KR20180064861A - Organic compound and organic electroluminescent device using the same - Google Patents
Organic compound and organic electroluminescent device using the same Download PDFInfo
- Publication number
- KR20180064861A KR20180064861A KR1020160165270A KR20160165270A KR20180064861A KR 20180064861 A KR20180064861 A KR 20180064861A KR 1020160165270 A KR1020160165270 A KR 1020160165270A KR 20160165270 A KR20160165270 A KR 20160165270A KR 20180064861 A KR20180064861 A KR 20180064861A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- mmol
- aryl
- compound
- mixture
- Prior art date
Links
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 218
- -1 aryl phosphine oxide Chemical compound 0.000 claims description 146
- 239000012044 organic layer Substances 0.000 claims description 112
- 239000010410 layer Substances 0.000 claims description 80
- 125000003118 aryl group Chemical group 0.000 claims description 71
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 125000004429 atom Chemical group 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 125000004104 aryloxy group Chemical group 0.000 claims description 13
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 13
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 12
- 125000005104 aryl silyl group Chemical group 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 11
- 150000004982 aromatic amines Chemical class 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 8
- 229910052796 boron Inorganic materials 0.000 claims description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 7
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000005264 aryl amine group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000011368 organic material Substances 0.000 abstract description 14
- 230000001747 exhibiting effect Effects 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 306
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 300
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 204
- 239000000203 mixture Substances 0.000 description 185
- 238000002360 preparation method Methods 0.000 description 128
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 121
- 239000002904 solvent Substances 0.000 description 105
- 230000015572 biosynthetic process Effects 0.000 description 104
- 238000003786 synthesis reaction Methods 0.000 description 104
- 238000006243 chemical reaction Methods 0.000 description 102
- 239000011541 reaction mixture Substances 0.000 description 102
- 238000004440 column chromatography Methods 0.000 description 101
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 60
- 239000000463 material Substances 0.000 description 48
- UCFSYHMCKWNKAH-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OBOC1(C)C UCFSYHMCKWNKAH-UHFFFAOYSA-N 0.000 description 31
- FRYRJNHMRVINIZ-UHFFFAOYSA-N B1CCOO1 Chemical compound B1CCOO1 FRYRJNHMRVINIZ-UHFFFAOYSA-N 0.000 description 22
- 238000005160 1H NMR spectroscopy Methods 0.000 description 21
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 20
- 238000010992 reflux Methods 0.000 description 14
- JWWMUTCXVNBWGP-UHFFFAOYSA-N 4-chloro-2-phenyl-6-(4-phenylphenyl)pyrimidine Chemical compound C1(=CC=C(C=C1)C1=NC(=NC(=C1)Cl)C1=CC=CC=C1)C1=CC=CC=C1 JWWMUTCXVNBWGP-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- VDIHPLIBGUXRLI-UHFFFAOYSA-N 2-chloro-4-phenyl-6-(4-phenylphenyl)pyrimidine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=CC=1C(C=C1)=CC=C1C1=CC=CC=C1 VDIHPLIBGUXRLI-UHFFFAOYSA-N 0.000 description 10
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 10
- SFKMVPQJJGJCMI-UHFFFAOYSA-N 2-chloro-4-phenylquinazoline Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1C1=CC=CC=C1 SFKMVPQJJGJCMI-UHFFFAOYSA-N 0.000 description 9
- 125000006575 electron-withdrawing group Chemical group 0.000 description 9
- NCYOZUAKVJOZNM-UHFFFAOYSA-N 2,3-dibromo-1,1-dimethylindene Chemical compound BrC=1C(C2=CC=CC=C2C=1Br)(C)C NCYOZUAKVJOZNM-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 238000005401 electroluminescence Methods 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 7
- YBFCBQMICVOSRW-UHFFFAOYSA-N 1-phenylindole Chemical compound C1=CC2=CC=CC=C2N1C1=CC=CC=C1 YBFCBQMICVOSRW-UHFFFAOYSA-N 0.000 description 6
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- FRDOMQZQFJXSJN-UHFFFAOYSA-N CC1(C)BOOC1(C)C Chemical compound CC1(C)BOOC1(C)C FRDOMQZQFJXSJN-UHFFFAOYSA-N 0.000 description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 125000005647 linker group Chemical group 0.000 description 5
- JKHCVYDYGWHIFJ-UHFFFAOYSA-N Clc1nc(nc(n1)-c1ccc(cc1)-c1ccccc1)-c1ccccc1 Chemical compound Clc1nc(nc(n1)-c1ccc(cc1)-c1ccccc1)-c1ccccc1 JKHCVYDYGWHIFJ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HIYWOHBEPVGIQN-UHFFFAOYSA-N 1h-benzo[g]indole Chemical group C1=CC=CC2=C(NC=C3)C3=CC=C21 HIYWOHBEPVGIQN-UHFFFAOYSA-N 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- 0 CC(*)Cc1c(C)[n](*)c2ccccc12 Chemical compound CC(*)Cc1c(C)[n](*)c2ccccc12 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 2
- KOFLVDBWRHFSAB-UHFFFAOYSA-N 1,2,4,5-tetrahydro-1-(phenylmethyl)-5,9b(1',2')-benzeno-9bh-benz(g)indol-3(3ah)-one Chemical compound C1C(C=2C3=CC=CC=2)C2=CC=CC=C2C23C1C(=O)CN2CC1=CC=CC=C1 KOFLVDBWRHFSAB-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- JPYBOGFQEPDJRZ-UHFFFAOYSA-N 2,3-dibromo-1-benzofuran Chemical compound C1=CC=C2C(Br)=C(Br)OC2=C1 JPYBOGFQEPDJRZ-UHFFFAOYSA-N 0.000 description 2
- TWZSIAFEFBKCNN-UHFFFAOYSA-N 2,3-dibromo-1-benzothiophene Chemical compound C1=CC=C2C(Br)=C(Br)SC2=C1 TWZSIAFEFBKCNN-UHFFFAOYSA-N 0.000 description 2
- ISONHWXRIWVASO-UHFFFAOYSA-N 2,3-dibromo-1H-indene Chemical compound BrC=1CC2=CC=CC=C2C=1Br ISONHWXRIWVASO-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 2
- ZKVNLTGYNFJYDF-UHFFFAOYSA-N BrC=1C2(C3=CC=CC=C3C=1Br)CCCC2 Chemical compound BrC=1C2(C3=CC=CC=C3C=1Br)CCCC2 ZKVNLTGYNFJYDF-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- BYPCJJONRMPERB-UHFFFAOYSA-N C1(=CC(=CC=C1)C1=NC(=NC(=N1)Cl)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C1(=CC(=CC=C1)C1=NC(=NC(=N1)Cl)C1=CC=CC=C1)C1=CC=CC=C1 BYPCJJONRMPERB-UHFFFAOYSA-N 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 150000003003 phosphines Chemical group 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- PEZQQSSHQCXWBQ-UHFFFAOYSA-N spiro[cyclohexane-1,1'-indene] Chemical compound C1CCCCC21C1=CC=CC=C1C=C2 PEZQQSSHQCXWBQ-UHFFFAOYSA-N 0.000 description 2
- JUPFIGGSENJBQL-UHFFFAOYSA-N spiro[cyclopentane-1,1'-indene] Chemical compound C1CCCC21C1=CC=CC=C1C=C2 JUPFIGGSENJBQL-UHFFFAOYSA-N 0.000 description 2
- XTGPJCNIOPWATL-UHFFFAOYSA-N spiro[cyclopropane-1,1'-indene] Chemical compound C1CC11C2=CC=CC=C2C=C1 XTGPJCNIOPWATL-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- SDEAGACSNFSZCU-UHFFFAOYSA-N (3-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Cl)=C1 SDEAGACSNFSZCU-UHFFFAOYSA-N 0.000 description 1
- DQXKOHDUMJLXKH-PHEQNACWSA-N (e)-n-[2-[2-[[(e)-oct-2-enoyl]amino]ethyldisulfanyl]ethyl]oct-2-enamide Chemical compound CCCCC\C=C\C(=O)NCCSSCCNC(=O)\C=C\CCCCC DQXKOHDUMJLXKH-PHEQNACWSA-N 0.000 description 1
- 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 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KRVWTVYQGIOXQE-UHFFFAOYSA-N 1-(2,6-diphenoxyphenoxy)naphthalene Chemical group C=1C=CC(OC=2C=CC=CC=2)=C(OC=2C3=CC=CC=C3C=CC=2)C=1OC1=CC=CC=C1 KRVWTVYQGIOXQE-UHFFFAOYSA-N 0.000 description 1
- SBPIDKODQVLBGV-UHFFFAOYSA-N 1h-imidazole;pyridine Chemical compound C1=CNC=N1.C1=CC=NC=C1 SBPIDKODQVLBGV-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 1
- CJHQIEXZHOYDST-UHFFFAOYSA-N CC(Cc1c(C)[o]c2c1cccc2)N Chemical compound CC(Cc1c(C)[o]c2c1cccc2)N CJHQIEXZHOYDST-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- 229910001573 adamantine Inorganic materials 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000004653 anthracenylene group Chemical group 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000005564 oxazolylene group Chemical group 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000007774 positive electrode material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000005557 thiazolylene group Chemical group 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000005559 triazolylene group Chemical group 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- MBMQEIFVQACCCH-QBODLPLBSA-N zearalenone Chemical compound O=C1O[C@@H](C)CCCC(=O)CCC\C=C\C2=CC(O)=CC(O)=C21 MBMQEIFVQACCCH-QBODLPLBSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- 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
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H01L51/0067—
-
- H01L51/5012—
-
- H01L51/5072—
-
- 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
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
Abstract
Description
본 발명은 신규한 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자에 관한 것으로, 보다 상세하게는 발광능 및 전자 수송능이 우수한 화합물 및 이를 하나 이상의 유기물층에 포함함으로써 발광효율, 구동 전압, 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same. More particularly, the present invention relates to a compound having excellent light emitting ability and electron transporting ability, To an improved organic electroluminescent device.
1950년대 Bernanose의 유기 박막 발광 관측을 시점으로 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계 발광(electroluminescent) 소자에 대한 연구는 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층구조의 유기 전계 발광 소자가 제시되었다. 이후, 고효율, 고수명의 유기 전계 발광 소자를 만들기 위하여, 소자 내 각각의 특징적인 유기물층을 도입하는 형태로 발전하여 왔으며, 이에 사용되는 특화된 물질의 개발로 이어졌다.A study on organic electroluminescent devices that resulted in blue electroluminescence using anthracene single crystals in 1965 based on observation of organic thin film emission of Bernanose in the 1950s was made by Tang in 1987 divided by the functional layer of the hole layer and the light emitting layer An organic electroluminescent device having a laminated structure has been proposed. Thereafter, in order to form a high efficiency and high number of organic electroluminescent devices, each organic material layer has been developed into a form in which each organic material layer has been introduced into the device, leading to the development of specialized materials used therefor.
유기 전계 발광 소자에서는 두 전극 사이에 전압을 걸어 주면 양극에서는 정공이 주입되고, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 이때 유기물층으로 사용되는 물질은 그 기능에 따라, 발광 물질, 정공 주입 물질, 정공 수송 물질, 전자 수송 물질, 전자 주입 물질 등으로 분류될 수 있다.In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the anode and electrons are injected into the organic layer at the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. The material used as the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on its function.
유기 전계 발광 소자의 발광층 형성 재료는 발광색에 따라 청색, 녹색, 적색 발광 재료로 구분될 수 있다. 그밖에, 보다 나은 천연색을 구현하기 위한 발광재료로 노란색 및 주황색 발광 재료도 사용된다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 재료로서 호스트/도펀트 계를 사용할 수 있다.The light emitting layer forming material of the organic electroluminescent device can be classified into blue, green and red light emitting materials according to the luminescent color. In addition, yellow and orange light emitting materials are also used as light emitting materials for realizing better color. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material.
도판트 물질은 유기 물질을 사용하는 형광 도판트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도판트로 나눌 수 있다. 이러한 인광 재료의 개발은 이론적으로 형광에 비해 4배까지의 발광 효율을 향상시킬 수 있어 인광 도판트 뿐만 아니라 인광 호스트 재료들에 대해 관심이 집중되고 있다.The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The development of such a phosphorescent material can theoretically improve the luminous efficiency up to 4 times as compared with that of fluorescence, and attention is focused on phosphorescent host materials as well as phosphorescent dopants.
현재까지 정공 주입층, 정공 수송층. 정공 차단층, 전자 수송층으로 사용되는 물질은, 하기 화학식으로 표현된 NPB, BCP, Alq3 등이 널리 알려져 있고, 발광 물질로는 안트라센 유도체들이 형광 도판트/호스트 재료로서 보고되고 있다. 특히 발광 재료 중 효율 향상 측면에서 큰 장점을 가지고 있는 인광 도펀트 재료로서는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 청색, 녹색, 적색 도판트 재료로 사용되고 있다. 현재까지는 CBP가 인광 호스트 재료로 우수한 특성을 나타내고 있다.Up to now, hole injecting layer, hole transporting layer. NPB, BCP, Alq 3 and the like represented by the following chemical formulas are widely known as substances used as a hole blocking layer and an electron transporting layer, and anthracene derivatives as a luminescent material have been reported as fluorescent dopant / host materials. As a phosphorescent dopant material having a great advantage in terms of efficiency improvement of a light emitting material, a metal complex compound containing Ir such as Firpic, Ir (ppy) 3 , (acac) Ir (btp) 2 and the like is a blue, green, It is used as a material. So far, CBP has shown excellent properties as a phosphorescent host material.
그러나, 종래 발광 물질들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮고 열적 안정성이 매우 좋지 않기 때문에, 유기 전계 발광 소자에서의 수명 측면에서 만족할만한 수준이 되지 못하고 있다. 따라서, 우수한 성능을 가지는 발광 물질의 개발이 요구되고 있다.However, conventional luminescent materials are advantageous from the viewpoint of luminescence characteristics, but they are not satisfactory in terms of lifetime in an organic electroluminescent device because the glass transition temperature is low and the thermal stability is not very good. Therefore, development of a luminescent material having excellent performance is required.
상기한 문제점을 해결하기 위해, 본 발명은 유기 전계 발광 소자에 적용할 수 있으며, 발광능 및 전자 수송능이 우수한 신규 유기 화합물을 제공하는 것을 목적으로 한다.In order to solve the above problems, it is an object of the present invention to provide a novel organic compound which can be applied to an organic electroluminescent device and has excellent light emitting ability and electron transporting ability.
또한, 본 발명은 상기 신규 유기 화합물을 포함하여 낮은 구동전압과 높은 발광효율을 나타내며, 수명이 향상되는 유기 전계 발광 소자를 제공하는 것을 목적으로 한다.It is another object of the present invention to provide an organic electroluminescent device including the novel organic compound and exhibiting a low driving voltage and a high luminous efficiency and having an improved lifetime.
상기 목적을 달성하기 위하여, 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다.In order to achieve the above object, the present invention provides a compound represented by the following general formula (1).
상기 화학식 1에서,In Formula 1,
X는 C(R2)(R3), O, S 및 N(R4)로 이루어진 군에서 선택되고, X is selected from the group consisting of C (R 2 ) (R 3 ), O, S and N (R 4 )
L1 및 L2는 서로 동일하거나 상이하며, 각각 독립적으로 단일결합이거나, 혹은 C6~C18의 아릴렌기 및 핵원자수 5 내지 18의 헤테로아릴렌기로 이루어진 군에서 선택되고,L 1 and L 2 are the same or different and are each independently a single bond or a group selected from the group consisting of a C 6 to C 18 arylene group and a heteroarylene group having 5 to 18 nucleus atoms,
Ar1 및 Ar2는 서로 동일하거나 상이하며, 각각 독립적으로 질소를 함유하는 핵원자수 5 내지 60의 헤테로아릴기이고,Ar 1 and Ar 2 are the same or different and each is a heteroaryl group having 5 to 60 nuclear atoms and containing nitrogen,
n 은 0 내지 4 의 정수이고,n is an integer from 0 to 4,
R1 내지 R4는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 혹은 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, R 1 to R 4 are the same or different, each independently represent hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C 1 ~ alkenyl group of the C 40 alkyl group, C 2 ~ C 40 of, C 2 ~ alkynyl group of C 40, C 3 ~ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyl silyl group, the group C 6 ~ C 60 aryl silyl, C 1 ~ group alkylboronic of C 40, C 6 ~ C group of 60 arylboronic, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ selected from the group consisting of an aryl amine of the C 60 of or, or adjacent groups bonded fused to the A ring can be formed,
상기 L1 및 L2의 아릴렌기 및 헤테로아릴렌기와, 상기 Ar1 및 Ar2, R1 내지 R4의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.Wherein L 1, and arylene group of L 2 and a heteroarylene group, an alkyl group of said Ar 1 and Ar 2, R 1 to R 4, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, An alkyl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, A nitro group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C An aryl group having 6 to 60 carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 ~ C 60 aryl silyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C of the group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ aryl phosphine oxide of the C 60 group And C 6 -C An arylamine group having 1 to 60 carbon atoms, and when the substituent is plural, they may be the same or different from each other.
또한, 본 발명은 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하고, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 것인 유기 전계 발광 소자를 제공한다. 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자 수송층 및 전자 주입층으로 이루어진 군에서 선택될 수 있다. 이때, 상기 화학식 1로 표시되는 화합물은 발광층의 인광 호스트 또는 전자 수송층 재료로 사용될 수 있다.The present invention also provides an organic electroluminescent device comprising a cathode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes a compound represented by the general formula An electroluminescent device is provided. The organic material layer containing the compound represented by Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, a light emission assisting layer, a light emitting layer, an electron transport layer, and an electron injection layer. At this time, the compound represented by Formula 1 may be used as a phosphorescent host or an electron transport layer material of the light emitting layer.
본 발명의 화학식 1로 표시되는 화합물은 열적 안정성 및 발광 특성이 우수하기 때문에 유기 전계 발광 소자의 유기물층의 재료로 사용될 수 있다.The compound represented by the general formula (1) of the present invention has excellent thermal stability and luminescent properties and can be used as a material of an organic material layer of an organic electroluminescent device.
특히, 본 발명의 화학식 1로 표시되는 화합물을 인광 호스트 재료 또는 전자 수송 재료로 사용할 경우, 종래의 호스트 재료 또는 전자 수송 재료에 비해 낮은 구동전압 및 높은 효율을 갖는 유기 전계 발광 소자를 제조할 수 있고, 나아가 성능 및 수명이 향상된 풀 칼라 디스플레이 패널도 제조할 수 있다.In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host material or an electron transporting material, an organic electroluminescent device having a lower driving voltage and higher efficiency than a conventional host material or an electron transporting material can be manufactured And further, a full color display panel having improved performance and lifetime can be manufactured.
본 발명에 따른 신규 유기 화합물은 인덴, 벤조퓨란, 티오펜, 인돌, 벤조인돌 모이어티를 코어(core)로 하며, 상기 코어의 5원 고리에 두 개의 전자 끌개기(electron withdrawing group, EWG)가 연결기(linker)를 통해 연결된 구조를 기본 골격으로 하며, 이러한 기본 골격에 다양한 치환기가 도입된 상기 화학식 1로 표시되는 것을 특징으로 한다.The novel organic compound according to the present invention is characterized in that an electron withdrawing group (EWG) is added to the five-membered ring of the core using indene, benzofuran, thiophene, indole and benzoindole moiety as a core A structure connected through a linker is taken as a basic skeleton, and the basic skeleton is represented by the above formula (1) in which various substituents are introduced.
상기 화학식 1로 표시되는 화합물에서, 코어(
또한, 상기 화학식 1로 표시되는 화합물은 두 개의 전자 끌개기를 포함함으로써 하나의 전자 끌개기를 포함하는 화합물에 비해 전자 흡수성(EWG power)이 우수하고 유리전이온도가 높아 열적 안정성이 우수할 뿐만 아니라, 캐리어 수송능, 특히 전자 수송능, 발광능 등이 우수하다. 이러한 화학식 1의 화합물을 유기 전계 발광 소자에 사용할 경우에는 소자의 구동전압, 효율, 수명 등이 향상될 수 있다. 또한, 이러한 화학식 1의 화합물은 삼중항 에너지가 높기 때문에 유기 전계 발광 소자에 사용될 경우, 최신의 전자 수송층(electron transfer layer, ETL) 재료에 있어 TTF(triplet-triplet fusion) 효과로 인해 우수한 효율 상승을 나타낼 수 있다.In addition, the compound represented by Formula (1) includes two electron attracting groups, so that it has an excellent electron absorbing property (EWG power) and a high glass transition temperature as compared with the compound including one electron attracting group, Transporting ability, particularly electron transporting ability, and light emitting ability. When the compound of Formula 1 is used in an organic electroluminescent device, the driving voltage, efficiency, lifetime, etc. of the device can be improved. When the compound of Formula 1 is used in an organic electroluminescent device due to its high triplet energy, the efficiency of the electron transfer layer (ETL) is improved due to the triplet-triplet fusion (TTF) effect. .
이때, 전자 끌개기는 질소 함유 헤테로고리와 같이 전자 흡수성이 큰 치환기일 수 있고, 전자의 더 빠른 이동성(mobility)을 구현하기 위해 전자 수송능이 우수한 트리아졸로피리딘, 이미다졸피리딘, 트리아진, 피리미딘 등인 것이 바람직하다. 이러한 전자 끌개기를 포함하는 상기 화학식 1의 화합물은 유기 전계 발광 소자의 전자 수송층 재료로 사용되어, 높은 효율과 빠른 이동성(mobility)를 나타낼 수 있다.At this time, the electron-withdrawing group may be a substituent having a high electron absorbing property such as a nitrogen-containing heterocycle, and may be substituted with triazolepolydine, imidazole pyridine, triazine, pyrimidine, or the like having excellent electron transporting ability to realize faster mobility of electrons . The compound of Formula 1 including such an electron-withdrawing group can be used as an electron transport layer material of an organic electroluminescent device, and can exhibit high efficiency and fast mobility.
