WO2016099037A2 - Organic compound and organic electroluminescent device comprising same - Google Patents
Organic compound and organic electroluminescent device comprising same Download PDFInfo
- Publication number
- WO2016099037A2 WO2016099037A2 PCT/KR2015/012394 KR2015012394W WO2016099037A2 WO 2016099037 A2 WO2016099037 A2 WO 2016099037A2 KR 2015012394 W KR2015012394 W KR 2015012394W WO 2016099037 A2 WO2016099037 A2 WO 2016099037A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- aryl
- alkyl
- boron
- formula
- Prior art date
Links
- 150000002894 organic compounds Chemical class 0.000 title abstract description 8
- 239000011368 organic material Substances 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims description 97
- 150000001875 compounds Chemical class 0.000 claims description 97
- 229910052757 nitrogen Inorganic materials 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 125000001424 substituent group Chemical group 0.000 claims description 39
- 125000004429 atom Chemical group 0.000 claims description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 29
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 23
- 125000004104 aryloxy group Chemical group 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 23
- 125000005264 aryl amine group Chemical group 0.000 claims description 22
- 125000005104 aryl silyl group Chemical group 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 18
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 17
- -1 alkyl boron Chemical compound 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 13
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 230000005525 hole transport Effects 0.000 claims description 11
- 229910052796 boron Inorganic materials 0.000 claims description 10
- 150000004982 aromatic amines Chemical class 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 135
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 88
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 84
- 230000015572 biosynthetic process Effects 0.000 description 78
- 238000003786 synthesis reaction Methods 0.000 description 78
- 239000012044 organic layer Substances 0.000 description 70
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
- 239000010410 layer Substances 0.000 description 52
- 238000006243 chemical reaction Methods 0.000 description 45
- 238000004440 column chromatography Methods 0.000 description 45
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 44
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 32
- 239000002904 solvent Substances 0.000 description 27
- 238000005160 1H NMR spectroscopy Methods 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- 230000000052 comparative effect Effects 0.000 description 21
- 239000000463 material Substances 0.000 description 19
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 18
- 239000000758 substrate Substances 0.000 description 15
- 238000002347 injection Methods 0.000 description 13
- 239000007924 injection Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- OVNPUJOZNPAVJQ-UHFFFAOYSA-N 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound ClC1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 OVNPUJOZNPAVJQ-UHFFFAOYSA-N 0.000 description 11
- WDECIBYCCFPHNR-UHFFFAOYSA-N Chrysene Natural products C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 10
- SFUIGUOONHIVLG-UHFFFAOYSA-N (2-nitrophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1[N+]([O-])=O SFUIGUOONHIVLG-UHFFFAOYSA-N 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- GMJNODHAAPUIHL-UHFFFAOYSA-N 25-chloro-22-azahexacyclo[12.11.0.02,11.05,10.015,23.016,21]pentacosa-1(25),2(11),3,5,7,9,12,14,16,18,20,23-dodecaene Chemical compound ClC1=CC=2NC=3C=CC=CC=3C=2C2=C1C=1C=CC3=CC=CC=C3C=1C=C2 GMJNODHAAPUIHL-UHFFFAOYSA-N 0.000 description 7
- FXLYFBFEQBVUQA-UHFFFAOYSA-N 4-chloro-1-(2-nitrophenyl)chrysene Chemical compound ClC1=CC=C(C=2C=CC3=C4C=CC=CC4=CC=C3C1=2)C1=C(C=CC=C1)[N+](=O)[O-] FXLYFBFEQBVUQA-UHFFFAOYSA-N 0.000 description 7
- XRYSCSFJNUNNAU-UHFFFAOYSA-N n-chloro-n-phenylaniline Chemical compound C=1C=CC=CC=1N(Cl)C1=CC=CC=C1 XRYSCSFJNUNNAU-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- YMXOBGNBCRJINU-UHFFFAOYSA-N 1-(2-nitrophenyl)chrysene Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)C1=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC1=2 YMXOBGNBCRJINU-UHFFFAOYSA-N 0.000 description 6
- 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 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- HRRMKZWYKMIUEI-UHFFFAOYSA-N sodium 2-methylpropan-2-olate toluene Chemical compound [Na+].CC(C)(C)[O-].CC1=CC=CC=C1 HRRMKZWYKMIUEI-UHFFFAOYSA-N 0.000 description 6
- 239000011521 glass Substances 0.000 description 5
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- VWHGISJMCYJWLL-UHFFFAOYSA-N 1-(5-bromo-2-nitrophenyl)chrysene Chemical compound BrC=1C=CC(=C(C=1)C1=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC1=2)[N+](=O)[O-] VWHGISJMCYJWLL-UHFFFAOYSA-N 0.000 description 4
- OHPGQYITCAGTTQ-UHFFFAOYSA-N 18-bromo-22-azahexacyclo[12.11.0.02,11.05,10.015,23.016,21]pentacosa-1(14),2(11),3,5,7,9,12,15(23),16(21),17,19,24-dodecaene Chemical compound BrC1=CC=2C=3C4=C(C=CC=3NC=2C=C1)C=1C=CC2=CC=CC=C2C=1C=C4 OHPGQYITCAGTTQ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical group C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 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
- 238000011156 evaluation Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 0.000 description 4
- AMEAOPJZOVYOHS-UHFFFAOYSA-N 1-chlorochrysene Chemical compound C1=CC2=C3C=CC=CC3=CC=C2C2=C1C(Cl)=CC=C2 AMEAOPJZOVYOHS-UHFFFAOYSA-N 0.000 description 3
- FPJRIOPPDDLMCV-UHFFFAOYSA-N 2-(2-nitrophenyl)chrysene Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)C1=CC=2C=CC3=C4C=CC=CC4=CC=C3C=2C=C1 FPJRIOPPDDLMCV-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
- YFVCVISJBIINTQ-UHFFFAOYSA-N 22-azahexacyclo[12.11.0.02,11.05,10.015,23.016,21]pentacosa-1(14),2(11),3,5,7,9,12,15(23),16,18,20,24-dodecaene Chemical compound C1=C2C=3C=CC4=C(C=CC=5NC=6C=CC=CC=6C4=5)C=3C=CC2=CC=C1 YFVCVISJBIINTQ-UHFFFAOYSA-N 0.000 description 3
- RJUKKDPKJJYVQZ-UHFFFAOYSA-N 25-(2-nitrophenyl)-22-azahexacyclo[12.11.0.02,11.05,10.015,23.016,21]pentacosa-1(14),2(11),3,5,7,9,12,15(23),16,18,20,24-dodecaene Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)C1=CC=2NC=3C=CC=CC=3C=2C2=C1C=1C=CC3=CC=CC=C3C=1C=C2 RJUKKDPKJJYVQZ-UHFFFAOYSA-N 0.000 description 3
- RSYANEPGVYTDPR-UHFFFAOYSA-N 25-(2-nitrophenyl)-22-phenyl-22-azahexacyclo[12.11.0.02,11.05,10.015,23.016,21]pentacosa-1(14),2(11),3,5,7,9,12,15(23),16,18,20,24-dodecaene Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)C1=CC=2N(C=3C=CC=CC=3C=2C2=C1C=1C=CC3=CC=CC=C3C=1C=C2)C1=CC=CC=C1 RSYANEPGVYTDPR-UHFFFAOYSA-N 0.000 description 3
- KYEDBZMRGODDBG-UHFFFAOYSA-N 3-(2-nitrophenyl)chrysene Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)C=1C=CC=2C=CC3=C4C=CC=CC4=CC=C3C=2C=1 KYEDBZMRGODDBG-UHFFFAOYSA-N 0.000 description 3
- KLNRSJOIQHWLDS-UHFFFAOYSA-N 4-(2-nitrophenyl)chrysene Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)C1=CC=CC=2C=CC3=C4C=CC=CC4=CC=C3C1=2 KLNRSJOIQHWLDS-UHFFFAOYSA-N 0.000 description 3
- RAZNBUYJDZEDNT-UHFFFAOYSA-N 4-bromo-22-azahexacyclo[12.11.0.02,11.05,10.015,23.016,21]pentacosa-1(14),2(11),3,5,7,9,12,15(23),16,18,20,24-dodecaene Chemical compound BrC=1C2=CC=CC=C2C=2C=CC3=C(C=CC=4NC=5C=CC=CC=5C3=4)C=2C=1 RAZNBUYJDZEDNT-UHFFFAOYSA-N 0.000 description 3
- 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 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 238000004506 ultrasonic cleaning Methods 0.000 description 3
- VQPNISXVFCDEFK-UHFFFAOYSA-N 1,4-dichlorochrysene Chemical compound ClC1=CC=C(C=2C3=CC=C4C=CC=CC4=C3C=CC1=2)Cl VQPNISXVFCDEFK-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 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
- 230000004888 barrier function Effects 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002950 monocyclic 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
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- NEMREOMRDJWSPU-UHFFFAOYSA-N (5-bromo-2-nitrophenyl)boronic acid Chemical compound OB(O)C1=CC(Br)=CC=C1[N+]([O-])=O NEMREOMRDJWSPU-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-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
- AELZBFQHFNMGJS-UHFFFAOYSA-N 1h-1-benzosilole Chemical compound C1=CC=C2[SiH2]C=CC2=C1 AELZBFQHFNMGJS-UHFFFAOYSA-N 0.000 description 1
- HTFNVAVTYILUCF-UHFFFAOYSA-N 2-[2-ethoxy-4-[4-(4-methylpiperazin-1-yl)piperidine-1-carbonyl]anilino]-5-methyl-11-methylsulfonylpyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound CCOc1cc(ccc1Nc1ncc2N(C)C(=O)c3ccccc3N(c2n1)S(C)(=O)=O)C(=O)N1CCC(CC1)N1CCN(C)CC1 HTFNVAVTYILUCF-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- GEYDEIDXDHSFPX-UHFFFAOYSA-N 2-chlorochrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=C(Cl)C=C4C=CC3=C21 GEYDEIDXDHSFPX-UHFFFAOYSA-N 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
- GLWRUZZCCWGEMX-UHFFFAOYSA-N 3-chlorochrysene Chemical compound C1=CC=CC2=CC=C(C=3C(=CC=C(C=3)Cl)C=C3)C3=C21 GLWRUZZCCWGEMX-UHFFFAOYSA-N 0.000 description 1
- VCXHFEFJCBXXHL-UHFFFAOYSA-N 4-chlorochrysene Chemical compound ClC1=CC=CC=2C=CC3=C4C=CC=CC4=CC=C3C1=2 VCXHFEFJCBXXHL-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
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
- 229910006404 SnO 2 Inorganic materials 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
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-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
- 239000010405 anode material Substances 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- KBHLMJRLOXVWIC-UHFFFAOYSA-N c(cc1)cc2c1[nH]c1c2ccc2ccc(c3ccccc3cc3)c3c12 Chemical compound c(cc1)cc2c1[nH]c1c2ccc2ccc(c3ccccc3cc3)c3c12 KBHLMJRLOXVWIC-UHFFFAOYSA-N 0.000 description 1
- PIACUICEWWJGJP-UHFFFAOYSA-N c(cc1)ccc1-[n]1c2c3[nH]c4ccccc4c3c3c4ccc(cccc5)c5c4ccc3c2c2ccccc12 Chemical compound c(cc1)ccc1-[n]1c2c3[nH]c4ccccc4c3c3c4ccc(cccc5)c5c4ccc3c2c2ccccc12 PIACUICEWWJGJP-UHFFFAOYSA-N 0.000 description 1
- PFUYYCXQMVAZIW-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2cc(-[n](c3c4cccc3)c3c4c(c4c(cc5)c(cccc6)c6cc4)c5c(c4ccccc44)c3[n]4-c3ccccc3)ccc2)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c1nc(-c2cc(-[n](c3c4cccc3)c3c4c(c4c(cc5)c(cccc6)c6cc4)c5c(c4ccccc44)c3[n]4-c3ccccc3)ccc2)nc(-c2ccccc2)n1 PFUYYCXQMVAZIW-UHFFFAOYSA-N 0.000 description 1
- KCBQSZJOBDRAQC-UHFFFAOYSA-N c(cc1)ccc1N(c1ccccc1)[n]1c(c2c(cc3)ccc4c2ccc2ccccc42)c3c2ccccc12 Chemical compound c(cc1)ccc1N(c1ccccc1)[n]1c(c2c(cc3)ccc4c2ccc2ccccc42)c3c2ccccc12 KCBQSZJOBDRAQC-UHFFFAOYSA-N 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
- 125000005578 chrysene group Chemical group 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005684 electric field 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
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 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
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 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
- 238000010345 tape casting Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl 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
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- 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
-
- 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]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Definitions
- the present invention relates to a novel organic compound and an organic electroluminescent device comprising the same.
- the organic electroluminescent device when a voltage is applied between two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine.
- the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.
- hole injection materials hole transport materials.
- NPB, BCP, Alq 3 and the like are known as hole blocking materials and electron transporting materials, and metals containing Ir such as anthracene derivatives, Firpic, Ir (ppy) 3 , (acac) Ir (btp) 2, etc.
- Complex compounds, CBP, and the like are known.
- An object of the present invention is to provide a novel organic compound that can increase the hole injection / transport ability, the light emitting ability and the like of the organic electroluminescent device.
- Another object of the present invention is to provide an organic electroluminescent device comprising the novel organic compound.
- the present invention to achieve the above object provides a compound represented by the following formula (1).
- At least one of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 may be bonded to each other to form a condensed ring represented by Formula 2 below;
- the dotted line is the part where condensation takes place
- X 1 is selected from the group consisting of O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ),
- R 1 to R 4 and R 5 to R 16 which do not form a condensed ring are the same or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, alkyl group of C 1 to C 40 , C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to the 60 heteroaryl group, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 3 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C of 40 groups of an alkyl boron, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 ary
- Ar 1 to Ar 5 are each independently a C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atoms 3 to 40 Heterocycloalkyl group, C 6 ⁇ C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ C 40 Alkyl silyl group, C 6 ⁇ C 60 aryl silyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 Aryl phosphine oxide group and C 6 ⁇ C 60 It is selected from the group consisting of arylamine group,
- Alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alky group, C 3 ⁇ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 hetero cycloalkyl, heteroaryl of C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 aryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ aryloxy C 60, C 3
- the present invention also provides an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer
- an organic electroluminescent device comprising a compound represented by the formula (1).
- alkyl refers to a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
- Alkenyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
- Alkynyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
- aryl means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms combined with a single ring or two or more rings.
- a form in which two or more rings are attached to each other (pendant) or condensed may also be included. Examples thereof include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
- Heteroaryl in the present invention means a monovalent substituent derived from monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se.
- a form in which two or more rings are pendant or condensed with each other may be included, and may also include a form in which the two or more rings are condensed with an aryl group.
- 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl, Polycyclic rings such as purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2- Pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
- aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 6 to 60 carbon atoms. Examples thereof include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
- alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means alkyl having 1 to 40 carbon atoms, and includes a linear, branched or cyclic structure. can do. Examples thereof include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
- arylamine means an amine substituted with aryl having 6 to 60 carbon atoms.
- Cycloalkyl in the present invention means monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms. Examples thereof include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
- 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 carbon in the ring, preferably 1 to 3 carbons is N, O, S or Se Is substituted with a hetero atom such as Examples thereof include, but are not limited to, morpholine, piperazine, and the like.
- alkylsilyl is silyl substituted with alkyl having 1 to 40 carbon atoms
- arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms.
- the condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
- the compound represented by Formula 1 of the present invention may be used as a material of the organic material layer of the organic electroluminescent device because of its excellent thermal stability and luminescence properties.
- an organic EL device having excellent light emission performance, driving voltage, and lifespan characteristics may be manufactured, and further, a full color display panel having improved performance and lifespan may also be used. It can manufacture.
- the present invention provides a novel chrysene compound having a linear structure by condensing an aromatic ring or a hetero aromatic ring at positions 1, 2, 3, and 4 of the following chrysene.
- the organic compound of the present invention is represented by the formula (1).
- Chrysene-based compounds have low HOMO energy levels and wide energy band gaps, making them chemically stable. When a substituent having various functions is introduced into such a chrysene-based compound, it may have a wide energy band gap and chemical properties.
- the compound represented by Formula 1 of the present invention in which the aromatic ring or the heteroaromatic ring is condensed at positions 1, 2, 3, and 4 of the chrysene is selected from 5 and 6, or 11 and 12 Compared to the chrysene compound in which the aromatic ring or the hetero aromatic ring is condensed at the position, the intermolecular stacking is better and the electrons are smoothly moved.
- the compound represented by the general formula (1) of the present invention is introduced into the aryl group (phenyl, biphenyl, terphenyl, triphenylene, naphthalene, anthracene), or a substituent having excellent hole injection / transport properties such as arylamine group is introduced
- the transport is smooth, and the substituent which is excellent in electron injection / transportability such as heteroaryl group is introduced to facilitate the injection and transport of electrons.
- the compound represented by Chemical Formula 1 of the present invention has a low HOMO energy level due to the chrysene structure, which is effective in preventing exciton and hole movement.
- an organic material layer specifically, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole barrier layer, a light emitting layer
- An organic electroluminescent device having excellent efficiency, low driving voltage, and long life can be provided.
- R 1 and R 2 , R 2 and R 3 , R 3 and R 4 may be bonded to each other to form a condensed ring represented by Formula 2 above.
- one of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 are bonded to each other to include one or more of N, O, S and Si, a condensation indene, a condensation indole, a condensation benzothiophene, Condensed benzofuran, condensed benzosilol and the like can be formed.
- Such a compound represented by the formula (1) of the present invention may be embodied in any one of the compounds represented by the following formula 1-A to 1-J.
- X 1 and R 1 to R 16 are the same as defined in Formula 1, wherein a plurality of R 13 are the same or different from each other, a plurality of R 14 are the same or different from each other, a plurality of R 15 is the same or different from each other Different and a plurality of R 16 s are the same or different from each other.
- X 1 is selected from the group consisting of O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ), and Si (Ar 4 ) (Ar 5 ) there is, it is preferred that the of the N (Ar 1).
