CN110128329A - Nitrogenous heterocyclic aromatic amino-derivative and its application and organic electroluminescence device - Google Patents
Nitrogenous heterocyclic aromatic amino-derivative and its application and organic electroluminescence device Download PDFInfo
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- CN110128329A CN110128329A CN201810108437.5A CN201810108437A CN110128329A CN 110128329 A CN110128329 A CN 110128329A CN 201810108437 A CN201810108437 A CN 201810108437A CN 110128329 A CN110128329 A CN 110128329A
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- Prior art keywords
- substituted
- layer
- phenyl
- aromatic amino
- base
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- -1 Nitrogenous heterocyclic aromatic amino-derivative Chemical class 0.000 title claims abstract description 66
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 35
- 239000000463 material Substances 0.000 claims description 41
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000004076 pyridyl group Chemical group 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000000217 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 10
- 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 9
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 238000002347 injection Methods 0.000 claims description 7
- 239000007924 injection Substances 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 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 6
- 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 5
- 230000005540 biological transmission Effects 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 5
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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 3
- 125000001725 pyrenyl group Chemical group 0.000 claims description 3
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical compound C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 claims description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 2
- BGEVROQFKHXUQA-UHFFFAOYSA-N 71012-25-4 Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1C1=CC=CC=C1N2 BGEVROQFKHXUQA-UHFFFAOYSA-N 0.000 claims description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000005580 triphenylene group Chemical group 0.000 claims description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 33
- 238000000034 method Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000012265 solid product Substances 0.000 description 5
- 238000004611 spectroscopical analysis Methods 0.000 description 5
- 238000007738 vacuum evaporation Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 2
- DURJLUPGCSQXHV-UHFFFAOYSA-N 1-bromo-2-phenylanthracene Chemical compound C1(=CC=CC=C1)C1=C(C2=CC3=CC=CC=C3C=C2C=C1)Br DURJLUPGCSQXHV-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical group [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical group C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- NHQFCLUTVCQTDL-UHFFFAOYSA-N 1,3-diphenyl-2H-pyridine Chemical compound C1(=CC=CC=C1)N1CC(=CC=C1)C1=CC=CC=C1 NHQFCLUTVCQTDL-UHFFFAOYSA-N 0.000 description 1
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- QSOAYCUFEQGHDN-UHFFFAOYSA-N 9-naphthalen-1-ylcarbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=CC2=CC=CC=C12 QSOAYCUFEQGHDN-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- 102100024049 A-kinase anchor protein 13 Human genes 0.000 description 1
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 1
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 101100269519 Homo sapiens AKAP13 gene Proteins 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 101150075070 PFD1 gene Proteins 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium 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
- 125000002078 anthracen-1-yl 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 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002305 electric material Substances 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- ZEWMZYKTKNUFEF-UHFFFAOYSA-N indium;oxozinc Chemical compound [In].[Zn]=O ZEWMZYKTKNUFEF-UHFFFAOYSA-N 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- ZGYRTJADPPDDMY-UHFFFAOYSA-N titanium;tetrahydrate Chemical compound O.O.O.O.[Ti] ZGYRTJADPPDDMY-UHFFFAOYSA-N 0.000 description 1
- MEYZYGMYMLNUHJ-UHFFFAOYSA-N tunicamycin Natural products CC(C)CCCCCCCCCC=CC(=O)NC1C(O)C(O)C(CC(O)C2OC(C(O)C2O)N3C=CC(=O)NC3=O)OC1OC4OC(CO)C(O)C(O)C4NC(=O)C MEYZYGMYMLNUHJ-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
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Abstract
This disclosure relates to a kind of nitrogenous heterocyclic aromatic amino-derivative and its application and organic electroluminescence device, which has structure shown in following general formula (1) or formula (2):
Description
Technical field
This disclosure relates to field of organic electroluminescent materials, and in particular, to a kind of nitrogenous heterocyclic aromatic amino-derivative
And its application and organic electroluminescence device.
Background technique
Display of organic electroluminescence (hereinafter referred to as OLED) have from main light emission, low-voltage direct-current driving, all solidstate,
The a series of advantages such as visual angle is wide, light-weight, composition and simple process, compared with liquid crystal display, ORGANIC ELECTROLUMINESCENCE DISPLAYS
Device does not need backlight, and visual angle is big, and power is low, and for response speed up to 1000 times of liquid crystal display, manufacturing cost is low
In the liquid crystal display of same resolution ratio, therefore, organic electroluminescence device has broad application prospects.
