KR102184893B1 - Novel organic electroluminescent compounds and organic electroluminescent device comprising the same - Google Patents
Novel organic electroluminescent compounds and organic electroluminescent device comprising the same Download PDFInfo
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- KR102184893B1 KR102184893B1 KR1020130149733A KR20130149733A KR102184893B1 KR 102184893 B1 KR102184893 B1 KR 102184893B1 KR 1020130149733 A KR1020130149733 A KR 1020130149733A KR 20130149733 A KR20130149733 A KR 20130149733A KR 102184893 B1 KR102184893 B1 KR 102184893B1
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- KR
- South Korea
- Prior art keywords
- substituted
- unsubstituted
- group
- alkyl
- organic electroluminescent
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 104
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 125000001769 aryl amino group Chemical group 0.000 claims description 20
- -1 nitro, hydroxy Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 14
- 229910052805 deuterium Inorganic materials 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 12
- 125000005104 aryl silyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000002950 monocyclic group Chemical group 0.000 claims description 9
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 6
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Chemical group 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical compound C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 3
- 125000006835 (C6-C20) arylene group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 2
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
- 150000001720 carbohydrates Chemical class 0.000 claims 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- 239000010410 layer Substances 0.000 description 62
- 239000000463 material Substances 0.000 description 62
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 238000002360 preparation method Methods 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000002019 doping agent Substances 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 125000004429 atom Chemical group 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 239000011368 organic material Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 0 *I(*)[n]1c2ccccc2c2c1cccc2 Chemical compound *I(*)[n]1c2ccccc2c2c1cccc2 0.000 description 5
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 3
- HAEQAUJYNHQVHV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 HAEQAUJYNHQVHV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 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
- REAYFGLASQTHKB-UHFFFAOYSA-N [2-[3-(1H-pyrazol-4-yl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound N1N=CC(=C1)C=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 REAYFGLASQTHKB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 230000004888 barrier function Effects 0.000 description 3
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 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
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CTPUUDQIXKUAMO-UHFFFAOYSA-N 1-bromo-3-iodobenzene Chemical compound BrC1=CC=CC(I)=C1 CTPUUDQIXKUAMO-UHFFFAOYSA-N 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- HNZUKQQNZRMNGS-UHFFFAOYSA-N 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HNZUKQQNZRMNGS-UHFFFAOYSA-N 0.000 description 2
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 150000004770 chalcogenides Chemical class 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000005137 deposition process 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
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000005549 heteroarylene group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 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 2
- 150000002739 metals Chemical class 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 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
- 239000010409 thin film Substances 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- KEOLYBMGRQYQTN-UHFFFAOYSA-N (4-bromophenyl)-phenylmethanone Chemical compound C1=CC(Br)=CC=C1C(=O)C1=CC=CC=C1 KEOLYBMGRQYQTN-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 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
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 1
- KTADSLDAUJLZGL-UHFFFAOYSA-N 1-bromo-2-phenylbenzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1 KTADSLDAUJLZGL-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
- VOZBMWWMIQGZGM-UHFFFAOYSA-N 2-[4-(9,10-dinaphthalen-2-ylanthracen-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=C(C=2C=C3C(C=4C=C5C=CC=CC5=CC=4)=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C3=CC=2)C=C1 VOZBMWWMIQGZGM-UHFFFAOYSA-N 0.000 description 1
- PJRGCJBBXGNEGD-UHFFFAOYSA-N 2-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC=C(Br)C=C3NC2=C1 PJRGCJBBXGNEGD-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
- KTERPBUFTWOSJB-UHFFFAOYSA-N 4-naphthalen-1-yl-1-N,1-N-diphenylcyclohexa-1,5-diene-1,4-diamine Chemical compound C1(=CC=CC2=CC=CC=C12)C1(CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=CC=C1)N KTERPBUFTWOSJB-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- JMRGXJPONZJZQP-UHFFFAOYSA-N Cc1ccc(-c2c(C)ccc3c2[o]c2c3cccc2)nc1 Chemical compound Cc1ccc(-c2c(C)ccc3c2[o]c2c3cccc2)nc1 JMRGXJPONZJZQP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
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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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- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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Abstract
본 발명은 신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로, 본 발명의 유기 전계 발광 화합물은 발광층에 사용될 수 있고, 발광 효율이 우수하여, 구동 수명이 길고 전류 효율 및 전력 효율이 개선된 유기 전계 발광 소자를 제조할 수 있다.The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device including the same, and the organic electroluminescent compound of the present invention can be used in a light emitting layer, has excellent luminous efficiency, and has a long driving life, current efficiency and power efficiency. This improved organic electroluminescent device can be manufactured.
Description
본 발명은 신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다. The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device including the same.
전계 발광 소자(electroluminescence device: EL 소자)는 자체 발광형 표시 소자로서 시야각이 넓고 콘트라스트가 우수할 뿐만 아니라 응답속도가 빠르다는 장점을 가지고 있다. 1987년 이스트만 코닥(Eastman Kodak)사는 발광층 형성용 재료로서 저분자인 방향족 다이아민과 알루미늄 착물을 이용하고 있는 유기 EL 소자를 처음으로 개발하였다[참조: Appl. Phys. Lett. 51, 913, 987].An electroluminescence device (EL device) is a self-luminous display device that has a wide viewing angle, excellent contrast, and a high response speed. In 1987, Eastman Kodak Co., Ltd. first developed an organic EL device using a low-molecular aromatic diamine and an aluminum complex as a material for forming a light emitting layer [See Appl. Phys. Lett. 51, 913, 987].
유기 EL 소자는 통상 애노드 및 캐소드와 이들 사이에 유기물층을 포함하는 구조를 가지며, 애노드와 캐소드에서 각각 주입된 정공과 전자의 재결합에 의해 여기 상태를 형성한 후, 여기 상태가 기저 상태로 되돌아갈 때 발광이 일어난다. 유기 EL 소자의 유기물층은 정공주입층, 정공전달층, 전자장벽층, 발광층, 정공장벽층, 전자전달층, 전자주입층 등으로 이루어질 수 있으며, 유기물층에 사용되는 재료는 정공주입 재료, 정공전달 재료, 전자장벽 재료, 발광 재료, 정공장벽 재료, 전자전달 재료, 전자주입 재료 등으로 나뉜다. An organic EL device usually has a structure including an anode and a cathode, and an organic material layer therebetween, and when an excited state is formed by recombination of holes and electrons injected from the anode and the cathode, respectively, and the excited state returns to the ground state. Light emission occurs. The organic material layer of the organic EL device may be composed of a hole injection layer, a hole transport layer, an electron barrier layer, a light emitting layer, a factory wall layer, an electron transport layer, an electron injection layer, etc., and the material used for the organic material layer is a hole injection material, a hole transport material. , Electron barrier material, light emitting material, factory wall material, electron transport material, electron injection material, etc.
유기 EL 소자의 발광 재료는 소자의 발광 효율을 결정하는 가장 중요한 요인으로서, 발광 재료는 양자 효율이 높고 전자와 정공의 이동도가 커야 하고, 형성된 발광 재료층은 균일하고 안정해야 한다. 발광 재료는 색순도, 발광 효율 및 안정성을 향상시키기 위해 호스트와 도판트를 혼합하여 사용할 수 있다. 이와 같은 도판트/호스트 재료 체계를 사용할 때, 호스트 재료는 발광 소자의 효율과 성능에 큰 영향을 미치므로, 그 선택이 중요하다. 종래 기술에서, 인광용 호스트 재료로는 4,4'-N,N'-다이카바졸-바이페닐(CBP)이 가장 널리 알려져 있었다. 최근에는, 일본의 파이오니어 등이 정공차단층의 재료로 사용되던 바토큐프로인(Bathocuproine, BCP) 및 알루미늄(III) 비스(2-메틸-8-퀴놀리네이트)(4-페닐페놀레이트)(Balq) 등을 호스트 재료로 이용해 고성능의 유기 EL 소자를 개발한 바 있다.The light-emitting material of an organic EL device is the most important factor in determining the light-emitting efficiency of the device. The light-emitting material must have high quantum efficiency and high mobility of electrons and holes, and the formed light-emitting material layer must be uniform and stable. The light-emitting material may be used by mixing a host and a dopant to improve color purity, luminous efficiency, and stability. When using such a dopant/host material system, the host material has a great influence on the efficiency and performance of the light emitting device, so the selection is important. In the prior art, 4,4'-N,N'-dicarbazole-biphenyl (CBP) was most widely known as a host material for phosphorescence. In recent years, Bathocuproine (BCP) and aluminum (III) bis (2-methyl-8-quinolinate) (4-phenylphenolate), which were used as materials for hole blocking layers by Japanese pioneers, etc. Balq) has been used as a host material to develop high-performance organic EL devices.
그러나, 기존의 이러한 인광용 호스트 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 다음과 같은 단점이 있다: (1) 유리 전이 온도가 낮고 열적 안정성이 낮아서, 진공 하에서 고온 증착 공정을 거칠 때, 물질이 변한다. (2) 유기 EL 소자에서 전력 효율 = [(π/전압) × 전류 효율]의 관계에 있으므로 전력 효율은 전압에 반비례한다. 인광용 호스트 재료를 사용한 유기 EL 소자는 형광 호스트 재료를 사용한 유기 EL 소자에 비해 전류 효율(cd/A)은 높으나, 구동 전압 역시 상당히 높기 때문에 전력 효율(lm/w) 면에서 큰 이점이 없다. (3) 유기 EL 소자에 사용할 경우, 작동 수명 측면에서도 만족스럽지 못하며, 발광 효율도 여전히 개선이 요구된다.However, the existing host materials for phosphorescence have advantages in terms of light emission characteristics, but have the following disadvantages: (1) The glass transition temperature is low and the thermal stability is low. Changes. (2) In an organic EL device, power efficiency = [(π/voltage) × current efficiency], so power efficiency is inversely proportional to voltage. An organic EL device using a phosphorescent host material has a higher current efficiency (cd/A) than an organic EL device using a fluorescent host material, but has no significant advantage in terms of power efficiency (lm/w) because the driving voltage is also considerably high. (3) When used in an organic EL device, the operating life is not satisfactory, and the luminous efficiency is still required to be improved.
본 발명에서는 재료의 열 안정성을 증가시켜 고온 증착 공정과 고온 증착 후 열에 의한 결정화를 최소화할 수 있었다. In the present invention, by increasing the thermal stability of the material, it is possible to minimize crystallization due to heat after a high-temperature deposition process and high-temperature deposition.
