CN106170477A - 2 amino-metadiazine compounds, organic electroluminescence device and display device - Google Patents
2 amino-metadiazine compounds, organic electroluminescence device and display device Download PDFInfo
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- CN106170477A CN106170477A CN201580000029.2A CN201580000029A CN106170477A CN 106170477 A CN106170477 A CN 106170477A CN 201580000029 A CN201580000029 A CN 201580000029A CN 106170477 A CN106170477 A CN 106170477A
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- Prior art keywords
- substitution
- phenyl
- anthryl
- carbazole
- substituted
- Prior art date
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- 238000005401 electroluminescence Methods 0.000 title claims abstract description 91
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical class NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 49
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 43
- 125000003118 aryl group Chemical group 0.000 claims abstract description 38
- 230000027756 respiratory electron transport chain Effects 0.000 claims abstract description 35
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- -1 amino-metadiazine compound Chemical class 0.000 claims abstract description 8
- 238000006467 substitution reaction Methods 0.000 claims description 142
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 96
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 66
- 239000000463 material Substances 0.000 claims description 64
- 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 60
- 150000001875 compounds Chemical class 0.000 claims description 52
- 125000001624 naphthyl group Chemical group 0.000 claims description 51
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 47
- 230000005540 biological transmission Effects 0.000 claims description 29
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 21
- 125000005561 phenanthryl group Chemical group 0.000 claims description 18
- 235000010290 biphenyl Nutrition 0.000 claims description 15
- 239000004305 biphenyl Substances 0.000 claims description 15
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 6
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 claims description 6
- 125000006267 biphenyl group Chemical group 0.000 claims description 6
- 150000001721 carbon Chemical class 0.000 claims description 6
- 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 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- FBTOLQFRGURPJH-UHFFFAOYSA-N 1-phenyl-9h-carbazole Chemical compound C1=CC=CC=C1C1=CC=CC2=C1NC1=CC=CC=C12 FBTOLQFRGURPJH-UHFFFAOYSA-N 0.000 claims description 3
- 230000037429 base substitution Effects 0.000 claims description 3
- 150000001716 carbazoles Chemical class 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- 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 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 9
- 239000010410 layer Substances 0.000 description 129
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 238000001704 evaporation Methods 0.000 description 19
- 230000008020 evaporation Effects 0.000 description 19
- 238000007738 vacuum evaporation Methods 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 13
- 239000000758 substrate Substances 0.000 description 12
- 238000001819 mass spectrum Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 239000011521 glass Substances 0.000 description 8
- 239000011368 organic material Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical class [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 5
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 5
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 230000005311 nuclear magnetism Effects 0.000 description 4
- BRUOAURMAFDGLP-UHFFFAOYSA-N 9,10-dibromoanthracene Chemical class C1=CC=C2C(Br)=C(C=CC=C3)C3=C(Br)C2=C1 BRUOAURMAFDGLP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000012459 cleaning agent Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000005083 Zinc sulfide Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- 125000005266 diarylamine group Chemical group 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 125000005259 triarylamine group Chemical group 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- WTHNRYPHMCDZBE-UHFFFAOYSA-N 1-phenyl-2H-pyrimidin-2-amine Chemical class NC1N=CC=CN1C1=CC=CC=C1 WTHNRYPHMCDZBE-UHFFFAOYSA-N 0.000 description 1
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 description 1
- AVXFJPFSWLMKSG-UHFFFAOYSA-N 2,7-dibromo-9h-fluorene Chemical class BrC1=CC=C2C3=CC=C(Br)C=C3CC2=C1 AVXFJPFSWLMKSG-UHFFFAOYSA-N 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 230000005525 hole transport Effects 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
- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 1
- 230000009191 jumping Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000005036 potential barrier Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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- 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
- C07D213/60—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02E10/50—Photovoltaic [PV] energy
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Abstract
The invention discloses a kind of 2 amino-metadiazine compounds and include organic electroluminescence device and the display device of this 2 amino-metadiazine compound.2 amino-metadiazine compounds of the present invention are as shown in logical formula (I), wherein, and Ar1、Ar2And Ar3Separately being selected from carbon number is the aryl of 6 30；X1、X2、X3、X4Separately selected from the alkyl that hydrogen, carbon number are 1 12, carbon number be the aryl of 6 12.2 amino-metadiazine compounds of the present invention can be applied in organic electroluminescence device, is used as electron transfer layer or organic luminous layer, is conducive to improving brightness and the luminous efficiency of organic electroluminescence device, and can reduce driving voltage.
Description
The present invention relates to display technology field, more particularly to 2- amino-metadiazine compounds, organic electroluminescence device and display device.
Organic electroluminescence device (Organic Light Emitting Display, abbreviation OLED) it is used as new flat-panel monitor and liquid crystal display (Liquid Crystal Display, abbreviation LCD) compare, there is luminous thin, light, wide viewing angle, active, glow color continuously adjustabe, low cost, fast response time, energy consumption is small, driving voltage is low, operating temperature range is wide, simple production process, luminous efficiency high and can Flexible Displays.OLED is just because of the very big concern that industrial circle and scientific circles have been obtained with the incomparable advantage of other displays and fine application prospect.
Electro optical phenomenon is just had discovered that early in nineteen thirties, initial luminescent material is zinc sulphide (ZnS) powder, has thus developed LED technology, present LED technology is widely used on energy-conserving light source.Organic electroluminescent phenomenon is found that earliest in Pope in 1963 et al., they have found that the single layer crystal of anthracene under the driving of more than 100V voltages, can send faint blue light.Until 1987, bi-layer devices are made in organic fluorescent dye by doctor Deng Qingyun of Kodak et al. in the way of vacuum evaporation, it is less than in driving voltage under 10V voltage, external quantum efficiency (External quantum efficiency, abbreviation EQE) reach 1%, so that electroluminescent organic material and its device are provided with the possibility of practicality, the research of OLED material and its device has been promoted significantly from this.
