KR20140049186A - Organic electroluminescence compounds and organic electroluminescence device comprising the same - Google Patents
Organic electroluminescence compounds and organic electroluminescence device comprising the same Download PDFInfo
- Publication number
- KR20140049186A KR20140049186A KR1020120114912A KR20120114912A KR20140049186A KR 20140049186 A KR20140049186 A KR 20140049186A KR 1020120114912 A KR1020120114912 A KR 1020120114912A KR 20120114912 A KR20120114912 A KR 20120114912A KR 20140049186 A KR20140049186 A KR 20140049186A
- Authority
- KR
- South Korea
- Prior art keywords
- substituted
- unsubstituted
- group
- membered
- alkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 65
- 238000005401 electroluminescence Methods 0.000 title abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 75
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 38
- 125000000732 arylene group Chemical group 0.000 claims abstract description 10
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- -1 cyano, carbazolyl Chemical group 0.000 claims description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 16
- 229910052805 deuterium Inorganic materials 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 125000005104 aryl silyl group Chemical group 0.000 claims description 10
- 229910052717 sulfur Chemical group 0.000 claims description 10
- 125000001769 aryl amino group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000002723 alicyclic group Chemical group 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 239000011593 sulfur Chemical group 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 3
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000010410 layer Substances 0.000 description 49
- 239000000463 material Substances 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000002019 doping agent Substances 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000001771 vacuum deposition Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- 0 *(C(C=C=C1)=C1c1c2)c1cc1c2cc(CCCC2)c2c1 Chemical compound *(C(C=C=C1)=C1c1c2)c1cc1c2cc(CCCC2)c2c1 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000001454 anthracenes Chemical class 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical group C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 2
- WHGGVVHVBFMGSG-UHFFFAOYSA-N 9-bromo-10-phenylanthracene Chemical compound C12=CC=CC=C2C(Br)=C2C=CC=CC2=C1C1=CC=CC=C1 WHGGVVHVBFMGSG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- UPBKHTAHMFYJSM-UHFFFAOYSA-N (1-phenylanthracen-9-yl)boronic acid Chemical compound C1(=CC=CC=C1)C1=CC=CC2=CC3=CC=CC=C3C(=C12)B(O)O UPBKHTAHMFYJSM-UHFFFAOYSA-N 0.000 description 1
- XHZUPQUVMGRPDC-UHFFFAOYSA-N 1,2,3,4-tetratert-butylperylene Chemical group C1=CC(C2=C(C(C(C)(C)C)=C(C=3C2=C2C=CC=3C(C)(C)C)C(C)(C)C)C(C)(C)C)=C3C2=CC=CC3=C1 XHZUPQUVMGRPDC-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- NDBKAUOQVJMBSH-UHFFFAOYSA-N Bc1c(cccc2)c2c(-c2ccccc2)c2ccccc12 Chemical compound Bc1c(cccc2)c2c(-c2ccccc2)c2ccccc12 NDBKAUOQVJMBSH-UHFFFAOYSA-N 0.000 description 1
- NCEDTMHPBMLCOH-UHFFFAOYSA-N CC1(C)c(cc(c(c2cc(Br)ccc22)c3)[n]2-c2ccccc2)c3-c2ccccc12 Chemical compound CC1(C)c(cc(c(c2cc(Br)ccc22)c3)[n]2-c2ccccc2)c3-c2ccccc12 NCEDTMHPBMLCOH-UHFFFAOYSA-N 0.000 description 1
- RFTRFDMRINNTSI-UHFFFAOYSA-N CC1(C)c(cc(cc2)Nc3ccccc3)c2-c2ccccc12 Chemical compound CC1(C)c(cc(cc2)Nc3ccccc3)c2-c2ccccc12 RFTRFDMRINNTSI-UHFFFAOYSA-N 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N Cc1ccccc1C Chemical compound Cc1ccccc1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-N aluminum;quinolin-8-ol Chemical compound [Al+3].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005872 benzooxazolyl group Chemical group 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001893 coumarin derivatives Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000000469 dry deposition Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical class [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 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
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
-
- 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
- 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
- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
-
- 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
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
본 발명은 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to an organic electroluminescent compound and an organic electroluminescent device including the same.
표시 소자 중, 전기 발광 소자(electroluminescence device: EL device)는 자체 발광형 표시 소자로서 LCD에 비해 시야각이 넓고 콘트라스트가 우수할 뿐만 아니라 응답속도가 빠르다는 장점을 가지고 있다. 1987년 이스트만 코닥(Eastman Kodak)사에서는 발광층 형성용 재료로서 저분자인 방향족 디아민과 알루미늄 착물을 이용하고 있는 유기 EL 소자를 처음으로 개발하였다[참조: Appl. Phys. Lett. 51, 913, 1987].Among electroluminescence devices, electroluminescence device (EL device) is a self-emissive type display device which has a wide viewing angle and excellent contrast as well as a high response speed. In 1987, Eastman Kodak Company first developed an organic EL device using an aromatic diamine and an aluminum complex having a low molecular weight as a material for forming a light emitting layer (Appl. Phys. Lett. 51, 913, 1987].
유기 EL 소자에서 발광 효율을 결정하는 가장 중요한 요인은 발광 재료이다. 발광 재료는 기능적인 측면에서 호스트 재료와 도판트 재료로 구분될 수 있는데 일반적으로 EL 특성이 가장 우수한 소자 구조로는 호스트에 도판트를 도핑하여 발광층을 만드는 것으로 알려져 있다. 최근에 고효율, 장수명 유기 EL 소자의 개발이 시급한 과제로 대두되고 있는데, 특히 중대형 OLED 패널에서 요구하고 있는 EL 특성 수준을 고려해 볼 때 기존의 발광 재료에 비해 매우 우수한 재료의 개발이 시급한 실정이다.The most important factor for determining the luminous efficiency in the organic EL device is the luminescent material. The luminescent material can be divided into a host material and a dopant material in terms of function. Generally, it is known that an EL material has the best EL structure to form a light emitting layer by doping a host with a dopant. In recent years, development of high-efficiency, long-life organic EL devices has become an urgent task. In particular, considering the level of EL characteristics required for middle- or large-sized OLED panels, it is urgent to develop materials superior to conventional light-emitting materials.
이를 위하여 고체 상태의 용매 및 에너지 전달자 역할을 하는 호스트 물질의 바람직한 특성은 순도가 높아야 하며, 진공증착이 가능하도록 적당한 분자량을 가져야 한다. 또한 유리 전이온도와 열분해온도가 높아 열적 안정성을 확보해야 하며, 장수명화를 위해 높은 전기화학적 안정성이 요구되며, 무정형 박막을 형성하기 용이해야 하며, 인접한 다른 층의 재료들과는 접착력이 좋은 반면 층간 이동은 하지 않아야 한다.For this purpose, the desirable characteristics of the host material acting as a solid state solvent and energy transfer agent should be high purity and have a proper molecular weight to enable vacuum deposition. In addition, the glass transition temperature and thermal decomposition temperature must be high to ensure thermal stability, high electrochemical stability is required for longevity improvement, amorphous thin film should be easy to form and adhesion with other adjacent layer materials is good, You should not.
발광 재료로는 현재까지 형광 재료가 널리 사용되고 있다. 청색 재료의 경우, 이데미쓰 고산의 4,4'-비스(2,2'-디페닐비닐)-1,1'-비페닐(DPVBi) 이후로 많은 재료들이 개발되어 상업화되어 있으며, 이데미쓰 고산의 청색 재료 시스템과 코닥의 디나프틸안트라센, 테트라(t-부틸)페릴렌 시스템 등이 알려져 있으나, 아직도 많은 연구 개발이 이루어져야 할 것으로 판단된다.Fluorescent materials are widely used as light emitting materials. In the case of blue materials, many materials have been developed and commercialized since 4,4'-bis (2,2'-diphenylvinyl) -1,1'-biphenyl (DPVBi) of Idemitsu Kosan. Although the blue material system and Kodak's dinaphthylanthracene and tetra (t-butyl) perylene systems are known, much research and development is still required.
한국등록특허 KR10-0987822 B, 한국공개특허 KR10-2010-0108903 A, KR10-2010-0109050 A 및 KR10-2012-0038402 A 등에는 여러 안트라센 유도체를 개시하고 있다.Korean Patent Registration KR10-0987822 B, Korean Patent Publication KR10-2010-0108903 A, KR10-2010-0109050 A, KR10-2012-0038402 A and the like disclose various anthracene derivatives.
본 발명자들이 예의 연구한 결과, 상기 문헌들에는 기재되어 있지 않은 특정 구조의 안트라센 유도체가 고효율 및 장수명의 유기 전계 발광 소자의 제조에 적합함을 발견하고 본 발명을 완성하게 되었다.As a result of diligent research by the present inventors, the present inventors have found that anthracene derivatives having a specific structure, which are not described in the above documents, are suitable for the production of high efficiency and long life organic electroluminescent devices, and have completed the present invention.
본 발명의 목적은 수명이 길고 발광 효율이 높은 유기 전계 발광 소자를 실현하도록 발광층의 형광 호스트로 사용될 수 있는 특정 구조의 안트라센 유도체를 제공하는 것이다.An object of the present invention is to provide an anthracene derivative having a specific structure that can be used as a fluorescent host of a light emitting layer to realize an organic electroluminescent device having a long lifetime and high luminous efficiency.
상기의 기술적 과제를 해결하기 위해 예의 연구한 결과, 본 발명자들은 하기 화학식 1로 표시되는 유기 전계 발광 화합물이 상술한 목적을 달성함을 발견하여 본 발명을 완성하였다.As a result of intensive studies to solve the above technical problems, the present inventors have found that an organic electroluminescent compound represented by the following general formula (1) achieves the above-mentioned object and completed the present invention.
