CN111377930A - Organic compound and application thereof - Google Patents
Organic compound and application thereof Download PDFInfo
- Publication number
- CN111377930A CN111377930A CN201811629859.3A CN201811629859A CN111377930A CN 111377930 A CN111377930 A CN 111377930A CN 201811629859 A CN201811629859 A CN 201811629859A CN 111377930 A CN111377930 A CN 111377930A
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- 150000002894 organic compounds Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 239000000463 material Substances 0.000 claims abstract description 44
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 10
- -1 nitro, hydroxyl Chemical group 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 5
- 239000012044 organic layer Substances 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 2
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000000732 arylene group Chemical group 0.000 abstract 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 abstract 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- 125000001769 aryl amino group Chemical group 0.000 abstract 1
- 125000005241 heteroarylamino group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 54
- 238000006243 chemical reaction Methods 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 230000005525 hole transport Effects 0.000 description 11
- 238000002347 injection Methods 0.000 description 11
- 239000007924 injection Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 9
- 239000011368 organic material Substances 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- 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 8
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 229960005544 indolocarbazole Drugs 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 5
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229910000160 potassium phosphate Inorganic materials 0.000 description 5
- 235000011009 potassium phosphates Nutrition 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002019 doping agent 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
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- JNGKNTZYAKKNLQ-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1h-triazine Chemical compound N=1N(Cl)NC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 JNGKNTZYAKKNLQ-UHFFFAOYSA-N 0.000 description 3
- GXVYYKSNVXVMNS-UHFFFAOYSA-N 9-(3-bromophenyl)phenanthrene Chemical compound BrC1=CC=CC(C=2C3=CC=CC=C3C3=CC=CC=C3C=2)=C1 GXVYYKSNVXVMNS-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 101000930898 Cryphonectria parasitica Glyceraldehyde-3-phosphate dehydrogenase Proteins 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- JZAFCDUOMYNXTO-UHFFFAOYSA-N 9-(4-bromophenyl)phenanthrene Chemical compound C1=CC(Br)=CC=C1C1=CC2=CC=CC=C2C2=CC=CC=C12 JZAFCDUOMYNXTO-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 101000766357 Ruditapes philippinarum Big defensin Proteins 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy 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
- 230000003321 amplification Effects 0.000 description 1
- 238000012863 analytical testing Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 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
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000002346 layers by function Substances 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
- 229920002521 macromolecule Polymers 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012046 mixed solvent Substances 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
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- 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
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- 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
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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
-
- 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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
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Abstract
The present invention discloses compounds of the general formula (1):
X1～X5each independently selected from N or CR4And at least one is N; y is1～Y8Selected from the group consisting of CR3Or N; r1And R2Selected from hydrogen, C1-C12 alkyl, C1-C12 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, aminoOne of aryl amino of C6-C30, heteroaryl amino of C3-C30, aryl of C6-C30 and heteroaryl of C3-C30; a is 1 or 2; b is an integer of 1-9; l is1One selected from substituted or unsubstituted C6-C30 arylene or substituted or unsubstituted C3-C30 heteroarylene; l is2One selected from single bond, substituted or unsubstituted C6-C30 arylene or substituted or unsubstituted C3-C30 heteroarylene. The compound of the present invention shows excellent device performance and stability when used as a light emitting material in an OLED device. The invention also protects the organic electroluminescent device adopting the compound with the general formula.
Description
Technical Field
The invention relates to an organic compound, in particular to a compound for an organic electroluminescent device and application of the compound in the organic electroluminescent device.
Background
Compared with a liquid crystal display, the organic electroluminescent display does not need a backlight source, has a large viewing angle and low power, has the response speed which can reach 1000 times that of the liquid crystal display, and has the manufacturing cost which is lower than that of the liquid crystal display with the same resolution, so the organic electroluminescent device has wide application prospect.
