JP6680675B2 - Organic electroluminescent compound and organic electroluminescent device containing the same - Google Patents
Organic electroluminescent compound and organic electroluminescent device containing the same Download PDFInfo
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- JP6680675B2 JP6680675B2 JP2016532095A JP2016532095A JP6680675B2 JP 6680675 B2 JP6680675 B2 JP 6680675B2 JP 2016532095 A JP2016532095 A JP 2016532095A JP 2016532095 A JP2016532095 A JP 2016532095A JP 6680675 B2 JP6680675 B2 JP 6680675B2
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- unsubstituted
- substituted
- aryl
- alkyl
- membered
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- 150000001875 compounds Chemical class 0.000 title claims description 129
- 125000003118 aryl group Chemical group 0.000 claims description 86
- 125000001072 heteroaryl group Chemical group 0.000 claims description 54
- -1 phenylnaphthyl Chemical group 0.000 claims description 46
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 41
- 125000005842 heteroatom Chemical group 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 125000000732 arylene group Chemical group 0.000 claims description 19
- 125000005549 heteroarylene group Chemical group 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 15
- 229910052717 sulfur Chemical group 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 group 0.000 claims description 14
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 13
- 235000010290 biphenyl Nutrition 0.000 claims description 11
- 239000004305 biphenyl Substances 0.000 claims description 11
- 125000001769 aryl amino group Chemical group 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
- 125000005104 aryl silyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000003367 polycyclic group Chemical group 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000005509 dibenzothiophenyl 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
- 239000001301 oxygen Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 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 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 claims description 4
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 3
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000005878 benzonaphthofuranyl group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 claims description 2
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 claims description 2
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 claims description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 2
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 2
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims 2
- QUHIUAFQBFDMIQ-UHFFFAOYSA-N 1,3-dimethyl-5-phenylbenzene Chemical group CC1=CC(C)=CC(C=2C=CC=CC=2)=C1 QUHIUAFQBFDMIQ-UHFFFAOYSA-N 0.000 claims 1
- ALLIZEAXNXSFGD-UHFFFAOYSA-N 1-methyl-2-phenylbenzene Chemical group CC1=CC=CC=C1C1=CC=CC=C1 ALLIZEAXNXSFGD-UHFFFAOYSA-N 0.000 claims 1
- NPDIDUXTRAITDE-UHFFFAOYSA-N 1-methyl-3-phenylbenzene Chemical group CC1=CC=CC(C=2C=CC=CC=2)=C1 NPDIDUXTRAITDE-UHFFFAOYSA-N 0.000 claims 1
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical group C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 claims 1
- 239000005864 Sulphur Chemical group 0.000 claims 1
- 125000006267 biphenyl group Chemical group 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 68
- 239000000463 material Substances 0.000 description 60
- 239000000203 mixture Substances 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 230000005525 hole transport Effects 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 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 16
- 239000002019 doping agent Substances 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 13
- 238000002347 injection Methods 0.000 description 11
- 239000007924 injection Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 238000002390 rotary evaporation Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N Dibenzofuran Natural products C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 5
- 229910052741 iridium Inorganic materials 0.000 description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 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 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
- 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 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000004826 dibenzofurans Chemical class 0.000 description 3
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 3
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-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
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 3
- 229940078552 o-xylene Drugs 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- 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
- JHNLZOVBAQWGQU-UHFFFAOYSA-N 380814_sial Chemical compound CS(O)(=O)=O.O=P(=O)OP(=O)=O JHNLZOVBAQWGQU-UHFFFAOYSA-N 0.000 description 2
- SQTLUXJWUCHKMT-UHFFFAOYSA-N 4-bromo-n,n-diphenylaniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 SQTLUXJWUCHKMT-UHFFFAOYSA-N 0.000 description 2
- JAUCIDPGGHZXRP-UHFFFAOYSA-N 4-phenyl-n-(4-phenylphenyl)aniline Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC(C=C1)=CC=C1C1=CC=CC=C1 JAUCIDPGGHZXRP-UHFFFAOYSA-N 0.000 description 2
- SEQHEDQNODAFIU-UHFFFAOYSA-N 6-bromo-2,3-dihydroinden-1-one Chemical compound BrC1=CC=C2CCC(=O)C2=C1 SEQHEDQNODAFIU-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
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 2
- HAPOJKSPCGLOOD-UHFFFAOYSA-N Benzo[b]fluorene Chemical compound C1=CC=C2C=C3CC4=CC=CC=C4C3=CC2=C1 HAPOJKSPCGLOOD-UHFFFAOYSA-N 0.000 description 2
- FRIJWEQBTIZQMD-UHFFFAOYSA-N Benzo[c]fluorene Chemical compound C1=CC2=CC=CC=C2C2=C1CC1=CC=CC=C12 FRIJWEQBTIZQMD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- MLMNDNOSVOKYMT-UHFFFAOYSA-N benzo[b]fluoren-11-one Chemical compound C1=CC=C2C=C3C(=O)C4=CC=CC=C4C3=CC2=C1 MLMNDNOSVOKYMT-UHFFFAOYSA-N 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 239000012776 electronic material Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 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
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
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- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
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- 239000002344 surface layer Substances 0.000 description 2
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- 239000010409 thin film Substances 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
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- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
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- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
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- 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
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
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- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- GKTLHQFSIDFAJH-UHFFFAOYSA-N 3-(9h-carbazol-3-yl)-9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=C(C=3C=C4C5=CC=CC=C5NC4=CC=3)C=C2C2=CC=CC=C21 GKTLHQFSIDFAJH-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
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- KSONICAHAPRCMV-UHFFFAOYSA-N 5-bromo-2,3-dihydroinden-1-one Chemical compound BrC1=CC=C2C(=O)CCC2=C1 KSONICAHAPRCMV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
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- 239000002841 Lewis acid Substances 0.000 description 1
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- 229910003564 SiAlON Inorganic materials 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
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- ADSXDBCZNVXTRD-UHFFFAOYSA-N [Mg]C1=CC=CC=C1 Chemical compound [Mg]C1=CC=CC=C1 ADSXDBCZNVXTRD-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-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
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- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- UUESRJFGZMCELZ-UHFFFAOYSA-K aluminum;2-methylquinoline-8-carboxylate;4-phenylphenolate Chemical compound [Al+3].C1=CC([O-])=CC=C1C1=CC=CC=C1.C1=CC=C(C([O-])=O)C2=NC(C)=CC=C21.C1=CC=C(C([O-])=O)C2=NC(C)=CC=C21 UUESRJFGZMCELZ-UHFFFAOYSA-K 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
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- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
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- 239000000872 buffer Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 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
- 238000000354 decomposition reaction Methods 0.000 description 1
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- 238000003618 dip coating Methods 0.000 description 1
- 238000000469 dry deposition Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005401 electroluminescence 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
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- 125000000524 functional group Chemical group 0.000 description 1
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- 230000009477 glass transition Effects 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- AOZVYCYMTUWJHJ-UHFFFAOYSA-K iridium(3+) pyridine-2-carboxylate Chemical compound [Ir+3].[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1 AOZVYCYMTUWJHJ-UHFFFAOYSA-K 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 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
- 229910052744 lithium Inorganic materials 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
- 230000007246 mechanism Effects 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 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
- 239000011368 organic material Substances 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
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- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
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- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
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- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
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- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Description
本開示は、有機電界発光化合物、及びそれを含む有機電界発光デバイスに関する。 The present disclosure relates to organic electroluminescent compounds and organic electroluminescent devices containing the same.
電界発光（ＥＬ）デバイスは、それが、より広い視角、より優れたコントラスト比、及びより高速な応答時間を提供するという点で、利点を有する自己発光デバイスである。有機ＥＬデバイスは、発光層を形成するために芳香族ジアミン小分子とアルミニウムとの錯体を材料として使用することによって、Ｅａｓｔｍａｎ Ｋｏｄａｋによって初めて開発された［Ａｐｐｌ．Ｐｈｙｓ．Ｌｅｔｔ．５１，９１３，１９８７］。 Electroluminescent (EL) devices are self-luminous devices that have the advantage in that they provide wider viewing angles, better contrast ratios, and faster response times. Organic EL devices were first developed by Eastman Kodak by using a complex of an aromatic diamine small molecule and aluminum as a material to form a light emitting layer [Appl. Phys. Lett. 51, 913, 1987].
有機ＥＬデバイスにおいて発光効率を決定する最も重要な要因は、発光材料である。これまで、蛍光性材料が発光材料として広く使用されてきた。しかしながら、電界発光機構の点から見て、リン光性材料は、理論上、蛍光性材料と比較して発光効率を４倍向上させるため、リン光性発光材料が広く研究されている。イリジウム（ＩＩＩ）錯体は、ビス（２−（２’−ベンゾチエニル）−ピリジナト−Ｎ，Ｃ−３’）イリジウム（アセチルアセトネート）（（ａｃａｃ）Ｉｒ（ｂｔｐ）２）、トリス（２−フェニルピリジン）イリジウム（Ｉｒ（ｐｐｙ）３）、及びビス（４，６−ジフルオロフェニルピリジナト−Ｎ，Ｃ２）ピコリネートイリジウム（Ｆｉｒｐｉｃ）を、それぞれ、赤色、緑色、及び青色を放出する材料として含む、リン光性材料として広く知られている。 The most important factor that determines the luminous efficiency in an organic EL device is the light emitting material. Until now, fluorescent materials have been widely used as light emitting materials. However, from the viewpoint of the electroluminescence mechanism, the phosphorescent material theoretically improves the luminous efficiency four times as compared with the fluorescent material, and thus the phosphorescent material has been widely studied. The iridium (III) complex includes bis (2- (2′-benzothienyl) -pyridinato-N, C-3 ′) iridium (acetylacetonate) ((acac) Ir (btp) 2 ), tris (2-phenyl). Pyridine) iridium (Ir (ppy) 3 ) and bis (4,6-difluorophenylpyridinato-N, C2) picolinate iridium (Firpic) as the red, green, and blue emitting materials, respectively. , Is widely known as a phosphorescent material.
現在のところ、４，４’−Ｎ，Ｎ’−ジカルバゾール−ビフェニル（ＣＢＰ）が、リン光性材料の最も広く知られたホスト材料である。最近、Ｐｉｏｎｅｅｒ（日本）らが、正孔阻止材料として知られていたバソクプロイン（ＢＣＰ）及びアルミニウム（ＩＩＩ）ビス（２−メチル−８−キノリネート）（４−フェニルフェノレート）（ＢＡｌｑ）などをホスト材料として使用する高性能有機ＥＬデバイスを開発した。 At present, 4,4'-N, N'-dicarbazole-biphenyl (CBP) is the most widely known host material for phosphorescent materials. Recently, Pioneer (Japan) et al. Have hosted bathocuproine (BCP) and aluminum (III) bis (2-methyl-8-quinolinate) (4-phenylphenolate) (BAlq), which have been known as hole blocking materials. We have developed a high-performance organic EL device used as a material.
これらの材料は良好な発光特徴を提供するが、それらは、以下の欠点を有する。（１）それらの低ガラス転移温度及び熱安定性の低さに起因して、真空でも高温蒸着処理中にそれらの分解が生じ得、これは、短い寿命をもたらす。（２）有機ＥＬデバイスの電力効率は、［（π／電圧）×電流効率］によって得られ、この電力効率は、電圧に反比例する。リン光性ホスト材料を含む有機ＥＬデバイスは蛍光性材料を含むものよりも高い電流効率（ｃｄ／Ａ）を提供するが、極めて高い駆動電圧が必要である。したがって、電力効率（ｌｍ／Ｗ）の観点では利点がない。（３）さらに、有機ＥＬデバイスの動作寿命は短く、発光効率は依然として改善を要する。 Although these materials provide good emission characteristics, they have the following drawbacks. (1) Due to their low glass transition temperature and poor thermal stability, their decomposition can occur even during vacuum during the high temperature vapor deposition process, resulting in a short lifetime. (2) The power efficiency of the organic EL device is obtained by [(π / voltage) × current efficiency], and the power efficiency is inversely proportional to the voltage. Organic EL devices containing phosphorescent host materials offer higher current efficiencies (cd / A) than those containing fluorescent materials, but require very high drive voltages. Therefore, there is no advantage in terms of power efficiency (lm / W). (3) Furthermore, the operating life of the organic EL device is short, and the luminous efficiency still needs improvement.
効率及び安定性を改善するために、有機ＥＬデバイスは、正孔注入層、正孔輸送層、発光層、電子輸送層、及び電子注入層などが含まれる多層構造で製造され得る。この構造において、正孔輸送層のための化合物が、正孔を発光層に輸送するための効率、発光効率、及び寿命等のデバイスの特徴を向上させるのに重要である。 To improve efficiency and stability, the organic EL device may be manufactured in a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In this structure, the compound for the hole transport layer is important for improving device characteristics such as efficiency for transporting holes to the light emitting layer, luminous efficiency, and lifetime.
その際、銅フタロシアニン（ＣｕＰｃ）、４，４’−ビス［Ｎ−（１−ナフチル）−Ｎ−フェニルアミノ］ビフェニル（ＮＰＢ）、Ｎ，Ｎ’−ジフェニル−Ｎ，Ｎ’−ビス（３−メチルフェニル）−（１，１’−ビフェニル）−４，４’−ジアミン（ＴＰＤ）、４，４’，４’’−トリス（３−メチルフェニルフェニルアミノ）トリフェニルアミン（ＭＴＤＡＴＡ）などが、有機ＥＬデバイスの正孔注入及び輸送材料として使用されてきた。しかしながら、これらの材料を使用する有機ＥＬデバイスは、量子効率及び寿命の点で問題がある。これは、有機ＥＬデバイスが高電流の下で駆動されるときに、アノードと正孔注入層との間で起こる熱応力に起因する。熱応力は、デバイスの寿命を著しく低減させる。さらに、正孔注入層に使用される有機材料は、非常に高い正孔移動度を有するため、正孔−電子電荷のバランスが崩れる可能性があり、量子収率（ｃｄ／Ａ）が低下し得る。 At that time, copper phthalocyanine (CuPc), 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB), N, N′-diphenyl-N, N′-bis (3-) Methylphenyl)-(1,1′-biphenyl) -4,4′-diamine (TPD), 4,4 ′, 4 ″ -tris (3-methylphenylphenylamino) triphenylamine (MTDATA), etc. It has been used as a hole injection and transport material in organic EL devices. However, organic EL devices using these materials have problems in quantum efficiency and lifetime. This is due to the thermal stress that occurs between the anode and the hole injection layer when the organic EL device is driven under high current. Thermal stress significantly reduces device life. Furthermore, since the organic material used for the hole injection layer has a very high hole mobility, the hole-electron charge balance may be lost, and the quantum yield (cd / A) may decrease. obtain.
韓国特許出願公開第１０−２０１２−００２９４４６号、国際公開第２０１３−０６５５８９号、及び国際公開第２００７−１１９８００号は、有機ＥＬデバイスのための化合物として、ベンゾフルオレン系置換基を有するアミン誘導体を開示する。しかしながら、これらの参考文献のベンゾフルオレン系置換基は、ベンゾ［ａ］フルオレン−またはベンゾ［ｃ］フルオレン系置換基である。ベンゾ［ｂ］フルオレン系置換基を有するアミン誘導体は、参考文献中に特に開示されていない。 Korean Patent Application Publication No. 10-2012-0029446, International Publication No. 2013-065589, and International Publication No. 2007-119800 disclose amine derivatives having benzofluorene-based substituents as compounds for organic EL devices. To do. However, the benzofluorene-based substituents in these references are benzo [a] fluorene- or benzo [c] fluorene-based substituents. No amine derivative having a benzo [b] fluorene-based substituent is specifically disclosed in the reference.
本開示の目的は、電流効率等の発光効率を示す有機電界発光化合物、及びそれを含む有機電界発光デバイスを提供することである。 An object of the present disclosure is to provide an organic electroluminescent compound exhibiting luminous efficiency such as current efficiency, and an organic electroluminescent device including the same.
