WO2018012762A1 - Organic compound and organic electroluminescent device comprising same - Google Patents
Organic compound and organic electroluminescent device comprising same Download PDFInfo
- Publication number
- WO2018012762A1 WO2018012762A1 PCT/KR2017/006854 KR2017006854W WO2018012762A1 WO 2018012762 A1 WO2018012762 A1 WO 2018012762A1 KR 2017006854 W KR2017006854 W KR 2017006854W WO 2018012762 A1 WO2018012762 A1 WO 2018012762A1
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- WIPO (PCT)
- Prior art keywords
- group
- aryl
- alkyl
- groups
- boron
- Prior art date
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- 150000002894 organic compounds Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 209
- 125000003118 aryl group Chemical group 0.000 claims description 216
- 125000000217 alkyl group Chemical group 0.000 claims description 160
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 122
- 125000001072 heteroaryl group Chemical group 0.000 claims description 89
- 125000000304 alkynyl group Chemical group 0.000 claims description 81
- 125000001424 substituent group Chemical group 0.000 claims description 79
- 125000003342 alkenyl group Chemical group 0.000 claims description 77
- 125000005264 aryl amine group Chemical group 0.000 claims description 76
- 125000004429 atom Chemical group 0.000 claims description 76
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 76
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 76
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 75
- 125000004104 aryloxy group Chemical group 0.000 claims description 75
- 125000003545 alkoxy group Chemical group 0.000 claims description 73
- 125000005104 aryl silyl group Chemical group 0.000 claims description 71
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 51
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 51
- 229910052805 deuterium Inorganic materials 0.000 claims description 51
- 229910052736 halogen Inorganic materials 0.000 claims description 51
- 150000002367 halogens Chemical class 0.000 claims description 51
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 50
- 239000000126 substance Substances 0.000 claims description 45
- -1 alkyl boron Chemical compound 0.000 claims description 41
- 239000011368 organic material Substances 0.000 claims description 34
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 33
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims description 31
- 229910052796 boron Inorganic materials 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000000732 arylene group Chemical group 0.000 claims description 20
- 125000005549 heteroarylene group Chemical group 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 238000002347 injection Methods 0.000 claims description 17
- 239000007924 injection Substances 0.000 claims description 17
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical group CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 claims description 17
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 15
- 239000008280 blood Substances 0.000 claims description 15
- 210000004369 blood Anatomy 0.000 claims description 15
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 230000005525 hole transport Effects 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 125000000061 phosphanyl group Chemical group [H]P([H])* 0.000 claims description 14
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 229910052710 silicon Inorganic materials 0.000 claims description 9
- 238000009833 condensation Methods 0.000 claims description 8
- 230000005494 condensation Effects 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 150000004982 aromatic amines Chemical class 0.000 claims description 5
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 4
- 150000001336 alkenes Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 125000006267 biphenyl group Chemical group 0.000 claims description 3
- 230000006872 improvement Effects 0.000 claims description 3
- 125000005647 linker group Chemical group 0.000 claims description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 239000010410 layer Substances 0.000 abstract description 117
- 239000012044 organic layer Substances 0.000 abstract description 31
- 238000006243 chemical reaction Methods 0.000 description 149
- 239000000463 material Substances 0.000 description 51
- 230000015572 biosynthetic process Effects 0.000 description 49
- 238000003786 synthesis reaction Methods 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 238000012937 correction Methods 0.000 description 35
- 239000012153 distilled water Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000011734 sodium Substances 0.000 description 23
- 230000000052 comparative effect Effects 0.000 description 22
- 239000000243 solution Substances 0.000 description 19
- 238000004440 column chromatography Methods 0.000 description 17
- 238000004519 manufacturing process Methods 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 17
- 239000000758 substrate Substances 0.000 description 17
- 230000005684 electric field Effects 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 12
- 239000002019 doping agent Substances 0.000 description 12
- 239000012299 nitrogen atmosphere Substances 0.000 description 12
- 230000008569 process Effects 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000002131 composite material Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 9
- JWJQEUDGBZMPAX-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 JWJQEUDGBZMPAX-UHFFFAOYSA-N 0.000 description 8
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- HHRUSDSAHBAKFW-UHFFFAOYSA-N 1-bromo-4-[2-(4-phenylphenyl)phenyl]benzene Chemical compound C1=CC(Br)=CC=C1C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 HHRUSDSAHBAKFW-UHFFFAOYSA-N 0.000 description 5
- 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 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 5
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 5
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000000859 sublimation Methods 0.000 description 5
- 230000008022 sublimation Effects 0.000 description 5
- 238000004506 ultrasonic cleaning Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 0 *c1c(*c(c-2c3*)c(*)c4c3Sc(c(*)c(*)c(*)c3*)c3S4)c-2c(*)c(*)c1* Chemical compound *c1c(*c(c-2c3*)c(*)c4c3Sc(c(*)c(*)c(*)c3*)c3S4)c-2c(*)c(*)c1* 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- 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 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- MDYDGUOQFUQOGE-UHFFFAOYSA-N 2-methylpropanethioic acid S-[7-oxo-7-[(4-phenyl-2-thiazolyl)amino]heptyl] ester Chemical class S1C(NC(=O)CCCCCCSC(=O)C(C)C)=NC(C=2C=CC=CC=2)=C1 MDYDGUOQFUQOGE-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
- 238000011161 development Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- GCSOJZMPHLRBMJ-UHFFFAOYSA-N thianthren-2-ylboronic acid Chemical compound C1=CC=C2SC3=CC(B(O)O)=CC=C3SC2=C1 GCSOJZMPHLRBMJ-UHFFFAOYSA-N 0.000 description 3
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- NCWDBNBNYVVARF-UHFFFAOYSA-N 1,3,2-dioxaborolane Chemical compound B1OCCO1 NCWDBNBNYVVARF-UHFFFAOYSA-N 0.000 description 2
- OTJZMNIBLUCUJZ-UHFFFAOYSA-N 2,4-diphenyl-1,3,5-triazine Chemical compound C1=CC=CC=C1C1=NC=NC(C=2C=CC=CC=2)=N1 OTJZMNIBLUCUJZ-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- JAUCIDPGGHZXRP-UHFFFAOYSA-N 4-phenyl-n-(4-phenylphenyl)aniline Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC(C=C1)=CC=C1C1=CC=CC=C1 JAUCIDPGGHZXRP-UHFFFAOYSA-N 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-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
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- BIECSXCXIXHDBC-UHFFFAOYSA-N methyl 2-bromo-5-chlorobenzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1Br BIECSXCXIXHDBC-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- RUIIQTRTGLKGMK-UHFFFAOYSA-N (3-dibenzofuran-2-ylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=C3C4=CC=CC=C4OC3=CC=2)=C1 RUIIQTRTGLKGMK-UHFFFAOYSA-N 0.000 description 1
- YSDJLONVLIHBRC-UHFFFAOYSA-N (3-triphenylen-2-ylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=C3C4=CC=CC=C4C4=CC=CC=C4C3=CC=2)=C1 YSDJLONVLIHBRC-UHFFFAOYSA-N 0.000 description 1
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-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
- OPCMVVKRCLOEDQ-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(methylamino)pentan-1-one Chemical compound ClC1=CC=C(C=C1)C(C(CCC)NC)=O OPCMVVKRCLOEDQ-UHFFFAOYSA-N 0.000 description 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- YFTHTJAPODJVSL-UHFFFAOYSA-N 2-(1-benzothiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(SC=C2)C2=C1 YFTHTJAPODJVSL-UHFFFAOYSA-N 0.000 description 1
- KWXFBIBEVROWEF-UHFFFAOYSA-N 2-(3-bromophenyl)triphenylene Chemical group BrC1=CC=CC(C=2C=C3C4=CC=CC=C4C4=CC=CC=C4C3=CC=2)=C1 KWXFBIBEVROWEF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NTEIZPBYXABJKN-UHFFFAOYSA-N 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound C1=CC(Cl)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 NTEIZPBYXABJKN-UHFFFAOYSA-N 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000004332 silver Substances 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
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- 238000010189 synthetic method Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
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- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
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- 239000010936 titanium Substances 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered 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
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C—CHEMISTRY; METALLURGY
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Definitions
- the present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.
- 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.
- the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials for better natural colors according to light emission colors.
- a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
- the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
- a metal complex compound containing heavy atoms such as Ir and Pt.
- NPB hole blocking layer
- BCP hole blocking layer
- electron transporting layer material anthracene derivatives have been reported as the light emitting layer material.
- metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 , which have advantages in terms of efficiency improvement among the light emitting layer materials, are blue, green, and red. (red) is used as the phosphorescent dopant material, 4,4-dicarbazolybiphenyl (CBP) is used as the phosphorescent host material.
- the conventional organic material has an advantageous aspect in terms of light emission characteristics, but the thermal stability is not very good due to the low glass transition temperature, it is not a satisfactory level in terms of the life of the organic EL device. Therefore, development of an organic material layer material excellent in performance is desired.
- an object of the present invention is to provide a novel compound and an organic electroluminescent device using the compound which can improve the efficiency, lifespan and stability of the organic electroluminescent device.
- the present invention 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 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 is condensed and condensed with a ring represented by the following formula (2) To form a ring;
- R 1 to R 8 which do not form a ring and a condensed ring represented by the following formula (2) are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenes group, C 2 ⁇ C 40 of the 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 60 heteroaryl group , C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group , C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphanyl group, C 6 ⁇ C 60 mono or diary
- alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 1 to R 8 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear
- the dotted line is the part where condensation takes place
- X 1 is selected from the group consisting of C (Ar 1 ) (Ar 2 ), N (Ar 3 ), O, S and Si (Ar 4 ) (Ar 5 );
- Ar 1 and Ar 2 are each independently C 1 -C 40 alkyl group or C 6 -C 60 aryl group;
- Ar 3 to Ar 5 are each independently a substituent represented by the following formula (3);
- Y 1 to Y 4 are each independently N or C (R 9 );
- R 9 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, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phospha Or a C 6 to C 60 mono or diarylphosphinyl group and a C 6 to C 60 arylamine group, or combine with an adjacent group to form a condensed ring, and a plurality of R 9 plural R 9 are the same as or
- alkyl group and aryl group of Ar 1 and Ar 2 the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group of R 9 , Alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, an aryloxy group of C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ⁇ C 60 of, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryl
- L 1 and L 2 are each independently 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;
- R 10 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, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phospha A aryl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring;
- the amine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40
- 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 provides an organic electroluminescent device comprising the compound of Formula 1. .
- Alkyl in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl And the like, but are not limited thereto.
- Alkenyl in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having at least one carbon-carbon double bond, and examples thereof include vinyl, Allyl, isopropenyl, 2-butenyl, and the like, but is not limited thereto.
- Alkynyl in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having at least one carbon-carbon triple bond, examples of which are ethynyl. , 2-propynyl, and the like, but is not limited thereto.
- Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined.
- Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and the like.
- Heteroaryl in the present invention means a monovalent substituent derived from a 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 selected from N, O, P, S and Se. In addition, two or more rings are simply pendant or condensed with each other, and in addition to carbon as a ring forming atom, a hetero atom selected from N, O, P, S and Se, the entire molecule is non-aromatic (non- It is also interpreted to include monovalent groups having aromacity).
- heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; 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 5 to 60 carbon atoms.
- R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
- alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl, and is linear, branched or cyclic structure.
- alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
- Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
- cycloalkyl in the present invention is meant monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms.
- examples of such cycloalkyl 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 3 to 40 non-aromatic hydrocarbons of nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or Se.
- heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
- alkylsilyl means silyl substituted with alkyl having 1 to 40 carbon atoms
- arylsilyl means silyl substituted with aryl having 5 to 60 carbon atoms.
- Condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.
- the compound of the present invention has excellent thermal stability, carrier transporting ability, light emitting ability, and the like, it can be usefully applied as an organic material layer material of an organic EL device.
- the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full color display panel since the aspect of light emission performance, driving voltage, lifespan, efficiency, etc. is greatly improved.
- At least one of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 is condensed and condensed with a ring represented by the following formula (2) To form a ring;
- R 1 to R 8 which do not form a ring and a condensed ring represented by the following formula (2) are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenes group, C 2 ⁇ C 40 of the 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 60 heteroaryl group , C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group , C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphanyl group, C 6 ⁇ C 60 mono or diary
- alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 1 to R 8 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear
- the dotted line is the part where condensation takes place
- X 1 is selected from the group consisting of C (Ar 1 ) (Ar 2 ), N (Ar 3 ), O, S and Si (Ar 4 ) (Ar 5 );
- Ar 1 and Ar 2 are each independently C 1 -C 40 alkyl group or C 6 -C 60 aryl group;
- Ar 3 to Ar 5 are each independently a substituent represented by the following formula (3);
- Y 1 to Y 4 are each independently N or C (R 9 );
- R 9 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, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phospha Or a C 6 to C 60 mono or diarylphosphinyl group and a C 6 to C 60 arylamine group, or combine with an adjacent group to form a condensed ring, and a plurality of R 9 plural R 9 are the same as or
- alkyl group and aryl group of Ar 1 and Ar 2 the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group of R 9 , Alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, an aryloxy group of C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ⁇ C 60 of, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryl
- L 1 and L 2 are each independently 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;
- R 10 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, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phospha A aryl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring;
- the amine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40
- novel compounds of the present invention can be 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 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 is condensed and condensed with a ring represented by the following formula (2) Form a ring, but at least two of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 are represented by the following Chemical Formula 2 When condensed with a ring, the rings represented by the formula (2) which are respectively condensed are the same or different;
- R 1 to R 8 which do not form a ring and a condensed ring represented by the following formula (2) are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenes group, C 2 ⁇ C 40 of the 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 60 heteroaryl group , C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group , C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphanyl group, C 6 ⁇ C 60 mono or diary
- alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 1 to R 8 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear
- the dotted line is the part where condensation takes place
- X 1 is selected from the group consisting of C (Ar 1 ) (Ar 2 ), N (Ar 3 ), O, S and Si (Ar 4 ) (Ar 5 ), and when there are a plurality of X 1 , they are the same as each other or Different, preferably C (Ar 1 ) (Ar 2 ) or N (Ar 3 );
- Ar 1 and Ar 2 are each independently C 1 -C 40 alkyl group or C 6 -C 60 aryl group;
- Ar 3 to Ar 5 are each independently a substituent represented by the following formula (3);
- Y 1 to Y 4 are each independently N or C (R 9 );
- R 9 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, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phospha Or a C 6 to C 60 mono or diarylphosphinyl group and a C 6 to C 60 arylamine group, or combine with an adjacent group to form a condensed ring, and a plurality of R 9 plural R 9 are the same as or
- alkyl group and aryl group of Ar 1 and Ar 2 the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group of R 9 , Alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, an aryloxy group of C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ⁇ C 60 of, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryl
- L 1 and L 2 are each independently 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;
- R 10 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, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phospha A aryl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring;
- the amine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40
- the phosphorescent light emitting layer of the organic material layer included in the organic electroluminescent device includes a host and a dopant to increase the color purity and the luminous efficiency.
- the host should have a triplet energy gap higher than the dopant. That is, in order to effectively provide phosphorescence from the dopant, the energy of the lowest excited state of the host must be higher than the energy of the lowest emission state of the dopant.
- the structural portion of the cyanrene has a wide singlet energy level and a high triplet energy level. Furthermore, by introducing a specific substituent such as indene or indole moiety condensed into such cyanrene, when the compound of Formula 1 is applied as a host of the light emitting layer, it may exhibit a higher energy level than the dopant.
- an organic material layer (hereinafter, referred to as a 'light emitting auxiliary layer') is formed between the hole transport layer and the light emitting layer by using the compound of Formula 1, or an organic material layer (hereinafter referred to as an 'electron transport auxiliary layer') between the light emitting layer and the electron transporting layer.
- the excitons Since the diffusion of the exciton is prevented by the compound, unlike the conventional organic electroluminescent device that does not include the light emitting auxiliary layer or the electron transporting auxiliary layer, the excitons substantially contribute to light emission in the light emitting layer. The number can be increased to improve the luminous efficiency of the device.
- the compound represented by Chemical Formula 1 may have HOMO and LUMO energy levels controlled according to substituents introduced into the basic skeleton, thereby having a wide bandgap and high carrier transport properties.
- EWG electron withdrawing group
- the compound represented by the general formula (1) of the present invention has a significant increase in the molecular weight of the compound by introducing a variety of substituents, in particular aryl group and / or heteroaryl group to the basic skeleton, thus improving the glass transition temperature It may have a higher thermal stability than the organic material of the material (for example, CBP).
- the compound represented by the formula (1) of the present invention is also effective in suppressing the crystallization of the organic material layer.
- the compound represented by Chemical Formula 1 in the present invention may be an organic material layer material of an organic electroluminescent device, preferably an emission layer material (blue, green and / or red phosphorescent host material), an electron transport layer / injection layer material, a hole transport layer / When applied as an injection layer material, a light emission auxiliary layer material, or a life improvement layer material, the performance and life characteristics of the organic EL device may be greatly improved. As a result, the organic EL device may maximize the performance of the full color organic light emitting panel.
- Y 1 to Y 4 is C (R 9 ), a plurality of C (R 9 ) is It may be the same or different from each other.
- the condensed ring represented by the formula (2) may be a condensed ring represented by the following formula (4):
- the dotted line is the part where condensation takes place
- X 2 is selected from the group consisting of C (Ar 1 ) (Ar 2 ), N (Ar 3 ), O, S and Si (Ar 4 ) (Ar 5 ), preferably C (Ar 1 ) (Ar 2 ) Or N (Ar 3 );
- Ar 1 and Ar 2 are each independently C 1 -C 40 alkyl group or C 6 -C 60 aryl group;
- Ar 3 to Ar 5 are each independently a substituent represented by the following formula (3);
- R 11 to R 14 are each independently a substituent represented by Formula 5, or combine with an adjacent group to form a condensed ring;
- L 1 to L 4 are each independently 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;
- R 10 and R 19 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, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ for C 60 aryl phosphazene group, C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ is selected from the group consisting of an aryl amine of the C 60 of the;
- Alkyl, arylamine, alkylsilyl, alkylboron, arylboron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1- C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 6 -C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 6 -C 60 aryl Oxy group, C 1 -C 40 alkyloxy group, C 6 -C 60 arylamine group, C 3 -C 40 cycloal
- At least one of the R 11 and R 12 , R 12 and R 13 , R 13 and R 14 may be condensed with a ring represented by the following formula (6) to form a condensed ring, Wherein when two or more of R 11 and R 12 , R 12 and R 13 , R 13 and R 14 are condensed with a ring represented by the following Chemical Formula 6, the rings represented by Chemical Formula 6 to be condensed are the same or different;
- the dotted line is the part where condensation takes place
- X 3 is selected from the group consisting of C (Ar 6 ) (Ar 7 ), N (Ar 8 ), O, S and Si (Ar 9 ) (Ar 10 ), preferably C (Ar 6 ) (Ar 7 ) ) Or N (Ar 8 );
- Ar 6 and Ar 7 are each independently an alkyl group of C 1 to C 40 or an aryl group of C 6 to C 60 ;
- Ar 8 to Ar 10 and R 15 to R 18 are each independently a substituent represented by formula (7);
- L 5 and L 6 are each independently 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;
- R 20 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, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phospha A silyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group;
- the amine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40
- the compound may be a compound represented by any one of the following Formula 8 to 20:
- X 2 , X 3 , R 1 to R 5 , R 7 , R 8 and R 11 to R 18 are each as defined in Chemical Formulas 1, 4, and 6.
- each of L 1 to L 6 may be independently a single bond or a linker represented by any one of the following Formulas A-1 to A-6:
- X 4 and X 5 are each independently O, S, N (R 22 ) or C (R 23 ) (R 24 );
- X 6 is N or C (R 25 );
- p is an integer from 0 to 4.
- R 21 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 groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups, C An alkylsilyl group of 3 to C 40 , an arylsilyl group of C 6 to C 60 , an alkyl boron group of C 1 to C 40, an aryl boron group of C 6 to C 60 , an arylphosphanyl group of C 6 to C 60 , A C 6 ⁇ C 60 mono or diaryl phosphinyl group and C 6 ⁇ C 60 arylamine group may be selected from the group consisting of or combined with adjacent groups to form a con
- R 22 to R 25 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 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 aryl phosphazene group, selected from the group consisting arylsilyl a C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ C 60 of, or by combining tile adjacent to which they are attached may form a con
- alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 21 to R 25 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear
- Z 1 to Z 5 are each independently N or C (R 30 );
- T 1 and T 2 are each independently selected from the group consisting of a single bond, C (R 31 ) (R 32 ), N (R 33 ), O and S, but not both T 1 and T 2 are single bonds;
- q and r are each independently integers of 0 to 4.
- R 26 and R 27 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 60 the aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an aryloxy group of C 6 ⁇ C 60, C 1 ⁇ C 40 alkyloxy group of, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 Heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylsilyl group, or
- R 28 to R 33 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 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 aryl phosphazene group, selected from the group consisting of C 6 ⁇ C 60 mono or diaryl the Phosphinicosuccinic group and a C 6 ⁇ with an aryl silyl group of C 60, or combine tile adjacent to which they are attached may form
- alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 26 to R 33 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear
- At least one of the R 10 , R 19 and R 20 may be a substituent represented by any one of the formulas C-1 to C-24, the R 10 , R 19 and R 20 may be the same or different from each other:
- t is an integer from 0 to 5
- u is an integer from 0 to 4.
- v is an integer from 0 to 3;
- w is an integer from 0 to 2;
- R 34 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 6 ⁇ C 60 aryl group, nuclear atom C 5 to C 60 aryloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 arylamine group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 ⁇ C 60 It is selected from the group consisting of mono or diaryl phosphinyl group and C 6 ⁇ C 60 arylsilyl group, or may be combined with adjacent groups to form a condensed ring, when
- R 26 , R 27 , R 30 to R 33 , q and r are as defined in Chemical Formulas B-1 to B-7.
- At least one of the R 10 , R 19 and R 20 may be a substituent represented by the following formula (B-4):
- R 28 and R 29 each independently represent hydrogen, an alkyl group of C 1 to C 40 , an aryl group of C 6 to C 60 , a heteroaryl group of 5 to 60 nuclear atoms, an aryloxy group of C 6 to C 60 , and C It may be selected from the group consisting of 6 ⁇ C 60 arylamine group;
- the alkyl group, aryl group, heteroaryl group and arylamine group of R 28 and R 29 are each independently C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group and When substituted or unsubstituted with one or more substituents selected from the group consisting of C 6 to C 60 arylamine groups, and substituted with a plurality of substituents, they may be the same or different from each other.
- At least one of R 28 and R 29 may be a substituent represented by the following formula 21 or 22:
- L 7 and L 8 are each independently 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;
- Z 6 to Z 10 are each independently N or C (R 37 );
- R 35 to R 37 are each independently hydrogen, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 6 -C 60 aryl group, nuclear atom 5 To 60 heteroaryl groups and C 6 to C 60 arylamine groups, and when there are a plurality of R 37 groups, they are the same as or different from each other;
- the arylene group and heteroarylene group of L 7 and L 8 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, and arylamine group of R 35 to R 37 are each independently C 1 to C 40 .
- An alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 6 to C 60 aryl group, a nuclear atom having 5 to 60 heteroaryl groups, and a C 6 to C 60 arylamine group When substituted or unsubstituted and substituted with a plurality of substituents, they are the same as or different from each other.
- R 28 and R 29 are each independently a phenyl group, a biphenyl group, a naphthalenyl group, a carbazolyl group unsubstituted or substituted with an alkyl group of C 1 ⁇ C 10 and the formula 21 It may be selected from the group consisting of substituents represented.
- R 35 and R 36 may be each independently selected from the group consisting of a phenyl group, a biphenyl group and a naphthalenyl group.
- Compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:
- an organic electroluminescent device comprising a compound represented by the formula (1).
- the present invention includes (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 organic layers is It includes a compound represented by the formula (1).
- the compound represented by Formula 1 may be used alone or two or more kinds are mixed.
- the one or more organic material layers may include any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer is represented by the formula (1) It may include a compound.
- the organic material layer including the compound represented by Formula 1 may be a light emitting layer or a hole transport layer, and more preferably, when the compound represented by Formula 1 is included in the light emitting layer, the luminous efficiency and luminance of the organic EL device It can greatly improve power efficiency, thermal stability and device life.
- the compound represented by Chemical Formula 1 may be a phosphorescent host, a fluorescent host, or a dopant material of the light emitting layer, and preferably, a phosphorescent host of the light emitting layer.
- the one or more organic material layers may include any one or more of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer is It may include a compound represented by the formula (1).
- the organic material layer including the compound represented by Chemical Formula 1 may be a light emission auxiliary layer.
- the efficiency (light emitting efficiency and power efficiency), lifetime, and luminance of the organic light emitting diode are further improved, and the driving voltage is further improved. Can be lowered.
- the one or more organic material layers may include any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer May include a compound represented by Chemical Formula 1.
- the organic material layer including the compound represented by Formula 1 may be an electron transport auxiliary layer.
- the efficiency (light emitting efficiency and power efficiency), lifespan and luminance of the organic electroluminescent device are further improved, and the driving voltage is more fragile. Can be.
- the structure of the organic EL device of the present invention is not particularly limited, and for example, the anode, one or more organic material layers and the cathode are sequentially stacked on the substrate, and an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer. Can be.
- the organic EL device may have a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked on a substrate, and, if necessary, between the hole transport layer and the light emitting layer.
- An emission auxiliary layer may be inserted, and an electron injection layer may be positioned on the electron transport layer.
- the organic electroluminescent device of the present invention is at least one of the one or more organic material layers, for example, a light emitting layer or a light emitting auxiliary layer is formed so as to include a compound represented by the formula (1), and materials known in the art It can be prepared by forming an organic material layer and an electrode using a method.
- 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.
- Examples of the substrate that can be used in the manufacture of the organic EL device in the present invention include a silicon wafer, quartz or glass plate, a metal plate, a plastic film or sheet, but is not limited thereto.
- 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 metals and oxides 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 and polyaniline; Or carbon black, but is 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 metals and oxides such as ZnO: Al or SnO 2 : Sb
- Conductive polymers such as polythiophene, poly (3-methylthiophene
- examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
- the material used as the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, and any material known in the art may be used without limitation.
- Methyl 2- (5H-benzo [5,6] [1,4] dithiino [2,3-b] carbazole-2 obtained in ⁇ Step 2> under a nitrogen atmosphere in a three-necked round bottom flask heated under vacuum -Yl) benzoate (87.9g, 0.20mol) was added and dissolved in 900mL THF, and then cooled and stirred to -10 °C. 166 mL (in Ether, 0.5 mol) of 3.0 M CH 3 MgBr was slowly added thereto for 30 minutes. The reaction solution was heated to room temperature and stirred for 12 hours under a nitrogen atmosphere.
- Example 2 The same process as in Example 1 was carried out, except for (9- (4,6-diphenyl-1,3,5-triazine-2-) instead of (9-phenyl-9H-carbazol-3-yl) boronic acid.
- Compound Cpd 34 (4.3 g, yield 86%) was obtained using yl) -9H-carbazol-3-yl) boronic acid.
- Example 2 The same process as in Example 1 was carried out, except for (9- (3- (4,6-diphenyl-1,3,5-triazine) instead of (9-phenyl-9H-carbazol-3-yl) boronic acid. 2-yl) phenyl) -9H-carbazol-3-yl) boronic acid was used to give compound Cpd 43 (5.1 g, yield 81%).
- a compound Cpd 46 (3.5 g, yield 80%) was obtained in the same manner as in Example 1 except that Inv 3 was used instead of Inv 1.
- a compound Cpd 55 (4.0 g, 85% yield) was obtained in the same manner as in Example 4 except that Inv 3 was used instead of Inv 1.
- a compound Cpd 56 (4.2 g, yield 92%) was obtained in the same manner as in Example 5 except that Inv 3 was used instead of Inv 1.
- a compound Cpd 73 (4.2 g, yield 86%) was obtained in the same manner as in Example 7, except that Inv 3 was used instead of Inv 1.
- a compound Cpd 84 (4.9 g, yield 80%) was obtained in the same manner as in Example 9 except that Inv 3 was used instead of Inv 1.
- a compound Cpd 91 (3.5 g, yield 80%) was obtained in the same manner as in Example 11, except that Inv 2 was used instead of Inv 3.
- a compound Cpd 96 (4.8 g, yield 85%) was obtained in the same manner as in Example 12, using Inv 2 instead of Inv 3.
- a compound Cpd 100 (4.0 g, yield 85%) was obtained in the same manner as in Example 13, using Inv 2 instead of Inv 3.
- a compound Cpd 101 (4.2 g, yield 92%) was obtained in the same manner as in Example 14, except that Inv 2 was used instead of Inv 3.
