있다. 예컨대, "헤테로고리기"는 다음 화합물을 포함한다. In addition, "heterocyclic group" may include a ring containing SO 2 instead of carbon forming a ring. For example, "heterocyclic group" includes the following compounds.
다른 설명이 없는 한, 본 발명에 사용된 용어 "지방족"은 탄소수 1 내지 60의 지방족 탄화수소를 의미하며, "지방족고리"는 탄소수 3 내지 60의 지방족 탄화수소 고리를 의미한다.Unless otherwise specified, the term "aliphatic" as used herein refers to an aliphatic hydrocarbon having 1 to 60 carbon atoms, and "aliphatic ring" means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.
다른 설명이 없는 한, 본 발명에 사용된 용어 "고리"는 탄소수 3 내지 60의 지방족고리 또는 탄소수 6 내지 60의 방향족고리 또는 탄소수 2 내지 60의 헤테로고리 또는 이들의 조합으로 이루어진 융합 고리를 말하며, 포화 또는 불포화고리를 포함한다.Unless otherwise specified, the term "ring" used in the present invention refers to an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocyclic ring having 2 to 60 carbon atoms or a combination thereof, and It contains a saturated or unsaturated ring.
전술한 헤테로화합물 이외의 그 밖의 다른 헤테로화합물 또는 헤테로라디칼은 하나 이상의 헤테로원자를 포함하며, 여기에 제한되는 것은 아니다.Other hetero compounds or hetero radicals other than the above-described hetero compounds include one or more hetero atoms, but are not limited thereto.
다른 설명이 없는 한, 본 발명에 사용된 용어 "카르보닐"이란 -COR'로 표시되는 것이며, 여기서 R'은 수소, 탄소수 1 내지 20의 알킬기, 탄소수 6 내지 30의 아릴기, 탄소수 3 내지 30의 사이클로알킬기, 탄소수 2 내지 20의 알켄일기, 탄소수 2 내지 20의 알킨일기, 또는 이들의 조합인 것이다.Unless otherwise specified, the term "carbonyl" used in the present invention is represented by -COR ', where R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, 3 to 30 carbon atoms. Is a cycloalkyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.
다른 설명이 없는 한, 본 발명에 사용된 용어 "에테르"란 -R-O-R'로 표시되는 것이며, 여기서 R 또는 R'은 각각 서로 독립적으로 수소, 탄소수 1 내지 20의 알킬기, 탄소수 6 내지 30의 아릴기, 탄소수 3 내지 30의 사이클로알킬기, 탄소수 2 내지 20의 알켄일기, 탄소수 2 내지 20의 알킨일기, 또는 이들의 조합인 것이다.Unless otherwise specified, the term "ether" used in the present invention is represented by -RO-R ', wherein R or R' are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, or 6 to 30 carbon atoms. It is an aryl group, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.
또한 명시적인 설명이 없는 한, 본 발명에서 사용된 용어 "치환 또는 비치환된"에서 "치환"은 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1~C20의 알킬기, C1~C20의 알콕실기, C1~C20의 알킬아민기, C1~C20의 알킬티오펜기, C6~C20의 아릴티오펜기, C2~C20의 알켄일기, C2~C20의 알킨일기, C3~C20의 시클로알킬기, C6~C20의 아릴기, 중수소로 치환된 C6~C20의 아릴기, C8~C20의 아릴알켄일기, 실란기, 붕소기, 게르마늄기, 및 C2~C20의 헤테로고리기로 이루어진 군으로부터 선택되는 1개 이상의 치환기로 치환됨을 의미하며, 이들 치환기에 제한되는 것은 아니다.Also, unless expressly stated, the term "substituted" in the term "substituted or unsubstituted" used in the present invention is deuterium, halogen, amino group, nitrile group, nitro group, C 1 ~ C 20 alkyl group, C 1 ~ C 20 alkoxyl group, C 1 ~ C 20 alkylamine group, C 1 ~ C 20 alkylthiophene group, C 6 ~ C 20 arylthiophene group, C 2 ~ C 20 alkenyl group, C 2 ~ C 20 alkynyl group, C 3 ~ C 20 cycloalkyl group, C 6 ~ C 20 aryl group, substituted with deuterium C 6 ~ C 20 aryl group, C 8 ~ C 20 aryl alkenyl group, silane group, boron Means a group, a germanium group, and one or more substituents selected from the group consisting of C 2 to C 20 heterocyclic groups, and is not limited to these substituents.
또한 명시적인 설명이 없는 한, 본 발명에서 사용되는 화학식은 하기 화학식의 지수 정의에 의한 치환기 정의와 동일하게 적용된다.In addition, unless otherwise specified, the formula used in the present invention is applied in the same manner as the substituent definition by the exponent definition of the following formula.
여기서, a가 0의 정수인 경우 치환기 R1은 부존재하는 것을 의미하는데, 즉 a가 0인 경우는 벤젠고리를 형성하는 탄소에 모두 수소가 결합된 것을 의미하며, 이때 탄소에 결합된 수소의 표시를 생략하고 화학식이나 화합물을 기재할 수 있다. a가 1의 정수인 경우 하나의 치환기 R1은 벤젠 고리를 형성하는 탄소 중 어느 하나의 탄소에 결합하며, a가 2 또는 3의 정수인 경우 각각 다음과 같이 결합하며 이때 R1은 서로 동일하거나 다를 수 있으며, a가 4 내지 6의 정수인 경우 이와 유사한 방식으로 벤젠 고리의 탄소에 결합하며, 한편 벤젠 고리를 형성하는 탄소에 결합된 수소의 표시는 생략한다.Here, when a is an integer of 0, the substituent R 1 means non-existent, that is, when a is 0, it means that hydrogen is bonded to all of the carbons forming the benzene ring. The formula or compound may be omitted. When a is an integer of 1, one substituent R 1 is bound to any one of carbons forming a benzene ring, and when a is an integer of 2 or 3, each of them is bonded as follows, where R 1 may be the same or different from each other. When a is an integer of 4 to 6, it binds to the carbon of the benzene ring in a similar manner, while the indication of hydrogen bound to the carbon forming the benzene ring is omitted.
이하, 본 발명의 일 측면에 따른 화합물 및 이를 포함하는 유기전기소자에 대하여 설명한다. Hereinafter, a compound according to an aspect of the present invention and an organic electric device including the same will be described.
본 발명은 제 1전극, 제 2전극, 및 상기 제 1전극과 상기 제 2전극 사이에 형성된 유기물층을 포함하는 유기전기소자에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 인광성 발광층으로서 화학식 (1)로 표시되는 제 1호스트 및 화학식 (2)로 표시되는 제 2호스트를 포함하는 것을 특징으로 하는 유기전기소자를 제공한다. The present invention relates to an organic electric device comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, and the light emitting layer is a phosphorescent light emitting layer. It provides an organic electric device comprising a first host represented by (1) and a second host represented by the formula (2).
화학식 (1) 화학식 (2) 화학식 (2-1)Formula (1) Formula (2) Formula (2-1)
{상기 화학식 (1), (2) 및 (2-1)에서,{In the formulas (1), (2) and (2-1) above,
1) W, X 및 Y는 각각 독립적으로 O, S, CR'R", SiR'R" 또는 Se이고,1) W, X and Y are each independently O, S, CR'R ", SiR'R" or Se,
2) a 및 b는 각각 독립적으로 0 또는 1이며, 단 a+b는 1 이상이고,2) a and b are each independently 0 or 1, provided that a + b is 1 or more,
3) R' 및 R"는 각각 독립적으로 수소; C1~C50의 알킬기; C6~C60의 아릴기; 및 C2~C60의 헤테로아릴기;로 이루어진 군에서 선택되거나, R' 및 R"은 서로 고리를 형성하여 스파이로(spiro) 고리를 형성하고, 3) R 'and R "are each independently hydrogen; an alkyl group of C 1 to C 50 ; an aryl group of C 6 to C 60 ; and a heteroaryl group of C 2 to C 60 ; or R' And R "form a ring with each other to form a spiro ring,
4) L1, L2 및 L'은 각각 독립적으로 단일결합; C6~C60의 아릴렌기; 또는 C2~C60의 헤테로아릴렌기;이고4) L 1 , L 2 and L 'are each independently a single bond; C 6 ~ C 60 Arylene group; Or a C 2 ~ C 60 heteroarylene group; and
5) Ar1, Ar2 및 Ar3는 각각 독립적으로 수소; 중수소; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리와 C6~C60의 방향족고리의 융합고리기; C1~C50의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C30의 알콕실기; C6~C30의 아릴옥시기; 및 -L'-NR'R";로 이루어진 군에서 선택되고,5) Ar 1 , Ar 2 and Ar 3 are each independently hydrogen; heavy hydrogen; C 6 ~ C 60 Aryl group; Fluorenyl group; C 2 ~ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C 3 ~ C 60 aliphatic ring and C 6 ~ C 60 aromatic ring fused ring group; C 1 ~ C 50 alkyl group; C 2 ~ C 20 alkenyl group; C 2 ~ C 20 alkynyl group; C 1 ~ C 30 Alkoxy group; C 6 ~ C 30 Aryloxy group; And -L'-NR'R ";
6) Z는 NR', O, S, CR'R", SiR'R", 또는 Se이고,6) Z is NR ', O, S, CR'R ", SiR'R", or Se,
7) R1 내지 R5은 각각 독립적으로 수소; 중수소; 할로겐; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리와 C6~C60의 방향족고리의 융합고리기; C1~C50의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C30의 알콕실기; C6~C30의 아릴옥시기; 및 -L'-N(Ra)(Rb);로 이루어진 군에서 선택되고, 7) R 1 to R 5 are each independently hydrogen; heavy hydrogen; halogen; C 6 ~ C 60 Aryl group; Fluorenyl group; C 2 ~ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C 3 ~ C 60 aliphatic ring and C 6 ~ C 60 aromatic ring fused ring group; C 1 ~ C 50 alkyl group; C 2 ~ C 20 alkenyl group; C 2 ~ C 20 alkynyl group; C 1 ~ C 30 Alkoxy group; C 6 ~ C 30 Aryloxy group; And -L'-N (R a ) (R b ); is selected from the group consisting of,
상기 Ra 및 Rb 은 서로 독립적으로 C6~C60의 아릴기; 플루오렌일기; C3~C60의 지방족고리와 C6~C60의 방향족고리의 융합고리기; 및 O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기;로 이루어진 군에서 선택되고, R a and R b are independently of each other C 6 ~ C 60 aryl group; Fluorenyl group; C 3 ~ C 60 aliphatic ring and C 6 ~ C 60 aromatic ring fused ring group; And O, N, S, Si, and C 2 ~ C 60 heterocyclic group containing at least one heteroatom; is selected from the group consisting of,
상기 l, m, n, o 및 p가 2 이상인 경우 각각 복수로서 서로 동일하거나 상이하며 복수의 R1끼리, 복수의 R2끼리, 복수의 R3끼리, 복수의 R4끼리, 복수의 R5끼리는 서로 결합하여 방향족 및 헤테로방향족 고리를 형성할 수 있고, Wherein l, m, n, o and identical to or different from each other as a plurality each of not less than p 2, and a plurality of R 1 each other, a plurality of R 2 to each other, a plurality of R 3 to each other, a plurality of R 4 with each other, a plurality of R 5 They may combine with each other to form an aromatic and heteroaromatic ring,
8) R12, R13 및 R14는 각각 독립적으로 수소; 중수소; 할로겐; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리와 C6~C60의 방향족고리의 융합고리기; C1~C50의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C30의 알콕실기; C6~C30의 아릴옥시기; 및 -L'-N(Ra)(Rb);로 이루어진 군에서 선택되고, 8) R 12 , R 13 and R 14 are each independently hydrogen; heavy hydrogen; halogen; C 6 ~ C 60 Aryl group; Fluorenyl group; C 2 ~ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C 3 ~ C 60 aliphatic ring and C 6 ~ C 60 aromatic ring fused ring group; C 1 ~ C 50 alkyl group; C 2 ~ C 20 alkenyl group; C 2 ~ C 20 alkynyl group; C 1 ~ C 30 Alkoxy group; C 6 ~ C 30 Aryloxy group; And -L'-N (R a ) (R b ); is selected from the group consisting of,
상기 g, h 및 i가 2 이상인 경우 각각 복수로서 서로 동일하거나 상이하며 인접한 복수의 R12끼리, 복수의 R13끼리, 복수의 R14끼리는 서로 결합하여 방향족 및 헤테로방향족 고리를 형성할 수 있고, 인접한 R12, 인접한 R13, 및 인접한 R14 중 적어도 한쌍은 고리를 형성하고,When the g, h and i are 2 or more, a plurality of each of the same or different and adjacent to each other, a plurality of adjacent R 12 , a plurality of R 13 , and a plurality of R 14 may combine with each other to form an aromatic and heteroaromatic ring, At least one pair of contiguous R 12 , contiguous R 13 , and contiguous R 14 forms a ring,
9) g 및 i는 0~4 중 어느 하나의 정수이고, h는 0~2 중 어느 하나의 정수이며, n, l 및 p은 0~4 중 어느 하나의 정수이고, m은 0 또는 1이며, o는 0~3 중 어느 하나의 정수이고, 9) g and i are integers from 0 to 4, h is an integer from 0 to 2, n, l and p are integers from 0 to 4, m is 0 or 1 , o is an integer from 0 to 3,
10) 상기 화학식 (2)의 인접한 2개의 *와 화학식 (2-1)의 *와 결합하여 고리를 형성하며,10) the adjacent two * of formula (2) and the * of formula (2-1) combine to form a ring,
여기서, 상기 아릴기, 플루오렌닐기, 아릴렌기, 헤테로고리기, 플루오렌일렌기, 융합고리기, 알킬기, 알케닐기, 알콕시기 및 아릴옥시기는 각각 중수소; 할로겐; 실란기; 실록산기; 붕소기; 게르마늄기; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕실기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C20의 아릴기; 중수소로 치환된 C6-C20의 아릴기; 플루오렌일기; C2-C20의 헤테로고리기; C3-C20의 시클로알킬기; C7-C20의 아릴알킬기; 및 C8-C20의 아릴알켄일기;로 이루어진 군에서 선택된 하나 이상의 치환기로 더욱 치환될 수 있으며, 또한 이들 치환기들은 서로 결합하여 고리를 형성할 수도 있으며, 여기서 '고리'란 C3-C60의 지방족고리 또는 C6-C60의 방향족고리 또는 C2-C60의 헤테로고리 또는 이들의 조합으로 이루어진 융합 고리를 말하며, 포화 또는 불포화 고리를 포함한다.}Here, the aryl group, fluorenyl group, arylene group, heterocyclic group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group each deuterium; halogen; Silane group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; C 1 -C 20 alkylthio; Alkoxyl group of C 1 -C 20 ; C 1 -C 20 alkyl group; Alkenyl group of C 2 -C 20 ; Alkynyl group of C 2 -C 20 ; C 6 -C 20 Aryl group; A C 6 -C 20 aryl group substituted with deuterium; Fluorenyl group; C 2 -C 20 heterocyclic group; C 3 -C 20 cycloalkyl group; C 7 -C 20 Arylalkyl group; And C 8 -C 20 arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, and these substituents may also combine with each other to form a ring, wherein 'ring' means C 3 -C 60 Refers to an aliphatic ring of C or an aromatic ring of C 6 -C 60 or a heterocycle of C 2 -C 60 or a combination thereof, and includes a saturated or unsaturated ring.}
본 발명에서 상기 화학식 (1)로 나타낸 화합물은 하기 화학식 (3) 또는 (4)로 표시되는 화합물을 포함하는 유기전기소자를 제공한다.The compound represented by the formula (1) in the present invention provides an organic electric device comprising a compound represented by the following formula (3) or (4).
화학식 (3) 화학식 (4)Formula (3) Formula (4)
(상기 화학식 (3) 및 (4)에서, X, Y, Z, Ar1, L1, R1, R2, R3, R4, R5, l, m, n, o, 및 p는 상기에서 정의된 바와 동일하다)(In the formulas (3) and (4), X, Y, Z, Ar 1 , L 1 , R 1 , R 2 , R 3 , R 4 , R 5 , l, m, n, o, and p are Same as defined above)
또 다른 구체적인 예로, 본 발명은 상기 화학식 (1)로 나타낸 화합물이 하기 화학식 (5) 내지 (12) 중 어느 하나로 표시되는 화합물을 포함하는 유기전기소자를 제공한다.As another specific example, the present invention provides an organic electric device in which the compound represented by the formula (1) includes a compound represented by any one of the following formulas (5) to (12).
화학식 (5) 화학식 (6) 화학식 (7) 화학식 (8) Formula (5) Formula (6) Formula (7) Formula (8)
화학식 (9) 화학식 (10) 화학식 (11) 화학식 (12) Formula (9) Formula (10) Formula (11) Formula (12)
(상기 화학식 (5) 내지 (12)에서, X, Y, Z, Ar1, L1, R1, R2, R3, R4, R5, l, m, n, o, 및 p는 상기에서 정의된 바와 동일하다)(In the formulas (5) to (12), X, Y, Z, Ar 1 , L 1 , R 1 , R 2 , R 3 , R 4 , R 5 , l, m, n, o, and p are Same as defined above)
또한 본 발명은 상기 화학식 (1)에서 상기 l, m, n, o 및 p가 모두 0인 화합물을 포함하는 유기전기소자를 제공한다.In addition, the present invention provides an organic electric device including a compound in which all of l, m, n, o and p are 0 in the formula (1).
또 다른 예로, 본 발명은 상기 화학식 (1)에서 상기 R1, R2, R3, R4 및 R5 중 어느 하나는 이웃한 한 쌍이 서로 결합하여 고리를 형성하는 화합물을 포함하는 유기전기소자를 제공한다.As another example, the present invention in the formula (1), any one of the R 1 , R 2 , R 3 , R 4 and R 5 is an organic electric device comprising a compound in which a pair of neighboring pairs to each other to form a ring Provides
또한, 본 발명은 상기 화학식 (1)에서, 상기 X 및 Y는 S 또는 O인 화합물을 포함하는 유기전기소자를 제공한다.In addition, the present invention in the formula (1), X and Y provides an organic electric device comprising a compound of S or O.
구체적인 예로, 본 발명에서 상기 화학식 (1)은 하기 화합물을 포함한다.As a specific example, the formula (1) in the present invention includes the following compound.
한편 본 발명은 상기 화학식 (2)로 나타낸 화합물이 하기 화학식 (13) 내지 (17) 중 어느 하나로 표시되는 화합물을 포함하는 유기전기소자를 제공한다.Meanwhile, the present invention provides an organic electric device in which the compound represented by the formula (2) includes a compound represented by any one of the following formulas (13) to (17).
화학식 (13) 화학식 (14) 화학식 (15) 화학식 (16) 화학식 (17)Formula (13) Formula (14) Formula (15) Formula (16) Formula (17)
(상기 화학식 (13) 내지 (17)에서, Ar2, Ar3, L2, g, h, i, R' 및 R"는 상기에서 정의한 바와 같고,(In the formulas (13) to (17), Ar 2 , Ar 3 , L 2 , g, h, i, R 'and R "are as defined above,
R12', R13' 및 R14'은 상기 R12, R13 및 R14의 정의와 같다.)R 12 ' , R 13' and R 14 ' are as defined in R 12 , R 13 and R 14 above .)
또 다른 예로, 본 발명은 상기 화학식 (2)로 나타낸 화합물이 하기 화학식 (18) 내지 (57) 중 어느 하나로 표시되는 화합물을 포함한다.As another example, the present invention includes a compound represented by any one of the following formulas (18) to (57).
화학식 (18) 화학식 (19) 화학식 (20) 화학식 (21)Formula (18) Formula (19) Formula (20) Formula (21)
화학식 (22) 화학식 (23) 화학식 (24) 화학식 (25)Formula (22) Formula (23) Formula (24) Formula (25)
화학식 (26) 화학식 (27) 화학식 (28) 화학식 (29)Formula (26) Formula (27) Formula (28) Formula (29)
화학식 (30) 화학식 (31) 화학식 (32) 화학식 (33)Formula (30) Formula (31) Formula (32) Formula (33)
화학식 (34) 화학식 (35) 화학식 (36) 화학식 (37)Formula (34) Formula (35) Formula (36) Formula (37)
화학식 (38) 화학식 (39) 화학식 (40) 화학식 (41) Formula (38) Formula (39) Formula (40) Formula (41)
화학식 (42) 화학식 (43) 화학식 (44) 화학식 (45)Formula (42) Formula (43) Formula (44) Formula (45)
화학식 (46) 화학식 (47) 화학식 (48) 화학식 (49)Formula (46) Formula (47) Formula (48) Formula (49)
화학식 (50) 화학식 (51) 화학식 (52) 화학식 (53)Formula (50) Formula (51) Formula (52) Formula (53)
화학식 (54) 화학식 (55) 화학식 (56) 화학식 (57)Formula (54) Formula (55) Formula (56) Formula (57)
(상기 화학식 (18) 내지 (57)에서, Ar2, Ar3, L2, R12', R13', R14', W, g, h 및 i는 상기에서 정의한 바와 같고,(In the formulas (18) to (57), Ar 2 , Ar 3 , L 2 , R 12 ' , R 13' , R 14 ' , W, g, h and i are as defined above,
R12', R13' 및 R14'은 상기 R12, R13 및 R14의 정의와 같으며,R 12 ' , R 13' and R 14 ' are as defined in R 12 , R 13 and R 14 above ,
t는 0 내지 4 중 어느 하나의 정수이고, s 및 u는 각각 독립적으로 0 내지 6 중 어느 하나의 정수이다.)t is an integer from 0 to 4, and s and u are each independently an integer from 0 to 6.)
구체적인 예로, 본 발명에서 상기 화학식 (2)는 하기 화합물을 포함한다. As a specific example, the formula (2) in the present invention includes the following compound.
도 1을 참조하여 설명하면, 본 발명에 따른 유기전기소자(100)는 기판(110) 상에 형성된 제 1전극(120), 제 2전극(180) 및 제 1전극(120)과 제 2전극(180) 사이에 화학식 1 및 2로 표시되는 화합물을 포함하는 유기물층을 구비한다. 이때, 제 1전극(120)은 애노드(양극)이고, 제 2전극(180)은 캐소드(음극)일 수 있으며, 인버트형의 경우에는 제 1전극이 캐소드이고 제 2전극이 애노드일 수 있다.Referring to FIG. 1, the organic electric device 100 according to the present invention includes a first electrode 120, a second electrode 180 and a first electrode 120 and a second electrode formed on the substrate 110. Between (180) it is provided with an organic layer containing the compound represented by the formula (1) and (2). At this time, the first electrode 120 may be an anode (anode), the second electrode 180 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.
유기물층은 제 1전극(120) 상에 순차적으로 정공주입층(130), 정공수송층(140), 발광층(150), 발광보조층(151), 전자수송층(160) 및 전자주입층(170)을 포함할 수 있다. 이때, 발광층(150)을 제외한 나머지 층들이 형성되지 않을 수 있다. 정공저지층, 전자저지층, 발광보조층(151), 전자수송보조층, 버퍼층(141) 등을 더 포함할 수 있고, 전자수송층(160) 등이 정공저지층의 역할을 할 수도 있다.The organic material layer sequentially comprises a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, a light emitting auxiliary layer 151, an electron transport layer 160 and an electron injection layer 170 on the first electrode 120. It can contain. At this time, layers other than the emission layer 150 may not be formed. A hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, an electron transport auxiliary layer, a buffer layer 141, and the like may be further included, and the electron transport layer 160, etc. may also serve as a hole blocking layer.
또한, 미도시하였지만 본 발명에 따른 유기전기소자는 제 1전극과 제 2전극중 적어도 일면 중 상기 유기물층과 반대되는 일면에 형성된 보호층을 더 포함할 수 있다. 본 발명의 상기 화학식 1을 포함하는 화합물은 광효율개선층 또는 보호층의 재료로서 사용될수 있다.In addition, although not shown, the organic electric device according to the present invention may further include a protective layer formed on one surface opposite to the organic material layer among at least one surface of the first electrode and the second electrode. The compound containing Formula 1 of the present invention may be used as a material for the light efficiency improving layer or the protective layer.
한편, 동일한 코어일지라도 어느 위치에 어느 치환기를 결합시키냐에 따라 밴드갭(band gap), 전기적 특성, 계면 특성 등이 달라질 수 있으므로, 코어의 선택 및 이에 결합된 서브(sub)-치환체의 조합도 아주 중요하며, 특히 각 유기물층 간의 에너지 level 및 T1 값, 물질의 고유특성(mobility, 계면특성 등) 등이 최적의 조합을 이루었을 때 긴 수명과 높은 효율을 동시에 달성할 수 있다.On the other hand, even in the same core, the band gap, electrical properties, and interfacial properties may vary depending on which substituents are attached to which positions, so the selection of the core and the combination of sub-substituents coupled thereto are also very good. It is important, especially when the energy level and T1 value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined, long life and high efficiency can be achieved simultaneously.
본 발명의 일 실시예에 따른 유기전기발광소자는 PVD(physical vapor deposition) 방법을 이용하여 제조될 수 있다. 예컨대, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공주입층(130), 정공수송층(140), 발광층(150), 전자수송층(160) 및 전자주입층(170)을 포함하는 유기물층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 또한, 정공수송층(140)과 발광층(150) 사이에 발광보조층(151)을, 발광층(150)과 전자수송층(160) 사이에 전자수송보조층을 추가로 더 형성할 수 있다. The organic electroluminescent device according to an embodiment of the present invention may be manufactured using a physical vapor deposition (PVD) method. For example, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode, and a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, and an electron transport layer 160 are formed thereon. After forming an organic material layer including the electron injection layer 170, it can be manufactured by depositing a material that can be used as a cathode thereon. In addition, the light emitting auxiliary layer 151 may be further formed between the hole transport layer 140 and the light emitting layer 150, and the electron transport auxiliary layer may be further formed between the light emitting layer 150 and the electron transport layer 160.
이에 따라, 본 발명은 상기 화학식 (1) 및 상기 화학식 (2)로 나타내는 화합물이 1:9 내지 9:1 중 어느 하나의 비율로 혼합되어 상기 발광층에 포함되는 유기전기소자를 제공하며, 바람직하게는 1:9 내지 5:5로, 보다 바람직하게는 2:8 내지 3:7 비율로 혼합되어 상기 발광층에 포함된다.Accordingly, the present invention provides a compound represented by the formula (1) and the formula (2) in an ratio of any one of 1: 9 to 9: 1 to provide an organic electric device included in the light emitting layer, preferably Is 1: 9 to 5: 5, more preferably mixed in a ratio of 2: 8 to 3: 7 and included in the light emitting layer.
본 발명은 상기 유기전기소자에서 상기 제 1전극의 일측면 중 상기 유기물층과 반대되는 일측 또는 상기 제 2전극의 일측면 중 상기 유기물층과 반대되는 일측 중 적어도 하나에 형성되는 광효율개선층을 더 포함하는 유기전기소자를 제공한다.The present invention further comprises a light efficiency improving layer formed on at least one of one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer from one side of the first electrode in the organic electric device. An organic electric device is provided.
또한 본 발명에서 상기 유기물층은 스핀코팅 공정, 노즐 프린팅 공정, 잉크젯 프린팅 공정, 슬롯코팅 공정, 딥코팅 공정 및 롤투롤 공정 중 어느 하나에 의해 형성되며, 본 발명에 따른 유기물층은 다양한 방법으로 형성될 수 있으므로, 그 형성방법에 의해 본 발명의 권리범위가 제한되는 것은 아니다. In addition, in the present invention, the organic material layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process and a roll-to-roll process, and the organic material layer according to the present invention can be formed by various methods Therefore, the scope of the present invention is not limited by the forming method.
본 발명의 일 실시예에 따른 유기전기소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic electric device according to an embodiment of the present invention may be a front emission type, a back emission type, or a double-sided emission type depending on the material used.
WOLED(White Organic Light Emitting Device)는 고해상도 실현이 용이하고 공정성이 우수한 한편, 기존의 LCD의 칼라필터 기술을 이용하여 제조될 수 있는 이점이 있다. 주로 백라이트 장치로 사용되는 백색 유기발광소자에 대한 다양한 구조들이 제안되고 특허화되고 있다. 대표적으로, R(Red), G(Green), B(Blue) 발광부들을 상호평면적으로 병렬배치(side-by-side) 방식, R, G, B 발광층이 상하로 적층되는 적층(stacking) 방식이 있고, 청색(B) 유기발광층에 의한 전계발광과 이로부터의 광을 이용하여 무기형광체의 자발광(photo-luminescence)을 이용하는 색변환물질(color conversion material, CCM) 방식 등이 있는데, 본 발명은 이러한 WOLED에도 적용될 수 있을 것이다.WOLED (White Organic Light Emitting Device) has the advantage of being easy to realize high resolution and excellent processability, and can be manufactured using the color filter technology of the existing LCD. Various structures for white organic light emitting devices mainly used as backlight devices have been proposed and patented. Typically, the R (Red), G (Green), B (Blue) light emitting units are arranged in a mutually planar side-by-side manner, and the stacking method in which the R, G, and B light-emitting layers are stacked up and down. There is, there is a color conversion material (CCM) method using electroluminescence of the blue (B) organic light-emitting layer and photo-luminescence of the inorganic phosphor using light therefrom, the present invention Can be applied to such WOLED.
또한 본 발명은 상기한 유기전기소자를 포함하는 디스플레이장치; 및 상기 디스플레이장치를 구동하는 제어부;를 포함하는 전자장치를 제공한다. In addition, the present invention is a display device comprising the above-described organic electric device; And a control unit for driving the display device.
또 다른 측면에서 상기 유기전기소자는 유기전기발광소자, 유기태양전지, 유기감광체, 유기트랜지스터, 및 단색 또는 백색 조명용 소자 중 적어도 하나인 것을 특징으로 하는 전자장치를 본 발명에서 제공한다. 이때, 전자장치는 현재 또는 장래의 유무선 통신단말기일 수 있으며, 휴대폰 등의 이동 통신 단말기, PDA, 전자사전, PMP, 리모콘, 네비게이션, 게임기, 각종 TV, 각종 컴퓨터 등 모든 전자장치를 포함한다.In another aspect, the present invention provides an electronic device characterized in that the organic electroluminescent device is at least one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and a monochromatic or white lighting device. At this time, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation, game machines, various TVs, and various computers.
이하에서, 본 발명의 상기 화학식 (1) 및 (2)로 표시되는 화합물의 합성예 및 본 발명의 유기전기소자의 제조예에 관하여 실시예를 들어 구체적으로 설명하지만, 본 발명의 하기 실시예로 한정되는 것은 아니다.Hereinafter, examples of the synthesis of the compounds represented by the formulas (1) and (2) of the present invention and the production examples of the organic electroluminescent device of the present invention will be specifically described with reference to the following examples of the present invention. It is not limited.
[합성예 1][Synthesis Example 1]
본 발명에 따른 화학식 (1)로 표시되는 화합물(final product 1)은 하기 반응식 1과 같이 Sub 1 과 Sub 2가 반응하여 제조된다.The compound represented by Chemical Formula (1) according to the present invention (final product 1) is prepared by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1 below.