本発明者らは、上の目的が、以下の式１によって表される有機電界発光化合物によって達成され得ることを見出し、 The inventors have found that the above objects can be achieved by an organic electroluminescent compound represented by Formula 1 below,
式中、
Ａｒ１〜Ａｒ４は、それぞれ独立して、置換もしくは非置換（Ｃ６−Ｃ３０）アリール、または置換もしくは非置換（５〜３０員）ヘテロアリールを表し、Ａｒ１及びＡｒ２は、互いに縮合して環を形成し得、
Ａｒ５は、置換もしくは非置換（Ｃ１−Ｃ３０）アルキル、置換もしくは非置換（Ｃ６−Ｃ３０）アリール、または置換もしくは非置換（５〜３０員）ヘテロアリールを表し、
Ｌ１は、単結合、置換もしくは非置換（Ｃ６−Ｃ３０）アリーレン、または置換もしくは非置換（５〜３０員）ヘテロアリーレンを表し、
Ｌ２は、置換もしくは非置換（Ｃ１−Ｃ３０）アルキレン、置換もしくは非置換（Ｃ６−Ｃ３０）アリーレン、または置換もしくは非置換（５〜３０員）ヘテロアリーレンを表し、
Ｒ１及びＲ２は、それぞれ独立して、水素、重水素、ハロゲン、置換もしくは非置換（Ｃ１−Ｃ３０）アルキル、置換もしくは非置換（Ｃ６−Ｃ３０）アリール、置換もしくは非置換（５〜３０員）ヘテロアリール、置換もしくは非置換（Ｃ３−Ｃ３０）シクロアルキル、置換もしくは非置換（３〜７員）ヘテロシクロアルキル、置換もしくは非置換（Ｃ６−Ｃ３０）アリール（Ｃ１−Ｃ３０）アルキル、−Ｎ（Ｒ１１）（Ｒ１２）、−Ｓｉ（Ｒ１３）（Ｒ１４）（Ｒ１５）、−Ｓ（Ｒ１６）、−Ｏ（Ｒ１７）、シアノ、ニトロ、またはヒドロキシルを表すか、あるいは隣接する置換基（複数可）と連結して、（３〜３０員）の単環式もしくは多環式の、脂環式もしくは芳香族の環を形成し得、その炭素原子（複数可）は窒素、酸素、及び硫黄から選択される少なくとも１つのヘテロ原子と置き換えられてもよく、
Ｒ１１〜Ｒ１７は、それぞれ独立して、水素、重水素、ハロゲン、置換もしくは非置換（Ｃ１−Ｃ３０）アルキル、置換もしくは非置換（Ｃ６−Ｃ３０）アリール、置換もしくは非置換（５〜３０員）ヘテロアリール、置換もしくは非置換（３〜７員）ヘテロシクロアルキル、または置換もしくは非置換（Ｃ３−Ｃ３０）シクロアルキルを表すか、あるいは隣接する置換基（複数可）と連結して、（３〜３０員）の単環式もしくは多環式の、脂環式もしくは芳香族の環を形成し得、その炭素原子（複数可）は、窒素、酸素、及び硫黄から選択される少なくとも１つのヘテロ原子と置き換えられてもよく、
ｎ及びｍは、それぞれ独立して、０または１を表すが、但し、ｎ及びｍの両方が、同時に０になることができないことを条件とし、
ａは、１〜３の整数を表し、ａが２以上の整数である場合、Ｒ１のそれぞれは同じであっても異なってもよく、
ｂは、１〜６の整数を表し、ｂが２以上の整数である場合、Ｒ２のそれぞれは同じであっても異なってもよく、
ヘテロアリール（エン）は、Ｂ、Ｎ、Ｏ、Ｓ、Ｐ（＝Ｏ）、Ｓｉ、及びＰから選択される少なくとも１つのヘテロ原子を含有し、
ヘテロシクロアルキルは、Ｏ、Ｓ、及びＮから選択される少なくとも１つのヘテロ原子を含有する。
Where:
Ar 1 to Ar 4 each independently represent a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5 to 30 membered) heteroaryl, and Ar 1 and Ar 2 are condensed with each other. Can form a ring,
Ar 5 represents substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5 to 30 membered) heteroaryl,
L 1 represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5 to 30 membered) heteroarylene,
L 2 represents a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5 to 30 membered) heteroarylene,
R 1 and R 2 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5 to 30 members). ) Heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl (C1-C30) alkyl, -N ( R 11 ) (R 12 ), —Si (R 13 ) (R 14 ) (R 15 ), —S (R 16 ), —O (R 17 ), cyano, nitro, or hydroxyl. It may be linked to a substituent (s) to form a (3-30 member) mono- or polycyclic, alicyclic or aromatic ring, the carbon atom (s) of which is nitrogen, acid And may be replaced with at least one heteroatom selected from elemental and sulfur,
R 11 to R 17 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5 to 30 members). ) Represents heteroaryl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, or substituted or unsubstituted (C3-C30) cycloalkyl, or is linked to adjacent substituent (s), (3 To 30 members) may form a monocyclic or polycyclic, alicyclic or aromatic ring, the carbon atom (s) of which is at least one heteroatom selected from nitrogen, oxygen, and sulfur. May be replaced by an atom,
n and m each independently represent 0 or 1, provided that both n and m cannot be 0 at the same time,
a represents an integer of 1 to 3, and when a is an integer of 2 or more, each R 1 may be the same or different,
b represents an integer of 1 to 6, and when b is an integer of 2 or more, each R 2 may be the same or different,
Heteroaryl (ene) contains at least one heteroatom selected from B, N, O, S, P (= O), Si, and P,
Heterocycloalkyl contains at least one heteroatom selected from O, S, and N.
発明の有利な効果
本開示の有機電界発光化合物は、電流効率等の発光効率において卓越性を示す有機電界発光デバイスを提供することができる。
Advantageous Effects of the Invention The organic electroluminescent compound of the present disclosure can provide an organic electroluminescent device that exhibits excellence in luminous efficiency such as current efficiency.
以降に、本開示を詳細に記載する。しかしながら、以下の記載は、本発明を説明することを意図するものであり、決して本発明の範囲を制限することを意味するものではない。 Hereinafter, the present disclosure will be described in detail. However, the following description is intended to illustrate the invention and is not meant to limit the scope of the invention in any way.
本開示は、上記の式１の有機電界発光化合物、本有機電界発光化合物を含む有機電界発光材料、及び本有機電界発光化合物を含む有機電界発光デバイスを提供する。 The present disclosure provides an organic electroluminescent compound of Formula 1 above, an organic electroluminescent material comprising the present organic electroluminescent compound, and an organic electroluminescent device comprising the present organic electroluminescent compound.
式１の有機電界発光化合物の詳細は、下記の通りである。 Details of the organic electroluminescent compound of Formula 1 are as follows.
本明細書で、「アルキル」には、メチル、エチル、ｎ−プロピル、イソプロピル、ｎ−ブチル、イソブチル、ｔｅｒｔ−ブチルなどが挙げられる。「アルケニル」には、ビニル、１−プロペニル、２−プロペニル、１−ブテニル、２−ブテニル、３−ブテニル、２−メチルブタ−２−エニル、などが挙げられる。「アルキニル」には、エチニル、１−プロピニル、２−プロピニル、１−ブチニル、２−ブチニル、３−ブチニル、１−メチルペント−２−イニルなどが挙げられる。「シクロアルキル」には、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシルなどが挙げられる。「（３〜７員）ヘテロシクロアルキル」は、Ｂ、Ｎ、Ｏ、Ｓ、Ｐ（＝Ｏ）、Ｓｉ、及びＰ、好ましくはＯ、Ｓ、及びＮから選択される少なくとも１つのヘテロ原子を含む３〜７個の環骨格原子を有するシクロアルキルを示し、テトラヒドロフラン、ピロリジン、チオラン、テトラヒドロピランなどが挙げられる。さらに、「アリール（エン）」は、芳香族炭化水素に由来する単環式環または縮合環を示し、フェニル、ビフェニル、ターフェニル、ナフチル、ビナフチル、フェニルナフチル、ナフチルフェニル、フルオレニル、フェニルフルオレニル、ベンゾフルオレニル、ジベンゾフルオレニル、フェナントレニル、フェニルフェナントレニル、アントラセニル、インデニル、トリフェニレニル、ピレニル、テトラセニル、ペリレニル、クリセニル、ナフタセニル、フルオランテニルなどが挙げられる。「（５〜３０員）ヘテロアリール（エン）」は、Ｂ、Ｎ、Ｏ、Ｓ、Ｐ（＝Ｏ）、Ｓｉ、及びＰからなる群から選択される少なくとも１個、好ましくは１〜４個のヘテロ原子を含む５〜３０個の環骨格原子を有するアリール基を示し、これは単環式環または少なくとも１つのベンゼン環と縮合した縮合環であり得、部分的に飽和であり得、少なくとも１つのヘテロアリールまたはアリール基を単結合（複数可）によってヘテロアリール基と連結させることによって形成されるものであり得、フリル、チオフェニル、ピロリル、イミダゾリル、ピラゾリル、チアゾリル、チアジアゾリル、イソチアゾリル、イソオキサゾリル、オキサゾリル、オキサジアゾリル、トリアジニル、テトラジニル、トリアゾリル、テトラゾリル、フラザニル、ピリジル、ビピラジル、ピラジニル、ピリミジニル、ピリダジニルなどの単環式環型ヘテロアリール及びベンゾフラニル、ベンゾチオフェニル、イソベンゾフラニル、ジベンゾフラニル、ジベンゾチオフェニル、ナフトフラニル、ナフトチオフェニル、ベンゾナフトフラニル、ベンゾナフトチオフェニル、ベンズイミダゾリル、ベンゾチアゾリル、ベンゾイソチアゾリル、ベンゾイソオキサゾリル、ベンゾオキサゾリル、イソインドリル、インドリル、インドリニル、インダゾリル、ベンゾチアジアゾリル、キノリル、イソキノリル、シノリニル、キナゾリニル、キノキサリニル、カルバゾリル、フェノキサジニル、フェナントリジニル、ベンゾジオキソリルなどの縮合環型ヘテロアリールが挙げられる。さらに、「ハロゲン」には、Ｆ、Ｃｌ、Ｂｒ、及びＩが挙げられる。 In the present specification, “alkyl” includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and the like. "Alkenyl" includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like. "Alkynyl" includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl and the like. “Cycloalkyl” includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. "(3-7 membered) heterocycloalkyl" means at least one heteroatom selected from B, N, O, S, P (= O), Si, and P, preferably O, S, and N. It represents a cycloalkyl having 3 to 7 ring skeleton atoms, including tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran and the like. Furthermore, "aryl (ene)" represents a monocyclic ring or a condensed ring derived from an aromatic hydrocarbon, and is phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl. , Benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl and the like. "(5 to 30 membered) heteroaryl (ene)" is at least one, preferably 1 to 4 selected from the group consisting of B, N, O, S, P (= O), Si and P. Represents an aryl group having 5 to 30 ring skeleton atoms containing a heteroatom, which may be a monocyclic ring or a fused ring fused with at least one benzene ring, may be partially saturated, at least It may be formed by linking one heteroaryl or an aryl group with a heteroaryl group by a single bond (s), furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl. , Oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, flazanyl, pyridyl Bicyclic, heterocyclic aryl such as bipyrazyl, pyrazinyl, pyrimidinyl, pyridazinyl and benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, naphthofuranyl, naphthothiophenyl, benzonaphthofuranyl, benzonaphthothiol Phenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indolinyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, Examples thereof include fused ring type heteroaryls such as phenanthridinyl and benzodioxolyl. Further, "halogen" includes F, Cl, Br, and I.
本明細書において、「置換もしくは非置換」という表現における「置換」とは、ある特定の官能基中の水素原子が、別の原子または基、すなわち置換基で置き換えられることを意味する。式１の、Ａｒ１〜Ａｒ５、Ｌ１、Ｌ２、Ｒ１、Ｒ２、及びＲ１１〜Ｒ１７の、置換アルキル（エン）、置換アリール（エン）、置換ヘテロアリール（エン）、置換シクロアルキル、置換ヘテロシクロアルキル、及び置換アリールアルキルの置換基が、それぞれ独立して、重水素、ハロゲン、非置換またはハロゲンで置換された（Ｃ１−Ｃ３０）アルキル、（Ｃ１−Ｃ３０）アルコキシ、（Ｃ６−Ｃ３０）アリール、非置換または（Ｃ６−Ｃ３０）アリールで置換された（３〜３０員）ヘテロアリール、（Ｃ３−Ｃ３０）シクロアルキル、（３〜７員）ヘテロシクロアルキル、トリ（Ｃ１−Ｃ３０）アルキルシリル、トリ（Ｃ６−Ｃ３０）アリールシリル、ジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリル、（Ｃ１−Ｃ３０）アルキルジ（Ｃ６−Ｃ３０）アリールシリル、（Ｃ２−Ｃ３０）アルケニル、（Ｃ２−Ｃ３０）アルキニル、シアノ、ジ（Ｃ１−Ｃ３０）アルキルアミノ、非置換または（Ｃ１−Ｃ３０）アルキルで置換されたジ（Ｃ６−Ｃ３０）アリールアミノ、（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールアミノ、ジ（Ｃ６−Ｃ３０）アリールボロニル、ジ（Ｃ１−Ｃ３０）アルキルボロニル、（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールボロニル、（Ｃ６−Ｃ３０）アリール（Ｃ１−Ｃ３０）アルキル、（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリール、カルボキシル、ニトロ、及びヒドロキシルからなる群から選択される少なくとも１つであり、好ましくは、それぞれ独立して、（Ｃ１−Ｃ３０）アルキル、（Ｃ６−Ｃ２１）アリール、非置換または（Ｃ６−Ｃ１２）アリールで置換された（５〜２１員）ヘテロアリール、及びジ（Ｃ６−Ｃ２１）アリールアミノからなる群から選択される少なくとも１つである。 In the present specification, “substituted” in the expression “substituted or unsubstituted” means that a hydrogen atom in a specific functional group is replaced with another atom or group, that is, a substituent. In Formula 1, Ar 1 to Ar 5 , L 1 , L 2 , R 1 , R 2 , and R 11 to R 17 are substituted alkyl (ene), substituted aryl (ene), substituted heteroaryl (ene), or substituted. The substituents of cycloalkyl, substituted heterocycloalkyl, and substituted arylalkyl are each independently deuterium, halogen, unsubstituted or substituted (C1-C30) alkyl, (C1-C30) alkoxy, ( C6-C30) aryl, (3-30 membered) heteroaryl, unsubstituted or substituted with (C6-C30) aryl, (C3-C30) cycloalkyl, (3-7 membered) heterocycloalkyl, tri (C1-). C30) alkylsilyl, tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1-C3) 0) Alkyldi (C6-C30) arylsilyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, di (C1-C30) alkylamino, unsubstituted or substituted with (C1-C30) alkyl. (C6-C30) Arylamino, (C1-C30) alkyl (C6-C30) arylamino, di (C6-C30) arylboronyl, di (C1-C30) alkylboronyl, (C1-C30) alkyl (C6 -C30) aryl boronyl, (C6-C30) aryl (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, at least one selected from the group consisting of carboxyl, nitro, and hydroxyl. And preferably each independently, (C1-C30) alkyl, (C6-C2) ) Aryl, unsubstituted or (C6-C12) substituted with an aryl (5 to 21 membered) heteroaryl, and at least one selected from the group consisting of di (C6-C21) arylamino.
本開示の一態様に従って、式１の化合物は、以下の式２〜４、好ましくは以下の式２または３のうちのいずれか１つによって表され、 According to one aspect of the present disclosure, the compound of formula 1 is represented by any one of formulas 2-4 below, preferably formula 2 or 3 below:
式中、Ａｒ１〜Ａｒ５、Ｌ１、Ｌ２、Ｒ１、Ｒ２、ａ、及びｂは、上記の式１で定義される通りである。 In the formula, Ar 1 to Ar 5 , L 1 , L 2 , R 1 , R 2 , a, and b are as defined in Formula 1 above.