Relative to phosphor, electroluminescent organic material has advantages below：Organic material good processability, can by evaporation or spin coating method on any substrate film forming；The diversity of organic molecular structure allows to adjust the heat endurance of organic material, engineering properties, luminous and electric conductivity by Molecular Design and the method for modification so that material is significantly improved space.
The principle of luminosity of organic electroluminescent diode is similar with inorganic light-emitting diode.When element is by straight
Derived from stream electricity during forward bias voltage drop, additional voltage energy will drive electronics (Electron) with hole (Hole) respectively by negative electrode and anode injection element, met in luminescent layer when both, with reference to when, form so-called electron-hole and be combined exciton, exciton returns to ground state by the form of luminescence relaxation, so as to reach luminous purpose.
What the generation of organic electroluminescent was leaned on is the restructuring of the carrier (electronics and hole) transmitted in organic semiconducting materials, it is well-known, the electric conductivity of organic material is very poor, from unlike inorganic semiconductor, there is no the energy band continued in organic semiconductor, the transmission of carrier is conventional to jump theory to describe, i.e. under the driving of an electric field, electronics is being excited or is being injected into the lumo energy of molecule, via lumo energy (the Highest Occupied Molecular Orbital for jumping to another molecule, abbreviation HOMO) come reach electric charge transmission purpose.In order to be able to make organic electroluminescence device reach breakthrough in application aspect, it is necessary to overcome organic material electric charge to inject and the poor difficulty of transmittability.The adjustment that scientists pass through device architecture, for example increase the number of device organic material layer, and different organic layers is played the part of different device layers, the functional material for example having can promote electronics to be injected from negative electrode and promote hole to be injected from anode, some materials can promote the transmission of electric charge, the material played the role of can then play stop electronics and hole transport, the luminescent material of certain a variety of colors most important in organic electroluminescence device will also reach the purpose matched with adjacent functional material, the organic electroluminescence device of one excellent in efficiency long lifespan is typically the result of the optimization collocation of device architecture and various organic materials, this functionalization material for just designing and developing various structures for chemists provides great opportunities and challenges.
Existing organic electroluminescence device generally comprises the negative electrode being arranged in order from top to bottom, electron transfer layer (Electron transport Layer, abbreviation ETL), organic luminous layer (Emitting Layer, abbreviation EML), hole transmission layer, anode and substrate.The raising of organic electroluminescence device efficiency, mainly improves the formation probability of exciton as far as possible in organic luminous layer.Therefore, the material of the organic luminous layer of organic electroluminescence device and electron transfer layer adjacent thereto plays vital effect to the luminous efficiency of organic electroluminescence device and brightness, therefore, a kind of suitable material of expectation is needed badly to improve luminous efficiency and the brightness of organic electroluminescence device.
The content of the invention
The invention provides 2- amino-metadiazine compounds, the organic electroluminescence device comprising the compound and the display device with the organic electroluminescence device, to solve the problem of luminous efficiency of organic electroluminescence device in the prior art and relatively low brightness.
The present invention provides 2- amino-metadiazine compounds, and the compound is as shown in logical formula (I)：
Wherein, Ar1、Ar2And Ar3The aryl that the aryl for being separately 6-30 selected from carbon number, the carbon number of substitution are 6-30；X1、X2、X3、X4The aryl that aryl that the alkyl for being separately 1-12 selected from hydrogen, carbon number, carbon number are 6-12, the carbon number of substitution are 6-12.
It is preferred that, the aryl that described substituted carbon number is 6-30 be specially carbon number be 1-12 alkyl-substituted carbon number be 6-30 aryl.
It is preferred that, Ar1、Ar2And Ar3The aryl that the aryl for being separately 6-24 selected from carbon number, the carbon number of substitution are 6-24；X1、X2、X3、X4The aryl that aryl that the alkyl for being separately 1-12 selected from hydrogen, carbon number, carbon number are 6, the carbon number of substitution are 6.
It is preferred that, described Ar1、Ar2And Ar3Separately it is selected from phenyl, alkyl-substituted phenyl, the phenyl of phenyl substitution, the phenyl of naphthyl substituted, the phenyl of anthryl substitution, the phenyl of fluorenyl substitution, the carbazyl of N- phenyl substitution, the phenyl of phenanthryl substitution, naphthyl, alkyl-substituted naphthyl, the naphthyl of phenyl substitution, the naphthyl of naphthyl substituted, the naphthyl of anthryl substitution, the naphthyl of fluorenyl substitution, the naphthyl of carbazole N- substitutions, the naphthyl of carbazole 3- substitutions, the naphthyl of phenanthryl substitution, anthryl, alkyl-substituted anthryl, the anthryl of phenyl substitution, the anthryl of naphthyl substituted, the anthryl of anthryl substitution, the anthryl of fluorenyl substitution, the anthryl of carbazole N- substitutions, the anthryl of carbazole 3- substitutions, the anthryl of phenanthryl substitution, fluorenyl, alkyl-substituted fluorenyl, the fluorenyl of phenyl substitution, the fluorenyl of naphthyl substituted, the fluorenyl of anthryl substitution, the fluorenyl of phenanthryl substitution, the fluorenyl of carbazole N- substitutions, the fluorenyl of carbazole 3- substitutions, the fluorenyl of fluorenyl substitution, carbazole, it is alkyl-substituted
Carbazole, the carbazole of phenyl substitution, the carbazole of naphthyl substituted, the carbazole of anthryl substitution, the carbazole of phenanthryl substitution, the carbazole of carbazole N- substitutions, the carbazole of carbazole 3- substitutions, terphenyl, alkyl-substituted terphenyl, the xenyl of naphthyl substituted, the xenyl of anthryl substitution, the xenyl of phenanthryl substitution, the xenyl of fluorenyl substitution, the xenyl of carbazole substitution, the phenyl of diphenyl substitution, the phenyl of phenyl napthyl substitution, the phenyl of phenyl carbazole base substitution, the naphthyl of xenyl substitution, the fluorenyl of biphenyl substitution, the carbazyl of biphenyl substitution, the phenyl of binaphthyl substitution, the binaphthyl of phenyl substitution, the anthryl of diphenyl substitution, the anthryl of phenyl napthyl substitution, the anthryl of dinaphthyl substitution, the anthryl of triaryl substitution, it is Spirofluorene-based；
Described X1、X2、X3、X4Separately it is selected from hydrogen, methyl, ethyl, propyl group, isopropyl, normal-butyl, isobutyl group, amyl group, isopentyl, cyclopenta, alkyl-substituted cyclopenta, n-hexyl, cyclohexyl, alkyl-substituted cyclohexyl, phenyl, alkyl-substituted phenyl.
