CN112430226A - Arylamine naphthofuran compound and preparation method and application thereof - Google Patents
Arylamine naphthofuran compound and preparation method and application thereof Download PDFInfo
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- CN112430226A CN112430226A CN202011331449.8A CN202011331449A CN112430226A CN 112430226 A CN112430226 A CN 112430226A CN 202011331449 A CN202011331449 A CN 202011331449A CN 112430226 A CN112430226 A CN 112430226A
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- -1 Arylamine naphthofuran compound Chemical class 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 239000000376 reactant Substances 0.000 claims abstract description 36
- 238000001035 drying Methods 0.000 claims abstract description 18
- 238000010438 heat treatment Methods 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000005406 washing Methods 0.000 claims abstract description 13
- 238000001914 filtration Methods 0.000 claims abstract description 10
- 239000012299 nitrogen atmosphere Substances 0.000 claims abstract description 10
- 238000002386 leaching Methods 0.000 claims abstract description 7
- 238000001704 evaporation Methods 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- 239000010410 layer Substances 0.000 claims description 55
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 48
- 239000000463 material Substances 0.000 claims description 47
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
- 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
- 239000007787 solid Substances 0.000 claims description 18
- 230000005525 hole transport Effects 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 239000012065 filter cake Substances 0.000 claims description 13
- 239000012153 distilled water Substances 0.000 claims description 12
- 238000002347 injection Methods 0.000 claims description 12
- 239000007924 injection Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 239000012074 organic phase 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
- 239000003054 catalyst 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
- 238000000034 method Methods 0.000 claims description 9
- 239000012044 organic layer Substances 0.000 claims description 9
- 239000003208 petroleum Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 238000000967 suction filtration Methods 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 230000000903 blocking effect Effects 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 239000005416 organic matter Substances 0.000 claims description 5
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229910052805 deuterium Inorganic materials 0.000 claims description 4
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 230000008020 evaporation Effects 0.000 claims description 3
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 238000011110 re-filtration Methods 0.000 claims description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 229940125904 compound 1 Drugs 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 7
- 238000004949 mass spectrometry Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 238000001514 detection method Methods 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 4
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 3
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 3
- WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 3
- 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
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940125810 compound 20 Drugs 0.000 description 3
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 3
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 3
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- MFMVRILBADIIJO-UHFFFAOYSA-N benzo[e][1]benzofuran Chemical compound C1=CC=C2C(C=CO3)=C3C=CC2=C1 MFMVRILBADIIJO-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N benzofuran Natural products C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000000750 progressive effect Effects 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- HONWGFNQCPRRFM-UHFFFAOYSA-N 2-n-(3-methylphenyl)-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C(=CC=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HONWGFNQCPRRFM-UHFFFAOYSA-N 0.000 description 1
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical compound C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 101150088517 TCTA gene Proteins 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- HAQFCILFQVZOJC-UHFFFAOYSA-N anthracene-9,10-dione;methane Chemical compound C.C.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 HAQFCILFQVZOJC-UHFFFAOYSA-N 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 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
- 150000004696 coordination complex Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 1
- QZXNDEONRUSYFB-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]-3-methylaniline Chemical compound CC1=CC=CC(NC=2C=CC(=CC=2)C=2C=CC(N)=CC=2)=C1 QZXNDEONRUSYFB-UHFFFAOYSA-N 0.000 description 1
- ZTLUNQYQSIQSFK-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]naphthalen-1-amine Chemical compound C1=CC(N)=CC=C1C(C=C1)=CC=C1NC1=CC=CC2=CC=CC=C12 ZTLUNQYQSIQSFK-UHFFFAOYSA-N 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 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
- 150000003918 triazines Chemical class 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-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
Classifications
-
- 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
- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
-
- 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
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Abstract
The invention discloses an arylamine naphthofuran compound, a preparation method and application thereof, wherein the structural general formula of the compound is shown as formula I:
formula I; the preparation method comprises the following steps: dissolving reactant A and reactant B in an organic solvent, and adding Pd under the nitrogen atmosphere2(dba)3、P(t‑Bu)3Heating to 110 deg.C for reaction with t-BuONa, suction filtering, washing, extracting, evaporating, dissolving and separating outAnd filtering, leaching and drying to obtain the compound of the chemical formula I. The organic electroluminescent device prepared by the luminescent compound has greatly reduced driving voltage and obviously improved service life and efficiency.