式１〜４において、Ａｒ１〜Ａｒ４は、それぞれ独立して、置換もしくは非置換（Ｃ６−Ｃ３０）アリール、または置換もしくは非置換（５〜３０員）ヘテロアリールを表し、Ａｒ１及びＡｒ２は、互いに縮合して環を形成し得る。好ましくは、Ａｒ１〜Ａｒ４は、それぞれ独立して、置換もしくは非置換（Ｃ６−Ｃ２１）アリール、または置換もしくは非置換（５〜２１員）ヘテロアリールを表し、Ａｒ１及びＡｒ２は、互いに縮合して環を形成し得、より好ましくは、置換もしくは非置換（Ｃ６−Ｃ２１）アリールを表し、（Ｃ６−Ｃ２１）アリールの置換基は、（Ｃ１−Ｃ３０）アルキル、非置換または（Ｃ１−Ｃ１０）アルキルで置換された（Ｃ６−Ｃ２１）アリール、及び非置換または（Ｃ６−Ｃ１２）アリールで置換された（５〜２１員）ヘテロアリールからなる群から選択される少なくとも１つであり得、Ａｒ１及びＡｒ２は、互いに縮合して環を形成し得る。特に、Ａｒ１〜Ａｒ４は、それぞれ独立して、フェニル、ビフェニル、ターフェニル、ナフチル、フルオレニル、またはベンゾフルオレニルを表し得、Ａｒ１及びＡｒ２は、互いに縮合して環を形成し得る。特に、Ａｒ１〜Ａｒ４の置換基は、（Ｃ１−Ｃ４）アルキル、フェニル、ナフチル、フルオレニル、９，９−ジメチル−９Ｈ−フルオレニル、ピリジル、ピリミジル、キノリニル、イソキノリニル、キナゾリニル、キノキサリニル、９−フェニルカルバゾリル、ジベンゾチオフェニル、及びジベンゾフラニルからなる群から選択される少なくとも１つであり得る。 In Formulas 1 to 4, Ar 1 to Ar 4 each independently represent substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (5 to 30 membered) heteroaryl, and Ar 1 and Ar 2 May be fused together to form a ring. Preferably, Ar 1 to Ar 4 each independently represent a substituted or unsubstituted (C6-C21) aryl or a substituted or unsubstituted (5 to 21 membered) heteroaryl, and Ar 1 and Ar 2 are mutually different. It may be condensed to form a ring, and more preferably represents a substituted or unsubstituted (C6-C21) aryl, and the substituent of the (C6-C21) aryl is (C1-C30) alkyl, unsubstituted or (C1-C30) alkyl. C10) alkyl-substituted (C6-C21) aryl, and unsubstituted or (C6-C12) aryl-substituted (5-21 membered) heteroaryl may be at least one selected from the group consisting of: Ar 1 and Ar 2 may be fused with each other to form a ring. In particular, Ar 1 to Ar 4 may each independently represent phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, or benzofluorenyl, Ar 1 and Ar 2 may be condensed with each other to form a ring. . In particular, the substituents of Ar 1 to Ar 4 are (C1-C4) alkyl, phenyl, naphthyl, fluorenyl, 9,9-dimethyl-9H-fluorenyl, pyridyl, pyrimidyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, 9-phenyl. It may be at least one selected from the group consisting of carbazolyl, dibenzothiophenyl, and dibenzofuranyl.
特に、Ａｒ１及びＡｒ２によって形成された環は、以下の式５によって表され得、 In particular, the ring formed by Ar 1 and Ar 2 may be represented by Formula 5 below:
式中、Ｒ３及びＲ４は、それぞれ独立して、水素、（Ｃ１−Ｃ３０）アルキル、（Ｃ６−Ｃ３０）アリール、または非置換もしくは（Ｃ６−Ｃ３０）アリールで置換された（３〜３０員）ヘテロアリールを表し、＊は、Ｌ１に接続するための部位を表す。 In the formula, R 3 and R 4 each independently represent hydrogen, (C 1 -C 30) alkyl, (C 6 -C 30) aryl, or unsubstituted or (C 6 -C 30) aryl-substituted (3 to 30 members). ) Represents a heteroaryl, and * represents a site for connecting to L 1 .
特に、Ｒ３及びＲ４のうちの一方は、水素を表し、他方は、（Ｃ１−Ｃ４）アルキル、フェニル、ビフェニル、ナフチル、非置換またはフェニル、ビフェニル、もしくはナフチルで置換されたカルバゾリル、非置換またはフェニル、ビフェニル、もしくはナフチルで置換されたジベンゾチオフェニル、及び非置換またはフェニル、ビフェニル、もしくはナフチルで置換されたジベンゾフラニルからなる群から選択され得る。 In particular, one of R 3 and R 4 represents hydrogen and the other is (C1-C4) alkyl, phenyl, biphenyl, naphthyl, unsubstituted or carbazolyl substituted with phenyl, biphenyl or naphthyl, unsubstituted Or it may be selected from the group consisting of dibenzothiophenyl substituted with phenyl, biphenyl, or naphthyl, and dibenzofuranyl unsubstituted or substituted with phenyl, biphenyl, or naphthyl.
Ａｒ５は、置換もしくは非置換（Ｃ１−Ｃ３０）アルキル、置換もしくは非置換（Ｃ６−Ｃ３０）アリール、または置換もしくは非置換（５〜３０員）ヘテロアリールを表す。好ましくは、Ａｒ５は、置換もしくは非置換（Ｃ１−Ｃ２０）アルキル、置換もしくは非置換（Ｃ６−Ｃ２１）アリール、または置換もしくは非置換（５〜２１員）ヘテロアリールを表す。より好ましくは、Ａｒ５は、非置換（Ｃ１−Ｃ１０）アルキル；非置換（Ｃ６−Ｃ１８）アリール、あるいは（Ｃ１−Ｃ１０）アルキル、（Ｃ６−Ｃ２１）アリール、非置換または（Ｃ６−Ｃ１３）アリールもしくはジ（Ｃ６−Ｃ１８）アリールアミノで置換された（６〜２１員）ヘテロアリールで置換された（Ｃ６−Ｃ１８）アリール；あるいは非置換（６〜２１員）ヘテロアリール、または（Ｃ１−Ｃ１０）アルキルもしくは（Ｃ６−Ｃ１８）アリールで置換され、かつＮ、Ｏ、及びＳから選択されるヘテロ原子（複数可）を含有する（６〜２１員）ヘテロアリールを表す。特に、Ａｒ５は、（Ｃ１−Ｃ４）アルキル；非置換、あるいは（Ｃ１−Ｃ４）アルキル、フェニル、カルバゾリル、ジフェニルピリミジル、ジフェニルトリアジニル、フェニルベンズイミダゾリル、ジフェニルアミノ、（フェニル）（ビフェニル）アミノ、ジ（ビフェニル）アミノ、もしくは（フェニル）（ナフチル）アミノで置換されたフェニル、ビフェニル、ナフチル、ターフェニル、フェナントレニル、アントラセニル、またはフルオレニル；あるいは非置換、またはフェニルで置換されたカルバゾリル、ベンゾカルバゾリル、ジベンゾチオフェニル、ベンゾナフトチオフェニル、ジベンゾフラニル、もしくはベンゾナフトフラニルを表す。 Ar 5 is a substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (5-30 membered) heteroaryl. Preferably, Ar 5 represents a substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C21) aryl, or a substituted or unsubstituted (5-21 membered) heteroaryl. More preferably, Ar 5 is unsubstituted (C1-C10) alkyl; unsubstituted (C6-C18) aryl, or (C1-C10) alkyl, (C6-C21) aryl, unsubstituted or (C6-C13) aryl. Or (C6-C18) aryl substituted with (6-21 membered) heteroaryl substituted with di (C6-C18) arylamino; or unsubstituted (6-21 membered) heteroaryl, or (C1-C10) Represents (6-21 membered) heteroaryl substituted with alkyl or (C6-C18) aryl and containing the heteroatom (s) selected from N, O, and S. In particular, Ar 5 is (C1-C4) alkyl; unsubstituted or (C1-C4) alkyl, phenyl, carbazolyl, diphenylpyrimidyl, diphenyltriazinyl, phenylbenzimidazolyl, diphenylamino, (phenyl) (biphenyl) ) Amino, di (biphenyl) amino, or (phenyl) (naphthyl) amino substituted phenyl, biphenyl, naphthyl, terphenyl, phenanthrenyl, anthracenyl, or fluorenyl; or unsubstituted or phenyl substituted carbazolyl, benzo Represents carbazolyl, dibenzothiophenyl, benzonaphthothiophenyl, dibenzofuranyl, or benzonaphthofuranyl.
Ｌ１は、単結合、置換もしくは非置換（Ｃ６−Ｃ３０）アリーレン、または置換もしくは非置換（５〜３０員）ヘテロアリーレンを表す。好ましくは、Ｌ１は、単結合、置換もしくは非置換（Ｃ６−Ｃ２１）アリーレン、または置換もしくは非置換（５〜２１員）ヘテロアリーレンを表す。より好ましくは、Ｌ１は、単結合、非置換もしくは（Ｃ１−Ｃ１０）アルキルで置換された（Ｃ６−Ｃ１８）アリーレン、または非置換もしくは（Ｃ１−Ｃ１０）アルキルで置換され、かつ窒素をヘテロ原子として含有する（５〜１８員）ヘテロアリーレンを表す。特に、Ｌ１は、単結合、フェニル、またはピリミジルを表す。 L 1 represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5 to 30 membered) heteroarylene. Preferably, L 1 represents a single bond, a substituted or unsubstituted (C6-C21) arylene, or a substituted or unsubstituted (5 to 21 membered) heteroarylene. More preferably, L 1 is a single bond, unsubstituted or (C1-C10) alkyl-substituted (C6-C18) arylene, or unsubstituted or (C1-C10) alkyl-substituted and the nitrogen is a heteroatom. Represents a heteroarylene (5 to 18 members) contained as. In particular, L 1 represents a single bond, phenyl or pyrimidyl.
Ｌ２は、置換もしくは非置換（Ｃ１−Ｃ３０）アルキレン、置換もしくは非置換（Ｃ６−Ｃ３０）アリーレン、または置換もしくは非置換（５〜３０員）ヘテロアリーレンを表す。好ましくは、Ｌ２は、置換もしくは非置換（Ｃ１−Ｃ２０）アルキレン、置換もしくは非置換（Ｃ６−Ｃ２１）アリーレン、または置換もしくは非置換（５〜２１員）ヘテロアリーレンを表す。より好ましくは、Ｌ２は、非置換（Ｃ１−Ｃ１０）アルキレン、非置換もしくは（Ｃ１−Ｃ１０）アルキルで置換された（Ｃ６−Ｃ１８）アリーレン、または非置換もしくは（Ｃ１−Ｃ１０）アルキルで置換され、かつ酸素をヘテロ原子として含有する（６〜２１員）ヘテロアリーレンを表す。特に、Ｌ２は、（Ｃ１−Ｃ４）アルキル、フェニル、ビフェニル、ナフチル、フルオレニル、９，９−ジメチル−９Ｈ−フルオレニル、またはジベンゾフラニルを表す。 L 2 is a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene or substituted or unsubstituted (5-30 membered) heteroarylene. Preferably, L 2 is a substituted or unsubstituted (C1-C20) alkylene, a substituted or unsubstituted (C6-C21) arylene or substituted or unsubstituted (5-21 membered) heteroarylene. More preferably, L 2 is unsubstituted (C1-C10) alkylene, unsubstituted or (C1-C10) alkyl substituted (C6-C18) arylene, or unsubstituted or (C1-C10) alkyl substituted. , And (6 to 21 membered) heteroarylene containing oxygen as a hetero atom. In particular, L 2 represents alkyl, phenyl, biphenyl, naphthyl, fluorenyl, 9,9-dimethyl -9H- fluorenyl or dibenzofuranyl, (C1-C4).
Ｒ１及びＲ２は、それぞれ独立して、水素、重水素、ハロゲン、置換もしくは非置換（Ｃ１−Ｃ３０）アルキル、置換もしくは非置換（Ｃ６−Ｃ３０）アリール、置換もしくは非置換（５〜３０員）ヘテロアリール、置換もしくは非置換（Ｃ３−Ｃ３０）シクロアルキル、置換もしくは非置換（３〜７員）ヘテロシクロアルキル、置換もしくは非置換（Ｃ６−Ｃ３０）アリール（Ｃ１−Ｃ３０）アルキル、−Ｎ（Ｒ１１）（Ｒ１２）、−Ｓｉ（Ｒ１３）（Ｒ１４）（Ｒ１５）、−Ｓ（Ｒ１６）、−Ｏ（Ｒ１７）、シアノ、ニトロ、またはヒドロキシルを表すか、あるいは隣接する置換基（複数可）と連結して、（３〜３０員）の単環式もしくは多環式の、脂環式もしくは芳香族の環を形成し得、その炭素原子（複数可）は窒素、酸素、及び硫黄から選択される少なくとも１つのヘテロ原子と置き換えられてもよい。Ｒ１１〜Ｒ１７は、それぞれ独立して、水素、重水素、ハロゲン、置換もしくは非置換（Ｃ１−Ｃ３０）アルキル、置換もしくは非置換（Ｃ６−Ｃ３０）アリール、置換もしくは非置換（５〜３０員）ヘテロアリール、置換もしくは非置換（３〜７員）ヘテロシクロアルキル、または置換もしくは非置換（Ｃ３−Ｃ３０）シクロアルキルを表すか、あるいは隣接する置換基（複数可）と連結して、（３〜３０員）の単環式もしくは多環式の、脂環式もしくは芳香族の環を形成し得、その炭素原子（複数可）は、窒素、酸素、及び硫黄から選択される少なくとも１つのヘテロ原子と置き換えられてもよい。好ましくは、Ｒ１及びＲ２は、それぞれ独立して、水素、置換もしくは非置換（Ｃ１−Ｃ２０）アルキル、置換もしくは非置換（Ｃ６−Ｃ２１）アリール、置換もしくは非置換（５〜２１員）ヘテロアリール、または−Ｎ（Ｒ１１）（Ｒ１２）を表す。好ましくは、Ｒ１１及びＲ１２は、それぞれ独立して、置換もしくは非置換（Ｃ６−Ｃ２１）アリールを表す。より好ましくは、Ｒ１及びＲ２、それぞれ独立して、水素、非置換（Ｃ６−Ｃ１８）アリール、窒素をヘテロ原子として含有する非置換（６〜１８員）ヘテロアリール、または−Ｎ（Ｒ１１）（Ｒ１２）を表す。より好ましくは、Ｒ１１及びＲ１２は、それぞれ独立して、非置換（Ｃ６−Ｃ１８）アリールを表す。特に、Ｒ１及びＲ２は、それぞれ独立して、水素、フェニル、ピリジル、ピリミジル、カルバゾリル、ジフェニルアミノ、（フェニル）（ビフェニル）アミノ、ジ（ビフェニル）アミノ、または（フェニル）（ナフチル）アミノを表す。 R 1 and R 2 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5 to 30 members). ) Heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl (C1-C30) alkyl, -N ( R 11 ) (R 12 ), —Si (R 13 ) (R 14 ) (R 15 ), —S (R 16 ), —O (R 17 ), cyano, nitro, or hydroxyl. It may be linked to a substituent (s) to form a (3-30 member) mono- or polycyclic, alicyclic or aromatic ring, the carbon atom (s) of which is nitrogen, acid And at least one heteroatom selected from elemental and sulfur. R 11 to R 17 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5 to 30 members). ) Represents heteroaryl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, or substituted or unsubstituted (C3-C30) cycloalkyl, or is linked to adjacent substituent (s), (3 To 30 members) may form a monocyclic or polycyclic, alicyclic or aromatic ring, the carbon atom (s) of which is at least one heteroatom selected from nitrogen, oxygen, and sulfur. It may be replaced with an atom. Preferably, R 1 and R 2 are each independently hydrogen, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C21) aryl, substituted or unsubstituted (5 to 21 membered) hetero. Aryl or -N (R < 11 >) (R < 12 >) is represented. Preferably, R 11 and R 12 each independently represent substituted or unsubstituted (C6-C21) aryl. More preferably, R 1 and R 2 are each independently hydrogen, unsubstituted (C 6 -C 18) aryl, unsubstituted (6-18 membered) heteroaryl containing nitrogen as a heteroatom, or —N (R 11). ) (R 12 ). More preferably, R 11 and R 12 each independently represent unsubstituted (C6-C18) aryl. In particular, R 1 and R 2 are each independently hydrogen, phenyl, pyridyl, pyrimidyl, carbazolyl, diphenylamino, (phenyl) (biphenyl) amino, di (biphenyl) amino, or (phenyl) (naphthyl) amino. Represent
ｎ及びｍは、それぞれ独立して、０または１を表すが、但し、ｎ及びｍの両方が、同時に０になることができないことを条件とする。 n and m each independently represent 0 or 1 with the proviso that both n and m cannot both be 0 at the same time.
