CN114507219A - Organic compound based on naphthalimide and application thereof - Google Patents
Organic compound based on naphthalimide and application thereof Download PDFInfo
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- CN114507219A CN114507219A CN202210247731.0A CN202210247731A CN114507219A CN 114507219 A CN114507219 A CN 114507219A CN 202210247731 A CN202210247731 A CN 202210247731A CN 114507219 A CN114507219 A CN 114507219A
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- substituted
- naphthalimide
- unsubstituted
- organic compound
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 34
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 239000000463 material Substances 0.000 claims abstract description 43
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 230000003111 delayed effect Effects 0.000 claims abstract description 7
- -1 diphenylacridinyl Chemical group 0.000 claims description 15
- 239000010410 layer Substances 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 7
- 239000012044 organic layer Substances 0.000 claims description 7
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 6
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 6
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 6
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 6
- 125000001725 pyrenyl group Chemical group 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 229910052805 deuterium Inorganic materials 0.000 claims description 4
- 125000004431 deuterium atom Chemical group 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000005561 phenanthryl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000004623 carbolinyl group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000005504 styryl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims 1
- 238000004020 luminiscence type Methods 0.000 abstract description 5
- 238000007725 thermal activation Methods 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 238000001514 detection method Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N deuterated chloroform Substances [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 239000005457 ice water Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000000967 suction filtration Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- WKBALTUBRZPIPZ-UHFFFAOYSA-N 2,6-di(propan-2-yl)aniline Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N WKBALTUBRZPIPZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000004537 pulping Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Substances BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
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- 238000006467 substitution reaction Methods 0.000 description 2
- 238000009210 therapy by ultrasound Methods 0.000 description 2
- YRIZYWQGELRKNT-UHFFFAOYSA-N 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione Chemical compound ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O YRIZYWQGELRKNT-UHFFFAOYSA-N 0.000 description 1
- MICMHFIQSAMEJG-UHFFFAOYSA-N 1-bromopyrrolidine-2,5-dione Chemical compound BrN1C(=O)CCC1=O.BrN1C(=O)CCC1=O MICMHFIQSAMEJG-UHFFFAOYSA-N 0.000 description 1
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 description 1
- 229910002548 FeFe Inorganic materials 0.000 description 1
- FSNCEEGOMTYXKY-JTQLQIEISA-N Lycoperodine 1 Natural products N1C2=CC=CC=C2C2=C1CN[C@H](C(=O)O)C2 FSNCEEGOMTYXKY-JTQLQIEISA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-PWCQTSIFSA-N Tritiated water Chemical compound [3H]O[3H] XLYOFNOQVPJJNP-PWCQTSIFSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical group OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
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- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000013461 design Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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Abstract
The organic compound based on the naphthalimide has good luminescence characteristics, so that an organic electroluminescent device using the organic compound based on the naphthalimide has lower driving voltage and higher luminescence efficiency, and the compound with the TADF luminescence characteristics can be used as a thermal activation delayed fluorescence luminescent material to realize high internal quantum efficiency.
Description
Technical Field
The invention belongs to the field of organic electroluminescent materials, and relates to a naphthalimide-based organic compound and application thereof.
Background
Organic Light Emitting Diodes (OLEDs) are considered to be the most promising display and lighting technology, and a typical OLED consists of a glass substrate, ITO, an anode, an organic light emitting layer, and a cathode, wherein a light emitting material is the most important factor determining the light emitting efficiency of the OLED. OLED emissive material development has so far gone through the fluorescent material phase, the phosphorescent material phase and the latest Thermally Activated Delayed Fluorescence phase (TADF). The first class of phosphors can only utilize 25% of singlet S1 excitons, which results in a significant loss of quantum efficiency during device operation. The second generation of phosphorescent materials can theoretically achieve 100% internal quantum efficiency by utilizing 75% of triplet energy. Compared with the first generation fluorescent material, the phosphorescent material has remarkable technical advantages, and is beneficial to reducing the electric power consumption of the device, reducing the heat generation, improving the stability of the device and prolonging the service life of the device. The defects in the United states are that heavy metals such as Ir are expensive, pollute the environment and are limited to store on the whole earth. In 2012, professor Adachi at kyusha university published in Nature reported a class of pure organic molecules with electron donor and acceptor planes connected perpendicularly, with very small triplet and singlet energy band gaps (Δ EST), such that 75% of the triplet state that is not available for small molecules to emit light is utilized, and electrons in the triplet state can efficiently cross back to the singlet state through reverse intersystem crossing, and transition from the singlet state back to the ground state and fluoresce. Since Δ EST, even if small, requires an external force to cross from triplet to singlet, which is heat, the whole process is called thermally activated delayed fluorescence TADF. Through the development of the last decade, the material structure of TADF has expanded, but at present such materials still need further development.
