WO2014088347A1 - Organic electroluminescent compounds and organic electroluminescent device comprising the same - Google Patents
Organic electroluminescent compounds and organic electroluminescent device comprising the same Download PDFInfo
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- WO2014088347A1 WO2014088347A1 PCT/KR2013/011228 KR2013011228W WO2014088347A1 WO 2014088347 A1 WO2014088347 A1 WO 2014088347A1 KR 2013011228 W KR2013011228 W KR 2013011228W WO 2014088347 A1 WO2014088347 A1 WO 2014088347A1
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- substituted
- unsubstituted
- organic electroluminescent
- alkyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 65
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [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 compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000003367 polycyclic group Chemical group 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000005104 aryl silyl group Chemical group 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 125000005566 carbazolylene group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 44
- 239000000463 material Substances 0.000 description 34
- -1 2-methylbut-2-enyl Chemical group 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000002019 doping agent Substances 0.000 description 16
- 239000012044 organic layer Substances 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 238000000151 deposition Methods 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 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
- 239000007983 Tris buffer Substances 0.000 description 2
- 150000001454 anthracenes Chemical class 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000002344 surface layer Substances 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
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-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
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-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
- LTBWKAYPXIIVPC-UHFFFAOYSA-N 3-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC(Br)=CC=C3NC2=C1 LTBWKAYPXIIVPC-UHFFFAOYSA-N 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
- ACWCQHMRMXMMRT-UHFFFAOYSA-N CC(C)(C)c(cc1c2c3ccc(-c4cc(-c5c6[o]c(C=CCC7)c7c6ccc5)ccc4)c2)ccc1[n]3-c(cc1)ccc1-c1c(cccc2)c2c(-c2ccccc2)c2c1cccc2 Chemical compound CC(C)(C)c(cc1c2c3ccc(-c4cc(-c5c6[o]c(C=CCC7)c7c6ccc5)ccc4)c2)ccc1[n]3-c(cc1)ccc1-c1c(cccc2)c2c(-c2ccccc2)c2c1cccc2 ACWCQHMRMXMMRT-UHFFFAOYSA-N 0.000 description 1
- RUACVPLOLZYDCS-UHFFFAOYSA-N Cc(cc1c2c3ccc(-c4cc(-c5c6[o]c(cccc7)c7c6ccc5)ccc4)c2)ccc1[n]3-c(cc1)ccc1-c1c(cccc2)c2c(-c2ccccc2)c2c1cccc2 Chemical compound Cc(cc1c2c3ccc(-c4cc(-c5c6[o]c(cccc7)c7c6ccc5)ccc4)c2)ccc1[n]3-c(cc1)ccc1-c1c(cccc2)c2c(-c2ccccc2)c2c1cccc2 RUACVPLOLZYDCS-UHFFFAOYSA-N 0.000 description 1
- KOPBYBDAPCDYFK-UHFFFAOYSA-N Cs2O Inorganic materials [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 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
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 1
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 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
- 125000000217 alkyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 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
- 150000001412 amines Chemical class 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
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=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
- 230000015572 biosynthetic process Effects 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
- WSTBTNHGQJQRMH-UHFFFAOYSA-N c(cc1)ccc1-c1c(cccc2)c2c(-c(cc2)ccc2-[n](c(c(c2c3)c4)ccc4-c4cc(-c5c6[o]c(cccc7)c7c6ccc5)ccc4)c2ccc3-c2cc(cccc3)c3cc2)c2c1cccc2 Chemical compound c(cc1)ccc1-c1c(cccc2)c2c(-c(cc2)ccc2-[n](c(c(c2c3)c4)ccc4-c4cc(-c5c6[o]c(cccc7)c7c6ccc5)ccc4)c2ccc3-c2cc(cccc3)c3cc2)c2c1cccc2 WSTBTNHGQJQRMH-UHFFFAOYSA-N 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000013522 chelant Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001893 coumarin derivatives Chemical class 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
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- AKUNKIJLSDQFLS-UHFFFAOYSA-M dicesium;hydroxide Chemical compound [OH-].[Cs+].[Cs+] AKUNKIJLSDQFLS-UHFFFAOYSA-M 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000002451 electron ionisation mass spectrometry 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
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000003838 furazanyl group Chemical group 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
- 125000004435 hydrogen atom Chemical group [H]* 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
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 239000007788 liquid Substances 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 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
- 229910001635 magnesium fluoride Inorganic materials 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
- 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
- 230000000737 periodic effect Effects 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
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 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
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 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
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010703 silicon Substances 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
- 125000005504 styryl group Chemical group 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
- 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
- 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
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000007740 vapor deposition 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
- 238000005406 washing Methods 0.000 description 1
Classifications
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C07B59/001—Acyclic or carbocyclic compounds
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- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
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- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
- C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
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- C07D209/56—Ring systems containing three or more rings
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
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- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- 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
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- C07D333/76—Dibenzothiophenes
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- 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
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Definitions
- the present invention relates to organic electroluminescent compounds and an organic electroluminescent device comprising the same.
- an electroluminescent (EL) device is a self-light-emitting device with the advantage of providing a wider viewing angle, a greater contrast ratio, and a faster response time compared with a liquid crystalline display (LCD).
- An organic EL device was first developed by Eastman Kodak, by using small aromatic diamine molecules and aluminum complexes as material for forming a light-emitting layer [see Appl. Phys. Lett. 51, 913, 1987].
