CN109651312A - One kind containing pyrene compound and organic light emitting diode device - Google Patents
One kind containing pyrene compound and organic light emitting diode device Download PDFInfo
- Publication number
- CN109651312A CN109651312A CN201811650063.6A CN201811650063A CN109651312A CN 109651312 A CN109651312 A CN 109651312A CN 201811650063 A CN201811650063 A CN 201811650063A CN 109651312 A CN109651312 A CN 109651312A
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- Prior art keywords
- substituted
- unsubstituted
- phenyl
- fluorine
- aryl
- Prior art date
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- -1 pyrene compound Chemical class 0.000 title claims abstract description 69
- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 title claims abstract description 51
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 229910052731 fluorine Inorganic materials 0.000 claims description 67
- 239000011737 fluorine Chemical group 0.000 claims description 67
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 41
- 229910052710 silicon Inorganic materials 0.000 claims description 39
- 239000010703 silicon Substances 0.000 claims description 39
- 229910052805 deuterium Inorganic materials 0.000 claims description 36
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 32
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 30
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 30
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 17
- 125000003944 tolyl group Chemical group 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 claims description 14
- 238000006467 substitution reaction Methods 0.000 claims description 14
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 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 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 150000004982 aromatic amines Chemical class 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 102100031807 F-box DNA helicase 1 Human genes 0.000 claims description 6
- 101001065291 Homo sapiens F-box DNA helicase 1 Proteins 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- MUEHGEQAMLEEID-UHFFFAOYSA-N 1-pentyl-2-phenylbenzene Chemical group CCCCCC1=CC=CC=C1C1=CC=CC=C1 MUEHGEQAMLEEID-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 claims description 3
- OKHRPUBUEJQKIG-UHFFFAOYSA-N 1-hexyl-2-phenylbenzene Chemical group CCCCCCC1=CC=CC=C1C1=CC=CC=C1 OKHRPUBUEJQKIG-UHFFFAOYSA-N 0.000 claims description 3
- ALLIZEAXNXSFGD-UHFFFAOYSA-N 1-methyl-2-phenylbenzene Chemical group CC1=CC=CC=C1C1=CC=CC=C1 ALLIZEAXNXSFGD-UHFFFAOYSA-N 0.000 claims description 3
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000005581 pyrene group Chemical group 0.000 claims description 3
- KXFSUVJPEQYUGN-UHFFFAOYSA-N trimethyl(phenyl)silane Chemical compound C[Si](C)(C)C1=CC=CC=C1 KXFSUVJPEQYUGN-UHFFFAOYSA-N 0.000 claims description 3
- BZLZKLMROPIZSR-UHFFFAOYSA-N triphenylsilicon Chemical compound C1=CC=CC=C1[Si](C=1C=CC=CC=1)C1=CC=CC=C1 BZLZKLMROPIZSR-UHFFFAOYSA-N 0.000 claims description 3
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 claims 2
- HKTCLPBBJDIBGF-UHFFFAOYSA-N 1-phenyl-2-propan-2-ylbenzene Chemical group CC(C)C1=CC=CC=C1C1=CC=CC=C1 HKTCLPBBJDIBGF-UHFFFAOYSA-N 0.000 claims 1
- DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 claims 1
- XDLDASNSMGOEMX-UHFFFAOYSA-N benzene benzene Chemical compound C1=CC=CC=C1.C1=CC=CC=C1 XDLDASNSMGOEMX-UHFFFAOYSA-N 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 27
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 abstract description 6
- 125000001725 pyrenyl group Chemical group 0.000 abstract description 6
- 125000001624 naphthyl group Chemical group 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
- 239000010410 layer Substances 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 238000000034 method Methods 0.000 description 17
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 14
- 238000004770 highest occupied molecular orbital Methods 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 9
- 238000006392 deoxygenation reaction Methods 0.000 description 8
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000010792 warming Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000011574 phosphorus Substances 0.000 description 6
- 238000004321 preservation Methods 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 230000008859 change Effects 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002484 cyclic voltammetry Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000691 measurement method Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 230000027756 respiratory electron transport chain Effects 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- JRCJYPMNBNNCFE-UHFFFAOYSA-N 1,6-dibromopyrene Chemical compound C1=C2C(Br)=CC=C(C=C3)C2=C2C3=C(Br)C=CC2=C1 JRCJYPMNBNNCFE-UHFFFAOYSA-N 0.000 description 2
- DLMYHUARHITGIJ-UHFFFAOYSA-N 1-ethyl-2-phenylbenzene Chemical group CCC1=CC=CC=C1C1=CC=CC=C1 DLMYHUARHITGIJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000003775 Density Functional Theory Methods 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 2
- BWHOZHOGCMHOBV-UHFFFAOYSA-N benzylideneacetone Chemical class CC(=O)C=CC1=CC=CC=C1 BWHOZHOGCMHOBV-UHFFFAOYSA-N 0.000 description 2
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001903 differential pulse voltammetry Methods 0.000 description 2
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000000103 photoluminescence spectrum Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000004402 ultra-violet photoelectron spectroscopy Methods 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- VOZBMWWMIQGZGM-UHFFFAOYSA-N 2-[4-(9,10-dinaphthalen-2-ylanthracen-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=C(C=2C=C3C(C=4C=C5C=CC=CC5=CC=4)=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C3=CC=2)C=C1 VOZBMWWMIQGZGM-UHFFFAOYSA-N 0.000 description 1
- XSUNFLLNZQIJJG-UHFFFAOYSA-N 2-n-naphthalen-2-yl-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical class C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C=C2C=CC=CC2=CC=1)C1=CC=CC=C1 XSUNFLLNZQIJJG-UHFFFAOYSA-N 0.000 description 1
- 238000004057 DFT-B3LYP calculation Methods 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000003679 aging effect Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000037429 base substitution Effects 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005090 crystal field Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 125000005241 heteroarylamino group Chemical group 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- NCWQJOGVLLNWEO-UHFFFAOYSA-N methylsilicon Chemical compound [Si]C NCWQJOGVLLNWEO-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 238000012946 outsourcing Methods 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 239000002096 quantum dot Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005406 washing Methods 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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Abstract
One kind containing pyrene compound and organic light emitting diode device.The invention belongs to field of organic electroluminescent materials, disclose a kind of containing pyrene compound and its application.Remarkable advantage provided by the present invention containing pyrene compound is: pyrenyl contained by molecular center is luminophore, contain benzofuran and naphthalene structure in the outside of the luminophore, this kind of outer pendant groups have very big rigidity, so that the luminous pyrenyl group of molecular center is by external influence very little, to ensure that the pyrene compound provided by the present invention that contains has preferable luminous efficiency, while significantly improving the luminescent lifetime of device.