Description
Technical Field
The invention relates to the technical field of luminescent materials, in particular to an arylamine naphthofuran compound, a preparation method thereof and application of the compound in hole transport materials and organic electroluminescent devices.
Background
The twenty-first century is the century of information. With the progressive social informatization, people are urgently waiting for more efficient, energy-saving and environment-friendly lighting and display technologies as an important component of the information society. Organic Light-emitting diodes (OLEDs), also called Organic Light-emitting devices (Organic Light-emitting devices), have attracted much attention because of their advantages of self-luminescence, low driving voltage, high brightness, wide viewing angle, full-color emission, fast response, thin and Light Device, and the ability to fabricate large-area flexible devices. To date, OLEDs have been successfully used in commerce, such as cell phone displays, for example, and have found very wide application.
In order to improve the device performance of the OLED, a multilayer sandwich structure is usually adopted when designing the device structure, i.e. the anode, the cathode and the organic functional layer together form a complete device. Hole transport materials are materials that accept and efficiently transport positively charged hole carriers, typically with high hole mobility and low ionization potential. Is a very important part of organic electroluminescent devices.
The research on the hole-type material mainly focuses on the arylamine-type compound. The arylamine compound has high hole mobility and is an ideal hole transport material. The focus of the research at present is mainly to improve the thermal stability of the compounds and the stability of the film form of the compounds. Commonly used small molecule hole-blocking materials are mainly 1, 1-bis [4- [ N, N-di (p-tolylene) amino ] phenyl ] cyclohexane (TAPC), tris (4-carbazol-9-ylphenyl) amine (TcTa), N, N, N ', N' -Tetraphenylbenzidine (TPB), n, N ' -diphenyl-N, N ' - (1-naphthyl) -1,1 ' -biphenyl-4, 4' -diamine (α -NPD), N ' -diphenyl-N, N ' - (3-methylphenyl) -1,1 ' -biphenyl-4, 4' -diamine (TPD), 4',4 ″ -tris (N-3-methylphenyl-N-phenylamino) triphenylamine (m-MTDATA), and the like.
However, in organic electroluminescent devices using these materials, whether for fluorescent OLEDs or phosphorescent OLEDs, further improvements are still required in terms of luminous efficiency, lifetime, operating voltage, and the like.
Disclosure of Invention
In view of the above, the present invention provides an aromatic amine naphthofuran organic light emitting compound, a preparation method thereof, and an organic electroluminescent device, which have high light emitting efficiency and long lifetime.
In order to achieve the purpose, the invention adopts the following technical scheme:
an arylamine naphthofuran compound is shown as a formula I:
wherein,
when a is 1, b is 0, the formula is shown as II:
when b is 1, a is 0, the formula is shown in III:
R1，R2the position of the substituent is any position of the benzene ring, R1，R2The number of (A) is 0-3;
R1，R2each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstitutedSubstituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted 3-30 membered cycloalkyl, substituted or unsubstituted 3-30 membered heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-30 membered heteroaryl, substituted or unsubstituted 3-30 membered heteroarylamino, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C60 aryloxy; or are linked to an adjacent substituent(s) to form a mono-or polycyclic C3-C30 aliphatic ring or 3-30 membered aromatic ring, the carbon atoms of which may be replaced by one or more of nitrogen, oxygen, sulfur heteroatoms;
Ar1-Ar5each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-30 membered heteroaryl, substituted or unsubstituted C10-C30 fused ring, substituted or unsubstituted 3-30 membered heteroarylamino, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 aryloxy; substituted or unsubstituted C10-C30 spiro ring group, or C3-C30 aliphatic ring or C6-C30 aromatic ring connected with adjacent substituent to form single ring, wherein carbon atom can be replaced by one or more of nitrogen, oxygen, sulfur and silicon heteroatom;
L，Ar6independently represent a connecting bond; alternatively, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted 3-30 membered heteroaryl, a substituted or unsubstituted C10-C60 fused ring group, or a substituted or unsubstituted C10-C60 spiro ring group.
