CN111960954A - Organic electroluminescent compound of benzanthracene derivative and preparation method and application thereof - Google Patents
Organic electroluminescent compound of benzanthracene derivative and preparation method and application thereof Download PDFInfo
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- CN111960954A CN111960954A CN202010947851.2A CN202010947851A CN111960954A CN 111960954 A CN111960954 A CN 111960954A CN 202010947851 A CN202010947851 A CN 202010947851A CN 111960954 A CN111960954 A CN 111960954A
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- organic electroluminescent
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 46
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical class C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims description 14
- 239000000463 material Substances 0.000 claims abstract description 31
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 239000000126 substance Substances 0.000 claims abstract description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 5
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
- 125000001769 aryl amino group Chemical group 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 2
- 239000010410 layer Substances 0.000 claims description 60
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 42
- 239000000376 reactant Substances 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 239000012044 organic layer Substances 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 18
- 239000000706 filtrate Substances 0.000 claims description 18
- 239000012074 organic phase Substances 0.000 claims description 17
- 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 claims description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 16
- 238000005406 washing Methods 0.000 claims description 15
- 239000012153 distilled water Substances 0.000 claims description 12
- 238000004440 column chromatography Methods 0.000 claims description 11
- 238000001816 cooling Methods 0.000 claims description 11
- 230000005525 hole transport Effects 0.000 claims description 11
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 10
- 239000012065 filter cake Substances 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000008346 aqueous phase Substances 0.000 claims description 9
- 238000002347 injection Methods 0.000 claims description 9
- 239000007924 injection Substances 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 9
- 235000019341 magnesium sulphate Nutrition 0.000 claims description 9
- 239000003208 petroleum Substances 0.000 claims description 9
- 238000000967 suction filtration Methods 0.000 claims description 9
- 239000003480 eluent Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
- 238000002386 leaching Methods 0.000 claims description 6
- 239000012046 mixed solvent Substances 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 239000002019 doping agent Substances 0.000 claims description 4
- 238000003810 ethyl acetate extraction Methods 0.000 claims description 4
- 239000002346 layers by function Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000012071 phase Substances 0.000 claims description 4
- 125000003003 spiro group Chemical group 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000012295 chemical reaction liquid Substances 0.000 claims description 2
- 150000001924 cycloalkanes Chemical class 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 238000009776 industrial production Methods 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 21
- 238000004020 luminiscence type Methods 0.000 description 11
- 230000009286 beneficial effect Effects 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 239000012467 final product Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 230000000717 retained effect Effects 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- -1 dimethylphenyl Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- KCBAMQOKOLXLOX-BSZYMOERSA-N CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O Chemical compound CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O KCBAMQOKOLXLOX-BSZYMOERSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- POFVJRKJJBFPII-UHFFFAOYSA-N N-cyclopentyl-5-[2-[[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]amino]-5-fluoropyrimidin-4-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C1(CCCC1)NC=1SC(=C(N=1)C)C1=NC(=NC=C1F)NC1=NC=C(C=C1)CN1CCN(CC1)CC POFVJRKJJBFPII-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 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
- 230000000903 blocking effect Effects 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
- 239000006227 byproduct Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 125000002560 nitrile group Chemical group 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
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 238000005036 potential barrier Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
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- 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
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- 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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- 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
- C07D405/02—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 two hetero rings
- C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
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Abstract
The invention discloses an organic electroluminescent compound of a benzanthracene derivative, which has a structural general formula shown in chemical formula 1:x is a bond, O, S, Si (R)4R5),C(R6R7) Or NR8;Ar1、Ar2、R1‑R3Each independently selected from: hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C10-C30 fused ring, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkylmercapto, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C6-C30 aryloxy. The organic electroluminescent compound has short synthetic route and simple processThe material is easy to obtain, the cost is low, and the method is suitable for industrial production.
Description
Technical Field
The invention relates to the technical field of luminescent materials, in particular to an organic electroluminescent compound of a benzanthracene derivative, and a preparation method and application thereof.