Ar1Selected from xenyl, anthryl, fluorenyl；Ar2And Ar3Separately selected from phenyl, naphthyl, adjacent 3,5-dimethylphenyl；X1、X2、X3、X4Separately it is selected from hydrogen, methyl.
It is preferred that, the compound is selected from：
The embodiment of the present invention also provides a kind of organic electroluminescence device based on above-mentioned 2- amino-metadiazine compounds, including electron transfer layer, and the material of the electron transfer layer is the 2- amino-metadiazine compounds described in any of the above-described embodiment.
By further preferred, the material of the electron transfer layer is selected from：
It is preferred that, described organic electroluminescence device, in addition to anode, hole transmission layer, organic luminous layer, electron injecting layer and negative electrode；Wherein, the anode, hole transmission layer, organic luminous layer, electron transfer layer, electron injecting layer and negative electrode are arranged in order from bottom to up.
The embodiment of the present invention also provides a kind of display device, including any of the above-described kind of organic electroluminescence device.
The embodiment of the present invention still further provides a kind of organic electroluminescence device, including organic luminous layer, and the material of main part of the organic luminous layer is the 2- amino-metadiazine compounds described in any of the above-described embodiment.
It is preferred that, the organic luminous layer is green light emitting layer, and the material of main part of the green light emitting layer is selected from any of the above-described described 2- amino-metadiazine compounds.
It is preferred that, the organic luminous layer is red light luminescent layer, and the material of main part of the red light luminescent layer is selected from any of the above-described described 2- amino-metadiazine compounds.
It is preferred that, described organic electroluminescence device, in addition to anode, hole transmission layer, electron transfer layer, electron injecting layer and negative electrode；Wherein, the anode, hole transmission layer, organic luminous layer, electron transfer layer, electron injecting layer and negative electrode are arranged in order from bottom to up.
The embodiment of the present invention also provides a kind of display device, including this another organic electroluminescence device.
The present invention has the beneficial effect that：
The 2- amino-metadiazine compounds that the present invention is provided can be applied in the electron transfer layer and organic luminous layer of organic electroluminescence device, found through experiment, using 2- amino-metadiazine compounds, be conducive to improving brightness and the luminous efficiency of organic electroluminescence device, and driving voltage can be reduced.
Fig. 1 is the general structure of 2- amino-metadiazine compounds provided in an embodiment of the present invention；
Fig. 2 is compound P1 prepared by the embodiment of the present invention 1 nuclear magnetic spectrogram；
Fig. 3 is compound P2 prepared by the embodiment of the present invention 2 nuclear magnetic spectrogram；
Fig. 4 is compound P4 prepared by the embodiment of the present invention 4 nuclear magnetic spectrogram；
Fig. 5 is compound P6 prepared by the embodiment of the present invention 6 nuclear magnetic spectrogram.
The embodiments of the invention provide 2- amino-metadiazine compounds, the organic electroluminescence device comprising the compound and the display device with the organic electroluminescence device.In order that the object, technical solutions and advantages of the present invention are clearer, below the present invention is described in further detail, it is clear that described embodiment is only a part of embodiment of the invention, rather than whole embodiments.Based on the embodiment in the present invention, all other embodiment that those of ordinary skill in the art are obtained under the premise of creative work is not made belongs to the scope of protection of the invention.
What it is firstly the need of explanation is, in organic electroluminescence device, hole mobile material (the Hole Injection Material of hole transmission layer, abbreviation HTM), it is required that with high heat endurance (high Tg), there is less potential barrier with anode or hole-injecting material, higher cavity transmission ability can vacuum evaporation formation pin-hole free films.Conventional HTM is aromatic multi-amine class compound, mainly derivative of tri-arylamine group.
Electron transport material (the Electron transport Material of electron transfer layer, abbreviation ETM) require that ETM has reversible and sufficiently high electrochemical reduction current potential, suitable HOMO energy levels and LUMO (Lowest Unoccupied Molecular Orbital, lowest unoccupied molecular orbital) energy level value enables electronics preferably to inject, and it is preferably provided with hole blocking ability；Higher electron transport ability, the film forming having had and heat endurance.ETM is typically the aromatic compound of the conjugate planes of short of electricity minor structure.
Organic luminous layer includes material of main part (host) and guest materials, and wherein guest materials is luminescent material, and such as dyestuff, material of main part needs to have following characteristics：Reversible electrochemical redox current potential, the HOMO energy levels and lumo energy matched with adjacent hole transmission layer and electron transfer layer, it is good and
The hole matched and electron transport ability, good high heat endurance and film forming, and suitable singlet or triplet state energy gap are used for controlling exciton in luminescent layer, also have energy transfer good between corresponding fluorescent dye or phosphorescent coloring.
The luminescent material of organic luminous layer, it is necessary to possess following characteristics by taking dyestuff as an example：With high fluorescence or phosphorescence quantum efficiency；It is overlapping that the absorption spectrum of dyestuff and the emission spectrum of main body have had, i.e., main body is adapted to dyestuff energy, can effectively energy transmission from main body to dyestuff；The emission peak of red, green, blue is as narrow as possible, with the excitation obtained；Stability is good, can be deposited etc..