Preferably, the substituted group is selected from: deuterium, a halogen group, a nitrile group, a hydroxyl group, a carbonyl group, an ester group, a silyl group, a boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted heterocyclylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclyl group, or a group formed by connecting two or more of the above-shown substituents.
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.
As a further preferred aspect of the present invention, the luminescent compound is selected from any one of the following structures:
the invention also discloses a preparation method of the arylamine naphthofuran compound, which comprises the following steps:
(1) dissolving reactant A and reactant B in an organic solvent, and adding Pd under the nitrogen atmosphere2(dba)3、P(t-Bu)3Heating the mixture and t-BuONa to 110 ℃ for reaction, and after the reaction is finished, carrying out suction filtration, washing, extraction, evaporation, dissolution, precipitation, re-filtration, leaching and drying to obtain a compound of a chemical formula I;
wherein,
the reactant A is a reactant A-II or a reactant A-III;
the reactant B is a reactant B-II or a reactant B-III;
synthetic route to formula II:
synthetic route to formula III:
preferably, reactant A and reactant B, Pd2(dba)3、P(t-Bu)3The molar ratio of t-BuONa to t-BuONa is 1: 1.0-1.2: 0.01-0.015: 0.05-0.06: 1.5-2.
Preferably, after the reaction is completed, suction filtration is performed by using diatomite while hot, salts and a catalyst are removed, the filtrate is cooled to room temperature, then distilled water is added into the filtrate for washing, an organic phase is retained after liquid separation, an aqueous phase is extracted by using ethyl acetate, then a combined organic layer is dried by using magnesium sulfate, a solvent is removed by using a rotary evaporator, the organic phase is placed into toluene, the temperature is increased to 90-100 ℃ to completely dissolve a solid organic matter, then the temperature is gradually reduced until most of solid is separated out, filtration is performed, a filter cake is rinsed by using petroleum ether, and the filter cake is placed into a 65-75 ℃ oven for drying for 8-12 hours, so that a chemical formula II or a chemical formula III is obtained.
The invention also discloses application of the arylamine naphthofuran compound in preparing a hole transport material.
Furthermore, the invention also discloses application of the arylamine naphthofuran compound in preparation of organic electroluminescent devices.
An organic electroluminescent device comprises a first electrode, an organic electroluminescent material layer and a second electrode which are sequentially evaporated; the organic electroluminescent material layer comprises an arylamine naphthofuran compound shown in a general formula I.
Preferably, the organic electroluminescent material layer comprises one or more layers of a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer which are sequentially evaporated, and at least one layer of the organic electroluminescent material layer comprises the arylamine naphthofuran compound shown in the general formula I.
The first electrode serves as an anode, which preferably comprises a material having a high work function. Indium Tin Oxide (ITO) or Indium Zinc Oxide (IZO) is preferable.
The electron blocking layer may be disposed between the hole transport layer and the light emitting layer. As the electron blocking layer, a material known in the art, for example, an arylamine-based organic material, may be used.
The material of the light emitting layer is a material capable of emitting visible light by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining the received holes and electrons. In addition, the light emitting layer may include a host material and a dopant material; the mass ratio of the main material to the doping material is 90-99.5: 0.5-10; the doping material may include fluorescent doping and phosphorescent doping.
The light emitting layer may emit red, green or blue light, and may be formed of a phosphorescent material or a fluorescent material. The light emitting material is a material capable of emitting light in the visible light region by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining the holes and the electrons.
The phosphorescent dopant material is a phosphorescent material including a metal complex of iridium, platinum, or the like. For example, Ir (ppy)3Isogreen phosphorescent materials, FIrpic, FIr6Iso-blue phosphorescent material and Btp2Red phosphorescent materials such as ir (acac). As the fluorescent dopant material, a compound having an electron transporting action known in the art can be used.
As the hole-blocking layer material, a compound having a hole-blocking effect known in the art, for example, a phenanthroline derivative such as Bathocuproine (BCP), an oxazole derivative, a triazole derivative, a triazine derivative, or the like can be used, but the invention is not limited thereto.