이러한 두 개의 전자 끌개기가 인덴/벤조퓨란/티오펜/인돌/벤조인돌 모이어티(core)에 연결된 화합물은 두 개의 전자 끌개기가 직접 연결되거나 페닐렌을 통해 연결된 화합물에 비해 분자량이 증가하여 유리전이온도가 향상될 수 있을 뿐만 아니라, 밴드갭의 감소로 인해 반응성이 향상되어 유기 전기 발광 소자의 전자 수송층 재료로 사용될 수 있다(하기 표 1 참조).Compounds in which these two electron-withdrawing groups are connected to an indene / benzofuran / thiophene / indole / benzoindole moiety have a molecular weight higher than that of a compound in which two electron-withdrawing groups are directly connected or connected via phenylene, Can be improved as well as the reactivity is improved due to the reduction of the bandgap and can be used as an electron transport layer material of the organic electroluminescence device (see Table 1 below).
또한, 상기 화학식 1로 표시되는 화합물은 연결기 및 코어(core)에 도입되는 치환기(특히, 알킬기)에 의해 화합물의 용매에 대한 용해도가 개선됨으로써 유기 전계 발광 소자의 유기물층 재료(특히, 발광층 및 전자 수송층)로 사용될 수 있다.In addition, the compound represented by Formula 1 is improved in solubility of a compound in a solvent by a substituent (particularly, an alkyl group) introduced into a linking group and a core, thereby improving the solubility of the compound in an organic layer material of the organic electroluminescence device ).
또한, 상기 화학식 1로 표시되는 화합물은 상기 기본 골격에 도입되는 다양한 치환기(예컨대, 방향족고리)에 의해 화합물의 분자량이 유의적으로 증대됨으로써 유리전이온도가 향상될 수 있고, 이를 포함하는 유기 전계 발광 소자의 내구성 및 수명 특성을 크게 향상시킬 수 있다. 이러한 화학식 1의 화합물은 유기 전계 발광 소자의 유기물층 재료, 특히 발광층 재료 및 전자 수송층 재료로 사용될 수 있다. In addition, the compound represented by the formula (1) can increase the glass transition temperature by significantly increasing the molecular weight of the compound due to various substituents (for example, aromatic rings) introduced into the basic skeleton, and the organic electroluminescence The durability and lifetime characteristics of the device can be greatly improved. The compound of the formula (1) can be used as an organic material layer material of an organic electroluminescence device, particularly a light emitting layer material and an electron transporting layer material.
이와 같은 화학식 1로 표시되는 화합물은 종래 유기 전계 발광 소자용 재료[예: 4,4-dicarbazolybiphenyl (이하, ‘CBP’라 함)]에 비해 높은 분자량을 갖기 때문에, 유리전이온도가 높아 열적 안정성이 우수할 뿐만 아니라 발광능이 우수하다. 따라서, 상기 화학식 1의 화합물을 유기 전계 발광 소자의 유기물층에 적용할 경우에는 소자의 구동전압, 효율, 수명 등이 향상될 수 있다. 이러한 화학식 1의 화합물은 유기 전계 발광 소자의 유기물층 재료로 사용될 수 있으며, 바람직하게는 발광층 재료(녹색의 인광 호스트 재료) 및 전자 수송층 재료로 사용될 수 있다.Since the compound represented by Chemical Formula 1 has a higher molecular weight than conventional materials for organic electroluminescence devices [for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')], the glass transition temperature is high, It is not only excellent but also excellent in luminous efficiency. Accordingly, when the compound of Formula 1 is applied to an organic material layer of an organic electroluminescent device, the driving voltage, efficiency, lifetime, etc. of the device can be improved. The compound of the formula (1) can be used as an organic layer material of an organic electroluminescence device, and can be preferably used as a light emitting layer material (green phosphorescent host material) and an electron transporting layer material.
보다 구체적으로, 본 발명에 따른 화학식 1로 표시되는 화합물은 '인덴, 벤조퓨란, 티오펜, 인돌, 벤조인돌 모이어티'의 5원 고리에 '두 개의 전자 끌개기(EWG)'가 연결기를 통해 연결되면서 다양한 치환기 도입된다.More specifically, the compound represented by the formula (1) according to the present invention is characterized in that two electron attracting groups (EWG) are bonded to a five-membered ring of indene, benzofuran, thiophene, indole and benzoindole moiety via a linking group Various substituents are introduced as they are connected.
상기 화학식 1로 표시되는 화합물에서, L1 및 L2는 서로 동일하거나 상이하며, 각각 독립적으로 단일결합이거나, 혹은 2가의 연결기일 수 있다. 이때, 상기 2가 연결기는 C6~C18의 아릴렌기 및 핵원자수 5 내지 18의 헤테로아릴렌기로, 페닐렌기, 비페닐렌기, 나프틸렌기, 안트라세닐렌기, 인데닐렌기, 피란트레닐렌기, 카르바졸릴렌기, 티오페닐렌기, 인돌일렌기, 푸리닐렌기, 퀴놀리닐렌기, 피롤일렌기, 이미다졸릴렌기, 옥사졸릴렌기, 티아졸릴렌기, 트리아졸릴렌기, 피리디닐렌기, 피리미디닐렌기 등일 수 있다.In the compound represented by the general formula (1), L 1 and L 2 may be the same or different and each independently a single bond or a divalent linking group. The divalent linking group is a C 6 to C 18 arylene group and a heteroarylene group having 5 to 18 nucleus atoms, and examples thereof include a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, a pyranthrenyl group A thiophenylene group, an indolylene group, a pyrrolylene group, a quinolinylene group, a pyrrolylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a pyridinylene group, And a methylene group.
바람직하게는, 상기 L1 및 L2는 서로 동일하거나 상이하며, 각각 독립적으로 C6~C18의 아릴렌기일 수 있다.Preferably, the L 1 and L 2, and are the same or different, each independently can be an arylene date of C 6 ~ C 18.
Ar1 및 Ar2는 전자 흡수성이 큰 전자 끌개기로서 서로 동일하거나 상이하며, 각각 독립적으로 질소를 함유하는 핵원자수 5 내지 60의 헤테로아릴기일 수 있다. Ar 1 and Ar 2 may be the same or different and each independently represent a heteroaryl group having 5 to 60 nuclear atoms and containing nitrogen.
바람직하게는, 상기 Ar1 및 Ar2는 서로 동일하며, 우수한 전자 흡수성을 나타내기 위해 질소를 두 개 이상 함유하는 핵원자수 5 내지 60의 헤테로아릴기일 수 있다. Preferably, Ar 1 and Ar 2 are the same as each other, and may be a heteroaryl group having 5 to 60 nuclear atoms containing two or more nitrogen atoms to exhibit excellent electron-absorbing properties.
이러한 Ar1 및 Ar2는 서로 동일하거나 상이하며, 각각 독립적으로 하기 A1 내지 A16, B1 내지 B25 중 어느 하나의 치환체로 보다 구체화될 수 있다. 그러나, 이에 특별히 한정되지 않는다.These Ar 1 and Ar 2 may be the same or different from each other, and each may be independently substituted with any one of the substituents of the following formulas A1 to A16 and B1 to B25. However, it is not particularly limited.
상기 A1 내지 A16, B1 내지 B25에서, p는 0 내지 4의 정수이다. 상기 p가 0일 경우에는 수소가 R6으로 치환되지 않은 것을 의미하고, 상기 p가 1 내지 4의 정수일 경우에는 수소가 R6으로 치환되는 것을 의미한다.In the above-mentioned A1 to A16 and B1 to B25, p is an integer of 0 to 4. When p is 0, it means that hydrogen is not substituted with R 6 , and when p is an integer from 1 to 4, it means that hydrogen is replaced with R 6 .
R5 및 R6은 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 혹은 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며, 상기 R5가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있으며, 상기 R6이 복수인 경우, 이들은 서로 동일하거나 상이할 수 있고,R 5 and R 6 are the same or different and are each independently hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C 1 ~ alkenyl group of the C 40 alkyl group, C 2 ~ C 40 of, C 2 ~ alkynyl group of C 40, C 3 ~ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyl silyl group, the group C 6 ~ C 60 aryl silyl, C 1 ~ group alkylboronic of C 40, C 6 ~ C group of 60 arylboronic, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ selected from the group consisting of an aryl amine of the C 60 of or, or adjacent groups bonded fused to the case can form a ring, wherein R 5 is plural, they may be the same or different from each other, and when the R 6 is a plurality, they may be the same or different from each other,
상기 R5 및 R6의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.Alkyl groups of the R 5 and R 6, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkenyl group, an aryl group, A C 3 to C 40 cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkynyl group, ~ C 40 alkyloxy group of, C 6 ~ aryloxy C 60, C 1 ~ C 40 alkyl silyl group, C 6 ~ aryl silyl group of C 60, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ one or more substituents selected from the group consisting of C 60 arylamine It may be substituted, and wherein when the substituent is plural, they may be the same or different from each other.
바람직하게는, 상기 R5 및 R6은 서로 동일하거나 상이하며, 각각 독립적으로 수소, C6~C60의 아릴기 및 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군에서 선택될 수 있다.Preferably, R 5 and R 6 are the same or different from each other and each independently selected from the group consisting of hydrogen, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms.
또한, 상기 화학식 1로 표시되는 화합물에서, n은 0 내지 4 의 정수이다. 상기 n이 0일 경우에는 수소가 R1으로 치환되지 않은 것을 의미하고, 상기 n이 1 내지 4의 정수일 경우에는 수소가 R1으로 치환되는 것을 의미한다.In the compounds represented by the above formula (1), n is an integer of 0 to 4. When n is 0, it means that hydrogen is not substituted by R 1 , and when n is an integer from 1 to 4, it means that hydrogen is substituted with R 1 .
R1 내지 R4는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 혹은 인접하는 기와 결합하여 축합 고리를 형성할 수 있다.R 1 to R 4 are the same or different, each independently represent hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C 1 ~ alkenyl group of the C 40 alkyl group, C 2 ~ C 40 of, C 2 ~ alkynyl group of C 40, C 3 ~ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyl silyl group, the group C 6 ~ C 60 aryl silyl, C 1 ~ group alkylboronic of C 40, C 6 ~ C group of 60 arylboronic, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ selected from the group consisting of an aryl amine of the C 60 of or, or adjacent groups bonded fused to the A ring can be formed.
바람직하게는, R1 내지 R3은 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기 및 C2~C40의 알키닐기로 이루어진 군에서 선택되거나, 혹은 인접하는 기와 결합하여 축합 고리를 형성할 수 있다. 더욱 바람직하게는, R1 내지 R3은 수소 또는 C1~C40의 알킬기이거나, 혹은 인접하는 기와 결합하여 축합 고리를 형성할 수 있다.Preferably, R 1 to R 3 are the same or different and each independently represents hydrogen, deuterium (D), halogen, cyano, nitro, C 1 to C 40 alkyl, C 2 to C 40 alkenyl And an alkynyl group of C 2 to C 40 , or may be bonded to an adjacent group to form a condensed ring. More preferably, R 1 to R 3 are hydrogen or a C 1 to C 40 alkyl group, or may combine with adjacent groups to form a condensed ring.
바람직하게는, R4는 수소, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택될 수 있다. 더욱 바람직하게는, R4는 C6~C60의 아릴기일 수 있다.Preferably, R 4 may be selected from the group consisting of hydrogen, C 6 ~ C 60 aryl group, an aryl nuclear atoms of 5 to 60 heteroaryl group, and a C 6 ~ C 60 aryl amine. More preferably, R 4 may be aryl date of C 6 ~ C 60.
이러한 화학식 1로 표시되는 화합물은 하기 화학식 2 내지 5 중에서 적어도 어느 하나로 구체화될 수 있다.The compound represented by the formula (1) may be represented by at least one of the following formulas (2) to (5).
상기 화학식 2 내지 5에서, L1, L2, Ar1, Ar2, n, R1 내지 R4는 각각 상기 화학식 1에서 정의한 바와 같다.L 1 , L 2 , Ar 1 , Ar 2 , n, and R 1 to R 4 are as defined in Formula 1, respectively.
또한, 상기 화학식 1로 표시되는 화합물은 하기 화학식 6 내지 15 중에서 적어도 어느 하나로 보다 구체화될 수 있다. 그러나, 이에 특별히 한정되지 않는다.The compound represented by the formula (1) may be further represented by at least one of the following formulas (6) to (15). However, it is not particularly limited.
상기 화학식 6 내지 15에서, L1, L2, Ar1, Ar2, n 및 R1는 각각 상기 화학식 1에서 정의한 바와 같다.Wherein L 1 , L 2 , Ar 1 , Ar 2 , n and R 1 are the same as defined in the above formula (1).
A는 R1과 다른 R1이 결합하여 축합 고리를 형성하는 것으로, 6원 방향족 고리인 것이 바람직하다.A is a 6-membered aromatic ring in which R 1 and the other R 1 bond to form a condensed ring.
Ar3은 C6~C18의 아릴기로, 페닐기, 비페닐기, 나프틸기, 페난트렌기, 안트라센기, 트라이페닐렌기, 피렌기 등일 수 있다.Ar 3 is a C 6 to C 18 aryl group, and may be a phenyl group, a biphenyl group, a naphthyl group, a phenanthrene group, an anthracene group, a triphenylene group, a pyrene group, or the like.
이상에서 설명한 본 발명의 화학식 1로 표시되는 화합물은 하기 예시되는 화합물 A-1 내지 A-48, B-1 내지 B-48, C-1 내지 C-48, D-1 내지 D-48, E-1 내지 E-48, F-1 내지 F-48, G-1 내지 G-48, H-1 내지 H-48, I-1 내지 I-48, J-1 내지 J-48 중 어느 하나로 표시되는 화합물로 보다 구체화될 수 있다. 그러나, 본 발명의 화학식 1로 표시되는 화합물이 하기 예시된 것들에 의해 한정되는 것은 아니다.The compound represented by the formula (1) of the present invention is represented by the following compounds A-1 to A-48, B-1 to B-48, C-1 to C-48, D-1 to D- 1 to E-48, F-1 to F-48, G-1 to G-48, H-1 to H-48, I-1 to I-48 and J-1 to J-48 ≪ / RTI > However, the compounds represented by formula (1) of the present invention are not limited by the following examples.
본 발명에서 “알킬”은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이러한 알킬의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, " alkyl " means a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples of such alkyl include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl.
본 발명에서 “알케닐(alkenyl)”은 탄소-탄소 이중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이러한 알케닐의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "alkenyl" means a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples of such alkenyl include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
본 발명에서“알키닐(alkynyl)”은 탄소-탄소 삼중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이러한 알키닐의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, " alkynyl " means a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples of such alkynyls include, but are not limited to, ethynyl, 2-propynyl, and the like.
본 발명에서 “아릴”은 단독 고리 또는 2 이상의 고리가 조합된 탄소수 6 내지 60의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있다. 이러한 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴 등을 들 수 있으나, 이에 한정되지는 않는다.&Quot; Aryl " in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
본 발명에서 “헤테로아릴”은 핵원자수 5 내지 60의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있고, 나아가 아릴기와의 축합된 형태도 포함될 수 있다. 이러한 헤테로아릴의 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6-원 모노사이클릭 고리, 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리 및 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등을 들 수 있으나, 이에 한정되지는 않는다.&Quot; Heteroaryl " in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are pendant or condensed with each other may be included, and further, a condensed form with an aryl group may be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, and heterocyclic rings such as 2-furanyl, N-imidazolyl, 2- , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
본 발명에서 “아릴옥시”는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 6 내지 60의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, "aryloxy" is a monovalent substituent represented by RO-, and R represents aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
본 발명에서 “알킬옥시”는 R’O-로 표시되는 1가의 치환기로, 상기 R’는 탄소수 1 내지 40의 알킬을 의미한다. 이러한 알킬옥시는 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함할 수 있다. 이러한 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, " alkyloxy " means a monovalent substituent group represented by R'O-, and R 'means alkyl having 1 to 40 carbon atoms. Such alkyloxy may include linear, branched or cyclic structures. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy and pentoxy.
본 발명에서 “아릴아민”은 탄소수 6 내지 60의 아릴로 치환된 아민을 의미한다.&Quot; Arylamine " in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
본 발명에서 “시클로알킬”은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 노르보닐(norbornyl), 아다만틴(adamantine) 등을 들 수 있으나, 이에 한정되지는 않는다.&Quot; Cycloalkyl " in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
본 발명에서 “헤테로시클로알킬”은 핵원자수 3 내지 40의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로 원자로 치환된다. 이러한 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등을 들 수 있으나, 이에 한정되지는 않는다.&Quot; Heterocycloalkyl " in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one of the carbons, preferably one to three carbons, Or < RTI ID = 0.0 > Se. ≪ / RTI > Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
본 발명에서 “알킬실릴”은 탄소수 1 내지 40의 알킬로 치환된 실릴이고, “아릴실릴”은 탄소수 6 내지 60의 아릴로 치환된 실릴을 의미한다.In the present invention, "alkylsilyl" is silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 6 to 60 carbon atoms.
본 발명에서 “알킬보론”은 탄소수 1 내지 40의 알킬로 치환된 보론이고, “아릴보론”은 탄소수 6 내지 60의 아릴로 치환된 보론을 의미한다.In the present invention, "alkyl boron" is boron substituted with alkyl having 1 to 40 carbon atoms, and "aryl boron" means boron substituted with aryl having 6 to 60 carbon atoms.
본 발명에서 "아릴포스핀"은 탄소수 6 내지 60의 아릴로 치환된 포스핀을 의미하고, "아릴포스핀옥사이드"는 탄소수 6 내지 60의 아릴로 치환된 포스핀이 O를 포함하는 것을 의미한다.In the present invention, "arylphosphine" means a phosphine substituted with aryl having 6 to 60 carbon atoms, and "arylphosphine oxide" means that the phosphine substituted with aryl having 6 to 60 carbon atoms includes O .
본 발명에서 “축합 고리”는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.In the present invention, the term "condensed rings" means condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.
이와 같은 본 발명의 화학식 1로 표시되는 화합물은 하기 실시예의 합성과정을 참고하여 다양하게 합성할 수 있다.The compound represented by formula (1) of the present invention can be synthesized in various ways with reference to the synthesis process of the following examples.
2. 유기 2. Organic 전계Field 발광 소자 Light emitting element
본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.The present invention provides an organic electroluminescent device comprising a compound represented by the above formula (1).
보다 구체적으로, 본 발명에 따른 유기 전계 발광 소자는 양극(anode), 음극(cathode) 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화합물은 단독으로 사용되거나, 또는 2 이상이 혼합되어 사용될 수 있다.More specifically, the organic electroluminescent device according to the present invention includes at least one anode, an anode, and at least one organic layer sandwiched between the anode and the cathode, and at least one of the one or more organic layers Include the compounds represented by the above formula (1). At this time, the compounds may be used alone or in combination of two or more.
상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자 수송층 및 전자 주입층 중 어느 하나 이상일 수 있고, 이 중에서 적어도 하나의 유기물층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 구체적으로, 상기 화학식 1의 화합물을 포함하는 유기물층은 발광층 및 전자 수송층인 것이 바람직하다.The at least one organic material layer may include at least one of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. have. Specifically, the organic material layer containing the compound of Formula 1 is preferably a light emitting layer and an electron transporting layer.
본 발명의 유기 전계 발광 소자의 발광층은 호스트 재료(바람직하게는, 인광 호스트 재료)를 포함할 수 있다. 또한, 본 발명의 유기 전계 발광 소자의 발광층은 상기 화학식 1의 화합물 이외의 화합물을 호스트로 포함할 수 있다.The light emitting layer of the organic electroluminescence device of the present invention may include a host material (preferably, a phosphorescent host material). The light emitting layer of the organic electroluminescent device of the present invention may contain a compound other than the compound of Formula 1 as a host.
이러한 본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 비제한적인 예로 기판, 양극, 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자 수송층 및 음극이 순차적으로 적층된 구조일 수 있다. 이때, 상기 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자 수송층 및 전자 주입층 중 하나 이상은 상기 화학식 1로 표시되는 화합물을 포함할 수 있고, 바람직하게는 발광층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 여기서, 상기 전자 수송층 위에는 전자 주입층이 추가로 적층될 수 있다. 또한, 본 발명의 유기 전계 발광 소자의 구조는 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조일 수 있다.The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer and a cathode are sequentially stacked . At least one of the hole injecting layer, the hole transporting layer, the light-emitting auxiliary layer, the light emitting layer, the electron transporting layer, and the electron injecting layer may include the compound represented by Formula 1, ≪ / RTI > compounds. Here, an electron injection layer may be further stacked on the electron transport layer. Further, the structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic layer.
한편, 본 발명의 유기 전계 발광 소자는 상기 유기물층 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는, 당업계에 공지된 재료 및 방법으로 유기물층 및 전극을 형성하여 제조할 수 있다.Meanwhile, the organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by the above formula have.
상기 유기물층은 진공 증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이에 한정되지는 않는다.The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
본 발명의 유기 전계 발광 소자 제조시 사용되는 기판은 특별히 한정되지 않으나, 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등을 사용할 수 있다.The substrate used in the fabrication of the organic electroluminescent device of the present invention is not particularly limited, but silicon wafer, quartz, glass plate, metal plate, plastic film and sheet can be used.
또한, 양극 물질로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 또는 폴리아닐린과 같은 전도성 고분자; 및 카본블랙 등을 들 수 있으나, 이에 한정되지는 않는다.Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO: Al or SnO2: Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
또한, 음극 물질로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; 및 LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등을 들 수 있으나, 이에 한정되지는 않는다.Examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; And multi-layer structure materials such as LiF / Al or LiO2 / Al, but are not limited thereto.
또한, 정공 주입층, 정공 수송층 및 발광 보조층은 특별히 한정되는 것은 아니며, 당 업계에 알려진 통상의 물질을 사용할 수 있다.The hole injecting layer, the hole transporting layer, and the light emitting auxiliary layer are not particularly limited, and ordinary materials known in the art can be used.
이하, 본 발명을 실시예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐, 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail with reference to the following examples. However, the following examples are illustrative of the present invention, and the present invention is not limited by the following examples.