- a compound Cpd 118 (4.2 g, yield 86%) was obtained in the same manner as in Example 15, except that Inv 2 was used instead of Inv 3.
- a compound Cpd 129 (4.9 g, 80% yield) was obtained in the same manner as in Example 16, except that Inv 2 was used instead of Inv 3.
- a compound Cpd 133 (5.1 g, 81% yield) was obtained in the same manner as in Example 17, except that Inv 2 was used instead of Inv 3.
- Example 35 The same procedure as in Example 35 was carried out, except that Inv 13 was used instead of Inv 9 to obtain compound Cpd 231 (11.6 g, yield 80%).
- Example 32 The same procedure as in Example 32 was carried out, except that Inv 8 was used instead of Inv 9 to obtain Compound Cpd 266 (11.6 g, 80% yield).
- a compound Cpd 300 (11.6 g, yield 80%) was obtained in the same manner as in Example 34 except that Inv 12 was used instead of Inv 9.
- a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. 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, Hwasin Tech), and then the substrate using UV for 5 minutes The substrate was cleaned and transferred to a vacuum evaporator.
- ITO Indium tin oxide
- An organic electroluminescent device was manufactured in the same manner as in Example 1, except that each of the compounds shown in Table 1 was used instead of the compound Cpd137 used in Example 1.
- a green organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound Cpd137, which was used in Example 1, was not used.
- Example 1 Cpd 137 6.85 518 41.9
- Example 2 Cpd 138 6.71 520 41.5
- Example 3 Cpd 140 6.85 518 41.8
- Example 4 Cpd 149 6.85 520 41.8
- Example 5 Cpd 152 6.80 519 41.5
- Example 6 Cpd 161 6.90 518 41.8
- Example 7 Cpd 164 6.85 520 41.5
- Example 8 Cpd 170 6.73 518 41.5
- Example 9 Cpd 171 6.74 520 41.8
- Example 10 Cpd 194 6.75 518 41.8
- Example 11 Cpd 195 6.80 517 41.5
- Example 12 Cpd 218 6.77 518 42.0
- Example 13 Cpd 219 6.72 520 41.9
- Example 14 Cpd 242 6.80 518 41.5
- Example 15 Cpd 243 6.69 520 41.8
- Example 16 Cpd 266 6.82 517 41.8
- Example 17 Cpd 267 6.75 518 41.8
- the green organic electroluminescent device of Examples 1 to 29 using the compound according to the present invention as a light emitting auxiliary layer material, the green organic electric field of Comparative Example 1 using only CBP as a light emitting layer material without a light emitting auxiliary layer The driving voltage was slightly lower than that of the light emitting device, and the current efficiency was better than that of the green organic electroluminescent device of Comparative Example 1.
- a glass substrate coated with ITO Indium tin oxide
- ITO Indium tin oxide
- a solvent such as isopropyl alcohol, acetone, methanol, etc.
- UV OZONE cleaner Powersonic 405, Hwasin Tech
- a red organic electroluminescent device was manufactured in the same manner as in Example 30, except that each of the compounds shown in Table 2 was used instead of the compound Cpd137 used in Example 30.
- a red organic electroluminescent device was manufactured in the same manner as in Example 30, except that Compound Cpd137, which was used in Example 30, was not used.
- Example 30 Cpd 137 5.10 11.0
- Example 31 Cpd 138 5.15 11.3
- Example 32 Cpd 140 5.10 11.0
- Example 33 Cpd 149 5.15 11.3
- Example 34 Cpd 152 5.20 10.8
- Example 35 Cpd 161 5.13 11.1
- Example 36 Cpd 164 5.16 11.5
- Example 37 Cpd 170 5.17 11.6
- Example 38 Cpd 171 5.14 11.0
- Example 39 Cpd 194 5.15 10.8
- Example 40 Cpd 195 5.10 11.2
- Example 41 Cpd 218 5.15 11.0
- Example 42 Cpd 219 5.20 11.3
- Example 43 Cpd 242 5.15 11.0
- Example 44 Cpd 243 5.10 11.3
- Example 45 Cpd 266 5.15 10.8
- Example 46 Cpd 267 5.10 11.1
- Example 47 Cpd 290 5.15 11.5
- Example 48 Cpd 291 5.20 10.8
- Example 49 Cpd 314 5.
- the red organic electroluminescent devices of Examples 30 to 58 using the compound according to the present invention as the light emitting auxiliary layer material, the red organic electric field of Comparative Example 2 using only CBP as the light emitting layer material without a light emitting auxiliary layer It was found that the driving voltage was slightly lower than that of the light emitting device, and the current efficiency was better.
- a glass substrate coated with ITO Indium tin oxide
- ITO Indium tin oxide
- a solvent such as isopropyl alcohol, acetone, methanol, and drying was carried out, and then transferred to a UV OZONE cleaner (Powersonic 405, Hwasin Tech).
- the substrate was transferred to the evaporator.
- DS-205 Doosan (80 nm) / NPB (15 nm) / Compound Cpd 137 (15 nm) / ADN + 5% DS-405 (Doosan) (30 nm) / BCP (10 nm ) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) was laminated in order to prepare an organic EL device.
- the BCP used was as described in Example 1, and the structures of NPB and ADN are as follows.
- a blue organic electroluminescent device was manufactured in the same manner as in Example 59, except for using the compounds shown in Table 3 below instead of the compound Cpd137 used in Example 59.
- a blue organic electroluminescent device was manufactured in the same manner as in Example 59, except that Compound Cpd137, which was used in Example 59, was not used.
- Example 59 Cpd 137 5.60 6.6
- Example 60 Cpd 138 5.55 6.8
- Example 61 Cpd 140 5.60 6.9
- Example 62 Cpd 149 5.51 6.6
- Example 63 Cpd 152 5.55 6.8
- Example 64 Cpd 161 5.51 6.0
- Example 65 Cpd 164 5.55 6.4
- Example 66 Cpd 170 5.60 6.0
- Example 67 Cpd 171 5.65 6.4
- Example 68 Cpd 194 5.53 6.5
- Example 69 Cpd 195 5.56 6.8
- Example 70 Cpd 218 5.49 6.1
- Example 71 Cpd 219 5.50 6.9
- Example 72 Cpd 242 5.60 6.6
- Example 73 Cpd 243 5.55 6.8
- Example 74 Cpd 266 5.60 6.9
- Example 75 Cpd 267 5.51 6.6
- Example 76 Cpd 290 5.55 6.8
- Example 77 Cpd 291 5.
- a glass substrate coated with ITO Indium tin oxide
- ITO Indium tin oxide
- a solvent such as isopropyl alcohol, acetone, methanol, and drying
- UV OZONE cleaner Power sonic 405, Hwasin Tech
- M-MTDATA 60 nm) / TCTA (80 nm) / Compound Cpd1 + 10% Ir (ppy) 3 (30nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF ( 1 nm) / Al (200 nm) was laminated in order to manufacture an organic EL device.
- a green organic electroluminescent device was manufactured in the same manner as in Example 88, except for using the compounds described in Table 4 below instead of the compounds Cpd 1 used in Example 88.
- a green organic electroluminescent device was manufactured in the same manner as in Example 88, except that CBP was used instead of the compound Cdp1 used as the light emitting host material in forming the emission layer in Example 88.
- Example 88 Cpd 1 6.63 518 40.5
- Example 89 Cpd 8 6.78 515 42.4
- Example 90 Cpd 10 6.81 518 41.1
- Example 91 Cpd 11 6.79 517 40.8
- Example 92 Cpd 24 6.81 518 41.1
- Example 93 Cpd 28 6.79 517 40.8
- Example 94 Cpd 34 6.78 515 42.4
- Example 95 Cpd 39 6.81 518 41.1
- Example 96 Cpd 43 6.79 517 40.8
- Example 97 Cpd 46 6.81 518 41.1
- Example 98 Cpd 55 6.79 517 40.8
- Example 99 Cpd 56 6.79 517 40.8
- Example 100 Cpd 73 6.81 518 41.1
- Example 101 Cpd 84 6.79 517 40.8
- Example 102 Cpd 88 6.81 518 41.1
- Example 103 Cpd 100 6.78 515 42.4
- Example 104 Cpd 101 6.79 517 40.8
- a glass substrate coated with ITO Indium tin oxide
- ITO Indium tin oxide
- a solvent such as isopropyl alcohol, acetone, methanol, and drying
- UV OZONE cleaner Power sonic 405, Hwasin Tech
- a blue organic electroluminescent device was manufactured in the same manner as in Example 149, except for using CBP instead of the compound Cdp 1 used as a light emitting host material in forming the emission layer in Example 149.
- the blue organic electroluminescent devices of Examples 149 to 162 using the compound according to the present invention as a light emitting layer material compared with the blue organic electroluminescent device of Comparative Example 5, which uses a conventional CBP, have a current efficiency and drive. It was found that the better performance in terms of voltage.
- the present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.
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Abstract
The present invention relates to a novel compound and an organic electroluminescent device comprising same. The compound, according to the present invention, can be used in an organic layer, preferably a light-emitting layer, of an organic electroluminescent device and can enhance the light-emitting efficiency, driving voltage, life and the like of the organic electroluminescent device.
Description
본 발명은 유기 전계 발광 소자용 재료로서 사용될 수 있는 신규 유기 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.
1950년대 베르나소스(Bernanose)의 유기 박막 발광 관측을 시점으로 하여, 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계 발광(electroluminescent, EL) 소자에 대한 연구가 이어져 오다가, 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층구조의 유기 전계 발광 소자가 제시되었다. 이후, 고효율, 고수명의 유기 전계 발광 소자를 만들기 위하여, 소자 내 각각의 특징적인 유기물층을 도입하는 형태로 발전하여 왔으며, 이에 사용되는 특화된 물질의 개발로 이어졌다.Investigating organic electroluminescent (EL) devices that led to blue electroluminescence using anthracene single crystals in 1965, based on observation of Bernanose's organic thin-film emission, followed by Tang in 1987. ), An organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer is proposed. Since then, in order to make a high efficiency, high-life organic electroluminescent device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therein.
유기 전계 발광 소자는 두 전극 사이에 전압을 걸어주면 양극에서는 정공이 유기물층으로 주입되고, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 이때, 유기물층으로 사용되는 물질은 그 기능에 따라, 발광물질, 정공주입 물질, 정공수송 물질, 전자수송 물질, 전자주입 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 at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. In this case, 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.
발광 물질은 발광색에 따라 청색, 녹색, 적색 발광 물질과, 보다 나은 천연색을 구현하기 위한 노란색 및 주황색 발광 물질로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도펀트 계를 사용할 수 있다.The light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials for better natural colors according to light emission colors. In addition, a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
도펀트 물질은 유기 물질을 사용하는 형광 도펀트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도펀트로 나눌 수 있다. 이때, 인광 재료의 개발은 이론적으로 형광에 비해 4배까지 발광 효율을 향상시킬 수 있기 때문에, 인광 도펀트 뿐만 아니라 인광 호스트 재료들에 대한 연구도 많이 진행되고 있다.The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times compared to the fluorescence, studies on phosphorescent host materials as well as phosphorescent dopants have been conducted.
현재까지 정공 주입층, 정공 수송층. 정공 차단층, 전자 수송층 재료로는 NPB, BCP, Alq3 등이 널리 알려져 있으며, 발광층 재료로는 안트라센 유도체들이 보고되고 있다. 특히, 발광층 재료 중 효율 향상 측면에서 장점을 가지고 있는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 청색(blue), 녹색(green), 적색(red)의 인광 도판트 재료로 사용되고 있으며, 4,4-디카바졸리비페닐(4,4-dicarbazolybiphenyl, CBP)은 인광 호스트 재료로 사용되고 있다.Hole injection layer, hole transport layer to date. NPB, BCP, Alq 3 and the like are widely known as the hole blocking layer and the electron transporting layer material, and anthracene derivatives have been reported as the light emitting layer material. Particularly, metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 , which have advantages in terms of efficiency improvement among the light emitting layer materials, are blue, green, and red. (red) is used as the phosphorescent dopant material, 4,4-dicarbazolybiphenyl (CBP) is used as the phosphorescent host material.
그러나 종래의 유기물층 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮아 열적 안정성이 매우 좋지 않기 때문에, 유기 전계 발광 소자의 수명 측면에서 만족할 만한 수준이 되지 못하고 있다. 따라서, 성능이 뛰어난 유기물층 재료의 개발이 요구되고 있다.However, the conventional organic material has an advantageous aspect in terms of light emission characteristics, but the thermal stability is not very good due to the low glass transition temperature, it is not a satisfactory level in terms of the life of the organic EL device. Therefore, development of an organic material layer material excellent in performance is desired.
본 발명은 상기한 문제점을 해결하기 위해, 유기 전계 발광 소자의 효율, 수명 및 안정성 등을 향상시킬 수 있는 신규 화합물 및 상기 화합물을 이용한 유기 전계 발광 소자를 제공하는 것을 목적으로 한다.In order to solve the above problems, an object of the present invention is to provide a novel compound and an organic electroluminescent device using the compound which can improve the efficiency, lifespan and stability of the organic electroluminescent device.
상기한 목적을 달성하기 위해, 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:In order to achieve the above object, the present invention provides a compound represented by the following formula (1):
[화학식 1][Formula 1]
상기 화학식 1에서,In Chemical Formula 1,
R1과 R2, R2와 R3, R3와 R4, R5와 R6, R6과 R7, R7과 R8 중 적어도 하나는 하기 화학식 2로 표시되는 고리와 축합되어 축합 고리를 형성하며;At least one of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 is condensed and condensed with a ring represented by the following formula (2) To form a ring;
하기 화학식 2로 표시되는 고리와 축합 고리를 형성하지 않는 R1 내지 R8은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되며; R 1 to R 8 which do not form a ring and a condensed ring represented by the following formula (2) are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenes group, C 2 ~ C 40 of the 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 60 heteroaryl group , C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group , C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylamine group is selected from ;
상기 R1 내지 R8의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하며;The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 1 to R 8 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ selected from the group consisting of C 60 aryl silyl Substituted with one or more substituents being unsubstituted or, if substituted by a plurality of substituents, they are same or different from each other;
[화학식 2][Formula 2]
상기 화학식 2에서, In Chemical Formula 2,
점선은 축합이 이루어지는 부분이며;The dotted line is the part where condensation takes place;
X1은 C(Ar1)(Ar2), N(Ar3), O, S 및 Si(Ar4)(Ar5)로 이루어진 군에서 선택되며;X 1 is selected from the group consisting of C (Ar 1 ) (Ar 2 ), N (Ar 3 ), O, S and Si (Ar 4 ) (Ar 5 );
Ar1 및 Ar2는 각각 독립적으로 C1~C40의 알킬기 또는 C6~C60의 아릴기이고; Ar 1 and Ar 2 are each independently C 1 -C 40 alkyl group or C 6 -C 60 aryl group;
Ar3 내지 Ar5는 각각 독립적으로 하기 화학식 3으로 표시되는 치환기이며;Ar 3 to Ar 5 are each independently a substituent represented by the following formula (3);
Y1 내지 Y4는 각각 독립적으로 N 또는 C(R9)이며;Y 1 to Y 4 are each independently N or C (R 9 );
R9는 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하고, 상기 R9가 복수 개인 경우 복수 개의 R9는 서로 동일하거나 상이하며; R 9 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, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phospha Or a C 6 to C 60 mono or diarylphosphinyl group and a C 6 to C 60 arylamine group, or combine with an adjacent group to form a condensed ring, and a plurality of R 9 plural R 9 are the same as or different from each other;
상기 Ar1 및 Ar2의 알킬기 및 아릴기와, 상기 R9의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하며;The alkyl group and aryl group of Ar 1 and Ar 2, the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group of R 9 , Alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, an aryloxy group of C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ C 60 of, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl group of boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ C 60 aryl It substituted with one or more substituents selected from the group consisting of a reel or is unsubstituted, in the case where the substitution of a plurality of substituents, they are same or different from each other;
[화학식 3][Formula 3]
상기 화학식 3에서,In Chemical Formula 3,
*는 상기 화학식 2에 결합되는 부분을 의미하고;* Means a moiety bonded to Formula 2;
L1 및 L2는 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되며; L 1 and L 2 are each independently 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;
R10은 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하며; R 10 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, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phospha A aryl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring;
상기 L1 및 L2의 아릴렌기 및 헤테로아릴렌기와, 상기 R10의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다. Wherein L 1 and the L 2 arylene group and a heteroarylene group, an alkyl group of the R 10, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl The amine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 An alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 6 to C 60 aryl group, a nuclear atom having 5 to 60 heteroaryl groups, a C 6 to C 60 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phosphanyl group, C 6 ~ C 60 Mono or diaryl phosphinyl group and C 6 ~ C 6 When unsubstituted or substituted with one or more substituents selected from the group consisting of 0 arylsilyl groups, they are the same or different from each other.
본 발명은 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중에서 적어도 하나는 상기 화학식 1의 화합물을 포함하는 유기 전계 발광 소자를 제공한다.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 provides an organic electroluminescent device comprising the compound of Formula 1. .
본 발명에서의 "알킬"은 탄소수 1 내지 40개의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등이 있는데, 이에 한정되지 않는다."Alkyl" in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl And the like, but are not limited thereto.
본 발명에서의 "알케닐(alkenyl)"은 탄소-탄소 이중 결합을 1개 이상 가진, 탄소수 2 내지 40개의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등이 있는데, 이에 한정되지 않는다."Alkenyl" in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having at least one carbon-carbon double bond, and examples thereof include vinyl, Allyl, isopropenyl, 2-butenyl, and the like, but is not limited thereto.
본 발명에서의 "알키닐(alkynyl)"은 탄소-탄소 삼중 결합을 1개 이상 가진, 탄소수 2 내지 40개의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등이 있는데, 이에 한정되지 않는다."Alkynyl" in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having at least one carbon-carbon triple bond, examples of which are ethynyl. , 2-propynyl, and the like, but is not limited thereto.
본 발명에서의 "아릴"은 단독 고리 또는 2 이상의 고리가 조합된, 탄소수 6 내지 60개의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 축합되어 있고, 고리 형성 원자로서 탄소만을 포함(예를 들어, 탄소수는 8 내지 60일 수 있음)하고, 분자 전체가 비-방향족성(non-aromacity)를 갖는 1가 치환기도 포함될 수 있다. 이러한 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴, 플루오레닐 등이 있는데, 이에 한정되지 않는다. 본 발명에서의 "헤테로아릴"은 핵원자수 5 내지 60개의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, P, S 및 Se 중에서 선택된 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합되어 있고, 고리 형성 원자로서 탄소 외에 N, O, P, S 및 Se 중에서 선택된 헤테로 원자를 포함하고, 분자 전체가 비-방향족성(non-aromacity)를 갖는 1가 그룹도 포함하는 것으로 해석된다. 이러한 헤테로아릴의 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6-원 모노사이클릭 고리; 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리; 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등이 있는데, 이에 한정되지 않는다."Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. In addition, monovalent having two or more rings condensed with each other, containing only carbon as a ring forming atom (for example, carbon number may be 8 to 60), and the whole molecule is non-aromacity. Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and the like. "Heteroaryl" in the present invention means a monovalent substituent derived from a 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 selected from N, O, P, S and Se. In addition, two or more rings are simply pendant or condensed with each other, and in addition to carbon as a ring forming atom, a hetero atom selected from N, O, P, S and Se, the entire molecule is non-aromatic (non- It is also interpreted to include monovalent groups having aromacity). Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
본 발명에서의 "아릴옥시"는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 5 내지 60개의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등이 있는데, 이에 한정되지 않는다.In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
본 발명에서의 "알킬옥시"는 R'O-로 표시되는 1가의 치환기로, 상기 R'는 1 내지 40개의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함하는 것으로 해석한다. 이러한 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등이 있는데, 이에 한정되지 않는다.In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl, and is linear, branched or cyclic structure. Interpret as including. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
본 발명에서의 "아릴아민"은 탄소수 6 내지 60개의 아릴로 치환된 아민을 의미한다."Arylamine" in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
본 발명에서의 "시클로알킬"은 탄소수 3 내지 40개의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 놀보닐(norbornyl), 아다만틴(adamantine) 등이 있는데, 이에 한정되지 않는다.By "cycloalkyl" in the present invention is meant monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
본 발명에서의 "헤테로시클로알킬"은 핵원자수 3 내지 40개의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로 원자로 치환된다. 이러한 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등이 있는데, 이에 한정되지 않는다."Heterocycloalkyl" in the present invention means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons of nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
본 발명에서의 "알킬실릴"은 탄소수 1 내지 40개의 알킬로 치환된 실릴이고, "아릴실릴"은 탄소수 5 내지 60개의 아릴로 치환된 실릴을 의미한다.In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 60 carbon atoms.
본 발명에서의 "축합 고리"는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다."Condensed ring" in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.
본 발명의 화합물은 열적 안정성, 캐리어 수송능, 발광능 등이 우수하기 때문에 유기 전계 발광 소자의 유기물층 재료로 유용하게 적용될 수 있다.Since the compound of the present invention has excellent thermal stability, carrier transporting ability, light emitting ability, and the like, it can be usefully applied as an organic material layer material of an organic EL device.
또한, 본 발명의 화합물을 유기물층에 포함하는 유기 전계 발광 소자는 발광성능, 구동전압, 수명, 효율 등의 측면이 크게 향상되어 풀 칼라 디스플레이 패널 등에 효과적으로 적용될 수 있다.In addition, the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full color display panel since the aspect of light emission performance, driving voltage, lifespan, efficiency, etc. is greatly improved.
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, R5와 R6, R6과 R7, R7과 R8 중 적어도 하나는 하기 화학식 2로 표시되는 고리와 축합되어 축합 고리를 형성하며;At least one of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 is condensed and condensed with a ring represented by the following formula (2) To form a ring;
하기 화학식 2로 표시되는 고리와 축합 고리를 형성하지 않는 R1 내지 R8은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되며; R 1 to R 8 which do not form a ring and a condensed ring represented by the following formula (2) are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenes group, C 2 ~ C 40 of the 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 60 heteroaryl group , C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group , C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylamine group is selected from ;
상기 R1 내지 R8의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하며;The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 1 to R 8 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ selected from the group consisting of C 60 aryl silyl Substituted with one or more substituents being unsubstituted or, if substituted by a plurality of substituents, they are same or different from each other;
[화학식 2][Formula 2]
상기 화학식 2에서, In Chemical Formula 2,
점선은 축합이 이루어지는 부분이며;The dotted line is the part where condensation takes place;
X1은 C(Ar1)(Ar2), N(Ar3), O, S 및 Si(Ar4)(Ar5)로 이루어진 군에서 선택되며;X 1 is selected from the group consisting of C (Ar 1 ) (Ar 2 ), N (Ar 3 ), O, S and Si (Ar 4 ) (Ar 5 );
Ar1 및 Ar2는 각각 독립적으로 C1~C40의 알킬기 또는 C6~C60의 아릴기이고; Ar 1 and Ar 2 are each independently C 1 -C 40 alkyl group or C 6 -C 60 aryl group;
Ar3 내지 Ar5는 각각 독립적으로 하기 화학식 3으로 표시되는 치환기이며;Ar 3 to Ar 5 are each independently a substituent represented by the following formula (3);
Y1 내지 Y4는 각각 독립적으로 N 또는 C(R9)이며;Y 1 to Y 4 are each independently N or C (R 9 );
R9는 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하고, 상기 R9가 복수 개인 경우 복수 개의 R9는 서로 동일하거나 상이하며; R 9 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, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phospha Or a C 6 to C 60 mono or diarylphosphinyl group and a C 6 to C 60 arylamine group, or combine with an adjacent group to form a condensed ring, and a plurality of R 9 plural R 9 are the same as or different from each other;
상기 Ar1 및 Ar2의 알킬기 및 아릴기와, 상기 R9의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하며;The alkyl group and aryl group of Ar 1 and Ar 2, the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group of R 9 , Alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, an aryloxy group of C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ C 60 of, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl group of boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ C 60 aryl It substituted with one or more substituents selected from the group consisting of a reel or is unsubstituted, in the case where the substitution of a plurality of substituents, they are same or different from each other;
[화학식 3][Formula 3]
상기 화학식 3에서,In Chemical Formula 3,
*는 상기 화학식 2에 결합되는 부분을 의미하고;* Means a moiety bonded to Formula 2;
L1 및 L2는 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되며; L 1 and L 2 are each independently 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;
R10은 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하며; R 10 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, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phospha A aryl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring;
상기 L1 및 L2의 아릴렌기 및 헤테로아릴렌기와, 상기 R10의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다. Wherein L 1 and the L 2 arylene group and a heteroarylene group, an alkyl group of the R 10, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl The amine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 An alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 6 to C 60 aryl group, a nuclear atom having 5 to 60 heteroaryl groups, a C 6 to C 60 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phosphanyl group, C 6 ~ C 60 Mono or diaryl phosphinyl group and C 6 ~ C 6 When unsubstituted or substituted with one or more substituents selected from the group consisting of 0 arylsilyl groups, they are the same or different from each other.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
1.One.
신규 유기 화합물New organic compounds
본 발명의 신규 화합물은 하기 화학식 1로 표시될 수 있다:The novel compounds of the present invention can be represented by the following formula (1):
[화학식 1][Formula 1]
상기 화학식 1에서,In Chemical Formula 1,
R1과 R2, R2와 R3, R3와 R4, R5와 R6, R6과 R7, R7과 R8 중 적어도 하나는 하기 화학식 2로 표시되는 고리와 축합되어 축합 고리를 형성하나, 상기 R1과 R2, R2와 R3, R3와 R4, R5와 R6, R6과 R7, R7과 R8 중 2 이상이 하기 화학식 2로 표시되는 고리와 축합되는 경우, 각각 축합되는 화학식 2로 표시되는 고리는 동일하거나 상이하며;At least one of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 is condensed and condensed with a ring represented by the following formula (2) Form a ring, but at least two of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 are represented by the following Chemical Formula 2 When condensed with a ring, the rings represented by the formula (2) which are respectively condensed are the same or different;
하기 화학식 2로 표시되는 고리와 축합 고리를 형성하지 않는 R1 내지 R8은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되며; R 1 to R 8 which do not form a ring and a condensed ring represented by the following formula (2) are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenes group, C 2 ~ C 40 of the 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 60 heteroaryl group , C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group , C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylamine group is selected from ;
상기 R1 내지 R8의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하며;The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 1 to R 8 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ selected from the group consisting of C 60 aryl silyl Substituted with one or more substituents being unsubstituted or, if substituted by a plurality of substituents, they are same or different from each other;
[화학식 2][Formula 2]
상기 화학식 2에서, In Chemical Formula 2,
점선은 축합이 이루어지는 부분이며;The dotted line is the part where condensation takes place;
X1은 C(Ar1)(Ar2), N(Ar3), O, S 및 Si(Ar4)(Ar5)로 이루어진 군에서 선택되고, 상기 X1이 복수 개인 경우 이들은 서로 동일하거나 상이하고, 바람직하게는 C(Ar1)(Ar2) 또는 N(Ar3)이며;X 1 is selected from the group consisting of C (Ar 1 ) (Ar 2 ), N (Ar 3 ), O, S and Si (Ar 4 ) (Ar 5 ), and when there are a plurality of X 1 , they are the same as each other or Different, preferably C (Ar 1 ) (Ar 2 ) or N (Ar 3 );
Ar1 및 Ar2는 각각 독립적으로 C1~C40의 알킬기 또는 C6~C60의 아릴기이고; Ar 1 and Ar 2 are each independently C 1 -C 40 alkyl group or C 6 -C 60 aryl group;
Ar3 내지 Ar5는 각각 독립적으로 하기 화학식 3으로 표시되는 치환기이며;Ar 3 to Ar 5 are each independently a substituent represented by the following formula (3);
Y1 내지 Y4는 각각 독립적으로 N 또는 C(R9)이며;Y 1 to Y 4 are each independently N or C (R 9 );
R9는 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하고, 상기 R9가 복수 개인 경우 복수 개의 R9는 서로 동일하거나 상이하며; R 9 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, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phospha Or a C 6 to C 60 mono or diarylphosphinyl group and a C 6 to C 60 arylamine group, or combine with an adjacent group to form a condensed ring, and a plurality of R 9 plural R 9 are the same as or different from each other;
상기 Ar1 및 Ar2의 알킬기 및 아릴기와, 상기 R9의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하며;The alkyl group and aryl group of Ar 1 and Ar 2, the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group of R 9 , Alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, an aryloxy group of C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ C 60 of, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl group of boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ C 60 aryl It substituted with one or more substituents selected from the group consisting of a reel or is unsubstituted, in the case where the substitution of a plurality of substituents, they are same or different from each other;
[화학식 3][Formula 3]
상기 화학식 3에서,In Chemical Formula 3,
*는 상기 화학식 2에 결합되는 부분을 의미하고;* Means a moiety bonded to Formula 2;
L1 및 L2는 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되며; L 1 and L 2 are each independently 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;
R10은 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하며; R 10 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, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phospha A aryl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring;
상기 L1 및 L2의 아릴렌기 및 헤테로아릴렌기와, 상기 R10의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다. Wherein L 1 and the L 2 arylene group and a heteroarylene group, an alkyl group of the R 10, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl The amine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 An alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 6 to C 60 aryl group, a nuclear atom having 5 to 60 heteroaryl groups, a C 6 to C 60 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phosphanyl group, C 6 ~ C 60 Mono or diaryl phosphinyl group and C 6 ~ C 6 When unsubstituted or substituted with one or more substituents selected from the group consisting of 0 arylsilyl groups, they are the same or different from each other.