Therefore, in the art, the development of TADF materials with high performance is the focus of research.
Disclosure of Invention
In view of the shortcomings of the prior art, the invention aims to provide a naphthalimide-based organic compound and application thereof. The organic compound is used as an organic electroluminescent material for an OLED device, and can improve the performance of the device.
In order to achieve the purpose, the invention adopts the following technical scheme:
in one aspect, the present invention provides a naphthalimide-based organic compound having a structure represented by formula (1):
wherein: r1、R2、R3And R4Each independently represents a hydrogen atom, a deuterium atom, a cyano group, a nitro group, a fluorine atom, a chlorine atom, a bromine atom, an Ar or a D group; r1、R2、R3And R4At least two of which are selected from the group consisting of D groups;
the Ar groups are independently selected from substituted or unsubstituted C6-C20 (e.g., C6, C8, C10, C12, C15, C18, or C20) aryl groups;
the D group is independently selected from substituted or unsubstituted carbazolyl, substituted or unsubstituted acridinyl, substituted or unsubstituted dimethylazinyl, substituted or unsubstituted diphenylacridinyl, substituted or unsubstituted trianilino, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted disubstituted amino substituted with substituted or unsubstituted aromatic hydrocarbon group, or substituted aromatic hydrocarbon group;
R5selected from substituted or unsubstituted straight or branched alkyl groups, substituted or unsubstituted phenyl groups.
Preferably, in the naphthalimide-based organic compound according to the present invention, R is1And R4Both are selected from the group D, or R2And R3Both are selected from the group D, or R1、R2And R4Three are selected from the group D, or R1-R4Are all selected from the group D.
In the compound of the present invention having a structure represented by the formula (1), R1、R2、R3And R4At least two of which are selected from the group D, the introduction of such multiple donors having more sterically hindered groups D enabling the molecule to obtain a very small Delta ESTIt is beneficial to realize efficient intersystem crossing of excitons from T1 to S1 and high internal quantum efficiency. This is also the first consideration in the design of TADF organic materials that is currently generally recognized. If only unsubstituted amino groups are used for substitution or disubstituted amino groups which are not substituted by aromatic hydrocarbon groups are used as donors for bonding, the molecules can be used as fluorescent molecules due to lack of sufficient steric hindrance of the bond between the donor and the acceptor, but the TADF material is hardly possible.
In the present invention, the "aromatic hydrocarbon group" in the disubstituted amino group substituted with the substituted or unsubstituted aromatic hydrocarbon group is selected from: any one or combination of at least two of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, indenyl, pyrenyl and perylenyl.
In the present invention, the substituents in the substituted carbazolyl, substituted acridinyl, substituted dimethylazinyl, substituted diphenylacridinyl, substituted triphenylamine, substituted phenoxazinyl, substituted phenothiazinyl, substituted aromatic hydrocarbon are independently selected from the group consisting of: deuterium atom, cyano group, nitro group, fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, methoxy group, ethoxy group, propoxy group, vinyl group, allyl group, phenoxy group, tolyloxy group, benzyloxy group, phenethyloxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, pyrimidinyl group, triazinyl group, thienyl group, furyl group, pyrrolyl group, quinolyl group, isoquinolyl group, benzofuryl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalyl group, benzimidazolyl group, pyrazolyl group, dibenzofuryl group, phenoxazinyl group, phenothiazinyl group, carbolinyl group, acridinyl group, phenazinyl group, styryl group, Any one or a combination of at least two of naphthylvinyl, acetyl, benzoyl, dimethylamino, diethylamino, diphenylamino, dinaphthylamino, dibenzylamino, diphenylethylamino, dipyridylamino, dithienylamino or diallylamino.
In the present invention, the "aromatic hydrocarbon group" in the "substituted aromatic hydrocarbon group" is selected from: any one of phenyl, 2-methylphenyl, 2, 6-dimethylphenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, indenyl, pyrenyl and perylenyl.
Preferably, the Ar groups are independently selected from phenyl or naphthyl;
preferably, said R is5Selected from methyl, isopropyl, tert-butyl, cyclohexyl or phenyl substituted by at least one of fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, isopropyl, tert-butyl and cyano.
In the present invention, the phenyl group substituted by at least one of fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, isopropyl, tert-butyl and cyano means that the phenyl group may be mono-substituted or poly-substituted, and the substituent is selected from at least one of fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, isopropyl, tert-butyl and cyano.