- the most important factor for determining luminescent efficiency of an organic EL device is a light-emitting material.
- the light-emitting material is classified into a host material and a dopant material in the functional aspect.
- the light-emitting layer, wherein a dopant is doped onto a host was known.
- an urgent task is the development of an organic EL device having high efficacy and a long operating lifespan.
- the development of highly excellent light-emitting material over conventional light-emitting materials is urgent considering EL properties required in medium- and large-sized OLED panels.
- the host material as a solvent in a solid state and an energy messenger is preferably required to have the following features: high purity, suitable molecular weight possible for vacuum deposition, high glass transition temperature and thermal breakdown temperature for securing thermal stability, high electrochemical stability for long lifespan, easy formation of an amorphous thin film, good adhesion with the materials of an adjacent layer(s) and no movement between layers.
- blue fluorescent host materials a blue light-emitting material system by using 4,4’-bis(2,2’-diphenylvinyl)-1,1’-biphenyl (DPVBi)(Idemitsu Kosan), and blue light-emitting material systems of dinaphthylanthracene and tetra(t-butyl)perylene (Eastman Kodak) were known.
- DPVBi 4,4’-bis(2,2’-diphenylvinyl)-1,1’-biphenyl
- Eastman Kodak blue light-emitting material systems of dinaphthylanthracene and tetra(t-butyl)perylene
- anthracene derivatives having a specific structure are suitable to prepare an organic electroluminescent device having high efficiency.
- the objective of the present invention is to provide an organic electroluminescent compound which can be used as a blue fluorescent host material in preparing an organic electroluminescent device having high current efficiency and high luminescent efficiency.
- L 1 represents a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted 3- to 30-membered heteroarylene group, with the proviso that carbazolylene and heteroarylene partially containing carbazole in the structure are excluded;
- Ar 1 to Ar 8 each independently represent hydrogen, deuterium, a halogen, a cyano group, 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; or each of Ar 5 to Ar 8 is linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
- X represents -NR 1 -, -S-, -O-, -CR 2 R 3 - or -SiR 4 R 5 -;
- R 1 to R 5 each independently represent hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C2-C30)alkynyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C3-C30)cycloalkenyl group, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 3- to 30-
- a represents an integer of 1 to 5; b to e and h each independently represent an integer of 1 to 4; f and g each independently represent an integer of 1 to 3; where a to h is an integer of 2 or more, each of Ar 1 to Ar 8 can be the same or different; and
- An organic electroluminescent device having high current efficiency and high luminescent efficiency can be prepared by using the organic electroluminescent compounds according to the present invention.
- the present invention relates to an organic electroluminescent compound represented by formula 1 above, an organic electroluminescent material comprising the organic electroluminescent compound, and an organic electroluminescent device comprising the material.
- the organic electroluminescent compound represented by formula 1 is described in detail below.
- alkyl includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
- alkenyl includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2- butenyl, 3- butenyl, 2-methylbut-2-enyl, etc.
- alkynyl includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2- butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
- cycloalkyl cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
- aryl(ene) is a monocyclic or fused ring derived from an aromatic hydrocarbon and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.
- substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e., a substituent.
- L 1 represents a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted 3- to 30-membered heteroarylene group, with the proviso that carbazolylene and heteroarylene partially containing carbazole in the structure are excluded.
- L 1 represents a substituted or unsubstituted (C6-C21)arylene group, and more preferably a (C6-C12)arylene group.
- Ar 1 to Ar 8 each independently represent hydrogen, deuterium, a halogen, a cyano group, 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; or each of Ar 5 to Ar 8 is linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur.
- Ar 1 to Ar 8 each independently represent hydrogen, a substituted or unsubstituted (C1-C6)alkyl group, or a substituted or unsubstituted (C6-C21)aryl group; and more preferably hydrogen, a (C1-C4)alkyl group, or a (C6-C13)aryl group which is unsubstituted or substituted with a (C1-C4)alkyl group.
- X represents -NR 1 -, -S-, -O-, -CR 2 R 3 - or -SiR 4 R 5 -.
- R 1 to R 5 each independently represent hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C2-C30)alkynyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C3-C30)cycloalkenyl group, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted
- R 1 to R 5 each independently represent a substituted or unsubstituted (C1-C6)alkyl group, or a substituted or unsubstituted (C6-C21)aryl group; and more preferably a (C1-C4)alkyl group or a (C6-C12)aryl group.
- L 1 represents a substituted or unsubstituted (C6-C21)arylene group
- Ar 1 to Ar 8 each independently represent hydrogen, a substituted or unsubstituted (C1-C6)alkyl group, or a substituted or unsubstituted (C6-C21)aryl group
- X represents -NR 1 -, -S-, -O-, -CR 2 R 3 - or -SiR 4 R 5 -
- R 1 to R 5 each independently represent a substituted or unsubstituted (C1-C6)alkyl group, or a substituted or unsubstituted (C6-C21)aryl group.
- L 1 represents a (C6-C12)arylene group
- Ar 1 to Ar 8 each independently represent hydrogen, a (C1-C4)alkyl group, or a (C6-C13)aryl group which is unsubstituted or substituted with a (C1-C4)alkyl group
- X represents -NR 1 -, -S-, -O-, -CR 2 R 3 - or -SiR 4 R 5 -
- R 1 to R 5 each independently represent a (C1-C4)alkyl group or a (C6-C12)aryl group.