As OLED technology is in the continuous propulsion for illuminating and showing two big fields, people are for influencing OLED device performance
The research of efficient organic material focus more on, an excellent in efficiency service life long organic electroluminescence device is usually device junction
The result of the optimization collocation of structure and various organic materials.In the most common OLED device structure, following type is generally included
Organic material: hole-injecting material, hole mobile material, electron transport material, and assorted luminescent material (dyestuff or
Adulterate guest materials) and corresponding material of main part etc..
The electron transport material that tradition uses in electroluminescent device is Alq3, but the electron mobility of Alq3 compares
It is low (about 10-6cm2/Vs).In order to improve the electronic transmission performance of electroluminescence device, researcher has done a large amount of exploration
Journal of Sex Research work.
Ideal electron transport material, it should the characteristic with following several respects: anti-with reversible electrochemical reduction
It answers, HOMO and lumo energy are suitable, electron mobility is high, good film-forming property, Tg high, are preferably able to stop hole.It is currently known
Electron transport material performance is unsatisfactory, and industry is still badly in need of developing new electron transport material.
Summary of the invention
Purpose of this disclosure is to provide a kind of nitrogenous heterocyclic aromatic amino-derivative and its application and organic electroluminescences
Part, the nitrogenous heterocyclic aromatic amino-derivative are applied in organic electroluminescence device, can reduce raising organic electroluminescent
The operating voltage of device improves luminescent properties and extends device lifetime.To achieve the goals above, disclosure first aspect mentions
For a kind of nitrogenous heterocyclic aromatic amino-derivative, which has following general formula (1) or formula (2)
Shown in structure:
Wherein, R1、R2And R3It is each independently selected from hydrogen, C1~C12Aliphatic alkyl, C3~C12Naphthenic base, substitution or not
Substituted C6~C30Aromatic radical and substituted or unsubstituted C2~C30At least one of heteroaryl；
L is selected from substituted or unsubstituted C6~C30Arlydene and substituted or unsubstituted C2~C30In inferior heteroaryl extremely
Few one kind；
Ar1、Ar2、Ar3And Ar4It is each independently selected from substituted or unsubstituted C6~C30Aryl and substituted or unsubstituted
C2~C30At least one of nitrogenous heteroaryl；
X1、X2、X3、X4And X5It is each independently selected from N or CRX, and X1、X2、X3、X4And X5In at least one be N, RXIt is selected from
Hydrogen, C1~C12Aliphatic alkyl, C3~C12Naphthenic base, substituted or unsubstituted C6~C30Aromatic radical and substituted or unsubstituted
C2~C30At least one of heteroaryl.
The nitrogenous heterocyclic aromatic amino-derivative that disclosure second aspect provides above-mentioned first aspect is preparing organic electroluminescence
Application in luminescent device.
The disclosure third aspect provides a kind of organic electroluminescence device, including substrate, anode layer, cathode layer, Yi Jijie
At least one layer of organic function layer between anode layer and cathode layer, the organic function layer include hole injection layer, hole biography
The electron transport layer materials of defeated layer, organic luminous layer, electron transfer layer and electron injecting layer, the electron transfer layer contain
Nitrogenous heterocyclic aromatic amino-derivative described in disclosure first aspect.
Through the above technical solutions, the structure coplanarity of the nitrogenous heterocyclic aromatic amino-derivative of the disclosure is good, have
Higher carrier transport, which, which is used for organic electroluminescence device, can significantly reduce the operating voltage of device；
Meanwhile the compound has high mobility, and the thickness of material is enable to adjust in a wider range, the film thickness for increasing material can
Indistinctively to influence the operating voltage of device, the electron transport material being suitable for use as in organic electroluminescence device, with hair
The LUMO level-density parameter degree of photosphere material of main part is high, can be effectively reduced device operating voltages, improve device light emitting efficiency and
Device lifetime can effectively be extended.
Other feature and advantage of the disclosure will the following detailed description will be given in the detailed implementation section.
Specific embodiment
The specific embodiment of the disclosure is described in detail below.It should be understood that described herein specific
Embodiment is only used for describing and explaining the disclosure, is not limited to the disclosure.