With the continuous advance of the OLED technology in the two fields of illumination and display, people pay more attention to the research on high-efficiency organic materials affecting the performance of OLED devices, and an organic electroluminescent device with good efficiency and long service life is generally the result of the optimized matching of the device structure and various organic materials. In the most common OLED device structures, the following classes of organic materials are typically included: hole injection materials, hole transport materials, electron transport materials, and light emitting materials (dyes or doped guest materials) and corresponding host materials of each color. Currently used phosphorescent host materials have single carrier transport capability, such as hole-based transport hosts and electron-based transport hosts. The carrier transport capability of a single one can cause a mismatch of electrons and holes in the light emitting layer, resulting in severe roll-off of efficiency and shortened lifetime. At present, in the use process of a phosphorescent host, a bipolar material or a double-host material matching mode is adopted to solve the problem of unbalanced carriers of a single-host material.
Disclosure of Invention
In order to solve the problems in the prior art, the inventors have studied and designed a novel class of compounds suitable for use in organic electroluminescent devices.
The present invention provides a compound of the general formula (1):
wherein: denotes Ar1And L2The attachment site of (a);
X1～X5each independently selected from N or CR4And at least one is N; further preferably, X1～X5Three of which are N.
Y1～Y8Are each independently selected from CR3Or N; preferably, Y is1～Y8Are all CR3。
Further preferably, Ar1One selected from the following formulae (2-1) and (2-2):
wherein Z is1～Z5Each independently selected from N, CH or CR5，Z6～Z13Each independently selected from N, C, CH or CR5(ii) a The R is5Independently selected from C1～C12Alkyl radical, C1～C12Alkoxy, halogen, cyano, nitro, hydroxy, silyl, amino, substituted or unsubstituted C6～C30Arylamino, substituted or unsubstituted C3～C30Heteroarylamino, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30One of heteroaryl;
and said Z is1～Z5At least 2 of which are N; and said Z is6～Z13At least 2 of which are N.
Further, in the formula (1), Ar1The following substituted or unsubstituted groups are preferred: a pyrimidine, quinazoline, quinoxaline, or triazine. Ar (Ar)1More preferably a triazine.
In the formula (1), R1～R4Are identical or different from each other and are each independently selected from hydrogen, C1～C12Alkyl radical, C1～C12Alkoxy, halogen, cyano, nitro, hydroxy, silyl, amino, substituted or unsubstituted C6～C30Arylamino, substituted or unsubstituted C3～C30Heteroarylamino, substituted or unsubstituted C6～C30Aryl or substituted or unsubstituted C3～C30One of heteroaryl;
R1～R4each independently may be fused to the attached phenyl ring to form C9～C30Aryl or C9～C30Heteroaryl, the aryl or heteroaryl formed being optionally substituted or unsubstituted C with 0, 1, 2, 3,4 or 5 each independently1～C12Alkyl, halogen, cyano, nitro, hydroxy, silyl, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30Substituents in heteroaryl groups.
b is an integer of 1-9; a is 1 or 2;
in the formula (1), L1Selected from substituted or unsubstituted C6～C30Arylene or substituted or unsubstituted C3～C30One of heteroarylenes; l is2Selected from single bond, substituted or unsubstituted C6～C30Arylene or substituted or unsubstituted C3～C30One of heteroarylenes.
Further preferred, L1Selected from substituted or unsubstituted C6～C18Arylene or substituted or unsubstituted C3～C18One of heteroarylenes;
further preferred, L2Selected from single bond, substituted or unsubstituted C6～C18Arylene or substituted or unsubstituted C3～C18One of a heteroarylene group; even more preferably, L2Selected from single bonds or phenylene.
Further, L1Selected from the following structural formulas S1-S6:
wherein,
indicating the connection location.
When the above groups have substituents, the substituents are respectively and independently selected from halogen, cyano, C1-C10Alkyl or cycloalkyl of, C2-C6Alkenyl or cycloalkenyl of1-C6Alkoxy or thioalkoxy of C6-C30Aryl of (C)3-C30One of the heteroaryl groups of (a).