<반응식 1><Scheme 1>
1. Sub 1의 합성 예시1. Synthesis Example of Sub 1
반응식 1의 sub 1은 하기 반응식 2의 반응경로에 의해 합성될 수 있으며 이에 한정된 것은 아니다. Sub 1 of Scheme 1 may be synthesized by the following Reaction Scheme 2, but is not limited thereto.
<반응식 2> (X'= I, Br, Cl)<Reaction Scheme 2> (X '= I, Br, Cl)
상기 반응식 2의 Sub 1에 속하는 화합물의 합성예는 다음과 같다.Synthesis examples of compounds belonging to Sub 1 of Scheme 2 are as follows.
1. Sub 1-1의 합성예 (a=1, b= 0, X= S 일 때)1. Synthesis Example of Sub 1-1 (when a = 1, b = 0, X = S)
Sub 1-I-1의 합성법Synthesis of Sub 1-I-1
둥근바닥플라스크에 2-Chloroaniline (67.2g, 525mmol), 1,4-Dibromodibenzothiophene (150g, 438mmol), Pd2(dba)3
(16.2g, 17.4mmol), P(t-Bu)3 (15g, 43.8mmol), NaO(t-Bu) (126g, 1317mmol), Toluene (1.5L)을 넣는다. 그런 후에 70℃ 상태에서 4시간 동안 가열 환류시킨다. 반응이 완료되면 상온에서 증류수를 넣어 희석시키고 Methylene chloride와 물로 추출한다. 유기층을 MgSO4로 건조하여 농축한 후 생성된 화합물을 Methylene chloride와 Hexane으로 재결정하여 생성물 Sub 1-I-1 (135g, 79%)을 얻었다.2-Chloroaniline (67.2g, 525mmol), 1,4-Dibromodibenzothiophene (150g, 438mmol), Pd 2 (dba) 3 in a round bottom flask (16.2g, 17.4mmol), P (t-Bu) 3 (15g, 43.8mmol), NaO (t-Bu) (126g, 1317mmol), and Toluene (1.5L) are added. Then, the mixture was heated to reflux for 4 hours at 70 ° C. When the reaction is complete, dilute it with distilled water at room temperature and extract with Methylene chloride and water. The organic layer was dried over MgSO 4 and concentrated, and the resulting compound was recrystallized from Methylene chloride and Hexane to obtain the product Sub 1-I-1 (135 g, 79%).
Sub 1-II-1의 합성법Synthesis of Sub 1-II-1
둥근바닥플라스크에 Sub 1-I-1 (135g, 348mmol), PPh3
(228g, 867mmol), o-Dichlorobenzene (900mL)을 넣는다. 그런 후에 180℃ 상태에서 24시간 동안 가열 환류시킨다. 반응이 종결되면 상온으로 식힌 후, 농축한다. 농축되어 생성된 화합물을 silica column 및 재결정하여 생성물 Sub 1-II-1 (91.8g, 75%)를 얻었다.Round bottom flask Sub 1-I-1 (135g, 348mmol), PPh 3 (228g, 867mmol), o -Dichlorobenzene (900mL) is added. Then, the mixture was heated to reflux for 24 hours at 180 ° C. After the reaction is completed, it is cooled to room temperature and concentrated. The resulting compound was concentrated to silica column and recrystallized to obtain the product Sub 1-II-1 (91.8g, 75%).
Sub 1-1의 합성법Synthesis of Sub 1-1
둥근바닥플라스크에 Sub 1-II-1 (30.6g 87mmol), 1-Bromonaphthalene (21.5g, 104mmol), Pd2(dba)3
(3.2g, 3.5mmol), P(t-Bu)3 (1.8g, 8.7mmol), NaO(t-Bu) (25g, 261mmol), Toluene (300mL)을 넣는다. 그런 후에 110℃ 상태에서 8시간 동안 가열 환류시킨다. 반응이 완료되면 상온에서 증류수를 넣어 희석시키고 Methylene chloride와 물로 추출한다. 유기층을 MgSO4로 건조하여 농축한 후 생성된 화합물을 Methylene chloride와 Hexane으로 재결정하여 생성물 Sub 1-1 (31.6g, 74%)를 얻었다.Round bottom flask Sub 1-II-1 (30.6g 87mmol), 1-Bromonaphthalene (21.5g, 104mmol), Pd 2 (dba) 3 (3.2g, 3.5mmol), P (t-Bu) 3 (1.8g, 8.7mmol), NaO (t-Bu) (25g, 261mmol), Toluene (300mL) is added. Then, the mixture was heated to reflux for 8 hours at 110 ° C. When the reaction is complete, dilute it with distilled water at room temperature and extract with Methylene chloride and water. The organic layer was dried over MgSO 4 and concentrated, and the resulting compound was recrystallized from Methylene chloride and Hexane to obtain the product Sub 1-1 (31.6 g, 74%).
2. Sub 1-2의 합성예 (a=1, b= 0, X= S 일 때)2. Synthesis Example of Sub 1-2 (when a = 1, b = 0, X = S)
Sub 1-2의 합성법Synthesis of Sub 1-2
둥근바닥플라스크에 Sub 1-II-1 (30g, 84mmol), Iodobenzene (20.7g, 102mmol), Pd2(dba)3
(3g, 3.3mmol), P(t-Bu)3 (1.8g, 8.4mmol), NaO(t-Bu) (24.6g, 255mmol), Toluene (240mL)을 상기 Sub 1-1의 합성방법을 사용하여 생성물 Sub 1-2 (28g, 76%)를 얻었다.Round bottom flask Sub 1-II-1 (30g, 84mmol), Iodobenzene (20.7g, 102mmol), Pd 2 (dba) 3 (3g, 3.3mmol), P (t-Bu) 3 (1.8g, 8.4mmol), NaO (t-Bu) (24.6g, 255mmol), Toluene (240mL) using the synthesis method of Sub 1-1 To give the product Sub 1-2 (28g, 76%).
Sub 1-3의 합성예 (a=1, b= 0, X= S 일 때)Synthesis Example of Sub 1-3 (when a = 1, b = 0, X = S)
Sub 1-3의 합성법Synthesis of Sub 1-3
둥근바닥플라스크에 Sub 1-II-1 (30.6g 87mmol), 4-Iodo-1,1'-biphenyl (29.2g, 104mmol), Pd2(dba)3
(3.2g, 3.5mmol), P(t-Bu)3 (1.8g, 8.7mmol), NaO(t-Bu) (25g, 261mmol), Toluene (300mL)을 상기 Sub 1-1의 합성방법을 사용하여 생성물 Sub 1-3 (32g, 74%)을 얻었다.Round bottom flask Sub 1-II-1 (30.6g 87mmol), 4-Iodo-1,1'-biphenyl (29.2g, 104mmol), Pd 2 (dba) 3 (3.2g, 3.5mmol), P (t-Bu) 3 (1.8g, 8.7mmol), NaO (t-Bu) (25g, 261mmol), Toluene (300mL) using the synthesis method of Sub 1-1 To give the product Sub 1-3 (32g, 74%).
Sub 1-5의 합성예 (a=1, b= 0, X= S 일 때)Synthesis Example of Sub 1-5 (when a = 1, b = 0, X = S)
Sub 1-5의 합성법Synthesis of Sub 1-5
둥근바닥플라스크에 Sub 1-II-1 (30.6g 87mmol), 2-Bromonaphthalene (21.5g, 104mmol), Pd2(dba)3
(3.2g, 3.5mmol), P(t-Bu)3 (1.8g, 8.7mmol), NaO(t-Bu) (25g, 261mmol), Toluene (300mL)을 상기 Sub 1-1의 합성방법을 사용하여 생성물 Sub 1-5 (29.1g, 70%)를 얻었다.Round bottom flask Sub 1-II-1 (30.6g 87mmol), 2-Bromonaphthalene (21.5g, 104mmol), Pd 2 (dba) 3 (3.2g, 3.5mmol), P (t-Bu) 3 (1.8g, 8.7mmol), NaO (t-Bu) (25g, 261mmol), Toluene (300mL) using the synthesis method of Sub 1-1 To give the product Sub 1-5 (29.1g, 70%).
Sub 1-6 합성예 (a=1, b= 0, X= S 일 때)Synthesis Example of Sub 1-6 (when a = 1, b = 0, X = S)
Sub 1-I-6의 합성법 (a=1, b= 0, X= S 일 때)Synthesis of Sub 1-I-6 (when a = 1, b = 0, X = S)
둥근바닥플라스크에 2-Chloroaniline (22.4g, 175mmol), 2,4-Dibromodibenzothiophene (50g, 146mmol), Pd2(dba)3
(5.4g, 5.8mmol), P(t-Bu)3 (5g, 14.6mmol), NaO(t-Bu) (42g, 439mmol), Toluene (500mL)을 상기 Sub 1-I-1의 합성방법을 사용하여 생성물 Sub 1-I-6 (46g, 90%)을 얻었다.2-Chloroaniline (22.4g, 175mmol), 2,4-Dibromodibenzothiophene (50g, 146mmol), Pd 2 (dba) 3 in a round bottom flask (5.4g, 5.8mmol), P (t-Bu) 3 (5g, 14.6mmol), NaO (t-Bu) (42g, 439mmol), Toluene (500mL) to the synthesis method of Sub 1-I-1 The product Sub 1-I-6 (46 g, 90%) was obtained.
Sub 1-II-6의 합성법Synthesis of Sub 1-II-6
둥근바닥플라스크에 Sub 1-I-6 (45g, 116mmol), PPh3
(76g, 289mmol), o-Dichlorobenzene (300mL)을 상기 Sub 1-II-1의 합성방법을 사용하여 생성물 Sub 1-II-6 (32.6g, 80%)을 얻었다.Round bottom flask Sub 1-I-6 (45g, 116mmol), PPh 3 (76 g, 289 mmol), o -Dichlorobenzene (300 mL) was obtained using the synthesis method of Sub 1-II-1 to obtain the product Sub 1-II-6 (32.6 g, 80%).
Sub 1-6의 합성법Synthesis of Sub 1-6
둥근바닥플라스크에 Sub 1-II-6 (10g, 28mmol), Iodobenzene (6.9g, 34mmol), Pd2(dba)3
(1g, 1.1mmol), P(t-Bu)3 (0.6g, 2.8mmol), NaO(t-Bu) (8.2g, 85mmol), Toluene (80mL)을 상기 Sub 1-1의 합성방법을 사용하여 생성물 Sub 1-6 (10g, 84%)를 얻었다.Round bottom flask Sub 1-II-6 (10g, 28mmol), Iodobenzene (6.9g, 34mmol), Pd 2 (dba) 3 (1g, 1.1mmol), P (t-Bu) 3 (0.6g, 2.8mmol), NaO (t-Bu) (8.2g, 85mmol), Toluene (80mL) using the synthesis method of Sub 1-1 To give the product Sub 1-6 (10g, 84%).
Sub 1-7 합성예 (a=1, b= 0, X= S 일 때)Synthesis example of Sub 1-7 (when a = 1, b = 0, X = S)
Sub 1-7의 합성법 Synthesis of Sub 1-7
둥근바닥플라스크에 Sub 1-II-6 (10g, 28mmol), 4-Iodo-1,1'-biphenyl (9.5g, 34mmol), Pd2(dba)3
(1g, 1.1mmol), P(t-Bu)3 (0.6g, 2.8mmol), NaO(t-Bu) (8.2g, 85mmol), Toluene (80mL)을 상기 Sub 1-1의 합성방법을 사용하여 생성물 Sub 1-7 (10g, 71%)를 얻었다.Round bottom flask Sub 1-II-6 (10g, 28mmol), 4-Iodo-1,1'-biphenyl (9.5g, 34mmol), Pd 2 (dba) 3 (1g, 1.1mmol), P (t-Bu) 3 (0.6g, 2.8mmol), NaO (t-Bu) (8.2g, 85mmol), Toluene (80mL) using the synthesis method of Sub 1-1 To obtain the product Sub 1-7 (10g, 71%).
Sub 1-14 합성예 (a=1, b= 0, X= S 일 때)Synthesis example of Sub 1-14 (when a = 1, b = 0, X = S)
Sub 1-I-14의 합성법Synthesis of Sub 1-I-14
둥근바닥플라스크에 2-Chloronaphthalen-1-amine (31g, 175mmol), 2,4-Dibromodibenzothiophene (50g, 146mmol), Pd2(dba)3
(5.4g, 5.8mmol), P(t-Bu)3 (5g, 14.6mmol), NaO(t-Bu) (42g, 439mmol), Toluene (500mL)을 상기 Sub 1-I-1의 합성방법을 사용하여 생성물 Sub 1-I-14 (48g, 75%)을 얻었다.2-Chloronaphthalen-1-amine (31g, 175mmol), 2,4-Dibromodibenzothiophene (50g, 146mmol), Pd 2 (dba) 3 in a round bottom flask (5.4g, 5.8mmol), P (t-Bu) 3 (5g, 14.6mmol), NaO (t-Bu) (42g, 439mmol), Toluene (500mL) to the synthesis method of Sub 1-I-1 Product Sub 1-I-14 (48 g, 75%) was obtained.
Sub 1-II-14의 합성법Synthesis of Sub 1-II-14
둥근바닥플라스크에 Sub 1-I-14 (30g, 68mmol), PPh3
(45g, 171mmol), o-Dichlorobenzene (150mL)을 넣는다. 그런 후에 180℃ 상태에서 24시간 동안 가열 환류시킨다. 반응이 종결되면 상온으로 식힌 후, 농축한다. 농축되어 생성된 화합물을 silica column 및 재결정하여 생성물 Sub 1-II-14 (25g, 93%)을 얻었다.Round bottom flask Sub 1-I-14 (30g, 68mmol), PPh 3 (45g, 171mmol), o -Dichlorobenzene (150mL) is added. Then, the mixture was heated to reflux for 24 hours at 180 ° C. After the reaction is completed, it is cooled to room temperature and concentrated. The resulting compound was concentrated to silica column and recrystallized to obtain the product Sub 1-II-14 (25g, 93%).
Sub 1-14의 합성Synthesis of Sub 1-14
둥근바닥플라스크에 Sub 1-II-14 (25g, 62mmol), Iodobenzene (15g 75mmo), Pd2(dba)3 (2.g, 2.5mmol), P(t-Bu)3 (1.3g (6.2mmol), NaO(t-Bu) (18g, 186mmol), Toluene (300mL)을 넣는다. 그런 후에 110℃ 상태에서 8시간 동안 가열 환류시킨다. 반응이 완료되면 상온에서 증류수를 넣어 희석시키고 Methylene chloride와 물로 추출한다. 유기층을 MgSO4로 건조하여 농축한 후 생성된 화합물을 Methylene chloride와 Hexane으로 재결정하여 생성물 Sub 1-14 (20g, 67%)를 얻었다.Round bottom flask Sub 1-II-14 (25g, 62mmol), Iodobenzene (15g 75mmo), Pd 2 (dba) 3 (2.g, 2.5mmol), P (t-Bu) 3 (1.3g (6.2mmol) ), NaO (t-Bu) (18g, 186mmol), Toluene (300mL) is added, and then heated to reflux for 8 hours at 110 ° C. When the reaction is complete, dilute with distilled water at room temperature and dilute with Methylene chloride and water. The organic layer was dried over MgSO 4 and concentrated, and the resulting compound was recrystallized from Methylene chloride and Hexane to obtain the product Sub 1-14 (20 g, 67%).
Sub 1-29 합성예 (a=1, b= 0, X= C 일 때)Synthesis example of Sub 1-29 (when a = 1, b = 0, X = C)
Sub 1-I-29의 합성법Synthesis of Sub 1-I-29
둥근바닥플라스크에 2-Chloronaphthalen-1-amine (31g, 175mmol), 1,4-dibromo-9,9-dimethyl-9H-fluorene (51g, 146mmol), Pd2(dba)3
(5.4g, 5.8mmol), P(t-Bu)3 (5g, 14.6mmol), NaO(t-Bu) (42g, 439mmol), Toluene (500mL)을 상기 Sub 1-I-1의 합성방법을 사용하여 생성물 Sub 1-I-29 (36g, 63%)을 얻었다.2-Chloronaphthalen-1-amine (31g, 175mmol), 1,4-dibromo-9,9-dimethyl-9H-fluorene (51g, 146mmol), Pd 2 (dba) 3 in a round bottom flask (5.4g, 5.8mmol), P (t-Bu) 3 (5g, 14.6mmol), NaO (t-Bu) (42g, 439mmol), Toluene (500mL) was synthesized in the synthesis method of Sub 1-I-1. Product Sub 1-I-29 (36 g, 63%) was obtained.
Sub 1-II-29의 합성법Synthesis of Sub 1-II-29
둥근바닥플라스크에 Sub 1-I-29 (27g, 68mmol), PPh3
(45g, 171mmol), o-Dichlorobenzene (150mL)을 상기 Sub 1-II-1의 합성방법을 사용하여 생성물 Sub 1-II-29 (22g, 92%)을 얻었다.Round bottom flask Sub 1-I-29 (27g, 68mmol), PPh 3 (45 g, 171 mmol), o -Dichlorobenzene (150 mL) was obtained using the synthesis method of Sub 1-II-1 to obtain the product Sub 1-II-29 (22 g, 92%).
Sub 1-29의 합성Synthesis of Sub 1-29
둥근바닥플라스크에 Sub 1-II-29 (22g, 62mmol), 2-Bromonaphthalene (15g 74mmo), Pd2(dba)3
(2.g, 2.5mmol), P(t-Bu)3 (1.3g (6.2mmol), NaO(t-Bu) (18g, 186mmol), Toluene (300mL)을 상기 Sub 1-1의 합성방법을 사용하여 생성물 Sub 1-29 (20g, 67%)를 얻었다.Round bottom flask Sub 1-II-29 (22g, 62mmol), 2-Bromonaphthalene (15g 74mmo), Pd 2 (dba) 3 (2.g, 2.5mmol), P (t-Bu) 3 (1.3g (6.2mmol), NaO (t-Bu) (18g, 186mmol), Toluene (300mL), the synthesis method of Sub 1-1 Product Sub 1-29 (20 g, 67%) was obtained.
Sub 1-25 합성예 (a= 1, b= 0, X= O 일 때)Synthesis example of Sub 1-25 (when a = 1, b = 0, X = O)
Sub 1-I-25의 합성법Synthesis of Sub 1-I-25
둥근바닥플라스크에 2-Chloronaphthalen-1-amine (23.45 g, 183.85 mmol), 1,4-dibromodibenzo[b,d]furan (50 g, 153.4 mmol), Pd2(dba)3
(5.58 g, 6.1 mmol), P(t-Bu)3 (3.1 g, 15.34 mmol), NaO(t-Bu) (44.32 g, 461.2 mmol), Toluene (340 mL)을 상기 Sub 1-I-1의 합성방법을 이용하여 생성물 Sub 1-I-25 (41.7 g, 73%)을 얻었다.2-Chloronaphthalen-1-amine (23.45 g, 183.85 mmol), 1,4-dibromodibenzo [b, d] furan (50 g, 153.4 mmol), Pd 2 (dba) 3 in a round bottom flask (5.58 g, 6.1 mmol), P (t-Bu) 3 (3.1 g, 15.34 mmol), NaO (t-Bu) (44.32 g, 461.2 mmol), Toluene (340 mL) above Sub 1-I-1 Synthesis of to obtain the product Sub 1-I-25 (41.7 g, 73%).
Sub 1-II-25의 합성법Synthesis of Sub 1-II-25
둥근바닥플라스크에 Sub 1-I-25 (47 g, 126.1 mmol), PPh3
(82.7 g, 315.3 mmol), o-Dichlorobenzene (505 mL)을 상기 Sub 1-II-1의 합성방법을 이용하여 생성물 Sub 1-II-25 (35.62 g, 84 %)을 얻었다.Round bottom flask with Sub 1-I-25 (47 g, 126.1 mmol), PPh 3 (82.7 g, 315.3 mmol), o -Dichlorobenzene (505 mL) was obtained using the synthesis method of Sub 1-II-1 to obtain the product Sub 1-II-25 (35.62 g, 84%).
Sub 1-25의 합성Synthesis of Sub 1-25
둥근바닥플라스크에 Sub 1-II-25 (47 g, 126.13 mmol), Bromobenzene (19.59 g 124.79 mmol), Pd2(dba)3
(3.79 g, 4.14 mmol), P(t-Bu)3 (2.11 g, 10.4 mmol), NaO(t-Bu) (30.08 g, 313.045 mmol), Toluene (230 mL)을 상기 Sub 1-1의 합성방법을 사용하여 생성물 Sub 1-25 (34.77 g, 82 %)를 얻었다.Round bottom flask Sub 1-II-25 (47 g, 126.13 mmol), Bromobenzene (19.59 g 124.79 mmol), Pd 2 (dba) 3 Synthesis of Sub 1-1 (3.79 g, 4.14 mmol), P (t-Bu) 3 (2.11 g, 10.4 mmol), NaO (t-Bu) (30.08 g, 313.045 mmol), Toluene (230 mL) Using the method the product Sub 1-25 (34.77 g, 82%) was obtained.
Sub 1의 예시Sub 1 example
한편, Sub 1에 속하는 화합물은 아래와 같은 화합물일 수 있으나, 이에 한정되는 것은 아니며, 표 1은 Sub 1에 속하는 화합물의 FD-MS 값을 나타낸 것이다.Meanwhile, the compound belonging to Sub 1 may be the following compound, but is not limited thereto, and Table 1 shows the FD-MS value of the compound belonging to Sub 1.
| 화합물compound | FD-MSFD-MS | 화합물compound | FD-MSFD-MS |
| Sub 1-1Sub 1-1 | m/z=477.02(C28H16BrNS=478.40)m / z = 477.02 (C 28 H 16 BrNS = 478.40) | Sub 1-2Sub 1-2 | m/z=427.00(C24HBrNS=428.34)m / z = 427.00 (C24HBrNS = 428.34) |
| Sub 1-3Sub 1-3 | m/z=503.03(C30H18BrNS=504.44)m / z = 503.03 (C 30 H 18 BrNS = 504.44) | Sub 1-4Sub 1-4 | m/z=503.03(C30H18BrNS=504.44)m / z = 503.03 (C 30 H 18 BrNS = 504.44) |
| Sub 1-5Sub 1-5 | m/z=477.02(C28H16BrNS=478.40)m / z = 477.02 (C 28 H 16 BrNS = 478.40) | Sub 1-6Sub 1-6 | m/z=427.00(C24HBrNS=428.34)m / z = 427.00 (C24HBrNS = 428.34) |
| Sub 1-7Sub 1-7 | m/z=503.03(C30H18BrNS=504.44)m / z = 503.03 (C 30 H 18 BrNS = 504.44) | Sub 1-8Sub 1-8 | m/z=503.03(C30H18BrNS=504.44)m / z = 503.03 (C 30 H 18 BrNS = 504.44) |
| Sub 1-9Sub 1-9 | m/z=477.02(C28H16BrNS=478.40))m / z = 477.02 (C 28 H 16 BrNS = 478.40) | Sub 1-10Sub 1-10 | m/z=477.02(C28H16BrNS=478.40)m / z = 477.02 (C 28 H 16 BrNS = 478.40) |
| Sub 1-11Sub 1-11 | m/z=605.06(C36H20BrN3S =606.53)m / z = 605.06 (C 36 H 20 BrN 3 S = 606.53) | Sub 1-12Sub 1-12 | m/z=555.04(C32H18BrN3S=556.47)m / z = 555.04 (C 32 H 18 BrN 3 S = 556.47) |
| Sub 1-13Sub 1-13 | m/z=603.07(C38H22BrNS=604.56)m / z = 603.07 (C 38 H 22 BrNS = 604.56) | Sub 1-14Sub 1-14 | m/z=477.02(C28H16BrNS=478.40)m / z = 477.02 (C 28 H 16 BrNS = 478.40) |
| Sub 1-15Sub 1-15 | m/z=527.03(C32H18BrNS=528.46)m / z = 527.03 (C 32 H 18 BrNS = 528.46) | Sub 1-16Sub 1-16 | m/z=629.08(C40H24BrNS=630.59)m / z = 629.08 (C 40 H 24 BrNS = 630.59) |
| Sub 1-17Sub 1-17 | m/z=554.05C33H19BrN2S=555.49)m / z = 554.05C 33 H 19 BrN 2 S = 555.49) | Sub 1-18Sub 1-18 | m/z=734.11(C45H27BrN4S=735.69)m / z = 734.11 (C 45 H 27 BrN 4 S = 735.69) |
| Sub 1-19Sub 1-19 | m/z=721.08(C44H24BrN3OS=722.65)m / z = 721.08 (C 44 H 24 BrN 3 OS = 722.65) | Sub 1-20Sub 1-20 | m/z=629.08(C40H24BrNS=630.59)m / z = 629.08 (C 40 H 24 BrNS = 630.59) |
| Sub 1-21Sub 1-21 | m/z=529.02(C30H16BrN3S=530.44)m / z = 529.02 (C 30 H 16 BrN 3 S = 530.44) | Sub 1-22Sub 1-22 | m/z=555.04(C32H18BrN3S=556.47)m / z = 555.04 (C 32 H 18 BrN 3 S = 556.47) |
| Sub 1-23Sub 1-23 | m/z=581.06(C34H20BrN3S=582.51)m / z = 581.06 (C 34 H 20 BrN 3 S = 582.51) | Sub 1-24Sub 1-24 | m/z=600.06(C33H21BrN4OS=601.52)m / z = 600.06 (C 33 H 21 BrN 4 OS = 601.52) |
| Sub 1-25Sub 1-25 | m/z=411.03(C24H14BrNO=412.28)m / z = 411.03 (C 24 H 14 BrNO = 412.28) | Sub 1-26Sub 1-26 | m/z=671.07(C40H22BrN3OS=672.59)m / z = 671.07 (C 40 H 22 BrN 3 OS = 672.59) |
| Sub 1-27Sub 1-27 | m/z=593.04(C36H20BrNOS=594.52)m / z = 593.04 (C 36 H 20 BrNOS = 594.52) | Sub 1-28Sub 1-28 | m/z=437.08(C27H20BrN=438.36)m / z = 437.08 (C 27 H 20 BrN = 438.36) |
| Sub 1-29Sub 1-29 | m/z=487.09(C31H22BrN=488.42)m / z = 487.09 (C 31 H 22 BrN = 488.42) | Sub 1-30Sub 1-30 | m/z=453.05(C26H20BrNSi=454.43)m / z = 453.05 (C 26 H 20 BrNSi = 454.43) |
| Sub 1-31Sub 1-31 | m/z=474.95(C24H14BrNSe=475.24)m / z = 474.95 (C 24 H 14 BrNSe = 475.24) |
2. Sub 2의 합성 예시2. Synthesis Example of Sub 2
반응식 1의 sub 2는 하기 반응식 3의 반응경로에 의해 합성될 수 있으며 이에 한정된 것은 아니다. Sub 2 of Scheme 1 may be synthesized by the following Reaction Scheme 3, but is not limited thereto.
<반응식 3> (X'= I, Br, Cl)<Scheme 3> (X '= I, Br, Cl)
상기 반응식 3의 Sub 2에 속하는 화합물의 합성예는 다음과 같다.Synthesis examples of compounds belonging to Sub 2 of Scheme 3 are as follows.
Sub 2-1 합성예 (a= 0, b=1, Y= S인 경우)Synthesis example of Sub 2-1 (when a = 0, b = 1, Y = S)
Sub 2-I-1의 합성법Synthesis of Sub 2-I-1
둥근바닥플라스크에 2-Bromodibenzothiophene (100g, 380mmol), 2-Nitrophenyl boronic acid (76g, 456mmol), Pd(PPh3)4
(18g, 15mmol), NaOH (46g, 1140mmol), THF (1.2L)/H2O (0.6L)을 넣는다. 그런 후에 70℃ 상태에서 4시간 동안 가열 환류시킨다. 반응이 완료되면 상온에서 증류수를 넣어 희석시키고 Methylene chloride와 물로 추출한다. 유기층을 MgSO4로 건조하여 농축한 후 생성된 화합물을 Methylene chloride와 Hexane으로 재결정하여 생성물 Sub 2-I-1 (99g, 85%)을 얻었다.2-Bromodibenzothiophene (100g, 380mmol), 2-Nitrophenyl boronic acid (76g, 456mmol), Pd (PPh 3 ) 4 in a round bottom flask 4 (18 g, 15 mmol), NaOH (46 g, 1140 mmol), and THF (1.2 L) / H 2 O (0.6 L) are added. Then, the mixture was heated to reflux for 4 hours at 70 ° C. When the reaction is complete, dilute it with distilled water at room temperature and extract with Methylene chloride and water. The organic layer was dried over MgSO 4 and concentrated, and the resulting compound was recrystallized from Methylene chloride and Hexane to obtain the product Sub 2-I-1 (99 g, 85%).
Sub 2-II-1의 합성법Synthesis of Sub 2-II-1
둥근바닥플라스크에 Sub 2-I-1 (99g, 323mmol), PPh3
(218g, 808mmol), o-Dichlorobenzene (1.0L)을 넣는다. 그런 후에 180℃ 상태에서 24시간 동안 가열 환류시킨다. 반응이 종결되면 상온으로 식힌 후, 농축한다. 농축되어 생성된 화합물을 silica column 및 재결정하여 생성물 Sub 2-II-1 (70g, 80%)을 얻었다. Round bottom flask Sub 2-I-1 (99g, 323mmol), PPh 3 (218 g, 808 mmol) and o -Dichlorobenzene (1.0 L) are added. Then, the mixture was heated to reflux for 24 hours at 180 ° C. After the reaction is completed, it is cooled to room temperature and concentrated. The resulting compound was concentrated to silica column and recrystallized to obtain the product Sub 2-II-1 (70 g, 80%).
Sub 2-III-1의 합성법Synthesis of Sub 2-III-1
둥근바닥플라스크에 Sub 2-II-1 (70g, 293mmol), N-Bromosuccinimide (52g, 293mmol), Methylene chloride (1L)를 넣는다. 그런 후에 상온에서 4시간 동안 교반한다. 반응이 완료되면 증류수를 넣은 후, Methylene chloride와 물로 추출한다. 유기층을 MgSO4로 건조하여 농축한 후 생성된 화합물을 Methylene chloride와 Hexane으로 재결정하여 생성물 Sub 2-III-1 (86g, 83%)을 얻었다.To the round bottom flask, add Sub 2-II-1 (70g, 293mmol), N-Bromosuccinimide (52g, 293mmol), and Methylene chloride (1L). Then, the mixture was stirred at room temperature for 4 hours. After the reaction is completed, distilled water is added and then extracted with Methylene chloride and water. The organic layer was dried with MgSO 4 and concentrated, and the resulting compound was recrystallized from Methylene chloride and Hexane to obtain the product Sub 2-III-1 (86 g, 83%).