- organic electroluminescent compounds of formula 1 above include the following compounds, but are not limited thereto:
- organic electroluminescent compounds according to the present invention can be prepared by known methods to one skilled in the art, and can be prepared, for example, according to the following reaction scheme 1.
- L 1 , Ar 1 to Ar 8 , X, a, b, c, d, e, f, g and h are as defined in formula 1 above.
- the present invention further provides an organic electroluminescent material comprising the organic electroluminescent compound of formula 1, and an organic electroluminescent device comprising the material.
- the material can be comprised of the organic electroluminescent compound of the present invention alone, or can further include conventional materials generally included in organic electroluminescent materials.
- the organic electroluminescent device may comprise a first electrode, a second electrode, and at least one organic layer between the first and second electrodes, wherein the organic layer comprises at least one organic electroluminescent compound of formula 1 above.
- the organic layer may comprise a light-emitting layer, and may further comprise at least one layer 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.
- the organic layer may comprise a light-emitting layer, wherein the light-emitting layer can include the organic electroluminescent compound of formula 1 above as a host material.
- the light-emitting layer may comprise fluorescent dopant materials together with the host material according to the present invention.
- the fluorescent dopant is the luminescent compounds from a singlet exciton.
- the fluorescent dopant is preferably selected from amine-based compounds, aromatic compounds, chelate complexes such as tris(8-quinolinolate)aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives, oxadiazole derivatives, etc.; and more preferably styrylamine compounds, styryldiamine compounds, arylamine compounds or aryldiamine compounds; and most preferably condensed polycyclic amine derivatives.
- the fluorescent dopant can be used alone or in combination with each other.
- the condensed polycyclic amine derivatives as the fluorescent dopant included in the organic electroluminescent device of the present invention may be the compound represented by the following formula 2:
- Ar 21 represents a substituted or unsubstituted (C6-C50)aryl group, or a styryl group
- L represents a single bond, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group
- Ar 22 and Ar 23 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group, or are linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur; and n is 1 or 2, where n is 2, each
- the preferable aryl group as Ar 21 includes a substituted or unsubstituted phenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrisenyl group, a substituted or unsubstituted benzofluorenyl group, etc.
- DPMS diphenylmethylsilyl
- TPS triphenylsilyl
- the organic electroluminescent device of the present invention comprises the organic electroluminescent compounds of formula 1 and may further include at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
- the organic layer may further comprise, in addition to the organic electroluminescent compounds of formula 1 above, at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides, and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising the metal.
- the organic layer may further comprise a light-emitting layer or a charge generating layer.
- the organic electroluminescent device of the present invention may emit white light by further comprising at least one organic light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound, or a green electroluminescent compound, besides the organic electroluminescent compound of the present invention.
- a surface layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on an inner surface(s) of one or both electrode(s).
- a chalcogenide (includes oxides) layer of silicon or aluminum is placed on an anode surface of an electroluminescent medium layer, and a metal halide layer or metal oxide layer is placed on a cathode surface of an electroluminescent medium layer.
- the surface layer provides operating stability for the organic electroluminescent device.
- the chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.;
- the metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and the metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
- a mixed region of an electron transport compound and an reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes.
- the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium.
- the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
- the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
- a reductive dopant layer may be employed as a charge generating layer to prepare an organic electroluminescent device having two or more electroluminescent layers and emitting white light.
- dry film-forming methods such as vacuum deposition, sputtering, plasma, ion plating methods, etc.
- wet film-forming methods such as spin coating, dip coating, flow coating methods, etc.
- a thin film is formed by dissolving or dispersing the material constituting each layer in suitable solvents, such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
- suitable solvents such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
- the solvents are not specifically limited as long as the material constituting each layer is soluble or dispersible in the solvents, which do not cause any problems in forming a layer.
- An OLED device was produced using the organic electroluminescent compound according to the present invention.
- a transparent electrode indium tin oxide (ITO) thin film (15 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing by using trichloroethylene, acetone, ethanol and distilled water, sequentially, and then was stored in isopropanol. Then, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus.
- 4,4’,4”-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine was introduced into a cell of the vacuum vapor depositing apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
- N,N’-bis( ⁇ -naphthyl)-N,N’-diphenyl-4,4’-diamine was introduced into another cell of the vacuum vapor depositing apparatus, and was evaporated by applying electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
- compound C-3 according to the present invention as a host was introduced into one cell of the vacuum vapor depositing apparatus, and compound D-9 as a dopant was introduced into another cell.
- the two materials were evaporated at different rates and the dopant was deposited in a doping amount of 3 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. Then, tris(8-hydroxyquinoline)-aluminum(III) was introduced into one cell to form an electron transport layer having a thickness of 30 nm on the light-emitting layer. Then, after depositing lithium quinolate as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 150 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED device was produced. All the materials used for producing the OLED device were purified by vacuum sublimation at 10 -6 torr prior to use.
- the produced OLED device showed blue emission having a luminance of 890 cd/m 2 and a current density of 28.7 mA/cm 2 .