일반적으로 열 안정성을 증가시키기 위해서는 Tg(유리 전이 온도)를 올려야 한다. Tg를 올리기 위해서는 여러 가지 치환기를 붙여야 한다. 그렇지만 치환기를 많이 붙이면 증착 온도가 너무 높아지게 되고, 증착 과정에서 재료가 분해되고 손상되게 된다. 따라서 치환기를 적절하게 도입하여 적절한 Tg를 확보하고, 큰 분자량에 비해서 낮은 증착 온도를 유지해야 한다. 따라서 본 발명은 플루오렌의 9번 위치에 카바졸을 도입하는 것을 해결책으로 제시하였다. 본 발명의 재료들은 분자량이 큰 편이지만 비슷한 분자량을 갖는 카바졸 유도체보다 증착 온도가 낮는 것이 특징이다. 그리고 본 발명의 재료들은 높은 Tg를 갖고 있다. 이런 특징은 카바졸을 플루오렌의 9번 위치에 치환시킴으로써 플루오렌의 입체장애(steric hindrance)가 크게 작용했기 때문이다. 입체장애가 클수록 분자간의 상호작용(interaction)이 줄어 들고 증착 온도는 낮아지게 된다.In general, it is necessary to raise the Tg (glass transition temperature) to increase the thermal stability. In order to raise Tg, various substituents must be attached. However, if a large number of substituents are attached, the deposition temperature becomes too high, and the material is decomposed and damaged during the deposition process. Therefore, it is necessary to properly introduce a substituent to secure an appropriate Tg and maintain a low deposition temperature compared to a large molecular weight. Therefore, the present invention suggested the introduction of carbazole at the 9th position of fluorene as a solution. Although the materials of the present invention have a large molecular weight, they are characterized by a lower deposition temperature than a carbazole derivative having a similar molecular weight. And the materials of the present invention have a high Tg. This characteristic is because fluorene's steric hindrance greatly worked by substituting carbazole at the 9th position of fluorene. As the steric hindrance increases, the interaction between molecules decreases and the deposition temperature decreases.
따라서, 유기 EL 소자의 우수한 특성을 구현하기 위해서는 소자내 유기물층을 구성하는 재료들, 특히 발광 재료를 구성하는 호스트 또는 도판트를 적절히 선택해야 한다. 한편, 대한민국 특허공보 제10-0957288호, 제10-0948700호 및 제10-0955993호는 발광층 호스트 재료로서 각각 카바졸 그룹에 질소 함유 헤테로사이클 그룹이 결합된 화합물, 아릴카바졸 그룹 또는 카바졸릴알킬렌 그룹에 질소 함유 헤테로사이클 그룹이 결합된 화합물, 및 특정 구조의 인돌로카바졸 유도체를 기재하고 있는데, 상기 특허공보에 개시된 화합물들을 포함한 유기 EL 소자들은 전력 효율, 발광 효율, 수명 등의 측면에서 여전히 만족스럽지 않다. 이에, 본원 발명자들은 발광 소자에 상기 특허공보에 기재된 화합물보다 우수한 성능을 제공할 수 있는 유기 전계 발광 화합물을 찾고자 연구한 결과, 카바졸을 플루오렌 9번 위치에 치환시켜서 높은 Tg와 낮은 증착온도를 갖는 재료를 개발함으로써 발광 효율이 높고 우수한 소자 성능을 제공할 수 있음을 밝혀냈다. Therefore, in order to implement excellent characteristics of the organic EL device, materials constituting the organic material layer in the device, particularly, a host or dopant constituting a light emitting material, must be appropriately selected. Meanwhile, Korean Patent Publications Nos. 10-0957288, 10-0948700, and 10-0955993 are light emitting layer host materials, respectively, as a compound in which a nitrogen-containing heterocycle group is bonded to a carbazole group, an arylcarbazole group, or a carbazolylalkyl. A compound in which a nitrogen-containing heterocycle group is bonded to a ren group, and an indolocarbazole derivative having a specific structure are described. Organic EL devices including the compounds disclosed in the above patent publications are Still not satisfied. Accordingly, the inventors of the present application researched to find an organic electroluminescent compound capable of providing better performance to the light emitting device than the compound described in the above patent publication. As a result, carbazole was substituted at the fluorene 9 position to achieve high Tg and low deposition temperature. It has been found that by developing a material having high luminous efficiency, excellent device performance can be provided.
따라서, 본 발명의 목적은, 첫째로 발광 효율이 높은 유기 전계 발광 화합물을 제공하는 것이며, 둘째로 상기 유기 전계 발광 화합물을 포함하는, 구동 수명이 길고, 전력 효율 및 전류 효율이 개선된 유기 전계 발광 소자를 제공하는 것이다. Accordingly, an object of the present invention is to firstly provide an organic electroluminescent compound having high luminous efficiency, and secondly, an organic electroluminescent compound containing the organic electroluminescent compound, which has a long driving life, and has improved power efficiency and current efficiency. It is to provide the device.
상기 기술적 과제를 해결하기 위해 예의 연구한 결과, 본원 발명자들은 하기 화학식 1로 표시되는 화합물이 상술한 목적을 달성함을 발견하여 본 발명을 완성하였다.As a result of intensive research in order to solve the above technical problem, the present inventors have completed the present invention by finding that the compound represented by the following formula (1) achieves the above object.
[화학식 1][Formula 1]
상기 화학식 1에서,In Formula 1,
A1은 치환 또는 비치환 (5-30원)헤테로아릴기이고;A 1 is a substituted or unsubstituted (5-30 membered) heteroaryl group;
L1은 단일결합, 치환 또는 비치환 (C6-C30)아릴렌기, 또는 치환 또는 비치환 (5-30원)헤테로아릴렌기이며;L 1 is a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (5-30 membered) heteroarylene group;
R1은 치환 또는 비치환 (C1-C30)알킬기, 치환 또는 비치환 (C6-C30)아릴기, 치환 또는 비치환 (5-30원)헤테로아릴기, 치환 또는 비치환 (C3-C30)시클로알킬기, 치환 또는 비치환 (C1-C30)알킬아미노기, 치환 또는 비치환 (C6-C30)아릴아미노기, 또는 치환 또는 비치환 (C1-C30)알킬(C6-C30)아릴아미노기이고;R 1 is a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (5-30 membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cyclo An alkyl group, a substituted or unsubstituted (C1-C30)alkylamino group, a substituted or unsubstituted (C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group;
R2는 수소, 중수소, 할로겐, 시아노기, 치환 또는 비치환 (C1-C30)알킬기, 치환 또는 비치환 (C6-C30)아릴기, 치환 또는 비치환 (5-30원)헤테로아릴기, 치환 또는 비치환 (C3-C30)시클로알킬기, 치환 또는 비치환 (C1-C30)알콕시기, 치환 또는 비치환 (C1-C30)알킬실릴기, 치환 또는 비치환 (C6-C30)아릴실릴기, 치환 또는 비치환 (C6-C30)아르(C1-C30)알킬실릴기, 치환 또는 비치환 (C1-C30)알킬아미노기, 치환 또는 비치환 (C6-C30)아릴아미노기, 치환 또는 비치환 (C1-C30)알킬(C6-C30)아릴아미노기, 또는 화학식 2이거나;R 2 is hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C6-C30) aryl group, substituted or unsubstituted (5-30 membered) heteroaryl group, substituted Or an unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted (C1-C30) alkylsilyl group, a substituted or unsubstituted (C6-C30) arylsilyl group, a substituted Or an unsubstituted (C6-C30) are (C1-C30) alkylsilyl group, a substituted or unsubstituted (C1-C30) alkylamino group, a substituted or unsubstituted (C6-C30) arylamino group, a substituted or unsubstituted (C1-C30) ) Alkyl (C6-C30) arylamino group, or formula 2;
[화학식 2][Formula 2]
R2는 카바졸 골격에 융합되어 벤조카바졸을 형성하고; R 2 is fused to the carbazole backbone to form benzocarbazole;
R3은 수소, 중수소, 할로겐, 시아노기, 치환 또는 비치환 (C1-C30)알킬기, 치환 또는 비치환 (C6-C30)아릴기, 치환 또는 비치환 (5-30원)헤테로아릴기, 치환 또는 비치환 (C3-C30)시클로알킬기, 치환 또는 비치환 (C1-C30)알콕시기, 치환 또는 비치환 (C1-C30)알킬실릴기, 치환 또는 비치환 (C6-C30)아릴실릴기, 치환 또는 비치환 (C6-C30)아르(C1-C30)알킬실릴기, 치환 또는 비치환 (C1-C30)알킬아미노기, 치환 또는 비치환 (C6-C30)아릴아미노기, 또는 치환 또는 비치환 (C1-C30)알킬(C6-C30)아릴아미노기이고;R 3 is hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C6-C30) aryl group, substituted or unsubstituted (5-30 membered) heteroaryl group, substituted Or an unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted (C1-C30) alkylsilyl group, a substituted or unsubstituted (C6-C30) arylsilyl group, a substituted Or an unsubstituted (C6-C30) are (C1-C30) alkylsilyl group, a substituted or unsubstituted (C1-C30) alkylamino group, a substituted or unsubstituted (C6-C30) arylamino group, or a substituted or unsubstituted (C1- C30) alkyl (C6-C30) arylamino group;
X는 O, S, CR11R12, NR13 또는 SiR13R14이고;X is O, S, CR 11 R 12 , NR 13 or SiR 13 R 14 ;
R4, R5 및 R6은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 치환 또는 비치환 (C1-C30)알킬기, 치환 또는 비치환 (C6-C30)아릴기, 치환 또는 비치환 (5-30원)헤테로아릴기, 치환 또는 비치환 (C3-C30)시클로알킬기, 치환 또는 비치환 (C1-C30)알콕시기, 치환 또는 비치환 (C1-C30)알킬실릴기, 치환 또는 비치환 (C6-C30)아릴실릴기, 치환 또는 비치환 (C6-C30)아르(C1-C30)알킬실릴기, 치환 또는 비치환 (C1-C30)알킬아미노기, 치환 또는 비치환 (C6-C30)아릴아미노기, 또는 치환 또는 비치환 (C1-C30)알킬(C6-C30)아릴아미노기이거나, 서로 인접한 치환체와 연결되어 (C3-C30) 단일환 또는 다환의 지환족 또는 방향족 환을 형성할 수 있고, 상기 형성된 지환족 또는 방향족 환의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고;R 4 , R 5 and R 6 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 membered) Heteroaryl group, substituted or unsubstituted (C3-C30) cycloalkyl group, substituted or unsubstituted (C1-C30) alkoxy group, substituted or unsubstituted (C1-C30)alkylsilyl group, substituted or unsubstituted ( C6-C30) arylsilyl group, substituted or unsubstituted (C6-C30) ar (C1-C30) alkylsilyl group, substituted or unsubstituted (C1-C30) alkylamino group, substituted or unsubstituted (C6-C30) arylamino group , Or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group, or connected with a substituent adjacent to each other to form a (C3-C30) monocyclic or polycyclic alicyclic or aromatic ring, and the formed The carbon atom of the alicyclic or aromatic ring may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur;
R11 내지 R14는 각각 독립적으로 치환 또는 비치환 (C1-C30)알킬기, 치환 또는 비치환 (C6-C30)아릴기, 또는 치환 또는 비치환 (5-30원)헤테로아릴기이거나, 서로 인접한 치환체와 연결되어 (C3-C30) 단일환 또는 다환의 지환족 또는 방향족 환을 형성할 수 있고, 상기 형성된 지환족 또는 방향족 환의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고;R 11 to R 14 are each independently a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-30 membered) heteroaryl group, or adjacent to each other It is connected with a substituent to form a (C3-C30) monocyclic or polycyclic alicyclic or aromatic ring, and the carbon atom of the formed alicyclic or aromatic ring may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur. There is;
a, c, d 및 e는 각각 독립적으로 1 내지 4의 정수이고, a, c, d 또는 e가 2이상인 경우 각각의 R2, R4, R5 또는 R6은 동일하거나 상이할 수 있으며;a, c, d and e are each independently an integer of 1 to 4, and when a, c, d or e is 2 or more, each of R 2 , R 4 , R 5 or R 6 may be the same or different;
b는 1 내지 3의 정수이고, b가 2 이상인 경우 각각의 R3은 동일하거나 상이할 수 있고;b is an integer of 1 to 3, and when b is 2 or more, each R 3 may be the same or different;
n은 0 또는 1의 정수이며;n is an integer of 0 or 1;
m은 1 또는 2의 정수이고;m is an integer of 1 or 2;
상기 헤테로아릴(렌)은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함한다.The heteroaryl (ene) includes one or more heteroatoms selected from B, N, O, S, P(=O), Si and P.