- the compound represented by the formula (1) of the present invention is a R 1 to R 4 which does not form a condensed ring, at least one of R 5 to R 16 and Ar 1 to Ar 5 is an alkyl group of C 1 ⁇ C 40 , C 6 ⁇ it is a C 60 aryl group, the number of nuclear atoms of 5 to 60 in which a heteroaryl group and a C 6 ⁇ selected from the group consisting of an arylamine C 60 are preferred.
- At least one of R 1 to R 4 and R 5 to R 16 and Ar 1 to Ar 5 (particularly, at least one of Ar 1 to Ar 5 ) which do not form a condensed ring is a substituent represented by the following general formula (3): Is preferably.
- L 1 is selected from the group consisting of a heteroarylene of a single bond, a C 6 ⁇ C 18 arylene group and a nuclear atoms of 5 to 18 (preferably a single bond, phenylene group, biphenylene group, carbazole group),
- Y 1 to Y 5 are the same as or different from each other, and each independently N or C (R 21 ), wherein when C (R 21 ) is plural, R 21 is the same as or different from each other,
- R 21 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 aryl group , nuclear atoms of 5 to 40 heteroaryl group, C 6 ⁇ aryloxy C 40 C 1 ⁇ C 40 alkyloxy group of, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group of , C 6 ⁇ C 40 arylamine group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 40 aryl boron group, C 6 ⁇ C 40 aryl phosphine group , C 6 ⁇ C 40 aryl phosphine oxide group and C 6 ⁇ C 40 arylsilyl group selected from the group consisting of, or combine with
- the arylphosphine group, the arylphosphine oxide group and the arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alky Neyl group, C 6 ⁇ C 40 aryl group, C 5 ⁇ C 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 arylamine group, an aryl
- Substituents represented by Formula 3 may be embodied by any one of the substituents represented by the following A-1 to A-16.
- L 1 and R 21 are the same as defined in Formula 2,
- R 22 is deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 ⁇ C 40 aryl group, an aryloxy group of nuclear atoms of 5 to 40 heteroaryl group, C 6 ⁇ C 40-C 1 ⁇ alkyloxy group of C 40 of, C 6 C 40 -C arylamine group, C 1 -C 40 alkylsilyl group, C 1 -C 40 alkyl boron group, C 6 -C 40 aryl boron group, C 6 -C 40 arylphosphine group, C 6 ⁇ C 40 aryl phosphine oxide group, and a C 6 ⁇ C 40 selected from an aryl silyl group the group consisting of or of, by combining together
- n is an integer of 0-4.
- the arylphosphine group, the arylphosphine oxide group and the arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alky Neyl group, C 6 ⁇ C 40 aryl group, C 5 ⁇ C 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 arylamine group, an aryl
- At least one of R 1 to R 4 and R 5 to R 16 and Ar 1 to Ar 5 that do not form a condensed ring is a substituent represented by the following general formula (4): It is preferable.
- L 2 is selected from the group consisting of a heteroarylene of a single bond, a C 6 ⁇ C 18 arylene group and a nuclear atoms of 5 to 18 (preferably a single bond, phenylene group, biphenylene group, carbazole group),
- R 23 and R 24 are each independently a C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 40 aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, and a C 6 ⁇ selected from the group consisting of an aryl amine of the C 60 Or combine with each other to form a condensed ring,
- the alkyl group, aryl group, heteroaryl group and arylamine group of R 23 and R 24 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C 6 ⁇ C 40, alkyloxy group of C 1 ⁇ C 40 of, C 6 ⁇ C 40 aryl amine group, C 3 ⁇ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group 1 ⁇ C 40 alkyl silyl, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C 40 aryl boron group, C 6 ⁇ C 40 aryl phosphine group, C 6 ⁇ C 40
- Specific examples of the compound represented by Formula 1 of the present invention include, but are not limited to, the following compounds (R1 to R180).
- the present invention provides an organic electroluminescent device comprising a compound represented by the formula (1).
- the organic electroluminescent device of the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers is It includes a compound represented by the formula (1).
- the compound may be used alone, or two or more may be used in combination.
- the one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a hole barrier layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer is a compound represented by Formula 1 It may include.
- the organic material layer including the compound of Formula 1 is preferably a light emitting layer, an electron transport layer, a hole transport layer.
- the emission layer may include a host, wherein the host may include a compound represented by Formula 1 or a compound other than the compound represented by Formula 1 as a host.
- the structure of the organic EL device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked.
- an electron injection layer may be further stacked on the electron transport layer.
- An insulating layer or an adhesive layer may be further inserted at an interface between the anode, the cathode, and the organic material layer.
- Such an organic electroluminescent device of the present invention may be manufactured by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1. .
- the organic material layer may be formed by a vacuum deposition method or a solution coating method.
- the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
- the substrate used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, but a silicon wafer, quartz, glass plate, metal plate, plastic film, or the like can be used.
- examples of the anode 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), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SnO 2: 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.
- metals such as vanadium, chromium, copper, zinc and gold or alloys thereof.
- Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SnO 2: Sb
- Conductive polymers such as polythiophene, poly (3-methylthiophene), poly
- the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
- the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound A8 (1.4g, 3.4mmol, 82% yield).
- the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound A10 (1.6g, 4.0mmol, 79% yield).
- the compound synthesized in the synthesis example was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured according to the following procedure.
- a glass substrate coated with ITO Indium tin oxide having a thickness of 1500 ⁇ was ultrasonically washed with distilled water. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.
- ITO Indium tin oxide
- UV OZONE cleaner Power sonic 405, Hwasin Tech
- M-MTDATA 60 nm) / TCTA (80 nm) / R1, R26, R51, R76, R101, R126, R151, R166, R171, R176 each compound + 10% Ir ( ppy) 3 (30 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) was laminated in order to prepare a green organic EL device.
- a green organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound R1 as a light emitting host material when forming the light emitting layer.
- Example 1 Sample Host Drive voltage (V) EL peak (nm) Current efficiency (cd / A)
- Example 1 R1 6.2 515 41.4
- Example 2 R26 6.1 514 40.3
- Example 3 R51 6.4 513 40.7
- Example 4 R76 6.8 514 41.3
- Example 5 R101 6.4 515 40.1
- Example 6 R126 6.5 515 42.7
- Example 7 R151 6.4 514 41.9
- Example 8 R166 6.3 515 40.2
- Example 9 R171 6.9 514 41.2
- Example 10 R176 6.6 515 40.9 Comparative Example 1 CBP 7.1 517 37.0
- a red organic electroluminescent device was manufactured according to the following procedure.
- a glass substrate coated with ITO Indium tin oxide having a thickness of 1500 ⁇ was ultrasonically washed with distilled water. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.
- ITO Indium tin oxide
- UV OZONE cleaner Power sonic 405, Hwasin Tech
- M-MTDATA 60 nm) / TCTA (80 nm) / R6, R31, R56, R81, R106, R131 each compound + 10% (piq) 2 Ir (acac) (30nm) on the prepared ITO transparent substrate (electrode) ) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) were laminated in order to prepare a red organic EL device.
- a red organic electroluminescent device was manufactured in the same manner as in Example 11, except that CBP was used instead of the compound R6 as a light emitting host material when forming the emission layer.
- Example 11 Sample Host Drive voltage (V) EL peak (nm) Current efficiency (cd / A)
- Example 11 R6 4.4 621 10.8
- Example 12 R31 4.3 621 11.5
- Example 13 R56 4.1 620 11.3
- Example 14 R81 3.8 621 11.9
- Example 15 R106 4.4 621 11.0
- Example 16 R131 4.0 621 12.8 Comparative Example 2 CBP 5.5 622 9,1
- the compound synthesized in the synthesis example was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured according to the following procedure.
- a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 ⁇ was ultrasonically washed with distilled water. After washing with distilled water, ultrasonic washing with a solvent such as isopropyl alcohol, acetone, methanol, and drying was carried out, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and the substrate was cleaned for 5 minutes using UV. The substrate was then transferred to a vacuum depositor.
- ITO Indium tin oxide
- M-MTDATA 60nm) / R11, R36, R61, R66, R86, R111, R136 Compound (80nm) / 95% DS-H522 (Doosan Electronics Co., Ltd.) + 5 on the prepared ITO transparent substrate (electrode)
- a green organic electroluminescent device was manufactured by stacking DS-501 (Doosan Electronics Co., Ltd.) (30 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) in this order.
- a green organic electroluminescent device was manufactured in the same manner as in Example 17, except that NPB was used instead of the compound R11 used as the hole transport layer to form the hole transport layer.
- the compound synthesized in the synthesis example was subjected to high purity sublimation purification by a conventionally known method, and then a blue organic EL device was manufactured according to the following procedure.
- a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 ⁇ was ultrasonically washed with distilled water. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then the substrate using UV for 5 minutes The substrate was cleaned and transferred to a vacuum evaporator.
- ITO Indium tin oxide
- DS-205 Doosan Electronics Co., Ltd. (80 nm) / NPB (15 nm) / R1, R26, R51, R76, R101, R126, R151, R166, R171, R176
- Each compound (15nm) / ADN + 5% DS-405 Doosan Electronics Co., Ltd.) (300nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm)
- An organic electroluminescent device was manufactured.
- a blue organic electroluminescent device was manufactured in the same manner as in Example 23, except that Compound R1, which was used as the emission auxiliary layer material, was not used.
- a blue organic electroluminescent device was manufactured in the same manner as in Example 23, except that Compound A was used instead of Compound R1 used as the emission auxiliary layer material.
- NPB and BCP used in Examples 23 to 32 and Comparative Examples 4 and 5 are as described above, and the structures of ADN and Compound A are as follows.
- Example 23 R1 4.3 9.3 458
- Example 24 R26 4.0 8.4 458
- Example 25 R51 4.1 8.3 458
- Example 26 R76 4.1 8.9 458
- Example 27 R101 4,2 8.8 458
- Example 28 R126 3.9 7.5 459
- Example 29 R151 3.5 6.7 459
- Example 30 R166 3.0 6.5 458
- Example 31 R171 3.3 6.9 458
- Example 32 R176 3.2 6.3 458 Comparative Example 4 - 4.3 4.5 458 Comparative Example 5 A 5.5 5.3 458
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The present invention relates to an organic compound, and an organic electroluminescent device having improved characteristics, such as luminous efficiency, driving voltage, and lifespan, by containing the organic compound in one or more organic material layers.
Description
본 발명은 신규한 유기 화합물 및 이를 포함한 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic compound and an organic electroluminescent device comprising the same.
유기 전계 발광 소자는 두 전극 사이에 전압을 걸어 주면 양극에서는 정공이, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 상기 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 organic material layer from the anode and electrons from the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. The material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.
현재까지 정공 주입 물질, 정공 수송 물질. 정공 차단 물질, 전자 수송 물질로는 NPB, BCP, Alq3 등이 알려져 있고, 발광 물질로는 안트라센 유도체, Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물, CBP등이 알려져 있다.To date hole injection materials, hole transport materials. NPB, BCP, Alq 3 and the like are known as hole blocking materials and electron transporting materials, and metals containing Ir such as anthracene derivatives, Firpic, Ir (ppy) 3 , (acac) Ir (btp) 2, etc. Complex compounds, CBP, and the like are known.
그러나 이러한 물질들은 유리전이온도가 낮고 열적 안정성이 좋지 않아, 유기 전계 발광 소자의 수명 측면에서 만족할 만한 수준이 되지 못하고 있다.However, these materials have low glass transition temperatures and poor thermal stability, and thus are not satisfactory in terms of lifespan of the organic EL device.
본 발명은 유기 전계 발광 소자의 정공 주입/수송능, 발광능 등을 높일 수 있는 신규 유기 화합물을 제공하는 것을 목적으로 한다.An object of the present invention is to provide a novel organic compound that can increase the hole injection / transport ability, the light emitting ability and the like of the organic electroluminescent device.
또한 본 발명은 상기 신규 유기 화합물을 포함하는 유기 전계 발광 소자를 제공하는 것도 목적으로 한다.Another object of the present invention is to provide an organic electroluminescent device comprising the novel organic compound.
상기한 목적을 달성하기 위하여 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다.The present invention to achieve the above object provides a compound represented by the following formula (1).
[화학식 1][Formula 1]
상기 화학식 1에서,In Chemical Formula 1,
R1과 R2, R2와 R3, R3와 R4 중 하나 이상은 서로 결합하여 하기 화학식 2로 표시되는 축합 고리를 형성하고,At least one of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 may be bonded to each other to form a condensed ring represented by Formula 2 below;
[화학식 2][Formula 2]
상기 화학식 2에서,In Chemical Formula 2,
점선은 축합이 이루어지는 부분이고,The dotted line is the part where condensation takes place
X1은 O, S, Se, N(Ar1), C(Ar2)(Ar3) 및 Si(Ar4)(Ar5)로 이루어진 군에서 선택되고,X 1 is selected from the group consisting of O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ),
축합 고리를 형성하지 않는 R1 내지 R4와, R5 내지 R16은 서로 동일 또는 상이하며, 각각 독립적으로 수소, 중수소, 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, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고,R 1 to R 4 and R 5 to R 16 which do not form a condensed ring are the same or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, alkyl group of C 1 to C 40 , C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to the 60 heteroaryl group, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 3 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C of 40 groups of an alkyl boron, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ from the group consisting of an aryl amine of the C 60 Selected,
Ar1 내지 Ar5는 각각 독립적으로 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, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고,Ar 1 to Ar 5 are each independently a C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, nuclear atoms 3 to 40 Heterocycloalkyl group, C 6 ~ C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 Alkyl silyl group, C 6 ~ C 60 aryl silyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 Aryl phosphine oxide group and C 6 ~ C 60 It is selected from the group consisting of arylamine group,
상기 R1 내지 R16 및 Ar1 내지 Ar5의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로, 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, C3~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 치환 또는 비치환되며, 이때, 복수의 치환기로 치환될 경우 복수의 치환기는 서로 동일 또는 상이하다.The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group of R 1 to R 16 and Ar 1 to Ar 5 , Alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alky group, C 3 ~ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 hetero cycloalkyl, heteroaryl of C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 aryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ aryloxy C 60, C 3 ~ C 40 alkyl silyl group, an aryl boronic of C 6 ~ C aryl silyl group of 60, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 60 group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ substituted by one or more substituents selected from the group consisting of C 60 aryl amine, or unsubstituted of He said, at this time, when a plurality of substituents to be substituted by a plurality of the substituents are the same or different from each other.
또한, 본 발명은 (i) 양극, (ii) 음극, 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.The present invention also provides an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer One provides an organic electroluminescent device comprising a compound represented by the formula (1).
본 발명에서 알킬은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, alkyl refers to a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
본 발명에서 알케닐(alkenyl)은 탄소-탄소 이중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등을 들 수 있으나, 이에 한정되지는 않는다.Alkenyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
본 발명에서 알키닐(alkynyl)은 탄소-탄소 삼중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등을 들 수 있으나, 이에 한정되지는 않는다.Alkynyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
본 발명에서 아릴은 단독 고리 또는 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. 이의 예로는 페닐, 나프틸, 페난트릴, 안트릴 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, aryl means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms combined with a single ring or two or more rings. In addition, a form in which two or more rings are attached to each other (pendant) or condensed may also be included. Examples thereof include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
본 발명에서 헤테로아릴은 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. 이의 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.Heteroaryl in the present invention means a monovalent substituent derived from monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with 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 may also include a form in which the two or more rings are condensed with an aryl group. Examples thereof include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl, Polycyclic rings such as purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2- Pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
본 발명에서 아릴옥시는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 6 내지 60의 아릴을 의미한다. 이의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 6 to 60 carbon atoms. Examples thereof include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
본 발명에서 알킬옥시는 R'O-로 표시되는 1가의 치환기로, 상기 R'는 탄소수 1 내지 40의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함할 수 있다. 이의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means alkyl having 1 to 40 carbon atoms, and includes a linear, branched or cyclic structure. can do. Examples thereof include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
본 발명에서 아릴아민은 탄소수 6 내지 60의 아릴로 치환된 아민을 의미한다.In the present invention, arylamine means an amine substituted with aryl having 6 to 60 carbon atoms.
본 발명에서 시클로알킬은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 노르보닐(norbornyl), 아다만틴(adamantine) 등을 들 수 있으나, 이에 한정되지는 않는다.Cycloalkyl in the present invention means monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms. Examples thereof include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
본 발명에서 헤테로시클로알킬은 핵원자수 3 내지 40의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로 원자로 치환된다. 이의 예로는 모르폴린, 피페라진 등을 들 수 있으나, 이에 한정되지는 않는다.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 carbon in the ring, preferably 1 to 3 carbons is N, O, S or Se Is substituted with a hetero atom such as Examples thereof include, but are not limited to, morpholine, piperazine, and the like.
본 발명에서 알킬실릴은 탄소수 1 내지 40의 알킬로 치환된 실릴이고, 아릴실릴은 탄소수 6 내지 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 축합고리는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.In the present invention, the condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
본 발명의 화학식 1로 표시되는 화합물은 열적 안정성 및 발광 특성이 우수하기 때문에 유기 전계 발광 소자의 유기물층의 재료로 사용될 수 있다. 특히, 본 발명의 화학식 1로 표시되는 화합물을 발광층의 인광 호스트로 사용할 경우 발광 성능, 구동전압 및 수명 특성이 우수한 유기 전계 발광 소자를 제조할 수 있고, 나아가 성능 및 수명이 향상된 풀 칼라 디스플레이 패널도 제조할 수 있다.The compound represented by Formula 1 of the present invention may be used as a material of the organic material layer of the organic electroluminescent device because of its excellent thermal stability and luminescence properties. In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host of the light emitting layer, an organic EL device having excellent light emission performance, driving voltage, and lifespan characteristics may be manufactured, and further, a full color display panel having improved performance and lifespan may also be used. It can manufacture.
이하, 본 발명을 설명한다.Hereinafter, the present invention will be described.