- Comparative Example 1 Production of an OLED device by using conventional organic electroluminescent compound
- OLED device was produced in the same manner as in Device Example 1, except for using the following compound as a host and compound D-9 as a dopant in the light-emitting material.
- the produced OLED device showed blue emission having a luminance of 820 cd/m 2 and a current density of 31.5 mA/cm 2 .
- the organic electroluminescent device of the present invention provides high current efficiency and high luminescent efficiency by using the organic electroluminescent compounds of the present invention as a host material.
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Abstract
The present invention relates to organic electroluminescent compounds and an organic electroluminescent device comprising the same. An organic electroluminescent device having excellent current efficiency and luminescent efficiency can be prepared by using the organic electroluminescent compounds according to the present invention.
Description
The present invention relates to organic electroluminescent compounds and an organic electroluminescent device comprising the same.
Among display devices, an electroluminescent (EL) device is a self-light-emitting device with the advantage of providing a wider viewing angle, a greater contrast ratio, and a faster response time compared with a liquid crystalline display (LCD). An organic EL device was first developed by Eastman Kodak, by using small aromatic diamine molecules and aluminum complexes as material for forming a light-emitting layer [see Appl. Phys. Lett. 51, 913, 1987].
The most important factor for determining luminescent efficiency of an organic EL device is a light-emitting material. The light-emitting material is classified into a host material and a dopant material in the functional aspect. Generally, as a structure of the device having the most excellent EL properties, the light-emitting layer, wherein a dopant is doped onto a host, was known. Recently, an urgent task is the development of an organic EL device having high efficacy and a long operating lifespan. In particular, the development of highly excellent light-emitting material over conventional light-emitting materials is urgent considering EL properties required in medium- and large-sized OLED panels.
The host material as a solvent in a solid state and an energy messenger is preferably required to have the following features: high purity, suitable molecular weight possible for vacuum deposition, high glass transition temperature and thermal breakdown temperature for securing thermal stability, high electrochemical stability for long lifespan, easy formation of an amorphous thin film, good adhesion with the materials of an adjacent layer(s) and no movement between layers.
Until now, fluorescent host materials have been widely used as a host material. As blue fluorescent host materials, a blue light-emitting material system by using 4,4’-bis(2,2’-diphenylvinyl)-1,1’-biphenyl (DPVBi)(Idemitsu Kosan), and blue light-emitting material systems of dinaphthylanthracene and tetra(t-butyl)perylene (Eastman Kodak) were known. However, in order to develop blue fluorescent host materials for providing better properties in the device, further studies are still being conducted.
European Patent Application Laying-open No. 1972619 A discloses various anthracene derivatives as blue fluorescent host materials, but the derivatives do not have satisfactory luminescent efficiency and lifespan property.
The present inventors have worked to overcome said problems and consequently, found that anthracene derivatives having a specific structure are suitable to prepare an organic electroluminescent device having high efficiency.
The objective of the present invention is to provide an organic electroluminescent compound which can be used as a blue fluorescent host material in preparing an organic electroluminescent device having high current efficiency and high luminescent efficiency.
The present inventors found that the above objective can be achieved by a compound represented by the following formula 1:
wherein
L1 represents a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted 3- to 30-membered heteroarylene group, with the proviso that carbazolylene and heteroarylene partially containing carbazole in the structure are excluded;
Ar1 to Ar8 each independently represent hydrogen, deuterium, a halogen, a cyano group, 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; or each of Ar5 to Ar8 is linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
X represents -NR1-, -S-, -O-, -CR2R3- or -SiR4R5-;
R1 to R5 each independently represent hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C2-C30)alkynyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C3-C30)cycloalkenyl group, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
a represents an integer of 1 to 5; b to e and h each independently represent an integer of 1 to 4; f and g each independently represent an integer of 1 to 3; where a to h is an integer of 2 or more, each of Ar1 to Ar8 can be the same or different; and
the heteroaryl(ene) group and heterocycloalkyl group contain at least one hetero atom selected from B, N, O, S, P(=O), Si and P.
An organic electroluminescent device having high current efficiency and high luminescent efficiency can be prepared by using the organic electroluminescent compounds according to the present invention.
Hereinafter, the present invention will be described in detail. However, the following description is intended to explain the invention, and is not meant in any way to restrict the scope of the invention.
The present invention relates to an organic electroluminescent compound represented by formula 1 above, an organic electroluminescent material comprising the organic electroluminescent compound, and an organic electroluminescent device comprising the material.
The organic electroluminescent compound represented by formula 1 is described in detail below.
Herein, “alkyl” includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. “alkenyl” includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2- butenyl, 3- butenyl, 2-methylbut-2-enyl, etc. “alkynyl” includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2- butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc. “cycloalkyl” cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. “3- to 7-membered heterocycloalkyl” is a cycloalkyl having at least one heteroatom selected from the group consisting of B, N, O, S, P(=O), Si and P, preferably O, S and N, and 3 to 7 ring backbone atoms, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc. “aryl(ene)” is a monocyclic or fused ring derived from an aromatic hydrocarbon and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc. “3- to 30-membered heteroaryl(ene)” is an aryl group having at least one, preferably 1 to 4 heteroatom selected from the group consisting of B, N, O, S, P(=O), Si and P, and 3 to 30 ring backbone atoms; is a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and includes a monocyclic ring-type heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl including benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, etc. “Halogen” includes F, Cl, Br and I.