본 발명에 따른 유기 전계 발광 화합물은 발광 효율이 종래 재료에 비해 좋아, 이러한 화합물을 발광용 호스트 재료로서 포함하는 유기 전계 발광 소자는 구동 수명이 길고 전류 효율이 매우 양호하여 소비 전력을 개선시킬 수 있다.The organic electroluminescent compound according to the present invention has better luminous efficiency than conventional materials, and an organic electroluminescent device including such a compound as a host material for light emission has a long driving life and very good current efficiency, so that power consumption can be improved. .
이하에서 본 발명을 더욱 상세히 설명하나, 이는 설명을 위한 것으로 본 발명의 범위를 제한하는 것으로 해석되어서는 안된다.Hereinafter, the present invention will be described in more detail, but this is for illustrative purposes and should not be construed as 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 Chemical Formula 1, an organic electroluminescent material including the organic electroluminescent compound, and an organic electroluminescent device including the material.
본원에 기재되어 있는 "(C1-C30)알킬(렌)"은 탄소수가 1 내지 30개인 직쇄 또는 분지쇄 알킬(렌)을 의미하고, 여기에서 탄소수가 1 내지 20개인 것이 바람직하고, 1 내지 10개인 것이 더 바람직하다. 상기 알킬의 구체적인 예로서, 메틸, 에틸, n-프로필, 이소프로필, n-부틸, 이소부틸 및 3급-부틸 등이 있다. 본원에서 "(C2-C30)알케닐"은 탄소수가 2 내지 30개인 직쇄 또는 분지쇄 알케닐을 의미하고, 여기에서 탄소수가 2 내지 20개인 것이 바람직하고, 2 내지 10개인 것이 더 바람직하다. 상기 알케닐의 구체적인 예로서, 비닐, 1-프로페닐, 2-프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 2-메틸부트-2-에닐 등이 있다. 본원에서 "(C2-C30)알키닐"은 탄소수가 2 내지 30개인 직쇄 또는 분지쇄 알키닐을 의미하고, 여기에서 탄소수가 2 내지 20개인 것이 바람직하고, 2 내지 10개인 것이 더 바람직하다. 상기 알키닐의 예로서, 에티닐, 1-프로피닐, 2-프로피닐, 1-부티닐, 2-부티닐, 3-부티닐, 1-메틸펜트-2-이닐 등이 있다. 본원에서 "(C3-C30)시클로알킬"은 탄소수가 3 내지 30개인 단일환 또는 다환 탄화수소를 의미하고, 여기에서 탄소수가 3 내지 20개인 것이 바람직하고, 3 내지 7개인 것이 더 바람직하다. 상기 시클로알킬의 예로서, 시클로프로필, 시클로부틸, 시클로펜틸, 시클로헥실 등이 있다. 본원에서 "(3-7원)헤테로시클로알킬"은 환 골격 원자수가 3 내지 7개, 바람직하게는 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, 테트라하이드로푸란, 피롤리딘, 티올란, 테트라하이드로피란 등이 있다. 본원에서 "(C6-C30)아릴(렌)"은 탄소수가 6 내지 30개인 방향족 탄화수소에서 유래된 단일환 또는 융합환계 라디칼을 의미하고, 여기에서 환 골격 탄소수가 6 내지 20개인 것이 바람직하고, 6 내지 15개인 것이 더 바람직하다. 상기 아릴의 예로서, 페닐, 비페닐, 터페닐, 나프틸, 플루오레닐, 페난트레닐, 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. 여기에서 환 골격 원자수가 3 내지 20개인 것이 바람직하고, 3 내지 15개인 것이 더 바람직하다. 헤테로원자수는 바람직하게는 1 내지 4개이고, 단일환계이거나 하나 이상의 벤젠환과 축합된 융합환계일 수 있으며, 부분적으로 포화될 수도 있다. 또한, 본원에서 상기 헤테로아릴(렌)은 하나 이상의 헤테로아릴기 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 단일환계 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 융합환계 헤테로아릴 등이 있다. 본원에서 "할로겐"은 F, Cl, Br 및 I 원자를 포함한다."(C1-C30)alkyl (ene)" as described herein means a straight-chain or branched-chain alkyl (ene) having 1 to 30 carbon atoms, where it is preferably 1 to 20 carbon atoms, and 1 to 10 Personal is more preferable. Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl. As used herein, "(C2-C30)alkenyl" refers to a straight-chain or branched alkenyl having 2 to 30 carbon atoms, preferably having 2 to 20 carbon atoms, and more preferably having 2 to 10 carbon atoms. Specific examples of the alkenyl include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, and 2-methylbut-2-enyl. As used herein, "(C2-C30)alkynyl" refers to a straight-chain or branched-chain alkynyl having 2 to 30 carbon atoms, wherein the carbon number is preferably 2 to 20, more preferably 2 to 10. Examples of the alkynyl include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, and the like. As used herein, "(C3-C30)cycloalkyl" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms, and preferably 3 to 20 carbon atoms, and more preferably 3 to 7 carbon atoms. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. As used herein, "(3-7 membered) heterocycloalkyl" has 3 to 7, preferably 5 to 7 ring skeleton atoms, and consists of B, N, O, S, P(=O), Si and P It means a cycloalkyl containing one or more heteroatoms selected from the group, preferably one or more heteroatoms selected from O, S, and N, and, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, etc. There is this. As used herein, "(C6-C30)aryl (ene)" refers to a monocyclic or fused cyclic radical derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, wherein the cyclic skeletal carbon number is preferably 6 to 20, and 6 It is more preferably 15 to 15. Examples of the aryl include phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl And fluoranthenyl. As used herein, "(3-30 membered) heteroaryl (ene)" has 3 to 30 ring skeleton atoms, and at least one hetero selected from the group consisting of B, N, O, S, P(=O), Si and P It means an aryl group containing an atom. Here, the number of ring skeleton atoms is preferably 3 to 20, and more preferably 3 to 15. The number of heteroatoms is preferably 1 to 4, and may be a monocyclic system or a fused ring system condensed with one or more benzene rings, and may be partially saturated. In addition, the heteroaryl (ene) herein also includes a form in which one or more heteroaryl groups or aryl groups are connected to a heteroaryl group by a single bond. Examples of the heteroaryl include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl , Triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, and monocyclic heteroaryl such as pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, Dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, Fused ring heteroaryl such as cynnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazineyl, phenanthridinyl, and benzodioxolyl. "Halogen" herein 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. 본 발명의 화학식 1의 A1, L1, R1 내지 R6 및 R11 내지 R14에서 치환 (C1-C30)알킬, 치환 (C1-C30)알콕시, 치환 (C3-C30)시클로알킬, 치환 (C6-C30)아릴(렌), 치환 (5-30원)헤테로아릴(렌) 및 치환 (C6-C30)아르(C1-C30)알킬의 치환체는 각각 독립적으로 중수소, 할로겐, 시아노, 카르복실, 니트로, 히드록시, (C1-C30)알킬, 할로(C1-C30)알킬, (C2-C30)알케닐, (C2-C30)알키닐, (C1-C30)알콕시, (C1-C30)알킬티오, (C3-C30)시클로알킬, (C3-C30)시클로알케닐, (3-7원)헤테로시클로알킬, (C6-C30)아릴옥시, (C6-C30)아릴티오, (C6-C30)아릴로 치환 또는 비치환된 (3-30원)헤테로아릴, (3-30원)헤테로아릴로 치환 또는 비치환된 (C6-C30)아릴, 트리(C1-C30)알킬실릴, 트리(C6-C30)아릴실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, (C1-C30)알킬디(C6-C30)아릴실릴, 아미노, 모노- 또는 디-(C1-C30)알킬아미노, 모노- 또는 디-(C6-C30)아릴아미노, (C1-C30)알킬(C6-C30)아릴아미노, (C1-C30)알킬카보닐, (C1-C30)알콕시카보닐, (C6-C30)아릴카보닐, 디(C6-C30)아릴보로닐, 디(C1-C30)알킬보로닐, (C1-C30)알킬(C6-C30)아릴보로닐, (C6-C30)아르(C1-C30)알킬, 및 (C1-C30)알킬(C6-C30)아릴로 이루어진 군으로부터 선택되는 하나 이상의 것이다.In addition, in the description of "substituted or unsubstituted" described in the present invention, "substituted" means that a hydrogen atom is replaced by another atom or another functional group (ie, a substituent) in a certain functional group. Substituted (C1-C30)alkyl, substituted (C1-C30)alkoxy, substituted (C3-C30)cycloalkyl, substituted in A 1 , L 1 , R 1 to R 6 and R 11 to R 14 of Formula 1 of the present invention (C6-C30) aryl (ene), substituted (5-30 membered) heteroaryl (ene) and substituted (C6-C30) ar (C1-C30) alkyl substituents are each independently deuterium, halogen, cyano, car Boxyl, nitro, hydroxy, (C1-C30)alkyl, halo (C1-C30)alkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30) Alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, (3-7 member)heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, (C6-C30 ) Aryl substituted or unsubstituted (3-30 membered) heteroaryl, (3-30 membered) heteroaryl substituted or unsubstituted (C6-C30) aryl, tri(C1-C30)alkylsilyl, tri(C6) -C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, amino, mono- or di-(C1-C30)alkylamino , Mono- or di-(C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30) ) Arylcarbonyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6-C30)ar( One or more selected from the group consisting of C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl.
상기 화학식 1의 화합물은 하기 화학식 3 내지 5로 표시될 수 있다.The compound of Formula 1 may be represented by the following Formulas 3 to 5.
[화학식 3] [화학식 4] [화학식 5] [Formula 3] [Formula 4] [Formula 5]
상기 화학식 3 내지 5에서,In Formulas 3 to 5,
A1, L1, R1, R2, R3, R4, R5, a, b, c, d, m 및 n은 화학식 1에서의 정의와 동일하다.A 1 , L 1 , R 1 , R 2 , R 3 , R 4 , R 5 , a, b, c, d, m and n are the same as defined in Formula 1.