1. 유기 화합물1. Organic Compound
본 발명은 하기 크라이센의 1, 2, 3, 4 번 위치에 방향족 고리 또는 헤테로 방향족 고리가 축합되어 linear한 구조를 가지는 신규 크라이센계 화합물을 제공한다. 구체적으로, 본 발명의 유기 화합물은 상기 화학식 1로 표시된다.The present invention provides a novel chrysene compound having a linear structure by condensing an aromatic ring or a hetero aromatic ring at positions 1, 2, 3, and 4 of the following chrysene. Specifically, the organic compound of the present invention is represented by the formula (1).
크라이센계 화합물은 낮은 HOMO 에너지 레벨과 넓은 에너지 밴드 갭을 가져 화학적으로 구조가 안정하다. 이러한 크라이센계 화합물에 다양한 기능을 가지는 치환기가 도입될 경우 넓은 에너지 밴드갭 및 화학적 특성을 가질 수 있다.Chrysene-based compounds have low HOMO energy levels and wide energy band gaps, making them chemically stable. When a substituent having various functions is introduced into such a chrysene-based compound, it may have a wide energy band gap and chemical properties.
구체적으로, 크라이센의 1, 2, 3, 4 번 위치에 방향족 고리 또는 헤테로 방향족 고리가 축합된 본 발명의 화학식 1로 표시되는 화합물은 크라이센의 5번과 6번, 또는 11번과 12번의 위치에 방향족 고리, 또는 헤테로 방향족 고리가 축합된 크라이센계 화합물에 비해 분자간 stacking이 잘 일어나 전자의 이동이 원활하다.Specifically, the compound represented by Formula 1 of the present invention in which the aromatic ring or the heteroaromatic ring is condensed at positions 1, 2, 3, and 4 of the chrysene is selected from 5 and 6, or 11 and 12 Compared to the chrysene compound in which the aromatic ring or the hetero aromatic ring is condensed at the position, the intermolecular stacking is better and the electrons are smoothly moved.
또한 본 발명의 화학식 1로 표시되는 화합물은 아릴기(페닐, 비페닐, 터페닐, 트리페닐렌, 나프탈렌, 안트라센), 또는 아릴아민기와 같은 정공 주입/수송성이 우수한 치환기가 도입되어 정공의 주입 및 수송이 원활하며, 헤테로아릴기와 같은 전자 주입/수송성이 우수한 치환기가 도입되어 전자의 주입 및 수송도 원활하다. 또 본 발명의 화학식 1로 표시되는 화합물은 크라이센 구조로 인해 낮은 HOMO 에너지 레벨을 가져 exciton과 정공의 이동을 저지하는데도 효율적이다.In addition, the compound represented by the general formula (1) of the present invention is introduced into the aryl group (phenyl, biphenyl, terphenyl, triphenylene, naphthalene, anthracene), or a substituent having excellent hole injection / transport properties such as arylamine group is introduced The transport is smooth, and the substituent which is excellent in electron injection / transportability such as heteroaryl group is introduced to facilitate the injection and transport of electrons. In addition, the compound represented by Chemical Formula 1 of the present invention has a low HOMO energy level due to the chrysene structure, which is effective in preventing exciton and hole movement.
따라서 본 발명의 화학식 1로 표시되는 화합물을 유기 전계 발광 소자의 유기물층(구체적으로, 정공 주입층, 정공 수송층, 전자 주입층, 전자 수송층, 정공 장벽층, 발광층)을 형성하는 재료로 사용할 경우, 발광 효율이 우수하고, 구동 전압이 낮으며, 장수명을 가지는 유기 전계 발광 소자를 제공할 수 있다.Therefore, when the compound represented by Formula 1 of the present invention is used as a material for forming an organic material layer (specifically, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole barrier layer, a light emitting layer) of the organic electroluminescent device, An organic electroluminescent device having excellent efficiency, low driving voltage, and long life can be provided.
이러한 본 발명의 화학식 1로 표시되는 화합물은, R1과 R2, R2와 R3, R3와 R4 중 하나 이상이 서로 결합하여 상기 화학식 2로 표시되는 축합 고리를 형성할 수 있다. 구체적으로, R1과 R2, R2와 R3, R3와 R4 중 하나는 서로 결합하여 N, O, S 및 Si 중 하나 이상을 포함하는 축합 인덴, 축합 인돌, 축합 벤조싸이오펜, 축합 벤조퓨란, 축합 벤조실롤 등을 형성할 수 있다.In the compound represented by Formula 1 of the present invention, one or more of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 may be bonded to each other to form a condensed ring represented by Formula 2 above. Specifically, one of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 are bonded to each other to include one or more of N, O, S and Si, a condensation indene, a condensation indole, a condensation benzothiophene, Condensed benzofuran, condensed benzosilol and the like can be formed.
이와 같은 본 발명의 화학식 1로 표시되는 화합물은 하기 화학식 1-A 내지 1-J로 표시되는 화합물 중 어느 하나로 구체화될 수 있다. Such a compound represented by the formula (1) of the present invention may be embodied in any one of the compounds represented by the following formula 1-A to 1-J.
상기 화학식 1-A 내지 1-J에서,In Chemical Formulas 1-A to 1-J,
X1 및 R1 내지 R16는 상기 화학식 1에서 정의한 바와 동일하며, 이때, 복수의 R13은 서로 동일 또는 상이하고, 복수의 R14는 서로 동일 또는 상이하며, 복수의 R15는 서로 동일 또는 상이하고, 복수의 R16은 서로 동일 또는 상이하다.X 1 and R 1 to R 16 are the same as defined in Formula 1, wherein a plurality of R 13 are the same or different from each other, a plurality of R 14 are the same or different from each other, a plurality of R 15 is the same or different from each other Different and a plurality of R 16 s are the same or different from each other.
상기 화학식 1-A 내지 1-J에서, X1은 O, S, Se, N(Ar1), C(Ar2)(Ar3) 및 Si(Ar4)(Ar5)로 이루어진 군에서 선택되는데, 그 중 N(Ar1)인 것이 바람직하다.In Formulas 1-A to 1-J, X 1 is selected from the group consisting of O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ), and Si (Ar 4 ) (Ar 5 ) there is, it is preferred that the of the N (Ar 1).
한편 본 발명의 화학식 1로 표시되는 화합물은 축합 고리를 형성하지 않는 R1 내지 R4와, R5 내지 R16 및 Ar1 내지 Ar5 중 적어도 하나가 C1~C40의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되는 것이 바람직하다.On the other hand, the compound represented by the formula (1) of the present invention is a R 1 to R 4 which does not form a condensed ring, at least one of R 5 to R 16 and Ar 1 to Ar 5 is an alkyl group of C 1 ~ C 40 , C 6 ~ it is a C 60 aryl group, the number of nuclear atoms of 5 to 60 in which a heteroaryl group and a C 6 ~ selected from the group consisting of an arylamine C 60 are preferred.
구체적으로, 축합 고리를 형성하지 않는 R1 내지 R4와, R5 내지 R16 및 Ar1 내지 Ar5 중 적어도 하나(특히, Ar1 내지 Ar5 중 적어도 하나)는 하기 화학식 3으로 표시되는 치환체인 것이 바람직하다.Specifically, at least one of R 1 to R 4 and R 5 to R 16 and Ar 1 to Ar 5 (particularly, at least one of Ar 1 to Ar 5 ) which do not form a condensed ring is a substituent represented by the following general formula (3): Is preferably.
[화학식 3][Formula 3]
상기 화학식 3에서,In Chemical Formula 3,
*는 상기 화학식 1에 결합되는 부분을 의미하고,* Means a moiety bonded to Formula 1,
L1은 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18의 헤테로아릴렌기로 이루어진 군에서 선택되고(바람직하게는 단일결합, 페닐렌기, 비페닐렌기, 카바졸렌기),L 1 is selected from the group consisting of a heteroarylene of a single bond, a C 6 ~ C 18 arylene group and a nuclear atoms of 5 to 18 (preferably a single bond, phenylene group, biphenylene group, carbazole group),
Y1 내지 Y5는 서로 동일, 또는 상이하고, 각각 독립적으로 N 또는 C(R21)이며, 이때, C(R21)이 복수인 경우, R21은 서로 동일, 또는 상이하며,Y 1 to Y 5 are the same as or different from each other, and each independently N or C (R 21 ), wherein when C (R 21 ) is plural, R 21 is the same as or different from each other,
상기 R21은 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기 C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C40의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기(예컨대, L, 또는 인접하는 다른 R21)와 결합하여 축합 고리를 형성한다.R 21 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group , nuclear atoms of 5 to 40 heteroaryl group, C 6 ~ aryloxy C 40 C 1 ~ C 40 alkyloxy group of, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group of , C 6 ~ C 40 arylamine group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 40 aryl boron group, C 6 ~ C 40 aryl phosphine group , C 6 ~ C 40 aryl phosphine oxide group and C 6 ~ C 40 arylsilyl group selected from the group consisting of, or combine with an adjacent group (for example, L, or adjacent other R 21 ) to form a condensed ring do.
상기 R21의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되고, 이때 복수의 치환기로 치환될 경우, 복수의 치환기는 서로 동일 또는 상이하다.An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group of R 21 , a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, the arylphosphine oxide group and the arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alky Neyl group, C 6 ~ C 40 aryl group, C 5 ~ C 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamine group, an aryl boronic of C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 40 group, C 6 ~ C 40 aryl substituted with a phosphine group, C 6 ~ C 40 aryl phosphine oxide groups and one or more substituents selected from the group consisting of aryl silyl C 6 ~ C 40 of It is unsubstituted, wherein if substituted with a plurality of substituents, the plurality of substituents are the same or different from each other.
이러한 화학식 3으로 표시되는 치환체는 하기 A-1 내지 A-16으로 표시되는 치환체 중 어느 하나로 구체화될 수 있다.Substituents represented by Formula 3 may be embodied by any one of the substituents represented by the following A-1 to A-16.
상기 A-1 내지 A-16에서,In the above A-1 to A-16,
L1 및 R21은 상기 화학식 2에서 정의한 바와 같고,L 1 and R 21 are the same as defined in Formula 2,
R22는 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기 C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기(예컨대, L1, R21, 또는 다른 R22)와 결합하여 축합 고리를 형성하며,R 22 is deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 ~ C 40 aryl group, an aryloxy group of nuclear atoms of 5 to 40 heteroaryl group, C 6 ~ C 40-C 1 ~ alkyloxy group of C 40 of, C 6 C 40 -C arylamine group, C 1 -C 40 alkylsilyl group, C 1 -C 40 alkyl boron group, C 6 -C 40 aryl boron group, C 6 -C 40 arylphosphine group, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ C 40 selected from an aryl silyl group the group consisting of or of, by combining together with the adjacent group (e. g., L 1, R 21, or other R 22) to form a condensed ring ,
n은 0 내지 4의 정수이다.n is an integer of 0-4.
상기 R22의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되고, 이때, 복수의 치환기로 치환될 경우, 복수의 치환기는 서로 동일 또는 상이하다.An alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group of R 22 , The arylphosphine group, the arylphosphine oxide group and the arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alky Neyl group, C 6 ~ C 40 aryl group, C 5 ~ C 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamine group, an aryl boronic of C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 40 group, C 6 ~ C 40 aryl substituted with a phosphine group, C 6 ~ C 40 aryl phosphine oxide groups and one or more substituents selected from the group consisting of aryl silyl C 6 ~ C 40 of Is unsubstituted, In this case, if substituted with a plurality of substituents, the plurality of substituents are the same or different from each other.
또한, 축합 고리를 형성하지 않는 R1 내지 R4와, R5 내지 R16 및 Ar1 내지 Ar5 중 적어도 하나(특히, Ar1 내지 Ar5 중 적어도 하나)는 하기 화학식 4로 표시되는 치환체인 것이 바람직하다.In addition, at least one of R 1 to R 4 and R 5 to R 16 and Ar 1 to Ar 5 that do not form a condensed ring (in particular, at least one of Ar 1 to Ar 5 ) is a substituent represented by the following general formula (4): It is preferable.
[화학식 4][Formula 4]
상기 화학식 4에서,In Chemical Formula 4,
*는 상기 화학식 1에 결합되는 부분을 의미하고,* Means a moiety bonded to Formula 1,
L2은 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18의 헤테로아릴렌기로 이루어진 군에서 선택되고(바람직하게 단일결합, 페닐렌기, 비페닐렌기, 카바졸렌기),L 2 is selected from the group consisting of a heteroarylene of a single bond, a C 6 ~ C 18 arylene group and a nuclear atoms of 5 to 18 (preferably a single bond, phenylene group, biphenylene group, carbazole group),
R23 및 R24는 각각 독립적으로 C1~C40의 알킬기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 서로 결합하여 축합 고리를 형성하며,R 23 and R 24 are each independently a C 1 ~ C 40 alkyl group, C 6 ~ C 40 aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, and a C 6 ~ selected from the group consisting of an aryl amine of the C 60 Or combine with each other to form a condensed ring,
상기 R23 및 R24의 알킬기, 아릴기, 헤테로아릴기 및 아릴아민기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되고, 이때 복수의 치환기로 치환될 경우, 복수의 치환기는 서로 동일 또는 상이하다.The alkyl group, aryl group, heteroaryl group and arylamine group of R 23 and R 24 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C 6 ~ C 40, alkyloxy group of C 1 ~ C 40 of, C 6 ~ C 40 aryl amine group, C 3 ~ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group 1 ~ C 40 alkyl silyl, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 40 aryl boron group, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ C 40 aryl silyl group substituted or by one substituent at least one selected from the group consisting of When unsubstituted and substituted with a plurality of substituents, the plurality of substituents are the same or different from each other.
본 발명의 화학식 1로 표시되는 화합물의 구체적인 예로는 하기 화합물들(R1 내지 R180)을 들 수 있으나, 이에 한정되는 것은 아니다.Specific examples of the compound represented by Formula 1 of the present invention include, but are not limited to, the following compounds (R1 to R180).
2. 유기 2. Organic
전계Electric field
발광 소자 Light emitting element
본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.The present invention provides an organic electroluminescent device comprising a compound represented by the formula (1).
구체적으로, 본 발명의 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.Specifically, the organic electroluminescent device of the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers is It includes a compound represented by the formula (1). In this case, the compound may be used alone, or two or more may be used in combination.
상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 정공 장벽층, 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, 전자 수송층, 정공 수송층인 것이 바람직하다. 상기 발광층은 호스트를 포함할 수 있는데, 이때 호스트로서 상기 화학식 1로 표시되는 화합물, 또는 상기 화학식 1로 표시되는 화합물 이외의 다른 화합물을 호스트로 포함할 수 있다.The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a hole barrier layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer is a compound represented by Formula 1 It may include. Specifically, the organic material layer including the compound of Formula 1 is preferably a light emitting layer, an electron transport layer, a hole transport layer. The emission layer may include a host, wherein the host may include a compound represented by Formula 1 or a compound other than the compound represented by Formula 1 as a host.
이러한 본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 기판, 양극, 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자 수송층 및 음극이 순차적으로 적층된 구조일 수 있다. 이때, 상기 전자 수송층 위에는 전자 주입층이 추가로 적층될 수 있다. 상기 양극 및 음극과 유기물층의 계면에는 절연층 또는 접착층이 추가로 삽입될 수 있다.The structure of the organic EL device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. In this case, an electron injection layer may be further stacked on the electron transport layer. An insulating layer or an adhesive layer may be further inserted at an interface between the anode, the cathode, and the organic material layer.
이러한 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.Such an organic electroluminescent device of the present invention may be manufactured by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1. .
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 제조 시 사용되는 기판은 특별히 한정되지 않으나, 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 등을 사용할 수 있다.The substrate used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, but a silicon wafer, quartz, glass plate, metal plate, plastic film, or the like can be used.
또, 양극 물질로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 또는 폴리아닐린과 같은 전도성 고분자; 및 카본블랙 등을 들 수 있으나, 이에 한정되지는 않는다.In addition, examples of the anode 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), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SnO 2: 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.
또, 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.The negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
이하 본 발명을 실시예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐, 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail with reference to Examples. However, the following examples are merely to illustrate the invention, the present invention is not limited by the following examples.
[[
준비예Preparation
1] A1의 합성 1] Synthesis of A1
<단계 1> 1-(2-<Step 1> 1- (2-
nitrophenylnitrophenyl
))
chrysene의chrysene
합성 synthesis
질소 기류 하에서 1-chlorochrysene 3.7g (10.8mmol), 2-nitrophenylboronic acid 1.8g (10.8mmol), Pd(PPh3)4
0.6g (5 mol%), potassium carbonate 4.5g (32.3mmol) 및 80ml/40ml/40ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.1-chlorochrysene 3.7g (10.8mmol), 2-nitrophenylboronic acid 1.8g (10.8mmol), Pd (PPh 3 ) 4 under nitrogen stream 0.6g (5 mol%), potassium carbonate 4.5g (32.3mmol) and 80ml / 40ml / 40ml of Toluene / H 2 O / Ethanol were added thereto and stirred at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 1-(2-nitrophenyl)chrysene (3.1g, 8,8mmol, 수율 82%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound 1- (2-nitrophenyl) chrysene (3.1g, 8,8mmol, 82% yield).
GC-Mass (이론치: 349.38g/mol, 측정치: 349g/mol)GC-Mass (Theoretical value: 349.38 g / mol, Measured value: 349 g / mol)
1H-NMR: δ 7.66(t, 1H), 7.71(s, 2H), 7.83~7.94(m, 7H), 8.12(d, 2H), 8.88~8.92(m, 3H) 1 H-NMR: δ 7.66 (t, 1H), 7.71 (s, 2H), 7.83 to 7.74 (m, 7H), 8.12 (d, 2H), 8.88 to 8.92 (m, 3H)
<단계 2> A1의 합성<Step 2> Synthesis of A1
질소 기류 하에서 1-(2-nitrophenyl)chrysene 3.1g (8.8 mmol), triphenylphosphine 5.8g (22.0 mmol), 1,2-dichlorobenzene 30 ml를 넣은 후 12시간 동안 교반하였다. 반응 종료 후 1,2-dichlorobenzene를 제거하고 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A1 (2.1g, 6.5mmol, 수율 74%)을 얻었다.Under nitrogen stream, 1- (2-nitrophenyl) chrysene 3.1g (8.8 mmol), triphenylphosphine 5.8g (22.0 mmol), and 30 ml of 1,2-dichlorobenzene were added thereto, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound A1 (2.1g, 6.5mmol, 74% yield).
