CN107501193A - 一种蒽类化合物及其合成方法和有机发光器件 - Google Patents
一种蒽类化合物及其合成方法和有机发光器件 Download PDFInfo
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- CN107501193A CN107501193A CN201710839856.1A CN201710839856A CN107501193A CN 107501193 A CN107501193 A CN 107501193A CN 201710839856 A CN201710839856 A CN 201710839856A CN 107501193 A CN107501193 A CN 107501193A
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- Prior art keywords
- unsubstituted
- substituted
- luminescent device
- anthracene compound
- substitution
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 title claims abstract description 38
- -1 anthracene compound Chemical class 0.000 title claims abstract description 30
- 238000010189 synthetic method Methods 0.000 title claims abstract description 27
- 238000006467 substitution reaction Methods 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 239000005416 organic matter Substances 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 150000001454 anthracenes Chemical class 0.000 claims description 3
- 230000005611 electricity Effects 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 239000000463 material Substances 0.000 abstract description 13
- 238000005516 engineering process Methods 0.000 abstract description 4
- 230000009477 glass transition Effects 0.000 abstract description 2
- 230000005693 optoelectronics Effects 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 25
- 230000000052 comparative effect Effects 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 8
- 229940125782 compound 2 Drugs 0.000 description 7
- 239000012153 distilled water Substances 0.000 description 7
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 3
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 3
- LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 3
- DQAZPZIYEOGZAF-UHFFFAOYSA-N 4-ethyl-n-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]piperazine-1-carboxamide Chemical compound C1CN(CC)CCN1C(=O)NC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=CC(C#C)=C1 DQAZPZIYEOGZAF-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- QBYJBZPUGVGKQQ-SJJAEHHWSA-N aldrin Chemical compound C1[C@H]2C=C[C@@H]1[C@H]1[C@@](C3(Cl)Cl)(Cl)C(Cl)=C(Cl)[C@@]3(Cl)[C@H]12 QBYJBZPUGVGKQQ-SJJAEHHWSA-N 0.000 description 3