[화학식 1][Chemical Formula 1]
상기 화학식 1에서,In Formula 1,
L1은 단일결합, 치환 또는 비치환 (C6-C30)아릴렌기, 또는 치환 또는 비치환 (5-30원) 헤테로아릴렌기이고;L 1 is a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (5- to 30-membered) heteroarylene group;
Ar1은 치환 또는 비치환 (C6-C30)아릴기, 또는 치환 또는 비치환 (5-30원) 헤테로아릴기이며;Ar 1 is a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (5- to 30-membered) heteroaryl group;
Ar2 및 Ar3은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 치환 또는 비치환 (C1-C30)알킬기, 치환 또는 비치환 (C6-C30)아릴기, 치환 또는 비치환 (5-30원) 헤테로아릴기 또는 -NR1R2이고;Ar 2 and Ar 3 are each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C6-C30) aryl group, substituted or unsubstituted (5- to 30-membered) ) Heteroaryl group or -NR 1 R 2 ;
R1 및 R2은 각각 독립적으로 수소, 치환 또는 비치환 (C6-C30)아릴기, 또는 치환 또는 비치환 (5-30원) 헤테로아릴기이거나; 서로 결합하여 (3-30원) 단일환 또는 다환의 지환족 또는 방향족 고리를 형성할 수 있고, 상기 형성된 지환족 또는 방향족 환의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있으며;R 1 and R 2 are each independently hydrogen, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5- to 30-membered) heteroaryl group; May be combined with each other to form a (3- to 30-membered) monocyclic or polycyclic alicyclic or aromatic ring, and the carbon atoms of the formed alicyclic or aromatic rings may be replaced with one or more heteroatoms selected from nitrogen, oxygen and sulfur And;
A고리 및 C고리는 각각 독립적으로 하기 식 1a로 표시되는 방향족환을 나타내고;A ring and C ring each independently represent an aromatic ring represented by the following formula 1a;
B고리는 하기 식 1b로 표시되는 5원환을 나타내며;Ring B represents a 5-membered ring represented by the following Formula 1b;
[식 1a][Formula 1a]
[식 1b][Equation 1b]
X 및 Y는 각각 독립적으로 -O-, -S-, -N(R21)- 또는 -C(R22)(R23)-이고, X가 -C(R22)(R23)-인 경우 Y는 -O-, -S- 또는 -N(R21)-이며, X가 -O- 또는 -S-인 경우 Y는 -N(R21)- 또는 -C(R22)(R23)-이고, X가 -N(R21)-인 경우 Y는 -O-, -S- 또는 -C(R22)(R23)-이며;X and Y are each independently -O-, -S-, -N (R 21 )-or -C (R 22 ) (R 23 )-, and X is -C (R 22 ) (R 23 )- Y is -O-, -S- or -N (R 21 )-and X is -O- or -S- and Y is -N (R 21 )-or -C (R 22 ) (R 23 ). ) And when X is -N (R 21 )-then Y is -O-, -S- or -C (R 22 ) (R 23 )-;
R은 수소, 중수소, 할로겐, 치환 또는 비치환 (C1-C30)알킬기, 치환 또는 비치환 (C6-C30)아릴기, 또는 치환 또는 비치환 (5-30원) 헤테로아릴기이고;R is hydrogen, deuterium, halogen, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5- to 30-membered) heteroaryl group;
R21 내지 R23은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환 (C1-C30)알킬기, 치환 또는 비치환 (C6-C30)아릴기, 또는 치환 또는 비치환 (5-30원) 헤테로아릴기이거나; 인접 치환체와 연결되어 (3-30원) 단일환 또는 다환의 지환족 또는 방향족 고리를 형성할 수 있고, 상기 형성된 지환족 또는 방향족 환의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있으며;R 21 to R 23 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C6-C30) aryl group, or substituted or unsubstituted (5- to 30-membered) hetero group Aryl group; Linked to adjacent substituents (3-30 members) to form a monocyclic or polycyclic alicyclic or aromatic ring, wherein the carbon atoms of the formed alicyclic or aromatic rings are replaced with one or more heteroatoms selected from nitrogen, oxygen and sulfur Can be;
a는 1 또는 2이고, a가 2인 경우 각각의 R은 동일하거나 상이할 수 있다.a is 1 or 2, and when a is 2, each R may be the same or different.
본 발명의 유기 전계 발광 화합물을 발광층의 형광호스트로 사용하면, 수명이 길고 발광 효율이 높은 유기 전계 발광 소자를 얻을 수 있다.When the organic electroluminescent compound of the present invention is used as a fluorescent host of a light emitting layer, an organic electroluminescent device having a long lifetime and high luminous efficiency can be obtained.
이하에서 본 발명을 더욱 상세히 설명하나, 이는 설명을 위한 것으로 본 발명의 범위를 제한하는 방법으로 해석되어서는 안 된다.Hereinafter, the present invention will be described in more detail, but this is for explanation and should not be construed as a method of limiting the scope of the present invention.
본 발명은 상기 화학식 1로 표시되는 유기 전계 발광 화합물, 상기 유기 전계 발광 화합물을 포함하는 유기 전계 발광 재료 및 상기 재료를 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to an organic electroluminescent compound represented by Formula 1, an organic electroluminescent material including the organic electroluminescent compound, and an organic electroluminescent device comprising the material.
본 발명의 상기 화학식 1로 표시되는 유기 전계 발광 화합물에 대해 보다 구체적으로 설명하면 다음과 같다.The organic electroluminescent compound represented by Formula 1 of the present invention will be described in more detail as follows.
본 발명에 기재되어 있는 "알킬"의 구체적인 예로서, 메틸, 에틸, n-프로필, 이소프로필, n-부틸, 이소부틸 및 tert-부틸 등이 있다. 본원에서 "알케닐"의 구체적인 예로서, 비닐, 1-프로페닐, 2-프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 2-메틸부트-2-에닐 등이 있다. 본원에서 "알키닐"의 예로서, 에티닐, 1-프로피닐, 2-프로피닐, 1-부티닐, 2-부티닐, 3-부티닐, 1-메틸펜트-2-이닐 등이 있다. 본원에서 "시클로알킬"의 예로서, 시클로프로필, 시클로부틸, 시클로펜틸, 시클로헥실 등이 있다. 본원에서 "(5-7원) 헤테로시클로알킬"은 환 골격 원자수가 5 내지 7개이고, B, N, O, S, P(=O), Si 및 P로 이루어진 군에서 선택된 하나 이상의 헤테로원자, 바람직하게는 O, S 및 N에서 선택되는 하나 이상의 헤테로원자를 포함하는 시클로알킬을 의미하고, 예를 들어, 테트라히드로푸란, 피롤리딘, 티올란, 테트라히드로피란 등이 있다. 본원에서 "아릴(렌)"은 방향족 탄화수소에서 유래된 단일환 또는 융합환계 라디칼을 의미하고, 예로서 페닐, 비페닐, 터페닐, 나프틸, 비나프틸, 페닐나프틸, 나프틸페닐, 플루오레닐, 페닐플루오레닐, 벤조플루오레닐, 디벤조플루오레닐, 페난트레닐, 페닐페난트레닐, 안트라세닐, 인데닐, 트리페닐레닐, 피레닐, 테트라세닐, 페릴레닐, 크라이세닐, 나프타세닐, 플루오란테닐 등이 있다. 본원에서 "(3-30원) 헤테로아릴(렌)"은 환 골격 원자수가 3 내지 30개이고, B, N, O, S, P(=O), Si 및 P로 이루어진 군에서 선택된 하나 이상의 헤테로원자를 포함하는 아릴기를 의미한다. 헤테로원자수는 바람직하게는 1 내지 4개이고, 단일 환계이거나 하나 이상의 벤젠환과 축합된 융합환계일 수 있으며, 부분적으로 포화될 수도 있다. 또한, 본원에서 상기 헤테로아릴(렌)은 하나 이상의 헤테로아릴 또는 아릴기가 단일 결합에 의해 헤테로아릴기와 연결된 형태도 포함한다. 상기 헤테로아릴의 예로서, 푸릴, 티오펜일, 피롤릴, 이미다졸릴, 피라졸릴, 티아졸릴, 티아디아졸릴, 이소티아졸릴, 이속사졸릴, 옥사졸릴, 옥사디아졸릴, 트리아진일, 테트라진일, 트리아졸릴, 테트라졸릴, 푸라잔일, 피리딜, 피라진일, 피리미딘일, 피리다진일 등의 단일 환계 헤테로아릴, 벤조푸란일, 벤조티오펜일, 이소벤조푸란일, 디벤조푸란일, 디벤조티오펜일, 벤조이미다졸릴, 벤조티아졸릴, 벤조이소티아졸릴, 벤조이속사졸릴, 벤조옥사졸릴, 이소인돌릴, 인돌릴, 인다졸릴, 벤조티아디아졸릴, 퀴놀릴, 이소퀴놀릴, 신놀리닐, 퀴나졸리닐, 퀴녹살리닐, 카바졸릴, 페녹사진일, 페난트리딘일, 벤조디옥솔릴 등의 융합 환계 헤테로아릴 등이 있다. 본원에서 "할로겐"은 F, Cl, Br 및 I 원자를 포함한다.Specific examples of the "alkyl" described in the present invention include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl. Specific examples of the "alkenyl" herein include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like. Examples of "alkynyl" herein include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2- Examples of "cycloalkyl" herein include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. The term "(5-7 membered) heterocycloalkyl" as used herein means an aromatic heterocycle having 5 to 7 ring skeletal atoms and at least one heteroatom selected from the group consisting of B, N, O, S, P (= O) Preferably one or more heteroatoms selected from O, S and N, and includes, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran and the like. Means a single ring or fused ring radical derived from an aromatic hydrocarbon and includes, for example, phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, Anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, and cricenyl < RTI ID = 0.0 > , Naphthacenyl, fluoranthenyl and the like. The term "(3-30) heteroaryl (phenylene)" used herein refers to a heteroaryl group having 3 to 30 ring skeletal atoms and one or more heteroatoms selected from the group consisting of B, N, O, S, P Quot; means an aryl group containing an atom. The number of heteroatoms is preferably 1 to 4, and may be a monocyclic ring system or a fused ring system condensed with at least one benzene ring, and may be partially saturated. In addition, the heteroaryl (phenylene) also includes a heteroaryl group in which at least one heteroaryl or aryl group is linked to a heteroaryl group by a single bond. Examples of such heteroaryls include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl , Monocyclic heteroaryl such as triazolyl, tetrazolyl, furanzyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, di Benzoimidazolyl, benzothiazolyl, benzothiazolyl, benzoisothiazolyl, benzooxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, Fused heterocyclic heteroaryl such as norbornyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxaphyl, phenanthridinyl, benzodioxolyl and the like. As used herein, "halogen" includes F, Cl, Br, and I atoms.