Herein, “substituted” in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e., a substituent. Substituents of the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group, the substituted alkoxy group, the substituted cycloalkyl group, the substituted cycloalkenyl group, the substituted heterocycloalkyl group, the substituted aryl(ene) group and the substituted heteroaryl(ene) group in L1, Ar1 to Ar8, and R1 to R5 of formula 1 each independently are at least one selected from the group consisting of deuterium; a halogen; a (C1-C30)alkyl group which is unsubstituted or substituted with a halogen; a (C1-C30)alkoxy group; a (C6-C30)aryl group; a 3- to 30-membered heteroaryl group which is unsubstituted or substituted with a (C6-C30)aryl group; a (C3-C30)cycloalkyl group; a 5- to 7-membered heterocycloalkyl group; a tri(C1-C30)alkylsilyl group; a tri(C6-C30)arylsilyl group; a di(C1-C30)alkyl(C6-C30)arylsilyl group; a (C1-C30)alkyldi(C6-C30)arylsilyl group; a (C2-C30)alkenyl group; a (C2-C30)alkynyl group; a cyano group; a di(C1-C30)alkylamino group; a di(C6-C30)arylamino group; a (C1-C30)alkyl(C6-C30)arylamino group; a di(C6-C30)arylboronyl group; a di(C1-C30)alkylboronyl group; a (C1-C30)alkyl(C6-C30)arylboronyl group; a (C6-C30)aryl(C1-C30)alkyl group; a (C1-C30)alkyl(C6-C30)aryl group; a carboxyl group; a nitro group; and a hydroxyl group; and preferably at least one selected from the group consisting of (C1-C6)alkyl group; a (C6-C21)aryl group; and a 3- to 21-membered heteroaryl group, and more preferably (C1-C4)alkyl group.
In formula 1 above, L1 represents a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted 3- to 30-membered heteroarylene group, with the proviso that carbazolylene and heteroarylene partially containing carbazole in the structure are excluded. Preferably, L1 represents a substituted or unsubstituted (C6-C21)arylene group, and more preferably a (C6-C12)arylene group.
In formula 1 above, Ar1 to Ar8 each independently represent hydrogen, deuterium, a halogen, a cyano group, 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; or each of Ar5 to Ar8 is linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur. Preferably, Ar1 to Ar8 each independently represent hydrogen, a substituted or unsubstituted (C1-C6)alkyl group, or a substituted or unsubstituted (C6-C21)aryl group; and more preferably hydrogen, a (C1-C4)alkyl group, or a (C6-C13)aryl group which is unsubstituted or substituted with a (C1-C4)alkyl group.
In formula 1 above, X represents -NR1-, -S-, -O-, -CR2R3- or -SiR4R5-.
In formula 1 above, R1 to R5 each independently represent hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C2-C30)alkynyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C3-C30)cycloalkenyl group, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur. Preferably, R1 to R5 each independently represent a substituted or unsubstituted (C1-C6)alkyl group, or a substituted or unsubstituted (C6-C21)aryl group; and more preferably a (C1-C4)alkyl group or a (C6-C12)aryl group.
According to one embodiment of the present invention, in formula 1 above, L1 represents a substituted or unsubstituted (C6-C21)arylene group; Ar1 to Ar8 each independently represent hydrogen, a substituted or unsubstituted (C1-C6)alkyl group, or a substituted or unsubstituted (C6-C21)aryl group; X represents -NR1-, -S-, -O-, -CR2R3- or -SiR4R5-; and R1 to R5 each independently represent a substituted or unsubstituted (C1-C6)alkyl group, or a substituted or unsubstituted (C6-C21)aryl group.
According to another embodiment of the present invention above, in formula 1, L1 represents a (C6-C12)arylene group; Ar1 to Ar8 each independently represent hydrogen, a (C1-C4)alkyl group, or a (C6-C13)aryl group which is unsubstituted or substituted with a (C1-C4)alkyl group; X represents -NR1-, -S-, -O-, -CR2R3- or -SiR4R5-; and R1 to R5 each independently represent a (C1-C4)alkyl group or a (C6-C12)aryl group.
The organic electroluminescent compounds of formula 1 above include the following compounds, but are not limited thereto:
The organic electroluminescent compounds according to the present invention can be prepared by known methods to one skilled in the art, and can be prepared, for example, according to the following reaction scheme 1.
[Reaction Scheme 1]
wherein L1, Ar1 to Ar8, X, a, b, c, d, e, f, g and h are as defined in formula 1 above.
The present invention further provides an organic electroluminescent material comprising the organic electroluminescent compound of formula 1, and an organic electroluminescent device comprising the material. The material can be comprised of the organic electroluminescent compound of the present invention alone, or can further include conventional materials generally included in organic electroluminescent materials.
The organic electroluminescent device according to the present invention may comprise a first electrode, a second electrode, and at least one organic layer between the first and second electrodes, wherein the organic layer comprises at least one organic electroluminescent compound of formula 1 above.
One of the first electrode and the second electrode can be an anode and the other can be a cathode. The organic layer may comprise a light-emitting layer, and may further comprise at least one layer 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.
The organic layer may comprise a light-emitting layer, wherein the light-emitting layer can include the organic electroluminescent compound of formula 1 above as a host material. The light-emitting layer may comprise fluorescent dopant materials together with the host material according to the present invention.