일반적으로 유기 전계 발광 소자에 포함되는 유기물층 중에서 인광 발광층은 색순도의 증가와 발광 효율을 증가시키기 위해 호스트 및 도펀트를 포함한다. 이때, 상기 호스트는 삼중항 에너지 갭이 도펀트보다 높아야 한다. 즉, 도펀트로부터 효과적으로 인광 발광을 제공하기 위해서는 호스트의 가장 낮은 여기 상태의 에너지가 도펀트의 가장 낮은 방출 상태의 에너지보다 높아야 한다.In general, the phosphorescent light emitting layer of the organic material layer included in the organic electroluminescent device includes a host and a dopant to increase the color purity and the luminous efficiency. At this time, the host should have a triplet energy gap higher than the dopant. That is, in order to effectively provide phosphorescence from the dopant, the energy of the lowest excited state of the host must be higher than the energy of the lowest emission state of the dopant.
그런데, 본 발명에서 제공하는 상기 화학식 1로 표시되는 화합물의 경우, 싸이안스렌의 구조 부분이 넓은 일중항 에너지 준위와 높은 삼중항 에너지 준위를 갖는다. 더 나아가 이러한 싸이안스렌에 축합된 인덴 또는 인돌 모이어티 등에 특정의 치환기가 도입됨으로써, 상기 화학식 1의 화합물이 발광층의 호스트로 적용될 경우, 도펀트보다 높은 에너지 준위를 나타낼 수 있다.By the way, in the case of the compound represented by the formula (1) provided in the present invention, the structural portion of the cyanrene has a wide singlet energy level and a high triplet energy level. Furthermore, by introducing a specific substituent such as indene or indole moiety condensed into such cyanrene, when the compound of Formula 1 is applied as a host of the light emitting layer, it may exhibit a higher energy level than the dopant.
또한, 상기 화학식 1로 표시되는 화합물은 상기한 바와 같이 높은 삼중항 에너지를 갖기 때문에, 발광층에서 생성된 엑시톤(exciton)이 인접하는 전자 수송층 또는 정공 수송층으로 확산(이동)되는 것을 방지할 수 있다. 따라서, 상기 화학식 1의 화합물을 이용하여 정공 수송층과 발광층 사이에 유기물층(이하, '발광 보조층'이라 함)을 형성하거나 또는 발광층과 전자 수송층 사이에 유기물층(이하, '전자 수송 보조층'이라 함)을 형성할 경우, 상기 화합물에 의해 엑시톤의 확산이 방지되기 때문에, 상기 발광 보조층이나 전자 수송 보조층을 포함하지 않은 종래 유기 전계 발광 소자와 달리, 실질적으로 발광층 내에서 발광에 기여하는 엑시톤의 수가 증가되어 소자의 발광 효율이 개선될 수 있다. In addition, since the compound represented by Chemical Formula 1 has a high triplet energy as described above, it is possible to prevent the exciton generated in the light emitting layer from being diffused (moved) to the adjacent electron transport layer or the hole transport layer. Therefore, an organic material layer (hereinafter, referred to as a 'light emitting auxiliary layer') is formed between the hole transport layer and the light emitting layer by using the compound of Formula 1, or an organic material layer (hereinafter referred to as an 'electron transport auxiliary layer') between the light emitting layer and the electron transporting layer. ), Since the diffusion of the exciton is prevented by the compound, unlike the conventional organic electroluminescent device that does not include the light emitting auxiliary layer or the electron transporting auxiliary layer, the excitons substantially contribute to light emission in the light emitting layer. The number can be increased to improve the luminous efficiency of the device.
더욱이, 상기 화학식 1로 표시되는 화합물은 상기 기본 골격에 도입되는 치환기에 따라 HOMO 및 LUMO에너지 레벨이 조절될 수 있어, 넓은 밴드갭 및 높은 캐리어 수송성을 가질 수 있다. Furthermore, the compound represented by Chemical Formula 1 may have HOMO and LUMO energy levels controlled according to substituents introduced into the basic skeleton, thereby having a wide bandgap and high carrier transport properties.
게다가, 본 발명의 상기 화학식 1로 표시되는 화합물에서 큰 전자 주게기(electron donating group, EDG)가 결합될 경우, 정공 수송층 재료로 용이하게 사용할 수 있다. 또한, 상기 화학식 1로 표시되는 화합물의 기본 골격에 전자 흡수성이 큰 전자 끌개기(electron withdrawing group, EWG)가 결합될 경우, 분자 전체가 양극성의(bipolar) 특성을 가져 정공과 전자의 결합력을 높일 수 있다. In addition, when a large electron donating group (EDG) is combined in the compound represented by Chemical Formula 1 of the present invention, it may be easily used as a hole transport layer material. In addition, when an electron withdrawing group (EWG) having high electron absorption is coupled to the basic skeleton of the compound represented by Chemical Formula 1, the entire molecule has a bipolar characteristic to increase the binding force between holes and electrons. Can be.
더 나아가, 본 발명의 화학식 1로 표시되는 화합물은 상기 기본 골격에 다양한 치환기, 특히 아릴기 및/또는 헤테로아릴기가 도입됨으로써, 화합물의 분자량이 유의적으로 증대되고, 따라서 유리 전이온도가 향상되어 종래의 유기물층 재료(예를 들어, CBP)보다 높은 열적 안정성을 가질 수 있다. 또한, 본 발명의 화학식 1로 표시되는 화합물은 유기물층의 결정화 억제에도 효과가 있다.Furthermore, the compound represented by the general formula (1) of the present invention has a significant increase in the molecular weight of the compound by introducing a variety of substituents, in particular aryl group and / or heteroaryl group to the basic skeleton, thus improving the glass transition temperature It may have a higher thermal stability than the organic material of the material (for example, CBP). In addition, the compound represented by the formula (1) of the present invention is also effective in suppressing the crystallization of the organic material layer.
이렇듯, 본 발명에서 상기 화학식 1로 표시되는 화합물을 유기 전계 발광 소자의 유기물층 재료, 바람직하게는 발광층 재료(청색, 녹색 및/또는 적색의 인광 호스트 재료), 전자 수송층/주입층 재료, 정공 수송층/주입층 재료, 발광 보조층 재료, 수명 개선층 재료로 적용할 경우, 유기 전계 발광 소자의 성능 및 수명 특성이 크게 향상될 수 있다. 이러한 유기 전계 발광 소자는 결과적으로 풀 칼라 유기 발광 패널의 성능을 극대화시킬 수 있다.As such, the compound represented by Chemical Formula 1 in the present invention may be an organic material layer material of an organic electroluminescent device, preferably an emission layer material (blue, green and / or red phosphorescent host material), an electron transport layer / injection layer material, a hole transport layer / When applied as an injection layer material, a light emission auxiliary layer material, or a life improvement layer material, the performance and life characteristics of the organic EL device may be greatly improved. As a result, the organic EL device may maximize the performance of the full color organic light emitting panel.
본 발명의 바람직한 한 구현 예에 따르면, 넓은 밴드갭과 발광 특성 및 열적 안정성을 고려했을 때, 상기 Y1 내지 Y4 모두가 C(R9)인 것이 바람직하며, 복수 개의 C(R9)는 서로 동일하거나 상이할 수 있다.According to a preferred embodiment of the present invention, in consideration of the wide bandgap, luminescence properties and thermal stability, it is preferable that all of Y 1 to Y 4 is C (R 9 ), a plurality of C (R 9 ) is It may be the same or different from each other.
또한, 본 발명의 바람직한 한 구현 예에 따르면, 상기 화학식 2로 표시되는 축합 고리는 하기 화학식 4로 표시되는 축합 고리일 수 있다:In addition, according to a preferred embodiment of the present invention, the condensed ring represented by the formula (2) may be a condensed ring represented by the following formula (4):
[화학식 4][Formula 4]
상기 화학식 4에서, In Chemical Formula 4,
점선은 축합이 이루어지는 부분이며;The dotted line is the part where condensation takes place;
X2는 C(Ar1)(Ar2), N(Ar3), O, S 및 Si(Ar4)(Ar5)로 이루어진 군에서 선택되고, 바람직하게는 C(Ar1)(Ar2) 또는 N(Ar3)이며;X 2 is selected from the group consisting of C (Ar 1 ) (Ar 2 ), N (Ar 3 ), O, S and Si (Ar 4 ) (Ar 5 ), preferably C (Ar 1 ) (Ar 2 ) Or N (Ar 3 );
Ar1 및 Ar2는 각각 독립적으로 C1~C40의 알킬기 또는 C6~C60의 아릴기이고; Ar 1 and Ar 2 are each independently C 1 -C 40 alkyl group or C 6 -C 60 aryl group;
Ar3 내지 Ar5는 각각 독립적으로 하기 화학식 3으로 표시되는 치환기이며;Ar 3 to Ar 5 are each independently a substituent represented by the following formula (3);
R11 내지 R14는 각각 독립적으로 하기 화학식 5으로 표시되는 치환기이거나, 인접하는 기와 결합하여 축합 고리를 형성하며; R 11 to R 14 are each independently a substituent represented by Formula 5, or combine with an adjacent group to form a condensed ring;
[화학식 3][Formula 3]
[화학식 5][Formula 5]
상기 화학식 3 및 5에서,In Chemical Formulas 3 and 5,
*는 상기 화학식 4에 결합되는 부분을 의미하고;* Means a moiety bound to Formula 4;
L1 내지 L4는 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되며; L 1 to L 4 are each independently 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;
R10 및 R19는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되며; R 10 and R 19 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, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ for C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ is selected from the group consisting of an aryl amine of the C 60 of the;
상기 L1 내지 L4의 아릴렌기 및 헤테로아릴렌기와, 상기 R10 및 R19의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.The arylene group and heteroarylene group of L 1 to L 4 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl of R 10 and R 19 Alkyl, arylamine, alkylsilyl, alkylboron, arylboron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1- C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 6 -C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 6 -C 60 aryl Oxy group, C 1 -C 40 alkyloxy group, C 6 -C 60 arylamine group, C 3 -C 40 cycloalkyl group, nuclear atom of 3-40 heterocycloalkyl group, C 1 -C 40 alkyl Silyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diarylphosphinyl group And when substituted or unsubstituted with one or more substituents selected from the group consisting of C 6 ~ C 60 arylsilyl group, and substituted with a plurality of substituents, they are the same or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R11과 R12, R12와 R13, R13과 R14 중 적어도 하나는 하기 화학식 6으로 표시되는 고리와 축합되어 축합고리를 형성할 수 있고, 여기서 상기 R11과 R12, R12와 R13, R13과 R14 중 2 이상이 하기 화학식 6으로 표시되는 고리와 축합되는 경우, 각각 축합되는 화학식 6으로 표시되는 고리는 동일하거나 상이하며;According to one preferred embodiment of the present invention, at least one of the R 11 and R 12 , R 12 and R 13 , R 13 and R 14 may be condensed with a ring represented by the following formula (6) to form a condensed ring, Wherein when two or more of R 11 and R 12 , R 12 and R 13 , R 13 and R 14 are condensed with a ring represented by the following Chemical Formula 6, the rings represented by Chemical Formula 6 to be condensed are the same or different;
[화학식 6] [Formula 6]
상기 화학식 6에서,In Chemical Formula 6,
점선은 축합이 이루어지는 부분이며;The dotted line is the part where condensation takes place;
X3는 C(Ar6)(Ar7), N(Ar8), O, S 및 Si(Ar9)(Ar10)으로 이루어진 군에서 선택되고, 바람직하게는 C(Ar6)(Ar7) 또는 N(Ar8)이며;X 3 is selected from the group consisting of C (Ar 6 ) (Ar 7 ), N (Ar 8 ), O, S and Si (Ar 9 ) (Ar 10 ), preferably C (Ar 6 ) (Ar 7 ) ) Or N (Ar 8 );
Ar6 및 Ar7는 각각 독립적으로 C1~C40의 알킬기 또는 C6~C60의 아릴기이며;Ar 6 and Ar 7 are each independently an alkyl group of C 1 to C 40 or an aryl group of C 6 to C 60 ;
Ar8 내지 Ar10과 R15 내지 R18은 각각 독립적으로 하기 화학식 7로 표시되는 치환기이며;Ar 8 to Ar 10 and R 15 to R 18 are each independently a substituent represented by formula (7);
[화학식 7][Formula 7]
상기 화학식 7에서,In Chemical Formula 7,
*는 상기 화학식 6에 결합되는 부분을 의미하고;* Means a moiety bound to Formula 6;
L5 및 L6은 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되며; L 5 and L 6 are each independently 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;
R20은 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되며; R 20 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, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phospha A silyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group;
상기 L5 및 L6의 아릴렌기 및 헤테로아릴렌기와, 상기 R20의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.Alkyl groups of the L 5 and L 6 arylene group and a heteroarylene group, the R 20 of the group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl The amine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 An alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 6 to C 60 aryl group, a nuclear atom having 5 to 60 heteroaryl groups, a C 6 to C 60 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phosphanyl group, C 6 ~ C 60 Mono or diaryl phosphinyl group and C 6 ~ C 6 When unsubstituted or substituted with one or more substituents selected from the group consisting of 0 arylsilyl groups, they are the same or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 화합물은 하기 화학식 8내지 20 중 어느 하나로 표시되는 화합물일 수 있다:According to one preferred embodiment of the present invention, the compound may be a compound represented by any one of the following Formula 8 to 20:
[화학식 8][Formula 8]
[화학식 9][Formula 9]
[화학식 10][Formula 10]
[화학식 11][Formula 11]
[화학식 12][Formula 12]
[화학식 13][Formula 13]
[화학식 14][Formula 14]
[화학식 15][Formula 15]
[화학식 16][Formula 16]
[화학식 17][Formula 17]
[화학식 18][Formula 18]
[화학식 19][Formula 19]
[화학식 20][Formula 20]
상기 화학식 8 내지 20에서, In Chemical Formulas 8 to 20,
X2, X3, R1 내지 R5, R7, R8 및 R11 내지 R18 각각은 상기 화학식 1, 4 및 6에서 정의된 바와 같다.X 2 , X 3 , R 1 to R 5 , R 7 , R 8 and R 11 to R 18 are each as defined in Chemical Formulas 1, 4, and 6.
본 발명의 바람직한 한 구현 예에 따르면, 상기 L1 내지 L6은 각각 독립적으로 단일결합이거나 하기 화학식 A-1 내지 A-6 중 어느 하나로 표시되는 링커일 수 있다:According to one preferred embodiment of the present invention, each of L 1 to L 6 may be independently a single bond or a linker represented by any one of the following Formulas A-1 to A-6:
상기 화학식 A-1 내지 A-6에서,In Chemical Formulas A-1 to A-6,
*는 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
X4 및 X5은 각각 독립적으로 O, S, N(R22) 또는 C(R23)(R24)이며;X 4 and X 5 are each independently O, S, N (R 22 ) or C (R 23 ) (R 24 );
X6는 N 또는 C(R25)이며;X 6 is N or C (R 25 );
p는 0 내지 4의 정수이며;p is an integer from 0 to 4;
R21은 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R21이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 21 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 groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups, C An alkylsilyl group of 3 to C 40 , an arylsilyl group of C 6 to C 60 , an alkyl boron group of C 1 to C 40, an aryl boron group of C 6 to C 60 , an arylphosphanyl group of C 6 to C 60 , A C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylamine group may be selected from the group consisting of or combined with adjacent groups to form a condensed ring, when there are a plurality of R 21 They are mutually Same or different;
R22 내지 R25는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고;R 22 to R 25 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 6 ~ C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 aryl phosphazene group, selected from the group consisting arylsilyl a C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 of, or by combining tile adjacent to which they are attached may form a condensed ring;
상기 R21 내지 R25의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 21 to R 25 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 Aryl boron group of ~ C 60 , C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylsilyl group When substituted or unsubstituted with one or more substituents, and substituted with a plurality of substituents, they may be the same or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R10, R19 및 R20 중 적어도 하나는 하기 화학식 B-1 내지 B-7 중 어느 하나로 표시되는 치환기이며, 상기 R10, R19 및 R20은 서로 동일하거나 상이할 수 있다:According to one embodiment, the preferred of the invention, the R 10, R 19 and R 20 of an at least one substituent represented by any one of the following formulas B-1 to B-7, wherein R 10, R 19 and R 20 is It can be the same or different from each other:
상기 화학식 B-1 내지 B-7에서,In Chemical Formulas B-1 to B-7,
*는 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
Z1 내지 Z5는 각각 독립적으로 N 또는 C(R30)이며;Z 1 to Z 5 are each independently N or C (R 30 );
T1 및 T2는 각각 독립적으로 단일결합, C(R31)(R32), N(R33), O 및 S로 이루어진 군에서 선택되나, T1 및 T2 모두가 단일결합은 아니며;T 1 and T 2 are each independently selected from the group consisting of a single bond, C (R 31 ) (R 32 ), N (R 33 ), O and S, but not both T 1 and T 2 are single bonds;
q 및 r은 각각 독립적으로 0 내지 4의 정수이며;q and r are each independently integers of 0 to 4;
R26 및 R27은 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 또는 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R26 및 R27 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 26 and R 27 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 60 the aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an aryloxy group of C 6 ~ C 60, C 1 ~ C 40 alkyloxy group of, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 Heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylsilyl group, or may be combined with an adjacent group to form a condensed ring, and When there are a plurality of R 26 and R 27 s , they are the same as or different from each other;
R28 내지 R33은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R30 내지 R33 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 28 to R 33 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 6 ~ C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 aryl phosphazene group, selected from the group consisting of C 6 ~ C 60 mono or diaryl the Phosphinicosuccinic group and a C 6 ~ with an aryl silyl group of C 60, or combine tile adjacent to which they are attached may form a fused ring, When each of R 30 to R 33 is plural, they are the same as or different from each other;
상기 R26 내지 R33의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 26 to R 33 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 Aryl boron group of ~ C 60 , C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylsilyl group When substituted or unsubstituted with one or more substituents, and substituted with a plurality of substituents, they may be the same or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R10, R19 및 R20 중 적어도 하나는 하기 화학식 C-1 내지 C-24 중 어느 하나로 표시되는 치환기일 수 있고, 상기 R10, R19 및 R20은 서로 동일하거나 상이할 수 있다:According to one preferred embodiment of the present invention, at least one of the R 10 , R 19 and R 20 may be a substituent represented by any one of the formulas C-1 to C-24, the R 10 , R 19 and R 20 may be the same or different from each other:
상기 화학식 C-1 내지 C-24에서,In Chemical Formulas C-1 to C-24,
*은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
t는 0 내지 5의 정수이며,t is an integer from 0 to 5,
u는 0 내지 4의 정수이며;u is an integer from 0 to 4;
v는 0 내지 3의 정수이며;v is an integer from 0 to 3;
w는 0 내지 2의 정수이며;w is an integer from 0 to 2;
R34는 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R34가 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 34 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 6 ~ C 60 aryl group, nuclear atom C 5 to C 60 aryloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 arylamine group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 ~ C 60 It is selected from the group consisting of mono or diaryl phosphinyl group and C 6 ~ C 60 arylsilyl group, or may be combined with adjacent groups to form a condensed ring, when there are a plurality of R 34 Same or different from each other;
상기 R34의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있으며, 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 34 , a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, Arylphosphanyl group, mono or diarylphosphinyl group and 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 alkynyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 Arylamine group, C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 Alkylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 At least one member selected from the group consisting of an aryl boron group, a C 6 to C 60 arylphosphanyl group, a C 6 to C 60 mono or diaryl phosphinyl group, and a C 6 to C 60 arylsilyl group When unsubstituted or substituted with a substituent on the substituent, and substituted with a plurality of substituents, they may be the same as or different from each other,
R26, R27, R30 내지 R33, q 및 r은 상기 화학식 B-1 내지 B-7에서 정의된 바와 같다.R 26 , R 27 , R 30 to R 33 , q and r are as defined in Chemical Formulas B-1 to B-7.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R10, R19 및 R20 중 적어도 하나는 하기 화학식 B-4로 표시되는 치환기일 수 있다: According to one preferred embodiment of the present invention, at least one of the R 10 , R 19 and R 20 may be a substituent represented by the following formula (B-4):
상기 화학식 B-4에서,In Chemical Formula B-4,
R28 및 R29는 각각 독립적으로 수소, C1~C40의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택될 수 있으며;R 28 and R 29 each independently represent hydrogen, an alkyl group of C 1 to C 40 , an aryl group of C 6 to C 60 , a heteroaryl group of 5 to 60 nuclear atoms, an aryloxy group of C 6 to C 60 , and C It may be selected from the group consisting of 6 ~ C 60 arylamine group;
상기 R28 및 R29의 알킬기, 아릴기, 헤테로아릴기 및 아릴아민기는 각각 독립적으로 C1~C40의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, aryl group, heteroaryl group and arylamine group of R 28 and R 29 are each independently C 1 ~ C 40 alkyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group and When substituted or unsubstituted with one or more substituents selected from the group consisting of C 6 to C 60 arylamine groups, and substituted with a plurality of substituents, they may be the same or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R28 및 R29 중 적어도 하나는 하기 화학식 21 또는 22로 표시되는 치환기일 수 있다:According to one preferred embodiment of the present invention, at least one of R 28 and R 29 may be a substituent represented by the following formula 21 or 22:
[화학식 21][Formula 21]
[화학식 22][Formula 22]
상기 화학식 21 및 22에서,In Chemical Formulas 21 and 22,
*는 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
L7 및 L8은 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되며; L 7 and L 8 are each independently 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;
Z6 내지 Z10은 각각 독립적으로 N 또는 C(R37)이며;Z 6 to Z 10 are each independently N or C (R 37 );
R35 내지 R37은 각각 독립적으로 수소, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 상기 R37이 복수 개인 경우 이들은 서로 동일하거나 상이하며; R 35 to R 37 are each independently hydrogen, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 6 -C 60 aryl group, nuclear atom 5 To 60 heteroaryl groups and C 6 to C 60 arylamine groups, and when there are a plurality of R 37 groups, they are the same as or different from each other;
상기 L7 및 L8의 아릴렌기 및 헤테로아릴렌기와, 상기 R35 내지 R37의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 및 아릴아민기는 각각 독립적으로 C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, 및 C6~C60의 아릴아민기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.The arylene group and heteroarylene group of L 7 and L 8 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, and arylamine group of R 35 to R 37 are each independently C 1 to C 40 . An alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 6 to C 60 aryl group, a nuclear atom having 5 to 60 heteroaryl groups, and a C 6 to C 60 arylamine group When substituted or unsubstituted and substituted with a plurality of substituents, they are the same as or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R28 및 R29는 각각 독립적으로 페닐기, 비페닐기, 나프탈레닐기, C1~C10의 알킬기로 치환 또는 비치환된 카바졸릴기 및 상기 화학식 21로 표시되는 치환기로 이루어진 군에서 선택될 수 있다.According to a preferred embodiment of the present invention, R 28 and R 29 are each independently a phenyl group, a biphenyl group, a naphthalenyl group, a carbazolyl group unsubstituted or substituted with an alkyl group of C 1 ~ C 10 and the formula 21 It may be selected from the group consisting of substituents represented.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R35 및 R36 은 각각 독립적으로 페닐기, 비페닐기 및 나프탈레닐기로 이루어진 군에서 선택될 수 있다. According to a preferred embodiment of the present invention, R 35 and R 36 may be each independently selected from the group consisting of a phenyl group, a biphenyl group and a naphthalenyl group.
본 발명의 화학식1로 표시되는 화합물은 하기 화합물로 나타낼 수 있으나 이에 한정되는 것은 아니다:Compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
본 발명의 화학식 1의 화합물은 일반적인 합성방법에 따라 합성될 수 있다(Chem. Rev., 60:313 (1960); J.
Chem
. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) 등 참조). 본 발명의 화합물에 대한 상세한 합성 과정은 후술하는 합성예에서 구체적으로 기술하도록 한다. Compounds of formula 1 of the present invention can be synthesized according to general synthetic methods ( Chem. Rev. , 60 : 313 (1960); J. Chem . SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995) ) And so on). Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
2. 유기 전계 발광 소자2. Organic electroluminescent device
한편, 본 발명의 다른 측면은 상기한 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.On the other hand, another aspect of the present invention provides an organic electroluminescent device comprising a compound represented by the formula (1).
구체적으로, 본 발명은 (i) 양극(anode), (ii) 음극(cathode) 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화학식 1로 표시되는 화합물은 단독 또는 2종 이상이 혼합되어 사용될 수 있다.Specifically, the present invention includes (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 organic layers is It includes a compound represented by the formula (1). In this case, the compound represented by Formula 1 may be used alone or two or more kinds are mixed.
본 발명의 일례에 따르면, 상기 1층 이상의 유기물층은 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층 중 어느 하나 이상을 포함할 수 있는데, 이 중에서 적어도 하나의 유기물층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.According to an embodiment of the present invention, the one or more organic material layers may include any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer is represented by the formula (1) It may include a compound.
바람직하게는 상기 화학식 1로 표시되는 화합물이 포함되는 유기물층은 발광층 또는 정공 수송층일 수 있고, 더욱 바람직하게는, 상기 화학식 1로 표시되는 화합물이 발광층에 포함될 경우, 유기 전계 발광 소자의 발광효율, 휘도, 전력효율, 열적 안정성 및 소자 수명을 매우 향상시킬 수 있다.Preferably, the organic material layer including the compound represented by Formula 1 may be a light emitting layer or a hole transport layer, and more preferably, when the compound represented by Formula 1 is included in the light emitting layer, the luminous efficiency and luminance of the organic EL device It can greatly improve power efficiency, thermal stability and device life.
예를 들어, 상기 화학식 1로 표시되는 화합물은 발광층의 인광 호스트, 형광 호스트 또는 도펀트 재료일 수 있으며, 바람직하게는 발광층의 인광 호스트일 수 있다.For example, the compound represented by Chemical Formula 1 may be a phosphorescent host, a fluorescent host, or a dopant material of the light emitting layer, and preferably, a phosphorescent host of the light emitting layer.
본 발명의 다른 일례에 따르면, 상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자 수송층 및 전자 주입층 중 어느 하나 이상을 포함할 수 있는데, 이때 적어도 하나의 유기물층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.According to another example of the present invention, the one or more organic material layers may include any one or more of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer is It may include a compound represented by the formula (1).
바람직하게는 상기 화학식 1로 표시되는 화합물이 포함되는 유기물층은 발광 보조층일 수 있다. 특히, 상기 화학식 1로 표시되는 화합물이 유기 전계 발광 소자의 발광 보조층 물질에 포함되는 경우, 유기 전계 발광 소자의 효율(발광 효율 및 전력 효율), 수명 및 휘도는 보다 향상시키고, 구동 전압은 더욱 낮출 수 있다.Preferably, the organic material layer including the compound represented by Chemical Formula 1 may be a light emission auxiliary layer. In particular, when the compound represented by Chemical Formula 1 is included in the light emitting auxiliary layer material of the organic light emitting diode, the efficiency (light emitting efficiency and power efficiency), lifetime, and luminance of the organic light emitting diode are further improved, and the driving voltage is further improved. Can be lowered.
본 발명의 또 다른 일례에 따르면, 상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 발광층, 전자 수송 보조층, 전자 수송층 및 전자 주입층 중 어느 하나 이상을 포함할 수 있는데, 이때 적어도 하나의 유기물층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. According to another example of the present invention, the one or more organic material layers may include any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer May include a compound represented by Chemical Formula 1.
바람직하게는, 상기 화학식 1로 표시되는 화합물이 포함되는 유기물층은전자 수송 보조층일 수 있다. 특히 상기 화학식 1로 표시되는 화합물이 유기 전계 발광 소자의 전자수송보조층에 포함되는 경우, 유기 전계 발광 소자의 효율(발광 효율 및 전력 효율), 수명 및 휘도는 보다 향상시키고, 구동 전압은 더욱 낯출 수 있다.Preferably, the organic material layer including the compound represented by Formula 1 may be an electron transport auxiliary layer. In particular, when the compound represented by Formula 1 is included in the electron transport auxiliary layer of the organic electroluminescent device, the efficiency (light emitting efficiency and power efficiency), lifespan and luminance of the organic electroluminescent device are further improved, and the driving voltage is more fragile. Can be.