또한 본 발명에 기재되어 있는 "치환 또는 비치환"이라는 기재에서 '치환'은 어떤 작용기에서 수소 원자가 다른 원자 또는 다른 작용기 (즉, 치환체)로 대체되는 것을 뜻한다. 상기 화학식 1의 L1, Ar1 내지 Ar3, R, R1, R2, R21 내지 R23에서 치환 알킬, 치환 아릴(렌) 및 치환 헤테로아릴(렌)의 치환체는 각각 독립적으로 중수소, 할로겐, 할로겐으로 치환 또는 비치환된 (C1-C30)알킬, (C1-C30)알콕시, (C6-C30)아릴, (C6-C30)아릴로 치환 또는 비치환된 (3-30 원)헤테로아릴, (C3-C30)시클로알킬, (5-7 원) 헤테로시클로알킬, 트리(C1-C30)알킬실릴, 트리(C6-C30)아릴실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, (C1-C30)알킬디(C6-C30)아릴실릴, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, 카바졸릴, 디(C1-C30)알킬아미노, (C1-C30)알킬로 치환 또는 비치환된 디(C6-C30)아릴아미노, (C1-C30)알킬(C6-C30)아릴아미노, 디(C6-C30)아릴보로닐, 디(C1-C30)알킬보로닐, (C1-C30)알킬(C6-C30)아릴보로닐, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, 카르복실, 니트로 및 히드록시로 이루어진 군으로부터 선택되는 하나 이상인 것을 의미하고, 각각 독립적으로 중수소, 할로겐, (C1-C6)알킬, (C1-C6)알콕시, (C6-C21)아릴, (C3-C21)시클로알킬, 트리(C6-C12)아릴실릴, 시아노, 디(C6-C12)아릴아미노 및 히드록시로 이루어진 군으로부터 선택되는 하나 이상인 것이 바람직하다.Also, in the phrase "substituted or unsubstituted" described in the present invention, "substituted" means that a hydrogen atom is replaced with another atom or another functional group (ie, a substituent) in a certain functional group. Substituents of substituted alkyl, substituted aryl (lene) and substituted heteroaryl (lene) in L 1 , Ar 1 to Ar 3 , R, R 1 , R 2 , R 21 to R 23 of Formula 1 may each independently be deuterium, (3-30 membered) heteroaryl unsubstituted or substituted with halogen, halogen-substituted or unsubstituted (C1-C30) alkyl, (C1-C30) alkoxy, (C6-C30) aryl, (C6-C30) aryl , (C3-C30) cycloalkyl, (5-7 membered) heterocycloalkyl, tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) aryl Silyl, (C1-C30) alkyldi (C6-C30) arylsilyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, carbazolyl, di (C1-C30) alkylamino, (C1 Di (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino, di (C6-C30) arylboronyl, di (C1-C30) unsubstituted or substituted with alkyl Alkylboronyl, (C1-C30) alkyl (C6-C30) arylboronyl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxyl, In groups consisting of nitro and hydroxy It means one or more selected from, and each independently deuterium, halogen, (C1-C6) alkyl, (C1-C6) alkoxy, (C6-C21) aryl, (C3-C21) cycloalkyl, tri (C6-C12) ) At least one selected from the group consisting of arylsilyl, cyano, di (C6-C12) arylamino and hydroxy.
또한 상기 화학식 1에서 구체적으로 
상기 X, Y, R 및 a는 상기 화학식 1에서의 정의와 동일하다.X, Y, R and a are the same as defined in the formula (1).
상기 화학식 1에서, 상기 L1은 단일결합, 치환 또는 비치환 (C6-C30)아릴렌기, 또는 치환 또는 비치환 (5-30원) 헤테로아릴렌기이고, 바람직하게는 단일결합, 치환 또는 비치환 (C6-C21)아릴렌기, 또는 치환 또는 비치환 (5-21원) 헤테로아릴렌기이며, 더욱 바람직하게는 단일결합, (C1-C6)알킬로 치환 또는 비치환된 (C6-C21)아릴렌기, 또는 비치환 (5-21원) 헤테로아릴렌기이다.In Formula 1, L 1 is a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (5- to 30-membered) heteroarylene group, preferably a single bond, a substituted or unsubstituted (C6-C21) arylene group or a substituted or unsubstituted (5- to 21-membered) heteroarylene group, more preferably a (C6-C21) arylene group unsubstituted or substituted with a single bond, (C1-C6) alkyl Or an unsubstituted (5-21 membered) heteroarylene group.
상기 Ar1은 치환 또는 비치환 (C6-C30)아릴기, 또는 치환 또는 비치환 (5-30원) 헤테로아릴기이고, 바람직하게는 치환 또는 비치환 (C6-C21)아릴기, 또는 치환 또는 비치환 (5-21원) 헤테로아릴기이며, 더욱 바람직하게는 중수소, 할로겐, (C1-C6)알킬, (C1-C6)알콕시, (C6-C21)아릴, (C3-C21)시클로알킬, 트리(C6-C12)아릴실릴, 시아노, 디(C6-C12)아릴아미노, 또는 히드록시로 치환 또는 비치환된 (C6-C21)아릴기; 또는 (C6-C21)아릴로 치환 또는 비치환 (5-21원) 헤테로아릴기이다.Ar 1 is a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5- to 30-membered) heteroaryl group, preferably a substituted or unsubstituted (C6-C21) aryl group, or substituted or Unsubstituted (5-21 membered) heteroaryl group, more preferably deuterium, halogen, (C1-C6) alkyl, (C1-C6) alkoxy, (C6-C21) aryl, (C3-C21) cycloalkyl, A (C6-C21) aryl group unsubstituted or substituted with tri (C6-C12) arylsilyl, cyano, di (C6-C12) arylamino, or hydroxy; Or a (5- to 21-membered) heteroaryl group unsubstituted or substituted with (C6-C21) aryl.
상기 Ar2 및 Ar3은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 치환 또는 비치환 (C1-C30)알킬기, 치환 또는 비치환 (C6-C30)아릴기, 치환 또는 비치환 (5-30원) 헤테로아릴기 또는 -NR1R2이고, 바람직하게는 각각 독립적으로 수소, 치환 또는 비치환 (C6-C21)아릴기, 치환 또는 비치환 (5-21원) 헤테로아릴기 또는 -NR1R2이며, 더욱 바람직하게는 각각 독립적으로 수소, 비치환 (C6-C21)아릴기, 비치환 (5-21원) 헤테로아릴기 또는 -NR1R2이다.Ar 2 and Ar 3 are each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C6-C30) aryl group, substituted or unsubstituted (5-30 And a heteroaryl group or -NR 1 R 2 , preferably each independently hydrogen, a substituted or unsubstituted (C6-C21) aryl group, a substituted or unsubstituted (5- to 21-membered) heteroaryl group or -NR 1 R 2 , and more preferably each independently represents hydrogen, an unsubstituted (C6-C21) aryl group, an unsubstituted (5-21 membered) heteroaryl group, or -NR 1 R 2 .
상기 R1 및 R2은 각각 독립적으로 수소, 치환 또는 비치환 (C6-C30)아릴기, 또는 치환 또는 비치환 (5-30원) 헤테로아릴기이거나; 서로 결합하여 (3-30원) 단일환 또는 다환의 지환족 또는 방향족 고리를 형성할 수 있고, 상기 형성된 지환족 또는 방향족 환의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고, 바람직하게는 각각 독립적으로 수소 또는 치환 또는 비치환 (C6-C21)아릴기이며, 더욱 바람직하게는 각각 독립적으로 수소 또는 (C1-C6)알킬로 치환 또는 비치환된 (C6-C21)아릴기이다.R 1 and R 2 are each independently hydrogen, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5- to 30-membered) heteroaryl group; May be combined with each other to form a (3- to 30-membered) monocyclic or polycyclic alicyclic or aromatic ring, and the carbon atoms of the formed alicyclic or aromatic rings may be replaced with one or more heteroatoms selected from nitrogen, oxygen and sulfur And preferably each independently hydrogen or a substituted or unsubstituted (C6-C21) aryl group, and more preferably each independently substituted or unsubstituted (C6-C21) aryl with hydrogen or (C1-C6) alkyl. Qi.
상기 X 및 Y는 각각 독립적으로 -O-, -S-, -N(R21)- 또는 -C(R22)(R23)-이고, X가 -C(R22)(R23)-인 경우 Y는 -O-, -S- 또는 -N(R21)-이며, X가 -O- 또는 -S-인 경우 Y는 -N(R21)- 또는 -C(R22)(R23)-이고, X가 -N(R21)-인 경우 Y는 -O-, -S- 또는 -C(R22)(R23)-이다.X and Y are each independently -O-, -S-, -N (R 21 )-or -C (R 22 ) (R 23 )-, and X is -C (R 22 ) (R 23 )- Y is -O-, -S- or -N (R 21 )-when X is -O- or -S- and Y is -N (R 21 )-or -C (R 22 ) (R 23 )-and when X is -N (R 21 )-then Y is -O-, -S- or -C (R 22 ) (R 23 )-.
상기 R은 수소, 중수소, 할로겐, 치환 또는 비치환 (C1-C30)알킬기, 치환 또는 비치환 (C6-C30)아릴기, 또는 치환 또는 비치환 (5-30원) 헤테로아릴기이고, 바람직하게는 수소이다.R is hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C6-C30) aryl group, or substituted or unsubstituted (5- to 30-membered) heteroaryl group, preferably Is hydrogen.
상기 R21 내지 R23은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환 (C1-C30)알킬기, 치환 또는 비치환 (C6-C30)아릴기, 또는 치환 또는 비치환 (5-30원) 헤테로아릴기이거나; 인접 치환체와 연결되어 (3-30원) 단일환 또는 다환의 지환족 또는 방향족 고리를 형성할 수 있고, 상기 형성된 지환족 또는 방향족 환의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고, 바람직하게는 각각 독립적으로 치환 또는 비치환 (C1-C6)알킬기 또는 치환 또는 비치환 (C6-C21)아릴기이며, 더욱 바람직하게는 각각 독립적으로 비치환 (C1-C6)알킬기 또는 비치환 (C6-C21)아릴기이다.R 21 to R 23 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C6-C30) aryl group, or substituted or unsubstituted (5- to 30-membered) Heteroaryl group; Linked to adjacent substituents (3-30 members) to form a monocyclic or polycyclic alicyclic or aromatic ring, wherein the carbon atoms of the formed alicyclic or aromatic rings are replaced with one or more heteroatoms selected from nitrogen, oxygen and sulfur And preferably each independently a substituted or unsubstituted (C1-C6) alkyl group or a substituted or unsubstituted (C6-C21) aryl group, more preferably each independently an unsubstituted (C1-C6) alkyl group or It is an unsubstituted (C6-C21) aryl group.