Background
An organic electric element utilizing an organic light emitting phenomenon generally has an anode, a cathode, and a structure including an organic layer therebetween. Here, the organic layer is generally formed as a multilayer structure composed of various different materials in order to improve efficiency and stability of the organic electric device, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
Among them, hole transport materials generally have a low Highest Occupied Molecular Orbital (HOMO) value, which tends to reduce efficiency when a material having fast hole mobility is used to reduce a driving voltage. In the OLED, since hole mobility is faster than electron mobility, charge imbalance in the light emitting layer occurs, and efficiency and lifetime degradation occurs. The technical problem can be effectively avoided by introducing a light-emitting auxiliary layer between the light-emitting layer and the hole transport layer.
However, at present, the materials used as the light-emitting auxiliary layer are limited, the red light-emitting auxiliary layer on the panel production line is mostly made of materials related to deshan and dupont dowii, such materials are mostly made of fluorene ring structures, and the light-emitting auxiliary layer is made of materials capable of solving the problem of the hole transport layer and has a suitable hole mobility to provide a suitable driving current. These requirements are not met, however, only by structural features with respect to the core of the luminescence auxiliary layer material.
Therefore, it is an urgent technical problem to provide a material for a light-emitting auxiliary layer having a high T1 energy value and a wide band gap to improve the efficiency and lifetime of an organic electronic device.
Disclosure of Invention
In view of the above, the invention provides a material for obtaining a luminescence auxiliary layer with more excellent performance by using a benzanthracene derivative as a mother nucleus and connecting different active sites on the benzanthracene derivative with side chains, which can solve the technical problems of unsatisfactory luminous efficiency and service life of the conventional organic electroluminescent device.
In order to achieve the purpose, the invention adopts the following technical scheme:
an organic electroluminescent compound of a benzanthracene derivative, the structural general formula of the organic electroluminescent compound of the benzanthracene derivative is shown in chemical formula 1:
wherein X is a bond, or X is selected from O, S, Si (R)4R5),C(R6R7) Or NR8;
The R is1-R3Each independently selected from: hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C10-C30 fused ring, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkylmercapto, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C6-C30 aryloxy;
the R is1-R3Each independently preferably selected from methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, alkoxy, aryloxy, phenyl, biphenyl or naphthyl; r1-R3The position of the substituent is any position of the benzene ring, R1The number of (2) is 0 to 4, R2、R3The number of (a) is 0 to 3.
The R is4-R8Each independently selected from: substituted or unsubstituted C1-C10 alkyl, C3-C15 cycloalkane, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C10-C30 fused ring, substituted or unsubstituted C1-C30 alkoxy;
R4-R8each independently preferably selected from methyl, ethyl, naphthyl, adamantyl, biphenyl, phenyl, heteroAryl, and the like;
ar is1、Ar2Independently selected from: substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C10-C30 fused ring, substituted or unsubstituted C5-C30 spiro ring, or Ar1、Ar2Each independently connects with adjacent substituent to form single ring or multiple ring;
Ar1and Ar2Each independently is preferably naphthyl, phenanthryl, phenyl, methylphenyl, fluorenyl, dimethylphenyl, dimethylfluorenyl, terphenyl, biphenyl, dibenzofuran, dibenzothiophene, and derivatives thereof.
Further, the mono-or polycyclic ring is a C3-C30 aliphatic ring or a C6-C30 aromatic ring; at least one carbon atom in the aliphatic ring or aromatic ring is replaced by nitrogen, oxygen, sulfur or silicon.
Adopt above-mentioned further beneficial effect to lie in: the performance of the benzanthracene mother nucleus is modified by the group limited by the invention, and the obtained compound is beneficial to improving the performance of a device.
The L is a connecting bond, or the L is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C10-C30 condensed ring, substituted or unsubstituted C5-C30 spiro ring.