Sub 2-1의 합성법Synthesis of Sub 2-1
둥근바닥플라스크에 Sub 2-III-1 (30g, 84mmol), Iodobenzene (20.7g, 102mmol), Pd2(dba)3
(3g, 3.3mmol), P(t-Bu)3 (1.8g, 8.4mmol), NaO(t-Bu) (24.6g, 255mmol), Toluene (240mL)을 넣는다. 그런 후에 110℃ 상태에서 8시간 동안 가열 환류시킨다. 반응이 완료되면 상온에서 증류수를 넣어 희석시키고 Methylene chloride와 물로 추출한다. 유기층을 MgSO4로 건조하여 농축한 후 생성된 화합물을 Methylene chloride와 Hexane으로 재결정하여 생성물 Sub 2-1 (28g, 76%)를 얻었다.Round bottom flask Sub 2-III-1 (30g, 84mmol), Iodobenzene (20.7g, 102mmol), Pd 2 (dba) 3 (3g, 3.3mmol), P (t-Bu) 3 (1.8g, 8.4mmol), NaO (t-Bu) (24.6g, 255mmol), Toluene (240mL) was added. Then, the mixture was heated to reflux for 8 hours at 110 ° C. When the reaction is complete, dilute it with distilled water at room temperature and extract with Methylene chloride and water. The organic layer was dried over MgSO 4 and concentrated, and the resulting compound was recrystallized from Methylene chloride and Hexane to obtain the product Sub 2-1 (28 g, 76%).
Sub 2-2 합성예 (a= 0, b=1, Y= S인 경우)Synthesis Example of Sub 2-2 (a = 0, b = 1, Y = S)
Sub 2-2의 합성법Synthesis of Sub 2-2
둥근바닥플라스크에 Sub 2-III-1 (30g, 84mmol), 4-Iodo-1,1'-biphenyl (28.6g, 102mmol), Pd2(dba)3
(3g, 3.3mmol), P(t-Bu)3 (1.8g, 8.4mmol), NaO(t-Bu) (24.6g, 255mmol), Toluene (240mL)을 상기 Sub 2-1의 합성방법을 사용하여 생성물 Sub 2-2 (32g, 76%)를 얻었다.Round bottom flask Sub 2-III-1 (30g, 84mmol), 4-Iodo-1,1'-biphenyl (28.6g, 102mmol), Pd 2 (dba) 3 (3g, 3.3mmol), P (t-Bu) 3 (1.8g, 8.4mmol), NaO (t-Bu) (24.6g, 255mmol), Toluene (240mL) using the synthesis method of Sub 2-1 To give the product Sub 2-2 (32g, 76%).
Sub 2-3 합성예 (a= 0, b=1, Y= S인 경우)Synthesis of Sub 2-3 (when a = 0, b = 1, Y = S)
Sub 2-3의 합성법Synthesis of Sub 2-3
둥근바닥플라스크에 Sub 2-III-1 (30g, 84mmol), 3-Bromo-1,1'-biphenyl (23.8g, 102mmol), Pd2(dba)3
(3g, 3.3mmol), P(t-Bu)3 (1.8g, 8.4mmol), NaO(t-Bu) (24.6g, 255mmol), Toluene (240mL)을 상기 Sub 2-1의 합성방법을 사용하여 생성물 Sub 2-3 (34g, 80%)를 얻었다.Round bottom flask Sub 2-III-1 (30g, 84mmol), 3-Bromo-1,1'-biphenyl (23.8g, 102mmol), Pd 2 (dba) 3 (3g, 3.3mmol), P (t-Bu) 3 (1.8g, 8.4mmol), NaO (t-Bu) (24.6g, 255mmol), Toluene (240mL) using the synthesis method of Sub 2-1 To give the product Sub 2-3 (34g, 80%).
Sub 2-37 합성예 (a= 0, b=1, Y= O인 경우)Synthesis Example of Sub 2-37 (a = 0, b = 1, Y = O)
Sub 2-I-37의 합성법Synthesis of Sub 2-I-37
둥근바닥플라스크에 2-Bromodibenzofuran (50g, 202mmol), 2-Nitrophenyl boronic acid (40.5g, 242mmol), Pd(PPh3)4
(9.3g, 8mmol), NaOH (24g, 606mmol), THF (600mL)/H2O (300mL)을 상기 Sub 2-I-1의 합성방법을 사용하여 생성물 Sub 2-I-37 (43g, 74%)을 얻었다.2-Bromodibenzofuran (50g, 202mmol), 2-Nitrophenyl boronic acid (40.5g, 242mmol), Pd (PPh 3 ) 4 in a round bottom flask 4 (9.3 g, 8 mmol), NaOH (24 g, 606 mmol), THF (600 mL) / H 2 O (300 mL) using the synthesis method of Sub 2-I-1, the product Sub 2-I-37 (43 g, 74 %).
Sub 2-II-37의 합성법Synthesis of Sub 2-II-37
둥근바닥플라스크에 Sub 2-I-37 (43g, 110mmol), PPh3
(72g, 276mmol), o-Dichlorobenzene (350mL)을 상기 Sub 2-II-1의 합성방법을 사용하여 생성물 Sub 2-II-37 (23g, 82%)을 얻었다. Round bottom flask Sub 2-I-37 (43g, 110mmol), PPh 3 (72g, 276mmol), o -Dichlorobenzene (350mL) was obtained using the synthesis method of Sub 2-II-1, product Sub 2-II-37 (23g, 82%).
Sub 2-III-37의 합성법Synthesis of Sub 2-III-37
둥근바닥플라스크에 Sub 2-II-37 (23g, 89mmol), N-Bromosuccinimide (16g, 89mmol), Methylene chloride (300mL)를 상기 Sub 2-III-1의 합성방법을 사용하여 생성물 Sub 2-III-37 (21g, 70%)을 얻었다.To the round bottom flask, Sub 2-II-37 (23g, 89mmol), N-Bromosuccinimide (16g, 89mmol), and Methylene chloride (300mL) were synthesized using the synthesis method of Sub 2-III-1. 37 (21 g, 70%).
Sub 2-37의 합성법Synthesis of Sub 2-37
둥근바닥플라스크에 Sub 2-III-37 (21g, 62mmol), Iodobenzene (15.3g, 75mmol), Pd2(dba)3
(2.3g, 2.5mmol), P(t-Bu)3 (1.3g, 6.2mmol), NaO(t-Bu) (18g, 187mmol), Toluene (200mL)을 상기 Sub 2-1의 합성방법을 사용하여 생성물 Sub 2-37 (16g, 63%)를 얻었다.Round bottom flask Sub 2-III-37 (21g, 62mmol), Iodobenzene (15.3g, 75mmol), Pd 2 (dba) 3 (2.3g, 2.5mmol), P (t-Bu) 3 (1.3g, 6.2mmol), NaO (t-Bu) (18g, 187mmol), Toluene (200mL) using the synthesis method of Sub 2-1 To give the product Sub 2-37 (16g, 63%).
Sub 2-144의 합성예 (a= 0, b=1, Y= C인 경우)Synthesis Example of Sub 2-144 (a = 0, b = 1, Y = C)
Sub 2-I-144의 합성법Synthesis of Sub 2-I-144
둥근바닥플라스크에 3-bromo-9,9-dimethyl-9H-fluorene (50g, 183.04 mmol), 2-Nitrophenyl boronic acid (36.6 g, 219.28 mmol), Pd(PPh3)4
(8.4 g, 7.25 mmol), NaOH (22 g, 549.11 mmol), THF (805 mL)/H2O (402 mL)을 상기 Sub 2-I-1 합성방법을 사용하여 생성물 Sub 2-I-144 (47.72 g, 69 %)을 얻었다.3-bromo-9,9-dimethyl-9H-fluorene (50g, 183.04 mmol), 2-Nitrophenyl boronic acid (36.6 g, 219.28 mmol), Pd (PPh 3 ) 4 in a round bottom flask 4 (8.4 g, 7.25 mmol), NaOH (22 g, 549.11 mmol), THF (805 mL) / H 2 O (402 mL) using the above Sub 2-I-1 synthesis method, product Sub 2-I-144 (47.72 g, 69%).
Sub 2-II-144의 합성법Synthesis of Sub 2-II-144
둥근바닥플라스크에 Sub 2-I-144 (47 g, 149 mmol), PPh3
(97.7 g, 372.48 mmol), o-Dichlorobenzene (596 mL)을 상기 Sub 2-II-1의 합성방법을 사용하여 생성물 Sub 2-II-144 (30.41 g, 72 %)을 얻었다. Round bottom flask with Sub 2-I-144 (47 g, 149 mmol), PPh 3 (97.7 g, 372.48 mmol), o -Dichlorobenzene (596 mL) was obtained using the synthesis method of Sub 2-II-1 to obtain the product Sub 2-II-144 (30.41 g, 72%).
Sub 2-III-144의 합성법Synthesis of Sub 2-III-144
둥근바닥플라스크에 Sub 2-II-144 (30g, 89mmol), N-Bromosuccinimide (18.8 g, 105.9 mmol), Methylene chloride (318 mL)를 상기 Sub 2-III-1의 합성방법을 이용하여 생성물 Sub 2-III-144 (18.24 g, 53 %)을 얻었다.To the round bottom flask, Sub 2-II-144 (30g, 89mmol), N-Bromosuccinimide (18.8 g, 105.9 mmol), Methylene chloride (318 mL) was synthesized using the synthesis method of Sub 2-III-1. -III-144 (18.24 g, 53%).
Sub 2-144의 합성법Synthesis of Sub 2-144
둥근바닥플라스크에 Sub 2-III-144 (18 g, 49.7 mmol), Iodobenzene (12.26 g, 60.1 mmol), Pd2(dba)3
(1.83 g, 2 mmol), P(t-Bu)3 (1.01 g, 4.97 mmol), NaO(t-Bu) (14.4 g, 149.9 mmol), Toluene (109 mL)을 상기 Sub 2-1의 합성방법을 사용하여 생성물 Sub 2-144 (15.03 g, 69%)를 얻었다.Round bottom flask Sub 2-III-144 (18 g, 49.7 mmol), Iodobenzene (12.26 g, 60.1 mmol), Pd 2 (dba) 3 Synthesis of Sub 2-1 (1.83 g, 2 mmol), P (t-Bu) 3 (1.01 g, 4.97 mmol), NaO (t-Bu) (14.4 g, 149.9 mmol), Toluene (109 mL) The method was used to give the product Sub 2-144 (15.03 g, 69%).
Sub 2의 예시Sub 2 example
한편, Sub 2에 속하는 화합물은 아래와 같은 화합물일 수 있으나, 이에 한정되는 것은 아니며, 표 2는 Sub 2에 속하는 화합물의 FD-MS 값을 나타낸 것이다.Meanwhile, the compound belonging to Sub 2 may be the following compound, but is not limited thereto, and Table 2 shows the FD-MS value of the compound belonging to Sub 2.
| 화합물compound | FD-MSFD-MS | 화합물compound | FD-MSFD-MS |
| Sub 2-1Sub 2-1 | m/z=427.00(C24HBrNS=428.34)m / z = 427.00 (C24HBrNS = 428.34) | Sub 2-2Sub 2-2 | m/z=503.03(C30H18BrNS=504.44)m / z = 503.03 (C 30 H 18 BrNS = 504.44) |
| Sub 2-3Sub 2-3 | m/z=503.03(C30H18BrNS=504.44)m / z = 503.03 (C 30 H 18 BrNS = 504.44) | Sub 2-4Sub 2-4 | m/z=477.02(C28H16BrNS=478.40)m / z = 477.02 (C 28 H 16 BrNS = 478.40) |
| Sub 2-5Sub 2-5 | m/z=477.02(C28H16BrNS=478.40)m / z = 477.02 (C 28 H 16 BrNS = 478.40) | Sub 2-6Sub 2-6 | m/z=483.07(C28H22BrNS=484.45)m / z = 483.07 (C 28 H 22 BrNS = 484.45) |
| Sub 2-7Sub 2-7 | m/z=507.03(C29H18BrNOS=508.43)m / z = 507.03 (C 29 H 18 BrNOS = 508.43) | Sub 2-8Sub 2-8 | m/z=467.03(C27H18BrNS=468.41)m / z = 467.03 (C 27 H 18 BrNS = 468.41) |
| Sub 2-9Sub 2-9 | m/z=503.03(C30H18BrNS=504.44)m / z = 503.03 (C 30 H 18 BrNS = 504.44) | Sub 2-10Sub 2-10 | m/z=427.00(C24HBrNS=428.34)m / z = 427.00 (C24HBrNS = 428.34) |
| Sub 2-11Sub 2-11 | m/z=503.03(C30H18BrNS=504.44)m / z = 503.03 (C 30 H 18 BrNS = 504.44) | Sub 2-12Sub 2-12 | m/z=503.03(C30H18BrNS=504.44)m / z = 503.03 (C 30 H 18 BrNS = 504.44) |
| Sub 2-13Sub 2-13 | m/z=477.02(C28H16BrNS=478.40)m / z = 477.02 (C 28 H 16 BrNS = 478.40) | Sub 2-14Sub 2-14 | m/z=477.02(C28H16BrNS=478.40)m / z = 477.02 (C 28 H 16 BrNS = 478.40) |
| Sub 2-15Sub 2-15 | m/z=582.05(C33H19BrN4S=583.50)m / z = 582.05 (C 33 H 19 BrN 4 S = 583.50) | Sub 2-16Sub 2-16 | m/z=581.06(C34H20BrN3S=582.51)m / z = 581.06 (C 34 H 20 BrN 3 S = 582.51) |
| Sub 2-17Sub 2-17 | m/z=581.06(C34H20BrN3S=582.51)m / z = 581.06 (C 34 H 20 BrN 3 S = 582.51) | Sub 2-18Sub 2-18 | m/z=581.06(C34H20BrN3S=582.51)m / z = 581.06 (C 34 H 20 BrN 3 S = 582.51) |
| Sub 2-19Sub 2-19 | m/z=555.04(C32H18BrN3S=556.47)m / z = 555.04 (C 32 H 18 BrN 3 S = 556.47) | Sub 2-20Sub 2-20 | m/z=611.01(C34H18BrN3S2=612.56)m / z = 611.01 (C 34 H 18 BrN 3 S 2 = 612.56) |
| Sub 2-21Sub 2-21 | m/z=681.09(C42H24BrN3S=682.63)m / z = 681.09 (C 42 H 24 BrN 3 S = 682.63) | Sub 2-22Sub 2-22 | m/z=542.05(C32H19BrN2S=543.48)m / z = 542.05 (C 32 H 19 BrN 2 S = 543.48) |
| Sub 2-23Sub 2-23 | m/z=665.08(C43H24BrNS=666.63)m / z = 665.08 (C 43 H 24 BrNS = 666.63) | Sub 2-24Sub 2-24 | m/z=599.11(C36H18D5BrN2S=600.58)m / z = 599.11 (C 36 H 18 D 5 BrN 2 S = 600.58) |
| Sub 2-25Sub 2-25 | m/z=503.03(C30H18BrNS=504.44)m / z = 503.03 (C 30 H 18 BrNS = 504.44) | Sub 2-26Sub 2-26 | m/z=502.01(C29H15BrN2S=503.41)m / z = 502.01 (C 29 H 15 BrN 2 S = 503.41) |
| Sub 2-27Sub 2-27 | m/z=629.08(C40H24BrNS=630.59)m / z = 629.08 (C 40 H 24 BrNS = 630.59) | Sub 2-28Sub 2-28 | m/z=605.06(C36H20BrN3S =606.53)m / z = 605.06 (C 36 H 20 BrN 3 S = 606.53) |
| Sub 2-29Sub 2-29 | m/z=657.09(C40H24BrN3S=658.61)m / z = 657.09 (C 40 H 24 BrN 3 S = 658.61) | Sub 2-30Sub 2-30 | m/z=631.07(C38H22BrN3S=632.57)m / z = 631.07 (C 38 H 22 BrN 3 S = 632.57) |
| Sub 2-31Sub 2-31 | m/z=720.09(C45H25BrN2OS=721.66)m / z = 720.09 (C 45 H 25 BrN 2 OS = 721.66) | Sub 2-32Sub 2-32 | m/z=593.08(C37H24BrNS=594.56)m / z = 593.08 (C 37 H 24 BrNS = 594.56) |
| Sub 2-33Sub 2-33 | m/z=471.99(C24H13BrN2O2S=473.34)m / z = 471.99 (C 24 H 13 BrN 2 O 2 S = 473.34) | Sub 2-34Sub 2-34 | m/z=503.03(C30H18BrNS=504.44)m / z = 503.03 (C 30 H 18 BrNS = 504.44) |
| Sub 2-35Sub 2-35 | m/z=477.02(C28H16BrNS=478.40)m / z = 477.02 (C 28 H 16 BrNS = 478.40) | Sub 2-36Sub 2-36 | m/z=508.07(C30H13D5BrNS=509.47)m / z = 508.07 (C 30 H 13 D 5 BrNS = 509.47) |
| Sub 2-37Sub 2-37 | m/z=411.03(C24H14BrNO=412.28)m / z = 411.03 (C 24 H 14 BrNO = 412.28) | Sub 2-38Sub 2-38 | m/z=655.09(C40H22BrN3O2=656.53)m / z = 655.09 (C 40 H 22 BrN 3 O 2 = 656.53) |
| Sub 2-39Sub 2-39 | m/z=539.06(C32H18BrN3O=540.41)m / z = 539.06 (C 32 H 18 BrN 3 O = 540.41) | Sub 2-40Sub 2-40 | m/z=645.05(C38H20BrN3OS=646.55)m / z = 645.05 (C 38 H 20 BrN 3 OS = 646.55) |
| Sub 2-41Sub 2-41 | m/z=461.04(C28H16BrNO=462.34)m / z = 461.04 (C 28 H 16 BrNO = 462.34) | Sub 2-42Sub 2-42 | m/z=487.06(C30H18BrNO=488.37)m / z = 487.06 (C 30 H 18 BrNO = 488.37) |
| Sub 2-43Sub 2-43 | m/z=537.07(C34H20BrNO=538.43)m / z = 537.07 (C 34 H 20 BrNO = 538.43) | Sub 2-44Sub 2-44 | m/z=437.08(C27H20BrN=438.36)m / z = 437.08 (C 27 H 20 BrN = 438.36) |
| Sub 2-45Sub 2-45 | m/z=453.05(C20H20BrNSi=453.43)m / z = 453.05 (C 20 H 20 BrNSi = 453.43) | Sub 2-46Sub 2-46 | m/z=474.95(C24H14BrNSi=478.24)m / z = 474.95 (C 24 H 14 BrNSi = 478.24) |
Sub 3의 예시Sub 3 example
한편, Sub 3에 속하는 화합물은 아래와 같은 화합물일 수 있으나, 이에 한정되는 것은 아니며, 표 3은 Sub 3에 속하는 화합물의 FD-MS 값을 나타낸 것이다.Meanwhile, the compound belonging to Sub 3 may be the following compound, but is not limited thereto, and Table 3 shows the FD-MS value of the compound belonging to Sub 3.
| 화합물compound | FD-MSFD-MS | 화합물compound | FD-MSFD-MS |
| Sub 3-1Sub 3-1 | m/z=287.11(C18H14BNO2=287.12)m / z = 287.11 (C 18 H 14 BNO 2 = 287.12) | Sub 3-2Sub 3-2 | m/z=287.11(C18H14BNO2=287.12)m / z = 287.11 (C 18 H 14 BNO 2 = 287.12) |
| Sub 3-3Sub 3-3 | m/z=287.11(C18H14BNO2=287.12)m / z = 287.11 (C 18 H 14 BNO 2 = 287.12) | Sub 3-4Sub 3-4 | m/z=287.11(C18H14BNO2=287.12)m / z = 287.11 (C 18 H 14 BNO 2 = 287.12) |
| Sub 3-5Sub 3-5 | m/z=337.13(C22H16BNO2=337.18)m / z = 337.13 (C 22 H 16 BNO 2 = 337.18) | Sub 3-6Sub 3-6 | m/z=337.13(C22H16BNO2=337.18)m / z = 337.13 (C 22 H 16 BNO 2 = 337.18) |
| Sub 3-7Sub 3-7 | m/z=337.13(C22H16BNO2=337.18)m / z = 337.13 (C 22 H 16 BNO 2 = 337.18) | Sub 3-8Sub 3-8 | m/z=337.13(C22H16BNO2=337.18)m / z = 337.13 (C 22 H 16 BNO 2 = 337.18) |
| Sub 3-9Sub 3-9 | m/z=337.13(C22H16BNO2=337.18)m / z = 337.13 (C 22 H 16 BNO 2 = 337.18) | Sub 3-10Sub 3-10 | m/z=363.14(C24H18BNO2=363.22)m / z = 363.14 (C 24 H 18 BNO 2 = 363.22) |
| Sub 3-11Sub 3-11 | m/z=363.14(C24H18BNO2=363.22)m / z = 363.14 (C 24 H 18 BNO 2 = 363.22) | Sub 3-12Sub 3-12 | m/z=368.17(C24H13D5BNO2=368.25)m / z = 368.17 (C 24 H 13 D 5 BNO 2 = 368.25) |
| Sub 3-13Sub 3-13 | m/z=387.14(C26H18BNO2=387.24)m / z = 387.14 (C 26 H 18 BNO 2 = 387.24) | Sub 3-14Sub 3-14 | m/z=437.16(C30H20BNO2=437.30)m / z = 437.16 (C 30 H 20 BNO 2 = 437.30) |
| Sub 3-15Sub 3-15 | m/z=413.16(C28H20BNO2=413.27)m / z = 413.16 (C 28 H 20 BNO 2 = 413.27) | Sub 3-16Sub 3-16 | m/z=429.13(C28H17BFNO2=429.25)m / z = 429.13 (C 28 H 17 BFNO 2 = 429.25) |
| Sub 3-17Sub 3-17 | m/z=368.17(C24H13D5BNO2=368.25)m / z = 368.17 (C 24 H 13 D 5 BNO 2 = 368.25) | Sub 3-18Sub 3-18 | m/z=482.18(C31H23BNO3=482.34)m / z = 482.18 (C 31 H 23 BNO 3 = 482.34) |
| Sub 3-19Sub 3-19 | m/z=452.17(C30H21BN2O2=452.31)m / z = 452.17 (C 30 H 21 BN 2 O 2 = 452.31) | Sub 3-20Sub 3-20 | m/z=364.14(C23H17BN2O2=364.20)m / z = 364.14 (C 23 H 17 BN 2 O 2 = 364.20) |
| Sub 3-21Sub 3-21 | m/z=442.16(C27H19BN4O2=442.28)m / z = 442.16 (C 27 H 19 BN 4 O 2 = 442.28) | Sub 3-22Sub 3-22 | m/z=441.16(C28H20BN3O2=441.29)m / z = 441.16 (C 28 H 20 BN 3 O 2 = 441.29) |
| Sub 3-23Sub 3-23 | m/z=441.26(C28H20BN3O2=441.29)m / z = 441.26 (C 28 H 20 BN 3 O 2 = 441.29) | Sub 3-24Sub 3-24 | m/z=442.16(C27H19BN4O2=442.28)m / z = 442.16 (C 27 H 19 BN 4 O 2 = 442.28) |
| Sub 3-25Sub 3-25 | m/z=441.16(C28H20BN3O2=441.29)m / z = 441.16 (C 28 H 20 BN 3 O 2 = 441.29) | Sub 3-26Sub 3-26 | m/z=517.20(C34H24BN3O2=517.38)m / z = 517.20 (C 34 H 24 BN 3 O 2 = 517.38) |
| Sub 3-27Sub 3-27 | m/z=528.25(C33H13D10BN4O2=528.43)m / z = 528.25 (C 33 H 13 D 10 BN 4 O 2 = 528.43) | Sub 3-28Sub 3-28 | m/z=455.14(C28H18BN3O3=455.27)m / z = 455.14 (C 28 H 18 BN 3 O 3 = 455.27) |
| Sub 3-29Sub 3-29 | m/z=505.16(C32H20BN3O3=505.33)m / z = 505.16 (C 32 H 20 BN 3 O 3 = 505.33) | Sub 3-30Sub 3-30 | m/z=444.11(C27H17BN2O2S=444.31)m / z = 444.11 (C 27 H 17 BN 2 O 2 S = 444.31) |
| Sub 3-31Sub 3-31 | m/z=547.15(C34H22BN3O2S=547.43)m / z = 547.15 (C 34 H 22 BN 3 O 2 S = 547.43) | Sub 3-32Sub 3-32 | m/z=415.15(C26H18BN3O2=415.25)m / z = 415.15 (C 26 H 18 BN 3 O 2 = 415.25) |
| Sub 3-33Sub 3-33 | m/z=465.16(C30H20BN3O2=465.31)m / z = 465.16 (C 30 H 20 BN 3 O 2 = 465.31) | Sub 3-34Sub 3-34 | m/z=565.20(C38H24BN3O2=565.43)m / z = 565.20 (C 38 H 24 BN 3 O 2 = 565.43) |
| Sub 3-35Sub 3-35 | m/z=465.16(C30H20BN3O2=465.31)m / z = 465.16 (C 30 H 20 BN 3 O 2 = 465.31) | Sub 3-36Sub 3-36 | m/z=228.04(C12H9BO2S=228.07)m / z = 228.04 (C 12 H 9 BO 2 S = 228.07) |
| Sub 3-37Sub 3-37 | m/z=228.04(C12H9BO2S=228.07)m / z = 228.04 (C 12 H 9 BO 2 S = 228.07) | Sub 3-38Sub 3-38 | m/z=228.04(C12H9BO2S=228.07)m / z = 228.04 (C 12 H 9 BO 2 S = 228.07) |
| Sub 3-39Sub 3-39 | m/z=278.06(C16H11BN2S=278.13)m / z = 278.06 (C 16 H 11 BN 2 S = 278.13) | Sub 3-40Sub 3-40 | m/z=278.06(C16H11BO2S=278.13)m / z = 278.06 (C 16 H 11 BO 2 S = 278.13) |
| Sub 3-41Sub 3-41 | m/z=278.06(C16H11BO2S=278.13)m / z = 278.06 (C 16 H 11 BO 2 S = 278.13) | Sub 3-42Sub 3-42 | m/z=305.07(C17H12BNO2S=305.16)m / z = 305.07 (C 17 H 12 BNO 2 S = 305.16) |
| Sub 3-43Sub 3-43 | m/z=212.06(C12H9BO3=212.01)m / z = 212.06 (C 12 H 9 BO 3 = 212.01) | Sub 3-44Sub 3-44 | m/z=212.06(C12H9BO3=212.01)m / z = 212.06 (C 12 H 9 BO 3 = 212.01) |
| Sub 3-45Sub 3-45 | m/z=212.06(C12H9BO3=212.01)m / z = 212.06 (C 12 H 9 BO 3 = 212.01) | Sub 3-46Sub 3-46 | m/z=262.08(C16H11BO3=262.07)m / z = 262.08 (C 16 H 11 BO 3 = 262.07) |
| Sub 3-47Sub 3-47 | m/z=312.10(C20H13BO3=312.13)m / z = 312.10 (C 20 H 13 BO 3 = 312.13) | Sub 3-48Sub 3-48 | m/z=289.09(C17H12BNO3=289.09)m / z = 289.09 (C 17 H 12 BNO 3 = 289.09) |
| Sub 3-49Sub 3-49 | m/z=238.12(C15H15BO2=238.09)m / z = 238.12 (C 15 H 15 BO 2 = 238.09) | Sub 3-50Sub 3-50 | m/z=238.12(C15H15BO2=238.09)m / z = 238.12 (C 15 H 15 BO 2 = 238.09) |
| Sub 3-51Sub 3-51 | m/z=266.15(C17H19BO2=266.14)m / z = 266.15 (C 17 H 19 BO 2 = 266.14) | Sub 3-52Sub 3-52 | m/z=362.15(C25H19BO2=362.23)m / z = 362.15 (C 25 H 19 BO 2 = 362.23) |
| Sub 3-53Sub 3-53 | m/z=438.18(C31H23BO2=438.32)m / z = 438.18 (C 31 H 23 BO 2 = 438.32) | Sub 3-54Sub 3-54 | m/z=360.13(C24H17BO2=360.21)m / z = 360.13 (C 24 H 17 BO 2 = 360.21) |
| Sub 3-55Sub 3-55 | m/z=410.15(C29H19BO2=410.27)m / z = 410.15 (C 29 H 19 BO 2 = 410.27) | Sub 3-56Sub 3-56 | m/z=254.09(C14H15BO2Si=254.16)m / z = 254.09 (C 14 H 15 BO 2 Si = 254.16) |
| Sub 3-57Sub 3-57 | m/z=254.09(C14H15BO2Si=254.16)m / z = 254.09 (C 14 H 15 BO 2 Si = 254.16) | Sub 3-58Sub 3-58 | m/z=282.12(C16H19BO2Si=282.22)m / z = 282.12 (C 16 H 19 BO 2 Si = 282.22) |
| Sub 3-59Sub 3-59 | m/z=378.12(C24H19BO2Si=387.30)m / z = 378.12 (C 24 H 19 BO 2 Si = 387.30) | Sub 3-60Sub 3-60 | m/z=378.12(C24H19BO2Si=378.30)m / z = 378.12 (C 24 H 19 BO 2 Si = 378.30) |
| Sub 3-61Sub 3-61 | m/z=376.11(C24H17BO2Si=376.29)m / z = 376.11 (C 24 H 17 BO 2 Si = 376.29) | Sub 3-62Sub 3-62 | m/z=275.99(C12H9BO2Se=274.97)m / z = 275.99 (C 12 H 9 BO 2 Se = 274.97) |
| Sub 3-63Sub 3-63 | m/z=275.99(C12H9BO2Se=274.97)m / z = 275.99 (C 12 H 9 BO 2 Se = 274.97) | Sub 3-64Sub 3-64 | m/z=326.00(C16H11BO2Se=325.03)m / z = 326.00 (C 16 H 11 BO 2 Se = 325.03) |
화학식 1의 Product의 합성법Synthesis of Product of Formula 1
둥근바닥플라스크에 Sub 1 또는 Sub 2 화합물(1당량)을 넣고, Sub 3 화합물을 (1당량), Pd(PPh3)4 (0.03~0.05당량), NaOH (3당량), THF (3 mL / 1 mmol), 물 (1.5 mL / 1 mmol)을 넣는다. 그런 후에 80℃ 상태에서 가열 환류시킨다. 반응이 완료되면 상온에서 증류수를 넣어 희석시키고 Methylene chloride와 물로 추출한다. 유기층을 MgSO4로 건조하여 농축한 후 생성된 화합물을 Toluene과 Acetone으로 재결정하여 생성물을 얻었다.Put the Sub 1 or Sub 2 compound (1 eq) into the round bottom flask, and add the Sub 3 compound (1 eq), Pd (PPh 3 ) 4 (0.03 to 0.05 eq), NaOH (3 eq), THF (3 mL / 1 mmol) and water (1.5 mL / 1 mmol). Then, the mixture was heated to reflux at 80 ° C. When the reaction is complete, dilute it with distilled water at room temperature and extract with Methylene chloride and water. The organic layer was dried over MgSO 4 and concentrated, and the resulting compound was recrystallized from Toluene and Acetone to obtain a product.