본원 발명의 일실시예에 따르면, 상기 화학식 1에서, 상기 L1은 단일결합, 치환 또는 비치환 (C6-C21)아릴렌기, 또는 치환 또는 비치환 (5-21원) 헤테로아릴렌기이고; Ar1은 치환 또는 비치환 (C6-C21)아릴기, 또는 치환 또는 비치환 (5-21원) 헤테로아릴기이며; Ar2 및 Ar3은 각각 독립적으로 수소, 치환 또는 비치환 (C6-C21)아릴기, 치환 또는 비치환 (5-21원) 헤테로아릴기 또는 -NR1R2이고; R1 및 R2은 각각 독립적으로 수소 또는 치환 또는 비치환 (C6-C21)아릴기이며; X 및 Y는 각각 독립적으로 -O-, -S-, -N(R21)- 또는 -C(R22)(R23)-이고, X가 -C(R22)(R23)-인 경우 Y는 -O-, -S- 또는 -N(R21)-이며, X가 -O- 또는 -S-인 경우 Y는 -N(R21)- 또는 -C(R22)(R23)-이고, X가 -N(R21)-인 경우 Y는 -O-, -S- 또는 -C(R22)(R23)-이고; R은 수소이며; R21 내지 R23은 각각 독립적으로 치환 또는 비치환 (C1-C6)알킬기 또는 치환 또는 비치환 (C6-C21)아릴기이다.According to an embodiment of the present invention, in formula 1, L 1 is a single bond, a substituted or unsubstituted (C6-C21) arylene group, or a substituted or unsubstituted (5-21 membered) heteroarylene group; Ar 1 is a substituted or unsubstituted (C6-C21) aryl group or a substituted or unsubstituted (5-21 membered) heteroaryl group; Ar 2 and Ar 3 are each independently hydrogen, a substituted or unsubstituted (C6-C21) aryl group, a substituted or unsubstituted (5-21 membered) heteroaryl group, or -NR 1 R 2 ; R 1 and R 2 are each independently hydrogen or a substituted or unsubstituted (C6-C21) aryl group; X and Y are each independently -O-, -S-, -N (R 21 )-or -C (R 22 ) (R 23 )-, and X is -C (R 22 ) (R 23 )- Y is -O-, -S- or -N (R 21 )-and X is -O- or -S- and Y is -N (R 21 )-or -C (R 22 ) (R 23 ). ) And when X is -N (R 21 )-then Y is -O-, -S- or -C (R 22 ) (R 23 )-; R is hydrogen; R 21 to R 23 are each independently a substituted or unsubstituted (C1-C6) alkyl group or a substituted or unsubstituted (C6-C21) aryl group.
본원 발명의 다른 일실시예에 따르면, 상기 화학식 1에서, 상기 L1은 단일결합, (C1-C6)알킬로 치환 또는 비치환된 (C6-C21)아릴렌기, 또는 비치환된 (5-21원) 헤테로아릴렌기이고; Ar1은 중수소, 할로겐, (C1-C6)알킬, (C1-C6)알콕시, (C6-C21)아릴, (C3-C21)시클로알킬, 트리(C6-C12)아릴실릴, 시아노, 디(C6-C12)아릴아미노, 또는 히드록시로 치환 또는 비치환된 (C6-C21)아릴기; 또는 (C6-C21)아릴로 치환 또는 비치환 (5-21원) 헤테로아릴기이며; Ar2 및 Ar3은 각각 독립적으로 수소, 비치환 (C6-C21)아릴기, 비치환 (5-21원) 헤테로아릴기 또는 -NR1R2이고; R1 및 R2은 각각 독립적으로 수소 또는 (C1-C6)알킬로 치환 또는 비치환된 (C6-C21)아릴기이며; X 및 Y는 각각 독립적으로 -O-, -S-, -N(R21)- 또는 -C(R22)(R23)-이고, X가 -C(R22)(R23)-인 경우 Y는 -O-, -S- 또는 -N(R21)-이며, X가 -O- 또는 -S-인 경우 Y는 -N(R21)- 또는 -C(R22)(R23)-이고, X가 -N(R21)-인 경우 Y는 -O-, -S- 또는 -C(R22)(R23)-이고; R은 수소이며; R21 내지 R23은 각각 독립적으로 비치환 (C1-C6)알킬기 또는 비치환 (C6-C21)아릴기이다.According to another embodiment of the present invention, in Chemical Formula 1, L 1 is a single bond, a (C6-C21) arylene group unsubstituted or substituted with (C1-C6) alkyl, or an unsubstituted (5-21) Circle) heteroarylene group; Ar 1 is deuterium, halogen, (C1-C6) alkyl, (C1-C6) alkoxy, (C6-C21) aryl, (C3-C21) cycloalkyl, tri (C6-C12) arylsilyl, cyano, di ( C6-C12) arylamino or a (C6-C21) aryl group unsubstituted or substituted with hydroxy; Or a (5- to 21-membered) heteroaryl group substituted or unsubstituted with (C6-C21) aryl; Ar 2 and Ar 3 are each independently hydrogen, unsubstituted (C6-C21) aryl group, unsubstituted (5-21 membered) heteroaryl group, or -NR 1 R 2 ; R 1 and R 2 are each independently a (C6-C21) aryl group unsubstituted or substituted with hydrogen or (C1-C6) alkyl; X and Y are each independently -O-, -S-, -N (R 21 )-or -C (R 22 ) (R 23 )-, and X is -C (R 22 ) (R 23 )- Y is -O-, -S- or -N (R 21 )-and X is -O- or -S- and Y is -N (R 21 )-or -C (R 22 ) (R 23 ). ) And when X is -N (R 21 )-then Y is -O-, -S- or -C (R 22 ) (R 23 )-; R is hydrogen; R 21 to R 23 are each independently an unsubstituted (C1-C6) alkyl group or an unsubstituted (C6-C21) aryl group.
상기 화학식 1의 유기 전계 발광 화합물은 보다 구체적으로 하기의 화합물로서 예시될 수 있으나, 이들에 한정되는 것은 아니다.The organic electroluminescent compound of Formula 1 may be more specifically exemplified by the following compounds, but is not limited thereto.
본 발명에 따른 유기 전계 발광 화합물은 당업자에게 공지된 합성 방법으로 제조할 수 있으며, 예를 들면 하기 반응식 1 또는 2에 나타난 바와 같이 제조할 수 있다.The organic electroluminescent compounds according to the present invention can be prepared by synthetic methods known to those skilled in the art, for example, as shown in Schemes 1 or 2 below.
[반응식 1][Reaction Scheme 1]
[반응식 2][Reaction Scheme 2]
상기 반응식 1 및 2에서, Ar1, Ar2, Ar3, L1, X, A고리, B고리 및 C고리는 화학식 1에서의 정의와 동일하고, Hal는 할로겐이다.In Schemes 1 and 2, Ar 1 , Ar 2 , Ar 3 , L 1 , X, A ring, B ring and C ring are the same as defined in the formula (1), Hal is halogen.
또한, 본 발명은 화학식 1의 유기 전계 발광 화합물을 포함하는 유기 전계 발광 재료 및 상기 재료를 포함하는 유기 전계 발광 소자를 제공한다.The present invention also provides an organic electroluminescent material comprising an organic electroluminescent compound of Formula 1 and an organic electroluminescent device comprising the same.
상기 재료는 본 발명의 유기 전계 발광 화합물 단독으로 이루어질 수 있고, 유기 전계 발광 재료에 포함되는 통상의 물질들을 추가로 포함할 수도 있다.The material may be composed of the organic electroluminescent compound of the present invention alone, and may further include conventional materials included in the organic electroluminescent material.
본 발명에 따른 유기 전계 발광 소자는 제1전극; 제2전극; 및 상기 제1전극 및 제2전극 사이에 개재되는 1층 이상의 유기물층을 갖고, 상기 유기물층은 상기 화학식 1의 유기 전계 발광 화합물을 하나 이상 포함할 수 있다.An organic electroluminescent device according to the present invention includes a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, and the organic material layer may include at least one organic electroluminescent compound represented by Formula 1.
상기 제1전극과 제2전극 중 하나는 애노드이고 다른 하나는 캐소드일 수 있다. 상기 유기물층은 발광층을 포함하고, 정공주입층, 정공전달층, 전자전달층, 전자주입층, 계면층(interlayer), 정공차단층 및 전자차단층에서 선택되는 1층 이상을 더 포함할 수 있다.One of the first electrode and the second electrode may be an anode and the other may be a cathode. The organic material layer may further include one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer.
또한 상기 유기물층은 발광층을 포함하고, 이 발광층에서 상기 화학식 1의 유기 전계 발광 화합물을 호스트 물질로 사용할 수 있다.The organic layer may include a light emitting layer, and the organic electroluminescent compound of Formula 1 may be used as a host material in the light emitting layer.
또한 본 발명에 따른 호스트 물질과 함께 형광성 도판트 물질을 포함할 수 있다.It may also comprise a fluorescent dopant material with the host material according to the invention.
형광성 도펀트는 1중항 여기자로부터 발광할 수 있는 화합물이다. 형광성 도펀트로서는 아민계 화합물, 방향족 화합물, 트리스(8-퀴놀리노레이트)알루미늄 착체 등의 킬레이트 착체, 쿠마린 유도체, 테트라페닐부타디엔 유도체, 비스스티릴아릴렌 유도체, 옥사디아졸 유도체 등으로부터 요구되는 발광색에 맞게 선택되는 화합물인 것이 바람직하고, 스티릴아민 화합물, 스티릴디아민 화합물, 아릴아민 화합물, 아릴디아민 화합물이 보다 바람직하고, 축합 다환 아민 유도체가 더욱 바람직하다. 이들 형광성 도펀트는 단독으로도 또한 복수 조합하여 사용할 수도 있다.Fluorescent dopants are compounds capable of emitting light from monomodal excitons. Examples of the fluorescent dopant include luminescent colors required from chelate complexes such as amine compounds, aromatic compounds, tris (8-quinolinolate) aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, bistyrylarylene derivatives, oxadiazole derivatives, A styrylamine compound, a styryldiamine compound, an arylamine compound, and an aryldiamine compound are more preferable, and a condensed polycyclic amine derivative is more preferable. These fluorescent dopants may be used singly or in combination.