이러한 본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으며, 예컨대 기판 위에, 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층될 뿐만 아니라, 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조일 수 있다.The structure of the organic EL device of the present invention is not particularly limited, and for example, the anode, one or more organic material layers and the cathode are sequentially stacked on the substrate, and an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer. Can be.
일례에 따르면, 상기 유기 전계 발광 소자는 기판 위에, 양극, 정공 주입층, 정공 수송층, 발광층, 전자 수송층 및 음극이 순차적으로 적층된 구조일 수 있고, 필요에 따라서는, 상기 정공 수송층과 발광층 사이에는 발광 보조층이 삽입될 수 있으며 또, 상기 전자 수송층 위에는 전자 주입층이 위치할 수도 있다.According to an example, the organic EL device may have a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked on a substrate, and, if necessary, between the hole transport layer and the light emitting layer. An emission auxiliary layer may be inserted, and an electron injection layer may be positioned on the electron transport layer.
본 발명의 유기 전계 발광 소자는 상기 1층 이상의 유기물층 중에서 적어도 하나로, 예컨대, 발광층 또는 발광 보조층은 상기 화학식 1로 표시되는 화합물을 포함하도록 형성하는 것을 제외하고는, 당 기술 분야에 알려져 있는 재료 및 방법을 이용하여 유기물층 및 전극을 형성함으로써 제조될 수 있다.The organic electroluminescent device of the present invention is at least one of the one or more organic material layers, for example, a light emitting layer or a light emitting auxiliary layer is formed so as to include a compound represented by the formula (1), and materials known in the art It can be prepared by forming an organic material layer and an electrode using a method.
상기 유기물층은 진공증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이들에 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 발명에서 유기 전계 발광 소자의 제조 시 사용 가능한 기판의 예로는 실리콘 웨이퍼, 석영 또는 유리판, 금속판, 플라스틱 필름이나 시트 등이 있는데, 이에 한정되지 않는다.Examples of the substrate that can be used in the manufacture of the organic EL device in the present invention include a silicon wafer, quartz or glass plate, a metal plate, a plastic film or sheet, but is not limited thereto.
또한, 양극 물질의 예로는 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 및 폴리아닐린과 같은 전도성 고분자; 또는 카본블랙 등이 있으나, 이들에 한정되는 것은 아니다.Further, 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 metals and oxides 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 and polyaniline; Or carbon black, but is not limited thereto.
또한, 음극 물질의 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이에 한정되는 것은 아니다.Further, examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
또한, 정공 주입층, 정공 수송층, 전자 주입층 및 전자 수송층으로 사용되는 물질은 특별히 한정되는 것은 아니며, 당업계에 알려진 통상의 물질이라면 제한없이 사용할 수 있다.In addition, the material used as the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, and any material known in the art may be used without limitation.
이하 본 발명을 실시예를 통하여 상세히 설명하나, 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, but the following Examples are merely illustrative of the present invention, and the present invention is not limited by the following Examples.
[[
준비예Preparation
1] 화합물 1] Compound
Inv1Inv1
및 And
Inv2의Inv2
합성 synthesis
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
<단계 1> <Step 1>
메틸methyl
5- 5-
클로로Chloro
-2-(-2-(
싸이안트렌Cyantre
-2-일)-2 days)
벤조에이트Benzoate
합성 synthesis
싸이안트렌-2-일보로닉산 (20g, 76.88mmol), 메틸 2-브로모-5-클로로벤조에이트 (21.1g, 84.57mmol) 및 Pd(PPh3)4 (0.89g, 0.769mmol)을 플라스크에 넣고 질소 분위기 THF 257mL에 용해 시킨 후 K2CO3
17g (115.3mmol)을 녹인 수용액 128ml를 첨가 시킨 후 8시간 동안 70℃에서 환류 교반 하였다. 반응 종료 후 에틸아세테이트로 추출 한 후 얻은 유기층을 Na2SO4로 건조시키고 감압 증류한 다음, 컬럼 크로마토그래피로 정제하여 화합물 메틸 5-클로로-2-(싸이안트렌-2-일)벤조에이트를 26.9g(수율 91%)을 수득하였다.Thianthrene-2-ylboronic acid (20 g, 76.88 mmol), methyl 2-bromo-5-chlorobenzoate (21.1 g, 84.57 mmol) and Pd (PPh 3 ) 4 (0.89 g, 0.769 mmol) And dissolve in 257mL of nitrogen atmosphere THF and then K 2 CO 3 128 ml of an aqueous solution of 17 g (115.3 mmol) was added thereto, followed by stirring under reflux at 70 ° C. for 8 hours. After completion of the reaction, the obtained organic layer was extracted with ethyl acetate, dried over Na 2 SO 4 , distilled under reduced pressure, and purified by column chromatography to give the compound methyl 5-chloro-2- (thiatren-2-yl) benzoate. 26.9 g (91% yield) were obtained.
<단계 2> 화합물 <Step 2> Compound
Inv1Inv1
, 및 , And
Inv2의Inv2
합성 synthesis
진공 하에서 가열 건조한 3구 둥근 바닥 플라스크에 질소 분위기 하에서 상기 <단계 1>에서 얻은 메틸 5-클로로-2-(싸이안트렌-2-일)벤조에이트 25g(64.95mmol)을 넣고 THF 325mL를 가하여 용해시킨 후 -10℃로 냉각 및 교반 하였다. 여기에 3.0M CH3MgBr 54mL(in Ether, 162.4mmol) 을 30분간 천천히 가한다. 반응액을 상온으로 승온하고 질소 분위기 하에 12시간 교반 하였다. 반응액을 0℃로 냉각한 후 여기에 NH4Cl(10.4g, 194.85mmol)을 증류수 100mL에 녹인 수용액을 천천히 가한다. 반응액을 증류수와 에테르로 추출하고 유기층 용액을 Na2SO4로 건조, 여과하고 여과액을 감압 농축하였다. 건조된 잔사를 3구 둥근 바닥플라스크에 넣은 후 질소분위기 하에서 CH2Cl2 325mL를 가하여 용해시킨 후 0℃로 냉각 및 교반 하였다. 여기에 보론 트리플루오라이드 디에틸 에테레이트 (4mL, 32.5mmol)을 10분간 천천히 가하고 실온으로 승온한 후 12시간 동안 교반한다. 반응이 종료되면 중탄산나트륨 수용액을 0℃에서 천천히 가한후 30분간 교반한다. 반응액을 CH2Cl2/ H2O로 추출한 추출액을 Na2SO4로 건조시키고 감압 증류한 다음, 컬럼 크로마토그래피로 정제하여 화합물 Inv1(15.5g, 수율 65 %), 및 화합물 Inv2 (12.4g, 수율 11 %)를 수득 하였다.25 g (64.95 mmol) of methyl 5-chloro-2- (canthren-2-yl) benzoate obtained in the above <Step 1> was added to a 3-necked round bottom flask heated under vacuum under nitrogen atmosphere, and 325 mL of THF was added thereto to dissolve. After cooling to -10 ℃ and stirred. To this was slowly added 3.0 mL CH 3 MgBr 54 mL (in Ether, 162.4 mmol) for 30 minutes. The reaction solution was heated to room temperature and stirred for 12 hours under a nitrogen atmosphere. After cooling the reaction solution to 0 ° C., an aqueous solution of NH 4 Cl (10.4 g, 194.85 mmol) in 100 mL of distilled water was slowly added thereto. The reaction solution was extracted with distilled water and ether, the organic layer solution was dried over Na 2 SO 4 , filtered and the filtrate was concentrated under reduced pressure. The dried residue was put into a three-necked round bottom flask, and then dissolved by adding 325 mL of CH 2 Cl 2 under a nitrogen atmosphere, and then cooled and stirred to 0 ° C. Boron trifluoride diethyl etherate (4 mL, 32.5 mmol) was slowly added thereto for 10 minutes, warmed to room temperature, and stirred for 12 hours. After the reaction was completed, the aqueous solution of sodium bicarbonate was slowly added at 0 ° C. and stirred for 30 minutes. The reaction solution was extracted with CH 2 Cl 2 / H 2 O, dried over Na 2 SO 4 , distilled under reduced pressure, and purified by column chromatography to obtain Compound Inv1 (15.5g, 65% yield), and Compound Inv2 (12.4g , Yield 11%) was obtained.
[[
준비예Preparation
2] 화합물 2] compound
Inv3Inv3
및 And
Inv4의Inv4
합성 synthesis
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
<단계 1> <Step 1>
메틸methyl
4- 4-
클로로Chloro
-2-(-2-(
싸이안트렌Cyantre
-2-일)-2 days)
벤조에이트Benzoate
합성 synthesis
싸이안트렌-2-일보로닉산 (20g, 76.88mmol), 메틸 2-브로모-4-클로로벤조에이트 (21.1g, 84.57mmol) 및 Pd(PPh3)4 (0.89g, 0.769mmol)을 플라스크에 넣고 질소 분위기 THF 257mL에 용해 시킨 후 K2CO3
17g (115.3mmol)을 녹인 수용액 128ml를 첨가 시킨 후 8시간 동안 70℃에서 환류 교반 하였다. 반응 종료 후 에틸아세테이트로 추출 한 후 얻은 유기층을 Na2SO4로 건조시키고 감압 증류한 다음, 컬럼 크로마토그래피로 정제하여 화합물 메틸 4-클로로-2-(싸이안트렌-2-일)벤조에이트를 26.9g(수율 91%)을 수득하였다.Thianthrene-2-ylboronic acid (20 g, 76.88 mmol), methyl 2-bromo-4-chlorobenzoate (21.1 g, 84.57 mmol) and Pd (PPh 3 ) 4 (0.89 g, 0.769 mmol) And dissolve in 257mL of nitrogen atmosphere THF and then K 2 CO 3 128 ml of an aqueous solution of 17 g (115.3 mmol) was added thereto, followed by stirring under reflux at 70 ° C. for 8 hours. After completion of the reaction, the obtained organic layer was extracted with ethyl acetate, dried over Na 2 SO 4 , distilled under reduced pressure, and purified by column chromatography to give the compound methyl 4-chloro-2- (thiatren-2-yl) benzoate. 26.9 g (91% yield) were obtained.
<단계 2> 화합물 <Step 2> Compound
Inv3Inv3
, 및 , And
Inv4의Inv4
합성 synthesis
진공 하에서 가열 건조한 3구 둥근 바닥 플라스크에 질소 분위기 하에서 상기 <단계 1>에서 얻은 메틸 4-클로로-2-(싸이안트렌-2-일)벤조에이트 25g(64.95mmol)을 넣고 THF 325mL를 가하여 용해시킨 후 -10℃로 냉각 및 교반 하였다. 여기에 3.0M CH3MgBr 54mL(in Ether, 162.4mmol) 을 30분간 천천히 가한다. 반응액을 상온으로 승온하고 질소 분위기 하에 12시간 교반 하였다. 반응액을 0℃로 냉각한 후 여기에 NH4Cl(10.4g, 194.85mmol)을 증류수 100mL에 녹인 수용액을 천천히 가한다. 반응액을 증류수와 에테르로 추출하고 유기층 용액을 Na2SO4로 건조, 여과하고 여과액을 감압 농축하였다. 건조된 잔사를 3구 둥근 바닥플라스크에 넣은 후 질소분위기 하에서 CH2Cl2 325mL를 가하여 용해시킨 후 0℃로 냉각 및 교반 하였다. 여기에 보론 트리플루오라이드 디에틸 에테레이트 (4mL, 32.5mmol)을 10분간 천천히 가하고 실온으로 승온한 후 12시간 동안 교반한다. 반응이 종료되면 중탄산나트륨 수용액을 0℃에서 천천히 가한후 30분간 교반한다. 반응액을 CH2Cl2/ H2O로 추출한 추출액을 Na2SO4로 건조시키고 감압 증류한 다음, 컬럼 크로마토그래피로 정제하여 화합물 Inv3(14.3, 수율 60 %), 및 화합물 Inv4 (2.4g, 수율 10 %)를 수득 하였다.25 g (64.95 mmol) of methyl 4-chloro-2- (canthren-2-yl) benzoate obtained in the above <Step 1> was added to a three-necked round bottom flask heated under vacuum under nitrogen atmosphere, and 325 mL of THF was added thereto to dissolve. After cooling to -10 ℃ and stirred. To this was slowly added 3.0 mL CH 3 MgBr 54 mL (in Ether, 162.4 mmol) for 30 minutes. The reaction solution was heated to room temperature and stirred for 12 hours under a nitrogen atmosphere. After cooling the reaction solution to 0 ° C., an aqueous solution of NH 4 Cl (10.4 g, 194.85 mmol) in 100 mL of distilled water was slowly added thereto. The reaction solution was extracted with distilled water and ether, the organic layer solution was dried over Na 2 SO 4 , filtered and the filtrate was concentrated under reduced pressure. The dried residue was put into a three-necked round bottom flask, and then dissolved by adding 325 mL of CH 2 Cl 2 under a nitrogen atmosphere, and then cooled and stirred to 0 ° C. Boron trifluoride diethyl etherate (4 mL, 32.5 mmol) was slowly added thereto for 10 minutes, warmed to room temperature, and stirred for 12 hours. After the reaction was completed, the aqueous solution of sodium bicarbonate was slowly added at 0 ° C. and stirred for 30 minutes. The reaction solution was extracted with CH 2 Cl 2 / H 2 O, dried over Na 2 SO 4 , distilled under reduced pressure, and purified by column chromatography to obtain Compound Inv3 (14.3, yield 60%), and Compound Inv4 (2.4g, Yield 10%).
[[
준비예Preparation
3] 화합물 3] compound
Inv5Inv5
, 및 , And
Inv6의Inv6
합성 synthesis
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
<단계 1> 2-(5-<Step 1> 2- (5-
클로로Chloro
-2--2-
니트로페닐Nitrophenyl
))
싸이안트렌의Psychedelic
합성 synthesis
싸이안트렌-2-일보로닉산 (100g, 0.384mol), 2-브로모-4-클로로-1-니트로벤젠 (109g, 0.461mol) 및 Pd(PPh3)4 (13.5g, 0.011mol)을 플라스크에 넣고, 여기에 2M Na2CO3 포화 수용액 (576㎖)과 1,4-디옥산 (2L)을 넣어 녹인 후, 8시간 동안 가열 교반하였다. 반응 종료 후, 증류수를 넣고 에틸아세테이트로 유기층을 추출하였다. 얻은 유기층을 Na2SO4로 건조시키고 감압 증류한 다음, 컬럼 크로마토그래피로 정제하여 화합물 2-(5-클로로-2-니트로페닐)싸이안트렌 (124g, 수율 87%)을 얻었다.Thianthrene-2-ylboronic acid (100 g, 0.384 mol), 2-bromo-4-chloro-1-nitrobenzene (109 g, 0.461 mol) and Pd (PPh 3 ) 4 (13.5 g, 0.011 mol) Into the flask, 2M Na 2 CO 3 saturated aqueous solution (576ml) and 1,4-dioxane (2L) were dissolved therein, followed by heating and stirring for 8 hours. After the reaction was completed, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and then purified by column chromatography to obtain compound 2- (5-chloro-2-nitrophenyl) thiarene (124 g, yield 87%).
<단계 2> 화합물 <Step 2> Compound
Inv5Inv5
및 And
Inv6의Inv6
합성 synthesis
질소 기류 하에서 상기 <단계 1>에서 2-(5-클로로-2-니트로페닐)싸이안트렌 (124g, 0.334mol), PPh3 (219g, 0.835mol), 및 1,2-디클로로벤젠 (1.5L)을 혼합한 후, 12시간 동안 교반하였다. 반응 종료 후, 1,2-디클로로벤젠을 제거하고 CH2Cl2으로 유기층을 추출하였다. 얻은 유기층을 Na2SO4로 건조시키고 감압 증류한 다음, 컬럼 크로마토그래피로 정제하여 화합물 Inv5(58g, 수율 51 %), 및 화합물 Inv6 (27 g, 수율 24 %)을 획득하였다.2- (5-chloro-2-nitrophenyl) thianthrene (124g, 0.334mol), PPh 3 (219g, 0.835mol), and 1,2-dichlorobenzene (1.5L in the above <Step 1> under nitrogen stream ) Was mixed and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed and the organic layer was extracted with CH 2 Cl 2 . The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and purified by column chromatography to obtain Compound Inv5 (58 g, yield 51%), and Compound Inv6 (27 g, yield 24%).
[[
준비예Preparation
4] 화합물 4] compound
Inv7Inv7
, 및 , And
Inv8의Inv8
합성 synthesis
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
<단계 1> 2-(11,11-디메틸-11H-<Step 1> 2- (11,11-dimethyl-11H-
인데노[1,2-b]싸이안트렌Indeno [1,2-b] cyanthrene
-9-일)-4,4,5,5--9-day) -4,4,5,5-
테트라메틸Tetramethyl
-1,3,2-디옥산보로란의 합성Synthesis of -1,3,2-dioxaneborolane
Inv1 (139g, 0.38mol), 4,4,4',4',5,5,5',5'-옥타메틸-2,2'-비(1,3,2-디옥사보로란) (115.8g, 0.46mol), Pd(dppf)Cl2 (31g, 0.038mol) 및, KOAc(111.9g, 1.14mol)을 플라스크에 넣은 다음, 여기에 1,4-디옥산 (2L)를 넣어 녹인 후 8시간 동안 가열 교반하였다. 반응 종료 후, 증류수를 넣고 에틸아세테이트로 유기층을 추출하였다. 얻은 유기층을 Na2SO4로 건조시키고 감압 증류한 다음, 컬럼 크로마토그래피로 정제하여 화합물 2-(11,11-디메틸-11H-인데노[1,2-b]싸이안트렌-9-일)-4,4,5,5-테트라메틸-1,3,2-디옥사보로란 (149g, 수율 62%)을 얻었다.Inv1 (139g, 0.38mol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-ratio (1,3,2-dioxaborolane) (115.8g, 0.46mol), Pd (dppf) Cl 2 (31g, 0.038mol) and KOAc (111.9g, 1.14mol) were added to the flask, and 1,4-dioxane (2L) was added thereto to dissolve it. After stirring for 8 hours. After the reaction was completed, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and then purified by column chromatography to give compound 2- (11,11-dimethyl-11H-indeno [1,2-b] thiathren-9-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (149 g, yield 62%) was obtained.
<단계 2> 11,11-디메틸-9-(2-<Step 2> 11,11-dimethyl-9- (2-
니트로페닐Nitrophenyl
)-11H-) -11H-
인데노[1,2-b]싸이안트렌의Of indeno [1,2-b] cyanthrene
합성 synthesis
상기 <단계 1>에서 얻은 2-(11,11-디메틸-11H-인데노[1,2-b]싸이안트렌-9-일)-4,4,5,5-테트라메틸-1,3,2-디옥사보로란 (149g, 0.235mol), 1-브로모-2-니트로벤젠 (67g, 0.282mol) 및 Pd(PPh3)4 (13.5g, 0.011mol)을 플라스크에 넣고, 여기에 2M Na2CO3 포화 수용액 (352㎖)과 1,4-dioxane (2L)을 넣어 녹인 후, 8시간 동안 가열 교반하였다. 반응 종료 후, 증류수를 넣고 에틸아세테이트로 유기층을 추출하였다. 얻은 유기층을 Na2SO4로 건조시키고 감압 증류한 다음, 컬럼 크로마토그래피로 정제하여 화합물 11,11-디메틸-9-(2-니트로페닐)-11H-인데노[1,2-b]싸이안트렌 (96g, 수율 91%)을 얻었다.2- (11,11-dimethyl-11H-indeno [1,2-b] canthren-9-yl) -4,4,5,5-tetramethyl-1,3 obtained in <Step 1> above , 2-Dioxaborolane (149g, 0.235mol), 1-bromo-2-nitrobenzene (67g, 0.282mol) and Pd (PPh 3 ) 4 (13.5g, 0.011mol) were added to the flask, and 2M Na 2 CO 3 saturated aqueous solution (352 ml) and 1,4-dioxane (2 L) were added thereto, dissolved, and heated and stirred for 8 hours. After the reaction was completed, distilled water was added and the organic layer was extracted with ethyl acetate. The resulting organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and purified by column chromatography to give compound 11,11-dimethyl-9- (2-nitrophenyl) -11H-indeno [1,2-b] cyan Tren (96 g, 91% yield) was obtained.
<단계 3> 화합물 <Step 3> Compound
Inv7Inv7
, 및 , And
Inv8의Inv8
합성 synthesis
질소 기류 하에서 상기 <단계 2>에서 11,11-디메틸-9-(2-니트로페닐)-11H-인데노[1,2-b]싸이안트렌 (96g, 0.212mol)과 PPh3 (67g, 0.255mol), 1,2-디클로로벤젠(1L)을 혼합한 후, 12시간 동안 교반하였다. 반응 종료 후, 1,2-디클로로벤젠 을 제거하고 디클로로메탄으로 유기층을 추출하였다. 얻은 유기층을 Na2SO4로 건조시키고 감압 증류한 다음, 컬럼 크로마토그래피로 정제하여 화합물 Inv7(36g, 수율 40 %), 및 화합물 Inv8 (31 g, 수율 35 %)을 획득하였다.Under nitrogen stream, 11,11-dimethyl-9- (2-nitrophenyl) -11H-indeno [1,2-b] cyanthrene (96g, 0.212mol) and PPh 3 (67g, 0.255 mol), 1,2-dichlorobenzene (1 L) were mixed and then stirred for 12 hours. After the reaction was completed, 1,2-dichlorobenzene was removed, and the organic layer was extracted with dichloromethane. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and purified by column chromatography to obtain Compound Inv7 (36 g, 40% yield), and Compound Inv8 (31 g, 35% yield).
[[
준비예Preparation
5] 화합물 5] compound
Inv9Inv9
, 및 , And
Inv10의Inv10
합성 synthesis
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
상기 준비예 4과 동일한 과정을 수행하되, <단계 1>에서 Inv1 대신 Inv2를 사용하여 화합물 Inv9(33.6g, 수율 35 %), 및 화합물 Inv10 (28.8 g, 수율 30 %)을 수득 하였다 The same procedure as in Preparation Example 4 was performed, except that Inv2 was used instead of Inv1 in <Step 1> to obtain Compound Inv9 (33.6g, 35% yield), and Compound Inv10 (28.8 g, 30% yield).
[[
준비예Preparation
6] 화합물 6] compound
Inv11Inv11
, 및 , And
Inv12의Inv12
합성 synthesis
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
상기 준비예 4과 동일한 과정을 수행하되, <단계 1>에서 Inv1 대신 Inv3를 사용하여 화합물 Inv11(48g, 수율 50 %), 및 화합물 Inv12 (28.8 g, 수율 30 %)을 수득 하였다 The same procedure as in Preparation Example 4 was performed, except that Inv3 was used instead of Inv1 in <Step 1> to obtain Compound Inv11 (48 g, yield 50%), and Compound Inv12 (28.8 g, yield 30%).
[[
준비예Preparation
7] 화합물 7] compound
Inv13Inv13
, 및 , And
Inv14의Of Inv14
합성 synthesis
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
상기 준비예 4과 동일한 과정을 수행하되, <단계 1>에서 Inv1 대신 Inv3를 사용하여 화합물 Inv13(19.2g, 수율 20 %), 및 화합물 Inv14 (38 g, 수율 40 %)을 수득 하였다 In the same procedure as in Preparation Example 4, Inv3 was used instead of Inv1 in <Step 1> to obtain Compound Inv13 (19.2g, 20% yield), and Compound Inv14 (38 g, 40% yield).
[[
준비예Preparation
8] 화합물 8] compound
Inv15Inv15
, 및 , And
Inv16의Inv16
합성 synthesis
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
<단계 1> 2-(4,4,5,5-<Step 1> 2- (4,4,5,5-
테트라메틸Tetramethyl
-1,3,2--1,3,2-
디옥사보로란Dioxaboloran
-2-일)-5H--2-yl) -5H-
벤조[5,6][1,4]디티이노[2,3-b]카바졸의Of benzo [5,6] [1,4] dithiino [2,3-b] carbazole
합성 synthesis
lnv5(129g, 0.38mol), 4,4,4',4',5,5,5',5'-옥타메틸-2,2'-비(1,3,2-디옥사보로란) (115.8g, 0.46mol), Pd(dppf)Cl2 (31g, 0.038mol) 및 KOAc(111.9g, 1.14mol)을 플라스크에 넣은 다음, 여기에 1,4-디옥산 (2L)를 넣어 녹인 후, 8시간 동안 가열 교반하였다. 반응 종료 후, 증류수를 넣고 에틸아세테이트로 유기층을 추출하였다. 얻은 유기층을 Na2SO4로 건조시키고 감압 증류한 다음, 컬럼 크로마토그래피로 정제하여 화합물 2-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)-5H-벤조[5,6][1,4]디티이노[2,3-b]카바졸 (101.6g, 수율 62%)을 얻었다. lnv5 (129 g, 0.38 mol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-ratio (1,3,2-dioxaborolane) (115.8g, 0.46mol), Pd (dppf) Cl 2 (31g, 0.038mol) and KOAc (111.9g, 1.14mol) were added to the flask, and 1,4-dioxane (2L) was added thereto to dissolve it. And stirred for 8 hours. After the reaction was completed, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and purified by column chromatography to give compound 2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2- Il) -5H-benzo [5,6] [1,4] dithiino [2,3-b] carbazole (101.6 g, yield 62%) was obtained.
<단계 2> <Step 2>
메틸methyl
2-(5H- 2- (5H-
벤조[5,6][1,4]디티이노[2,3-b]카바졸Benzo [5,6] [1,4] dithiino [2,3-b] carbazole
-2-일)-2 days)
벤조에이트의Benzoate
합성 synthesis
상기 <단계 1>에서 얻은 2-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)-5H-벤조[5,6][1,4]디티이노[2,3-b]카바졸 (101.6g, 0.23mol), 메틸 2-브로모-5-클로로벤조에이트 (55.7g, 0.26mol) 및 Pd(PPh3)4 (8.1g, 7mmol)을 플라스크에 넣고 질소 분위기 THF (1L)에 용해 시킨 후 K2CO3
95.3g (0.69mol)을 녹인 수용액 350ml를 첨가 시킨 후 8시간 동안 80℃에서 환류 교반 하였다. 반응 종료 후 에틸아세테이트로 추출 한 후 얻은 유기층을 Na2SO4로 건조시키고 감압 증류한 다음, 컬럼 크로마토그래피로 정제하여 화합물 메틸 2-(5H-벤조[5,6][1,4]디티이노[2,3-b]카바졸-2-일)벤조에이트 87.9g(수율 87%)을 수득 하였다.2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5H-benzo [5,6] [1,4 obtained in <Step 1> above ] Dithiino [2,3-b] carbazole (101.6 g, 0.23 mol), methyl 2-bromo-5-chlorobenzoate (55.7 g, 0.26 mol) and Pd (PPh 3 ) 4 (8.1 g, 7 mmol ) Into the flask and dissolved in nitrogen atmosphere THF (1 L), and then K 2 CO 3 350 ml of an aqueous solution of 95.3 g (0.69 mol) was added thereto, followed by stirring under reflux at 80 ° C. for 8 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, dried over Na 2 SO 4 , distilled under reduced pressure, and purified by column chromatography to give the compound methyl 2- (5H-benzo [5,6] [1,4] ditinoin 87.9 g (87% yield) of [2,3-b] carbazol-2-yl) benzoate were obtained.