Disclosure first aspect provides a kind of nitrogenous heterocyclic aromatic amino-derivative, and the nitrogenous heterocyclic arylamine class is derivative
Object has structure shown in following general formula (1) or formula (2):
Wherein, R1、R2And R3It is each independently selected from hydrogen, C1~C12Aliphatic alkyl, C3~C12Naphthenic base, substitution or not
Substituted C6~C30Aromatic radical and substituted or unsubstituted C2~C30At least one of heteroaryl；L is selected from substituted or unsubstituted
C6~C30Arlydene and substituted or unsubstituted C2~C30At least one of inferior heteroaryl；Ar1、Ar2、Ar3And Ar4Respectively
Independently selected from substituted or unsubstituted C6~C30Aryl and substituted or unsubstituted C2~C30At least one in nitrogenous heteroaryl
Kind；X1、X2、X3、X4And X5It is each independently selected from N or CRX, and X1、X2、X3、X4And X5In at least one be N, RXSelected from hydrogen, C1
~C12Aliphatic alkyl, C3~C12Naphthenic base, substituted or unsubstituted C6~C30Aromatic radical and substituted or unsubstituted C2~C30
At least one of heteroaryl.
The structure coplanarity of the nitrogenous heterocyclic aromatic amino-derivative of the disclosure is good, carrier transport with higher
Property, which, which is used for organic electroluminescence device, can significantly reduce the operating voltage of device；Meanwhile the compound has
Standby high mobility, enables the thickness of material to adjust in a wider range, the film thickness for increasing material can indistinctively influence device
The operating voltage of part, the electron transport material being suitable for use as in organic electroluminescence device, with luminescent layer material of main part
Lumo energy matching degree is high, can be effectively reduced device operating voltages, improves device light emitting efficiency and can effectively extend device
Service life.
According to the disclosure, substituted C6~C30Aryl, substituted C2~C30Heteroaryl, substituted C2~C30Inferior heteroaryl
With substituted C2~C30Substituent group in nitrogenous heteroaryl can be each independently halogen group, cyano, C1~C6Alkyl,
C1~C6Alkoxy, C6~C30Aromatic radical or C2~C30Substituent group in heteroaryl is each independently halogen group, cyanogen
Base, C1~C6Alkyl, C1~C6Alkoxy, C6~C30Aromatic radical or C2~C30Heteroaryl, wherein halogen group can be with
For at least one of-F ,-Cl ,-Br ,-I, C1~C6Alkyl be preferably methyl, ethyl, n-propyl, isopropyl, positive fourth
At least one of base, isobutyl group, n-pentyl, n-hexyl, cyclopenta and cyclohexyl, C1~C6Alkoxy be preferably methoxy
At least one of base, ethyoxyl, propoxyl group and isopropoxy.
According to the disclosure, C6~C30Aryl be it is well-known to those skilled in the art, that is, have 6~30 skeleton carbon originals
Son aryl, preferably have 6~20 backbone carbon atoms, such as can for selected from phenyl, xenyl, terphenyl, naphthalene,
Anthryl, fluoranthene base, phenanthryl, indenyl, benzo fluorenyl, fluorenyl, triphenylene, pyrenyl, base,In base and aphthacene base extremely
Few one kind, wherein xenyl may include selected from 2- xenyl, 3- xenyl and 4- xenyl；Terphenyl may include
P- terphenyl -4- base, p- terphenyl -3- base, p- terphenyl -2- base, m- terphenyl -4- base, m- three
At least one of phenyl -3- base and m- terphenyl -2- base, naphthalene may include 1- naphthalene and/or 2- naphthalene, anthryl
It may include at least one of 1- anthryl, 2- anthryl and 9- anthryl, fluorenyl derivative may include 9,9 '-dimethyl fluorenes, 9,
At least one of 9 '-spiral shell, two fluorenes, benzfluorene and indenofluorene, pyrenyl may include in 1- pyrenyl, 2- pyrenyl and 4- pyrenyl
At least one.
According to the disclosure, heteroaryl refers to at least one hetero atom and with the list of certain amount ring skeleton atom
Ring or polycyclic aromatic group, hetero atom may include one or more hetero atoms selected from B, N, O, S, P (=O), Si and P；It is excellent
Selection of land, hetero atom may include one or more hetero atoms for being selected from O, S and N.C2~C30Heteroaryl has 2~30 skeletons
Carbon atom, preferably have 4~20 backbone carbon atoms, such as can for selected from furyl, thienyl, pyrrole radicals, pyridyl group,
Carbazyl, benzofuranyl, benzothienyl, isobenzofuran-base, indyl, quinolyl, isoquinolyl, dibenzofurans
Base, dibenzothiophene, 9- phenyl carbazole base, 9- naphthyl carbazole base, benzo carbazole base, dibenzo-carbazole base, indolocarbazole
At least one of base and benzodioxole group, preferably pyridyl group.
According to the disclosure, C1~C12Aliphatic alkyl be it is well-known to those skilled in the art, that is, have 1~12 carbon
The aliphatic alkyl of atom, can be for selected from methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, octyl, nonyl, the last of the ten Heavenly stems
Base, undecyl and dodecyl, wherein alkyl can be direct-connected alkyl or the alkyl with branch, further preferably first
At least one of base, ethyl, n-propyl, isopropyl, normal-butyl, isobutyl group, n-pentyl and n-hexyl.