ａは、１〜３の整数を表し、ａが２以上の整数である場合、Ｒ１のそれぞれは同じであっても異なってもよい。好ましくは、ａは、１を表す。 a represents an integer of 1 to 3, and when a is an integer of 2 or more, each R 1 may be the same or different. Preferably, a represents 1.
ｂは、１〜６の整数を表し、ｂが２以上の整数である場合、Ｒ２のそれぞれは同じであっても異なってもよい。好ましくは、ｂは、１を表す。 b represents an integer of 1 to 6, and when b is an integer of 2 or more, each R 2 may be the same or different. Preferably, b represents 1.
本開示の一実施形態に従って、式１〜４中、Ａｒ１〜Ａｒ４は、それぞれ独立して、置換もしくは非置換（Ｃ６−Ｃ２１）アリール、または置換もしくは非置換（５〜２１員）ヘテロアリールを表し、Ａｒ１及びＡｒ２は、互いに縮合して環を形成し得、Ａｒ５は、置換もしくは非置換（Ｃ１−Ｃ２０）アルキル、置換もしくは非置換（Ｃ６−Ｃ２１）アリール、または置換もしくは非置換（５〜２１員）ヘテロアリールを表し、Ｌ１は、単結合、置換もしくは非置換（Ｃ６−Ｃ２１）アリーレン、または置換もしくは非置換（５〜２１員）ヘテロアリーレンを表し、Ｌ２は、置換もしくは非置換（Ｃ１−Ｃ２０）アルキレン、置換もしくは非置換（Ｃ６−Ｃ２１）アリーレン、または置換もしくは非置換（５〜２１員）ヘテロアリーレンを表し、Ｒ１及びＲ２は、それぞれ独立して、水素、置換もしくは非置換（Ｃ１−Ｃ２０）アルキル、置換もしくは非置換（Ｃ６−Ｃ２１）アリール、置換もしくは非置換（５〜２１員）ヘテロアリール、または−Ｎ（Ｒ１１）（Ｒ１２）を表し、Ｒ１１及びＲ１２は、それぞれ独立して、置換もしくは非置換（Ｃ６−Ｃ２１）アリールを表し、ｎ及びｍは、それぞれ独立して、０または１を表すが、但し、ｎ及びｍの両方が同時に０になることができないことを条件とし、ａは１〜３の整数を表し、ａが２以上の整数である場合、Ｒ１のそれぞれは同じであっても異なってもよく、ｂは１〜６の整数を表し、ｂが２以上の整数である場合、Ｒ２のそれぞれは同じであっても異なってもよく、ヘテロアリール（エン）は、Ｎ、Ｏ、及びＳから選択される少なくとも１つのヘテロ原子を含有する。 According to one embodiment of the present disclosure, in Formulas 1-4, Ar 1 to Ar 4 are each independently substituted or unsubstituted (C6-C21) aryl, or substituted or unsubstituted (5 to 21 membered) heteroaryl. And Ar 1 and Ar 2 may be fused with each other to form a ring, and Ar 5 is substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C21) aryl, or substituted or unsubstituted. Represents a substituted (5 to 21 membered) heteroaryl, L 1 represents a single bond, a substituted or unsubstituted (C6-C21) arylene, or a substituted or unsubstituted (5 to 21 membered) heteroarylene, and L 2 represents Substituted or unsubstituted (C1-C20) alkylene, substituted or unsubstituted (C6-C21) arylene, or substituted or unsubstituted (5 to 21 membered) heteroaryl Represents down, R 1 and R 2 are each independently hydrogen, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C21) aryl, substituted or unsubstituted (5-21 membered) heteroaryl or -N (R 11) represents (R 12),, R 11 and R 12 each independently represent a substituted or unsubstituted (C6-C21) aryl, n and m are each independently Represents 0 or 1, provided that both n and m cannot be 0 at the same time, a represents an integer of 1 to 3, and when a is an integer of 2 or more, R Each of 1 may be the same or different, b represents an integer of 1 to 6, and when b is an integer of 2 or more, each of R 2 may be the same or different; Aryl (ene) is N, O, Containing at least one heteroatom selected from finely S.
本開示の別の実施形態に従って、式１〜４中、Ａｒ１〜Ａｒ４は、それぞれ独立して、置換もしくは非置換（Ｃ６−Ｃ２１）アリールを表し、（Ｃ６−Ｃ２１）アリールの置換基は、（Ｃ１−Ｃ３０）アルキル、非置換または（Ｃ１−Ｃ１０）アルキルで置換された（Ｃ６−Ｃ２１）アリール、及び非置換または（Ｃ６−Ｃ１２）アリールで置換された（５〜２１員）ヘテロアリールからなる群から選択される少なくとも１つであり得、Ａｒ１及びＡｒ２は、互いに縮合して環を形成し得、Ａｒ５は、非置換（Ｃ１−Ｃ１０）アルキル、非置換（Ｃ６−Ｃ１８）アリール、あるいは（Ｃ１−Ｃ１０）アルキル、（Ｃ６−Ｃ２１）アリール、非置換または（Ｃ６−Ｃ１３）アリールもしくはジ（Ｃ６−Ｃ１８）アリールアミノで置換された（６〜２１員）ヘテロアリールで置換された（Ｃ６−Ｃ１８）アリール、あるいは非置換または（Ｃ１−Ｃ１０）アルキルもしくは（Ｃ６−Ｃ１８）アリールで置換され、かつＮ、Ｏ、及びＳから選択されるヘテロ原子（複数可）を含有する（６〜２１員）ヘテロアリールを表し、Ｌ１は、単結合、非置換もしくは（Ｃ１−Ｃ１０）アルキルで置換された（Ｃ６−Ｃ１８）アリーレン、または非置換もしくは（Ｃ１−Ｃ１０）アルキルで置換され、かつ窒素をヘテロ原子として含有する（５〜１８員）ヘテロアリーレンを表し、Ｌ２は、非置換（Ｃ１−Ｃ１０）アルキレン、非置換もしくは（Ｃ１−Ｃ１０）アルキルで置換された（Ｃ６−Ｃ１８）アリーレン、または非置換もしくは（Ｃ１−Ｃ１０）アルキルで置換され、かつ酸素をヘテロ原子として含有する（６〜２１員）ヘテロアリーレンを表し、Ｒ１及びＲ２は、それぞれ独立して、水素、非置換（Ｃ６−Ｃ１８）アリール、窒素をヘテロ原子として含有する非置換（６〜１８員）ヘテロアリール、または−Ｎ（Ｒ１１）（Ｒ１２）を表し、Ｒ１１及びＲ１２は、それぞれ独立して、非置換（Ｃ６−Ｃ１８）アリールを表し、ｎ及びｍは、それぞれ独立して、０または１を表すが、但し、ｎ及びｍの両方が同時に０になることができないことを条件とし、ａは１を表し、ｂは１を表す。 According to another embodiment of the present disclosure, in Formulas 1-4, Ar 1 to Ar 4 each independently represent substituted or unsubstituted (C6-C21) aryl, wherein the substituent of (C6-C21) aryl is , (C1-C30) alkyl, unsubstituted or (C1-C10) alkyl-substituted (C6-C21) aryl, and unsubstituted or (C6-C12) aryl-substituted (5-21 membered) heteroaryl Ar 1 and Ar 2 may be fused with each other to form a ring, Ar 5 may be an unsubstituted (C 1 -C 10) alkyl, an unsubstituted (C 6 -C 18). ) Aryl, or (C1-C10) alkyl, (C6-C21) aryl, unsubstituted or substituted with (C6-C13) aryl or di (C6-C18) arylamino (C21-membered) heteroaryl-substituted (C6-C18) aryl, or unsubstituted or (C1-C10) alkyl or (C6-C18) aryl, and selected from N, O, and S Represents (6-21 membered) heteroaryl containing heteroatom (s), L 1 is a single bond, unsubstituted or (C 1 -C 10) alkyl substituted (C 6 -C 18) arylene, or unsubstituted Alternatively, it represents a (5- to 18-membered) heteroarylene substituted with (C1-C10) alkyl and containing nitrogen as a heteroatom, L 2 is an unsubstituted (C1-C10) alkylene, an unsubstituted or (C1-C10) ) Alkyl-substituted (C6-C18) arylene, or unsubstituted or (C1-C10) alkyl-substituted and oxygen-hetero. Represents a (6- to 21-membered) heteroarylene containing as an atom, and R 1 and R 2 are each independently hydrogen, unsubstituted (C 6 -C 18) aryl, or unsubstituted (6 to 18-membered) heteroaryl or -N (R 11,) represent (R 12), R 11 and R 12 are each independently unsubstituted (C6-C18) aryl, n and m are each independently Then 0 or 1 is provided, provided that both n and m cannot be 0 at the same time, a represents 1, and b represents 1.
より具体的には、式１の有機電界発光化合物は、以下を含むが、それらに限定されない。 More specifically, organic electroluminescent compounds of Formula 1 include, but are not limited to:
本開示の有機電界発光化合物は、当業者に既知の合成方法によって調製され得る。例えば、それは、以下の反応スキーム１または２に従って調製され得る。 The organic electroluminescent compounds of the present disclosure can be prepared by synthetic methods known to those skilled in the art. For example, it can be prepared according to Reaction Scheme 1 or 2 below.
さらに、本開示は、式１の有機電界発光化合物を含む有機電界発光材料及びこの材料を含む有機電界発光デバイスを提供する。 Further, the present disclosure provides organic electroluminescent materials that include the organic electroluminescent compound of Formula 1 and organic electroluminescent devices that include the materials.
材料は、本開示の有機電界発光化合物からなり得る。さもなければ、材料は、本開示の化合物に加え、有機電界発光材料に含まれている従来の化合物（複数可）をさらに含み得る。好ましくは、有機電界発光材料は、ホスト材料または正孔輸送材料であり得る。 The material may consist of an organic electroluminescent compound of the present disclosure. Otherwise, the material may further comprise, in addition to the compounds of this disclosure, conventional compound (s) included in organic electroluminescent materials. Preferably, the organic electroluminescent material can be a host material or a hole transport material.
本開示の有機電界発光デバイスは、第１の電極、第２の電極、及び第１の電極と第２の電極との間に設置された少なくとも１つの有機層を備え得る。有機層は、式１の少なくとも１つの化合物を含み得る。 The organic electroluminescent device of the present disclosure may include a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode. The organic layer may include at least one compound of Formula 1.
第１の電極及び第２の電極のうちの一方はアノードであり得、他方はカソードであり得る。有機層は、発光層を含み得、また、正孔注入層、正孔輸送層、電子輸送層、電子注入層、中間層、正孔阻止層、電子緩衝層、及び電子阻止層から選択される少なくとも１つの層をさらに含み得る。 One of the first electrode and the second electrode can be the anode and the other can be the cathode. The organic layer may include a light emitting layer and is selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an intermediate layer, a hole blocking layer, an electron buffer layer, and an electron blocking layer. It may further include at least one layer.
本開示の有機電界発光化合物は、発光層及び正孔輸送層のうちの少なくとも１つの中に含まれ得る。正孔輸送層中に使用されるとき、本開示の有機電界発光化合物は、正孔輸送材料として含まれ得る。発光層中に使用されるとき、本開示の有機電界発光化合物は、ホスト材料として含まれ得る。 The organic electroluminescent compound of the present disclosure may be included in at least one of a light emitting layer and a hole transporting layer. When used in a hole transport layer, the organic electroluminescent compound of the present disclosure can be included as a hole transport material. When used in a light emitting layer, the organic electroluminescent compound of the present disclosure can be included as a host material.
本開示の有機電界発光化合物が正孔輸送材料として含まれるとき、発光層は、正孔輸送材料として使用されるもの以外に、当分野で既知の発光材料、または本開示の有機電界発光化合物を含み得る。当分野で既知の発光材料は、当分野で既知のホスト材料であり得、少なくとも１つのドーパントをさらに含み得る。当分野で既知のホスト材料は、当分野で既知の蛍光性またはリン光性ホスト材料であり得る。 When the organic electroluminescent compound of the present disclosure is included as a hole transport material, the light emitting layer may include a light emitting material known in the art, or an organic electroluminescent compound of the present disclosure, in addition to those used as the hole transport material. May be included. Emissive materials known in the art can be host materials known in the art and can further comprise at least one dopant. The host materials known in the art can be fluorescent or phosphorescent host materials known in the art.
本開示の有機電界発光化合物が発光層中にホスト材料（第１のホスト材料）として含まれるとき、少なくとも１つのドーパントが、さらに含まれ得、必要に応じて、別の化合物が、第２のホスト材料として含まれ得る。第１のホスト材料と第２のホスト材料との間の重量比は、１：９９〜９９：１の範囲である。 When the organic electroluminescent compound of the present disclosure is included as a host material (first host material) in the light emitting layer, at least one dopant may further be included, and optionally, another compound is added to the second material. It may be included as a host material. The weight ratio between the first host material and the second host material ranges from 1:99 to 99: 1.
以下の式６〜８の化合物からなる群から選択される化合物は、発光効率の点から見て、既知のホスト材料または第２のホスト材料として好ましい。
Ｈ−（Ｃｚ−Ｌ４）ｈ−Ｍ （６）
Ｈ−（Ｃｚ）ｉ−Ｌ４−Ｍ （７）
The compound selected from the group consisting of the compounds of the following formulas 6 to 8 is preferable as the known host material or the second host material from the viewpoint of luminous efficiency.
H- (Cz-L 4) h -M (6)
H- (Cz) i -L 4 -M (7)
式中、Ｃｚは、以下の構造を表し、 In the formula, Cz represents the following structure,
Ｒ２１〜Ｒ２４は、それぞれ独立して、水素、重水素、ハロゲン、置換もしくは非置換（Ｃ１−Ｃ３０）アルキル、置換もしくは非置換（Ｃ６−Ｃ３０）アリール、置換もしくは非置換（３〜３０員）ヘテロアリール、またはＲ２５Ｒ２６Ｒ２７Ｓｉ−を表し、Ｒ２５〜Ｒ２７は、それぞれ独立して、置換もしくは非置換（Ｃ１−Ｃ３０）アルキル、または置換もしくは非置換（Ｃ６−Ｃ３０）アリールを表し、Ｌ４は、単結合、置換もしくは非置換（Ｃ６−Ｃ３０）アリーレン、または置換もしくは非置換（５〜３０員）ヘテロアリーレンを表し、Ｍは、置換もしくは非置換（Ｃ６−Ｃ３０）アリール、または置換もしくは非置換（５〜３０員）ヘテロアリールを表し、Ｙ１及びＹ２は、それぞれ独立して、−Ｏ−、−Ｓ−、−Ｎ（Ｒ３１）−、または−Ｃ（Ｒ３２）（Ｒ３３）−を表すが、但し、Ｙ１及びＹ２が、同時に存在しないことを条件とし、Ｒ３１〜Ｒ３３は、それぞれ独立して、置換もしくは非置換（Ｃ１−Ｃ３０）アルキル、置換もしくは非置換（Ｃ６−Ｃ３０）アリール、または置換もしくは非置換（５〜３０員）ヘテロアリールを表し、Ｒ３２及びＲ３３は同じであっても異なってもよく、ｈ及びｉは、それぞれ独立して、１〜３の整数を表し、ｊ、ｋ、ｌ、及びｒは、それぞれ独立して、０〜４の整数を表し、ｈ、ｉ、ｊ、ｋ、ｌ、またはｒが、２以上の整数である場合、（Ｃｚ−Ｌ４）のそれぞれ、（Ｃｚ）のそれぞれ、Ｒ２１のそれぞれ、Ｒ２２のそれぞれ、Ｒ２３のそれぞれ、またはＲ２４のそれぞれは同じであっても異なってもよい。 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 (3 to 30 member). ) heteroaryl, or R 25 R 26 R 27 Si- and represents, R 25 to R 27 are each independently a substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl, the stands, L 4 represents a single bond, a substituted or unsubstituted (C6-C30) arylene or substituted or unsubstituted (5-30 membered) represents a heteroarylene, M is a substituted or unsubstituted (C6-C30) aryl , or a substituted or represents unsubstituted (5-30 membered) heteroaryl, Y 1 and Y 2 are each independently, -O -, - S -, - (R 31) -, or -C (R 32) (R 33 ) - represents a proviso, Y 1 and Y 2, with the proviso that there is no simultaneous, R 31 to R 33 are each independently Represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5 to 30 membered) heteroaryl, even if R 32 and R 33 are the same. May be different, h and i each independently represent an integer of 1 to 3, j, k, l, and r each independently represent an integer of 0 to 4, h, i, When j, k, l, or r is an integer of 2 or more, each of (Cz-L 4 ), each of (Cz), each of R 21 , each of R 22 , each of R 23 , or R each of the 24 different even in the same It may be.