GC-Mass (이론치: 317.38g/mol, 측정치: 317g/mol)GC-Mass (Theoretical value: 317.38 g / mol, Measured value: 317 g / mol)
1H-NMR: δ 7.28(t, 1H), 7.49(t, 1H), 7.64(d, 1H), 7.71(s, 2H), 7.83~7.88(m, 4H), 8.12(d, 2H), 8.88~8.92(m, 3H), 10.01(s, 1H) 1 H-NMR: δ 7.28 (t, 1H), 7.49 (t, 1H), 7.64 (d, 1H), 7.71 (s, 2H), 7.83-7.88 (m, 4H), 8.12 (d, 2H), 8.88-8.92 (m, 3H), 10.01 (s, 1H)
[준비예 2] A2, A3의 합성Preparation Example 2 Synthesis of A2, A3
<단계 1> 2-(2-nitrophenyl)chrysene의 합성<Step 1> Synthesis of 2- (2-nitrophenyl) chrysene
질소 기류 하에서 2-chlorochrysene 3.7g, (10.8mmol), 2-nitrophenylboronic acid 1.8g (10.8mmol), Pd(PPh3)4
0.6g (5 mol%), potassium carbonate 4.5g (32.3 mmol) 및 80ml/40ml/40ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.2-chlorochrysene under nitrogen stream, 3.7 g, (10.8 mmol), 2-nitrophenylboronic acid 1.8 g (10.8 mmol), Pd (PPh 3 ) 4 0.6g (5 mol%), potassium carbonate 4.5g (32.3 mmol) and 80ml / 40ml / 40ml of Toluene / H 2 O / Ethanol were added thereto, and the mixture was stirred at 110 ° C for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 2-(2-nitrophenyl)chrysene (3.2g, 9.0mmol, 수율 84%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound 2- (2-nitrophenyl) chrysene (3.2g, 9.0mmol, 84% yield).
GC-Mass (이론치: 349.38g/mol, 측정치: 349g/mol)GC-Mass (Theoretical value: 349.38 g / mol, Measured value: 349 g / mol)
1H-NMR: δ 7.66(m, 1H), 7.71(s, 2H), 7.83~8.12(m, 8H), 8.33(s, 1H), 8.92~8.98(m, 3H) 1 H-NMR: δ 7.66 (m, 1H), 7.71 (s, 2H), 7.83-8.12 (m, 8H), 8.33 (s, 1H), 8.92-8.98 (m, 3H)
<단계 2> A2, A3의 합성<Step 2> Synthesis of A2, A3
질소 기류 하에서 2-(2-nitrophenyl)chrysene 3.2g (9.0mmol), triphenylphosphine 5.9g (22.6 mmol) 및 1,2-dichlorobenzene 30 ml를 넣은 후 12시간 동안 교반하였다. 반응 종료 후 1,2-dichlorobenzene를 제거하고 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A2 (0.9g, 3.0mmol, 수율 33%) 및 A3 (0.8g, 2.5mmol, 수율 28%)를 얻었다.Under nitrogen stream, 3.2 g (9.0 mmol) of 2- (2-nitrophenyl) chrysene, 5.9 g (22.6 mmol) of triphenylphosphine, and 30 ml of 1,2-dichlorobenzene were added thereto, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compounds A2 (0.9g, 3.0mmol, 33% yield) and A3 (0.8g, 2.5mmol, 28% yield).
A2: GC-Mass (이론치: 317.38g/mol, 측정치: 317g/mol)A2: GC-Mass (Theoretical value: 317.38 g / mol, Measured value: 317 g / mol)
1H-NMR: δ 7.28(t, 1H), 7.49(t, 1H), 7.64(d, 1H), 7.71(s, 2H), 7.83~7.88(m, 3H), 8.12(d, 3H), 8.91~8.92(m, 3H), 10.01(s, 1H) 1 H-NMR: δ 7.28 (t, 1H), 7.49 (t, 1H), 7.64 (d, 1H), 7.71 (s, 2H), 7.83-7.88 (m, 3H), 8.12 (d, 3H), 8.91-8.92 (m, 3H), 10.01 (s, 1H)
A3:GC-Mass (이론치: 317.38g/mol, 측정치: 317g/mol)A3: GC-Mass (Theoretical value: 317.38 g / mol, Measured value: 317 g / mol)
1H-NMR: δ 7.28(t, 1H), 7.49(t, 1H), 7.64(d, 1H), 7.71(s, 2H), 7.83~7.88(m, 4H), 8.12(d, 2H), 8.91~8.92(m, 3H), 10.01(s, 1H) 1 H-NMR: δ 7.28 (t, 1H), 7.49 (t, 1H), 7.64 (d, 1H), 7.71 (s, 2H), 7.83-7.88 (m, 4H), 8.12 (d, 2H), 8.91-8.92 (m, 3H), 10.01 (s, 1H)
[준비예 3] A4, A5의 합성Preparation Example 3 Synthesis of A4 and A5
<단계 1> 3-(2-nitrophenyl)chrysene의 합성<Step 1> Synthesis of 3- (2-nitrophenyl) chrysene
질소 기류 하에서 3-chlorochrysene 3.7g (10.8mmol), 2-nitrophenylboronic acid 1.8g (10.8mmol), Pd(PPh3)4
0.6g (5 mol%), potassium carbonate 4.5g (32.3 mmol) 및 80ml/40ml/40ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.3-chlorochrysene under nitrogen stream, 3.7 g (10.8 mmol), 2-nitrophenylboronic acid 1.8 g (10.8 mmol), Pd (PPh 3 ) 4 0.6g (5 mol%), potassium carbonate 4.5g (32.3 mmol) and 80ml / 40ml / 40ml of Toluene / H 2 O / Ethanol were added thereto, and the mixture was stirred at 110 ° C for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 3-(2-nitrophenyl)chrysene (3.2g, 9.0mmol, 수율 84%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound 3- (2-nitrophenyl) chrysene (3.2g, 9.0mmol, 84% yield).
GC-Mass (이론치: 349.38g/mol, 측정치: 349g/mol)GC-Mass (Theoretical value: 349.38 g / mol, Measured value: 349 g / mol)
1H-NMR: δ 7.66(t, 1H), 7.71(s, 2H), 7.83~8.17(m, 9H), 8.91(d, 2H), 9.13(s, 1H) 1 H-NMR: δ 7.66 (t, 1H), 7.71 (s, 2H), 7.83 to 8.17 (m, 9H), 8.91 (d, 2H), 9.13 (s, 1H)
<단계 2> A4, A5의 합성<Step 2> Synthesis of A4, A5
질소 기류 하에서 3-(2-nitrophenyl)chrysene 3.2g (9.0mmol), triphenylphosphine 5.9g (22.6 mmol) 및 1,2-dichlorobenzene 30 ml를 넣은 후 12시간 동안 교반하였다. 반응 종료 후 1,2-dichlorobenzene를 제거하고 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A4 (0.9g, 2.9mmol, 수율 31%) 및 A5 (0.8g, 2.6mmol, 수율 29%)를 얻었다.Under nitrogen stream, 3.2 g (9.0 mmol) of 3- (2-nitrophenyl) chrysene, 5.9 g (22.6 mmol) of triphenylphosphine, and 30 ml of 1,2-dichlorobenzene were added thereto, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compounds A4 (0.9g, 2.9mmol, 31% yield) and A5 (0.8g, 2.6mmol, 29% yield).
A4: GC-Mass (이론치: 317.38g/mol, 측정치: 317g/mol)A4: GC-Mass (Theoretical value: 317.38 g / mol, Measured value: 317 g / mol)
1H-NMR: δ 7.28(m, 1H), 7.49(m, 1H), 7.62(d, 1H), 7.72(s, 2H), 7.82~7.87(m, 4H), 8.10~8.12(m, 3H), 8.91(d, 2H), 10.0(s, 1H) 1 H-NMR: δ 7.28 (m, 1H), 7.49 (m, 1H), 7.62 (d, 1H), 7.72 (s, 2H), 7.82-7.87 (m, 4H), 8.10-8.12 (m, 3H ), 8.91 (d, 2H), 10.0 (s, 1H)
A5: GC-Mass (이론치: 317.38g/mol, 측정치: 317g/mol)A5: GC-Mass (Theoretical value: 317.38 g / mol, Measured value: 317 g / mol)
1H-NMR: δ 7.28(m, 1H), 7.49(m, 1H), 7.62(d, 1H), 7.72(s, 2H), 7.82~7.87(m, 3H), 8.10~8.12(m, 3H), 8.91(d, 3H), 10.0(s, 1H) 1 H-NMR: δ 7.28 (m, 1H), 7.49 (m, 1H), 7.62 (d, 1H), 7.72 (s, 2H), 7.82-7.87 (m, 3H), 8.10-8.12 (m, 3H) ), 8.91 (d, 3H), 10.0 (s, 1H)
[준비예 4] A6의 합성Preparation Example 4 Synthesis of A6
<단계 1> 4-(2-nitrophenyl)chrysene의 합성<Step 1> Synthesis of 4- (2-nitrophenyl) chrysene
질소 기류 하에서 4-chlorochrysene 3.7g, (10.8mmol), 2-nitrophenylboronic acid 1.8g (10.8mmol), Pd(PPh3)4
0.6g (5 mol%), potassium carbonate 4.5g (32.3 mmol) 및 80ml/40ml/40ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.4-chlorochrysene under nitrogen stream, 3.7 g, (10.8 mmol), 2-nitrophenylboronic acid 1.8 g (10.8 mmol), Pd (PPh 3 ) 4 0.6g (5 mol%), potassium carbonate 4.5g (32.3 mmol) and 80ml / 40ml / 40ml of Toluene / H 2 O / Ethanol were added thereto, and the mixture was stirred at 110 ° C for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 4-(2-nitrophenyl)chrysene (3.1g, 8.8mmol, 수율 82%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound 4- (2-nitrophenyl) chrysene (3.1g, 8.8mmol, 82% yield).
GC-Mass (이론치: 349.38g/mol, 측정치: 349g/mol)GC-Mass (Theoretical value: 349.38 g / mol, Measured value: 349 g / mol)
1H-NMR: δ 7.66(t, 1H), 7.71(s, 2H), 7.83~8.11(m, 10H), 8.91(d, 2H) 1 H-NMR: δ 7.66 (t, 1H), 7.71 (s, 2H), 7.83 to 8.11 (m, 10H), 8.91 (d, 2H)
<단계 2> A6의 합성<Step 2> Synthesis of A6
질소 기류 하에서 4-(2-nitrophenyl)chrysene 3.1g (8.8mmol), triphenylphosphine 5.8g (22.0mmol) 및 1,2-dichlorobenzene 30 ml를 넣은 후 12시간 동안 교반하였다. 반응 종료 후 1,2-dichlorobenzene를 제거하고 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A6 (2.1g, 6.7 mmol, 수율 76%)를 얻었다.Under nitrogen stream, 3.1 g (8.8 mmol) of 4- (2-nitrophenyl) chrysene, 5.8 g (22.0 mmol) of triphenylphosphine, and 30 ml of 1,2-dichlorobenzene were added thereto, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound A6 (2.1g, 6.7 mmol, 76% yield).
GC-Mass (이론치: 317.38g/mol, 측정치: 317g/mol)GC-Mass (Theoretical value: 317.38 g / mol, Measured value: 317 g / mol)
1H-NMR: δ 7.28(m, 1H), 7.49(m, 1H), 7.62(d, 1H), 7.72(s, 2H), 7.82~7.88(m, 4H), 8.10~8.11(m, 3H), 8.91(d, 2H), 10.0(s, 1H) 1 H-NMR: δ 7.28 (m, 1H), 7.49 (m, 1H), 7.62 (d, 1H), 7.72 (s, 2H), 7.82-7.88 (m, 4H), 8.10-8.11 (m, 3H ), 8.91 (d, 2H), 10.0 (s, 1H)
[준비예 5] A7의 합성Preparation Example 5 Synthesis of A7
<단계 1> 4-chloro-1-(2-nitrophenyl)chrysene의 합성<Step 1> Synthesis of 4-chloro-1- (2-nitrophenyl) chrysene
질소 기류 하에서 1,4-dichlorochrysene 3.2g (10.8mmol), 2-nitrophenylboronic acid 1.8g (10.8mmol), Pd(PPh3)4
0.6g (5 mol%), potassium carbonate 4.5g (32.3mmol) 및 80ml/40ml/40ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.1,4-dichlorochrysene 3.2g (10.8mmol), 2-nitrophenylboronic acid 1.8g (10.8mmol), Pd (PPh 3 ) 4 under nitrogen stream 0.6g (5 mol%), potassium carbonate 4.5g (32.3mmol) and 80ml / 40ml / 40ml of Toluene / H 2 O / Ethanol were added thereto and stirred at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 4-chloro-1-(2-nitrophenyl)chrysene (2.2g, 5.6mmol, 수율 52%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound 4-chloro-1- (2-nitrophenyl) chrysene (2.2g, 5.6mmol, 52% yield).
GC-Mass (이론치: 383.83g/mol, 측정치: 349g/mol)GC-Mass (Theoretical value: 383.83 g / mol, Measured value: 349 g / mol)
1H-NMR: δ 7.66(m, 1H), 7.71(s, 2H), 7.83~8.12(m, 9H), 8.92~8.98(m, 2H) 1 H-NMR: δ 7.66 (m, 1H), 7.71 (s, 2H), 7.83-8.12 (m, 9H), 8.92-8.98 (m, 2H)
<단계 2> 7-chloro-9H-phenanthro[1,2-c]carbazole의 합성<Step 2> Synthesis of 7-chloro-9H-phenanthro [1,2-c] carbazole
질소 기류 하에서 4-chloro-1-(2-nitrophenyl)chrysene 2.2g (5.6mmol), triphenylphosphine 3.7g (14.0mmol), 1,2-dichlorobenzene 20 ml를 넣은 후 12시간 동안 교반하였다. 반응 종료 후 1,2-dichlorobenzene를 제거하고 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 7-chloro-9H-phenanthro[1,2-c]carbazole (1.5g, 4.2mmol, 수율 75%)을 얻었다.Under nitrogen stream, 2.2 g (5.6 mmol) of 4-chloro-1- (2-nitrophenyl) chrysene, 3.7 g (14.0 mmol) of triphenylphosphine, and 20 ml of 1,2-dichlorobenzene were added thereto, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound 7-chloro-9H-phenanthro [1,2-c] carbazole (1.5g, 4.2mmol, 75% yield).
GC-Mass (이론치: 351.83g/mol, 측정치: 351g/mol)GC-Mass (Theoretical value: 351.83 g / mol, Measured value: 351 g / mol)
1H-NMR: δ 7.28(t, 1H), 7.49(t, 1H), 7.64(d, 1H), 7.71(s, 2H), 7.83~7.88(m, 4H), 8.12(d, 2H), 8.91~8.92(m, 2H), 10.01(s, 1H) 1 H-NMR: δ 7.28 (t, 1H), 7.49 (t, 1H), 7.64 (d, 1H), 7.71 (s, 2H), 7.83-7.88 (m, 4H), 8.12 (d, 2H), 8.91-8.92 (m, 2H), 10.01 (s, 1H)
<단계 3> 7-(2-nitrophenyl)-9H-phenanthro[1,2-c]carbazole의 합성Step 3 Synthesis of 7- (2-nitrophenyl) -9H-phenanthro [1,2-c] carbazole
질소 기류 하에서 7-chloro-9H-phenanthro[1,2-c]carbazole 1.5g, (4.2mmol), 2-nitrophenylboronic acid 0.7g (4.2 mmol), Pd(PPh3)4
0.2g (5 mol%), potassium carbonate 1.7g (12.3 mmol) 및 80ml/40ml/40ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.Under nitrogen stream, 7-chloro-9H-phenanthro [1,2-c] carbazole 1.5g, (4.2mmol), 2-nitrophenylboronic acid 0.7g (4.2 mmol), Pd (PPh 3 ) 4 0.2 g (5 mol%), 1.7 g (12.3 mmol) of potassium carbonate and 80 ml / 40 ml / 40 ml of Toluene / H 2 O / Ethanol were added thereto and stirred at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 7-(2-nitrophenyl)-9H-phenanthro[1,2-c]carbazole (1.5g, 3.4mmol, 수율 82%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound 7- (2-nitrophenyl) -9H-phenanthro [1,2-c] carbazole (1.5g, 3.4mmol, 82% yield).
GC-Mass (이론치: 438.83g/mol, 측정치: 438g/mol)GC-Mass (Theoretical value: 438.83 g / mol, Measured value: 438 g / mol)
1H-NMR: δ 7.28(t, 1H), 7.49(t, 1H), 7.64(m, 2H), 7.71(s, 2H), 7.83~8.10(m, 9H), 8.91~8.92(d, 2H), 10.01(s, 1H) 1 H-NMR: δ 7.28 (t, 1H), 7.49 (t, 1H), 7.64 (m, 2H), 7.71 (s, 2H), 7.83-8.10 (m, 9H), 8.91-8.82 (d, 2H) ), 10.01 (s, 1H)
<단계 4> 7-(2- nitrophenyl )-9-phenyl-9H- phenanthro[1,2-c]carbazole의 합성 <Step 4> 7- (2- nitrophenyl) -9 -phenyl-9H- phenanthro [1,2-c] carbazole sum of the castle
질소 기류 하에서 7-(2-nitrophenyl)-9H-phenanthro[1,2-c]carbazole 1.5g (3.4mmol), iodobenzene 2.1g (10.3mmol), Cu powder 0.2g (2.4mmol), K2CO3 1.0g (6.9mmol), nitrobenzene 10 ml을 혼합하고 200 ℃에서 12시간 동안 교반하였다.Under nitrogen stream, 7- (2-nitrophenyl) -9H-phenanthro [1,2-c] carbazole 1.5g (3.4mmol), iodobenzene 2.1g (10.3mmol), Cu powder 0.2g (2.4mmol), K 2 CO 3 1.0 g (6.9 mmol) and 10 ml of nitrobenzene were mixed and stirred at 200 ° C. for 12 hours.