- 229940125797 compound 12 Drugs 0.000 description 3
- 229940125851 compound 27 Drugs 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000002346 layers by function Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- GAGIQOAHYUJVFT-UHFFFAOYSA-N CC1(C)c(ccc(N)c2)c2-c2c1cccc2 Chemical compound CC1(C)c(ccc(N)c2)c2-c2c1cccc2 GAGIQOAHYUJVFT-UHFFFAOYSA-N 0.000 description 2
- 0 CCCC(c(c1c2cccc1)c(ccc(-c1nc(cccc3)c3[n]1-c1ccccc1)c1)c1c2N(*)[C@@](CC)C*)I Chemical compound CCCC(c(c1c2cccc1)c(ccc(-c1nc(cccc3)c3[n]1-c1ccccc1)c1)c1c2N(*)[C@@](CC)C*)I 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 238000000434 field desorption mass spectrometry Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 235000021419 vinegar Nutrition 0.000 description 2
- 239000000052 vinegar Substances 0.000 description 2
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 1
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical class C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 1
- WAXCVVDVEOOCHE-UHFFFAOYSA-N Bc1c(cc(cc2)-c3nc(C=CCC4)c4[n]3-c3ccccc3)c2cc2c1cccc2 Chemical compound Bc1c(cc(cc2)-c3nc(C=CCC4)c4[n]3-c3ccccc3)c2cc2c1cccc2 WAXCVVDVEOOCHE-UHFFFAOYSA-N 0.000 description 1
- QJXJEWDIELCMSU-UHFFFAOYSA-N BrC(C=CC1C2)=CC1=CC1=C2C=CCC1 Chemical compound BrC(C=CC1C2)=CC1=CC1=C2C=CCC1 QJXJEWDIELCMSU-UHFFFAOYSA-N 0.000 description 1
- ACZZVBGVVNUROR-UHFFFAOYSA-N BrC1=CCC=NC=C1 Chemical compound BrC1=CCC=NC=C1 ACZZVBGVVNUROR-UHFFFAOYSA-N 0.000 description 1
- RZNSKCZTGWLEFV-UHFFFAOYSA-N C1=CC=C2C=CC=CC2C1c(cc1)ccc1N(c1ccncc1)c1c(cccc2)c2c(-c2ccccc2)c(cc2)c1cc2-c1nc(cccc2)c2[n]1-c1ccccc1 Chemical compound C1=CC=C2C=CC=CC2C1c(cc1)ccc1N(c1ccncc1)c1c(cccc2)c2c(-c2ccccc2)c(cc2)c1cc2-c1nc(cccc2)c2[n]1-c1ccccc1 RZNSKCZTGWLEFV-UHFFFAOYSA-N 0.000 description 1
- UDMSIRWWSNUWPX-UHFFFAOYSA-N CC1(C)c(ccc(NC2=CC=NCC2)c2)c2-c2c1cccc2 Chemical compound CC1(C)c(ccc(NC2=CC=NCC2)c2)c2-c2c1cccc2 UDMSIRWWSNUWPX-UHFFFAOYSA-N 0.000 description 1
- ONWZKYOPQOQNBW-UHFFFAOYSA-N CC1(C)c2c(C)cccc2-c2cc(N(c3ccncc3)c3c(cccc4)c4cc(cc4)c3cc4-c3nc(cccc4)c4[n]3-c3ccccc3)ccc12 Chemical compound CC1(C)c2c(C)cccc2-c2cc(N(c3ccncc3)c3c(cccc4)c4cc(cc4)c3cc4-c3nc(cccc4)c4[n]3-c3ccccc3)ccc12 ONWZKYOPQOQNBW-UHFFFAOYSA-N 0.000 description 1
