CN113527330A - Compound and application thereof - Google Patents
Compound and application thereof Download PDFInfo
- Publication number
- CN113527330A CN113527330A CN202010294719.6A CN202010294719A CN113527330A CN 113527330 A CN113527330 A CN 113527330A CN 202010294719 A CN202010294719 A CN 202010294719A CN 113527330 A CN113527330 A CN 113527330A
- Authority
- CN
- China
- Prior art keywords
- substituted
- unsubstituted
- compound
- group
- cyano
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 174
- 230000002950 deficient Effects 0.000 claims abstract description 23
- 239000010410 layer Substances 0.000 claims description 84
- 239000000463 material Substances 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- -1 nitro, hydroxyl Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 6
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 5
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000001769 aryl amino group Chemical group 0.000 claims description 5
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 5
- 239000010409 thin film Substances 0.000 claims description 5
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004306 triazinyl group Chemical group 0.000 claims description 3
- 125000006761 (C6-C60) arylene group Chemical group 0.000 claims description 2
- 125000004653 anthracenylene group Chemical group 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 238000002347 injection Methods 0.000 abstract description 35
- 239000007924 injection Substances 0.000 abstract description 35
- 238000013508 migration Methods 0.000 abstract description 11
- 230000005012 migration Effects 0.000 abstract description 11
- 230000021615 conjugation Effects 0.000 abstract description 5
- 230000002349 favourable effect Effects 0.000 abstract description 3
- LOTCVJJDZFMQGB-UHFFFAOYSA-N [N].[O].[S] Chemical compound [N].[O].[S] LOTCVJJDZFMQGB-UHFFFAOYSA-N 0.000 abstract description 2
- 239000004305 biphenyl Substances 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 75
- 238000006243 chemical reaction Methods 0.000 description 75
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
- 239000007787 solid Substances 0.000 description 39
- 229910052757 nitrogen Inorganic materials 0.000 description 36
- 238000002360 preparation method Methods 0.000 description 34
- 238000004440 column chromatography Methods 0.000 description 30
- 238000003756 stirring Methods 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 23
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- 238000010992 reflux Methods 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 238000001704 evaporation Methods 0.000 description 18
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- 230000005525 hole transport Effects 0.000 description 16
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 15
- 230000008020 evaporation Effects 0.000 description 14
- 238000012544 monitoring process Methods 0.000 description 13
- 238000001035 drying Methods 0.000 description 12
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000005516 engineering process Methods 0.000 description 11
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 9
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 9
- 239000010408 film Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000005695 Ammonium acetate Substances 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 235000019257 ammonium acetate Nutrition 0.000 description 8
- 229940043376 ammonium acetate Drugs 0.000 description 8
- 239000012362 glacial acetic acid Substances 0.000 description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 8
- 238000002386 leaching Methods 0.000 description 8
- 239000011368 organic material Substances 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 230000000903 blocking effect Effects 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 230000001376 precipitating effect Effects 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000009286 beneficial effect Effects 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 235000011056 potassium acetate Nutrition 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
- 238000002390 rotary evaporation Methods 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- IBXMKLPFLZYRQZ-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 IBXMKLPFLZYRQZ-UHFFFAOYSA-N 0.000 description 4
- AJOAHIKYBSZIEV-UHFFFAOYSA-N 2-bromo-4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C(Br)=C1 AJOAHIKYBSZIEV-UHFFFAOYSA-N 0.000 description 4
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical class OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 4
- 239000011162 core material Substances 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
- UNXISIRQWPTTSN-UHFFFAOYSA-N boron;2,3-dimethylbutane-2,3-diol Chemical compound [B].[B].CC(C)(O)C(C)(C)O UNXISIRQWPTTSN-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 238000010549 co-Evaporation Methods 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000008204 material by function Substances 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 2
- 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 2
- 230000003321 amplification Effects 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 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
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000002346 layers by function Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 238000003199 nucleic acid amplification method Methods 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 1
- 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
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- UTWIBGSFPYIOQU-UHFFFAOYSA-N 1,5-diphenyl-2H-pyrazin-3-amine Chemical compound NC(C1)=NC(C2=CC=CC=C2)=CN1C1=CC=CC=C1 UTWIBGSFPYIOQU-UHFFFAOYSA-N 0.000 description 1
- TUQSVSYUEBNNKQ-UHFFFAOYSA-N 2,4-dichloroquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(Cl)=C21 TUQSVSYUEBNNKQ-UHFFFAOYSA-N 0.000 description 1
- VHFAOWAVVYWLCS-UHFFFAOYSA-N 2-bromo-3-phenylbenzenethiol Chemical class BrC1=C(C=CC=C1C1=CC=CC=C1)S VHFAOWAVVYWLCS-UHFFFAOYSA-N 0.000 description 1
- SYTBIFURTZACKR-UHFFFAOYSA-N 2-bromo-4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1Br SYTBIFURTZACKR-UHFFFAOYSA-N 0.000 description 1
- NDOPHXWIAZIXPR-UHFFFAOYSA-N 2-bromobenzaldehyde Chemical class BrC1=CC=CC=C1C=O NDOPHXWIAZIXPR-UHFFFAOYSA-N 0.000 description 1
- BHVHKOVPWZKVCC-UHFFFAOYSA-N 4-(4-bromophenyl)benzonitrile Chemical group C1=CC(Br)=CC=C1C1=CC=C(C#N)C=C1 BHVHKOVPWZKVCC-UHFFFAOYSA-N 0.000 description 1
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
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- 101000930898 Cryphonectria parasitica Glyceraldehyde-3-phosphate dehydrogenase Proteins 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-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
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