상기 화학식 1에서, 바람직하게는, A1은 피리딘, 피리미딘, 트리아진, 피라진, 퀴놀린, 퀴나졸린, 퀴녹살린 또는 나프틸리딘 구조를 갖고; L1은 단일결합 또는 (C6-C20)아릴렌기이고; R1은 (C1-C20)알킬기, (C6-C20)아릴기 또는 (5-20원)헤테로아릴기이고; R2는 수소, 중수소, (C6-C20)아릴기, (5-20원)헤테로아릴기, (C6-C20)아릴아미노기 또는 화학식 2이거나, 카바졸 골격에 융합되어 벤조카바졸을 형성하고; R3, R4, R5 및 R6은 각각 수소 또는 (C1-C20)알킬기이고; R11 내지 R14는 각각 (C1-C20)알킬기, (C6-C20)아릴기 또는 (5-20원)헤테로아릴기이다. In Formula 1, preferably, A 1 has a structure of pyridine, pyrimidine, triazine, pyrazine, quinoline, quinazoline, quinoxaline or naphthylidine; L 1 is a single bond or a (C6-C20)arylene group; R 1 is a (C1-C20) alkyl group, a (C6-C20) aryl group or a (5-20 membered) heteroaryl group; R 2 is hydrogen, deuterium, (C6-C20) aryl group, (5-20 membered) heteroaryl group, (C6-C20) arylamino group, or Formula 2, or is fused to a carbazole skeleton to form benzocarbazole; R 3 , R 4 , R 5 and R 6 are each hydrogen or a (C1-C20)alkyl group; R 11 to R 14 are each a (C1-C20) alkyl group, a (C6-C20) aryl group, or a (5-20 membered) heteroaryl group.
상기 화학식 1로 표시되는 화합물은 하기 화합물로부터 선택된다.The compound represented by Formula 1 is selected from the following compounds.
본 발명에 따른 유기 전계 발광 화합물은 당업자에게 공지된 합성 방법으로 제조할 수 있으며, 예를 들면 하기 반응식 1에 따라 제조할 수 있다.The organic electroluminescent compound according to the present invention can be prepared by a synthetic method known to those skilled in the art, for example, can be prepared according to the following Scheme 1.
[반응식 1][Scheme 1]
상기 반응식 1 에서, A1, L1, R1, R2, R3, R4, R5, a, b, c, d, m 및 n은 화학식 1에서의 정의와 동일하고, Hal는 할로겐이다.In Reaction Scheme 1, A 1 , L 1 , R 1 , R 2 , R 3 , R 4 , R 5 , a, b, c, d, m and n are the same as defined in Formula 1, and Hal is halogen to be.
본 발명은 추가의 양태로 상기 화학식 1의 유기 전계 발광 화합물을 포함하는 유기 전계 발광 재료 및 상기 재료를 포함하는 유기 전계 발광 소자를 제공한다. 상기 재료는 본 발명의 유기 전계 발광 화합물 단독으로 이루어질 수 있고, 유기 전계 발광 재료에 포함되는 물질들을 추가로 포함할 수 있다. 본 발명에 따른 유기 전계 발광 소자는 제1 전극; 제2 전극; 및 상기 제1 전극과 제2 전극 사이에 개재되는 1층 이상의 유기물층을 갖고, 상기 유기물층은 상기 화학식 1의 화합물을 하나 이상 포함한다.In a further aspect, the present invention provides an organic electroluminescent material comprising the organic electroluminescent compound of Formula 1 and an organic electroluminescent device comprising the material. The material may be formed of the organic electroluminescent compound of the present invention alone, and may further include materials included in the organic electroluminescent material. The 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, wherein the organic material layer includes at least one compound of Formula 1 above.
상기 제1 전극과 제2 전극 중 하나는 애노드이고 다른 하나는 캐소드일 수 있다. 상기 유기물층은 발광층을 포함하고, 정공주입층, 정공전달층, 전자장벽층, 전자전달층, 전자주입층, 계면층(interlayer) 및 정공차단층에서 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 includes an emission layer, and may further include at least one layer selected from a hole injection layer, a hole transport layer, an electron barrier layer, an electron transport layer, an electron injection layer, an interlayer, and a hole blocking layer.
본 발명의 화학식 1의 유기 전계 발광 화합물은 상기 발광층에 호스트 재료로서 포함될 수 있다. 바람직하게는 상기 발광층은 하나 이상의 도판트를 추가로 포함할 수 있으며, 필요한 경우, 본 발명의 화학식 1의 유기 전계 발광 화합물 이외의 다른 화합물을 제2 호스트 재료로 추가로 포함할 수 있다.The organic electroluminescent compound of Formula 1 of the present invention may be included as a host material in the emission layer. Preferably, the emission layer may further include one or more dopants, and if necessary, may further include a compound other than the organic electroluminescent compound of Formula 1 of the present invention as a second host material.
본 발명은 추가의 양태로 유기 전계 발광 소자 제조용 재료를 제공한다. 상기 재료는 제1 호스트 재료 및 제2 호스트 재료를 포함하며, 상기 제1 호스트 재료는 본 발명의 유기 전계 발광 화합물을 포함한다. 이때 제1 호스트 재료와 제2 호스트 재료의 중량비는 1:99 내지 99:1 범위이다.The present invention provides a material for manufacturing an organic electroluminescent device in a further aspect. The material includes a first host material and a second host material, and the first host material includes the organic electroluminescent compound of the present invention. In this case, the weight ratio of the first host material and the second host material is in the range of 1:99 to 99:1.
상기 제2 호스트 재료는 공지된 인광 호스트라면 어느 것이든 사용가능하며, 바람직하게는 하기 화학식 6 내지 10으로 표시되는 화합물로 구성된 군으로부터 선택되는 것이 발광 효율면에서 특히 바람직하다.Any known phosphorescent host may be used as the second host material, and it is particularly preferable in terms of luminous efficiency to be selected from the group consisting of compounds represented by the following Chemical Formulas 6 to 10.
[화학식 6][Formula 6]
H-(Cz-L4)h-M H-(Cz-L 4 ) h -M
[화학식 7][Formula 7]
H-(Cz)i-L4-MH-(Cz) i -L 4 -M
[화학식 8][Formula 8]
[화학식 9][Formula 9]
[화학식 10][Formula 10]
상기 화학식 6 내지 10에서,In Formulas 6 to 10,
Cz는 하기 구조이며,Cz is the following structure,
X는 O 또는 S이고;X is O or S;
R21 내지 R24는 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환 (C1-C30)알킬, 치환 또는 비치환 (C6-C30)아릴, 치환 또는 비치환 (5-30 원)헤테로아릴 또는 R25R26R27Si-이거나; 인접한 치환체와 연결되어 (5-30원) 단일환 또는 다환의 지환족 또는 방향족 환을 형성할 수 있고, 이 때 상기 형성된 지환족 또는 방향족 환의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고; R25 내지 R27은 각각 독립적으로 치환 또는 비치환 (C1-C30)알킬, 또는 치환 또는 비치환 (C6-C30)아릴이고; L4는 단일결합, 치환 또는 비치환 (C6-C30)아릴렌, 또는 치환 또는 비치환 (5-30원)헤테로아릴렌이며; M은 치환 또는 비치환 (C6-C30)아릴, 또는 치환 또는 비치환 (5-30원)헤테로아릴이고; Y1 및 Y2는 각각 독립적으로 -O-, -S-, -N(R31)- 또는 -C(R32)(R33)-이며, Y1과 Y2가 동시에 존재하지는 않고; R31 내지 R33은 각각 독립적으로 치환 또는 비치환 (C1-C30)알킬, 치환 또는 비치환 (C6-C30)아릴, 또는 치환 또는 비치환 (5-30원)헤테로아릴이거나; 인접한 치환체와 연결되어 (5-30원) 단일환 또는 다환의 지환족 또는 방향족 환을 형성할 수 있고, 이 때 상기 형성된 지환족 또는 방향족 환의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고; R32 및 R33은 동일하거나 상이할 수 있고; h 및 i는 각각 독립적으로 1 내지 3의 정수이고; j, k, l 및 m은 각각 독립적으로 0 내지 4의 정수이며; h, i, j, k, l 또는 m이 2 이상의 정수인 경우 각각의 (Cz-L4), 각각의 (Cz), 각각의 R21, 각각의 R22, 각각의 R23 또는 각각의 R24는 동일하거나 상이할 수 있다.R 21 to R 24 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-30 membered) heteroaryl, or Is R 25 R 26 R 27 Si-; It is connected with an adjacent substituent (5-30 membered) to form a monocyclic or polycyclic alicyclic or aromatic ring, wherein the carbon atom of the formed alicyclic or aromatic ring is at least one hetero selected from nitrogen, oxygen, and sulfur. Can be replaced by atoms; R 25 to R 27 are each independently substituted or unsubstituted (C1-C30)alkyl, or substituted or unsubstituted (C6-C30)aryl; L 4 is a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5-30 membered) heteroarylene; M is a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-30 membered) heteroaryl; Y 1 and Y 2 are each independently -O-, -S-, -N(R 31 )- or -C(R 32 )(R 33 )-, and Y 1 and Y 2 are not present at the same time; R 31 to R 33 are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (5-30 membered)heteroaryl; It is connected with an adjacent substituent (5-30 membered) to form a monocyclic or polycyclic alicyclic or aromatic ring, wherein the carbon atom of the formed alicyclic or aromatic ring is at least one hetero selected from nitrogen, oxygen, and sulfur. Can be replaced by atoms; R 32 and R 33 may be the same or different; h and i are each independently an integer of 1 to 3; j, k, l and m are each independently an integer of 0 to 4; When h, i, j, k, l, or m is an integer of 2 or more, each (Cz-L 4 ), each (Cz), each R 21 , each R 22 , each R 23 or each R 24 May be the same or different.
구체적으로 상기 제2 호스트 재료의 바람직한 예는 다음과 같다.Specifically, preferred examples of the second host material are as follows.
(여기서, TPS는 트리페닐실릴이다) (Where, TPS is triphenylsilyl)
상기 도판트로는 하나 이상의 인광 도판트가 바람직하다. 본 발명의 유기 전계 발광 소자에 적용되는 인광 도판트 재료는 특별히 제한되지는 않으나, 이리듐(Ir), 오스뮴(Os), 구리(Cu) 및 백금(Pt)으로부터 선택되는 금속 원자의 착체 화합물이 바람직하고, 이리듐(Ir), 오스뮴(Os), 구리(Cu) 및 백금(Pt)으로부터 선택되는 금속 원자의 오르토 메탈화 착체 화합물이 더욱 바람직하며, 오르토 메탈화 이리듐 착체 화합물이 더더욱 바람직하다.As the dopant, at least one phosphorescent dopant is preferable. The phosphorescent dopant material applied to the organic electroluminescent device of the present invention is not particularly limited, but a complex compound of metal atoms selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt) is preferred. And, an ortho-metallized complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt) is more preferable, and an ortho-metalized iridium complex compound is even more preferable.
본 발명의 유기 전계 발광 소자에 포함되는 도판트로 하기 화학식 11 내지 13으로 표시되는 화합물을 사용할 수 있다.Compounds represented by the following Formulas 11 to 13 may be used as a dopant included in the organic electroluminescent device of the present invention.