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N Cc1ccncc1 Chemical compound Cc1ccncc1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 235000006508 Nelumbo nucifera Nutrition 0.000 description 1
- 240000002853 Nelumbo nucifera Species 0.000 description 1
- 235000006510 Nelumbo pentapetala Nutrition 0.000 description 1
- HBWDWGMBZIFBQE-UHFFFAOYSA-N OB(Cc1ccccc1)O Chemical compound OB(Cc1ccccc1)O HBWDWGMBZIFBQE-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- VLBHRBCWXCMOFD-UHFFFAOYSA-N c(cc1)ccc1N1c(cccc2)c2NC1c(cc1)cc2c1cc(cccc1)c1c2 Chemical compound c(cc1)ccc1N1c(cccc2)c2NC1c(cc1)cc2c1cc(cccc1)c1c2 VLBHRBCWXCMOFD-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000006392 deoxygenation reaction Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- LGLJXZWEUGZQRX-UHFFFAOYSA-N n,n-diphenyl-6-[4-(n-phenylanilino)phenyl]pyren-1-amine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C2=CC=C3C=CC(=C4C=CC(C2=C43)=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 LGLJXZWEUGZQRX-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
-
- 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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- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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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
- H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen 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
- 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
- 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
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
-
- 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
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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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
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Abstract
本发明提供一种蒽类化合物及其合成方法和有机发光器件,涉及有机光电材料技术领域。本发明通过在蒽的主体结构上连接不同的配体,调节材料的分子量、π共轭程度及亲电性,使得电荷传输能力增强,玻璃化温度提高,不易结晶,成膜性更好,材料更加稳定。合成方法简单易操作。该材料可用于制备有机发光器件,尤其可作为有机发光器件的电子传输层材料,其有机发光器件具有发光效率高,寿命长的优点。
Description
技术领域
本发明涉及有机光电材料技术领域,尤其涉及一种蒽类化合物及其合成方法和有机发光器件。
背景技术