<단계 3> 화합물 <Step 3> Compound
Inv15Inv15
, 및 , And
Inv16의Inv16
합성 synthesis
진공 하에서 가열 건조한 3구 둥근 바닥 플라스크에 질소 분위기 하에서 상기 <단계 2>에서 얻은 메틸 2-(5H-벤조[5,6][1,4]디티이노[2,3-b]카바졸-2-일)벤조에이트 (87.9g, 0.20mol)을 넣고 THF 900mL를 가하여 용해시킨 후 -10℃로 냉각 및 교반 하였다. 여기에 3.0M CH3MgBr 166mL(in Ether, 0.5mol)을 30분간 천천히 가한다. 반응액을 상온으로 승온하고 질소 분위기 하에 12시간 교반 하였다. 반응액을 0℃로 냉각한 후 여기에 NH4Cl(32g, 0.6mol)을 증류수 100mL에 녹인 수용액을 천천히 가한다. 반응액을 증류수와 CH2Cl2로 추출하고 유기층 용액을 Na2SO4로 건조, 여과하고 여과액을 감압 농축하였다. 건조된 잔사를 3구 둥근 바닥플라스크에 넣은 후 질소분위기 하에서 CH2Cl2 900mL를 가하여 용해시킨 후 0℃로 냉각 및 교반 하였다. 여기에 보론 트리플루오라이드 디에틸 에테레이트 (12.3mL, 0.1mol)을 10분간 천천히 가하고 실온으로 승온한 후 12시간 동안 교반한다. 반응이 종료되면 중탄산나트륨 수용액을 0℃에서 천천히 가한후 30분간 교반한다. 반응액을 CH2Cl2/증류수로 추출한 추출액을 Na2SO4로 건조시키고 감압 증류한 다음, 컬럼 크로마토그래피로 정제하여 화합물 Inv15(21g, 수율 25 %), 및 화합물 Inv16 (42 g, 수율 50 %)을 수득 하였다.Methyl 2- (5H-benzo [5,6] [1,4] dithiino [2,3-b] carbazole-2 obtained in <Step 2> under a nitrogen atmosphere in a three-necked round bottom flask heated under vacuum -Yl) benzoate (87.9g, 0.20mol) was added and dissolved in 900mL THF, and then cooled and stirred to -10 ℃. 166 mL (in Ether, 0.5 mol) of 3.0 M CH 3 MgBr was slowly added thereto for 30 minutes. The reaction solution was heated to room temperature and stirred for 12 hours under a nitrogen atmosphere. After cooling the reaction solution to 0 ° C, an aqueous solution of NH 4 Cl (32 g, 0.6 mol) dissolved in 100 mL of distilled water was slowly added thereto. The reaction solution was extracted with distilled water and CH 2 Cl 2 , the organic layer solution was dried over Na 2 SO 4 , filtered, and the filtrate was concentrated under reduced pressure. The dried residue was put into a three-necked round bottom flask, and then dissolved by adding 900 mL of CH 2 Cl 2 under a nitrogen atmosphere, and then cooled and stirred at 0 ° C. Boron trifluoride diethyl etherate (12.3 mL, 0.1 mol) was slowly added thereto for 10 minutes, warmed to room temperature, and stirred for 12 hours. After the reaction was completed, the aqueous solution of sodium bicarbonate was slowly added at 0 ° C. and stirred for 30 minutes. The extract was extracted with CH 2 Cl 2 / distilled water, dried over Na 2 SO 4 , distilled under reduced pressure, and purified by column chromatography to obtain Compound Inv15 (21 g, yield 25%), and Compound Inv16 (42 g, yield 50). %) Was obtained.
[[
준비예Preparation
9] 화합물 9] Compound
Inv17Inv17
, 및 , And
Inv18의Inv18
합성 synthesis
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
상기 준비예 8과 동일한 과정을 수행하되, <단계 1>에서 Inv5 대신 Inv6를 사용하여 화합물 Inv17(25.2, 수율 30 %), 및 화합물 Inv18 (25.2 g, 수율 30 %)을 수득 하였다 In the same procedure as in Preparation Example 8, Inv6 was used instead of Inv5 in Step 1 to obtain Compound Inv17 (25.2, yield 30%), and Compound Inv18 (25.2 g, Yield 30%).
[[
반응예Example of reaction
1] One]
CpdCpd
1의 합성 1, Synthesis
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
준비예 에서 얻은 Inv 1 (2.8g, 7.70 mmol), (9-페닐-9H-카바졸-3-일)보로닉산 (2.8 g, 9.67 mmol), NaOH (1.06g, 26.4 mmol), 및 THF/H2O (100 ml/50 ml)를 넣고 교반하였다. 이후, 40℃에서 Pd(PPh3)4 (5 mol%, 0.51 g)를 넣고, 80℃에서 12시간 동안 교반하였다. Inv 1 (2.8 g, 7.70 mmol) obtained in the preparation example, (9-phenyl-9H-carbazol-3-yl) boronic acid (2.8 g, 9.67 mmol), NaOH (1.06 g, 26.4 mmol), and THF / H 2 O (100 ml / 50 ml) was added and stirred. Then, Pd (PPh 3 ) 4 (5 mol%, 0.51 g) was added at 40 ° C., and stirred at 80 ° C. for 12 hours.
TLC로 반응이 종결되는 것을 확인한 후, 상온으로 식혔다. 반응 종료 후, 증류수를 넣고 에틸아세테이트로 유기층을 추출하였다. 얻어진 유기층을 Na2SO4 로 건조시키고 감압 증류한 다음, 컬럼 크로마토그래피로 정제하여 화합물 Cpd 1 3.5g, 수율 80%)을 얻었다. HRMS [M]+: 573.158After confirming that the reaction was terminated by TLC, it was cooled to room temperature. After the reaction was completed, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and purified by column chromatography to obtain 3.5 g of compound Cpd 1, yield 80%). HRMS [M] + : 573.158
[[
반응예Example of reaction
2] 2]
CpdCpd
6의 합성 6, composite
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
준비예 에서 얻은 Inv 1 (3.1g, 8.5 mmol), 9H-3,9'-비카바졸 (3.4 g, 10.2 mmol)을 Toluene (85 ㎖)에 녹인 다음, Pd2(dba)3 (0.76g, 0.8mmol)을 질소 하에서 투입하였다. 이 후, 여기에 NaOtBu (2.4g, 25mmol)을 넣은 후, (t-Bu)3P (0.8 ㎖, 0.8mmol)을 상기 반응액에 투입한 다음, 혼합물을 5시간 동안 환류 교반하였다. Inv 1 (3.1 g, 8.5 mmol) and 9H-3,9'-bicarbazole (3.4 g, 10.2 mmol) obtained in Preparation Example were dissolved in Toluene (85 mL), and then Pd 2 (dba) 3 (0.76 g). , 0.8 mmol) was added under nitrogen. Thereafter, NaOtBu (2.4 g, 25 mmol) was added thereto, and (t-Bu) 3 P (0.8 mL, 0.8 mmol) was added to the reaction solution, and the mixture was stirred under reflux for 5 hours.
TLC로 반응이 종결되는 것을 확인한 후, 상온으로 식혔다. 반응 종료 후, 증류수를 넣고 에틸아세테이트로 유기층을 추출하였다. 얻어진 유기층을 Na2SO4 로 건조시키고 감압 증류한 다음, 컬럼 크로마토그래피로 정제하여 화합물 Cpd 6 (4.8g, 수율 85%)을 얻었다. HRMS [M]+: 662.185After confirming that the reaction was terminated by TLC, it was cooled to room temperature. After the reaction was completed, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and purified by column chromatography to obtain compound Cpd 6 (4.8 g, yield 85%). HRMS [M] + : 662.185
[[
반응예Example of reaction
3] 3]
CpdCpd
8의 합성 8, composite
상기 반응예 1과 동일한 과정을 수행하되, (9-페닐-9H-카바졸-3-일)보로닉산 대신 (3-(다이벤조[b,d]퓨란-2-일)페닐)보로닉산을 사용하여 화합물 Cpd 8 (4.0g, 수율 90%)을 얻었다. The same procedure as in Reaction Example 1 was carried out, except for (3- (dibenzo [b, d] furan-2-yl) phenyl) boronic acid instead of (9-phenyl-9H-carbazol-3-yl) boronic acid. Compound Cpd 8 (4.0 g, yield 90%) was obtained.
HRMS [M]+: 574.142HRMS [M] + : 574.142
[[
반응예Example of reaction
4] 4]
CpdCpd
10의 합성 10 composite
상기 반응예 1과 동일한 과정을 수행하되, (9-페닐-9H-카바졸-3-일)보로닉산 대신 (3-(트리페닐렌-2-일)페닐)보로닉산을 사용하여 화합물 Cpd 10 (4.0g, 수율 85%)을 얻었다. The same procedure as in Reaction Example 1 was carried out, but using (3- (triphenylen-2-yl) phenyl) boronic acid instead of (9-phenyl-9H-carbazol-3-yl) boronic acid, Compound Cpd 10 (4.0 g, yield 85%) was obtained.
HRMS [M]+: 634.179HRMS [M] + : 634.179
[[
반응예Example of reaction
5] 5]
CpdCpd
11의 합성 11, synthesis
상기 반응예 1과 동일한 과정을 수행하되, (9-페닐-9H-카바졸-3-일)보로닉산 대신 (3-(다이벤조[b,d]사이오펜-2-일)페닐)보로닉산을 사용하여 화합물 Cpd 11 (4.2g, 수율 92%)을 얻었다. The same process as in Reaction Example 1 was carried out, except for (9-phenyl-9H-carbazol-3-yl) boronic acid (3- (dibenzo [b, d] thiophen-2-yl) phenyl) boronic acid Compound Cpd 11 (4.2 g, yield 92%) was obtained using.
HRMS [M]+: 590.120HRMS [M] + : 590.120
[[
반응예Example of reaction
6] 6]
CpdCpd
24의 합성 24 composites
상기 반응예 1과 동일한 과정을 수행하되, (9-페닐-9H-카바졸-3-일)보로닉산 대신 (4-(4,6-다이페닐-1,3,5-트리아진-2-일)페닐)보로닉산을 사용하여 화합물 Cpd 24 (4.0g, 수율 82%)을 얻었다. The same process as in Example 1 was carried out, except for (9-phenyl-9H-carbazol-3-yl) boronic acid (4- (4,6-diphenyl-1,3,5-triazine-2- Il) phenyl) boronic acid was used to give compound Cpd 24 (4.0 g, yield 82%).
HRMS [M]+: 639.180HRMS [M] + : 639.180
[[
반응예Example of reaction
7] 7]
CpdCpd
28의 합성 28 Synthesis
상기 반응예 1과 동일한 과정을 수행하되, (9-페닐-9H-카바졸-3-일)보로닉산 대신 ((3-(4,6-다이페닐-1,3,5-트리아진-2-일)페닐)보로닉산을 사용하여 화합물 Cpd 28 (4.2g, 수율 86%)을 얻었다. Performing the same process as in Example 1, except for (9-phenyl-9H-carbazol-3-yl) boronic acid ((3- (4,6-diphenyl-1,3,5-triazine-2) Compound Cpd 28 (4.2 g, yield 86%) was obtained using -yl) phenyl) boronic acid.
HRMS [M]+: 639.180HRMS [M] + : 639.180
[[
반응예Example of reaction
8] 8]
CpdCpd
34의 합성 Synthesis of 34
상기 반응예 1과 동일한 과정을 수행하되, (9-페닐-9H-카바졸-3-일)보로닉산 대신 (9-(4,6-다이페닐-1,3,5-트리아진-2-일)-9H-카바졸-3-일)보로닉산을 사용하여 화합물 Cpd 34 (4.3g, 수율 86%)을 얻었다. The same process as in Example 1 was carried out, except for (9- (4,6-diphenyl-1,3,5-triazine-2-) instead of (9-phenyl-9H-carbazol-3-yl) boronic acid. Compound Cpd 34 (4.3 g, yield 86%) was obtained using yl) -9H-carbazol-3-yl) boronic acid.
HRMS [M]+: 728.207HRMS [M] + : 728.207
[[
반응예Example of reaction
9] 9]
CpdCpd
39의 합성 Synthesis of 39
상기 반응예 1과 동일한 과정을 수행하되, (9-페닐-9H-카바졸-3-일)보로닉산 대신 (9-(4-(4,6-다이페닐-1,3,5-트리아진-2-일)페닐)-9H-카바졸-3-일)보로닉산을 사용하여 화합물 Cpd 39 (4.9g, 수율 80%)을 얻었다. The same procedure as in Example 1 was carried out, except for (9- (4- (4,6-diphenyl-1,3,5-triazine) instead of (9-phenyl-9H-carbazol-3-yl) boronic acid. 2-yl) phenyl) -9H-carbazol-3-yl) boronic acid gave compound Cpd 39 (4.9 g, yield 80%).
HRMS [M]+: 804.238HRMS [M] + : 804.238
[[
반응예Example of reaction
10] 10]
CpdCpd
43의 합성 Synthesis of 43
상기 반응예 1과 동일한 과정을 수행하되, (9-페닐-9H-카바졸-3-일)보로닉산 대신 (9-(3-(4,6-다이페닐-1,3,5-트리아진-2-일)페닐)-9H-카바졸-3-일)보로닉산을 사용하여 화합물 Cpd 43 (5.1g, 수율 81%)을 얻었다. The same process as in Example 1 was carried out, except for (9- (3- (4,6-diphenyl-1,3,5-triazine) instead of (9-phenyl-9H-carbazol-3-yl) boronic acid. 2-yl) phenyl) -9H-carbazol-3-yl) boronic acid was used to give compound Cpd 43 (5.1 g, yield 81%).
HRMS [M]+: 804.238HRMS [M] + : 804.238
[[
반응예Example of reaction
11] 11]
CpdCpd
46의 합성 Synthesis of 46
상기 반응예 1과 동일한 과정을 수행하되, Inv 1 대신 Inv 3을 사용하여 화합물 Cpd 46 (3.5g, 수율 80%)을 얻었다. A compound Cpd 46 (3.5 g, yield 80%) was obtained in the same manner as in Example 1 except that Inv 3 was used instead of Inv 1.
HRMS [M]+: 573.158HRMS [M] + : 573.158
[[
반응예Example of reaction
12] 12]
CpdCpd
51의 합성 51 composites
상기 반응예 2과 동일한 과정을 수행하되, Inv 1 대신 Inv 3을 사용하여 화합물 Cpd 51 (4.8g, 수율 85%)을 얻었다. The same process as in Example 2 was carried out, except that Inv 3 was used to obtain Compound Cpd 51 (4.8 g, yield 85%).
HRMS [M]+: 662.185HRMS [M] + : 662.185
[[
반응예Example of reaction
13] 13]
CpdCpd
55의 합성 55 composites
상기 반응예 4과 동일한 과정을 수행하되, Inv 1 대신 Inv 3을 사용하여 화합물 Cpd 55 (4.0g, 수율 85%)을 얻었다. A compound Cpd 55 (4.0 g, 85% yield) was obtained in the same manner as in Example 4 except that Inv 3 was used instead of Inv 1.
HRMS [M]+: 634.179HRMS [M] + : 634.179
[[
반응예Example of reaction
14] 14]
CpdCpd
56의 합성 56 composites
상기 반응예 5과 동일한 과정을 수행하되, Inv 1 대신 Inv 3을 사용하여 화합물 Cpd 56 (4.2g, 수율 92%)을 얻었다. A compound Cpd 56 (4.2 g, yield 92%) was obtained in the same manner as in Example 5 except that Inv 3 was used instead of Inv 1.
HRMS [M]+: 590.120HRMS [M] + : 590.120
[[
반응예Example of reaction
15] 15]
CpdCpd
73의 합성 Synthesis of 73
상기 반응예 7과 동일한 과정을 수행하되, Inv 1 대신 Inv 3을 사용하여 화합물 Cpd 73 (4.2g, 수율 86%)을 얻었다. A compound Cpd 73 (4.2 g, yield 86%) was obtained in the same manner as in Example 7, except that Inv 3 was used instead of Inv 1.
HRMS [M]+: 639.180HRMS [M] + : 639.180
[[
반응예Example of reaction
16] 16]
CpdCpd
84의 합성 84 composites
상기 반응예 9과 동일한 과정을 수행하되, Inv 1 대신 Inv 3을 사용하여 화합물 Cpd 84 (4.9g, 수율 80%)을 얻었다. A compound Cpd 84 (4.9 g, yield 80%) was obtained in the same manner as in Example 9 except that Inv 3 was used instead of Inv 1.
HRMS [M]+: 804.238HRMS [M] + : 804.238
[[
반응예Example of reaction
17] 17]
CpdCpd
88의 합성 Synthesis of 88
상기 반응예 10과 동일한 과정을 수행하되, Inv 1 대신 Inv 3을 사용하여 화합물 Cpd 88 (5.1g, 수율 81%)을 얻었다. The same procedure as in Reaction Example 10 was performed, except that Inv 3 was used to obtain Compound Cpd 88 (5.1 g, 81% yield).
HRMS [M]+: 804.238HRMS [M] + : 804.238
[[
반응예Example of reaction
18] 18]
CpdCpd
91의 합성 Synthesis of 91
상기 반응예 11과 동일한 과정을 수행하되, Inv 3 대신 Inv 2을 사용하여 화합물 Cpd 91 (3.5g, 수율 80%)을 얻었다. A compound Cpd 91 (3.5 g, yield 80%) was obtained in the same manner as in Example 11, except that Inv 2 was used instead of Inv 3.
HRMS [M]+: 573.158HRMS [M] + : 573.158
[[
반응예Example of reaction
19] 19]
CpdCpd
96의 합성 96 composites
상기 반응예 12과 동일한 과정을 수행하되, Inv 3 대신 Inv 2을 사용하여 화합물 Cpd 96 (4.8g, 수율 85%)을 얻었다. A compound Cpd 96 (4.8 g, yield 85%) was obtained in the same manner as in Example 12, using Inv 2 instead of Inv 3.
HRMS [M]+: 662.185HRMS [M] + : 662.185
[[
반응예Example of reaction
20] 20]
CpdCpd
100의 합성 100 synthetic
상기 반응예 13과 동일한 과정을 수행하되, Inv 3 대신 Inv 2을 사용하여 화합물 Cpd 100 (4.0g, 수율 85%)을 얻었다. A compound Cpd 100 (4.0 g, yield 85%) was obtained in the same manner as in Example 13, using Inv 2 instead of Inv 3.
HRMS [M]+: 634.179HRMS [M] + : 634.179
[[
반응예Example of reaction
21] 21]
CpdCpd
101의 합성 Synthesis of 101
상기 반응예 14과 동일한 과정을 수행하되, Inv 3 대신 Inv 2을 사용하여 화합물 Cpd 101 (4.2g, 수율 92%)을 얻었다. A compound Cpd 101 (4.2 g, yield 92%) was obtained in the same manner as in Example 14, except that Inv 2 was used instead of Inv 3.
HRMS [M]+: 590.120HRMS [M] + : 590.120
[[
반응예Example of reaction
22] 22]
CpdCpd
118의 합성 Synthesis of 118
상기 반응예 15과 동일한 과정을 수행하되, Inv 3 대신 Inv 2을 사용하여 화합물 Cpd 118 (4.2g, 수율 86%)을 얻었다. A compound Cpd 118 (4.2 g, yield 86%) was obtained in the same manner as in Example 15, except that Inv 2 was used instead of Inv 3.
HRMS [M]+: 639.180HRMS [M] + : 639.180
[[
반응예Example of reaction
23] 23]
CpdCpd
129의 합성 Synthesis of 129
상기 반응예 16과 동일한 과정을 수행하되, Inv 3 대신 Inv 2을 사용하여 화합물 Cpd 129 (4.9g, 수율 80%)을 얻었다. A compound Cpd 129 (4.9 g, 80% yield) was obtained in the same manner as in Example 16, except that Inv 2 was used instead of Inv 3.
HRMS [M]+: 804.238HRMS [M] + : 804.238
[[
반응예Example of reaction
24] 24]
CpdCpd
133의 합성 Synthesis of 133
상기 반응예 17과 동일한 과정을 수행하되, Inv 3 대신 Inv 2을 사용하여 화합물 Cpd 133 (5.1g, 수율 81%)을 얻었다. A compound Cpd 133 (5.1 g, 81% yield) was obtained in the same manner as in Example 17, except that Inv 2 was used instead of Inv 3.
HRMS [M]+: 804.238HRMS [M] + : 804.238
[[
반응예Example of reaction
25] 25]
CpdCpd
137의 합성 Synthesis of 137
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
준비예 에서 얻은 Inv 1 (7.3g, 20.0 mmol), (4-(다이([1,1'-바이페닐]-4-일)아미노)페닐)보로닉산 (10.6g, 24.0 mmol), NaOH (2.4g, 60.0 mmol), 및 THF/H2O (100 ml/50 ml)를 넣고 교반하였다. 이후, 40℃에서 Pd(PPh3)4 (5 mol%, 1.2 g)를 넣고, 80℃에서 12시간 동안 교반하였다. Inv 1 (7.3g, 20.0 mmol), (4- (di ([1,1'-biphenyl] -4-yl) amino) phenyl) boronic acid (10.6g, 24.0 mmol), NaOH ( 2.4 g, 60.0 mmol), and THF / H 2 O (100 ml / 50 ml) were added and stirred. Then, Pd (PPh 3 ) 4 (5 mol%, 1.2 g) was added at 40 ° C., and stirred at 80 ° C. for 12 hours.
TLC로 반응이 종결되는 것을 확인한 후, 상온으로 식혔다. 반응 종료 후, 증류수를 넣고 에틸아세테이트로 유기층을 추출하였다. 얻어진 유기층을 Na2SO4 로 건조시키고 감압 증류한 다음, 컬럼 크로마토그래피로 정제하여 화합물 Cpd 137(12.6g, 수율 87%)을 얻었다. After confirming that the reaction was terminated by TLC, it was cooled to room temperature. After the reaction was completed, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and purified by column chromatography to obtain compound Cpd 137 (12.6 g, yield 87%).
HRMS [M]+: 727.237HRMS [M] + : 727.237
[[
반응예Example of reaction
26] 26]
CpdCpd
138의 합성 Synthesis of 138
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
준비예 에서 얻은 Inv 1 (7.3g, 20.0 mmol), 다이([1,1'-바이페닐]-4-일)아민 (7.0 g, 22.0 mmol)을 Toluene (100 ㎖)에 녹인 다음, Pd2(dba)3 (0.9g, 1.0mmol)을 질소 하에서 투입하였다. 이 후, 여기에 NaOtBu (3.8g, 40mmol)을 넣은 후, (t-Bu)3P (1.0 ㎖, 1.0mmol)을 상기 반응액에 투입한 다음, 혼합물을 5시간 동안 환류 교반하였다. Inv 1 (7.3 g, 20.0 mmol) and di ([1,1'-biphenyl] -4-yl) amine (7.0 g, 22.0 mmol) obtained in Preparation Example were dissolved in Toluene (100 mL), and then Pd 2. (dba) 3 (0.9 g, 1.0 mmol) was added under nitrogen. Thereafter, NaOtBu (3.8 g, 40 mmol) was added thereto, and (t-Bu) 3 P (1.0 mL, 1.0 mmol) was added to the reaction solution, and the mixture was stirred under reflux for 5 hours.
TLC로 반응이 종결되는 것을 확인한 후, 상온으로 식혔다. 반응 종료 후, 증류수를 넣고 에틸아세테이트로 유기층을 추출하였다. 얻어진 유기층을 Na2SO4 로 건조시키고 감압 증류한 다음, 컬럼 크로마토그래피로 정제하여 화합물 Cpd 138 (11.0g, 수율 85%)을 얻었다. After confirming that the reaction was terminated by TLC, it was cooled to room temperature. After the reaction was completed, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and purified by column chromatography to obtain compound Cpd 138 (11.0 g, yield 85%).
HRMS [M]+: 651.205HRMS [M] + : 651.205
[[
반응예Example of reaction
27] 27]
CpdCpd
140 합성 140 synthetic
상기 반응예 25과 동일한 과정을 수행하되, ((4-(다이([1,1'-바이페닐]-4-일)아미노)페닐)보로닉산 대신 (4-([1,1'-바이페닐]-4-일(9,9-다이메틸-9H-프로렌-2-일)아미노)페닐)보로닉산을 사용하여 화합물 Cpd 140 (12.2g, 수율 80%)을 얻었다. The same procedure as in Example 25 was carried out, except for ((4-([1,1'-biphenyl] -4-yl) amino) phenyl) boronic acid (4-([1,1'-bi). Phenyl] -4-yl (9,9-dimethyl-9H-proren-2-yl) amino) phenyl) boronic acid gave compound Cpd 140 (12.2 g, yield 80%).
HRMS [M]+: 767.268HRMS [M] + : 767.268
[[
반응예Example of reaction
28] 28]
CpdCpd
149 합성 149 synthetic
상기 반응예 25과 동일한 과정을 수행하되, Inv 1 대신 Inv 3을 사용하여 화합물 Cpd 149 (12.9g, 수율 89%)을 얻었다. A compound Cpd 149 (12.9 g, yield 89%) was obtained in the same manner as in Example 25, but using Inv 3 instead of Inv 1.
HRMS [M]+: 727.237HRMS [M] + : 727.237
[[
반응예Example of reaction
29] 29]
CpdCpd
152 합성 152 synthetic
상기 반응예 27과 동일한 과정을 수행하되, Inv 1 대신 Inv 3을 사용하여 화합물 Cpd 152 (12.7g, 수율 83%)을 얻었다. Compound Cpd 152 (12.7 g, yield 83%) was obtained in the same manner as in Example 27, but using Inv 3 instead of Inv 1.
HRMS [M]+: 767.268HRMS [M] + : 767.268
[[
반응예Example of reaction
30] 30]
CpdCpd
161 합성 161 synthetic
상기 반응예 28과 동일한 과정을 수행하되, Inv 3 대신 Inv 2을 사용하여 화합물 Cpd 161 (12.3g, 수율 85%)을 얻었다. A compound Cpd 161 (12.3 g, yield 85%) was obtained in the same manner as in Reaction Example 28, using Inv 2 instead of Inv 3.
HRMS [M]+: 727.237HRMS [M] + : 727.237
[[
반응예Example of reaction
31] 31]
CpdCpd
164 합성 164 synthetic
상기 반응예 27과 동일한 과정을 수행하되, Inv 3 대신 Inv 2을 사용하여 화합물 Cpd 164 (12.4g, 수율 81%)을 얻었다. Compound Cpd 164 (12.4 g, yield 81%) was obtained by performing the same procedure as in Example 27, but using Inv 2 instead of Inv 3.
HRMS [M]+: 767.268HRMS [M] + : 767.268
[[
반응예Example of reaction
32] 32]
CpdCpd
170의 합성 170 composites
[규칙 제91조에 의한 정정 01.09.2017]
[Correction under Article 91 of the Rule 01.09.2017]
준비예 에서 얻은 Inv 9 (8.4g, 20.0 mmol), N,N-다이 ([1,1'-바이페닐]-4-일)-4'-브로모-[1,1'-바이페닐]-4-아민 (12.1g, 22.0 mmol)을 Toluene (100 ㎖)에 녹인 다음, Pd2(dba)3 (0.9g, 1.0mmol)을 질소 하에서 투입하였다. 이 후, 여기에 NaOtBu (3.8g, 40mmol)을 넣은 후, (t-Bu)3P (1.0 ㎖, 1.0mmol)을 상기 반응액에 투입한 다음, 혼합물을 5시간 동안 환류 교반하였다. Inv 9 (8.4 g, 20.0 mmol) obtained in Preparation Example, N, N-di ([1,1'-biphenyl] -4-yl) -4'-bromo- [1,1'-biphenyl] 4-amine (12.1 g, 22.0 mmol) was dissolved in Toluene (100 mL), and then Pd 2 (dba) 3 (0.9 g, 1.0 mmol) was added under nitrogen. Thereafter, NaOtBu (3.8 g, 40 mmol) was added thereto, and (t-Bu) 3 P (1.0 mL, 1.0 mmol) was added to the reaction solution, and the mixture was stirred under reflux for 5 hours.
TLC로 반응이 종결되는 것을 확인한 후, 상온으로 식혔다. 반응 종료 후, 증류수를 넣고 에틸아세테이트로 유기층을 추출하였다. 얻어진 유기층을 Na2SO4 로 건조시키고 감압 증류한 다음, 컬럼 크로마토그래피로 정제하여 화합물 Cpd 170 (14.3g, 수율 80%)을 얻었다. After confirming that the reaction was terminated by TLC, it was cooled to room temperature. After the reaction was completed, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and purified by column chromatography to obtain compound Cpd 170 (14.3 g, yield 80%).
HRMS [M]+: 892.295HRMS [M] + : 892.295
[[
반응예Example of reaction
33] 33]
CpdCpd
171 합성 171 Synthesis
상기 반응예 32과 동일한 과정을 수행하되, N,N-다이 ([1,1'-바이페닐]-4-일)-4'-브로모-[1,1'-바이페닐]-4-아민 대신 N-([1,1'-바이페닐]-4-일)-N-(4'-브로모-[1,1'-바이페닐]-4-일)-9,9-다이메틸-9H-플로렌-2-아민 을 사용하여 화합물 Cpd 171 (14.0g, 수율 75%)을 얻었다. The same process as in Reaction Example 32 was performed, except that N, N-di ([1,1'-biphenyl] -4-yl) -4'-bromo- [1,1'-biphenyl] -4- N-([1,1'-biphenyl] -4-yl) -N- (4'-bromo- [1,1'-biphenyl] -4-yl) -9,9-dimethyl instead of an amine Compound Cpd 171 (14.0 g, yield 75%) was obtained using -9H-floren-2-amine.