The fluorescent dopant is the luminescent compounds from a singlet exciton. In order to comply with the required luminescent color, the fluorescent dopant is preferably selected from amine-based compounds, aromatic compounds, chelate complexes such as tris(8-quinolinolate)aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives, oxadiazole derivatives, etc.; and more preferably styrylamine compounds, styryldiamine compounds, arylamine compounds or aryldiamine compounds; and most preferably condensed polycyclic amine derivatives. The fluorescent dopant can be used alone or in combination with each other.
The condensed polycyclic amine derivatives as the fluorescent dopant included in the organic electroluminescent device of the present invention may be the compound represented by the following formula 2:
wherein
Ar21 represents a substituted or unsubstituted (C6-C50)aryl group, or a styryl group; L represents a single bond, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group; Ar22 and Ar23 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group, or are linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur; and n is 1 or 2, where n is 2, each
The preferable aryl group as Ar21 includes a substituted or unsubstituted phenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrisenyl group, a substituted or unsubstituted benzofluorenyl group, etc.
The specific compounds of formula 2 above include the following compounds, but are not limited thereto:
wherein DPMS means diphenylmethylsilyl and TPS means triphenylsilyl.
The organic electroluminescent device of the present invention comprises the organic electroluminescent compounds of formula 1 and may further include at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
In the organic electroluminescent device of the present invention, the organic layer may further comprise, in addition to the organic electroluminescent compounds of formula 1 above, at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4th period, transition metals of the 5th period, lanthanides, and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising the metal. Furthermore, the organic layer may further comprise a light-emitting layer or a charge generating layer.
In addition, the organic electroluminescent device of the present invention may emit white light by further comprising at least one organic light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound, or a green electroluminescent compound, besides the organic electroluminescent compound of the present invention.
Preferably, in the organic electroluminescent device according to the present invention, at least one layer (hereinafter, "a surface layer”) selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on an inner surface(s) of one or both electrode(s). Specifically, it is preferred that a chalcogenide (includes oxides) layer of silicon or aluminum is placed on an anode surface of an electroluminescent medium layer, and a metal halide layer or metal oxide layer is placed on a cathode surface of an electroluminescent medium layer. The surface layer provides operating stability for the organic electroluminescent device. Preferably, the chalcogenide includes SiOX(1≤X≤2), AlOX(1≤X≤1.5), SiON, SiAlON, etc.; the metal halide includes LiF, MgF2, CaF2, a rare earth metal fluoride, etc.; and the metal oxide includes Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
Preferably, in the organic electroluminescent device according to the present invention, a mixed region of an electron transport compound and an reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium. Furthermore, the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. Furthermore, a reductive dopant layer may be employed as a charge generating layer to prepare an organic electroluminescent device having two or more electroluminescent layers and emitting white light.
In order to form each layer constituting the organic electroluminescent device according to the present invention, dry film-forming methods, such as vacuum deposition, sputtering, plasma, ion plating methods, etc., or wet film-forming methods, such as spin coating, dip coating, flow coating methods, etc., can be used.
When using a wet film-forming method, a thin film is formed by dissolving or dispersing the material constituting each layer in suitable solvents, such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvents are not specifically limited as long as the material constituting each layer is soluble or dispersible in the solvents, which do not cause any problems in forming a layer.
Hereinafter, the organic electroluminescent compound of the present invention, the preparation method of the compound, and the luminescent properties of the device comprising the compound will be explained in detail with reference to the following examples:
Example 1: Preparation of compound C-3
Preparation of compound 1-2
A mixture of compound 1-1 (10.0 g, 34.7 mmol), 3-bromocarbazole (7.1 g, 28.9 mmol), tetrakis(triphenylphosphine)palladium(O) (Pd(PPh3)4) (1.0 g, 0.88 mmol), 2M Na2CO3 (27.0 mL), toluene (100.0 mL) and ethanol (27.0 mL) was reflux stirred for 5 hours. After cooling the mixture to room temperature, distilled water was added to the mixture. The organic layer was extracted with ethyl acetate (EA) and was dried over MgSO4. The organic layer was distilled under the reduced pressure and was recrystallized with EA and methanol to obtain compound 1-2 (8.3 g, 20.2 mmol, 71 %).
Preparation of compound 1-3
Compound 1-2 (8.3 g, 20.2 mmol), 1-bromo-4-iodobenzene (11.4 g, 40.4 mmol), CuI (4.7 g, 9.4 mmol), ethylenediamine (3.3 mL, 48.9 mmol) and K3PO4 (32.0 g, 146.8 mmol) were dissolved in toluene (300.0 mL) and was refluxed for 24 hours at 120 ℃. After completing the reaction, the organic layer was extracted with EA and was dried by removing the remaining moisture with MgSO4. The organic layer was separated through column to obtain compound 1-3 (8.0 g, 14.1 mmol, 70 %).
Preparation of compound C-3
A mixture of compound 1-3 (8.0 g, 14.1 mmol), compound 1-4 (5.0 g, 17.0 mmol), Pd(PPh3)4 (1.0 g, 0.88 mmol), 2M Na2CO3 (27.0 mL), toluene (100.0 mL) and ethanol (27.0 mL) was reflux stirred for 5 hours. After cooling the mixture to room temperature, distilled water was added to the mixture. The organic layer was extracted with EA and was dried over MgSO4. The organic layer was distilled under the reduced pressure and was recrystallized with EA and methanol to obtain compound C-3 (4.0 g, 5.4 mmol, 38 %).