반응 종결 후 nitrobenzene을 제거하고 메틸렌클로라이드로 유기층을 분리하여 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 7-(2-nitrophenyl)-9-phenyl-9H-phenanthro[1,2-c]carbazole (1.4g, 2.7 mmol, 수율 79%)을 얻었다.After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer and purified by column chromatography to give the title compound 7- (2-nitrophenyl) -9-phenyl-9H-phenanthro [1,2-c] carbazole (1.4g, 2.7 mmol, 79% yield). Got it.
GC-Mass (이론치: 514.57g/mol, 측정치: 514g/mol)GC-Mass (Theoretical value: 514.57g / mol, Measured value: 514g / mol)
1H-NMR: δ 7.24~7.32(m, 2H), 7.45~7.66(m, 6H), 7.71(s, 2H), 7.92~8.10(m, 9H), 8.51(d, 1H), 8.91~8.92(d, 2H) 1 H-NMR: δ 7.24 to 7.32 (m, 2H), 7.45 to 7.62 (m, 6H), 7.71 (s, 2H), 7.92 to 8.10 (m, 9H), 8.51 (d, 1H), 8.91 to 8.92 (d, 2H)
<단계 5> A7의 합성Step 5 Synthesis of A7
질소 기류 하에서 7-(2-nitrophenyl)-9-phenyl-9H-phenanthro[1,2-c]carbazole 1.4g (2.7mmol), triphenylphosphine 1.8g (6.8mmol) 및 1,2-dichlorobenzene 20 ml를 넣은 후 12시간 동안 교반하였다. 반응 종료 후 1,2-dichlorobenzene를 제거하고 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A7 (1.0g, 2.0mmol, 수율 75%)를 얻었다.7- (2-nitrophenyl) -9-phenyl-9H-phenanthro [1,2-c] carbazole 1.4g (2.7mmol), triphenylphosphine 1.8g (6.8mmol) and 20 ml of 1,2-dichlorobenzene under nitrogen stream After stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound A7 (1.0g, 2.0mmol, 75% yield).
GC-Mass (이론치: 482.57g/mol, 측정치: 482g/mol)GC-Mass (Theoretical value: 482.57 g / mol, Measured value: 482 g / mol)
1H-NMR: δ 7.24~7.32(m, 3H), 7.45~7.66(m, 7H), 7.71(s, 2H), 7.88~7.93(m, 4H), 8.11(d, 2H), 8.51(d, 1H), 8.91~8.92(d, 2H), 10.01(s, 1H) 1 H-NMR: δ 7.24 to 7.32 (m, 3H), 7.45 to 7.62 (m, 7H), 7.71 (s, 2H), 7.88 to 7.73 (m, 4H), 8.11 (d, 2H), 8.51 (d , 1H), 8.91-8.92 (d, 2H), 10.01 (s, 1H)
[준비예 6] A8의 합성Preparation Example 6 Synthesis of A8
<단계 1> 4-chloro-1-(2-nitrophenyl)chrysene의 합성<Step 1> Synthesis of 4-chloro-1- (2-nitrophenyl) chrysene
질소 기류 하에서 1,4-dichlorochrysene 3.2g (10.8mmol), 2-nitrophenylboronic acid 1.8g (10.8mmol), Pd(PPh3)4
0.6g (5 mol%), potassium carbonate 4.5g (32.3mmol) 및 80ml/40ml/40ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.1,4-dichlorochrysene 3.2g (10.8mmol), 2-nitrophenylboronic acid 1.8g (10.8mmol), Pd (PPh 3 ) 4 under nitrogen stream 0.6g (5 mol%), potassium carbonate 4.5g (32.3mmol) and 80ml / 40ml / 40ml of Toluene / H 2 O / Ethanol were added thereto and stirred at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 4-chloro-1-(2-nitrophenyl)chrysene (2.2g, 5.6mmol, 수율 52%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound 4-chloro-1- (2-nitrophenyl) chrysene (2.2g, 5.6mmol, 52% yield).
GC-Mass (이론치: 383.83g/mol, 측정치: 349g/mol)GC-Mass (Theoretical value: 383.83 g / mol, Measured value: 349 g / mol)
1H-NMR: δ 7.66(m, 1H), 7.71(s, 2H), 7.83~8.12(m, 9H), 8.92~8.98(m, 2H) 1 H-NMR: δ 7.66 (m, 1H), 7.71 (s, 2H), 7.83-8.12 (m, 9H), 8.92-8.98 (m, 2H)
<단계 2> 7-chloro-9H-phenanthro[1,2-c]carbazole의 합성<Step 2> Synthesis of 7-chloro-9H-phenanthro [1,2-c] carbazole
질소 기류 하에서 4-chloro-1-(2-nitrophenyl)chrysene 2.2g (5.6mmol), triphenylphosphine 3.7g (14.0mmol) 및 1,2-dichlorobenzene 20 ml를 넣은 후 12시간 동안 교반하였다. 반응 종료 후 1,2-dichlorobenzene를 제거하고 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 7-chloro-9H-phenanthro[1,2-c]carbazole (1.5g, 4.2mmol, 수율 75%)를 얻었다.Under nitrogen stream, 2.2 g (5.6 mmol) of 4-chloro-1- (2-nitrophenyl) chrysene, 3.7 g (14.0 mmol) of triphenylphosphine and 20 ml of 1,2-dichlorobenzene were added thereto, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound 7-chloro-9H-phenanthro [1,2-c] carbazole (1.5g, 4.2mmol, 75% yield).
GC-Mass (이론치: 351.83g/mol, 측정치: 351g/mol)GC-Mass (Theoretical value: 351.83 g / mol, Measured value: 351 g / mol)
1H-NMR: δ 7.28(t, 1H), 7.49(t, 1H), 7.64(d, 1H), 7.71(s, 2H), 7.83~7.88(m, 4H), 8.12(d, 2H), 8.91~8.92(m, 2H), 10.01(s, 1H) 1 H-NMR: δ 7.28 (t, 1H), 7.49 (t, 1H), 7.64 (d, 1H), 7.71 (s, 2H), 7.83-7.88 (m, 4H), 8.12 (d, 2H), 8.91-8.92 (m, 2H), 10.01 (s, 1H)
<단계 3> A8의 합성<Step 3> Synthesis of A8
질소 기류 하에서 7-chloro-9H-phenanthro[1,2-c]carbazole 1.5g (4.2mmol), phenylboronic acid 0.5g (4.2mmol), Pd(PPh3)4
0.2g (5mol%), potassium carbonate 1.7g (12.3mmol) 및 80ml/40ml/40ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.Under nitrogen stream, 7-chloro-9H-phenanthro [1,2-c] carbazole 1.5g (4.2mmol), phenylboronic acid 0.5g (4.2mmol), Pd (PPh 3 ) 4 0.2g (5mol%), 1.7g (12.3mmol) of potassium carbonate and 80ml / 40ml / 40ml of Toluene / H 2 O / Ethanol were added and stirred at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A8 (1.4g, 3.4mmol, 수율 82%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound A8 (1.4g, 3.4mmol, 82% yield).
GC-Mass (이론치: 438.83g/mol, 측정치: 438g/mol)GC-Mass (Theoretical value: 438.83 g / mol, Measured value: 438 g / mol)
1H-NMR: δ 7.24~7.32(m, 3H), 7.45~7.66(m, 7H), 7.71(s, 2H), 7.88~7.93(m, 4H), 8.11(d, 2H), 8.51(d, 1H), 8.91~8.92(d, 2H), 10.01(s, 1H) 1 H-NMR: δ 7.24 to 7.32 (m, 3H), 7.45 to 7.62 (m, 7H), 7.71 (s, 2H), 7.88 to 7.73 (m, 4H), 8.11 (d, 2H), 8.51 (d , 1H), 8.91-8.92 (d, 2H), 10.01 (s, 1H)
[준비예 7] A9의 합성Preparation Example 7 Synthesis of A9
<단계 1> 1-(5-bromo-2-nitrophenyl)chrysene의 합성<Step 1> Synthesis of 1- (5-bromo-2-nitrophenyl) chrysene
질소 기류 하에서 1-chlorochrysene 3.7g (10.8mmol), 5-bromo-2-nitrophenylboronic acid 2.6g (10.8mmol), Pd(PPh3)4
0.6g (5mol%), potassium carbonate 4.5g (32.3mmol) 및 80ml/40ml/40ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.3.7 g (10.8 mmol) of 1-chlorochrysene, 2.6 g (10.8 mmol) of 5-bromo-2-nitrophenylboronic acid, Pd (PPh 3 ) 4 under nitrogen stream 0.6g (5mol%), 4.5g (32.3mmol) of potassium carbonate and 80ml / 40ml / 40ml of Toluene / H 2 O / Ethanol were added thereto and stirred at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 1-(5-bromo-2-nitrophenyl)chrysene (3.4g, 8.6mmol, 수율 80%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound 1- (5-bromo-2-nitrophenyl) chrysene (3.4g, 8.6mmol, 80% yield).
GC-Mass (이론치: 428.28g/mol, 측정치: 328g/mol)GC-Mass (Theoretical value: 428.28 g / mol, Measured value: 328 g / mol)
1H-NMR: δ 7.71(s, 3H), 7.83~8.11(m, 7H), 8.20(d, 1H), 8.92~8.93(m, 3H) 1 H-NMR: δ 7.71 (s, 3H), 7.83 to 8.11 (m, 7H), 8.20 (d, 1H), 8.92 to 8.83 (m, 3H)
<단계 2> 12-bromo-9H-phenanthro[1,2-c]carbazole의 합성<Step 2> Synthesis of 12-bromo-9H-phenanthro [1,2-c] carbazole
질소 기류 하에서 1-(5-bromo-2-nitrophenyl)chrysene 3.7g (8.6mmol), triphenylphosphine 5.6g (21.5mmol) 및 1,2-dichlorobenzene 40 ml를 넣은 후 12시간 동안 교반하였다. 반응 종료 후 1,2-dichlorobenzene를 제거하고 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 12-bromo-9H-phenanthro[1,2-c]carbazole (2.6g, 6.5mmol, 수율 75%)을 얻었다.Under nitrogen stream, 3.7g (8.6mmol) of 1- (5-bromo-2-nitrophenyl) chrysene, 5.6g (21.5mmol) of triphenylphosphine and 40 ml of 1,2-dichlorobenzene were added and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound 12-bromo-9H-phenanthro [1,2-c] carbazole (2.6g, 6.5mmol, 75% yield).
GC-Mass (이론치: 396.28g/mol, 측정치: 396g/mol)GC-Mass (Theoretical value: 396.28 g / mol, Measured value: 396 g / mol)
1H-NMR: δ 7.40(d, 1H), 7.51(d, 1H), 7.71(s, 2H), 7.83~7.88(m, 4H), 7.79(s, 1H), 8.12(d, 1H), 8.92~8.93(m, 3H), 10.01(s, 1H) 1 H-NMR: δ 7.40 (d, 1H), 7.51 (d, 1H), 7.71 (s, 2H), 7.83-7.88 (m, 4H), 7.79 (s, 1H), 8.12 (d, 1H), 8.92-8.83 (m, 3H), 10.01 (s, 1H)
<단계 3> A9의 합성Step 3 Synthesis of A9
질소 기류 하에서 12-bromo-9H-phenanthro[1,2-c]carbazole 2.6g (6.5mmol), phenylboronic acid 0.8g (6.5mmol), Pd(PPh3)4
0.4g (5mol%), potassium carbonate 2.7g (19.4mmol) 및 80ml/40ml/40ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.12-bromo-9H-phenanthro [1,2-c] carbazole 2.6g (6.5mmol), phenylboronic acid 0.8g (6.5mmol), Pd (PPh 3 ) 4 under nitrogen stream 0.4g (5mol%), potassium carbonate 2.7g (19.4mmol) and 80ml / 40ml / 40ml of Toluene / H 2 O / Ethanol were added and stirred at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A9 (2.0g, 5.2mmol, 수율 80%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound A9 (2.0g, 5.2mmol, 80% yield).
GC-Mass (이론치: 393.48g/mol, 측정치: 393g/mol)GC-Mass (Theoretical value: 393.48 g / mol, Measured value: 393 g / mol)
1H-NMR: δ 7.40~7.51(m, 5H), 7.69(d, 1H), 7.71(s, 2H), 7.77~7.88(m, 6H), 8.12(d, 1H), 8.92~8.93(m, 3H), 10.01(s, 1H) 1 H-NMR: δ 7.40-7.51 (m, 5H), 7.69 (d, 1H), 7.71 (s, 2H), 7.77-7.88 (m, 6H), 8.12 (d, 1H), 8.92-8.83 (m , 3H), 10.01 (s, 1H)
[준비예 8] A10의 합성Preparation Example 8 Synthesis of A10
<단계 1> 1-(2-nitrophenyl)chrysene의 합성Step 1 Synthesis of 1- (2-nitrophenyl) chrysene
질소 기류 하에서 1-chlorochrysene 3.7g (10.8mmol), 2-nitrophenylboronic acid 1.8g (10.8mmol), Pd(PPh3)4
0.6g (5mol%), potassium carbonate 4.5g (32.3mmol) 및 80ml/40ml/40ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.1-chlorochrysene 3.7g (10.8mmol), 2-nitrophenylboronic acid 1.8g (10.8mmol), Pd (PPh 3 ) 4 under nitrogen stream 0.6g (5mol%), 4.5g (32.3mmol) of potassium carbonate and 80ml / 40ml / 40ml of Toluene / H 2 O / Ethanol were added thereto and stirred at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 1-(2-nitrophenyl)chrysene (3.1g, 8.8mmol, 수율 82%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound 1- (2-nitrophenyl) chrysene (3.1g, 8.8mmol, 82% yield).
GC-Mass (이론치: 349.38g/mol, 측정치: 349g/mol)GC-Mass (Theoretical value: 349.38 g / mol, Measured value: 349 g / mol)
1H-NMR: δ 7.67(m, 1H), 7.71(s, 2H), 7.87~8.10(m, 9H), 8.92~8.93(m, 3H) 1 H-NMR: δ 7.67 (m, 1H), 7.71 (s, 2H), 7.87-8.10 (m, 9H), 8.92-8.33 (m, 3H)
<단계 2> 9H-phenanthro[1,2-c]carbazole의 합성Step 2 Synthesis of 9H-phenanthro [1,2-c] carbazole
질소 기류 하에서 1-(2-nitrophenyl)chrysene 3.1g (8.8mmol), triphenylphosphine 5.8g (22.0mmol) 및 1,2-dichlorobenzene 30 ml를 넣은 후 12시간 동안 교반하였다. 반응 종료 후 1,2-dichlorobenzene를 제거하고 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 9H-phenanthro[1,2-c]carbazole (2.1g, 6.5 mmol, 수율 74%)을 얻었다.Under nitrogen stream, 1- (2-nitrophenyl) chrysene 3.1g (8.8mmol), triphenylphosphine 5.8g (22.0mmol) and 1,2 ml of 1,2-dichlorobenzene were added and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, the organic layer was separated using methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound 9H-phenanthro [1,2-c] carbazole (2.1g, 6.5 mmol, 74% yield).
GC-Mass (이론치: 317.28g/mol, 측정치: 317g/mol)GC-Mass (Theoretical value: 317.28 g / mol, Measured value: 317 g / mol)
1H-NMR: δ 7.30(m, 1H), 7.50(m, 1H), 7.64(d, 1H), 7.71(s, 2H), 7.82~7.88(m, 4H), 8.10(d, 2H), 8.92~8.93(m, 3H), 10.01(s, 1H) 1 H-NMR: δ 7.30 (m, 1H), 7.50 (m, 1H), 7.64 (d, 1H), 7.71 (s, 2H), 7.82-7.88 (m, 4H), 8.10 (d, 2H), 8.92-8.83 (m, 3H), 10.01 (s, 1H)
<단계 3> 5-bromo-9H-phenanthro[1,2-c]carbazole의 합성Step 3 Synthesis of 5-bromo-9H-phenanthro [1,2-c] carbazole
질소 기류 하에서 9H-phenanthro[1,2-c]carbazole 2.1g (6.5mmol), NBS(N-bromosuccinimide) 1.2g (6.5mmol), DMF 20 ml을 혼합하고 60 ℃에서 3시간 동안 교반하였다.Under nitrogen stream, 2.1 g (6.5 mmol) of 9H-phenanthro [1,2-c] carbazole, 1.2 g (6.5 mmol) of N-bromosuccinimide (NBS), and 20 ml of DMF were mixed and stirred at 60 ° C. for 3 hours.
반응 종결 후 DMF을 제거하고 메틸렌클로라이드로 유기층을 분리하여 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 5-bromo-9H-phenanthro[1,2-c]carbazole (2.0g, 5.0mmol, 수율 77%)을 얻었다.After completion of the reaction, DMF was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound 5-bromo-9H-phenanthro [1,2-c] carbazole (2.0g, 5.0mmol, 77% yield).