화합물 1-2의 합성Synthesis of Compound 1-2
둥근바닥플라스크에 Sub 1-2 (5g, 11.5mmol), Sub 3-3 (3.9g, 11.5mmol), Pd(PPh3)4 (0.5g, 0.5mmol), NaOH (1.4g, 35mmol), THF (30mL)/H2O (15mL)을 넣는다. 그런 후에 80℃ 상태에서 8시간 동안 가열 환류시킨다. 반응이 완료되면 상온에서 증류수를 넣어 희석시키고 Methylene chloride와 물로 추출한다. 유기층을 MgSO4로 건조하여 농축한 후 생성된 화합물을 Toluene과 Acetone으로 재결정하여 생성물 1-2 (5.4g, 80%)을 얻었다.Round bottom flask Sub 1-2 (5g, 11.5mmol), Sub 3-3 (3.9g, 11.5mmol), Pd (PPh 3 ) 4 (0.5g, 0.5mmol), NaOH (1.4g, 35mmol), THF Add (30 mL) / H 2 O (15 mL). Then, the mixture was heated to reflux for 8 hours at 80 ° C. When the reaction is complete, dilute it with distilled water at room temperature and extract with Methylene chloride and water. The organic layer was dried over MgSO 4 and concentrated, and the resulting compound was recrystallized from Toluene and Acetone to obtain product 1-2 (5.4 g, 80%).
화합물 1-7의 합성Synthesis of Compound 1-7
Sub 1-3 (10g, 20mmol), Sub 3-3 (5.7g, 20mmol), Pd(PPh3)4
(0.9g, 0.8mmol), NaOH (2.4g, 59mmol), THF (40mL)/H2O (20mL)을 상기 1-2 합성방법을 사용하여 생성물 1-7 (11.3g, 85%)을 얻었다.Sub 1-3 (10g, 20mmol), Sub 3-3 (5.7g, 20mmol), Pd (PPh 3 ) 4 (0.9g, 0.8mmol), NaOH (2.4g, 59mmol), THF (40mL) / H 2 O (20mL) were obtained using the 1-2 synthesis method above to obtain products 1-7 (11.3g, 85%). .
화합물 1-14의 합성Synthesis of Compound 1-14
Sub 1-5 (10g, 21mmol), Sub 3-10 (7.6g, 21mmol), Pd(PPh3)4
(1g, 0.8mmol), NaOH (2.5g, 63mmol), THF (40mL)/H2O (20mL)을 상기 1-2 합성방법을 사용하여 생성물 1-14 (12.3g, 82%)을 얻었다.Sub 1-5 (10g, 21mmol), Sub 3-10 (7.6g, 21mmol), Pd (PPh 3 ) 4 (1 g, 0.8 mmol), NaOH (2.5 g, 63 mmol), THF (40 mL) / H 2 O (20 mL) were obtained using the 1-2 synthesis method above to obtain products 1-14 (12.3 g, 82%).
화합물 1-20의 합성Synthesis of Compound 1-20
Sub 1-1 (10g, 21mmol), Sub 3-11 (7.6g, 21mmol), Pd(PPh3)4
(1g, 0.8mmol), NaOH (2.5g, 63mmol), THF (40mL)/H2O (20mL)을 상기 1-2 합성방법을 사용하여 생성물 1-20 (12.5g, 83%)을 얻었다.Sub 1-1 (10g, 21mmol), Sub 3-11 (7.6g, 21mmol), Pd (PPh 3 ) 4 (1 g, 0.8 mmol), NaOH (2.5 g, 63 mmol), THF (40 mL) / H 2 O (20 mL) were obtained using the 1-2 synthesis method above to obtain products 1-20 (12.5 g, 83%).
화합물 1-26의 합성Synthesis of Compound 1-26
Sub 1-6 (5g, 11.5mmol), Sub 3-3 (3.9g, 11.5mmol), Pd(PPh3)4
(0.5g, 0.5mmol), NaOH (1.4g, 35mmol), THF (30mL)/H2O (15mL)을 상기 1-2 합성방법을 사용하여 생성물 1-26 (4.9g, 72%)을 얻었다.Sub 1-6 (5g, 11.5mmol), Sub 3-3 (3.9g, 11.5mmol), Pd (PPh 3 ) 4 (0.5g, 0.5mmol), NaOH (1.4g, 35mmol), THF (30mL) / H 2 O (15mL) was obtained by using the above 1-2 synthesis method to obtain product 1-26 (4.9g, 72%). .
화합물 1-27의 합성Synthesis of Compound 1-27
Sub 1-6 (5g, 11.5mmol), Sub 3-10 (4.2g, 11.5mmol), Pd(PPh3)4
(0.5g, 0.5mmol), NaOH (1.4g, 35mmol), THF (30mL)/H2O (15mL)을 상기 1-2 합성방법을 사용하여 생성물 1-27 (6.5g, 85%)을 얻었다.Sub 1-6 (5g, 11.5mmol), Sub 3-10 (4.2g, 11.5mmol), Pd (PPh 3 ) 4 (0.5g, 0.5mmol), NaOH (1.4g, 35mmol), THF (30mL) / H 2 O (15mL) was obtained by using the above 1-2 synthesis method to obtain products 1-27 (6.5g, 85%). .
화합물 1-33의 합성Synthesis of Compound 1-33
Sub 1-7 (10g, 20mmol), Sub 3-11 (7.3g, 20mmol), Pd(PPh3)4
(0.9g, 0.8mmol), NaOH (2.4g, 59mmol), THF (40mL)/H2O (20mL)을 상기 1-2 합성방법을 사용하여 생성물 1-33 (13.5g, 91%)을 얻었다.Sub 1-7 (10g, 20mmol), Sub 3-11 (7.3g, 20mmol), Pd (PPh 3 ) 4 (0.9g, 0.8mmol), NaOH (2.4g, 59mmol), THF (40mL) / H 2 O (20mL) was obtained by using the synthesis method 1-2, 1-33 (13.5g, 91%). .
화합물 1-51의 합성Synthesis of Compound 1-51
Sub 1-6 (5g, 11.5mmol), Sub 3-1 (3.9g, 11.5mmol), Pd(PPh3)4
(0.5g, 0.5mmol), NaOH (1.4g, 35mmol), THF (30mL)/H2O (15mL)을 상기 1-2 합성방법을 사용하여 생성물 1-51 (3.5g, 51%)을 얻었다.Sub 1-6 (5g, 11.5mmol), Sub 3-1 (3.9g, 11.5mmol), Pd (PPh 3 ) 4 (0.5g, 0.5mmol), NaOH (1.4g, 35mmol), THF (30mL) / H 2 O (15mL) was obtained by using the above 1-2 synthesis method to obtain products 1-51 (3.5g, 51%). .
화합물 1-52의 합성Synthesis of Compound 1-52
Sub 1-6 (5g, 11.5mmol), Sub 3-2 (3.9g, 11.5mmol), Pd(PPh3)4
(0.5g, 0.5mmol), NaOH (1.4g, 35mmol), THF (30mL)/H2O (15mL)을 상기 1-2 합성방법을 사용하여 생성물 1-52 (3.8g, 56%)을 얻었다.Sub 1-6 (5g, 11.5mmol), Sub 3-2 (3.9g, 11.5mmol), Pd (PPh 3 ) 4 (0.5g, 0.5mmol), NaOH (1.4g, 35mmol), THF (30mL) / H 2 O (15mL) were obtained by using the above 1-2 synthesis method to obtain products 1-52 (3.8g, 56%). .
화합물 1-53의 합성Synthesis of Compound 1-53
Sub 1-6 (5g, 11.5mmol), Sub 3-4 (3.9g, 11.5mmol), Pd(PPh3)4
(0.5g, 0.5mmol), NaOH (1.4g, 35mmol), THF (30mL)/H2O (15mL)을 상기 1-2 합성방법을 사용하여 생성물 1-53 (4.2g, 62%)을 얻었다.Sub 1-6 (5g, 11.5mmol), Sub 3-4 (3.9g, 11.5mmol), Pd (PPh 3 ) 4 (0.5g, 0.5mmol), NaOH (1.4g, 35mmol), THF (30mL) / H 2 O (15mL) was obtained by using the above 1-2 synthesis method to give products 1-53 (4.2g, 62%). .
화합물 1-66의 합성Synthesis of Compound 1-66
Sub 1-14 (10g, 21mmol), Sub 3-3 (7.6g, 21mmol), Pd(PPh3)4
(1g, 0.8mmol), NaOH (2.5g, 63mmol), THF (40mL)/H2O (20mL)을 상기 1-2 합성방법을 사용하여 생성물 1-66 (8.5g, 63%)을 얻었다.Sub 1-14 (10g, 21mmol), Sub 3-3 (7.6g, 21mmol), Pd (PPh 3 ) 4 (1 g, 0.8 mmol), NaOH (2.5 g, 63 mmol), THF (40 mL) / H 2 O (20 mL) were obtained using the 1-2 synthesis method above to obtain products 1-66 (8.5 g, 63%).
화합물 1-71의 합성Synthesis of Compound 1-71
둥근바닥플라스크에 Sub 1-1 (5g, 11.5mmol), Sub 3-46 (3.0g, 11.5mmol), Pd(PPh3)4 (0.5g, 0.5mmol), NaOH (1.4g, 35mmol), THF (30mL)/H2O (15mL)을 상기 1-2 합성방법을 사용하여 생성물 1-71 (4.7g, 73%)을 얻었다.Round bottom flask Sub 1-1 (5g, 11.5mmol), Sub 3-46 (3.0g, 11.5mmol), Pd (PPh 3 ) 4 (0.5g, 0.5mmol), NaOH (1.4g, 35mmol), THF (30 mL) / H 2 O (15 mL) was obtained product 1-71 (4.7 g, 73%) using the above 1-2 synthesis method.
화합물 1-78의 합성Synthesis of Compound 1-78
둥근바닥플라스크에 Sub 1-4 (5g, 9.9mmol), Sub 3-53 (4.3g, 9.9mmol), Pd(PPh3)4 (0.5g, 0.4mmol), NaOH (1.2g, 29.7mmol), THF (40mL)/H2O (20mL)을 상기 1-2 합성방법을 사용하여 생성물 1-78 (5.3g, 65%)을 얻었다.Round bottom flask Sub 1-4 (5g, 9.9mmol), Sub 3-53 (4.3g, 9.9mmol), Pd (PPh 3 ) 4 (0.5g, 0.4mmol), NaOH (1.2g, 29.7mmol), THF (40 mL) / H 2 O (20 mL) was obtained using the 1-2 synthesis method above to obtain product 1-78 (5.3 g, 65%).
화합물 1-90의 합성Synthesis of Compound 1-90
둥근바닥플라스크에 Sub 1-39 (10g, 20.5mmol), Sub 3-38 (5.9g, 20.5mmol), Pd(PPh3)4 (1g, 0.8mmol), NaOH (2.5g, 61mmol), THF (40mL)/H2O (20mL)을 상기 1-2 합성방법을 사용하여 생성물 1-90 (5.8g, 48%)을 얻었다.Round bottom flask Sub 1-39 (10g, 20.5mmol), Sub 3-38 (5.9g, 20.5mmol), Pd (PPh 3 ) 4 (1g, 0.8mmol), NaOH (2.5g, 61mmol), THF ( 40 mL) / H 2 O (20 mL) was obtained using the above 1-2 synthesis method to obtain product 1-90 (5.8 g, 48%).
화합물 2-1의 합성Synthesis of Compound 2-1
둥근바닥플라스크에 Sub 2-1 (5g, 11.5mmol), Sub 3-3 (3.9g, 11.5mmol), Pd(PPh3)4 (0.5g, 0.5mmol), NaOH (1.4g, 35mmol), THF (30mL)/H2O (15mL)을 상기 1-2 합성방법을 사용하여 생성물 2-1 (5.5g, 81%)을 얻었다.Round bottom flask Sub 2-1 (5g, 11.5mmol), Sub 3-3 (3.9g, 11.5mmol), Pd (PPh 3 ) 4 (0.5g, 0.5mmol), NaOH (1.4g, 35mmol), THF (30 mL) / H 2 O (15 mL) was obtained using the above 1-2 synthesis method to obtain product 2-1 (5.5 g, 81%).
화합물 2-2의 합성Synthesis of Compound 2-2
둥근바닥플라스크에 Sub 2-1 (5g, 11.5mmol), Sub 3-10 (4.2g, 11.5mmol), Pd(PPh3)4 (0.5g, 0.5mmol), NaOH (1.4g, 35mmol), THF (30mL)/H2O (15mL)을 상기 1-2 합성방법을 사용하여 생성물 2-2 (6.1g, 80%)를 얻었다.Round bottom flask Sub 2-1 (5g, 11.5mmol), Sub 3-10 (4.2g, 11.5mmol), Pd (PPh 3 ) 4 (0.5g, 0.5mmol), NaOH (1.4g, 35mmol), THF (30 mL) / H 2 O (15 mL) was obtained using the above 1-2 synthesis method to obtain product 2-2 (6.1 g, 80%).
화합물 2-3의 합성Synthesis of Compound 2-3
둥근바닥플라스크에 Sub 2-1 (5g, 11.5mmol), Sub 3-11 (4.2g, 11.5mmol), Pd(PPh3)4 (0.5g, 0.5mmol), NaOH (1.4g, 35mmol), THF (30mL)/H2O (15mL)을 상기 1-2 합성방법을 사용하여 생성물 2-3 (5.8g, 76%)을 얻었다.Round bottom flask Sub 2-1 (5g, 11.5mmol), Sub 3-11 (4.2g, 11.5mmol), Pd (PPh 3 ) 4 (0.5g, 0.5mmol), NaOH (1.4g, 35mmol), THF (30 mL) / H 2 O (15 mL) was obtained product 2-3 (5.8 g, 76%) using the above 1-2 synthesis method.
화합물 2-6의 합성Synthesis of Compound 2-6
둥근바닥플라스크에 Sub 2-2 (10g, 20mmol), Sub 3-3 (5.7g, 20mmol), Pd(PPh3)4 (0.9g, 0.8mmol), NaOH (2.4g, 59mmol), THF (40mL)/H2O (20mL)을 상기 1-2 합성방법을 사용하여 생성물 2-6 (10.3g, 81%)을 얻었다.Round bottom flask Sub 2-2 (10g, 20mmol), Sub 3-3 (5.7g, 20mmol), Pd (PPh 3 ) 4 (0.9g, 0.8mmol), NaOH (2.4g, 59mmol), THF (40mL) ) / H 2 O (20 mL) was obtained product 2-6 (10.3 g, 81%) using the above 1-2 synthesis method.
화합물 2-7의 합성Synthesis of Compound 2-7
둥근바닥플라스크에 Sub 2-2 (10g, 20mmol), Sub 3-10 (7.3g, 20mmol), Pd(PPh3)4 (0.9g, 0.8mmol), NaOH (2.4g, 59mmol), THF (40mL)/H2O (20mL)을 상기 1-2 합성방법을 사용하여 생성물 2-7 (11g, 74%)을 얻었다.Round bottom flask Sub 2-2 (10g, 20mmol), Sub 3-10 (7.3g, 20mmol), Pd (PPh 3 ) 4 (0.9g, 0.8mmol), NaOH (2.4g, 59mmol), THF (40mL) ) / H 2 O (20 mL) was obtained product 2-7 (11 g, 74%) using the above 1-2 synthesis method.
화합물 2-8의 합성Synthesis of Compound 2-8
둥근바닥플라스크에 Sub 2-2 (10g, 20mmol), Sub 3-11 (7.3g, 20mmol), Pd(PPh3)4 (0.9g, 0.8mmol), NaOH (2.4g, 59mmol), THF (40mL)/H2O (20mL)을 상기 1-2 합성방법을 사용하여 생성물 2-8 (12g, 81%)을 얻었다.Round bottom flask Sub 2-2 (10g, 20mmol), Sub 3-11 (7.3g, 20mmol), Pd (PPh 3 ) 4 (0.9g, 0.8mmol), NaOH (2.4g, 59mmol), THF (40mL) ) / H 2 O (20 mL) was obtained product 2-8 (12 g, 81%) using the above 1-2 synthesis method.
화합물 2-33의 합성Synthesis of Compound 2-33
둥근바닥플라스크에 Sub 2-1 (5g, 11.5mmol), Sub 3-38 (2.6g, 11.5mmol), Pd(PPh3)4 (0.5g, 0.5mmol), NaOH (1.4g, 35mmol), THF (30mL)/H2O (15mL)을 상기 1-2 합성방법을 사용하여 생성물 2-33 (5.0g, 82%)을 얻었다.Round bottom flask Sub 2-1 (5g, 11.5mmol), Sub 3-38 (2.6g, 11.5mmol), Pd (PPh 3 ) 4 (0.5g, 0.5mmol), NaOH (1.4g, 35mmol), THF (30 mL) / H 2 O (15 mL) was obtained using the above 1-2 synthesis method to obtain product 2-33 (5.0 g, 82%).
화합물 2-38의 합성Synthesis of Compound 2-38
둥근바닥플라스크에 Sub 2-1 (5g, 11.5mmol), Sub 3-45 (2.4g, 11.5mmol), Pd(PPh3)4 (0.5g, 0.5mmol), NaOH (1.4g, 35mmol), THF (30mL)/H2O (15mL)을 상기 1-2 합성방법을 사용하여 생성물 2-38 (4.4g, 74%)을 얻었다.Round bottom flask Sub 2-1 (5g, 11.5mmol), Sub 3-45 (2.4g, 11.5mmol), Pd (PPh 3 ) 4 (0.5g, 0.5mmol), NaOH (1.4g, 35mmol), THF (30 mL) / H 2 O (15 mL) was obtained product 2-38 (4.4 g, 74%) using the above 1-2 synthesis method.
화합물 2-133의 합성Synthesis of Compound 2-133
둥근바닥플라스크에 Sub 2-37 (5g, 12mmol), Sub 3-10 (4.4g, 12mmol), Pd(PPh3)4 (0.6g, 0.5mmol), NaOH (1.5g, 36mmol), THF (30mL)/H2O (15mL)을 상기 1-2 합성방법을 사용하여 생성물 2-133 (5.6g, 72%)을 얻었다.Round bottom flask Sub 2-37 (5g, 12mmol), Sub 3-10 (4.4g, 12mmol), Pd (PPh 3 ) 4 (0.6g, 0.5mmol), NaOH (1.5g, 36mmol), THF (30mL ) / H 2 O (15 mL) was obtained product 2-133 (5.6 g, 72%) using the above 1-2 synthesis method.
| 화합물compound | FD-MSFD-MS | 화합물compound | FD-MSFD-MS |
| 1-11-1 | m/z=690.21(C50H30N2S=690.85)m / z = 690.21 (C 50 H 30 N 2 S = 690.85) | 1-21-2 | m/z=590.18(C42H26N2S=590.73)m / z = 590.18 (C 42 H 26 N 2 S = 590.73) |
| 1-31-3 | m/z=666.21(C48H30N2S=666.83)m / z = 666.21 (C 48 H 30 N 2 S = 666.83) | 1-41-4 | m/z=666.21(C48H30N2S=666.83)m / z = 666.21 (C 48 H 30 N 2 S = 666.83) |
| 1-51-5 | m/z=640.20(C46H28N2S=640.79)m / z = 640.20 (C 46 H 28 N 2 S = 640.79) | 1-61-6 | m/z=640.20(C46H28N2S=640.79)m / z = 640.20 (C 46 H 28 N 2 S = 640.79) |
| 1-71-7 | m/z=666.21(C48H30N2S=666.83)m / z = 666.21 (C 48 H 30 N 2 S = 666.83) | 1-81-8 | m/z=742.24(C54H34N2S=742.93)m / z = 742.24 (C 54 H 34 N 2 S = 742.93) |
| 1-91-9 | m/z=742.24(C54H34N2S=742.93)m / z = 742.24 (C 54 H 34 N 2 S = 742.93) | 1-101-10 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) |
| 1-111-11 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) | 1-121-12 | m/z=666.21(C48H30N2S=666.83)m / z = 666.21 (C 48 H 30 N 2 S = 666.83) |
| 1-131-13 | m/z=640.20(C46H28N2S=640.79)m / z = 640.20 (C 46 H 28 N 2 S = 640.79) | 1-141-14 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) |
| 1-151-15 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) | 1-161-16 | m/z=690.21(C50H30N2S=690.85)m / z = 690.21 (C 50 H 30 N 2 S = 690.85) |
| 1-171-17 | m/z=690.21(C50H30N2S=690.85)m / z = 690.21 (C 50 H 30 N 2 S = 690.85) | 1-181-18 | m/z=640.20(C46H28N2S=640.79)m / z = 640.20 (C 46 H 28 N 2 S = 640.79) |
| 1-191-19 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) | 1-201-20 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) |
| 1-211-21 | m/z=690.21(C50H30N2S=690.85)m / z = 690.21 (C 50 H 30 N 2 S = 690.85) | 1-221-22 | m/z=690.21(C50H30N2S=690.85)m / z = 690.21 (C 50 H 30 N 2 S = 690.85) |
| 1-231-23 | m/z=590.18(C42H26N2S=590.73)m / z = 590.18 (C 42 H 26 N 2 S = 590.73) | 1-241-24 | m/z=590.18(C42H26N2S=590.73)m / z = 590.18 (C 42 H 26 N 2 S = 590.73) |
| 1-251-25 | m/z=590.18(C42H26N2S=590.73)m / z = 590.18 (C 42 H 26 N 2 S = 590.73) | 1-261-26 | m/z=590.18(C42H26N2S=590.73)m / z = 590.18 (C 42 H 26 N 2 S = 590.73) |
| 1-271-27 | m/z=666.21(C48H30N2S=666.83)m / z = 666.21 (C 48 H 30 N 2 S = 666.83) | 1-281-28 | m/z=666.21(C48H30N2S=666.83)m / z = 666.21 (C 48 H 30 N 2 S = 666.83) |
| 1-291-29 | m/z=640.20(C46H28N2S=640.79)m / z = 640.20 (C 46 H 28 N 2 S = 640.79) | 1-301-30 | m/z=640.20(C46H28N2S=640.79)m / z = 640.20 (C 46 H 28 N 2 S = 640.79) |
| 1-311-31 | m/z=666.21(C48H30N2S=666.83)m / z = 666.21 (C 48 H 30 N 2 S = 666.83) | 1-321-32 | m/z=742.24(C54H34N2S=742.93)m / z = 742.24 (C 54 H 34 N 2 S = 742.93) |
| 1-331-33 | m/z=742.24(C54H34N2S=742.93)m / z = 742.24 (C 54 H 34 N 2 S = 742.93) | 1-341-34 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) |
| 1-351-35 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) | 1-361-36 | m/z=666.21(C48H30N2S=666.83)m / z = 666.21 (C 48 H 30 N 2 S = 666.83) |
| 1-371-37 | m/z=742.24(C54H34N2S=742.93)m / z = 742.24 (C 54 H 34 N 2 S = 742.93) | 1-381-38 | m/z=742.24(C54H34N2S=742.93)m / z = 742.24 (C 54 H 34 N 2 S = 742.93) |
| 1-391-39 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) | 1-401-40 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) |
| 1-411-41 | m/z=640.20(C46H28N2S=640.79)m / z = 640.20 (C 46 H 28 N 2 S = 640.79) | 1-421-42 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) |
| 1-431-43 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) | 1-441-44 | m/z=690.21(C50H30N2S=690.85)m / z = 690.21 (C 50 H 30 N 2 S = 690.85) |
| 1-451-45 | m/z=690.21(C50H30N2S=690.85)m / z = 690.21 (C 50 H 30 N 2 S = 690.85) | 1-461-46 | m/z=640.20(C46H28N2S=640.79)m / z = 640.20 (C 46 H 28 N 2 S = 640.79) |
| 1-471-47 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) | 1-481-48 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) |
| 1-491-49 | m/z=690.21(C50H30N2S=690.85)m / z = 690.21 (C 50 H 30 N 2 S = 690.85) | 1-501-50 | m/z=690.21(C50H30N2S=690.85)m / z = 690.21 (C 50 H 30 N 2 S = 690.85) |
| 1-511-51 | m/z=590.18(C42H26N2S=590.73)m / z = 590.18 (C 42 H 26 N 2 S = 590.73) | 1-521-52 | m/z=590.18(C42H26N2S=590.73)m / z = 590.18 (C 42 H 26 N 2 S = 590.73) |
| 1-531-53 | m/z=590.18(C42H26N2S=590.73)m / z = 590.18 (C 42 H 26 N 2 S = 590.73) | 1-541-54 | m/z=531.11(C36H21NS2=531.69)m / z = 531.11 (C 36 H 21 NS 2 = 531.69) |
| 1-551-55 | m/z=531.11(C36H21NS2=531.69)m / z = 531.11 (C 36 H 21 NS 2 = 531.69) | 1-561-56 | m/z=515.13(C36H21NOS=515.62)m / z = 515.13 (C 36 H 21 NOS = 515.62) |
| 1-571-57 | m/z=744.23(C52H32N4S=743.90)m / z = 744.23 (C 52 H 32 N 4 S = 743.90) | 1-581-58 | m/z=870.28(C62H38N4S=871.06)m / z = 870.28 (C 62 H 38 N 4 S = 871.06) |
| 1-591-59 | m/z=768.23(C54H32N4S=768.92)m / z = 768.23 (C 54 H 32 N 4 S = 768.92) | 1-601-60 | m/z=718.22(C50H30N4S=718.87)m / z = 718.22 (C 50 H 30 N 4 S = 718.87) |
| 1-611-61 | m/z=931.30(C68H41N3S=932.14)m / z = 931.30 (C 68 H 41 N 3 S = 932.14) | 1-621-62 | m/z=808.23(C56H32N4OS=808.94)m / z = 808.23 (C 56 H 32 N 4 OS = 808.94) |
| 1-631-63 | m/z=850.22(C58H34N4S2=851.05)m / z = 850.22 (C 58 H 34 N 4 S 2 = 851.05) | 1-641-64 | m/z=831.32(C57H25D10N5S=832.05)m / z = 831.32 (C 57 H 25 D 10 N 5 S = 832.05) |
| 1-651-65 | m/z=768.23(C54H32N4S=768.92)m / z = 768.23 (C 54 H 32 N 4 S = 768.92) | 1-661-66 | m/z=640.20(C46H28N2S=640.79)m / z = 640.20 (C 46 H 28 N 2 S = 640.79) |
| 1-671-67 | m/z=531.11(C36H21NS2=531.69)m / z = 531.11 (C 36 H 21 NS 2 = 531.69) | 1-681-68 | m/z=708.17(C49H28N2S2=708.89)m / z = 708.17 (C 49 H 28 N 2 S 2 = 708.89) |
| 1-691-69 | m/z=733.19(C52H31NS2=733.94)m / z = 733.19 (C 52 H 31 NS 2 = 733.94) | 1-701-70 | m/z=708.17(C49H28N2S2=708.89)m / z = 708.17 (C 49 H 28 N 2 S 2 = 708.89) |
| 1-711-71 | m/z=565.15(C40H23NOS=565.68)m / z = 565.15 (C 40 H 23 NOS = 565.68) | 1-721-72 | m/z=822.25(C57H34N4OS=822.97)m / z = 822.25 (C 57 H 34 N 4 OS = 822.97) |
| 1-731-73 | m/z=809.21(C56H31N3O2S=809.93)m / z = 809.21 (C 56 H 31 N 3 O 2 S = 809.93) | 1-741-74 | m/z=781.13(C52H31NSSe=780.83)m / z = 781.13 (C 52 H 31 NSSe = 780.83) |
| 1-751-75 | m/z=681.08(C42H23N3SSe=680.68)m / z = 681.08 (C4 2 H 23 N 3 SSe = 680.68) | 1-761-76 | m/z=585.19(C40H31NSSi=585.83)m / z = 585.19 (C 40 H 31 NSSi = 585.83) |
| 1-771-77 | m/z=809.23(C56H35N3SSi=810.05)m / z = 809.23 (C 56 H 35 N 3 SSi = 810.05) | 1-781-78 | m/z=817.28(C61H39NS=818.03)m / z = 817.28 (C 61 H 39 NS = 818.03) |
| 1-791-79 | m/z=817.26(C59H35N3S=817.99)m / z = 817.26 (C 59 H 35 N 3 S = 817.99) | 1-801-80 | m/z=742.28(C50H30N4OS=742.93)m / z = 742.28 (C 50 H 30 N 4 OS = 742.93) |
| 1-811-81 | m/z=574.20(C42H26N2O=574.67)m / z = 574.20 (C 42 H 26 N 2 O = 574.67) | 1-821-82 | m/z=624.22(C46H28N2O=624.73)m / z = 624.22 (C 46 H 28 N 2 O = 624.73) |
| 1-831-83 | m/z=852.29(C62H36N4O=852.98)m / z = 852.29 (C 62 H 36 N 4 O = 852.98) | 1-841-84 | m/z=834.25(C58H34N4OS=834.98)m / z = 834.25 (C 58 H 34 N 4 OS = 834.98) |
| 1-851-85 | m/z=649.24(C49H31NO=649.78)m / z = 649.24 (C 49 H 31 NO = 649.78) | 1-861-86 | m/z=829.24(C61H35NOS=830.00)m / z = 829.24 (C 61 H 35 NOS = 830.00) |
| 1-871-87 | m/z=665.22(C48H31NOSi=665.85)m / z = 665.22 (C 48 H 31 NOSi = 665.85) | 1-881-88 | m/z=563.08(C36H21NOSe=562.52)m / z = 563.08 (C 36 H 21 NOSe = 562.52) |
| 1-891-89 | m/z=600.26(C45H32N2=600.75)m / z = 600.26 (C 45 H 32 N 2 = 600.75) | 1-901-90 | m/z=591.20(C43H29NS=591.76)m / z = 591.20 (C 43 H 29 NS = 591.76) |
| 1-911-91 | m/z=525.21(C39H27NO=525.64)m / z = 525.21 (C 39 H 27 NO = 525.64) | 1-921-92 | m/z=551.26(C42H33N=551.72)m / z = 551.26 (C 42 H 33 N = 551.72) |
| 1-931-93 | m/z=616.23(C44H32N2Si=616.82)m / z = 616.23 (C 44 H 32 N 2 Si = 616.82) | 1-941-94 | m/z=541.19(C38H27NOSi=541.71)m / z = 541.19 (C 38 H 27 NOSi = 541.71) |
| 1-951-95 | m/z=557.16(C38H27NSSi=557.78)m / z = 557.16 (C 38 H 27 NSSi = 557.78) | 1-961-96 | m/z=638.13(C42H26N2Se=637.63)m / z = 638.13 (C 42 H 26 N 2 Se = 637.63) |
| 1-971-97 | m/z=563.08(C36H21NOSe=562.52)m / z = 563.08 (C 36 H 21 NOSe = 562.52) | 1-981-98 | m/z=589.13(C39H27NSe=588.60)m / z = 589.13 (C 39 H 27 NSe = 588.60) |
| 2-12-1 | m/z=590.18(C42H26N2S=590.73)m / z = 590.18 (C 42 H 26 N 2 S = 590.73) | 2-22-2 | m/z=666.21(C48H30N2S=666.83)m / z = 666.21 (C 48 H 30 N 2 S = 666.83) |
| 2-32-3 | m/z=666.21(C48H30N2S=666.83)m / z = 666.21 (C 48 H 30 N 2 S = 666.83) | 2-42-4 | m/z=640.20(C46H28N2S=640.79)m / z = 640.20 (C 46 H 28 N 2 S = 640.79) |
| 2-52-5 | m/z=640.20(C46H28N2S=640.79)m / z = 640.20 (C 46 H 28 N 2 S = 640.79) | 2-62-6 | m/z=666.21(C48H30N2S=666.83)m / z = 666.21 (C 48 H 30 N 2 S = 666.83) |
| 2-72-7 | m/z=742.24(C54H34N2S=742.93)m / z = 742.24 (C 54 H 34 N 2 S = 742.93) | 2-82-8 | m/z=742.24(C54H34N2S=742.93)m / z = 742.24 (C 54 H 34 N 2 S = 742.93) |
| 2-92-9 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) | 2-102-10 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) |