Description
Technical field
The invention belongs to field of organic electroluminescent materials, in particular to a kind of to contain pyrene compound and Organic Light Emitting Diode
Device.
Background technique
Various organic electronic devices are prepared using organic material, it is such as common especially for the function element of photoelectric respone
Organic electroluminescence device, organic solar batteries device, organic field effect tube device and organic photosensitive sensor device
Part is increasingly valued by people.
For organic electronic light emitting device, the technical issues of facing be how and meanwhile realize high-luminous-efficiency, low drive
Dynamic voltage and long life.For high efficiency light-emitting device, if common mode can be by adulterating in material of main part
Dry guest materials forms luminescent layer.For material of main part, it is desirable that high carrier mobility, uniform film forming etc.；For object
Material, it is desirable that high fluorescence quantum efficiency and with dispersibility good in material of main part etc..For the photophore of low driving voltage
Part, can be by introducing dopant in hole transmission layer or electron transfer layer.However, the luminescent device heavy dependence of long-life is steady
Qualitative high luminescent material, thus it is very urgent for the demand of the luminescent material of high stability energy in this field.
Using different luminous organic materials and combinations thereof, the light of a variety of different colours can be obtained.In red, green and
In these three blue primary colors luminescent materials, blue emitting material is by especially more attention.Existing blue fluorescent material is usual
It is the aromatic amine material of parent nucleus with pyrene, anthracene or fluorenes.Wherein, the aromatic amine compound of pyrene series is easily obtained higher luminous effect
Rate is particularly subject to attention in the industry.Long-life efficient luminophor containing pyrene needs further to be developed.
Summary of the invention
It is an object of the invention to a kind of containing pyrene compound and organic light emitting diode device to overcome above-mentioned deficiency to provide.
The purpose of the present invention is achieved through the following technical solutions:
Embodiments of the present invention provide one kind containing pyrene compound, with structure shown in formula (I):
Wherein, R1-R10It each independently represents hydrogen, deuterium, fluorine, chlorine, bromine, iodine, substituted or unsubstituted C1-C24 alkyl, take
Generation or unsubstituted C6-C36 aryl, substituted or unsubstituted C3-C36 heteroaryl, substituted or unsubstituted C1-C24 alkoxy,
Substituted or unsubstituted C6-C36 aryloxy group, substituted or unsubstituted C3-C36 heteroaryloxy, substituted or unsubstituted C2-C24
Alkylamino radical, substituted or unsubstituted C7-C36 aryl amine, substituted or unsubstituted C4-C36 heteroaryl amido, and R1-R10In extremely
Few one has structure shown in formula (II):
* indicate that formula (II) is connect by the position with the pyrene residue in structure shown in formula (I)；Ap, Aq table each independently
Show substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C3-C36 heteroaryl
Base, and at least one of Ap, Aq have structure shown in formula (III):
Nitrogen-atoms in formula (II) is connected with 10 carbon atoms in formula (III)；Hydrogen atom in formula (III) is unsubstituted
Or each independently by deuterium, fluorine, the alkyl of substituted or unsubstituted C1-C12, substituted or unsubstituted C6-C24 aryl, substitution
Or one or more substitutions in unsubstituted C3-C24 heteroaryl.
Optionally, in structure containing pyrene compound provided by embodiments of the present invention, the substituted or unsubstituted C1-
It is C24 alkyl, substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C3-C36 heteroaryl, substituted or unsubstituted
C1-C24 alkoxy, substituted or unsubstituted C6-C36 aryloxy group, substituted or unsubstituted C3-C36 heteroaryloxy, replace or
Unsubstituted C2-C24 alkylamino radical, substituted or unsubstituted C7-C36 aryl amine, substituted or unsubstituted C4-C36 heteroaryl amido,
The alkyl of substituted or unsubstituted C1-C12, substituted or unsubstituted C6-C24 aryl, substituted or unsubstituted C3-C24 heteroaryl
Substitution in base refers to: replacing alkyl, deuterium to replace alkane by deuterium, fluorine, alkyl, alkoxy, aryl, heteroaryl, fluorine each independently
Base, silicon replace alkyl, fluorine substituted alkoxy, deuterium substituted alkoxy, silicon substituted alkoxy, fluorine substituted aryl, deuterium substituted aryl, silicon
One of substituted aryl, fluorine substituted heteroaryl, deuterium substituted heteroaryl or silicon substituted heteroaryl replace.
Optionally, pyrene compound is contained provided by embodiments of the present invention, have formula (Ia), (Ib), (Ic), (Id),
(Ie), structure shown in (If) or (Ig):
Wherein, R1-R10Each independently represent hydrogen, deuterium, substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted
C6-C36 aryl, substituted or unsubstituted C3-C36 heteroaryl；Ar1-Ar8Each independently represent substituted or unsubstituted C1-
C24 alkyl, substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C3-C36 heteroaryl, and Ar1-Ar8In at least
One has structure shown in formula (III):
10 carbon originals in nitrogen-atoms and formula (III) in formula (Ia), (Ib), (Ic), (Id), (Ie), (If) or (Ig)
Son is connected；Hydrogen atom in formula (III) it is unsubstituted or each independently by deuterium, fluorine, substituted or unsubstituted C1-C12 alkane
Base, substituted or unsubstituted C6-C24 aryl, one or more in substituted or unsubstituted C3-C24 heteroaryl replace.