Preferably, the organic compound based on naphthalimide is any one of the following compounds:
wherein Me is methyl, C4H9Is straight chain or branched C4An alkyl group.
The organic compounds based on naphthalimides according to the invention can be prepared by reference to the following reaction scheme:
synthetic route 1:
synthesis route 2:
synthesis route 3:
synthesis route 4:
synthesis pathway 5:
in another aspect, the present invention provides an organic electroluminescent material comprising the naphthalimide-based organic compound as described above.
In another aspect, the present invention provides a thermally activated delayed fluorescence emitting material including the naphthalimide-based organic compound as described above.
In another aspect, the present invention provides an organic electroluminescent device comprising the naphthalimide-based organic compound as described above.
Preferably, the organic electroluminescent device comprises an anode, a cathode and an organic layer between the anode and the cathode, the organic layer comprising the naphthalimide-based organic compound as described above.
Preferably, the organic layer includes a light-emitting layer containing the naphthalimide-based organic compound as described above.
In another aspect, the present invention provides a display panel comprising the naphthalimide-based organic compound as described above.
In the present invention, the display panel may be a screen or a display.
In the invention, the organic compound based on the naphthalimide has good light-emitting characteristics, so that an organic electroluminescent device using the organic compound has lower driving voltage and higher light-emitting efficiency, and further research shows that the molecules have the light-emitting characteristics of TADF. Through optimization of the electron donating capability and the number of donor groups of a molecule donor, TADF (TADF) characteristics of molecules can be further regulated, and a substituent group with certain steric hindrance is used in combination, so that the molecules obtain small delta EST, high-efficiency trans-system crossing of excitons from T1 to S1 can be realized, high internal quantum efficiency is realized, and further verification is also obtained in a subsequent OLED device. Meanwhile, series of compounds with maximum emission wavelengths in different color regions of a visible light region can be obtained, and the spectral coverage range of the compounds is very wide. It should be noted that we do not systematically optimize the device structure in the device test, and the values of various data also adopt a relatively harsh condition, so that the device results still have room for further improvement.
Compared with the prior art, the invention has the following beneficial effects:
the organic compound of the invention has good luminescence property, so that an organic electroluminescent device using the organic compound has lower driving voltage, higher luminous efficiency and better device service life, and the compound with TADF luminescence property can be used as a thermal activation delayed fluorescence luminescent material to realize high internal quantum efficiency.
Drawings
Fig. 1 is a single crystal diffractogram of primary intermediate M6.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Synthetic examples
Intermediate synthesis
1, 8-naphthalic anhydride (4.00g, 20.0mmol) was dissolved in concentrated sulfuric acid (20.0mL), N-bromosuccinimide NBS (7.83g, 44.0mmol) was added, and the mixture was reacted at 60 ℃ for 10 hours. After the reaction was completed, the reaction solution was cooled to room temperature, poured into ice water, filtered with suction, dried, and recrystallized from N, N-dimethylformamide to obtain white intermediate product M1(1.5g, yield 20%).
M1(3.5g, 10.0mmol) was suspended in a mixed solution of acetic acid and N-methylpyrrolidone (NMP) (1: 1, 20mL), 2, 6-diisopropylaniline (4.43g,25.0mL) was added, and the mixture was reacted at 150 ℃ for 3 hours under nitrogen. After the reaction was completed, the reaction solution was cooled to room temperature, poured into ice water, filtered with suction, dried, and subjected to column chromatography to obtain M2(4.0g, 78%) as a white solid. C24H21Br2NO 2HR-MS detection value: 512.9959, respectively; calculated values: 512.9939.1H NMR(500MHz,CDCl3in ppm, δ is 8.68(s,2H),8.33(s,2H),7.50(t, J is 7.8Hz,1H),7.33(d, J is 7.8Hz,2H),2.63(hept, J is 6.8Hz,2H),1.15(d, J is 6.9Hz,12H) (ref synthesis: anion-reactive π -Electronic Systems inhibiting conversion formulations and stoichimetric in inhibition Binding, Yohei Haketa, Atsushi Nagnawa, Shinya Sugiura, Nobuhiro Yasuda, Hiromitsu Maeda, European Journal of Organic Chemistry 2020,23, 3491).
1, 8-naphthalic anhydride (50mmol, 13.85g), NBS (160mmol, 28.48g) was added to 100mL of concentrated sulfuric acid and stirred at 60 ℃ overnight. After the reaction, the mixture was poured into 2L of ice-water mixture to precipitate a solid, which was then filtered off with suction and washed with water. The chlorobenzene is pulped once to obtain a target intermediate M3 for later use.
