CN111683935B - Heterocyclic compound and organic light-emitting device comprising same - Google Patents
Heterocyclic compound and organic light-emitting device comprising same Download PDFInfo
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- CN111683935B CN111683935B CN201980011590.9A CN201980011590A CN111683935B CN 111683935 B CN111683935 B CN 111683935B CN 201980011590 A CN201980011590 A CN 201980011590A CN 111683935 B CN111683935 B CN 111683935B
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 36
- 239000000126 substance Substances 0.000 claims abstract description 54
- 239000010410 layer Substances 0.000 claims description 118
- 125000003118 aryl group Chemical group 0.000 claims description 65
- 238000002347 injection Methods 0.000 claims description 50
- 239000007924 injection Substances 0.000 claims description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims description 47
- 239000012044 organic layer Substances 0.000 claims description 27
- -1 dibenzofuranyl Chemical group 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
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000002560 nitrile group Chemical group 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 12
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 12
- 235000010290 biphenyl Nutrition 0.000 claims description 11
- 239000004305 biphenyl Substances 0.000 claims description 11
- 150000002431 hydrogen Chemical group 0.000 claims description 11
- 125000002950 monocyclic group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 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 7
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004957 naphthylene group Chemical group 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000005580 triphenylene group Chemical group 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001725 pyrenyl group Chemical group 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims 4
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 14
- 150000001875 compounds Chemical class 0.000 description 55
- 125000001072 heteroaryl group Chemical group 0.000 description 23
- 239000000463 material Substances 0.000 description 22
- 230000005525 hole transport Effects 0.000 description 17
- 238000000034 method Methods 0.000 description 16
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 7
- 230000000903 blocking effect Effects 0.000 description 7
- 229910052805 deuterium Inorganic materials 0.000 description 7
- 230000033228 biological regulation Effects 0.000 description 6
- 125000003367 polycyclic group Chemical group 0.000 description 6
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 6
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000005416 organic matter Substances 0.000 description 5
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000005264 aryl amine group Chemical group 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 4
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 3
- 125000005581 pyrene group Chemical group 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 125000004653 anthracenylene group Chemical group 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- 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 2
- 125000005562 phenanthrylene group Chemical group 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- KPQDSYXEIPINCS-UHFFFAOYSA-N 1-(4-bromophenyl)-2-ethylbenzimidazole Chemical compound CCC1=NC2=CC=CC=C2N1C1=CC=C(Br)C=C1 KPQDSYXEIPINCS-UHFFFAOYSA-N 0.000 description 1
- GZZLAPUQZCXKKT-UHFFFAOYSA-N 1-bromo-3-diphenylphosphorylbenzene Chemical compound BrC1=CC=CC(P(=O)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 GZZLAPUQZCXKKT-UHFFFAOYSA-N 0.000 description 1
- JLGXRQBMJFAZRY-UHFFFAOYSA-N 2-(4-bromonaphthalen-1-yl)-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC=C(C2=CC=CC=C12)C1=NC(=NC(=N1)C1=CC=CC=C1)C1=CC=CC=C1 JLGXRQBMJFAZRY-UHFFFAOYSA-N 0.000 description 1
- AYHGAQGOMUQMTR-UHFFFAOYSA-N 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound C1=CC(Br)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 AYHGAQGOMUQMTR-UHFFFAOYSA-N 0.000 description 1
- IWCVNBQCPBEDGY-UHFFFAOYSA-N 2-(5-bromopyridin-2-yl)-4,6-diphenyl-1,3,5-triazine Chemical compound BrC=1C=CC(=NC1)C1=NC(=NC(=N1)C1=CC=CC=C1)C1=CC=CC=C1 IWCVNBQCPBEDGY-UHFFFAOYSA-N 0.000 description 1
- MVNIQFVQTWBXTI-UHFFFAOYSA-N 2-(6-bromopyridin-3-yl)-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=NC=C(C=C1)C1=NC(=NC(=N1)C1=CC=CC=C1)C1=CC=CC=C1 MVNIQFVQTWBXTI-UHFFFAOYSA-N 0.000 description 1
- JUQINHGATSWHAN-UHFFFAOYSA-N 2-chloro-4-(3-dibenzofuran-2-ylphenyl)-6-phenyl-1,3,5-triazine Chemical compound ClC1=NC(=NC(=N1)C1=CC=CC(=C1)C1=CC=C2OC3=C(C=CC=C3)C2=C1)C1=CC=CC=C1 JUQINHGATSWHAN-UHFFFAOYSA-N 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- BCGDHDNNAPHFMT-UHFFFAOYSA-N 3-(4-bromophenyl)-5-naphthalen-2-ylpyridazine Chemical compound BrC1=CC=C(C=C1)C=1N=NC=C(C1)C1=CC2=CC=CC=C2C=C1 BCGDHDNNAPHFMT-UHFFFAOYSA-N 0.000 description 1
- OBPRUAWRVSBWHQ-UHFFFAOYSA-N 3-[3-(4-bromo-6-phenyl-1,3,5-triazin-2-yl)phenyl]-1,10-phenanthroline Chemical compound BrC1=NC(=NC(=N1)C1=CC=CC=C1)C=1C=C(C=CC1)C=1C=NC2=C3N=CC=CC3=CC=C2C1 OBPRUAWRVSBWHQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- UKAFKJGPPNZFHJ-UHFFFAOYSA-N CC1(OB(OC1(C)C)C1=CC=C(C=2C=CC=NC12)C=1C=CC=C2C=CC=NC12)C Chemical compound CC1(OB(OC1(C)C)C1=CC=C(C=2C=CC=NC12)C=1C=CC=C2C=CC=NC12)C UKAFKJGPPNZFHJ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
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- 229910006404 SnO 2 Inorganic materials 0.000 description 1
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000003609 aryl vinyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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- 230000002457 bidirectional effect Effects 0.000 description 1
- 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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- 150000001638 boron Chemical class 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
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- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
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- 229940125904 compound 1 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 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
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
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- Chemical & Material Sciences (AREA)
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- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
本说明书涉及化学式1的杂环化合物、包含其的有机发光器件及其制造方法。
This specification relates to the heterocyclic compound of Chemical Formula 1, an organic light-emitting device containing the same, and a manufacturing method thereof.
Description
技术领域Technical Field
本发明主张于2018年6月11日向韩国专利局提交的韩国专利第10-2018-0066879号的优先权，其全部内容包含在本说明书中。This application claims the priority of Korean Patent No. 10-2018-0066879 filed with the Korean Intellectual Property Office on June 11, 2018, the entire contents of which are incorporated herein by reference.
本说明书涉及杂环化合物及包含其的有机发光器件。The present invention relates to a heterocyclic compound and an organic light-emitting device comprising the same.
背景技术Background Art
通常情况下，有机发光现象是指利用有机物质将电能转换为光能的现象。利用有机发光现象的有机发光器件通常具有包括阳极和阴极以及位于它们之间的有机物层的结构。在这里，为了提高有机发光器件的效率和稳定性，有机物层大多情况下由分别利用不同的物质构成的多层结构形成，例如，可以由空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等形成。对于这样的有机发光器件的结构而言，如果在两电极之间施加电压，则空穴从阳极注入至有机物层，电子从阴极注入至有机物层，当所注入的空穴和电子相遇时会形成激子(exciton)，并且当该激子重新跃迁至基态时就会发出光。Generally speaking, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic light-emitting device using the organic light-emitting phenomenon generally has a structure including an anode and a cathode and an organic layer located between them. Here, in order to improve the efficiency and stability of the organic light-emitting device, the organic layer is mostly formed by a multilayer structure composed of different substances, for example, it can be formed by a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. For the structure of such an organic light-emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons re-transition to the ground state, light is emitted.
持续要求开发用于如上所述的有机发光器件的新的材料。There is a continuous demand for the development of new materials for organic light-emitting devices as described above.
发明内容Summary of the invention
技术课题Technical issues
本说明书提供杂环化合物及包含其的有机发光器件。The present specification provides a heterocyclic compound and an organic light-emitting device including the same.
课题的解决方法Solution to the problem
本说明书的一实施方式提供由下述化学式1表示的杂环化合物。One embodiment of the present specification provides a heterocyclic compound represented by the following Chemical Formula 1.