特に、式６〜８によって表されるホスト材料は、以下： In particular, the host materials represented by Formulas 6-8 include the following:
を含む（式中、ＴＰＳは、トリフェニルシリルを表す）。 (Wherein TPS represents triphenylsilyl).
ドーパントは、好ましくは少なくとも１つのリン光性ドーパントである。本開示の有機電界発光デバイスのためのリン光性ドーパント材料は、限定されるものではないが、好ましくは、イリジウム（Ｉｒ）、オスミウム（Ｏｓ）、銅（Ｃｕ）、または白金（Ｐｔ）の金属化錯体化合物から選択され得、より好ましくは、イリジウム（Ｉｒ）、オスミウム（Ｏｓ）、銅（Ｃｕ）、または白金（Ｐｔ）のオルト−金属化錯体化合物、さらにより好ましくは、オルト−金属化イリジウム錯体化合物から選択され得る。 The dopant is preferably at least one phosphorescent dopant. Phosphorescent dopant materials for organic electroluminescent devices of the present disclosure are preferably, but not exclusively, iridium (Ir), osmium (Os), copper (Cu), or platinum (Pt) metals. Complexed complex compound, more preferably an ortho-metallated complex compound of iridium (Ir), osmium (Os), copper (Cu), or platinum (Pt), even more preferably an ortho-metallated iridium. It may be selected from complex compounds.
リン光性ドーパントは、好ましくは、以下の式９〜１１によって表される化合物からなる群から選択され、 The phosphorescent dopant is preferably selected from the group consisting of compounds represented by formulas 9-11 below,
式中、Ｌは、以下の構造から選択され、 Where L is selected from the following structures:
Ｒ１００は、水素、置換もしくは非置換（Ｃ１−Ｃ３０）アルキル、または置換もしくは非置換（Ｃ３−Ｃ３０）シクロアルキルを表し、Ｒ１０１〜Ｒ１０９及びＲ１１１〜Ｒ１２３は、それぞれ独立して、水素、重水素、ハロゲン、非置換もしくはハロゲンで置換された（Ｃ１−Ｃ３０）アルキル、シアノ、置換もしくは非置換（Ｃ３−Ｃ３０）シクロアルキル、置換もしくは非置換（Ｃ６−Ｃ３０）アリール、または置換もしくは非置換（Ｃ１−Ｃ３０）アルコキシを表すか、またはＲ１０６〜Ｒ１０９が、隣接する置換基（複数可）と連結して、置換もしくは非置換縮合環、例えば、置換もしくは非置換フルオレン、置換もしくは非置換ジベンゾチオフェン、または置換もしくは非置換ジベンゾフランを形成し得るか、またはＲ１２０〜Ｒ１２３が、隣接する置換基（複数可）と連結して、置換もしくは非置換縮合環、例えば、置換もしくは非置換キノリンを形成し得、Ｒ１２４〜Ｒ１２７は、それぞれ独立して、水素、重水素、ハロゲン、置換もしくは非置換（Ｃ１−Ｃ３０）アルキル、または置換もしくは非置換（Ｃ６−Ｃ３０）アリールを表し、Ｒ１２４〜Ｒ１２７は、隣接する置換基（複数可）と連結して、置換もしくは非置換縮合環、例えば、置換もしくは非置換フルオレン、置換もしくは非置換ジベンゾチオフェン、または置換もしくは非置換ジベンゾフランを形成し得、Ｒ２０１〜Ｒ２１１は、それぞれ独立して、水素、重水素、ハロゲン、非置換もしくはハロゲンで置換された（Ｃ１−Ｃ３０）アルキル、置換もしくは非置換（Ｃ３−Ｃ３０）シクロアルキル、または置換もしくは非置換（Ｃ６−Ｃ３０）アリールを表すか、またはＲ２０８〜Ｒ２１１は、隣接する置換基（複数可）と連結して、置換もしくは非置換縮合環、例えば、置換もしくは非置換フルオレン、置換もしくは非置換ジベンゾチオフェン、または置換もしくは非置換ジベンゾフランを形成し得、ｏ及びｐは、それぞれ独立して、１〜３の整数を表し、ｏまたはｐが２以上の整数の場合、Ｒ１００のそれぞれは同じであっても異なってもよく、ｄは、１〜３の整数を表す。 R 100 represents hydrogen, substituted or unsubstituted (C 1 -C 30) alkyl, or substituted or unsubstituted (C 3 -C 30) cycloalkyl, and R 101 to R 109 and R 111 to R 123 are each independently, Hydrogen, deuterium, halogen, (C1-C30) alkyl unsubstituted or substituted with halogen, cyano, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or Represents an unsubstituted (C1-C30) alkoxy, or R 106 to R 109 are linked to adjacent substituent (s) to form a substituted or unsubstituted fused ring, such as substituted or unsubstituted fluorene, substituted or May form an unsubstituted dibenzothiophene, or a substituted or unsubstituted dibenzofuran, or R 120 to R 123 may be linked to adjacent substituent (s) to form a substituted or unsubstituted fused ring, for example a substituted or unsubstituted quinoline, R 124 to R 127 are each independently Represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl, R 124 to R 127 are linked to adjacent substituent (s). To form a substituted or unsubstituted fused ring, for example, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzothiophene, or a substituted or unsubstituted dibenzofuran, and R 201 to R 211 are each independently hydrogen, heavy or deuterium. Hydrogen, halogen, unsubstituted or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) Cycloalkyl or substituted or unsubstituted (C6-C30) or aryl, or R 208 to R 211, is coupled with an adjacent substituent (s), a substituted or unsubstituted fused ring, for example, substituted or Unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, or substituted or unsubstituted dibenzofuran can be formed, and o and p each independently represent an integer of 1 to 3, and when o or p is an integer of 2 or more. , R 100 may be the same or different, and d represents an integer of 1 to 3.
具体的には、リン光性ドーパント材料は、以下を含む。 Specifically, the phosphorescent dopant material includes:
本開示の追加の態様に従って、有機電界発光デバイスを調製するための混合物または化合物が提供される。混合物または化合物は、本開示の化合物を含む。混合物または化合物は、有機電界発光デバイスの発光層または正孔輸送層を調製するための混合物または化合物であり得る。本開示の化合物が、有機電界発光デバイスの発光層を調製するための混合物または化合物中に含まれるとき、本開示の化合物は、ホスト材料として含まれ得る。本開示の化合物がホスト材料として含まれるとき、混合物または化合物は、第２のホスト材料、例えば、式６〜８によって表される化合物から選択されるものをさらに含み得る。本開示の化合物が、有機電界発光デバイスの正孔輸送層を調製するための混合物または化合物中に含まれるとき、本開示の化合物は、正孔輸送材料として含まれ得る。 According to an additional aspect of the present disclosure, a mixture or compound for preparing an organic electroluminescent device is provided. The mixture or compound comprises a compound of the present disclosure. The mixture or compound can be a mixture or compound for preparing a light emitting layer or a hole transport layer of an organic electroluminescent device. When the compound of the present disclosure is included in a mixture or compound for preparing a light emitting layer of an organic electroluminescent device, the compound of the present disclosure can be included as a host material. When the compounds of the present disclosure are included as host materials, the mixture or compound can further include a second host material, such as those selected from compounds represented by Formulas 6-8. When the compound of the present disclosure is included in a mixture or compound for preparing a hole transport layer of an organic electroluminescent device, the compound of the present disclosure may be included as a hole transport material.
本開示の有機電界発光デバイスは、第１の電極、第２の電極、及び第１の電極と第２の電極との間に設置された少なくとも１つの有機層を含み得、有機層が、本開示の有機電界発光デバイスを調製するための混合物または化合物を含み得る発光層または発光層及び正孔輸送層の両方を含み得る。 The organic electroluminescent device of the present disclosure may include a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, the organic layer comprising: It may include a light emitting layer or both a light emitting layer and a hole transporting layer that may include a mixture or compound for preparing the disclosed organic electroluminescent devices.
本開示の有機電界発光デバイスは、式１の化合物に加えて、アリールアミン系化合物及びスチリルアリールアミン系化合物からなる群から選択される少なくとも１つの化合物をさらに含み得る。 The organic electroluminescent device of the present disclosure may further include, in addition to the compound of Formula 1, at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound.
本開示の有機電界発光デバイスにおいて、有機層は、式１の化合物に加えて、周期表の第１族の金属、第２族の金属、第４周期の遷移金属、第５周期の遷移金属、ランタニド、及びｄ軌道遷移元素の有機金属からなる群から選択される少なくとも１つの金属、またはこれらの金属を含む少なくとも１つの錯体化合物をさらに含み得る。有機層は、発光層及び電荷発生層をさらに含み得る。 In the organic electroluminescent device of the present disclosure, the organic layer includes, in addition to the compound of Formula 1, a metal of Group 1 of the periodic table, a metal of Group 2 of the periodic table, a transition metal of the fourth period, a transition metal of the fifth period, It may further include at least one metal selected from the group consisting of lanthanides and organometals of d-orbital transition elements, or at least one complex compound containing these metals. The organic layer may further include a light emitting layer and a charge generating layer.
その上、本開示の有機電界発光デバイスは、本開示の化合物の他に、当分野で既知の青色電界発光化合物、赤色電界発光化合物、または緑色電界発光化合物を含む、少なくとも１つの発光層をさらに含むことによって、白色光を放出し得る。 Moreover, the organic electroluminescent device of the present disclosure further comprises at least one light emitting layer comprising a blue electroluminescent compound, a red electroluminescent compound, or a green electroluminescent compound known in the art in addition to the compound of the present disclosure. By including, white light may be emitted.
本開示の有機電界発光デバイスにおいて、好ましくは、少なくとも１つの層（以降「表面層」）は、カルコゲニド層、金属ハロゲン化物層、及び金属酸化物層から選択される１つまたは両方の電極（複数可）の内部表面（複数可）上に配置され得る。特に、シリコンまたはアルミニウムのカルコゲニド（酸化物を含む）層は、好ましくは、電界発光媒体層のアノード表面上に配置され、金属ハロゲン化物層または金属酸化物層は、好ましくは、電界発光媒体層のカソード表面上に配置される。かかる表面層は、有機電界発光デバイスに動作安定性を提供する。好ましくは、カルコゲニドは、ＳｉＯＸ（１≦Ｘ≦２）、ＡｌＯＸ（１≦Ｘ≦１．５）、ＳｉＯＮ、ＳｉＡｌＯＮなどを含み、金属ハロゲン化物層は、ＬｉＦ、ＭｇＦ２、ＣａＦ２、希土類金属フッ化物などを含み、金属酸化物は、Ｃｓ２Ｏ、Ｌｉ２Ｏ、ＭｇＯ、ＳｒＯ、ＢａＯ、ＣａＯなどを含む。 In the organic electroluminescent device of the present disclosure, preferably at least one layer (hereinafter "surface layer") is one or both electrodes (plurality) selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer. Can be disposed on the inner surface (s). In particular, a chalcogenide (including oxide) layer of silicon or aluminum is preferably disposed on the anode surface of the electroluminescent medium layer and a metal halide layer or metal oxide layer is preferably of the electroluminescent medium layer. Located on the cathode surface. Such a surface layer provides operational stability to the organic electroluminescent device. Preferably, the chalcogenide includes SiO X (1 ≦ X ≦ 2), AlO X (1 ≦ X ≦ 1.5), SiON, SiAlON, and the like, and the metal halide layer includes LiF, MgF 2 , CaF 2 , and rare earth. It includes metal fluorides and the like, and the metal oxides include Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO and the like.
本開示の有機電界発光デバイスにおいて、電子輸送化合物と還元性ドーパントとの混合領域、または正孔輸送化合物と酸化性ドーパントとの混合領域が、１対の電極の少なくとも１つの表面上に配置され得る。この場合、電子輸送化合物が還元されてアニオンとなり、したがって、混合領域から電界発光媒体に電子を注入及び輸送するのがより容易となる。さらに、正孔輸送化合物は、酸化されてカチオンとなり、したがって、混合領域から電界発光媒体に正孔を注入及び輸送するのがより容易となる。好ましくは、酸化性ドーパントは、様々なルイス酸及び受容体化合物を含み、還元性ドーパントは、アルカリ金属、アルカリ金属化合物、アルカリ土類金属、希土類金属、及びこれらの混合物を含む。還元性ドーパント層は、２つ以上の発光層を有し、白色光を発光する、電界発光デバイスを調製するために、電荷発生層として用いられ得る。 In the organic electroluminescent device of the present disclosure, a mixed region of an electron transport compound and a reducing dopant or a mixed region of a hole transport compound and an oxidizing dopant may be arranged on at least one surface of a pair of electrodes. . In this case, the electron transport compound is reduced to an anion, thus making it easier to inject and transport electrons from the mixed region to the electroluminescent medium. Further, the hole transport compound is oxidized to cations, thus making it easier to inject and transport holes from the mixed region to the electroluminescent medium. Preferably, the oxidizing dopant comprises various Lewis acids and acceptor compounds, and the reducing dopant comprises alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reducing dopant layer can be used as a charge generating layer to prepare an electroluminescent device that has two or more emitting layers and emits white light.
本開示の有機電界発光デバイスの各層を形成するためには、真空蒸着、スパッタリング、プラズマ及びイオンプレーティング法などの乾式成膜法、またはインクジェット印刷、ノズル印刷、スロットコーティング、スピンコーティング、ディップコーティング、及びフローコーティング法などの湿式成膜法が使用され得る。 In order to form each layer of the organic electroluminescent device of the present disclosure, dry deposition methods such as vacuum deposition, sputtering, plasma and ion plating methods, or inkjet printing, nozzle printing, slot coating, spin coating, dip coating, And wet deposition methods such as flow coating methods can be used.
湿式成膜法を使用するとき、各層を形成する材料を、エタノール、クロロホルム、テトラヒドロフラン、ジオキサンなどの任意の好適な溶媒中に溶解または拡散させることによって、薄膜が形成され得る。溶媒は、各層を形成する材料が溶解または拡散され得、かつ成膜能力に何の問題もない、いずれの溶媒であってもよい。 When using the wet deposition method, the thin film can be formed by dissolving or diffusing the material forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane. The solvent may be any solvent capable of dissolving or diffusing the material forming each layer and having no problem in film forming ability.
以降に、本開示の有機電界発光化合物、本化合物の調製方法、デバイスの発光特性を、以下の実施例を参照して詳細に説明する。 Hereinafter, the organic electroluminescent compound of the present disclosure, the method for preparing the present compound, and the light emission characteristics of the device will be described in detail with reference to the following examples.
実施例１：化合物Ｃ−１の調製 Example 1: Preparation of compound C-1
化合物１−１の調製
６−ブロモインダノン（５０ｇ、２３７ｍｍｏｌ）、フタルアルデヒド（３５ｇ、２６１ｍｍｏｌ）、及びエタノール６００ｍＬを反応槽内に導入した後、混合物を、３時間還流下においた。反応混合物を、０℃に冷却した。結晶化した固形物を濾過し、冷たいメタノールで洗浄して、化合物１−１（４７ｇ、６４％）を得た。
Preparation of Compound 1-1 6-bromoindanone (50 g, 237 mmol), phthalaldehyde (35 g, 261 mmol), and 600 mL of ethanol were introduced into the reaction vessel, and then the mixture was refluxed for 3 hours. The reaction mixture was cooled to 0 ° C. The crystallized solid was filtered and washed with cold methanol to give compound 1-1 (47 g, 64%).