M3(50mmol, 21.75g) and 2, 6-diethylaniline (100mmol, 14.90g) were added to 150mL of NMP and 150mL of acetic acid and stirred at 150 ℃ under reflux for 3 h. After the reaction is finished, pouring the mixture into water, performing suction filtration, and washing the mixture with ethanol until the filtrate is colorless. Pulping with ethyl acetate. Column chromatography gave about 6.30g of the desired product M4, with a combined yield of about 25% in the two-step reaction (cf. synthetic references: Dioxin-isolated 1,8-naphthalimides-Synthesis, spectral and electrochemical properties, and application in OLED, Yulian Zagranyarski, Monika Mutovska, Petia Petrova, Reni Tomova, Petar Ivanov, Stanimir Stoyanov, Dyes and Pigments,2021,184,108585).
M4(11mmol, 6.30g) and potassium iodide (55mmol, 3.19g) were added to 120mL of DMF and stirred at 130 ℃ for 24 h. After the reaction is finished, the temperature is reduced to room temperature and the mixture is poured into 500mL of ethanol/water mixture, the mixture is stirred and filtered, and a filter cake is washed by proper amount of water and ethanol to obtain crude intermediate M5.
The crude M5, carbazole (16mmol), potassium carbonate (66mmol,9.11g), and potassium iodide (9mmol,1.49g) were added to 40mL of DMF, and the reaction was stirred at 85 ℃ for 2 hours. After the reaction is finished, pouring a large amount of ice water, performing suction filtration, washing and drying. Pulping with ethanol, and recrystallizing with toluene. About 2.7g of brown target product M6 was obtained in a combined yield of about 50% in two steps.
C34H24Br2N2O 2HR-MS detection value: 650.0220, respectively; calculated values: 650.0205.1H NMR(500MHz,DMSO-d6)δ8.88(s,1H),8.62(s,1H),8.37(d,J＝7.6Hz,2H),7.52(s,1H),7.43(td,J＝14.9,14.5,7.3Hz,4H),7.38(d,J＝7.3Hz,1H),7.33(d,J＝7.6Hz,2H),7.04(s,2H),2.44(q,J＝7.5Hz,4H),1.09(t,J＝7.6Hz,6H).
the single crystal of the main intermediate M6 was obtained by the method of mixed solvent evaporation, and the single crystal diffraction pattern thereof is shown in fig. 1, from which it can be seen that the structure of the intermediate 6 is consistent with our judgment. When the F-Br exchange reaction is carried out, the bromine atom at peri site of naphthalene ring is more active, while the bromine atom at meso site does not participate in the reaction.
1, 8-naphthalic anhydride (50mmol, 10.00g), NBS (300mmol, 53.40g) was added to 200mL of concentrated sulfuric acid and stirred at room temperature overnight. After the reaction, the mixture was poured into 3L of ice-water mixture to precipitate a yellow solid, which was then filtered off with suction and washed with water. The chlorobenzene was beaten once to give about 19g of the target product M7 in a grey green color with a yield of about 75%.
Compound M7(10mmol, 5.14g) and 2, 6-diisopropylaniline (20mmol,3.54g) were added to 30mL of NMP and 30mL of AcOH and stirred at 150 ℃ under reflux for 2 h. After the reaction is finished, pouring the mixture into water, performing suction filtration, and washing the mixture with ethanol until the filtrate is colorless. Column chromatography can obtain about 3.40g of target product M8 with a yield of about 50% (refer to synthetic literature: [ FeFe ]]-Hydrogenase H-cluster mimics mediated by naphthalene monoimide derivatives of peri-substituted dichalcogenides,Hassan Abul-Futouh,Yulian Zagranyarski,Carolin Mü ller,Martin Schulz,Stephan Kupfer,Helmar 
Mohammad El-khateeb,Stefanie 
Benjamin Dietzek,Kalina Peneva,Wolfgang Weigand,Dalton Transactions,2017,46(34),11180)。
Compound M8(5mmol, 3.37g) and cesium fluoride (33mmol,5.02g) were added to 70mL of DMF and stirred at 85 ℃ for 2 h. After the reaction, the temperature was reduced to room temperature. And (3) enabling the reaction solution to pass through a rapid column, and performing rotary evaporation and concentration to obtain a viscous liquid with the target product M9 for later use.