[[ 준비예Preparation Example 1] 2,2'-((1,1- 1] 2,2 ' - ((1,1- dimethyldimethyl -1H--1H- indeneindene -2,3--2,3- diyldiyl )bis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)의 합성) bis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
<단계 1> 2,3-bis(4-≪ Step 1 > 2,3-bis (4- chlorophenylklorophenyl )-1,1-) -1,1- dimethyldimethyl -1H--1H- indene의indene 합성 synthesis
2,3-dibromo-1,1-dimethyl-1H-indene (100.0g, 331.1 mmol), (4-chlorophenyl)boronic acid (113.9 g, 728.4 mmol) 및 Pd(PPh3)4 (19.1 g, 16.5 mmol), K2CO3 (91.5 g, 662.2 mmol)을 Toluene 1000ml, EtOH 200ml, H2O 200ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 2,3-bis(4-chlorophenyl)-1,1-dimethyl-1H-indene (99.2 g, 수율 82 %)을 얻었다.2,3-dibromo-1,1-dimethyl- 1H-indene (100.0g, 331.1 mmol), (4-chlorophenyl) boronic acid (113.9 g, 728.4 mmol) and Pd (PPh 3) 4 (19.1 g, 16.5 mmol ) And K 2 CO 3 (91.5 g, 662.2 mmol) were placed in 1000 ml of toluene, 200 ml of EtOH and 200 ml of H 2 O, and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, 2,3-bis (4-chlorophenyl) -1,1-dimethyl-1H-indene (99.2 g, yield 82%) was obtained by column chromatography.
1H-NMR: δ 1.69 (s, 6H), 7.22 (t, 1H), 7.27-7.30 (m, 2H), 7.42 (d, 1H), 7.44 (q, 4H), 7.49 (q, 4H) 1 H-NMR: δ 1.69 ( s, 6H), 7.22 (t, 1H), 7.27-7.30 (m, 2H), 7.42 (d, 1H), 7.44 (q, 4H), 7.49 (q, 4H)
[LCMS] : 366 [LCMS]: 366
<단계 2> 2,2'-((1,1-≪ Step 2 > 2,2 '- ((1,1- dimethyldimethyl -1H--1H- indeneindene -2,3--2,3- diyldiyl )bis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)의 합성) bis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
2,3-bis(4-chlorophenyl)-1,1-dimethyl-1H-indene (99.2 g, 271.5 mmol)와 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (151.4 g, 597.4 mmol) 및 Pd(dppf)Cl2 (11.1 g, 8.1 mmol), KOAc (53.3 g, 543.1 mmol), Xphos (12.9 g, 27.1 mmol)을 1,4-Dioxane 1000ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 2,2'-((1,1-dimethyl-1H-indene-2,3-diyl)bis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (90.8 g, 수율 61 %)을 얻었다.A mixture of 2,3-bis (4-chlorophenyl) -1,1-dimethyl-1H-indene (99.2 g, 271.5 mmol) and 4,4,4 ', 4', 5,5,5 ' Dioxaborolane (151.4 g, 597.4 mmol) and Pd (dppf) Cl 2 (11.1 g, 8.1 mmol), KOAc (53.3 g, 543.1 mmol), Xphos (12.9 g, , 27.1 mmol) were dissolved in 1000 ml of 1,4-dioxane and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, the target compound, 2,2 '- ((1,1-dimethyl-1H-indene-2,3-diyl) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (90.8 g, yield 61%).
1H-NMR: δ 1.24 (s, 24H), 1.69 (s, 6H), 7.22 (t, 1H), 7.27-7.30 (m, 2H), 7.42 (d, 1H), 7.50 (d, 4H), 7.75 (d, 4H) 1 H-NMR: δ 1.24 ( s, 24H), 1.69 (s, 6H), 7.22 (t, 1H), 7.27-7.30 (m, 2H), 7.42 (d, 1H), 7.50 (d, 4H), 7.75 (d, 4H)
[LCMS] : 549 [LCMS]: 549
[[ 준비예Preparation Example 2] 2,2'-((1,1- 2] 2,2 ' - ((1,1- dimethyldimethyl -1H--1H- indeneindene -2,3--2,3- diyldiyl )bis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)의 합성) bis (3,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
<단계 1>의 반응물로 (4-chlorophenyl)boronic acid 대신 (3-chlorophenyl)boronic acid을 사용한 것을 제외하고는 준비예 1과 동일한 과정을 수행하여 목적 화합물 89.3g (final 수율 47 %)을 얻었다.89.3 g (final yield: 47%) of the desired compound was obtained by carrying out the same procedure as described in Preparation Example 1, except that (3-chlorophenyl) boronic acid was used instead of (4-chlorophenyl) boronic acid as a reactant in Step 1.
1H-NMR: δ 1.24 (s, 24H), 1.69 (s, 6H), 6.95(s, 1H), 7.22 (t, 1H), 7.27-7.30 (m, 2H), 7.42 (d, 1H), 7.45-7.46 (m, 2H), 7.50 (d, 1H), 7.60-7.61 (m, 4H) 1 H-NMR: δ 1.24 ( s, 24H), 1.69 (s, 6H), 6.95 (s, 1H), 7.22 (t, 1H), 7.27-7.30 (m, 2H), 7.42 (d, 1H), 7.45-7.46 (m, 2H), 7.50 (d, 1H), 7.60-7.61 (m, 4H)
[LCMS] : 549 [LCMS]: 549
[[ 준비예Preparation Example 3] 2,2'-((1,1-diethyl-1H- 3] 2,2 ' - ((1,1-diethyl-1H- indeneindene -2,3--2,3- diyldiyl )bis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)의 합성) bis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
<단계 1>의 반응물로 2,3-dibromo-1,1-dimethyl-1H-indene 대신 2,3-dibromo-1,1-diethyl-1H-indene을 사용한 것을 제외하고는 준비예 1과 동일한 과정을 수행하여 목적 화합물 90.7g (final 수율 58 %)을 얻었다.The procedure of Preparation Example 1 was repeated except that 2,3-dibromo-1,1-diethyl-1H-indene was used instead of 2,3-dibromo-1,1-dimethyl-1H- To give 90.7 g (final yield 58%) of the desired compound.
1H-NMR: δ 0.90 (s, 6H), 1.24 (s, 24H), 1.62 (s, 4H), 7.22 (t, 1H), 7.27-7.30 (m, 2H), 7.42 (d, 1H), 7.50 (d, 4H), 7.75 (d, 4H) 1 H-NMR: δ 0.90 ( s, 6H), 1.24 (s, 24H), 1.62 (s, 4H), 7.22 (t, 1H), 7.27-7.30 (m, 2H), 7.42 (d, 1H), 7.50 (d, 4H), 7.75 (d, 4H)
[LCMS] : 577 [LCMS]: 577
[[ 준비예Preparation Example 4] 2,2'-((1,1-diethyl-1H- 4] 2,2 '- ((1,1-diethyl-1H- indeneindene -2,3--2,3- diyldiyl )bis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)의 합성) bis (3,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
<단계 1>의 반응물로 2,3-dibromo-1,1-dimethyl-1H-indene 대신 2,3-dibromo-1,1-diethyl-1H-indene을 사용한 것을 제외하고는 준비예 2와 동일한 과정을 수행하여 목적 화합물 72.8g (overall 수율 47 %)을 얻었다.The same procedure as in Preparation Example 2 was carried out except that 2,3-dibromo-1,1-diethyl-1H-indene was used instead of 2,3-dibromo-1,1-dimethyl- To obtain 72.8 g (overall yield: 47%) of the target compound.
1H-NMR: δ 0.90 (s, 6H), 1.24 (s, 24H), 1.62 (s, 4H), 6.95(s, 1H), 7.22 (t, 1H), 7.27-7.30 (m, 2H), 7.42 (d, 1H), 7.45-7.46 (m, 2H), 7.50 (d, 1H), 7.60-7.61 (m, 4H) 1 H-NMR: δ 0.90 ( s, 6H), 1.24 (s, 24H), 1.62 (s, 4H), 6.95 (s, 1H), 7.22 (t, 1H), 7.27-7.30 (m, 2H), 7.42 (d, 1H), 7.45-7.46 (m, 2H), 7.50 (d, 1H), 7.60-7.61 (m, 4H)
[LCMS] : 577[LCMS]: 577
[[ 준비예Preparation Example 5] 2,2'-( 5] 2,2 '- ( spirospiro [[ cyclopropanecyclopropane -1,1'--1,1'- indeneindene ]-2',3'-] -2 ', 3'- diylbis(4,1-phenylene))bisdiylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane)의 합성(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
<단계 1>의 반응물로 2,3-dibromo-1,1-dimethyl-1H-indene 대신 2',3'-dibromospiro[cyclopropane-1,1'-indene]을 사용한 것을 제외하고는 준비예 1과 동일한 과정을 수행하여 목적 화합물 90.5g (final 수율 61 %)을 얻었다.Preparation Example 1 was repeated except that 2 ', 3'-dibromospiro [cyclopropane-1,1'-indene] was used instead of 2,3-dibromo-1,1-dimethyl-1H- The same procedure was carried out to obtain 90.5 g (final yield: 61%) of the target compound.
1H-NMR: δ 0.39-0.40 (m, 2H), 0.63-0.64 (m, 2H), 1.24 (s, 24H), 7.22 (t, 1H), 7.27-7.30 (m, 2H), 7.42 (d, 1H), 7.50 (d, 4H), 7.75 (d, 4H) 1 H-NMR: δ 0.39-0.40 ( m, 2H), 0.63-0.64 (m, 2H), 1.24 (s, 24H), 7.22 (t, 1H), 7.27-7.30 (m, 2H), 7.42 (d , 7.50 (d, 4H), 7.75 (d, 4H)
[LCMS] : 547 [LCMS]: 547
[[ 준비예Preparation Example 6] 2,2'-( 6] 2,2 ' - ( spirospiro [[ cyclopropanecyclopropane -1,1'--1,1'- indeneindene ]-2',3'-] -2 ', 3'- diylbis(3,1-phenylene))bisdiylbis (3,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane)의 합성(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
<단계 1>의 반응물로 2,3-dibromo-1,1-dimethyl-1H-indene 대신 2',3'-dibromospiro[cyclopropane-1,1'-indene]을 사용한 것을 제외하고는 준비예 2와 동일한 과정을 수행하여 목적 화합물 83.1g (final 수율 56 %)을 얻었다.Preparation Example 2 was repeated except that 2 ', 3'-dibromospiro [cyclopropane-1,1'-indene] was used instead of 2,3-dibromo-1,1-dimethyl- The same procedure was followed to obtain 83.1 g of the target compound (final yield 56%).
1H-NMR: δ 0.39-0.40 (m, 2H), 0.63-0.64 (m, 2H), 1.24 (s, 24H), 6.95(s, 1H), 7.22 (t, 1H), 7.27-7.30 (m, 2H), 7.42 (d, 1H), 7.45-7.46 (m, 2H), 7.50 (d, 1H), 7.60-7.61 (m, 4H) 1 H-NMR:? 0.39-0.40 (m, 2H), 0.63-0.64 (m, 2H), 1.24 (s, 24H), 6.95 , 7.42 (d, 1H), 7.45-7.46 (m, 2H), 7.50 (d, 1H), 7.60-7.61
[LCMS] : 547[LCMS]: 547
[[ 준비예Preparation Example 7] 2,2'-( 7] 2,2 '- ( spirospiro [[ cyclopentanecyclopentane -1,1'--1,1'- indeneindene ]-2',3'-] -2 ', 3'- diylbis(4,1-diylbis (4,1- phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)의 합성phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
<단계 1>의 반응물로 2,3-dibromo-1,1-dimethyl-1H-indene 대신 2',3'-dibromospiro[cyclopentane-1,1'-indene]을 사용한 것을 제외하고는 준비예 1과 동일한 과정을 수행하여 목적 화합물 85.7g (final 수율 55 %)을 얻었다.Preparation Example 1 was repeated except that 2 ', 3'-dibromospiro [cyclopentane-1,1'-indene] was used instead of 2,3-dibromo-1,1-dimethyl- The same procedure was followed to obtain 85.7 g (final yield 55%) of the desired compound.
1H-NMR: δ 1.24 (s, 24H), 1.46-1.47 (m, 2H), 1,56-1.57 (m, 2H), 1.68-1.69 (m, 2H), 1.93-1.94 (m, 2H), 7.22 (t, 1H), 7.27-7.30 (m, 2H), 7.42 (d, 1H), 7.50 (d, 4H), 7.75 (d, 4H) 1 H-NMR: δ 1.24 ( s, 24H), 1.46-1.47 (m, 2H), 1,56-1.57 (m, 2H), 1.68-1.69 (m, 2H), 1.93-1.94 (m, 2H) , 7.22 (t, IH), 7.27-7.30 (m, 2H), 7.42 (d,
[LCMS] : 575 [LCMS]: 575
[[ 준비예Preparation Example 8] 2,2'-( 8] 2,2 ' - ( spirospiro [[ cyclopentanecyclopentane -1,1'--1,1'- indeneindene ]-2',3'-] -2 ', 3'- diylbis(3,1-phenylene))bisdiylbis (3,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane)의 합성(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
<단계 1>의 반응물로 2,3-dibromo-1,1-dimethyl-1H-indene 대신 2',3'-dibromospiro[cyclopentane-1,1'-indene]을 사용한 것을 제외하고는 준비예 2와 동일한 과정을 수행하여 목적 화합물 90.4 g (final 수율 58 %)을 얻었다.Preparation Example 2 was repeated except that 2 ', 3'-dibromospiro [cyclopentane-1,1'-indene] was used instead of 2,3-dibromo-1,1-dimethyl-1H- The same procedure was followed to obtain 90.4 g (final yield 58%) of the desired compound.
1H-NMR: δ 1.24 (s, 24H), 1.46-1.47 (m, 2H), 1,56-1.57 (m, 2H), 1.68-1.69 (m, 2H), 1.93-1.94 (m, 2H), 6.95(s, 1H), 7.22 (t, 1H), 7.27-7.30 (m, 2H), 7.42 (d, 1H), 7.45-7.46 (m, 2H), 7.50 (d, 1H), 7.60-7.61 (m, 4H) 1 H-NMR: δ 1.24 ( s, 24H), 1.46-1.47 (m, 2H), 1,56-1.57 (m, 2H), 1.68-1.69 (m, 2H), 1.93-1.94 (m, 2H) , 6.95 (s, 1H), 7.22 (t, 1H), 7.27-7.30 (m, 2H), 7.42 (d, 1H), 7.45-7.46 (m, 4H)
[LCMS] : 575[LCMS]: 575
[[ 준비예Preparation Example 9] 2,2'-( 9] 2,2 '- ( spirospiro [[ cyclohexanecyclohexane -1,1'--1,1'- indeneindene ]-2',3'-] -2 ', 3'- diylbis(4,1-phenylene))bisdiylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane)의 합성(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
<단계 1>의 반응물로 2,3-dibromo-1,1-dimethyl-1H-indene 대신 2',3'-dibromospiro[cyclohexane-1,1'-indene]을 사용한 것을 제외하고는 준비예 1과 동일한 과정을 수행하여 목적 화합물 102.2g (final 수율 55 %)을 얻었다.Preparation Example 1 was repeated except that 2 ', 3'-dibromospiro [cyclohexane-1,1'-indene] was used instead of 2,3-dibromo-1,1-dimethyl- The same procedure was followed to obtain 102.2 g of the target compound (final yield 55%).
1H-NMR: δ 1.24 (s, 24H), 1.43-1.44 (m, 2H), 1.47-1.49 (m, 2H), 1.53-1.54 (m, 2H), 1.61-1.62 (m, 2H), 1.86-1.87 (m, 2H), 7.22 (t, 1H), 7.27-7.30 (m, 2H), 7.42 (d, 1H), 7.50 (d, 4H), 7.75 (d, 4H) 1 H-NMR: δ 1.24 ( s, 24H), 1.43-1.44 (m, 2H), 1.47-1.49 (m, 2H), 1.53-1.54 (m, 2H), 1.61-1.62 (m, 2H), 1.86 2H), 7.42 (d, 1H), 7.50 (d, 4H), 7.75 (d, 4H)
[LCMS] : 589 [LCMS]: 589
[[ 준비예Preparation Example 10] 2,2'-( 10] 2,2 '- ( spirospiro [[ cyclohexanecyclohexane -1,1'--1,1'- indeneindene ]-2',3'-] -2 ', 3'- diylbis(3,1-phenylene))bisdiylbis (3,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane)의 합성(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
<단계 1>의 반응물로 2,3-dibromo-1,1-dimethyl-1H-indene 대신 2',3'-dibromospiro[cyclohexane-1,1'-indene]을 사용한 것을 제외하고는 준비예 2와 동일한 과정을 수행하여 목적 화합물 90.4 g (final 수율 58 %)을 얻었다.Preparation Example 2 was repeated except that 2 ', 3'-dibromospiro [cyclohexane-1,1'-indene] was used instead of 2,3-dibromo-1,1-dimethyl- The same procedure was followed to obtain 90.4 g (final yield 58%) of the desired compound.
1H-NMR: δ 1.24 (s, 24H), 1.43-1.44 (m, 2H), 1.47-1.49 (m, 2H), 1.53-1.54 (m, 2H), 1.61-1.62 (m, 2H), 1.86-1.87 (m, 2H), 6.95(s, 1H), 7.22 (t, 1H), 7.27-7.30 (m, 2H), 7.42 (d, 1H), 7.45-7.46 (m, 2H), 7.50 (d, 1H), 7.60-7.61 (m, 4H) 1 H-NMR: δ 1.24 ( s, 24H), 1.43-1.44 (m, 2H), 1.47-1.49 (m, 2H), 1.53-1.54 (m, 2H), 1.61-1.62 (m, 2H), 1.86 2H), 7.45-7.46 (m, 2H), 7.50 (d, 1H), 7.27-7.30 (m, , ≪ / RTI > 1H), 7.60-7.61 (m, 4H)
[LCMS] : 589[LCMS]: 589
[[ 준비예Preparation Example 11] 2,2'-((1H- 11] 2,2 ' - ((1H- indeneindene -2,3--2,3- diyldiyl )bis(4,1-) bis (4,1- phenylenehenylene ))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)의 합성)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
<단계 1>의 반응물로 2,3-dibromo-1,1-dimethyl-1H-indene 대신 2,3-dibromo-1H-indene을 사용한 것을 제외하고는 준비예 1과 동일한 과정을 수행하여 목적 화합물 84.7 g (final 수율 60 %)을 얻었다.The procedure of Preparation Example 1 was repeated except that 2,3-dibromo-1H-indene was used instead of 2,3-dibromo-1,1-dimethyl-1H-indene as a reactant in Step 1, g (final yield 60%).
1H-NMR: δ 1.24 (s, 24H), 3.20 (s, 2H), 7.22 (t, 1H), 7.27-7.30 (m, 2H), 7.42 (d, 1H), 7.50 (d, 4H), 7.75 (d, 4H) 1 H-NMR: δ 1.24 ( s, 24H), 3.20 (s, 2H), 7.22 (t, 1H), 7.27-7.30 (m, 2H), 7.42 (d, 1H), 7.50 (d, 4H), 7.75 (d, 4H)
[LCMS] : 521 [LCMS]: 521
[[ 준비예Preparation Example 12] 2,2'-((1H- 12] 2,2 ' - ((1H- indeneindene -2,3--2,3- diyldiyl )bis(3,1-) bis (3,1- phenylenehenylene ))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)의 합성)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
<단계 1>의 반응물로 2,3-dibromo-1,1-dimethyl-1H-indene 대신 2,3-dibromo-1H-indene을 사용한 것을 제외하고는 준비예 2와 동일한 과정을 수행하여 목적 화합물 79.2 g (final 수율 56 %)을 얻었다.The procedure of Preparation Example 2 was repeated except that 2,3-dibromo-1H-indene was used instead of 2,3-dibromo-1,1-dimethyl-1H-indene as a reactant in Step 1, g (final yield: 56%).
1H-NMR: δ 1.24 (s, 24H), 3.20 (s, 2H), 6.95(s, 1H), 7.22 (t, 1H), 7.27-7.30 (m, 2H), 7.42 (d, 1H), 7.45-7.46 (m, 2H), 7.50 (d, 1H), 7.60-7.61 (m, 4H) 1 H-NMR: δ 1.24 ( s, 24H), 3.20 (s, 2H), 6.95 (s, 1H), 7.22 (t, 1H), 7.27-7.30 (m, 2H), 7.42 (d, 1H), 7.45-7.46 (m, 2H), 7.50 (d, 1H), 7.60-7.61 (m, 4H)
[LCMS] : 521[LCMS]: 521
[[ 준비예Preparation Example 13] 1-phenyl-2,3-bis(4-(4,4,5,5- 13] 1-phenyl-2,3-bis (4- (4,4,5,5- tetramethyltetramethyl -1,3,2--1,3,2- dioxaborolandioxaborolan -2-yl)phenyl)-1H-indole의 합성-2-yl) phenyl) -1H-indole < / RTI >
<단계 1>의 반응물로 2,3-dibromo-1,1-dimethyl-1H-indene 대신 2,3-dibromo-1-phenyl-1H-indole을 사용한 것을 제외하고는 준비예 1과 동일한 과정을 수행하여 목적 화합물 90.8 g (final 수율 56 %)을 얻었다.The procedure of Preparation Example 1 was repeated except that 2,3-dibromo-1-phenyl-1H-indole was used instead of 2,3-dibromo-1,1-dimethyl-1H- To obtain 90.8 g (final yield 56%) of the desired compound.