The hole transport layer comprises an arylamine naphthofuran compound shown in a general formula I.
The electron injection layer may function to promote electron injection. Has the ability of transporting electrons and prevents excitons generated in the light emitting layer from migrating to the hole injection layer. The electron injecting material used in the present invention includes fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complexes.
The second electrode, which serves as a cathode, preferably comprises a metal alloy or a multilayer structure of metals having a low work function, for example Ca, Ba, Mg, Al, In, Mg, Yb, Sm.
The device of the invention can be used for an organic light-emitting device, an organic solar cell, electronic paper, an organic photoreceptor or an organic thin film transistor.
According to the technical scheme, the invention discloses an arylamine naphthofuran compound, compared with the prior art, the compound is a benzofuran compound, the naphthofuran compound increases the overall steric hindrance of the compound, and the asymmetric specific spatial structure is beneficial to reducing intermolecular cohesion, reducing crystallization possibility and improving glass transition temperature. The introduced arylamine side chain group is an electron donating group, and has good hole transmission characteristics, namely higher hole mobility; the compound of the material has a proper HOMO value, so that holes have small injection barriers, the driving voltage of the organic electroluminescent device prepared by using the luminescent compound is greatly reduced, and the service life and the efficiency are obviously improved.
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: synthesis of Compound 6
After adding reactant A-6(50mmol) and reactant B-6(60mmol) in dry toluene to a reaction vessel, Pd was added under a nitrogen atmosphere2(dba)3(0.55mmol)、P(t-Bu)3(3mmol) and t-BuONa (100 mmol); heating to 110 deg.C, stirring the mixture for 10h, suction filtering with diatomaceous earth while hot, removing salt and catalyst, and cooling the filtrate to room temperatureWarm, distilled water was then added to the filtrate for washing, the organic phase remained after liquid separation, the aqueous phase was extracted with ethyl acetate, the combined organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator, placed in toluene, warmed to 100 ℃ to completely dissolve the solid organic, and then gradually cooled to a temperature where most of the solid precipitated, filtered, the filter cake was rinsed with petroleum ether, and placed in a 65 ℃ oven for drying for 12h to give compound 6(29.8g, yield: 83%).
The compound 6 thus obtained was subjected to assay, and the results were as follows:
mass spectrometry test: a theoretical value of 717.30; the test value was 717.45.
Elemental analysis:
theoretical value: c, 90.34; h, 5.48; n, 1.95; o,2.23
Test values are: c, 90.30; h, 5.49; n, 1.97; o,2.25
Example 2: synthesis of Compound 20
After adding reactant A-20(50mmol) and reactant B-20(60mmol) in dry toluene to a reaction vessel, Pd was added under nitrogen atmosphere2(dba)3(0.55mmol)、P(t-Bu)3(3mmol) and t-BuONa (100 mmol); heating to 110 ℃, stirring the mixture for 10h, performing suction filtration with diatomite while hot to remove salts and catalysts, cooling the filtrate to room temperature, adding distilled water to the filtrate for washing, separating the liquid and retaining an organic phase, extracting an aqueous phase with ethyl acetate, drying the combined organic layers with magnesium sulfate, removing the solvent with a rotary evaporator, placing the mixture in toluene, heating to 100 ℃ to completely dissolve solid organic matters, gradually reducing the temperature until most of solid is separated out, filtering, leaching the filter cake with petroleum ether, and placing the filter cake in a 65 ℃ oven for drying for 12h to obtain the compound 20(31.5g, yield: 86%).
The compound 20 obtained was subjected to detection analysis, and the results were as follows:
mass spectrometry test: a theoretical value of 733.33; the test value was 733.62.