The above viscous liquid with compound M9, carbazole (15mmol), potassium carbonate (30mmol,4.14g), and potassium iodide (4.50mmol,0.75g) were added to 20mL of DMF, and the reaction was stirred at 85 ℃ for 2 hours. After the reaction is finished, pouring a large amount of ice water, performing suction filtration, washing and drying. Pulping with ethanol, and recrystallizing with toluene. About 2g of brown target product M10 was obtained in a combined yield of about 50% in two steps. C48H35Br2N3O2HR-MS detection value: 843.1105; calculated values are: 843.1096.1H NMR(500MHz,DMSO-d6)δ8.90(s,2H),8.23(d,J＝7.7Hz,4H),7.53(t,J＝7.8Hz,1H),7.30(d,J＝7.8Hz,2H),6.97–6.88(m,4H),6.83(d,J＝9.5Hz,8H),2.44(q,J＝7.5Hz,4H),1.09(t,J＝7.6Hz,6H).
naphthalenetetracarboxylic anhydride (263mmol, 80g) was added to 120mL of water and stirred. A22% NaOH solution (1086mmol, 160mL) was added. After stirring for 30min, acetic acid (105mmol, 6mL) was slowly added dropwise. After stirring for 30min, liquid bromine (626mmol, 100g) was slowly added dropwise over 4-6 h, with attention paid to the reaction temperature and pressure. After the addition was complete, the reaction was allowed to proceed overnight. The next day of reaction, the system was warmed to 70 ℃ and stirred for 2 hours. When the temperature of the system is reduced to less than 45 ℃, precooled concentrated sulfuric acid (60mL) is slowly dripped, and the mixture is stirred for 1 hour. The temperature of the system is raised to 70 ℃ and the mixture is stirred for 2 hours. After the reaction, the temperature was reduced to room temperature. The reaction mixture was filtered, washed with water and dried to obtain about 100g of the desired product M11.
M11(42mmol,15g) was added to 400mL ethanol and heated at 85 ℃ under reflux for 1 h. 400mL of an ethanol solution of n-butylamine (50mmol,3.65g) was slowly added dropwise thereto. Stir overnight. Suction filtration and washing with ethanol until the filtrate is colorless can obtain about 9.88g of target product M12 in light yellow with about 55% yield.
Compound M12(20mmol,9.50g) and potassium iodide (130mmol,7.54g) were added to 180mL of DMSO and refluxed at 130 ℃ overnight. After the reaction, the temperature was reduced to room temperature. Pouring into a large amount of water to separate out solid. And (5) carrying out suction filtration and washing. Column chromatography gave the desired product M13 in about 1.16g, yield about 20%. C16H13F2NO2HR-MS detection value: 289.0928, respectively; calculated values:289.0914。1H NMR(500MHz,CDCl3,in ppm, 8.63(d,2H, J ═ 8.4Hz), 7.45-7.28 (m,2H), 874.16 (t,2H, J ═ 7.6Hz), 1.72-1.68 (m,2H), 1.25-1.46 (m,2H),0.97-0.88(t,3H, J ═ 7.2Hz) (see synthetic references: Jie Huang, Di Wu, Hao-Jie Ge, Sheng-Hua Liu, Jun Yin, Fluorinated1,8-naphthalimides: Synthesis, solid structures and properties, Chinese Chemical Letters 2014,25, 1399).
1, 8-naphthalic anhydride (40mmol, 7.93g) and TCCA (60mmol, 13.95g) trichloroisocyanate were added to 200mL of concentrated sulfuric acid and reacted at 150 ℃ for 2 hours. After the reaction, the mixture was poured into 1L of ice-water mixture to precipitate a gray solid, which was filtered off with suction and washed with water. The chlorobenzene was beaten once to give about 12g of the target product M13 in a grayish green color with a yield of about 90%.
Compound M13(10mmol,5.14g) and 2, 6-diisopropylaniline (20mmol,3.54g) were added to 30mL of NMP and 30mL of AcOH and stirred at 150 ℃ under reflux for 2 h. After the reaction is finished, pouring the mixture into water, performing suction filtration, and washing the mixture with ethanol until the filtrate is colorless. Column chromatography gave about 5.45g of the desired product M14 in about 81% yield (ref: Dalton Transactions, 2017,46(34), 11180).