有机电致发光器件(OLED)作为一种新兴的平面面板显示,其具有自发光、视角宽、全固化、全彩化、反应速度快、高亮度、低驱动电压、厚度薄、质量轻、可制作大尺寸与弯曲面板等特点,近年来,OLED在显示器市场得到了越来越多的应用,成为目前最具潜力的面板显示技术。
有机发光器件其结构一般包括阴极、阳极及处于二者之间的有机物层,其中有机物层主要包括发光层和平衡载流子注入和传输的空穴注入层、空穴传输层、电子注入层、电子传输层等功能层。添加各功能层的目的主要是平衡从阴阳两极注入的空穴和电子,从而利于空穴和电子在发光层的复合,提高器件的激子利用率,最终提高器件的发光效率和使用寿命。由于载流子中电子的传输速度低于空穴的传输速度,导致电子和空穴复合效率低和复合区域的偏移,从而导致有机电致发光器件的发光效率低下、光色不均匀、寿命低,各功能层的载流子传输良莠不齐,并不能有效的平衡载流子的注入,随着市场对OLED器件要求的进一步提高,更高发光效率、更长寿命、更低成本成为OLED器件发展的趋势,所以如何提高电子迁移率,使得载流子注入平衡成为迫在眉睫的问题。
发明内容
本发明的目的是提供一种蒽类化合物及其合成方法和有机发光器件,本发明提供的蒽类化合物在蒽类主体上连接不同配体,其结构易于电荷的分散及迁移,稳定性好,玻璃化温度高,成膜性好,合成方法简单易操作,使用该蒽类化合物制备的有机发光器件有良好的发光效率和寿命表现。
本发明提供了一种蒽类化合物,其分子结构通式如化学式Ⅰ或Ⅱ所示:
其中,Ar1、Ar2、Ar3独立地选自氢、取代或未取代的C1~C60的烷基、取代或未取代的C1~C60的烷氧基、取代或未取代的C6~C60的芳基、取代或未取代C7~C60的芳胺基、取代或未取代的C3~C60的杂环基、取代或未取代的C10-C60稠环基中的一种。
优选的,Ar1、Ar2、Ar3独立地选自氢、取代或未取代的C1~C30的烷基、取代或未取代的C1~C30的烷氧基、取代或未取代的C6~C30的芳基、取代或未取代C12~C30的芳胺基、取代或未取代的C3~C30的杂环基、取代或未取代的C10-C30稠环基中的一种。
再优选,Ar1、Ar2、Ar3可独立地选自C1~C4的烷基或如下所示基团中的任意一种:
X、Y、Z独立地选自氢、氰基、硝基、C1~C30的烷基、C1~C30的烷氧基、C6~C30芳基、C10~C30的稠环基或C3~C30的杂环基。
再优选,本发明的蒽类化合物,选自如下所示化学结构中的任意一种:
。
本发明提供了一种蒽类化合物的合成方法,合成路线如下所示:
其中,Ar1、Ar2、Ar3独立地选自氢、取代或未取代的C1~C60的烷基、取代或未取代的C1~C60的烷氧基、取代或未取代的C6~C60的芳基、取代或未取代C7~C60的芳胺基、取代或未取代的C3~C60的杂环基、取代或未取代的C10-C60稠环基中的一种。
本发明还提供了一种有机发光器件,所述有机发光器件包括阴极、阳极和置于所述两电极之间的一个或多个有机物层,所述的有机物层含有本发明所述的蒽类化合物。
优选的,所述有机物层包括电子传输层,电子传输层中含有本发明所述的蒽类化合物。
本发明的有益效果:
本发明提供一种蒽类化合物及其合成方法和有机发光器件。本发明通过在蒽的主体结构上连接不同的配体,调节材料的分子量、π共轭程度及亲电性,分子共轭体系增大,电荷更易分散,使得材料的电荷迁移定向性增强,材料体系更加稳定;分子量增加使得材料的玻璃化温度提高,且通过连接不同的配体,降低分子的平面性,使材料不易结晶,成膜性更好。该材料可有效地应用于制备有机发光器件,尤其可作为有机发光器件的电子传输层,其有机发光器件具有发光效率高,寿命长的优点。
具体实施方式:
下面将结合本发明实施例的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明的保护范围。
本发明提供了一种蒽类化合物,其分子结构通式如化学式Ⅰ或Ⅱ所示:
优选的,Ar1、Ar2、Ar3独立地选自氢、取代或未取代的C1~C60的烷基、取代或未取代的C1~C60的烷氧基、取代或未取代的C6~C60的芳基、取代或未取代C7~C60的芳胺基、取代或未取代的C3~C60的杂环基、取代或未取代的C10-C60稠环基中的一种。
优选的,Ar1、Ar2、Ar3独立地选自氢、取代或未取代的C1~C30的烷基、取代或未取代的C1~C30的烷氧基、取代或未取代的C6~C30的芳基、取代或未取代C12~C30的芳胺基、取代或未取代的C3~C30的杂环基、取代或未取代的C10-C30稠环基中的一种。
按照本发明,所述取代的烷基、取代的烷氧基、取代的芳基、取代的芳胺基、取代的杂环基、取代的稠环基中,所述取代基独立地选自氘、C1-C10烷基、氰基、卤素、硝基、C6-C24芳基或C3-C20杂环基。
优选的,Ar1、Ar2、Ar3可独立地选自C1~C4的烷基或如下所示基团中的任意一种:
X、Y、Z独立地选自氢、氰基、硝基、C1~C30的烷基、C1~C30的烷氧基、C6~C30芳基、C10~C30的稠环基或C3~C30的杂环基。
作为举例,没有特别限定,本发明所述的一种蒽类化合物选自如下所示化学结构中的任意一种:
。
本发明还提供了一种蒽类化合物的合成方法,合成路线如下所示:
其中,Ar1、Ar2、Ar3独立地选自氢、取代或未取代的C1~C60的烷基、取代或未取代的C1~C60的烷氧基、取代或未取代的C6~C60的芳基、取代或未取代C7~C60的芳胺基、取代或未取代的C3~C60的杂环基、取代或未取代的C10-C60稠环基中的一种。
本发明的蒽类化合物通过一系列溴化、Buchward偶联、Suziki偶联反应合成本发明所述的化学式Ⅰ或化学式Ⅱ结构的蒽类化合物。
本发明对上述反应没有特殊的限制,采用本领域技术人员所熟知的常规反应即可,该制备方法简单,易于操作。
本发明还提供了一种有机发光器件,所述有机发光器件包括阴极、阳极和置于所述两电极之间的一个或多个有机物层,所述的有机物层含有本发明所述的蒽类化合物。
优选的,所述有机物层包括电子传输层,电子传输层中含有本发明所述的蒽类化合物。
本发明所述的的有机发光器件结构优选具体为:ADN/DPAP-DPPA用作发光层物质,本发明所述的蒽类化合物用作电子传输层,用以制造有以下相同构造的有机发光器件:ITO/2-TNATA(80nm)/NPB(30nm)/ADN:DPAP-DPPA(30nm)/本发明所述的蒽类化合物(30nm)/LiF(0.5nm)/Al(500nm)。
本发明所述有机发光器件可广泛应用于面板显示、照明OLED、柔性OLED、电子纸、有机感光体或有机薄膜晶体管等领域。
[实施例1]化合物2的合成
Step1:氮气保护下,反应容器里加入2-溴蒽(2.16g,8.4mmol)、1-苯基-1H-苯并咪唑硼酸(2.19g,9.2mmol)、四三苯基膦钯(0.09g,0.08mmol)、碳酸钾(3.48g,25.2mmol),甲苯60mL,乙醇20mL及蒸馏水20mL,在120℃条件下搅拌3h。反应结束以后蒸馏水停止反应,乙酸乙酯萃取,有机层用MgSO4干燥,减压蒸馏去掉溶剂,之后用硅胶柱层析提纯得到中间体2-2(2.04g,67%)。
Step2:氮气无光条件下,反应器中加入2-2(3.7g,10.0mmol),DMF溶液60mL,冰醋酸60mL,氯仿50mL,加入NBS(2.22g,12.5mmol),室温条件下搅拌2h,得到粗产物沉淀,过滤,甲醇洗涤,得到中间体2-3(3.46g,77%)。
Step3:反应容器里加入中间体2-3(3.77g,8.4mmol)、二苯胺2-1(1.56g,9.2mmol)、叔丁醇钾(2.83g,25.2mmol)、Pd2(dba)3(0.07g,0.08mmol)、超声除氧的二甲苯40mL,搅拌溶解,置换空气三次,加入P(t-Bu)3(0.07g,0.34mmol),再次置换空气三次,回流反应6h,冷却至室温,加入足量的二氯甲烷使得产品完全溶解,过少量硅胶漏斗,除掉催化剂和盐,滤液浓缩至粘稠状,过柱层析,得到化合物2-4(3.16g,70%)。
Step4:氮气无光条件下,反应器中加入2-4(5.38g,10.0mmol),DMF溶液60mL,冰醋酸60mL,氯仿50mL,加入NBS(2.22g,12.5mmol),室温条件下搅拌2h,得到粗产物沉淀,过滤,甲醇洗涤,得到中间体2-5(4.44g,72%)。
Step5:氮气保护下,反应容器里加入2-5(5.18g,8.4mmol)、苯硼酸(1.12g,9.2mmol)、四三苯基膦钯(0.09g,0.08mmol)、碳酸钾(3.48g,25.2mmol),甲苯60mL,乙醇20mL及蒸馏水20mL,在120℃条件下搅拌3h。反应结束以后蒸馏水停止反应,乙酸乙酯萃取,有机层用MgSO4干燥,减压蒸馏去掉溶剂,之后用硅胶柱层析提纯得到中间体2(3.25g,63%)。
[实施例2]化合物8的合成
Step1:反应器中加入9,9-二甲基-9H-芴-3-胺(1.67g,8mmol)的甲苯溶液、4-溴吡啶(1.05g,6.67mmol)、Pd2(dba)3(0.17g,0.2mmol)、P(t-Bu)3(0.14,0.67mmol)、NaOt-Bu(2.24g,20mmol)、甲苯溶液100mL,100℃条件下反应24h,反应结束后用乙醚和水萃取有机相,有机层用MgSO4干燥,浓缩有机物,过柱层析、重结晶得到中间体8-1(1.43g,75%)。
Step2:按照中间体2-2的合成方法得到中间体8-2。
Step3:按照中间体2-3的合成方法得到中间体8-3。
Step4:按照中间体2-4的合成方法得到中间体8-4。
Step5:按照中间体2-5的合成方法得到中间体8-5。
Step6:按照中间体2的合成方法得到中间体8(3.61g,60%)。
[实施例3]化合物12的合成
按照化合物8的合成方法得到化合物12(4.05g,65%)。
[实施例4]化合物27的合成
按照化合物2的合成方法得到化合物27(3.47g,67%)。
[实施例5]化合物54的合成
按照化合物2的合成方法得到化合物54(3.76g,64%)。
[实施例6]化合物68的合成
Step1:按照中间体8-1的合成方法得到中间体68-1。
Step2:按照中间体2-2的合成方法得到中间体68-2。
Step3:按照中间体2-3的合成方法得到中间体68-3。
Step4:按照化合物2的合成方法得到中间体68-4。
Step5:按照中间体2-5的合成方法得到中间体68-5。
Step6:按照中间体2-4的合成方法得到化合物68(3.65g,58%)。