Further, in the general formula (1) of the present invention, the following compounds of specific structures can be preferably selected: A1-A36, these compounds being representative only.
The invention also provides, as another aspect thereof, the use of a compound as described above in an organic electroluminescent device. In particular, the compound can be used as a luminescent host material in an organic electroluminescent device.
As still another aspect of the present invention, the present invention also provides an organic electroluminescent device comprising a first electrode, a second electrode and a plurality of organic layers interposed between the first electrode and the second electrode, characterized in that the organic layers contain an organic compound selected from the above-mentioned general formula (1) of the present invention.
Researches show that the compound with the general formula has good film-forming property and is suitable for being used as a luminescent main body material. The principle is not clear, and it is presumed that the following reasons may be:
by introducing phenanthrene fragments with excellent charge transport performance into a compound taking indolocarbazole as a parent nucleus structure, the charge transport performance of the whole material is improved, carrier balance in a system can be realized, and the luminous efficiency and the service life of the material are improved.
The invention has a structure of phenanthrene segment substituted indolocarbazole, wherein the indolocarbazole segment has good structural stability, and the application of the indolocarbazole segment in a main body material shows that the indolocarbazole segment has a proper energy level and is beneficial to matching with a functional layer material. In addition, the indolocarbazole fragment has high charge transport performance, and in the invention, the mother nucleus of indolocarbazole is connected with the phenanthrene fragment with high-efficiency electron transport performance, so that the charge transport efficiency can be improved, and the luminous efficiency of the main material can be improved. And on the mother nucleus of indolocarbazole, when the phenanthrene segment is directly connected with the mother nucleus, due to the influence of steric hindrance, the HOMO distribution overlapping part in the molecule is less, and when phenanthrene is connected with the mother nucleus through phenylene, the HOMO distribution is obviously overlapped on the phenylene, and the molecular structure can effectively improve the luminous efficiency of the material. Meanwhile, the mobility of the charges is improved, and the voltage is reduced. The collocation of the phenanthrene segment and the triazine substituent enables the charge transport performance of the whole molecule to be very efficient and keeps the balance of current carriers, and the specific expression is that the luminous efficiency and the service life of the main material are improved.
In addition, the preparation process of the compound is simple and feasible, the raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
Detailed Description
The present invention will be described in further detail below with reference to specific embodiments in order to make the present invention better understood by those skilled in the art.
Compounds of synthetic methods not mentioned in the present invention are all starting products obtained commercially. The solvent and reagent used in the present invention, such as methylene chloride, petroleum ether, ethanol, tetrahydrofuran, N-dimethylacetamide, anhydrous magnesium sulfate, carbazole, benzimidazole and the like, can be purchased from domestic chemical product markets, such as reagents from national drug group, TCI, shanghai Bidi medicine, carbofuran, and the like. In addition, they can be synthesized by a known method by those skilled in the art.
The analytical testing of intermediates and compounds in the present invention uses an abciex mass spectrometer (4000QTRAP) and a siemens analyzer.
The synthesis of the compounds of the present invention is briefly described below.
Synthetic examples
Representative synthetic route 1:
the above synthesis methods are mainly used for C-C coupling and C-N coupling, but the method is not limited to this coupling method, and those skilled in the art can select other methods, but not limited to these methods, and all of them can be selected according to the needs.
More specifically, the following gives synthetic methods of representative compounds of the present invention.
Synthesis example 1:
synthesis of Compound A1
Under the protection of nitrogen, adding 38.1g (100mmol) of indolo [ 3,2A ] carbazole and 21.1g (100mmol) of 3- (9-phenanthryl) bromobenzene into a reaction bottle, dissolving in xylene, adding cuprous iodide, 1, 10-phenanthroline and potassium phosphate, heating and refluxing, reacting for 12h, washing with water, concentrating, and performing column chromatography to obtain an M1-1 intermediate.