Compound M14(5mmol,3.37g) and cesium fluoride (33mmol,5.02g) were added to 70mL of DMF and stirred at 80 ℃ for 2 h. After the reaction, the temperature was reduced to room temperature. And (3) enabling the reaction solution to pass through a rapid column, and performing rotary evaporation and concentration to obtain a solid with the target product M15 for later use. C24H19Cl2F2NO 2HR-MS detection: 461.0766, respectively; calculated values: 461.0761.1H NMR(500MHz,CDCl3,ppm):δ＝8.70(s,2H),7.53(t,J＝7.8Hz,1H),7.30(d,J＝7.8Hz,2H),2.60(hept,J＝6.8Hz,2H),1.15(d,J＝6.9Hz,12H).
compound Synthesis example 1
Starting material M2(510mg,1.0mmol), cesium carbonate (1.625g,5mmol)N-phenyl-3-carbazolboronic acid (631mg,2.2mmol) and palladium acetate (10mg,0.005mmol) were dissolved in toluene (20mL) and reacted at 120 ℃ for 8 hours under nitrogen. After the reaction was complete, it was cooled to room temperature, extracted with ethyl acetate, and column chromatographed to give product P1(610mg, 72%). C60H45N3O 2HR-MS detection value: 839.3588, respectively; calculated values: 839.3512.1H NMR(500MHz,CDCl3)δ:9.09(s,2H),8.70(s,2H),8.66(s,2H),8.32(d,J＝5Hz,2H),7.93((d,J＝5Hz,2H)),7.70-7.65(m,10H),7.60(s,1H),7.58(s,1H),7.55(t,J＝5Hz 3H),7.49(s,3H),7.41(s,1H),7.40(m,2H),2.93-2.85(m,2H),1.28-1.20(m,12H)。
compound Synthesis example 2
The starting material M2(510mg,1.0mmol), cesium carbonate (1.625g,5mmol), carbazole (501mg,3mmol), 2-dicyclohexylphosphonium-2 ',4',6' -triisopropylbiphenyl (47mg, 0.01mmol), palladium acetate (10mg,0.005mmol) were dissolved in toluene (20mL) and reacted at 120 ℃ for 24 hours under nitrogen. After the reaction was complete, it was cooled to room temperature, extracted with ethyl acetate, and column chromatographed to give product P2(360mg, 52%). C48H37N3O 2HR-MS detection value: 687.2930, respectively; calculated values: 687.2886.1H NMR(500MHz,Chloroform-d)δ8.98(d,J＝2.0Hz,2H),8.56(d,J＝2.0Hz,2H),8.23(d,J＝7.7Hz,4H),7.58(s,4H),7.53(d,J＝7.1Hz,4H),7.50(s,1H),7.40(t,J＝7.5Hz,6H),2.95-2.86(m,J＝6.8Hz,2H),1.36-1.22(m,J＝6.8Hz,12H).
compound Synthesis example 3
Compound M13(1mmol, 289mg), carbazole (3mmol), potassium carbonate (6mmol, 828mg), potassium iodide was added a little to 10mL DMSO, and stirred at 150 ℃ for 2 h. After the reaction, the temperature was reduced to room temperature. Pouring into a large amount of water, filtering, and washing. And performing column chromatography and toluene recrystallization to obtain a target product P3. C40H29N3O 2HR-MS detection value: 583.2250, respectively; calculated values: 583.2260。1H NMR(500MHz,DMSO-d6)δ8.82(s,2H),7.94(dd,J＝7.8,2.6Hz,2H),7.56(s,4H),6.97–6.88(m,4H),6.83(d,J＝9.5Hz,8H),4.24–4.14(m,2H),1.75(t,J＝7.8Hz,2H),1.46(q,J＝7.9Hz,2H),1.24(s,2H),1.01(t,J＝7.4Hz,3H)。
The other compounds were synthesized as in synthesis example 1, synthesis example 2 or synthesis example 3, except that N-phenyl-3-carbazole boronic acid or carbazole was replaced with other corresponding raw materials, as shown in table 1 below:
TABLE 1
The HR-MS (WATER, XEVO G2-XS Qtof) is adopted to carry out structural identification analysis on the material, and the characterization data of the compounds P4-P19 of each synthetic example are shown in the following table 2:
TABLE 2
As in the above table, the structure of the compounds is as follows:
as can be seen from the data in the above tables, the compounds shown in the synthesis examples have been successfully obtained in the present invention.
The compound of the invention can be used as a luminescent layer material, and the compound P1-P18 of the invention is carried out in a toluene dilute solution (10)-6mol/L) fluorescence maximum emission spectrum detection (by Bruker, S2 Puma instrument), the results are shown in Table 3.
TABLE 3
As can be seen from the data in the table above, by adjusting the electron donating ability and the number of donors of the parent nucleus, the maximum emission wavelength of the obtained series of compounds can be located in different color regions of a visible light region, and the spectrum coverage range is very wide.
Device example 1
The organic electroluminescent device adopts the following structure:
ITO/Hole Injection Layer (HIL)/Hole Transport Layer (HTL)/organic emission layer (EML)/Electron Transport Layer (ETL)/electron injection layer (EIL/LiF)/cathode (Al).