[화학식 11] [화학식 12] [화학식 13] [Formula 11] [Formula 12] [Formula 13]
상기 화학식 11내지 13에서, L은 하기 구조에서 선택되고;In Formulas 11 to 13, L is selected from the following structures;
R100은 수소, 치환 또는 비치환 (C1-C30)알킬, 또는 치환 또는 비치환 (C3-C30)시클로알킬이며; R101 내지 R109 및 R111 내지 R123은 각각 독립적으로 수소, 중수소, 할로겐, 할로겐으로 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환 (C3-C30)시클로알킬, 시아노, 또는 치환 또는 비치환 (C1-C30)알콕시이고; R120 내지 R123은 인접 치환기가 서로 연결되어 융합고리를 형성하는데, 예를 들어 퀴놀린 형성이 가능하며; R124 내지 R127은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환 (C1-C30)알킬, 또는 치환 또는 비치환 (C6-C30)아릴이며; R124 내지 R127이 아릴기인 경우 인접기가 서로 연결되어 융합고리를 형성하는데, 예를 들어 플루오렌 형성이 가능하며; R201 내지 R211은 각각 독립적으로 수소, 중수소, 할로겐, 또는 할로겐으로 치환 또는 비치환된 (C1-C30)알킬, 또는 치환 또는 비치환 (C3-C30)시클로알킬이며; f 및 g는 각각 독립적으로 1 내지 3의 정수이며, f 또는 g가 각각 2 이상의 정수인 경우 각각의 R100은 서로 동일하거나 상이할 수 있고; n은 1 내지 3의 정수이다. R 100 is hydrogen, substituted or unsubstituted (C1-C30)alkyl, or substituted or unsubstituted (C3-C30)cycloalkyl; R 101 to R 109 and R 111 to R 123 are each independently hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, cyano, Or substituted or unsubstituted (C1-C30)alkoxy; R 120 to R 123 are adjacent substituents linked to each other to form a fused ring, for example, quinoline can be formed; R 124 to R 127 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, or substituted or unsubstituted (C6-C30)aryl; When R 124 to R 127 are an aryl group, adjacent groups are connected to each other to form a fused ring, for example, fluorene can be formed; R 201 to R 211 are each independently hydrogen, deuterium, halogen, or halogen-substituted or unsubstituted (C1-C30)alkyl, or substituted or unsubstituted (C3-C30)cycloalkyl; f and g are each independently an integer of 1 to 3, and when f or g is an integer of 2 or more, each R 100 may be the same as or different from each other; n is an integer of 1 to 3.
상기 도판트 재료의 구체적인 예는 다음과 같다. A specific example of the dopant material is as follows.
본 발명의 유기 전계 발광 소자는 유기물층에 화학식 1의 유기 전계 발광 화합물을 포함하고, 이와 동시에 아릴아민계 화합물 및 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 화합물을 포함할 수 있다. The organic electroluminescent device of the present invention may include an organic electroluminescent compound of Formula 1 in the organic material layer, and at the same time include at least one compound selected from the group consisting of an arylamine compound and a styrylarylamine compound.
또한, 본 발명의 유기 전계 발광 소자에 있어서, 유기물층에 상기 화학식 1의 유기 전계 발광 화합물 이외에 1족, 2족, 4주기 전이금속, 5주기 전이금속, 란탄 계열 금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속, 또는 이러한 금속을 포함하는 하나 이상의 착체 화합물을 더 포함할 수도 있다.In addition, in the organic electroluminescent device of the present invention, in the organic material layer, in addition to the organic electroluminescent compound of Formula 1, a group 1, a group 2, a period 4 transition metal, a period 5 transition metal, a lanthanum metal, and an organic metal of a d-transition element One or more metals selected from the group consisting of, or one or more complex compounds containing such metals may be further included.
또한, 본 발명의 유기 전계 발광 소자는 본 발명의 유기 전계 발광 화합물 이외에 당업계에 알려진 청색, 적색 또는 녹색 발광 화합물을 포함하는 발광층을 하나 이상 더 포함함으로써 백색 발광을 할 수 있다. 또한, 필요에 따라, 노란색 또는 주황색 발광층을 더 포함할 수도 있다.In addition, the organic electroluminescent device of the present invention may emit white light by further including one or more light-emitting layers including blue, red, or green light-emitting compounds known in the art in addition to the organic electroluminescent compound of the present invention. Further, if necessary, a yellow or orange light emitting layer may be further included.
본 발명의 유기 전계 발광 소자에 있어서, 한 쌍의 전극의 적어도 한쪽의 내측 표면에, 칼코제나이드(chalcogenide)층, 할로겐화 금속층 및 금속 산화물층으로부터 선택되는 하나 이상의 층(이하, 이들을 "표면층"이라고 지칭함)을 배치하는 것이 바람직하다. 구체적으로는, 발광 매체층 측의 양극 표면에 규소 및 알루미늄의 칼코제나이드(산화물을 포함한다)층을, 또한 발광 매체층 측의 음극 표면에 할로겐화 금속층 또는 금속 산화물층을 배치하는 것이 바람직하다. 상기 표면층에 의해 유기 전계 발광 소자의 구동 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, on at least one inner surface of the pair of electrodes, at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as "surface layer" It is preferable to place). Specifically, it is preferable to provide a silicon and aluminum chalcogenide (including oxide) layer on the anode surface on the side of the light-emitting medium layer, and a metal halide layer or a metal oxide layer on the cathode surface on the side of the light-emitting medium layer. Stabilization of driving of the organic electroluminescent device can be obtained by the surface layer. Preferred examples of the chalcogenide include SiO X (1≤X≤2), AlO X (1≤X≤1.5), SiON or SiAlON, and preferred examples of the metal halide include LiF, MgF 2 , CaF 2 , fluoride Rare earth metals and the like, and preferred examples of metal oxides include Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, and the like.
또한, 본 발명의 유기 전계 발광 소자에 있어서, 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 발광을 하는 유기 전계 발광소자를 제작할 수 있다.In addition, in the organic electroluminescent device of the present invention, it is also preferable to arrange a mixed region of an electron transfer compound and a reducing dopant, or a mixed region of a hole transport compound and an oxidizing dopant on at least one surface of the pair of electrodes. . 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. In addition, since the hole transport compound is oxidized to become a cation, it becomes easy to inject and transfer holes from the mixed region to the light emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, and preferable reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, an organic electroluminescent device having two or more light emitting layers and emitting white light can be manufactured by using the reducing dopant layer as a charge generation layer.
본 발명의 유기 전계 발광 소자의 각 층의 형성은 진공증착, 스퍼터링, 플라즈마, 이온플레이팅 등의 건식 성막법이나, 스핀코팅, 침지 코팅(dip coating), 플로우 코팅 등의 습식 성막법 중 어느 하나의 방법을 적용할 수 있다.The formation of each layer of the organic electroluminescent device of the present invention is either a dry film formation method such as vacuum deposition, sputtering, plasma, ion plating, or a wet film formation method such as spin coating, dip coating, and flow coating. The method of can be applied.
습식 성막법의 경우, 각 층을 형성하는 재료를 에탄올, 클로로포름, 테트라하이드로푸란, 디옥산 등의 적절한 용매에 용해 또는 분산시켜 박막을 형성하는데, 그 용매는 각 층을 형성하는 재료가 용해 또는 분산될 수 있고, 성막성에 문제가 없는 것이라면 어느 것이어도 된다.In the case of wet film formation, a thin film is formed by dissolving or dispersing the material forming each layer in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc., and the solvent is dissolved or dispersed in the material forming each layer. It can be made, and any one may be used as long as there is no problem with the film forming property.
이하에서, 본 발명의 상세한 이해를 위하여 본 발명의 대표 화합물을 들어 본 발명에 따른 유기 전계 발광 화합물, 이의 제조방법 및 소자의 발광 특성을 설명한다.
Hereinafter, for a detailed understanding of the present invention, an organic electroluminescent compound according to the present invention, a method of manufacturing the same, and light emission characteristics of the device will be described with reference to the representative compound of the present invention.
[실시예 1] 화합물 H-34의 제조[Example 1] Preparation of Compound H-34
화합물 1-2의 제조Preparation of compound 1-2
3L 둥근 플라스크에 2-브로모바이페닐(50g, 214mmol)을 넣고 테트라하이드로푸란(THF) 1L를 넣고 -78℃로 냉각시켰다. 2.5M n-부틸 리튬(103mL, 257mmol)을 넣고 2시간 후 (4-브로모페닐)(페닐)메탄온(56g, 214mmol)을 넣었다. 17시간 후 메틸렌 클로라이드(MC)와 H2O로 추출하고 MC층을 MgSO4로 건조시켰다. MC층을 농축하여 화합물 1-1을 얻었다. In a 3L round flask, 2-bromobiphenyl (50g, 214mmol) was added, and 1L of tetrahydrofuran (THF) was added, followed by cooling to -78°C. 2.5M n-butyl lithium (103mL, 257mmol) was added and 2 hours later (4-bromophenyl) (phenyl)methanone (56g, 214mmol) was added. After 17 hours, the mixture was extracted with methylene chloride (MC) and H 2 O, and the MC layer was dried over MgSO 4 . The MC layer was concentrated to obtain compound 1-1.
3L 둥근 플라스크에 화합물 1-1, 염산(100mL) 및 아세트산(1L)을 넣고 환류 교반하였다. 14시간 후 생성된 고체를 여과하고 여과된 고체를 클로로포름(CHCl3)에 녹여 컬럼하여 화합물 1-2(35g, 42%)를 얻었다. Compound 1-1, hydrochloric acid (100 mL), and acetic acid (1 L) were added to a 3 L round flask and stirred under reflux. After 14 hours, the resulting solid was filtered, and the filtered solid was dissolved in chloroform (CHCl 3 ) and column to obtain compound 1-2 (35g, 42%).
화합물 1-3의 제조Preparation of compound 1-3
1L 둥근 플라스크에 화합물 1-2(35g, 89mmol), 비스(피나콜라토)디보란(27g, 106mmol), 비스(트리페닐포스핀)팔라듐(II) 디클로라이드(Pd(PPh3)2Cl2)(3.1g, 4.45mmol), 칼륨 아세테이트(KOAc)(22g, 222mmol) 및 1,4-디옥산(445mL)을 넣고 환류 교반하였다. 3시간 후 디클로로메탄(DCM)과 H2O로 추출하고 DCM층을 MgSO4로 건조시킨 후 여과하였다. 얻어진 고체를 CHCl3에 녹여 컬럼하여 화합물 1-3(22g, 56%)을 얻었다. In a 1L round flask, compound 1-2 (35g, 89mmol), bis(pinacolato)diborane (27g, 106mmol), bis(triphenylphosphine)palladium(II) dichloride (Pd(PPh 3 ) 2 Cl 2 ) ) (3.1g, 4.45mmol), potassium acetate (KOAc) (22g, 222mmol) and 1,4-dioxane (445mL) were added and stirred under reflux. After 3 hours, the mixture was extracted with dichloromethane (DCM) and H 2 O, and the DCM layer was dried over MgSO 4 and filtered. The obtained solid was dissolved in CHCl 3 and subjected to column to obtain compound 1-3 (22g, 56%).