HRMS [M]+: 932.326HRMS [M] + : 932.326
[[
반응예Example of reaction
34] 34]
CpdCpd
180 합성 180 synthetic
상기 반응예 32과 동일한 과정을 수행하되, N,N-다이 ([1,1'-바이페닐]-4-일)-4'-브로모-[1,1'-바이페닐]-4-아민 대신 2-(4-클로로페닐)-4,6-다이페닐-1,3,5-트리아진을 사용하여 화합물 Cpd 180 (11.6g, 수율 80%)을 얻었다. The same process as in Reaction Example 32 was performed, except that N, N-di ([1,1'-biphenyl] -4-yl) -4'-bromo- [1,1'-biphenyl] -4- Compound Cpd 180 (11.6 g, yield 80%) was obtained using 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine in place of amine.
HRMS [M]+: 728.207HRMS [M] + : 728.207
[[
반응예Example of reaction
35] 35]
CpdCpd
183 합성 183 synthetic
상기 반응예 32과 동일한 과정을 수행하되, N,N-다이 ([1,1'-바이페닐]-4-일)-4'-브로모-[1,1'-바이페닐]-4-아민 대신 2-(3- 클로로페닐)-4,6-다이페닐 -1,3,5-트리아진을 사용하여 화합물 Cpd 183 (11.6g, 수율 80%)을 얻었다. The same process as in Reaction Example 32 was performed, except that N, N-di ([1,1'-biphenyl] -4-yl) -4'-bromo- [1,1'-biphenyl] -4- Compound Cpd 183 (11.6 g, yield 80%) was obtained using 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine in place of amine.
HRMS [M]+: 728.207HRMS [M] + : 728.207
[[
반응예Example of reaction
36] 36]
CpdCpd
186 합성 186 synthetic
상기 반응예 32과 동일한 과정을 수행하되, N,N-다이 ([1,1'-바이페닐]-4-일)-4'-브로모-[1,1'-바이페닐]-4-아민 대신 2-(3-브로모페닐)트리페닐렌을 사용하여 화합물 Cpd 186 (11.8g, 수율 82%)을 얻었다. The same process as in Reaction Example 32 was performed, except that N, N-di ([1,1'-biphenyl] -4-yl) -4'-bromo- [1,1'-biphenyl] -4- Compound Cpd 186 (11.8 g, yield 82%) was obtained using 2- (3-bromophenyl) triphenylene instead of amine.
HRMS [M]+: 723.205HRMS [M] + : 723.205
[[
반응예Example of reaction
37] 37]
CpdCpd
187 합성 187 synthetic
상기 반응예 32과 동일한 과정을 수행하되, N,N-다이 ([1,1'-바이페닐]-4-일)-4'-브로모-[1,1'-바이페닐]-4-아민 대신 3-브로모-9-페닐-9H-카바졸을 사용하여 화합물 Cpd 187 (11.9g, 수율 90%)을 얻었다. The same process as in Reaction Example 32 was performed, except that N, N-di ([1,1'-biphenyl] -4-yl) -4'-bromo- [1,1'-biphenyl] -4- 3-Bromo-9-phenyl-9H-carbazole was used instead of the amine to give compound Cpd 187 (11.9 g, 90% yield).
HRMS [M]+: 662.185HRMS [M] + : 662.185
[[
반응예Example of reaction
38] 38]
CpdCpd
194의 합성 194 Synthesis
상기 반응예 32과 동일한 과정을 수행하되, Inv 9 대신 Inv 14를 사용하여 화합물 Cpd 194 (11.6g, 수율 80%)을 얻었다. Compound Cpd 194 (11.6 g, yield 80%) was obtained in the same manner as in Example 32, but using Inv 14 instead of Inv 9.
HRMS [M]+: 892.295HRMS [M] + : 892.295
[[
반응예Example of reaction
33] 33]
CpdCpd
195 합성 195 synthetic
상기 반응예 33과 동일한 과정을 수행하되, Inv 9 대신 Inv 14를 사용하여 화합물 Cpd 195 (14.0g, 수율 75%)을 얻었다. Compound Cpd 195 (14.0 g, yield 75%) was obtained in the same manner as in Example 33, but using Inv 14 instead of Inv 9.
HRMS [M]+: 932.326HRMS [M] + : 932.326
[[
반응예Example of reaction
34] 34]
CpdCpd
204 합성 204 synthetic
상기 반응예 34과 동일한 과정을 수행하되, Inv 9 대신 Inv 14를 사용하여 화합물 Cpd 204 (11.6g, 수율 80%)을 얻었다. Compound Cpd 204 (11.6 g, yield 80%) was obtained in the same manner as in Example 34, but using Inv 14 instead of Inv 9.
HRMS [M]+: 728.207HRMS [M] + : 728.207
[[
반응예Example of reaction
35] 35]
CpdCpd
207 합성 207 synthetic
상기 반응예 35과 동일한 과정을 수행하되, Inv 9 대신 Inv 14를 사용하여 화합물 Cpd 207 (11.6g, 수율 80%)을 얻었다. HRMS [M]+: 728.207A compound Cpd 207 (11.6 g, yield 80%) was obtained in the same manner as in Example 35, but using Inv 14 instead of Inv 9. HRMS [M] + : 728.207
[[
반응예Example of reaction
36] 36]
CpdCpd
210 합성 210 synthetic
상기 반응예 36과 동일한 과정을 수행하되, Inv 9 대신 Inv 14를 사용하여 화합물 Cpd 210 (11.8g, 수율 82%)을 얻었다. Compound Cpd 210 (11.8g, yield 82%) was obtained in the same manner as in Example 36, but using Inv 14 instead of Inv 9.
HRMS [M]+: 723.205HRMS [M] + : 723.205
[[
반응예Example of reaction
37] 37]
CpdCpd
211 합성 211 synthesis
상기 반응예 37과 동일한 과정을 수행하되, Inv 9 대신 Inv 14를 사용하여 화합물 Cpd 211 (11.9g, 수율 90%)을 얻었다. Compound Cpd 211 (11.9 g, yield 90%) was obtained in the same manner as in Example 37, but using Inv 14 instead of Inv 9.
HRMS [M]+: 662.185HRMS [M] + : 662.185
[[
반응예Example of reaction
38] 38]
CpdCpd
218의 합성 218 synthesis
상기 반응예 32과 동일한 과정을 수행하되, Inv 9 대신 Inv 13을 사용하여 화합물 Cpd 218 (11.6g, 수율 80%)을 얻었다. Compound Cpd 218 (11.6 g, yield 80%) was obtained in the same manner as in Example 32, but using Inv 13 instead of Inv 9.
HRMS [M]+: 892.295HRMS [M] + : 892.295
[[
반응예Example of reaction
39] 39]
CpdCpd
219 합성 219 synthetic
상기 반응예 33과 동일한 과정을 수행하되, Inv 9 대신 Inv 13을 사용하여 화합물 Cpd 219 (14.0g, 수율 75%)을 얻었다. Compound Cpd 219 (14.0 g, yield 75%) was obtained in the same manner as in Example 33, but using Inv 13 instead of Inv 9.
HRMS [M]+: 932.326HRMS [M] + : 932.326
[[
반응예Example of reaction
40] 40]
CpdCpd
228 합성 228 synthetic
상기 반응예 34과 동일한 과정을 수행하되, Inv 9 대신 Inv 13을 사용하여 화합물 Cpd 228 (11.6g, 수율 80%)을 얻었다. Compound Cpd 228 (11.6 g, yield 80%) was obtained in the same manner as in Example 34, but using Inv 13 instead of Inv 9.
HRMS [M]+: 728.207HRMS [M] + : 728.207
[[
반응예Example of reaction
41] 41]
CpdCpd
231 합성 231 synthetic
상기 반응예 35과 동일한 과정을 수행하되, Inv 9 대신 Inv 13을 사용하여 화합물 Cpd 231 (11.6g, 수율 80%)을 얻었다. The same procedure as in Example 35 was carried out, except that Inv 13 was used instead of Inv 9 to obtain compound Cpd 231 (11.6 g, yield 80%).
HRMS [M]+: 728.207HRMS [M] + : 728.207
[[
반응예Example of reaction
42] 42]
CpdCpd
234 합성 234 synthetic
상기 반응예 36과 동일한 과정을 수행하되, Inv 9 대신 Inv 13을 사용하여 화합물 Cpd 234 (11.8g, 수율 82%)을 얻었다. Compound Cpd 234 (11.8 g, yield 82%) was obtained in the same manner as in Example 36, but using Inv 13 instead of Inv 9.
HRMS [M]+: 723.205HRMS [M] + : 723.205
[[
반응예Example of reaction
43] 43]
CpdCpd
235 합성 235 synthetic
상기 반응예 37과 동일한 과정을 수행하되, Inv 9 대신 Inv 13을 사용하여 화합물 Cpd 235 (11.9g, 수율 90%)을 얻었다. Compound Cpd 235 (11.9 g, yield 90%) was obtained in the same manner as in Example 37, but using Inv 13 instead of Inv 9.
HRMS [M]+: 662.185HRMS [M] + : 662.185
[[
반응예Example of reaction
44] 44]
CpdCpd
242 합성 242 synthetic
상기 반응예 32과 동일한 과정을 수행하되, Inv 9 대신 Inv 7을 사용하여 화합물 Cpd 242 (11.6g, 수율 80%)을 얻었다. Compound Cpd 242 (11.6 g, yield 80%) was obtained in the same manner as in Example 32, but using Inv 7 instead of Inv 9.
HRMS [M]+: 892.295HRMS [M] + : 892.295
[[
반응예Example of reaction
45] 45]
CpdCpd
243 합성 243 synthetic
상기 반응예 33과 동일한 과정을 수행하되, Inv 9 대신 Inv 7을 사용하여 화합물 Cpd 243 (14.0g, 수율 75%)을 얻었다. Compound Cpd 243 (14.0 g, yield 75%) was obtained in the same manner as in Example 33, but using Inv 7 instead of Inv 9.
HRMS [M]+: 932.326HRMS [M] + : 932.326
[[
반응예Example of reaction
46] 46]
CpdCpd
252 합성 252 Synthesis
상기 반응예 34과 동일한 과정을 수행하되, Inv 9 대신 Inv 7을 사용하여 화합물 Cpd 252 (11.6g, 수율 80%)을 얻었다. Compound Cpd 252 (11.6 g, yield 80%) was obtained in the same manner as in Example 34, but using Inv 7 instead of Inv 9.
HRMS [M]+: 728.207HRMS [M] + : 728.207
[[
반응예Example of reaction
47] 47]
CpdCpd
255 합성 255 composite
상기 반응예 35과 동일한 과정을 수행하되, Inv 9 대신 Inv 7을 사용하여 화합물 Cpd 255 (11.6g, 수율 80%)을 얻었다. A compound Cpd 255 (11.6 g, yield 80%) was obtained in the same manner as in Example 35, but using Inv 7 instead of Inv 9.
HRMS [M]+: 728.207HRMS [M] + : 728.207
[[
반응예Example of reaction
48] 48]
CpdCpd
258 합성 258 synthetic
상기 반응예 36과 동일한 과정을 수행하되, Inv 9 대신 Inv 7을 사용하여 화합물 Cpd 258 (11.8g, 수율 82%)을 얻었다. Compound Cpd 258 (11.8 g, yield 82%) was obtained in the same manner as in Example 36, but using Inv 7 instead of Inv 9.
HRMS [M]+: 723.205HRMS [M] + : 723.205
[[
반응예Example of reaction
49] 49]
CpdCpd
259 합성 259 synthetic
상기 반응예 37과 동일한 과정을 수행하되, Inv 9 대신 Inv 7을 사용하여 화합물 Cpd 259 (11.9g, 수율 90%)을 얻었다. Compound Cpd 259 (11.9 g, yield 90%) was obtained in the same manner as in Example 37, but using Inv 7 instead of Inv 9.
HRMS [M]+: 662.185HRMS [M] + : 662.185
[[
반응예Example of reaction
50] 50]
CpdCpd
266 합성 266 synthetic
상기 반응예 32과 동일한 과정을 수행하되, Inv 9 대신 Inv 8을 사용하여 화합물 Cpd 266 (11.6g, 수율 80%)을 얻었다. The same procedure as in Example 32 was carried out, except that Inv 8 was used instead of Inv 9 to obtain Compound Cpd 266 (11.6 g, 80% yield).
HRMS [M]+: 892.295HRMS [M] + : 892.295
[[
반응예Example of reaction
51] 51]
CpdCpd
267 합성 267 synthetic
상기 반응예 33과 동일한 과정을 수행하되, Inv 9 대신 Inv 8을 사용하여 화합물 Cpd 267 (14.0g, 수율 75%)을 얻었다. Compound Cpd 267 (14.0 g, yield 75%) was obtained in the same manner as in Example 33, but using Inv 8 instead of Inv 9.
HRMS [M]+: 932.326HRMS [M] + : 932.326
[[
반응예Example of reaction
52] 52]
CpdCpd
276 합성 276 Synthesis
상기 반응예 34과 동일한 과정을 수행하되, Inv 9 대신 Inv 8을 사용하여 화합물 Cpd 276 (11.6g, 수율 80%)을 얻었다. Compound Cpd 276 (11.6 g, yield 80%) was obtained in the same manner as in Example 34, but using Inv 8 instead of Inv 9.
HRMS [M]+: 728.207HRMS [M] + : 728.207
[[
반응예Example of reaction
53] 53]
CpdCpd
279 합성 279 synthetic
상기 반응예 35과 동일한 과정을 수행하되, Inv 9 대신 Inv 8을 사용하여 화합물 Cpd 279 (11.6g, 수율 80%)을 얻었다. A compound Cpd 279 (11.6 g, yield 80%) was obtained in the same manner as in Example 35, but using Inv 8 instead of Inv 9.
HRMS [M]+: 728.207HRMS [M] + : 728.207
[[
반응예Example of reaction
54] 54]
CpdCpd
282 합성 282 synthetic
상기 반응예 36과 동일한 과정을 수행하되, Inv 9 대신 Inv 8을 사용하여 화합물 Cpd 282 (11.8g, 수율 82%)을 얻었다. Compound Cpd 282 (11.8 g, yield 82%) was obtained in the same manner as in Example 36, but using Inv 8 instead of Inv 9.
HRMS [M]+: 723.205HRMS [M] + : 723.205
[[
반응예Example of reaction
55] 55]
CpdCpd
283 합성 283 synthetic
상기 반응예 37과 동일한 과정을 수행하되, Inv 9 대신 Inv 8을 사용하여 화합물 Cpd 283 (11.9g, 수율 90%)을 얻었다. Compound Cpd 283 (11.9 g, yield 90%) was obtained in the same manner as in Example 37, but using Inv 8 instead of Inv 9.
HRMS [M]+: 662.185HRMS [M] + : 662.185
[[
반응예Example of reaction
56] 56]
CpdCpd
290 합성 290 synthetic
상기 반응예 32과 동일한 과정을 수행하되, Inv 9 대신 Inv 12을 사용하여 화합물 Cpd 290 (11.6g, 수율 80%)을 얻었다. Compound Cpd 290 (11.6 g, yield 80%) was obtained by performing the same process as in Reaction Example 32, but using Inv 12 instead of Inv 9.
HRMS [M]+: 892.295HRMS [M] + : 892.295
[[
반응예Example of reaction
57] 57]
CpdCpd
291 합성 291 synthetic
상기 반응예 33과 동일한 과정을 수행하되, Inv 9 대신 Inv 12을 사용하여 화합물 Cpd 291 (14.0g, 수율 75%)을 얻었다. Compound Cpd 291 (14.0 g, yield 75%) was obtained in the same manner as in Example 33, but using Inv 12 instead of Inv 9.
HRMS [M]+: 932.326HRMS [M] + : 932.326
[[
반응예Example of reaction
58] 58]
CpdCpd
300 합성 300 synthetic
상기 반응예 34과 동일한 과정을 수행하되, Inv 9 대신 Inv 12을 사용하여 화합물 Cpd 300 (11.6g, 수율 80%)을 얻었다. A compound Cpd 300 (11.6 g, yield 80%) was obtained in the same manner as in Example 34 except that Inv 12 was used instead of Inv 9.
HRMS [M]+: 728.207HRMS [M] + : 728.207
[[
반응예Example of reaction
59] 59]
CpdCpd
303 합성 303 Synthesis
상기 반응예 35과 동일한 과정을 수행하되, Inv 9 대신 Inv 12을 사용하여 화합물 Cpd 303 (11.6g, 수율 80%)을 얻었다. A compound Cpd 303 (11.6 g, yield 80%) was obtained in the same manner as in Example 35, but using Inv 12 instead of Inv 9.
HRMS [M]+: 728.207HRMS [M] + : 728.207
[[
반응예Example of reaction
60] 60]
CpdCpd
306 합성 306 synthetic
상기 반응예 36과 동일한 과정을 수행하되, Inv 9 대신 Inv 12을 사용하여 화합물 Cpd 306 (11.8g, 수율 82%)을 얻었다. Compound Cpd 306 (11.8 g, yield 82%) was obtained in the same manner as in Example 36, but using Inv 12 instead of Inv 9.
HRMS [M]+: 723.205HRMS [M] + : 723.205
[[
반응예Example of reaction
61] 61]
CpdCpd
307 합성 307 synthesis
상기 반응예 37과 동일한 과정을 수행하되, Inv 9 대신 Inv 12을 사용하여 화합물 Cpd 307 (11.9g, 수율 90%)을 얻었다. Compound Cpd 307 (11.9 g, yield 90%) was obtained in the same manner as in Example 37, but using Inv 12 instead of Inv 9.
HRMS [M]+: 662.185HRMS [M] + : 662.185
[[
반응예Example of reaction
62] 62]
CpdCpd
314 합성 314 synthetic
상기 반응예 32과 동일한 과정을 수행하되, Inv 9 대신 Inv 11을 사용하여 화합물 Cpd 314 (11.6g, 수율 80%)을 얻었다. Compound Cpd 314 (11.6 g, yield 80%) was obtained by performing the same procedure as in Reaction Example 32, but using Inv 11 instead of Inv 9.
HRMS [M]+: 892.295HRMS [M] + : 892.295
[[
반응예Example of reaction
63] 63]
CpdCpd
315 합성 315 synthetic
상기 반응예 33과 동일한 과정을 수행하되, Inv 9 대신 Inv 11을 사용하여 화합물 Cpd 315 (14.0g, 수율 75%)을 얻었다. Compound Cpd 315 (14.0 g, yield 75%) was obtained in the same manner as in Example 33, but using Inv 11 instead of Inv 9.
HRMS [M]+: 932.326HRMS [M] + : 932.326
[[
반응예Example of reaction
64] 64]
CpdCpd
324 합성 324 synthetic
상기 반응예 34과 동일한 과정을 수행하되, Inv 9 대신 Inv 11을 사용하여 화합물 Cpd 324 (11.6g, 수율 80%)을 얻었다. Compound Cpd 324 (11.6 g, yield 80%) was obtained in the same manner as in Example 34, but using Inv 11 instead of Inv 9.
HRMS [M]+: 728.207HRMS [M] + : 728.207
[[
반응예Example of reaction
65] 65]
CpdCpd
327 합성 327 synthetic
상기 반응예 35과 동일한 과정을 수행하되, Inv 9 대신 Inv 11을 사용하여 화합물 Cpd 327 (11.6g, 수율 80%)을 얻었다. A compound Cpd 327 (11.6 g, yield 80%) was obtained in the same manner as in Example 35, but using Inv 11 instead of Inv 9.
HRMS [M]+: 728.207HRMS [M] + : 728.207
[[
반응예Example of reaction
66] 66]
CpdCpd
330 합성 330 synthetic
상기 반응예 36과 동일한 과정을 수행하되, Inv 9 대신 Inv 11을 사용하여 화합물 Cpd 330 (11.8g, 수율 82%)을 얻었다. Compound Cpd 330 (11.8 g, yield 82%) was obtained in the same manner as in Example 36, but using Inv 11 instead of Inv 9.
HRMS [M]+: 723.205HRMS [M] + : 723.205
[[
반응예Example of reaction
67] 67]
CpdCpd
331 합성 331 synthetic
상기 반응예 37과 동일한 과정을 수행하되, Inv 9 대신 Inv 11을 사용하여 화합물 Cpd 331 (11.9g, 수율 90%)을 얻었다. Compound Cpd 331 (11.9 g, yield 90%) was obtained in the same manner as in Example 37, but using Inv 11 instead of Inv 9.
HRMS [M]+: 662.185HRMS [M] + : 662.185
[[
반응예Example of reaction
68] 68]
CpdCpd
338 합성 338 synthetic
상기 반응예 32과 동일한 과정을 수행하되, Inv 9 대신 Inv 16을 사용하여 화합물 Cpd 338 (11.6g, 수율 80%)을 얻었다. Compound Cpd 338 (11.6 g, yield 80%) was obtained in the same manner as in Example 32, but using Inv 16 instead of Inv 9.
HRMS [M]+: 892.295HRMS [M] + : 892.295
[[
반응예Example of reaction
69] 69]
CpdCpd
339 합성 339 synthetic
상기 반응예 33과 동일한 과정을 수행하되, Inv 9 대신 Inv 16을 사용하여 화합물 Cpd 339 (14.0g, 수율 75%)을 얻었다. Compound Cpd 339 (14.0 g, yield 75%) was obtained in the same manner as in Example 33, but using Inv 16 instead of Inv 9.
HRMS [M]+: 932.326HRMS [M] + : 932.326
[[
반응예Example of reaction
70] 70]
CpdCpd
348 합성 348 synthetic
상기 반응예 34과 동일한 과정을 수행하되, Inv 9 대신 Inv 16을 사용하여 화합물 Cpd 348 (11.6g, 수율 80%)을 얻었다. Compound Cpd 348 (11.6 g, yield 80%) was obtained by performing the same procedure as in Example 34, but using Inv 16 instead of Inv 9.
HRMS [M]+: 728.207HRMS [M] + : 728.207
[[
반응예Example of reaction
71] 71]
CpdCpd
351 합성 351 synthetic
상기 반응예 35과 동일한 과정을 수행하되, Inv 9 대신 Inv 16을 사용하여 화합물 Cpd 351 (11.6g, 수율 80%)을 얻었다. A compound Cpd 351 (11.6 g, yield 80%) was obtained in the same manner as in Example 35, but using Inv 16 instead of Inv 9.
HRMS [M]+: 728.207HRMS [M] + : 728.207
[[
반응예Example of reaction
72] 72]
CpdCpd
354 합성 354 synthetic
상기 반응예 36과 동일한 과정을 수행하되, Inv 9 대신 Inv 16을 사용하여 화합물 Cpd 354 (11.8g, 수율 82%)을 얻었다. Compound Cpd 354 (11.8 g, yield 82%) was obtained in the same manner as in Example 36, but using Inv 16 instead of Inv 9.
HRMS [M]+: 723.205HRMS [M] + : 723.205
[[
반응예Example of reaction
73] 73]
CpdCpd
355 합성 355 synthetic
상기 반응예 37과 동일한 과정을 수행하되, Inv 9 대신 Inv 16을 사용하여 화합물 Cpd 355 (11.9g, 수율 90%)을 얻었다. Compound Cpd 355 (11.9 g, yield 90%) was obtained in the same manner as in Example 37, but using Inv 16 instead of Inv 9.
HRMS [M]+: 662.185HRMS [M] + : 662.185
[[
반응예Example of reaction
68] 68]
CpdCpd
362 합성 362 synthetic
상기 반응예 32과 동일한 과정을 수행하되, Inv 9 대신 Inv 15을 사용하여 화합물 Cpd 362 (11.6g, 수율 80%)을 얻었다. Compound Cpd 362 (11.6 g, yield 80%) was obtained by performing the same procedure as in Reaction Example 32, but using Inv 15 instead of Inv 9.
HRMS [M]+: 892.295HRMS [M] + : 892.295
[[
반응예Example of reaction
69] 69]
CpdCpd
363 합성 363 synthetic
상기 반응예 33과 동일한 과정을 수행하되, Inv 9 대신 Inv 15을 사용하여 화합물 Cpd 363 (14.0g, 수율 75%)을 얻었다. Compound Cpd 363 (14.0 g, yield 75%) was obtained in the same manner as in Example 33, but using Inv 15 instead of Inv 9.
HRMS [M]+: 932.326HRMS [M] + : 932.326
[[
반응예Example of reaction
70] 70]
CpdCpd
372 합성 372 synthetic
상기 반응예 34과 동일한 과정을 수행하되, Inv 9 대신 Inv 15을 사용하여 화합물 Cpd 372 (11.6g, 수율 80%)을 얻었다. Compound Cpd 372 (11.6 g, yield 80%) was obtained in the same manner as in Example 34, but using Inv 15 instead of Inv 9.
HRMS [M]+: 728.207HRMS [M] + : 728.207
[[
반응예Example of reaction
71] 71]
CpdCpd
375 합성 375 synthetic
상기 반응예 35과 동일한 과정을 수행하되, Inv 9 대신 Inv 15을 사용하여 화합물 Cpd 375 (11.6g, 수율 80%)을 얻었다. A compound Cpd 375 (11.6 g, yield 80%) was obtained in the same manner as in Example 35, but using Inv 15 instead of Inv 9.
HRMS [M]+: 728.207HRMS [M] + : 728.207
[[
반응예Example of reaction
72] 72]
CpdCpd
378 합성 378 synthetic
상기 반응예 36과 동일한 과정을 수행하되, Inv 9 대신 Inv 15을 사용하여 화합물 Cpd 378 (11.8g, 수율 82%)을 얻었다. Compound Cpd 378 (11.8 g, yield 82%) was obtained in the same manner as in Example 36, but using Inv 15 instead of Inv 9.
HRMS [M]+: 723.205HRMS [M] + : 723.205
[[
반응예Example of reaction
73] 73]
CpdCpd
379 합성 379 synthetic
상기 반응예 37과 동일한 과정을 수행하되, Inv 9 대신 Inv 15을 사용하여 화합물 Cpd 379 (11.9g, 수율 90%)을 얻었다. Compound Cpd 379 (11.9 g, yield 90%) was obtained in the same manner as in Example 37, but using Inv 15 instead of Inv 9.
HRMS [M]+: 662.185HRMS [M] + : 662.185
[[
반응예Example of reaction
74] 74]
CpdCpd
386 합성 386 synthetic
상기 반응예 32과 동일한 과정을 수행하되, Inv 9 대신 Inv 18을 사용하여 화합물 Cpd 386 (11.6g, 수율 80%)을 얻었다. Compound Cpd 386 (11.6 g, yield 80%) was obtained in the same manner as in Example 32, but using Inv 18 instead of Inv 9.
HRMS [M]+: 892.295HRMS [M] + : 892.295
[[
반응예Example of reaction
75] 75]
CpdCpd
387 합성 387 synthetic
상기 반응예 33과 동일한 과정을 수행하되, Inv 9 대신 Inv 18을 사용하여 화합물 Cpd 387 (14.0g, 수율 75%)을 얻었다. Compound Cpd 387 (14.0 g, yield 75%) was obtained in the same manner as in Example 33, but using Inv 18 instead of Inv 9.
HRMS [M]+: 932.326HRMS [M] + : 932.326
[[
반응예Example of reaction
76] 76]
CpdCpd
396 합성 396 synthetic
상기 반응예 34과 동일한 과정을 수행하되, Inv 9 대신 Inv 18을 사용하여 화합물 Cpd 396 (11.6g, 수율 80%)을 얻었다. Compound Cpd 396 (11.6 g, yield 80%) was obtained in the same manner as in Example 34, but using Inv 18 instead of Inv 9.
HRMS [M]+: 728.207HRMS [M] + : 728.207
[[
반응예Example of reaction
77] 77]
CpdCpd
399 합성 399 synthetic
상기 반응예 35과 동일한 과정을 수행하되, Inv 9 대신 Inv 18을 사용하여 화합물 Cpd 399 (11.6g, 수율 80%)을 얻었다. A compound Cpd 399 (11.6 g, yield 80%) was obtained in the same manner as in Example 35, but using Inv 18 instead of Inv 9.
HRMS [M]+: 728.207HRMS [M] + : 728.207
[[
반응예Example of reaction
78] 78]
CpdCpd
402 합성 402 synthetic
상기 반응예 36과 동일한 과정을 수행하되, Inv 9 대신 Inv 18을 사용하여 화합물 Cpd 402 (11.8g, 수율 82%)을 얻었다. Compound Cpd 402 (11.8 g, yield 82%) was obtained in the same manner as in Example 36, but using Inv 18 instead of Inv 9.
HRMS [M]+: 723.205HRMS [M] + : 723.205
[[
반응예Example of reaction
79] 79]
CpdCpd
403 합성 403 Synthesis
상기 반응예 37과 동일한 과정을 수행하되, Inv 9 대신 Inv 18을 사용하여 화합물 Cpd 403 (11.9g, 수율 90%)을 얻었다. Compound Cpd 403 (11.9 g, yield 90%) was obtained in the same manner as in Example 37, but using Inv 18 instead of Inv 9.