Optionally, in structure containing pyrene compound provided by embodiments of the present invention, R1-R10Each independently represent first
Base, ethyl, propyl, butyl, amyl, hexyl, fluorine substituent methyl, fluorine replace ethyl, fluorine substituted propyl, fluorine that butyl, fluorine is replaced to take
Replace hexyl, phenyl, tolyl, ethylbenzene, propyl phenyl, butylbenzene base, penta phenyl or own phenyl for amyl, fluorine；Ar1-Ar8Respectively
Independently indicate phenyl, tolyl, ethylbenzene, propyl phenyl, butylbenzene base, penta phenyl, own phenyl, benzene phenyl, fluorine substituted-phenyl, fluorine
Replace tolyl, fluorine replace ethylbenzene, fluorine replace propyl phenyl, fluorine replace butylbenzene base, fluorine replace penta phenyl, fluorine replace own phenyl,
Fluorine substituted benzene phenyl, silicon substituted-phenyl, silicon replace tolyl, silicon replace ethylbenzene, silicon replace propyl phenyl, silicon replace butylbenzene base,
Silicon replaces penta phenyl, silicon to replace own phenyl, silicon substituted benzene phenyl or alkyl-substituted benzene phenyl；The fluorine substitution refers to: replacing
The hydrogen on hydrogen or substitution alkyl on aromatic rings；The referring to for silicon substitution is replaced by trimethyl silicane or triphenyl silicon；The alkane
Base substitution refers to: being replaced by methyl, ethyl, propyl, butyl, amyl or hexyl；The substituent group is one or more, when taking
For group be it is multiple when, substituent group is identical or different.
Optionally, pyrene compound is contained provided by embodiments of the present invention, there is structure shown in formula (Iba):
Wherein, Rw indicates hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C24 aryl；
Aw indicates substituted or unsubstituted C6-C24 aryl, substituted or unsubstituted C6-C24 heteroaryl.
Optionally, in structure shown in formula (Iba), Rw indicates hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, tertiary fourth
Base, normal-butyl, isobutyl group, phenyl, p-methylphenyl, aminomethyl phenyl, o-methyl-phenyl, the Aw indicate phenyl, tolyl,
Ethylbenzene, propyl phenyl, butylbenzene base, penta phenyl, own phenyl, naphthalene, xenyl, methyl biphenyl, ethyl biphenyl base, pentylbiphenyl
Base, butyl biphenyl base, pentylbiphenyl base, hexyl biphenyl base, aphthofurans base, halogen trimethylsilylbenzene base.
Optionally, have containing pyrene compound selected from one of following structure provided by embodiments of the present invention:
Embodiments of the present invention also provide a kind of Organic Light Emitting Diode, the luminescent layer packet of the Organic Light Emitting Diode
Contain pyrene compound containing above-mentioned.
Optionally, in the luminescent layer of the Organic Light Emitting Diode provided by embodiments of the present invention, contain comprising described
Pyrene compound and formula (IV) compound represented:
Wherein, R51-R58Each independently represent hydrogen, deuterium, C1-12 alkyl, C6-C18 aryl；R59、R60Table each independently
Show C6-C36 aryl or C6-C36 heteroaryl.
Optionally, formula (IV) compound represented has the structure selected from one of FBH1~FBH40:
In terms of existing technologies, contain in pyrene compound provided by embodiments of the present invention, contained by molecular center
Pyrenyl be main luminophore, contain benzofuran and naphthalene structure in the outside of the luminophore, this kind of outer pendant groups have
Very big rigidity, so that the luminous pyrenyl group of molecular center is by external influence very little, to ensure that provided by the present invention
There is preferable luminous efficiency containing pyrene compound, while significantly improving the luminescent lifetime of device.
In addition, being mixed with containing pyrene compound provided by embodiments of the present invention with logical formula (IV) compound represented
It is miscellaneous, as the luminescent layer of organic light emitting diode device, the good characteristic of the invention containing pyrene compound can be given full play to.
Detailed description of the invention
Fig. 1 is the spatial configuration figure of the compound C-1 in the specific embodiment of the invention；
Fig. 2 is the spatial configuration figure of the compound C-2 in the specific embodiment of the invention；
Fig. 3 is the spatial configuration figure of the compound C-3 in the specific embodiment of the invention；
Fig. 4 is the spatial configuration figure of the compound P-1 in the specific embodiment of the invention；
Fig. 5 is the spatial configuration figure of the compound P-13 in the specific embodiment of the invention；
Fig. 6 is the spatial configuration figure of the compound P-77 in the specific embodiment of the invention.
Specific embodiment
To make the object, technical solutions and advantages of the present invention clearer, below in conjunction with embodiment to of the invention each
Specific embodiment is explained in detail.However, it will be understood by those skilled in the art that in each embodiment party of the present invention
In formula, many technical details are proposed in order to make reader more fully understand the present invention.But even if without these technical details
And various changes and modifications based on the following respective embodiments, each claim skill claimed of the present invention also may be implemented
Art scheme.
Compound
It is provided to contain pyrene compound in certain specific embodiments of the invention, there is structure shown in formula (I):
Wherein,
R1-R10Each independently represent hydrogen, deuterium, fluorine, chlorine, bromine, iodine, substituted or unsubstituted C1-C24 alkyl, replace or
Unsubstituted C6-C36 aryl, substituted or unsubstituted C1-C24 alkoxy, replaces substituted or unsubstituted C3-C36 heteroaryl
Or unsubstituted C6-C36 aryloxy group, substituted or unsubstituted C3-C36 heteroaryloxy, substituted or unsubstituted C2-C24 alkanamine
Base, substituted or unsubstituted C7-C36 aryl amine, substituted or unsubstituted C4-C36 heteroaryl amido, and R1-R10In at least one
It is a that there is structure shown in formula (II):
* indicate that formula (II) is connect by the position with the pyrene residue in structure shown in formula (I)；
Ap, Aq each independently represent substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted C6-C36 aryl,
Substituted or unsubstituted C3-C36 heteroaryl, and at least one of Ap, Aq have structure shown in formula (III):
Nitrogen-atoms in formula (II) is connected with 10 carbon atoms in formula (III)；
Hydrogen atom in formula (III) it is unsubstituted or each independently by deuterium, fluorine, substituted or unsubstituted C1-C12 alkane
Base, substituted or unsubstituted C6-C24 aryl, one or more in substituted or unsubstituted C3-C24 heteroaryl replace.