[实施例7]化合物118的合成
按照化合物2的合成方法得到化合物118(3.51g,58%)。
[实施例8]化合物123的合成
按照化合物2的合成方法得到化合物123(3.26g,55%)。
本发明实施例合成的蒽类化合物FD-MS值如表1所示。
【表1】
实施例 | FD-MS |
实施例1 | m/z=613.17(C45H31N3=613.25) |
实施例2 | m/z=715.33(C52H35N4=715.29) |
实施例3 | m/z=740.21(C54H36N4=740.29) |
实施例4 | m/z=615.28(C43H29N5=615.24) |
实施例5 | m/z=698.27(C50H42N4=698.34) |
实施例6 | m/z=749.17(C51H31N3S2=749.20) |
实施例7 | m/z=719.29(C51H33N3S=719.24) |
实施例8 | m/z=705.22(C49H31N5O=705.25) |
[对比实施例1]器件制备实施例:
将ITO玻璃基板放在蒸馏水中清洗2次,超声波洗涤30分钟,用蒸馏水反复清洗2次,超声波洗涤10分钟,蒸馏水清洗结束后,异丙醇、丙酮、甲醇等溶剂按顺序超声波洗涤以后干燥,转移到等离子体清洗机里,将上述基板洗涤5分钟,送到蒸镀机里。
在已经准备好的ITO透明电极上逐层蒸镀空穴注入层2-TNATA/80nm、蒸镀空穴传输层NPB/30nm、蒸镀主体ADN(9,10-Di(2-naphthyl)anthracene):掺杂DPAP-DPPA(6-(4-(diphenylamino)phenyl)-N,N-diphenyl pyren-1-amine)5%混合/30nm、然后蒸镀电子传输层TPBi/30nm、阴极LiF/0.5nm、Al/500nm。
[实施例9]器件制备实施例:
将对比实施例1中的TPBi换成实施例1的化合物2。
[实施例10]器件制备实施例:
将对比实施例1中的ADN换成实施例2的化合物8。
[实施例11]器件制备实施例:
将对比实施例1中的ADN换成实施例3的化合物12。
[实施例12]器件制备实施例:
将对比实施例1中的ADN换成实施例4的化合物27。
[实施例13]器件制备实施例:
将对比实施例1中的ADN换成实施例5的化合物54。
[实施例14]器件制备实施例:
将对比实施例1中的ADN换成实施例6的化合物68。
[实施例15]器件制备实施例:
将对比实施例1中的ADN换成实施例6的化合物118。
[实施例16]器件制备实施例:
将对比实施例1中的ADN换成实施例6的化合物123。
本发明实施例9-16以及对比实施例1制备的发光器件的发光特性测试结果如表2所示。
[表2]
以上结果表明,本发明的蒽类化合物应用于有机发光器件中,尤其是用作电子传输层,其有机电光器件的发光效率和寿命有显著提高,本发明的蒽类化合物是性能良好的有机发光材料。
应当指出,本发明用个别实施方案进行了特别描述,但在不脱离本发明原理的前提下,本领域普通技术人可对本发明进行各种形式或细节上的改进,这些改进也落入本发明的保护范围内。
Claims (7)
1.一种蒽类化合物,其特征在于,其分子结构通式如化学式Ⅰ或Ⅱ所示:
其中,Ar1、Ar2、Ar3独立地选自氢、取代或未取代的C1~C60的烷基、取代或未取代的C1~C60的烷氧基、取代或未取代的C6~C60的芳基、取代或未取代C7~C60的芳胺基、取代或未取代的C3~C60的杂环基、取代或未取代的C10-C60稠环基中的一种。
2.根据权利要求1所述的一种蒽类化合物,其特征在于,Ar1、Ar2、Ar3独立地选自氢、取代或未取代的C1~C30的烷基、取代或未取代的C1~C30的烷氧基、取代或未取代的C6~C30的芳基、取代或未取代C12~C30的芳胺基、取代或未取代的C3~C30的杂环基、取代或未取代的C10-C30稠环基中的一种。
3.根据权利要求1所述的一种蒽类化合物,其特征在于,Ar1、Ar2、Ar3可独立地选自C1~C4的烷基或如下所示基团中的任意一种:
X、Y、Z独立地选自氢、氰基、硝基、C1~C30的烷基、C1~C30的烷氧基、C6~C30芳基、C10~C30的稠环基或C3~C30的杂环基。
4.根据权利要求1所述的一种蒽类化合物,其特征在于,选自如下所示化学结构中的任意一种:
。
5.权利要求1~4任一项所述的一种蒽类化合物的合成方法,其特征在于,通过如下路线合成得到所述蒽类化合物:
其中,Ar1、Ar2、Ar3独立地选自氢、取代或未取代的C1~C60的烷基、取代或未取代的C1~C60的烷氧基、取代或未取代的C6~C60的芳基、取代或未取代C7~C60的芳胺基、取代或未取代的C3~C60的杂环基、取代或未取代的C10-C60稠环基中的一种。
6.一种有机发光器件,其特征在于,所述有机发光器件包括阴极、阳极和置于所述两电极之间的一个或多个有机物层,所述的有机物层含有权利要求1~4任一项所述的蒽类化合物。
7.根据权利要求6中所述的一种有机发光器件,其特征在于,所述有机物层包括电子传输层,电子传输层中含有权利要求1~4任一项所述的蒽类化合物。
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