화합물 1-4의 제조Preparation of compound 1-4
500mL 둥근 플라스크에 화합물 1-3(22g, 50mmol), 2-브로모니트로벤젠(12g, 60mmol), 테트라키스(트리페닐포스핀)팔라듐(O)(Pd(PPh3)4)(1.7g, 1.5mmol), K2CO3(13.7g, 99.4mmol), 톨루엔(100mL), 에탄올(EtOH)(25mL) 및 H2O(25L)를 넣고 환류 교반하였다. 5시간 후 DCM과 H2O로 추출하고 DCM층을 MgSO4로 건조시킨 후 여과하였다. 얻어진 고체를 CHCl3에 녹여 컬럼하여 화합물 1-4(15g, 70%)를 얻었다. In a 500 mL round flask, compound 1-3 (22 g, 50 mmol), 2-bromonitrobenzene (12 g, 60 mmol), tetrakis (triphenylphosphine) palladium (O) (Pd (PPh 3 ) 4 ) (1.7 g, 1.5 mmol), K 2 CO 3 (13.7 g, 99.4 mmol), toluene (100 mL), ethanol (EtOH) (25 mL), and H 2 O (25 L) were added and stirred under reflux. After 5 hours, the mixture was extracted with DCM and H 2 O, and the DCM layer was dried over MgSO 4 and filtered. The obtained solid was dissolved in CHCl 3 and then column to obtain compound 1-4 (15g, 70%).
화합물 1-5의 제조Preparation of compound 1-5
500mL 둥근 플라스크에 화합물 1-4(15g, 35mmol), 트리에틸포스파이트(P(OEt)3)(100mL) 및 1,2-디클로로벤젠(1,2-DCB)(50mL)을 넣고 환류 교반하였다. 13시간 후 용매를 증류하고 CHCl3에 녹여 컬럼하여 화합물 1-5(8.42g, 59%)를 얻었다. Compound 1-4 (15g, 35mmol), triethylphosphite (P(OEt) 3 ) (100mL) and 1,2-dichlorobenzene (1,2-DCB) (50mL) were added to a 500mL round flask and stirred under reflux. . After 13 hours, the solvent was distilled off, dissolved in CHCl 3 , and column to give compound 1-5 (8.42g, 59%).
화합물 1-6의 제조Preparation of compound 1-6
500mL 둥근 플라스크에 화합물 1-5(8.4g, 21mmol), 1-브로모-3-요오도벤젠(8.7g, 31mmol), CuI(2g, 10.3mmol), 에틸렌디아민(1.4mL, 21mmol), K3PO4(13g, 62mmol) 및 톨루엔(103mL)을 넣고 23시간 동안 환류 교반하였다. 반응이 종료되면 상온으로 냉각시킨 후 DCM과 H2O로 추출한 후 DCM층을 MgSO4로 건조시켰다. DCM층을 감압 농축 후 얻어진 용액을 컬럼하여 화합물 1-6(9.5g, 94%)을 얻었다.Compound 1-5 (8.4g, 21mmol), 1-bromo-3-iodobenzene (8.7g, 31mmol), CuI (2g, 10.3mmol), ethylenediamine (1.4mL, 21mmol), K in a 500mL round flask. 3 PO 4 (13 g, 62 mmol) and toluene (103 mL) were added and stirred under reflux for 23 hours. When the reaction was completed, the mixture was cooled to room temperature, extracted with DCM and H 2 O, and then the DCM layer was dried over MgSO 4 . The DCM layer was concentrated under reduced pressure and the resulting solution was columned to obtain compound 1-6 (9.5g, 94%).
화합물 1-7의 제조Preparation of compound 1-7
500mL 둥근 플라스크에 화합물 1-6(9.5g, 19.5mmol), 비스(피나콜라토)디보란(6.4g, 25mmol), Pd(PPh3)2Cl2(684mg, 0.97mmol), KOAc(4.8g, 49mmol) 및 1,4-디옥산(196mL)을 넣고 환류 교반하였다. 6시간 후 DCM과 H2O로 추출하고 DCM층을 MgSO4로 건조시킨 후 여과하였다. 얻어진 고체를 CHCl3에 녹여 컬럼하여 화합물 1-7(8g, 69%)을 얻었다. In a 500 mL round flask, compound 1-6 (9.5g, 19.5mmol), bis(pinacolato)diborane (6.4g, 25mmol), Pd(PPh 3 ) 2 Cl 2 (684mg, 0.97mmol), KOAc (4.8g) , 49mmol) and 1,4-dioxane (196 mL) were added and stirred under reflux. After 6 hours, the mixture was extracted with DCM and H 2 O, and the DCM layer was dried over MgSO 4 and filtered. The obtained solid was dissolved in CHCl 3 and subjected to column to obtain compound 1-7 (8g, 69%).
화합물 H-34의 제조Preparation of compound H-34
250mL 둥근 플라스크에 화합물 1-7(8g, 13mmol), 2-클로로-4,6-디페닐-1,3,5-트리아진(4.2g, 15.7mmol), Pd(PPh3)4(454mg, 0.39mmol), K2CO3(3.6g, 26mmol), 톨루엔(30mL), EtOH(7mL) 및 H2O(7mL)를 넣고 환류 교반하였다. 3시간 후 DCM과 H2O로 추출하고 DCM층을 MgSO4로 건조시킨 후 여과하였다. 얻어진 고체를 CHCl3에 녹여 컬럼하여 화합물 H-34(3.95g, 42%)를 얻었다. In a 250 mL round flask, compound 1-7 (8g, 13mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.2g, 15.7mmol), Pd(PPh 3 ) 4 (454mg, 0.39mmol), K 2 CO 3 (3.6 g, 26 mmol), toluene (30 mL), EtOH (7 mL) and H 2 O (7 mL) were added and stirred under reflux. After 3 hours, the mixture was extracted with DCM and H 2 O, and the DCM layer was dried over MgSO 4 and filtered. The obtained solid was dissolved in CHCl 3 and subjected to column to obtain compound H-34 (3.95 g, 42%).
물성 데이타: mp 288℃, UV 290nm(톨루엔 중), PL 430nm(톨루엔 중), MS/EIMS 714.28
Physical property data: mp 288°C, UV 290 nm (in toluene), PL 430 nm (in toluene), MS/EIMS 714.28
[실시예 2] 화합물 H-57의 제조[Example 2] Preparation of Compound H-57
화합물 2-1의 제조Preparation of compound 2-1
2L 둥근 바닥 플라스크(RBF)에 화합물 1-3, 35g(78mmol), 2,5-디브로모니트로벤젠 26.2g(93mmol), Pd(PPh3)4 3.6g(3.1mmol), Na2CO3 20.6g(195 mmol), 톨루엔 400mL, 에탄올 50mL 및 물 100mL를 녹인 뒤, 130℃ 하에서 밤새 교반하였다. 반응 혼합물은 에틸 아세테이트(EA)/H2O로 후처리하고, MgSO4로 수분을 제거한 후, 감압증류하였다. 조 생성물은 메틸렌 클로라이드(MC):헥산(Hx)으로 컬럼하여 화합물 2-1, 30g(75%)의 고체를 얻었다. In a 2L round bottom flask (RBF) compound 1-3, 35g (78mmol), 2,5-dibromonnitrobenzene 26.2g (93mmol), Pd (PPh 3 ) 4 3.6g (3.1mmol), Na 2 CO 3 After dissolving 20.6g (195 mmol), 400 mL of toluene, 50 mL of ethanol and 100 mL of water, the mixture was stirred overnight at 130°C. The reaction mixture was worked up with ethyl acetate (EA)/H 2 O, dried with MgSO 4 , and then distilled under reduced pressure. The crude product was columned with methylene chloride (MC):hexane (Hx) to obtain compound 2-1, 30 g (75%) of a solid.
화합물 2-2의 제조Preparation of compound 2-2
1L RBF에 화합물 2-1, 30g(57.8 mmol), 트리에틸포스파이트 200mL 및 1,2-DCB 200mL를 넣고, 150℃ 하에서 2시간 동안 교반하였다. 반응 혼합물은 증류하여 고체를 얻었다. 조 생성물은 MC:Hx로 컬럼하여 화합물 2-2, 19g(68%)의 하얀색 고체를 얻었다. Compound 2-1, 30g (57.8 mmol), 200 mL of triethylphosphite and 200 mL of 1,2-DCB were added to 1L RBF, and stirred at 150° C. for 2 hours. The reaction mixture was distilled to obtain a solid. The crude product was columned with MC:Hx to obtain compound 2-2, 19 g (68%) of a white solid.
화합물 2-3의 제조Preparation of compound 2-3
500mL RBF에 화합물 2-2, 5.7g(47mmol), Pd(PPh3)4 1.8g(1.5mmol), K2CO3 13.5g(97mmol), 톨루엔 200mL, 에탄올 50mL 및 물 50mL를 넣고, 120℃ 하에서 2.5시간 동안 교반하였다. 반응 혼합물은 EA/H2O로 후처리하고, MgSO4로 수분을 제거한 후, 감압증류하였다. 조 생성물은 MC:Hx로 컬럼하여 화합물 2-3, 16g(84%)의 하얀색 고체를 얻었다. Compound 2-2, 5.7 g (47 mmol), Pd (PPh 3 ) 4 1.8 g (1.5 mmol), K 2 CO 3 13.5 g (97 mmol), toluene 200 mL, ethanol 50 mL, and water 50 mL were added to 500 mL RBF, and 120°C Stirred for 2.5 hours under. The reaction mixture was worked up with EA/H 2 O, dried with MgSO 4 , and then distilled under reduced pressure. The crude product was columned with MC:Hx to obtain compound 2-3, 16g (84%) of a white solid.
화합물 H-57의 제조Preparation of compound H-57
500mL RBF에 화합물 2-3, 10g(20.6mmol), 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 9.6g(24.8mmol), 팔라듐(II) 아세테이트(Pd(OAc)2) 232mg(1.0mmol), 2-디사이클로헥실포스피노-2', 6'-디메톡시바이페닐(s-phos) 850mg(2.0mmol), 나트륨 3급 부톡사이드(NaOtBu) 5g(51.6mmol) 및 o-크실렌 200mL를 넣고, 180℃ 하에서 2시간 동안 교반하였다. 반응 혼합물은 EA/H2O로 후처리하고, MgSO4로 수분을 제거한 후, 감압증류하였다. 조 생성물은 MC:Hx로 컬럼하여 화합물 H-57, 7.3g(45%)의 하얀색 고체를 얻었다.Compound 2-3, 10g (20.6mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine 9.6g (24.8mmol), palladium (II) in 500mL RBF Acetate (Pd(OAc)2) 232mg (1.0mmol), 2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl (s-phos) 850mg (2.0mmol), sodium tertiary butoxide (NaOtBu ) 5g (51.6mmol) and 200 mL of o-xylene were added, and stirred at 180° C. for 2 hours. The reaction mixture was worked up with EA/H 2 O, dried with MgSO 4 , and then distilled under reduced pressure. The crude product was columned with MC:Hx to obtain compound H-57, 7.3 g (45%) of a white solid.
물성 데이타: mp 312℃, UV 344nm(톨루엔 중), PL 427nm(톨루엔 중), MS/EIMS 791
Physical data: mp 312°C, UV 344 nm (in toluene), PL 427 nm (in toluene), MS/EIMS 791
[실시예 3] 화합물 H-90의 제조[Example 3] Preparation of Compound H-90
화합물 3-1의 제조Preparation of compound 3-1
플라스크에 9-플루오렌온(20g, 111mmol)을 넣고 THF 554mL로 녹인 후 0℃에서 페닐마그네슘 브로마이드(36.9mL)를 천천히 넣고 24시간 동안 실온해서 교반하였다. 반응이 끝나면 에틸 아세테이트로 유기층을 추출하고 마그네슘 설페이트를 이용하여 잔여 수분을 제거한 뒤 건조시키고 컬럼으로 분리하여 화합물 3-1, 20g(70%)을 얻었다.9-fluorenone (20g, 111mmol) was added to the flask, dissolved in THF 554mL, phenylmagnesium bromide (36.9mL) was slowly added at 0°C and stirred at room temperature for 24 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by a column to obtain compound 3-1, 20 g (70%).