In the above technical solutions, the term "substituted or unsubstituted" means substituted by one, two or more substituents selected from: deuterium; a halogen group; a nitrile group; a hydroxyl group; a carbonyl group; an ester group; a silyl group; a boron group; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted alkenyl; substituted or unsubstituted alkylamino; substituted or unsubstituted heterocyclylamino; substituted or unsubstituted arylamine; substituted or unsubstituted aryl; and a substituted or unsubstituted heterocyclic group, or a substituent in which two or more substituents among the above-shown substituents are connected, or no substituent. For example, "a substituent in which two or more substituents are linked" may include a biphenyl group. In other words, biphenyl can be an aryl group, or can be interpreted as a substituent with two phenyl groups attached.
In the above technical solution, the organic electroluminescent compound is preferably selected from any one of the following structures:
the invention also provides a preparation method of the organic electroluminescent compound of the benzanthracene derivative,
wherein:
the synthetic route is as follows when L is a substituent group:
the method comprises the following steps: (1) dissolving a reactant A and a reactant B in a reaction vessel containing dry toluene, and adding Pd into the reaction vessel under the nitrogen atmosphere2(dba)3、P(t-Bu)3t-BuONa, heating to 110 ℃, reacting for 10 hours under the condition of stirring, and after the reaction is finished, performing suction filtration by using diatomite while the diatomite is hot, and removing salt and a catalyst; then cooling the filtrate to room temperature and washing the filtrate with distilled water;separating the washing liquid, retaining an organic phase, extracting an aqueous phase by using ethyl acetate, combining the organic phase and an ethyl acetate extraction phase, drying the combined organic phase by using magnesium sulfate, and removing the solvent by using a rotary evaporator; then purifying the residual substance by adopting a column chromatography to obtain an intermediate C;
(2) respectively adding the intermediate C, the reactant D, tetrakis (triphenylphosphine) palladium and potassium carbonate into a mixed solvent of toluene, ethanol and water in a nitrogen atmosphere, heating to 100 ℃, carrying out reflux reaction for 8 hours, cooling to room temperature after the reaction is finished, carrying out suction filtration on reaction liquid after solid is separated out, washing with water to remove salt, then carrying out leaching with ethanol to obtain a filter cake, drying the filter cake, and then placing the filter cake into 1, 4-dioxane for recrystallization to obtain a compound shown in a general formula I;
or the like, or, alternatively,
the synthetic route is as follows when L is a connecting bond:
the method comprises the following steps: (1) dissolving a reactant a and a reactant b in a reaction vessel containing dry toluene, and adding Pd into the reaction vessel under the nitrogen atmosphere2(dba)3、P(t-Bu)3t-BuONa, heating to 110 ℃, stirring the mixture to react for 10 hours, and after the reaction is finished, performing suction filtration by using diatomite while the diatomite is hot, and removing salt and the catalyst; then cooling the filtrate to room temperature and washing the filtrate with distilled water; separating the washing liquid, retaining an organic phase, extracting an aqueous phase by using ethyl acetate, combining the organic phase and an ethyl acetate extraction phase, drying the combined organic phase by using magnesium sulfate, and removing the solvent by using a rotary evaporator; the remaining material was then purified by column chromatography to give the compound of formula I.
Further, when L is a substituent, the molar ratio of the reactant A to the reactant B is 1: 1.1;
the intermediate C, a reactant D, tetrakis (triphenylphosphine) palladium and potassium carbonate in a molar ratio of 1:1.1:0.01: 2.4;
when L is a chemical bond, the molar ratio of the reactant a to the reactant b is 1: 1.1.
Further, when L is a substituent or a chemical bond, the reactants a and P (t-Bu)3The molar ratio of t-BuONa is 1:0.01-0.02:0.056: 3;
reactants a and P (t-Bu)3The molar ratio of t-BuONa is preferably 1:0.0112:0.056: 3;
adopt above-mentioned further beneficial effect to lie in: the reaction under the limited proportion of the invention obtains a few by-products, has high speed and is easy to purify.