[化学式1][Chemical formula 1]
在上述化学式1中，In the above chemical formula 1,
X1至X7为N或CR1，上述X1至X7中的至少一个为N， X1 to X7 are N or CR1, at least one of the above X1 to X7 is N,
Y1至Y7为N或CR2，上述Y1至Y7中的至少任一个为N， Y1 to Y7 are N or CR2, at least one of the above Y1 to Y7 is N,
R1为氢或-Ln-Ar，R1 is hydrogen or -L n -Ar,
R2为氢，R2 is hydrogen,
L为直接键合、取代或未取代的亚芳基、或者取代或未取代的碳原子数3至30的单环的亚杂芳基，L is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted monocyclic heteroarylene group having 3 to 30 carbon atoms,
Ar为氢、氘、腈基、卤素基团、取代或未取代的烷基、取代或未取代的烷氧基、取代或未取代的甲硅烷基、取代或未取代的氧化膦基、取代或未取代的胺基、取代或未取代的芳基、被芳基取代或未取代的吡啶基、被芳基取代或未取代的嘧啶基、被芳基或杂芳基取代或未取代的三嗪基、被芳基取代或未取代的哒嗪基、被烷基取代或未取代的苯并咪唑基、咪唑基、二苯并呋喃基、二苯并噻吩基、或菲咯啉基，Ar is hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a pyridyl group substituted or unsubstituted by an aryl group, a pyrimidinyl group substituted or unsubstituted by an aryl group, a triazine group substituted or unsubstituted by an aryl group or a heteroaryl group, a pyridazine group substituted or unsubstituted by an aryl group, a benzimidazolyl group substituted or unsubstituted by an alkyl group, an imidazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a phenanthroline group,
n为1至3的整数，n为2以上时，L彼此相同或不同。n is an integer of 1 to 3, and when n is 2 or more, L's are the same as or different from each other.
本说明书的另一实施方式提供一种有机发光器件，其中，包括：第一电极、与上述第一电极对置而具备的第二电极、以及具备在上述第一电极与第二电极之间的一层或两层以上的有机物层，上述有机物层中的一层以上包含上述化合物1的杂环化合物。Another embodiment of the present specification provides an organic light-emitting device, comprising: a first electrode, a second electrode opposite to the first electrode, and one or more organic layers between the first electrode and the second electrode, wherein one or more of the organic layers contains a heterocyclic compound of the compound 1.
发明效果Effects of the Invention
根据本说明书的一实施方式的杂环化合物可以用作有机发光器件的有机物层的材料，通过使用该化合物，从而在有机发光器件中能够实现效率的提高、低驱动电压和/或寿命特性的提高。The heterocyclic compound according to one embodiment of the present specification can be used as a material of an organic layer of an organic light-emitting device, and by using the compound, improved efficiency, low driving voltage, and/or improved lifespan characteristics can be achieved in the organic light-emitting device.
附图说明BRIEF DESCRIPTION OF THE DRAWINGS
图1图示了根据本说明书的一实施方式的有机发光器件。FIG. 1 illustrates an organic light emitting device according to one embodiment of the present specification.
图2图示了根据本说明书的一实施方式的有机发光器件。FIG. 2 illustrates an organic light emitting device according to an embodiment of the present specification.
[符号说明][Explanation of symbols]
1：基板1: Substrate
2：第一电极2: First electrode
3：有机物层3: Organic layer
4：第二电极4: Second electrode
5：空穴注入层5: Hole injection layer
6：空穴传输层6: Hole transport layer
7：电子抑制层7: Electronic suppression layer
8：发光层8: Luminous layer
9：空穴阻挡层9: Hole blocking layer
10：电子注入和传输层10: Electron injection and transport layer
具体实施方式DETAILED DESCRIPTION
下面，对本说明书更详细地进行说明。Next, this specification is described in more detail.
本说明书提供由上述化学式1表示的杂环化合物。The present specification provides a heterocyclic compound represented by the above Chemical Formula 1.
本说明书的杂环化合物的特征在于，具有包含1个以上的N的六元环稠合而成的环结构。The heterocyclic compound of the present specification is characterized by having a ring structure in which six-membered rings containing one or more N are condensed.
通常情况下，化合物的电子迁移率根据分子的3D结构上的取向性(orientation)而不同，在为相对水平的结构(horizontal structure)时，电子迁移率加强。Generally, the electron mobility of a compound varies depending on the orientation of the 3D structure of the molecule, and the electron mobility is enhanced in a relatively horizontal structure.
根据本说明书的一实施方式的取代有一个-Ln-Ar的由化学式1表示的杂环化合物与取代有两个-L1-Ar1的化合物相比，分子的水平结构趋向强烈，因此具有电子迁移率提高的优点。The heterocyclic compound represented by Chemical Formula 1 substituted with one -Ln- Ar according to one embodiment of the present specification has an advantage of improved electron mobility because the horizontal structure of the molecule tends to be stronger than that of the compound substituted with two -L1-Ar1.
由此，在将由化学式1表示的杂环化合物利用于有机发光器件时，具有驱动电压低、高效率和长寿命的效果(参照APPLIED PHYSICS LETTERS 95,243303(2009))。Therefore, when the heterocyclic compound represented by Chemical Formula 1 is used in an organic light-emitting device, it has the effects of low driving voltage, high efficiency, and long life (see APPLIED PHYSICS LETTERS 95, 243303 (2009)).
在本说明书中，当指出某一部分“包含/包括”某一构成要素时，只要没有特别相反的记载，则意味着可以进一步包含其它构成要素，而不是将其它构成要素排除。In the present specification, when it is indicated that a certain part “includes/comprises” a certain constituent element, unless there is a particular description to the contrary, it means that other constituent elements may be further included, rather than excluding other constituent elements.
在本说明书中，当指出某一构件位于另一个构件“上”时，其不仅包含某一构件与另一构件接触的情况，还包括两构件之间存在其它构件的情况。In this specification, when it is mentioned that a certain member is located “on” another member, it not only includes the case where the certain member is in contact with the other member, but also includes the case where other members are present between the two members.
在本说明书中，取代基的示例在下文中进行说明，但并不限定于此。In the present specification, examples of substituents are described below, but are not limited thereto.
上述“取代”这一用语的意思是指结合于化合物的碳原子上的氢原子被替换成其它取代基，被取代的位置只要是氢原子可以被取代的位置、即取代基可以取代的位置就没有限定，当取代2个以上时，2个以上的取代基可以彼此相同或不同。The term "substituted" mentioned above means that the hydrogen atom bonded to the carbon atom of the compound is replaced by another substituent. The substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted. When there are more than two substitutions, the two or more substituents may be the same or different from each other.
在本说明书中，“取代或未取代的”这一用语是指被选自氘、腈基、取代或未取代的烷基、取代或未取代的甲硅烷基、取代或未取代的芳基、以及取代或未取代的杂环基中的1个或2个以上的取代基取代，或者被上述例示的取代基中的2个以上的取代基连接而成的取代基取代，或者不具有任何取代基。例如，“2个以上的取代基连接而成的取代基”可以为被芳基取代的芳基、被杂芳基取代的芳基、被芳基取代的杂环基、被烷基取代的芳基等。In this specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium, nitrile, substituted or unsubstituted alkyl, substituted or unsubstituted silyl, substituted or unsubstituted aryl, and substituted or unsubstituted heterocyclic, or substituted with a substituent formed by connecting two or more substituents among the substituents exemplified above, or having no substituents. For example, "a substituent formed by connecting two or more substituents" may be an aryl substituted with an aryl, an aryl substituted with a heteroaryl, a heterocyclic substituted with an aryl, an aryl substituted with an alkyl, and the like.
在本说明书中，上述烷基可以为直链或支链，碳原子数没有特别限定，但优选为1至30。In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
在本说明书中，甲硅烷基具体有三甲基甲硅烷基、三乙基甲硅烷基、叔丁基二甲基甲硅烷基、乙烯基二甲基甲硅烷基、丙基二甲基甲硅烷基、三苯基甲硅烷基、二苯基甲硅烷基、苯基甲硅烷基等，但并不限定于此。In the present specification, specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl, but are not limited thereto.
在本说明书中，芳基没有特别限定，但优选碳原子数6至30的芳基，上述芳基可以为单环或多环。In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
上述芳基为单环芳基时，碳原子数没有特别限定，但优选碳原子数为6至30。When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 6 to 30.
上述芳基为多环芳基时，碳原子数没有特别限定，但优选碳原子数为10至30。When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 10 to 30.