According to the disclosure, C3~C12Naphthenic base be it is well-known to those skilled in the art, that is, have 3~12 carbon atoms
Naphthenic base, preferably cyclopenta or cyclohexyl.
According to the disclosure, in structure shown in formula (1) or formula (2), X1It can be N, X2、X3、 X4And X5It can be CRX；
Alternatively, X2It can be N, X1、X3、X4And X5It can be CRX；Alternatively, X3It can be N, X1、X2、X4And X5It can be CRX；Or
Person, X2And X3It can be N, X1、X4And X5It can be CRX；Alternatively, X1And X4It can be N, X2、X3And X5Can be
CRX, wherein RXPreferably H.
According to the disclosure, R1、R2And R3H, methyl, ethyl, isopropyl, n-propyl, positive fourth can be each independently selected from
Base, n-pentyl, n-hexyl, cyclopenta, cyclohexyl, phenyl, aminomethyl phenyl, ethylphenyl, xenyl, naphthalene, pyridyl group, click
At least one of oxazolyl, carbazyl phenyl, fluorenyl, N- fluorenyl carbazyl, methoxyl group, ethyoxyl and trifluoromethyl, preferably
H, at least one of ethyl, isopropyl, cyclohexyl, phenyl and pyridyl group.Specifically, in a kind of specific implementation of the disclosure
In mode, R2And R3It can simultaneously be H, in other implementations, R2And R3It is not simultaneously H； R2And R3Can it is identical or
Difference, it is further preferred that R2And R3It is identical, and in H, ethyl, isopropyl, cyclohexyl, phenyl and pyridyl group at least
It is a kind of.
According to the disclosure, Ar1、Ar2、Ar3And Ar4Can be each independently selected from phenyl, aminomethyl phenyl, ethylphenyl,
At least one in xenyl, naphthalene, pyridyl group, carbazyl, carbazyl phenyl, pyridinylphenyl, fluorenyl and N- fluorenyl carbazyl
Kind, preferably at least one of phenyl, xenyl, naphthalene, pyridyl group and pyridinylphenyl.Ar2And Ar3It can be identical or not
Together, it is preferable that Ar2And Ar3It is identical, and can in phenyl, xenyl, naphthalene, pyridyl group and pyridinylphenyl at least one
Kind.
Preferably, Ar1It can be at least one of phenyl, pyridyl group, naphthalene and xenyl；
Preferably, Ar4It can be at least one of phenyl, xenyl, naphthalene, pyridyl group and pyridinylphenyl.
According to the disclosure, L can have structure shown in formula (3), wherein Y1、Y2、Y3And Y4It can select each independently
From N or C；* connection site is indicated.Wherein, Y1、Y2、Y3And Y4It can be each independently selected from
N or CRY, RYH, C can be selected from1~C6Aliphatic alkyl, C3~C6Naphthenic base, substituted or unsubstituted C6~C20It aromatic radical and takes
Generation or unsubstituted C2~C20At least one of heteroaryl, it is preferable that Y1、Y2、Y3And Y4It can be CRY, further excellent
Selection of land, RYIt can be H, i.e. L is phenylene.
According to the disclosure, nitrogenous heterocyclic aromatic amino-derivative preferably is selected from one of following structural formula:
The nitrogenous heterocyclic aromatic amino-derivative that disclosure second aspect provides above-mentioned first aspect is preparing organic electroluminescence
Application in luminescent device.
The disclosure third aspect provides a kind of organic electroluminescence device, including substrate, anode layer, cathode layer, Yi Jijie
At least one layer of organic function layer between anode layer and cathode layer, the organic function layer include hole injection layer, hole biography
Defeated layer, organic luminous layer, electron transfer layer and electron injecting layer, the hole injection layer, hole transmission layer, You Jifa
According to being formed on the anode layer, the cathode layer is formed in described for photosphere, electron transfer layer and electron injecting layer
On electron transfer layer, the electron transport layer materials of the electron transfer layer contain nitrogen-containing heterocycle described in disclosure first aspect
Aromatic amino-derivative, preferably comprise compound P1~P46.
Excellent properties of the organic electroluminescence device of the disclosure based on disclosure compound, compared with the prior art, this
Short of electricity subbase group in invention compound is located at molecule periphery, and whole electron mobility improves, while in short of electricity group
Nitrogen-atoms increases on space structure with the nitrogen-atoms distance on arylamine, increases the redox stability of molecule itself, body
It is now embodied in reduction device operating voltages in the devices, extends device lifetime.