It is described substituted or unsubstituted in the structure containing pyrene compound provided by certain specific embodiments of the invention
It is C1-C24 alkyl, substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C3-C36 heteroaryl, substituted or unsubstituted
C1-C24 alkoxy, substituted or unsubstituted C6-C36 aryloxy group, substituted or unsubstituted C3-C36 heteroaryloxy, replace
Or unsubstituted C2-C24 alkylamino radical, substituted or unsubstituted C7-C36 aryl amine, substituted or unsubstituted C4-C36 heteroaryl amine
Base, the alkyl of substituted or unsubstituted C1-C12, substituted or unsubstituted C6-C24 aryl, substituted or unsubstituted C3-C24 are miscellaneous
Substitution in aryl refers to: replacing alkyl, deuterium to replace by deuterium, fluorine, alkyl, alkoxy, aryl, heteroaryl, fluorine each independently
Alkyl, silicon replace alkyl, fluorine substituted alkoxy, deuterium substituted alkoxy, silicon substituted alkoxy, fluorine substituted aryl, deuterium substituted aryl,
One of silicon substituted aryl, fluorine substituted heteroaryl, deuterium substituted heteroaryl or silicon substituted heteroaryl replace.
In certain specific embodiments of the invention, it is provided containing pyrene compound have formula (Ia), (Ib), (Ic),
(Id), structure shown in (Ie), (If) or (Ig):
Wherein,
R1-R10Each independently represent hydrogen, deuterium, substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted C6-
C36 aryl, substituted or unsubstituted C3-C36 heteroaryl；
Ar1-Ar8Each independently represent substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted C6-C36 virtue
Base, substituted or unsubstituted C3-C36 heteroaryl, and Ar1-Ar8At least one of have formula (III) shown in structure:
10 carbon originals in nitrogen-atoms and formula (III) in formula (Ia), (Ib), (Ic), (Id), (Ie), (If) or (Ig)
Son is connected；Hydrogen atom in formula (III) it is unsubstituted or each independently by deuterium, fluorine, substituted or unsubstituted C1-C12 alkane
Base, substituted or unsubstituted C6-C24 aryl, one or more in substituted or unsubstituted C3-C24 heteroaryl replace.
In the structure containing pyrene compound provided by certain specific embodiments of the invention, R1-R10Table each independently
Show methyl, ethyl, propyl, butyl, amyl, hexyl, fluorine substituent methyl, fluorine replace ethyl, fluorine substituted propyl, fluorine replace butyl,
Fluorine replaces amyl, fluorine to replace hexyl, phenyl, tolyl, ethylbenzene, propyl phenyl, butylbenzene base, penta phenyl or own phenyl；
Ar1-Ar8Each independently represent phenyl, tolyl, ethylbenzene, propyl phenyl, butylbenzene base, penta phenyl, own phenyl, benzene
Phenyl, fluorine substituted-phenyl, fluorine replace tolyl, fluorine that ethylbenzene, fluorine is replaced to replace propyl phenyl, fluorine that butylbenzene base, fluorine is replaced to replace penta
Phenyl, fluorine replace own phenyl, fluorine substituted benzene phenyl, silicon substituted-phenyl, silicon to replace tolyl, silicon that ethylbenzene, silicon is replaced to replace third
Phenyl, silicon replace butylbenzene base, silicon that penta phenyl, silicon is replaced to replace own phenyl, silicon substituted benzene phenyl or alkyl-substituted benzene phenyl；
The fluorine replaces and refers to: the hydrogen on hydrogen or substitution alkyl on substituted aroma ring；What the silicon replaced refers to by three
Methyl silicon or triphenyl silicon replace；The alkyl substitution refers to: being replaced by methyl, ethyl, propyl, butyl, amyl or hexyl；Institute
Substituent group is stated as one or more, when substituent group is multiple, substituent group is identical or different.
It is provided that there is structure shown in formula (Iba) containing pyrene compound in certain specific embodiments of the invention:
Wherein,
Rw indicates hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C24 aryl；
Aw indicates substituted or unsubstituted C6-C24 aryl, substituted or unsubstituted C6-C24 heteroaryl.
Optionally, in structure shown in formula (Iba), Rw indicates hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, tertiary fourth
Base, normal-butyl, isobutyl group, phenyl, p-methylphenyl, aminomethyl phenyl, o-methyl-phenyl, the Aw indicate phenyl, tolyl,
Ethylbenzene, propyl phenyl, butylbenzene base, penta phenyl, own phenyl, naphthalene, xenyl, methyl biphenyl, ethyl biphenyl base, pentylbiphenyl
Base, butyl biphenyl base, pentylbiphenyl base, hexyl biphenyl base, aphthofurans base, halogen trimethylsilylbenzene base.
It is provided to have containing pyrene compound selected from one of following knot in certain specific embodiments of the invention
Structure:
In certain specific embodiments of the invention, a kind of Organic Light Emitting Diode, the organic light emission two are also provided
The luminescent layer of pole pipe includes above-mentioned containing pyrene compound.
In certain specific embodiments of the invention, contain pyrene comprising described in the luminescent layer of the Organic Light Emitting Diode
Compound and formula (IV) compound represented:
Wherein,
R51-R58Each independently represent hydrogen, deuterium, C1-12 alkyl, C6-C18 aryl；
R59、R60Each independently represent C6-C36 aryl or C6-C36 heteroaryl.