Elemental analysis:
theoretical value: c, 90.01; h, 5.91; n, 1.91; o,2.18
Test values are: c, 90.00; h, 5.93; n, 1.90; o,2.18
Example 3: synthesis of Compound 35
After adding reactant A-35(50mmol) and reactant B-35(60mmol) in dry toluene to a reaction vessel, Pd was added under nitrogen atmosphere2(dba)3(0.55mmol)、P(t-Bu)3(3mmol) and t-BuONa (100 mmol); heating to 110 ℃, stirring the mixture for 10h, performing suction filtration with diatomite while hot, removing salts and catalyst, cooling the filtrate to room temperature, adding distilled water to the filtrate for washing, separating the liquid, retaining the organic phase, extracting the aqueous phase with ethyl acetate, drying the combined organic layers with magnesium sulfate, removing the solvent with a rotary evaporator, placing in toluene, heating to 100 ℃ to completely dissolve the solid organic matter, gradually reducing the temperature until most of the solid is separated out, filtering, leaching the filter cake with petroleum ether, and placing in a 65 ℃ oven for drying for 12h to obtain a compound 35(30.5, yield: 85%).
The compound 35 thus obtained was subjected to detection analysis, and the results were as follows:
mass spectrometry test: a theoretical value of 717.30; the test value was 717.43.
Elemental analysis:
theoretical value: c, 90.01; h, 5.91; n, 1.91; o,2.18
Test values are: c, 90.00; h, 5.93; n, 1.90; o,2.18
Example 4: synthesis of Compound 55
Adding a reactant A into a reaction vesselAfter-55 (50mmol) and reactant B-55(60mmol) were dissolved in dry toluene, Pd was added under nitrogen atmosphere2(dba)3(0.55mmol)、P(t-Bu)3(3mmol) and t-BuONa (100 mmol); the temperature was raised to 110 ℃ and the mixture was stirred for 10h, suction filtration was carried out with celite while hot to remove salts and catalyst, the filtrate was cooled to room temperature, then distilled water was added to the filtrate for washing, the organic phase was retained after separation, the aqueous phase was extracted with ethyl acetate, then the combined organic layers were dried with magnesium sulfate and the solvent was removed using a rotary evaporator, placed in toluene, heated to 100 ℃ to completely dissolve the solid organic, after which the temperature was gradually lowered to precipitate most of the solid, filtered, the filter cake was rinsed with petroleum ether and placed in a 65 ℃ oven for drying for 12h to give compound 55(33.3g, yield: 84%).
The compound 55 thus obtained was subjected to assay, and the results were as follows:
mass spectrometry test: a theoretical value of 793.33; the test value was 793.41.
Elemental analysis:
theoretical value: c, 90.76; h, 5.46; n, 1.76; o,2.01
Test values are: c, 90.77; h, 5.43; n, 1.78; o,2.01
Example 5: synthesis of Compound 70
After adding reactant A-70(50mmol) and reactant B-70(60mmol) in dry toluene to a reaction vessel, Pd was added under nitrogen atmosphere2(dba)3(0.55mmol)、P(t-Bu)3(3mmol) and t-BuONa (100 mmol); heating to 110 deg.C, stirring the mixture for 10h, vacuum filtering with diatomaceous earth, removing salt and catalyst, cooling the filtrate to room temperature, adding distilled water to the filtrate, washing, separating to obtain organic phase, extracting the aqueous phase with ethyl acetate, drying the combined organic layers with magnesium sulfate, removing solvent with rotary evaporator, placing in toluene, heating to 100 deg.C to completely dissolve solid organic matter, and gradually dissolvingThe temperature was gradually lowered until most of the solid precipitated, filtered, and the filter cake was rinsed with petroleum ether and placed in an oven at 65 ℃ for drying for 12 hours to obtain compound 70(31.5g, yield: 82%).
The compound 70 obtained was subjected to detection analysis, and the results were as follows:
mass spectrometry test: a theoretical value of 767.32; the test value was 767.66.