Further, when L is a substituent or a chemical bond, the eluent for column chromatography purification is dichloromethane and petroleum ether; the volume ratio of the dichloromethane to the petroleum ether is 1: 9.
Adopt above-mentioned further beneficial effect to lie in: under the limited eluent ratio, the invention can separate impurity points from products and obtain substances with high purity.
The invention has the beneficial effects that: the organic electroluminescent compound has the advantages of short synthetic route, simple process, easily obtained raw materials and low cost, and is suitable for industrial production.
The invention also provides application of the organic electroluminescent compound of the benzanthracene derivative in preparation of organic electroluminescent devices.
An organic electroluminescent device comprises a first electrode, a plurality of organic layers and a second electrode in sequence; at least one of the organic layers is an organic electroluminescent compound of the above-mentioned benzanthracene derivative.
Further, the organic layer includes one or more layers of a hole injection layer, a hole transport layer, a light emission auxiliary layer, a hole injection-hole transport functional layer, a light emitting layer, an electron transport layer, and an electron injection layer, and at least one layer includes the organic electroluminescent compound; preferably, at least one of the organic layers comprises a hole injecting substance, a hole transporting substance, a light-emitting auxiliary substance, or a hole injecting-hole transporting functional layer.
When the organic layer is of a single-layer structure, the organic layer is a light-emitting layer, and when the organic layer is of a multilayer structure, the organic layer comprises the light-emitting layer;
adopt above-mentioned further beneficial effect to lie in: the matching of different functional layers makes the energy level matching more reasonable.
Furthermore, the light-emitting layer is one or more of a phosphorescent host, a fluorescent host, a phosphorescent doped material and a fluorescent doped material. When the organic layer includes a hole transport layer or a light emission auxiliary layer, the hole transport layer includes an organic light emitting compound represented by chemical formula 1.
Adopt above-mentioned further beneficial effect to lie in: the use of the light-emitting auxiliary layer limited by the invention can enable the energy level transition between the hole transport layer and the light-emitting layer to be smoother, effectively reduce the potential barrier, reduce the driving voltage, prolong the service life and simultaneously improve the light-emitting efficiency.
Compared with the prior art, the invention has the beneficial effects that: the organic electroluminescent device provided by the invention has the advantages of high luminous efficiency, low driving voltage and longer service life.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1: preparation of Compound 9
After adding reactant A-9(50mmol) and reactant B-9(55mmol) in 200ml of toluene in a reaction vessel, Pd was added under a nitrogen atmosphere2(dba)3(0.56mmol)、P(t-Bu)3(2.8mmol) and t-BuONa (150 mmol). After the addition, the reaction temperature was slowly raised to 110 ℃ and the mixture was stirred for 10 h. Filtering with diatomite, removing salt and catalyst, cooling the filtrate to room temperatureThen, distilled water was added to the filtrate to wash the mixture, and after separating the liquid, the organic phase was retained and the aqueous phase was extracted with ethyl acetate. The combined organic layers were then dried over magnesium sulfate and the solvent was removed using a rotary evaporator. Mixing with dichloromethane: the remaining material was purified by column chromatography using petroleum ether at a volume ratio of 1:9 as an eluent to obtain the final product 9(21.7g, yield 78%, MS: 557.27).
Example 2: preparation of Compound 23
Step 1:
after adding reactant A-23(50mmol) and reactant B-23(55mmol) of the formula in 200ml of toluene in a reaction vessel, Pd was added under a nitrogen atmosphere2(dba)3(0.56mmol)、P(t-Bu)3(2.8mmol) and t-BuONa (150 mmol). After the addition, the reaction temperature was slowly raised to 110 ℃ and the mixture was stirred for 10 h. The filtrate was cooled to room temperature, then distilled water was added to the filtrate to wash, the organic phase was retained after liquid separation, and the aqueous phase was extracted with ethyl acetate. The combined organic layers were then dried over magnesium sulfate and the solvent was removed using a rotary evaporator. Mixing with dichloromethane: the remaining material was purified by column chromatography using petroleum ether at a volume ratio of 9 as an eluent to obtain intermediate C-23(27.2g, 75% yield).