在本说明书中，作为芳基胺基的例子，有取代或未取代的单芳基胺基、取代或未取代的二芳基胺基、或者取代或未取代的三芳基胺基。上述芳基胺基中的芳基可以为单环芳基，可以为多环芳基。上述包含2个以上芳基的芳基胺基可以包含单环芳基、多环芳基，或者可以同时包含单环芳基和多环芳基。例如，上述芳基胺基中的芳基可以选自上述的芳基的例示。In this specification, examples of arylamine groups include substituted or unsubstituted monoarylamine groups, substituted or unsubstituted diarylamine groups, or substituted or unsubstituted triarylamine groups. The aryl group in the above-mentioned arylamine groups may be a monocyclic aryl group or a polycyclic aryl group. The above-mentioned arylamine groups containing more than two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or may contain a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the above-mentioned arylamine groups may be selected from the examples of the above-mentioned aryl groups.
在本说明书中，杂芳基包含一个以上非碳原子即杂原子，具体而言，上述杂原子可以包含一个以上选自O、N、Se和S等中的原子。碳原子数没有特别限定，但优选碳原子数为2至30，上述杂芳基可以为单环或多环。In the present specification, the heteroaryl group contains one or more non-carbon atoms, i.e., heteroatoms. Specifically, the heteroatoms may contain one or more atoms selected from O, N, Se, and S. The number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 30. The heteroaryl group may be monocyclic or polycyclic.
在本说明书中，亚芳基除了是2价以外，与芳基的定义相同。In the present specification, the arylene group has the same definition as the aryl group except that it is divalent.
在本说明书中，亚杂芳基除了是2价以外，与杂芳基的定义相同。In the present specification, the heteroarylene group has the same definition as the heteroaryl group except that it is divalent.
在本说明书的一实施方式中，上述化学式1可以由下述化学式2表示。In one embodiment of the present specification, the above Chemical Formula 1 may be represented by the following Chemical Formula 2.
[化学式2][Chemical formula 2]
在上述化学式2中，上述X1、X2、X4至X7、Y1至Y7、L、Ar和n的定义与上述化学式1中的定义相同。In the above Chemical Formula 2, the definitions of X 1 , X 2 , X 4 to X 7 , Y 1 to Y 7 , L, Ar and n are the same as those in the above Chemical Formula 1.
根据本说明书的一实施方式，上述X1至X7中的任一个以上为N，其余为CR1。According to one embodiment of the present specification, at least one of X1 to X7 is N, and the rest are CR1.
根据本说明书的一实施方式，上述X1至X7中的任一个为N，其余为CR1。According to one embodiment of the present specification, any one of X1 to X7 is N, and the others are CR1.
根据本说明书的一实施方式，上述Y1至Y7中的任一个以上为N，其余为CR1。According to one embodiment of the present specification, at least one of Y1 to Y7 is N, and the rest are CR1.
根据本说明书的一实施方式，上述Y1至Y7中的任一个为N，其余为CR1。According to one embodiment of the present specification, any one of Y1 to Y7 is N, and the others are CR1.
根据本说明书的一实施方式，上述X1为N，X2至X7为CR1。According to one embodiment of the present specification, X1 is N, and X2 to X7 are CR1.
根据本说明书的一实施方式，上述X2为N，X1以及X3至X7为CR1。According to one embodiment of the present specification, X2 is N, and X1 and X3 to X7 are CR1.
根据本说明书的一实施方式，上述X3为N，X1、X2、以及X4至X7为CR1。According to one embodiment of the present specification, X3 is N, and X1 , X2 , and X4 to X7 are CR1.
根据本说明书的一实施方式，上述X4为N，X1至X3、以及X5至X7为CR1。According to one embodiment of the present specification, X4 is N, and X1 to X3 , and X5 to X7 are CR1.
根据本说明书的一实施方式，上述X5为N，X1至X4、X6、以及X7为CR1。According to one embodiment of the present specification, X5 is N, and X1 to X4 , X6 , and X7 are CR1.
根据本说明书的一实施方式，上述X6为N，X1至X5、以及X7为CR1。According to one embodiment of the present specification, X6 is N, and X1 to X5 , and X7 are CR1.
根据本说明书的一实施方式，上述X7为N，X1至X6为CR1。According to one embodiment of the present specification, X7 is N, and X1 to X6 are CR1.
根据本说明书的一实施方式，上述Y1为N，Y2至Y7为CR2。According to one embodiment of the present specification, Y1 is N, and Y2 to Y7 are CR2.
根据本说明书的一实施方式，上述Y2为N，Y1、以及Y3至Y7为CR2。According to one embodiment of the present specification, Y2 is N, and Y1 , and Y3 to Y7 are CR2.
根据本说明书的一实施方式，上述Y3为N，Y1、Y2、以及Y4至Y7为CR2。According to one embodiment of the present specification, Y 3 is N, and Y 1 , Y 2 , and Y 4 to Y 7 are CR2.
根据本说明书的一实施方式，上述Y4为N，Y1至Y3、以及Y5至Y7为CR2。According to one embodiment of the present specification, Y4 is N, and Y1 to Y3 , and Y5 to Y7 are CR2.
根据本说明书的一实施方式，上述Y5为N，Y1至Y4、Y6、以及Y7为CR2。According to one embodiment of the present specification, Y5 is N, and Y1 to Y4 , Y6 , and Y7 are CR2.
根据本说明书的一实施方式，上述Y6为N，Y1至Y5、以及Y7为CR2。According to one embodiment of the present specification, Y6 is N, and Y1 to Y5 , and Y7 are CR2.
根据本说明书的一实施方式，上述Y7为N，Y1至Y6为CR2。According to one embodiment of the present specification, Y7 is N, and Y1 to Y6 are CR2.
在本说明书的一实施方式中，上述化学式1可以由下述化学式3至9中的任一个表示。In one embodiment of the present specification, the above Chemical Formula 1 may be represented by any one of the following Chemical Formulas 3 to 9.
在上述化学式3至9中，上述L、n和Ar的定义与上述化学式1中的定义相同。In the above Chemical Formulae 3 to 9, the definitions of L, n and Ar are the same as those in the above Chemical Formula 1.
在本说明书的一实施方式中，上述化学式1可以由下述化学式1-1表示。In one embodiment of the present specification, the above Chemical Formula 1 may be represented by the following Chemical Formula 1-1.
[化学式1-1][Chemical formula 1-1]
在上述化学式1-1中，X1至X7、以及Y1至Y7与上述定义相同，In the above Chemical Formula 1-1, X1 to X7 , and Y1 to Y7 are the same as defined above.
Z1至Z3彼此相同或不同，各自独立地为N或CH2， Z1 to Z3 are the same as or different from each other, and are each independently N or CH2 ,
上述Z1至Z3中的一个以上为N，At least one of the above Z1 to Z3 is N,
L101为直接键合、取代或未取代的亚芳基、或亚杂芳基，L 101 is a direct bond, a substituted or unsubstituted arylene group, or a heteroarylene group,
Ar101和Ar102彼此相同或不同，各自独立地为氢、氘、腈基、卤素基团、取代或未取代的烷基、取代或未取代的烷氧基、取代或未取代的甲硅烷基、取代或未取代的氧化膦基、取代或未取代的胺基、取代或未取代的芳基、或者取代或未取代的杂芳基，Ar 101 and Ar 102 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
m为1至2的整数，上述m为2时，上述L101彼此相同或不同。m is an integer of 1 to 2. When m is 2, the L 101 are the same as or different from each other.
在本说明书的一实施方式中，上述化学式1可以由下述化学式1-2表示。In one embodiment of the present specification, the above Chemical Formula 1 may be represented by the following Chemical Formula 1-2.
[化学式1-2][Chemical formula 1-2]
在上述化学式1-2中，上述X1至X7、以及Y1至Y7与上述定义相同，In the above chemical formula 1-2, X1 to X7 and Y1 to Y7 are the same as defined above.
上述R3为取代或未取代的氧化膦基、取代或未取代的芳基、或者取代或未取代的杂芳基，The above R 3 is a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
o为0至3的整数，o为2以上时，R3彼此相同或不同。o is an integer of 0 to 3, and when o is 2 or more, R3 are the same as or different from each other.
根据本说明书的一实施方式，上述R1和R2为氢。According to one embodiment of the present specification, R 1 and R 2 are hydrogen.
根据本说明书的一实施方式，上述R3为被碳原子数6至30的芳基取代的氧化膦基、取代或未取代的碳原子数6至30的芳基、或者取代或未取代的碳原子数3至30的杂芳基。According to one embodiment of the present specification, R 3 is a phosphine oxide group substituted with an aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
根据本说明书的一实施方式，上述R3为被碳原子数6至30的芳基取代的氧化膦基；被芳基或杂芳基取代或未取代的碳原子数6至30的芳基；或者被芳基或杂芳基取代或未取代的包含N、O和S中的任一种以上的杂芳基。According to one embodiment of the present specification, R3 is a phosphine oxide group substituted by an aryl group having 6 to 30 carbon atoms; an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted by an aryl group or a heteroaryl group; or a heteroaryl group containing any one or more of N, O and S which is substituted or unsubstituted by an aryl group or a heteroaryl group.