Elemental analysis:
theoretical value: c, 90.71; h, 5.38; n, 1.82; o,2.08
Test values are: c, 90.73; h, 5.39; n, 1.80; o,2.07
Example 6: synthesis of Compound 85
After adding reactant A-85(50mmol) and reactant B-85(60mmol) in dry toluene to a reaction vessel, Pd was added under nitrogen atmosphere2(dba)3(0.55mmol)、P(t-Bu)3(3mmol) and t-BuONa (100 mmol); heating to 110 ℃, stirring the mixture for 10h, performing suction filtration with diatomite while hot to remove salts and catalysts, cooling the filtrate to room temperature, adding distilled water to the filtrate for washing, separating the liquid and retaining an organic phase, extracting an aqueous phase with ethyl acetate, drying the combined organic layers with magnesium sulfate, removing the solvent with a rotary evaporator, placing the mixture in toluene, heating to 100 ℃ to completely dissolve solid organic matters, gradually reducing the temperature until most of solid is separated out, filtering, leaching the filter cake with petroleum ether, and placing the filter cake in a 65 ℃ oven for drying for 12h to obtain a compound 85(28.3g, yield: 83%).
The compound 85 obtained was subjected to detection analysis, and the results were as follows:
mass spectrometry test: a theoretical value of 681.88; the test value was 681.46.
Elemental analysis:
theoretical value: c, 89.83; h, 5.77; n, 2.05; o,2.35
Test values are: c, 89.80; h, 5.79; n, 2.04; o,2.37
Example 7: synthesis of Compound 105
After adding reactant A-105(50mmol) and reactant B-105(60mmol) in dry toluene to a reaction vessel, Pd was added under nitrogen atmosphere2(dba)3(0.55mmol)、P(t-Bu)3(3mmol) and t-BuONa (100 mmol); heating to 110 ℃, stirring the mixture for 10h, performing suction filtration with diatomite while hot to remove salts and catalysts, cooling the filtrate to room temperature, then adding distilled water to the filtrate for washing, separating the liquid and retaining the organic phase, extracting the aqueous phase with ethyl acetate, then drying the combined organic layers with magnesium sulfate, removing the solvent with a rotary evaporator, placing in toluene, heating to 100 ℃ to completely dissolve the solid organic matter, then gradually reducing the temperature until most of the solid is separated out, filtering, leaching the filter cake with petroleum ether, and placing in a 65 ℃ oven for drying for 12h to obtain compound 105(32.9g, yield: 85%).
The compound 105 thus obtained was subjected to detection analysis, and the results were as follows:
mass spectrometry test: a theoretical value of 774.36; the test value was 774.55.
Elemental analysis:
theoretical value: c, 88.34; h, 5.98; n, 3.61; o,2.06
Test values are: c, 88.37; h, 5.94; n, 3.61; o,2.06
Example 8 to example 27
The synthesis, mass spectra and molecular formulae and yields for compounds 1, 4, 10, 13, 18, 24, 28, 32, 36, 40, 45, 50, 58, 62, 66, 83, 90, 95, 100, 110 were performed according to the synthetic methods of examples 1 to 7 as shown in table 1.
Table 1:
in addition, other compounds of the present application can be obtained by the synthetic methods according to the above-mentioned examples, and therefore, they are not illustrated herein.
The following are examples of the present invention, which are provided to aid understanding of the present invention and are not intended to limit the scope of the present invention. In addition, the preparation methods of the compounds which are not specifically listed in the embodiments of the present invention are methods generally applied in the related industries, and the methods described in the embodiments can be referred to when preparing other compounds.
To further illustrate the present invention, more specific device embodiments are listed below.
[ device example 1 ]: production of organic electroluminescent devices containing Compound 1
Coating with a thickness of
The 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. 4,4' -tri [ 2-naphthyl phenylamino ] with the thickness of 50nm is evaporated on the prepared ITO transparent electrode]Triphenylamine (2-TNATA) as a hole injection layer. Then, compound 1 prepared in example 8 was vacuum-evaporated on the formed hole injection layer to form a hole transport layer having a thickness of 30 nm. Then, a host material mCP and a blue light doping material FIrpic with the thickness of 30nm are evaporated on the hole transport layer. The weight ratio of host material to dopant material was 95: 5. Then, bis (2-methyl-8-hydroxyquinoline-N1, 08) - (1, 1' -biphenyl-4-hydroxy) aluminum (BALq) as a hole-blocking layer was vacuum-evaporated on the above light-emitting layer to a thickness of 10 nm. Alq3 was vacuum-deposited on the hole-blocking layer to a thickness of 40nm as an electron-transporting layer.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.