The substrate in conventional organic luminescence device can be used in the substrate of disclosure organic electroluminescence device, such as: glass
Glass, polymer material and glass with TFT component and polymer material etc. are, it is preferable to use glass substrate.
Anode layer material can use indium tin oxygen (ITO), indium zinc oxygen (IZO), stannic oxide (SnO2), zinc oxide (ZnO)
Equal transparent conductive materials are also possible to the metal materials such as silver and its alloy, aluminium and its alloy, are also possible to that PEDOT etc. is organic to be led
The multilayered structure of electric material and above-mentioned material.Cathode layer materials can be the metals, metal such as magnesium silver mixture, LiF/Al, ITO
Mixture, oxide.
Hole injection layer material and hole transport layer material can be each independently selected from following compound HT1~HT31
At least one of:
According to the disclosure, the organic luminous layer of organic electroluminescence device can be also possible to multiple light for single-shot photosphere
Layer structure；Luminescent color is unlimited, can be to be such as red, yellow, blue, green, and organic luminous layer may include that material of main part and doping contaminate
Material, wherein blue-fluorescence main body may include at least one of following compound BFH-1~BFH-14:
Blue fluorescent dyes may include at least one of following compound BFD-1~BFD-9:
The compound of the present invention can be, but not limited to be used in mixed way with the following electron transport material enumerated.
It can also include the electron injecting layer between electron transfer layer and cathode, electron injecting layer material in device
The including but not limited to following one or more combinations enumerated.
LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca.
Brief description is carried out to the synthetic method of disclosure compound below.
The nitrogenous heterocyclic aromatic amino-derivative of the disclosure is obtained by coupling reaction；
Representative synthesis path 1 is as follows, corresponds to the nitrogenous heterocyclic arylamine class that synthesis has structure shown in general formula (1)
Derivative, wherein X represents halogen (chlorine, bromine or iodine), R1、Ar1、Ar2、Ar3、 X1、X2、X3、X4And X5It is as defined above literary institute
It states；
Representative synthesis path 2 is as follows, corresponds to the nitrogenous heterocyclic arylamine class that synthesis has structure shown in general formula (2)
Derivative, wherein X represents halogen (chlorine, bromine or iodine), R2、R3、Ar1、Ar4、 X1、X2、X3、X4And X5It is as defined above described in text；
Different target compounds can be obtained by the coupling reactant for replacing different.It should be noted that above-mentioned conjunction
Buchwald-Hartwig is used to be coupled in method, but be not restricted to that the coupling method, those skilled in the art can also be with
Method known to other methods, such as Liv Ullmann etc. is chosen, but is not limited to these methods, any equivalent synthetic method, all
It can according to need selection.
Unless otherwise indicated, raw materials used, intermediate is commercial goods in the disclosure；Mass spectrum uses in the disclosure
ZAB-HS type mass spectrograph measures (manufacture of Micromass company, Britain), and elemental analysis is surveyed using vario EL type elemental analyser
Fixed (manufacture of Elementar Analysensysteme GmbH company, Britain).
Synthetic example 1: the synthesis of compound P4
Under nitrogen protection, in equipped in churned mechanically four-hole bottle, thermometer, in the 1000mL four-hole bottle of condenser pipe plus
Enter bis- (2- naphthalene) anthracene (compound M2) 45.8g (0.09mol, 1eq) of bromo- 9, the 10- of product 2-, N- phenyl -4- (pyridine -3-
Base) aniline (compound N 3) 24.4g (0.099mol, 1.1eq), Pd2(dba)30.4g (0.00045mol, 0.5%), s-
Phos0.4g, sodium tert-butoxide 17.3g (0.18mol, 2eq), toluene 500mL, reaction mixture back flow reaction 6h, TLC monitoring are anti-
It should complete.
It is cooled to room temperature, water and methylene chloride extraction, organic phase concentration is added, concentrate column chromatography for separation obtains solid
Product.
The magnetic resonance spectroscopy data of product:1H NMR(500MHz,Chloroform)δ9.28–9.19(m, 1H),8.75–
8.66 (m, 1H), 8.33 (dt, J=15.0,3.0Hz, 1H), 8.29-8.17 (m, 2H), 8.14-7.94 (m, 6H), 7.69-
7.52 (m, 9H), 7.47 (dt, J=15.0,7.5Hz, 2H), 7.42-7.19 (m, 9H), 7.13-6.94 (m, 3H)；
The Elemental analysis data of product: C, 90.77%, H, 5.08%, N, 4.15%.