In certain specific embodiments of the invention, formula (IV) compound represented have selected from FBH1~FBH40 it
One structure:
General synthetic routes:
The present invention also provides the preparation method of the compounds of this invention, the general synthesis about pyrene compound be it is common, can
With with reference to the method in the document and patent published, citing such as: 2011057008 A of patent KR, CN107162916A,
US20160155952A1、US20150349265A1、US20110248246A1、KR1020140059705A、
WO2010013675A1、CN105037173A、US20130153867A1、TW201134787A、TWI601803B、
CN106883203A, document J.Org.Chem.2015,80,5658-5665, Bull.Chem.Soc.Jpn., 1983,56,
775-779、Journal of Molecular Structure 1127(2017)237-246、Journal of Applied
Physics 2005,98,074506、ACS Appl.Mater.Interfaces 2018,10,10246-10253。
More specifically, for present invention compound shown in general formula (Iba), its general synthetic routes is provided:
Wherein, group definition and formula (Iba) are consistent.
The acquisition pattern of two raw materials in synthetic route can be obtained by outsourcing or customization synthesis, and citing can also be with
Synthesis obtains in the following way:
Wherein, G1、G2、G3It is independent to indicate different reaction leaving group, react leaving group type be not by
Limit, reaction leaving group can all leave away during the reaction, such as halogen, can also partially leave away, such as two on amino
A hydrogen is only left away a hydrogen.It is preferred that but be not to limit, G1For fluorine, chlorine, bromine, iodine, more preferably bromine；G2For amino；G3For boric acid
Ester, halogen, more preferably chlorine or bromine.Work as G3When for halogen, magnesium halide leaving group can be further converted into or lithium is left away
Group, raw material are also converted to grignard reagent or lithium reagent accordingly.
Synthesize example:
The preparation method of disclosed compound of present invention provided below.But present disclosure is not intended to be limited to institute herein
The method of narration it is any.Those skilled in the art can easily modify described method or utilize different sides
Method prepares the one or more of disclosed compound.Following aspect is merely exemplary, and is not intended to limit in the disclosure
The range of appearance.Temperature, catalyst, concentration, reactant composition and other process conditions are changeable, and match for desired
Object is closed, present disclosure those skilled in the art can readily select suitable reactant and condition.
The preparation of embodiment 1:P-89
(1) intermediate M1 is prepared
Under nitrogen protection, 10- bromobenzofuran and naphthalene 1.5g, 4- isopropyl aniline 3.0g are added into 75ml reactor,
Three (double benzylideneacetones) two palladiums (Pd2 (dba) 3), bis- (diphenylphosphine) -1 0.15g, 1 '-dinaphthalene (BINAP) 0.20g, the tert-butyl alcohol
Sodium 2.0g, toluene 30ml after nitrogen deoxygenation 30min, are warming up to 100 degree, keep the temperature 24.0h.After being cooled to room temperature, filtering, filter cake
It with being concentrated after eluent methylene chloride, is refined by silica gel chromatograph, obtains faint yellow solid 1.45g, as intermediate M1, m/z=
351。
(2) target compound P-89 is prepared
Under nitrogen protection, 800mg intermediate M1,1,6- bis- bromo- 3,8- diisopropyl pyrene are added into 75ml reactor
492mg, sodium tert-butoxide 300mg, palladium acetate 30mg after tri-tert phosphorus 37mg, toluene 18ml, nitrogen deoxygenation 30min, are warming up to
110 degree, heat preservation is for 24 hours.It after being cooled to room temperature, filters, filtrate concentration filters after washing material with ethyl acetate, obtains yellow solid
627mg, as compound P-89.M/z=984.The maximum emission peak of photoluminescence spectra in room-temperature toluene solution is
471nm。
The preparation of embodiment 2:P-13
Under nitrogen protection, 800mg intermediate M1,1,6- dibromo pyrene 400mg, sodium tert-butoxide are added into 75ml reactor
180mg, palladium acetate 15mg after tri-tert phosphorus 20mg, toluene 12ml, nitrogen deoxygenation 30min, are warming up to 85 degree, heat preservation is for 24 hours.
After being cooled to room temperature, organic phase filtering, after merging organic phase concentration, refined with silica gel chromatograph (n-hexane: methylene chloride=
1:1), it is dried under reduced pressure to obtain 578mg yellow solid, as compound P-13.M/z=900.
The preparation of embodiment 3:P-37
Under nitrogen protection, 800mg intermediate M1,1,6- bis- bromo- 3,8- di-t-butyl pyrene are added into 75ml reactor
524mg, sodium tert-butoxide 180mg, palladium acetate 15mg after tri-tert phosphorus 20mg, toluene 12ml, nitrogen deoxygenation 30min, are warming up to
85 degree, heat preservation is for 24 hours.After being cooled to room temperature, organic phase filtering, after merging organic phase concentration, refined with silica gel chromatograph (just oneself
Alkane: methylene chloride=1:1), it is dried under reduced pressure to obtain 602mg yellow solid, as compound P-37.M/z=1012.
The preparation of embodiment 4:P-18
(1) intermediate M2 is prepared
Under nitrogen protection, it is added 10- bromobenzofuran and naphthalene 1.5g, 4- phenylaniline 3.8g into 75ml reactor, three
(double benzylideneacetones) two palladiums (Pd2 (dba) 3), bis- (diphenylphosphine) -1 0.15g, 1 '-dinaphthalene (BINAP) 0.20g, sodium tert-butoxide
2.0g, toluene 30ml after nitrogen deoxygenation 30min, are warming up to 100 degree, keep the temperature 24.0h.After being cooled to room temperature, filtering, filter cake is used
It is concentrated after eluent methylene chloride, is refined by silica gel chromatograph, obtain faint yellow solid 1.31g, as intermediate M2, m/z=385.