化合物１−２の調製
ヨウ素（１３．５ｇ、５３．２ｍｍｏｌ）、次亜リン酸（２５ｍＬ、２４３ｍｍｏｌ、５０％の水溶液）、及び酢酸８００ｍＬを反応槽内に導入した後、混合物を１００℃で３０分間撹拌した。化合物１−１を緩徐に滴加した後、混合物を一晩撹拌した。反応混合物を、室温まで冷却した。結晶化した固形物を濾過し、冷たいメタノールで洗浄して、化合物１−２（４１．５ｇ、９２％）を得た。
Preparation of Compound 1-2 Iodine (13.5 g, 53.2 mmol), hypophosphorous acid (25 mL, 243 mmol, 50% aqueous solution), and acetic acid 800 mL were introduced into the reaction vessel, and then the mixture was heated at 100 ° C. for 30 minutes. Stir for minutes. After slowly adding compound 1-1 dropwise, the mixture was stirred overnight. The reaction mixture was cooled to room temperature. The crystallized solid was filtered and washed with cold methanol to give compound 1-2 (41.5 g, 92%).
化合物１−３の調製
化合物１−２（３９ｇ、１３２ｍｍｏｌ）、水酸化カリウム（３７ｇ、６６０ｍｍｏｌ）、ヨウ化カリウム（２．２ｇ、１３．３ｍｍｏｌ）、塩化ベンジルトリエチルアンモニウム（１．５ｇ、６．６ｍｍｏｌ）、蒸留水７００ｍＬ、及びジメチルスルホキシド７００ｍＬを反応槽内に導入した後、混合物を室温で１５分間撹拌した。ヨウ化メチル（３７ｇ、３３０ｍｍｏｌ）の添加後、混合物を室温で一晩撹拌した。反応混合物を、酢酸エチルで希釈し、蒸留水で洗浄した。抽出した有機層を硫酸マグネシウムで乾燥させ、回転式蒸発器によってそれから溶媒を除去した。生成物をカラムクロマトグラフィーによって精製して、化合物１−３（３３ｇ、７７％）を得た。
Preparation of Compound 1-3 Compound 1-2 (39 g, 132 mmol), potassium hydroxide (37 g, 660 mmol), potassium iodide (2.2 g, 13.3 mmol), benzyltriethylammonium chloride (1.5 g, 6.6 mmol). ), 700 mL of distilled water, and 700 mL of dimethyl sulfoxide were introduced into the reaction tank, and then the mixture was stirred at room temperature for 15 minutes. After addition of methyl iodide (37 g, 330 mmol), the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and washed with distilled water. The extracted organic layer was dried over magnesium sulfate and the solvent was removed from it by rotary evaporation. The product was purified by column chromatography to give compound 1-3 (33g, 77%).
化合物Ｃ−１の調製
化合物１−３（１０ｇ、３１ｍｍｏｌ）、ジビフェニル−４−イルアミン（９．９ｇ、３１ｍｍｏｌ）、酢酸パラジウム（ＩＩ）（０．２５ｇ、１．２４ｍｍｏｌ）、トリ−ｔ−ブチルホスフィン（１ｍＬ、３．１ｍｍｏｌ ５０％のキシレン溶液）、ナトリウムｔ−ブトキシド（４．５ｇ、４６．５ｍｍｏｌ）、及びｏ−キシレン１５０ｍＬを反応槽内に導入した後、混合物を、１時間還流下においた。室温まで冷却した後、反応混合物を酢酸エチルで希釈し、水で数回洗浄し無水硫酸マグネシウムで乾燥させ、減圧下で蒸留しカラムクロマトグラフィーによって精製して、化合物Ｃ−１（９．６ｇ、５５％）を得た。化合物Ｃ−１の物理特性は、下記表１に示す。
Preparation of Compound C-1 Compound 1-3 (10 g, 31 mmol), dibiphenyl-4-ylamine (9.9 g, 31 mmol), palladium (II) acetate (0.25 g, 1.24 mmol), tri-t-butyl. After introducing phosphine (1 mL, 3.1 mmol 50% xylene solution), sodium t-butoxide (4.5 g, 46.5 mmol), and 150 mL of o-xylene into the reaction vessel, the mixture was placed under reflux for 1 hour. It was After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed several times with water, dried over anhydrous magnesium sulfate, distilled under reduced pressure and purified by column chromatography to give compound C-1 (9.6 g, 55%). The physical properties of compound C-1 are shown in Table 1 below.
実施例２：化合物Ｃ−４３の調製 Example 2: Preparation of compound C-43
化合物２−１の調製
化合物２−１を化合物１−１〜１−３の調製のための実施例１と同じ方式で調製したが、但し、６−ブロモインダノンの代わりに５−ブロモインダノンを使用したことを除く。
Preparation of Compound 2-1 Compound 2-1 was prepared in the same manner as in Example 1 for the preparation of compounds 1-1 to 1-3, except that 5-bromoindanone was used instead of 6-bromoindanone. Except that was used.
化合物Ｃ−４３の調製
化合物２−１（１０ｇ、３１ｍｍｏｌ）、ジビフェニル−４−イルアミン（９．９ｇ、３１ｍｍｏｌ）、酢酸パラジウム（ＩＩ）（０．２５ｇ、１．２４ｍｍｏｌ）、トリ−ｔ−ブチルホスフィン（１ｍＬ、３．１ｍｍｏｌ、５０％のキシレン溶液）、ナトリウムｔ−ブトキシド（４．５ｇ、４６．５ｍｍｏｌ）、及びｏ−キシレン１５０ｍＬを反応槽内に導入した後、混合物を、１時間還流下においた。室温まで冷却した後、反応混合物を酢酸エチルで希釈し、水で数回洗浄し無水硫酸マグネシウムで乾燥させ、減圧下で蒸留しカラムクロマトグラフィーによって精製して、化合物Ｃ−４３（１０．８ｇ、６２％）を得た。化合物Ｃ−４３の物理特性は、下記表１に示す。
Preparation of Compound C-43 Compound 2-1 (10 g, 31 mmol), dibiphenyl-4-ylamine (9.9 g, 31 mmol), palladium (II) acetate (0.25 g, 1.24 mmol), tri-t-butyl. Phosphine (1 mL, 3.1 mmol, 50% xylene solution), sodium t-butoxide (4.5 g, 46.5 mmol), and 150 mL of o-xylene were introduced into the reaction vessel, and then the mixture was refluxed for 1 hour. I smelled it. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed several times with water, dried over anhydrous magnesium sulfate, distilled under reduced pressure and purified by column chromatography to give compound C-43 (10.8 g, 62%) was obtained. The physical properties of Compound C-43 are shown in Table 1 below.
実施例３：化合物Ｃ−７１の調製 Example 3: Preparation of compound C-71
化合物３−１の調製
１１Ｈ−ベンゾ［ｂ］フルオレン−１１−オン（４１．５ｇ、１８１ｍｍｏｌ）、及びテトラヒドロフラン５５０ｍＬを反応槽内に導入した後、反応混合物を、０℃に冷却し、次いでフェニルマグネシウムブロミド（７８ｍＬ、２３５ｍｍｏｌ、３Ｍのジエチルエーテル溶液）を、それに緩徐に滴加した。反応混合物を室温で１時間撹拌した。塩化アンモニウム水溶液を反応混合物に添加して、反応を終了させた後、混合物を酢酸エチルで希釈し、水で洗浄し無水硫酸マグネシウムで乾燥させ、減圧下で蒸留しカラムクロマトグラフィーによって精製して、化合物３−１（５６ｇ、９９％）を得た。
Preparation of Compound 3-1 After introducing 11H-benzo [b] fluoren-11-one (41.5 g, 181 mmol) and 550 mL of tetrahydrofuran into the reaction vessel, the reaction mixture was cooled to 0 ° C. and then phenylmagnesium. Bromide (78 mL, 235 mmol, 3M solution in diethyl ether) was added slowly to it dropwise. The reaction mixture was stirred at room temperature for 1 hour. Aqueous ammonium chloride solution was added to the reaction mixture to terminate the reaction, then the mixture was diluted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate, distilled under reduced pressure and purified by column chromatography, Compound 3-1 (56 g, 99%) was obtained.
化合物３−２の調製
化合物３−１（２８ｇ、９０．３ｍｍｏｌ）、４−ブロモトリフェニルアミン（８８ｇ、２７１ｍｍｏｌ）、及び塩化メチレン（ＭＣ）（６００ｍＬ）を反応槽内に導入した後、混合物を窒素雰囲気内に供した。Ｅａｔｏｎの試薬３ｍＬを、混合物に緩徐に滴加した。混合物を室温で２時間撹拌した。蒸留水を添加して反応を終了させた後、混合物を塩化メチレンで抽出した。抽出した有機層を硫酸マグネシウムで乾燥させ、回転式蒸発器によってそれから溶媒を除去した。生成物をカラムクロマトグラフィーによって精製して、化合物３−２（３８．９ｇ、７０％）を得た。
Preparation of Compound 3-2 Compound 3-1 (28 g, 90.3 mmol), 4-bromotriphenylamine (88 g, 271 mmol), and methylene chloride (MC) (600 mL) were introduced into the reaction vessel, and then the mixture was mixed. It was subjected to a nitrogen atmosphere. 3 mL of Eaton's reagent was slowly added dropwise to the mixture. The mixture was stirred at room temperature for 2 hours. After the reaction was terminated by adding distilled water, the mixture was extracted with methylene chloride. The extracted organic layer was dried over magnesium sulfate and the solvent was removed from it by rotary evaporation. The product was purified by column chromatography to give compound 3-2 (38.9g, 70%).
化合物Ｃ−７１の調製
化合物３−２（１０ｇ、１６．２７ｍｍｏｌ）、２−ナフチルボロン酸（３．４ｇ、１９．５ｍｍｏｌ）、テトラキス（トリフェニルホスフィン）パラジウム（０．７ｇ、０．６５ｍｍｏｌ）、炭酸カリウム（５．６ｇ、４０．７ｍｍｏｌ）、トルエン６０ｍＬ、及びエタノール２０ｍＬを反応槽内に導入した後、蒸留水２０ｍＬを混合物に添加した。混合物を、１２０℃で３時間撹拌した。反応完了後、混合物を蒸留水で洗浄し、酢酸エチルで抽出した。抽出した有機層を硫酸マグネシウムで乾燥させ、回転式蒸発器によってそれから溶媒を除去した。生成物をカラムクロマトグラフィーによって精製して、化合物Ｃ−７１（７．６ｇ、７１％）を得た。化合物Ｃ−７１の物理特性は、下記表１に示す。
Preparation of Compound C-71 Compound 3-2 (10 g, 16.27 mmol), 2-naphthylboronic acid (3.4 g, 19.5 mmol), tetrakis (triphenylphosphine) palladium (0.7 g, 0.65 mmol), After introducing potassium carbonate (5.6 g, 40.7 mmol), 60 mL of toluene, and 20 mL of ethanol into the reaction tank, 20 mL of distilled water was added to the mixture. The mixture was stirred at 120 ° C. for 3 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate and the solvent was removed from it by rotary evaporation. The product was purified by column chromatography to give compound C-71 (7.6g, 71%). The physical properties of Compound C-71 are shown in Table 1 below.
実施例４：化合物Ｃ−８９の調製 Example 4: Preparation of compound C-89
化合物Ｃ−８９の調製
化合物１−３（５ｇ、１５．４ｍｍｏｌ）、９−フェニル−９Ｈ，９’Ｈ−３，３’−ビカルバゾール（６．６ｇ、１６．２ｍｍｏｌ）、ヨウ化銅（１．４７ｇ、７．７３ｍｍｏｌ）、ジアミノシクロヘキサン（３．７ｍＬ、３０．９ｍｍｏｌ）、リン酸三カリウム（９．８５ｇ、４６．４ｍｍｏｌ）、及びｏ−キシレン１００ｍＬを反応槽内に導入した後、混合物を、２時間還流下においた。室温まで冷却した後、混合物を酢酸エチルで希釈し、水で数回洗浄し無水硫酸マグネシウムで乾燥させ、減圧下で蒸留しカラムクロマトグラフィーによって精製して、化合物Ｃ−８９（４．８ｇ、４７％）を得た。化合物Ｃ−８９の物理特性は、下記表１に示す。
Preparation of Compound C-89 Compound 1-3 (5 g, 15.4 mmol), 9-phenyl-9H, 9′H-3,3′-bicarbazole (6.6 g, 16.2 mmol), copper iodide (1 0.47 g, 7.73 mmol), diaminocyclohexane (3.7 mL, 30.9 mmol), tripotassium phosphate (9.85 g, 46.4 mmol), and 100 mL of o-xylene were introduced into the reaction vessel, and then the mixture was added. Placed under reflux for 2 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate, washed with water several times, dried over anhydrous magnesium sulfate, distilled under reduced pressure and purified by column chromatography to give compound C-89 (4.8 g, 47). %) Was obtained. The physical properties of Compound C-89 are shown in Table 1 below.
実施例５：化合物Ｃ−１２５の調製 Example 5: Preparation of compound C-125
化合物５−１の調製
ジベンゾフラン（２１ｇ、１２７ｍｍｏｌ）及びテトラヒドロフラン３３０ｍＬを反応槽内に導入した後、混合物を窒素雰囲気内に供し、−７８℃に冷却した。ｎ−ブチルリチウム（５０ｍＬ、２．５Ｍ、１１５ｍｍｏｌ）を緩徐に滴加した後、混合物を−７８℃で２時間撹拌した。テトラヒドロフラン３３０ｍＬ中に溶解した１１Ｈ−ベンゾ［Ｂ］フルオレン−１１−オン（２６ｇ、１１５ｍｍｏｌ）を緩徐に滴加した後、混合物を緩徐に室温まで温め、一晩撹拌した。塩化アンモニウム水溶液を反応混合物に添加して反応を終了させた後、混合物を塩化メチレン（ＭＣ）で抽出した。抽出した有機層を硫酸マグネシウムで乾燥させ、回転式蒸発器によってそれから溶媒を除去した。生成物をカラムクロマトグラフィーによって精製して、化合物５−１（４４ｇ、９６％）を得た。
Preparation of Compound 5-1 After introducing dibenzofuran (21 g, 127 mmol) and 330 mL of tetrahydrofuran into the reaction vessel, the mixture was put into a nitrogen atmosphere and cooled to -78 ° C. After slowly adding n-butyllithium (50 mL, 2.5 M, 115 mmol) dropwise, the mixture was stirred at −78 ° C. for 2 hours. After slowly adding 11H-benzo [B] fluoren-11-one (26 g, 115 mmol) dissolved in 330 mL of tetrahydrofuran, the mixture was slowly warmed to room temperature and stirred overnight. Aqueous ammonium chloride solution was added to the reaction mixture to terminate the reaction, and then the mixture was extracted with methylene chloride (MC). The extracted organic layer was dried over magnesium sulfate and the solvent was removed from it by rotary evaporation. The product was purified by column chromatography to give compound 5-1 (44g, 96%).
化合物５−２の調製
化合物５−１（４４ｇ、１１０ｍｍｏｌ）、４−ブロモトリフェニルアミン（８９ｇ、２７６ｍｍｏｌ）、及びＭＣ５５０ｍＬを反応槽内に導入した後、混合物を０℃に冷却した。Ｅａｔｏｎの試薬（２．４ｍＬ、２．２ｍｍｏｌ）を添加後、混合物を室温へと温め、次いで３時間撹拌した。塩化アンモニウム水溶液を反応混合物に添加して反応を終了させた後、混合物をＭＣで抽出した。抽出した有機層を硫酸マグネシウムで乾燥させ、回転式蒸発器によってそれから溶媒を除去した。生成物をカラムクロマトグラフィーによって精製して、化合物５−２（５５ｇ、７１％）を得た。
Preparation of Compound 5-2 Compound 5-1 (44 g, 110 mmol), 4-bromotriphenylamine (89 g, 276 mmol), and MC550 mL were introduced into the reaction tank, and then the mixture was cooled to 0 ° C. After the addition of Eaton's reagent (2.4 mL, 2.2 mmol), the mixture was warmed to room temperature and then stirred for 3 hours. Aqueous ammonium chloride solution was added to the reaction mixture to terminate the reaction, and then the mixture was extracted with MC. The extracted organic layer was dried over magnesium sulfate and the solvent was removed from it by rotary evaporation. The product was purified by column chromatography to give compound 5-2 (55g, 71%).