根据本说明书的一实施方式，上述R3为菲基、氧化膦基、菲咯啉基、哒嗪基、或苯并咪唑基，According to one embodiment of the present specification, the above R 3 is a phenanthryl group, a phosphine oxide group, a phenanthroline group, a pyridazine group, or a benzimidazolyl group.
上述菲基、氧化膦基、菲咯啉基、哒嗪基、或苯并咪唑基被碳原子数1至10的烷基；碳原子数6至30的芳基、或碳原子数3至30的包含N、O和S中的任一种以上的杂芳基取代或未取代。The phenanthrenyl, phosphine oxide, phenanthroline, pyridazinyl, or benzimidazolyl group may be substituted or unsubstituted by an alkyl group having 1 to 10 carbon atoms; an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms and containing any one or more of N, O and S.
根据本说明书的一实施方式，上述R3为菲基、氧化膦基、菲咯啉基、哒嗪基、或苯并咪唑基，According to one embodiment of the present specification, the above R 3 is a phenanthryl group, a phosphine oxide group, a phenanthroline group, a pyridazine group, or a benzimidazolyl group.
上述菲基、氧化膦基、菲咯啉基、哒嗪基、或苯并咪唑基被甲基、乙基、丙基、丁基、叔丁基、苯基、联苯基、三联苯基、萘基、蒽基、菲基、芘基、三亚苯基、吡啶基、嘧啶基、三嗪基、咔唑基、二苯并呋喃基、或二苯并噻吩基取代或未取代。The above-mentioned phenanthryl, phosphine oxide, phenanthroline, pyridazinyl, or benzimidazolyl may be substituted or unsubstituted by methyl, ethyl, propyl, butyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, pyrene, triphenylene, pyridyl, pyrimidinyl, triazine, carbazolyl, dibenzofuranyl, or dibenzothiophenyl.
根据本说明书的一实施方式，上述R3为菲基、被芳基取代的氧化膦基、菲咯啉基、被芳基取代或未取代的哒嗪基、或者被烷基取代或未取代的苯并咪唑基。According to one embodiment of the present specification, R 3 is a phenanthryl group, a phosphine oxide group substituted with an aryl group, a phenanthroline group, a pyridazinyl group substituted or unsubstituted with an aryl group, or a benzimidazolyl group substituted or unsubstituted with an alkyl group.
根据本说明书的一实施方式，上述R3为被苯基取代的氧化膦基、菲咯啉基、被苯基或萘基取代或未取代的哒嗪基、或者被甲基取代或未取代的苯并咪唑基。According to one embodiment of the present specification, R 3 is a phosphine oxide group substituted with a phenyl group, a phenanthroline group, a pyridazinyl group substituted or unsubstituted with a phenyl group or a naphthyl group, or a benzimidazolyl group substituted or unsubstituted with a methyl group.
根据本说明书的一实施方式，上述L为直接键合；取代或未取代的碳原子数6至30的亚芳基；或者取代或未取代的碳原子数3至30的包含N、O和S中的任一种以上的单环的亚杂芳基。According to one embodiment of the present specification, L is a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic heteroarylene group having 3 to 30 carbon atoms containing at least one of N, O and S.
根据本说明书的一实施方式，上述L为直接键合；碳原子数6至30的亚芳基；或者碳原子数3至30的包含N、O和S中的任一种以上的亚杂芳基。According to one embodiment of the present specification, L is a direct bond; an arylene group having 6 to 30 carbon atoms; or a heteroarylene group containing any one or more of N, O and S having 3 to 30 carbon atoms.
根据本说明书的一实施方式，上述L为直接键合、亚苯基、2价的联苯基、2价的三联苯基、亚萘基、亚蒽基、亚菲基、或2价的芘基。According to one embodiment of the present specification, L is a direct bond, a phenylene group, a divalent biphenyl group, a divalent terphenyl group, a naphthylene group, an anthrylene group, a phenanthrylene group, or a divalent pyrene group.
根据本说明书的一实施方式，上述L为直接键合、亚苯基、亚萘基、或2价的芘基。According to one embodiment of the present specification, the above-mentioned L is a direct bond, a phenylene group, a naphthylene group, or a divalent pyrenyl group.
根据本说明书的一实施方式，上述L101为直接键合；取代或未取代的碳原子数6至30的亚芳基；或者取代或未取代的碳原子数3至30的包含N、O和S中的任一种以上的亚杂芳基。According to one embodiment of the present specification, L 101 is a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group containing any one or more of N, O and S having 3 to 30 carbon atoms.
根据本说明书的一实施方式，上述L101为直接键合；碳原子数6至30的亚芳基；或者碳原子数3至30的包含N、O和S中的任一种以上的亚杂芳基。According to one embodiment of the present specification, L 101 is a direct bond; an arylene group having 6 to 30 carbon atoms; or a heteroarylene group containing any one or more of N, O and S having 3 to 30 carbon atoms.
根据本说明书的一实施方式，上述L101为直接键合、亚苯基、2价的联苯基、2价的三联苯基、亚萘基、亚蒽基、亚菲基、或2价的芘基。According to one embodiment of the present specification, L 101 is a direct bond, a phenylene group, a divalent biphenyl group, a divalent terphenyl group, a naphthylene group, an anthrylene group, a phenanthrylene group, or a divalent pyrene group.
根据本说明书的一实施方式，上述L101为直接键合、亚苯基、或亚萘基。According to one embodiment of the present specification, the above-mentioned L 101 is a direct bond, a phenylene group, or a naphthylene group.
根据本说明书的一实施方式，上述Ar为氢、氘、腈基、烷基、被芳基取代或未取代的氧化膦基、被烷基取代的甲硅烷基、被腈基取代或未取代的芳基、被烷基取代或未取代的杂芳基、或者被芳基取代或未取代的杂芳基。According to one embodiment of the present specification, Ar is hydrogen, deuterium, a nitrile group, an alkyl group, a phosphine oxide group substituted or unsubstituted by an aryl group, a silyl group substituted by an alkyl group, an aryl group substituted or unsubstituted by a nitrile group, a heteroaryl group substituted or unsubstituted by an alkyl group, or a heteroaryl group substituted or unsubstituted by an aryl group.
根据本说明书的一实施方式，上述Ar为氢、氘、腈基、烷基、被芳基取代或未取代的氧化膦基、被烷基取代的甲硅烷基、被腈基取代或未取代的芳基、被烷基取代或未取代的杂芳基、或者被芳基取代或未取代的杂芳基。According to one embodiment of the present specification, Ar is hydrogen, deuterium, a nitrile group, an alkyl group, a phosphine oxide group substituted or unsubstituted by an aryl group, a silyl group substituted by an alkyl group, an aryl group substituted or unsubstituted by a nitrile group, a heteroaryl group substituted or unsubstituted by an alkyl group, or a heteroaryl group substituted or unsubstituted by an aryl group.
根据本说明书的一实施方式，上述Ar为被碳原子数6至30的芳基取代或未取代的氧化膦基、被腈基取代或未取代的碳原子数6至30的芳基、或者被碳原子数1至10的烷基或碳原子数6至30的芳基取代或未取代的碳原子数3至30的杂芳基。According to one embodiment of the present specification, the above-mentioned Ar is a phosphine oxide group which is substituted or unsubstituted by an aryl group having 6 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted by a nitrile group, or a heteroaryl group having 3 to 30 carbon atoms which is substituted or unsubstituted by an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms.
根据本说明书的一实施方式，上述Ar为被碳原子数6至30的芳基取代或未取代的氧化膦基、被腈基取代或未取代的碳原子数6至30的芳基、被芳基取代或未取代的吡啶基、被芳基取代或未取代的嘧啶基、被芳基或杂芳基取代或未取代的三嗪基、被芳基取代或未取代的哒嗪基、被烷基取代或未取代的苯并咪唑基、咪唑基、二苯并呋喃基、二苯并噻吩基、或菲咯啉基。According to one embodiment of the present specification, the above-mentioned Ar is a phosphine oxide group substituted or unsubstituted by an aromatic group having 6 to 30 carbon atoms, an aromatic group having 6 to 30 carbon atoms substituted or unsubstituted by a nitrile group, a pyridyl group substituted or unsubstituted by an aromatic group, a pyrimidyl group substituted or unsubstituted by an aromatic group, a triazine group substituted or unsubstituted by an aromatic group or a heteroaryl group, a pyridazine group substituted or unsubstituted by an aromatic group, a benzimidazolyl group substituted or unsubstituted by an alkyl group, an imidazolyl group, a dibenzofuranyl group, a dibenzothiophene group, or a phenanthroline group.