Step 2:
N2under protection, respectively adding the intermediate C-23(35mmol), the intermediate D-23(38.5mmol), the tetrakis (triphenylphosphine) palladium (0.35mmol) and the potassium carbonate (84mmol) into a mixed solvent of 150mL of methylbenzene, 50mL of ethanol and 50mL of water, heating and refluxing for 8h, cooling to room temperature after the reaction is finished, after the solid is separated out, performing suction filtration, washing with water to remove the salt, leaching with a small amount of ethanol, and drying a filter cake. Recrystallization from 1, 4-dioxane (150mL) gave the final product 23(23.0g, 82% yield, MS: 800.38).
Example 3: preparation of Compound 44
Step 1:
after adding reactant A-44(50mmol) and reactant B-44(55mmol) of the formula in 200ml of toluene in a reaction vessel, Pd was added under nitrogen atmosphere2(dba)3(0.56mmol)、P(t-Bu)3(2.8mmol) and t-BuONa (150 mmol). After the addition, the reaction temperature was slowly raised to 110 ℃ and the mixture was stirred for 10 h. The filtrate was cooled to room temperature, then distilled water was added to the filtrate to wash, the organic phase was retained after liquid separation, and the aqueous phase was extracted with ethyl acetate. The combined organic layers were then dried over magnesium sulfate and the solvent was removed using a rotary evaporator. Mixing with dichloromethane: the remaining material was purified by column chromatography using petroleum ether at a volume ratio of 1:9 as an eluent to obtain intermediate C-44(22.0g, 77% yield).
Step 2:
N2under protection, respectively adding the intermediate C-44(35mmol), the intermediate D-44(38.5mmol), the tetrakis (triphenylphosphine) palladium (0.35mmol) and the potassium carbonate (84mmol) into a mixed solvent of 150mL of methylbenzene, 50mL of ethanol and 50mL of water, heating and refluxing for 8h, cooling to room temperature after the reaction is finished, after the solid is separated out, performing suction filtration, washing with water to remove the salt, leaching with a small amount of ethanol, and drying a filter cake. Recrystallization from 1, 4-dioxane (150mL) gave the final product 44(25.3g, 81% yield, MS: 894.40).
Example 4: preparation of Compound 100
Step 1:
after adding reactant A-100(50mmol) and reactant B-100(55mmol) of the formula in 200ml of toluene in a reaction vessel, Pd was added under nitrogen atmosphere2(dba)3(0.56mmol)、P(t-Bu)3(2.8mmol) and t-BuONa (150mmol) were added, the reaction temperature was slowly raised to 110 ℃ and the mixture was stirred for 10 h. The filtrate was cooled to room temperature, then distilled water was added to the filtrate to wash, the organic phase was retained after liquid separation, and the aqueous phase was extracted with ethyl acetate. The combined organic layers were then dried over magnesium sulfate and the solvent was removed using a rotary evaporator. Mixing with dichloromethane: the remaining material was purified by column chromatography using petroleum ether at a volume ratio of 1:9 as an eluent to obtain intermediate C-100(23.4g, 73% yield).
Step 2:
N2under protection, respectively adding the intermediate C-100(35mmol), the intermediate D-100(38.5mmol), tetrakis (triphenylphosphine) palladium (0.35mmol) and potassium carbonate (84mmol) into a mixed solvent of 150mL of toluene, 50mL of ethanol and 50mL of water, heating up and refluxing for 8h, cooling to room temperature after the reaction is finished, after the solid is separated out, performing suction filtration, washing with water to remove salt, leaching with a small amount of ethanol, and drying a filter cake. Recrystallization from 1, 4-dioxane (150mL) gave the final product 100(26.9g, 85% yield, MS: 904.21).