HRMS [M]+: 662.185HRMS [M] + : 662.185
[ [
반응예Example of reaction
80] 80]
CpdCpd
410 합성 410 synthetic
상기 반응예 32과 동일한 과정을 수행하되, Inv 9 대신 Inv 17을 사용하여 화합물 Cpd 410 (11.6g, 수율 80%)을 얻었다. Compound Cpd 410 (11.6 g, yield 80%) was obtained by performing the same procedure as in Reaction Example 32, but using Inv 17 instead of Inv 9.
HRMS [M]+: 892.295HRMS [M] + : 892.295
[[
반응예Example of reaction
81] 81]
CpdCpd
411 합성 411 synthetic
상기 반응예 33과 동일한 과정을 수행하되, Inv 9 대신 Inv 17을 사용하여 화합물 Cpd 411 (15.1g, 수율 81%)을 얻었다. Compound Cpd 411 (15.1 g, 81% yield) was obtained in the same manner as in Example 33, but using Inv 17 instead of Inv 9.
HRMS [M]+: 932.326HRMS [M] + : 932.326
[[
반응예Example of reaction
82] 82]
CpdCpd
420 합성 420 synthetic
상기 반응예 34과 동일한 과정을 수행하되, Inv 9 대신 Inv 17을 사용하여 화합물 Cpd 420 (12.2g, 수율 84%)을 얻었다. Compound Cpd 420 (12.2 g, yield 84%) was obtained by performing the same procedure as in Example 34, but using Inv 17 instead of Inv 9.
HRMS [M]+: 728.207HRMS [M] + : 728.207
[[
반응예Example of reaction
83] 83]
CpdCpd
423 합성 423 Synthesis
상기 반응예 35과 동일한 과정을 수행하되, Inv 9 대신 Inv 17을 사용하여 화합물 Cpd 423 (11.6g, 수율 80%)을 얻었다. A compound Cpd 423 (11.6 g, yield 80%) was obtained in the same manner as in Example 35, but using Inv 17 instead of Inv 9.
HRMS [M]+: 728.207HRMS [M] + : 728.207
[[
반응예Example of reaction
84] 84]
CpdCpd
426 합성 426 synthetic
상기 반응예 36과 동일한 과정을 수행하되, Inv 9 대신 Inv 17을 사용하여 화합물 Cpd 426 (11.8g, 수율 82%)을 얻었다. Compound Cpd 426 (11.8 g, yield 82%) was obtained in the same manner as in Example 36, but using Inv 17 instead of Inv 9.
HRMS [M]+: 723.205HRMS [M] + : 723.205
[[
반응예Example of reaction
85] 85]
CpdCpd
427 합성 427 synthetic
상기 반응예 37과 동일한 과정을 수행하되, Inv 9 대신 Inv 17을 사용하여 화합물 Cpd 427 (11.4g, 수율 86%)을 얻었다. Compound Cpd 427 (11.4 g, yield 86%) was obtained in the same manner as in Example 37, but using Inv 17 instead of Inv 9.
HRMS [M]+: 662.185HRMS [M] + : 662.185
[[
실시예Example
1] 녹색 유기 1] Green Organic
전계Electric field
발광 소자의 제조 Manufacture of light emitting device
화합물 Cpd137을 통상적으로 알려진 방법으로 고순도 승화 정제를 한 후, 하기와 같이 녹색 유기 전계 발광 소자를 제조하였다.After high purity sublimation purification of compound Cpd137 by a commonly known method, a green organic electroluminescent device was manufactured as follows.
ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면, 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고, 건조시킨 후, UV OZONE 세정기(Power sonic 405, 화신테크)로 이송시킨 다음, UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.A glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonically. 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, Hwasin Tech), and then the substrate using UV for 5 minutes The substrate was cleaned and transferred to a vacuum evaporator.
이와 같이 준비된 ITO 투명 전극 위에, m-MTDATA (60nm) / TCTA (80 nm) / 화합물 cpd137 (40nm) / CBP+10%Ir(ppy)3
(30nm) / BCP (10nm) / Alq3
(30nm) / LiF (1nm) / Al (200nm) 순으로 적층하여 유기 전계 발광 소자를 제조하였다.On the prepared ITO transparent electrode, m-MTDATA (60 nm) / TCTA (80 nm) / compound cpd137 (40 nm) / CBP + 10% Ir (ppy) 3 (30nm) / BCP (10nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) was laminated in order to manufacture an organic EL device.
여기서, 사용된 m-MTDATA, TCTA, Ir(ppy)3, CBP 및 BCP의 구조는 하기와 같다.Here, the structures of m-MTDATA, TCTA, Ir (ppy) 3 , CBP and BCP used are as follows.
[[
실시예Example
2 ~ 29] 녹색 유기 2 to 29] green organic
전계Electric field
발광 소자의 제조 Manufacture of light emitting device
실시예 1에서 사용된 화합물 Cpd137 대신 하기 표 1에 기재된 화합물을 각각 사용하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 유기 전계 발광 소자를 제조하였다.An organic electroluminescent device was manufactured in the same manner as in Example 1, except that each of the compounds shown in Table 1 was used instead of the compound Cpd137 used in Example 1.
[[
비교예Comparative example
1] 녹색 유기 1] Green Organic
전계Electric field
발광 소자의 제조 Manufacture of light emitting device
실시예 1에서 사용된 화합물 Cpd137을 사용하지 않은 것을 제외하고는, 실시예 1과 동일하게 수행하여 녹색 유기 전계 발광 소자를 제조하였다.A green organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound Cpd137, which was used in Example 1, was not used.
[[
평가예Evaluation example
1] One]
실시예 1 내지 29, 및 비교예 1에서 각각 제조된 녹색 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하였고, 그 결과를 하기 표 1에 나타내었다.For green organic electroluminescent devices prepared in Examples 1 to 29 and Comparative Example 1, driving voltage, current efficiency, and emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below. It was.
| 구분division | 발광보조층 재료Luminous auxiliary layer material | 구동 전압(V)Drive voltage (V) | 발광 피크(nm)Emission Peak (nm) | 전류효율(cd/A)Current efficiency (cd / A) |
| 실시예 1Example 1 | Cpd 137Cpd 137 | 6.856.85 | 518518 | 41.941.9 |
| 실시예 2Example 2 | Cpd 138Cpd 138 | 6.716.71 | 520520 | 41.541.5 |
| 실시예 3Example 3 | Cpd 140Cpd 140 | 6.856.85 | 518518 | 41.841.8 |
| 실시예 4Example 4 | Cpd 149Cpd 149 | 6.856.85 | 520520 | 41.841.8 |
| 실시예 5Example 5 | Cpd 152Cpd 152 | 6.806.80 | 519519 | 41.541.5 |
| 실시예 6Example 6 | Cpd 161Cpd 161 | 6.906.90 | 518518 | 41.841.8 |
| 실시예 7Example 7 | Cpd 164Cpd 164 | 6.856.85 | 520520 | 41.541.5 |
| 실시예 8Example 8 | Cpd 170Cpd 170 | 6.736.73 | 518518 | 41.541.5 |
| 실시예 9Example 9 | Cpd 171Cpd 171 | 6.746.74 | 520520 | 41.841.8 |
| 실시예 10Example 10 | Cpd 194Cpd 194 | 6.756.75 | 518518 | 41.841.8 |
| 실시예 11Example 11 | Cpd 195Cpd 195 | 6.806.80 | 517517 | 41.541.5 |
| 실시예 12Example 12 | Cpd 218Cpd 218 | 6.776.77 | 518518 | 42.042.0 |
| 실시예 13Example 13 | Cpd 219Cpd 219 | 6.726.72 | 520520 | 41.941.9 |
| 실시예 14Example 14 | Cpd 242Cpd 242 | 6.806.80 | 518518 | 41.541.5 |
| 실시예 15Example 15 | Cpd 243Cpd 243 | 6.696.69 | 520520 | 41.841.8 |
| 실시예 16Example 16 | Cpd 266Cpd 266 | 6.826.82 | 517517 | 41.841.8 |
| 실시예 17Example 17 | Cpd 267Cpd 267 | 6.756.75 | 518518 | 41.841.8 |
| 실시예 18Example 18 | Cpd 290Cpd 290 | 6.806.80 | 520520 | 42.042.0 |
| 실시예 19Example 19 | Cpd 291Cpd 291 | 6.776.77 | 518518 | 42.042.0 |
| 실시예 20Example 20 | Cpd 314Cpd 314 | 6.856.85 | 520520 | 41.541.5 |
| 실시예 21Example 21 | Cpd 315Cpd 315 | 6.806.80 | 519519 | 41.841.8 |
| 실시예 22Example 22 | Cpd 338Cpd 338 | 6.906.90 | 517517 | 41.841.8 |
| 실시예 23Example 23 | Cpd 339Cpd 339 | 6.706.70 | 518518 | 41.541.5 |
| 실시예 24Example 24 | Cpd 362Cpd 362 | 6.736.73 | 520520 | 41.841.8 |
| 실시예 25Example 25 | Cpd 363Cpd 363 | 6.746.74 | 518518 | 42.042.0 |
| 실시예 26Example 26 | Cpd 386Cpd 386 | 6.696.69 | 520520 | 41.841.8 |
| 실시예 27Example 27 | Cpd 387Cpd 387 | 6.736.73 | 518518 | 41.841.8 |
| 실시예 28Example 28 | Cpd 410Cpd 410 | 6.806.80 | 520520 | 41.541.5 |
| 실시예 29Example 29 | Cpd 411Cpd 411 | 6.716.71 | 519519 | 41.541.5 |
| 비교예 1Comparative Example 1 | -- | 6.936.93 | 516516 | 38.238.2 |
상기 표 1에 나타낸 바와 같이, 본 발명에 따른 화합물을 발광 보조층 재료로 사용한 실시예 1 내지 29의 녹색 유기 전계 발광 소자는, 발광 보조층 없이 CBP만을 발광층 재료로 사용한 비교예 1의 녹색 유기 전계 발광 소자에 비해 구동 전압이 약간 낮았으며, 비교예 1의 녹색 유기 전계 발광 소자에 비해 전류 효율이 더 우수하다는 것을 알 수 있었다.As shown in Table 1, the green organic electroluminescent device of Examples 1 to 29 using the compound according to the present invention as a light emitting auxiliary layer material, the green organic electric field of Comparative Example 1 using only CBP as a light emitting layer material without a light emitting auxiliary layer The driving voltage was slightly lower than that of the light emitting device, and the current efficiency was better than that of the green organic electroluminescent device of Comparative Example 1.
[ [
실시예Example
30] 적색 유기 30] red organic
전계Electric field
발광 소자의 제조 Manufacture of light emitting device
화합물 Cpd137을 통상적으로 알려진 방법으로 고순도 승화 정제를 한 후, 하기와 같이 녹색 유기 전계 발광 소자를 제조하였다.After high purity sublimation purification of compound Cpd137 by a commonly known method, a green organic electroluminescent device was manufactured as follows.
먼저, ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기 (Powersonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고진공 증착기로 기판을 이송하였다.First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 mm 3 was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a UV OZONE cleaner (Powersonic 405, Hwasin Tech), and then washed the substrate using UV for 5 minutes and vacuum The substrate was transferred.
이와 같이 준비된 ITO 투명 전극 위에, m-MTDATA (60 nm) / TCTA (80 nm) / 화합물 cpd137 (40nm) / CBP+10 %(piq)2Ir(acac) (30nm) / BCP (10 nm) /Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제조하였다.On the thus prepared ITO transparent electrode, m-MTDATA (60 nm) / TCTA (80 nm) / compound cpd137 (40 nm) / CBP + 10% (piq) 2 Ir (acac) (30 nm) / BCP (10 nm) / An organic electroluminescent device was manufactured by stacking in order of Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm).
여기서 사용된 m-MTDATA, TCTA, CBP 및 BCP의 구조는 실시예 1에 기재된 바와 같고, (piq)2Ir(acac)는 하기와 같다.The structures of m-MTDATA, TCTA, CBP and BCP used here are as described in Example 1, and (piq) 2 Ir (acac) is as follows.
[[
실시예Example
31 ~ 58] 적색 유기 31 ~ 58] red organic
전계Electric field
발광 소자의 제조 Manufacture of light emitting device
실시예 30에서 사용된 화합물 Cpd137 대신 하기 표 2에 기재된 화합물을 각각 사용하는 것을 제외하고는, 실시예 30와 동일하게 수행하여 적색 유기 전계 발광 소자를 제조하였다.A red organic electroluminescent device was manufactured in the same manner as in Example 30, except that each of the compounds shown in Table 2 was used instead of the compound Cpd137 used in Example 30.
[[
비교예Comparative example
2] 적색 유기 2] red organic
전계Electric field
발광 소자의 제작 Fabrication of light emitting device
실시예 30에서 사용된 화합물 Cpd137을 사용하지 않은 것을 제외하고는, 실시예 30과 동일하게 수행하여 적색 유기 전계 발광 소자를 제조하였다.A red organic electroluminescent device was manufactured in the same manner as in Example 30, except that Compound Cpd137, which was used in Example 30, was not used.
[[
평가예Evaluation example
2] 2]
실시예 30 ~ 58 및 비교예 2에서 제작된 각각의 적색 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압 및 전류효율을 측정하였고, 그 결과를 하기 표 2에 나타내었다.For each of the red organic EL devices manufactured in Examples 30 to 58 and Comparative Example 2, the driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured, and the results are shown in Table 2 below.
| 구분division | 발광보조층 재료Luminous auxiliary layer material | 구동 전압 (V)Driving voltage (V) | 전류효율 (cd/A)Current efficiency (cd / A) |
| 실시예 30Example 30 | Cpd 137Cpd 137 | 5.105.10 | 11.011.0 |
| 실시예 31Example 31 | Cpd 138Cpd 138 | 5.155.15 | 11.311.3 |
| 실시예 32Example 32 | Cpd 140Cpd 140 | 5.105.10 | 11.011.0 |
| 실시예 33Example 33 | Cpd 149Cpd 149 | 5.155.15 | 11.311.3 |
| 실시예 34Example 34 | Cpd 152Cpd 152 | 5.205.20 | 10.810.8 |
| 실시예 35Example 35 | Cpd 161Cpd 161 | 5.135.13 | 11.111.1 |
| 실시예 36Example 36 | Cpd 164Cpd 164 | 5.165.16 | 11.511.5 |
| 실시예 37Example 37 | Cpd 170Cpd 170 | 5.175.17 | 11.611.6 |
| 실시예 38Example 38 | Cpd 171Cpd 171 | 5.145.14 | 11.011.0 |
| 실시예 39Example 39 | Cpd 194Cpd 194 | 5.155.15 | 10.810.8 |
| 실시예 40Example 40 | Cpd 195Cpd 195 | 5.105.10 | 11.211.2 |
| 실시예 41Example 41 | Cpd 218Cpd 218 | 5.155.15 | 11.011.0 |
| 실시예 42Example 42 | Cpd 219Cpd 219 | 5.205.20 | 11.311.3 |
| 실시예 43Example 43 | Cpd 242Cpd 242 | 5.155.15 | 11.011.0 |
| 실시예 44Example 44 | Cpd 243Cpd 243 | 5.105.10 | 11.311.3 |
| 실시예 45Example 45 | Cpd 266Cpd 266 | 5.155.15 | 10.810.8 |
| 실시예 46Example 46 | Cpd 267Cpd 267 | 5.105.10 | 11.111.1 |
| 실시예 47Example 47 | Cpd 290Cpd 290 | 5.155.15 | 11.511.5 |
| 실시예 48Example 48 | Cpd 291Cpd 291 | 5.205.20 | 10.810.8 |
| 실시예 49Example 49 | Cpd 314Cpd 314 | 5.135.13 | 11.211.2 |
| 실시예 50Example 50 | Cpd 315Cpd 315 | 5.205.20 | 11.011.0 |
| 실시예 51Example 51 | Cpd 338Cpd 338 | 5.155.15 | 10.810.8 |
| 실시예 52Example 52 | Cpd 339Cpd 339 | 5.105.10 | 11.211.2 |
| 실시예 53Example 53 | Cpd 362Cpd 362 | 5.155.15 | 11.011.0 |
| 실시예 54Example 54 | Cpd 363Cpd 363 | 5.105.10 | 11.311.3 |
| 실시예 55Example 55 | Cpd 386Cpd 386 | 5.205.20 | 11.011.0 |
| 실시예 56Example 56 | Cpd 387Cpd 387 | 5.155.15 | 10.810.8 |
| 실시예 57Example 57 | Cpd 410Cpd 410 | 5.105.10 | 11.211.2 |
| 실시예 58Example 58 | Cpd 411Cpd 411 | 5.155.15 | 11.011.0 |
| 비교예 2Comparative Example 2 | -- | 5.255.25 | 8.28.2 |
상기 표 2에 나타낸 바와 같이, 본 발명에 따른 화합물을 발광 보조층 재료로 사용한 실시예 30 내지 58의 적색 유기 전계 발광 소자는, 발광 보조층 없이 CBP만을 발광층 재료로 사용한 비교예 2의 적색 유기 전계 발광 소자에 비해 구동 전압이 약간 낮을 뿐만 아니라, 전류 효율이 더 우수하다는 것을 알 수 있었다.As shown in Table 2, the red organic electroluminescent devices of Examples 30 to 58 using the compound according to the present invention as the light emitting auxiliary layer material, the red organic electric field of Comparative Example 2 using only CBP as the light emitting layer material without a light emitting auxiliary layer It was found that the driving voltage was slightly lower than that of the light emitting device, and the current efficiency was better.
[[
실시예Example
59] 청색 유기 59] blue organic
전계Electric field
발광 소자의 제조 Manufacture of light emitting device
화합물 Cpd137을 통상적으로 알려진 방법으로 고순도 승화 정제를 한 후, 하기와 같이 청색 유기 전계 발광 소자를 제조하였다.After high purity sublimation purification of compound Cpd137 by a commonly known method, a blue organic electroluminescent device was manufactured as follows.
먼저, ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후, UV OZONE 세정기 (Powersonic 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 mm 3 was washed with distilled water ultrasonic waves. After washing with distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, and drying was carried out, and then transferred to a UV OZONE cleaner (Powersonic 405, Hwasin Tech). The substrate was transferred to the evaporator.
이와 같이 준비된 ITO 투명 전극 위에, DS-205(두산社) (80 nm) / NPB (15nm) / 화합물 Cpd 137 (15nm) / ADN+5%DS-405(두산社) (30nm) / BCP (10nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제조하였다.On the thus prepared ITO transparent electrode, DS-205 (Doosan) (80 nm) / NPB (15 nm) / Compound Cpd 137 (15 nm) / ADN + 5% DS-405 (Doosan) (30 nm) / BCP (10 nm ) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) was laminated in order to prepare an organic EL device.
사용된 BCP는 실시예 1에 기재된 바와 같고, NPB 및 ADN의 구조는 하기와 같다.The BCP used was as described in Example 1, and the structures of NPB and ADN are as follows.
[[
실시예Example
60 ~ 87] 청색 유기 60 to 87] blue organic
전계Electric field
발광 소자의 제조 Manufacture of light emitting device
실시예 59에서 사용된 화합물 Cpd137 대신 하기 표 3에 기재된 화합물을 각각 사용하는 것을 제외하고는, 실시예 59과 동일하게 수행하여 청색 유기 전계 발광 소자를 제조하였다.A blue organic electroluminescent device was manufactured in the same manner as in Example 59, except for using the compounds shown in Table 3 below instead of the compound Cpd137 used in Example 59.
[[
비교예Comparative example
3] 청색 유기 3] blue organic
전계Electric field
발광 소자의 제작 Fabrication of light emitting device
실시예 59에서 사용된 화합물 Cpd137을 사용하지 않은 것을 제외하고는, 실시예 59과 동일하게 수행하여 청색 유기 전계 발광 소자를 제조하였다.A blue organic electroluminescent device was manufactured in the same manner as in Example 59, except that Compound Cpd137, which was used in Example 59, was not used.
[[
평가예Evaluation example
3] 3]
실시예 59 ~ 87 및 비교예 3 에서 제작된 각각의 청색 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압 및 전류효율을 측정하였고, 그 결과를 하기 표 3에 나타내었다.For each of the blue organic EL devices manufactured in Examples 59 to 87 and Comparative Example 3, the driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured, and the results are shown in Table 3 below.
| 구분division | 발광보조층 재료Luminous auxiliary layer material | 구동 전압 (V)Driving voltage (V) | 전류효율 (cd/A)Current efficiency (cd / A) |
| 실시예 59Example 59 | Cpd 137Cpd 137 | 5.605.60 | 6.66.6 |
| 실시예 60Example 60 | Cpd 138Cpd 138 | 5.555.55 | 6.86.8 |
| 실시예 61Example 61 | Cpd 140Cpd 140 | 5.605.60 | 6.96.9 |
| 실시예 62Example 62 | Cpd 149Cpd 149 | 5.515.51 | 6.66.6 |
| 실시예 63Example 63 | Cpd 152Cpd 152 | 5.555.55 | 6.86.8 |
| 실시예 64Example 64 | Cpd 161Cpd 161 | 5.515.51 | 6.06.0 |
| 실시예 65Example 65 | Cpd 164Cpd 164 | 5.555.55 | 6.46.4 |
| 실시예 66Example 66 | Cpd 170Cpd 170 | 5.605.60 | 6.06.0 |
| 실시예 67Example 67 | Cpd 171Cpd 171 | 5.655.65 | 6.46.4 |
| 실시예 68Example 68 | Cpd 194Cpd 194 | 5.535.53 | 6.56.5 |
| 실시예 69Example 69 | Cpd 195Cpd 195 | 5.565.56 | 6.86.8 |
| 실시예 70Example 70 | Cpd 218Cpd 218 | 5.495.49 | 6.16.1 |
| 실시예 71Example 71 | Cpd 219Cpd 219 | 5.505.50 | 6.96.9 |
| 실시예 72Example 72 | Cpd 242Cpd 242 | 5.605.60 | 6.66.6 |
| 실시예 73Example 73 | Cpd 243Cpd 243 | 5.555.55 | 6.86.8 |
| 실시예 74Example 74 | Cpd 266Cpd 266 | 5.605.60 | 6.96.9 |
| 실시예 75Example 75 | Cpd 267Cpd 267 | 5.515.51 | 6.66.6 |
| 실시예 76Example 76 | Cpd 290Cpd 290 | 5.555.55 | 6.86.8 |
| 실시예 77Example 77 | Cpd 291Cpd 291 | 5.515.51 | 6.06.0 |
| 실시예 78Example 78 | Cpd 314Cpd 314 | 5.555.55 | 6.46.4 |
| 실시예 79Example 79 | Cpd 315Cpd 315 | 5.605.60 | 6.56.5 |
| 실시예 80Example 80 | Cpd 338Cpd 338 | 5.655.65 | 6.86.8 |
| 실시예 81Example 81 | Cpd 339Cpd 339 | 5.535.53 | 6.16.1 |
| 실시예 82Example 82 | Cpd 362Cpd 362 | 5.565.56 | 6.96.9 |
| 실시예 83Example 83 | Cpd 363Cpd 363 | 5.495.49 | 6.66.6 |
| 실시예 84Example 84 | Cpd 386Cpd 386 | 5.505.50 | 6.86.8 |
| 실시예 85Example 85 | Cpd 387Cpd 387 | 5.505.50 | 6.86.8 |
| 실시예 86Example 86 | Cpd 410Cpd 410 | 5.605.60 | 6.96.9 |
| 실시예 87Example 87 | Cpd 411Cpd 411 | 5.555.55 | 6.46.4 |
| 비교예 3Comparative Example 3 | -- | 5.605.60 | 4.84.8 |
상기 표 3에 나타낸 바와 같이, 본 발명에 따른 화합물을 발광 보조층 재료로 사용한 실시예 59 내지 87의 청색 유기 전계 발광 소자는, 발광 보조층 없이 ADN을 발광층 재료로 사용한 비교예 3의 청색 유기 전계 발광 소자와 구동 전압이 유사하였으나, 비교예 3의 유기 전계 발광 소자에 비해 전류 효율이 더 우수하다는 것을 알 수 있었다.As shown in Table 3, the blue organic electroluminescent device of Examples 59 to 87 using the compound according to the present invention as the light emitting auxiliary layer material, the blue organic electric field of Comparative Example 3 using ADN as the light emitting layer material without the light emitting auxiliary layer Although the light emitting device and the driving voltage were similar, it was found that the current efficiency is better than that of the organic EL device of Comparative Example 3.
[[
실시예Example
88] 녹색 유기 88] Green Organic
전계Electric field
발광 소자의 제작 Fabrication of light emitting device
반응예 1로 합성된 화합물 Cpd 1을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 아래의 과정에 따라 녹색 유기 전계 발광 소자를 제작하였다.After compound Cpd 1 synthesized in Reaction Example 1 was subjected to high purity sublimation purification by a conventionally known method, a green organic electroluminescent device was manufactured according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후, UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음, UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 mm 3 was washed with distilled water ultrasonic waves. After washing with distilled water, ultrasonic cleaning 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 transferred to a vacuum evaporator.
이와 같이 준비된 ITO 투명 전극 위에 m-MTDATA (60 nm) / TCTA (80 nm) / 화합물 Cpd1 + 10%Ir(ppy)3 (30nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다. M-MTDATA (60 nm) / TCTA (80 nm) / Compound Cpd1 + 10% Ir (ppy) 3 (30nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF ( 1 nm) / Al (200 nm) was laminated in order to manufacture an organic EL device.
[[
실시예Example
89~ 148] 녹색 유기 89 ~ 148] Green Organic
전계Electric field
발광 소자의 제조 Manufacture of light emitting device
실시예 88에서 사용된 화합물 Cpd 1 대신 하기 표 4에 기재된 화합물을 각각 사용하는 것을 제외하고는, 실시예 88과 동일하게 수행하여 녹색 유기 전계 발광 소자를 제조하였다.A green organic electroluminescent device was manufactured in the same manner as in Example 88, except for using the compounds described in Table 4 below instead of the compounds Cpd 1 used in Example 88.
[[
비교예Comparative example
4] 녹색 유기 4] green organic
전계Electric field
발광 소자의 제작 Fabrication of light emitting device
실시예 88에서 발광층 형성시 발광 호스트 물질로 사용된 화합물 Cdp1 대신 CBP를 사용하는 것을 제외하고는, 상기 실시예 88과 동일한 과정으로 녹색 유기 전계 발광 소자를 제작하였다.A green organic electroluminescent device was manufactured in the same manner as in Example 88, except that CBP was used instead of the compound Cdp1 used as the light emitting host material in forming the emission layer in Example 88.