M1-133.2 g (100mmol) was charged into a reaction flask, and dissolved in 200ml of DMF, 4.8g (200mmol) of NaH was added to the reaction solution, and the mixture was stirred at room temperature for 2 hours, and 56.9g (110mmol) of 2-chloro-4, 6-diphenyltriazine was added thereto. And stopping the reaction after the reaction is finished. Water was added to the reaction solution to precipitate, and the precipitate was filtered, and the obtained solid was purified by recrystallization from toluene to obtain A1.
1H NMR(CDCl3,400MHz)1H NMR(400MHz,Chloroform)δ9.08(s,1H),8.84(s,1H),8.55(s, 2H),8.32(d,J＝12.0Hz,4H),8.21(d,J＝6.8Hz,4H),7.90(s,1H),7.73–7.50(m,12H),7.47(s,1H), 7.12(m,6H).
Synthesis example 2:
synthesis of Compound A8
Under the protection of nitrogen, adding 38.1g (100mmol) of indolo [ 3,2A ] carbazole and 21.1g (100mmol) of 3- (10-phenyl-9-phenanthryl) bromobenzene into a reaction bottle, dissolving in xylene, adding cuprous iodide, 1, 10-phenanthroline and potassium phosphate, heating and refluxing, reacting for 12h, washing with water, concentrating, and carrying out column chromatography to obtain an M-2 intermediate.
M-233.2 g (100mmol) was charged into a reaction flask, and dissolved in 200ml of DMF, 4.8g (200mmol) of NaH was added to the reaction solution, and stirred at room temperature for 2 hours, and 56.9g (110mmol) of 2-chloro-4, 6-diphenyltriazine was added thereto. And stopping the reaction after the reaction is finished. Water was added to the reaction solution to precipitate, and the precipitate was filtered, and the obtained solid was purified by recrystallization from toluene to obtain A8.
1H NMR(CDCl3,400MHz)1H NMR(400MHz,Chloroform)δ9.08(s,1H),8.55(s,1H),8.36(s,2H), 8.19(d,J＝16.0Hz,2H),7.72–7.44(m,8H),7.41(s,1H),7.18–6.90(m,3H).
Synthesis example 3:
synthesis of Compound A11
Under the protection of nitrogen, adding 38.1g (100mmol) of 2-N heteroandole [ 3,2A ] carbazole and 21.1g (100mmol) of 3- (9-phenanthryl) bromobenzene into a reaction bottle, dissolving in xylene, adding cuprous iodide, 1, 10-phenanthroline and potassium phosphate, heating and refluxing, reacting for 12h, washing with water, concentrating, and performing column chromatography to obtain an M-3 intermediate.
M-333.2 g (100mmol) was charged into a reaction flask, and dissolved in 200ml of DMF, 4.8g (200mmol) of NaH was added to the reaction solution, and stirred at room temperature for 2 hours, and 56.9g (110mmol) of 2-chloro-4, 6-diphenyltriazine was added thereto. And stopping the reaction after the reaction is finished. Water was added to the reaction solution to precipitate, and the precipitate was filtered, and the obtained solid was purified by recrystallization from toluene to obtain A11.
1H NMR(CDCl3,400MHz)1H NMR(400MHz,Chloroform)δ9.34(s,1H),9.08(s,1H),8.84(s,1H), 8.55(s,1H),8.43–8.38(m,4H),8.36(d,J＝4.0Hz,5H),8.30–7.97(m,4H),7.80(d,J＝10.0Hz,2H),7.68– 7.58(m,5H),7.55–7.19(m,10H),7.14(d,J＝10.0Hz,2H).
Synthesis example 4:
synthesis of Compound A16
Under the protection of nitrogen, adding 38.1g (100mmol) of indolo [ 3,2A ] carbazole and 21.1g (100mmol) of 4- (9-phenanthryl) bromobenzene into a reaction bottle, dissolving in xylene, adding cuprous iodide, 1, 10-phenanthroline and potassium phosphate, heating and refluxing, reacting for 12h, washing with water, concentrating, and performing column chromatography to obtain an M-4 intermediate.