The device structure is as follows: ITO/2-TNATA/compound 1/mCP FIrpic/BALq/Alq 3/LiF/Al.
After the OLED light emitting device was completed as described above, the anode and cathode were connected by a known driving circuit, and the current efficiency of the device and the lifetime of the device were measured. After the electroluminescent device is manufactured according to the steps, the driving voltage, the luminous efficiency and the service life of the device are measured.
The molecular structural formula of the related material is shown as follows:
device example 2 device example 27
Organic electroluminescent device example 2-device example 27 containing compounds were prepared in the same manner as in the other methods except that compound 1 in device example 1 was replaced with compounds 4, 6, 10, 13, 18, 20, 24, 28, 32, 35, 36, 40, 45, 50, 55, 58, 62, 66, 70, 83, 85, 90, 95, 100, 105, and 110, respectively.
Device comparative example 1 [ device comparative example 2]
The compound 1 in the device example 1 was replaced with the comparative compound 1 and the comparative compound 2, respectively, and organic electroluminescent devices were prepared in the same manner as in the device example 1, and the hole transport layer comparative compound 1 and the comparative compound 2 had the following structures:
for the organic electroluminescence prepared as aboveThe device was applied with a forward DC bias voltage, and the organic electroluminescent characteristics were measured with a PR-650 photometric measuring instrument of PhotoRes research, Inc., and had a luminance of 1000cd/m2The life of T95 was measured using a life measuring device available from McScience. The results are shown in Table 2.
Table 2: test results of light emitting characteristics (luminance value 1000 cd/m) of device examples 1 to 27 and device comparative examples 1 to 2 of the present invention2)
Compared with the traditional hole transport material (compared with the compound 1), the driving voltage is reduced by 1.2-1.8V, the luminous efficiency is improved by 2-3 times, the service life of the device is prolonged by 57-97h, the glass transition temperature is improved by 22-38 ℃, and the performance of the device is obviously improved.
Compared with a comparative compound 2 with a similar structure, the compound of the invention has the main difference that the mother nucleus adopted by the comparative compound is fluorene, the compound of the invention adopts a benzofuran compound, the overall steric hindrance of the compound is increased by the naphthofuran, and the asymmetric specific spatial structure is beneficial to reducing the intermolecular cohesion, reducing the crystallization possibility and improving the glass transition temperature. The introduced arylamine side chain group is an electron donating group, and has good hole transmission characteristics, namely higher hole mobility; the compound of the material has a proper HOMO value, so that holes have small injection barriers, the driving voltage of the organic electroluminescent device prepared by using the luminescent compound is greatly reduced, and the service life and the efficiency are obviously improved.
Therefore, the driving voltage is reduced by 0.8-1.4V, the efficiency is reduced by 15.3-24.1%, the service life is prolonged by 49-89h, and the glass transition temperature is increased by 5-21 ℃. From the results of the above table 2, it can be confirmed that the organic electroluminescent device prepared using the compound provided by the present invention as a hole transport material exhibits high luminous efficiency and long life and lowers the driving voltage, increasing the glass transition temperature.
The embodiments in the present description are described in a progressive manner, each embodiment focuses on differences from other embodiments, and the same and similar parts among the embodiments are referred to each other. The device disclosed by the embodiment corresponds to the method disclosed by the embodiment, so that the description is simple, and the relevant points can be referred to the method part for description.