(2) target compound P-18 is prepared
Under nitrogen protection, 900mg intermediate M2,1,6- dibromo pyrene 400mg, sodium tert-butoxide are added into 75ml reactor
180mg, palladium acetate 15mg after tri-tert phosphorus 20mg, toluene 12ml, nitrogen deoxygenation 30min, are warming up to 85 degree, heat preservation is for 24 hours.
After being cooled to room temperature, organic phase filtering, after merging organic phase concentration, refined with silica gel chromatograph (n-hexane: methylene chloride=
1:1), it is dried under reduced pressure to obtain 371mg yellow solid, as compound P-18.M/z=968.
The preparation of embodiment 5:P-94
Under nitrogen protection, 900mg intermediate M2,1,6- bis- bromo- 3,8- diisopropyl pyrene are added into 75ml reactor
492mg, sodium tert-butoxide 180mg, palladium acetate 15mg after tri-tert phosphorus 20mg, toluene 12ml, nitrogen deoxygenation 30min, are warming up to
85 degree, heat preservation is for 24 hours.After being cooled to room temperature, organic phase filtering, after merging organic phase concentration, refined with silica gel chromatograph (just oneself
Alkane: methylene chloride=1:1), it is dried under reduced pressure to obtain 473mg yellow solid, as compound P-94.M/z=1052.
The preparation of embodiment 6:P-42
Under nitrogen protection, 900mg intermediate M2,1,6- bis- bromo- 3,8- di-t-butyl pyrene are added into 75ml reactor
524mg, sodium tert-butoxide 180mg, palladium acetate 15mg after tri-tert phosphorus 20mg, toluene 12ml, nitrogen deoxygenation 30min, are warming up to
85 degree, heat preservation is for 24 hours.After being cooled to room temperature, organic phase filtering, after merging organic phase concentration, refined with silica gel chromatograph (just oneself
Alkane: methylene chloride=1:1), it is dried under reduced pressure to obtain 488mg yellow solid, as compound P-42.M/z=1080.
It should be noted that in addition to above-claimed compound, other compounds provided by the present invention are see also general synthesis
Route follows same method and steps according to the synthesis example with above compound and is prepared.
Luminescent properties
In embodiments of the present invention, the energy level information of organic material, such as triplet energy level (T1) and singlet level
(S1), highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO) illustrate but are not to limit, can obtain in the following way
It arrives.
HOMO and lumo energy can be measured by photoelectric effect, such as XPS (x-ray photoelectron spectroscopy), UPS
(ultraviolet photoelectron spectroscopy), CV (cyclic voltammetry) or DPV (differential pulse voltammetry).Quantum chemical methods meter can also be passed through
It obtains, such as density functional theory.These are all the effective methods for obtaining molecular orbital energy level.
The triplet energy level (T1) of organic material can be measured by low temperature time resolved spectroscopy, can also pass through quantum
Chemical method is calculated.The calculation method of quantum chemistry can be found in by business software, specific method
WO2011141110。
The singlet level (S1) of organic material can be measured by low temperature time resolved spectroscopy, can also pass through room temperature
Stable state spectrum measures, and can also be calculated by quantum chemical methods.The calculation method of quantum chemistry, can be by commercialization
Software, specific method can be found in US2013059924.
It should be noted that, the absolute value of HOMO, LUMO, T1 and S1 depend on measurement method or calculation method used, very
To for identical method, different processing steps, obtained numerical value is also discrepant.Such as it is originated on cyclic voltammetry curve
Point and peak dot can provide different oxidation-reduction potentials, and then obtain different HOMO and LUMO values.Therefore, rationally significant
Compare, it should with identical measurement method and identical processing method.
In the description of the embodiment of the present invention, the value of HOMO, LUMO, T1 and S1 are obtained based on Density function theory
's.HOMO and LUMO numerical value optimizes in the case where B3LYP/6-311G (d, p) is horizontal to be obtained, T1 and S1 numerical value on the basis of optimization,
It is obtained under PBE0/6-311G (d, p) is horizontal.Evaluation uses absolute value representation, and unit of account is used uniformly electron-volt
(eV)。
The spectral measurement of PL (photoluminescence spectra), can be measured by Fluorescence Spectrometer.EL's (electroluminescent spectrum)
Spectral measurement can be measured plus Electric drive module by Fluorescence Spectrometer, can also use special organic electroluminescent EL
Spectrum testing systems test.Likewise, rationally significant comparison, it should with identical measurement method and identical processing side
Method.
1. compound energy level data of table
| HOMO | LUMO | S1 | T1 | |
| P-1 | 5.02 | 1.93 | 2.77 | 1.79 |
| P-2 | 4.93 | 1.88 | 2.73 | 1.78 |
| P-10 | 5.03 | 1.93 | 2.78 | 1.80 |
| P-13 | 4.94 | 1.88 | 2.73 | 1.78 |
| P-14 | 4.94 | 1.88 | 2.73 | 1.79 |
| P-17 | 5.01 | 1.92 | 2.76 | 1.79 |
| P-19 | 4.97 | 1.89 | 2.76 | 1.79 |
| P-25 | 4.94 | 1.89 | 2.74 | 1.73 |
| P-77 | 4.93 | 1.87 | 2.76 | 1.74 |
When can be seen that structure of the invention compound from the energy level data of upper table using different substituent groups, HOMO
Numerical value change is no more than 0.1eV, and LUMO numerical value change is no more than 0.06eV, and S1 numerical value change is no more than 0.05eV, and T1 numerical value becomes
Change and be no more than 0.07eV, illustrates that substituent group is very little on the influence of the energy level of the compounds of this invention.
Compound spatial configuration
Fig. 1 to Fig. 6 is the spatial configuration figure of compound C-1, C-2, C-3, P-1, P-13, P-77 respectively.It is of the present invention
Spatial configuration figure, be the configuration picture of the optimum structure of theoretical modeling, method calculates side when HOMO energy level using the present invention
Method.It can be seen that, as the benzofuran of auxiliary light emission group and the group of naphthalene, being located at master in compound provided by the present invention
Emit the top of group pyrenyl group, so that mainly transmitting group is smaller by external action, and control compounds, auxiliary hair
Light group extends outwardly or is located only within the side of pyrenyl group, is affected by extraneous aging action.