Embodiments of the invention provide 2- amino-metadiazine compounds first, and the compound is as shown in logical formula (I) (i.e. general structure (I) shown in Fig. 1)：
Wherein, Ar1、Ar2And Ar3The aryl that the aryl for being separately 6-30 selected from carbon number, the carbon number of substitution are 6-30；X1、X2、X3、X4The aryl that aryl that the alkyl for being separately 1-12 selected from hydrogen, carbon number, carbon number are 6-12, the carbon number of substitution are 6-12.
In the technical scheme, " separately selected from " refers to that group can be selected independently, for example, Ar with identical or difference1、Ar2And Ar3Separately selected from the aryl that carbon number is 6-30, i.e. Ar1、Ar2And Ar3It is the aryl that carbon number is 6-30, and Ar1、Ar2And Ar3It is able to can also be differed with identical.Carbon number is 6-30 aryl, i.e. the carbon number with aroma properties is 6-30 compound, such as phenyl, naphthyl, xenyl, anthryl, carbon number refers to unsubstituted for 6-30 aryl, i.e. no substituent, and the carbon number replaced refers to substitution, such as tolyl for 6-30 aryl.Carbon number is the alkyl for the straight or branched that 1-12 alkyl, i.e. the total number of carbon atoms are 1-12, for example, methyl, ethyl, n-propyl, isopropyl, normal-butyl, isobutyl group etc..
It is preferred that, the aryl that described substituted carbon number is 6-30 be specially carbon number be 1-12 alkyl-substituted carbon number be 6-30 aryl.
It is preferred that, Ar1、Ar2And Ar3The aryl that the aryl for being separately 6-24 selected from carbon number, the carbon number of substitution are 6-24；X1、X2、X3、X4The aryl that aryl that the alkyl for being separately 1-12 selected from hydrogen, carbon number, carbon number are 6, the carbon number of substitution are 6.
It is preferred that, described Ar1、Ar2And Ar3Separately it is selected from phenyl,Alkyl-substituted phenyl,The phenyl of phenyl substitution,The phenyl of naphthyl substituted,The phenyl of anthryl substitution,The phenyl of fluorenyl substitution,The carbazyl of N- phenyl substitution,The phenyl of phenanthryl substitution,Naphthyl,Alkyl-substituted naphthyl,The naphthyl of phenyl substitution,The naphthyl of naphthyl substituted,The naphthyl of anthryl substitution,The naphthyl of fluorenyl substitution,The naphthyl of carbazole N- substitutions,The naphthyl of carbazole 3- substitutions,The naphthyl of phenanthryl substitution,Anthryl,Alkyl-substituted anthryl,The anthryl of phenyl substitution,The anthryl of naphthyl substituted,The anthryl of anthryl substitution,The anthryl of fluorenyl substitution,The anthryl of carbazole N- substitutions,The anthryl of carbazole 3- substitutions,The anthryl of phenanthryl substitution,Fluorenyl,Alkyl-substituted fluorenyl,The fluorenyl of phenyl substitution,The fluorenyl of naphthyl substituted,The fluorenyl of anthryl substitution,The fluorenyl of phenanthryl substitution,The fluorenyl of carbazole N- substitutions,The fluorenyl of carbazole 3- substitutions,The fluorenyl of fluorenyl substitution,Carbazole,Alkyl-substituted carbazole,The carbazole of phenyl substitution,The carbazole of naphthyl substituted,The carbazole of anthryl substitution,The carbazole of phenanthryl substitution,The carbazole of carbazole N- substitutions,The carbazole of carbazole 3- substitutions,Terphenyl,Alkyl-substituted terphenyl,The xenyl of naphthyl substituted,The xenyl of anthryl substitution,The xenyl of phenanthryl substitution,The xenyl of fluorenyl substitution,The xenyl of carbazole substitution,The phenyl of diphenyl substitution,The phenyl of phenyl napthyl substitution,The phenyl of phenyl carbazole base substitution,The naphthyl of xenyl substitution,The fluorenyl of biphenyl substitution,The carbazyl of biphenyl substitution,The phenyl of binaphthyl substitution,The binaphthyl of phenyl substitution,The anthryl of diphenyl substitution,The anthryl of phenyl napthyl substitution,The anthryl of dinaphthyl substitution,The anthryl of triaryl substitution,It is Spirofluorene-based；
Described X1、X2、X3、X4Separately it is selected from hydrogen, methyl, ethyl, propyl group, isopropyl, normal-butyl, isobutyl group, amyl group, isopentyl, cyclopenta, alkyl-substituted cyclopenta, n-hexyl, cyclohexyl, alkyl-substituted cyclohexyl, phenyl, alkyl-substituted phenyl.
Inventor has found, in formula, it is preferred that Ar1Selected from xenyl, anthryl, fluorenyl；Ar2And Ar3Separately selected from phenyl, naphthyl, adjacent 3,5-dimethylphenyl；X1、X2、X3、X4Separately it is selected from hydrogen, methyl.
It is preferred that, the compound is selected from：
The embodiment of the present invention also provides a kind of organic electroluminescence device based on above-mentioned 2- amino-metadiazine compounds, including electron transfer layer, and the material of the electron transfer layer is the 2- amino-metadiazine compounds described in any of the above-described embodiment.
By further preferred, the material of the electron transfer layer is selected from：
In the present invention, it can be top radiation organic EL part that the type of organic electroluminescence device, i.e. organic electroluminescence device are not limited, or bottom emitting organic electroluminescence device.It is preferred that, described organic electroluminescence device, in addition to anode, hole transmission layer, organic luminous layer, electron injecting layer and negative electrode；Wherein, the anode, hole transmission layer, organic luminous layer, electron transfer layer, electron injecting layer and negative electrode are arranged in order from bottom to up.