The preparation method of the device comprises the following steps:
substrate cleaning:
the ITO-coated transparent motor substrate is subjected to ultrasonic treatment in a commercial cleaning agent, washed in deionized water, and subjected to ultrasonic treatment in acetone: ultrasonic degreasing is carried out in an ethanol mixed solvent (volume ratio is 1: 1), baking is carried out in a clean environment until water is completely removed, and then ultraviolet light and ozone are used for cleaning.
Preparation of an organic layer:
transferring the ITO transparent substrate into an evaporation device, and evaporating a 5nm HIL layer, a 60nm HTL layer, a 40nm EML layer, a 40nm ETL layer, a 0.5nm EIL layer and 100nm aluminum in sequence as a cathode, wherein the EML layer is composed of three materials of host, D1(P3) and D2 in a ratio of 80:20: 1.
The materials involved in the device are as follows:
device example 2
This embodiment differs from device embodiment 1 in that: the D1(P3) material of the electroluminescent device was replaced by the compound P8 according to the invention. The Host and P8 materials were composed in a ratio of 80: 20.
Device example 3
This embodiment differs from device embodiment 1 in that: the D1(P3) material of the electroluminescent device was replaced by the compound P6 of the invention. The Host and P6 materials were composed in a ratio of 80: 20.
Device example 4
This embodiment differs from device embodiment 1 in that: the D1(P3) and D2 materials of the electroluminescent device were replaced with the compound P9 of the invention. The Host and P9 materials were composed in a ratio of 80: 20.
Device example 5
This embodiment differs from device embodiment 1 in that: the D1(P3) and D2 materials of the electroluminescent device were replaced with the compound P13 of the invention. The Host and P13 materials were composed in a ratio of 80: 20.
Device example 6
This embodiment differs from device embodiment 1 in that: the D1(P3) and D2 materials of the electroluminescent device were replaced with the compound P14 of the invention. The Host and P14 materials were composed in a ratio of 80: 20.
Device example 7
This embodiment differs from device embodiment 1 in that: the D1(P3) and D2 materials of the electroluminescent device were replaced with the compound P5 of the invention. The Host and P5 materials were composed in a ratio of 80: 20.
Comparative example 1
This comparative example differs from device example 1 in that: the D1(P3) and D2 materials of the electroluminescent devices were replaced by the compound R1 shown below (ref: Achieving New 30% External Quantum Efficiency for Orange-Red Organic Light Emitting Diodes Emitting thermoplastic active Delayered fluorescent Emitters Compound of1, 8-sodium-Acridine hybrids Weiixutan Zeng, Hsin-Yu Lai, Wei-Kai Lee, Min Jiano, Yi-Jiun Shiu, Cheng Zhong, Shaolong Gong, Tao Zhou, Guohua Xie, unima rma, Ken-ung, Chung-Chung Yah Woo, Woo 17061, Tsuv mount Woo, Tsuv mount). The two materials Host and R1 were composed in a ratio of 80: 20.
Comparative example 2
This comparative example differs from device example 1 in that: the electroluminescent device was replaced by the compounds R2.host and R1, shown below, with the materials D1(P3) and D2 being composed in a ratio of 80: 20.
The devices were tested for performance and incompletely optimized OLED devices were characterized using standard methods and measuring electroluminescence spectra. Calculating the external quantum efficiency EQE depending on the intensity according to the light and current detected by the photodiode, wherein the value is that the current density is 10mA/cm2Under the conditions. Similarly, the current efficiency CE and the voltage were also set at a current density of 10mA/cm2The measurement and calculation were carried out under the conditions of (1). LT (J50) value corresponds to a current density of 50mA/cm2The time required for the measured luminance to decrease to 95% of the initial luminance. The EL peak reading is similar to the method of maximum fluorescence spectrum in solution. The test results are shown in table 4.
TABLE 4
From the performances of the device embodiments, compared with comparative example 1, the doped material designed by the patent can show certain luminous efficiency (the current efficiency is more than 1.19cd/A, the external quantum efficiency EQE is more than 1.26%), lower voltage (less than 4.85V) and obviously improved device life (more than 1 h). Considering that comparative example 1 is a TADF material with excellent performance reported in the literature (refer to the 24-page reference), the performance of the newly designed molecule under the same test conditions can be close to that of comparative example 1, and more importantly, the lifetime is greatly improved, which is very helpful for potential applications. The device results show an overall improvement in voltage, current efficiency, EQE and lifetime parameters using the doped materials of the present invention compared to comparative example 2. Since the phenyl group attached to the naphthalene ring in comparative example 2 does not belong to the donor group, it is largely demonstrated that the molecules designed in this invention with at least two donors do help to improve the performance.