Example 5: preparation of Compound 116
Step 1:
after adding reactant A-116(50mmol) and reactant B-116(55mmol) of the formula in 200ml of toluene in a reaction vessel, Pd was added under a nitrogen atmosphere2(dba)3(0.56mmol)、P(t-Bu)3(2.8mmol) and t-BuONa (150 mmol). After the addition, the reaction temperature was slowly raised to 110 ℃ and the mixture was stirred for 10 h. The filtrate was cooled to room temperature, then distilled water was added to the filtrate to wash, the organic phase was retained after liquid separation, and the aqueous phase was extracted with ethyl acetate. The combined organic layers were then dried over magnesium sulfate and the solvent was removed using a rotary evaporator. By dichloro-chlorineMethane: the remaining material was purified by column chromatography using petroleum ether at a volume ratio of 1:9 as an eluent to obtain intermediate C-116(22.1g, 74% yield).
Step 2:
N2under protection, respectively adding the intermediate C-116(35mmol), the intermediate D-116(38.5mmol), the tetrakis (triphenylphosphine) palladium (0.35mmol) and the potassium carbonate (84mmol) into a mixed solvent of 150mL of methylbenzene, 50mL of ethanol and 50mL of water, heating and refluxing for 8h, cooling to room temperature after the reaction is finished, after the solid is separated out, performing suction filtration, washing with water to remove the salt, leaching with a small amount of ethanol, and drying a filter cake. Recrystallization from 1, 4-dioxane (150mL) provided the final product 116(25.5g, 82% yield, MS: 888.21).
The synthesis of the other compounds was the same as in the above-mentioned examples, and thus, they are not illustrated, and some of the mass spectra and molecular formulae are shown in Table 1 below.
Table 1:
[ device example 1 ]: production of organic electroluminescent device containing Compound 9
Coating with a thickness ofThe ITO glass substrate of (1) was washed in distilled water for 2 times, ultrasonically for 30 minutes, repeatedly washed in distilled water for 2 times, ultrasonically for 10 minutes, and after the washing with distilled water was completed, solvents such as isopropyl alcohol, acetone, and methanol were ultrasonically washed in this order, dried, transferred to a plasma cleaning machine, and the substrate was washed for 5 minutes and sent to an evaporation coater. Compounds NPB and F4-TCNQ (doping ratio 97:3) with a thickness of 50nm were vapor-deposited on the prepared ITO transparent electrode as a hole injection layer. Then the compound NPB is placed inA hole transport layer having a thickness of 50nm was vacuum-deposited on the formed hole injection layer. Compound 9 with the thickness of 20nm is evaporated on the hole transport layer to be used as a luminescence auxiliary layer;
then, a host material CBP and a dopant material (btfmp) were vapor-deposited on the luminescence auxiliary layer to a thickness of 20nm2Ir (dbm). The weight ratio of host material to dopant material was 95: 5. Then, BAlq with a thickness of 10nm as a hole blocking layer and an electron transport layer Alq with a thickness of 40nm were vacuum-deposited on the light-emitting layer3. Lithium fluoride (LiF) was vacuum-deposited on the electron transport layer to a thickness of 0.5nm as an electron injection layer. And finally, evaporating aluminum with the thickness of 150nm as a cathode, thereby completing the preparation of the organic electroluminescent device.
Organic electroluminescent device example 2-device example 24 containing the compounds 10, 18, 21, 23, 25, 32, 38, 40, 44, 45, 51, 73, 78, 80, 85, 90, 95, 98, 100, 102, 111, 116, 118 were prepared in the same manner as in the other methods except that the compound 9 in the device example 1 was replaced with the compounds 10, 18, 21, 23, 25, 32, 38, 40, 44, 45, 51, 73, 78, 80, 85, 90, 95, 98, 100, 102, 111, 116, 118, respectively.