根据本说明书的一实施方式，上述Ar为苯基、联苯基、三联苯基、萘基、荧蒽基、芘基、三亚苯基、氧化膦基、喹啉基、喹唑啉基、吡啶基、嘧啶基、三嗪基、哒嗪基、苯并咪唑基、咪唑基、二苯并呋喃基、二苯并噻吩基、或菲咯啉基，According to one embodiment of the present specification, Ar is phenyl, biphenyl, terphenyl, naphthyl, fluoranthenyl, pyrene, triphenylene, phosphine oxide, quinolyl, quinazolinyl, pyridyl, pyrimidinyl, triazine, pyridazine, benzimidazolyl, imidazolyl, dibenzofuranyl, dibenzothiophenyl, or phenanthroline,
上述Ar的示例可以被选自氘、腈基、氟基团、氯基团、溴基团、碘基团、碳原子数1至10的烷基、碳原子数6至30的芳基、以及碳原子数3至30的杂芳基中的任一种以上取代或未取代。The examples of Ar mentioned above may be substituted or unsubstituted by any one or more selected from deuterium, a nitrile group, a fluorine group, a chlorine group, a bromine group, an iodine group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 3 to 30 carbon atoms.
根据本说明书的一实施方式，上述Ar为被腈基取代或未取代的苯基；被腈基取代或未取代的联苯基；三联苯基；被苯基或萘基取代的氧化膦基；被苯基取代或未取代的喹唑啉基；被苯基取代或未取代的哒嗪基；被甲基取代或未取代的苯并咪唑基；荧蒽基；吡啶基；被苯基、苯甲腈基或吡啶基取代或未取代的三嗪基。According to one embodiment of the present specification, the above-mentioned Ar is a phenyl group substituted or unsubstituted by a nitrile group; a biphenyl group substituted or unsubstituted by a nitrile group; a terphenyl group; a phosphine oxide group substituted by a phenyl or naphthyl group; a quinazoline group substituted or unsubstituted by a phenyl group; a pyridazine group substituted or unsubstituted by a phenyl group; a benzimidazolyl group substituted or unsubstituted by a methyl group; a fluoranthene group; a pyridyl group; a triazine group substituted or unsubstituted by a phenyl group, a benzonitrile group or a pyridyl group.
根据本说明书的一实施方式，上述Ar101和Ar102彼此相同或不同，各自独立地为取代或未取代的碳原子数6至30的芳基、或者取代或未取代的碳原子数3至30的杂芳基。According to one embodiment of the present specification, Ar 101 and Ar 102 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
根据本说明书的一实施方式，上述Ar101和Ar102彼此相同或不同，各自独立地为碳原子数6至30的芳基、或碳原子数3至30的杂芳基，According to one embodiment of the present specification, Ar 101 and Ar 102 are the same or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.
上述碳原子数6至30的芳基、或碳原子数3至30的杂芳基被选自氘、卤素基团、腈基、烷基、芳基、或杂芳基中的一种以上的取代基取代或未取代。The aryl group having 6 to 30 carbon atoms or the heteroaryl group having 3 to 30 carbon atoms may be substituted or unsubstituted with one or more substituents selected from deuterium, a halogen group, a nitrile group, an alkyl group, an aryl group, or a heteroaryl group.
根据本说明书的一实施方式，上述Ar101和Ar102彼此相同或不同，各自独立地为苯基、联苯基、萘基、吡啶基、嘧啶基、或三嗪基，According to one embodiment of the present specification, Ar 101 and Ar 102 are the same as or different from each other, and are each independently phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl, or triazine.
上述苯基、联苯基、萘基、吡啶基、嘧啶基、或三嗪基可以被选自腈基、苯基、联苯基、三联苯基、萘基、蒽基、芘基、菲基、三亚苯基、菲咯啉基、吡啶基、嘧啶基、二苯并呋喃基、以及二苯并噻吩基中的任一种以上的取代基取代或未取代。The above-mentioned phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl, or triazine group may be substituted or unsubstituted by any one or more substituents selected from nitrile group, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, pyrene group, phenanthrenyl, triphenylene group, phenanthroline group, pyridyl, pyrimidyl, dibenzofuranyl, and dibenzothiophenyl group.
根据本说明书的一实施方式，上述Ar101和Ar102彼此相同或不同，各自独立地为苯基、联苯基、萘基、或吡啶基，According to one embodiment of the present specification, Ar 101 and Ar 102 are the same or different from each other, and are each independently a phenyl group, a biphenyl group, a naphthyl group, or a pyridyl group.
上述苯基、联苯基、萘基、或吡啶基可以被选自腈基、苯基、联苯基、萘基、芘基、菲基、菲咯啉基、吡啶基、嘧啶基、二苯并呋喃基、以及二苯并噻吩基中的任一种以上的取代基取代或未取代。The above-mentioned phenyl, biphenyl, naphthyl, or pyridyl group may be substituted or unsubstituted with any one or more substituents selected from nitrile group, phenyl, biphenyl, naphthyl, pyrenyl, phenanthrenyl, phenanthroline group, pyridyl group, pyrimidinyl group, dibenzofuranyl group, and dibenzothiophenyl group.
根据本说明书另一实施方式，上述化学式1的杂环化合物可以由下述结构式中的任一个表示。According to another embodiment of the present specification, the heterocyclic compound of the above Chemical Formula 1 can be represented by any one of the following structural formulas.
本发明的有机发光器件利用上述的化合物形成一层以上的有机物层，除此以外，可以利用通常的有机发光器件的制造方法和材料进行制造。The organic light-emitting device of the present invention uses the above-mentioned compound to form one or more organic layers, and can be manufactured using conventional organic light-emitting device manufacturing methods and materials.
另外，根据本发明的有机电致发光器件，其特征在于，包括：第一电极、与上述第一电极对置而具备的第二电极、以及具备在上述第一电极与第二电极之间的一层或两层以上的有机物层，上述有机物层中的一层以上包含由上述化学式1表示的杂环化合物。In addition, the organic electroluminescent device according to the present invention is characterized in that it includes: a first electrode, a second electrode opposite to the first electrode, and one or more organic layers between the first electrode and the second electrode, and one or more of the organic layers contains the heterocyclic compound represented by the above chemical formula 1.
根据本发明的一实施方式，上述有机物层包括电子注入层、电子传输层、或电子注入和传输层，上述电子注入层、电子传输层、或电子注入和传输层包含上述化学式1的杂环化合物。According to one embodiment of the present invention, the organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the heterocyclic compound of Chemical Formula 1.
根据本发明的一实施方式，上述电子注入层、电子传输层、或电子注入和传输层可以包含上述化学式1的杂环化合物和其他的化合物。According to one embodiment of the present invention, the electron injection layer, the electron transport layer, or the electron injection and transport layer may include the heterocyclic compound of Chemical Formula 1 and other compounds.
根据本发明的一实施方式，上述电子注入层、电子传输层、或电子注入和传输层可以包含上述化学式1的杂环化合物，并且可以与金属配合物一同使用。According to one embodiment of the present invention, the electron injection layer, the electron transport layer, or the electron injection and transport layer may include the heterocyclic compound of Chemical Formula 1, and may be used together with a metal complex.
根据本发明的一实施方式，上述电子注入层、电子传输层、或电子注入和传输层可以包含上述化学式1的杂环化合物，并且可以与锂配合物一同使用。According to an embodiment of the present invention, the electron injection layer, the electron transport layer, or the electron injection and transport layer may include the heterocyclic compound of Chemical Formula 1, and may be used together with a lithium complex.
根据本发明的一实施方式，上述电子注入层、电子传输层、或电子注入和传输层以1:1至2:1的重量比使用上述化合物1的杂环化合物和喹啉锂-8-油酸盐。According to one embodiment of the present invention, the electron injection layer, the electron transport layer, or the electron injection and transport layer uses the heterocyclic compound of Compound 1 and lithium quinolate-8-oleate at a weight ratio of 1:1 to 2:1.
根据本发明的一实施方式，上述有机物层包括空穴注入层、空穴传输层、或空穴注入和传输层，上述空穴注入层、空穴传输层、或空穴注入和传输层包含上述化学式1的杂环化合物。According to one embodiment of the present invention, the organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer includes the heterocyclic compound of Chemical Formula 1.