In a reaction flask, 24g (100mmol) of 2- (4-bromobenzene) -4, 6-diphenyltriazine, M-432 g (100mmol), 200ml of xylene, 43.3g (314mmol) of sodium tert-butoxide, Pd (dba) 5%, and 2ml of tri-tert-butylphosphine were added and reacted at 140 ℃ for 8 hours. And stopping the reaction after the reaction is finished. After cooling to room temperature, water was added to the reaction solution, followed by liquid separation and concentration of the organic phase, the obtained solid was purified by recrystallization from toluene to obtain a 16.
1H NMR(CDCl3,400MHz)9.08(s,2H),8.84(s,2H),8.55(s,4H),8.36(s,7H),8.27(s,3H),7.91(t, J＝4.0Hz,4H),7.81(s,2H),7.66(d,J＝12.0Hz,10H),7.51(d,J＝8.0Hz,6H),7.19–6.90(m,10H)。
Synthesis example 5:
synthesis of Compound A19
Under the protection of nitrogen, adding 38.1g (100mmol) of indolo [ 3,2A ] carbazole and 21.1g (100mmol) of 3- (9-phenanthryl) bromobenzene into a reaction bottle, dissolving in xylene, adding cuprous iodide, 1, 10-phenanthroline and potassium phosphate, heating and refluxing, reacting for 12h, washing with water, concentrating, and performing column chromatography to obtain an M-5 intermediate.
In a reaction flask, 24g (100mmol) of 2- (3-bromobenzene) -4-phenyl-6- (2-yl-9, 9-dimethylfluorene) triazine, 200ml of xylene, 43.3g (314mmol) of sodium tert-butoxide, 5% of Pd (dba) and 2ml of tri-tert-butylphosphine were added and reacted at 140 ℃ for 8 hours. And stopping the reaction after the reaction is finished. After cooling to room temperature, water was added to the reaction solution, followed by liquid separation and concentration of the organic phase, the obtained solid was purified by recrystallization from toluene to obtain a 19.
1H NMR(CDCl3,400MHz)9.08(s,2H),8.84(s,2H),8.55(s,4H),8.36(s,3H),8.33–8.12(m,11H), 8.09(s,2H),7.96(s,2H),7.90(s,4H),7.80–7.42(m,35H),7.58–7.42(m,15H),7.58–7.43(m,15H),7.34(s, 1H),7.24(s,1H),7.18–6.89(m,10H),1.69(s,12H).
Device embodiments
Detailed description of the preferred embodiments
The OLED includes first and second electrodes, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), or any combination thereof may be used. When the first electrode is used as a cathode, a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof can be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compound used as the organic material layer may be an organic small molecule, an organic large molecule, and a polymer, and a combination thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as compounds shown below in HT-1 to HT-34; or any combination thereof.
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more compounds of HT-1 to HT-34 described above, or one or more compounds of HI1-HI3 described below; one or more of the compounds HT-1 to HT-34 may also be used to dope one or more of the compounds HI1-HI3 described below.
The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The single color light emitting layers of a plurality of different colors may be arranged in a planar manner in a pixel pattern, or may be stacked to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light-emitting layer may be a single color light-emitting layer capable of emitting red, green, blue, or the like at the same time.
According to different technologies, the luminescent layer material can be different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescent luminescent material, and the like. In an OLED device, a single light emitting technology may be used, or a combination of a plurality of different light emitting technologies may be used. These technically classified different luminescent materials may emit light of the same color or of different colors.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer can be selected from, but is not limited to, one or more of GPD-1 to GPD-47 listed below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer thereof may be selected from, but not limited to, a combination of one or more of RPD-1 to RPD-28 listed below.
The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single-layer structure including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, the combination of one or more of ET-1 through ET-57 listed below.
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer materials including, but not limited to, combinations of one or more of the following.