Device application
In certain specific embodiments of the invention, additionally provide it is above-mentioned containing pyrene compound Organic Light Emitting Diode,
Organic crystal field, organic solar batteries, the application in light emitting diode with quantum dots.
In certain specific embodiments of the invention, a kind of organic light emitting diode device is additionally provided, organic hair
The emitting layer material of optical diode device includes above-mentioned containing pyrene compound.
In certain specific embodiments of the invention, comprising above-mentioned in the luminescent layer of provided Organic Light Emitting Diode
Containing pyrene compound and formula (IV) compound represented.
Device example
Device provided by embodiments of the present invention, adopts and prepare with the conventional methods in the field: selection is suitable first
Anode, for introducing hole, anode surface can be deposited the work function that other materials changes anode, organic layer then be deposited, so
After continue evaporation cathode, play the role of introduce electronics.The organic layer can be one layer, be also possible to multilayer.Further,
Organic layer includes hole transmission layer, luminescent layer and electron transfer layer.The hole transmission layer can also have hole function of injecting,
Electronic blocking function or exciton blocking function, the electron transfer layer can also have the function of electronics injecting function, hole barrier
Or exciton blocking function, the luminescent layer can be doped structure.When the luminescent layer is doped structure, by weight percent height
Be known as material of main part, by weight percent it is low be known as guest materials.Material of main part can be only a kind of, or more
Kind.When using doped structure, the doping ratio of guest materials is 0.1-49.9%, preferably 0.5-20%.
It citing but does not limit, can prepare in accordance with the following steps:
Cleaned ito glass substrate is placed in vacuum chamber, is evacuated to 10-5The 4,4' of one layer of 60nm are deposited in Pa,
4 "-three (2- naphthylphenyl amino) triphenylamines (2-TNATA)；Continue N, N, N' that one layer of 20nm is deposited, N'- tetra- (2- naphthalene)-
1,1'- biphenyl -4,4'- diamines (TNB)；Continue the material of main part of total one layer of 40nm of vapor deposition and the luminescent layer of guest materials doping,
Doping concentration is 5wt%；Continue 2- [4- (9,10- dinaphthyl -2- anthracene -2- base) phenyl] -1- phenyl -1H- that one layer of 40nm is deposited
Benzimidazole (ZADN)；Continue the lithium fluoride that one layer of 1nm is deposited；Continue the aluminium electrode that one layer of 200nm is deposited.
Wherein, the dopant material is (containing with above-mentioned preparation in the present embodiment provided by the present invention containing pyrene compound
For pyrene compound P-89 and P-13)；The material of main part is documented formula (IV) compound represented (this reality in the present invention
It applies in example by taking FBH1:9- (1- naphthalene) -10- (4- (2- naphthalene) phenyl) anthracene as an example).
In addition, in order to illustrate the significant effect provided by the present invention containing pyrene compound as the dopant material in luminescent layer
Fruit is also the doped compound of comparison with C-1 in the present embodiment, equally is doped to form luminescent layer with FBH1, be prepared
The organic light emitting diode device of comparison.
Carry out the measurement of maximum external quantum efficiency respectively to the organic light emitting diode device of above-mentioned acquisition: by organic
Light emitting diode applies electric current and device is shone, and as the current density increases, external quantum efficiency increases or decreases therewith, record
Its maximum value, as maximum external quantum efficiency.
It carries out the measurement of device lifetime respectively to the organic light emitting diode device of above-mentioned acquisition: being with starting brightness
1000cd/m2, record its time for decaying to starting brightness 95%.
2 external quantum efficiency of table and device lifetime
| Device embodiments 1 | Dopant material | Maximum external quantum efficiency | Device lifetime |
| 1 | P-89 | 8.6% | 45 hours |
| 2 | P-13 | 8.4% | 34 hours |
| Comparative device | C-1 | 8.3% | 9.5 hour |
As seen from the above table, using it is provided by the present invention containing pyrene compound as dopant material, with formula (IV) compound (such as
FBH1 it) is doped the organic light emitting diode device for obtaining luminescent layer and being further prepared, relative to comparative device
For, maximum external quantum efficiency increases, and the service life of device significantly extends.
It will be understood by those skilled in the art that the respective embodiments described above are to realize specific embodiments of the present invention,
And in practical applications, can to it, various changes can be made in the form and details, without departing from the spirit and scope of the present invention.
Claims (10)
1. one kind contains pyrene compound, which is characterized in that have structure shown in formula (I):
Wherein,
R1-R10Hydrogen is each independently represented, deuterium, fluorine, chlorine, bromine, iodine, substituted or unsubstituted C1-C24 alkyl, replaces or does not take
The C6-C36 aryl in generation, substituted or unsubstituted C3-C36 heteroaryl, substituted or unsubstituted C1-C24 alkoxy, replace or not
Substituted C6-C36 aryloxy group, substituted or unsubstituted C2-C24 alkylamino radical, takes substituted or unsubstituted C3-C36 heteroaryloxy
Generation or unsubstituted C7-C36 aryl amine, substituted or unsubstituted C4-C36 heteroaryl amido, and R1-R10At least one of have
Structure shown in formula (II):
* indicate that formula (II) is connect by the position with the pyrene residue in structure shown in formula (I)；
Ap, Aq each independently represent substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted C6-C36 aryl, replace
Or unsubstituted C3-C36 heteroaryl, and at least one of Ap, Aq have structure shown in formula (III):
Nitrogen-atoms in formula (II) is connected with 10 carbon atoms in formula (III)；
Hydrogen atom in formula (III) it is unsubstituted or each independently by deuterium, fluorine, substituted or unsubstituted C1-C12 alkyl,
One or more substitutions in substituted or unsubstituted C6-C24 aryl, substituted or unsubstituted C3-C24 heteroaryl.