根据本发明的一实施方式，上述有机物层包括发光层，上述发光层包含上述化学式1的杂环化合物。According to an embodiment of the present invention, the organic layer includes a light-emitting layer, and the light-emitting layer includes the heterocyclic compound of Chemical Formula 1.
图1例示了在基板1上依次层叠有第一电极2、有机物层3、以及第二电极4的有机发光器件的结构。上述化学式1的杂环化合物包含在上述有机物层3中。1 illustrates a structure of an organic light emitting device in which a first electrode 2, an organic layer 3, and a second electrode 4 are sequentially stacked on a substrate 1. The heterocyclic compound of the above Chemical Formula 1 is contained in the above organic layer 3.
图2例示了在基板1上依次层叠有第一电极2、空穴注入层5、空穴传输层6、电子抑制层7、发光层8、空穴阻挡层9、电子注入和传输层10、以及第二电极4的有机发光器件的结构。上述化学式1的杂环化合物优选地可以包含在空穴阻挡层9或电子注入和传输层10中。2 illustrates a structure of an organic light-emitting device in which a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light-emitting layer 8, a hole blocking layer 9, an electron injection and transport layer 10, and a second electrode 4 are sequentially stacked on a substrate 1. The heterocyclic compound of the above Chemical Formula 1 may preferably be contained in the hole blocking layer 9 or the electron injection and transport layer 10.
但是，根据本说明书的一实施方式的有机发光器件的结构并不限定于图1和2，可以为下述结构中的任一个。However, the structure of the organic light-emitting device according to one embodiment of the present specification is not limited to FIGS. 1 and 2 , and may be any of the following structures.
(1)阳极/空穴传输层/发光层/电子传输层/阴极(1) Anode/hole transport layer/light-emitting layer/electron transport layer/cathode
(2)阳极/空穴传输层/发光层/电子传输层/电子注入层/阴极(2) Anode/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode
(3)阳极/空穴注入层/空穴传输层/发光层/电子传输层/电子注入层/阴极(3) Anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode
(4)阳极/空穴传输层/空穴调节层/发光层/电子传输层/电子注入层/阴极(4) Anode/hole transport layer/hole regulation layer/light-emitting layer/electron transport layer/electron injection layer/cathode
(5)阳极/空穴注入层/空穴传输层/空穴调节层/发光层/电子传输层/电子注入层/阴极(5) Anode/hole injection layer/hole transport layer/hole regulation layer/light-emitting layer/electron transport layer/electron injection layer/cathode
(6)阳极/空穴传输层/发光层/电子调节层/电子传输层/阴极(6) Anode/hole transport layer/light-emitting layer/electron regulation layer/electron transport layer/cathode
(7)阳极/空穴传输层/发光层/电子调节层/电子传输层/电子注入层/阴极(7) Anode/hole transport layer/light-emitting layer/electron regulation layer/electron transport layer/electron injection layer/cathode
(8)阳极/空穴注入层/空穴传输层/发光层/电子调节层/电子传输层/阴极(8) Anode/hole injection layer/hole transport layer/light-emitting layer/electron regulation layer/electron transport layer/cathode
(9)阳极/空穴注入层/空穴传输层/发光层/电子调节层/电子传输层/电子注入层/阴极(9) Anode/hole injection layer/hole transport layer/light-emitting layer/electron regulation layer/electron transport layer/electron injection layer/cathode
根据本发明的一实施方式，上述第一电极为阳极，上述第二电极为阴极。According to one embodiment of the present invention, the first electrode is an anode, and the second electrode is a cathode.
根据本发明的一实施方式，上述第二电极为阳极，上述第一电极为阴极。According to an embodiment of the present invention, the second electrode is an anode, and the first electrode is a cathode.
在本发明的一实施方式中，包含上述化学式1的杂环化合物的有机物层包括电子注入层、电子传输层、同时进行电子注入和电子传输的层中的至少一层，上述层中的至少一层可以包含上述化学式1的杂环化合物。In one embodiment of the present invention, the organic layer containing the heterocyclic compound of the above Chemical Formula 1 includes at least one of an electron injection layer, an electron transport layer, and a layer that simultaneously performs electron injection and electron transport, and at least one of the above layers may contain the heterocyclic compound of the above Chemical Formula 1.
作为上述阳极物质，通常为了使空穴能够顺利地向有机物层注入，优选为功函数大的物质。作为本发明中可以使用的阳极物质的具体例，有钒、铬、铜、锌、金等金属或它们的合金；氧化锌、氧化铟、氧化铟锡(ITO)、氧化铟锌(IZO)等金属氧化物；ZnO:Al或SnO2:Sb等金属与氧化物的组合；聚(3-甲基化合物的)、聚[3,4-(亚乙基-1,2-二氧)噻吩](PEDT)、聚吡咯和聚苯胺等导电性高分子等，但不仅限于此。As the above-mentioned anode material, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is generally preferred. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; conductive polymers such as poly(3-methyl thiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto.
作为上述阴极物质，通常为了使电子容易地向有机物层注入，优选为功函数小的物质。作为阴极物质的具体例，有镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅等金属或它们的合金；LiF/Al或LiO2/Al等多层结构物质等，但不仅限于此。The cathode material is preferably a material with a small work function in order to facilitate electron injection into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF/Al or LiO2 /Al, but are not limited thereto.
上述空穴注入物质是能够在低电压下从阳极良好地注入空穴的物质，优选空穴注入物质的HOMO(最高占有分子轨道，highest occupied molecular orbital)介于阳极物质的功函数与周围有机物层的HOMO之间。作为空穴注入物质的具体例，有金属卟啉(porphyrine)、低聚噻吩、芳基胺系有机物、六腈六氮杂苯并菲系有机物、喹吖啶酮(quinacridone)系有机物、苝(perylene)系有机物、蒽醌及聚苯胺和聚化合物的系导电性高分子等，但不仅限于此。The hole injection material is a material that can well inject holes from the anode at a low voltage, and the HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine organic matter, hexanitrile hexaazatriphenylene organic matter, quinacridone organic matter, perylene organic matter, anthraquinone, polyaniline and poly compound conductive polymers, but are not limited to these.
上述空穴传输物质是能够接收来自阳极或空穴注入层的空穴并将其转移至发光层的物质，对空穴的迁移率大的物质是合适的。作为具体例，有芳基胺系有机物、导电性高分子、以及同时存在共轭部分和非共轭部分的嵌段共聚物等，但不仅限于此。The hole transport material is a material that can receive holes from the anode or hole injection layer and transfer them to the light-emitting layer, and a material with a large hole mobility is suitable. As specific examples, there are arylamine organic substances, conductive polymers, and block copolymers with conjugated parts and non-conjugated parts at the same time, but are not limited to these.
上述发光物质是能够分别接收来自空穴传输层和电子传输层的空穴和电子并使它们结合而发出可见光区域的光的物质，优选对于荧光或磷光的量子效率高的物质。作为具体例，有8-羟基喹啉铝配合物(Alq3)；咔唑系化合物；二聚苯乙烯基(dimerized styryl)化合物；BAlq；10-羟基苯并喹啉-金属化合物；苯并唑、苯并噻唑及苯并咪唑系化合物；聚(对亚苯基亚乙烯基)(PPV)系高分子；螺环(spiro)化合物；聚芴、红荧烯等，但不仅限于此。The luminescent material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer, respectively, and combine them to emit light in the visible light region. It is preferably a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complex (Alq 3 ); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo azole, benzothiazole and benzimidazole compounds; poly(p-phenylene vinylene) (PPV) polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited to these.
上述发光层可以包含主体材料和掺杂剂材料。作为主体材料，有芳香族稠环衍生物或含杂环化合物等。具体而言，作为芳香族稠环衍生物，有蒽衍生物、芘衍生物、萘衍生物、并五苯衍生物、菲化合物、荧蒽化合物等，作为含杂环化合物，有杂环化合物、二苯并呋喃衍生物、梯型呋喃化合物嘧啶衍生物等，但并不限定于此。The above-mentioned light-emitting layer may include a host material and a dopant material. As the host material, there are aromatic fused ring derivatives or heterocyclic compounds. Specifically, as aromatic fused ring derivatives, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and as heterocyclic compounds, there are heterocyclic compounds, dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited to these.