The embodiment of the present invention also provides a kind of display device, including this organic electroluminescence device.Brightness and luminous efficiency due to above-mentioned organic electroluminescence device are improved, and driving voltage is reduced, therefore the display effect of display device is improved, and reduce energy consumption.
The embodiment of the present invention still further provides a kind of organic electroluminescence device, including organic luminous layer, institute
It is the 2- amino-metadiazine compounds described in any of the above-described embodiment to state the material of main part of organic luminous layer.Organic luminous layer can be phosphorescence luminescent layer, or fluorescent light-emitting layer, wherein material of main part are using the 2- amino-metadiazine compounds described in any of the above-described embodiment.
By it is further preferred that the organic luminous layer is green light emitting layer, the material of main part of the green light emitting layer is selected from any of the above-described described 2- amino-metadiazine compounds.
It is preferred that, the organic luminous layer is red light luminescent layer, and the material of main part of the red light luminescent layer is selected from any of the above-described described 2- amino-metadiazine compounds.
It is further preferred that when the organic luminous layer is green luminescence, the material of main part of the organic luminous layer is selected from：
When the organic luminous layer is red light-emitting, the material of main part of the organic luminous layer is selected from：
In the present invention, it can be top radiation organic EL part that the type of organic electroluminescence device, i.e. organic electroluminescence device are not limited, or bottom emitting organic electroluminescence device.It is preferred that, described organic electroluminescence device, in addition to anode, hole transmission layer, electron transfer layer, electron injecting layer and negative electrode；Wherein, the anode, hole transmission layer, organic luminous layer, electron transfer layer, electron injecting layer and negative electrode are arranged in order from bottom to up.
The embodiment of the present invention also provides a kind of display device, including this another organic electroluminescence device.
Brightness and luminous efficiency due to above-mentioned organic electroluminescence device are improved, and driving voltage is reduced, therefore the display effect of display device is improved, and reduce energy consumption.
It is described in more detail 2- amino-metadiazine compounds, organic electroluminescence device and the display device of the present invention with embodiment, but the present invention and is not limited to the examples restriction.
Embodiment：2- amino-metadiazine compounds and its synthesis
The synthesis of embodiment 1, compound P1
In 500 milliliters of there-necked flasks, under nitrogen protection, 300 milliliters of dry toluene are added; 16.8 grams of N, N`- biphenyl diamines, 12.1 grams of 2- chlorine pyrimidines; 10.1 grams of sodium tert-butoxides, 0.28 gram of double (dibenzalacetone) palladium, the toluene solution of 1 gram 10% of tri-butyl phosphine; it is heated to back flow reaction 6 hours; room temperature is down to, solid is filtrated to get, solid dichloromethane dissolves; silica gel post separation, petroleum ether：Ethyl acetate：Dichloromethane=6：2：2 elutions, obtain 15.0 grams of product.Detected through mass spectrum and nuclear-magnetism, mass spectrum MS (m/e)：492, compound P1 nuclear magnetic spectrogram (1H) as shown in Figure 2.
The synthesis of embodiment 2, compound P2
In 500 milliliters of there-necked flasks, under nitrogen protection, 300 milliliters of dry toluene are added; 16.8 grams of N, N`- biphenyl diamines, 15.2 grams of 2- chloro- 4; 6- dimethyl pyrimidines, 10.1 grams of sodium tert-butoxides, 0.28 gram of double (dibenzalacetone) palladium; the toluene solution of 1 gram 10% of tri-butyl phosphine, is heated to back flow reaction 6 hours, is down to room temperature; it is filtrated to get solid; solid dichloromethane dissolves, silica gel post separation, petroleum ether：Ethyl acetate：Dichloromethane=6：2：2 elutions, obtain 16.1 grams of product.Detected through mass spectrum and nuclear-magnetism, mass spectrum MS (m/e)：548, compound P2 nuclear magnetic spectrogram (1H) as shown in Figure 3.
The synthesis of embodiment 3, compound P3
In 500 milliliters of there-necked flasks, under nitrogen protection, 300 milliliters of dry toluene are added; 21.8 grams of N, N`- bis- (1- naphthyls) benzidine, 15.2 grams of 2- chloro- 4; 6- dimethyl pyrimidines, 10.1 grams of sodium tert-butoxides, 0.28 gram of double (dibenzalacetone) palladium; the toluene solution of 1 gram 10% of tri-butyl phosphine, is heated to back flow reaction 6 hours, is down to room temperature; it is filtrated to get solid; solid dichloromethane dissolves, silica gel post separation, petroleum ether：Ethyl acetate：Dichloromethane=6：2：2 elutions, obtain 23.9 grams of product, through Mass Spectrometer Method, mass spectrum MS (m/e)：648.
The synthesis of embodiment 4, compound P4
1st, aniline and 2- chlorine pyrimidine reaction generation intermediate P4-1.
In 500 milliliters of there-necked flasks, under nitrogen protection, 300 milliliters of dry toluene are added; 22.9 grams of 2- chlorine pyrimidines, 23 grams of aniline, 20 grams of sodium tert-butoxides; 0.56 gram of double (dibenzalacetone) palladium; the toluene solution of 2 gram 10% of tri-butyl phosphine is heated to back flow reaction 6 hours, is down to room temperature, organic layer washing; divide liquid; after being concentrated to dryness, silica gel post separation, petroleum ether：Ethyl acetate：Dichloromethane=6：2：2 elutions, obtain 29.1 grams of product, through Mass Spectrometer Method, mass spectrum MS (m/e)：171.
2nd, P4-1 and 9,10- dibromoanthracenes reaction generation target product P4.