Device comparative example 1 [ device comparative example 4]
Device comparative example 1: an organic electroluminescent device containing comparative compound 1 was fabricated.
An organic electroluminescent device containing comparative compound 1 was fabricated in the same manner as in device example 1 except that compound 9 of the luminescence auxiliary layer was replaced with comparative compound 1.
Device comparative example 2: an organic electroluminescent device containing comparative compound 2 was fabricated.
An organic electroluminescent device containing comparative compound 2 was fabricated in the same manner as in device example 1 except that compound 9 of the luminescence auxiliary layer was replaced with comparative compound 2.
Device comparative example 3: device comparative example 3 was made following the procedure of device example 1. Except that the luminescence assistance layer is not included.
Device comparative example 4: an organic electroluminescent device containing comparative compound 3 was fabricated.
An organic electroluminescent device containing comparative compound 2 was fabricated in the same manner as in device example 1 except that compound 9 of the luminescence auxiliary layer was replaced with comparative compound 3.
Table 2 shows the results of the test of the light emitting characteristics (luminance value of 5000 cd/m) of the devices of examples 1 to 24 and comparative devices 1 to 4 of the present invention2)。
As can be seen from table 2, the organic electroluminescent devices prepared using the compounds provided by the present invention as the material of the luminescence auxiliary layer have significantly improved driving voltage, luminous efficiency and lifetime compared to the organic electroluminescent devices using the comparative compounds 1 to 3 as the material of the luminescence auxiliary layer and without the luminescence auxiliary layer.
Compared with the comparative examples 1-2, the driving voltage of the device example is reduced by about 1.0V, the luminous efficiency is improved by about 7-13%, and the service life of the device is improved by 27-60 h.
Compared with the device performance, the driving voltage of the compound is higher than that of the comparative example 4, the luminous efficiency is comparable to that of the comparative example 4, the service life of the device is greatly prolonged, and the maximum service life can reach 160 h.
The reason for the obvious difference between the device data obtained from the same parent nucleus and the same device preparation method is probably that the spatial structure of the compound is changed due to the different connection positions of the 'L' in the side chain structure.
It will be apparent to those skilled in the art that many modifications and variations can be made in the present invention without departing from the spirit and scope of the invention. It is therefore contemplated that the present invention cover the modifications and variations of this invention provided they come within the scope of the appended claims and their equivalents.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (10)
1. An organic electroluminescent compound of a benzanthracene derivative, characterized in that the structural general formula of the organic electroluminescent compound of the benzanthracene derivative is shown as general formula 1:
wherein X is a bond, or X is selected from O, S, Si (R)4R5),C(R6R7) Or NR8;
The R is1-R3Each independently selected from: hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C10-C30 fused ring, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkylmercapto, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C6-C30 aryloxy;
the R is4-R8Each independently selected from: substituted or unsubstituted C1-C10 alkyl, C3-C15 cycloalkane, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C10-C30 fused ring, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy;
ar is1、Ar2Independently selected from: substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C10-C30 fused ring, substituted or unsubstituted C5-C30 spiro ring, or Ar1、Ar2Each independently connects with adjacent substituent to form single ring or multiple ring;
the L is a connecting bond, or the L is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted C10-C30 condensed ring, substituted or unsubstituted C5-C30 spiro ring.
2. The organic electroluminescent compound of a benzanthracene derivative according to claim 1, wherein the monocyclic or polycyclic ring is a C3-C30 aliphatic ring or a C6-C30 aromatic ring;
at least one carbon atom in the aliphatic ring or aromatic ring is replaced by nitrogen, oxygen, sulfur or silicon.