Synthetic example 2: the synthesis of compound P12
Using the method for synthetic example 1, the difference is that compound M1 is replaced with to the compound M12 of equivalent,
Obtain solid product.
The magnetic resonance spectroscopy data of product:1H NMR(500MHz,Chloroform)δ9.27–9.20(m, 1H),8.74–
8.65 (m, 1H), 8.33 (dt, J=15.0,3.0Hz, 1H), 8.29-8.16 (m, 2H), 7.81-7.69 (m, 4H), 7.63-
7.19(m,26H),7.14–6.93(m,3H)；
The Elemental analysis data of product: C, 90.88%, H, 5.27%, N, 3.85%.
Synthetic example 3: the synthesis of compound P15
Using the method for synthetic example 1, the difference is that compound N 1 is replaced with to the compound N 15 of equivalent,
Obtain solid product.
The magnetic resonance spectroscopy data of product:1H NMR (500MHz, Chloroform) δ 8.37 (dd, J=15.0,3.1Hz,
1H), 8.28-8.18 (m, 2H), 8.16-7.88 (m, 10H), 7.59 (ddq, J=9.9,3.9,3.4Hz, 7H), 7.47 (d, J
=15.0Hz, 1H), 7.44-7.21 (m, 9H), 7.14 (dd, J=15.0,3.1Hz, 1H), 7.06 (dt, J=15.0,
3.1Hz, 1H), 6.90 (td, J=15.0,3.1Hz, 1H)；
The Elemental analysis data of product: C, 88.86%, H, 4.92%, N, 6.22%.
Synthetic example 4: the synthesis of compound P23
Under nitrogen protection, in equipped in churned mechanically four-hole bottle, thermometer, in the 1000mL four-hole bottle of condenser pipe plus
Enter product 9- (2- naphthalene) -10- bromine anthracene (compound M23) 34.4g (0.09mol, 1eq), N- phenyl -4- (pyridin-3-yl) benzene
Amine (compound N 3) 24.4g (0.099mol, 1.1eq), Pd2(dba)30.4g (0.00045mol, 0.5%), s-phos0.4g,
Sodium tert-butoxide 17.3g (0.18mol, 2eq), toluene 500ml, reaction mixture back flow reaction 6h, TLC monitoring reaction are completed.
It is cooled to room temperature, water and methylene chloride extraction, organic phase concentration is added, concentrate column chromatography for separation obtains solid
Product.
The magnetic resonance spectroscopy data of product:1H NMR(500MHz,Chloroform)δ9.28–9.20(m, 1H),8.74–
8.65 (m, 1H), 8.33 (dt, J=15.0,3.0Hz, 1H), 8.25-8.12 (m, 4H), 8.12-8.02 (m, 2H), 7.99
(dd, J=15.0,2.9Hz, 1H), 7.69-7.51 (m, 5H), 7.51-7.40 (m, 5H), 7.41-7.33 (m, 3H), 7.30-
7.18(m,2H),7.14–6.92(m,3H)；
The Elemental analysis data of product: C, 89.75%, H, 5.14%, N, 5.11%.
Synthetic example 33: the synthesis of compound P33
Using the method for synthetic example 23, the difference is that by compound M23 replace with corresponding equivalent 9- [1,
1'- biphenyl] the bromo- 2- phenylanthracene (compound M33) of -4- base -10-, obtain solid product.
The magnetic resonance spectroscopy data of product:1H NMR(500MHz,Chloroform)δ9.26–9.20(m, 1H),8.96(d,
J=2.9Hz, 1H), 8.74-8.66 (m, 1H), 8.44 (d, J=15.0Hz, 1H), 8.33 (dt, J=15.0,3.0Hz, 1H),
8.16 (ddd, J=19.9,14.2,3.7Hz, 2H), 7.79-7.70 (m, 4H), 7.62 (dd, J=15.0,2.9Hz, 1H),
7.59–7.34(m,13H),7.30–7.18(m, 6H),7.13–6.93(m,3H)；
The Elemental analysis data of product: C, 90.43%, H, 5.27%, N, 4.30%.
Device embodiments 1
Using compound P1 as electron transport layer materials.