In 1000 milliliters of there-necked flasks; under nitrogen protection; add 600 milliliters of dry toluene; 17.1 grams of N- phenyl -2- aminopyrimidines, 15.0 grams of 9,10- dibromoanthracenes; 10.2 gram sodium tert-butoxide; 0.28 gram of double (dibenzalacetone) palladium, the toluene solution of 1 gram 10% of tri-butyl phosphine is heated to back flow reaction 6 hours, is down to
Room temperature, is filtrated to get solid, and solid dichloromethane dissolves, silica gel post separation, petroleum ether：Ethyl acetate：Dichloromethane=6：2：2 elutions, obtain 16.0 grams of product.Detected through mass spectrum and nuclear-magnetism, mass spectrum MS (m/e)：516, compound P4 nuclear magnetic spectrogram (1H) as shown in Figure 4.
The synthesis of embodiment 5, compound P5
Compound P5 synthesis is similar with compound P4, only changes 2- chlorine pyrimidines into 3,5- dimethyl -2- chlorine pyrimidines, obtains product P5, through Mass Spectrometer Method, mass spectrum MS (m/e)：628.
The synthesis of embodiment 6, compound P6
Compound P6 synthesis is similar with compound P4, only changes 9,10- dibromoanthracenes into 2,7- dibromo fluorenes, obtains product P6.Detected through mass spectrum and nuclear-magnetism, mass spectrum MS (m/e)：532, compound P6 nuclear magnetic spectrogram (1H) as shown in Figure 5.
Embodiment 7~21, embodiment 23~25, embodiment 27~29：Compound P7~P21, P23~P25, P27~P29 synthesis
Reference compound P4 synthetic method, is reacted using different bromo-derivatives and diaryl amine, following 21 compounds of synthesis, is listed as follows：
Embodiment 22 and embodiment 26：Compound P22 and P26 synthesis
Reference compound P1 synthetic method, is reacted using different bromo-derivatives and diaryl amine, following 2 compounds of synthesis, is listed as follows：
Embodiment：Organic electroluminescence device and its preparation
The typical structure of OLED organic electroluminescence devices is：
Substrate/anode/hole transmission layer (HTL)/organic luminous layer (EL)/electron transfer layer (ETL)/negative electrode
Substrate can use the substrate in conventional organic luminescence organic electroluminescence device, for example：Glass or plastics.Anode material can use transparent high conductivity material, such as indium tin oxygen (ITO), indium zinc oxygen (IZO), tin ash (SnO2), zinc oxide (ZnO) etc..Glass substrate is selected in the organic electroluminescence device of the present invention makes, ITO makees anode material.
Hole transmission layer can use N, N '-two (3- tolyls)-N, N '-diphenyl-[1,1- xenyls] -4,4 '-diamines (TPD) or N, N '-diphenyl-N, N '-two (1- naphthyls)-(1,1 '-xenyl) the tri-arylamine group material such as -4,4 '-diamines (NPB).Wherein NPB is conventional hole mobile material, and selected hole mobile material selects NPB in the organic electroluminescence device of the present invention makes.
Organic electroluminescence device structure can also be able to be multi-luminescent layer structure for single-shot photosphere.
Electron transfer layer uses Alq3(8-hydroxyquinoline aluminium) or TAZ (3- phenyl -4- (1 '-naphthyl) -5- benzene -1,2,4- triazoles) or TPBi (1,3,5- tri- (N- phenyl -2- benzimidazoles) benzene) or any two kinds of collocation for being derived from these three materials.
Selected cathode material is LiF/Al in the organic electroluminescence device of the present invention makes.
The EM1 used in the present invention concrete structure is seen below：
First, the compound of the embodiment of the present invention 1~29 in organic electroluminescence device as electron transfer layer application
In embodiments, 12 organic electroluminescence devices are prepared for altogether, wherein organic electroluminescence device A1-A11 (being prepared respectively by embodiment 30~40) is used as electron transfer layer from the compound of the present invention, organic electroluminescence device A12 (being prepared by comparative example 1) is using conventional electron transport layer materials Bphen (4,7-diphenyl-1,10-phenanthroline, 4,7- diphenyl -1,10- o-phenanthroline) it is used as electron transfer layer.
The organic electroluminescence device A1-A12 of preparation structure is：ITO/NPB(40nm)/EM1(30nm)/ETL(20nm)/LiF(0.5nm)/Al(150nm).
Organic electroluminescence device A1-A12 preparation process is as follows：
The glass substrate for being coated with transparent conductive layer (as anode) is carried out in cleaning agent ultrasonically treated, then rinse in deionized water, the ultrasonic oil removing in acetone and alcohol mixed solvent again, it is baked to again under clean environment and removes moisture content completely, with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface, to improve the surface nature on surface, improve the binding ability with follow-up hole transmission layer；
Above-mentioned glass substrate is placed in vacuum chamber, 1 × 10 is evacuated to-5-9×10-3Pa, vacuum evaporation NPB is as hole transmission layer on anode, and evaporation rate is 0.1nm/s, and evaporation thickness is 50nm；
Vacuum evaporation EM1 is as the organic luminous layer of device on hole transmission layer, and evaporation rate is 0.1nm/s, and evaporation total film thickness is 30nm；
The compound and Bphen of the vacuum evaporation present invention are distinguished on organic luminous layer as the electron transfer layer of organic electroluminescence device, its evaporation rate is 0.1nm/s, and evaporation total film thickness is 50nm；
Vacuum evaporation 0.5nm LiF is used as electron injecting layer on electron transfer layer (ETL)；
Vacuum evaporation 150nm aluminium (Al) is used as negative electrode on electron injecting layer.
Device performance testing result such as table 1.
The organic electroluminescence device A1-A12 performance tables of table 1
As shown in Table 1, under conditions of same requirement brightness, using the compound of the present invention as organic electroluminescence device made from electron transfer layer, it has relatively low driving voltage, and with higher current efficiency.