The applicant states that the present invention is illustrated by the above examples of the organic compounds of the present invention and their applications, but the present invention is not limited to the above examples, i.e. it is not meant that the present invention must rely on the above examples to be practiced. It will be apparent to those skilled in the art that any modification of the present invention, equivalent substitutions of selected materials and additions of auxiliary components, selection of specific modes and the like, which are within the scope and disclosure of the present invention, are contemplated by the present invention.
Claims (10)
1. An organic compound based on naphthalimide, characterized in that it has the structure shown in formula (1):
wherein: r1、R2、R3And R4Each independently represents a hydrogen atom, a deuterium atom, a cyano group, a nitro group, a fluorine atom, a chlorine atom, a bromine atom, an Ar group or a D group; r1、R2、R3And R4At least two of which are selected from the group consisting of D groups;
ar groups are independently selected from substituted or unsubstituted C6-C20 aryl;
the D group is independently selected from substituted or unsubstituted carbazolyl, substituted or unsubstituted acridinyl, substituted or unsubstituted dimethylazinyl, substituted or unsubstituted diphenylacridinyl, substituted or unsubstituted trianilino, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted disubstituted amino substituted with substituted or unsubstituted aromatic hydrocarbon group, or substituted aromatic hydrocarbon group;
R5selected from substituted or unsubstituted straight or branched alkyl groups, substituted or unsubstituted phenyl groups.
2. The naphthalimide-based organic compound according to claim 1, wherein R is1And R4Both are selected from the group D, or R2And R3Both are selected from the group D, or R1、R2And R4Three are selected from the group D, or R1-R4Are all selected from D groups;
preferably, the aromatic hydrocarbon group in the disubstituted amino group substituted by the substituted or unsubstituted aromatic hydrocarbon group is selected from: any one or combination of at least two of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, indenyl, pyrenyl and perylenyl.
3. The naphthalimide-based organic compound according to claim 1 or 2, wherein the substituents in the substituted carbazolyl, substituted acridinyl, substituted dimethylazinyl, substituted diphenylacridinyl, substituted triphenylamine, substituted phenoxazinyl, substituted phenothiazinyl, substituted aromatic hydrocarbon are independently selected from the group consisting of: deuterium atom, cyano group, nitro group, fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, methoxy group, ethoxy group, propoxy group, vinyl group, allyl group, phenoxy group, tolyloxy group, benzyloxy group, phenethyloxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, pyrimidinyl group, triazinyl group, thienyl group, furyl group, pyrrolyl group, quinolyl group, isoquinolyl group, benzofuryl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalyl group, benzimidazolyl group, pyrazolyl group, dibenzofuryl group, phenoxazinyl group, phenothiazinyl group, carbolinyl group, acridinyl group, phenazinyl group, styryl group, Any one or a combination of at least two of naphthylvinyl, acetyl, benzoyl, dimethylamino, diethylamino, diphenylamino, dinaphthylamino, dibenzylamino, diphenylethylamino, dipyridylamino, dithienylamino or diallylamino.
4. The naphthalimide-based organic compound according to any of claims 1 to 3, wherein the aromatic hydrocarbon groups of the substituted aromatic hydrocarbon groups are selected from: any one of phenyl, 2-methylphenyl, 2, 6-dimethylphenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, indenyl, pyrenyl or perylenyl;
preferably, the Ar groups are independently selected from phenyl or naphthyl;
preferably, said R is5Selected from methyl, isopropyl, tert-butyl, cyclohexyl or phenyl substituted by at least one of fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, isopropyl, tert-butyl and cyano.
5. The naphthalimide-based organic compound according to any of claims 1 to 4, wherein the naphthalimide-based organic compound is any one of the following compounds:
wherein Me is methyl.
6. An organic electroluminescent material comprising the naphthalimide-based organic compound according to any one of claims 1 to 5.
7. A thermally activated delayed fluorescence luminescent material, wherein the thermally activated delayed fluorescence luminescent material comprises the naphthalimide-based organic compound according to any one of claims 1 to 5.
8. An organic electroluminescent device characterized in that it comprises the naphthalimide-based organic compound according to any one of claims 1 to 5.
9. The organic electroluminescent device according to claim 8, characterized in that it comprises an anode, a cathode and an organic layer between the anode and the cathode, the organic layer comprising a naphthalimide-based organic compound according to any one of claims 1 to 5;
preferably, the organic layer includes a light-emitting layer containing the naphthalimide-based organic compound according to any one of claims 1 to 5.
10. A display panel comprising the naphthalimide-based organic compound according to any one of claims 1 to 5.
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