The glass plate for being coated with transparent conductive layer is ultrasonically treated in commercial detergent, is rushed in deionized water
It washes, in acetone: ultrasonic oil removing in alcohol mixed solvent is baked under clean environment and completely removes moisture content, with ultraviolet light and smelly
Oxygen cleaning, and with low energy cation beam bombarded surface；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, upper
Vacuum evaporation HT-11 is stated on anode tunic as hole injection layer, evaporation rate 0.1nm/s, vapor deposition film thickness is 10nm；
Hole transmission layer of the vacuum evaporation HT-2 as device on hole injection layer, evaporation rate 0.1nm/s,
Vapor deposition total film thickness is 80nm；
The luminescent layer of vacuum evaporation device on hole transmission layer, luminescent layer include material of main part and dye materials, benefit
The method steamed altogether with multi-source, adjusting material of main part BFH-4 evaporation rate are 0.1nm/s, 3% ratio of dyestuff PFD-1 evaporation rate
Setting, vapor deposition total film thickness are 30nm；
The electron transport layer materials (compound P1) of vacuum evaporation device, evaporation rate are on luminescent layer
0.1nm/s, vapor deposition total film thickness are 30nm；
On electron transfer layer (ETL) vacuum evaporation with a thickness of the LiF of 0.5nm as electron injecting layer, with a thickness of
Cathode of the Al layer of 150nm as device, obtains the organic electroluminescence device of the present embodiment, the measurement result of device performance
It is shown in Table 1.
Device embodiments 2~6
Respectively using compound P4, P12, P15, P23, P33 and P36 as electron transport layer materials, this implementation is respectively obtained
The organic electroluminescence device of example, the measurement result of device performance are shown in Table 1.
Device comparative example 1
Organic electroluminescence device is prepared using method identical with device embodiments 1, difference is, by electronics
Transport layer material compound P1 replaces with compound ET-58, and the measurement result of device performance is shown in Table 1.
Device comparative example 2
Organic electroluminescence device is prepared using method identical with device embodiments 1, difference is, by electronics
Transport layer material compound P1 replaces with compound ET-59, and the measurement result of device performance is shown in Table 1.
Testing example
Following performance measurement is carried out to the organic electroluminescence device prepared by the above process:
Under same brightness, is measured in Examples 1 to 6 and comparative example 1~2 and prepared using digital sourcemeter and luminance meter
The driving voltage and current efficiency of obtained organic electroluminescence device and the service life of device.Specifically, with 0.1V per second
Rate promote voltage, measure voltage i.e. driving voltage when the brightness of organic electroluminescence device reaches 1000cd/m2,
Current density at this time is measured simultaneously；The ratio of brightness and current density is current efficiency；The life test of LT95 is as follows:
Using luminance meter under 1000cd/m2 brightness, the electric current kept constant, the brightness for measuring organic electroluminescence device is reduced to
The time of 950cd/m2, unit are hour.
Table 1
The above result shows that new organic materials of the invention are used for organic electroluminescence device, can effectively reduce
Landing voltage is electron transport material of good performance.
The preferred embodiment of the disclosure is described in detail above, still, during the disclosure is not limited to the above embodiment
Detail a variety of simple variants can be carried out to the technical solution of the disclosure in the range of the technology design of the disclosure,
These simple variants belong to the protection scope of the disclosure.
It is further to note that specific technical features described in the above specific embodiments, in not lance
In the case where shield, it can be combined in any appropriate way.In order to avoid unnecessary repetition, the disclosure is to various
No further explanation will be given for possible combination.
In addition, any combination can also be carried out between a variety of different embodiments of the disclosure, as long as it is without prejudice to originally
Disclosed thought equally should be considered as disclosure disclosure of that.
Claims (10)
1. a kind of nitrogenous heterocyclic aromatic amino-derivative, which is characterized in that the nitrogenous heterocyclic aromatic amino-derivative has as follows
Structure shown in general formula (1) or formula (2):
Wherein, R1、R2And R3It is each independently selected from hydrogen, C1~C12Aliphatic alkyl, C3~C12It is naphthenic base, substituted or unsubstituted
C6~C30Aromatic radical and substituted or unsubstituted C2~C30At least one of heteroaryl；
L is selected from substituted or unsubstituted C6~C30Arlydene and substituted or unsubstituted C2~C30At least one in inferior heteroaryl
Kind；
Ar1、Ar2、Ar3And Ar4It is each independently selected from substituted or unsubstituted C6~C30Aryl and substituted or unsubstituted C2~
C30At least one of nitrogenous heteroaryl；
X1、X2、X3、X4And X5It is each independently selected from N or CRX, and X1、X2、X3、X4And X5In at least one be N, RXSelected from hydrogen, C1
~C12Aliphatic alkyl, C3~C12Naphthenic base, substituted or unsubstituted C6~C30Aromatic radical and substituted or unsubstituted C2~C30
At least one of heteroaryl.