2nd, the compound of the embodiment of the present invention 1~29 in organic electroluminescence device as organic luminous layer green glow material of main part application, organic luminescent device be green phosphorescent organic electroluminescence device
In the present embodiment, 20 organic electroluminescence devices are prepared for altogether, respectively organic electroluminescence device B1-B20, wherein organic electroluminescence device B1-B19 (being prepared respectively by embodiment 41~49) is from material of main part of the compounds of this invention as organic luminous layer, organic electroluminescence device B20 (being prepared by comparative example 2) is using conventional material of main part CBP (4,4 '-Bis (9-carbazolyl) -1,1 '-biphenyl, 4,4 '-two (9- carbazoles) -1,1 '-biphenyl) it is used as material of main part.
The organic electroluminescence device B1-B20 of preparation structure is：ITO/NPB (20nm)/green glow material of main part：Ir(ppy)3[7%] (30nm)/TPBI (10nm)/Alq3(15nm)/LiF(0.5nm)/Al(150nm)。
Organic electroluminescence device B1-B20 preparation process is as follows：
The glass substrate for being coated with transparent conductive layer (as anode) is carried out in cleaning agent ultrasonically treated, then rinse in deionized water, the ultrasonic oil removing in acetone and alcohol mixed solvent again, it is baked to again under clean environment and removes moisture content completely, with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface, to improve the surface nature on surface, improve the binding ability with follow-up hole transmission layer；
Above-mentioned glass substrate is placed in vacuum chamber, 1 × 10 is evacuated to-5-9×10-3Pa, vacuum evaporation NPB is as hole transmission layer in above-mentioned anode film layer, and evaporation rate is 0.1nm/s, and evaporation thickness is 20nm；
Vacuum evaporation light emitting host material and guest materials Ir (ppy) on hole transmission layer3As the green glow organic luminous layer of organic electroluminescence device, evaporation rate is 0.1nm/s, and evaporation total film thickness is 30nm；
The vacuum evaporation electron transfer layer TPBI and Alq successively on organic luminous layer3As electron transfer layer, its evaporation rate is 0.1nm/s, and evaporation thickness is respectively 10nm and 15nm；
Vacuum evaporation 0.5nm LiF is used as electron injecting layer on the electron transport layer；
Vacuum evaporation 150nm Al is used as negative electrode on electron injecting layer.
Device performance testing result such as table 2.
The organic electroluminescence device B1-B20 performance tables of table 2
As shown in Table 2, under conditions of same requirement brightness, preferable effect is obtained as organic electroluminescence device made from material of main part relative to using CBP as the organic electroluminescence device of phosphorescence host made from the material of main part of organic luminous layer using the compound of the present invention, higher current efficiency and relatively low driving voltage is obtained.
3rd, the compound of the embodiment of the present invention 1~29 in organic electroluminescence device as organic luminous layer feux rouges material of main part application, organic luminescent device be red phosphorescent organic electroluminescence device
In the present embodiment, 16 organic electroluminescence devices are prepared for altogether, respectively organic electroluminescence device C1-C16, wherein organic electroluminescence device C1-C15 (being prepared respectively by embodiment 60~74) is respectively from material of main part of the compounds of this invention as organic luminous layer, and organic electroluminescence device C16 (being prepared by comparative example 3) is using conventional material of main part CBP as material of main part.
The organic electroluminescence device C1-C16 of preparation structure is：ITO/NPB (20nm)/feux rouges material of main part：Ir(piq)3[5%] (30nm)/TPBI (10nm)/Alq3(15nm)/LiF(0.5nm)/Al(150nm)。
Organic electroluminescence device C1-C16 preparation process is as follows：
The glass substrate for being coated with transparent conductive layer (as anode) is carried out in cleaning agent ultrasonically treated, then rinse in deionized water, the ultrasonic oil removing in acetone and alcohol mixed solvent again, it is baked to again under clean environment and removes moisture content completely, with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface, to improve the surface nature on surface, improve the binding ability with follow-up hole transmission layer；
Above-mentioned glass substrate is placed in vacuum chamber, 1 × 10 is evacuated to-5-9×10-3Pa, vacuum evaporation NPB is as hole transmission layer in above-mentioned anode film layer, and evaporation rate is 0.1nm/s, and evaporation thickness is 20nm；
Vacuum evaporation light emitting host material and guest materials Ir (piq) on hole transmission layer3(three (1- phenyl-isoquinolin) close iridium (III)), as the feux rouges organic luminous layer of organic electroluminescence device, evaporation rate is 0.1nm/s, and evaporation total film thickness is 30nm；
The vacuum evaporation electron transfer layer TPBI and Alq successively on organic luminous layer3As electron transfer layer, its evaporation rate is 0.1nm/s, and evaporation thickness is respectively 10nm and 15nm；
Vacuum evaporation 0.5nm LiF is used as electron injecting layer on the electron transport layer；
Vacuum evaporation 150nm Al is used as negative electrode on electron injecting layer.
Device performance testing result such as table 3.
The organic electroluminescence device C1-C16 performance tables of table 3
As shown in Table 3, under conditions of same requirement brightness, preferable effect is obtained as organic electroluminescence device made from material of main part relative to using CBP as the organic electroluminescence device of phosphorescence host made from the material of main part of organic luminous layer using the compound of the present invention, higher current efficiency and relatively low driving voltage is obtained.
Obviously, those skilled in the art can carry out various changes and modification to the present invention without departing from the spirit and scope of the present invention.So, if these modifications and variations of the present invention belong within the scope of the claims in the present invention and its equivalent technologies, then the present invention is also intended to comprising including these changes and modification.
Claims (12)
- A kind of 2- amino-metadiazine compounds, it is characterised in that the compound is as shown in logical formula (I)：Wherein, Ar1、Ar2And Ar3The aryl that the aryl for being separately 6-30 selected from carbon number, the carbon number of substitution are 6-30；X1、X2、X3、X4The aryl that aryl that the alkyl for being separately 1-12 selected from hydrogen, carbon number, carbon number are 6-12, the carbon number of substitution are 6-12.
- Compound as claimed in claim 1, it is characterised in that the aryl that described substituted carbon number is 6-30 be specially carbon number be 1-12 alkyl-substituted carbon number be 6-30 aryl.