LiQ,LiF,NaCl,CsF,Li2O,Cs2CO3,BaO,Na,Li,Ca。
The preparation process of the organic electroluminescent device in the embodiment is as follows:
the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, vacuum evaporating HT-11 on the anode layer film to form a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
evaporating HT-5 on the hole injection layer in vacuum to serve as a hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 80 nm;
a luminescent layer of the device is evaporated in vacuum on the hole transport layer, the luminescent layer comprises a main material and a dye material, the evaporation rate of the main material is adjusted to be 0.1nm/s by utilizing a multi-source co-evaporation method, the evaporation rate of the dye GPD-1 is set in a proportion of 3%, the main material adopts the compound disclosed by the invention or the compound in the prior art, and the total film thickness of the evaporation is 30 nm;
vacuum evaporating an electron transport layer material ET42 of the device on the light-emitting layer, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 30 nm;
LiF with the thickness of 0.5nm is vacuum-evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, and an Al layer with the thickness of 150nm is used as a cathode of the device.
Method of testing the device (including equipment and test conditions):
the organic electroluminescent device prepared by the above process was subjected to the following performance measurement:
the driving voltage and current efficiency of the organic electroluminescent devices of the examples and comparative examples and the lifetime of the devices were measured at the same luminance using a digital source meter and a luminance meter. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent device reached 10000cd/m2The current density is measured at the same time as the driving voltage; the ratio of the brightness to the current density is the current efficiency; life test of LT95The following were used: using a luminance meter at 10000cd/m2The luminance drop of the organic electroluminescent device was measured to be 9500cd/m at luminance, maintaining a constant current2Time in hours.
For the purpose of comparing device application properties of the light emitting material of the present invention, compounds R-1 and R-2 shown below were used as comparative materials.
Example 1
The compound A1 of the invention is used as a main material of a luminescent layer, an organic electroluminescent device is prepared according to the preparation process of the organic electroluminescent device, and the device performance test is carried out according to the organic electroluminescent device test method.
Example 2
An organic electroluminescent device was produced in the same manner as in example 1, except that compound a1 was replaced with A3.
Example 3
An organic electroluminescent device was produced in the same manner as in example 1, except that compound a1 was replaced with A8.
Example 4
An organic electroluminescent device was produced in the same manner as in example 1, except that compound a1 was replaced with a 11.
Example 5
An organic electroluminescent device was produced in the same manner as in example 1, except that compound a1 was replaced with a 16.
Example 6
An organic electroluminescent device was produced in the same manner as in example 1, except that compound a1 was replaced with a 19.
Comparative example 1
An organic electroluminescent device was produced in the same manner as in example 1, except that compound a1 was replaced with R-1.
Comparative example 2
An organic electroluminescent device was produced in the same manner as in example 1, except that compound a1 was replaced with R-2.
The properties of the organic electroluminescent devices prepared according to the above embodiments of the present invention are shown in table 1 below.
Table 1:
from the data in table 1 above, it can be seen that: as can be seen from a comparison of examples 1-6 with comparative examples 1-2, the compounds synthesized according to the present invention, when used as host materials in OLED devices, have superior performance, both in terms of current efficiency and device lifetime, compared to known OLED devices prepared using prior art materials, while having a relatively lower pull-off voltage.
Compared with R-1, the compound can realize the common transmission of holes and electrons and the transmission balance of the holes and the electrons, thereby reducing the voltage, improving the luminous efficiency, reducing exciton quenching and prolonging the service life.
Compared with R-2, the compound has stronger electric absorption property and higher triplet state energy level, can effectively realize the compounding of the main material and the dye, and improves the luminous efficiency.
Although the present invention has been described in connection with the embodiments, the present invention is not limited to the above-described embodiments, and it is to be understood that various modifications and improvements can be made by those skilled in the art within the spirit of the present invention, and the scope of the present invention is outlined by the appended claims.