1H-NMR: δ 1.24 (s, 24H), 7.42-7.43 (m, 2H), 7.45-7.46 (m, 1H), 7.50 (d, 2H), 7.58 (d, 2H), 7.71 (d, 1H), 7.79-7.83 (m, 8H), 8.17 (d, 1H) 1 H-NMR: δ 1.24 ( s, 24H), 7.42-7.43 (m, 2H), 7.45-7.46 (m, 1H), 7.50 (d, 2H), 7.58 (d, 2H), 7.71 (d, 1H ), 7.79-7.83 (m, 8 H), 8.17 (d, 1 H)
[LCMS] : 598 [LCMS]: 598
[[ 준비예Preparation Example 14] 1-phenyl-2,3-bis(3-(4,4,5,5- 14] 1-phenyl-2,3-bis (3- (4,4,5,5- tetramethyltetramethyl -1,3,2--1,3,2- dioxaborolandioxaborolan -2-yl)phenyl)-1H-indole의 합성-2-yl) phenyl) -1H-indole < / RTI >
<단계 1>의 반응물로 2,3-dibromo-1,1-dimethyl-1H-indene 대신 2,3-dibromo-1-phenyl-1H-indole을 사용한 것을 제외하고는 준비예 2와 동일한 과정을 수행하여 목적 화합물 87.6 g (final 수율 54 %)을 얻었다.The procedure of Preparation Example 2 was repeated except that 2,3-dibromo-1-phenyl-1H-indole was used instead of 2,3-dibromo-1,1-dimethyl-1H- 87.6 g (final yield 54%) of the desired compound was obtained.
1H-NMR: δ 1.24 (s, 24H), 7.42-7.43 (m, 2H), 7.45-7.46 (m, 1H), 7.50 (d, 2H), 7.58 (d, 2H), 7.51-7.52 (m, 3H), 7.66 (s, 2H), 7.71 (m, 3H), 7.79-7.80 (m, 1H), 8.17 (d, 1H) 1 H-NMR: δ 1.24 ( s, 24H), 7.42-7.43 (m, 2H), 7.45-7.46 (m, 1H), 7.50 (d, 2H), 7.58 (d, 2H), 7.51-7.52 (m 2H), 7.71 (m, 3H), 7.79-7.80 (m,
[LCMS] : 598 [LCMS]: 598
[[ 준비예Preparation Example 15] 3-phenyl-1,2-bis(4-(4,4,5,5- 15] 3-phenyl-1,2-bis (4- (4,4,5,5- tetramethyltetramethyl -1,3,2--1,3,2- dioxaborolandioxaborolan -2-yl)phenyl)-3H-benzo[e]indole의 합성-2-yl) phenyl) -3H-benzo [e] indole
<단계 1>의 반응물로 2,3-dibromo-1,1-dimethyl-1H-indene 대신 1,2-dibromo-3-phenyl-3H-benzo[e]indole을 사용한 것을 제외하고는 준비예 1과 동일한 과정을 수행하여 목적 화합물 94.9 g (final 수율 54 %)을 얻었다.Dibromo-3-phenyl-3H-benzo [e] indole was used instead of 2,3-dibromo-1,1-dimethyl-1H-indene as a reactant in <Step 1> The same procedure was followed to obtain 94.9 g of the desired compound (final yield 54%).
1H-NMR: δ 1.24 (s, 24H), 7.45-7.46 (m, 1H), 7.50 (d, 2H), 7.58 (d, 2H), 7.67 (d, 2H), 7.71 (d, 1H), 7.79-7.83 (m, 8H), 8.05 (d, 1H), 8.16-8.17 (m, 1H), 8.54-8.55 (m, 1H) 1 H-NMR: δ 1.24 ( s, 24H), 7.45-7.46 (m, 1H), 7.50 (d, 2H), 7.58 (d, 2H), 7.67 (d, 2H), 7.71 (d, 1H), (M, 1H), 8.05 (d, 1H), 8.16-8.17 (m, 1H), 8.54-8.55
[LCMS] : 648 [LCMS]: 648
[[ 준비예Preparation Example 16] 3-phenyl-1,2-bis(3-(4,4,5,5- 16] 3-phenyl-1,2-bis (3- (4,4,5,5- tetramethyltetramethyl -1,3,2--1,3,2- dioxaborolandioxaborolan -2-yl)phenyl)-3H-benzo[e]indole의 합성-2-yl) phenyl) -3H-benzo [e] indole
<단계 1>의 반응물로 2,3-dibromo-1,1-dimethyl-1H-indene 대신 1,2-dibromo-3-phenyl-3H-benzo[e]indole을 사용한 것을 제외하고는 준비예 2와 동일한 과정을 수행하여 목적 화합물 103.7 g (final 수율 59 %)을 얻었다.Preparation Example 2 was repeated except that 1,2-dibromo-3-phenyl-3H-benzo [e] indole was used instead of 2,3-dibromo-1,1-dimethyl-1H- The same procedure was carried out to obtain 103.7 g (final yield: 59%) of the target compound.
1H-NMR: δ 1.24 (s, 24H), 7.45-7.46 (m, 1H), 7.50 (d, 2H), 7.51-7.52 (m, 3H), 7.58 (d, 2H), 7.67-7.68 (m, 4H), 7.71-7.72 (m, 3H), 7.79-7.80 (m, 1H), 8.05 (d, 1H), 8.16-8.17 (m, 1H), 8.54-8.55 (m, 1H) 1 H-NMR: δ 1.24 ( s, 24H), 7.45-7.46 (m, 1H), 7.50 (d, 2H), 7.51-7.52 (m, 3H), 7.58 (d, 2H), 7.67-7.68 (m 1H), 8.16-8.17 (m, 1H), 8.54-8.55 (m, 1H), 7.71-7.72
[LCMS] : 648 [LCMS]: 648
[[ 준비예Preparation Example 17] 2,2'-( 17] 2,2 '- ( benzo[b]thiophenebenzo [b] thiophene -2,3--2,3- diylbis(4,1-phenylene))bisdiylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane)의 합성(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
<단계 1>의 반응물로 2,3-dibromo-1,1-dimethyl-1H-indene 대신 2,3-dibromobenzo[b]thiophene을 사용한 것을 제외하고는 준비예 1과 동일한 과정을 수행하여 목적 화합물 87.7 g (final 수율 60 %)을 얻었다.The procedure of Preparation Example 1 was repeated except that 2,3-dibromobenzo [b] thiophene was used instead of 2,3-dibromo-1,1-dimethyl-1H-indene as a reactant in Step 1 to obtain the desired compound 87.7 g (final yield 60%).
1H-NMR: δ 1.24 (s, 24H), 7.50 (t, 1H), 7.52 (t, 1H), 7.79 (d, 4H), 7.81 (d, 4H), 7.98 (d, 1H), 8.45 (d, 1H) 1 H-NMR: δ 1.24 ( s, 24H), 7.50 (t, 1H), 7.52 (t, 1H), 7.79 (d, 4H), 7.81 (d, 4H), 7.98 (d, 1H), 8.45 ( d, 1 H)
[LCMS] : 539 [LCMS]: 539
[[ 준비예Preparation Example 18] 2,2'-( 18] 2,2 '- ( benzo[b]thiophenebenzo [b] thiophene -2,3--2,3- diylbis(3,1-phenylene))bisdiylbis (3,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane)의 합성(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
<단계 1>의 반응물로 2,3-dibromo-1,1-dimethyl-1H-indene 대신 2,3-dibromobenzo[b]thiophene을 사용한 것을 제외하고는 준비예 2와 동일한 과정을 수행하여 목적 화합물 81.8 g (final 수율 56 %)을 얻었다.The procedure of Preparation Example 2 was repeated except that 2,3-dibromobenzo [b] thiophene was used instead of 2,3-dibromo-1,1-dimethyl-1H-indene as a reactant in Step 1 to obtain the desired compound 81.8 g (final yield: 56%).
1H-NMR: δ 1.24 (s, 24H), 7.50 (t, 1H), 7.51-7.53 (m, 4H), 7.66 (s, 2H), 7.71 (d, 2H), 7.79 (d, 1H), 7.98 (d, 1H), 8.45 (d, 1H) 1 H-NMR: δ 1.24 ( s, 24H), 7.50 (t, 1H), 7.51-7.53 (m, 4H), 7.66 (s, 2H), 7.71 (d, 2H), 7.79 (d, 1H), 7.98 (d, 1 H), 8.45 (d, 1 H)
[LCMS] : 539[LCMS]: 539
[[ 준비예Preparation Example 19] 2,2'-( 19] 2,2 '-( benzofuranbenzofuran -2,3--2,3- diylbis(4,1-phenylene))bisdiylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane)의 합성(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
<단계 1>의 반응물로 2,3-dibromo-1,1-dimethyl-1H-indene 대신 2,3-dibromobenzofuran을 사용한 것을 제외하고는 준비예 1과 동일한 과정을 수행하여 목적 화합물 90.7 g (final 수율 64 %)을 얻었다.The procedure of Preparation Example 1 was repeated except that 2,3-dibromobenzofuran was used instead of 2,3-dibromo-1,1-dimethyl-1H-indene as a reactant in Step 1 to obtain 90.7 g (final yield: 64%).
1H-NMR: δ 1.24 (s, 24H), 7.32 (t, 1H), 7.38 (t, 1H), 7.66 (d, 1H), 7.79 (d, 4H), 7.81 (d, 4H), 7.98 (d, 1H) 1 H-NMR: δ 1.24 ( s, 24H), 7.32 (t, 1H), 7.38 (t, 1H), 7.66 (d, 1H), 7.79 (d, 4H), 7.81 (d, 4H), 7.98 ( d, 1 H)
[LCMS] : 523 [LCMS]: 523
[[ 준비예Preparation Example 20] 2,2'-( 20] 2,2 '- ( benzofuranbenzofuran -2,3--2,3- diylbis(3,1-phenylene))bisdiylbis (3,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane)의 합성(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
<단계 1>의 반응물로 2,3-dibromo-1,1-dimethyl-1H-indene 대신 2,3-dibromobenzofuran을 사용한 것을 제외하고는 준비예 2와 동일한 과정을 수행하여 목적 화합물 85.1 g (final 수율 60 %)을 얻었다.The procedure of Preparation Example 2 was repeated except that 2,3-dibromobenzofuran was used instead of 2,3-dibromo-1,1-dimethyl-1H-indene as a reactant in Step 1 to obtain 85.1 g (final yield: 60%).
1H-NMR: δ 1.24 (s, 24H), 7.32 (t, 1H), 7.38 (t, 1H), 7.51-7.53 (m, 3H), 7.66-7.67 (m, 3H), 7.71 (d, 2H), 7.89 (d, 1H), 8.10 (d, 1H) 1 H-NMR:? 1.24 (s, 24H), 7.32 (t, IH), 7.38 (t, IH), 7.51-7.53 (m, 3H), 7.66-7.67 ), 7.89 (d, 1 H), 8.10 (d, 1 H)
[LCMS] : 523[LCMS]: 523
[[ 합성예Synthetic example 1] 화합물 A-1의 합성 1] Synthesis of Compound A-1
준비예 1의 2,2'-((1,1-dimethyl-1H-indene-2,3-diyl)bis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.1 mmol)와 2-chloro-4,6-diphenyl-1,3,5-triazine (5.4 g, 20.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.8 g, 27.3 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 A-1 (5.7 g, 수율 82 %)을 얻었다.Preparation of 2,2 '- ((1,1-dimethyl-1H-indene-2,3-diyl) bis (4,1-phenylene)) bis (4,4,5,5-tetramethyl- 3,2-dioxaborolane) (5 g, 9.1 mmol) and 2-chloro-4,6-diphenyl- 1,3,5-triazine (5.4 g, 20.1 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.8 g, 27.3 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removal of the solvent of the filtered organic layer, the target compound A-1 (5.7 g, yield 82%) was obtained by column chromatography.
[LCMS] : 759[LCMS]: 759
[[ 합성예Synthetic example 2] 화합물 A-2의 합성 2] Synthesis of Compound A-2
준비예 1의 2,2'-((1,1-dimethyl-1H-indene-2,3-diyl)bis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.1 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.9 g, 20.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.8 g, 27.3 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 A-2 (6.5 g, 수율 79 %)을 얻었다.Preparation of 2,2 '- ((1,1-dimethyl-1H-indene-2,3-diyl) bis (4,1-phenylene)) bis (4,4,5,5-tetramethyl- 3, 2-dioxaborolane (5 g, 9.1 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4-chloro- 20.1 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (3.8 g, 27.3 mmol) is put into a 80ml Toluene, EtOH 20ml, 20ml H 2 O was heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, the desired compound A-2 (6.5 g, yield 79%) was obtained by column chromatography.
[LCMS] : 912[LCMS]: 912
[[ 합성예Synthetic example 3] 화합물 A-3의 합성 3] Synthesis of Compound A-3
준비예 1의 2,2'-((1,1-dimethyl-1H-indene-2,3-diyl)bis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.1 mmol)와 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.9 g, 20.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.8 g, 27.3 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 A-3 (5.7 g, 수율 69 %)을 얻었다.Preparation of 2,2 '- ((1,1-dimethyl-1H-indene-2,3-diyl) bis (4,1-phenylene)) bis (4,4,5,5-tetramethyl- 3-yl-4-chloro-6-phenyl-1,3,5-triazine (6.9 g, 9.1 mmol) 20.1 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (3.8 g, 27.3 mmol) is put into a 80ml Toluene, EtOH 20ml, 20ml H 2 O was heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removal of the solvent of the filtered organic layer, the target compound A-3 (5.7 g, yield 69%) was obtained by column chromatography.
[LCMS] : 912[LCMS]: 912
[[ 합성예Synthetic example 4] 화합물 A-4의 합성 4] Synthesis of Compound A-4
준비예 2의 2,2'-((1,1-dimethyl-1H-indene-2,3-diyl)bis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.1 mmol)와 2-chloro-4,6-diphenyl-1,3,5-triazine (5.4 g, 20.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.8 g, 27.3 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 A-4 (6.9 g, 수율 73 %)을 얻었다.Preparation of 2,2 '- ((1,1-dimethyl-1H-indene-2,3-diyl) bis (3,1-phenylene)) bis (4,4,5,5-tetramethyl- 3,2-dioxaborolane) (5 g, 9.1 mmol) and 2-chloro-4,6-diphenyl- 1,3,5-triazine (5.4 g, 20.1 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.8 g, 27.3 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . The solvent of the filtered organic layer was removed, and the desired compound A-4 (6.9 g, yield 73%) was obtained by column chromatography.
[LCMS] : 759[LCMS]: 759
[[ 합성예Synthetic example 5] 화합물 A-5의 합성 5] Synthesis of Compound A-5
준비예 2의 2,2'-((1,1-dimethyl-1H-indene-2,3-diyl)bis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.1 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.9 g, 20.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.8 g, 27.3 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 A-5 (5.5 g, 수율 67 %)을 얻었다.Preparation of 2,2 '- ((1,1-dimethyl-1H-indene-2,3-diyl) bis (3,1-phenylene)) bis (4,4,5,5-tetramethyl- 3, 2-dioxaborolane (5 g, 9.1 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4-chloro- 20.1 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (3.8 g, 27.3 mmol) is put into a 80ml Toluene, EtOH 20ml, 20ml H 2 O was heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removal of the solvent of the filtered organic layer, the target compound A-5 (5.5 g, yield 67%) was obtained by column chromatography.
[LCMS] : 912[LCMS]: 912
[[ 합성예Synthetic example 6] 화합물 A-12의 합성 6] Synthesis of Compound A-12
준비예 1의 2,2'-((1,1-dimethyl-1H-indene-2,3-diyl)bis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.1 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (6.9 g, 20.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.8 g, 27.3 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 A-12 (5.5 g, 수율 67 %)을 얻었다.Preparation of 2,2 '- ((1,1-dimethyl-1H-indene-2,3-diyl) bis (4,1-phenylene)) bis (4,4,5,5-tetramethyl- 4-yl) -6-chloro-2-phenylpyrimidine (6.9 g, 20.1 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.8 g, 27.3 mmol) were placed in 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . The solvent of the filtered organic layer was removed, and the desired compound A-12 (5.5 g, yield 67%) was obtained by column chromatography.
[LCMS] : 910[LCMS]: 910
[[ 합성예Synthetic example 7] 화합물 A-15의 합성 7] Synthesis of Compound A-15
준비예 2의 2,2'-((1,1-dimethyl-1H-indene-2,3-diyl)bis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.1 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (6.9 g, 20.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.8 g, 27.3 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 A-15 (5.1 g, 수율 62 %)을 얻었다.Preparation of 2,2 '- ((1,1-dimethyl-1H-indene-2,3-diyl) bis (3,1-phenylene)) bis (4,4,5,5-tetramethyl- 4-yl) -6-chloro-2-phenylpyrimidine (6.9 g, 20.1 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.8 g, 27.3 mmol) were placed in 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . The solvent of the filtered organic layer was removed, and the desired compound A-15 (5.1 g, yield 62%) was obtained by column chromatography.
[LCMS] : 910[LCMS]: 910
[[ 합성예Synthetic example 8] 화합물 A-22의 합성 8] Synthesis of Compound A-22
준비예 1의 2,2'-((1,1-dimethyl-1H-indene-2,3-diyl)bis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.1 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (6.9 g, 20.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.8 g, 27.3 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 A-22 (5.5 g, 수율 67 %)을 얻었다.Preparation of 2,2 '- ((1,1-dimethyl-1H-indene-2,3-diyl) bis (4,1-phenylene)) bis (4,4,5,5-tetramethyl- 4-yl) -2-chloro-6-phenylpyrimidine (6.9 g, 20.1 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.8 g, 27.3 mmol) were placed in 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . The solvent of the filtered organic layer was removed, and the desired compound A-22 (5.5 g, yield 67%) was obtained by column chromatography.
[LCMS] : 910[LCMS]: 910
[[ 합성예Synthetic example 9] 화합물 A-25의 합성 9] Synthesis of Compound A-25
준비예 2의 2,2'-((1,1-dimethyl-1H-indene-2,3-diyl)bis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.1 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (6.9 g, 20.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.8 g, 27.3 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 A-25 (5.1 g, 수율 62 %)을 얻었다.Preparation of 2,2 '- ((1,1-dimethyl-1H-indene-2,3-diyl) bis (3,1-phenylene)) bis (4,4,5,5-tetramethyl- 4-yl) -2-chloro-6-phenylpyrimidine (6.9 g, 20.1 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.8 g, 27.3 mmol) were placed in 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, the target compound A-25 (5.1 g, yield 62%) was obtained by column chromatography.
[LCMS] : 910[LCMS]: 910
[[ 합성예Synthetic example 10] 화합물 A-39의 합성 10] Synthesis of Compound A-39
준비예 1의 2,2'-((1,1-dimethyl-1H-indene-2,3-diyl)bis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.1 mmol)와 2-chloro-4-phenylquinazoline (4.8 g, 20.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.8 g, 27.3 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 A-39 (3.9 g, 수율 61 %)을 얻었다.Preparation of 2,2 '- ((1,1-dimethyl-1H-indene-2,3-diyl) bis (4,1-phenylene)) bis (4,4,5,5-tetramethyl- 3,2-dioxaborolane) (5 g, 9.1 mmol) and 2-chloro-4-phenylquinazoline ( 4.8 g, 20.1 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (3.8 g , 27.3 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After the solvent of the filtered organic layer was removed, the desired compound A-39 (3.9 g, yield 61%) was obtained by column chromatography.
[LCMS] : 705[LCMS]: 705
[[ 합성예Synthetic example 11] 화합물 B-1의 합성 11] Synthesis of Compound B-1
준비예 3의 2,2'-((1,1-diethyl-1H-indene-2,3-diyl)bis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.7 mmol)와 2-chloro-4,6-diphenyl-1,3,5-triazine (5.1 g, 19.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.0 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 B-1 (5.1 g, 수율 75 %)을 얻었다.Bis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,1-diethyl-1H-indene- 3,2-dioxaborolane) (5 g, 8.7 mmol) and 2-chloro-4,6-diphenyl- 1,3,5-triazine (5.1 g, 19.1 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.6 g, 26.0 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, the target compound B-1 (5.1 g, yield 75%) was obtained by column chromatography.
[LCMS] : 787[LCMS]: 787
[[ 합성예Synthetic example 12] 화합물 B-2의 합성 12] Synthesis of Compound B-2
준비예 3의 2,2'-((1,1-diethyl-1H-indene-2,3-diyl)bis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.7 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.6 g, 19.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.0 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 B-2 (6.1 g, 수율 75 %)을 얻었다.Bis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,1-diethyl-1H-indene- 3,6-dioxaborolane (5 g, 8.7 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4-chloro- 19.1 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (3.6 g, 26.0 mmol) is put into a 80ml Toluene, EtOH 20ml, 20ml H 2 O was heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, the target compound B-2 (6.1 g, yield 75%) was obtained by column chromatography.
[LCMS] : 940[LCMS]: 940
[[ 합성예Synthetic example 13] 화합물 B-3의 합성 13] Synthesis of Compound B-3
준비예 3의 2,2'-((1,1-diethyl-1H-indene-2,3-diyl)bis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.7 mmol)와 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.6 g, 19.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.0 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 B-3 (5.8 g, 수율 69 %)을 얻었다.Bis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,1-diethyl-1H-indene- 3,6-dioxaborolane (5 g, 8.7 mmol) and 2 - ([1,1'-biphenyl] -3-yl) -4- 19.1 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (3.6 g, 26.0 mmol) is put into a 80ml Toluene, EtOH 20ml, 20ml H 2 O was heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . The solvent of the filtered organic layer was removed, and the desired compound B-3 (5.8 g, yield 69%) was obtained by column chromatography.
[LCMS] : 940[LCMS]: 940
[[ 합성예Synthetic example 14] 화합물 B-4의 합성 14] Synthesis of Compound B-4
준비예 4의 2,2'-((1,1-diethyl-1H-indene-2,3-diyl)bis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.1 mmol)와 2-chloro-4,6-diphenyl-1,3,5-triazine (5.1 g, 19.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.0 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 B-4 (4.8 g, 수율 70 %)을 얻었다.(1,1-diethyl-1H-indene-2,3-diyl) bis (3,1-phenylene)) bis (4,4,5,5-tetramethyl- 3,2-dioxaborolane) (5 g, 9.1 mmol) and 2-chloro-4,6-diphenyl- 1,3,5-triazine (5.1 g, 19.1 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.6 g, 26.0 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, the target compound B-4 (4.8 g, yield 70%) was obtained by column chromatography.