MS/EIMS Found 737.8, Calculated 737.27, UV 282 nm, PL 430 nm, mp 289 ℃
Device Example 1: Production of an OLED device by using the
organic electroluminescent compound according to the present invention
An OLED device was produced using the organic electroluminescent compound according to the present invention. A transparent electrode indium tin oxide (ITO) thin film (15 Ω/sq) on a glass substrate for an organic light-emitting diode (OLED) device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing by using trichloroethylene, acetone, ethanol and distilled water, sequentially, and then was stored in isopropanol. Then, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus. 4,4’,4”-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine was introduced into a cell of the vacuum vapor depositing apparatus, and then the pressure in the chamber of the apparatus was controlled to 10-6 torr. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate. Then, N,N’-bis(α-naphthyl)-N,N’-diphenyl-4,4’-diamine was introduced into another cell of the vacuum vapor depositing apparatus, and was evaporated by applying electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. Thereafter, compound C-3 according to the present invention as a host was introduced into one cell of the vacuum vapor depositing apparatus, and compound D-9 as a dopant was introduced into another cell. The two materials were evaporated at different rates and the dopant was deposited in a doping amount of 3 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. Then, tris(8-hydroxyquinoline)-aluminum(III) was introduced into one cell to form an electron transport layer having a thickness of 30 nm on the light-emitting layer. Then, after depositing lithium quinolate as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 150 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED device was produced. All the materials used for producing the OLED device were purified by vacuum sublimation at 10-6 torr prior to use.
The produced OLED device showed blue emission having a luminance of 890 cd/m2 and a current density of 28.7 mA/cm2.
Comparative Example 1: Production of an OLED device by using conventional organic electroluminescent compound
An OLED device was produced in the same manner as in Device Example 1, except for using the following compound as a host and compound D-9 as a dopant in the light-emitting material.
The produced OLED device showed blue emission having a luminance of 820 cd/m2 and a current density of 31.5 mA/cm2.
The organic electroluminescent device of the present invention provides high current efficiency and high luminescent efficiency by using the organic electroluminescent compounds of the present invention as a host material.
Claims (6)
- An organic electroluminescent compound represented by the following formula 1:
whereinL1 represents a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted 3- to 30-membered heteroarylene group, with the proviso that carbazolylene and heteroarylene partially containing carbazole in the structure are excluded;Ar1 to Ar8 each independently represent hydrogen, deuterium, a halogen, a cyano group, 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; or each of Ar5 to Ar8 is linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;X represents -NR1-, -S-, -O-, -CR2R3- or -SiR4R5-;R1 to R5 each independently represent hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C2-C30)alkynyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C3-C30)cycloalkenyl group, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30-membered alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;a represents an integer of 1 to 5; b to e and h each independently represent an integer of 1 to 4; f and g each independently represent an integer of 1 to 3; where a to h is an integer of 2 or more, each of Ar1 to Ar8 can be the same or different; andthe heteroaryl(ene) group and heterocycloalkyl group contain at least one hetero atom selected from B, N, O, S, P(=O), Si and P. - The organic electroluminescent compound according to claim 1, wherein the substituents of the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group, the substituted alkoxy group, the substituted cycloalkyl group, the substituted cycloalkenyl group, the substituted heterocycloalkyl group, the substituted aryl(ene) group and the substituted heteroaryl(ene) group in L1, Ar1 to Ar8, and R1 to R5 each independently are at least one selected from the group consisting of deuterium; a halogen; a (C1-C30)alkyl group which is unsubstituted or substituted with a halogen; a (C1-C30)alkoxy group; a (C6-C30)aryl group; a 3- to 30-membered heteroaryl group which is unsubstituted or substituted with a (C6-C30)aryl group; a (C3-C30)cycloalkyl group; a 5- to 7-membered heterocycloalkyl group; a tri(C1-C30)alkylsilyl group; a tri(C6-C30)arylsilyl group; a di(C1-C30)alkyl(C6-C30)arylsilyl group; a (C1-C30)alkyldi(C6-C30)arylsilyl group; a (C2-C30)alkenyl group; a (C2-C30)alkynyl group; a cyano group; a di(C1-C30)alkylamino group; a di(C6-C30)arylamino group; a (C1-C30)alkyl(C6-C30)arylamino group; a di(C6-C30)arylboronyl group; a di(C1-C30)alkylboronyl group; a (C1-C30)alkyl(C6-C30)arylboronyl group; a (C6-C30)aryl(C1-C30)alkyl group; a (C1-C30)alkyl(C6-C30)aryl group; a carboxyl group; a nitro group; and a hydroxyl group.
- The organic electroluminescent compound according to claim 1, wherein L1 represents a substituted or unsubstituted (C6-C21)arylene group; Ar1 to Ar8 each independently represent hydrogen, a substituted or unsubstituted (C1-C6)alkyl group, or a substituted or unsubstituted (C6-C21)aryl group; X represents -NR1-, -S-, -O-, -CR2R3- or -SiR4R5-; and R1 to R5 each independently represent a substituted or unsubstituted (C1-C6)alkyl group, or a substituted or unsubstituted (C6-C21)aryl group.