GC-Mass (이론치: 396.38g/mol, 측정치: 396g/mol)GC-Mass (Theoretical value: 396.38 g / mol, Measured value: 396 g / mol)
1H-NMR: δ 7.30(m, 1H), 7.50(m, 1H), 7.64(d, 1H), 7.71(s, 2H), 7.82~7.87(m, 3H), 8.10(d, 2H), 8.92~8.93(m, 2H), 9.08(s, 1H), 10.01(s, 1H) 1 H-NMR: δ 7.30 (m, 1H), 7.50 (m, 1H), 7.64 (d, 1H), 7.71 (s, 2H), 7.82-7.87 (m, 3H), 8.10 (d, 2H), 8.92-8.83 (m, 2H), 9.08 (s, 1H), 10.01 (s, 1H)
<단계 4> A10의 합성Step 4 Synthesis of A10
질소 기류 하에서 5-bromo-9H-phenanthro[1,2-c]carbazole 2.0g (5.0mmol), phenylboronic acid 0.6g (5.0mmol), Pd(PPh3)4
0.3g (5mol%), potassium carbonate 2.1g (15.1mmol) 및 80ml/40ml/40ml의 Toluene/H2O/Ethanol를 넣고 110℃에서 3시간 동안 교반하였다.5-bromo-9H-phenanthro [1,2-c] carbazole 2.0g (5.0mmol), phenylboronic acid 0.6g (5.0mmol), Pd (PPh 3 ) 4 under nitrogen stream 0.3g (5mol%), 2.1g (15.1mmol) of potassium carbonate and 80ml / 40ml / 40ml of Toluene / H 2 O / Ethanol were added and stirred at 110 ° C. for 3 hours.
반응 종료 후, 메틸렌클로라이드를 이용하여 유기층을 분리하고 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 A10 (1.6g, 4.0mmol, 수율 79%)을 얻었다.After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound A10 (1.6g, 4.0mmol, 79% yield).
GC-Mass (이론치: 393.48g/mol, 측정치: 393g/mol)GC-Mass (Theoretical value: 393.48 g / mol, Measured value: 393 g / mol)
1H-NMR: δ 7.29(m, 1H), 7.42~7.50(m, 4H), 7.64(d, 1H), 7.71(s, 2H), 7.79~7.87(m, 5H), 8.10(d, 2H), 8.92~8.93(m, 2H), 9.08(s, 1H), 10.01(s, 1H) 1 H-NMR: δ 7.29 (m, 1H), 7.42 to 7.50 (m, 4H), 7.64 (d, 1H), 7.71 (s, 2H), 7.79 to 7.87 (m, 5H), 8.10 (d, 2H ), 8.92-8.83 (m, 2H), 9.08 (s, 1H), 10.01 (s, 1H)
[합성예 1] R1의 합성Synthesis Example 1 Synthesis of R1
질소 기류 하에서 A1 2.1g (6.5mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 2.5g (7.2mmol), Pd2(dba)3
0.3g (5mol%), tri-tert-butylphosphine 0.1g (0.3mmol), Sodium tert-butoxide 1.9g (19.6mmol), 50ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.2.1 g (6.5 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine 2.5 g (7.2 mmol), Pd 2 (dba) 3 under nitrogen stream 0.3g (5mol%), tri- tert -butylphosphine 0.1g (0.3mmol), Sodium tert-butoxide 1.9g (19.6mmol), put in 50ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R1 (2.8g, 4.5mmol, 수율 69%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R1 (2.8g, 4.5mmol, 69% yield).
GC-Mass (이론치: 624.73g/mol, 측정치: 624g/mol)GC-Mass (Theoretical value: 624.73 g / mol, Measured value: 624 g / mol)
[합성예 2] R6의 합성Synthesis Example 2 Synthesis of R6
질소 기류 하에서 A1 2.1g (6.5mmol), 2-chloro-4-phenylquinazoline 1.7g (7.2mmol), Pd2(dba)3
0.3g (5mol%), tri-tert-butylphosphine 0.1g (0.3mmol), Sodium tert-butoxide 1.9g (19.6mmol) 및 50ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.2.1g (6.5mmol), 2-chloro-4-phenylquinazoline 1.7g (7.2mmol), Pd 2 (dba) 3 under nitrogen stream 0.3g (5mol%), tri- tert -butylphosphine 0.1g (0.3mmol), Sodium tert-butoxide 1.9g (19.6mmol) and placed in 50ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R6 (2.5g, 4.7mmol, 수율 72%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R6 (2.5g, 4.7mmol, 72% yield).
GC-Mass (이론치: 521.61g/mol, 측정치: 521g/mol)GC-Mass (Theoretical value: 521.61 g / mol, Measured value: 521 g / mol)
[합성예 3] R11의 합성Synthesis Example 3 Synthesis of R11
질소 기류 하에서 A1 2.1g (6.5mmol), N-chloro-N-phenylaniline 1.2g (7.2mmol), Pd2(dba)3 0.3g (5mol%), tri-tert-butylphosphine 0.1g (0.3mmol), Sodium tert-butoxide 1.9g (19.6mmol) 및 50ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.In a nitrogen stream A1 2.1g (6.5mmol), N- chloro-N-phenylaniline 1.2g (7.2mmol), Pd 2 (dba) 3 0.3g (5mol%), tri- tert -butylphosphine 0.1g (0.3mmol), 1.9 g (19.6 mmol) of sodium tert-butoxide and 50 ml of toluene were added thereto, and the mixture was stirred at 110 ° C. for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R11 (2.3g, 4.7mmol, 수율 72%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R11 (2.3g, 4.7mmol, 72% yield).
GC-Mass (이론치: 484.59g/mol, 측정치: 484g/mol)GC-Mass (Theoretical value: 484.59 g / mol, Measured value: 484 g / mol)
[합성예 4] R26의 합성Synthesis Example 4 Synthesis of R26
질소 기류 하에서 A2 1.0g (3.0mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 1.1g (7.2mmol), Pd2(dba)3
0.1g (5mol%), tri-tert-butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.9g (8.9mmol), 20ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.1.0 g (3.0 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine 1.1 g (7.2 mmol), Pd 2 (dba) 3 under nitrogen stream 0.1g (5mol%), tri- tert -butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.9g (8.9mmol), put in 20ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R26 (1.2g, 1.9mmol, 수율 65%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R26 (1.2g, 1.9mmol, 65% yield).
GC-Mass (이론치: 624.73g/mol, 측정치: 624g/mol)GC-Mass (Theoretical value: 624.73 g / mol, Measured value: 624 g / mol)
[합성예 5] R31의 합성Synthesis Example 5 Synthesis of R31
질소 기류 하에서 A2 1.0g (3.0mmol), 2-chloro-4-phenylquinazoline 1.1g (3.3mmol), Pd2(dba)3
0.1g (5mol%), tri-tert-butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.9g (8.9mmol) 및 30ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.1.0 g (3.0 mmol) A2, 2-chloro-4-phenylquinazoline 1.1 g (3.3 mmol), Pd 2 (dba) 3 under nitrogen stream 0.1g (5mol%), tri- tert -butylphosphine 0.1g (0.1mmol), placed in Toluene Sodium tert-butoxide 0.9g (8.9mmol) and 30ml was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R31 (1.0g, 1.9mmol, 수율 65%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R31 (1.0g, 1.9mmol, 65% yield).
GC-Mass (이론치: 521.61g/mol, 측정치: 521g/mol)GC-Mass (Theoretical value: 521.61 g / mol, Measured value: 521 g / mol)
[합성예 6] R36의 합성Synthesis Example 6 Synthesis of R36
질소 기류 하에서 A2 1.0g (3.0mmol), N-chloro-N-phenylaniline 0.7g (3.3mmol), Pd2(dba)3
0.1g (5mol%), tri-tert-butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.9g (8.9mmol), 및 30ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.A2 1.0 g (3.0 mmol), N-chloro-N-phenylaniline 0.7 g (3.3 mmol), Pd 2 (dba) 3 under nitrogen stream 0.1g (5mol%), tri- tert -butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.9g (8.9mmol), and put in a 30ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R36 (0.9g, 1.9mmol, 수율 64%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R36 (0.9g, 1.9mmol, 64% yield).
GC-Mass (이론치: 484.59g/mol, 측정치: 484g/mol)GC-Mass (Theoretical value: 484.59 g / mol, Measured value: 484 g / mol)
[합성예 7] R51의 합성Synthesis Example 7 Synthesis of R51
질소 기류 하에서 A3 0.8g (2,5mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 1.0g (2.8mmol), Pd2(dba)3
0.1g (5mol%), tri-tert-butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.7g (7.6mmol), 20ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.0.8 g (2,5 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine 1.0 g (2.8 mmol), Pd 2 (dba) 3 under nitrogen stream 0.1g (5mol%), tri- tert -butylphosphine 0.1g (0.1mmol), sodium tert-butoxide 0.7g (7.6mmol), 20ml of Toluene was added and stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R51 (1.1g, 1.7mmol, 수율 67%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R51 (1.1g, 1.7mmol, 67% yield).
GC-Mass (이론치: 624.73g/mol, 측정치: 624g/mol)GC-Mass (Theoretical value: 624.73 g / mol, Measured value: 624 g / mol)
[합성예 8] R56의 합성Synthesis Example 8 Synthesis of R56
질소 기류 하에서 A3 0.8g (2.5mmol), 2-chloro-4-phenylquinazoline 0.7g (2.8mmol), Pd2(dba)3
0.1g (5mol%), tri-tert-butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.7g (7.6mmol), 30ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.Under nitrogen stream, A3 0.8g (2.5mmol), 2-chloro-4-phenylquinazoline 0.7g (2.8mmol), Pd 2 (dba) 3 0.1g (5mol%), tri- tert -butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.7g (7.6mmol), put in 30ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R56 (0.9g, 1.7mmol, 수율 67%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R56 (0.9g, 1.7mmol, 67% yield).
GC-Mass (이론치: 521.61g/mol, 측정치: 521g/mol)GC-Mass (Theoretical value: 521.61 g / mol, Measured value: 521 g / mol)
[합성예 9] R61의 합성Synthesis Example 9 Synthesis of R61
질소 기류 하에서 A3 0.8g (2.5mmol), N-chloro-N-phenylaniline 0.6g (2.8mmol), Pd2(dba)3
0.1g (5mol%), tri-tert-butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.7g (7.6mmol), 30ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.Under nitrogen stream, A3 0.8g (2.5mmol), N-chloro-N-phenylaniline 0.6g (2.8mmol), Pd 2 (dba) 3 0.1g (5mol%), tri- tert -butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.7g (7.6mmol), put in 30ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R61 (0.8g, 1.6mmol, 수율 65%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R61 (0.8g, 1.6mmol, 65% yield).
GC-Mass (이론치: 484.59g/mol, 측정치: 484g/mol)GC-Mass (Theoretical value: 484.59 g / mol, Measured value: 484 g / mol)
[합성예 10] R76의 합성Synthesis Example 10 Synthesis of R76
질소 기류 하에서 A4 0.9g (2,8mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 1.1g (3.1mmol), Pd2(dba)3
0.1g (5mol%), tri-tert-butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.8g (8.4mmol) 및 20ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.0.9g (2,8mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine 1.1g (3.1mmol), Pd 2 (dba) 3 under nitrogen stream 0.1g (5mol%), tri- tert -butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.8g (8.4mmol) and placed in 20ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R76 (1.1g, 1.8mmol, 수율 63%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R76 (1.1g, 1.8mmol, 63% yield).
GC-Mass (이론치: 624.73g/mol, 측정치: 624g/mol)GC-Mass (Theoretical value: 624.73 g / mol, Measured value: 624 g / mol)
[합성예 11] R81의 합성Synthesis Example 11 Synthesis of R81
질소 기류 하에서 A4 0.9g (2.8mmol), 2-chloro-4-phenylquinazoline 0.7g (3.1mmol), Pd2(dba)3
0.1g (5mol%), tri-tert-butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.8g (8.4mmol) 및 30ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.0.9g (2.8mmol), 2-chloro-4-phenylquinazoline 0.7g (3.1mmol), Pd 2 (dba) 3 under nitrogen stream 0.1g (5mol%), tri- tert -butylphosphine 0.1g (0.1mmol), placed in Toluene Sodium tert-butoxide 0.8g (8.4mmol) and 30ml was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R81 (0.9g, 1.8mmol, 수율 63%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R81 (0.9g, 1.8mmol, 63% yield).
GC-Mass (이론치: 521.61g/mol, 측정치: 521g/mol)GC-Mass (Theoretical value: 521.61 g / mol, Measured value: 521 g / mol)
[합성예 12] R86의 합성Synthesis Example 12 Synthesis of R86
질소 기류 하에서 A4 0.9g (2.8mmol), N-chloro-N-phenylaniline 0.6g (3.1mmol), Pd2(dba)3
0.1g (5mol%), tri-tert-butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.8g (8.4mmol) 및 30ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.A4 0.9 g (2.8 mmol), N-chloro-N-phenylaniline 0.6 g (3.1 mmol), Pd 2 (dba) 3 under nitrogen stream 0.1g (5mol%), tri- tert -butylphosphine 0.1g (0.1mmol), placed in Toluene Sodium tert-butoxide 0.8g (8.4mmol) and 30ml was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R86 (0.9g, 1.8mmol, 수율 65%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R86 (0.9g, 1.8mmol, 65% yield).
GC-Mass (이론치: 484.59g/mol, 측정치: 484g/mol)GC-Mass (Theoretical value: 484.59 g / mol, Measured value: 484 g / mol)
[합성예 13] R101의 합성Synthesis Example 13 Synthesis of R101
질소 기류 하에서 A5 0.8g (2,6mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 1.0g (2.9mmol), Pd2(dba)3
0.1g (5mol%), tri-tert-butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.8g (7.9mmol) 및 20ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.0.85 (2,6mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine 1.0g (2.9mmol), Pd 2 (dba) 3 under nitrogen stream 0.1g (5mol%), tri- tert -butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.8g (7.9mmol) and placed in 20ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R101 (1.0g, 1.7mmol, 수율 64%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R101 (1.0g, 1.7mmol, 64% yield).
GC-Mass (이론치: 624.73g/mol, 측정치: 624g/mol)GC-Mass (Theoretical value: 624.73 g / mol, Measured value: 624 g / mol)
[합성예 14] R106의 합성Synthesis Example 14 Synthesis of R106
질소 기류 하에서 A5 0.8g (2.6mmol), 2-chloro-4-phenylquinazoline 0.7g (2.9mmol), Pd2(dba)3
0.1g (5mol%), tri-tert-butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.8g (7.9mmol) 및 30ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.0.85 (2.6mmol), 2-chloro-4-phenylquinazoline 0.7g (2.9mmol), Pd 2 (dba) 3 under nitrogen stream 0.1g (5mol%), tri- tert -butylphosphine 0.1g (0.1mmol), placed in Toluene Sodium tert-butoxide 0.8g (7.9mmol) and 30ml was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R106 (0.9g, 1.7mmol, 수율 66%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R106 (0.9g, 1.7mmol, 66% yield).
GC-Mass (이론치: 521.61g/mol, 측정치: 521g/mol)GC-Mass (Theoretical value: 521.61 g / mol, Measured value: 521 g / mol)
[합성예 15] R111의 합성Synthesis Example 15 Synthesis of R111
질소 기류 하에서 A5 0.9g (2.6mmol), N-chloro-N-phenylaniline 0.6g (2.9mmol), Pd2(dba)3
0.1g (5mol%), tri-tert-butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.8g (7.9mmol) 및 30ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.0.95 (2.6mmol), N-chloro-N-phenylaniline 0.6g (2.9mmol), Pd 2 (dba) 3 under nitrogen stream 0.1g (5mol%), tri- tert -butylphosphine 0.1g (0.1mmol), placed in Toluene Sodium tert-butoxide 0.8g (7.9mmol) and 30ml was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R111 (0.9g, 1.8mmol, 수율 68%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R111 (0.9g, 1.8mmol, 68% yield).
GC-Mass (이론치: 484.59g/mol, 측정치: 484g/mol)GC-Mass (Theoretical value: 484.59 g / mol, Measured value: 484 g / mol)
[합성예 16] R126의 합성Synthesis Example 16 Synthesis of R126
질소 기류 하에서 A5 2.1g (6.7mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 2.5g (7.4mmol), Pd2(dba)3
0.3g (5mol%), tri-tert-butylphosphine 0.1g (0.3mmol), Sodium tert-butoxide 1.9g (20.1mmol) 및 50ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.2.1 g (6.7 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine 2.5 g (7.4 mmol), Pd 2 (dba) 3 under nitrogen stream 0.3g (5mol%), tri- tert -butylphosphine 0.1g (0.3mmol), Sodium tert-butoxide 1.9g (20.1mmol) and placed in 50ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R126 (2.9g, 4.6mmol, 수율 69%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R126 (2.9g, 4.6mmol, 69% yield).
GC-Mass (이론치: 624.73g/mol, 측정치: 624g/mol)GC-Mass (Theoretical value: 624.73 g / mol, Measured value: 624 g / mol)
[합성예 17] R131의 합성Synthesis Example 17 Synthesis of R131
질소 기류 하에서 A6 2.1g (6.7mmol), 2-chloro-4-phenylquinazoline 1.8g (7.4mmol), Pd2(dba)3
0.3g (5mol%), tri-tert-butylphosphine 0.3g (0.3mmol), Sodium tert-butoxide 1.9g (20.1mmol) 및 50ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.A6 2.1g (6.7mmol), 2-chloro-4-phenylquinazoline 1.8g (7.4mmol), Pd 2 (dba) 3 under nitrogen stream 0.3g (5mol%), tri- tert -butylphosphine 0.3g (0.3mmol), Sodium tert-butoxide 1.9g (20.1mmol) and placed in 50ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R131 (2.4g, 4.6mmol, 수율 69%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R131 (2.4g, 4.6mmol, 69% yield).
GC-Mass (이론치: 521.61g/mol, 측정치: 521g/mol)GC-Mass (Theoretical value: 521.61 g / mol, Measured value: 521 g / mol)
[합성예 18] R136의 합성Synthesis Example 18 Synthesis of R136
질소 기류 하에서 A6 2.1g (6.7mmol), N-chloro-N-phenylaniline 1.5g (7.4mmol), Pd2(dba)3
0.3g (5mol%), tri-tert-butylphosphine 0.1g (0.3mmol), Sodium tert-butoxide 1.9g (20.1mmol) 및 50ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.A6 2.1g (6.7mmol), N-chloro-N-phenylaniline 1.5g (7.4mmol), Pd 2 (dba) 3 under nitrogen stream 0.3g (5mol%), tri- tert -butylphosphine 0.1g (0.3mmol), Sodium tert-butoxide 1.9g (20.1mmol) and placed in 50ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R136 (2.0g, 4.2mmol, 수율 63%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R136 (2.0g, 4.2mmol, 63% yield).