| 2-112-11 | m/z=666.21(C48H30N2S=666.83)m / z = 666.21 (C 48 H 30 N 2 S = 666.83) | 2-122-12 | m/z=742.24(C54H34N2S=742.93)m / z = 742.24 (C 54 H 34 N 2 S = 742.93) |
| 2-132-13 | m/z=742.24(C54H34N2S=742.93)m / z = 742.24 (C 54 H 34 N 2 S = 742.93) | 2-142-14 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) |
| 2-152-15 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) | 2-162-16 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) |
| 2-172-17 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) | 2-182-18 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) |
| 2-192-19 | m/z=690.21(C50H30N2S=690.85)m / z = 690.21 (C 50 H 30 N 2 S = 690.85) | 2-202-20 | m/z=690.21(C50H30N2S=690.85)m / z = 690.21 (C 50 H 30 N 2 S = 690.85) |
| 2-212-21 | m/z=640.20(C46H28N2S=640.79)m / z = 640.20 (C 46 H 28 N 2 S = 640.79) | 2-222-22 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) |
| 2-232-23 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) | 2-242-24 | m/z=690.21(C50H30N2S=690.85)m / z = 690.21 (C 50 H 30 N 2 S = 690.85) |
| 2-252-25 | m/z=742.24(C54H34N2S=742.93)m / z = 742.24 (C 54 H 34 N 2 S = 742.93) | 2-262-26 | m/z=742.24(C54H34N2S=742.93)m / z = 742.24 (C 54 H 34 N 2 S = 742.93) |
| 2-272-27 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) | 2-282-28 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) |
| 2-292-29 | m/z=746.28(C54H38N2S=746.96)m / z = 746.28 (C 54 H 38 N 2 S = 746.96) | 2-302-30 | m/z=796.25(C57H36N2OS=796.97)m / z = 796.25 (C 57 H 36 N 2 OS = 796.97) |
| 2-312-31 | m/z=780.26(C57H36N2S=780.97)m / z = 780.26 (C 57 H 36 N 2 S = 780.97) | 2-322-32 | m/z=743.24(C53H33N3S=743.91)m / z = 743.24 (C 53 H 33 N 3 S = 743.91) |
| 2-332-33 | m/z=531.11(C36H21NS2=531.69)m / z = 531.11 (C 36 H 21 NS 2 = 531.69) | 2-342-34 | m/z=607.14(C42H25NS2=607.78)m / z = 607.14 (C 42 H 25 NS 2 = 607.78) |
| 2-352-35 | m/z=607.14(C42H25NS2=607.78)m / z = 607.14 (C 42 H 25 NS 2 = 607.78) | 2-362-36 | m/z=581.13(C40H23NS2=581.75)m / z = 581.13 (C 40 H 23 NS 2 = 581.75) |
| 2-372-37 | m/z=581.13(C40H23NS2=581.75)m / z = 581.13 (C 40 H 23 NS 2 = 581.75) | 2-382-38 | m/z=515.13(C36H21NOS=515.62)m / z = 515.13 (C 36 H 21 NOS = 515.62) |
| 2-392-39 | m/z=591.17(C42H25NOS=591.72)m / z = 591.17 (C 42 H 25 NOS = 591.72) | 2-402-40 | m/z=591.17(C42H25NOS=591.72)m / z = 591.17 (C 42 H 25 NOS = 591.72) |
| 2-412-41 | m/z=565.15(C40H23NOS=565.68)m / z = 565.15 (C 40 H 23 NOS = 565.68) | 2-422-42 | m/z=565.15(C40H23NOS=565.68)m / z = 565.15 (C 40 H 23 NOS = 565.68) |
| 2-432-43 | m/z=541.19(C39H27NS=541.70)m / z = 541.19 (C 39 H 27 NS = 541.70) | 2-442-44 | m/z=617.21(C45H31NS=617.80)m / z = 617.21 (C 45 H 31 NS = 617.80) |
| 2-452-45 | m/z=617.21(C45H31NS=617.80)m / z = 617.21 (C 45 H 31 NS = 617.80) | 2-462-46 | m/z=591.20(C43H29NS=591.76)m / z = 591.20 (C 43 H 29 NS = 591.76) |
| 2-472-47 | m/z=591.20(C43H29NS=591.76)m / z = 591.20 (C 43 H 29 NS = 591.76) | 2-482-48 | m/z=590.18(C42H26N2S=590.73)m / z = 590.18 (C 42 H 26 N 2 S = 590.73) |
| 2-492-49 | m/z=590.18(C42H26N2S=590.73)m / z = 590.18 (C 42 H 26 N 2 S = 590.73) | 2-502-50 | m/z=590.18(C42H26N2S=590.73)m / z = 590.18 (C 42 H 26 N 2 S = 590.73) |
| 2-512-51 | m/z=590.18(C42H26N2S=590.73)m / z = 590.18 (C 42 H 26 N 2 S = 590.73) | 2-522-52 | m/z=666.21(C48H30N2S=666.83)m / z = 666.21 (C 48 H 30 N 2 S = 666.83) |
| 2-532-53 | m/z=666.21(C48H30N2S=666.83)m / z = 666.21 (C 48 H 30 N 2 S = 666.83) | 2-542-54 | m/z=640.20(C46H28N2S=640.79)m / z = 640.20 (C 46 H 28 N 2 S = 640.79) |
| 2-552-55 | m/z=640.20(C46H28N2S=640.79)m / z = 640.20 (C 46 H 28 N 2 S = 640.79) | 2-562-56 | m/z=666.21(C48H30N2S=666.83)m / z = 666.21 (C 48 H 30 N 2 S = 666.83) |
| 2-572-57 | m/z=742.24(C54H34N2S=742.93)m / z = 742.24 (C 54 H 34 N 2 S = 742.93) | 2-582-58 | m/z=742.24(C54H34N2S=742.93)m / z = 742.24 (C 54 H 34 N 2 S = 742.93) |
| 2-592-59 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) | 2-602-60 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) |
| 2-612-61 | m/z=666.21(C48H30N2S=666.83)m / z = 666.21 (C 48 H 30 N 2 S = 666.83) | 2-622-62 | m/z=742.24(C54H34N2S=742.93)m / z = 742.24 (C 54 H 34 N 2 S = 742.93) |
| 2-632-63 | m/z=742.24(C54H34N2S=742.93)m / z = 742.24 (C 54 H 34 N 2 S = 742.93) | 2-642-64 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) |
| 2-652-65 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) | 2-662-66 | m/z=640.20(C46H28N2S=640.79)m / z = 640.20 (C 46 H 28 N 2 S = 640.79) |
| 2-672-67 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) | 2-682-68 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) |
| 2-692-69 | m/z=690.21(C50H30N2S=690.85)m / z = 690.21 (C 50 H 30 N 2 S = 690.85) | 2-702-70 | m/z=690.21(C50H30N2S=690.85)m / z = 690.21 (C 50 H 30 N 2 S = 690.85) |
| 2-712-71 | m/z=640.20(C46H28N2S=640.79)m / z = 640.20 (C 46 H 28 N 2 S = 640.79) | 2-722-72 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) |
| 2-732-73 | m/z=716.23(C52H32N2S=716.89)m / z = 716.23 (C 52 H 32 N 2 S = 716.89) | 2-742-74 | m/z=690.21(C50H30N2S=690.85)m / z = 690.21 (C 50 H 30 N 2 S = 690.85) |
| 2-752-75 | m/z=690.21(C50H30N2S=690.85)m / z = 690.21 (C 50 H 30 N 2 S = 690.85) | 2-762-76 | m/z=590.18(C42H26N2S=590.73)m / z = 590.18 (C 42 H 26 N 2 S = 590.73) |
| 2-772-77 | m/z=590.18(C42H26N2S=590.73)m / z = 590.18 (C 42 H 26 N 2 S = 590.73) | 2-782-78 | m/z=590.18(C42H26N2S=590.73)m / z = 590.18 (C 42 H 26 N 2 S = 590.73) |
| 2-792-79 | m/z=581.13(C40H23NS2=581.75)m / z = 581.13 (C 40 H 23 NS 2 = 581.75) | 2-802-80 | m/z=581.13(C40H23NS2=581.75)m / z = 581.13 (C 40 H 23 NS 2 = 581.75) |
| 2-812-81 | m/z=515.13(C36H21NOS=515.62)m / z = 515.13 (C 36 H 21 NOS = 515.62) | 2-822-82 | m/z=591.17(C42H25NOS=591.72)m / z = 591.17 (C 42 H 25 NOS = 591.72) |
| 2-832-83 | m/z=591.17(C42H25NOS=591.72)m / z = 591.17 (C 42 H 25 NOS = 591.72) | 2-842-84 | m/z=565.15(C40H23NOS=565.68)m / z = 565.15 (C 40 H 23 NOS = 565.68) |
| 2-852-85 | m/z=565.15(C40H23NOS=565.68)m / z = 565.15 (C 40 H 23 NOS = 565.68) | 2-862-86 | m/z=541.19(C39H27NS=541.70)m / z = 541.19 (C 39 H 27 NS = 541.70) |
| 2-872-87 | m/z=617.21(C45H31NS=617.80)m / z = 617.21 (C 45 H 31 NS = 617.80) | 2-882-88 | m/z=617.21(C45H31NS=617.80)m / z = 617.21 (C 45 H 31 NS = 617.80) |
| 2-892-89 | m/z=531.11(C36H21NS2=531.69)m / z = 531.11 (C 36 H 21 NS 2 = 531.69) | 2-902-90 | m/z=607.14(C42H25NS2=607.78)m / z = 607.14 (C 42 H 25 NS 2 = 607.78) |
| 2-912-91 | m/z=607.14(C42H25NS2=607.78)m / z = 607.14 (C 42 H 25 NS 2 = 607.78) | 2-922-92 | m/z=591.20(C43H29NS=591.76)m / z = 591.20 (C 43 H 29 NS = 591.76) |
| 2-932-93 | m/z=591.20(C43H29NS=591.76)m / z = 591.20 (C 43 H 29 NS = 591.76) | 2-942-94 | m/z=745.23(C51H31N5S=745.89)m / z = 745.23 (C 51 H 31 N 5 S = 745.89) |
| 2-952-95 | m/z=744.23(C52H32N4S=744.90)m / z = 744.23 (C 52 H 32 N 4 S = 744.90) | 2-962-96 | m/z=744.23(C52H32N4S=744.90)m / z = 744.23 (C 52 H 32 N 4 S = 744.90) |
| 2-972-97 | m/z=744.23(C52H32N4S=744.90)m / z = 744.23 (C 52 H 32 N 4 S = 744.90) | 2-982-98 | m/z=718.22(C50H30N4S=718.87)m / z = 718.22 (C 50 H 30 N 4 S = 718.87) |
| 2-992-99 | m/z=745.23(C51H31N5S=745.89)m / z = 745.23 (C 51 H 31 N 5 S = 745.89) | 2-1002-100 | m/z=744.23(C52H32N4S=744.90)m / z = 744.23 (C 52 H 32 N 4 S = 744.90) |
| 2-1012-101 | m/z=744.23(C52H32N4S=744.90)m / z = 744.23 (C 52 H 32 N 4 S = 744.90) | 2-1022-102 | m/z=744.23(C52H32N4S=744.90)m / z = 744.23 (C 52 H 32 N 4 S = 744.90) |
| 2-1032-103 | m/z=718.22(C50H30N4S=718.87)m / z = 718.22 (C 50 H 30 N 4 S = 718.87) | 2-1042-104 | m/z=768.24(C54H32N4S=768.92)m / z = 768.24 (C 54 H 32 N 4 S = 768.92) |
| 2-1052-105 | m/z=834.25(C58H34N4OS=834.98)m / z = 834.25 (C 58 H 34 N 4 OS = 834.98) | 2-1062-106 | m/z=900.24(C62H36N4S2=901.11)m / z = 900.24 (C 62 H 36 N 4 S 2 = 901.11) |
| 2-1072-107 | m/z=844.27(C60H36N4S=845.02)m / z = 844.27 (C 60 H 36 N 4 S = 845.02) | 2-1082-108 | m/z=847.25(C60H3FN3S=848.00)m / z = 847.25 (C 60 H 3 FN 3 S = 848.00) |
| 2-1092-109 | m/z=745.23(C51H31N5S=745.89)m / z = 745.23 (C 51 H 31 N 5 S = 745.89) | 2-1102-110 | m/z=909.32(C67H35D5N2S=910.14)m / z = 909.32 (C 67 H 35 D 5 N 2 S = 910.14) |
| 2-1112-111 | m/z=747.18(C51H29N3S2=747.93)m / z = 747.18 (C 51 H 29 N 3 S 2 = 747.93) | 2-1122-112 | m/z=762.29(C54H30D5N3S=762.97)m / z = 762.29 (C 54 H 30 D 5 N 3 S = 762.97) |
| 2-1132-113 | m/z=789.25(C59H35NS=789.98)m / z = 789.25 (C 59 H 35 NS = 789.98) | 2-1142-114 | m/z=860.26(C60H36N4OS=861.02)m / z = 860.26 (C 60 H 36 N 4 OS = 861.02) |
| 2-1152-115 | m/z=515.13(C36H21NOS=515.62)m / z = 515.13 (C 36 H 21 NOS = 515.62) | 2-1162-116 | m/z=717.21(C52H31NOS=717.87)m / z = 717.21 (C 52 H 31 NOS = 717.87) |
| 2-1172-117 | m/z=770.21(C53H30N4S=770.90)m / z = 770.21 (C 53 H 30 N 4 S = 770.90) | 2-1182-118 | m/z=845.25(C60H35N3OS=846.00)m / z = 845.25 (C 60 H 35 N 3 OS = 846.00) |
| 2-1192-119 | m/z=699.14(C46H25N3S2=699.84)m / z = 699.14 (C 46 H 25 N 3 S 2 = 699.84) | 2-1202-120 | m/z=581.13(C40H23NS2=581.75)m / z = 581.13 (C 40 H 23 NS 2 = 581.75) |
| 2-1212-121 | m/z=785.20(C54H31N3S2=785.97)m / z = 785.20 (C 54 H 31 N 3 S 2 = 785.97) | 2-1222-122 | m/z=824.20(C57H32N2OS2=825.01)m / z = 824.20 (C 57 H 32 N 2 OS 2 = 825.01) |
| 2-1232-123 | m/z=697.19(C49H31NS2=697.91)m / z = 697.19 (C 49 H 31 NS 2 = 697.91) | 2-1242-124 | m/z=624.04(C36H20N2O2SSe=623.58)m / z = 624.04 (C 36 H 20 N 2 O 2 SSe = 623.58) |
| 2-1252-125 | m/z=666.21(C48H30N2S=666.83)m / z = 666.21 (C 48 H 30 N 2 S = 666.83) | 2-1262-126 | m/z=640.20(C46H28N2S=640.79)m / z = 640.20 (C 46 H 28 N 2 S = 640.79) |
| 2-1272-127 | m/z=640.20(C46H28N2S=640.79)m / z = 640.20 (C 46 H 28 N 2 S = 640.79) | 2-1282-128 | m/z=671.24(C48H25D5N2S=671.86)m / z = 671.24 (C 48 H 25 D 5 N 2 S = 671.86) |
| 2-1292-129 | m/z=671.24(C48H25D5N2S=671.86)m / z = 671.24 (C 48 H 25 D 5 N 2 S = 671.86) | 2-1302-130 | m/z=557.16(C38H27NSSi=557.78)m / z = 557.16 (C 38 H 27 NSSi = 557.78) |
| 2-1312-131 | m/z=579.06(C36H21NSSe=579.58)m / z = 579.06 (C 36 H 21 NSSe = 579.58) | 2-1322-132 | m/z=681.19(C48H31NSSi=681.92)m / z = 681.19 (C 48 H 31 NSSi = 681.92) |
| 2-1332-133 | m/z=574.20(C42H26N2O=574.67)m / z = 574.20 (C 42 H 26 N 2 O = 574.67) | 2-1342-134 | m/z=650.24(C48H30N2O=650.76)m / z = 650.24 (C 48 H 30 N 2 O = 650.76) |
| 2-1352-135 | m/z=664.22(C48H28N2O2=664.75)m / z = 664.22 (C 48 H 28 N 2 O 2 = 664.75) | 2-1362-136 | m/z=818.27(C58H34N4O2=818.92)m / z = 818.27 (C 58 H 34 N 4 O 2 = 818.92) |
| 2-1372-137 | m/z=758.21(C52H30N4OS=758.89)m / z = 758.21 (C 52 H 30 N 4 OS = 758.89) | 2-1382-138 | m/z=702.24(C50H30N4O=702.80)m / z = 702.24 (C 50 H 30 N 4 O = 702.80) |
| 2-1392-139 | m/z=729.25(C51H31N5O=729.82)m / z = 729.25 (C 51 H 31 N 5 O = 729.82) | 2-1402-140 | m/z=759.23(C53H33N3OS=759.91)m / z = 759.23 (C 53 H 33 N 3 OS = 759.91) |
| 2-1412-141 | m/z=697.24(C53H31NO=697.82)m / z = 697.24 (C 53 H 31 NO = 697.82) | 2-1422-142 | m/z=739.23(C54H33NOSi=739.93)m / z = 739.23 (C 54 H 33 NOSi = 739.93) |
| 2-1432-143 | m/z=739.14(C50H29NOSe=738.73)m / z = 739.14 (C 50 H 29 NOSe = 738.73) | 2-1442-144 | m/z=650.27(C49H34N2=650.81)m / z = 650.27 (C 49 H 34 N 2 = 650.81) |
| 2-1452-145 | m/z=591.20(C43H29NO=591.76)m / z = 591.20 (C 43 H 29 NO = 591.76) | 2-1462-146 | m/z=525.21(C39H27NO=525.64)m / z = 525.21 (C 39 H 27 NO = 525.64) |
| 2-1472-147 | m/z=551.26(C42H33=551.72)m / z = 551.26 (C 42 H 33 = 551.72) | 2-1482-148 | m/z=616.23(C44H32N2Si=616.82)m / z = 616.23 (C 44 H 32 N 2 Si = 616.82) |
| 2-1492-149 | m/z=557.16(C38H27NSSi=557.78)m / z = 557.16 (C 38 H 27 NSSi = 557.78) | 2-1502-150 | m/z=541.19(C38H27NOSi=541.71)m / z = 541.19 (C 38 H 27 NOSi = 541.71) |
| 2-1512-151 | m/z=583.22(C40H33NSi2=583.87)m / z = 583.22 (C 40 H 33 NSi 2 = 583.87) | 2-1522-152 | m/z=638.13(C42H26N2Se=637.63)m / z = 638.13 (C 42 H 26 N 2 Se = 637.63) |
| 2-1532-153 | m/z=579.06(C36H21NSSe=578.58)m / z = 579.06 (C 36 H 21 NSSe = 578.58) | 2-1542-154 | m/z=589.13(C39H27NSe=588.60)m / z = 589.13 (C 39 H 27 NSe = 588.60) |
[[
합성예Synthetic example
2] 2]
본 발명에 따른 화학식 (2)로 표시되는 화합물(final product 2)은 하기 반응식 4와 같이 Sub 4와 Sub 5가 반응하여 제조된다.The compound represented by the formula (2) according to the present invention (final product 2) is prepared by reacting Sub 4 and Sub 5 as shown in Reaction Scheme 4.
<반응식 4><Reaction Scheme 4>
Sub 4 합성 예시Sub 4 synthesis example
반응식 4의 Sub 4는 하기 반응식 5의 반응경로에 의해 합성될 수 있으며 이에 한정된 것은 아니다. (Hal1는 Br, Cl, I이며, W, R12, R13, R14, g, h, i는 화학식2의 정의와 같다.)Sub 4 of Scheme 4 may be synthesized by the reaction route of Scheme 5 below, but is not limited thereto. (Hal 1 is Br, Cl, I, and W, R 12 , R 13 , R 14 , g, h, i are as defined in Chemical Formula 2.)
<반응식 5><Scheme 5>
1. Sub 4-1 합성예1. Sub 4-1 Synthesis Example
(1) Sub 4-c-1 합성(1) Sub 4-c-1 synthesis
둥근바닥플라스크에 4-bromodibenzo[b,d]furan (50.0 g, 202 mmol)을 Toluene으로 녹인 후에, 1-chloronaphthalen-2-amine (35.9 g, 202 mmol), Pd2(dba)3 (5.56 g, 6.07 mmol), P(t-Bu)3 (2.46 g, 12.1 mmol), NaOt-Bu (38.9 g, 405 mmol)을 첨가하고 100℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축한다. 이후, 생성된 화합물을 실리카겔 칼럼을 적용한 후 재결정하여 생성물 52.2 g (수율 : 75%)을 얻었다.After dissolving 4-bromodibenzo [b, d] furan (50.0 g, 202 mmol) in Toluene in a round bottom flask, 1-chloronaphthalen-2-amine (35.9 g, 202 mmol), Pd 2 (dba) 3 (5.56 g) , 6.07 mmol), P ( t -Bu) 3 (2.46 g, 12.1 mmol), NaO t -Bu (38.9 g, 405 mmol) was added and stirred at 100 ° C. When the reaction is completed, the mixture is extracted with CH 2 Cl 2 and water, and the organic layer is dried over MgSO 4 and concentrated. Thereafter, the resulting compound was recrystallized after applying a silica gel column to obtain 52.2 g (yield: 75%) of the product.
(2) Sub 4-1 합성(2) Sub 4-1 synthesis
Sub 4-c-1 (52.2 g, 152 mmol)을 DMA(300 mL)에 첨가한 뒤 Pd(OAc)2 (1.02 g, 4.55 mmol), K2CO3 (62.9 g, 455 mmol), P(t-Bu)3H·BF4 (11.4 mL, 9.11 mmol) 첨가하고 90℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축한다. 이후, 생성된 화합물을 실리카겔 칼럼을 적용한 후 재결정하여 생성물 37.8 g (수율 : 81%)을 얻었다.Sub 4-c-1 (52.2 g, 152 mmol) was added to DMA (300 mL) followed by Pd (OAc) 2 (1.02 g, 4.55 mmol), K 2 CO 3 (62.9 g, 455 mmol), P ( t-Bu) 3 H · BF 4 (11.4 mL, 9.11 mmol) was added and stirred at 90 ° C. When the reaction is completed, the mixture is extracted with CH 2 Cl 2 and water, and the organic layer is dried over MgSO 4 and concentrated. Thereafter, the resulting compound was recrystallized after applying a silica gel column to obtain 37.8 g (yield: 81%) of the product.
2. Sub 4-16 2. Sub 4-16
합성예Synthetic example
(1) Sub 4-c-16 합성(1) Sub 4-c-16 synthesis
6-bromodinaphtho[1,2-b:1',2'-d]thiophene (50.0 g, 138 mmol), 2-chloroaniline (17.6 g, 138 mmol), Pd2(dba)3 (3.78 g, 4.13 mmol), P(t-Bu)3 (1.67 g, 8.26mmol), NaOt-Bu (26.5 g, 275 mmol)을 Sub 4-c-1의 실험방법과 동일하게 진행하여 생성물 88.0 g (수율 : 78%)를 얻었다.6-bromodinaphtho [1,2-b: 1 ', 2'-d] thiophene (50.0 g, 138 mmol), 2-chloroaniline (17.6 g, 138 mmol), Pd 2 (dba) 3 (3.78 g, 4.13 mmol) ), P ( t -Bu) 3 (1.67 g, 8.26 mmol), NaO t -Bu (26.5 g, 275 mmol) was conducted in the same manner as in Sub 4-c-1, and the product was 88.0 g (yield: 78 %).
(2) Sub 4-16 합성(2) Sub 4-16 synthesis
Sub 4-c-16 (88.0 g, 215 mmol), Pd(OAc)2 (1.45 g, 6.44 mmol), K2CO3 (89.0 g, 644 mmol), P(t-Bu)3H·BF4 (16.1 mL, 12.9 mmol)을 Sub 4-1의 실험방법과 동일하게 진행하여 생성물 69.0 g (수율 : 86%)를 얻었다.Sub 4-c-16 (88.0 g, 215 mmol), Pd (OAc) 2 (1.45 g, 6.44 mmol), K 2 CO 3 (89.0 g, 644 mmol), P (t-Bu) 3 HBF 4 (16.1 mL, 12.9 mmol) was performed in the same manner as in the experiment method of Sub 4-1 to obtain 69.0 g of product (yield: 86%).
3. Sub 4-26 3. Sub 4-26
합성예Synthetic example
(1) Sub 4-c-26 합성(1) Sub 4-c-26 synthesis
6-bromobenzo[b]naphtho[2,1-d]thiophene (50.0 g, 160 mmol), 2-chloroaniline (20.4 g, 160 mmol), Pd2(dba)3 (4.39 g, 4.79 mmol), P(t-Bu)3 (1.94 g, 9.58 mmol), NaOt-Bu (30.7 g, 319 mmol)을 Sub 4-c-1의 실험방법과 동일하게 진행하여 생성물 41.4 g (수율 : 72%)를 얻었다.6-bromobenzo [b] naphtho [2,1-d] thiophene (50.0 g, 160 mmol), 2-chloroaniline (20.4 g, 160 mmol), Pd 2 (dba) 3 (4.39 g, 4.79 mmol), P ( t -Bu) 3 (1.94 g, 9.58 mmol) and NaO t -Bu (30.7 g, 319 mmol) were conducted in the same manner as in Sub 4-c-1, to obtain 41.4 g of product (yield: 72%). .
(2) Sub 4-26 합성(2) Sub 4-26 synthesis
Sub 4-c-26 (41.4 g, 115 mmol), Pd(OAc)2 (0.774 g, 3.45 mmol), K2CO3 (47.7 g, 345 mmol), P(t-Bu)3H·BF4 (8.63 mL, 6.90 mmol)을 Sub 4-1의 실험방법과 동일하게 진행하여 생성물 30.5 g (수율 : 82%)를 얻었다.Sub 4-c-26 (41.4 g, 115 mmol), Pd (OAc) 2 (0.774 g, 3.45 mmol), K 2 CO 3 (47.7 g, 345 mmol), P (t-Bu) 3 HBF 4 (8.63 mL, 6.90 mmol) was carried out in the same manner as in Sub 4-1, to obtain 30.5 g of product (yield: 82%).
4. Sub 4-39 4. Sub 4-39
합성예Synthetic example
(1) Sub 4-a-39 합성(1) Sub 4-a-39 synthesis
3-bromo-9,9-dimethyl-9H-fluorene (50.0 g, 183 mmol) 를 DMF (1 L)에 녹인 후, bis(pinacolato)diboron (51.1 g, 201 mmol), KOAc (53.9 g, 549 mmol), PdCl2(dppf) (4.02 g, 5.49 mmol)를 첨가하고 120oC에서 교반하였다. 반응이 완료되면 증류를 통해 DMF를 제거하고 CH2Cl2와 물로 추출한다. 추출이 완료되면 유기층을 MgSO4로 건조하고 농축한다. 이후, 생성된 화합물을 실리카겔 컬럼을 적용한 후 재결정하여 생성물 45.7 g (수율: 78%)을 얻었다.After dissolving 3-bromo-9,9-dimethyl-9H-fluorene (50.0 g, 183 mmol) in DMF (1 L), bis (pinacolato) diboron (51.1 g, 201 mmol), KOAc (53.9 g, 549 mmol) ), PdCl 2 (dppf) (4.02 g, 5.49 mmol) was added and stirred at 120 ° C. When the reaction is complete, DMF is removed by distillation and extracted with CH 2 Cl 2 and water. When extraction is completed, the organic layer is dried over MgSO 4 and concentrated. Thereafter, the resulting compound was recrystallized after applying a silica gel column to obtain 45.7 g (yield: 78%) of the product.
(2) Sub 4-b-39 합성(2) Sub 4-b-39 synthesis
상기 합성에서 얻어진 Sub 4-a-39 (45.7 g, 143 mmol)를 THF (600 mL)에 녹인 후, 2-bromo-3-nitronaphthalene (36.0 g, 143 mmol), K2CO3 (59.2 g, 428 mmol), Pd(PPh3)4 (9.90 g, 8.57 mmol), 물 (300 mL) 을 첨가하고 80oC에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 생성된 화합물을 실리카겔 칼럼을 적용한 후 재결정하여 생성물 43.3 g (수율: 83%)을 얻었다.Sub 4-a-39 (45.7 g, 143 mmol) obtained in the above synthesis was dissolved in THF (600 mL), 2-bromo-3-nitronaphthalene (36.0 g, 143 mmol), K 2 CO 3 (59.2 g, 428 mmol), Pd (PPh 3 ) 4 (9.90 g, 8.57 mmol), water (300 mL) was added and stirred at 80 ° C. After the reaction was completed, extracted with CH 2 Cl 2 and water, the organic layer was dried over MgSO 4 and concentrated. Thereafter, the resulting compound was recrystallized after applying a silica gel column to obtain 43.3 g (yield: 83%) of the product.
(3) Sub 4-39 합성(3) Sub 4-39 synthesis
상기 합성에서 얻어진 Sub 4-b-39 (43.3 g, 118 mmol)을 o-dichlorobenzene (500 mL)으로 녹인 후, triphenylphosphine (77.7 g, 296 mmol)을 첨가하고 200oC에서 교반하였다. 반응이 완료되면 증류를 통해 o-dichlorobenzene을 제거하고 CH2Cl2와 물로 추출하였다. 유기층을 MgSO4로 건조하고 농축하였다. 이후, 생성된 화합물을 실리카겔 칼럼을 적용한 후 재결정하여 생성물 34.0 g (수율: 86%)을 얻었다.Sub 4-b-39 (43.3 g, 118 mmol) obtained in the above synthesis was dissolved in o- dichlorobenzene (500 mL), triphenylphosphine (77.7 g, 296 mmol) was added and stirred at 200 ° C. When the reaction was completed, o- dichlorobenzene was removed through distillation, and extracted with CH 2 Cl 2 and water. The organic layer was dried over MgSO 4 and concentrated. Thereafter, the produced compound was recrystallized after applying a silica gel column to obtain 34.0 g (yield: 86%) of the product.