[LCMS] : 787[LCMS]: 787
[[ 합성예Synthetic example 15] 화합물 B-5의 합성 15] Synthesis of Compound B-5
준비예 4의 2,2'-((1,1-diethyl-1H-indene-2,3-diyl)bis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.1 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.6 g, 19.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.0 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 B-5 (6.1 g, 수율 75 %)을 얻었다.(1,1-diethyl-1H-indene-2,3-diyl) bis (3,1-phenylene)) bis (4,4,5,5-tetramethyl- 3,6-dioxaborolane (5 g, 9.1 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4- 19.1 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (3.6 g, 26.0 mmol) is put into a 80ml Toluene, EtOH 20ml, 20ml H 2 O was heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, B-5 (6.1 g, yield 75%) was obtained by column chromatography.
[LCMS] : 940[LCMS]: 940
[[ 합성예Synthetic example 16] 화합물 B-12의 합성 16] Synthesis of Compound B-12
준비예 3의 2,2'-((1,1-diethyl-1H-indene-2,3-diyl)bis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.7 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (6.6 g, 19.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.0 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 B-12 (5.6 g, 수율 69 %)을 얻었다.Bis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,1-diethyl-1H-indene- 4-yl) -6-chloro-2-phenylpyrimidine (6.6 g, 19.1 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.6 g, 26.0 mmol) were placed in 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . The solvent of the filtered organic layer was removed, and the desired compound B-12 (5.6 g, yield 69%) was obtained by column chromatography.
[LCMS] : 938[LCMS]: 938
[[ 합성예Synthetic example 17] 화합물 B-15의 합성 17] Synthesis of compound B-15
준비예 4의 2,2'-((1,1-diethyl-1H-indene-2,3-diyl)bis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.1 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (6.6 g, 19.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.0 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 B-15 (5.3 g, 수율 65 %)을 얻었다.(1,1-diethyl-1H-indene-2,3-diyl) bis (3,1-phenylene)) bis (4,4,5,5-tetramethyl- 4-yl) -6-chloro-2-phenylpyrimidine (6.6 g, 19.1 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.6 g, 26.0 mmol) were placed in 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After the solvent of the filtered organic layer was removed, the target compound B-15 (5.3 g, yield 65%) was obtained by column chromatography.
[LCMS] : 938[LCMS]: 938
[[ 합성예Synthetic example 18] 화합물 B-22의 합성 18] Synthesis of Compound B-22
준비예 3의 2,2'-((1,1-diethyl-1H-indene-2,3-diyl)bis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.7 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (6.6 g, 19.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.0 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 B-22 (5.6 g, 수율 69 %)을 얻었다.Bis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,1-diethyl-1H-indene- 4-yl) -2-chloro-6-phenylpyrimidine (6.6 g, 19.1 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.6 g, 26.0 mmol) were placed in 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, B-22 (5.6 g, yield 69%) was obtained by column chromatography.
[LCMS] : 938[LCMS]: 938
[[ 합성예Synthetic example 19] 화합물 B-25의 합성 19] Synthesis of Compound B-25
준비예 4의 2,2'-((1,1-diethyl-1H-indene-2,3-diyl)bis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.1 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (6.6 g, 19.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.0 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 B-25 (5.3 g, 수율 65 %)을 얻었다.(1,1-diethyl-1H-indene-2,3-diyl) bis (3,1-phenylene)) bis (4,4,5,5-tetramethyl- 4-yl) -2-chloro-6-phenylpyrimidine (6.6 g, 19.1 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.6 g, 26.0 mmol) were placed in 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, B-25 (5.3 g, yield 65%) was obtained by column chromatography.
[LCMS] : 938[LCMS]: 938
[[ 합성예Synthetic example 20] 화합물 B-39의 합성 20] Synthesis of compound B-39
준비예 3의 2,2'-((1,1-diethyl-1H-indene-2,3-diyl)bis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.7 mmol)와 2-chloro-4-phenylquinazoline (4.6 g, 19.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.0 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 B-39 (3.8 g, 수율 60 %)을 얻었다.Bis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,1-diethyl-1H-indene- 3,2-dioxaborolane) (5 g, 8.7 mmol) and 2-chloro-4-phenylquinazoline ( 4.6 g, 19.1 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (3.6 g , 26.0 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, B-39 (3.8 g, yield 60%) of the target compound was obtained by column chromatography.
[LCMS] : 733[LCMS]: 733
[[ 합성예Synthetic example 21] 화합물 C-1의 합성 21] Synthesis of Compound C-1
준비예 5의 2,2'-(spiro[cyclopropane-1,1'-indene]-2',3'-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.1 mmol)와 2-chloro-4,6-diphenyl-1,3,5-triazine (5.4 g, 20.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.8 g, 27.4 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-1 (5.2 g, 수율 76 %)을 얻었다.Preparation of 2,2'- (spiro [cyclopropane-1,1'-indene] -2 ', 3'-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl- , 3,2-dioxaborolane) (5 g , 9.1 mmol) and 2-chloro-4,6-diphenyl- 1,3,5-triazine (5.4 g, 20.1 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.8 g, 27.4 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removal of the solvent of the filtered organic layer, the target compound C-1 (5.2 g, yield 76%) was obtained by column chromatography.
[LCMS] : 757[LCMS]: 757
[[ 합성예Synthetic example 22] 화합물 C-2의 합성 22] Synthesis of Compound C-2
준비예 5의 2,2'-(spiro[cyclopropane-1,1'-indene]-2',3'-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.1 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.9 g, 20.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.8 g, 27.4 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-2 (6.1 g, 수율 74 %)을 얻었다.Preparation of 2,2'- (spiro [cyclopropane-1,1'-indene] -2 ', 3'-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl- , 3,2-dioxaborolane (5 g, 9.1 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4-chloro-6- , 20.1 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.8 g, 27.4 mmol) were placed in 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, the target compound C-2 (6.1 g, yield 74%) was obtained by column chromatography.
[LCMS] : 910[LCMS]: 910
[[ 합성예Synthetic example 23] 화합물 C-3의 합성 23] Synthesis of Compound C-3
준비예 5의 2,2'-(spiro[cyclopropane-1,1'-indene]-2',3'-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.1 mmol)와 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.9 g, 20.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.8 g, 27.4 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-3 (5.7 g, 수율 69 %)을 얻었다.Preparation of 2,2'- (spiro [cyclopropane-1,1'-indene] -2 ', 3'-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl- , 3,2-dioxaborolane (5 g, 9.1 mmol) and 2 - ([1,1'-biphenyl] -3-yl) -4-chloro-6- , 20.1 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.8 g, 27.4 mmol) were placed in 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After the solvent of the filtered organic layer was removed, the desired compound C-3 (5.7 g, yield 69%) was obtained by column chromatography.
[LCMS] : 910[LCMS]: 910
[[ 합성예Synthetic example 24] 화합물 C-4의 합성 24] Synthesis of Compound C-4
준비예 6의 2,2'-(spiro[cyclopropane-1,1'-indene]-2',3'-diylbis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.1 mmol)와 2-chloro-4,6-diphenyl-1,3,5-triazine (5.4 g, 20.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.8 g, 27.4 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-4 (4.9 g, 수율 72%)을 얻었다.Preparation of 2,2'- (spiro [cyclopropane-1,1'-indene] -2 ', 3'-diylbis (3,1-phenylene)) bis (4,4,5,5-tetramethyl- , 3,2-dioxaborolane) (5 g , 9.1 mmol) and 2-chloro-4,6-diphenyl- 1,3,5-triazine (5.4 g, 20.1 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.8 g, 27.4 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-4 (4.9 g, yield 72%) was obtained by column chromatography.
[LCMS] : 757[LCMS]: 757
[[ 합성예Synthetic example 25] 화합물 C-5의 합성 25] Synthesis of Compound C-5
준비예 6의 2,2'-(spiro[cyclopropane-1,1'-indene]-2',3'-diylbis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.1 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.9 g, 20.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.8 g, 27.4 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-5 (6.3 g, 수율 76 %)을 얻었다.Preparation of 2,2'- (spiro [cyclopropane-1,1'-indene] -2 ', 3'-diylbis (3,1-phenylene)) bis (4,4,5,5-tetramethyl- , 3,2-dioxaborolane (5 g, 9.1 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4-chloro-6- , 20.1 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.8 g, 27.4 mmol) were placed in 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . The solvent of the filtered organic layer was removed, and the desired compound C-5 (6.3 g, yield 76%) was obtained by column chromatography.
[LCMS] : 910[LCMS]: 910
[[ 합성예Synthetic example 26] 화합물 C-12의 합성 26] Synthesis of Compound C-12
준비예 5의 2,2'-(spiro[cyclopropane-1,1'-indene]-2',3'-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.1 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (6.9 g, 20.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.8 g, 27.4 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-12 (5.8 g, 수율 70 %)을 얻었다.Preparation of 2,2'- (spiro [cyclopropane-1,1'-indene] -2 ', 3'-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl- , 3,2-dioxaborolane (5 g, 9.1 mmol), 4 - ([1,1'-biphenyl] -4-yl) -6-chloro-2- phenylpyrimidine (6.9 g, 20.1 mmol) 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.8 g, 27.4 mmol) were placed in 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-12 (5.8 g, yield 70%) was obtained by column chromatography.
[LCMS] : 908[LCMS]: 908
[[ 합성예Synthetic example 27] 화합물 C-15의 합성 27] Synthesis of Compound C-15
준비예 6의 2,2'-(spiro[cyclopropane-1,1'-indene]-2',3'-diylbis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.1 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (6.9 g, 20.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.8 g, 27.4 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-15 (5.8 g, 수율 70 %)을 얻었다.Preparation of 2,2'- (spiro [cyclopropane-1,1'-indene] -2 ', 3'-diylbis (3,1-phenylene)) bis (4,4,5,5-tetramethyl- , 3,2-dioxaborolane (5 g, 9.1 mmol), 4 - ([1,1'-biphenyl] -4-yl) -6-chloro-2- phenylpyrimidine (6.9 g, 20.1 mmol) 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.8 g, 27.4 mmol) were placed in 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . The solvent of the filtered organic layer was removed, and the desired compound C-15 (5.8 g, yield 70%) was obtained by column chromatography.
[LCMS] : 908[LCMS]: 908
[[ 합성예Synthetic example 28] 화합물 C-22의 합성 28] Synthesis of Compound C-22
준비예 5의 2,2'-(spiro[cyclopropane-1,1'-indene]-2',3'-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.1 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (6.9 g, 20.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.8 g, 27.4 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-22 (5.9 g, 수율 72 %)을 얻었다.Preparation of 2,2'- (spiro [cyclopropane-1,1'-indene] -2 ', 3'-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl- 4-yl) -2-chloro-6-phenylpyrimidine (6.9 g, 20.1 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.8 g, 27.4 mmol) were placed in 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-22 (5.9 g, yield 72%) was obtained by column chromatography.
[LCMS] : 908[LCMS]: 908
[[ 합성예Synthetic example 29] 화합물 C-25의 합성 29] Synthesis of Compound C-25
준비예 6의 2,2'-(spiro[cyclopropane-1,1'-indene]-2',3'-diylbis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.1 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (6.9 g, 20.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.8 g, 27.4 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-25 (5.5 g, 수율 67 %)을 얻었다.Preparation of 2,2'- (spiro [cyclopropane-1,1'-indene] -2 ', 3'-diylbis (3,1-phenylene)) bis (4,4,5,5-tetramethyl- 4-yl) -2-chloro-6-phenylpyrimidine (6.9 g, 20.1 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.8 g, 27.4 mmol) were placed in 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-25 (5.5 g, yield 67%) was obtained by column chromatography.
[LCMS] : 908[LCMS]: 908
[[ 합성예Synthetic example 30] 화합물 C-39의 합성 30] Synthesis of Compound C-39
준비예 5의 2,2'-(spiro[cyclopropane-1,1'-indene]-2',3'-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.1 mmol)와 2-chloro-4-phenylquinazoline (4.8 g, 20.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.8 g, 27.4 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-39 (4.2 g, 수율 65 %)을 얻었다.Preparation of 2,2'- (spiro [cyclopropane-1,1'-indene] -2 ', 3'-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl- , 3,2-dioxaborolane) (5 g , 9.1 mmol) and 2-chloro-4-phenylquinazoline ( 4.8 g, 20.1 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (3.8 g, 27.4 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-39 (4.2 g, yield 65%) was obtained by column chromatography.
[LCMS] : 703[LCMS]: 703
[[ 합성예Synthetic example 31] 화합물 D-1의 합성 31] Synthesis of Compound D-1
준비예 7의 2,2'-(spiro[cyclopentane-1,1'-indene]-2',3'-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.7 mmol)와 2-chloro-4,6-diphenyl-1,3,5-triazine (5.1 g, 19.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 D-1 (4.7 g, 수율 70 %)을 얻었다.Preparation of 2,2'- (spiro [cyclopentane-1,1'-indene] -2 ', 3'-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl- , 3,2-dioxaborolane) (5 g , 8.7 mmol) and 2-chloro-4,6-diphenyl- 1,3,5-triazine (5.1 g, 19.1 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.6 g, 26.1 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, D-1 (4.7 g, yield 70%) was obtained by column chromatography.
[LCMS] : 785[LCMS]: 785
[[ 합성예Synthetic example 32] 화합물 D-2의 합성 32] Synthesis of Compound D-2
준비예 7의 2,2'-(spiro[cyclopentane-1,1'-indene]-2',3'-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.7 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.6 g, 19.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 D-2 (5.7 g, 수율 70 %)을 얻었다.Preparation of 2,2'- (spiro [cyclopentane-1,1'-indene] -2 ', 3'-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl- , 3,2-dioxaborolane (5 g, 8.7 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4-chloro-6- , 19.1 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.6 g, 26.1 mmol) were placed in 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, D-2 (5.7 g, yield 70%) was obtained by column chromatography.
[LCMS] : 938[LCMS]: 938
[[ 합성예Synthetic example 33] 화합물 D-3의 합성 33] Synthesis of Compound D-3
준비예 7의 2,2'-(spiro[cyclopentane-1,1'-indene]-2',3'-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.7 mmol)와 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.6 g, 19.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 D-3 (5.4 g, 수율 67 %)을 얻었다.Preparation of 2,2'- (spiro [cyclopentane-1,1'-indene] -2 ', 3'-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl- , 3,2-dioxaborolane (5 g, 8.7 mmol) and 2 - ([1,1'-biphenyl] -3-yl) -4-chloro-6- , 19.1 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.6 g, 26.1 mmol) were placed in 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, D-3 (5.4 g, yield 67%) was obtained by column chromatography.
[LCMS] : 938[LCMS]: 938
[[ 합성예Synthetic example 34] 화합물 D-4의 합성 34] Synthesis of Compound D-4
준비예 8의 2,2'-(spiro[cyclopentane-1,1'-indene]-2',3'-diylbis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.7 mmol)와 2-chloro-4,6-diphenyl-1,3,5-triazine (5.1 g, 19.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 D-4 (4.6 g, 수율 67%)을 얻었다.Preparation of 2,2 '- (spiro [cyclopentane-1,1'-indene] -2', 3'-diylbis (3,1-phenylene)) bis (4,4,5,5-tetramethyl- , 3,2-dioxaborolane) (5 g , 8.7 mmol) and 2-chloro-4,6-diphenyl- 1,3,5-triazine (5.1 g, 19.1 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.6 g, 26.1 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, D-4 (4.6 g, yield 67%) was obtained by column chromatography.
[LCMS] : 785[LCMS]: 785
[[ 합성예Synthetic example 35] 화합물 D-5의 합성 35] Synthesis of Compound D-5
준비예 8의 2,2'-(spiro[cyclopentane-1,1'-indene]-2',3'-diylbis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.7 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.6 g, 19.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 D-5 (5.3 g, 수율 65%)을 얻었다.Preparation of 2,2 '- (spiro [cyclopentane-1,1'-indene] -2', 3'-diylbis (3,1-phenylene)) bis (4,4,5,5-tetramethyl- , 3,2-dioxaborolane (5 g, 8.7 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4-chloro-6- , 19.1 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.6 g, 26.1 mmol) were placed in 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, D-5 (5.3 g, yield 65%) was obtained by column chromatography.
[LCMS] : 938[LCMS]: 938
[[ 합성예Synthetic example 36] 화합물 D-12의 합성 36] Synthesis of Compound D-12
준비예 7의 2,2'-(spiro[cyclopentane-1,1'-indene]-2',3'-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.7 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (6.6 g, 19.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 D-12 (5.6 g, 수율 69 %)을 얻었다.Preparation of 2,2'- (spiro [cyclopentane-1,1'-indene] -2 ', 3'-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl- 4-yl) -6-chloro-2-phenylpyrimidine (6.6 g, 19.1 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.6 g, 26.1 mmol) were added to 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, D-12 (5.6 g, yield 69%) was obtained by column chromatography.
[LCMS] : 936[LCMS]: 936
[[ 합성예Synthetic example 37] 화합물 D-15의 합성 37] Synthesis of Compound D-15
준비예 8의 2,2'-(spiro[cyclopentane-1,1'-indene]-2',3'-diylbis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.7 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (6.6 g, 19.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 D-15 (5.2 g, 수율 65 %)을 얻었다.Preparation of 2,2 '- (spiro [cyclopentane-1,1'-indene] -2', 3'-diylbis (3,1-phenylene)) bis (4,4,5,5-tetramethyl- 4-yl) -6-chloro-2-phenylpyrimidine (6.6 g, 19.1 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.6 g, 26.1 mmol) were added to 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, D-15 (5.2 g, yield 65%) was obtained by column chromatography.
[LCMS] : 936[LCMS]: 936
[[ 합성예Synthetic example 38] 화합물 D-22의 합성 38] Synthesis of Compound D-22
준비예 7의 2,2'-(spiro[cyclopentane-1,1'-indene]-2',3'-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.7 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (6.6 g, 19.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 D-22 (5.7 g, 수율 70 %)을 얻었다.Preparation of 2,2'- (spiro [cyclopentane-1,1'-indene] -2 ', 3'-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl- 4-yl) -2-chloro-6-phenylpyrimidine (6.6 g, 19.1 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.6 g, 26.1 mmol) were added to 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, D-22 (5.7 g, yield 70%) was obtained by column chromatography.
[LCMS] : 936[LCMS]: 936
[[ 합성예Synthetic example 39] 화합물 D-25의 합성 39] Synthesis of Compound D-25
준비예 8의 2,2'-(spiro[cyclopentane-1,1'-indene]-2',3'-diylbis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.7 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (6.6 g, 19.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 D-25 (5.7 g, 수율 70 %)을 얻었다.Preparation of 2,2 '- (spiro [cyclopentane-1,1'-indene] -2', 3'-diylbis (3,1-phenylene)) bis (4,4,5,5-tetramethyl- 4-yl) -2-chloro-6-phenylpyrimidine (6.6 g, 19.1 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.6 g, 26.1 mmol) were added to 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, D-25 (5.7 g, yield 70%) was obtained by column chromatography.
[LCMS] : 936[LCMS]: 936
[[ 합성예Synthetic example 40] 화합물 D-39의 합성 40] Synthesis of Compound D-39
준비예 7의 2,2'-(spiro[cyclopentane-1,1'-indene]-2',3'-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.7 mmol)와 2-chloro-4-phenylquinazoline (4.6 g, 19.1 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 D-39 (4.7 g, 수율 75 %)을 얻었다.Preparation of 2,2'- (spiro [cyclopentane-1,1'-indene] -2 ', 3'-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl- , 3,2-dioxaborolane) (5 g , 8.7 mmol) and 2-chloro-4-phenylquinazoline ( 4.6 g, 19.1 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (3.6 g, 26.1 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, D-39 (4.7 g, yield 75%) was obtained by column chromatography.
[LCMS] : 731[LCMS]: 731
[[ 합성예Synthetic example 41] 화합물 E-1의 합성 41] Synthesis of Compound E-1
준비예 9의 2,2'-(spiro[cyclohexane-1,1'-indene]-2',3'-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.5 mmol)와 2-chloro-4,6-diphenyl-1,3,5-triazine (5.0 g, 18.7 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.5 g, 25.5 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 E-1 (5.1 g, 수율 70 %)을 얻었다.Preparation of 2,2 '- (spiro [cyclohexane-1,1'-indene] -2', 3'-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl- , 3,2-dioxaborolane) (5 g , 8.5 mmol) and 2-chloro-4,6-diphenyl- 1,3,5-triazine (5.0 g, 18.7 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.5 g, 25.5 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, the target compound E-1 (5.1 g, yield 70%) was obtained by column chromatography.
[LCMS] : 799[LCMS]: 799
[[ 합성예Synthetic example 42] 화합물 E-2의 합성 42] Synthesis of Compound E-2
준비예 9의 2,2'-(spiro[cyclohexane-1,1'-indene]-2',3'-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.5 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.4 g, 18.7 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 E-2 (5.8 g, 수율 72 %)을 얻었다.Preparation of 2,2 '- (spiro [cyclohexane-1,1'-indene] -2', 3'-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl- , 3,2-dioxaborolane (5 g, 8.5 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4-chloro-6- , 18.7 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (3.6 g, 26.1 mmol) placed in Toluene 80ml, EtOH 20ml, H 2 O 20ml was heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removal of the solvent of the filtered organic layer, the target compound E-2 (5.8 g, yield 72%) was obtained by column chromatography.
[LCMS] : 952[LCMS]: 952
[[ 합성예Synthetic example 43] 화합물 E-3의 합성 43] Synthesis of Compound E-3
준비예 9의 2,2'-(spiro[cyclohexane-1,1'-indene]-2',3'-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.5 mmol)와 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.4 g, 18.7 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 E-3 (5.4 g, 수율 67 %)을 얻었다.Preparation of 2,2 '- (spiro [cyclohexane-1,1'-indene] -2', 3'-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl- , 3,2-dioxaborolane (5 g, 8.5 mmol) and 2 - ([1,1'-biphenyl] -3-yl) -4-chloro-6- , 18.7 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (3.6 g, 26.1 mmol) placed in Toluene 80ml, EtOH 20ml, H 2 O 20ml was heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, column chromatography E-3 (5.4 g, yield 67%) was obtained.