化合物Ｃ−１２５の調製
化合物５−２（１０ｇ、１４．１ｍｍｏｌ）、２−ナフタレニルボロン酸（２．６ｇ、１５．６ｍｍｏｌ）、テトラキス（トリフェニルホスフィン）パラジウム（０．８ｇ、０．７１ｍｍｏｌ）、炭酸カリウム（４．７ｇ、３４．１ｍｍｏｌ）、トルエン７０ｍＬ、及びエタノール１７ｍＬを反応槽内に導入した後、蒸留水１７ｍＬを混合物に添加した。混合物を、１２０℃で３時間撹拌した。反応完了後、混合物を蒸留水で洗浄し、ＭＣで抽出した。抽出した有機層を硫酸マグネシウムで乾燥させ、回転式蒸発器によってそれから溶媒を除去した。生成物をカラムクロマトグラフィーによって精製して、化合物Ｃ−１２５（８．４ｇ、８０％）を得た。化合物Ｃ−１２５の物理特性は、下記表１に示す。
Preparation of Compound C-125 Compound 5-2 (10 g, 14.1 mmol), 2-naphthalenylboronic acid (2.6 g, 15.6 mmol), tetrakis (triphenylphosphine) palladium (0.8 g, 0.71 mmol). ), Potassium carbonate (4.7 g, 34.1 mmol), 70 mL of toluene, and 17 mL of ethanol were introduced into the reaction tank, and then 17 mL of distilled water was added to the mixture. The mixture was stirred at 120 ° C. for 3 hours. After completion of the reaction, the mixture was washed with distilled water and extracted with MC. The extracted organic layer was dried over magnesium sulfate and the solvent was removed from it by rotary evaporation. The product was purified by column chromatography to give compound C-125 (8.4g, 80%). The physical properties of Compound C-125 are shown in Table 1 below.
［デバイス実施例１］本開示の化合物を使用したＯＬＥＤ
以下の通り本開示の材料を使用して、ＯＬＥＤを製造した。有機発光ダイオード（ＯＬＥＤ）（Ｇｅｏｍａｔｅｃ）用のガラス基板上の透明電極インジウムスズ酸化物（ＩＴＯ）薄膜（１０Ω／ｓｑ）を、アセトン及びイソプロパノールを順次用いた超音波洗浄に供し、次いで、イソプロパノール中で保管した。次いで、ＩＴＯ基板を、真空蒸着装置の基板ホルダに載置した。Ｎ１，Ｎ１’−（［１，１’−ビフェニル］−４，４’−ジイル）ビス（Ｎ１−（ナフタレン−１−イル）−Ｎ４，Ｎ４−ジフェニルベンゼン−１，４−ジアミン）を、該真空蒸着装置のセル内に導入し、次いで、該装置のチャンバ内の圧力を１０Ｅ−６トルに制御した。その後、電流をセルに印加して上の導入材料を蒸発させ、それによってＩＴＯ基板上に６０ｎｍの厚さを有する正孔注入層を形成した。次いで、化合物Ｃ−１を該真空蒸着装置の別のセル内に導入し、電流をセルに印加することによって蒸発させ、それによって、正孔注入層上に２０ｎｍの厚さを有する正孔輸送層を形成した。その後、下記表２に示す通りの化合物Ｈ−１をホスト材料として真空蒸着装置の１つのセル内に導入し、化合物Ｄ−１をドーパントとして別のセル内に導入した。ドーパントが、ホスト及びドーパントの総量に基づいて１５重量％のドーピング量で蒸着して、正孔輸送層上に３０ｎｍの厚さを有する発光層を形成するように、２つの材料を異なる速度で蒸発させた。次いで、２−（４−（９，１０−ジ（ナフタレン−２−イル）アントラセン−２−イル）フェニル）−１−フェニル−１Ｈ−ベンゾ［ｄ］イミダゾールを、１つのセル内に導入し、キノリン酸リチウムを別のセル内に導入した。２つの材料がそれぞれ５０重量％のドーピング量で蒸着して、発光層上に３０ｎｍの厚さを有する電子輸送層を形成するように、２つの材料を同じ速度で蒸発させた。キノリン酸リチウムを電子輸送層上に２ｎｍの厚さを有する電子注入層として蒸着させた後、次いで、１５０ｎｍの厚さを有するＡｌカソードを、別の真空蒸着装置によって電子注入層上に蒸着させた。その結果、ＯＬＥＤを製造した。ＯＬＥＤを製造するために使用した全ての材料は、１０Ｅ−６トルでの真空昇華によって精製したものであった。製造したＯＬＥＤは、１，５００ｃｄ／ｍ２の輝度及び３．５ｍＡ／ｃｍ２の電流密度を有する緑色発光を示した。
[Device Example 1] OLED using the compound of the present disclosure
OLEDs were made using the materials of the present disclosure as follows. A transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) on a glass substrate for an organic light emitting diode (OLED) (Geomatec) was subjected to ultrasonic cleaning using acetone and isopropanol sequentially, and then in isopropanol. I kept it. Next, the ITO substrate was placed on the substrate holder of the vacuum vapor deposition device. N 1, N 1 '- ( [1,1'- biphenyl] -4,4'-diyl) bis (N 1 - (naphthalen-1-yl) -N 4, N 4 - diphenyl-1,4 Diamine) was introduced into the cell of the vacuum deposition apparatus and the pressure in the chamber of the apparatus was then controlled to 10E- 6 Torr. Then, a current was applied to the cell to evaporate the introduced material above, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate. Then, the compound C-1 is introduced into another cell of the vacuum vapor deposition apparatus and vaporized by applying an electric current to the cell, whereby a hole transport layer having a thickness of 20 nm is formed on the hole injection layer. Was formed. Then, the compound H-1 as shown in the following Table 2 was introduced into one cell of the vacuum vapor deposition apparatus as a host material, and the compound D-1 was introduced into another cell as a dopant. The two materials are evaporated at different rates so that the dopant is deposited with a doping amount of 15% by weight based on the total amount of the host and the dopant to form a light emitting layer having a thickness of 30 nm on the hole transport layer. Let Then, 2- (4- (9,10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole was introduced into one cell, Lithium quinophosphate was introduced into another cell. The two materials were evaporated at the same rate so that the two materials were each deposited with a doping amount of 50% by weight to form an electron transport layer having a thickness of 30 nm on the light emitting layer. Lithium quinolinate was deposited on the electron transport layer as an electron injection layer having a thickness of 2 nm, and then an Al cathode having a thickness of 150 nm was deposited on the electron injection layer by another vacuum deposition apparatus. . As a result, an OLED was manufactured. All materials used to make OLEDs were purified by vacuum sublimation at 10E- 6 Torr. The manufactured OLED exhibited green emission with a brightness of 1,500 cd / m 2 and a current density of 3.5 mA / cm 2 .
［デバイス実施例２］本開示の化合物を使用したＯＬＥＤ
ＯＬＥＤをデバイス実施例１と同じ方式で製造したが、但し、化合物Ｃ−７１を使用して正孔輸送層を形成したことと、下記表２に示す通りの化合物Ｈ−２及びＨ−３をホストとして使用したことを除く。製造したＯＬＥＤは、７００ｃｄ／ｍ２の輝度及び１４．０ｍＡ／ｃｍ２の電流密度を有する青色発光を示した。
[Device Example 2] OLED using the compound of the present disclosure
An OLED was prepared in the same manner as in Device Example 1, except that compound C-71 was used to form the hole transport layer and compounds H-2 and H-3 as shown in Table 2 below. Except for being used as a host. The manufactured OLED exhibited blue emission with a brightness of 700 cd / m 2 and a current density of 14.0 mA / cm 2 .
［デバイス実施例３］本開示の化合物を使用したＯＬＥＤ
ＯＬＥＤをデバイス実施例１と同じ方式で製造したが、但し、化合物Ｃ−８９を使用して２０ｎｍの厚さを有する正孔輸送層を形成したことを除く。製造したＯＬＥＤは、９００ｃｄ／ｍ２の輝度及び１．９ｍＡ／ｃｍ２の電流密度を有する緑色発光を示した。
[Device Example 3] OLED using the compound of the present disclosure
An OLED was prepared in the same manner as Device Example 1, except that compound C-89 was used to form a hole transport layer having a thickness of 20 nm. The manufactured OLED exhibited green emission with a brightness of 900 cd / m 2 and a current density of 1.9 mA / cm 2 .
［デバイス実施例４］本開示の化合物を使用したＯＬＥＤ
ＯＬＥＤをデバイス実施例１と同じ方式で製造したが、但し、化合物Ｃ−１２５を使用して正孔輸送層を形成したことと、化合物Ｈ−２及びＨ−３をホストとして使用したことを除く。製造したＯＬＥＤは、１，２００ｃｄ／ｍ２の輝度及び２５．０ｍＡ／ｃｍ２の電流密度を有する青色発光を示した。
[Device Example 4] OLED using the compound of the present disclosure
An OLED was prepared in the same manner as Device Example 1, except that compound C-125 was used to form the hole transport layer and compounds H-2 and H-3 were used as hosts. . The manufactured OLED exhibited blue emission with a brightness of 1,200 cd / m 2 and a current density of 25.0 mA / cm 2 .
［比較デバイス実施例１］従来の化合物を使用するＯＬＥＤ
ＯＬＥＤをデバイス実施例１と同じ方式で製造したが、但し、下記の表２に示す通りの化合物Ｔ−１を使用して２０ｎｍの厚さを有する正孔輸送層を形成したことを除く。製造したＯＬＥＤは、９，８００ｃｄ／ｍ２の輝度及び２６．１ｍＡ／ｃｍ２の電流密度を有する緑色発光を示した。
Comparative device Example 1 OLEDs using conventional compounds
An OLED was prepared in the same manner as Device Example 1, except that compound T-1 as shown in Table 2 below was used to form a hole transport layer having a thickness of 20 nm. The manufactured OLED exhibited a green emission with a brightness of 9,800 cd / m 2 and a current density of 26.1 mA / cm 2 .
［比較デバイス実施例２］従来の化合物を使用するＯＬＥＤ
ＯＬＥＤをデバイス実施例１と同じ方式で製造したが、但し、化合物Ｔ−１を使用して正孔輸送層を形成したことと、化合物Ｈ−２及びＨ−３をホストとして使用したことを除く。製造したＯＬＥＤは、２，８００ｃｄ／ｍ２の輝度及び１４１．２ｍＡ／ｃｍ２の電流密度を有する青色発光を示した。
Comparative device Example 2 OLEDs using conventional compounds
An OLED was prepared in the same manner as Device Example 1, except that compound T-1 was used to form the hole transport layer and compounds H-2 and H-3 were used as hosts. . The manufactured OLED exhibited blue emission with a brightness of 2,800 cd / m 2 and a current density of 141.2 mA / cm 2 .
デバイス実施例によって確認された通り、本開示の有機電子材料のための化合物は、従来の化合物よりも良好な発光特徴を有する。本開示の有機電子材料のための化合物を含む有機電界発光デバイスは、発光特徴及び寿命において卓越性を示す。 As confirmed by the device examples, the compounds for the organic electronic materials of the present disclosure have better emission characteristics than conventional compounds. Organic electroluminescent devices that include compounds for the disclosed organic electronic materials exhibit excellence in emission characteristics and lifetime.
Claims (7)
Ａｒ１〜Ａｒ４は、それぞれ独立して、置換もしくは非置換（Ｃ６〜Ｃ３０）アリール、または置換もしくは非置換（５〜３０員）ヘテロアリールを表し、Ａｒ１及びＡｒ２は、互いに縮合して環を形成し得、
Ａｒ５は、置換もしくは非置換（Ｃ１−Ｃ３０）アルキル、置換もしくは非置換（Ｃ６−Ｃ３０）アリール、または置換もしくは非置換（５〜３０員）ヘテロアリールを表し、 Ｌ１は、単結合、置換もしくは非置換（Ｃ６−Ｃ３０）アリーレン、または置換もしくは非置換（５〜３０員）ヘテロアリーレンを表し、
Ｌ２は、置換もしくは非置換（Ｃ１−Ｃ３０）アルキレン、置換もしくは非置換（Ｃ６−Ｃ３０）アリーレン、または置換もしくは非置換（５〜３０員）ヘテロアリーレンを表し、
Ｒ１及びＲ２は、それぞれ独立して、水素、重水素、置換もしくは非置換（Ｃ１−Ｃ３０）アルキル、置換もしくは非置換（Ｃ６−Ｃ３０）アリール、置換もしくは非置換（５〜３０員）ヘテロアリール、置換もしくは非置換（Ｃ３−Ｃ３０）シクロアルキル、置換もしくは非置換（３〜７員）ヘテロシクロアルキル、置換もしくは非置換（Ｃ６−Ｃ３０）アリール（Ｃ１−Ｃ３０）アルキル、−Ｎ（Ｒ１１）（Ｒ１２）、またはシアノを表すか、あるいは隣接する置換基（複数可）と連結して、（３〜３０員）の単環式もしくは多環式の、脂環式もしくは芳香族の環を形成し得、その炭素原子（複数可）は窒素、酸素、及び硫黄から選択される少なくとも１つのヘテロ原子と置き換えられてもよく、
但し、ｍが１の場合、Ｒ １ 及びＲ ２ は、それぞれ独立して、水素、重水素、シアノ、置換もしくは非置換（Ｃ１−Ｃ３０）アルキル、置換もしくは非置換（Ｃ６−Ｃ３０）アリール、置換もしくは非置換（５〜３０員）ヘテロアリール、置換もしくは非置換（Ｃ３−Ｃ３０）シクロアルキル、置換もしくは非置換（３〜７員）ヘテロシクロアルキル、置換もしくは非置換（Ｃ６−Ｃ３０）アリール（Ｃ１−Ｃ３０）アルキル、または−Ｎ（Ｒ １１ ）（Ｒ １２ ）を表し、
Ｒ１１〜Ｒ １２ は、それぞれ独立して、水素、重水素、置換もしくは非置換（Ｃ１−Ｃ３０）アルキル、置換もしくは非置換（Ｃ６−Ｃ３０）アリール、置換もしくは非置換（５〜３０員）ヘテロアリール、置換もしくは非置換（３〜７員）ヘテロシクロアルキル、または置換もしくは非置換（Ｃ３−Ｃ３０）シクロアルキルを表すか、あるいは隣接する置換基（複数可）と連結して、（３〜３０員）の単環式もしくは多環式の、脂環式もしくは芳香族の環を形成し得、その炭素原子（複数可）は、窒素、酸素、及び硫黄から選択される少なくとも１つのヘテロ原子と置き換えられてもよく、
ｎ及びｍは、それぞれ独立して、０または１を表すが、但し、ｎ及びｍの両方が、同時に０になることができないことを条件とし、
ａは、１〜３の整数を表し、ａが２以上の整数である場合、Ｒ１のそれぞれは同じであっても異なってもよく、
ｂは、１〜６の整数を表し、ｂが２以上の整数である場合、Ｒ２のそれぞれは同じであっても異なってもよく、
前記ヘテロアリール（エン）は、Ｂ、Ｎ、Ｏ、Ｓ、Ｐ（＝Ｏ）、Ｓｉ、及びＰから選択される少なくとも１つのヘテロ原子を含有し、
前記ヘテロシクロアルキルは、Ｏ、Ｓ、及びＮから選択される少なくとも１つのヘテロ原子を含有し、
ｍが０の場合、
（ｉ）Ａｒ１及びＡｒ２は、それぞれ独立して、非置換アントラセニル、置換もしくは非置換（Ｃ６−Ｃ３０）アリール、または置換もしくは非置換（５〜３０員）ヘテロアリールを表し、前記（Ｃ６−Ｃ３０）アリールは、フェニル、ビフェニル、ターフェニル、ナフチル、ビナフチル、フェニルナフチル、ナフチルフェニル、フルオレニル、フェニルフルオレニル、ベンゾフルオレニル、ジベンゾフルオレニル、フェナントレニル、フェニルフェナントレニル、インデニル、トリフェニレニル、ピレニル、テトラセニル、ペリレニル、クリセニル、ナフタセニル、及びフルオランテニルからなる群から選択され、Ａｒ１及びＡｒ２の前記置換（Ｃ６−Ｃ３０）アリール及び前記置換（５〜３０員）ヘテロアリールの置換基は、それぞれ独立して、重水素、ハロゲン、非置換またはハロゲンで置換された（Ｃ１−Ｃ３０）アルキル、（Ｃ１−Ｃ３０）アルコキシ、（Ｃ６−Ｃ３０）アリール、非置換または（Ｃ６−Ｃ３０）アリールで置換された（３〜３０員）ヘテロアリール、（Ｃ３−Ｃ３０）シクロアルキル、（３〜７員）ヘテロシクロアルキル、トリ（Ｃ１−Ｃ３０）アルキルシリル、トリ（Ｃ６−Ｃ３０）アリールシリル、ジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリル、（Ｃ１−Ｃ３０）アルキルジ（Ｃ６−Ｃ３０）アリールシリル、（Ｃ２−Ｃ３０）アルケニル、（Ｃ２−Ｃ３０）アルキニル、シアノ、ジ（Ｃ１−Ｃ３０）アルキルアミノ、非置換または（Ｃ１−Ｃ３０）アルキルで置換されたジ（Ｃ６−Ｃ３０）アリールアミノ、（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールアミノ、ジ（Ｃ６−Ｃ３０）アリールボロニル、ジ（Ｃ１−Ｃ３０）アルキルボロニル、（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールボロニル、（Ｃ６−Ｃ３０）アリール（Ｃ１−Ｃ３０）アルキル、（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリール、カルボキシル、ニトロ、及びヒドロキシルからなる群から選択される少なくとも１つであり、Ａｒ１及びＡｒ２の前記（５〜３０員）ヘテロアリール並びにＡｒ１及びＡｒ２の置換基としての前記（３〜３０員）ヘテロアリールは、それぞれ独立して、フリル、チオフェニル、ピロリル、イミダゾリル、ピラゾリル、チアゾリル、チアジアゾリル、イソチアゾリル、イソオキサゾリル、オキサゾリル、オキサジアゾリル、トリアジニル、テトラジニル、トリアゾリル、テトラゾリル、フラザニル、ピリジル、ビピラジル、ピラジニル、ピリミジニル、ピリダジニル、ベンゾフラニル、ベンゾチオフェニル、イソベンゾフラニル、ジベンゾフラニル、ジベンゾチオフェニル、ナフトフラニル、ナフトチオフェニル、ベンゾナフトフラニル、ベンズイミダゾリル、ベンゾチアゾリル、ベンゾイソチアゾリル、ベンゾイソオキサゾリル、ベンゾオキサゾリル、イソインドリル、インドリル、インドリニル、インダゾリル、ベンゾチアジアゾリル、キノリル、イソキノリル、シノリニル、キナゾリニル、キノキサリニル、カルバゾリル、フェノキサジニル、フェナントリジニル、及びベンゾジオキソリルからなる群から選択され、但し、ｍが０でかつＡｒ１及びＡｒ２の一方がフェニル基、メチルフェニル基、３，５−ジメチルフェニル基、ビフェニル基、２−メチルビフェニル基、３−メチルビフェニル基、４−メチルビフェニル基、又は３，５−ジメチルビフェニル基の場合、Ａｒ１及びＡｒ２の他方は、下記：
（ｉｉ）Ｒ２は水素を表し、