2. nitrogenous heterocyclic aromatic amino-derivative according to claim 1, which is characterized in that the substituted C6~C30Virtue
Base, substituted C2~C30Heteroaryl, substituted C2~C30Inferior heteroaryl and substituted C2~C30Substituent group in nitrogenous heteroaryl
It is each independently halogen group, cyano, C1~C6Alkyl, C1~C6Alkoxy, C6~C30Aromatic radical or C2~C30It is miscellaneous
Aryl；
The C6~C30Aryl be selected from phenyl, xenyl, terphenyl, naphthalene, anthryl, fluoranthene base, phenanthryl, indenyl, fluorenyl,
Benzo fluorenyl, triphenylene, pyrenyl, base,At least one of base and aphthacene base；
The C2~C30Heteroaryl is selected from furyl, thienyl, pyrrole radicals, pyridyl group, carbazyl, benzofuranyl, benzo
Thienyl, isobenzofuran-base, indyl, quinolyl, isoquinolyl, dibenzofuran group, dibenzothiophene, benzo carbazole
At least one of base and dibenzo-carbazole base；
The C1~C12Aliphatic alkyl is at least one in methyl, ethyl, propyl, normal-butyl, n-pentyl and n-hexyl
Kind；
The C3~C12Naphthenic base is cyclopenta or cyclohexyl.
3. nitrogenous heterocyclic aromatic amino-derivative according to claim 1, which is characterized in that
X1For N, X2、X3、X4And X5For CRX；Or
X2For N, X1、X3、X4And X5For CRX；Or
X3For N, X1、X2、X4And X5For CRX；Or
X2And X3For N, X1、X4And X5For CRX；Or
X1And X4For N, X2、X3And X5For CRX。
4. nitrogenous heterocyclic aromatic amino-derivative according to claim 1, which is characterized in that R1、R2And R3Each independently
Selected from H, methyl, ethyl, isopropyl, n-propyl, normal-butyl, n-pentyl, n-hexyl, cyclopenta, cyclohexyl, phenyl, methylbenzene
Base, ethylphenyl, xenyl, naphthalene, pyridyl group, carbazyl, carbazyl phenyl, fluorenyl, N- fluorenyl carbazyl, methoxyl group, second
At least one at least one of oxygroup and trifluoromethyl, preferably H, ethyl, isopropyl, cyclohexyl, phenyl and pyridyl group
Kind；
It is further preferred that R2And R3It is identical, and at least one in H, ethyl, isopropyl, cyclohexyl, phenyl and pyridyl group
Kind.
5. nitrogenous heterocyclic aromatic amino-derivative according to claim 1, which is characterized in that Ar1、Ar2、Ar3And Ar4Respectively
Independently selected from phenyl, aminomethyl phenyl, ethylphenyl, xenyl, naphthalene, pyridyl group, carbazyl, carbazyl phenyl, pyridyl group
At least one of phenyl, fluorenyl and N- fluorenyl carbazyl；
Preferably, Ar2And Ar3It is identical, and selected from least one of phenyl, xenyl, naphthalene, pyridyl group and pyridinylphenyl；
Preferably, Ar1For at least one of phenyl, pyridyl group, naphthalene and xenyl；
Preferably, Ar4For at least one of phenyl, xenyl, naphthalene, pyridyl group and pyridinylphenyl.
6. nitrogenous heterocyclic aromatic amino-derivative according to claim 1, which is characterized in that L has to be tied shown in formula (3)
Structure, wherein Y1、Y2、Y3And Y4It is each independently selected from N or CRY, RYSelected from H, C1~C6Aliphatic alkyl, C3~C6Naphthenic base,
Substituted or unsubstituted C6~C20Aromatic radical and substituted or unsubstituted C2~C20At least one of heteroaryl；
Wherein, * indicates connection site；
Preferably, L is phenylene.
7. nitrogenous heterocyclic aromatic amino-derivative according to claim 1, which is characterized in that the nitrogenous heterocyclic arylamine
Analog derivative is selected from one of following structural formula:
8. nitrogenous heterocyclic aromatic amino-derivative described in any one of claim 1-7 is preparing organic electroluminescence device
In application.
9. application according to claim 8, which is characterized in that the nitrogenous heterocyclic aromatic amino-derivative has as described
The electron transport layer materials of organic electroluminescence devices.
10. a kind of organic electroluminescence device, including substrate, anode layer, cathode layer and between anode layer and cathode layer
At least one layer of organic function layer, the organic function layer includes hole injection layer, hole transmission layer, organic luminous layer, electronics
Transport layer and electron injecting layer, which is characterized in that the electron transport layer materials of the electron transfer layer contain claim 1-7
Any one of described in nitrogenous heterocyclic aromatic amino-derivative.
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