[LCMS] : 952[LCMS]: 952
[[ 합성예Synthetic example 44] 화합물 E-4의 합성 44] Synthesis of Compound E-4
준비예 10의 2,2'-(spiro[cyclohexane-1,1'-indene]-2',3'-diylbis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.5 mmol)와 2-chloro-4,6-diphenyl-1,3,5-triazine (5.0 g, 18.7 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 E-4 (4.7 g, 수율 69%)을 얻었다.Preparation Example 10 Preparation of 2,2'- (spiro [cyclohexane-1,1'-indene] -2 ', 3'-diylbis (3,1-phenylene)) bis (4,4,5,5-tetramethyl- , 3,2-dioxaborolane) (5 g , 8.5 mmol) and 2-chloro-4,6-diphenyl- 1,3,5-triazine (5.0 g, 18.7 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.6 g, 26.1 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After the solvent of the filtered organic layer was removed, the target compound E-4 (4.7 g, yield 69%) was obtained by column chromatography.
[LCMS] : 799[LCMS]: 799
[[ 합성예Synthetic example 45] 화합물 E-5의 합성 45] Synthesis of Compound E-5
준비예 10의 2,2'-(spiro[cyclohexane-1,1'-indene]-2',3'-diylbis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.5 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.4 g, 18.7 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 E-5 (5.6 g, 수율 69%)을 얻었다.Preparation Example 10 Preparation of 2,2'- (spiro [cyclohexane-1,1'-indene] -2 ', 3'-diylbis (3,1-phenylene)) bis (4,4,5,5-tetramethyl- , 3,2-dioxaborolane (5 g, 8.5 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4-chloro-6- , 18.7 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (3.6 g, 26.1 mmol) placed in Toluene 80ml, EtOH 20ml, H 2 O 20ml was heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After the solvent of the filtered organic layer was removed, the target compound E-5 (5.6 g, yield 69%) was obtained by column chromatography.
[LCMS] : 952[LCMS]: 952
[[ 합성예Synthetic example 46] 화합물 E-12의 합성 46] Synthesis of Compound E-12
준비예 9의 2,2'-(spiro[cyclohexane-1,1'-indene]-2',3'-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.5 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (6.4 g, 18.7 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 E-12 (5.6 g, 수율 69 %)을 얻었다.Preparation of 2,2 '- (spiro [cyclohexane-1,1'-indene] -2', 3'-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl- 4-yl) -6-chloro-2-phenylpyrimidine (6.4 g, 18.7 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.6 g, 26.1 mmol) were added to 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, E-12 (5.6 g, yield 69%) was obtained by column chromatography.
[LCMS] : 950[LCMS]: 950
[[ 합성예Synthetic example 47] 화합물 E-15의 합성 47] Synthesis of Compound E-15
준비예 10의 2,2'-(spiro[cyclohexane-1,1'-indene]-2',3'-diylbis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.5 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (6.4 g, 18.7 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 E-15 (5.8 g, 수율 72 %)을 얻었다.Preparation Example 10 Preparation of 2,2'- (spiro [cyclohexane-1,1'-indene] -2 ', 3'-diylbis (3,1-phenylene)) bis (4,4,5,5-tetramethyl- 4-yl) -6-chloro-2-phenylpyrimidine (6.4 g, 18.7 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.6 g, 26.1 mmol) were added to 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . The solvent of the filtered organic layer was removed, and the desired compound E-15 (5.8 g, yield 72%) was obtained by column chromatography.
[LCMS] : 950[LCMS]: 950
[[ 합성예Synthetic example 48] 화합물 E-22의 합성 48] Synthesis of Compound E-22
준비예 9의 2,2'-(spiro[cyclohexane-1,1'-indene]-2',3'-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.5 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (6.4 g, 18.7 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 E-22 (5.8 g, 수율 66 %)을 얻었다.Preparation of 2,2 '- (spiro [cyclohexane-1,1'-indene] -2', 3'-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl- , 3,2-dioxaborolane (5 g, 8.5 mmol), 4 - ([1,1'-biphenyl] -4-yl) -2-chloro-6- phenylpyrimidine (6.4 g, 18.7 mmol) 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.6 g, 26.1 mmol) were added to 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, E-22 (5.8 g, yield 66%) was obtained by column chromatography.
[LCMS] : 950[LCMS]: 950
[[ 합성예Synthetic example 49] 화합물 E-25의 합성 49] Synthesis of Compound E-25
준비예 10의 2,2'-(spiro[cyclohexane-1,1'-indene]-2',3'-diylbis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.5 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (6.4 g, 18.7 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 E-25 (5.2 g, 수율 65 %)을 얻었다.Preparation Example 10 Preparation of 2,2'- (spiro [cyclohexane-1,1'-indene] -2 ', 3'-diylbis (3,1-phenylene)) bis (4,4,5,5-tetramethyl- , 3,2-dioxaborolane (5 g, 8.5 mmol), 4 - ([1,1'-biphenyl] -4-yl) -2-chloro-6- phenylpyrimidine (6.4 g, 18.7 mmol) 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.6 g, 26.1 mmol) were added to 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, E-25 (5.2 g, yield 65%) was obtained by column chromatography.
[LCMS] : 950[LCMS]: 950
[[ 합성예Synthetic example 50] 화합물 E-39의 합성 50] Synthesis of Compound E-39
준비예 9의 2,2'-(spiro[cyclohexane-1,1'-indene]-2',3'-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 8.5 mmol)와 2-chloro-4-phenylquinazoline (4.5 g, 18.7 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.6 g, 26.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 D-39 (4.4 g, 수율 70 %)을 얻었다.Preparation of 2,2 '- (spiro [cyclohexane-1,1'-indene] -2', 3'-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl- , 3,2-dioxaborolane) (5 g , 8.5 mmol) and 2-chloro-4-phenylquinazoline ( 4.5 g, 18.7 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (3.6 g, 26.1 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, D-39 (4.4 g, yield 70%) was obtained by column chromatography.
[LCMS] : 745[LCMS]: 745
[[ 합성예Synthetic example 51] 화합물 F-1의 합성 51] Synthesis of Compound F-1
준비예 11의 2,2'-((1H-indene-2,3-diyl)bis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol)와 2-chloro-4,6-diphenyl-1,3,5-triazine (5.7 g, 21.1 mmol) 및 Pd(PPh3)4 (0.6 g, 0.5 mmol), K2CO3 (4.0 g, 28.8 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 F-1 (4.9 g, 수율 70 %)을 얻었다.(1H-indene-2,3-diyl) bis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) of Preparation Example 11 (5 g, 9.6 mmol) and 2-chloro-4,6-diphenyl- 1,3,5-triazine (5.7 g, 21.1 mmol) and Pd (PPh 3) 4 (0.6 g, 0.5 mmol), K 2 CO 3 (4.0 g, 28.8 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, F-1 (4.9 g, yield 70%) was obtained by column chromatography.
[LCMS] : 731[LCMS]: 731
[[ 합성예Synthetic example 52] 화합물 F-2의 합성 52] Synthesis of Compound F-2
준비예 11의 2,2'-((1H-indene-2,3-diyl)bis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.3 g, 21.1 mmol) 및 Pd(PPh3)4 (0.6 g, 0.5 mmol), K2CO3 (4.0 g, 28.8 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 F-2 (6.2 g, 수율 73 %)을 얻었다.(1H-indene-2,3-diyl) bis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) of Preparation Example 11 4-yl) -4-chloro-6-phenyl-1,3,5-triazine (7.3 g, 21.1 mmol) and Pd (5 g, 9.6 mmol) PPh 3) 4 (0.6 g, 0.5 mmol), K 2 CO 3 (4.0 g, 28.8 mmol) is put into a 80ml Toluene, EtOH 20ml, 20ml H 2 O was heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, F-2 (6.2 g, yield 73%) was obtained by column chromatography.
[LCMS] : 884 [LCMS]: 884
[[ 합성예Synthetic example 53] 화합물 F-3의 합성 53] Synthesis of Compound F-3
준비예 11의 2,2'-((1H-indene-2,3-diyl)bis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol)와 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.3 g, 21.1 mmol) 및 Pd(PPh3)4 (0.6 g, 0.5 mmol), K2CO3 (4.0 g, 28.8 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 F-3 (6.3 g, 수율 74 %)을 얻었다.(1H-indene-2,3-diyl) bis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) of Preparation Example 11 3-yl) -4-chloro-6-phenyl-1,3,5-triazine (7.3 g, 21.1 mmol) and Pd (5 g, 9.6 mmol) PPh 3) 4 (0.6 g, 0.5 mmol), K 2 CO 3 (4.0 g, 28.8 mmol) is put into a 80ml Toluene, EtOH 20ml, 20ml H 2 O was heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, the target compound F-3 (6.3 g, yield 74%) was obtained by column chromatography.
[LCMS] : 884[LCMS]: 884
[[ 합성예Synthetic example 54] 화합물 F-4의 합성 54] Synthesis of Compound F-4
준비예 12의 2,2'-((1H-indene-2,3-diyl)bis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol)와 2-chloro-4,6-diphenyl-1,3,5-triazine (5.7 g, 21.1 mmol) 및 Pd(PPh3)4 (0.6 g, 0.5 mmol), K2CO3 (4.0 g, 28.8 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 F-4 (4.9 g, 수율 70 %)을 얻었다.(1H-indene-2,3-diyl) bis (3,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) of Preparation Example 12 (5 g, 9.6 mmol) and 2-chloro-4,6-diphenyl- 1,3,5-triazine (5.7 g, 21.1 mmol) and Pd (PPh 3) 4 (0.6 g, 0.5 mmol), K 2 CO 3 (4.0 g, 28.8 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, the desired compound F-4 (4.9 g, yield 70%) was obtained by column chromatography.
[LCMS] : 731[LCMS]: 731
[[ 합성예Synthetic example 55] 화합물 F-5의 합성 55] Synthesis of Compound F-5
준비예 12의 2,2'-((1H-indene-2,3-diyl)bis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.3 g, 21.1 mmol) 및 Pd(PPh3)4 (0.6 g, 0.5 mmol), K2CO3 (4.0 g, 28.8 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 F-5 (5.8 g, 수율 69%)을 얻었다.(1H-indene-2,3-diyl) bis (3,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) of Preparation Example 12 4-yl) -4-chloro-6-phenyl-1,3,5-triazine (7.3 g, 21.1 mmol) and Pd (5 g, 9.6 mmol) PPh 3) 4 (0.6 g, 0.5 mmol), K 2 CO 3 (4.0 g, 28.8 mmol) is put into a 80ml Toluene, EtOH 20ml, 20ml H 2 O was heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, F-5 (5.8 g, yield 69%) was obtained by column chromatography.
[LCMS] : 884[LCMS]: 884
[[ 합성예Synthetic example 56] 화합물 F-12의 합성 56] Synthesis of Compound F-12
준비예 11의 2,2'-((1H-indene-2,3-diyl)bis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (7.3 g, 21.1 mmol) 및 Pd(PPh3)4 (0.6 g, 0.5 mmol), K2CO3 (4.0 g, 28.8 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 F-12 (6.0 g, 수율 71 %)을 얻었다.(1H-indene-2,3-diyl) bis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) of Preparation Example 11 (5 g, 9.6 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -6-chloro-2-phenylpyrimidine (7.3 g, 21.1 mmol) and Pd (PPh 3) 4 (0.6 g, 0.5 mmol) and K 2 CO 3 (4.0 g, 28.8 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, F-12 (6.0 g, yield 71%) was obtained by column chromatography.
[LCMS] : 882[LCMS]: 882
[[ 합성예Synthetic example 57] 화합물 F-15의 합성 57] Synthesis of Compound F-15
준비예 12의 2,2'-((1H-indene-2,3-diyl)bis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (7.3 g, 21.1 mmol) 및 Pd(PPh3)4 (0.6 g, 0.5 mmol), K2CO3 (4.0 g, 28.8 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 F-15 (6.1 g, 수율 72 %)을 얻었다.(1H-indene-2,3-diyl) bis (3,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) of Preparation Example 12 (5 g, 9.6 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -6-chloro-2-phenylpyrimidine (7.3 g, 21.1 mmol) and Pd (PPh 3) 4 (0.6 g, 0.5 mmol) and K 2 CO 3 (4.0 g, 28.8 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, F-15 (6.1 g, yield 72%) was obtained by column chromatography.
[LCMS] : 882[LCMS]: 882
[[ 합성예Synthetic example 58] 화합물 F-22의 합성 58] Synthesis of Compound F-22
준비예 11의 2,2'-((1H-indene-2,3-diyl)bis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (7.3 g, 21.1 mmol) 및 Pd(PPh3)4 (0.6 g, 0.5 mmol), K2CO3 (4.0 g, 28.8 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 F-22 (5.8 g, 수율 68 %)을 얻었다.(1H-indene-2,3-diyl) bis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) of Preparation Example 11 (5 g, 9.6 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2-chloro-6-phenylpyrimidine (7.3 g, 21.1 mmol) and Pd (PPh 3) 4 (0.6 g, 0.5 mmol) and K 2 CO 3 (4.0 g, 28.8 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, F-22 (5.8 g, yield 68%) was obtained by column chromatography.
[LCMS] : 882[LCMS]: 882
[[ 합성예Synthetic example 59] 화합물 F-25의 합성 59] Synthesis of Compound F-25
준비예 12의 2,2'-((1H-indene-2,3-diyl)bis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (7.3 g, 21.1 mmol) 및 Pd(PPh3)4 (0.6 g, 0.5 mmol), K2CO3 (4.0 g, 28.8 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 F-25 (5.2 g, 수율 62 %)을 얻었다.(1H-indene-2,3-diyl) bis (3,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) of Preparation Example 12 (5 g, 9.6 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2-chloro-6-phenylpyrimidine (7.3 g, 21.1 mmol) and Pd (PPh 3) 4 (0.6 g, 0.5 mmol) and K 2 CO 3 (4.0 g, 28.8 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, F-25 (5.2 g, yield 62%) was obtained by column chromatography.
[LCMS] : 882[LCMS]: 882
[[ 합성예Synthetic example 60] 화합물 F-39의 합성 60] Synthesis of Compound F-39
준비예 11의 2,2'-((1H-indene-2,3-diyl)bis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol)와 2-chloro-4-phenylquinazoline (5.1 g, 21.1 mmol) 및 Pd(PPh3)4 (0.6 g, 0.5 mmol), K2CO3 (4.0 g, 28.8 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 F-39 (4.3 g, 수율 67 %)을 얻었다.(1H-indene-2,3-diyl) bis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) of Preparation Example 11 (5 g, 9.6 mmol) and 2-chloro-4-phenylquinazoline ( 5.1 g, 21.1 mmol) and Pd (PPh 3) 4 (0.6 g, 0.5 mmol), K 2 CO 3 (4.0 g, 28.8 mmol) of Toluene 80 ml of EtOH, 20 ml of EtOH and 20 ml of H 2 O, and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After the solvent of the filtered organic layer was removed, the target compound F-39 (4.3 g, yield 67%) was obtained by column chromatography.
[LCMS] : 745[LCMS]: 745
[[ 합성예Synthetic example 61] 화합물 G-1의 합성 61] Synthesis of Compound G-1
준비예 13의 1-phenyl-2,3-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-indole (5 g, 8.4 mmol)와 2-chloro-4,6-diphenyl-1,3,5-triazine (4.9 g, 18.4 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.4 g, 25.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 G-1 (5.1 g, 수율 76 %)을 얻었다.1-phenyl-1H-indole (5 g, 8.4 mmol) in Preparation Example 13 mmol) and 2-chloro-4,6-diphenyl- 1,3,5-triazine (4.9 g, 18.4 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (3.4 g, 25.1 mmol) was added to 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O, and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, G-1 (5.1 g, yield 76%) was obtained by column chromatography.
[LCMS] : 808[LCMS]: 808
[[ 합성예Synthetic example 62] 화합물 G-2의 합성 62] Synthesis of Compound G-2
준비예 13의 1-phenyl-2,3-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-indole (5 g, 8.4 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.3 g, 18.4 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.4 g, 25.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 G-2 (5.7 g, 수율 71 %)을 얻었다.1-phenyl-1H-indole (5 g, 8.4 mmol) in Preparation Example 13 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine (6.3 g, 18.4 mmol) and Pd (PPh 3) 4 ( 0.5 g, 0.4 mmol) and K 2 CO 3 (3.4 g, 25.1 mmol) were dissolved in 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, G-2 (5.7 g, yield 71%) was obtained by column chromatography.
[LCMS] : 961 [LCMS]: 961
[[ 합성예Synthetic example 63] 화합물 G-3의 합성 63] Synthesis of Compound G-3
준비예 13의 1-phenyl-2,3-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-indole (5 g, 8.4 mmol)와 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.3 g, 18.4 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.4 g, 25.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 G-3 (5.3 g, 수율 66 %)을 얻었다.1-phenyl-1H-indole (5 g, 8.4 mmol) in Preparation Example 13 mmol) and 2 - ([1,1'-biphenyl] -3-yl) -4-chloro-6-phenyl-1,3,5-triazine (6.3 g, 18.4 mmol) and Pd (PPh 3) 4 ( 0.5 g, 0.4 mmol) and K 2 CO 3 (3.4 g, 25.1 mmol) were dissolved in 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, G-3 (5.3 g, yield 66%) was obtained by column chromatography.
[LCMS] : 961[LCMS]: 961
[[ 합성예Synthetic example 64] 화합물 G-4의 합성 64] Synthesis of Compound G-4
준비예 14의 1-phenyl-2,3-bis(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-indole (5 g, 8.4 mmol)와 2-chloro-4,6-diphenyl-1,3,5-triazine (4.9 g, 18.4 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.4 g, 25.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 G-4 (5.1 g, 수율 76 %)을 얻었다.1-phenyl-2,3-bis (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- mmol) and 2-chloro-4,6-diphenyl- 1,3,5-triazine (4.9 g, 18.4 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (3.4 g, 25.1 mmol) was added to 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O, and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, G-4 (5.1 g, yield 76%) was obtained by column chromatography.
[LCMS] : 808[LCMS]: 808
[[ 합성예Synthetic example 65] 화합물 G-5의 합성 65] Synthesis of Compound G-5
준비예 14의 1-phenyl-2,3-bis(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-indole (5 g, 8.4 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.3 g, 18.4 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.4 g, 25.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 G-5 (5.4 g, 수율 68%)을 얻었다.1-phenyl-2,3-bis (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine (6.3 g, 18.4 mmol) and Pd (PPh 3) 4 ( 0.5 g, 0.4 mmol) and K 2 CO 3 (3.4 g, 25.1 mmol) were dissolved in 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, G-5 (5.4 g, yield 68%) was obtained by column chromatography.
[LCMS] : 961[LCMS]: 961
[[ 합성예Synthetic example 66] 화합물 G-12의 합성 66] Synthesis of compound G-12
준비예 13의 1-phenyl-2,3-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-indole (5 g, 8.4 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (6.3 g, 18.4 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.4 g, 25.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 G-12 (5.3 g, 수율 67 %)을 얻었다.1-phenyl-1H-indole (5 g, 8.4 mmol) in Preparation Example 13 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -6-chloro-2-phenylpyrimidine (6.3 g, 18.4 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (3.4 g, 25.1 mmol) was added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, G-12 (5.3 g, yield 67%) was obtained by column chromatography.
[LCMS] : 959[LCMS]: 959
[[ 합성예Synthetic example 67] 화합물 G-15의 합성 67] Synthesis of compound G-15
준비예 14의 1-phenyl-2,3-bis(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-indole (5 g, 8.4 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (6.3 g, 18.4 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.4 g, 25.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 G-15 (5.6 g, 수율 70 %)을 얻었다.1-phenyl-2,3-bis (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- mmol) and 4 - ([1,1'-biphenyl] -4-yl) -6-chloro-2-phenylpyrimidine (6.3 g, 18.4 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (3.4 g, 25.1 mmol) was added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, G-15 (5.6 g, yield 70%) was obtained by column chromatography.
[LCMS] : 959[LCMS]: 959
[[ 합성예Synthetic example 68] 화합물 G-22의 합성 68] Synthesis of compound G-22
준비예 13의 1-phenyl-2,3-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-indole (5 g, 8.4 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (6.3 g, 18.4 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.4 g, 25.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 G-22 (6.0 g, 수율 75 %)을 얻었다.1-phenyl-1H-indole (5 g, 8.4 mmol) in Preparation Example 13 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2-chloro-6-phenylpyrimidine (6.3 g, 18.4 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (3.4 g, 25.1 mmol) was added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, G-22 (6.0 g, yield 75%) was obtained by column chromatography.
[LCMS] : 959[LCMS]: 959
[[ 합성예Synthetic example 69] 화합물 G-25의 합성 69] Synthesis of Compound G-25
준비예 14의 1-phenyl-2,3-bis(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-indole (5 g, 8.4 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (6.3 g, 18.4 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.4 g, 25.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 G-25 (4.9 g, 수율 62 %)을 얻었다.1-phenyl-2,3-bis (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2-chloro-6-phenylpyrimidine (6.3 g, 18.4 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (3.4 g, 25.1 mmol) was added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, G-25 (4.9 g, yield 62%) was obtained by column chromatography.
[LCMS] : 959[LCMS]: 959
[[ 합성예Synthetic example 70] 화합물 G-39의 합성 70] Synthesis of compound G-39
준비예 13의 1-phenyl-2,3-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-indole (5 g, 8.4 mmol)와 2-chloro-4-phenylquinazoline (4.4 g, 18.4 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.4 g, 25.1 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 G-39 (3.8 g, 수율 60 %)을 얻었다.1-phenyl-1H-indole (5 g, 8.4 mmol) in Preparation Example 13 mmol) and 2-chloro-4-phenylquinazoline ( 4.4 g, 18.4 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (3.4 g, 25.1 mmol) of Toluene 80ml, EtOH 20ml, H 2 O and heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, G-39 (3.8 g, yield 60%) of the target compound was obtained by column chromatography.