GC-Mass (이론치: 484.59g/mol, 측정치: 484g/mol)GC-Mass (Theoretical value: 484.59 g / mol, Measured value: 484 g / mol)
[합성예 19] R151의 합성Synthesis Example 19 Synthesis of R151
질소 기류 하에서 A7 1.0g (2.0mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 0.8g (2.2mmol), Pd2(dba)3
0.1g (5mol%), tri-tert-butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 0.6g (6.1mmol) 및 30ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.1.0 g (2.0 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine 0.8 g (2.2 mmol), Pd 2 (dba) 3 under nitrogen stream 0.1g (5mol%), tri- tert -butylphosphine 0.1g (0.1mmol), placed in Toluene Sodium tert-butoxide 0.6g (6.1mmol) and 30ml was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R151 (1.1g, 1.4mmol, 수율 71%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R151 (1.1g, 1.4mmol, 71% yield).
GC-Mass (이론치: 789.92g/mol, 측정치: 789g/mol)GC-Mass (Theoretical value: 789.92 g / mol, Measured value: 789 g / mol)
[합성예 20] R166의 합성Synthesis Example 20 Synthesis of R166
질소 기류 하에서 A8 1.4g (3.4mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 1.3g (3.8mmol), Pd2(dba)3
0.2g (5mol%), tri-tert-butylphosphine 0.1g (0.2mmol), Sodium tert-butoxide 1.0g (10.3mmol) 및 50ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.1.4g (3.4mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine 1.3g (3.8mmol), Pd 2 (dba) 3 A8 under nitrogen stream 0.2g (5mol%), tri- tert -butylphosphine 0.1g (0.2mmol), Sodium tert-butoxide 1.0g (10.3mmol) and placed in 50ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R166 (1.7g, 1.4mmol, 수율 69%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R166 (1.7g, 1.4mmol, 69% yield).
GC-Mass (이론치: 700.83g/mol, 측정치: 700g/mol)GC-Mass (Theoretical value: 700.83 g / mol, Measured value: 700 g / mol)
[합성예 21] R171의 합성Synthesis Example 21 Synthesis of R171
질소 기류 하에서 A9 2.0g (5.2mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 2.0g (5.7mmol), Pd2(dba)3
0.2g (5mol%), tri-tert-butylphosphine 0.1g (0.3mmol), Sodium tert-butoxide 1.5g (15.5mmol) 및 50ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.2.0 g (5.2 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine 2.0 g (5.7 mmol), Pd 2 (dba) 3 under nitrogen stream 0.2g (5mol%), tri- tert -butylphosphine 0.1g (0.3mmol), Sodium tert-butoxide 1.5g (15.5mmol) and placed in 50ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R171 (2.5g, 3.6mmol, 수율 69%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R171 (2.5g, 3.6mmol, 69% yield).
GC-Mass (이론치: 700.83g/mol, 측정치: 700g/mol)GC-Mass (Theoretical value: 700.83 g / mol, Measured value: 700 g / mol)
[합성예 22] R176의 합성Synthesis Example 22 Synthesis of R176
질소 기류 하에서 A10 1.6g (4.0mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 1.5g (4.4mmol), Pd2(dba)3
0.2g (5mol%), tri-tert-butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 1.1g (11.9mmol) 및 50ml의 Toluene을 넣고 110℃에서 4시간 동안 교반하였다.1.6 g (4.0 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine 1.5 g (4.4 mmol), Pd 2 (dba) 3 0.2g (5mol%), tri- tert -butylphosphine 0.1g (0.1mmol), Sodium tert-butoxide 1.1g (11.9mmol) and placed in 50ml Toluene was stirred at 110 ℃ for 4 hours.
반응이 종결된 후 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 컬럼크로마토그래피로 정제하여 목적 화합물인 R176 (1.8g, 2.6mmol, 수율 65%)을 얻었다.After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed using MgSO 4 . Purified by column chromatography to obtain the title compound R176 (1.8g, 2.6mmol, 65% yield).
GC-Mass (이론치: 700.83g/mol, 측정치: 700g/mol)GC-Mass (Theoretical value: 700.83 g / mol, Measured value: 700 g / mol)
[실시예 1 내지 10][Examples 1 to 10]
합성예에서 합성한 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 녹색 유기 전계 발광 소자를 제조하였다.The compound synthesized in the synthesis example was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수로 초음파 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 된 was ultrasonically washed with distilled water. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.
이렇게 준비된 ITO 투명 기판(전극) 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ R1, R26, R51, R76, R101, R126, R151, R166, R171, R176 각각의 화합물 + 10 % Ir(ppy)3 (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 녹색 유기 전계 발광 소자를 제조하였다.M-MTDATA (60 nm) / TCTA (80 nm) / R1, R26, R51, R76, R101, R126, R151, R166, R171, R176 each compound + 10% Ir ( ppy) 3 (30 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) was laminated in order to prepare a green organic EL device.
[비교예 1]Comparative Example 1
발광층 형성시 발광 호스트 물질로서 화합물 R1 대신 CBP를 사용하는 것을 제외하고는 실시예 1과 동일한 과정으로 녹색 유기 전계 발광 소자를 제조하였다.A green organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound R1 as a light emitting host material when forming the light emitting layer.
상기 실시예 1 내지 10 및 비교예 1에서 사용된 m-MTDATA, TCTA, Ir(ppy)3, BCP 및 CBP의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, Ir (ppy) 3 , BCP and CBP used in Examples 1 to 10 and Comparative Example 1 are as follows.
[평가예 1][Evaluation Example 1]
실시예 1 내지 10 및 비교예 1에서 제조한 각각의 녹색 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서 구동전압, 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 1에 나타내었다.For each of the green organic electroluminescent devices prepared in Examples 1 to 10 and Comparative Example 1, the driving voltage, current efficiency and emission peak were measured at a current density of 10 mA / cm 2, and the results are shown in Table 1 below.
| 샘플Sample | 호스트Host | 구동 전압(V)Drive voltage (V) | EL 피크(nm)EL peak (nm) | 전류효율(cd/A)Current efficiency (cd / A) |
| 실시예 1Example 1 | R1R1 | 6.26.2 | 515515 | 41.441.4 |
| 실시예 2Example 2 | R26R26 | 6.16.1 | 514514 | 40.340.3 |
| 실시예 3Example 3 | R51R51 | 6.46.4 | 513513 | 40.740.7 |
| 실시예 4Example 4 | R76R76 | 6.86.8 | 514514 | 41.341.3 |
| 실시예 5Example 5 | R101R101 | 6.46.4 | 515515 | 40.140.1 |
| 실시예 6Example 6 | R126R126 | 6.56.5 | 515515 | 42.742.7 |
| 실시예 7Example 7 | R151R151 | 6.46.4 | 514514 | 41.941.9 |
| 실시예 8Example 8 | R166R166 | 6.36.3 | 515515 | 40.240.2 |
| 실시예 9Example 9 | R171R171 | 6.96.9 | 514514 | 41.241.2 |
| 실시예 10Example 10 | R176R176 | 6.66.6 | 515515 | 40.940.9 |
| 비교예 1Comparative Example 1 | CBPCBP | 7.17.1 | 517517 | 37.037.0 |
상기 표 1에 나타낸 바와 같이, 본 발명의 화합물을 발광층에 적용한 경우(실시예 1 내지 10)가 종래 CBP를 적용한 경우(비교예 1)보다 전류효율 및 구동전압이 우수한 것을 알 수 있다.As shown in Table 1, it can be seen that when the compound of the present invention is applied to the light emitting layer (Examples 1 to 10), the current efficiency and the driving voltage are superior to those when applying the conventional CBP (Comparative Example 1).
[실시예 11 내지 16][Examples 11 to 16]
합성예에서 합성한 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 적색 유기 전계 발광 소자를 제조하였다.After the compound synthesized in the synthesis example was subjected to high purity sublimation purification by a commonly known method, a red organic electroluminescent device was manufactured according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수로 초음파 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 된 was ultrasonically washed with distilled water. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.
이렇게 준비된 ITO 투명 기판(전극) 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ R6, R31, R56, R81, R106, R131 각각의 화합물 + 10 % (piq)2Ir(acac) (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 적색 유기 전계 발광 소자를 제조하였다.M-MTDATA (60 nm) / TCTA (80 nm) / R6, R31, R56, R81, R106, R131 each compound + 10% (piq) 2 Ir (acac) (30nm) on the prepared ITO transparent substrate (electrode) ) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) were laminated in order to prepare a red organic EL device.
[비교예 2]Comparative Example 2
발광층 형성시 발광 호스트 물질로서 화합물 R6 대신 CBP를 사용하는 것을 제외하고는 상기 실시예 11과 동일한 과정으로 적색 유기 전계 발광 소자를 제조하였다.A red organic electroluminescent device was manufactured in the same manner as in Example 11, except that CBP was used instead of the compound R6 as a light emitting host material when forming the emission layer.
상기 실시예 11 내지 16 및 비교예 2에서 사용된 m-MTDATA, TCTA, BCP 및 CBP의 구조는 상기와 같고, (piq)2Ir(acac)의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, BCP and CBP used in Examples 11 to 16 and Comparative Example 2 are as described above, and the structure of (piq) 2 Ir (acac) is as follows.
[평가예 2][Evaluation Example 2]
실시예 11 내지 16 및 비교예 2에서 제조한 각각의 적색 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서 구동전압 및 전류효율을 측정하고, 그 결과를 하기 표 2에 나타내었다.For each of the red organic EL devices manufactured in Examples 11 to 16 and Comparative Example 2, the driving voltage and the current efficiency were measured at a current density of 10 mA / cm 2, and the results are shown in Table 2 below.
| 샘플Sample | 호스트Host | 구동 전압(V)Drive voltage (V) | EL 피크(nm)EL peak (nm) | 전류효율(cd/A)Current efficiency (cd / A) |
| 실시예 11Example 11 | R6R6 | 4.44.4 | 621621 | 10.810.8 |
| 실시예 12Example 12 | R31R31 | 4.34.3 | 621621 | 11.511.5 |
| 실시예 13Example 13 | R56R56 | 4.14.1 | 620620 | 11.311.3 |
| 실시예 14Example 14 | R81R81 | 3.83.8 | 621621 | 11.911.9 |
| 실시예 15Example 15 | R106R106 | 4.44.4 | 621621 | 11.011.0 |
| 실시예 16Example 16 | R131R131 | 4.04.0 | 621621 | 12.812.8 |
| 비교예 2Comparative Example 2 | CBPCBP | 5.55.5 | 622622 | 9,19,1 |
상기 표 2에 나타낸 바와 같이, 본 발명의 화합물을 발광층에 적용한 경우(실시예 11 내지 16)가 종래 CBP를 적용한 경우(비교예 2)보다 전류효율 및 구동전압이 우수한 것을 알 수 있다.As shown in Table 2, it can be seen that the current efficiency and driving voltage are superior to the case of applying the compound of the present invention to the light emitting layer (Examples 11 to 16) compared to the case of applying the conventional CBP (Comparative Example 2).
[[
실시예Example
17 내지 22] 17 to 22]
합성예에서 합성한 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 녹색 유기 전계 발광 소자를 제조하였다.The compound synthesized in the synthesis example was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured according to the following procedure.
ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수로 초음파 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후, UV OZONE 세정기(Power sonic 405, 화신테크)로 이송시킨 다음, UV를 이용하여 상기 기판을 5 분간 세정한 후 진공 층착기로 기판을 이송하였다.A glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 Å was ultrasonically washed with distilled water. After washing with distilled water, ultrasonic washing with a solvent such as isopropyl alcohol, acetone, methanol, and drying was carried out, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and the substrate was cleaned for 5 minutes using UV. The substrate was then transferred to a vacuum depositor.
상기와 같이 준비된 ITO 투명 기판(전극) 위에 m-MTDATA(60nm)/R11, R36, R61, R66, R86, R111, R136 각각의 화합물(80nm)/95% DS-H522(㈜두산전자) + 5% DS-501(㈜두산전자)(30nm)/BCP(10nm)/Alq3(30 nm)/LiF(1nm)/Al(200nm) 순으로 적층하여 녹색 유기 전계 발광 소자를 제조하였다.M-MTDATA (60nm) / R11, R36, R61, R66, R86, R111, R136 Compound (80nm) / 95% DS-H522 (Doosan Electronics Co., Ltd.) + 5 on the prepared ITO transparent substrate (electrode) A green organic electroluminescent device was manufactured by stacking DS-501 (Doosan Electronics Co., Ltd.) (30 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) in this order.
[비교예 3]Comparative Example 3
정공 수송층 형성시 정공 수송층 물질로 사용된 화합물 R11 대신 NPB를 사용하는 것을 제외하고는 실시예 17과 동일한 과정으로 녹색 유기 전계 발광 소자를 제조하였다.A green organic electroluminescent device was manufactured in the same manner as in Example 17, except that NPB was used instead of the compound R11 used as the hole transport layer to form the hole transport layer.
상기 실시예 17 내지 22 및 비교예 3에서 사용된 m-MTDATA, BCP의 구조는 상기와 같고, NPB의 구조는 하기와 같다.The structures of m-MTDATA and BCP used in Examples 17 to 22 and Comparative Example 3 are as described above, and the structure of NPB is as follows.
[평가예 3][Evaluation Example 3]
실시예 17 내지 22 및 비교예 3에서 제조한 각각의 녹색 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서 구동전압 및 전류효율을 측정하고, 그 결과를 하기 표 3에 나타내었다.For each of the green organic EL devices manufactured in Examples 17 to 22 and Comparative Example 3, the driving voltage and the current efficiency were measured at a current density of 10 mA / cm 2, and the results are shown in Table 3 below.
| 샘플Sample | 정공 수송층Hole transport layer | 구동 전압 (V)Driving voltage (V) | 전류효율 (cd/A)Current efficiency (cd / A) |
| 실시예 17Example 17 | R11R11 | 4.44.4 | 23.723.7 |
| 실시예 18Example 18 | R36R36 | 4.54.5 | 22.522.5 |
| 실시예 19Example 19 | R61R61 | 4.34.3 | 24.124.1 |
| 실시예 20Example 20 | R86R86 | 3.83.8 | 21.521.5 |
| 실시예 21Example 21 | R111R111 | 4.04.0 | 22.622.6 |
| 실시예 22Example 22 | R136R136 | 4.04.0 | 22.122.1 |
| 비교예 3Comparative Example 3 | NPBNPB | 5.25.2 | 18.118.1 |
상기 표 3에 나타낸 바와 같이, 본 발명의 화합물을 정공수송층에 적용한 경우(실시예 17 내지 22)가 종래 NPB를 적용한 경우(비교예3)보다 전류효율 및 구동전압이 우수한 것을 알 수 있다.As shown in Table 3, it can be seen that when the compound of the present invention is applied to the hole transport layer (Examples 17 to 22), the current efficiency and the driving voltage are superior to those when applying the conventional NPB (Comparative Example 3).
[실시예 23 내지 32][Examples 23 to 32]
합성예에서 합성한 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 청색 유기 전계 발광 소자를 제조하였다.The compound synthesized in the synthesis example was subjected to high purity sublimation purification by a conventionally known method, and then a blue organic EL device was manufactured according to the following procedure.
ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수로 초음파 세척하였다. 증류수 세척이 끝나면, 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고, 건조시킨 후, UV OZONE 세정기(Power sonic 405, 화신테크)로 이송시킨 다음, UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.A glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 Å was ultrasonically washed with distilled water. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then the substrate using UV for 5 minutes The substrate was cleaned and transferred to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 기판(전극) 위에, DS-205(㈜두산전자) (80 nm)/NPB (15 nm)/ R1, R26, R51, R76, R101, R126, R151, R166, R171, R176 각각의 화합물 (15nm)/ADN + 5 % DS-405(㈜두산 전자) (300nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제조하였다.On the prepared ITO transparent substrate (electrode), DS-205 (Doosan Electronics Co., Ltd.) (80 nm) / NPB (15 nm) / R1, R26, R51, R76, R101, R126, R151, R166, R171, R176 Each compound (15nm) / ADN + 5% DS-405 (Doosan Electronics Co., Ltd.) (300nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) An organic electroluminescent device was manufactured.
[비교예 4][Comparative Example 4]
발광 보조층 물질로 사용된 화합물 R1을 사용하지 않은 것을 제외하고는, 실시예 23과 동일하게 수행하여 청색 유기 전계 발광 소자를 제조하였다.A blue organic electroluminescent device was manufactured in the same manner as in Example 23, except that Compound R1, which was used as the emission auxiliary layer material, was not used.
[비교예 5][Comparative Example 5]
발광 보조층 물질로 사용된 화합물 R1 대신 화합물 A를 사용하는 것을 제외하고는 실시예 23과 동일하게 수행하여 청색 유기 전계 발광 소자를 제조하였다.A blue organic electroluminescent device was manufactured in the same manner as in Example 23, except that Compound A was used instead of Compound R1 used as the emission auxiliary layer material.
상기 실시예 23 내지 32 및 비교예 4, 5에서 사용된 NPB 및 BCP의 구조는 상기와 같고, ADN 및 화합물 A의 구조는 하기와 같다.The structures of NPB and BCP used in Examples 23 to 32 and Comparative Examples 4 and 5 are as described above, and the structures of ADN and Compound A are as follows.