본원 발명의 유기 전계 발광 소자에 포함되는 형광성 도판트로 축합 다환 아민 유도체로서는 하기 화학식 2로 표시되는 화합물을 사용할 수 있다.As the fluorescent dopant and the condensed polycyclic amine derivative contained in the organic electroluminescent device of the present invention, a compound represented by the following general formula (2) can be used.
[화학식 2](2)
상기 화학식 2에서,In Formula 2,
Ar21은 치환 또는 비치환된 (C6-C50)아릴 또는 스티릴이고; L은 단일결합, 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (3-30 원)헤테로아릴이며; Ar22 및 Ar23은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (3-30 원)헤테로아릴이거나; 인접한 치환체와 결합하여 (3-30원) 단일환 또는 다환의 지환족 또는 방향족 고리를 형성할 수 있고, 상기 형성된 지환족 또는 방향족 환의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고; n은 1 또는 2이며, n이 2인 경우 각각의 
Ar21에서 바람직한 아릴기로는 치환 또는 비치환의 페닐, 치환 또는 비치환의 플루오레닐기, 치환 또는 비치환의 안트릴기, 치환 또는 비치환의 피레닐기, 치환 또는 비치환의 크리세닐기 및 치환 또는 비치환의 벤조플루오레닐기 등이 있다.The preferred aryl group in Ar 21 is a substituted or unsubstituted phenyl, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, and a substituted or unsubstituted benzofluor Oleyl group and the like.
상기 화학식 2의 구체적인 화합물은 하기의 화합물로서 예시될 수 있으나 이들에 한정되는 것은 아니다.The specific compounds of Formula 2 may be exemplified as the following compounds, but are not limited thereto.
본 발명의 유기 전계 발광 소자는 화학식 1의 유기 전계 발광 화합물을 포함하고, 이와 동시에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 화합물을 포함할 수 있다.The organic electroluminescent device of the present invention includes the organic electroluminescent compound of Formula 1, and at the same time, may include at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound.
또한, 본 발명의 유기 전계 발광 소자에 있어서, 유기물층에 상기 화학식 1의 유기 전계 발광 화합물 이외에 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속 또는 착체화합물을 더 포함할 수도 있고, 나아가 상기 유기물층은 발광층 및 전하생성층을 더 포함할 수 있다.Further, in the organic electroluminescent device of the present invention, in addition to the organic electroluminescent compound of Formula 1, an organic electroluminescent compound of the group 1, 2, 4, 5 period transition metal, lanthanide series and d- The organic compound layer may further include at least one metal or complex compound selected from the group consisting of a light emitting layer and a charge generating layer.
또한, 상기 유기물층은 상기 유기 전계 발광 화합물 이외에 청색, 적색 또는 녹색 발광 화합물을 포함하는 유기발광층 하나 이상을 동시에 포함하여 백색 발광을 하는 유기 전계 발광 소자를 형성할 수 있다.In addition, the organic material layer may include at least one organic light emitting layer including a blue, red, or green light emitting compound in addition to the organic electroluminescent compound to form an organic electroluminescent device emitting white light.
본 발명의 유기 전계 발광 소자에 있어서, 한 쌍의 전극의 적어도 한쪽의 내측표면에, 칼코제나이드(chalcogenide)층, 할로겐화 금속층 및 금속 산화물층으로부터 선택되는 일층(이하, 이들을 “표면층”이라고 지칭함) 이상을 배치하는 것이 바람직하다. 구체적으로는, 발광 매체층 측의 양극 표면에 규소 및 알루미늄의 금속의 칼코제나이드(산화물을 포함한다)층을, 또한 발광매체층 측의 음극 표면에 할로겐화 금속층 또는 금속 산화물층을 배치하는 것이 바람직하다. 이것에 의해 구동의 안정화를 얻을 수 있다. 상기 칼코제나이드의 바람직한 예로는 SiOX(1≤X≤2), AlOX(1≤X≤1.5), SiON 또는 SiAlON 등이 있고, 할로겐화 금속의 바람직한 예로는 LiF, MgF2, CaF2, 불화 희토류 금속 등이 있으며, 금속 산화물의 바람직한 예로는 Cs2O, Li2O, MgO, SrO, BaO, CaO 등이 있다.In the organic electroluminescent device of the present invention, one layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer (hereinafter referred to as " surface layer ") is formed on the inner surface of at least one of the pair of electrodes, Or more. Concretely, it is preferable to dispose a halogenated metal layer or a metal oxide layer on the surface of the anode on the side of the light emitting medium layer and on the surface of the cathode on the side of the light emitting medium layer, with a chalcogenide (including oxide) layer of a metal of silicon and aluminum Do. Thus, stabilization of the drive can be obtained. Preferable examples of the chalcogenide include SiO X (1? X ? 2), AlO x (1? X ? 1.5), SiON or SiAlON. Preferred examples of the halogenated metal include LiF, MgF 2 , CaF 2 , Rare-earth metals, etc. Preferred examples of the metal oxides include Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO and the like.
또한, 본 발명의 유기 전계 발광 소자에 있어서, 이렇게 제작된 한 쌍의 전극의 적어도 한쪽의 표면에 전자 전달 화합물과 환원성 도판트의 혼합 영역 또는 정공 전달 화합물과 산화성 도판트의 혼합 영역을 배치하는 것도 바람직하다. 이러한 방식에 의해 전자 전달 화합물이 음이온으로 환원되므로 혼합 영역으로부터 발광 매체에 전자를 주입 및 전달하기 용이해진다. 또한, 정공 전달 화합물은 산화되어 양이온으로 되므로 혼합 영역으로부터 발광 매체에 정공을 주입 및 전달하기 용이해진다. 바람직한 산화성 도판트로서는 각종 루이스산 및 억셉터(acceptor) 화합물을 들 수 있고, 바람직한 환원성 도판트로는 알칼리 금속, 알칼리 금속 화합물, 알칼리 토류 금속, 희토류 금속 및 이들의 혼합물을 들 수 있다. 또한 환원성 도판트층을 전하생성층으로 사용하여 두 개 이상의 발광층을 가진 백색 유기 전계 발광소자를 제작할 수 있다.In addition, in the organic electroluminescent device of the present invention, a mixed region of the electron transfer compound and the reducing dopant or a mixed region of the hole transport compound and the oxidative dopant is disposed on at least one surface of the pair of electrodes thus fabricated desirable. In this way, since the electron transfer compound is reduced to an anion, it becomes easy to inject and transfer electrons from the mixed region to the light emitting medium. Further, since the hole transport compound is oxidized and becomes a cation, it becomes easy to inject and transport holes from the mixed region into the light emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, and preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Also, a white organic light emitting device having two or more light emitting layers can be manufactured using a reducing dopant layer as a charge generating layer.
본 발명의 유기 전계 발광 소자의 각 층의 형성은 진공증착, 스퍼터링, 플라즈마, 이온플레이팅 등의 건식 성막법이나, 스핀코팅, 디핑, 플로우 코팅 등의 습식 성막법 중 어느 하나의 방법을 적용할 수 있다.Formation of each layer of the organic electroluminescent device of the present invention may be carried out by any one of dry deposition methods such as vacuum deposition, sputtering, plasma, ion plating, and wet deposition methods such as spin coating, dipping, and flow coating. Can be.
습식 성막법의 경우, 각 층을 형성하는 재료를 에탄올, 클로로포름, 테트라하이드로퓨란, 디옥산 등의 적절한 용매에 용해 또는 분산시켜 박막을 형성하는데, 그 용매는 어느 것이어도 된다.In the case of the wet film formation method, a thin film is formed by dissolving or dispersing a material forming each layer in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc., and any solvent may be used.
이하에서, 본 발명의 상세한 이해를 위하여 본 발명의 대표 화합물을 들어 본 발명에 따른 유기 전계 발광 화합물, 이의 제조방법 및 소자의 발광특성을 설명한다.Hereinafter, the organic electroluminescent compound according to the present invention, the method for producing the same, and the luminescent characteristics of the device will be described with reference to the representative compound of the present invention for a detailed understanding of the present invention.
[[ 실시예Example 1] 화합물 H-44의 제조 1] Preparation of Compound H-44
화합물 A 5 g (15 mmol), 9-브로모-10-페닐안트라센 6.6 g (16.5 mmol), Pd(PPh3)4 1.0 g (0.9 mmol), K2CO3 (2M) 22 mL, 에탄올 22 mL, 톨루엔 44 mL를 플라스크에 넣고, 120℃에서 4시간 동안 환류 교반하였다. 반응이 끝나면 증류수로 씻어주고 에틸아세테이트(EA)로 추출한 뒤, 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼으로 정제하여 H-44, 4.4 g (48 %)를 얻었다.Compound A 5 g (15 mmol), 9-bromo-10-phenylanthracene 6.6 g (16.5 mmol), Pd (PPh 3 ) 4 1.0 g (0.9 mmol), K 2 CO 3 (2M) 22 mL, ethanol 22 mL and 44 mL of toluene were placed in a flask and stirred at reflux at 120 ° C. for 4 hours. After the reaction, the mixture was washed with distilled water, extracted with ethyl acetate (EA), the organic layer was dried over MgSO 4 , the solvent was removed using a rotary evaporator, and purified by column to obtain H-44 , 4.4 g (48%).