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 (9)
1. An arylamine naphthofuran compound is characterized in that the structural general formula of the compound is shown as formula I:
wherein,
when a is 1, b is 0, the formula is shown as II:
when b is 1, a is 0, the formula is shown in III:
R1，R2the position of the substituent isAt any position of the phenyl ring, R1，R2The number of (A) is 0-3;
R1，R2each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted 3-30 membered cycloalkyl, substituted or unsubstituted 3-30 membered heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-30 membered heteroaryl, substituted or unsubstituted 3-30 membered heteroarylamino, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C60 aryloxy; or are linked to an adjacent substituent(s) to form a mono-or polycyclic C3-C30 aliphatic ring or 3-30 membered aromatic ring, the carbon atoms of which may be replaced by one or more of nitrogen, oxygen, sulfur heteroatoms;
Ar1-Ar5each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-30 membered heteroaryl, substituted or unsubstituted C10-C30 fused ring, substituted or unsubstituted 3-30 membered heteroarylamino, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 aryloxy; substituted or unsubstituted C10-C30 spiro ring group, or C3-C30 aliphatic ring or C6-C30 aromatic ring connected with adjacent substituent to form single ring, wherein carbon atom can be replaced by one or more of nitrogen, oxygen, sulfur and silicon heteroatom;
L，Ar6independently represent a connecting bond; alternatively, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted 3-30 membered heteroaryl, a substituted or unsubstituted C10-C60 fused ring group, or a substituted or unsubstituted C10-C60 spiro ring group.
2. An arylamine naphthofuran compound of claim 1, wherein said substituted group is selected from: deuterium, a halogen group, a nitrile group, a hydroxyl group, a carbonyl group, an ester group, a silyl group, a boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted heterocyclylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclyl group, or a group formed by connecting two or more of the above-shown substituents.
3. The method for preparing the arylamine naphthofuran compound according to claim 1, comprising the steps of:
(1) dissolving reactant A and reactant B in an organic solvent, and adding Pd under the nitrogen atmosphere2(dba)3、P(t-Bu)3Heating the mixture and t-BuONa to 110 ℃ for reaction, and after the reaction is finished, carrying out suction filtration, washing, extraction, evaporation, dissolution, precipitation, re-filtration, leaching and drying to obtain a compound of a chemical formula I;
wherein,
the reactant A is a reactant A-II or a reactant A-III;
the reactant B is a reactant B-II or a reactant B-III;
synthetic route to formula II:
synthetic route to formula III:
4. the method for preparing the arylamine naphthofuran compound of claim 1, wherein the reactant A and the reactant B, Pd are2(dba)3、P(t-Bu)3The molar ratio of t-BuONa to t-BuONa is 1: 1.0-1.2: 0.01-0.015: 0.05-0.06: 1.5-2.
5. The method for preparing an aromatic amine naphthofuran compound as claimed in claim 1, wherein the method comprises the steps of performing suction filtration with diatomite while hot after the reaction is completed, removing salts and catalysts, cooling the filtrate to room temperature, adding distilled water into the filtrate for washing, retaining an organic phase after liquid separation, extracting an aqueous phase with ethyl acetate, drying the combined organic layer with magnesium sulfate, removing the solvent with a rotary evaporator, placing the solvent in toluene, heating to 90-100 ℃ to completely dissolve the solid organic matter, gradually reducing the temperature until most of the solid is separated out, filtering, rinsing the filter cake with petroleum ether, and placing the filter cake in a 65-75 ℃ oven for drying for 8-12 hours to obtain the compound of formula II or formula III.
6. The use of the aromatic amine naphthofuran compound of claim 1 in the preparation of a hole transport material.
7. Use of the arylamine naphthofuran compound of claim 1 in the preparation of an organic electroluminescent device.
8. An organic electroluminescent device is characterized by comprising a first electrode, an organic electroluminescent material layer and a second electrode which are sequentially evaporated; wherein the organic electroluminescent material layer comprises the aromatic amine naphthofuran compound of claim 1.
9. The organic electroluminescent device according to claim 8, wherein the organic electroluminescent material layer comprises one or more layers of a hole injection layer, a hole transport layer, a light emission auxiliary layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, which are sequentially deposited, and at least one layer of the layers comprises the arylamine naphthofuran compound according to claim 1.
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| CN114716329A (en) * | 2022-04-01 | 2022-07-08 | 上海钥熠电子科技有限公司 | Organic compound and organic photoelectric device |
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| CN114716329A (en) * | 2022-04-01 | 2022-07-08 | 上海钥熠电子科技有限公司 | Organic compound and organic photoelectric device |
| CN114685286A (en) * | 2022-04-19 | 2022-07-01 | 上海钥熠电子科技有限公司 | Triarylamine compound, organic electroluminescent device containing the same |
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