- Compound as claimed in claim 1 or 2, it is characterised in that Ar1、Ar2And Ar3The aryl that the aryl for being separately 6-24 selected from carbon number, the carbon number of substitution are 6-24；X1、X2、X3、X4The aryl that aryl that the alkyl for being separately 1-12 selected from hydrogen, carbon number, carbon number are 6, the carbon number of substitution are 6.
- Compound as claimed in claim 1, it is characterised in that described Ar1、Ar2And Ar3Separately it is selected from phenyl, alkyl-substituted phenyl, the phenyl of phenyl substitution, the phenyl of naphthyl substituted, the phenyl of anthryl substitution, the phenyl of fluorenyl substitution, the carbazyl of N- phenyl substitution, the phenyl of phenanthryl substitution, naphthyl, alkyl-substituted naphthyl, the naphthyl of phenyl substitution, the naphthyl of naphthyl substituted, the naphthyl of anthryl substitution, the naphthyl of fluorenyl substitution, the naphthyl of carbazole N- substitutions, the naphthyl of carbazole 3- substitutions, the naphthyl of phenanthryl substitution, anthryl, alkyl-substituted anthryl, the anthryl of phenyl substitution, the anthryl of naphthyl substituted, the anthryl of anthryl substitution, the anthryl of fluorenyl substitution, the anthryl of carbazole N- substitutions, the anthryl of carbazole 3- substitutions, the anthryl of phenanthryl substitution, fluorenyl, alkyl-substituted fluorenyl, the fluorenyl of phenyl substitution, the fluorenyl of naphthyl substituted, The fluorenyl of anthryl substitution, the fluorenyl of phenanthryl substitution, the fluorenyl of carbazole N- substitutions, the fluorenyl of carbazole 3- substitutions, the fluorenyl of fluorenyl substitution, carbazole, alkyl-substituted carbazole, the carbazole of phenyl substitution, the carbazole of naphthyl substituted, the carbazole of anthryl substitution, the carbazole of phenanthryl substitution, the carbazole of carbazole N- substitutions, the carbazole of carbazole 3- substitutions, terphenyl, alkyl-substituted terphenyl, the xenyl of naphthyl substituted, the xenyl of anthryl substitution, the xenyl of phenanthryl substitution, the xenyl of fluorenyl substitution, the xenyl of carbazole substitution, the phenyl of diphenyl substitution, the phenyl of phenyl napthyl substitution, the phenyl of phenyl carbazole base substitution, the naphthyl of xenyl substitution, the fluorenyl of biphenyl substitution, the carbazyl of biphenyl substitution, the phenyl of binaphthyl substitution, the binaphthyl of phenyl substitution, the anthryl of diphenyl substitution, the anthryl of phenyl napthyl substitution, the anthryl of dinaphthyl substitution, the anthryl of triaryl substitution, it is Spirofluorene-based；Described X1、X2、X3、X4Separately it is selected from hydrogen, methyl, ethyl, propyl group, isopropyl, normal-butyl, isobutyl group, amyl group, isopentyl, cyclopenta, alkyl-substituted cyclopenta, n-hexyl, cyclohexyl, alkyl-substituted cyclohexyl, phenyl, alkyl-substituted phenyl.
- Compound as claimed in claim 1, it is characterised in that the compound is selected from：
- A kind of organic electroluminescence device, including electron transfer layer, it is characterised in that the material of the electron transfer layer is the compound described in claim any one of 1-5.
- Organic electroluminescence device as claimed in claim 6, it is characterised in that the material of the electron transfer layer is selected from：
- A kind of organic electroluminescence device, including organic luminous layer, it is characterised in that the material of main part of the organic luminous layer is the compound as described in claim any one of 1-5.
- Organic electroluminescence device as claimed in claim 8, it is characterised in that the organic luminous layer is green light emitting layer, the material of main part of the green light emitting layer is selected from the compound described in any one of claim 1-5.
- Organic electroluminescence device as claimed in claim 8, it is characterised in that the organic luminous layer is red light luminescent layer, the material of main part of the red light luminescent layer is selected from the compound described in any one of claim 1-5.
- Organic electroluminescence device as claimed in claim 8, it is characterised in that also including anode, hole transmission layer, electron transfer layer, electron injecting layer and negative electrode；Wherein, the anode, hole transmission layer, organic luminous layer, electron transfer layer, electron injecting layer and negative electrode are arranged in order from bottom to up.
- A kind of display device, it is characterised in that including the organic electroluminescence device as described in claim any one of 6-11.
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| PCT/CN2015/071386 WO2016115718A1 (en) | 2015-01-23 | 2015-01-23 | 2-amino pyrimidine compound, organic electroluminescent device, and display device |
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|---|---|---|---|---|
| CN101613316A (en) * | 2008-02-29 | 2009-12-30 | 葛来西雅帝史派有限公司 | New organic electroluminescent compounds and the Organnic electroluminescent device that uses this compound |
| KR20110057078A (en) * | 2009-11-23 | 2011-05-31 | 에스에프씨 주식회사 | Heteroaryl amine compounds and organic light-emitting diode including the same |
| JP2013251480A (en) * | 2012-06-04 | 2013-12-12 | Udc Ireland Ltd | Material for organic electroluminescent element, organic electroluminescent element, light-emitting device using element, display device, and illumination device |
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| CN101613316A (en) * | 2008-02-29 | 2009-12-30 | 葛来西雅帝史派有限公司 | New organic electroluminescent compounds and the Organnic electroluminescent device that uses this compound |
| KR20110057078A (en) * | 2009-11-23 | 2011-05-31 | 에스에프씨 주식회사 | Heteroaryl amine compounds and organic light-emitting diode including the same |
| JP2013251480A (en) * | 2012-06-04 | 2013-12-12 | Udc Ireland Ltd | Material for organic electroluminescent element, organic electroluminescent element, light-emitting device using element, display device, and illumination device |
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