[LCMS] : 754[LCMS]: 754
[[ 합성예Synthetic example 71] 화합물 H-1의 합성 71] Synthesis of Compound H-1
준비예 15의 3-phenyl-1,2-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3H-benzo[e]indole (5 g, 7.7 mmol)와 2-chloro-4,6-diphenyl-1,3,5-triazine (4.6 g, 17.0 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.2 g, 23.2 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 H-1 (4.8 g, 수율 72 %)을 얻었다.Preparation of 3-phenyl-1,2-bis (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -3H-benzo [e] indole 5 g, 7.7 mmol) and 2-chloro-4,6-diphenyl- 1,3,5-triazine (4.6 g, 17.0 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (3.2 g, 23.2 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, H-1 (4.8 g, yield 72%) was obtained by column chromatography.
[LCMS] : 859[LCMS]: 859
[[ 합성예Synthetic example 72] 화합물 H-2의 합성 72] Synthesis of Compound H-2
준비예 15의 3-phenyl-1,2-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3H-benzo[e]indole (5 g, 7.7 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (5.8 g, 17.0 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.2 g, 23.2 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 H-2 (5.3 g, 수율 68 %)을 얻었다.Preparation of 3-phenyl-1,2-bis (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -3H-benzo [e] indole 4-yl) -4-chloro-6-phenyl-1,3,5-triazine (5.8 g, 17.0 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.2 g, 23.2 mmol) were added to 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, H-2 (5.3 g, yield 68%) was obtained by column chromatography.
[LCMS] : 1011 [LCMS]: 1011
[[ 합성예Synthetic example 73] 화합물 H-3의 합성 73] Synthesis of Compound H-3
준비예 15의 3-phenyl-1,2-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3H-benzo[e]indole (5 g, 7.7 mmol)와 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (5.8 g, 17.0 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.2 g, 23.2 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 H-3 (4.7 g, 수율 60 %)을 얻었다.Preparation of 3-phenyl-1,2-bis (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -3H-benzo [e] indole 3-yl) -4-chloro-6-phenyl-1,3,5-triazine (5.8 g, 17.0 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.2 g, 23.2 mmol) were added to 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, H-3 (4.7 g, yield 60%) was obtained by column chromatography.
[LCMS] : 1011[LCMS]: 1011
[[ 합성예Synthetic example 74] 화합물 H-4의 합성 74] Synthesis of Compound H-4
준비예 16의 3-phenyl-1,2-bis(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3H-benzo[e]indole (5 g, 7.7 mmol)와 2-chloro-4,6-diphenyl-1,3,5-triazine (4.6 g, 17.0 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.2 g, 23.2 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 H-4 (4.8 g, 수율 72 %)을 얻었다.Preparation of 16 3-phenyl-1,2-bis (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -3H-benzo [e] indole 5 g, 7.7 mmol) and 2-chloro-4,6-diphenyl- 1,3,5-triazine (4.6 g, 17.0 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol), K 2 CO 3 (3.2 g, 23.2 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, H-4 (4.8 g, yield 72%) was obtained by column chromatography.
[LCMS] : 859[LCMS]: 859
[[ 합성예Synthetic example 75] 화합물 H-5의 합성 75] Synthesis of Compound H-5
준비예 16의 3-phenyl-1,2-bis(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3H-benzo[e]indole (5 g, 7.7 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (5.8 g, 17.0 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.2 g, 23.2 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 H-5 (4.4 g, 수율 57%)을 얻었다.Preparation of 16 3-phenyl-1,2-bis (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -3H-benzo [e] indole 4-yl) -4-chloro-6-phenyl-1,3,5-triazine (5.8 g, 17.0 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.2 g, 23.2 mmol) were added to 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, H-5 (4.4 g, yield 57%) was obtained by column chromatography.
[LCMS] : 1011[LCMS]: 1011
[[ 합성예Synthetic example 76] 화합물 H-12의 합성 76] Synthesis of Compound H-12
준비예 15의 3-phenyl-1,2-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3H-benzo[e]indole (5 g, 7.7 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (5.8 g, 17.0 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.2 g, 23.2 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 H-12 (4.5 g, 수율 58 %)을 얻었다.Preparation of 3-phenyl-1,2-bis (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -3H-benzo [e] indole 5 g, 7.7 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -6-chloro-2-phenylpyrimidine (5.8 g, 17.0 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.2 g, 23.2 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, H-12 (4.5 g, yield: 58%) was obtained by column chromatography.
[LCMS] : 1009[LCMS]: 1009
[[ 합성예Synthetic example 77] 화합물 H-15의 합성 77] Synthesis of Compound H-15
준비예 16의 3-phenyl-1,2-bis(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3H-benzo[e]indole (5 g, 7.7 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (5.8 g, 17.0 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.2 g, 23.2 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 H-15 (4.6 g, 수율 60 %)을 얻었다.Preparation of 16 3-phenyl-1,2-bis (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -3H-benzo [e] indole 5 g, 7.7 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -6-chloro-2-phenylpyrimidine (5.8 g, 17.0 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.2 g, 23.2 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, H-15 (4.6 g, yield 60%) was obtained by column chromatography.
[LCMS] : 1009[LCMS]: 1009
[[ 합성예Synthetic example 78] 화합물 H-22의 합성 78] Synthesis of Compound H-22
준비예 15의 3-phenyl-1,2-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3H-benzo[e]indole (5 g, 7.7 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (5.8 g, 17.0 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.2 g, 23.2 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 H-22 (4.7 g, 수율 60 %)을 얻었다.Preparation of 3-phenyl-1,2-bis (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -3H-benzo [e] indole 5 g, 7.7 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2-chloro-6-phenylpyrimidine (5.8 g, 17.0 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.2 g, 23.2 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, H-22 (4.7 g, yield 60%) was obtained by column chromatography.
[LCMS] : 1009[LCMS]: 1009
[[ 합성예Synthetic example 79] 화합물 H-25의 합성 79] Synthesis of Compound H-25
준비예 16의 3-phenyl-1,2-bis(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3H-benzo[e]indole (5 g, 7.7 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (5.8 g, 17.0 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.2 g, 23.2 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 H-25 (4.4 g, 수율 56 %)을 얻었다.Preparation of 16 3-phenyl-1,2-bis (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -3H-benzo [e] indole 5 g, 7.7 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2-chloro-6-phenylpyrimidine (5.8 g, 17.0 mmol) and Pd (PPh 3) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.2 g, 23.2 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, H-25 (4.4 g, yield 56%) was obtained by column chromatography.
[LCMS] : 1009[LCMS]: 1009
[[ 합성예Synthetic example 80] 화합물 H-39의 합성 80] Synthesis of Compound H-39
준비예 15의 3-phenyl-1,2-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3H-benzo[e]indole (5 g, 7.7 mmol)와 2-chloro-4-phenylquinazoline (4.1 g, 17.0 mmol) 및 Pd(PPh3)4 (0.5 g, 0.4 mmol), K2CO3 (3.2 g, 23.2 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 H-39 (3.8 g, 수율 61 %)을 얻었다.Preparation of 3-phenyl-1,2-bis (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -3H-benzo [e] indole 2-chloroquinazoline (4.1 g, 17.0 mmol), Pd (PPh 3 ) 4 (0.5 g, 0.4 mmol) and K 2 CO 3 (3.2 g, 23.2 mmol) , 20 ml of EtOH and 20 ml of H 2 O, and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, H-39 (3.8 g, yield: 61%) was obtained by column chromatography.
[LCMS] : 804[LCMS]: 804
[[ 합성예Synthetic example 81] 화합물 I-1의 합성 81] Synthesis of Compound I-1
준비예 17의 2,2'-(benzo[b]thiophene-2,3-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 7.7 mmol)와 2-chloro-4,6-diphenyl-1,3,5-triazine (5.5 g, 20.4 mmol) 및 Pd(PPh3)4 (0.5 g, 0.5 mmol), K2CO3 (3.9 g, 27.9 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 I-1 (4.8 g, 수율 70 %)을 얻었다.Preparation of 2,2'- (benzo [b] thiophene-2,3-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 5 g, 7.7 mmol) and 2-chloro-4,6-diphenyl- 1,3,5-triazine (5.5 g, 20.4 mmol) and Pd (PPh 3) 4 (0.5 g, 0.5 mmol), K 2 CO 3 (3.9 g, 27.9 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, the target compound I-1 (4.8 g, yield 70%) was obtained by column chromatography.
[LCMS] : 749[LCMS]: 749
[[ 합성예Synthetic example 82] 화합물 I-2의 합성 82] Synthesis of Compound I-2
준비예 17의 2,2'-(benzo[b]thiophene-2,3-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 7.7 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.0 g, 20.4 mmol) 및 Pd(PPh3)4 (0.5 g, 0.5 mmol), K2CO3 (3.9 g, 27.9 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 I-2 (5.9 g, 수율 71 %)을 얻었다.Preparation of 2,2'- (benzo [b] thiophene-2,3-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 4-yl) -4-chloro-6-phenyl-1,3,5-triazine (7.0 g, 20.4 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.5 mmol) and K 2 CO 3 (3.9 g, 27.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, column chromatography I-2 (5.9 g, yield 71%) was obtained.
[LCMS] : 902 [LCMS]: 902
[[ 합성예Synthetic example 83] 화합물 I-3의 합성 83] Synthesis of Compound I-3
준비예 17의 2,2'-(benzo[b]thiophene-2,3-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 7.7 mmol)와 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.0 g, 20.4 mmol) 및 Pd(PPh3)4 (0.5 g, 0.5 mmol), K2CO3 (3.9 g, 27.9 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 I-3 (5.7 g, 수율 68 %)을 얻었다.Preparation of 2,2'- (benzo [b] thiophene-2,3-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 3-yl) -4-chloro-6-phenyl-1,3,5-triazine (7.0 g, 20.4 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.5 mmol) and K 2 CO 3 (3.9 g, 27.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, column chromatography I-3 (5.7 g, yield 68%) was obtained.
[LCMS] : 902[LCMS]: 902
[[ 합성예Synthetic example 84] 화합물 I-4의 합성 84] Synthesis of Compound I-4
준비예 18의 2,2'-(benzo[b]thiophene-2,3-diylbis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 7.7 mmol)와 2-chloro-4,6-diphenyl-1,3,5-triazine (5.5 g, 20.4 mmol) 및 Pd(PPh3)4 (0.5 g, 0.5 mmol), K2CO3 (3.9 g, 27.9 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 I-4 (4.8 g, 수율 70 %)을 얻었다.Preparation of 2,2'- (benzo [b] thiophene-2,3-diylbis (3,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 5 g, 7.7 mmol) and 2-chloro-4,6-diphenyl- 1,3,5-triazine (5.5 g, 20.4 mmol) and Pd (PPh 3) 4 (0.5 g, 0.5 mmol), K 2 CO 3 (3.9 g, 27.9 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, the target compound I-4 (4.8 g, yield 70%) was obtained by column chromatography.
[LCMS] : 749[LCMS]: 749
[[ 합성예Synthetic example 85] 화합물 I-5의 합성 85] Synthesis of Compound I-5
준비예 18의 2,2'-(benzo[b]thiophene-2,3-diylbis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 7.7 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.0 g, 20.4 mmol) 및 Pd(PPh3)4 (0.5 g, 0.5 mmol), K2CO3 (3.9 g, 27.9 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 I-5 (5.4 g, 수율 65%)을 얻었다.Preparation of 2,2'- (benzo [b] thiophene-2,3-diylbis (3,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 4-yl) -4-chloro-6-phenyl-1,3,5-triazine (7.0 g, 20.4 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.5 mmol) and K 2 CO 3 (3.9 g, 27.9 mmol) were added to 80 ml of toluene, 20 ml of EtOH and 20 ml of H 2 O and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After the solvent of the filtered organic layer was removed, the target compound I-5 (5.4 g, yield 65%) was obtained by column chromatography.
[LCMS] : 902[LCMS]: 902
[[ 합성예Synthetic example 86] 화합물 I-12의 합성 86] Synthesis of Compound I-12
준비예 17의 2,2'-(benzo[b]thiophene-2,3-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 7.7 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (7.0 g, 20.4 mmol) 및 Pd(PPh3)4 (0.5 g, 0.5 mmol), K2CO3 (3.9 g, 27.9 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 I-12 (5.3 g, 수율 65 %)을 얻었다.Preparation of 2,2'- (benzo [b] thiophene-2,3-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 5 g, 7.7 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -6-chloro-2-phenylpyrimidine (7.0 g, 20.4 mmol) and Pd (PPh 3) 4 (0.5 g, 0.5 mmol) and K 2 CO 3 (3.9 g, 27.9 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, the target compound I-12 (5.3 g, yield 65%) was obtained by column chromatography.
[LCMS] : 890[LCMS]: 890
[[ 합성예Synthetic example 87] 화합물 I-15의 합성 87] Synthesis of Compound I-15
준비예 18의 2,2'-(benzo[b]thiophene-2,3-diylbis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 7.7 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (7.0 g, 20.4 mmol) 및 Pd(PPh3)4 (0.5 g, 0.5 mmol), K2CO3 (3.9 g, 27.9 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 I-15 (5.3 g, 수율 65 %)을 얻었다.Preparation of 2,2'- (benzo [b] thiophene-2,3-diylbis (3,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 5 g, 7.7 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -6-chloro-2-phenylpyrimidine (7.0 g, 20.4 mmol) and Pd (PPh 3) 4 (0.5 g, 0.5 mmol) and K 2 CO 3 (3.9 g, 27.9 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . The solvent of the filtered organic layer was removed, and the desired compound I-15 (5.3 g, yield 65%) was obtained by column chromatography.
[LCMS] : 890[LCMS]: 890
[[ 합성예Synthetic example 88] 화합물 I-22의 합성 88] Synthesis of Compound I-22
준비예 17의 2,2'-(benzo[b]thiophene-2,3-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 7.7 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (7.0 g, 20.4 mmol) 및 Pd(PPh3)4 (0.5 g, 0.5 mmol), K2CO3 (3.9 g, 27.9 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 I-22 (5.3 g, 수율 64 %)을 얻었다.Preparation of 2,2'- (benzo [b] thiophene-2,3-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 4-yl) -2-chloro-6-phenylpyrimidine (7.0 g, 20.4 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.5 mmol) and K 2 CO 3 (3.9 g, 27.9 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removal of the solvent of the filtered organic layer, the target compound I-22 (5.3 g, yield 64%) was obtained by column chromatography.
[LCMS] : 890[LCMS]: 890
[[ 합성예Synthetic example 89] 화합물 I-25의 합성 89] Synthesis of Compound I-25
준비예 18의 2,2'-(benzo[b]thiophene-2,3-diylbis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 7.7 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (7.0 g, 20.4 mmol) 및 Pd(PPh3)4 (0.5 g, 0.5 mmol), K2CO3 (3.9 g, 27.9 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 I-25 (5.0 g, 수율 60 %)을 얻었다.Preparation of 2,2'- (benzo [b] thiophene-2,3-diylbis (3,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 4-yl) -2-chloro-6-phenylpyrimidine (7.0 g, 20.4 mmol) and Pd (PPh 3 ) 4 (0.5 g, 0.5 mmol) and K 2 CO 3 (3.9 g, 27.9 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, I-25 (5.0 g, yield 60%) was obtained by column chromatography.
[LCMS] : 890[LCMS]: 890
[[ 합성예Synthetic example 90] 화합물 I-39의 합성 90] Synthesis of Compound I-39
준비예 17의 2,2'-(benzo[b]thiophene-2,3-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 7.7 mmol)와 2-chloro-4-phenylquinazoline (4.9 g, 20.4 mmol) 및 Pd(PPh3)4 (0.5 g, 0.5 mmol), K2CO3 (3.9 g, 27.9 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 I-39 (4.0 g, 수율 62 %)을 얻었다.Preparation of 2,2'- (benzo [b] thiophene-2,3-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 5 g, 7.7 mmol) and 2-chloro-4-phenylquinazoline ( 4.9 g, 20.4 mmol) and Pd (PPh 3) 4 (0.5 g, 0.5 mmol), K 2 CO 3 (3.9 g, 27.9 mmol) of Toluene 80ml , 20 ml of EtOH and 20 ml of H 2 O, and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, I-39 (4.0 g, yield 62%) was obtained by column chromatography.
[LCMS] : 695[LCMS]: 695
[[ 합성예Synthetic example 91] 화합물 J-1의 합성 91] Synthesis of Compound J-1
준비예 19의 2,2'-(benzofuran-2,3-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol)와 2-chloro-4,6-diphenyl-1,3,5-triazine (5.6 g, 21.1 mmol) 및 Pd(PPh3)4 (0.6 g, 0.5 mmol), K2CO3 (4.0 g, 28.7 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 J-1 (4.5 g, 수율 64 %)을 얻었다.Preparation of benzofuran-2,3-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol) and 2-chloro-4,6-diphenyl- 1,3,5-triazine (5.6 g, 21.1 mmol) and Pd (PPh 3) 4 (0.6 g, 0.5 mmol), K 2 CO 3 (4.0 g, 28.7 mmol) was added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, the target compound J-1 (4.5 g, yield 64%) was obtained by column chromatography.
[LCMS] : 733[LCMS]: 733
[[ 합성예Synthetic example 92] 화합물 J-2의 합성 92] Synthesis of Compound J-2
준비예 19의 2,2'-(benzofuran-2,3-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.3 g, 21.1 mmol) 및 Pd(PPh3)4 (0.6 g, 0.5 mmol), K2CO3 (4.0 g, 28.7 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 J-2 (5.7 g, 수율 67 %)을 얻었다.Preparation of benzofuran-2,3-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine (7.3 g, 21.1 mmol) and Pd (PPh 3) 4 ( 0.6 g, 0.5 mmol) and K 2 CO 3 (4.0 g, 28.7 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, the target compound J-2 (5.7 g, yield 67%) was obtained by column chromatography.
[LCMS] : 886 [LCMS]: 886
[[ 합성예Synthetic example 93] 화합물 J-3의 합성 93] Synthesis of Compound J-3
준비예 19의 2,2'-(benzofuran-2,3-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol)와 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.3 g, 21.1 mmol) 및 Pd(PPh3)4 (0.6 g, 0.5 mmol), K2CO3 (4.0 g, 28.7 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 J-3 (5.1 g, 수율 60 %)을 얻었다.Preparation of benzofuran-2,3-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol) and 2 - ([1,1'-biphenyl] -3-yl) -4-chloro-6-phenyl-1,3,5-triazine (7.3 g, 21.1 mmol) and Pd (PPh 3) 4 ( 0.6 g, 0.5 mmol) and K 2 CO 3 (4.0 g, 28.7 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, J-3 (5.1 g, yield 60%) was obtained by column chromatography.
[LCMS] : 886[LCMS]: 886
[[ 합성예Synthetic example 94] 화합물 J-4의 합성 94] Synthesis of Compound J-4
준비예 20의 2,2'-(benzofuran-2,3-diylbis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol)와 2-chloro-4,6-diphenyl-1,3,5-triazine (5.6 g, 21.1 mmol) 및 Pd(PPh3)4 (0.6 g, 0.5 mmol), K2CO3 (4.0 g, 28.7 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 J-4 (4.5 g, 수율 64 %)을 얻었다.Bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) of Preparation Example 20 (5 g, 9.6 mmol) and 2-chloro-4,6-diphenyl- 1,3,5-triazine (5.6 g, 21.1 mmol) and Pd (PPh 3) 4 (0.6 g, 0.5 mmol), K 2 CO 3 (4.0 g, 28.7 mmol) was added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, the target compound J-4 (4.5 g, yield 64%) was obtained by column chromatography.
[LCMS] : 733[LCMS]: 733
[[ 합성예Synthetic example 95] 화합물 J-5의 합성 95] Synthesis of Compound J-5
준비예 20의 2,2'-(benzofuran-2,3-diylbis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol)와 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (7.3 g, 21.1 mmol) 및 Pd(PPh3)4 (0.6 g, 0.5 mmol), K2CO3 (4.0 g, 28.7 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 J-5 (5.3 g, 수율 63%)을 얻었다.Bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) of Preparation Example 20 (5 g, 9.6 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine (7.3 g, 21.1 mmol) and Pd (PPh 3) 4 ( 0.6 g, 0.5 mmol) and K 2 CO 3 (4.0 g, 28.7 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removal of the solvent of the filtered organic layer, the target compound J-5 (5.3 g, yield 63%) was obtained by column chromatography.
[LCMS] : 886[LCMS]: 886
[[ 합성예Synthetic example 96] 화합물 J-12의 합성 96] Synthesis of Compound J-12
준비예 19의 2,2'-(benzofuran-2,3-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (7.2 g, 21.6 mmol) 및 Pd(PPh3)4 (0.6 g, 0.5 mmol), K2CO3 (4.0 g, 28.7 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 J-12 (5.5 g, 수율 65 %)을 얻었다.Preparation of benzofuran-2,3-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -6-chloro-2-phenylpyrimidine (7.2 g, 21.6 mmol) and Pd (PPh 3) 4 (0.6 g, 0.5 mmol), K 2 CO 3 (4.0 g, 28.7 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, J-12 (5.5 g, yield 65%) was obtained by column chromatography.
[LCMS] : 884[LCMS]: 884
[[ 합성예Synthetic example 97] 화합물 J-15의 합성 97] Synthesis of Compound J-15
준비예 20의 2,2'-(benzofuran-2,3-diylbis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol)와 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (7.2 g, 21.6 mmol) 및 Pd(PPh3)4 (0.6 g, 0.5 mmol), K2CO3 (4.0 g, 28.7 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 J-15 (5.2 g, 수율 62 %)을 얻었다.Bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) of Preparation Example 20 (5 g, 9.6 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -6-chloro-2-phenylpyrimidine (7.2 g, 21.6 mmol) and Pd (PPh 3) 4 (0.6 g, 0.5 mmol), K 2 CO 3 (4.0 g, 28.7 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, the target compound J-15 (5.2 g, yield 62%) was obtained by column chromatography.
[LCMS] : 884[LCMS]: 884
[[ 합성예Synthetic example 98] 화합물 J-22의 합성 98] Synthesis of compound J-22
준비예 19의 2,2'-(benzofuran-2,3-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (7.2 g, 21.6 mmol) 및 Pd(PPh3)4 (0.6 g, 0.5 mmol), K2CO3 (4.0 g, 28.7 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 J-22 (5.1 g, 수율 60 %)을 얻었다.Preparation of benzofuran-2,3-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2-chloro-6-phenylpyrimidine (7.2 g, 21.6 mmol) and Pd (PPh 3) 4 (0.6 g, 0.5 mmol), K 2 CO 3 (4.0 g, 28.7 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, J-22 (5.1 g, yield 60%) was obtained by column chromatography.