[평가예 4][Evaluation Example 4]
실시예 23 내지 32 및 비교예 4, 5에서 제조한 각각의 청색 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압 및 전류효율을 측정하고, 그 결과를 하기 표 4에 나타내었다.The driving voltage and current efficiency at the current density of 10 mA / cm 2 were measured for each of the blue organic electroluminescent devices prepared in Examples 23 to 32 and Comparative Examples 4 and 5, and the results are shown in Table 4 below.
| 샘플Sample | 발광보조층Luminous auxiliary layer | 구동전압(V)Driving voltage (V) | 전류효율(cd/A)Current efficiency (cd / A) | 발광피크(nm)Light emitting peak (nm) |
| 실시예 23Example 23 | R1R1 | 4.34.3 | 9.39.3 | 458458 |
| 실시예 24Example 24 | R26R26 | 4.04.0 | 8.48.4 | 458458 |
| 실시예 25Example 25 | R51R51 | 4.14.1 | 8.38.3 | 458458 |
| 실시예 26Example 26 | R76R76 | 4.14.1 | 8.98.9 | 458458 |
| 실시예 27Example 27 | R101R101 | 4,24,2 | 8.88.8 | 458458 |
| 실시예 28Example 28 | R126R126 | 3.93.9 | 7.57.5 | 459459 |
| 실시예 29Example 29 | R151R151 | 3.53.5 | 6.76.7 | 459459 |
| 실시예 30Example 30 | R166R166 | 3.03.0 | 6.56.5 | 458458 |
| 실시예 31Example 31 | R171R171 | 3.33.3 | 6.96.9 | 458458 |
| 실시예 32Example 32 | R176R176 | 3.23.2 | 6.36.3 | 458458 |
| 비교예 4Comparative Example 4 | -- | 4.34.3 | 4.54.5 | 458458 |
| 비교예 5Comparative Example 5 | AA | 5.55.5 | 5.35.3 | 458458 |
상기 표 4에 나타낸 바와 같이, 본 발명의 화합물을 발광 보조층에 적용한 경우(실시예 23 내지 32)가 구동전압 및 전류효율이 우수한 것을 알 수 있다.As shown in Table 4, it can be seen that the driving voltage and the current efficiency are excellent when the compound of the present invention is applied to the light emitting auxiliary layer (Examples 23 to 32).
Claims (11)
- 하기 화학식 1로 표시되는 화합물:Compound represented by the following formula (1):[화학식 1][Formula 1]
상기 화학식 1에서,In Chemical Formula 1,R1과 R2, R2와 R3, R3와 R4 중 하나 이상은 서로 결합하여 하기 화학식 2로 표시되는 축합 고리를 형성하고,At least one of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 may be bonded to each other to form a condensed ring represented by Formula 2 below;[화학식 2][Formula 2]
상기 화학식 2에서,In Chemical Formula 2,점선은 축합이 이루어지는 부분이고,The dotted line is the part where condensation takes placeX1은 O, S, Se, N(Ar1), C(Ar2)(Ar3) 및 Si(Ar4)(Ar5)로 이루어진 군에서 선택되고,X 1 is selected from the group consisting of O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ),축합 고리를 형성하지 않는 R1 내지 R4와, R5 내지 R16은 각각 독립적으로 수소, 중수소, 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, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고,R 1 to R 4 and R 5 to R 16 which do not form a condensed ring are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group , C 2 ~ C 40 Alkynyl group, C 3 ~ C 40 Cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 6 ~ C 60 Aryl group, Nuclear atoms 5 to 60 heteroaryl group, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 An aryloxy group, C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 An arylsilyl group, C 1 ~ C 40 Alkyl boron group, is selected from the group 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 ~ C 60 aryl amine, consisting of,Ar1 내지 Ar5는 각각 독립적으로 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, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고,Ar 1 to Ar 5 are each independently a C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, nuclear atoms 3 to 40 Heterocycloalkyl group, C 6 ~ C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 Alkyl silyl group, C 6 ~ C 60 aryl silyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 Aryl phosphine oxide group and C 6 ~ C 60 It is selected from the group consisting of arylamine group,상기 R1 내지 R16 및 Ar1 내지 Ar5의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로, 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, C3~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 치환 또는 비치환되며, 이때, 복수의 치환기로 치환될 경우 이들은 서로 동일 또는 상이하다.The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group of R 1 to R 16 and Ar 1 to Ar 5 , Alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alky group, C 3 ~ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 hetero cycloalkyl, heteroaryl of C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 aryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ aryloxy C 60, C 3 ~ C 40 alkyl silyl group, an aryl boronic of C 6 ~ C aryl silyl group of 60, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 60 group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ substituted by one or more substituents selected from the group consisting of C 60 aryl amine, or unsubstituted of He said, at this time, they are the same or different from each other when a plurality of substituents to be substituted. - 제1항에 있어서,The method of claim 1,상기 화학식 1로 표시되는 화합물이 하기 화학식 1-A 내지 화학식 1-J로 표시되는 화합물로 이루어진 군에서 선택되는 화합물.Compound represented by Formula 1 is selected from the group consisting of compounds represented by the following formula 1-A to formula 1-J.
상기 화학식 1-A 내지 1-J에서,In Chemical Formulas 1-A to 1-J,X1 및 R1 내지 R16는 제1항에서 정의한 바와 같고, 이때, 복수의 R13은 서로 동일 또는 상이하고, 복수의 R14는 서로 동일 또는 상이하며, 복수의 R15는 서로 동일 또는 상이하고, 복수의 R16은 서로 동일 또는 상이하다.X 1 and R 1 to R 16 are as defined in claim 1, wherein a plurality of R 13 are the same or different from each other, a plurality of R 14 are the same or different from each other, and a plurality of R 15 are the same or different from each other In addition, some R <16> is the same or different from each other. - 제1항에 있어서,The method of claim 1,상기 X1이 N(Ar1)인 화합물.X 1 is N (Ar 1 ).
- 제1항에 있어서,The method of claim 1,축합 고리를 형성하지 않는 R1 내지 R4, R5 내지 R16 및 Ar1 내지 Ar5 중 적어도 하나는 C1~C40의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되는 화합물.At least one of R 1 to R 4 , R 5 to R 16, and Ar 1 to Ar 5 , which does not form a condensed ring, may be an alkyl group of C 1 to C 40 , an aryl group of C 6 to C 60 , and a nuclear atom of 5 to 60 A compound selected from the group consisting of a heteroaryl group and C 6 ~ C 60 An arylamine group.
- 제1항에 있어서,The method of claim 1,축합 고리를 형성하지 않는 R1 내지 R4, R5 내지 R16 및 Ar1 내지 Ar5 중 적어도 하나는 하기 화학식 3으로 표시되는 치환체인 화합물.At least one of R 1 to R 4 , R 5 to R 16, and Ar 1 to Ar 5 that do not form a condensed ring is a substituent represented by the following formula (3).[화학식 3][Formula 3]
상기 화학식 3에서,In Chemical Formula 3,*는 상기 화학식 1에 결합되는 부분을 의미하고,* Means a moiety bonded to Formula 1,L1은 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18의 헤테로아릴렌기로 이루어진 군에서 선택되고,L 1 is selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms,Y1 내지 Y5는 각각 독립적으로 N 또는 C(R21)이며, 이때 C(R21)이 복수인 경우, 이들은 서로 동일 또는 상이하며,Y 1 to Y 5 are each independently N or C (R 21 ), wherein when there are a plurality of C (R 21 ), they are the same or different from each other,상기 R21은 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기 C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C40의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하고,R 21 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group , nuclear atoms of 5 to 40 heteroaryl group, C 6 ~ aryloxy C 40 C 1 ~ C 40 alkyloxy group of, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group of , C 6 ~ C 40 arylamine group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 40 aryl boron group, C 6 ~ C 40 aryl phosphine group And, C 6 ~ C 40 An aryl phosphine oxide group and C 6 ~ C 40 An arylsilyl group selected from the group, or combine with an adjacent group to form a condensed ring,상기 R21의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되고, 이때 복수의 치환기로 치환될 경우, 이들은 서로 동일 또는 상이하다.An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group of R 21 , a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, the arylphosphine oxide group and the arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alky Neyl group, C 6 ~ C 40 aryl group, C 5 ~ C 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamine group, an aryl boronic of C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 40 group, C 6 ~ C 40 aryl substituted with a phosphine group, C 6 ~ C 40 aryl phosphine oxide groups and one or more substituents selected from the group consisting of aryl silyl C 6 ~ C 40 of It is unsubstituted, wherein if substituted with a plurality of substituents, they are same or different from each other. - 제5항에 있어서,The method of claim 5,상기 화학식 3으로 표시되는 치환체가 하기 화학식 A-1 내지 A-16으로 표시되는 치환체로 이루어진 군에서 선택되는 화합물.Compound represented by the formula (3) is selected from the group consisting of substituents represented by the formula A-1 to A-16.
상기 A-1 내지 A-16에서,In the above A-1 to A-16,L1 및 R21은 제5항에서 정의한 바와 같고,L 1 and R 21 are as defined in claim 5,R22는 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하며,R 22 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 3 -C 40 cycloalkyl group, aryloxy be an aryl group, the nucleus of atoms of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 40 of from 5 to 40 heteroaryl group, C 6 ~ C 40, alkyloxy group of C 1 ~ C 40 , C 6 ~ C 40 arylamine group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 40 aryl boron group, C 6 ~ C 40 aryl phosphine group , C 6 ~ C 40 An aryl phosphine oxide group and C 6 ~ C 40 An arylsilyl group selected from the group, or combine with an adjacent group to form a condensed ring,상기 R22의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되고, 이때, 복수의 치환기로 치환될 경우, 이들은 서로 동일 또는 상이하고,An alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group of R 22 , The arylphosphine group, the arylphosphine oxide group and the arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alky Neyl group, C 6 ~ C 40 aryl group, C 5 ~ C 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamine group, an aryl boronic of C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 40 group, C 6 ~ C 40 aryl substituted with a phosphine group, C 6 ~ C 40 aryl phosphine oxide groups and one or more substituents selected from the group consisting of aryl silyl C 6 ~ C 40 of Is unsubstituted, In this case, and the case be substituted with plural substituents, they are same or different from each other,n은 0 내지 4의 정수이다.n is an integer of 0-4. - 제1항에 있어서,The method of claim 1,축합 고리를 형성하지 않는 R1 내지 R4, R5 내지 R16, Ar1 내지 Ar5 중 적어도 하나는 하기 화학식 4로 표시되는 치환체인 화합물.At least one of R 1 to R 4 , R 5 to R 16 , and Ar 1 to Ar 5 that do not form a condensed ring is a substituent represented by the following formula (4).[화학식 4][Formula 4]
상기 화학식 4에서,In Chemical Formula 4,*는 상기 화학식 1에 결합되는 부분을 의미하고,* Means a moiety bonded to Formula 1,L2은 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18의 헤테로아릴렌기로 이루어진 군에서 선택되고,L 2 is selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms,R23 및 R24는 각각 독립적으로 C1~C40의 알킬기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 서로 결합하여 축합 고리를 형성하며,R 23 and R 24 are each independently a C 1 ~ C 40 alkyl group, C 6 ~ C 40 aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, and a C 6 ~ selected from the group consisting of an aryl amine of the C 60 Or combine with each other to form a condensed ring,상기 R23 및 R24의 알킬기, 아릴기, 헤테로아릴기 및 아릴아민기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되고, 이때 복수의 치환기로 치환될 경우, 이들은 서로 동일 또는 상이하다.The alkyl group, aryl group, heteroaryl group and arylamine group of R 23 and R 24 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C 6 ~ C 40, alkyloxy group of C 1 ~ C 40 of, C 6 ~ C 40 aryl amine group, C 3 ~ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group 1 ~ C 40 alkyl silyl, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 40 aryl boron group, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ C 40 aryl silyl group substituted or by one substituent at least one selected from the group consisting of When unsubstituted and substituted with a plurality of substituents, they are the same or different from each other. - (i) 양극, (ii) 음극, 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서,An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more layers of organic material interposed between the anode and the cathode,상기 1층 이상의 유기물층 중에서 적어도 하나가 제1항 내지 제7항 중 어느 한 항에 기재된 화합물을 포함하는 유기 전계 발광 소자.An organic electroluminescent device comprising at least one of the at least one organic material layer comprising the compound according to any one of claims 1 to 7.
- 제8항에 있어서,The method of claim 8,상기 화합물을 포함하는 유기물층은 발광층이며,The organic material layer containing the compound is a light emitting layer,상기 화합물은 발광층의 인광 호스트인 유기 전계 발광 소자.The compound is an organic electroluminescent device which is a phosphorescent host of the light emitting layer.
- 제8항에 있어서,The method of claim 8,상기 화합물을 포함하는 유기물층은 발광 보조층인 유기 전계 발광 소자.The organic material layer containing the compound is an organic light emitting device that is a light emitting auxiliary layer.
- 제8항에 있어서,The method of claim 8,상기 화합물을 포함하는 유기물층은 정공 수송층인 유기 전계 발광 소자.The organic material layer containing the compound is an organic electroluminescent device which is a hole transport layer.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020140184580A KR102307370B1 (en) | 2014-12-19 | 2014-12-19 | Organic compound and organic electroluminescent device comprising the same |
| KR10-2014-0184580 | 2014-12-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2016099037A2 true WO2016099037A2 (en) | 2016-06-23 |
| WO2016099037A3 WO2016099037A3 (en) | 2016-10-06 |
Family
ID=56127794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2015/012394 WO2016099037A2 (en) | 2014-12-19 | 2015-11-18 | Organic compound and organic electroluminescent device comprising same |
Country Status (2)
| Country | Link |
|---|---|
| KR (1) | KR102307370B1 (en) |
| WO (1) | WO2016099037A2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018034242A1 (en) * | 2016-08-19 | 2018-02-22 | 出光興産株式会社 | Compound, organic electroluminescent element material, organic electroluminescent element, and electronic device |
| EP3680242A1 (en) * | 2019-01-10 | 2020-07-15 | Idemitsu Kosan Co., Ltd. | Organic light emitting device and compounds for use in same |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20110066763A (en) | 2009-12-11 | 2011-06-17 | 덕산하이메탈(주) | Compound containing indoloacridine and organic electronic element using the same, terminal thereof |
| JP2014086463A (en) * | 2012-10-19 | 2014-05-12 | Canon Inc | Novel fused polycyclic compound |
| KR102081280B1 (en) * | 2013-01-30 | 2020-05-28 | 삼성디스플레이 주식회사 | Organic light emitting diode comprising the same |
| KR102137472B1 (en) * | 2013-02-08 | 2020-07-27 | 삼성디스플레이 주식회사 | Organic light emitting diode comprising the same |
| CN104513660A (en) * | 2013-09-30 | 2015-04-15 | 北京鼎材科技有限公司 | Organic luminescence material and applications thereof |
-
2014
- 2014-12-19 KR KR1020140184580A patent/KR102307370B1/en active IP Right Grant
-
2015
- 2015-11-18 WO PCT/KR2015/012394 patent/WO2016099037A2/en active Application Filing
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018034242A1 (en) * | 2016-08-19 | 2018-02-22 | 出光興産株式会社 | Compound, organic electroluminescent element material, organic electroluminescent element, and electronic device |
| JPWO2018034242A1 (en) * | 2016-08-19 | 2019-06-20 | 出光興産株式会社 | Compound, material for organic electroluminescence device, organic electroluminescence device, and electronic device |
| EP3680242A1 (en) * | 2019-01-10 | 2020-07-15 | Idemitsu Kosan Co., Ltd. | Organic light emitting device and compounds for use in same |
| US11706981B2 (en) | 2019-01-10 | 2023-07-18 | Idemitsu Kosan Co., Ltd. | Organic light emitting device and compounds for use in same |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2016099037A3 (en) | 2016-10-06 |
| KR102307370B1 (en) | 2021-10-05 |
| KR20160075072A (en) | 2016-06-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2016105161A2 (en) | Organic compound and organic electroluminescent element comprising same | |
| WO2020159019A1 (en) | Organic light-emitting compound, and organic electroluminescent device using same | |
| WO2018230782A1 (en) | Organic compound and organic electroluminescent device comprising same | |
| WO2015122711A1 (en) | Organic compound and organic electroluminescent device comprising same | |
| WO2017111544A1 (en) | Organic compound and organic electroluminescent device comprising same | |
| WO2015111864A1 (en) | Organic compound, and organic electroluminescent device containing same | |
| WO2017209488A1 (en) | Organic compound and organic electroluminescent device comprising same | |
| WO2013168927A2 (en) | Novel compound and organic electroluminescent device comprising same | |
| WO2015133804A1 (en) | Organic compound and organic electroluminescent device comprising same | |
| WO2017111543A1 (en) | Organic compound and organic electroluminescent device comprising same | |
| WO2013100497A1 (en) | Organic light-emitting compound and organic electroluminescent device using same | |
| WO2015111943A1 (en) | Organic compound, and organic electroluminescent device containing same | |
| WO2019004584A1 (en) | Organic compound and organic electroluminescent device comprising same | |
| WO2020116881A1 (en) | Organic compound and organic electroluminescent element comprising same | |
| WO2016105123A2 (en) | Organic compound and organic electroluminescent device comprising same | |
| WO2012093861A2 (en) | Organic light emitting compound and organic electroluminescent device including same | |
| WO2017111389A1 (en) | Organic compound and organic electroluminescent diode including same | |
| WO2020218680A1 (en) | Organic compound and organic electroluminescent diode using same | |
| WO2016013894A2 (en) | Organic compound and organic electroluminescent device comprising same | |
| WO2019103397A1 (en) | Organic compound and organic electroluminescent device comprising same | |
| WO2016104954A2 (en) | Organic compound and organic electroluminescent device comprising same | |
| WO2015099477A2 (en) | Organic compound and organic light-emitting diode device using same | |
| WO2015133808A1 (en) | Organic compound and organic electroluminescent device comprising same | |
| WO2015046982A2 (en) | Organic compound and organic electroluminescent element comprising same | |
| WO2020130725A1 (en) | Organic compound and organic electroluminescent device comprising same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 15870205 Country of ref document: EP Kind code of ref document: A2 |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 32PN | Ep: public notification in the ep bulletin as address of the adressee cannot be established |
Free format text: NOTING OF LOSS OF RIGHTS PURSUANT TO RULE 112(1) EPC (EPO FORM 1205N DATED 25.08.2017) |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 15870205 Country of ref document: EP Kind code of ref document: A2 |