Claims (10)
1. A compound of the formula (1):
wherein: denotes Ar1And L2The attachment site of (a);
X1～X5are respectively independentIs selected from N or CR4And at least one is N;
Y1～Y8are each independently selected from CR3Or N;
R1～R4each independently selected from hydrogen and C1～C12Alkyl radical, C1～C12Alkoxy, halogen, cyano, nitro, hydroxy, silyl, amino, substituted or unsubstituted C6～C30Arylamino, substituted or unsubstituted C3～C30Heteroarylamino, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30One of heteroaryl; r1～R4Each independently may be fused to the attached aromatic ring to form a substituted or unsubstituted C9～C30Aryl, substituted or unsubstituted C9～C30One of heteroaryl;
a is 1 or 2; b is an integer of 1-9;
L1selected from substituted or unsubstituted C6～C30Arylene, substituted or unsubstituted C3～C30One of heteroarylenes;
L2selected from single bond, substituted or unsubstituted C6～C30Arylene, substituted or unsubstituted C3～C30One of heteroarylenes;
when the above groups have substituents, the substituents are respectively and independently selected from halogen, cyano, C1～C10Alkyl or cycloalkyl of, C2～C6Alkenyl or cycloalkenyl of1～C6Alkoxy or thioalkoxy of C6～C30Aryl of (C)3～C30The heteroaryl group of (a).
2. A compound of formula (la) according to claim 1, wherein in formula (1):
X1～X5three of which are N.
3. Root of herbaceous plantA compound of formula (1) according to claim 1, wherein in formula (1), Ar1One selected from the following formulae (2-1) and (2-2):
wherein Z is1～Z5Each independently selected from N, CH or CR5，Z6～Z13Each independently selected from N, carbon atom, CH or CR5(ii) a The R is5Independently selected from C1～C12Alkyl radical, C1～C12Alkoxy, halogen, cyano, nitro, hydroxy, silyl, amino, substituted or unsubstituted C6～C30Arylamino, substituted or unsubstituted C3～C30Heteroarylamino, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C3～C30One of heteroaryl;
and said Z is1～Z5At least 2 of which are N; and said Z is6～Z13At least 2 of which are N.
4. A compound of formula (la) according to any one of claims 1 to 3, wherein in formula (1), Y1～Y8Are all CR3。
5. A compound of formula (1) according to claim 1, wherein in formula (1), Ar1Selected from the following substituted or unsubstituted groups: one of a pyrimidine, quinazoline, quinoxaline, or triazine.
6. A compound of formula (la) according to any one of claims 1 to 3, wherein in formula (1):
L1selected from substituted or unsubstituted C6～C18Arylene or substituted or unsubstituted C3～C18One of heteroarylenes;
L2selected from single bond, substituted or unsubstituted C6～C18Arylene, substituted or unsubstituted C3～C18One of heteroarylenes;
preferably, L2Selected from single bonds or phenylene.
7. A compound of formula (la) according to any one of claims 1 to 3, wherein in formula (1), L1Selected from the following structural formulas S1-S6:
wherein,
indicating the connection location.
8. A compound of formula (la) according to claim 1, selected from the compounds of the following specific structures:
9. use of a compound of general formula (la) according to claim 1 or 8 as a light-emitting host material in an organic electroluminescent device.
10. An organic electroluminescent device comprising a first electrode, a second electrode and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layer comprises at least one compound selected from the group consisting of compounds represented by the general formula of claim 1, or the organic layer comprises at least one compound selected from the group consisting of compounds represented by claim 8.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113087714A (en) * | 2021-04-16 | 2021-07-09 | 王磊 | Axial chiral aryl indole carbazole derivative and preparation method and application thereof |
| CN114149429A (en) * | 2020-09-08 | 2022-03-08 | 三星Sdi株式会社 | Compound for organic photoelectric device, composition for organic photoelectric device, and display device |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114149429A (en) * | 2020-09-08 | 2022-03-08 | 三星Sdi株式会社 | Compound for organic photoelectric device, composition for organic photoelectric device, and display device |
| CN113087714A (en) * | 2021-04-16 | 2021-07-09 | 王磊 | Axial chiral aryl indole carbazole derivative and preparation method and application thereof |
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