- The organic electroluminescent compound according to claim 1, wherein L1 represents a (C6-C12)arylene group; Ar1 to Ar8 each independently represent hydrogen, a (C1-C4)alkyl group, or a (C6-C13)aryl group which is unsubstituted or substituted with a (C1-C4)alkyl group; X represents -NR1-, -S-, -O-, -CR2R3- or -SiR4R5-; and R1 to R5 each independently represent a (C1-C4)alkyl group or a (C6-C12)aryl group.
- The organic electroluminescent compound according to claim 1, wherein the compound represented by formula 1 is selected from the group consisting of the following compounds:
- An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020120141101A KR20140073695A (en) | 2012-12-06 | 2012-12-06 | Organic Electroluminescent Compounds and Organic Electroluminescent Device Comprising the Same |
| KR10-2012-0141101 | 2012-12-06 |
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| Publication Number | Publication Date |
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| WO2014088347A1 true WO2014088347A1 (en) | 2014-06-12 |
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| Application Number | Title | Priority Date | Filing Date |
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| PCT/KR2013/011228 WO2014088347A1 (en) | 2012-12-06 | 2013-12-05 | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
Country Status (3)
| Country | Link |
|---|---|
| KR (1) | KR20140073695A (en) |
| TW (1) | TW201432024A (en) |
| WO (1) | WO2014088347A1 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105061439A (en) * | 2015-08-03 | 2015-11-18 | 上海道亦化工科技有限公司 | Organic electroluminescent compound and organic electroluminescent device thereof |
| CN105390624A (en) * | 2015-11-11 | 2016-03-09 | 上海道亦化工科技有限公司 | Nitrogen-containing dibenzoheterocycle compound and organic electroluminescent device thereof |
| WO2019085687A1 (en) * | 2017-11-02 | 2019-05-09 | 广东阿格蕾雅光电材料有限公司 | 4,6-diphenyl sulphone dibenzofuran bipolar material-containing device |
| US11925113B2 (en) | 2018-04-24 | 2024-03-05 | Lg Chem, Ltd. | Heterocyclic compound and organic light emitting device comprising the same |
| US11991928B2 (en) | 2020-07-06 | 2024-05-21 | Samsung Electronics Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10367151B2 (en) | 2015-06-23 | 2019-07-30 | Samsung Electronics Co., Ltd. | Condensed cyclic compound and organic light-emitting device including the same |
| KR102587381B1 (en) * | 2015-12-21 | 2023-10-12 | 솔루스첨단소재 주식회사 | Organic compounds and organic electro luminescence device comprising the same |
| KR20230174709A (en) * | 2022-06-20 | 2023-12-28 | (주)피엔에이치테크 | Organic compound and electroluminescent device comprising the same |
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| US20120071668A1 (en) * | 2010-09-21 | 2012-03-22 | Semiconductor Energy Laboratory Co., Ltd. | Carbazole Derivative, Light-Emitting Element Material and Organic Semiconductor Material |
| EP1972619B1 (en) * | 2007-03-23 | 2012-08-15 | Semiconductor Energy Laboratory Co., Ltd. | Organic compound, anthracene derivative, and light-emitting element, light-emitting device, and electronic device using anthracene derivative |
-
2012
- 2012-12-06 KR KR1020120141101A patent/KR20140073695A/en not_active Application Discontinuation
-
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- 2013-12-05 WO PCT/KR2013/011228 patent/WO2014088347A1/en active Application Filing
- 2013-12-06 TW TW102144765A patent/TW201432024A/en unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1972619B1 (en) * | 2007-03-23 | 2012-08-15 | Semiconductor Energy Laboratory Co., Ltd. | Organic compound, anthracene derivative, and light-emitting element, light-emitting device, and electronic device using anthracene derivative |
| US20120071668A1 (en) * | 2010-09-21 | 2012-03-22 | Semiconductor Energy Laboratory Co., Ltd. | Carbazole Derivative, Light-Emitting Element Material and Organic Semiconductor Material |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105061439A (en) * | 2015-08-03 | 2015-11-18 | 上海道亦化工科技有限公司 | Organic electroluminescent compound and organic electroluminescent device thereof |
| CN105390624A (en) * | 2015-11-11 | 2016-03-09 | 上海道亦化工科技有限公司 | Nitrogen-containing dibenzoheterocycle compound and organic electroluminescent device thereof |
| WO2019085687A1 (en) * | 2017-11-02 | 2019-05-09 | 广东阿格蕾雅光电材料有限公司 | 4,6-diphenyl sulphone dibenzofuran bipolar material-containing device |
| JP2021501988A (en) * | 2017-11-02 | 2021-01-21 | 広東阿格蕾雅光電材料有限公司 | Devices containing bipolar host material based on 4,6-diphenylsulfone dibenzofuran |
| US11925113B2 (en) | 2018-04-24 | 2024-03-05 | Lg Chem, Ltd. | Heterocyclic compound and organic light emitting device comprising the same |
| US11991928B2 (en) | 2020-07-06 | 2024-05-21 | Samsung Electronics Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
Also Published As
| Publication number | Publication date |
|---|---|
| TW201432024A (en) | 2014-08-16 |
| KR20140073695A (en) | 2014-06-17 |
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