5. Sub 4-56 5. Sub 4-56
합성예Synthetic example
(1) Sub 4-a-56 합성(1) Sub 4-a-56 synthesis
3-bromo-5,5-dimethyl-5H-dibenzo[b,d]silole (50.0 g, 173 mmol), bis(pinacolato)diboron (48.3 g, 190 mmol), KOAc (50.9 g, 519 mmol), PdCl2(dppf) (3.79 g, 5.19 mmol)를 상기 Sub 4-a-39의 실험방법과 동일하게 진행하여 생성물 45.9 g (수율 : 79%)를 얻었다.3-bromo-5,5-dimethyl-5H-dibenzo [b, d] silole (50.0 g, 173 mmol), bis (pinacolato) diboron (48.3 g, 190 mmol), KOAc (50.9 g, 519 mmol), PdCl 2 (dppf) (3.79 g, 5.19 mmol) was carried out in the same manner as the experimental method of Sub 4-a-39 to obtain 45.9 g of product (yield: 79%).
(2) Sub 4-b-56 합성(2) Sub 4-b-56 synthesis
상기에서 얻은 Sub 4-a-56 (45.9 g, 137 mmol), 2-bromo-3-nitronaphthalene (34.4 g, 137 mmol), K2CO3 (56.6 g, 410 mmol), Pd(PPh3)4 (9.47 g, 8.19 mmol)을 상기 Sub 4-b-39의 실험방법과 동일하게 진행하여 생성물 43.2 g (수율 : 83%)를 얻었다.Sub 4-a-56 (45.9 g, 137 mmol) obtained above, 2-bromo-3-nitronaphthalene (34.4 g, 137 mmol), K 2 CO 3 (56.6 g, 410 mmol), Pd (PPh 3 ) 4 (9.47 g, 8.19 mmol) was conducted in the same manner as the experimental method of Sub 4-b-39 to obtain 43.2 g of product (yield: 83%).
(3) Sub 4-56 합성(3) Sub 4-56 synthesis
상기에서 얻은 Sub 4-b-56 (43.2 g, 113 mmol), triphenylphosphine (74.3 g, 283 mmol)를 상기 Sub 4-39의 실험방법과 동일하게 진행하여 생성물 33.7 g (수율 : 85%)를 얻었다.Sub 4-b-56 (43.2 g, 113 mmol) and triphenylphosphine (74.3 g, 283 mmol) obtained above were conducted in the same manner as the experimental method of Sub 4-39 to obtain 33.7 g of product (yield: 85%). .
6. Sub 4-69 합성예6. Sub 4-69 Synthesis Example
(1) Sub 4-a-69 합성 (1) Sub 4-a-69 synthesis
1-bromodibenzo[b,d]furan (50.0 g, 202 mmol), bis(pinacolato)diboron (56.5 g, 223 mmol), KOAc (59.6 g, 607 mmol), PdCl2(dppf) (4.44 g, 6.07 mmol)를 상기 Sub 4-a-39의 실험방법과 동일하게 진행하여 생성물 44.0 g (수율 : 74%)를 얻었다.1-bromodibenzo [b, d] furan (50.0 g, 202 mmol), bis (pinacolato) diboron (56.5 g, 223 mmol), KOAc (59.6 g, 607 mmol), PdCl 2 (dppf) (4.44 g, 6.07 mmol ) Was performed in the same manner as the experimental method of Sub 4-a-39 to obtain 44.0 g of product (yield: 74%).
(2) Sub 4-b-69 합성(2) Sub 4-b-69 synthesis
상기에서 얻은 Sub 4-a-69 (44.0 g, 150 mmol), 1-bromo-2-nitronaphthalene (37.7 g, 150 mmol), K2CO3 (62.1 g, 449 mmol), Pd(PPh3)4 (10.4 g, 8.98 mmol)을 상기 Sub 4-b-39의 실험방법과 동일하게 진행하여 생성물 39.6 g (수율 : 78%)를 얻었다.Sub 4-a-69 (44.0 g, 150 mmol) obtained above, 1-bromo-2-nitronaphthalene (37.7 g, 150 mmol), K 2 CO 3 (62.1 g, 449 mmol), Pd (PPh 3 ) 4 (10.4 g, 8.98 mmol) was carried out in the same manner as the experimental method of Sub 4-b-39 to obtain 39.6 g of product (yield: 78%).
(3) Sub 4-69 합성(3) Sub 4-69 synthesis
상기에서 얻은 Sub 4-b-69 (39.6 g, 117 mmol), triphenylphosphine (76.6 g, 292 mmol)를 상기 Sub 4-39의 실험방법과 동일하게 진행하여 생성물 31.2 g (수율 : 87%)를 얻었다.Sub 4-b-69 (39.6 g, 117 mmol) and triphenylphosphine (76.6 g, 292 mmol) obtained above were carried out in the same manner as the experimental method of Sub 4-39 to obtain 31.2 g of product (yield: 87%). .
7. Sub 4-82 7. Sub 4-82
합성예Synthetic example
(1) Sub 4-a-82 합성 (1) Sub 4-a-82 synthesis
6-bromobenzo[b]naphtho[2,1-d]thiophene (50.0 g, 160 mmol), bis(pinacolato)diboron (44.6 g, 176 mmol), KOAc (47.0 g, 479 mmol), PdCl2(dppf) (3.50 g, 4.79 mmol)를 상기 Sub 4-a-39의 실험방법과 동일하게 진행하여 생성물 40.3 g (수율 : 70%)를 얻었다.6-bromobenzo [b] naphtho [2,1-d] thiophene (50.0 g, 160 mmol), bis (pinacolato) diboron (44.6 g, 176 mmol), KOAc (47.0 g, 479 mmol), PdCl 2 (dppf) (3.50 g, 4.79 mmol) was carried out in the same manner as the experimental method of Sub 4-a-39 to obtain 40.3 g of product (yield: 70%).
(2) Sub 4-b-82 합성(2) Sub 4-b-82 synthesis
상기에서 얻은 Sub 4-a-82 (40.3 g, 112 mmol), 1-bromo-2-nitrobenzene (22.6 g, 112 mmol), K2CO3 (46.3 g, 335 mmol), Pd(PPh3)4 (7.75 g, 6.70 mmol)을 상기 Sub 4-b-39의 실험방법과 동일하게 진행하여 생성물 33.0 g (수율 : 83%)를 얻었다.Sub 4-a-82 (40.3 g, 112 mmol) obtained above, 1-bromo-2-nitrobenzene (22.6 g, 112 mmol), K 2 CO 3 (46.3 g, 335 mmol), Pd (PPh 3 ) 4 (7.75 g, 6.70 mmol) was carried out in the same manner as the experimental method of Sub 4-b-39 to obtain 33.0 g of product (yield: 83%).
(3) Sub 4-82 합성(3) Sub 4-82 synthesis
상기에서 얻은 Sub 4-b-82 (33.0 g, 92.7 mmol), triphenylphosphine (60.8 g, 232 mmol)를 상기 Sub 4-39의 실험방법과 동일하게 진행하여 생성물 24.0 g (수율 : 80%)를 얻었다.Sub 4-b-82 (33.0 g, 92.7 mmol) and triphenylphosphine (60.8 g, 232 mmol) obtained above were carried out in the same manner as the experimental method of Sub 4-39 to obtain 24.0 g of product (yield: 80%). .
8. Sub 4-98 8. Sub 4-98
합성예Synthetic example
(1) Sub 4-a-98 합성(1) Sub 4-a-98 synthesis
8-bromobenzo[b]naphtho[1,2-d]selenophene (50.0 g, 139 mmol), bis(pinacolato)diboron (38.8 g, 153 mmol), KOAc (40.9 g, 417 mmol), PdCl2(dppf) (3.05 g, 4.17 mmol)를 상기 Sub 4-a-39의 실험방법과 동일하게 진행하여 생성물 40.7 g (수율 : 72%)를 얻었다.8-bromobenzo [b] naphtho [1,2-d] selenophene (50.0 g, 139 mmol), bis (pinacolato) diboron (38.8 g, 153 mmol), KOAc (40.9 g, 417 mmol), PdCl 2 (dppf) (3.05 g, 4.17 mmol) was carried out in the same manner as the experimental method of Sub 4-a-39 to obtain 40.7 g of product (yield: 72%).
(2) Sub 4-b-98 합성(2) Sub 4-b-98 synthesis
상기에서 얻은 Sub 4-a-98 (40.7 g, 100 mmol), 1-bromo-2-nitrobenzene (20.2 g, 100 mmol), K2CO3 (41.5 g, 300 mmol), Pd(PPh3)4 (6.93 g, 6.00 mmol)을 상기 Sub 4-b-39의 실험방법과 동일하게 진행하여 진행하여 생성물 33.8 g (수율 : 84%)를 얻었다.Sub 4-a-98 (40.7 g, 100 mmol) obtained above, 1-bromo-2-nitrobenzene (20.2 g, 100 mmol), K 2 CO 3 (41.5 g, 300 mmol), Pd (PPh 3 ) 4 (6.93 g, 6.00 mmol) was performed in the same manner as the experimental method of Sub 4-b-39 to obtain 33.8 g (yield: 84%) of the product.
(3) Sub 4-98 합성(3) Sub 4-98 synthesis
상기에서 얻은 Sub 4-b-98 (33.8 g, 84.0 mmol), triphenylphosphine (55.2 g, 210 mmol)를 상기 Sub 4-39의 실험방법과 동일하게 진행하여 생성물 27.4 g (수율 : 88%)를 얻었다.Sub 4-b-98 (33.8 g, 84.0 mmol) and triphenylphosphine (55.2 g, 210 mmol) obtained above were carried out in the same manner as the experiment method of Sub 4-39 to obtain 27.4 g of product (yield: 88%). .
Sub 4의 예시는 다음과 같으나, 이에 한정되는 것은 아니며, 표 5는 Sub 4에 속하는 화합물의 FD-MS(Field Desorption-Mass Spectrometry) 값을 나타낸 것이다.Examples of Sub 4 are as follows, but are not limited thereto, and Table 5 shows FD-MS (Field Desorption-Mass Spectrometry) values of compounds belonging to Sub 4.
| 화합물compound | FD-MSFD-MS | 화합물compound | FD-MSFD-MS |
| Sub4-1Sub4-1 | m/z=307.10(C22H13NO=307.35)m / z = 307.10 (C 22 H 13 NO = 307.35) | Sub4-2Sub4-2 | m/z=323.08(C22H13NS=323.41)m / z = 323.08 (C 22 H 13 NS = 323.41) |
| Sub4-3Sub4-3 | m/z=333.15(C25H19N=333.43)m / z = 333.15 (C 25 H 19 N = 333.43) | Sub4-4Sub4-4 | m/z=349.13(C24H19NSi=349.51)m / z = 349.13 (C 24 H 19 NSi = 349.51) |
| Sub4-5Sub4-5 | m/z=333.15(C25H19N=333.43)m / z = 333.15 (C 25 H 19 N = 333.43) | Sub4-6Sub4-6 | m/z=349.13(C24H19NSi=349.51)m / z = 349.13 (C 24 H 19 NSi = 349.51) |
| Sub4-7Sub4-7 | m/z=307.10(C22H13NO=307.35)m / z = 307.10 (C 22 H 13 NO = 307.35) | Sub4-8Sub4-8 | m/z=323.08(C22H13NS=323.41)m / z = 323.08 (C 22 H 13 NS = 323.41) |
| Sub4-9Sub4-9 | m/z=307.10(C22H13NO=307.35)m / z = 307.10 (C 22 H 13 NO = 307.35) | Sub4-10Sub4-10 | m/z=323.08(C22H13NS=323.41)m / z = 323.08 (C 22 H 13 NS = 323.41) |
| Sub4-11Sub4-11 | m/z=333.15(C25H19N=333.43)m / z = 333.15 (C 25 H 19 N = 333.43) | Sub4-12Sub4-12 | m/z=349.13(C24H19NSi=349.51)m / z = 349.13 (C 24 H 19 NSi = 349.51) |
| Sub4-13Sub4-13 | m/z=307.10(C22H13NO=307.35)m / z = 307.10 (C 22 H 13 NO = 307.35) | Sub4-14Sub4-14 | m/z=323.08(C22H13NS=323.41)m / z = 323.08 (C 22 H 13 NS = 323.41) |
| Sub4-15Sub4-15 | m/z=399.14(C28H21NSi=399.57)m / z = 399.14 (C 28 H 21 NSi = 399.57) | Sub4-16Sub4-16 | m/z=373.09(C26H15NS=373.47)m / z = 373.09 (C 26 H 15 NS = 373.47) |
| Sub4-17Sub4-17 | m/z=383.17(C29H21N=383.49)m / z = 383.17 (C 29 H 21 N = 383.49) | Sub4-18Sub4-18 | m/z=357.12(C26H15NO=357.41)m / z = 357.12 (C 26 H 15 NO = 357.41) |
| Sub4-19Sub4-19 | m/z=307.10(C22H13NO=307.35)m / z = 307.10 (C 22 H 13 NO = 307.35) | Sub4-20Sub4-20 | m/z=323.08(C22H13NS=323.41)m / z = 323.08 (C 22 H 13 NS = 323.41) |
| Sub4-21Sub4-21 | m/z=333.15(C25H19N=333.43)m / z = 333.15 (C 25 H 19 N = 333.43) | Sub4-22Sub4-22 | m/z=349.13(C24H19NSi=349.51)m / z = 349.13 (C 24 H 19 NSi = 349.51) |
| Sub4-23Sub4-23 | m/z=455.17(C35H21N=455.56)m / z = 455.17 (C 35 H 21 N = 455.56) | Sub4-24Sub4-24 | m/z=371.02(C22H13NSe=370.31)m / z = 371.02 (C 22 H 13 NSe = 370.31) |
| Sub4-25Sub4-25 | m/z=307.10(C22H13NO=307.35)m / z = 307.10 (C 22 H 13 NO = 307.35) | Sub4-26Sub4-26 | m/z=323.08(C22H13NS=323.41)m / z = 323.08 (C 22 H 13 NS = 323.41) |
| Sub4-27Sub4-27 | m/z=307.10(C22H13NO=307.35)m / z = 307.10 (C 22 H 13 NO = 307.35) | Sub4-28Sub4-28 | m/z=323.08(C22H13NS=323.41)m / z = 323.08 (C 22 H 13 NS = 323.41) |
| Sub4-29Sub4-29 | m/z=307.10(C22H13NO=307.35)m / z = 307.10 (C 22 H 13 NO = 307.35) | Sub4-30Sub4-30 | m/z=323.08(C22H13NS=323.41)m / z = 323.08 (C 22 H 13 NS = 323.41) |
| Sub4-31Sub4-31 | m/z=333.15(C25H19N=333.43)m / z = 333.15 (C 25 H 19 N = 333.43) | Sub4-32Sub4-32 | m/z=323.08(C22H13NS=323.41)m / z = 323.08 (C 22 H 13 NS = 323.41) |
| Sub4-33Sub4-33 | m/z=357.12(C26H15NO=357.41)m / z = 357.12 (C 26 H 15 NO = 357.41) | Sub4-34Sub4-34 | m/z=373.09(C26H15NS=373.47)m / z = 373.09 (C 26 H 15 NS = 373.47) |
| Sub4-35Sub4-35 | m/z=407.13(C30H17NO=407.47)m / z = 407.13 (C 30 H 17 NO = 407.47) | Sub4-36Sub4-36 | m/z=423.11(C30H17NS=423.53)m / z = 423.11 (C 30 H 17 NS = 423.53) |
| Sub4-37Sub4-37 | m/z=307.10(C22H13NO=307.35)m / z = 307.10 (C 22 H 13 NO = 307.35) | Sub4-38Sub4-38 | m/z=323.08(C22H13NS=323.41)m / z = 323.08 (C 22 H 13 NS = 323.41) |
| Sub4-39Sub4-39 | m/z=333.15(C25H19N=333.43)m / z = 333.15 (C 25 H 19 N = 333.43) | Sub4-40Sub4-40 | m/z=349.13(C24H19NSi=349.51)m / z = 349.13 (C 24 H 19 NSi = 349.51) |
| Sub4-41Sub4-41 | m/z=307.10(C22H13NO=307.35)m / z = 307.10 (C 22 H 13 NO = 307.35) | Sub4-42Sub4-42 | m/z=323.08(C22H13NS=323.41)m / z = 323.08 (C 22 H 13 NS = 323.41) |
| Sub4-43Sub4-43 | m/z=307.10(C22H13NO=307.35)m / z = 307.10 (C 22 H 13 NO = 307.35) | Sub4-44Sub4-44 | m/z=323.08(C22H13NS=323.41)m / z = 323.08 (C 22 H 13 NS = 323.41) |
| Sub4-45Sub4-45 | m/z=333.15(C25H19N=333.43)m / z = 333.15 (C 25 H 19 N = 333.43) | Sub4-46Sub4-46 | m/z=349.13(C24H19NSi=349.51)m / z = 349.13 (C 24 H 19 NSi = 349.51) |
| Sub4-47Sub4-47 | m/z=307.10(C22H13NO=307.35)m / z = 307.10 (C 22 H 13 NO = 307.35) | Sub4-48Sub4-48 | m/z=323.08(C22H13NS=323.41)m / z = 323.08 (C 22 H 13 NS = 323.41) |
| Sub4-49Sub4-49 | m/z=357.12(C26H15NO=357.41)m / z = 357.12 (C 26 H 15 NO = 357.41) | Sub4-50Sub4-50 | m/z=373.09(C26H15NS=373.47)m / z = 373.09 (C 26 H 15 NS = 373.47) |
| Sub4-51Sub4-51 | m/z=357.12(C26H15NO=357.41)m / z = 357.12 (C 26 H 15 NO = 357.41) | Sub4-52Sub4-52 | m/z=373.09(C26H15NS=373.47)m / z = 373.09 (C 26 H 15 NS = 373.47) |
| Sub4-53Sub4-53 | m/z=307.10(C22H13NO=307.35)m / z = 307.10 (C 22 H 13 NO = 307.35) | Sub4-54Sub4-54 | m/z=323.08(C22H13NS=323.41)m / z = 323.08 (C 22 H 13 NS = 323.41) |
| Sub4-55Sub4-55 | m/z=457.18(C35H23N=457.58)m / z = 457.18 (C 35 H 23 N = 457.58) | Sub4-56Sub4-56 | m/z=349.13(C24H19NSi=349.51)m / z = 349.13 (C 24 H 19 NSi = 349.51) |
| Sub4-57Sub4-57 | m/z=333.15(C25H19N=333.43)m / z = 333.15 (C 25 H 19 N = 333.43) | Sub4-58Sub4-58 | m/z=473.16(C34H23NSi=473.65)m / z = 473.16 (C 34 H 23 NSi = 473.65) |
| Sub4-59Sub4-59 | m/z=307.10(C22H13NO=307.35)m / z = 307.10 (C 22 H 13 NO = 307.35) | Sub4-60Sub4-60 | m/z=323.08(C22H13NS=323.41)m / z = 323.08 (C 22 H 13 NS = 323.41) |
| Sub4-61Sub4-61 | m/z=333.15(C25H19N=333.43)m / z = 333.15 (C 25 H 19 N = 333.43) | Sub4-62Sub4-62 | m/z=349.13(C24H19NSi=349.51)m / z = 349.13 (C 24 H 19 NSi = 349.51) |
| Sub4-63Sub4-63 | m/z=307.10(C22H13NO=307.35)m / z = 307.10 (C 22 H 13 NO = 307.35) | Sub4-64Sub4-64 | m/z=323.08(C22H13NS=323.41)m / z = 323.08 (C 22 H 13 NS = 323.41) |
| Sub4-65Sub4-65 | m/z=483.17(C29H21N=383.49)m / z = 483.17 (C 29 H 21 N = 383.49) | Sub4-66Sub4-66 | m/z=399.14(C28H21NSi=399.57)m / z = 399.14 (C 28 H 21 NSi = 399.57) |
| Sub4-67Sub4-67 | m/z=507.20(C39H25N=507.64)m / z = 507.20 (C 39 H 25 N = 507.64) | Sub4-68Sub4-68 | m/z=523.18(C38H25NSi=523.71)m / z = 523.18 (C 38 H 25 NSi = 523.71) |
| Sub4-69Sub4-69 | m/z=307.10(C22H13NO=307.35)m / z = 307.10 (C 22 H 13 NO = 307.35) | Sub4-70Sub4-70 | m/z=323.08(C22H13NS=323.41)m / z = 323.08 (C 22 H 13 NS = 323.41) |
| Sub4-71Sub4-71 | m/z=333.15(C25H19N=333.43)m / z = 333.15 (C 25 H 19 N = 333.43) | Sub4-72Sub4-72 | m/z=471.14(C34H21NSi=471.63)m / z = 471.14 (C 34 H 21 NSi = 471.63) |
| Sub4-73Sub4-73 | m/z=307.10(C22H13NO=307.35)m / z = 307.10 (C 22 H 13 NO = 307.35) | Sub4-74Sub4-74 | m/z=323.08(C22H13NS=323.41)m / z = 323.08 (C 22 H 13 NS = 323.41) |
| Sub4-75Sub4-75 | m/z=333.15(C25H19N=333.43)m / z = 333.15 (C 25 H 19 N = 333.43) | Sub4-76Sub4-76 | m/z=371.02(C22H13NSe=370.31)m / z = 371.02 (C 22 H 13 NSe = 370.31) |
| Sub4-77Sub4-77 | m/z=307.10(C22H13NO=307.35)m / z = 307.10 (C 22 H 13 NO = 307.35) | Sub4-78Sub4-78 | m/z=323.08(C22H13NS=323.41)m / z = 323.08 (C 22 H 13 NS = 323.41) |
| Sub4-79Sub4-79 | m/z=333.15(C25H19N=333.43)m / z = 333.15 (C 25 H 19 N = 333.43) | Sub4-80Sub4-80 | m/z=349.13(C24H19NSi=349.51)m / z = 349.13 (C 24 H 19 NSi = 349.51) |
| Sub4-81Sub4-81 | m/z=307.10(C22H13NO=307.35)m / z = 307.10 (C 22 H 13 NO = 307.35) | Sub4-82Sub4-82 | m/z=323.08(C22H13NS=323.41)m / z = 323.08 (C 22 H 13 NS = 323.41) |
| Sub4-83Sub4-83 | m/z=383.17(C29H21N=383.49)m / z = 383.17 (C 29 H 21 N = 383.49) | Sub4-84Sub4-84 | m/z=421.04(C26H15NSe=420.37)m / z = 421.04 (C 26 H 15 NSe = 420.37) |
| Sub4-85Sub4-85 | m/z=373.09(C26H15NS=373.47)m / z = 373.09 (C 26 H 15 NS = 373.47) | Sub4-86Sub4-86 | m/z=357.12(C26H15NO=357.41)m / z = 357.12 (C 26 H 15 NO = 357.41) |
| Sub4-87Sub4-87 | m/z=307.10(C22H13NO=307.35)m / z = 307.10 (C 22 H 13 NO = 307.35) | Sub4-88Sub4-88 | m/z=323.08(C22H13NS=323.41)m / z = 323.08 (C 22 H 13 NS = 323.41) |
| Sub4-89Sub4-89 | m/z=333.15(C25H19N=333.43)m / z = 333.15 (C 25 H 19 N = 333.43) | Sub4-90Sub4-90 | m/z=349.13(C24H19NSi=349.51)m / z = 349.13 (C 24 H 19 NSi = 349.51) |
| Sub4-91Sub4-91 | m/z=307.10(C22H13NO=307.35)m / z = 307.10 (C 22 H 13 NO = 307.35) | Sub4-92Sub4-92 | m/z=323.08(C22H13NS=323.41)m / z = 323.08 (C 22 H 13 NS = 323.41) |
| Sub4-93Sub4-93 | m/z=333.15(C25H19N=333.43)m / z = 333.15 (C 25 H 19 N = 333.43) | Sub4-94Sub4-94 | m/z=349.13(C24H19NSi=349.51)m / z = 349.13 (C 24 H 19 NSi = 349.51) |
| Sub4-95Sub4-95 | m/z=307.10(C22H13NO=307.35)m / z = 307.10 (C 22 H 13 NO = 307.35) | Sub4-96Sub4-96 | m/z=323.08(C22H13NS=323.41)m / z = 323.08 (C 22 H 13 NS = 323.41) |
| Sub4-97Sub4-97 | m/z=333.15(C25H19N=333.43)m / z = 333.15 (C 25 H 19 N = 333.43) | Sub4-98Sub4-98 | m/z=371.02(C22H13NSe=370.31)m / z = 371.02 (C 22 H 13 NSe = 370.31) |
| Sub4-99Sub4-99 | m/z=307.10(C22H13NO=307.35)m / z = 307.10 (C 22 H 13 NO = 307.35) | Sub4-100Sub4-100 | m/z=323.08(C22H13NS=323.41)m / z = 323.08 (C 22 H 13 NS = 323.41) |
| Sub4-101Sub4-101 | m/z=383.17(C29H21N=383.49)m / z = 383.17 (C 29 H 21 N = 383.49) | Sub4-102Sub4-102 | m/z=399.14(C28H21NSi=399.57)m / z = 399.14 (C 28 H 21 NSi = 399.57) |
| Sub4-103Sub4-103 | m/z=373.09(C26H15NS=373.47)m / z = 373.09 (C 26 H 15 NS = 373.47) | Sub4-104Sub4-104 | m/z=357.12(C26H15NO=357.41)m / z = 357.12 (C 26 H 15 NO = 357.41) |
Sub 5의 예시Sub 5 example
반응식 4의 Sub 5의 예시는 하기와 같으며 이에 한정된 것은 아니다. Examples of Sub 5 of Scheme 4 are as follows and are not limited thereto.
| 화합물compound | FD-MSFD-MS | 화합물compound | FD-MSFD-MS |
| Sub5-1Sub5-1 | m/z=267.06(C15H10ClN3=267.72)m / z = 267.06 (C 15 H 10 ClN 3 = 267.72) | Sub5-2Sub5-2 | m/z=277.12(C15D10ClN3=277.78)m / z = 277.12 (C 15 D 10 ClN 3 = 277.78) |
| Sub5-3Sub5-3 | m/z=343.09(C21H14ClN3=343.81)m / z = 343.09 (C 21 H 14 ClN 3 = 343.81) | Sub5-4Sub5-4 | m/z=343.09(C21H14ClN3=343.81)m / z = 343.09 (C 21 H 14 ClN 3 = 343.81) |
| Sub5-5Sub5-5 | m/z=419.12(C27H18ClN3=419.91)m / z = 419.12 (C 27 H 18 ClN 3 = 419.91) | Sub5-6Sub5-6 | m/z=419.12(C27H18ClN3=419.91)m / z = 419.12 (C 27 H 18 ClN 3 = 419.91) |
| Sub5-7Sub5-7 | m/z=419.12(C27H18ClN3=419.91)m / z = 419.12 (C 27 H 18 ClN 3 = 419.91) | Sub5-8Sub5-8 | m/z=317.07(C19H12ClN3=317.78)m / z = 317.07 (C 19 H 12 ClN 3 = 317.78) |
| Sub5-9Sub5-9 | m/z=317.07(C19H12ClN3=317.78)m / z = 317.07 (C 19 H 12 ClN 3 = 317.78) | Sub5-10Sub5-10 | m/z=367.09(C23H14ClN3=367.84)m / z = 367.09 (C 23 H 14 ClN 3 = 367.84) |
| Sub5-11Sub5-11 | m/z=367.09(C23H14ClN3=367.84)m / z = 367.09 (C 23 H 14 ClN 3 = 367.84) | Sub5-12Sub5-12 | m/z=367.09(C23H14ClN3=367.84)m / z = 367.09 (C 23 H 14 ClN 3 = 367.84) |
| Sub5-13Sub5-13 | m/z=367.09(C23H14ClN3=367.84)m / z = 367.09 (C 23 H 14 ClN 3 = 367.84) | Sub5-14Sub5-14 | m/z=367.09(C23H14ClN3=367.84)m / z = 367.09 (C 23 H 14 ClN 3 = 367.84) |
| Sub5-15Sub5-15 | m/z=367.09(C23H14ClN3=367.84)m / z = 367.09 (C 23 H 14 ClN 3 = 367.84) | Sub5-16Sub5-16 | m/z=387.04(C21H14ClN3=388.27)m / z = 387.04 (C 21 H 14 ClN 3 = 388.27) |
| Sub5-17Sub5-17 | m/z=387.04(C21H14ClN3=388.27)m / z = 387.04 (C 21 H 14 ClN 3 = 388.27) | Sub5-18Sub5-18 | m/z=373.04(C21H12ClN3S=373.86)m / z = 373.04 (C 21 H 12 ClN 3 S = 373.86) |
| Sub5-19Sub5-19 | m/z=373.04(C21H12ClN3S=373.86)m / z = 373.04 (C 21 H 12 ClN 3 S = 373.86) | Sub5-20Sub5-20 | m/z=373.04(C21H12ClN3S=373.86)m / z = 373.04 (C 21 H 12 ClN 3 S = 373.86) |
| Sub5-21Sub5-21 | m/z=373.04(C21H12ClN3S=373.86)m / z = 373.04 (C 21 H 12 ClN 3 S = 373.86) | Sub5-22Sub5-22 | m/z=357.07(C21H12ClN3O=357.80)m / z = 357.07 (C 21 H 12 ClN 3 O = 357.80) |
| Sub5-23Sub5-23 | m/z=357.07(C21H12ClN3O=357.80)m / z = 357.07 (C 21 H 12 ClN 3 O = 357.80) | Sub5-24Sub5-24 | m/z=357.07(C21H12ClN3O=357.80)m / z = 357.07 (C 21 H 12 ClN 3 O = 357.80) |
| Sub5-25Sub5-25 | m/z=357.07(C21H12ClN3O=357.80)m / z = 357.07 (C 21 H 12 ClN 3 O = 357.80) | Sub5-26Sub5-26 | m/z=432.11(C27H17ClN4=432.91)m / z = 432.11 (C 27 H 17 ClN 4 = 432.91) |
| Sub5-27Sub5-27 | m/z=432.11(C27H17ClN4=432.91)m / z = 432.11 (C 27 H 17 ClN 4 = 432.91) | Sub5-28Sub5-28 | m/z=432.11(C27H17ClN4=432.91)m / z = 432.11 (C 27 H 17 ClN 4 = 432.91) |
| Sub5-29Sub5-29 | m/z=383.12(C24H18ClN3=383.88)m / z = 383.12 (C 24 H 18 ClN 3 = 383.88) | Sub5-30Sub5-30 | m/z=383.12(C24H18ClN3=383.88)m / z = 383.12 (C 24 H 18 ClN 3 = 383.88) |
| Sub5-31Sub5-31 | m/z=383.12(C24H18ClN3=383.88)m / z = 383.12 (C 24 H 18 ClN 3 = 383.88) | Sub5-32Sub5-32 | m/z=383.12(C24H18ClN3=383.88)m / z = 383.12 (C 24 H 18 ClN 3 = 383.88) |
| Sub5-33Sub5-33 | m/z=463.05(C27H14ClN3OS=463.94)m / z = 463.05 (C 27 H 14 ClN 3 OS = 463.94) | Sub5-34Sub5-34 | m/z=447.08(C27H14ClN3O2=447.88)m / z = 447.08 (C 27 H 14 ClN 3 O 2 = 447.88) |
Final products 2의 합성 예시Synthesis example of Final products 2
둥근바닥플라스크에 Sub 4 (1 당량)을 Toluene으로 녹인 후에, Sub 5 (1.1 당량), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.1 당량), NaOt-Bu (3 당량)을 첨가하고 100℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축한 후 생성된 화합물을 silicagel column 및 재결정하여 Final product 2를 얻었다.After dissolving Sub 4 (1 eq) in a round bottom flask with Toluene, Sub 5 (1.1 eq), Pd 2 (dba) 3 (0.03 eq), P ( t -Bu) 3 (0.1 eq), NaO t -Bu (3 eq.) Was added and stirred at 100 ° C. After the reaction was completed, the organic layer was extracted with CH 2 Cl 2 and water, dried and concentrated with MgSO 4 , and then the resulting compound was silicagel column and recrystallized to obtain Final product 2.