화합물 3-2의 제조Preparation of compound 3-2
플라스크에 2-브로모-9H-카바졸(20g, 81.2mmol), 페닐보론산 11.9g(97.5mmol), Pd(PPh3)4 4.7g(4.06mmol), 2M K2CO3 121mL, 톨루엔 250mL 및 에탄올 121mL를 넣고 5시간 동안 환류 교반하였다. 반응이 끝나면 에틸 아세테이트로 유기층을 추출하고 마그네슘 설페이트를 이용하여 잔여 수분을 제거한 뒤 건조시키고 컬럼으로 분리하여 화합물 3-2, 17g(86%)을 얻었다.In a flask, 2-bromo-9H-carbazole (20 g, 81.2 mmol), phenylboronic acid 11.9 g (97.5 mmol), Pd (PPh 3 ) 4 4.7 g (4.06 mmol), 2M K 2 CO 3 121 mL, toluene 250 mL And 121 mL of ethanol was added and stirred under reflux for 5 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column to obtain compound 3-2, 17g (86%).
화합물 3-3의 제조Preparation of compound 3-3
플라스크에 화합물 3-2(17g, 70.0 mmol), 1-요오도-3-브로모벤젠 17.7mL(140mmol), CuI 6.6g(35mmol), K3PO4 44.5g(210mmol), 에틸렌디아민(EDA) 4.7mL(70.0mmol) 및 톨루엔 350mL를 녹인 후 120℃에서 5시간 동안 환류시켰다. 반응이 끝나면 에틸 아세테이트로 유기층을 추출하고 마그네슘 설페이트를 이용하여 잔여 수분을 제거한 뒤 건조시키고 컬럼으로 분리하여 화합물 3-3, 27g(97%)을 얻었다.In a flask, compound 3-2 (17g, 70.0 mmol), 1-iodo-3-bromobenzene 17.7 mL (140 mmol), CuI 6.6 g (35 mmol), K 3 PO 4 44.5 g (210 mmol), ethylenediamine (EDA) ) After dissolving 4.7 mL (70.0 mmol) and 350 mL of toluene, it was refluxed at 120° C. for 5 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by a column to obtain compound 3-3, 27g (97%).
화합물 3-4의 제조Preparation of compound 3-4
플라스크에 화합물 3-3(27g, 67.7mmol) 및 화합물 3-1(17.5g, 67.7mmol)을 넣고 DCM 522mL로 녹였다. 메탄설폰산(MSA) 중 P2O5(0.04mL, 1.35mmol)를 넣어준 후 10분간 교반하였다. 반응이 끝나면 NaHCO3(aq)를 넣어준 후 DCM으로 유기층을 추출하였다. 마그네슘 설페이트를 이용하여 잔여 수분을 제거한 뒤 건조시키고 컬럼으로 분리하여 화합물 3-4, 40g(95%)을 얻었다.Compound 3-3 (27g, 67.7mmol) and compound 3-1 (17.5g, 67.7mmol) were added to a flask and dissolved in 522mL of DCM. P 2 O 5 (0.04 mL, 1.35 mmol) in methanesulfonic acid (MSA) was added, followed by stirring for 10 minutes. When the reaction was over, NaHCO 3 (aq) was added and the organic layer was extracted with DCM. After removing residual moisture using magnesium sulfate, it was dried and separated by a column to obtain compound 3-4, 40g (95%).
화합물 3-5의 제조Preparation of compound 3-5
플라스크에 화합물 3-4(15g, 23.4mmol), 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진(6.6g, 25.74mmol), 팔라듐(II) 클로라이드(PdCl2(PPh3)4)(659mg, 0.94mmol) 및 KOAc(10g, 102.9mmol)를 넣고 1,4-디옥산 156mL에 녹였다. 120℃에서 4시간 동안 환류시킨 후 반응이 끝나면 에틸 아세테이트로 유기층을 추출하고 마그네슘 설페이트를 이용하여 잔여 수분을 제거한 뒤 건조시키고 컬럼으로 분리하여 화합물 3-5, 10.6g(66%)을 얻었다.In a flask, compound 3-4 (15g, 23.4mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (6.6g, 25.74mmol), palladium (II) Chloride (PdCl 2 (PPh 3 ) 4 ) (659mg, 0.94mmol) and KOAc (10g, 102.9mmol) were added and dissolved in 1,4-dioxane 156mL. After refluxing at 120° C. for 4 hours, when the reaction was completed, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and separated by column to obtain compound 3-5, 10.6 g (66%).
화합물 H-90의 제조Preparation of compound H-90
플라스크에 화합물 3-5(10.6g, 15.4mmol), 2-클로로-4,6-디페닐-1,3,5-트리아진(3.8g, 14mmol) , Pd(PPh3)4(820mg, 0.77mmol), 2M K2CO3 60mL, EtOH 60mL 및 톨루엔 180mL를 넣고 120℃에서 5시간 동안 환류시켰다. 반응이 끝나면 에틸 아세테이트로 유기층을 추출하고 마그네슘 설페이트를 이용하여 잔여 수분을 제거한 뒤 건조시키고 EA 및 MeOH 로 재결정하여 화합물 H-90, 4g(32.7%)을 얻었다.In a flask, compound 3-5 (10.6g, 15.4mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.8g, 14mmol), Pd(PPh 3 ) 4 (820mg, 0.77 mmol), 2M K 2 CO 3 60 mL, EtOH 60 mL, and toluene 180 mL were added and refluxed at 120° C. for 5 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, dried, and recrystallized from EA and MeOH to obtain compound H-90, 4g (32.7%).
물성 데이타: mp 256℃, UV 324nm(톨루엔 중), PL 439nm(톨루엔 중), MS/EIMS 790.95
Physical data: mp 256°C, UV 324 nm (in toluene), PL 439 nm (in toluene), MS/EIMS 790.95
[소자 실시예 1] 본 발명에 따른 유기 전계 발광 화합물을 이용한 OLED 소자 제작[Device Example 1] Fabrication of an OLED device using the organic electroluminescent compound according to the present invention
본 발명의 유기 전계 발광 화합물을 이용한 구조의 OLED 소자를 제작하였다. 우선, OLED용 글래스(삼성-코닝사 제조)로부터 얻어진 투명 전극 ITO 박막(15Ω/□)을, 트리클로로에틸렌, 아세톤, 에탄올 및 증류수를 순차적으로 사용하여 초음파 세척을 실시한 후, 이소프로판올에 넣어 보관한 후 사용하였다. 다음으로 진공 증착 장비의 기판 홀더에 ITO 기판을 장착한 후, 진공 증착장비 내의 셀에 N1,N1-([1,1'-바이페닐]-4,4'-디일)비스(N1-(나프탈렌-1-일)-N4,N4-디페닐벤젠-1,4-디아민)을 넣고 챔버 내의 진공도가 10-6torr에 도달할 때까지 배기시킨 후, 셀에 전류를 인가하여 증발시켜 ITO 기판 위에 60nm 두께의 정공주입층을 증착하였다. 이어서, 진공 증착 장비 내의 다른 셀에 N,N'-디(4-바이페닐)-N,N'-디(4-바이페닐)-4,4'-디아미노바이페닐을 넣고, 셀에 전류를 인가하여 증발시켜 정공주입층 위에 20nm 두께의 정공전달층을 증착하였다. 진공 증착 장비 내의 한쪽 셀에 호스트로서 화합물 H-34를 넣고, 또 다른 셀에는 도판트로서 화합물 D-1을 넣은 후, 두 물질을 다른 속도로 증발시켜 호스트와 도판트 합계량에 대하여 도판트를 15중량%의 양으로 도핑함으로써 상기 정공전달층 위에 30nm 두께의 발광층을 증착하였다. 이어서 한쪽 셀에 2-(4-(9,10-디(나프탈렌-2-일)안트라센-2-일)페닐)-1-페닐-1H-벤조[d]이미다졸을 넣고, 또 다른 셀에는 리튬 퀴놀레이트(Lithium quinolate)를 넣은 후, 두 물질을 같은 속도로 증발시켜 각각 50중량%의 양으로 도핑함으로써 30nm의 전자전달층을 증착하였다. 이어서 전자주입층으로 리튬 퀴놀레이트를 2nm 두께로 증착한 후, 다른 진공 증착 장비를 이용하여 Al 음극을 150nm의 두께로 증착하여 OLED 소자를 제작하였다. 재료 별로 각 화합물은 10-6torr 하에서 진공 승화 정제하여 사용하였다. 그 결과, 2.5V의 전압에서 3.32mA/cm2의 전류가 흘렀으며, 1310cd/m2의 녹색 발광이 확인되었다.
An OLED device having a structure using the organic electroluminescent compound of the present invention was manufactured. First, the transparent electrode ITO thin film (15Ω/□) obtained from OLED glass (manufactured by Samsung-Corning) was ultrasonically washed sequentially using trichloroethylene, acetone, ethanol and distilled water, and then stored in isopropanol. Used. Next, after mounting the ITO substrate on the substrate holder of the vacuum evaporation equipment, N 1 ,N 1 -([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -(Naphthalen-1-yl)-N 4 ,N 4 -diphenylbenzene-1,4-diamine) was added and exhausted until the degree of vacuum in the chamber reached 10 -6 torr, and then a current was applied to the cell. After evaporation, a hole injection layer having a thickness of 60 nm was deposited on the ITO substrate. Then, N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl was put in another cell in the vacuum deposition equipment, and the current By applying and evaporation, a hole transport layer having a thickness of 20 nm was deposited on the hole injection layer. After putting compound H-34 as a host in one cell of the vacuum evaporation equipment and compound D-1 as a dopant in another cell, the two materials were evaporated at different rates to reduce the dopant to the total amount of the host and dopant. By doping in an amount of weight %, a light emitting layer having a thickness of 30 nm was deposited on the hole transport layer. Then put 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole in one cell, and in another cell After lithium quinolate was added, the two materials were evaporated at the same rate and doped in an amount of 50% by weight, respectively, to deposit an electron transport layer of 30 nm. Subsequently, lithium quinolate was deposited to a thickness of 2 nm as an electron injection layer, and then an Al cathode was deposited to a thickness of 150 nm using another vacuum deposition equipment to fabricate an OLED device. For each material, each compound was used by vacuum sublimation purification under 10 -6 torr. As a result, a current of 3.32 mA/cm 2 flowed at a voltage of 2.5 V, and green light emission of 1310 cd/m 2 was observed.
[소자 실시예 2] 본 발명에 따른 유기 전계 발광 화합물을 이용한 OLED 소자 제작[Device Example 2] Fabrication of an OLED device using the organic electroluminescent compound according to the present invention
발광 재료로서 호스트에 화합물 H-57을 사용한 것 외에는 소자 실시예 1과 동일한 방법으로 OLED 소자를 제작하였다. 그 결과, 2.6V의 전압에서 7.26mA/cm2의 전류가 흘렀으며, 2840cd/m2의 녹색 발광이 확인되었다.