물성데이터: 녹는점 332℃, UV 312nm (톨루엔 내에서), PL 426nm (톨루엔 내에서), 분자량 611.26
Physical property data: Melting point 332 ° C, UV 312nm (in toluene), PL 426nm (in toluene), molecular weight 611.26
[[ 실시예Example 2] 화합물 H-86의 제조 2] Preparation of Compound H-86
화합물 B 3.5 g (8.2 mmol), 10-페닐안트라센-9-일 보론산 2.3 g (8.6 mmol), Pd(PPh3)4 568 mg (0.5 mmol), K2CO3 (2M) 12 mL, 에탄올 12 mL, 톨루엔 24 mL를 플라스크에 넣고, 120℃에서 4시간 동안 환류 교반하였다. 반응이 끝나면 증류수로 씻어주고 EA로 추출한 뒤 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼으로 정제하여 H-86, 3.6 g (72 %)를 얻었다.Compound B 3.5 g (8.2 mmol), 10 g of phenylanthracene-9-yl boronic acid 2.3 g (8.6 mmol), Pd (PPh 3 ) 4 568 mg (0.5 mmol), K 2 CO 3 (2M) 12 mL, ethanol 12 mL and 24 mL of toluene were placed in a flask and stirred at reflux at 120 ° C. for 4 hours. After the reaction, the mixture was washed with distilled water, extracted with EA, dried over MgSO 4 , dried over MgSO 4 , solvent was removed on a rotary evaporator, and purified by column to obtain H-86 , 3.6 g (72%).
물성데이터: 녹는점 374℃, UV 292nm (톨루엔 내에서), PL 426nm (톨루엔 내에서), 분자량 601.19
Physical property data: Melting point 374 ° C, UV 292nm (in toluene), PL 426nm (in toluene), molecular weight 601.19
[[ 실시예Example 3] 화합물 H-101의 제조 3] Preparation of Compound H-101
화합물 C 6.7 g (13.9 mmol), 9-브로모-10-페닐안트라센 3.9 g (11.6 mmol)을 사용하여 화합물 H-44와 동일한 방법으로 합성하여 화합물 H-101, 3.9 g (48.7 %)을 얻었다.6.7 g (13.9 mmol) of compound C, 3.9 g (11.6 mmol) of 9-bromo-10-phenylanthracene was synthesized in the same manner as in Compound H-44 , to obtain Compound H-101 , 3.9 g (48.7%).
물성데이터: 녹는점 358℃, UV 257nm (메틸렌 클로라이드(MC) 내에서), PL 412nm (MC 내에서), 분자량 687.29Physical property data: Melting point 358 ° C, UV 257 nm (in methylene chloride (MC)), PL 412 nm (in MC), molecular weight 687.29
[소자 [device 제조예Manufacturing example 1] 본 발명에 따른 유기 1] The organic 전계Field 발광 화합물을 이용한 Using a luminescent compound OLEDOLED 소자 제작 Device fabrication
본 발명의 발광 재료를 이용한 구조의 OLED 소자를 제작하였다. 우선, OLED용 글래스(삼성-코닝사 제조)로부터 얻어진 투명전극 ITO 박막(15Ω/□)을, 트리클로로에틸렌, 아세톤, 에탄올, 증류수를 순차적으로 사용하여 초음파 세척을 실시한후, 이소프로판올에 넣어 보관한 후 사용하였다. 다음으로 진공 증착 장비의 기판홀더에 ITO기판을 장착한 후, 진공 증착장비 내의 셀에 4,4',4"-트리스(N,N-(2-나프틸)-페닐아미노)트리페닐아민을 넣고 챔버 내의 진공도가 10-6 torr에 도달할 때까지 배기시킨 후, 셀에 전류를 인가하여 증발시켜 ITO 기판 위에 60 nm두께의 정공주입층을 증착하였다. 이어서, 진공 증착 장비 내의 다른 셀에 N,N'-비스(α나프틸)-N,N'-디페닐-4,4'-디아민을 넣고, 셀에 전류를 인가하여 증발시켜 정공주입층 위에 20 nm 두께의 정공전달층을 증착하였다. 정공주입층, 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 한쪽 셀에 호스트로서 본 발명의 화합물 H-44을 넣고, 또 다른 셀에는 도판트로서 본 발명의 화합물 D-55을 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 도판트와 호스트 전체에 대하여 도판트를 3 중량%의 양으로 도핑함으로써 상기 정공전달층 위에 30 nm 두께의 발광층을 증착하였다. 이어서 상기 발광층 위에 전자 전달층으로써 한쪽 셀에 트리스(8-히드록시퀴놀린)-알루미늄(III)을 넣고 30 nm의 전자전달층을 증착하였다. 이어서 전자주입층으로 리튬 퀴놀레이트를 2 nm 두께로 증착한 후, 다른 진공 증착장비를 이용하여 Al 음극을 150 nm의 두께로 증착하여 OLED 소자를 제작하였다. 재료 별로 각 화합물은 10-6 torr 하에서 진공 승화 정제하여 사용하였다.An OLED device having a structure using the light emitting material of the present invention was fabricated. First, the transparent electrode ITO thin film (15Ω / □) obtained from OLED glass (manufactured by Samsung Corning Corporation) was subjected to ultrasonic cleaning using trichloroethylene, acetone, ethanol and distilled water sequentially, and then stored in isopropanol. Used. Next, the ITO substrate was mounted on the substrate holder of the vacuum deposition apparatus, and then 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine was added to the cell in the vacuum deposition apparatus. And evacuated until the vacuum in the chamber reached 10 −6 torr, followed by evaporation by applying current to the cell to deposit a 60 nm thick hole injection layer on the ITO substrate. , N'-bis (αnaphthyl) -N, N'-diphenyl-4,4'-diamine was added thereto, followed by evaporation by applying a current to the cell to deposit a 20 nm thick hole transport layer on the hole injection layer. After the hole injection layer and the hole transport layer were formed, the light emitting layer was deposited thereon as follows: Compound H-44 of the present invention was placed in one cell in a vacuum deposition apparatus as a host, and another cell was viewed as a dopant. After each compound D-55 of the invention was added, the two materials were evaporated at different rates to allow the dopant and the whole host to A 30 nm thick light emitting layer was deposited on the hole transport layer by doping the dopant in an amount of 3% by weight, followed by tris (8-hydroxyquinoline) -aluminum (III) in one cell as an electron transporting layer on the light emitting layer. And deposited an electron transport layer of 30 nm, followed by depositing lithium quinolate with a thickness of 2 nm as an electron injection layer, and then depositing an Al cathode with a thickness of 150 nm using another vacuum deposition apparatus to fabricate an OLED device. Each compound was used by vacuum sublimation purification under 10 -6 torr for each material.
그 결과, 23.6 mA/cm2의 전류가 흘렀으며, 590 cd/m2의 청색발광이 확인되었다.
As a result, a current of 23.6 mA / cm 2 flowed, and blue light emission of 590 cd / m 2 was confirmed.
[소자 [device 제조예Manufacturing example 2] 본 발명에 따른 유기 2] The organic 전계Field 발광 화합물을 이용한 Using a luminescent compound OLEDOLED 소자 제작 Device fabrication
발광재료로서 호스트에는 화합물 H-86, 도판트에는 화합물 D-99을 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Compound H-86 was used for the host and Compound D-99 for the dopant.
그 결과, 15.7 mA/cm2의 전류가 흘렀으며, 1080 cd/m2의 청색발광이 확인되었다.
As a result, a current of 15.7 mA / cm 2 flowed, and blue light emission of 1080 cd / m 2 was confirmed.
[소자 [device 제조예Manufacturing example 3] 본 발명에 따른 유기 3] The organic 전계Field 발광 화합물을 이용한 Using a luminescent compound OLEDOLED 소자 제작 Device fabrication
발광재료로서 호스트에는 화합물 H-101, 도판트에는 화합물 D-9을 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Compound H-101 was used for the host and Compound D-9 was used for the dopant.
그 결과, 22.5 mA/cm2의 전류가 흘렀으며, 630 cd/m2의 청색발광이 확인되었다.
As a result, a current of 22.5 mA / cm 2 flowed, and blue light emission of 630 cd / m 2 was confirmed.
본 발명의 물질들이 발광층의 형광호스트로서 청색 발광에 효과적임을 확인하였다.It was confirmed that the materials of the present invention are effective in emitting blue light as a fluorescent host of the light emitting layer.
Claims (7)
[화학식 1]
상기 화학식 1에서,
L1은 단일결합, 치환 또는 비치환 (C6-C30)아릴렌기, 또는 치환 또는 비치환 (5-30원) 헤테로아릴렌기이고;
Ar1은 치환 또는 비치환 (C6-C30)아릴기, 또는 치환 또는 비치환 (5-30원) 헤테로아릴기이며;
Ar2 및 Ar3은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 치환 또는 비치환 (C1-C30)알킬기, 치환 또는 비치환 (C6-C30)아릴기, 치환 또는 비치환 (5-30원) 헤테로아릴기 또는 -NR1R2이고;
R1 및 R2은 각각 독립적으로 수소, 치환 또는 비치환 (C6-C30)아릴기, 또는 치환 또는 비치환 (5-30원) 헤테로아릴기이거나; 서로 결합하여 (3-30원) 단일환 또는 다환의 지환족 또는 방향족 고리를 형성할 수 있고, 상기 형성된 지환족 또는 방향족 환의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있으며;
A고리 및 C고리는 각각 독립적으로 하기 식 1a로 표시되는 방향족환을 나타내고;
B고리는 하기 식 1b로 표시되는 5원환을 나타내며;
[식 1a]
[식 1b]
X 및 Y는 각각 독립적으로 -O-, -S-, -N(R21)- 또는 -C(R22)(R23)-이고, X가 -C(R22)(R23)-인 경우 Y는 -O-, -S- 또는 -N(R21)-이며, X가 -O- 또는 -S-인 경우 Y는 -N(R21)- 또는 -C(R22)(R23)-이고, X가 -N(R21)-인 경우 Y는 -O-, -S- 또는 -C(R22)(R23)-이며;
R은 수소, 중수소, 할로겐, 치환 또는 비치환 (C1-C30)알킬기, 치환 또는 비치환 (C6-C30)아릴기, 또는 치환 또는 비치환 (5-30원) 헤테로아릴기이고;
R21 내지 R23은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환 (C1-C30)알킬기, 치환 또는 비치환 (C6-C30)아릴기, 또는 치환 또는 비치환 (5-30원) 헤테로아릴기이거나; 인접 치환체와 연결되어 (3-30원) 단일환 또는 다환의 지환족 또는 방향족 고리를 형성할 수 있고, 상기 형성된 지환족 또는 방향족 환의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있으며;
a는 1 또는 2이고, a가 2인 경우 각각의 R은 동일하거나 상이할 수 있다.An organic electroluminescent compound represented by the following formula (1).