（ｉｉｉ）Ｌ１はアントラセニル、フェニルアントラセニル、及びアントラセニルフェニルではない、前記有機電界発光化合物。 An organic electroluminescent compound represented by Formula 1 below, wherein
Ar 1 to Ar 4 each independently represent a substituted or unsubstituted (C6 to C30) aryl, or a substituted or unsubstituted (5 to 30 membered) heteroaryl, and Ar 1 and Ar 2 are condensed with each other. Can form a ring,
Ar 5 represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5 to 30 membered) heteroaryl, L 1 represents a single bond or a substituted Or an unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5 to 30 membered) heteroarylene,
L 2 represents a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5 to 30 membered) heteroarylene,
R 1 and R 2 are each independently hydrogen, deuterium, substitution or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-30 membered) Heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3 to 7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl (C1-C30) alkyl, -N (R 11) (or R 12), or cyano, or in conjunction with an adjacent substituent (s), of the monocyclic or polycyclic, cycloaliphatic or aromatic (3 to 30-membered) A ring may be formed, the carbon atom (s) of which may be replaced by at least one heteroatom selected from nitrogen, oxygen and sulphur,
Provided that when m is 1, R 1 and R 2 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted Alternatively, unsubstituted (5 to 30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3 to 7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl (C1 -C30) represents alkyl, or -N a (R 11) (R 12) ,
R 11 to R 12 are each independently hydrogen, deuterium, substitution or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-30 membered) Represents heteroaryl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, or substituted or unsubstituted (C3-C30) cycloalkyl, or is linked to adjacent substituent (s) to form (3 to 30-membered) mono- or polycyclic, alicyclic or aromatic rings, the carbon atom (s) of which is at least one heteroatom selected from nitrogen, oxygen, and sulfur. May be replaced with
n and m each independently represent 0 or 1, provided that both n and m cannot be 0 at the same time,
a represents an integer of 1 to 3, and when a is an integer of 2 or more, each R 1 may be the same or different,
b represents an integer of 1 to 6, and when b is an integer of 2 or more, each R 2 may be the same or different,
The heteroaryl (ene) contains at least one heteroatom selected from B, N, O, S, P (= O), Si, and P,
Said heterocycloalkyl contains at least one heteroatom selected from O, S and N,
If m is 0,
(I) Ar 1 and Ar 2 each independently represent unsubstituted anthracenyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5 to 30 membered) heteroaryl, and (C6- C30) Aryl is phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, indenyl, triphenylenyl. Selected from the group consisting of :, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, and fluoranthenyl, the substituted (C6-C30) aryl and the substituted (5 to 30-membered) heteroaryl substituents of Ar 1 and Ar 2 Respectively Independently substituted with deuterium, halogen, unsubstituted or halogen substituted (C1-C30) alkyl, (C1-C30) alkoxy, (C6-C30) aryl, unsubstituted or (C6-C30) aryl. (3-30 membered) heteroaryl, (C3-C30) cycloalkyl, (3-7 membered) heterocycloalkyl, tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, di (C1-) C30) alkyl (C6-C30) arylsilyl, (C1-C30) alkyldi (C6-C30) arylsilyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, di (C1-C30) alkylamino, Di (C6-C30) arylamino, unsubstituted or (C1-C30) alkyl substituted, (C1-C30) Alkyl (C6-C30) arylamino, di (C6-C30) arylboronyl, di (C1-C30) alkylboronyl, (C1-C30) alkyl (C6-C30) arylboronyl, (C6-C30) aryl (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, at least one selected from the group consisting of carboxyl, nitro, and hydroxyl, and the aforementioned (5 to 30 of Ar 1 and Ar 2 ). Member) heteroaryl and the (3 to 30 membered) heteroaryl as a substituent for Ar 1 and Ar 2 each independently represent furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl. , Oxadiazolyl, triazinyl, Trazinyl, triazolyl, tetrazolyl, flazanyl, pyridyl, bipyrazyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, naphthofuranyl, naphthothiophenyl, benzonaphthofuranyl, benzimidazolyl , Benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indolinyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenanthridinyl. , And benzodioxolyl, provided that m is 0 and one of Ar 1 and Ar 2 is phenyl. Group, methylphenyl group, 3,5-dimethylphenyl group, biphenyl group, 2-methylbiphenyl group, 3-methylbiphenyl group, 4-methylbiphenyl group, or 3,5-dimethylbiphenyl group, Ar 1 and Ar The other of 2 is the following:
(Ii) R 2 represents hydrogen,
(Iii) The organic electroluminescent compound as described above, wherein L 1 is not anthracenyl, phenylanthracenyl, or anthracenylphenyl.
Ａｒ１〜Ａｒ５、Ｌ１、Ｌ２、Ｒ１、Ｒ２、ａ、及びｂは、請求項１で定義される通りである、請求項１に記載の有機電界発光化合物。 The compound of Formula 1 is represented by any one of the following Formulas 2-4,
The organic electroluminescent compound according to claim 1 , wherein Ar 1 to Ar 5 , L 1 , L 2 , R 1 , R 2 , a, and b are as defined in claim 1.
Ａｒ５は、置換もしくは非置換（Ｃ１−Ｃ２０）アルキル、置換もしくは非置換（Ｃ６−Ｃ２１）アリール、または置換もしくは非置換（５〜２１員）ヘテロアリールを表し、 Ｌ１は、単結合、置換もしくは非置換（Ｃ６−Ｃ２１）アリーレン、または置換もしくは非置換（５〜２１員）ヘテロアリーレンを表し、
Ｌ２は、置換もしくは非置換（Ｃ１−Ｃ２０）アルキレン、置換もしくは非置換（Ｃ６−Ｃ２１）アリーレン、または置換もしくは非置換（５〜２１員）ヘテロアリーレンを表し、
Ｒ１及びＲ２は、それぞれ独立して、水素、置換もしくは非置換（Ｃ１−Ｃ２０）アルキル、置換もしくは非置換（Ｃ６−Ｃ２１）アリール、置換もしくは非置換（５〜２１員）ヘテロアリール、または−Ｎ（Ｒ１１）（Ｒ１２）を表し、
Ｒ１１及びＲ１２は、それぞれ独立して、置換もしくは非置換（Ｃ６−Ｃ２１）アリールを表し、
ｎ及びｍは、それぞれ独立して、０または１を表すが、但し、ｎ及びｍの両方が、同時に０になることができないことを条件とし、
ａは、１〜３の整数を表し、ａが２以上の整数である場合、Ｒ１のそれぞれは同じであっても異なってもよく、
ｂは、１〜６の整数を表し、ｂが２以上の整数である場合、Ｒ２のそれぞれは同じであっても異なってもよく、
前記ヘテロアリール（エン）は、Ｎ、Ｏ、及びＳから選択される少なくとも１つのヘテロ原子を含有する、請求項１に記載の有機電界発光化合物。 Ar 1 to Ar 4 each independently represent a substituted or unsubstituted (C6-C21) aryl, or a substituted or unsubstituted (5 to 21 membered) heteroaryl, and Ar 1 and Ar 2 are condensed with each other. Can form a ring,
Ar 5 represents a substituted or unsubstituted (C1-C20) alkyl, a substituted or unsubstituted (C6-C21) aryl, or a substituted or unsubstituted (5 to 21 membered) heteroaryl, L 1 is a single bond or a substituted Or unsubstituted (C6-C21) arylene, or substituted or unsubstituted (5 to 21 membered) heteroarylene,
L 2 represents substituted or unsubstituted (C1-C20) alkylene, substituted or unsubstituted (C6-C21) arylene, or substituted or unsubstituted (5 to 21 membered) heteroarylene,
R 1 and R 2 are each independently hydrogen, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C21) aryl, substituted or unsubstituted (5 to 21 membered) heteroaryl, or Represents -N (R 11 ) (R 12 ),
R 11 and R 12 each independently represent a substituted or unsubstituted (C6-C21) aryl,
n and m each independently represent 0 or 1, provided that both n and m cannot be 0 at the same time,
a represents an integer of 1 to 3, and when a is an integer of 2 or more, each R 1 may be the same or different,
b represents an integer of 1 to 6, and when b is an integer of 2 or more, each R 2 may be the same or different,
The organic electroluminescent compound according to claim 1, wherein the heteroaryl (ene) contains at least one heteroatom selected from N, O, and S.
Ａｒ５は、非置換（Ｃ１−Ｃ１０）アルキル、非置換または（Ｃ１−Ｃ１０）アルキル、（Ｃ６−Ｃ２１）アリール、（６〜２１員）ヘテロアリール、もしくはジ（Ｃ６−Ｃ１８）アリールアミノで置換された（Ｃ６−Ｃ１８）アリール、あるいは非置換または（Ｃ１−Ｃ１０）アルキルもしくは（Ｃ６−Ｃ１８）アリールで置換され、かつＮ、Ｏ、及びＳから選択されるヘテロ原子を含有する（６〜２１員）ヘテロアリールを表し、
Ｌ１は、単結合、非置換もしくは（Ｃ１−Ｃ１０）アルキルで置換された（Ｃ６−Ｃ１８）アリーレン、または非置換もしくは（Ｃ１−Ｃ１０）アルキルで置換され、かつ窒素をヘテロ原子として含有する（５〜１８員）ヘテロアリーレンを表し、
Ｌ２は、非置換（Ｃ１−Ｃ１０）アルキレン、非置換もしくは（Ｃ１−Ｃ１０）アルキルで置換された（Ｃ６−Ｃ１８）アリーレン、または非置換もしくは（Ｃ１−Ｃ１０）アルキルで置換され、かつ酸素をヘテロ原子として含有する（６〜２１員）ヘテロアリーレンを表し、
Ｒ１及びＲ２は、それぞれ独立して、水素、非置換（Ｃ６−Ｃ１８）アリール、窒素をヘテロ原子として含有する非置換（６〜１８員）ヘテロアリール、または−Ｎ（Ｒ１１）（Ｒ１２）を表し、
Ｒ１１及びＲ１２は、それぞれ独立して、非置換（Ｃ６−Ｃ１８）アリールを表し、
ｎ及びｍは、それぞれ独立して、０または１を表すが、但し、ｎ及びｍの両方が、同時に０になることができないことを条件とし、
ａは、１を表し、
ｂは、１を表す、請求項１に記載の有機電界発光化合物。 Ar 1 to Ar 4 each independently represent a substituted or unsubstituted (C6-C21) aryl, and the substituent of the (C6-C21) aryl is (C1-C30) alkyl, unsubstituted or (C1-C30) alkyl. C10) alkyl-substituted (C6-C21) aryl, and unsubstituted or (C6-C12) aryl-substituted (5-21 membered) heteroaryl may be at least one selected from the group consisting of: Ar 1 and Ar 2 may be fused together to form a ring,
Ar 5 is substituted with unsubstituted (C1-C10) alkyl, unsubstituted or (C1-C10) alkyl, (C6-C21) aryl, (6-21 membered) heteroaryl, or di (C6-C18) arylamino. Substituted (C6-C18) aryl, or unsubstituted or substituted with (C1-C10) alkyl or (C6-C18) aryl and containing a heteroatom selected from N, O and S (6-21 Member) represents heteroaryl,
L 1 is a single bond, unsubstituted or (C1-C10) alkyl-substituted (C6-C18) arylene, or unsubstituted or (C1-C10) alkyl-substituted and contains a nitrogen as a heteroatom ( 5-18 members) represents heteroarylene,
L 2 is unsubstituted (C 1 -C 10) alkylene, unsubstituted or (C 1 -C 10) alkyl-substituted (C 6 -C 18) arylene, or unsubstituted or (C 1 -C 10) alkyl and is oxygenated. Represents a heteroarylene (6- to 21-membered) contained as a hetero atom,
R 1 and R 2 are each independently hydrogen, unsubstituted (C 6 -C 18) aryl, unsubstituted (6-18 membered) heteroaryl containing nitrogen as a heteroatom, or —N (R 11 ) (R 12 ),
R 11 and R 12 each independently represent an unsubstituted (C6-C18) aryl,
n and m each independently represent 0 or 1, provided that both n and m cannot be 0 at the same time,
a represents 1,
The organic electroluminescent compound according to claim 1, wherein b represents 1.
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2013
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2014
- 2014-12-05 CN CN202110960033.0A patent/CN113582856A/en active Pending
- 2014-12-05 CN CN201480063491.2A patent/CN105764876A/en active Pending
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- 2014-12-05 WO PCT/KR2014/011968 patent/WO2015084114A1/en active Application Filing
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2020073461A (en) * | 2013-12-06 | 2020-05-14 | メルク パテント ゲーエムベーハー | Compound and organic electronic element |
| US11056652B2 (en) | 2013-12-06 | 2021-07-06 | Merck Patent Gmbh | Compounds and organic electronic devices |
| JP7114530B2 (en) | 2013-12-06 | 2022-08-08 | メルク パテント ゲーエムベーハー | Compounds and organic electronic devices |
Also Published As
| Publication number | Publication date |
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| KR20150066202A (en) | 2015-06-16 |
| CN113582856A (en) | 2021-11-02 |
| KR101939552B1 (en) | 2019-01-17 |
| JP2017501566A (en) | 2017-01-12 |
| CN105764876A (en) | 2016-07-13 |
| TW201529539A (en) | 2015-08-01 |
| WO2015084114A1 (en) | 2015-06-11 |
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