1. 3-1 합성예1. 3-1 Synthesis Example
Sub 4-1 (37.8 g, 123 mmol), Toluene (500 mL), Sub 5-1 (32.9 g, 123 mmol), Pd2(dba)3 (3.38 g, 3.69 mmol), P(t-Bu)3 (1.49 g, 7.38 mmol), NaOt-Bu (23.6 g, 246 mmol)을 첨가하고 100℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축한 후 생성된 화합물을 silicagel column 및 재결정하여 생성물 51.7 g (수율: 78%)를 얻었다Sub 4-1 (37.8 g, 123 mmol), Toluene (500 mL), Sub 5-1 (32.9 g, 123 mmol), Pd 2 (dba) 3 (3.38 g, 3.69 mmol), P ( t -Bu) 3 (1.49 g, 7.38 mmol), NaO t -Bu (23.6 g, 246 mmol) was added and stirred at 100 ° C. After the reaction was completed, extracted with CH 2 Cl 2 and water, the organic layer was dried over MgSO 4 and concentrated, and the resulting compound was silicagel column and recrystallized to obtain 51.7 g of product (yield: 78%).
2. 3-16 합성예2. 3-16 Synthesis Example
Sub 4-16 (69.0 g, 185 mmol), Sub 5-1 (49.5 g, 185 mmol), Pd2(dba)3 (5.08 g, 5.54 mmol), P(t-Bu)3 (2.24 g, 11.1 mmol), NaOt-Bu (35.5 g, 370 mmol)을 상기 3-1의 합성방법을 이용하여 최종 생성물 79.3 g (수율: 71%)를 얻었다.Sub 4-16 (69.0 g, 185 mmol), Sub 5-1 (49.5 g, 185 mmol), Pd 2 (dba) 3 (5.08 g, 5.54 mmol), P ( t -Bu) 3 (2.24 g, 11.1 mmol), NaO t -Bu (35.5 g, 370 mmol) was obtained 79.3 g (yield: 71%) of the final product using the synthesis method of 3-1.
3. 3-26 합성예3. 3-26 Synthesis Example
Sub 4-26 (30.5 g, 94.3 mmol), Sub 5-3 (32.4 g, 94.3 mmol), Pd2(dba)3 (2.59 g, 2.83 mmol), P(t-Bu)3 (1.14 g, 5.66 mmol), NaOt-Bu (18.1 g, 189 mmol)을 상기 3-1의 합성방법을 이용하여 최종 생성물 39.9 g (수율: 67%)를 얻었다.Sub 4-26 (30.5 g, 94.3 mmol), Sub 5-3 (32.4 g, 94.3 mmol), Pd 2 (dba) 3 (2.59 g, 2.83 mmol), P ( t -Bu) 3 (1.14 g, 5.66 mmol), NaO t -Bu (18.1 g, 189 mmol) was obtained 39.9 g (yield: 67%) of the final product using the synthesis method of 3-1.
4. 3-39 합성예4. 3-39 Synthesis Example
Sub 4-39 (34.0 g, 102 mmol), Sub 5-1 (27.3 g, 102 mmol), Pd2(dba)3 (2.80 g, 3.06 mmol), P(t-Bu)3 (1.24 g, 6.12 mmol), NaOt-Bu (19.6 g, 204 mmol)을 상기 3-1의 합성방법을 이용하여 최종 생성물 45.5 g (수율: 79%)를 얻었다.Sub 4-39 (34.0 g, 102 mmol), Sub 5-1 (27.3 g, 102 mmol), Pd 2 (dba) 3 (2.80 g, 3.06 mmol), P ( t -Bu) 3 (1.24 g, 6.12 mmol), NaO t -Bu (19.6 g, 204 mmol) was obtained 45.5 g (yield: 79%) of the final product using the synthesis method of 3-1.
5. 3-56 합성예5. 3-56 Synthesis Example
Sub 4-56 (33.7 g, 96.4 mmol), Sub 5-8 (30.6 g, 96.4 mmol), Pd2(dba)3 (2.65 g, 2.89 mmol), P(t-Bu)3 (1.17 g, 5.79 mmol), NaOt-Bu (18.5 g, 193 mmol)을 상기 3-1의 합성방법을 이용하여 최종 생성물 45.0 g (수율: 74%)를 얻었다.Sub 4-56 (33.7 g, 96.4 mmol), Sub 5-8 (30.6 g, 96.4 mmol), Pd 2 (dba) 3 (2.65 g, 2.89 mmol), P ( t -Bu) 3 (1.17 g, 5.79 mmol), NaO t -Bu (18.5 g, 193 mmol) was obtained 45.0 g (yield: 74%) of the final product using the synthesis method of 3-1.
6. 3-69 합성예6. 3-69 Synthesis Example
Sub 4-69 (31.2 g, 102 mmol), Sub 5-9 (32.3 g, 102 mmol), Pd2(dba)3 (2.79 g, 3.05 mmol), P(t-Bu)3 (1.23 g, 6.09 mmol), NaOt-Bu (19.5 g, 203 mmol)을 상기 3-1의 합성방법을 이용하여 최종 생성물 46.0 g (수율: 77%)를 얻었다.Sub 4-69 (31.2 g, 102 mmol), Sub 5-9 (32.3 g, 102 mmol), Pd 2 (dba) 3 (2.79 g, 3.05 mmol), P ( t -Bu) 3 (1.23 g, 6.09 mmol), NaO t -Bu (19.5 g, 203 mmol) was obtained 46.0 g (yield: 77%) of the final product using the synthesis method of 3-1.
7. 3-82 합성예7. 3-82 Synthesis Example
Sub 4-82 (24.0 g, 74.2 mmol), Sub 5-1 (19.9 g, 74.2 mmol), Pd2(dba)3 (2.04 g, 2.23 mmol), P(t-Bu)3 (0.901 g, 4.45 mmol), NaOt-Bu (14.3 g, 148 mmol)을 상기 3-1의 합성방법을 이용하여 최종 생성물 29.6 g (수율: 72%)를 얻었다.Sub 4-82 (24.0 g, 74.2 mmol), Sub 5-1 (19.9 g, 74.2 mmol), Pd 2 (dba) 3 (2.04 g, 2.23 mmol), P ( t -Bu) 3 (0.901 g, 4.45 mmol), NaO t -Bu (14.3 g, 148 mmol) was obtained by using the synthesis method of 3-1 to obtain a final product 29.6 g (yield: 72%).
8. 3-98 합성예8. 3-98 Synthesis Example
Sub 4-98 (27.4 g, 74.0 mmol), Sub 5-1 (19.8 g, 74.0 mmol), Pd2(dba)3 (2.03 g, 2.22 mmol), P(t-Bu)3 (0.898 g, 4.44 mmol), NaOt-Bu (14.2 g, 148 mmol)을 상기 3-1의 합성방법을 이용하여 최종 생성물 34.2 g (수율: 77%)를 얻었다.Sub 4-98 (27.4 g, 74.0 mmol), Sub 5-1 (19.8 g, 74.0 mmol), Pd 2 (dba) 3 (2.03 g, 2.22 mmol), P ( t -Bu) 3 (0.898 g, 4.44 mmol), NaO t -Bu (14.2 g, 148 mmol) was obtained 34.2 g (yield: 77%) of the final product using the synthesis method of 3-1.
| 화합물compound | FD-MSFD-MS | 화합물compound | FD-MSFD-MS |
| 3-13-1 | m/z=538.18(C37H22N4O=538.61)m / z = 538.18 (C 37 H 22 N 4 O = 538.61) | 3-23-2 | m/z=554.16(C37H22N4S=554.67)m / z = 554.16 (C 37 H 22 N 4 S = 554.67) |
| 3-33-3 | m/z=614.25(C44H30N4=614.75)m / z = 614.25 (C 44 H 30 N 4 = 614.75) | 3-43-4 | m/z=630.22(C43H30N4Si=630.83)m / z = 630.22 (C 43 H 30 N 4 Si = 630.83) |
| 3-53-5 | m/z=640.26(C46H32N4=640.79)m / z = 640.26 (C 46 H 32 N 4 = 640.79) | 3-63-6 | m/z=656.24(C45H32N4Si=656.86)m / z = 656.24 (C 45 H 32 N 4 Si = 656.86) |
| 3-73-7 | m/z=538.18(C37H22N4O=538.61)m / z = 538.18 (C 37 H 22 N 4 O = 538.61) | 3-83-8 | m/z=554.16(C37H22N4S=554.67)m / z = 554.16 (C 37 H 22 N 4 S = 554.67) |
| 3-93-9 | m/z=538.18(C37H22N4O=538.61)m / z = 538.18 (C 37 H 22 N 4 O = 538.61) | 3-103-10 | m/z=554.16(C37H22N4S=554.67)m / z = 554.16 (C 37 H 22 N 4 S = 554.67) |
| 3-113-11 | m/z=716.29(C52H36N4=716.89)m / z = 716.29 (C 52 H 36 N 4 = 716.89) | 3-123-12 | m/z=732.27(C51H36N4Si=732.96)m / z = 732.27 (C 51 H 36 N 4 Si = 732.96) |
| 3-133-13 | m/z=538.18(C37H22N4O=538.61)m / z = 538.18 (C 37 H 22 N 4 O = 538.61) | 3-143-14 | m/z=554.16(C37H22N4S=554.67)m / z = 554.16 (C 37 H 22 N 4 S = 554.67) |
| 3-153-15 | m/z=730.16(C51H34N4Si=730.95)m / z = 730.16 (C 51 H 34 N 4 Si = 730.95) | 3-163-16 | m/z=604.17(C41H24N4S=604.73)m / z = 604.17 (C 41 H 24 N 4 S = 604.73) |
| 3-173-17 | m/z=714.28(C52H34N4=714.87)m / z = 714.28 (C 52 H 34 N 4 = 714.87) | 3-183-18 | m/z=588.20(C41H24N4O=588.67)m / z = 588.20 (C 41 H 24 N 4 O = 588.67) |
| 3-193-19 | m/z=538.18(C37H22N4O=538.61)m / z = 538.18 (C 37 H 22 N 4 O = 538.61) | 3-203-20 | m/z=554.16(C37H22N4S=554.67)m / z = 554.16 (C 37 H 22 N 4 S = 554.67) |
| 3-213-21 | m/z=564.23(C40H28N4=564.69)m / z = 564.23 (C 40 H 28 N 4 = 564.69) | 3-223-22 | m/z=580.21(C39H28N4Si=580.77)m / z = 580.21 (C 39 H 28 N 4 Si = 580.77) |
| 3-233-23 | m/z=686.25(C50H30N4=686.82)m / z = 686.25 (C 50 H 30 N 4 = 686.82) | 3-243-24 | m/z=602.10(C34H22N4Se=580.77)m / z = 602.10 (C 34 H 22 N 4 Se = 580.77) |
| 3-253-25 | m/z=686.25(C50H30N4=686.82)m / z = 686.25 (C 50 H 30 N 4 = 686.82) | 3-263-26 | m/z=630.19(C43H26N4S=630.77)m / z = 630.19 (C 43 H 26 N 4 S = 630.77) |
| 3-273-27 | m/z=614.21(C43H26N4O=630.71)m / z = 614.21 (C 43 H 26 N 4 O = 630.71) | 3-283-28 | m/z=630.19(C43H26N4S=630.77)m / z = 630.19 (C 43 H 26 N 4 S = 630.77) |
| 3-293-29 | m/z=538.18(C37H22N4O=538.61)m / z = 538.18 (C 37 H 22 N 4 O = 538.61) | 3-303-30 | m/z=554.16(C37H22N4S=554.67)m / z = 554.16 (C 37 H 22 N 4 S = 554.67) |
| 3-313-31 | m/z=614.255(C44H30N4=614.75)m / z = 614.255 (C 44 H 30 N 4 = 614.75) | 3-323-32 | m/z=630.19(C43H26N4S=630.77)m / z = 630.19 (C 43 H 26 N 4 S = 630.77) |
| 3-333-33 | m/z=588.20(C41H24N4O=588.67)m / z = 588.20 (C 41 H 24 N 4 O = 588.67) | 3-343-34 | m/z=680.20(C47H28N4S=680.83)m / z = 680.20 (C 47 H 28 N 4 S = 680.83) |
| 3-353-35 | m/z=688.23(C49H28N4O=688.79)m / z = 688.23 (C 49 H 28 N 4 O = 688.79) | 3-363-36 | m/z=704.20(C49H28N4S=704.85)m / z = 704.20 (C 49 H 28 N 4 S = 704.85) |
| 3-373-37 | m/z=538.18(C37H22N4O=538.61)m / z = 538.18 (C 37 H 22 N 4 O = 538.61) | 3-383-38 | m/z=554.16(C37H22N4S=554.67)m / z = 554.16 (C 37 H 22 N 4 S = 554.67) |
| 3-393-39 | m/z=564.23(C40H28N4=564.69)m / z = 564.23 (C 40 H 28 N 4 = 564.69) | 3-403-40 | m/z=580.21(C39H28N4Si=580.77)m / z = 580.21 (C 39 H 28 N 4 Si = 580.77) |
| 3-413-41 | m/z=644.17(C43H24N4OS=644.75)m / z = 644.17 (C 43 H 24 N 4 OS = 644.75) | 3-423-42 | m/z=654.19(C45H26N4S=654.79)m / z = 654.19 (C 45 H 26 N 4 S = 654.79) |
| 3-433-43 | m/z=538.18(C37H22N4O=538.61)m / z = 538.18 (C 37 H 22 N 4 O = 538.61) | 3-443-44 | m/z=630.19(C43H26N4S=630.77)m / z = 630.19 (C 43 H 26 N 4 S = 630.77) |
| 3-453-45 | m/z=729.29(C52H35N5=729.89)m / z = 729.29 (C 52 H 35 N 5 = 729.89) | 3-463-46 | m/z=686.20(C45H30N4SSi=686.91)m / z = 686.20 (C 45 H 30 N 4 SSi = 686.91) |
| 3-473-47 | m/z=538.18(C37H22N4O=538.61)m / z = 538.18 (C 37 H 22 N 4 O = 538.61) | 3-483-48 | m/z=630.19(C43H26N4S=630.77)m / z = 630.19 (C 43 H 26 N 4 S = 630.77) |
| 3-493-49 | m/z=664.23(C47H28N4O=664.77)m / z = 664.23 (C 47 H 28 N 4 O = 664.77) | 3-503-50 | m/z=654.19(C45H26N4S=654.79)m / z = 654.19 (C 45 H 26 N 4 S = 654.79) |
| 3-513-51 | m/z=638.21(C45H26N4O=638.73)m / z = 638.21 (C 45 H 26 N 4 O = 638.73) | 3-523-52 | m/z=704.20(C49H28N4S=704.85)m / z = 704.20 (C 49 H 28 N 4 S = 704.85) |
| 3-533-53 | m/z=538.18(C37H22N4O=538.61)m / z = 538.18 (C 37 H 22 N 4 O = 538.61) | 3-543-54 | m/z=554.16(C37H22N4S=554.67)m / z = 554.16 (C 37 H 22 N 4 S = 554.67) |
| 3-553-55 | m/z=738.28(C54H34N4=738.89)m / z = 738.28 (C 54 H 34 N 4 = 738.89) | 3-563-56 | m/z=630.22(C43H30N4Si=630.83)m / z = 630.22 (C 43 H 30 N 4 Si = 630.83) |
| 3-573-57 | m/z=640.26(C46H32N4=640.79)m / z = 640.26 (C 46 H 32 N 4 = 640.79) | 3-583-58 | m/z=780.27(C55H36N4Si=781.01)m / z = 780.27 (C 55 H 36 N 4 Si = 781.01) |
| 3-593-59 | m/z=644.17(C43H24N4OS=644.75)m / z = 644.17 (C 43 H 24 N 4 OS = 644.75) | 3-603-60 | m/z=554.16(C37H22N4S=554.67)m / z = 554.16 (C 37 H 22 N 4 S = 554.67) |
| 3-613-61 | m/z=564.23(C40H28N4=564.69)m / z = 564.23 (C 40 H 28 N 4 = 564.69) | 3-623-62 | m/z=580.21(C39H28N4Si=580.77)m / z = 580.21 (C 39 H 28 N 4 Si = 580.77) |
| 3-633-63 | m/z=654.24(C46H30N4O=654.77)m / z = 654.24 (C 46 H 30 N 4 O = 654.77) | 3-643-64 | m/z=554.16(C37H22N4S=554.67)m / z = 554.16 (C 37 H 22 N 4 S = 554.67) |
| 3-653-65 | m/z=614.25(C44H30N4=614.75)m / z = 614.25 (C 44 H 30 N 4 = 614.75) | 3-663-66 | m/z=630.22(C43H30N4Si=630.83)m / z = 630.22 (C 43 H 30 N 4 Si = 630.83) |
| 3-673-67 | m/z=738.28(C54H34N4=738.89)m / z = 738.28 (C 54 H 34 N 4 = 738.89) | 3-683-68 | m/z=754.26(C53H34N4Si=754.97)m / z = 754.26 (C 53 H 34 N 4 Si = 754.97) |
| 3-693-69 | m/z=588.20(C41H24N4O=588.67)m / z = 588.20 (C 41 H 24 N 4 O = 588.67) | 3-703-70 | m/z=554.16(C37H22N4S=554.67)m / z = 554.16 (C 37 H 22 N 4 S = 554.67) |
| 3-713-71 | m/z=614.25(C44H30N4=614.75)m / z = 614.25 (C 44 H 30 N 4 = 614.75) | 3-723-72 | m/z=702.22(C49H30N4Si=702.89)m / z = 702.22 (C 49 H 30 N 4 Si = 702.89) |
| 3-733-73 | m/z=588.20(C41H24N4O=588.67)m / z = 588.20 (C 41 H 24 N 4 O = 588.67) | 3-743-74 | m/z=554.16(C37H22N4S=554.67)m / z = 554.16 (C 37 H 22 N 4 S = 554.67) |
| 3-753-75 | m/z=664.26(C48H32N4=664.81)m / z = 664.26 (C 48 H 32 N 4 = 664.81) | 3-763-76 | m/z=602.10(C37H22N4Se=601.57)m / z = 602.10 (C 37 H 22 N 4 Se = 601.57) |
| 3-773-77 | m/z=628.19(C43H24N4O2=628.69)m / z = 628.19 (C 43 H 24 N 4 O 2 = 628.69) | 3-783-78 | m/z=654.19(C45H26N4S=654.79)m / z = 654.19 (C 45 H 26 N 4 S = 654.79) |
| 3-793-79 | m/z=664.26(C48H32N4=664.81)m / z = 664.26 (C 48 H 32 N 4 = 664.81) | 3-803-80 | m/z=580.21(C39H28N4Si=580.77)m / z = 580.21 (C 39 H 28 N 4 Si = 580.77) |
| 3-813-81 | m/z=538.18(C37H22N4O=538.61)m / z = 538.18 (C 37 H 22 N 4 O = 538.61) | 3-823-82 | m/z=554.16(C37H22N4S=554.67)m / z = 554.16 (C 37 H 22 N 4 S = 554.67) |
| 3-833-83 | m/z=714.28(C52H34N4=714.87)m / z = 714.28 (C 52 H 34 N 4 = 714.87) | 3-843-84 | m/z=662.18(C41H14D10N4Se=661.69)m / z = 662.18 (C 41 H 14 D 10 N 4 Se = 661.69) |
| 3-853-85 | m/z=680.20(C47H28N4S=680.83)m / z = 680.20 (C 47 H 28 N 4 S = 680.83) | 3-863-86 | m/z=588.20(C41H24N4O=588.67)m / z = 588.20 (C 41 H 24 N 4 O = 588.67) |
| 3-873-87 | m/z=614.21(C43H26N4O=614.71)m / z = 614.21 (C 43 H 26 N 4 O = 614.71) | 3-883-88 | m/z=630.19(C43H26N4S=630.77)m / z = 630.19 (C 43 H 26 N 4 S = 630.77) |
| 3-893-89 | m/z=614.25(C44H30N4=614.75)m / z = 614.25 (C 44 H 30 N 4 = 614.75) | 3-903-90 | m/z=680.24(C47H32N4Si=680.89)m / z = 680.24 (C 47 H 32 N 4 Si = 680.89) |
| 3-913-91 | m/z=638.21(C45H26N4O=638.73)m / z = 638.21 (C 45 H 26 N 4 O = 638.73) | 3-923-92 | m/z=554.16(C37H22N4S=554.67)m / z = 554.16 (C 37 H 22 N 4 S = 554.67) |
| 3-933-93 | m/z=729.29(C52H35N5=729.89)m / z = 729.29 (C 52 H 35 N 5 = 729.89) | 3-943-94 | m/z=580.21(C39H28N4Si=580.77)m / z = 580.21 (C 39 H 28 N 4 Si = 580.77) |
| 3-953-95 | m/z=690.24(C49H30N4O=690.81)m / z = 690.24 (C 49 H 30 N 4 O = 690.81) | 3-963-96 | m/z=554.16(C37H22N4S=554.67)m / z = 554.16 (C 37 H 22 N 4 S = 554.67) |
| 3-973-97 | m/z=564.23(C40H28N4=564.69)m / z = 564.23 (C 40 H 28 N 4 = 564.69) | 3-983-98 | m/z=602.10(C37H22N4Se=601.57)m / z = 602.10 (C 37 H 22 N 4 Se = 601.57) |
| 3-993-99 | m/z=538.18(C37H22N4O=538.61)m / z = 538.18 (C 37 H 22 N 4 O = 538.61) | 3-1003-100 | m/z=734.18(C49H26N4O2S=734.83)m / z = 734.18 (C 49 H 26 N 4 O 2 S = 734.83) |
| 3-1013-101 | m/z=614.25(C44H30N4=614.75)m / z = 614.25 (C 44 H 30 N 4 = 614.75) | 3-1023-102 | m/z=826.22(C55H34N4OSSi=827.05)m / z = 826.22 (C 55 H 34 N 4 OSSi = 827.05) |
| 3-1033-103 | m/z=654.19(C45H26N4S=654.79)m / z = 654.19 (C 45 H 26 N 4 S = 654.79) | 3-1043-104 | m/z=638.21(C45H26N4O=638.73)m / z = 638.21 (C 45 H 26 N 4 O = 638.73) |
유기전기소자의 제조평가Manufacturing evaluation of organic electric devices
실시 예 1) Example 1)
레드Red
유기 발광 소자의 제작 및 시험 Fabrication and testing of organic light emitting devices
먼저, 유리 기판에 형성된 ITO층(양극) 위에 우선 홀 주입층으로서 N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (2-TNATA로 약기함) 막을 진공증착하여 60 nm 두께로 형성하였다. 이어서, N,N'-Bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (이하 NPB로 약기함)을 60 nm 두께로 진공증착하여 홀 수송층을 형성하였다. 정공수송층 상부에 호스트로서 화학식 (1)과 화학식 (2)로 표시되는 상기 발명화합물을 50:50으로 혼합한 혼합물을 사용하였으며, 도판트로서는 (piq)2Ir(acac) [bis-(1-phenylisoquinolyl)iridium(Ⅲ)acetylacetonate] 을 95:5 중량으로 도핑함으로써 상기 정공수송층 위에 30nm 두께의 발광층을 증착하였다. 홀 저지층으로 (1,1'-비스페닐)-4-올레이토)비스(2-메틸-8-퀴놀린올레이토)알루미늄(이하 BAlq로 약기함)을 10 nm 두께로 진공증착하고, 전자수송층으로 트리스(8-퀴놀리놀)알루미늄(이하 Alq3로 약칭함)을 40 nm 두께로 성막하였다. 이후, 전자주입층으로 할로젠화 알칼리 금속인 LiF를 0.2 nm 두께로 증착하고, 이어서 Al을 150 nm의 두께로 증착하여 음극으로 사용함으로서 유기전기발광소자를 제조하였다.First, N 1- (naphthalen-2-yl) -N 4 , N 4 -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl as a hole injection layer first on the ITO layer (anode) formed on the glass substrate. ) -N 1 -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum deposited to form a thickness of 60 nm. Subsequently, N, N'-Bis (1-naphthalenyl) -N, N'-bis-phenyl- (1,1'-biphenyl) -4,4'-diamine (hereinafter abbreviated as NPB) to a thickness of 60 nm. Vacuum-deposited to form a hole transport layer. As a host on the hole transport layer, a mixture of the above-described compounds represented by Chemical Formulas (1) and (2) in a ratio of 50:50 was used, and as a dopant, (piq) 2 Ir (acac) [bis- (1- phenylisoquinolyl) iridium (Ⅲ) acetylacetonate] was deposited at a weight of 95: 5 to deposit a 30 nm thick light emitting layer on the hole transport layer. As the hole blocking layer, (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolineoleito) aluminum (hereinafter abbreviated as BAlq) is vacuum deposited to a thickness of 10 nm, and the electron transport layer Tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nm. Subsequently, an organic electroluminescent device was manufactured by depositing LiF, an alkali metal halide as an electron injection layer, to a thickness of 0.2 nm, and then depositing Al to a thickness of 150 nm to use as a cathode.
[[
비교예Comparative example
1~3] 1 ~ 3]
화학식 1로 표시되는 화합물을 단독으로 호스트로 사용하는 것을 제외하고는 상기 실시예와 동일한 방법으로 유기전기발광소자를 제작하였다. An organic electroluminescent device was manufactured in the same manner as in the above example, except that the compound represented by Chemical Formula 1 was used alone as a host.
[비교예 4~6][Comparative Examples 4-6]
화학식 2로 표시되는 화합물을 단독으로 호스트로 사용하는 것을 제외하고는 상기 실시예와 동일한 방법으로 유기전기발광소자를 제작하였다. An organic electroluminescent device was manufactured in the same manner as in the above example, except that the compound represented by Chemical Formula 2 was used alone as a host.
[비교예 7][Comparative Example 7]
화학식 1로 표시되는 화합물과 비교화합물 1을 혼합물로 사용하는 것을 제외하고는 상기 실시예와 동일한 방법으로 유기전기발광소자를 제작하였다. An organic electroluminescent device was manufactured in the same manner as in the above example, except that the compound represented by Chemical Formula 1 and Comparative Compound 1 were used as a mixture.
[비교예 8][Comparative Example 8]
화학식 2로 표시되는 화합물과 비교화합물 1을 혼합물로 사용하는 것을 제외하고는 상기 실시예와 동일한 방법으로 유기전기발광소자를 제작하였다. An organic electroluminescent device was manufactured in the same manner as in the above example, except that the compound represented by Chemical Formula 2 and Comparative Compound 1 were used as a mixture.
[비교예 9~11][Comparative Examples 9-11]
화학식 1로 표시되는 화합물과 비교화합물 3 내지 비교화합물 5를 혼합물로 사용하는 것을 제외하고는 상기 실시예와 동일한 방법으로 유기전기발광소자를 제작하였다. An organic electroluminescent device was manufactured in the same manner as in the above example, except that the compound represented by Chemical Formula 1 and Comparative Compound 3 to Comparative Compound 5 were used as a mixture.