2. according to claim 1 contain pyrene compound, which is characterized in that the substituted or unsubstituted C1-C24 alkyl,
Substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C3-C36 heteroaryl, substituted or unsubstituted C1-C24 alcoxyl
Base, substituted or unsubstituted C6-C36 aryloxy group, substituted or unsubstituted C3-C36 heteroaryloxy, substituted or unsubstituted C2-
C24 alkylamino radical, substituted or unsubstituted C4-C36 heteroaryl amido, replaces or does not take substituted or unsubstituted C7-C36 aryl amine
The alkyl of the C1-C12 in generation, substituted or unsubstituted C6-C24 aryl, the substitution in substituted or unsubstituted C3-C24 heteroaryl
Refer to: replacing alkyl, deuterium that alkyl, silicon is replaced to replace alkane by deuterium, fluorine, alkyl, alkoxy, aryl, heteroaryl, fluorine each independently
Base, fluorine substituted alkoxy, deuterium substituted alkoxy, silicon substituted alkoxy, fluorine substituted aryl, deuterium substituted aryl, silicon substituted aryl, fluorine
One of substituted heteroaryl, deuterium substituted heteroaryl or silicon substituted heteroaryl replace.
3. it is according to claim 1 contain pyrene compound, which is characterized in that have formula (Ia), (Ib), (Ic), (Id),
(Ie), structure shown in (If) or (Ig):
Wherein,
R1-R10Each independently represent hydrogen, deuterium, substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted C6-C36 virtue
Base, substituted or unsubstituted C3-C36 heteroaryl；
Ar1-Ar8It each independently represents substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted C6-C36 aryl, take
Generation or unsubstituted C3-C36 heteroaryl, and Ar1-Ar8At least one of have formula (III) shown in structure:
Nitrogen-atoms in formula (Ia), (Ib), (Ic), (Id), (Ie), (If) or (Ig) and 10 carbon atom phases in formula (III)
Even；Hydrogen atom in formula (III) it is unsubstituted or each independently by deuterium, fluorine, substituted or unsubstituted C1-C12 alkyl, take
One or more substitutions in generation or unsubstituted C6-C24 aryl, substituted or unsubstituted C3-C24 heteroaryl.
4. according to claim 3 contain pyrene compound, which is characterized in that R1-R10Each independently represent methyl, ethyl,
Propyl, butyl, amyl, hexyl, fluorine substituent methyl, fluorine replace ethyl, fluorine substituted propyl, fluorine that butyl, fluorine is replaced to replace amyl, fluorine
Replace hexyl, phenyl, tolyl, ethylbenzene, propyl phenyl, butylbenzene base, penta phenyl or own phenyl；
Ar1-Ar8Each independently represent phenyl, tolyl, ethylbenzene, propyl phenyl, butylbenzene base, penta phenyl, own phenyl, benzene benzene
Base, fluorine substituted-phenyl, fluorine replace tolyl, fluorine that ethylbenzene, fluorine is replaced to replace propyl phenyl, fluorine that butylbenzene base, fluorine is replaced to replace penta benzene
Base, fluorine replace own phenyl, fluorine substituted benzene phenyl, silicon substituted-phenyl, silicon to replace tolyl, silicon that ethylbenzene, silicon is replaced to replace propyl benzene
Base, silicon replace butylbenzene base, silicon that penta phenyl, silicon is replaced to replace own phenyl, silicon substituted benzene phenyl or alkyl-substituted benzene phenyl；
The fluorine replaces and refers to: the hydrogen on hydrogen or substitution alkyl on substituted aroma ring；What the silicon replaced refers to by trimethyl
Silicon or triphenyl silicon replace；The alkyl substitution refers to: being replaced by methyl, ethyl, propyl, butyl, amyl or hexyl；It is described to take
It is one or more for group, when substituent group is multiple, substituent group is identical or different.
5. according to claim 3 contain pyrene compound, which is characterized in that have structure shown in formula (Iba):
Wherein,
Rw indicates hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C24 aryl；
Aw indicates substituted or unsubstituted C6-C24 aryl, substituted or unsubstituted C6-C24 heteroaryl.
6. according to claim 5 contain pyrene compound, which is characterized in that the Rw indicates hydrogen, deuterium, methyl, ethyl, positive third
Base, isopropyl, tert-butyl, normal-butyl, isobutyl group, phenyl, p-methylphenyl, aminomethyl phenyl, o-methyl-phenyl, the Aw table
Show phenyl, tolyl, ethylbenzene, propyl phenyl, butylbenzene base, penta phenyl, own phenyl, naphthalene, xenyl, methyl biphenyl, ethyl
Xenyl, isopropylbiphenyl, butyl biphenyl base, pentylbiphenyl base, hexyl biphenyl base, aphthofurans base, halogen trimethylsilylbenzene base.
7. according to claim 1 contain pyrene compound, have selected from one of following structure:
8. a kind of Organic Light Emitting Diode, which is characterized in that the luminescent layer of the Organic Light Emitting Diode includes claim 1-7
Any one of described in contain pyrene compound.
9. Organic Light Emitting Diode according to claim 8, which is characterized in that the luminescent layer includes the chemical combination containing pyrene
Object and formula (IV) compound represented:
Wherein,
R51-R58Each independently represent hydrogen, deuterium, C1-12 alkyl, C6-C18 aryl；
R59、R60Each independently represent C6-C36 aryl or C6-C36 heteroaryl.
10. Organic Light Emitting Diode according to claim 9, which is characterized in that formula (IV) compound represented has choosing
From the structure of one of FBH1~FBH40:
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| CN115785042A (en) * | 2021-09-09 | 2023-03-14 | 广州华睿光电材料有限公司 | Pyrene organic compound, mixture, composition and organic electronic device |
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| CN108329272A (en) * | 2018-04-04 | 2018-07-27 | 长春海谱润斯科技有限公司 | A kind of electroluminescent organic material and its organic luminescent device of the structure containing pyrene |
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