上述有机发光器件包括复数个有机物层时，上述有机物层可以由相同的物质或不同的物质形成。When the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
本说明书的有机发光器件中，有机物层中的一层以上利用上述杂环化合物形成，除此以外，可以利用该技术领域中已知的材料和方法进行制造。In the organic light-emitting device of the present specification, at least one of the organic layers is formed using the above-mentioned heterocyclic compound, and other organic layers can be manufactured using materials and methods known in the technical field.
作为掺杂剂材料，有芳香族胺衍生物、苯乙烯基胺化合物、硼配合物、荧蒽化合物、金属配合物等。具体而言，芳香族胺衍生物是具有取代或未取代的芳基氨基的芳香族稠环衍生物，有具有芳基氨基的芘、蒽、二茚并芘等，苯乙烯基胺化合物是在取代或未取代的芳基胺上取代有至少一个芳基乙烯基的化合物，被选自芳基、甲硅烷基、烷基、环烷基和芳基氨基中的1个或2个以上的取代基取代或未取代。具体而言，有苯乙烯基胺、苯乙烯基二胺、苯乙烯基三胺、苯乙烯基四胺等，但并不限定于此。此外，作为金属配合物，有铱配合物、铂配合物等，但并不限定于此。As dopant materials, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are aromatic fused ring derivatives having substituted or unsubstituted arylamino groups, and there are pyrene, anthracene, The styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with one or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamino. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but not limited thereto. In addition, as a metal complex, there are iridium complexes, platinum complexes, etc., but not limited thereto.
上述空穴阻挡层是阻挡空穴到达阴极的层，一般可以通过与空穴注入层相同的条件形成。具体而言，有二唑衍生物或三唑衍生物、菲咯啉衍生物、BCP、铝配合物(aluminum complex)等，但并不限定于此。The hole blocking layer is a layer that blocks holes from reaching the cathode and can generally be formed under the same conditions as the hole injection layer. Examples of the compound include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.
根据所使用的材料，根据本说明书的有机发光器件可以为顶部发光型、底部发光型或双向发光型。The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a bidirectional emission type according to the materials used.
实施发明的方式Modes for Carrying Out the Invention
根据本说明书的一实施方式，上述化学式1的杂环化合物可以根据下述反应式进行制造，但不仅限于此。在下述反应式中，关于取代基的种类和个数，本领域技术人员可以根据适当选择公知的起始物质而合成各种中间体。反应种类和反应条件可以利用该技术领域中已知的技术。According to one embodiment of the present specification, the heterocyclic compound of the above chemical formula 1 can be manufactured according to the following reaction formula, but is not limited thereto. In the following reaction formula, regarding the type and number of substituents, those skilled in the art can synthesize various intermediates by appropriately selecting known starting materials. The reaction type and reaction conditions can utilize the techniques known in the art.
制造例1.化合物E1的合成Preparation Example 1. Synthesis of Compound E1
将上述化合物8-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)-5,8'-联喹啉(10.0g，26.2mmol)和2-氯-4,6-二苯基-1,3,5-三嗪(7.4g，27.5mmol)完全溶解于四氢呋喃(100ml)中后，将碳酸钾(14.4g，104.6mmol)溶解于43ml的水中后进行添加，加入四(三苯基膦)钯(907mg，0.79mmol)后，加热搅拌7小时。将温度降至常温，结束反应后，去除碳酸钾溶液，过滤了上述的白色固体。将过滤的白色的固体用四氢呋喃和乙酸乙酯分别洗涤2次，从而制造了上述化合物E1(10.2g，收率80％)。After the above compound 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,8'-biquinoline (10.0 g, 26.2 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (7.4 g, 27.5 mmol) were completely dissolved in tetrahydrofuran (100 ml), potassium carbonate (14.4 g, 104.6 mmol) was dissolved in 43 ml of water and added, tetrakis(triphenylphosphine)palladium (907 mg, 0.79 mmol) was added, and heated and stirred for 7 hours. The temperature was lowered to room temperature, and after the reaction was terminated, the potassium carbonate solution was removed and the above white solid was filtered. The filtered white solid was washed twice with tetrahydrofuran and ethyl acetate, respectively, to produce the above compound E1 (10.2 g, yield 80%).
MS[M+H]+＝488MS[M+H] + ＝488
制造例2.化合物E2的合成Preparation Example 2. Synthesis of Compound E2
在上述制造例1中，使用2-(4-溴苯基)-4,6-二苯基-1,3,5-三嗪代替2-氯-4,6-二苯基-1,3,5-三嗪，除此以外，通过与上述制造例1相同的方法制造了上述化合物E2。The compound E2 was produced by the same method as in Production Example 1, except that 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.
MS[M+H]+＝564MS[M+H] + ＝564
制造例3.化合物E3的合成Preparation Example 3. Synthesis of Compound E3
在上述制造例1中，使用2-(6-溴吡啶-3-基)-4,6-二苯基-1,3,5-三嗪代替2-氯-4,6-二苯基-1,3,5-三嗪，除此以外，通过与上述制造例1相同的方法制造了上述化合物E3。The compound E3 was produced by the same method as in Production Example 1, except that 2-(6-bromopyridin-3-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.
MS[M+H]+＝565MS[M+H] +＝ 565
制造例4.化合物E4的合成Preparation Example 4. Synthesis of Compound E4
在上述制造例1中，使用2-氯-4-(3-(二苯并[b,d]呋喃-2-基)苯基)-6-苯基-1,3,5-三嗪代替2-氯-4,6-二苯基-1,3,5-三嗪，除此以外，通过与上述制造例1相同的方法制造了上述化合物E4。Compound E4 was produced by the same method as in Production Example 1, except that 2-chloro-4-(3-(dibenzo[b,d]furan-2-yl)phenyl)-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.
MS[M+H]+＝654MS[M+H] + ＝654
制造例5.化合物E5的合成Preparation Example 5. Synthesis of Compound E5
在上述制造例1中，使用3-(4-溴苯基)-5-(萘-2-基)哒嗪代替2-氯-4,6-二苯基-1,3,5-三嗪，除此以外，通过与上述制造例1相同的方法制造了上述化合物E5。The compound E5 was produced by the same method as in Production Example 1, except that 3-(4-bromophenyl)-5-(naphthalen-2-yl)pyridazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.
MS[M+H]+＝537MS[M+H] + ＝537
制造例6.化合物E6的合成Preparation Example 6. Synthesis of Compound E6
在上述制造例1中，使用2-(3-溴苯基)-4-苯基-6-(4-(吡啶-4-基)苯基)-1,3,5-三嗪代替2-氯-4,6-二苯基-1,3,5-三嗪，除此以外，通过与上述制造例1相同的方法制造了上述化合物E6。The compound E6 was produced by the same method as in Production Example 1, except that 2-(3-bromophenyl)-4-phenyl-6-(4-(pyridin-4-yl)phenyl)-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.
MS[M+H]+＝641MS[M+H] + ＝641
制造例7.化合物E7的合成Preparation Example 7. Synthesis of Compound E7
在上述制造例1中，使用2-(4-溴萘-1-基)-4,6-二苯基-1,3,5-三嗪代替2-氯-4,6-二苯基-1,3,5-三嗪，除此以外，通过与上述制造例1相同的方法制造了上述化合物E7。The compound E7 was produced by the same method as in Production Example 1, except that 2-(4-bromonaphthalen-1-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.
MS[M+H]+＝614MS[M+H] + ＝614
制造例8.化合物E8的合成Preparation Example 8. Synthesis of Compound E8
在上述制造例1中，使用2-(5-溴吡啶-2-基)-4,6-二苯基-1,3,5-三嗪代替2-氯-4,6-二苯基-1,3,5-三嗪，除此以外，通过与上述制造例1相同的方法制造了上述化合物E8。The compound E8 was produced by the same method as in Production Example 1, except that 2-(5-bromopyridin-2-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.
MS[M+H]+＝641MS[M+H] + ＝641
制造例9.化合物E9的合成Preparation Example 9. Synthesis of Compound E9
在上述制造例1中，使用3-(4-(4-溴苯基)-6-苯基-1,3,5-三嗪-2-基)苄腈代替2-氯-4,6-二苯基-1,3,5-三嗪，除此以外，通过与上述制造例1相同的方法制造了上述化合物E9。Compound E9 was produced by the same method as in Production Example 1, except that 3-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazine-2-yl)benzonitrile was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.
MS[M+H]+＝589MS[M+H] + ＝589
制造例10.化合物E10的合成Preparation Example 10. Synthesis of Compound E10
在上述制造例1中，使用3-(3-(4-溴-6-苯基-1,3,5-三嗪-2-基)苯基)-1,10-菲咯啉代替2-氯-4,6-二苯基-1,3,5-三嗪，除此以外，通过与上述制造例1相同的方法制造了上述化合物E10。The compound E10 was produced by the same method as in Production Example 1, except that 3-(3-(4-bromo-6-phenyl-1,3,5-triazine-2-yl)phenyl)-1,10-phenanthroline was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.
MS[M+H]+＝666MS[M+H] + ＝666
制造例11.化合物E11的合成Preparation Example 11. Synthesis of Compound E11
在上述制造例1中，使用(3-溴苯基)二苯基氧化膦代替2-氯-4,6-二苯基-1,3,5-三嗪，除此以外，通过与上述制造例1相同的方法制造了上述化合物E11。The compound E11 was produced by the same method as in Production Example 1, except that (3-bromophenyl)diphenylphosphine oxide was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.
MS[M+H]+＝533MS[M+H] + ＝533
制造例12.化合物E12的合成Preparation Example 12. Synthesis of Compound E12
在上述制造例1中，使用1-(4-溴苯基)-2-乙基-1H-苯并[d]咪唑代替2-氯-4,6-二苯基-1,3,5-三嗪，除此以外，通过与上述制造例1相同的方法制造了上述化合物E12。Compound E12 was produced by the same method as in Production Example 1, except that 1-(4-bromophenyl)-2-ethyl-1H-benzo[d]imidazole was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.
MS[M+H]+＝477MS[M+H] + ＝477
将本说明书的实施例中记载的制造式和上述中间体基于通常的技术常识适当地组合，可以制造出全部的本说明书中记载的上述化学式1的杂环化合物。All heterocyclic compounds of the above Chemical Formula 1 described in the present specification can be produced by appropriately combining the production formulas described in the Examples of the present specification and the above intermediates based on common technical knowledge.
实施例1-1Example 1-1
将ITO(氧化铟锡，indium tin oxide)以的厚度被涂布成薄膜的玻璃基板放入溶解有洗涤剂的蒸馏水中，利用超声波进行洗涤。这时，洗涤剂使用菲希尔公司(Fischer Co.)制品，蒸馏水使用了利用密理博公司(Millipore Co.)制造的过滤器(Filter)过滤两次的蒸馏水。将ITO洗涤30分钟后，用蒸馏水重复两次而进行10分钟超声波洗涤。在蒸馏水洗涤结束后，用异丙醇、丙酮、甲醇的溶剂进行超声波洗涤并干燥后，输送至等离子体清洗机。此外，利用氧等离子体，将上述基板清洗5分钟后，将基板输送至真空蒸镀机。ITO (indium tin oxide) is used The glass substrate coated with a film of a thickness of 10000 mm was placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent used a product of Fischer Co., and the distilled water used distilled water filtered twice by a filter manufactured by Millipore Co. After ITO was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was carried out with a solvent of isopropanol, acetone, and methanol and dried, and then transported to a plasma cleaning machine. In addition, after the above-mentioned substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.
在这样准备的作为阳极的ITO透明电极上，将下述化合物HI1和下述化合物HI2的化合物以成为98:2(摩尔比)的比的方式以的厚度进行热真空蒸镀而形成空穴注入层。在上述空穴注入层上，将由下述化学式HT1表示的化合物进行真空蒸镀而形成空穴传输层。接着，在上述空穴传输层上，以膜厚度真空蒸镀EB1的化合物而形成电子抑制层。接着，在上述电子抑制层上，以膜厚度将由下述化学式BH表示的化合物和由下述化学式BD表示的化合物以50:1的重量比进行真空蒸镀而形成发光层。在上述发光层上，以膜厚度将由下述化学式HB1表示的化合物进行真空蒸镀而形成空穴阻挡层。接着，在上述空穴阻挡层上，将制造例1的化合物和由下述化学式LiQ表示的化合物以1:1的重量比进行真空蒸镀，从而以的厚度形成电子注入和传输层。在上述电子注入和传输层上，依次将氟化锂(LiF)以的厚度、将铝以的厚度进行蒸镀而形成阴极。On the ITO transparent electrode prepared as the anode, the following compound HI1 and the following compound HI2 were mixed in a ratio of 98:2 (molar ratio). A hole injection layer is formed by thermal vacuum deposition of a thickness of 1000 nm. On the hole injection layer, a compound represented by the following chemical formula HT1 is deposited Then, a film with a thickness of 1000 nm was deposited on the hole transport layer. The electron suppression layer is formed by vacuum evaporation of the EB1 compound. Next, a film having a film thickness of The compound represented by the following chemical formula BH and the compound represented by the following chemical formula BD were vacuum deposited at a weight ratio of 50:1 to form a light-emitting layer. The compound represented by the following chemical formula HB1 was vacuum-deposited to form a hole blocking layer. Next, the compound of Preparation Example 1 and the compound represented by the following chemical formula LiQ were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form a hole blocking layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added with The thickness of the aluminum A cathode is formed by vapor deposition of a thickness of .
在上述过程中，有机物的蒸镀速度维持阴极的氟化锂维持的蒸镀速度，铝维持的蒸镀速度，在蒸镀时，真空度维持2×10-7～5×10-6托，从而制作了有机发光器件。In the above process, the evaporation rate of organic matter is maintained Lithium fluoride at cathode maintains The evaporation speed of aluminum is maintained The evaporation speed is 2×10 -7 to 5×10 -6 torr, and the vacuum degree is maintained during evaporation, thereby producing an organic light-emitting device.
实施例1-2至实施例1-8Example 1-2 to Example 1-8
使用下述表1中记载的化合物代替化合物E1，除此以外，通过与上述实施例1-1相同的方法制造了有机发光器件。An organic light-emitting device was manufactured by the same method as in Example 1-1, except that the compounds described in the following Table 1 were used instead of Compound E1.
比较例1-1至1-4Comparative Examples 1-1 to 1-4
使用下述表1中记载的化合物代替制造例1的化合物，除此以外，通过与上述实施例1-1相同的方法制造了有机发光器件。下述表1中使用的ET1、ET2、ET3、ET4的化合物如下所示。An organic light-emitting device was manufactured by the same method as in Example 1-1, except that the compounds described in Table 1 below were used instead of the compounds in Preparation Example 1. The compounds ET1, ET2, ET3, and ET4 used in Table 1 below are as follows.
对通过实施例1-1至1-8、比较例1-1至比较例1-4制作的有机发光器件施加电流时，测定电压、效率、色坐标和寿命，将其结果示于下述[表1]。T95表示亮度从初始亮度(1600nit)减少至95％所需的时间。When current was applied to the organic light-emitting devices prepared in Examples 1-1 to 1-8 and Comparative Examples 1-1 to 1-4, voltage, efficiency, color coordinates and lifetime were measured, and the results are shown in [Table 1] T95 represents the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.
[表1][Table 1]
如上述表1所示，在将本申请发明的化合物用作电子注入和传输层而制造的有机发光器件的情况下，在有机发光器件的效率、驱动电压和/或稳定性方面显示出优异的特性。上述有机发光器件与将现有使用的核即ET1等联喹啉化合物及取代的化合物用作电子传输层而制造的有机发光器件相比，显示出低电压、高效率和长寿命的特性。As shown in Table 1, in the case of an organic light-emitting device manufactured by using the compound of the present invention as an electron injection and transport layer, excellent characteristics are shown in terms of efficiency, driving voltage and/or stability of the organic light-emitting device. The organic light-emitting device shows low voltage, high efficiency and long life compared to an organic light-emitting device manufactured by using a biquinoline compound such as ET1 and a substituted compound as an electron transport layer.
在使用了核不是联喹啉化合物的化合物、或不是在1、4号位置取代的联喹啉的化合物的比较例1-2和1-4、以及使用了R2不是氢的化合物的比较例1-3的情况下，与实施例1-1至1-8相比，确认了寿命显著降低，具有高电压。In the case of Comparative Examples 1-2 and 1-4 using compounds whose cores are not biquinoline compounds or compounds whose 1-4 positions are not biquinoline substituted, and Comparative Example 1-3 using compounds whose R2 is not hydrogen, it was confirmed that the life was significantly reduced and the voltage was high compared with Examples 1-1 to 1-8.
通过上述内容对本发明的优选实施例(电子注入和传输层)进行了说明，但本发明并不限定于此，在要求保护的范围和发明的详细说明的范围内可以变形为各种形态而实施，这也属于本发明的范畴。The above content describes the preferred embodiment of the present invention (electron injection and transport layer), but the present invention is not limited thereto and can be implemented in various forms within the scope of the protection required and the detailed description of the invention, which also belongs to the scope of the present invention.
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