이와 같이 제조된 실시예 및 비교예 유기전기발광소자들에 순바이어스 직류전압을 가하여 포토리서치(photoresearch)사의 PR-650으로 전기발광(EL) 특성을 측정하였으며, 그 측정 결과 2500cd/m2 기준 휘도에서 맥사이언스사에서 제조된 수명 측정 장비를 통해 T95 수명을 측정하였다. 하기 표는 소자제작 및 평가한 결과를 나타낸다.The electroluminescence (EL) characteristics were measured by the PR-650 of photoresearch by applying a net bias DC voltage to the organic electroluminescent elements of the Examples and Comparative Examples prepared as described above, and the measurement result showed a reference luminance of 2500 cd / m 2 In the T95 life was measured by a life measurement equipment manufactured by Max Science. The following table shows the results of device fabrication and evaluation.
| 제 1호스트Host 1 | 제 2호스트Host 2 | VoltageVoltage | Current DensityCurrent Density | Brightness(cd/m2)Brightness (cd / m 2 ) | EfficiencyEfficiency | LifetimeT(95)LifetimeT (95) | |
| 비교예(1)Comparative Example (1) | 화합물(1-56)Compound (1-56) | -- | 5.1 5.1 | 19.5 19.5 | 25002500 | 12.8 12.8 | 90.7 90.7 |
| 비교예(2)Comparative Example (2) | 화합물(2-43)Compound (2-43) | -- | 5.2 5.2 | 22.1 22.1 | 25002500 | 11.3 11.3 | 90.4 90.4 |
| 비교예(3)Comparative Example (3) | 화합물(2-133)Compound (2-133) | -- | 5.0 5.0 | 18.5 18.5 | 25002500 | 13.5 13.5 | 95.0 95.0 |
| 비교예(4)Comparative Example (4) | 화합물(3-8)Compound (3-8) | -- | 3.8 3.8 | 15.6 15.6 | 25002500 | 16.0 16.0 | 103.2 103.2 |
| 비교예(5)Comparative Example (5) | 화합물(3-43)Compound (3-43) | -- | 3.9 3.9 | 15.8 15.8 | 25002500 | 15.8 15.8 | 102.5 102.5 |
| 비교예(6)Comparative Example (6) | 화합물(3-97)Compound (3-97) | -- | 4.2 4.2 | 18.0 18.0 | 25002500 | 13.9 13.9 | 83.0 83.0 |
| 비교예(7)Comparative Example (7) | 화합물(2-133)Compound (2-133) | 비교화합물1Comparative Compound 1 | 4.7 4.7 | 11.3 11.3 | 25002500 | 22.1 22.1 | 100.0 100.0 |
| 비교예(8)Comparative Example (8) | 화합물(3-8)Compound (3-8) | 비교화합물2Comparative Compound 2 | 3.8 3.8 | 8.6 8.6 | 25002500 | 29.2 29.2 | 115.8 115.8 |
| 비교예(9)Comparative Example (9) | 화합물(2-133)Compound (2-133) | 비교화합물3Comparative Compound 3 | 4.6 4.6 | 9.4 9.4 | 25002500 | 26.6 26.6 | 110.4 110.4 |
| 비교예(10)Comparative Example (10) | 화합물(2-133)Compound (2-133) | 비교화합물 4Comparative Compound 4 | 4.5 4.5 | 9.4 9.4 | 25002500 | 26.6 26.6 | 112.7 112.7 |
| 비교예(11)Comparative Example (11) | 화합물(2-133)Compound (2-133) | 비교화합물 5Comparative Compound 5 | 4.6 4.6 | 9.2 9.2 | 25002500 | 27.2 27.2 | 111.0 111.0 |
| 실시예(1)Example (1) | 화합물(1-56)Compound (1-56) | 화합물(3-8)Compound (3-8) | 3.5 3.5 | 7.7 7.7 | 25002500 | 32.5 32.5 | 143.8 143.8 |
| 실시예(2)Example (2) | 화합물(2-43)Compound (2-43) | 화합물(3-8)Compound (3-8) | 3.5 3.5 | 7.6 7.6 | 25002500 | 32.9 32.9 | 144.4 144.4 |
| 실시예(3)Example (3) | 화합물(2-133)Compound (2-133) | 화합물(3-8)Compound (3-8) | 3.3 3.3 | 7.1 7.1 | 25002500 | 35.0 35.0 | 148.2 148.2 |
| 실시예(4)Example (4) | 화합물(1-56)Compound (1-56) | 화합물(3-43)Compound (3-43) | 3.6 3.6 | 7.6 7.6 | 25002500 | 32.8 32.8 | 144.1 144.1 |
| 실시예(5)Example (5) | 화합물(2-43)Compound (2-43) | 화합물(3-43)Compound (3-43) | 3.5 3.5 | 7.6 7.6 | 25002500 | 33.1 33.1 | 144.7 144.7 |
| 실시예(6)Example (6) | 화합물(2-133)Compound (2-133) | 화합물(3-43)Compound (3-43) | 3.4 3.4 | 7.3 7.3 | 25002500 | 34.1 34.1 | 148.0 148.0 |
| 실시예(7)Example (7) | 화합물(1-56)Compound (1-56) | 화합물(3-97)Compound (3-97) | 3.7 3.7 | 7.4 7.4 | 25002500 | 33.6 33.6 | 117.1 117.1 |
| 실시예(8)Example (8) | 화합물(2-43)Compound (2-43) | 화합물(3-97)Compound (3-97) | 3.7 3.7 | 7.4 7.4 | 25002500 | 34.0 34.0 | 118.6 118.6 |
| 실시예(9)Example (9) | 화합물(2-133)Compound (2-133) | 화합물(3-97)Compound (3-97) | 3.5 3.5 | 7.1 7.1 | 25002500 | 35.4 35.4 | 120.6 120.6 |
상기 표 8 결과로부터 알 수 있듯이, 화학식 1과 화학식 2로 표시되는 본 발명의 유기전기발광소자용 재료를 혼합하여 인광호스트로 사용할 경우 (실시예 1~9), 단일물질을 사용한 소자(비교예 1~6)와 비교화합물을 혼합하여 사용한 소자(비교예 7~11)에 비해 구동전압, 효율 및 수명을 현저히 개선시키는 것을 확인할 수 있었다. 다시 말해, 화학식 1과 화학식 2로 표시되는 본 발명의 화합물을 단독으로 인광호스트로 쓴 경우 (비교예 1~6)보다 비교화합물 1 또는 비교화합물 2를 혼합하여 인광호스트로 사용한 비교예 7~11의 결과가 효율 및 수명 면에서 대체적으로 우수했고, 이보다는 화학식 1과 화학식 2로 표시되는 본 발명의 화합물을 혼합한 실시예 1~9가 구동전압, 효율 및 수명 면에서 현저히 우수한 효과를 나타냄을 알 수 있다. 본 발명자들은 상기 실험결과를 근거로 화학식 1의 물질과 화학식 2의 물질을 혼합한 물질의 경우 각각 물질에 대한 특성 이외의 다른 신규한 특성을 갖는다고 판단하여, 화학식 1의 물질, 화학식 2의 물질, 본 발명 혼합물을 각각 사용하여 PL과 PL lifetime을 측정하였다. 그 결과 본 발명 화합물인 화학식 1과 화학식 2를 혼합하였을 경우 단독 화합물일 때와 달리 새로운 PL 파장이 형성되는 것을 확인할 수 있었으며, 새롭게 형성된 PL 파장의 감소 및 소멸 시간이 화학식 1 및 화학식 2 물질 각각의 감소 및 소멸시간보다 증가되는 것을 확인할 수 있었다. 이는 본 발명화합물을 혼합하여 사용할 경우 각각의 물질이 갖는 에너지 준위를 통해 전자와 정공이 이동되는 것뿐만 아니라, 혼합으로 인하여 형성된 새로운 에너지 준위를 갖는 신규 영역에(exciplex) 의한 전자, 정공 이동 또는 에너지 전달로 효율 및 수명이 증가하는 것으로 판단된다. 이는 결과적으로 상기 본 발명 혼합물을 사용할 경우 혼합 박막이 exciplex 에너지 전달 및 발광 프로세스를 보이는 중요한 예라고 할 수 있다.As can be seen from the results in Table 8, when the material for the organic electroluminescent device of the present invention represented by Formula 1 and Formula 2 is used as a phosphorescent host (Examples 1 to 9), a device using a single material (Comparative Example It was confirmed that the driving voltage, efficiency, and lifespan were significantly improved compared to the devices (Comparative Examples 7-11) used by mixing 1-6) and a comparative compound. In other words, when the compound of the present invention represented by Formula 1 and Formula 2 is used alone as a phosphorescent host, Comparative Examples 7 to 11 used as a phosphorescent host by mixing Comparative Compound 1 or Comparative Compound 2 rather than (Comparative Examples 1 to 6) The results of the results were generally excellent in terms of efficiency and life, and rather, Examples 1 to 9 in which the compounds of the present invention represented by Formula 1 and Formula 2 were mixed show remarkably excellent effects in terms of driving voltage, efficiency and life. Able to know. Based on the results of the above experiment, the present inventors determined that the substance of the substance of Formula 1 and the substance of Formula 2 has new characteristics other than the characteristics of the substance, respectively, and the substance of Formula 1 and the substance of Formula 2 , PL and PL lifetime were measured using the mixture of the present invention, respectively. As a result, when the compounds of the present invention, Formula 1 and Formula 2 were mixed, it was confirmed that a new PL wavelength was formed unlike that of a single compound, and the decrease and extinction time of the newly formed PL wavelength was determined for each of Formula 1 and Formula 2 materials. It was confirmed that it was increased than the reduction and extinction time. When the compound of the present invention is used in combination, not only electrons and holes are moved through the energy level of each substance, but also electrons, hole movement or energy due to exciplex of new regions having new energy levels formed due to mixing. It is judged that the efficiency and life of the furnace are increased. As a result, when using the mixture of the present invention, it can be said that the mixed thin film is an important example of exciplex energy transfer and luminescence processes.
또한 비교화합물을 혼합한 인광호스트로 사용한 비교예 7 내지 비교예 11보다 본 발명의 조합이 우수한 이유는 electron 뿐만 아니라 hole에 대한 안정성, 높은 T1등의 특징이 있는 화학식 2로 표시되는 다환고리 화합물에 hole 특성이 강한 화학식 1로 표시되는 화합물을 혼합할 경우, 높은 T1과 높은 LUMO 에너지 값으로 인해 전자 블로킹 능력이 향상되고, 발광층에 더 많은 hole이 빠르고 쉽게 이동하게 된다. 이에 따라 정공과 전자의 발광층 내 charge balance가 증가되어 정공수송층 계면이 아닌 발광층 내부에서 발광이 잘 이루어지고, 그로 인해 HTL 계면에 열화 또한 감소하여 소자 전체의 구동 전압, 효율 그리고 수명이 극대화 된다고 판단된다. 즉, 화학식 1과 화학식 2의 조합이 전기 화학적으로 시너지 작용을 하여 소자 전체의 성능을 향상된 것으로 사료된다.In addition, the reason why the combination of the present invention is superior to Comparative Examples 7 to 11 used as a phosphorescent host in which a comparative compound is mixed is because of the polycyclic ring compound represented by Chemical Formula 2, which has characteristics such as stability to hole and high T1 as well as electron. When the compound represented by Chemical Formula 1 having strong hole characteristics is mixed, the electron blocking ability is improved due to the high T1 and high LUMO energy values, and more holes are quickly and easily moved in the light emitting layer. Accordingly, it is judged that the charge balance in the light emitting layer of holes and electrons is increased, so that light emission is performed well inside the light emitting layer rather than the hole transport layer interface, thereby reducing deterioration at the HTL interface, thereby maximizing the driving voltage, efficiency, and lifetime of the entire device. . That is, the combination of Chemical Formula 1 and Chemical Formula 2 is thought to improve the performance of the entire device by synergistically electrochemically.
실시 예 2) Example 2)
혼합비율 별By mixing ratio
레드Red
유기 발광 소자의 제작 및 시험 Fabrication and testing of organic light emitting devices
| 제 1호스트 Host 1 | 제 2호스트 Host 2 | 혼합 비율(제 1 호스트 : 제 2호스트)Mixing ratio (first host: second host) | Voltage Voltage | Current DensityCurrent Density | Brightness(cd/m2)Brightness (cd / m 2 ) | Efficiency Efficiency | LifetimeT(95) LifetimeT (95) | |
| 실시예(10)Example (10) | 화합물(1-56)Compound (1-56) | 화합물(3-97)Compound (3-97) | 2:82: 8 | 3.3 3.3 | 8.3 8.3 | 25002500 | 30.030.0 | 114.3 114.3 |
| 실시예(11)Example (11) | 화합물(1-56)Compound (1-56) | 화합물(3-97)Compound (3-97) | 3:73: 7 | 3.5 3.5 | 7.9 7.9 | 25002500 | 31.831.8 | 115.1 115.1 |
| 실시예(12)Example (12) | 화합물(1-56)Compound (1-56) | 화합물(3-97)Compound (3-97) | 4:64: 6 | 3.5 3.5 | 7.8 7.8 | 25002500 | 32.132.1 | 116.7 116.7 |
| 실시예(14)Example (14) | 화합물(2-133)Compound (2-133) | 화합물(3-8)Compound (3-8) | 2:82: 8 | 3.1 3.1 | 7.7 7.7 | 25002500 | 32.532.5 | 146.1146.1 |
| 실시예(15)Example (15) | 화합물(2-133)Compound (2-133) | 화합물(3-8)Compound (3-8) | 3:73: 7 | 3.2 3.2 | 7.6 7.6 | 25002500 | 33.033.0 | 146.8 146.8 |
| 실시예(16)Example (16) | 화합물(2-133)Compound (2-133) | 화합물(3-8)Compound (3-8) | 4:64: 6 | 3.2 3.2 | 7.3 7.3 | 25002500 | 34.234.2 | 147.5 147.5 |
상기 표 9와 같이 본 발명의 화합물의 혼합물을 비율 별(2:8, 3:7, 4:6)로 소자를 제작하여 측정하였다. As shown in Table 9, the mixture of the compounds of the present invention was measured by fabricating the device by ratio (2: 8, 3: 7, 4: 6).
결과를 자세히 설명하면, 제 2호스트 비율이 증가할수록 구동전압의 결과가 더 향상되는 것을 확인하였지만 반대로 효율 및 수명에 있어서는 반대의 경향을 띄는 것을 확인하였다. 따라서 혼합물의 경우 혼합 비율의 양이 특성에 영향을 미치기 때문에 발광층 내 charge balance가 극대화 되는 혼합비율을 도출하는 것이 매우 중요한 과제라고 판단된다. When the results were described in detail, it was confirmed that as the second host ratio increased, the result of the driving voltage was further improved, but, on the contrary, it was confirmed that the opposite tendency was observed in efficiency and life. Therefore, in the case of a mixture, it is judged that it is a very important task to derive a mixing ratio in which the charge balance in the light emitting layer is maximized because the amount of the mixing ratio affects the characteristics.
이상의 설명은 본 발명을 예시적으로 설명한 것에 불과한 것으로, 본 발명이 속하는 기술분야에서 통상의 지식을 가지는 자라면 본 발명의 본질적인 특성에서 벗어나지 않는 범위에서 다양한 변형이 가능할 것이다. 따라서, 본 명세서에 개시된 실시 예들은 본 발명을 한정하기 위한 것이 아니라 설명하기 위한 것이고, 이러한 실시 예에 의하여 본 발명의 사상과 범위가 한정되는 것은 아니다. The above description is merely illustrative of the present invention, and those skilled in the art to which the present invention pertains will be capable of various modifications without departing from the essential characteristics of the present invention. Therefore, the embodiments disclosed herein are not intended to limit the present invention, but to explain the present invention, and the spirit and scope of the present invention are not limited by these embodiments.
본 발명의 보호범위는 아래의 청구범위에 의하여 해석되어야 하며, 그와 동등한 범위 내에 있는 모든 기술은 본 발명의 권리범위에 포함하는 것으로 해석되어야 할 것이다.The scope of protection of the present invention should be interpreted by the following claims, and all technologies within the equivalent range should be interpreted as being included in the scope of the present invention.
본 발명에 따르면, 고휘도, 고발광 및 고수명의 우수한 소자특성을 갖는 유기소자를 제조할 수 있어 산업상 이용가능성이 있다.According to the present invention, it is possible to manufacture an organic device having excellent device characteristics of high brightness, high light emission and high life, and thus there is industrial applicability.
Claims (15)
- 제 1전극, 제 2전극, 및 상기 제 1전극과 상기 제 2전극 사이에 형성된 유기물층을 포함하는 유기전기소자에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 인광성 발광층으로서 화학식 (1)로 표시되는 제 1호스트 및 화학식 (2)로 표시되는 제 2호스트를 포함하는 것을 특징으로 하는 유기전기소자.In an organic electric device including a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, the organic material layer includes a light emitting layer, and the light emitting layer is a phosphorescent light emitting layer (1) An organic electric device comprising a first host represented by and a second host represented by the formula (2).화학식 (1) 화학식 (2) 화학식 (2-1)Formula (1) Formula (2) Formula (2-1)
{상기 화학식 (1), (2) 및 (2-1)에서, {In the formulas (1), (2) and (2-1) above,1) W, X 및 Y는 각각 독립적으로 O, S, CR'R", SiR'R" 또는 Se이고,1) W, X and Y are each independently O, S, CR'R ", SiR'R" or Se,2) a 및 b는 각각 독립적으로 0 또는 1이며, 단 a+b는 1 이상이고,2) a and b are each independently 0 or 1, provided that a + b is 1 or more,3) R' 및 R"는 각각 독립적으로 수소; C1~C50의 알킬기; C6~C60의 아릴기; 및 C2~C60의 헤테로아릴기;로 이루어진 군에서 선택되거나, R' 및 R"은 서로 고리를 형성하여 스파이로(spiro) 고리를 형성하고, 3) R 'and R "are each independently hydrogen; an alkyl group of C 1 to C 50 ; an aryl group of C 6 to C 60 ; and a heteroaryl group of C 2 to C 60 ; or R' And R "form a ring with each other to form a spiro ring,4) L1, L2 및 L'은 각각 독립적으로 단일결합; C6~C60의 아릴렌기; 또는 C2~C60의 헤테로아릴렌기;이고4) L 1 , L 2 and L 'are each independently a single bond; C 6 ~ C 60 Arylene group; Or a C 2 ~ C 60 heteroarylene group; and5) Ar1, Ar2 및 Ar3는 각각 독립적으로 수소; 중수소; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리와 C6~C60의 방향족고리의 융합고리기; C1~C50의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C30의 알콕실기; C6~C30의 아릴옥시기; 및 -L'-NR'R";로 이루어진 군에서 선택되고,5) Ar 1 , Ar 2 and Ar 3 are each independently hydrogen; heavy hydrogen; C 6 ~ C 60 Aryl group; Fluorenyl group; C 2 ~ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C 3 ~ C 60 aliphatic ring and C 6 ~ C 60 aromatic ring fused ring group; C 1 ~ C 50 alkyl group; C 2 ~ C 20 alkenyl group; C 2 ~ C 20 alkynyl group; C 1 ~ C 30 Alkoxy group; C 6 ~ C 30 Aryloxy group; And -L'-NR'R ";6) Z는 NR', O, S, CR'R", SiR'R", 또는 Se이고,6) Z is NR ', O, S, CR'R ", SiR'R", or Se,7) 7) R1 내지 R5은 각각 독립적으로 수소; 중수소; 할로겐; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리와 C6~C60의 방향족고리의 융합고리기; C1~C50의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C30의 알콕실기; C6~C30의 아릴옥시기; 및 -L'-N(Ra)(Rb);로 이루어진 군에서 선택되고, 7) 7) R 1 to R 5 are each independently hydrogen; heavy hydrogen; halogen; C 6 ~ C 60 Aryl group; Fluorenyl group; C 2 ~ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C 3 ~ C 60 aliphatic ring and C 6 ~ C 60 aromatic ring fused ring group; C 1 ~ C 50 alkyl group; C 2 ~ C 20 alkenyl group; C 2 ~ C 20 alkynyl group; C 1 ~ C 30 Alkoxy group; C 6 ~ C 30 Aryloxy group; And -L'-N (R a ) (R b ); is selected from the group consisting of,상기 Ra 및 Rb 은 서로 독립적으로 C6~C60의 아릴기; 플루오렌일기; C3~C60의 지방족고리와 C6~C60의 방향족고리의 융합고리기; 및 O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기;로 이루어진 군에서 선택되고, R a and R b are independently of each other C 6 ~ C 60 aryl group; Fluorenyl group; C 3 ~ C 60 aliphatic ring and C 6 ~ C 60 aromatic ring fused ring group; And O, N, S, Si, and C 2 ~ C 60 heterocyclic group containing at least one heteroatom; is selected from the group consisting of,상기 l, m, n, o 및 p가 2 이상인 경우 각각 복수로서 서로 동일하거나 상이하며 복수의 R1끼리, 복수의 R2끼리, 복수의 R3끼리, 복수의 R4끼리, 복수의 R5끼리는 서로 결합하여 방향족 및 헤테로방향족 고리를 형성할 수 있고, Wherein l, m, n, o and identical to or different from each other as a plurality each of not less than p 2, and a plurality of R 1 each other, a plurality of R 2 to each other, a plurality of R 3 to each other, a plurality of R 4 with each other, a plurality of R 5 They may combine with each other to form an aromatic and heteroaromatic ring,8) R12, R13 및 R14는 각각 독립적으로 수소; 중수소; 할로겐; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리와 C6~C60의 방향족고리의 융합고리기; C1~C50의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C30의 알콕실기; C6~C30의 아릴옥시기; 및 -L'-N(Ra)(Rb);로 이루어진 군에서 선택되고, 8) R 12 , R 13 and R 14 are each independently hydrogen; heavy hydrogen; halogen; C 6 ~ C 60 Aryl group; Fluorenyl group; C 2 ~ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C 3 ~ C 60 aliphatic ring and C 6 ~ C 60 aromatic ring fused ring group; C 1 ~ C 50 alkyl group; C 2 ~ C 20 alkenyl group; C 2 ~ C 20 alkynyl group; C 1 ~ C 30 Alkoxy group; C 6 ~ C 30 Aryloxy group; And -L'-N (R a ) (R b ); is selected from the group consisting of,상기 g, h 및 i가 2 이상인 경우 각각 복수로서 서로 동일하거나 상이하며 인접한 복수의 R12끼리, 복수의 R13끼리, 복수의 R14끼리는 서로 결합하여 방향족 및 헤테로방향족 고리를 형성할 수 있고, 인접한 R12, 인접한 R13, 및 인접한 R14 중 적어도 한쌍은 고리를 형성하고,When the g, h and i are 2 or more, a plurality of each of the same or different and adjacent to each other, a plurality of adjacent R 12 , a plurality of R 13 , and a plurality of R 14 may combine with each other to form an aromatic and heteroaromatic ring, At least one pair of contiguous R 12 , contiguous R 13 , and contiguous R 14 forms a ring,9) g 및 i는 0~4 중 어느 하나의 정수이고, h는 0~2 중 어느 하나의 정수이며, n, l 및 p은 0~4 중 어느 하나의 정수이고, m은 0 또는 1이며, o는 0~3 중 어느 하나의 정수이고, 9) g and i are integers from 0 to 4, h is an integer from 0 to 2, n, l and p are integers from 0 to 4, m is 0 or 1 , o is an integer from 0 to 3,10) 상기 화학식 (2)의 인접한 2개의 *와 화학식 (2-1)의 *와 결합하여 고리를 형성하며,10) the adjacent two * of formula (2) and the * of formula (2-1) combine to form a ring,여기서, 상기 아릴기, 플루오렌닐기, 아릴렌기, 헤테로고리기, 플루오렌일렌기, 융합고리기, 알킬기, 알케닐기, 알콕시기 및 아릴옥시기는 각각 중수소; 할로겐; 실란기; 실록산기; 붕소기; 게르마늄기; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕실기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C20의 아릴기; 중수소로 치환된 C6-C20의 아릴기; 플루오렌일기; C2-C20의 헤테로고리기; C3-C20의 시클로알킬기; C7-C20의 아릴알킬기; 및 C8-C20의 아릴알켄일기;로 이루어진 군에서 선택된 하나 이상의 치환기로 더욱 치환될 수 있으며, 또한 이들 치환기들은 서로 결합하여 고리를 형성할 수도 있으며, 여기서 '고리'란 C3-C60의 지방족고리 또는 C6-C60의 방향족고리 또는 C2-C60의 헤테로고리 또는 이들의 조합으로 이루어진 융합 고리를 말하며, 포화 또는 불포화 고리를 포함한다.}Here, the aryl group, fluorenyl group, arylene group, heterocyclic group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group each deuterium; halogen; Silane group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; C 1 -C 20 alkylthio; Alkoxyl group of C 1 -C 20 ; C 1 -C 20 alkyl group; Alkenyl group of C 2 -C 20 ; Alkynyl group of C 2 -C 20 ; C 6 -C 20 Aryl group; A C 6 -C 20 aryl group substituted with deuterium; Fluorenyl group; C 2 -C 20 heterocyclic group; C 3 -C 20 cycloalkyl group; C 7 -C 20 Arylalkyl group; And C 8 -C 20 arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of, and these substituents may also combine with each other to form a ring, wherein 'ring' means C 3 -C 60 Refers to an aliphatic ring of C or an aromatic ring of C 6 -C 60 or a heterocycle of C 2 -C 60 or a combination thereof, and includes a saturated or unsaturated ring.} - 제1항에 있어서, 상기 화학식 (1)로 나타낸 화합물이 하기 화학식 (3) 또는 (4)로 표시되는 것을 특징으로 하는 유기전기소자.The organic electroluminescent device according to claim 1, wherein the compound represented by the formula (1) is represented by the following formula (3) or (4).화학식 (3) 화학식 (4) Formula (3) Formula (4)
(상기 화학식 (3) 및 (4)에서, X, Y, Z, Ar1, L1, R1, R2, R3, R4, R5, l, m, n, o, 및 p는 상기 청구항 1에서 정의된 바와 동일하다.)(In the formulas (3) and (4), X, Y, Z, Ar 1 , L 1 , R 1 , R 2 , R 3 , R 4 , R 5 , l, m, n, o, and p are It is the same as defined in claim 1 above.) - 제1항에 있어서, 상기 화학식 (1)로 나타낸 화합물이 하기 화학식 (5) 내지 (12) 중 어느 하나로 표시되는 것을 특징으로 하는 유기전기소자.The organic electroluminescent device according to claim 1, wherein the compound represented by the formula (1) is represented by any one of the following formulas (5) to (12).화학식 (5) 화학식 (6) 화학식 (7) 화학식 (8)Formula (5) Formula (6) Formula (7) Formula (8)
화학식 (9) 화학식 (10) 화학식 (11) 화학식 (12)Formula (9) Formula (10) Formula (11) Formula (12)
(상기 화학식 (5) 내지 (12)에서, X, Y, Z, Ar1, L1, R1, R2, R3, R4, R5, l, m, n, o, 및 p는 상기 청구항 1에서 정의된 바와 동일하다.)(In the formulas (5) to (12), X, Y, Z, Ar 1 , L 1 , R 1 , R 2 , R 3 , R 4 , R 5 , l, m, n, o, and p are It is the same as defined in claim 1 above.) - 제1항에 있어서, 상기 l, m, n, o 및 p가 모두 0인 것을 특징으로 하는 유기전기소자.The organic electroluminescent device according to claim 1, wherein the l, m, n, o and p are all 0.
- 제1항에 있어서, 상기 R1, R2, R3, R4 및 R5 중 어느 하나는 이웃한 한 쌍이 서로 결합하여 고리를 형성하는 것을 특징으로 하는 유기전기소자.The organic electroluminescent device according to claim 1, wherein any one of R 1 , R 2 , R 3 , R 4 and R 5 forms a ring by combining a pair of neighbors with each other.
- 제1항에 있어서, 상기 X 또는 Y는 S 또는 O인 것을 특징으로 하는 유기전기소자.The organic electric device according to claim 1, wherein X or Y is S or O.
- 제1항에 있어서, 상기 화학식 (1)은 하기 화합물 중 어느 하나인 것을 특징으로 하는 유기전기소자.The method of claim 1, wherein the formula (1) is an organic electric device, characterized in that any one of the following compounds.
- 제1항에 있어서, 상기 화학식 (2)로 나타낸 화합물이 하기 화학식 (13) 내지 (17) 중 어느 하나로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기전기소자.The organic electroluminescent device according to claim 1, wherein the compound represented by the formula (2) includes a compound represented by any one of the following formulas (13) to (17).화학식 (13) 화학식 (14) 화학식 (15) 화학식 (16) 화학식 (17)Formula (13) Formula (14) Formula (15) Formula (16) Formula (17)
(상기 화학식 (13) 내지 (17)에서, Ar2, Ar3, L2, g, h, i, R' 및 R"는 상기 청구항 1에서 정의한 바와 같고,(In the formulas (13) to (17), Ar 2 , Ar 3 , L 2 , g, h, i, R 'and R "are as defined in claim 1 above,R12', R13' 및 R14'은 상기 청구항 1에서 R12, R13 및 R14의 정의와 같다.)R 12 ' , R 13' and R 14 ' are as defined for R 12 , R 13 and R 14 in claim 1 above.) - 제1항에 있어서, 상기 화학식 (2)로 나타낸 화합물이 하기 화학식 (18) 내지 (57) 중 어느 하나로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기전기소자.The organic electroluminescent device according to claim 1, wherein the compound represented by the formula (2) includes a compound represented by any one of the following formulas (18) to (57).화학식 (18) 화학식 (19) 화학식 (20) 화학식 (21)Formula (18) Formula (19) Formula (20) Formula (21)
화학식 (22) 화학식 (23) 화학식 (24) 화학식 (25)Formula (22) Formula (23) Formula (24) Formula (25)
화학식 (26) 화학식 (27) 화학식 (28) 화학식 (29)Formula (26) Formula (27) Formula (28) Formula (29)
화학식 (30) 화학식 (31) 화학식 (32) 화학식 (33)Formula (30) Formula (31) Formula (32) Formula (33)
화학식 (34) 화학식 (35) 화학식 (36) 화학식 (37)Formula (34) Formula (35) Formula (36) Formula (37)
화학식 (38) 화학식 (39) 화학식 (40) 화학식 (41) Formula (38) Formula (39) Formula (40) Formula (41)
화학식 (42) 화학식 (43) 화학식 (44) 화학식 (45)Formula (42) Formula (43) Formula (44) Formula (45)
화학식 (46) 화학식 (47) 화학식 (48) 화학식 (49)Formula (46) Formula (47) Formula (48) Formula (49)
화학식 (50) 화학식 (51) 화학식 (52) 화학식 (53)Formula (50) Formula (51) Formula (52) Formula (53)
화학식 (54) 화학식 (55) 화학식 (56) 화학식 (57)Formula (54) Formula (55) Formula (56) Formula (57)
(상기 화학식 (18) 내지 (57)에서, Ar2, Ar3, L2, R12, R13, R14, R12', R13', R14', g, h, i 및 W는 상기 청구항 1에서 정의한 바와 같고,(In the formulas (18) to (57), Ar 2 , Ar 3 , L 2 , R 12 , R 13 , R 14 , R 12 ' , R 13' , R 14 ' , g, h, i and W are As defined in claim 1 above,R12', R13' 및 R14'은 상기 청구항 1에서 R12, R13 및 R14의 정의와 같으며,R 12 ' , R 13' and R 14 ' are the same as the definitions of R 12 , R 13 and R 14 in claim 1 above,t는 0 내지 4 중 어느 하나의 정수이고, s 및 u는 각각 독립적으로 0 내지 6 중 어느 하나의 정수이다.)t is an integer from 0 to 4, and s and u are each independently an integer from 0 to 6.) - 제1항에 있어서, 상기 화학식 (2)는 하기 화합물 중 하나인 것을 특징으로 하는 유기전기소자.The method of claim 1, wherein the formula (2) is an organic electric device, characterized in that one of the following compounds.
- 제1항에 있어서, 상기 화학식 (1) 및 상기 화학식 (2)로 나타내는 화합물이 중량비 1:9 내지 9:1 중 어느 하나의 비율로 혼합되는 것을 특징으로 하는 유기전기소자.The organic electroluminescent device according to claim 1, wherein the compounds represented by the formula (1) and the formula (2) are mixed in a ratio of any one of 1: 9 to 9: 1 by weight.
- 제1항에 있어서, 상기 화학식 (1) 및 상기 화학식 (2)로 나타내는 화합물이 중량비 1:9 내지 5:5로 혼합되는 것을 특징으로 하는 유기전기소자.The organic electroluminescent device according to claim 1, wherein the compounds represented by the formula (1) and the formula (2) are mixed in a weight ratio of 1: 9 to 5: 5.
- 제1항에 있어서, 상기 화학식 (1) 및 상기 화학식 (2)로 나타내는 화합물이 중량비 2:8 내지 3:7로 혼합되는 것을 특징으로 하는 유기전기소자.The organic electroluminescent device according to claim 1, wherein the compounds represented by the formula (1) and the formula (2) are mixed in a weight ratio of 2: 8 to 3: 7.
- 제1항에 따른 유기전기소자를 포함하는 디스플레이장치: 및 상기 디스플레이장치를 구동하는 제어부;를 포함하는 전자장치.An electronic device comprising: a display device comprising the organic electroluminescent device according to claim 1 and a control unit driving the display device.
- 제14항에 있어서, 상기 유기전기소자는 유기전기발광소자, 유기태양전지, 유기감광체, 유기트랜지스터, 및 단색 또는 백색 조명용소자 중 적어도 하나인 것을 특징으로 하는 전자장치.15. The electronic device of claim 14, wherein the organic electric element is at least one of an organic electroluminescent element, an organic solar cell, an organic photoreceptor, an organic transistor, and a monochromatic or white lighting element.
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