[Chemical Formula 1]
In Formula 1,
L 1 is a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (5- to 30-membered) heteroarylene group;
Ar 1 is a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (5- to 30-membered) heteroaryl group;
Ar 2 and Ar 3 are each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C6-C30) aryl group, substituted or unsubstituted (5- to 30-membered) ) Heteroaryl group or -NR 1 R 2 ;
R 1 and R 2 are each independently hydrogen, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5- to 30-membered) heteroaryl group; May be combined with each other to form a (3- to 30-membered) monocyclic or polycyclic alicyclic or aromatic ring, and the carbon atoms of the formed alicyclic or aromatic rings may be replaced with one or more heteroatoms selected from nitrogen, oxygen and sulfur And;
A ring and C ring each independently represent an aromatic ring represented by the following formula 1a;
Ring B represents a 5-membered ring represented by the following Formula 1b;
[Formula 1a]
[Equation 1b]
X and Y are each independently -O-, -S-, -N (R 21 )-or -C (R 22 ) (R 23 )-, and X is -C (R 22 ) (R 23 )- Y is -O-, -S- or -N (R 21 )-and X is -O- or -S- and Y is -N (R 21 )-or -C (R 22 ) (R 23 ). ) And when X is -N (R 21 )-then Y is -O-, -S- or -C (R 22 ) (R 23 )-;
R is hydrogen, deuterium, halogen, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5- to 30-membered) heteroaryl group;
R 21 to R 23 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C6-C30) aryl group, or substituted or unsubstituted (5- to 30-membered) hetero group Aryl group; Linked to adjacent substituents (3-30 members) to form a monocyclic or polycyclic alicyclic or aromatic ring, wherein the carbon atoms of the formed alicyclic or aromatic rings are replaced with one or more heteroatoms selected from nitrogen, oxygen and sulfur Can be;
a is 1 or 2, and when a is 2, each R may be the same or different.
상기 X, Y, R, 및 a는 제1항에서의 정의와 동일하다.The compound according to claim 1, wherein in Formula 1,
X, Y, R, and a are the same as defined in claim 1.
상기 Ar1은 치환 또는 비치환 (C6-C21)아릴기, 또는 치환 또는 비치환 (5-21원) 헤테로아릴기이며;
상기 Ar2 및 Ar3은 각각 독립적으로 수소, 치환 또는 비치환 (C6-C21)아릴기, 치환 또는 비치환 (5-21원) 헤테로아릴기 또는 -NR1R2이고;
상기 R1 및 R2은 각각 독립적으로 수소 또는 치환 또는 비치환 (C6-C21)아릴기이며;
상기 X 및 Y는 각각 독립적으로 -O-, -S-, -N(R21)- 또는 -C(R22)(R23)-이고, X가 -C(R22)(R23)-인 경우 Y는 -O-, -S- 또는 -N(R21)-이며, X가 -O- 또는 -S-인 경우 Y는 -N(R21)- 또는 -C(R22)(R23)-이고, X가 -N(R21)-인 경우 Y는 -O-, -S- 또는 -C(R22)(R23)-이고;
상기 R은 수소이며;
상기 R21 내지 R23은 각각 독립적으로 치환 또는 비치환 (C1-C6)알킬기 또는 치환 또는 비치환 (C6-C21)아릴기인 것을 특징으로 하는 유기 전계 발광 화합물.The compound of claim 1, wherein L 1 is a single bond, a substituted or unsubstituted (C6-C21) arylene group, or a substituted or unsubstituted (5-21 membered) heteroarylene group;
Ar 1 is a substituted or unsubstituted (C6-C21) aryl group, or a substituted or unsubstituted (5-21 membered) heteroaryl group;
Ar 2 and Ar 3 are each independently hydrogen, a substituted or unsubstituted (C6-C21) aryl group, a substituted or unsubstituted (5-21 membered) heteroaryl group, or -NR 1 R 2 ;
R 1 and R 2 are each independently hydrogen or a substituted or unsubstituted (C6-C21) aryl group;
X and Y are each independently -O-, -S-, -N (R 21 )-or -C (R 22 ) (R 23 )-, and X is -C (R 22 ) (R 23 )- Y is -O-, -S- or -N (R 21 )-when X is -O- or -S- and Y is -N (R 21 )-or -C (R 22 ) (R 23 )-and when X is -N (R 21 )-, then Y is -O-, -S- or -C (R 22 ) (R 23 )-;
R is hydrogen;
R 21 to R 23 are each independently a substituted or unsubstituted (C1-C6) alkyl group or a substituted or unsubstituted (C6-C21) aryl group.
상기 Ar1은 중수소, 할로겐, (C1-C6)알킬, (C1-C6)알콕시, (C6-C21)아릴, (C3-C21)시클로알킬, 트리(C6-C12)아릴실릴, 시아노, 디(C6-C12)아릴아미노, 또는 히드록시로 치환 또는 비치환된 (C6-C21)아릴기; 또는 (C6-C21)아릴로 치환 또는 비치환 (5-21원) 헤테로아릴기이며;
상기 Ar2 및 Ar3은 각각 독립적으로 수소, 비치환 (C6-C21)아릴기, 비치환 (5-21원) 헤테로아릴기 또는 -NR1R2이고;
상기 R1 및 R2은 각각 독립적으로 수소 또는 (C1-C6)알킬로 치환 또는 비치환된 (C6-C21)아릴기이며;
상기 X 및 Y는 각각 독립적으로 -O-, -S-, -N(R21)- 또는 -C(R22)(R23)-이고, X가 -C(R22)(R23)-인 경우 Y는 -O-, -S- 또는 -N(R21)-이며, X가 -O- 또는 -S-인 경우 Y는 -N(R21)- 또는 -C(R22)(R23)-이고, X가 -N(R21)-인 경우 Y는 -O-, -S- 또는 -C(R22)(R23)-이고;
상기 R은 수소이며;
상기 R21 내지 R23은 각각 독립적으로 비치환 (C1-C6)알킬기 또는 비치환 (C6-C21)아릴기인 것을 특징으로 하는 유기 전계 발광 화합물.The compound of claim 1, wherein L 1 is a single bond, a (C6-C21) arylene group unsubstituted or substituted with a (C1-C6) alkyl, or an unsubstituted (5-21 membered) heteroarylene group;
Ar 1 is deuterium, halogen, (C1-C6) alkyl, (C1-C6) alkoxy, (C6-C21) aryl, (C3-C21) cycloalkyl, tri (C6-C12) arylsilyl, cyano, di (C6-C12) arylamino or a (C6-C21) aryl group unsubstituted or substituted with hydroxy; Or a (5- to 21-membered) heteroaryl group substituted or unsubstituted with (C6-C21) aryl;
Ar 2 and Ar 3 are each independently hydrogen, an unsubstituted (C6-C21) aryl group, an unsubstituted (5-21 membered) heteroaryl group, or -NR 1 R 2 ;
R 1 and R 2 are each independently a (C6-C21) aryl group unsubstituted or substituted with hydrogen or (C1-C6) alkyl;
X and Y are each independently -O-, -S-, -N (R 21 )-or -C (R 22 ) (R 23 )-, and X is -C (R 22 ) (R 23 )- Y is -O-, -S- or -N (R 21 )-when X is -O- or -S- and Y is -N (R 21 )-or -C (R 22 ) (R 23 )-and when X is -N (R 21 )-, then Y is -O-, -S- or -C (R 22 ) (R 23 )-;
R is hydrogen;
R 21 to R 23 are each independently an unsubstituted (C1-C6) alkyl group or an unsubstituted (C6-C21) aryl group.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020120114912A KR20140049186A (en) | 2012-10-16 | 2012-10-16 | Organic electroluminescence compounds and organic electroluminescence device comprising the same |
| PCT/KR2013/009197 WO2014061963A1 (en) | 2012-10-16 | 2013-10-15 | Organic electroluminescence compounds and organic electroluminescence device comprising the same |
| TW102137277A TW201425529A (en) | 2012-10-16 | 2013-10-16 | Organic electroluminescence compounds and organic electroluminescence device comprising the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020120114912A KR20140049186A (en) | 2012-10-16 | 2012-10-16 | Organic electroluminescence compounds and organic electroluminescence device comprising the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20140049186A true KR20140049186A (en) | 2014-04-25 |
Family
ID=50488467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020120114912A KR20140049186A (en) | 2012-10-16 | 2012-10-16 | Organic electroluminescence compounds and organic electroluminescence device comprising the same |
Country Status (3)
| Country | Link |
|---|---|
| KR (1) | KR20140049186A (en) |
| TW (1) | TW201425529A (en) |
| WO (1) | WO2014061963A1 (en) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140145456A (en) * | 2013-06-13 | 2014-12-23 | 제일모직주식회사 | Organic compound and organic optoelectric device and display device |
| KR20150128583A (en) * | 2014-05-09 | 2015-11-18 | 에스에프씨 주식회사 | Novel aromatic compounds for organic light-emitting diode and organic light-emitting diode including the same |
| WO2017034303A1 (en) * | 2015-08-27 | 2017-03-02 | 주식회사 엘지화학 | Heterocyclic compound and organic light emitting element comprising same |
| WO2017043908A1 (en) * | 2015-09-10 | 2017-03-16 | 희성소재(주) | Heterocyclic compound and organic light emitting diode using same |
| WO2017146474A1 (en) * | 2016-02-23 | 2017-08-31 | 주식회사 엘지화학 | Heterocyclic compound and organic light emitting diode containing same |
| WO2017146483A1 (en) * | 2016-02-23 | 2017-08-31 | 주식회사 엘지화학 | Heterocyclic compound and organic light emitting diode containing same |
| KR20190042439A (en) * | 2017-10-16 | 2019-04-24 | 주식회사 엘지화학 | Anthracene derivative and organic light emitting device comprising the same |
| US10312449B2 (en) | 2015-05-27 | 2019-06-04 | Samsung Display Co., Ltd. | Organic light-emitting device |
| US10367147B2 (en) | 2015-05-27 | 2019-07-30 | Samsung Display Co., Ltd. | Organic light-emitting device |
| US10553800B2 (en) | 2016-01-05 | 2020-02-04 | Samsung Display Co., Ltd. | Condensed cyclic compound and an organic light-emitting device including the same |
| KR20210093753A (en) * | 2020-01-20 | 2021-07-28 | 주식회사 엘지화학 | Polycyclic compound and organic light emitting device comprising same |
| KR20210093784A (en) * | 2020-01-20 | 2021-07-28 | 주식회사 엘지화학 | Compound and organic light emitting device comprising same |
| KR20210093736A (en) * | 2020-01-20 | 2021-07-28 | 주식회사 엘지화학 | Polycyclic compound and organic light emitting device comprising same |
| US11367838B2 (en) | 2017-06-16 | 2022-06-21 | Lg Chem, Ltd. | Anthracene derivative and organic light-emitting device comprising same |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104640848B (en) | 2013-03-15 | 2018-01-26 | 出光兴产株式会社 | Anthracene derivative and organic electroluminescent element using same |
| JP6232419B2 (en) * | 2013-05-02 | 2017-11-15 | 出光興産株式会社 | COMPOUND, MATERIAL FOR ORGANIC ELECTROLUMINESCENT ELEMENT, ORGANIC ELECTROLUMINESCENT ELEMENT AND ELECTRONIC DEVICE |