An OLED device was manufactured in the same manner as in Device Example 1, except that the compound H-57 was used as the host as the light emitting material. As a result, a current of 7.26 mA/cm 2 flowed at a voltage of 2.6 V, and green light emission of 2840 cd/m 2 was observed.
[소자 실시예 3] 본 발명에 따른 유기 전계 발광 화합물을 이용한 OLED 소자 제작[Device Example 3] Fabrication of an OLED device using the organic electroluminescent compound according to the present invention
발광 재료로서 호스트에는 화합물 H-90을 사용한 것 외에는 소자 실시예 1과 동일한 방법으로 OLED 소자를 제작하였다. 그 결과, 2.7V의 전압에서 9.40mA/cm2의 전류가 흘렀으며, 3910cd/m2의 녹색 발광이 확인되었다.
An OLED device was fabricated in the same manner as in Device Example 1, except that Compound H-90 was used as the host as a light emitting material. As a result, a current of 9.40 mA/cm 2 flowed at a voltage of 2.7 V, and green light emission of 3910 cd/m 2 was observed.
[비교예 1] 종래의 발광 재료를 이용한 OLED 소자 제작[Comparative Example 1] Fabrication of OLED devices using conventional light emitting materials
발광 재료로서 호스트에는 Compound 1을 이용하고, 도판트에는 화합물 D-86을 사용한 것 외에는 소자 실시예 1과 동일한 방법으로 OLED 소자를 제작하였다. 그 결과, 4.3V의 전압에서 5.20mA/cm2의 전류가 흘렀으며, 1020cd/m2의 녹색 발광이 확인되었다. An OLED device was manufactured in the same manner as in Device Example 1, except that Compound 1 was used as a light emitting material and Compound D-86 was used as a dopant. As a result, a current of 5.20 mA/cm 2 flowed at a voltage of 4.3 V, and green light emission of 1020 cd/m 2 was observed.
본 발명의 유기 전계 발광 화합물들의 발광 특성이 종래의 재료에 비해 우수한 특성을 보였다. 또한 본 발명에 따른 유기 전계 발광 화합물을 발광용 호스트 재료로 사용한 소자는 발광 특성이 뛰어날 뿐만 아니라 구동 전압을 강하시켜줌으로써 전력효율의 상승을 유도하여 소비전력을 개선시킬 수 있었다.The organic electroluminescent compounds of the present invention exhibited superior luminescence properties compared to conventional materials. In addition, the device using the organic electroluminescent compound according to the present invention as a host material for light emission not only has excellent light emission characteristics, but also induces an increase in power efficiency by lowering the driving voltage, thereby improving power consumption.
Claims (6)
[화학식 1]
상기 화학식 1에서,
A1은 치환 또는 비치환 피리딜, 치환 또는 비치환 피리미딘일, 치환 또는 비치환 트리아진일, 치환 또는 비치환 피라진일, 치환 또는 비치환 퀴놀릴, 치환 또는 비치환 퀴나졸리닐, 치환 또는 비치환 퀴녹살리닐, 또는 치환 또는 비치환 나프티리디닐이고;
L1은 단일결합, 또는 치환 또는 비치환 (C6-C20)아릴렌기이며;
R1은 치환 또는 비치환 (C1-C30)알킬기, 또는 비치환 (C6-C30)아릴기이고;
R2는 수소, 중수소, 할로겐, 시아노기, 치환 또는 비치환 (C1-C30)알킬기, 치환 또는 비치환 (C6-C30)아릴기, 치환 또는 비치환 (5-30원)헤테로아릴기, 치환 또는 비치환 (C3-C30)시클로알킬기, 치환 또는 비치환 (C1-C30)알콕시기, 치환 또는 비치환 (C1-C30)알킬실릴기, 치환 또는 비치환 (C6-C30)아릴실릴기, 치환 또는 비치환 (C6-C30)아르(C1-C30)알킬실릴기, 치환 또는 비치환 (C1-C30)알킬아미노기, 치환 또는 비치환 (C6-C30)아릴아미노기, 치환 또는 비치환 (C1-C30)알킬(C6-C30)아릴아미노기, 또는 화학식 2이거나;
[화학식 2]
R2는 카바졸 골격에 융합되어 벤조카바졸을 형성하고;
R3은 수소, 중수소, 할로겐, 시아노기, 치환 또는 비치환 (C1-C30)알킬기, 치환 또는 비치환 (C6-C30)아릴기, 치환 또는 비치환 (5-30원)헤테로아릴기, 치환 또는 비치환 (C3-C30)시클로알킬기, 치환 또는 비치환 (C1-C30)알콕시기, 치환 또는 비치환 (C1-C30)알킬실릴기, 치환 또는 비치환 (C6-C30)아릴실릴기, 치환 또는 비치환 (C6-C30)아르(C1-C30)알킬실릴기, 치환 또는 비치환 (C1-C30)알킬아미노기, 치환 또는 비치환 (C6-C30)아릴아미노기, 또는 치환 또는 비치환 (C1-C30)알킬(C6-C30)아릴아미노기이고;
X는 O, S, CR11R12, NR13 또는 SiR13R14이고;
R4, R5 및 R6은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 치환 또는 비치환 (C1-C30)알킬기, 치환 또는 비치환 (C6-C30)아릴기, 치환 또는 비치환 (5-30원)헤테로아릴기, 치환 또는 비치환 (C3-C30)시클로알킬기, 치환 또는 비치환 (C1-C30)알콕시기, 치환 또는 비치환 (C1-C30)알킬실릴기, 치환 또는 비치환 (C6-C30)아릴실릴기, 치환 또는 비치환 (C6-C30)아르(C1-C30)알킬실릴기, 치환 또는 비치환 (C1-C30)알킬아미노기, 치환 또는 비치환 (C6-C30)아릴아미노기, 또는 치환 또는 비치환 (C1-C30)알킬(C6-C30)아릴아미노기이거나, 서로 인접한 치환체와 연결되어 (C3-C30) 단일환 또는 다환의 지환족 또는 방향족 환을 형성할 수 있고, 상기 형성된 지환족 또는 방향족 환의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고;
R11 내지 R14는 각각 독립적으로 치환 또는 비치환 (C1-C30)알킬기, 치환 또는 비치환 (C6-C30)아릴기, 또는 치환 또는 비치환 (5-30원)헤테로아릴기이거나, 서로 인접한 치환체와 연결되어 (C3-C30) 단일환 또는 다환의 지환족 또는 방향족 환을 형성할 수 있고, 상기 형성된 지환족 또는 방향족 환의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고;
a, c, d 및 e는 각각 독립적으로 1 내지 4의 정수이고, a, c, d 또는 e가 2 이상인 경우 각각의 R2, R4, R5 또는 R6은 동일하거나 상이할 수 있으며;
b는 1 내지 3의 정수이고, b가 2 이상인 경우 각각의 R3은 동일하거나 상이할 수 있고;
n은 0 또는 1의 정수이며;
m은 1 또는 2의 정수이고;
상기 헤테로아릴(렌)은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함한다.An organic electroluminescent compound represented by the following formula (1).
[Formula 1]
In Formula 1,
A 1 is substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted Cyclic quinoxalinyl, or substituted or unsubstituted naphthyridinyl;
L 1 is a single bond or a substituted or unsubstituted (C6-C20) arylene group;
R 1 is a substituted or unsubstituted (C1-C30) alkyl group, or an unsubstituted (C6-C30) aryl group;
R 2 is hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C6-C30) aryl group, substituted or unsubstituted (5-30 membered) heteroaryl group, substituted Or an unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted (C1-C30) alkylsilyl group, a substituted or unsubstituted (C6-C30) arylsilyl group, a substituted Or an unsubstituted (C6-C30) are (C1-C30) alkylsilyl group, a substituted or unsubstituted (C1-C30) alkylamino group, a substituted or unsubstituted (C6-C30) arylamino group, a substituted or unsubstituted (C1-C30) ) Alkyl (C6-C30) arylamino group, or formula 2;
[Formula 2]
R 2 is fused to the carbazole backbone to form benzocarbazole;
R 3 is hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C6-C30) aryl group, substituted or unsubstituted (5-30 membered) heteroaryl group, substituted Or an unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted (C1-C30) alkylsilyl group, a substituted or unsubstituted (C6-C30) arylsilyl group, a substituted Or an unsubstituted (C6-C30) are (C1-C30) alkylsilyl group, a substituted or unsubstituted (C1-C30) alkylamino group, a substituted or unsubstituted (C6-C30) arylamino group, or a substituted or unsubstituted (C1- C30) alkyl (C6-C30) arylamino group;
X is O, S, CR 11 R 12 , NR 13 or SiR 13 R 14 ;
R 4 , R 5 and R 6 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 membered) Heteroaryl group, substituted or unsubstituted (C3-C30) cycloalkyl group, substituted or unsubstituted (C1-C30) alkoxy group, substituted or unsubstituted (C1-C30)alkylsilyl group, substituted or unsubstituted ( C6-C30) arylsilyl group, substituted or unsubstituted (C6-C30) ar (C1-C30) alkylsilyl group, substituted or unsubstituted (C1-C30) alkylamino group, substituted or unsubstituted (C6-C30) arylamino group , Or a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group, or connected with a substituent adjacent to each other to form a (C3-C30) monocyclic or polycyclic alicyclic or aromatic ring, and the formed The carbon atom of the alicyclic or aromatic ring may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur;
R 11 to R 14 are each independently a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-30 membered) heteroaryl group, or adjacent to each other It is connected with a substituent to form a (C3-C30) monocyclic or polycyclic alicyclic or aromatic ring, and the carbon atom of the formed alicyclic or aromatic ring may be replaced by one or more heteroatoms selected from nitrogen, oxygen and sulfur. There is;
a, c, d and e are each independently an integer of 1 to 4, and when a, c, d or e is 2 or more, each of R 2 , R 4 , R 5 or R 6 may be the same or different;
b is an integer of 1 to 3, and when b is 2 or more, each R 3 may be the same or different;
n is an integer of 0 or 1;
m is an integer of 1 or 2;
The heteroaryl (ene) includes one or more heteroatoms selected from B, N, O, S, P(=O), Si and P.
[화학식 3] [화학식 4] [화학식 5]
상기 화학식 3 내지 5에서,
A1, L1, R1, R2, R3, R4, R5, a, b, c, d, m 및 n은 청구항 1에서의 정의와 동일하다.The organic electroluminescent compound of claim 1, wherein the compound of Formula 1 is represented by any one of the following Formulas 3 to 5.
[Formula 3] [Formula 4] [Formula 5]
In Formulas 3 to 5,
A 1 , L 1 , R 1 , R 2 , R 3 , R 4 , R 5 , a, b, c, d, m and n are the same as defined in claim 1.
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| JP2016532083A JP6599860B2 (en) | 2013-12-04 | 2014-12-02 | Novel organic electroluminescent compound and organic electroluminescent device including the same |
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Also Published As
| Publication number | Publication date |
|---|---|
| KR20150064878A (en) | 2015-06-12 |
| WO2015084021A1 (en) | 2015-06-11 |
| CN105745200A (en) | 2016-07-06 |
| TW201533036A (en) | 2015-09-01 |
| CN105745200B (en) | 2021-08-17 |
| JP6599860B2 (en) | 2019-10-30 |
| JP2017501127A (en) | 2017-01-12 |
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