[[
평가예Evaluation example
4] 4]
실시예 88~148 및 비교예 4에서 제작된 각각의 녹색 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하였고, 그 결과를 하기 표 4에 나타내었다.For each of the green organic electroluminescent devices fabricated in Examples 88 to 148 and Comparative Example 4, the driving voltage, current efficiency, and emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 4 below. It was.
| 구분division | 호스트Host | 구동 전압(V)Drive voltage (V) | EL 피크(nm)EL peak (nm) | 전류효율(cd/A)Current efficiency (cd / A) |
| 실시예 88Example 88 | Cpd 1Cpd 1 | 6.636.63 | 518518 | 40.540.5 |
| 실시예 89Example 89 | Cpd 8 Cpd 8 | 6.786.78 | 515515 | 42.442.4 |
| 실시예 90Example 90 | Cpd 10Cpd 10 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 91Example 91 | Cpd 11Cpd 11 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 92Example 92 | Cpd 24Cpd 24 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 93Example 93 | Cpd 28Cpd 28 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 94Example 94 | Cpd 34Cpd 34 | 6.786.78 | 515515 | 42.442.4 |
| 실시예 95Example 95 | Cpd 39Cpd 39 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 96Example 96 | Cpd 43Cpd 43 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 97Example 97 | Cpd 46Cpd 46 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 98Example 98 | Cpd 55Cpd 55 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 99Example 99 | Cpd 56Cpd 56 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 100Example 100 | Cpd 73Cpd 73 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 101Example 101 | Cpd 84Cpd 84 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 102Example 102 | Cpd 88Cpd 88 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 103Example 103 | Cpd 100Cpd 100 | 6.786.78 | 515515 | 42.442.4 |
| 실시예 104Example 104 | Cpd 101Cpd 101 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 105Example 105 | Cpd 118Cpd 118 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 106Example 106 | Cpd 133Cpd 133 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 107Example 107 | Cpd 180Cpd 180 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 108Example 108 | Cpd 183Cpd 183 | 6.786.78 | 515515 | 42.442.4 |
| 실시예 109Example 109 | Cpd 187Cpd 187 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 110Example 110 | Cpd 204Cpd 204 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 111Example 111 | Cpd 207Cpd 207 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 112Example 112 | Cpd 211Cpd 211 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 113Example 113 | Cpd 228Cpd 228 | 6.786.78 | 515515 | 42.442.4 |
| 실시예 114Example 114 | Cpd 231Cpd 231 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 115Example 115 | Cpd 234Cpd 234 | 6.636.63 | 518518 | 40.540.5 |
| 실시예 116Example 116 | Cpd 235Cpd 235 | 6.786.78 | 515515 | 42.442.4 |
| 실시예 117Example 117 | Cpd 252Cpd 252 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 118Example 118 | Cpd 255Cpd 255 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 119Example 119 | Cpd 258Cpd 258 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 120Example 120 | Cpd 259Cpd 259 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 121Example 121 | Cpd 276Cpd 276 | 6.786.78 | 515515 | 42.442.4 |
| 실시예 122Example 122 | Cpd 279Cpd 279 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 123Example 123 | Cpd 282Cpd 282 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 124Example 124 | Cpd 283Cpd 283 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 125Example 125 | Cpd 300Cpd 300 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 126Example 126 | Cpd 303Cpd 303 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 127Example 127 | Cpd 306Cpd 306 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 128Example 128 | Cpd 307Cpd 307 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 129Example 129 | Cpd 324Cpd 324 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 130Example 130 | Cpd 327Cpd 327 | 6.786.78 | 515515 | 42.442.4 |
| 실시예 131Example 131 | Cpd 330Cpd 330 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 132Example 132 | Cpd 331Cpd 331 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 133Example 133 | Cpd 348Cpd 348 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 134Example 134 | Cpd 351Cpd 351 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 135Example 135 | Cpd 354Cpd 354 | 6.786.78 | 515515 | 42.442.4 |
| 실시예 136Example 136 | Cpd 355Cpd 355 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 137Example 137 | Cpd 372Cpd 372 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 138Example 138 | Cpd 375Cpd 375 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 139Example 139 | Cpd 378Cpd 378 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 140Example 140 | Cpd 379Cpd 379 | 6.786.78 | 515515 | 42.442.4 |
| 실시예 141Example 141 | Cpd 396Cpd 396 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 142Example 142 | Cpd 399Cpd 399 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 143Example 143 | Cpd 402Cpd 402 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 144Example 144 | Cpd 403Cpd 403 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 145Example 145 | Cpd 420Cpd 420 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 146Example 146 | Cpd 423Cpd 423 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 147Example 147 | Cpd 426Cpd 426 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 148Example 148 | Cpd 427Cpd 427 | 6.796.79 | 517517 | 40.840.8 |
| 비교예 4Comparative Example 4 | CBPCBP | 6.936.93 | 516516 | 38.238.2 |
상기 표 4에 나타낸 바와 같이, 본 발명에 따른 화합물을 발광층 재료로 각각 사용한 실시예 88 내지 148의 녹색 유기 전계 발광 소자의 경우, 종래 CBP를 사용한 비교예 4의 녹색 유기 전계 발광 소자에 비해 전류 효율 및 구동 전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있었다.As shown in Table 4, in the case of the green organic electroluminescent devices of Examples 88 to 148, each using the compound according to the present invention as a light emitting layer material, the current efficiency compared to the green organic electroluminescent device of Comparative Example 4 using the conventional CBP And better performance in terms of driving voltage.
[[
실시예Example
149 ~ 162] 청색 유기 149 ~ 162] blue organic
전계Electric field
발광 소자의 제조 Manufacture of light emitting device
반응예 1로 합성된 화합물 Cpd 1를 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 아래의 과정에 따라 청색 유기 전계 발광 소자를 제작하였다.Compound Cpd 1 synthesized in Reaction Example 1 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.
먼저, ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후, UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음, UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 mm 3 was washed with distilled water ultrasonic waves. After washing with distilled water, ultrasonic cleaning 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 transferred to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에 CuPc (10 nm) / TPAC (30 nm) / 화합물 Cpd 1 + 7 % Flrpic (30nm) / Alq3 (30 nm) / LiF (0.2 nm) / Al (150 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다. CuPc (10 nm) / TPAC (30 nm) / Compound Cpd 1 + 7% Flrpic (30 nm) / Alq 3 (30 nm) / LiF (0.2 nm) / Al (150 nm) To produce an organic electroluminescent device.
여기서 사용된 CuPc, TPAC 및 Flrpic의 구조는 각각 하기와 같다.The structures of CuPc, TPAC and Flrpic used herein are as follows.
[비교예 5] 청색 유기 전계 발광 소자의 제작Comparative Example 5 Fabrication of Blue Organic Electroluminescent Device
실시예 149에서 발광층 형성시 발광 호스트 물질로 사용된 화합물 Cdp 1 대신 CBP를 사용하는 것을 제외하고는, 상기 실시예 149과 동일한 과정으로 청색 유기 전계 발광 소자를 제작하였다.A blue organic electroluminescent device was manufactured in the same manner as in Example 149, except for using CBP instead of the compound Cdp 1 used as a light emitting host material in forming the emission layer in Example 149.
[평가예 5][Evaluation Example 5]
실시예 149~162 및 비교예 5에서 제작된 각각의 청색 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하였고, 그 결과를 하기 표 5에 나타내었다.For each of the blue organic electroluminescent devices fabricated in Examples 149 to 162 and Comparative Example 5, driving voltage, current efficiency, and emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 5 below. It was.
| 구분division | 호스트Host | 구동 전압(V)Drive voltage (V) | EL 피크(nm)EL peak (nm) | 전류효율(cd/A)Current efficiency (cd / A) |
| 실시예 149Example 149 | Cpd 1Cpd 1 | 7.247.24 | 475475 | 6.556.55 |
| 실시예 150Example 150 | Cpd 6Cpd 6 | 7.247.24 | 475475 | 6.556.55 |
| 실시예 151Example 151 | Cpd 46Cpd 46 | 7.157.15 | 471471 | 6.946.94 |
| 실시예 152Example 152 | Cpd 51Cpd 51 | 7.237.23 | 472472 | 6.256.25 |
| 실시예 153Example 153 | Cpd 91Cpd 91 | 7.127.12 | 472472 | 5.855.85 |
| 실시예 154Example 154 | Cpd 96Cpd 96 | 7.007.00 | 472472 | 6.346.34 |
| 실시예 155Example 155 | Cpd 259Cpd 259 | 7.297.29 | 473473 | 6.906.90 |
| 실시예 156Example 156 | Cpd 283Cpd 283 | 7.307.30 | 474474 | 6.346.34 |
| 실시예 157Example 157 | Cpd 307Cpd 307 | 7.247.24 | 475475 | 6.556.55 |
| 실시예 158Example 158 | Cpd 331Cpd 331 | 7.157.15 | 471471 | 6.946.94 |
| 실시예 159Example 159 | Cpd 355Cpd 355 | 7.237.23 | 472472 | 6.256.25 |
| 실시예 160Example 160 | Cpd 379Cpd 379 | 7.307.30 | 474474 | 6.346.34 |
| 실시예 161Example 161 | Cpd 403Cpd 403 | 7.247.24 | 475475 | 6.556.55 |
| 실시예 162Example 162 | Cpd 427Cpd 427 | 7.157.15 | 471471 | 6.946.94 |
| 비교예 5Comparative Example 5 | CBPCBP | 7.807.80 | 474474 | 5.805.80 |
상기 표5에 나타낸 바와 같이, 본 발명에 따른 화합물을 발광층 재료로 사용한 실시예 149~162의 청색 유기 전계 발광 소자는 종래 CBP를 사용하는 비교예 5의 청색 유기 전계 발광 소자에 비해 전류 효율 및 구동 전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있었다.As shown in Table 5, the blue organic electroluminescent devices of Examples 149 to 162 using the compound according to the present invention as a light emitting layer material, compared with the blue organic electroluminescent device of Comparative Example 5, which uses a conventional CBP, have a current efficiency and drive. It was found that the better performance in terms of voltage.
이상을 통해 본 발명의 바람직한 실시예에 대하여 설명하였지만, 본 발명은 이에 한정되는 것이 아니고 특허청구범위와 발명의 상세한 설명의 범위 안에서 여러 가지로 변형하여 실시하는 것이 가능하고 이 또한 발명의 범주에 속하는 것은 당연하다.Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications and changes can be made within the scope of the claims and the detailed description of the invention, which also fall within the scope of the invention. It is natural.
본 발명은 유기 전계 발광 소자용 재료로서 사용될 수 있는 신규 유기 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.
Claims (13)
- 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, R5와 R6, R6과 R7, R7과 R8 중 적어도 하나는 하기 화학식 2로 표시되는 고리와 축합되어 축합 고리를 형성하며;At least one of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 is condensed and condensed with a ring represented by the following formula (2) To form a ring;하기 화학식 2로 표시되는 고리와 축합 고리를 형성하지 않는 R1 내지 R8은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되며; R 1 to R 8 which do not form a ring and a condensed ring represented by the following formula (2) are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenes group, C 2 ~ C 40 of the 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 60 heteroaryl group , C 1 ~ C 40 Alkyloxy group, C 6 ~ C 60 Aryloxy group, C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group , C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylamine group is selected from ;상기 R1 내지 R8의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하며;The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 1 to R 8 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ selected from the group consisting of C 60 aryl silyl Substituted with one or more substituents being unsubstituted or, if substituted by a plurality of substituents, they are same or different from each other;[화학식 2][Formula 2]
상기 화학식 2에서, In Chemical Formula 2,점선은 축합이 이루어지는 부분이며;The dotted line is the part where condensation takes place;X1은 C(Ar1)(Ar2), N(Ar3), O, S 및 Si(Ar4)(Ar5)로 이루어진 군에서 선택되며;X 1 is selected from the group consisting of C (Ar 1 ) (Ar 2 ), N (Ar 3 ), O, S and Si (Ar 4 ) (Ar 5 );Ar1 및 Ar2는 각각 독립적으로 C1~C40의 알킬기 또는 C6~C60의 아릴기이고; Ar 1 and Ar 2 are each independently C 1 -C 40 alkyl group or C 6 -C 60 aryl group;Ar3 내지 Ar5는 각각 독립적으로 하기 화학식 3으로 표시되는 치환기이며;Ar 3 to Ar 5 are each independently a substituent represented by the following formula (3);Y1 내지 Y4는 각각 독립적으로 N 또는 C(R9)이며;Y 1 to Y 4 are each independently N or C (R 9 );R9는 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하고, 상기 R9가 복수 개인 경우 복수 개의 R9는 서로 동일하거나 상이하며; R 9 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, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phospha Or a C 6 to C 60 mono or diarylphosphinyl group and a C 6 to C 60 arylamine group, or combine with an adjacent group to form a condensed ring, and a plurality of R 9 plural R 9 are the same as or different from each other;상기 Ar1 및 Ar2의 알킬기 및 아릴기와, 상기 R9의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하며;The alkyl group and aryl group of Ar 1 and Ar 2, the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group of R 9 , Alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, an aryloxy group of C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ C 60 of, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl group of boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ C 60 aryl It substituted with one or more substituents selected from the group consisting of a reel or is unsubstituted, in the case where the substitution of a plurality of substituents, they are same or different from each other;[화학식 3][Formula 3]
상기 화학식 3에서,In Chemical Formula 3,*는 상기 화학식 2에 결합되는 부분을 의미하고;* Means a moiety bonded to Formula 2;L1 및 L2는 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되며; L 1 and L 2 are each independently 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;R10은 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하며; R 10 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, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phospha A aryl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring;상기 L1 및 L2의 아릴렌기 및 헤테로아릴렌기와, 상기 R10의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다. Wherein L 1 and the L 2 arylene group and a heteroarylene group, an alkyl group of the R 10, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl The amine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 An alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 6 to C 60 aryl group, a nuclear atom having 5 to 60 heteroaryl groups, a C 6 to C 60 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phosphanyl group, C 6 ~ C 60 Mono or diaryl phosphinyl group and C 6 ~ C 6 When unsubstituted or substituted with one or more substituents selected from the group consisting of 0 arylsilyl groups, they are the same or different from each other. - 제1항에 있어서,The method of claim 1,상기 Y1 내지 Y4는 모두 C(R9)이고, 복수 개의 R9는 서로 동일하거나 상이한 화합물. Y 1 to Y 4 are all C (R 9 ), and a plurality of R 9 are the same or different from each other.
- 제1항에 있어서,The method of claim 1,상기 화학식 2로 표시되는 축합 고리는 하기 화학식 4로 표시되는 축합 고리인 화합물:The condensed ring represented by Formula 2 is a compound represented by Formula 4 below:[화학식 4][Formula 4]
상기 화학식 4에서, In Chemical Formula 4,점선은 축합이 이루어지는 부분이며;The dotted line is the part where condensation takes place;X2는 C(Ar1)(Ar2), N(Ar3), O, S 및 Si(Ar4)(Ar5)로 이루어진 군에서 선택되며;X 2 is selected from the group consisting of C (Ar 1 ) (Ar 2 ), N (Ar 3 ), O, S and Si (Ar 4 ) (Ar 5 );Ar1 및 Ar2는 각각 독립적으로 C1~C40의 알킬기 또는 C6~C60의 아릴기이고; Ar 1 and Ar 2 are each independently C 1 -C 40 alkyl group or C 6 -C 60 aryl group;Ar3 내지 Ar5는 각각 독립적으로 하기 화학식 3으로 표시되는 치환기이며;Ar 3 to Ar 5 are each independently a substituent represented by the following formula (3);R11과 R12, R12와 R13, R13과 R14 중 적어도 하나는 하기 화학식 6으로 표시되는 고리와 축합되어 축합고리를 형성하거나, 축합고리를 형성하지 않는 R11 내지 R14는 각각 독립적으로 하기 화학식 5로 표시되는 치환기이며;At least one of R 11 and R 12 , R 12 and R 13 , R 13 and R 14 is condensed with a ring represented by the following Formula 6 to form a condensed ring, or R 11 to R 14 which do not form a condensed ring are each Independently a substituent represented by formula (5);[화학식 3][Formula 3]
[화학식 5][Formula 5]
상기 화학식 3, 5 및 6에서,In Chemical Formulas 3, 5, and 6,*는 상기 화학식 4에 결합되는 부분을 의미하고;* Means a moiety bound to Formula 4;L1 내지 L4는 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되며; L 1 to L 4 are each independently 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;R10 및 R19는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되며; R 10 and R 19 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, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ for C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ is selected from the group consisting of an aryl amine of the C 60 of the;상기 L1 내지 L4의 아릴렌기 및 헤테로아릴렌기와, 상기 R10 및 R19의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하며;The arylene group and heteroarylene group of L 1 to L 4 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl of R 10 and R 19 Alkyl, arylamine, alkylsilyl, alkylboron, arylboron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1- C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 6 -C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 6 -C 60 aryl Oxy group, C 1 -C 40 alkyloxy group, C 6 -C 60 arylamine group, C 3 -C 40 cycloalkyl group, nuclear atom of 3-40 heterocycloalkyl group, C 1 -C 40 alkyl Silyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diarylphosphinyl group And when substituted or unsubstituted with one or more substituents selected from the group consisting of C 6 ~ C 60 An arylsilyl group, and when substituted with a plurality of substituents, they are the same or different from each other;[화학식 6][Formula 6]
점선은 축합이 이루어지는 부분이며;The dotted line is the part where condensation takes place;X3는 C(Ar6)(Ar7), N(Ar8), O, S 및 Si(Ar9)(Ar10)으로 이루어진 군에서 선택되며;X 3 is selected from the group consisting of C (Ar 6 ) (Ar 7 ), N (Ar 8 ), O, S and Si (Ar 9 ) (Ar 10 );Ar6 및 Ar7는 각각 독립적으로 C1~C40의 알킬기 또는 C6~C60의 아릴기이며;Ar 6 and Ar 7 are each independently an alkyl group of C 1 to C 40 or an aryl group of C 6 to C 60 ;Ar8 내지 Ar10과 R15 내지 R18은 각각 독립적으로 하기 화학식 7로 표시되는 치환기이며;Ar 8 to Ar 10 and R 15 to R 18 are each independently a substituent represented by formula (7);[화학식 7][Formula 7]
상기 화학식 7에서,In Chemical Formula 7,*는 상기 화학식 6에 결합되는 부분을 의미하고;* Means a moiety bound to Formula 6;L5 및 L6은 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되며; L 5 and L 6 are each independently 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;R20은 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되며; R 20 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, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phospha A silyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group;상기 L5 및 L6의 아릴렌기 및 헤테로아릴렌기와, 상기 R20의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.Alkyl groups of the L 5 and L 6 arylene group and a heteroarylene group, the R 20 of the group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl The amine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 An alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 6 to C 60 aryl group, a nuclear atom having 5 to 60 heteroaryl groups, a C 6 to C 60 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phosphanyl group, C 6 ~ C 60 Mono or diaryl phosphinyl group and C 6 ~ C 6 When unsubstituted or substituted with one or more substituents selected from the group consisting of 0 arylsilyl groups, they are the same or different from each other. - 제3항에 있어서,The method of claim 3,상기 화합물은 하기 화학식 8 내지 20 중 어느 하나로 표시되는 화합물:The compound is a compound represented by any one of the following formula 8 to 20:[화학식 8][Formula 8]
[화학식 9][Formula 9]
[화학식 10][Formula 10]
[화학식 11][Formula 11]
[화학식 12][Formula 12]
[화학식 13][Formula 13]
[화학식 14][Formula 14]
[화학식 15][Formula 15]
[화학식 16][Formula 16]
[화학식 17][Formula 17]
[화학식 18][Formula 18]
[화학식 19][Formula 19]
[화학식 20][Formula 20]
상기 화학식 8 내지 20에서, In Chemical Formulas 8 to 20,R1 내지 R5, R7 및 R8은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되며; R 1 to R 5 , R 7 and R 8 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, 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 60 heteroaryl group, an alkyl of C 1 ~ C 40 Oxy group, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl A boron group, a C 6 -C 60 arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group;상기 R1 내지 R5, R7 및 R8의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하며;Alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group of R 1 to R 5 , R 7 and R 8 , Alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and 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 to C 40 alkynyl group, C 6 to C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 Alkoxyoxy group, C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 Alkylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C group 60 arylboronic of, C 6 ~ C 60 aryl phosphazene group, C 6 ~ mono or diaryl phosphine of C 60 blood group and a C 6 ~ group consisting arylsilyl of C 60 Standing substituted with at least one selected more substituents or being unsubstituted, substituted, if a plurality of substituents, they are same or different from each other;X2, X3 및 R11 내지 R18 각각은 제3항에서 정의된 바와 같다.X 2 , X 3 and R 11 to R 18 are each as defined in claim 3. - 제3항에 있어서,The method of claim 3,상기 L1 내지 L6은 각각 독립적으로 단일결합이거나, 하기 화학식 A-1 내지 A-6 중 어느 하나로 표시되는 링커인 화합물:L 1 to L 6 are each independently a single bond or a linker represented by any one of the following Formulas A-1 to A-6:
상기 화학식 A-1 내지 A-6에서,In Chemical Formulas A-1 to A-6,*는 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;X4 및 X5는 각각 독립적으로 O, S, N(R22) 또는 C(R23)(R24)이며;X 4 and X 5 are each independently O, S, N (R 22 ) or C (R 23 ) (R 24 );X6은 N 또는 C(R25)이며;X 6 is N or C (R 25 );p는 0 내지 4의 정수이며;p is an integer from 0 to 4;R21은 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R21이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 21 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 groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups, C An alkylsilyl group of 3 to C 40 , an arylsilyl group of C 6 to C 60 , an alkyl boron group of C 1 to C 40, an aryl boron group of C 6 to C 60 , an arylphosphanyl group of C 6 to C 60 , C 6 ~ C 60 It is selected from the group consisting of mono or diaryl phosphinyl group and C 6 ~ C 60 arylamine group, or may be combined with adjacent groups to form a condensed ring, when there are a plurality of R 21 Same or different from each other;R22 내지 R25는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고;R 22 to R 25 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 6 ~ C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 aryl phosphazene group, selected from the group consisting arylsilyl a C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 of, or by combining tile adjacent to which they are attached may form a condensed ring;상기 R21 내지 R25의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 21 to R 25 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 Aryl boron group of ~ C 60 , C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylsilyl group When substituted or unsubstituted with one or more substituents, and substituted with a plurality of substituents, they may be the same or different from each other. - 제3항에 있어서,The method of claim 3,상기 R10, R19 및 R20 중 적어도 하나는 하기 화학식 B-1 내지 B-7 중 어느 하나로 표시되는 치환기이며, 상기 R10, R19 및 R20은 서로 동일하거나 상이한 화합물:Wherein R 10, R 19 and at least one of R 20 is a substituent represented by any of formulas to B-1 to B-7, wherein R 10, R 19 and R 20 are the same or different from each other compounds:
상기 화학식 B-1 내지 B-7에서,In Chemical Formulas B-1 to B-7,*는 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;Z1 내지 Z5는 각각 독립적으로 N 또는 C(R30)이며;Z 1 to Z 5 are each independently N or C (R 30 );T1 및 T2는 각각 독립적으로 단일결합, C(R31)(R32), N(R33), O 및 S로 이루어진 군에서 선택되나, T1 및 T2 모두가 단일결합은 아니며;T 1 and T 2 are each independently selected from the group consisting of a single bond, C (R 31 ) (R 32 ), N (R 33 ), O and S, but not both T 1 and T 2 are single bonds;q 및 r은 각각 독립적으로 0 내지 4의 정수이며;q and r are each independently integers of 0 to 4;R26 및 R27은 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R26 및 R27 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 26 and R 27 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 60 the aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an aryloxy group of C 6 ~ C 60, C 1 ~ C 40 alkyloxy group of, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 Heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 An arylphosphanyl group, a C 6 ~ C 60 mono or diaryl phosphinyl group and a C 6 ~ C 60 arylsilyl group, or may be combined with an adjacent group to form a condensed ring, wherein R When 26 and R 27 each are plural, they are the same as or different from each other;R28 내지 R33은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R30 내지 R33 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 28 to R 33 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 6 ~ C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 aryl phosphazene group, selected from the group consisting of C 6 ~ C 60 mono or diaryl the Phosphinicosuccinic group and a C 6 ~ with an aryl silyl group of C 60, or combine tile adjacent to which they are attached may form a fused ring, When each of R 30 to R 33 is plural, they are the same as or different from each other;상기 R26 내지 R33의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 26 to R 33 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 Aryl boron group of ~ C 60 , C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylsilyl group When substituted or unsubstituted with one or more substituents, and substituted with a plurality of substituents, they may be the same or different from each other. - 제3항에 있어서,The method of claim 3,상기 R10, R19 및 R20 중 적어도 하나는 하기 화학식 C-1 내지 C-24 중 어느 하나로 표시되는 치환기이며, 상기 R10, R19 및 R20은 서로 동일하거나 상이한 화합물: Wherein R 10, R 19 and at least one of R 20 is a substituent represented by any of formulas to C-1 to C-24, the R 10, R 19 and R 20 are the same or different from each other compounds:
상기 화학식 C-1 내지 C-24에서,In Chemical Formulas C-1 to C-24,*은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;t는 0 내지 5의 정수이며,t is an integer from 0 to 5,u는 0 내지 4의 정수이며;u is an integer from 0 to 4;v는 0 내지 3의 정수이며;v is an integer from 0 to 3;w는 0 내지 2의 정수이며;w is an integer from 0 to 2;q 및 r은 각각 독립적으로 0 내지 4의 정수이며;q and r are each independently integers of 0 to 4;R26, R27 및 R34는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R26, R27 및 R34 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 26, R 27 and R 34 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 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyloxy group of, C 3 ~ C 40 cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 ~ C 60 aryl phosphazene group, selected from the group consisting arylsilyl a C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 of, or by combining tile adjacent to which they are attached may form a condensed ring When R 26, R 27 and R 34 are each plural, they are the same as or different from each other;R30 내지 R33은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며;R 30 to R 33 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 6 ~ C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ~ C 60 of the blood group and a C 6 ~ C 60 selected from an aryl silyl group the group consisting of or of, by combining groups adjacent to form a condensed ring;상기 R26, R27 및 R30 내지 R34의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group of R 26 , R 27 and R 30 to R 34 , Alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and 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 to C 40 alkynyl group, C 6 to C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 Alkoxyoxy group, C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 Alkylsilyl group, C 1 ~ C 40 An alkylboron group, a C 6 to C 60 aryl boron group, a C 6 to C 60 arylphosphanyl group, a C 6 to C 60 mono or diarylphosphinyl group, and a C 6 to C 60 arylsilyl group When substituted or unsubstituted with one or more substituents selected from the group, and substituted with a plurality of substituents, they may be the same or different from each other. - 제3항에 있어서,The method of claim 3,상기 R10, R19 및 R20 중 적어도 하나는 하기 화학식 B-4로 표시되는 치환기이며, 상기 R10, R19 및 R20은 서로 동일하거나 상이한 화합물:Wherein R 10, R 19 and at least one of R 20 is a substituent represented by the following general formula B-4, wherein R 10, R 19 and R 20 are the same or different from each other compounds:
상기 화학식 B-4에서,In Chemical Formula B-4,R28 및 R29는 각각 독립적으로 수소, C1~C40의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택될 수 있으며;R 28 and R 29 each independently represent hydrogen, an alkyl group of C 1 to C 40 , an aryl group of C 6 to C 60 , a heteroaryl group of 5 to 60 nuclear atoms, an aryloxy group of C 6 to C 60 , and C It may be selected from the group consisting of 6 ~ C 60 arylamine group;상기 R28 및 R29의 알킬기, 아릴기, 헤테로아릴기 및 아릴아민기는 각각 독립적으로 C1~C40의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, aryl group, heteroaryl group and arylamine group of R 28 and R 29 are each independently C 1 ~ C 40 alkyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group and When substituted or unsubstituted with one or more substituents selected from the group consisting of C 6 to C 60 arylamine groups, and substituted with a plurality of substituents, they may be the same or different from each other. - 제8항에 있어서,The method of claim 8,상기 R28 및 R29 중 적어도 하나는 하기 화학식 21 또는 22로 표시되는 치환기인 화합물:At least one of R 28 and R 29 is a substituent represented by Formula 21 or 22 below:[화학식 21][Formula 21]
[화학식 22][Formula 22]
상기 화학식 21 및 22에서,In Chemical Formulas 21 and 22,*는 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;L7 및 L8은 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되며; L 7 and L 8 are each independently 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;Z6 내지 Z10은 각각 독립적으로 N 또는 C(R37)이며;Z 6 to Z 10 are each independently N or C (R 37 );R35 내지 R37은 각각 독립적으로 수소, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 상기 R37이 복수 개인 경우 이들은 서로 동일하거나 상이하며; R 35 to R 37 are each independently hydrogen, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 6 -C 60 aryl group, nuclear atom 5 To 60 heteroaryl groups and C 6 to C 60 arylamine groups, and when there are a plurality of R 37 groups, they are the same as or different from each other;상기 L7 및 L8의 아릴렌기 및 헤테로아릴렌기와, 상기 R35 내지 R37의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 및 아릴아민기는 각각 독립적으로 C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, 및 C6~C60의 아릴아민기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.The arylene group and heteroarylene group of L 7 and L 8 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, and arylamine group of R 35 to R 37 are each independently C 1 to C 40 . An alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 6 to C 60 aryl group, a nuclear atom having 5 to 60 heteroaryl groups, and a C 6 to C 60 arylamine group When substituted or unsubstituted and substituted with a plurality of substituents, they are the same as or different from each other. - 제9항에 있어서,The method of claim 9,상기 R35 및 R36은 각각 독립적으로 페닐기, 비페닐기 및 나프탈레닐기로 이루어진 군에서 선택되는 화합물.R 35 and R 36 are each independently selected from the group consisting of a phenyl group, a biphenyl group and a naphthalenyl group.
- 제1항에 있어서,The method of claim 1,상기 화합물은 아래의 화합물로 이루어진 군에서 선택되는 것을 특징으로 하는 화합물: The compound is selected from the group consisting of the following compounds:
- (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) at least one organic material layer interposed between the anode and the cathode,상기 1층 이상의 유기물층 중에서 적어도 하나는 제1항의 화학식 1로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.At least one of the one or more organic material layer is an organic electroluminescent device, characterized in that it comprises a compound represented by the formula (1) of claim 1.
- 제12항에 있어서,The method of claim 12,상기 화합물을 포함하는 유기물층은 정공 주입층, 정공 수송층, 전자 수송층, 전자 수송 보조층, 전자 주입층, 수명 개선층, 발광층 및 발광 보조층으로 이루어진 군에서 선택되는 유기 전계 발광 소자.The organic material layer including the compound is selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron transport auxiliary layer, an electron injection layer, a life improvement layer, a light emitting layer and a light emitting auxiliary layer.
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