| US20160211454A1 (en) * | 2015-01-20 | 2016-07-21 | Samsung Display Co., Ltd. | Organic light-emitting device |
| US11322705B2 (en) * | 2015-04-17 | 2022-05-03 | Samsung Display Co., Ltd. | Organic light-emitting device |
| CN104892487B (en) * | 2015-05-29 | 2017-11-24 | 上海道亦化工科技有限公司 | A kind of anthracene class organic electroluminescent compounds and its organic electroluminescence device |
| KR102002023B1 (en) * | 2015-07-14 | 2019-07-22 | 에스에프씨주식회사 | An organic light emitting diode for high efficiency |
| KR102087319B1 (en) * | 2016-03-24 | 2020-05-27 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| KR20180057109A (en) * | 2016-11-21 | 2018-05-30 | 주식회사 두산 | Organic light-emitting compound and organic electroluminescent device using the same |
| CN110330472B (en) * | 2019-07-10 | 2022-02-01 | 吉林奥来德光电材料股份有限公司 | Blue light material and preparation method and application thereof |
| US20230276706A1 (en) * | 2020-07-29 | 2023-08-31 | Sfc Co., Ltd. | Novel heterocyclic compound and light-emitting diode including same |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2141214A3 (en) * | 2008-06-25 | 2010-02-24 | Gracel Display Inc. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| KR101178219B1 (en) * | 2008-11-21 | 2012-08-29 | 롬엔드하스전자재료코리아유한회사 | Electroluminescent device using the electroluminescent compounds |
| KR20100109050A (en) * | 2009-03-31 | 2010-10-08 | 다우어드밴스드디스플레이머티리얼 유한회사 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| KR101477613B1 (en) * | 2009-03-31 | 2014-12-30 | 롬엔드하스전자재료코리아유한회사 | Novel Compounds for Organic Electronic Material and Organic Electronic Device Using the Same |
| KR20100108914A (en) * | 2009-03-31 | 2010-10-08 | 다우어드밴스드디스플레이머티리얼 유한회사 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| KR101427605B1 (en) * | 2009-03-31 | 2014-08-07 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| KR101368164B1 (en) * | 2009-05-29 | 2014-02-27 | 이데미쓰 고산 가부시키가이샤 | Anthracene derivative and organic electroluminescent element using the same |
| KR20110104765A (en) * | 2010-03-17 | 2011-09-23 | 다우어드밴스드디스플레이머티리얼 유한회사 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| KR101832171B1 (en) * | 2010-10-25 | 2018-04-16 | 삼성디스플레이 주식회사 | A condensed-cyclic compound, an organic light emitting diode comprising the same and flat display device |
| KR20120120886A (en) * | 2011-04-25 | 2012-11-02 | (주)씨에스엘쏠라 | Organic light compound and organic light device using the same |
| KR101566578B1 (en) * | 2012-02-27 | 2015-11-05 | 주식회사 엘지화학 | Organic light emitting diode |
-
2012
- 2012-10-16 KR KR1020120114912A patent/KR20140049186A/en not_active Application Discontinuation
-
2013
- 2013-10-15 WO PCT/KR2013/009197 patent/WO2014061963A1/en active Application Filing
- 2013-10-16 TW TW102137277A patent/TW201425529A/en unknown
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9653690B2 (en) | 2013-06-13 | 2017-05-16 | Samsung Sdi Co., Ltd. | Organic compound, organic optoelectronic device and display device |
| KR20140145456A (en) * | 2013-06-13 | 2014-12-23 | 제일모직주식회사 | Organic compound and organic optoelectric device and display device |
| KR20150128583A (en) * | 2014-05-09 | 2015-11-18 | 에스에프씨 주식회사 | Novel aromatic compounds for organic light-emitting diode and organic light-emitting diode including the same |
| US10312449B2 (en) | 2015-05-27 | 2019-06-04 | Samsung Display Co., Ltd. | Organic light-emitting device |
| US10367147B2 (en) | 2015-05-27 | 2019-07-30 | Samsung Display Co., Ltd. | Organic light-emitting device |
| WO2017034303A1 (en) * | 2015-08-27 | 2017-03-02 | 주식회사 엘지화학 | Heterocyclic compound and organic light emitting element comprising same |
| US10230056B2 (en) | 2015-08-27 | 2019-03-12 | Lg Chem, Ltd. | Heterocyclic compound and organic light emitting element comprising same |
| WO2017043908A1 (en) * | 2015-09-10 | 2017-03-16 | 희성소재(주) | Heterocyclic compound and organic light emitting diode using same |
| US10553800B2 (en) | 2016-01-05 | 2020-02-04 | Samsung Display Co., Ltd. | Condensed cyclic compound and an organic light-emitting device including the same |
| US11276827B2 (en) | 2016-01-05 | 2022-03-15 | Samsung Display Co., Ltd. | Condensed cyclic compound and an organic light-emitting device including the same |
| US11107999B2 (en) | 2016-01-05 | 2021-08-31 | Samsung Display Co., Ltd. | Condensed cyclic compound and an organic light-emitting device including the same |
| US10580999B2 (en) | 2016-01-05 | 2020-03-03 | Samsung Display Co., Ltd. | Condensed cyclic compound and an organic light-emitting device including the same |
| WO2017146474A1 (en) * | 2016-02-23 | 2017-08-31 | 주식회사 엘지화학 | Heterocyclic compound and organic light emitting diode containing same |
| US10873035B2 (en) | 2016-02-23 | 2020-12-22 | Lg Chem, Ltd. | Heterocyclic compound and organic light emitting diode containing same |
| CN108026061A (en) * | 2016-02-23 | 2018-05-11 | 株式会社Lg化学 | Heterocyclic compound and the Organic Light Emitting Diode for including it |
| WO2017146483A1 (en) * | 2016-02-23 | 2017-08-31 | 주식회사 엘지화학 | Heterocyclic compound and organic light emitting diode containing same |
| US11968897B2 (en) | 2016-02-23 | 2024-04-23 | Lg Chem, Ltd. | Heterocyclic compound and organic light emitting diode containing same |
| US11367838B2 (en) | 2017-06-16 | 2022-06-21 | Lg Chem, Ltd. | Anthracene derivative and organic light-emitting device comprising same |
| KR20190042439A (en) * | 2017-10-16 | 2019-04-24 | 주식회사 엘지화학 | Anthracene derivative and organic light emitting device comprising the same |
| KR20210093753A (en) * | 2020-01-20 | 2021-07-28 | 주식회사 엘지화학 | Polycyclic compound and organic light emitting device comprising same |
| KR20210093784A (en) * | 2020-01-20 | 2021-07-28 | 주식회사 엘지화학 | Compound and organic light emitting device comprising same |
| KR20210093736A (en) * | 2020-01-20 | 2021-07-28 | 주식회사 엘지화학 | Polycyclic compound and organic light emitting device comprising same |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2014061963A1 (en) | 2014-04-24 |
| TW201425529A (en) | 2014-07-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR20140049186A (en) | Organic electroluminescence compounds and organic electroluminescence device comprising the same | |
| JP6644708B2 (en) | Electron transport material and organic electroluminescent device containing the same | |
| KR101939552B1 (en) | Organic Electroluminescent Compound and Organic Electroluminescent Device Comprising the Same | |
| KR102411746B1 (en) | An organic electroluminescent compound and an organic electroluminescent device comprising the same | |
| KR102128702B1 (en) | Novel organic electroluminescence compounds and organic electroluminescence device containing the same | |
| KR102160902B1 (en) | An Organic Electroluminescent Compound and an Organic Electroluminescent Device Comprising the Same | |
| JP6644005B2 (en) | Electron transport material and organic electroluminescent device containing the same | |
| KR20140049181A (en) | Organic electroluminescence compounds and organic electroluminescence device comprising the same | |
| KR20150012488A (en) | An organic electroluminescent compound and an organic electroluminescent device comprising the same | |
| KR20150093440A (en) | Organic Electroluminescent Device | |
| KR102397506B1 (en) | An Organic Electroluminescent Compound and an Organic Electroluminescent Device Comprising the Same | |
| KR20140141933A (en) | An organic electroluminescent compound and an organic electroluminescent device comprising the same | |
| KR20190035503A (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| KR20230029748A (en) | Organic Electroluminescent Compound and Organic Electroluminescent Device Comprising the Same | |
| KR101427620B1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| KR20130118059A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| KR20120020816A (en) | Novel compounds for organic electronic material and organic electroluminescent device using the same | |
| KR20140125576A (en) | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| KR20100109293A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| JP7206228B2 (en) | Organic electroluminescent compound and organic electroluminescent device containing the same | |
| KR20140073695A (en) | Organic Electroluminescent Compounds and Organic Electroluminescent Device Comprising the Same | |
| KR20160029399A (en) | A Hole Transport Material and an Organic Electroluminescent Device Comprising the Same | |
| KR20160010333A (en) | Electron transport material and organic electroluminescent device comprising the same | |
| KR20160014556A (en) | Electron Buffering Material and Organic Electroluminescent Device | |
| KR20170115940A (en) | Organic Electroluminescent Compound and Organic Electroluminescent Device Comprising the Same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |