CN114144402A - 新型化合物及包含其的有机发光器件 - Google Patents
新型化合物及包含其的有机发光器件 Download PDFInfo
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- CN114144402A CN114144402A CN202180004646.5A CN202180004646A CN114144402A CN 114144402 A CN114144402 A CN 114144402A CN 202180004646 A CN202180004646 A CN 202180004646A CN 114144402 A CN114144402 A CN 114144402A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 107
- 239000010410 layer Substances 0.000 claims description 130
- 239000000126 substance Substances 0.000 claims description 104
- -1 naphthylphenyl Chemical group 0.000 claims description 90
- 239000012044 organic layer Substances 0.000 claims description 57
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 235000010290 biphenyl Nutrition 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 230000005525 hole transport Effects 0.000 claims description 18
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 17
- 229910052805 deuterium Inorganic materials 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000005842 heteroatom 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
- 125000001624 naphthyl group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 239000004305 biphenyl Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 230000001629 suppression Effects 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 7
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000005580 triphenylene group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- 125000004957 naphthylene group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 description 40
- 239000007924 injection Substances 0.000 description 40
- 238000004519 manufacturing process Methods 0.000 description 32
- 230000032258 transport Effects 0.000 description 24
- 125000004432 carbon atom Chemical group C* 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 239000000463 material Substances 0.000 description 18
- 239000000758 substrate Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 8
- 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 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical group 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000001771 vacuum deposition Methods 0.000 description 6
- 238000007738 vacuum evaporation Methods 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 239000010406 cathode material Substances 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000010405 anode material Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 229940126214 compound 3 Drugs 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 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
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- RBEWDLDDCSQHAO-UHFFFAOYSA-N Clc1ccc(cc1)N(c1ccccc1)c1ccc2ccccc2c1 Chemical compound Clc1ccc(cc1)N(c1ccccc1)c1ccc2ccccc2c1 RBEWDLDDCSQHAO-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 150000004696 coordination complex Chemical class 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 125000004185 ester group Chemical group 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
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- UVNPEUJXKZFWSJ-LMTQTHQJSA-N (R)-N-[(4S)-8-[6-amino-5-[(3,3-difluoro-2-oxo-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-yl]-2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](=O)N[C@@H]1COCC11CCN(CC1)c1cnc(Sc2ccnc3NC(=O)C(F)(F)c23)c(N)n1 UVNPEUJXKZFWSJ-LMTQTHQJSA-N 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- 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 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 2
- DZKGYFXJWUZUBZ-UHFFFAOYSA-N 4-naphthalen-1-yl-n-phenylaniline Chemical compound C=1C=C(C=2C3=CC=CC=C3C=CC=2)C=CC=1NC1=CC=CC=C1 DZKGYFXJWUZUBZ-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- NUGPIZCTELGDOS-QHCPKHFHSA-N N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclopentanecarboxamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CC[C@@H](C=1C=NC=CC=1)NC(=O)C1CCCC1)C NUGPIZCTELGDOS-QHCPKHFHSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl 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
- 125000005264 aryl amine group Chemical group 0.000 description 2
- 125000004391 aryl sulfonyl 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
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000004556 carbazol-9-yl group Chemical group C1=CC=CC=2C3=CC=CC=C3N(C12)* 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005241 heteroarylamino group Chemical group 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000005462 imide group Chemical group 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- 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 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-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
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- ZVFJWYZMQAEBMO-UHFFFAOYSA-N 1h-benzo[h]quinolin-10-one Chemical compound C1=CNC2=C3C(=O)C=CC=C3C=CC2=C1 ZVFJWYZMQAEBMO-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
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- 238000004544 sputter deposition Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 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
- 230000007704 transition Effects 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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 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
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 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
- 239000011787 zinc oxide Substances 0.000 description 1
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Abstract
本发明提供新型化合物及利用其的有机发光器件。
Description
技术领域
本发明涉及新型化合物及利用其的有机发光器件。
背景技术
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具有宽视角、优异的对比度、快速响应时间,亮度、驱动电压和响应速度特性优异,因此正在进行大量的研究。
有机发光器件通常具有包括阳极和阴极以及位于上述阳极与阴极之间的有机物层的结构。为了提高有机发光器件的效率和稳定性,上述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,则空穴从阳极注入有机物层,电子从阴极注入有机物层,当所注入的空穴和电子相遇时会形成激子(exciton),该激子重新跃迁至基态时就会发出光。
对用于如上所述的有机发光器件的有机物,持续要求开发新的材料。
现有技术文献
专利文献
(专利文献0001)韩国专利公开号第10-2013-073537号
发明内容
技术课题
本发明涉及新型化合物、包含其的有机发光器件。
课题的解决方法
本发明提供由下述化学式1表示的化合物:
[化学式1]
在上述化学式1中,
X为NR'、O或S,在这里,R'为氢、氘、取代或未取代的C1-10烷基、或者取代或未取代的C6-30芳基,
L为单键、或者取代或未取代的C6-60亚芳基,
Ar1为取代或未取代的C6-60芳基;或者包含选自N、O和S中的一种以上的杂原子的取代或未取代的C2-60杂芳基,
Ar2和Ar3各自独立地为取代或未取代的C6-60芳基;或者包含选自N、O和S中的一种以上的杂原子的取代或未取代的C2-60杂芳基,
R1和R2各自独立地为氢;氘;取代或未取代的C1-60烷基;取代或未取代的C6-60芳基;或者包含选自N、O和S中的一种以上的杂原子的取代或未取代的C2-60杂芳基,
m和n各自独立地为0至4的整数。
另外,本发明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设置的第二电极、以及设置在上述第一电极与上述第二电极之间的1层以上的有机物层,上述有机物层中的1层以上包含上述的本发明的化合物。
发明效果
由上述化学式1表示的化合物可以用作有机发光器件的有机物层的材料,在有机发光器件中可以实现效率的提高、低驱动电压和/或寿命特性的提高。特别是,由上述化学式1表示的化合物可以用作空穴注入、空穴传输、空穴注入和传输、发光、电子传输、或电子注入的材料。
附图说明
图1图示了由基板1、阳极2、发光层3和阴极4构成的有机发光器件的例子。
图2图示了由基板1、阳极2、空穴注入层5、空穴传输层6、电子抑制层7、发光层3、电子传输层8、电子注入层9、以及阴极4构成的有机发光器件的例子。
具体实施方式
下面,为了帮助理解本发明而更详细地进行说明。
(用语的说明)
在本说明书中,“取代或未取代的”这一用语是指被选自氘(D);卤素基团;腈基;硝基;羟基;羰基;酯基;酰亚胺基;氨基;氧化膦基;烷氧基;芳氧基;烷基硫氧基(Alkylthioxy);芳基硫氧基(Aryl thioxy);烷基磺酰基(Alkyl sulfoxy);芳基磺酰基(Arylsulfoxy);甲硅烷基;硼基;烷基;环烷基;烯基;芳基;芳烷基;芳烯基;烷基芳基;烷基胺基;芳烷基胺基;杂芳基胺基;芳基胺基;芳基膦基;或者包含N、O和S原子中的1个以上的杂环基中的1个以上的取代基取代或未取代,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未取代。例如,“2个以上的取代基连接而成的取代基”可以为联苯基。即,联苯基可以为芳基,也可以被解释为2个苯基连接而成的取代基。
在本说明书中,羰基的碳原子数没有特别限定,但优选碳原子数为1至40。具体而言,可以为如下结构的化合物,但并不限定于此。
在本说明书中,酯基中,酯基的氧可以被碳原子数1至25的直链、支链或环状的烷基、或者碳原子数6至25的芳基取代。具体而言,可以为下述结构式的化合物,但并不限定于此。
在本说明书中,酰亚胺基的碳原子数没有特别限定,但优选碳原子数为1至25。具体而言,可以为如下结构的化合物,但并不限定于此。
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。
在本说明书中,硼基具体有三甲基硼基、三乙基硼基、叔丁基二甲基硼基、三苯基硼基、苯基硼基等,但并不限定于此。
在本说明书中,作为卤素基团的例子,有氟、氯、溴或碘。
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60。根据一实施方式,上述烷基的碳原子数为1至40。根据一实施方式,上述烷基的碳原子数为1至20。根据另一实施方式,上述烷基的碳原子数为1至10。根据另一实施方式,上述烷基的碳原子数为1至6。作为烷基的具体例,有甲基、乙基、丙基、正丙基、异丙基、丁基、正丁基、异丁基、叔丁基、仲丁基、1-甲基-丁基、1-乙基-丁基、戊基、正戊基、异戊基、新戊基、叔戊基、己基、正己基、1-甲基戊基、2-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、庚基、正庚基、1-甲基己基、环戊基甲基、环己基甲基、辛基、正辛基、叔辛基、1-甲基庚基、2-乙基己基、2-丙基戊基、正壬基、2,2-二甲基庚基、1-乙基-丙基、1,1-二甲基-丙基、异己基、2-甲基戊基、4-甲基己基、5-甲基己基等,但并不限定于此。
在本说明书中,上述烯基可以为直链或支链,碳原子数没有特别限定,但优选为2至40。根据一实施方式,上述烯基的碳原子数为2至20。根据另一实施方式,上述烯基的碳原子数为2至10。根据另一实施方式,上述烯基的碳原子数为2至6。作为具体例,有乙烯基、1-丙烯基、异丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-戊烯基、2-戊烯基、3-戊烯基、3-甲基-1-丁烯基、1,3-丁二烯基、烯丙基、1-苯基乙烯-1-基、2-苯基乙烯-1-基、2,2-二苯基乙烯-1-基、2-苯基-2-(萘-1-基)乙烯-1-基、2,2-双(二苯-1-基)乙烯-1-基、茋基、苯乙烯基等,但并不限定于此。
在本说明书中,环烷基没有特别限定,但优选为碳原子数3至60的环烷基。根据一实施方式,上述环烷基的碳原子数为3至30。根据另一实施方式,上述环烷基的碳原子数为3至20。根据另一实施方式,上述环烷基的碳原子数为3至6。具体而言,有环丙基、环丁基、环戊基、3-甲基环戊基、2,3-二甲基环戊基、环己基、3-甲基环己基、4-甲基环己基、2,3-二甲基环己基、3,4,5-三甲基环己基、4-叔丁基环己基、环庚基、环辛基等,但并不限定于此。
在本说明书中,芳基没有特别限定,但优选为碳原子数6至60的芳基,可以为单环芳基或多环芳基。根据一实施方式,上述芳基的碳原子数为6至30。根据一实施方式,上述芳基的碳原子数为6至20。关于上述芳基,作为单环芳基,可以为苯基、联苯基、三联苯基等,但并不限定于此。作为上述多环芳基,可以为萘基、蒽基、菲基、芘基、苝基、基、芴基等,但并不限定于此。
在本说明书中,杂芳基是包含O、N、Si和S中的1个以上作为杂元素并具有芳香性(aromatic)的杂环基,碳原子数没有特别限定,但优选碳原子数为2至60。作为杂芳基的例子,有噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、唑基、二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、苯并呋喃基、菲咯啉基、噻唑基、异唑基、二唑基、噻二唑基、苯并噻唑基、吩噻嗪基和二苯并呋喃基等,但不仅限于此。
在本说明书中,芳烷基、芳烯基、烷基芳基、芳基胺基中的芳基与上述芳基的例示相同。在本说明书中,芳烷基、烷基芳基、烷基胺基中的烷基与上述烷基的例示相同。在本说明书中,杂芳基胺中的杂芳基可以适用上述的关于杂环基的说明。在本说明书中,芳烯基中的烯基与上述烯基的例示相同。在本说明书中,亚芳基为2价基团,除此以外,可以适用上述的关于芳基的说明。在本说明书中,亚杂芳基为2价基团,除此以外,可以适用上述的关于杂环基的说明。在本说明书中,烃环不是1价基团,而是2个取代基结合而成,除此以外,可以适用上述的关于芳基或环烷基的说明。在本说明书中,杂环不是1价基团,而是2个取代基结合而成,除此以外,可以适用上述的关于杂环基的说明。
(化合物)
本发明提供由下述化学式1表示的化合物:
[化学式1]
在上述化学式1中,胺基(*-L-N(Ar2)(Ar3))与1、2、3、4、5、6、7和8中的任一个碳原子连接。
X为NR'、O或S,在这里,R'为氢、氘、取代或未取代的C1-10烷基、或者取代或未取代的C6-30芳基,
L为单键、或者取代或未取代的C6-60亚芳基,
Ar1为取代或未取代的C6-60芳基;或者包含选自N、O和S中的一种以上的杂原子的取代或未取代的C2-60杂芳基,
Ar2和Ar3各自独立地为取代或未取代的C6-60芳基;或者包含选自N、O和S中的一种以上的杂原子的取代或未取代的C2-60杂芳基,
R1和R2各自独立地为氢;氘;取代或未取代的C1-60烷基;取代或未取代的C6-60芳基;或者包含选自N、O和S中的一种以上的杂原子的取代或未取代的C2-60杂芳基,
m和n各自独立地为0至4的整数。
优选地,由上述化学式1表示的化合物为由下述化学式1-1或1-8表示的化合物:
[化学式1-1]
[化学式1-2]
[化学式1-3]
[化学式1-4]
[化学式1-5]
[化学式1-6]
[化学式1-7]
[化学式1-8]
在上述化学式1-1至1-8中,
X、L、Ar1、Ar2、Ar3、R1、R2、m和n与上述的定义相同。
优选地,R'为氢、氘、苯基、联苯基或萘基。更优选地,R'为苯基。
优选地,L为单键、亚苯基、亚联苯基或亚萘基。
优选地,Ar1为苯基、联苯基、三联苯基、萘基、萘基苯基、苯基萘基、菲基、三亚苯基、二甲基芴基、二苯基芴基、二苯并呋喃基或二苯并噻吩基。它们各自独立地被一个以上的氘(D)取代或未取代。
更优选地,Ar1为被一个以上的氘取代或未取代的苯基、联苯基、萘基或二苯并呋喃基。
优选地,Ar2和Ar3各自独立地为苯基、联苯基、三联苯基、萘基、萘基苯基、苯基萘基、菲基、三亚苯基、二甲基芴基、二苯基芴基、二苯并呋喃基或二苯并噻吩基。
优选地,R1和R2各自独立地为氢、氘、苯基、联苯基、三联苯基、萘基、二苯并呋喃基或二苯并噻吩基。
优选地,m和n各自独立地为0至3的整数。更优选地,m和n各自独立地为0或1。
优选地,由上述化学式1表示的化合物可以为选自下述化合物中的任一个:
根据本发明的由化学式1表示的化合物包含菲并唑基、菲并噻唑基和菲并吡唑基核结构,这些结构具有电负性大、同时电子密度高的特性。不仅如此,由于稠合而成的结构具有刚性(rigid)特性,从而易于分子之间的电荷传递,特别是,在这里进一步连接有胺取代基,因此空穴传输能力优异。通过这样的优异的分子间堆叠(stacking)和电荷传输能力,能够迅速实现空穴电流特性。因此,当根据本发明的化合物在有机电致发光器件中用于主要传输空穴的空穴传输层、电子阻挡层(电子抑制层)、发光层的p型主体时,可以对低电压驱动和效率及寿命的提高作出较大的贡献,这样的器件特性的改善对在面板制作工序中暴露于高温时的稳定性的保障和性能的提高也具有较大的效果。
由上述化学式1表示的化合物可以通过下述反应式1进行制造:
[反应式1]
在上述反应式1中,除了X以外的其余变量与上述的定义相同,X各自独立地为卤素,优选为氯或溴。
上述反应式1中使用的反应物、催化剂、溶剂等可以基于目标生成物适当地变更。化学式1的化合物的制造方法可以在后述的制造例中更具体化。
(有机发光器件)
另外,本发明提供包含由上述化学式1表示的化合物的有机发光器件。作为一个例子,本发明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设置的第二电极、以及设置在上述第一电极与上述第二电极之间的1层以上的有机物层,上述有机物层中的1层以上包含由上述化学式1表示的化合物。
本发明的有机发光器件的有机物层可以由单层结构形成,也可以由层叠有两层以上的有机物层的多层结构形成。例如,本发明的有机发光器件可以具有包括空穴注入层、空穴传输层、电子抑制层、发光层、电子传输层、电子注入层等作为有机物层的结构。但是,有机发光器件的结构并不限定于此,可以包括更少数量的有机层。
另外,上述有机物层可以包括空穴注入层、空穴传输层、或者同时进行空穴注入和传输的层,上述空穴注入层、空穴传输层、或者同时进行空穴注入和传输的层包含由上述化学式1表示的化合物。
另外,上述有机物层可以包括电子抑制层,上述电子抑制层包含由上述化学式1表示的化合物。
另外,上述有机物层可以包括电子传输层、电子注入层、或者同时进行电子传输和电子注入的层,上述电子传输层、电子注入层、或者同时进行电子传输和电子注入的层包含由上述化学式1表示的化合物。
另外,上述有机物层包括空穴注入层、空穴传输层、电子抑制层和发光层,选自它们中的任一者以上包含由上述化学式1表示的化合物。
另外,上述有机物层可以包括发光层,上述发光层包含由上述化学式1表示的化合物。
优选地,上述发光层除了由化学式1表示的化合物以外,还包含由下述化学式2表示的化合物。
优选地,上述发光层使用2种以上的主体,上述主体中的一种为本申请化学式1的化合物,优选地,化学式1和化学式2的化合物同时用作主体化合物。
[化学式2]
在上述化学式2中,
A1和A2各自独立地为苯环或萘环,
Ar'1为包含选自N、O和S中的一种以上的杂原子的取代或未取代的C2-60杂芳基,但Ar'1包含至少一个以上的N。
L'1为单键;取代或未取代的C6-60亚芳基;或者包含选自N、O和S中的一种以上的杂原子的取代或未取代的C2-60亚杂芳基,
R'1和R'2各自独立地为氢;氘;卤素;氰基;硝基;氨基;取代或未取代的C1-60烷基;取代或未取代的C3-60环烷基;取代或未取代的C2-60烯基;取代或未取代的C6-60芳基;或者包含选自N、O和S中的一种以上的杂原子的取代或未取代的C2-60杂芳基,
o和p各自独立地为0至4的整数。
优选地,由上述化学式2表示的化合物为由下述化学式2-1至化学式2-4表示的化合物:
[化学式2-1]
[化学式2-2]
[化学式2-3]
[化学式2-4]
在上述化学式2-1至2-4中,
L'1、Ar'1、R'1、R'2、o和p与上述的定义相同。
优选地,L'1为单键、亚苯基、亚联苯基、亚萘基、亚咔唑基、亚9-苯基-9H-咔唑基、亚二苯并呋喃基或亚二苯并噻吩基。
优选地,Ar'1为选自下述基团中的任一个:
在上述化学式中,
X'各自独立地为CH或N,但它们中的一个以上为N,
R"各自独立地为苯基、联苯基、萘基、苯基萘基、萘基苯基、二甲基芴基、二苯并呋喃基、二苯并噻吩基、咔唑-9-基或9-苯基-9H-咔唑基。
优选地,R'1和R'2各自独立地为氢、氘、苯基、联苯基、萘基、二苯并呋喃基、二苯并噻吩基、咔唑-9-基、苯并咔唑-5-基、苯并咔唑-7-基、苯并咔唑-11-基、9-苯基-9H-咔唑基、5-苯基-5H-苯并咔唑基、7-苯基-7H-苯并咔唑基或11-苯基-11H-苯并咔唑基。
由上述化学式2表示的化合物为选自下述化合物中的任一个:
另外,根据本发明的有机发光器件可以是在基板上依次层叠有阳极、1层以上的有机物层和阴极的结构(正常型(normaLtype))的有机发光器件。此外,根据本发明的有机发光器件可以是在基板上依次层叠有阴极、1层以上的有机物层和阳极的逆向结构(倒置型(inverted type))的有机发光器件。例如,根据本发明的一实施例的有机发光器件的结构例示于图1和图2。
图1图示了由基板1、阳极2、发光层3、阴极4构成的有机发光器件的例子。在如上所述的结构中,由上述化学式1表示的化合物可以包含在上述发光层中。
图2图示了由基板1、阳极2、空穴注入层5、空穴传输层6、电子抑制层7、发光层3、电子传输层8、电子注入层9和阴极4构成的有机发光器件的例子。在如上所述的结构中,由上述化学式1表示的化合物可以包含在上述空穴注入层、空穴传输层、电子抑制层、发光层、电子传输层和电子注入层中的1层以上中。
在根据本发明的有机发光器件中,上述有机物层中的1层以上包含由上述化学式1表述的化合物,除此以外,可以利用本技术领域中已知的材料和方法进行制造。此外,在上述有机发光器件包括复数个有机物层的情况下,上述有机物层可以由相同的物质或不同的物质形成。
例如,根据本发明的有机发光器件可以通过在基板上依次层叠第一电极、有机物层和第二电极而制造。这时,可以如下制造:利用溅射法(sputtering)或电子束蒸发法(e-beam evaporation)之类的PVD(physical Vapor Deposition:物理气相沉积)方法,在基板上蒸镀金属或具有导电性的金属氧化物或它们的合金而形成阳极,然后在该阳极上形成包括空穴注入层、空穴传输层、发光层和电子传输层的有机物层,之后在该有机物层上蒸镀可用作阴极的物质而制造。除了这种方法以外,还可以在基板上依次蒸镀阴极物质、有机物层、阳极物质而制造有机发光器件。
另外,由上述化学式1表示的化合物在制造有机发光器件时不仅可以利用真空蒸镀法,还可以利用溶液涂布法来形成有机物层。在这里,所谓溶液涂布法是指旋涂法、浸涂法、刮涂法、喷墨印刷法、丝网印刷法、喷雾法、辊涂法等,但不仅限于此。
除了这些方法以外,还可以在基板上依次蒸镀阴极物质、有机物层、阳极物质而制造有机发光器件(WO 2003/012890)。但制造方法并不限定于此。
作为一个例子,上述第一电极为阳极,上述第二电极为阴极,或者上述第一电极为阴极,上述第二电极为阳极。
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。作为上述阳极物质的具体例,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-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧)噻吩](PEDOT)、聚吡咯和聚苯胺等导电性高分子等,但不仅限于此。
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。作为上述阴极物质的具体例,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。
上述空穴注入层是注入来自电极的空穴的层,作为空穴注入物质,优选为如下化合物:具有传输空穴的能力,具有注入来自阳极的空穴的效果,具有对于发光层或发光材料的优异的空穴注入效果,防止发光层中生成的激子向电子注入层或电子注入材料迁移,而且薄膜形成能力优异的化合物。优选空穴注入物质的HOMO(最高占有分子轨道,highestoccupied 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(porphyrin)、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、蒽醌及聚苯胺和聚噻吩系的导电性高分子等,但不仅限于此。
上述空穴传输层是从空穴注入层接收空穴并将空穴传输至发光层的层,空穴传输物质是能够从阳极或空穴注入层接收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。
上述电子抑制层是为了防止从阴极注入的电子没在发光层中再结合而转移至空穴传输层,从而置于空穴传输层与发光层之间的层的层,也称为电子阻挡层。电子抑制层优选为与电子传输层相比电子亲和力小的物质。
上述发光物质是能够从空穴传输层和电子传输层分别接收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。
上述发光层可以包含主体材料和掺杂剂材料。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,有咔唑衍生物、二苯并呋喃衍生物、梯形呋喃化合物、嘧啶衍生物等,但并不限定于此。
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1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。
上述电子传输层是从电子注入层接收电子并将电子传输至发光层的层,电子传输物质是能够从阴极良好地接收电子并将其转移至发光层的物质,对于电子的迁移率大的物质是合适的。作为具体例,有8-羟基喹啉的Al配合物、包含Alq3的配合物、有机自由基化合物、羟基黄酮-金属配合物等,但不仅限于此。电子传输层可以如现有技术中所使用的那样与任意需要的阴极物质一同使用。特别是,合适的阴极物质的例子是具有低功函数且伴有铝层或银层的通常的物质。具体为铯、钡、钙、镱和钐,在各情况下均伴有铝层或银层。
上述电子注入层是注入来自电极的电子的层,优选为如下化合物:具有传输电子的能力,具有注入来自阴极的电子的效果,具有对于发光层或发光材料的优异的电子注入效果,防止发光层中生成的激子向空穴注入层迁移,而且薄膜形成能力优异的化合物。具体而言,有芴酮、蒽醌二甲烷、联苯醌、噻喃二氧化物、唑、二唑、三唑、咪唑、苝四羧酸、亚芴基甲烷、蒽酮等和它们的衍生物、金属配位化合物、以及含氮五元环衍生物等,但并不限定于此。
作为上述金属配位化合物,有8-羟基喹啉锂、双(8-羟基喹啉)锌、双(8-羟基喹啉)铜、双(8-羟基喹啉)锰、三(8-羟基喹啉)铝、三(2-甲基-8-羟基喹啉)铝、三(8-羟基喹啉)镓、双(10-羟基苯并[h]喹啉)铍、双(10-羟基苯并[h]喹啉)锌、双(2-甲基-8-喹啉)氯化镓、双(2-甲基-8-喹啉)(邻甲酚)镓、双(2-甲基-8-喹啉)(1-萘酚)铝、双(2-甲基-8-喹啉)(2-萘酚)镓等,但并不限定于此。
根据所使用的材料,根据本发明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。
另外,由上述化学式1表示的化合物除了有机发光器件以外,还可以包含在有机太阳能电池或有机晶体管中。
在下面的实施例中对由上述化学式1表示的化合物及包含其的有机发光器件的制造具体地说明。但是,下述实施例用于例示本发明,本发明的范围并不限定于此。
[制造例]
制造例1:化合物1的合成
在氮气氛下,将5-溴-2-苯基菲并[9,10-d]唑(5-bromo-2-phenylphenanthro[9,10-d]oxazole)(15.0g,40.1mmol)和二([1,1'-联苯]-4-基)胺(di([1,1'-biphenyl]-4-yl)amine)(14.2g,44.1mmol)加入到300ml的甲苯(toluene)中,搅拌及回流。然后,投入叔丁醇钠(sodium tert-butoxide)(5.8g,60.1mmol)、双(三叔丁基膦)钯(0)(bis(tri-tert-butylphosphine)palladium(0))(0.6g,1.2mmol)。反应8小时后,冷却至常温,利用氯仿和水将有机层分离后,蒸馏有机层。将其再次溶解于氯仿,用水洗涤2次后,分离有机层,加入无水硫酸镁,搅拌后过滤,将滤液减压蒸馏。将浓缩的化合物用硅胶柱层析进行纯化后,通过升华纯化而制造了8.1g的化合物1。(收率33%,MS:[M+H]+=616)
制造例2:化合物2的合成
在制造例1中,将二([1,1’-联苯]-4-基)胺变更为9,9-二甲基-N-(萘-2-基)-9H-芴-2-胺(9,9-dimethyl-N-(naphthalen-2-yl)-9H-fluoren-2-amine)而使用,除此以外,通过与化合物1的制造方法相同的制造方法制造了化合物2。(MS:[M+H]+=630)
制造例3:化合物3的合成
步骤1)化合物3-1的合成
在氮气氛下,使5-溴-2-苯基菲并[9,10-d]唑(15.0g,40.1mmol)和双(频哪醇合)二硼(bis(pinacolato)diboron)(11.2g,44.1mmol)在300ml的1,4-二烷(1,4-dioxane)中回流,搅拌。然后,投入醋酸钾(potassium acetate)(5.9g,60.1mmol),充分搅拌后,投入双(二亚苄基丙酮)钯(0)(bis(dibenzylideneacetone)palladium(0))(0.7g,1.2mmol)和三环己基膦(tricyclohexylphosphine)(0.7g,2.4mmol)。反应5小时,冷却至常温,利用氯仿和水将有机层分离后,蒸馏有机层。将其再次溶解于氯仿,用水洗涤2次后,分离有机层,加入无水硫酸镁,搅拌后过滤,将滤液减压蒸馏。将浓缩的化合物用硅胶柱层析进行纯化,从而制造了10.8g的化合物3-1。(收率64%,MS:[M+H]+=422)
步骤2)化合物3的合成
在氮气氛下,将化合物3-1(15.0g,35.6mmol)和N-(4-氯苯基)-N-苯基萘-2-胺(N-(4-chlorophenyl)-N-phenylnaphthalen-2-amine)(12.9g,39.2mmol)加入到300ml的THF中,搅拌及回流。然后,将碳酸钾(potassium carbonate)(19.7g,142.4mmol)溶解于60ml的水而投入,充分搅拌后,投入四(三苯基膦)钯(0)(tetrakis(triphenylphosphine)palladium(0))(1.2g,1.1mmol)。反应8小时后,冷却至常温,将有机层和水层分离后,蒸馏有机层。将其再次溶解于氯仿,用水洗涤2次后,分离有机层,加入无水硫酸镁,搅拌后过滤,将滤液减压蒸馏。将浓缩的化合物用硅胶柱层析进行纯化,通过升华纯化而制造了14.0g的化合物3。(收率67%,MS:[M+H]+=590)
制造例4:化合物4的制造
在制造例3的步骤2中,将N-(4-氯苯基)-N-苯基萘-2-胺变更为N-(3-氯苯基)-N-(萘-1-基)二苯并[b,d]呋喃-1-胺(N-(3-chlorophenyl)-N-(naphthalen-1-yl)dibenzo[b,d]furan-1-amine)而使用,除此以外,通过与化合物3的制造方法相同的制造方法制造了化合物4。(MS:[M+H]+=680)
制造例5:化合物5的合成
在制造例1中,将5-溴-2-苯基菲并[9,10-d]唑变更为6-溴-2-苯基菲并[9,10-d]唑(6-bromo-2-phenylphenanthro[9,10-d]oxazole)、将二([1,1’-联苯]-4-基)胺变更为4-(萘-1-基)-N-苯基苯胺(4-(naphthalen-1-yl)-N-pheny laniline)而使用,除此以外,通过与化合物1的制造方法相同的制造方法制造了化合物5。(MS:[M+H]+=590)
制造例6:化合物6的合成
在制造例1中,将5-溴-2-苯基菲并[9,10-d]唑变更为6-溴-2-苯基菲并[9,10-d]唑、将二([1,1’-联苯]-4-基)胺变更为N-(萘-2-基)二苯并[b,d]呋喃-3-胺(N-(naphthalen-2-yl)dibenzo[b,d]furan-3-amine)而使用,除此以外,通过与化合物1的制造方法相同的制造方法制造了化合物6。(MS:[M+H]+=604)
制造例7:化合物7的合成
在制造例3中,将5-溴-2-苯基菲并[9,10-d]唑变更为6-溴-2-苯基菲并[9,10-d]唑、将N-(4-氯苯基)-N-苯基萘-2-胺变更为N-(4-氯苯基)-N-(萘-2-基)萘-2-胺(N-(4-chlorophenyl)-N-(naphthalen-2-yl)naphthalen-2-amine)而使用,除此以外,通过与化合物3的制造方法相同的制造方法制造了化合物7。(MS:[M+H]+=640)
制造例8:化合物8的合成
在制造例3的步骤2中,将化合物3-1变更为化合物7-1、将N-(4-氯苯基)-N-苯基萘-2-胺变更为N-([1,1'-联苯]-4-基)-N-(3-氯苯基)二苯并[b,d]噻吩-4-胺(N-([1,1'-biphenyl]-4-yl)-N-(3-chlorophenyl)dibenzo[b,d]thiophen-4-amine)而使用,除此以外,通过与化合物3的制造方法相同的制造方法制造了化合物8。(MS:[M+H]+=722)
制造例9:化合物9的合成
步骤1)化合物9-1的合成
在氮气氛下,将5,10-二溴-2-苯基菲并[9,10-d]唑(5,10-dibromo-2-phenylphenanthro[9,10-d]oxazole)(15.0g,33.1mmol)和4-(萘-1-基)-N-苯基苯胺(10.8g,36.4mmol)加入到300ml的甲苯中,搅拌及回流。然后,投入叔丁醇钠(4.8g,49.7mmol)、双(三叔丁基膦)钯(0)(0.5g,1mmol)。反应9小时后,冷却至常温,利用氯仿和水将有机层分离后,蒸馏有机层。将其再次溶解于氯仿,用水洗涤2次后,分离有机层,加入无水硫酸镁,搅拌后过滤,将滤液减压蒸馏。将浓缩的化合物用硅胶柱层析进行纯化,从而制造了7.1g的化合物9-1。(收率32%,MS:[M+H]+=669)
步骤2)化合物9的合成
在氮气氛下,将化合物9-1(15.0g,22.5mmol)和苯基硼酸(phenylboronic acid)(3.0g,24.7mmol)加入到300ml的THF中,搅拌及回流。然后,将碳酸钾(12.4g,89.9mmol)溶解于37ml的水而投入,充分搅拌后,投入四(三苯基膦)钯(0)(0.8g,0.7mmol)。反应10小时后,冷却至常温,将有机层和水层分离后,蒸馏有机层。将其再次溶解于氯仿,用水洗涤2次后,分离有机层,加入无水硫酸镁,搅拌后过滤,将滤液减压蒸馏。将浓缩的化合物用硅胶柱层析进行纯化后,通过升华纯化而制造了10.9g的化合物9。(收率73%,MS:[M+H]+=666)
制造例10:化合物10的合成
步骤1)化合物10-1的合成
在氮气氛下,将6,9-二溴-2-苯基菲并[9,10-d]唑(6,9-dibromo-2-phenylphenanthro[9,10-d]oxazole)(15.0g,33.1mmol)和N-苯基-N-(3-(4,4,5,5-四甲基-1,3,2-二氧环戊硼烷-2-基)苯基)萘-2-胺(N-phenyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)naphthalen-2-amine)(15.3g,36.4mmol)加入到300ml的THF中,搅拌及回流。然后,将碳酸钾(18.3g,132.4mmol)溶解于55ml的水而投入,充分搅拌后,投入四(三苯基膦)钯(0)(1.1g,1.0mmol)。反应10小时后,冷却至常温,将有机层和水层分离后,蒸馏有机层。将其再次溶解于氯仿,用水洗涤2次后,分离有机层,加入无水硫酸镁,搅拌后过滤,将滤液减压蒸馏。将浓缩的化合物用硅胶柱层析进行纯化,从而制造了14.4g的化合物10-1。(收率65%,MS:[M+H]+=669)
步骤2)化合物10的合成
在氮气氛下,将化合物10-1(15.0g,22.5mmol)和苯基硼酸(3.0g,24.7mmol)加入到300ml的THF中,搅拌及回流。然后,将碳酸钾(12.4g,89.9mmol)溶解于37ml的水而投入,充分搅拌后,投入四(三苯基膦)钯(0)(0.8g,0.7mmol)。反应9小时后,冷却至常温,将有机层和水层分离后,蒸馏有机层。将其再次溶解于氯仿,用水洗涤2次后,分离有机层,加入无水硫酸镁,搅拌后过滤,将滤液减压蒸馏。将浓缩的化合物用硅胶柱层析进行纯化后,通过升华纯化而制造了7.3g的化合物10。(收率49%,MS:[M+H]+=666)
制造例11:化合物11的合成
在制造例1中,将5-溴-2-苯基菲并[9,10-d]唑变更为6-溴-2-(二苯并[b,d]呋喃-2-基)菲并[9,10-d]噻唑(6-bromo-2-(dibenzo[b,d]furan-2-yl)phenanthro[9,10-d]thiazole)、将二([1,1’-联苯]-4-基)胺变更为N-([1,1'-联苯]-4-基)萘-2-胺(N-([1,1'-biphenyl]-4-yl)naphthalen-2-amine)而使用,除此以外,通过与化合物1的制造方法相同的制造方法制造了化合物11。(MS:[M+H]+=594)
[实施例]
比较例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.)的DeconTMCON705制品,蒸馏水使用了利用密理博公司(Millipore Co.)制造的0.22μm无菌过滤器(sterilizing 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、丙酮和甲醇的溶剂分别进行10分钟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。
在这样准备的ITO透明电极上,依次将下述HI-A和LG-101分别以的厚度进行热真空蒸镀而形成空穴注入层。作为空穴传输层,将下述HT-A以的厚度进行真空蒸镀后,作为电子阻挡层(电子抑制层),将下述EB-A以的厚度进行热真空蒸镀。接着,作为发光层,将BH-A和BD-A以96:4的重量比、以的厚度进行真空蒸镀。接着,作为空穴阻挡层,将HB-A以的厚度进行热真空蒸镀,作为电子传输层,将由ET-A和Liq表示的化合物以1:1的重量比、以的厚度进行热真空蒸镀,接着,将下述Liq化合物以的厚度进行真空蒸镀而形成电子注入层。在上述电子注入层上,依次将镁和银以10:1的重量比、以的厚度进行蒸镀、将铝以的厚度进行蒸镀而形成阴极,从而制作了有机发光器件。
实施例1-1至实施例1-11和比较例1-2至比较例1-4
在上述比较例1-1中,作为电子阻挡层(电子抑制层)的材料,使用表1中记载的化合物来进行代替,除此以外,利用与比较例1-1相同的方法而分别制作了实施例1-1至实施例1-11和比较例1-2至比较例1-4的有机发光器件。
对上述实施例1-1至实施例1-11和比较例1-1至比较例1-4中制作的有机发光器件施加电流,测定了电压、效率、寿命(T95),将其结果示于下述表1。在这里,电压、效率是施加10mA/cm2的电流密度而测定的,LT95是指在电流密度20mA/cm2下初始亮度下降至95%时的时间。
[表1]
比较例2-1
将ITO(氧化铟锡)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.)的DeconTMCON705制品,蒸馏水使用了利用密理博公司(Millipore Co.)制造的0.22μm无菌过滤器(sterilizing 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、丙酮和甲醇的溶剂分别进行10分钟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。
在这样准备的ITO透明电极上,依次将下述HI-A和LG-101分别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,作为空穴传输层,将下述HT-A以的厚度进行真空蒸镀后,作为电子阻挡层,将下述EB-A以的厚度进行热真空蒸镀。作为发光层,将RH-A和RD-A以98:2的重量比、以的厚度进行真空蒸镀。接着,作为电子传输和注入层,将下述ET-B和Liq以1:1的比率、以的厚度进行热真空蒸镀,接着,将Liq以的厚度进行真空蒸镀。
实施例2-1至实施例2-11和比较例2-2至比较例2-5
在上述比较例2-1中,作为发光层的主体材料,使用表2中记载的化合物代替RH-A,除此以外,利用与比较例2-1相同的方法而分别制作了实施例2-1至实施例2-11和比较例2-2至比较例2-4的有机发光器件。这时,使用两种化合物的混合物作为主体时,括号内是指主体化合物之间的重量比。
对上述实施例2-1至实施例2-11和比较例2-1至比较例2-5中制作的有机发光器件施加电流,测定了电压、效率、寿命,将其结果示于下述表2。这时,电压、效率是施加10mA/cm2的电流密度而测定的,LT97是指在电流密度20mA/cm2下初始亮度下降至97%时的时间。
[表2]
从上述表1和表2的结果可知在将具有化学式1的结构的化合物用于有机发光器件时,可以得到具有低电压、高效率、长寿命特性的器件。
符号说明
1:基板 2:阳极
3:发光层 4:阴极
5:空穴注入层 6:空穴传输层
7:电子抑制层 8:电子传输层
9:电子注入层。
Claims (15)
1.一种由下述化学式1表示的化合物:
化学式1
在所述化学式1中,
X为NR'、O或S,其中,R'为氢、氘、取代或未取代的C1-10烷基、或者取代或未取代的C6-30芳基,
L为单键、或者取代或未取代的C6-60亚芳基,
Ar1为取代或未取代的C6-60芳基;或者包含选自N、O和S中的一种以上的杂原子的取代或未取代的C2-60杂芳基,
Ar2和Ar3各自独立地为取代或未取代的C6-60芳基;或者包含选自N、O和S中的一种以上的杂原子的取代或未取代的C2-60杂芳基,
R1和R2各自独立地为氢;氘;取代或未取代的C1-60烷基;取代或未取代的C6-60芳基;或者包含选自N、O和S中的一种以上的杂原子的取代或未取代的C2-60杂芳基,
m和n各自独立地为0至4的整数。
3.根据权利要求1所述的化合物,其中,R'为氢、氘、苯基、联苯基或萘基。
4.根据权利要求1所述的化合物,其中,L为单键、亚苯基、亚联苯基或亚萘基。
5.根据权利要求1所述的化合物,其中,Ar1为苯基、联苯基、三联苯基、萘基、萘基苯基、苯基萘基、菲基、三亚苯基、二甲基芴基、二苯基芴基、二苯并呋喃基或二苯并噻吩基,
它们被一个以上的氘取代或未取代。
6.根据权利要求1所述的化合物,其中,Ar2和Ar3各自独立地为苯基、联苯基、三联苯基、萘基、萘基苯基、苯基萘基、菲基、三亚苯基、二甲基芴基、二苯基芴基、二苯并呋喃基或二苯并噻吩基。
7.根据权利要求1所述的化合物,其中,R1和R2各自独立地为氢、氘、苯基、联苯基、三联苯基、萘基、二苯并呋喃基或二苯并噻吩基。
8.根据权利要求1所述的化合物,其中,m和n各自独立地为0或1。
10.一种有机发光器件,其中,包括:第一电极、与所述第一电极对置而设置的第二电极、以及设置在所述第一电极与所述第二电极之间的1层以上的有机物层,其中所述有机物层中的1层以上包含权利要求1至9中任一项所述的化合物。
11.根据权利要求10所述的有机发光器件,其中,包含所述化合物的有机物层为空穴传输层或电子抑制层。
12.根据权利要求10所述的有机发光器件,其中,包含所述化合物的有机物层为发光层。
13.根据权利要求12所述的有机发光器件,其中,所述发光层还包含由下述化学式2表示的化合物:
化学式2
在所述化学式2中,
A1和A2各自独立地为苯环或萘环,
Ar'1为包含选自N、O和S中的一种以上的杂原子的取代或未取代的C2-60杂芳基,但Ar'1包含至少一个以上的N,
L'1为单键;取代或未取代的C6-60亚芳基;或者包含选自N、O和S中的一种以上的杂原子的取代或未取代的C2-60亚杂芳基,
R'1和R'2各自独立地为氢;氘;卤素;氰基;硝基;氨基;取代或未取代的C1-60烷基;取代或未取代的C3-60环烷基;取代或未取代的C2-60烯基;取代或未取代的C6-60芳基;或者包含选自N、O和S中的一种以上的杂原子的取代或未取代的C2-60杂芳基,
o和p各自独立地为0至4的整数。
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