3. A preparation method of organic electroluminescent compounds of benzanthracene derivatives is characterized in that,
the synthetic route is as follows when L is a substituent group:
the method comprises the following steps: (1) dissolving a reactant A and a reactant B in a reaction vessel containing dry toluene, and adding Pd into the reaction vessel under the nitrogen atmosphere2(dba)3、P(t-Bu)3t-BuONa, heating to 110 ℃, reacting for 10 hours under the condition of stirring, and using after the reaction is finishedFiltering the diatomite while the diatomite is hot, and removing salt and a catalyst; then cooling the filtrate to room temperature and washing the filtrate with distilled water; separating the washing liquid, retaining an organic phase, extracting an aqueous phase by using ethyl acetate, combining the organic phase and an ethyl acetate extraction phase, drying the combined organic phase by using magnesium sulfate, and removing the solvent by using a rotary evaporator; then purifying the residual substance by adopting a column chromatography to obtain an intermediate C;
(2) respectively adding the intermediate C, the reactant D, tetrakis (triphenylphosphine) palladium and potassium carbonate into a mixed solvent of toluene, ethanol and water in a nitrogen atmosphere, heating to 100 ℃, carrying out reflux reaction for 8 hours, cooling to room temperature after the reaction is finished, carrying out suction filtration on reaction liquid after solid is separated out, washing with water to remove salt, then carrying out leaching with ethanol to obtain a filter cake, drying the filter cake, and then placing the filter cake into 1, 4-dioxane for recrystallization to obtain a compound shown in a general formula I;
the synthetic route is as follows when L is a connecting bond:
the method comprises the following steps: (1) dissolving a reactant a and a reactant b in a reaction vessel containing dry toluene, and adding Pd into the reaction vessel under the nitrogen atmosphere2(dba)3、P(t-Bu)3t-BuONa, heating to 110 ℃, stirring the mixture to react for 10 hours, and after the reaction is finished, performing suction filtration by using diatomite while the diatomite is hot, and removing salt and the catalyst; then cooling the filtrate to room temperature and washing the filtrate with distilled water; separating the washing liquid, retaining an organic phase, extracting an aqueous phase by using ethyl acetate, combining the organic phase and an ethyl acetate extraction phase, drying the combined organic phase by using magnesium sulfate, and removing the solvent by using a rotary evaporator; the remaining material was then purified by column chromatography to give the compound of formula I.
4. The method for producing an organic electroluminescent compound of a benzanthracene derivative according to claim 3, wherein the molar ratio of the reactant A to the reactant B when L is a substituent is 1: 1.1;
the molar ratio of the intermediate C, the reactant D, the tetrakis (triphenylphosphine) palladium and the potassium carbonate is 1:1.1:0.01: 2.4;
when L is a chemical bond, the molar ratio of the reactant a to the reactant b is 1: 1.1.
5. The method for preparing the organic electroluminescent compound of benzanthracene derivative according to claim 3, wherein the reactants a and Pd are reacted when L is a substituent or a chemical bond2(dba)3、P(t-Bu)3And the molar ratio of t-BuONa is 1:0.01-0.02:0.056: 3.
6. The method for producing an organic electroluminescent compound of a benzanthracene derivative according to claim 3, wherein the column chromatography purification eluent when L is a substituent or a chemical bond is dichloromethane and petroleum ether;
the volume ratio of the dichloromethane to the petroleum ether is 1: 9.
7. Use of the benzanthracene derivative organic electroluminescent compound according to claim 1 or 2 for the preparation of an organic electroluminescent device.
8. An organic electroluminescent device is characterized by sequentially comprising a first electrode, a plurality of organic layers and a second electrode; at least one of the organic layers includes an organic electroluminescent compound of the benzanthracene derivative according to claim 1 or 2.
9. The organic electroluminescent device according to claim 8, wherein the organic layer comprises one or more layers selected from a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a hole injection-hole transport functional layer, a light-emitting layer, an electron transport layer, and an electron injection layer, and at least one layer comprises the organic electroluminescent compound according to claim 1 or 2.
10. The organic electroluminescent device according to claim 9, wherein the light-emitting layer comprises one or more of a phosphorescent host material, a fluorescent host material, a phosphorescent dopant material and a fluorescent dopant material.
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