[LCMS] : 884[LCMS]: 884
[[ 합성예Synthetic example 99] 화합물 J-25의 합성 99] Synthesis of Compound J-25
준비예 20의 2,2'-(benzofuran-2,3-diylbis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol)와 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine (7.2 g, 21.6 mmol) 및 Pd(PPh3)4 (0.6 g, 0.5 mmol), K2CO3 (4.0 g, 28.7 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 J-25 (4.9 g, 수율 58 %)을 얻었다.Bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) of Preparation Example 20 (5 g, 9.6 mmol) and 4 - ([1,1'-biphenyl] -4-yl) -2-chloro-6-phenylpyrimidine (7.2 g, 21.6 mmol) and Pd (PPh 3) 4 (0.6 g, 0.5 mmol), K 2 CO 3 (4.0 g, 28.7 mmol) were added to Toluene (80 ml), EtOH (20 ml) and H 2 O (20 ml), and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, J-25 (4.9 g, yield: 58%) was obtained by column chromatography.
[LCMS] : 884[LCMS]: 884
[[ 합성예Synthetic example 100] 화합물 J-39의 합성 100] Synthesis of compound J-39
준비예 19의 2,2'-(benzofuran-2,3-diylbis(4,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol)와 2-chloro-4-phenylquinazoline (5.1 g, 21.6 mmol) 및 Pd(PPh3)4 (0.6 g, 0.5 mmol), K2CO3 (4.0 g, 28.7 mmol)을 Toluene 80ml, EtOH 20ml, H2O 20ml에 넣고 12시간동안 가열환류하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 J-39 (4.2 g, 수율 64 %)을 얻었다.Preparation of benzofuran-2,3-diylbis (4,1-phenylene)) bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (5 g, 9.6 mmol) and 2-chloro-4-phenylquinazoline ( 5.1 g, 21.6 mmol) and Pd (PPh 3) 4 (0.6 g, 0.5 mmol), K 2 CO 3 (4.0 g, a 28.7 mmol) Toluene 80ml, EtOH 20ml , H 2 O and heated to reflux for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, J-39 (4.2 g, yield 64%) was obtained by column chromatography.
[LCMS] : 679[LCMS]: 679
[[ 실시예Example 1 내지 60] 청색 유기 1 to 60] blue organic 전계Field 발광 소자의 제작 Fabrication of light emitting device
합성예에서 합성된 화합물 A-1, A-2, A-3, A-12, A-22, A-39, B-1, B-2, B-3, B-12, B-22, B-39, C-1, C-2, C-3, C-12, C-22, C-39, D-1, D-2, D-3, D-12, D-22, D-39, E-1, E-2, E-3, E-12, E-22, E-39, F-1, F-2, F-3, F-12, F-22, F-39, G-1, G-2, G-3, G-12, G-22, G-39, H-1, H-2, H-3, H-12, H-22, H-39, I-1, I-2, I-3, I-12, I-22, I-39, J-1, J-2, J-3, J-12, J-22, J-39을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 하기와 같이 청색 유기 전계 발광 소자를 제작하였다.A-2, A-3, A-12, A-22, A-39, B-1, B-2, B-3, B- B-39, C-1, C-2, C-3, C-12, C-22, C-39, D-1, D- F-39, E-1, E-2, E-3, E-12, E-22, E-39, F-1, F- H-2, G-3, G-12, G-22, G-39, H-1, H-2, H- 1, I-2, I-3, I-12, I-22, I-39, J-1, J-2, J-3, J- , The blue organic electroluminescent device was fabricated as described below.
먼저, ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면, 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후, UV OZONE 세정기(Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, and methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) The substrate was transferred to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에, DS-205 (㈜두산전자, 80 nm)/NPB (15 nm)/ADN + 5 % DS-405 (㈜두산전자, 30 nm)/합성예에서 합성한 각각의 화합물 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다. NPN (15 nm) / ADN + 5% DS-405 (Doosan Electronics, 30 nm) / synthesized in Synthesis Example) on the ITO transparent electrode thus prepared Compound (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.
[[ 비교예Comparative Example 1] 청색 유기 1] Blue organic 전계Field 발광 소자의 제작 Fabrication of light emitting device
전자 수송층 물질로서 화합물 A-1 대신 Alq3을 사용하는 것을 제외하고는, 상기 실시예 1과 동일한 과정으로 청색 유기 전계 발광 소자를 제작하였다.A blue organic electroluminescent device was fabricated in the same manner as in Example 1, except that Alq3 was used instead of Compound A-1 as the electron transport layer material.
[[ 비교예Comparative Example 2] 청색 유기 2] Blue organic 전계Field 발광 소자의 제작 Fabrication of light emitting device
전자 수송층 물질로서 화합물 A-1을 사용하지 않은 것을 제외하고는, 상기 실시예 1과 동일한 과정으로 청색 유기 전계 발광 소자를 제작하였다.A blue organic electroluminescent device was fabricated in the same manner as in Example 1 except that the compound A-1 was not used as the electron transport layer material.
상기 실시예 1 내지 60, 비교예 1 및 2에서 사용된 NPB, ADN 및 Alq3의 구조는 하기와 같다. The structures of NPB, ADN and Alq3 used in Examples 1 to 60 and Comparative Examples 1 and 2 are as follows.
[[ 평가예Evaluation example 1] One]
실시예 1 내지 60, 비교예 1 및 2에서 제작한 각각의 청색 유기 전계 발광 소자에 대하여 전류밀도 (10) mA/㎠에서의 구동전압, 전류효율 및 발광피크를 측정하고, 그 결과를 하기 표 2에 나타내었다.Current efficiency and emission peak at current density (10) mA / cm < 2 > were measured for each of the blue organic electroluminescent devices manufactured in Examples 1 to 60 and Comparative Examples 1 and 2, Respectively.
상기 표 2에 나타낸 바와 같이, 본 발명의 화합물을 전자 수송층에 사용한 청색 유기 전계 발광 소자(실시예 1 내지 60)는 종래의 Alq3를 전자 수송층에 사용한 청색 유기 전계 발광 소자(비교예 1)와 전자 수송층이 없는 청색 유기 전계 발광 소자(비교예 2)에 비해 구동전압, 발광피크 및 전류효율 면에서 우수한 성능을 나타내는 것을 알 수 있었다.As shown in Table 2, the blue organic electroluminescent devices (Examples 1 to 60) using the compound of the present invention as the electron transport layer (Examples 1 to 60) Emitting layer exhibited excellent performance in terms of driving voltage, luminescent peak, and current efficiency as compared with the blue organic electroluminescent device having no transport layer (Comparative Example 2).
[[ 실시예Example 61 내지 100] 녹색 유기 61 to 100] Green organic 전계Field 발광 소자의 제작 Fabrication of light emitting device
합성예에서 합성한 화합물 A-4, A-5, A-15, A-25, B-4, B-5, B-15, B-25, C-4, C-5, C-15, C-25, D-4, D-5, D-15, D-25, E-4, E-5, E-15, E-25, F-4, F-5, F-15, F-25, G-4, G-5, G-15, G-25, H-4, H-5, H-15, H-25, I-4, I-5, I-15, I-25, J-4, J-5, J-15, J-25를 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 녹색 유기 전계 발광 소자를 제작하였다.A-5, A-15, A-25, B-4, B-5, B-15, B-25, C-4, C- F-5, F-15, F-15, D-25, D-5, D-15, D-25, E-4, E-5, E-15, E- 25, G-4, G-5, G-15, G-25, H-4, H-5, H-15, H-25, I- J-4, J-5, J-15 and J-25 were subjected to high purity sublimation purification by a known method, and then a green organic electroluminescent device was fabricated according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수로 초음파 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 5분간 세정하고 진공 증착기로 코팅된 유리 기판을 이송하였다.First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was ultrasonically washed with distilled water. After washing with distilled water, it was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, and methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), washed with UV for 5 minutes and then coated with a vacuum evaporator The substrate was transferred.
이렇게 준비된 ITO 투명 유리 기판(전극) 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ 90 %의 합성예에서 합성한 각각의 화합물 + 10 %의 Ir(ppy)3 (30 nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 녹색 유기 전계 발광 소자를 제작하였다.Each compound synthesized in a m-MTDATA (60 nm) / TCTA (80 nm) / 90% synthesis example + 10% Ir (ppy) 3 (30 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to prepare a green organic electroluminescent device.
[[ 비교예Comparative Example 3] 녹색 유기 3] Green organic 전계Field 발광 소자의 제작 Fabrication of light emitting device
발광층 형성시 발광 호스트 물질로서 A-4 대신 CBP를 사용하는 것을 제외하고는 실시예 61과 동일한 과정으로 녹색 유기 전계 발광 소자를 제작하였다.A green organic electroluminescent device was fabricated in the same manner as in Example 61, except that CBP was used instead of A-4 as a luminescent host material in forming the light emitting layer.
실시예 61 내지 100, 비교예 3에서 사용된 m-MTDATA, TCTA, Ir(ppy)3, CBP 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, Ir (ppy) 3 , CBP and BCP used in Examples 61 to 100 and Comparative Example 3 are as follows.
[[ 평가예Evaluation example 2] 2]
실시예 61 내지 100, 비교예 3에서 제작한 각각의 녹색 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 3에 나타내었다.The driving voltage, current efficiency and emission peak at each current density of 10 mA / cm 2 were measured for each of the green organic electroluminescent devices manufactured in Examples 61 to 100 and Comparative Example 3, and the results are shown in Table 3 below .
상기 표 3에 나타낸 바와 같이, 본 발명에 따른 화합물을 발광층에 사용한 녹색 유기 전계 발광 소자(실시예 61 내지 100)는 종래의 CBP를 발광층에 사용한 녹색 유기 전계 발광 소자(비교예 3)에 비해 전류효율 및 구동전압이 우수한 것을 알 수 있었다.As shown in Table 3, the green organic electroluminescent devices (Examples 61 to 100) using the compound according to the present invention in the light emitting layer exhibited a higher electric current than the green organic electroluminescent device using the conventional CBP as the light emitting layer (Comparative Example 3) The efficiency and the driving voltage were excellent.
Claims (8)
[화학식 1]
상기 화학식 1에서,
X는 C(R2)(R3), O, S 및 N(R4)로 이루어진 군에서 선택되고,
L1 및 L2는 서로 동일하거나 상이하며, 각각 독립적으로 단일결합이거나, 혹은 C6~C18의 아릴렌기 및 핵원자수 5 내지 18의 헤테로아릴렌기로 이루어진 군에서 선택되고,
Ar1 및 Ar2는 서로 동일하거나 상이하며, 각각 독립적으로 질소를 함유하는 핵원자수 5 내지 60의 헤테로아릴기이고,
n은 0 내지 4의 정수이고,
R1 내지 R4는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 혹은 인접하는 기와 결합하여 축합 고리를 형성할 수 있고,
상기 L1 및 L2의 아릴렌기 및 헤테로아릴렌기와, 상기 Ar1 및 Ar2, R1 내지 R4의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.A compound represented by the following formula (1):
[Chemical Formula 1]
In Formula 1,
X is selected from the group consisting of C (R 2 ) (R 3 ), O, S and N (R 4 )
L 1 and L 2 are the same or different and are each independently a single bond or a group selected from the group consisting of a C 6 to C 18 arylene group and a heteroarylene group having 5 to 18 nucleus atoms,
Ar 1 and Ar 2 are the same or different and each is a heteroaryl group having 5 to 60 nuclear atoms and containing nitrogen,
n is an integer from 0 to 4,
R 1 to R 4 are the same or different, each independently represent hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C 1 ~ alkenyl group of the C 40 alkyl group, C 2 ~ C 40 of, C 2 ~ alkynyl group of C 40, C 3 ~ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyl silyl group, the group C 6 ~ C 60 aryl silyl, C 1 ~ group alkylboronic of C 40, C 6 ~ C group of 60 arylboronic, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ selected from the group consisting of an aryl amine of the C 60 of or, or adjacent groups bonded fused to the A ring can be formed,
Wherein L 1, and arylene group of L 2 and a heteroarylene group, an alkyl group of said Ar 1 and Ar 2, R 1 to R 4, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, An alkyl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, A nitro group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C An aryl group having 6 to 60 carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 ~ C 60 aryl silyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C of the group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ aryl phosphine oxide of the C 60 group And C 6 -C An arylamine group having 1 to 60 carbon atoms, and when the substituent is plural, they may be the same or different from each other.
상기 Ar1 및 Ar2는 서로 동일하거나 상이하며, 각각 독립적으로 하기 A1 내지 A16, B1 내지 B25 중 어느 하나로 표시되는 치환체인 화합물.
상기 A1 내지 A16, B1 내지 B25에서,
p는 0 내지 4의 정수이고,
R5 및 R6은 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 혹은 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며, 상기 R5 또는 R6이 복수인 경우, 이들은 서로 동일하거나 상이할 수 있고,
상기 R5 및 R6의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.The method according to claim 1,
Wherein Ar 1 and Ar 2 are the same or different and are each independently a substituent represented by any one of the following A 1 to A 16 and B 1 to B 25.
In the above-mentioned A1 to A16 and B1 to B25,
p is an integer of 0 to 4,
R 5 and R 6 are the same or different and are each independently hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C 1 ~ alkenyl group of the C 40 alkyl group, C 2 ~ C 40 of, C 2 ~ alkynyl group of C 40, C 3 ~ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyl silyl group, the group C 6 ~ C 60 aryl silyl, C 1 ~ group alkylboronic of C 40, C 6 ~ C group of 60 arylboronic, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ selected from the group consisting of an aryl amine of the C 60 of or, or adjacent groups bonded fused to the And when R 5 or R 6 is plural, they may be the same or different from each other,
Alkyl groups of the R 5 and R 6, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkenyl group, an aryl group, A C 3 to C 40 cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkynyl group, ~ C 40 alkyloxy group of, C 6 ~ aryloxy C 60, C 1 ~ C 40 alkyl silyl group, C 6 ~ aryl silyl group of C 60, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ one or more substituents selected from the group consisting of C 60 arylamine It may be substituted, and wherein when the substituent is plural, they may be the same or different from each other.
상기 R1 내지 R3은 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소(D), 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기 및 C2~C40의 알키닐기로 이루어진 군에서 선택되거나, 혹은 인접하는 기와 결합하여 축합 고리를 형성할 수 있고,
상기 R4는 수소, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되는 것인 화합물.The method according to claim 1,
Wherein R 1 to R 3 are the same or different and are each independently hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C 1 ~ C 40 alkyl group, C 2 ~ alkenyl group and C 2 of the C 40 To C 40 alkynyl group, or may be bonded to adjacent groups to form a condensed ring,
The compound to the R 4 is hydrogen, C 6 ~ C 60 aryl group, nuclear atoms, an aryl group of 5 to 60 heteroaryl and C 6 ~ C 60 of which is selected from the group consisting of an aryl amine.
상기 화학식 1로 표시되는 화합물은 하기 화학식 2 내지 5 중 적어도 어느 하나로 표시되는 것인 화합물.
[화학식 2]
[화학식 3]
[화학식 4]
[화학식 5]
상기 화학식 2 내지 5에서,
L1, L2, Ar1, Ar2, n, R1 내지 R4는 각각 제1항에서 정의한 바와 같다.The method according to claim 1,
Wherein the compound represented by the formula (1) is represented by at least one of the following formulas (2) to (5).
(2)
(3)
[Chemical Formula 4]
[Chemical Formula 5]
In the above formulas 2 to 5,
L 1 , L 2 , Ar 1 , Ar 2 , n, and R 1 to R 4 are as defined in claim 1, respectively.
상기 화학식 1로 표시되는 화합물은 하기 화학식 6 내지 15 중 적어도 어느 하나로 표시되는 것인 화합물.
[화학식 6]
[화학식 7]
[화학식 8]
[화학식 9]
[화학식 10]
[화학식 11]
[화학식 12]
[화학식 13]
[화학식 14]
[화학식 15]
상기 화학식 6 내지 15에서,
L1, L2, Ar1, Ar2, n 및 R1는 각각 제1항에서 정의한 바와 같고,
A는 R1과 다른 R1이 결합하여 축합 고리를 형성한 것이고,
Ar3은 C6~C18의 아릴기이다.The method according to claim 1,
Wherein the compound represented by the formula (1) is represented by at least one of the following formulas (6) to (15).
[Chemical Formula 6]
(7)
[Chemical Formula 8]
[Chemical Formula 9]
[Chemical formula 10]
(11)
[Chemical Formula 12]
[Chemical Formula 13]
[Chemical Formula 14]
[Chemical Formula 15]
In the above formulas (6) to (15)
L 1 , L 2 , Ar 1 , Ar 2 , n and R 1 are as defined in claim 1,
A is one in which R 1 and the other R 1 are bonded to form a condensed ring,
Ar 3 is a C 6 to C 18 aryl group.
양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하고,
상기 1층 이상의 유기물층 중 적어도 하나는 제1항 내지 제5항 중 어느 한 항에 기재된 화합물을 포함하는 것인 유기 전계 발광 소자.The method according to claim 1,
An organic electroluminescent device comprising a cathode, a cathode, and at least one organic layer interposed between the anode and the cathode,
Wherein at least one of the one or more organic layers includes the compound according to any one of claims 1 to 5.
상기 화합물을 포함하는 유기물층은 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자 수송층 및 전자 주입층으로 이루어진 군에서 선택되는 것인 유기 전계 발광 소자.The method according to claim 6,
Wherein the organic compound layer containing the compound is selected from the group consisting of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, and an electron injecting layer.
상기 화합물을 포함하는 유기물층은 발광층 및 전자 수송층인 유기 전계 발광 소자.The method according to claim 6,
Wherein the organic compound layer containing the compound is a light emitting layer and an electron transporting layer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020160165270A KR20180064861A (en) | 2016-12-06 | 2016-12-06 | Organic compound and organic electroluminescent device using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020160165270A KR20180064861A (en) | 2016-12-06 | 2016-12-06 | Organic compound and organic electroluminescent device using the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20180064861A true KR20180064861A (en) | 2018-06-15 |
Family
ID=62628990
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020160165270A KR20180064861A (en) | 2016-12-06 | 2016-12-06 | Organic compound and organic electroluminescent device using the same |
Country Status (1)
| Country | Link |
|---|---|
| KR (1) | KR20180064861A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019198806A1 (en) * | 2018-04-13 | 2019-10-17 | 出光興産株式会社 | Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device |
| CN114635037A (en) * | 2022-03-10 | 2022-06-17 | 浙江大学 | Method for extracting and separating trivalent lanthanide and/or trivalent actinide |
| US11878968B2 (en) | 2021-07-09 | 2024-01-23 | Plexium, Inc. | Aryl compounds and pharmaceutical compositions that modulate IKZF2 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001160489A (en) | 1999-12-01 | 2001-06-12 | Toyota Central Res & Dev Lab Inc | Organic electroluminescent element |
-
2016
- 2016-12-06 KR KR1020160165270A patent/KR20180064861A/en not_active Application Discontinuation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001160489A (en) | 1999-12-01 | 2001-06-12 | Toyota Central Res & Dev Lab Inc | Organic electroluminescent element |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019198806A1 (en) * | 2018-04-13 | 2019-10-17 | 出光興産株式会社 | Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device |
| US11878968B2 (en) | 2021-07-09 | 2024-01-23 | Plexium, Inc. | Aryl compounds and pharmaceutical compositions that modulate IKZF2 |
| CN114635037A (en) * | 2022-03-10 | 2022-06-17 | 浙江大学 | Method for extracting and separating trivalent lanthanide and/or trivalent actinide |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR102350318B1 (en) | Organic compound and organic electro luminescence device comprising the same | |
| KR101614599B1 (en) | Organic compound and organic electroluminescent device comprising the same | |
| KR102283293B1 (en) | Organic compounds and organic electro luminescence device comprising the same | |
| JP2022064995A (en) | Organic light-emitting compound and organic electroluminescent device including the same | |
| KR20180069475A (en) | Organic light-emitting compound and organic electroluminescent device using the same | |
| KR102577617B1 (en) | Organic compounds and organic electro luminescence device comprising the same | |
| KR20150047858A (en) | Organic compounds and organic electro luminescence device comprising the same | |
| KR102199112B1 (en) | Organic compound and organic electroluminescent device using the same | |
| KR20230078604A (en) | Organic compounds and organic electro luminescence device comprising the same | |
| KR20200025382A (en) | Organic compound and organic electroluminescent device using the same | |
| KR20230040969A (en) | Organic compound and organic electroluminescent device using the same | |
| KR102559638B1 (en) | Organic light-emitting compound and organic electroluminescent device using the same | |
| KR102506419B1 (en) | Organic compound and organic electroluminescent device comprising the same | |
| KR20180064861A (en) | Organic compound and organic electroluminescent device using the same | |
| KR101585303B1 (en) | Organic lightingemitting compound and organic electroluminescent device using the same | |
| KR101603384B1 (en) | Organic compounds and organic electro luminescence device comprising the same | |
| KR102360504B1 (en) | Organic compound and organic electroluminescent device comprising the same | |
| KR102633478B1 (en) | Organic compound and organic electroluminescent device using the same | |
| KR20200005272A (en) | Organic compound and organic electroluminescent device including the same | |
| KR102507371B1 (en) | Organic light-emitting compound and organic electroluminescent device using the same | |
| KR102307370B1 (en) | Organic compound and organic electroluminescent device comprising the same | |
| KR20180041361A (en) | Organic compound and organic electroluminescent device using the same | |
| KR20170114369A (en) | Organic compound and organic electroluminescent device using the same | |
| KR101759439B1 (en) | Organic compounds and organic electro luminescence device comprising the same | |
| KR20200119648A (en) | Organic compound and organic electroluminescent device using the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| N231 | Notification of change of applicant | ||
| E902 | Notification of reason for refusal | ||
| E90F | Notification of reason for final refusal |