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- 101000766357 Ruditapes philippinarum Big defensin Proteins 0.000 description 1
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- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-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
- XEFCWBLINXJUIV-UHFFFAOYSA-N acetic acid;iodobenzene Chemical compound CC(O)=O.CC(O)=O.IC1=CC=CC=C1 XEFCWBLINXJUIV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 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
- 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 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 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
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 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
- 230000007812 deficiency Effects 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
- 238000013461 design Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- BDTDECDAHYOJRO-UHFFFAOYSA-N ethyl n-(sulfanylidenemethylidene)carbamate Chemical compound CCOC(=O)N=C=S BDTDECDAHYOJRO-UHFFFAOYSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 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
- 230000008569 process Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 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
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000007738 vacuum evaporation Methods 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
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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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- 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
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- 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
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- 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
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- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- 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
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- 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
Abstract
The invention relates to a compound and application thereof, wherein the compound has a structure shown in a formula (1), the compound takes an electron-deficient large conjugated structure of imidazo nitrogen sulfur (oxygen) heteroheptatomic ring dibenzo-biphenyl as a parent nucleus and is connected with an Ar group, the compound structure has stronger electron-deficient performance and is favorable for electron injection, and meanwhile, the electron-deficient group of the large conjugated structure enables molecules to have good plane conjugation, so that the mobility of electrons is favorably improved, and the molecules integrally show good electron injection and migration performances.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a compound and application thereof.
Background
Organic Light Emission Diodes (OLED) devices are a kind of devices with sandwich-like structure, which includes positive and negative electrode films and Organic functional material layers sandwiched between the electrode films. And applying voltage to the electrodes of the OLED device, injecting positive charges from the positive electrode and injecting negative charges from the negative electrode, and transferring the positive charges and the negative charges in the organic layer under the action of an electric field to meet for composite luminescence. Because the OLED device has the advantages of high brightness, fast response, wide viewing angle, simple process, flexibility and the like, the OLED device is concerned in the field of novel display technology and novel illumination technology. At present, the technology is widely applied to display panels of products such as novel lighting lamps, smart phones and tablet computers, and further expands the application field of large-size display products such as televisions, and is a novel display technology with fast development and high technical requirements.
With the continuous advance of OLEDs in both lighting and display areas, much attention has been paid to the research on their core materials. This is because an efficient, long-lived OLED device is generally the result of an optimized configuration of the device structure and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures. Common functionalized organic materials are: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, and light emitting host materials and light emitting objects (dyes), and the like.
In order to prepare an OLED light-emitting device with lower driving voltage, better light-emitting efficiency and longer service life, the performance of the OLED device is continuously improved, the structure and the manufacturing process of the OLED device need to be innovated, and photoelectric functional materials in the OLED device need to be continuously researched and innovated, so that functional materials with higher performance can be prepared. Based on this, the OLED material industry has been working on developing new organic electroluminescent materials to achieve low starting voltage, high luminous efficiency and better lifetime of the device.
In order to further satisfy the continuously increasing demand for the photoelectric properties of OLED devices and the energy saving demand of mobile electronic devices, new and efficient OLED materials need to be continuously developed, wherein the development of new electron transport materials with high electron injection capability and high mobility is of great significance.
Disclosure of Invention
An object of the present invention is to provide a compound, particularly a compound for an organic electroluminescent device, and more particularly, a compound used as an electron transport material for an organic electroluminescent device, which has high electron injection ability and electron mobility, and can improve current efficiency of the device and reduce driving voltage.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a compound, which has a structure shown in a formula (1);
in the formula (1), X is S or O;
in the formula (1), Ar is any one selected from substituted or unsubstituted C8-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl and cyano;
in the formula (1), L is selected from any one of single bond, substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene;
in the formula (1), R is1And R2Each independently selected from any one of hydrogen, deuterium, halogen, cyano, C2-C20 alkenyl, C2-C20 alkynyl, nitro, C1-C20 alkyl, C3-C21 cycloalkyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
in the formula (1), R is selected from any one of deuterium, halogen, cyano, C2-C20 alkenyl, C2-C20 alkynyl, nitro, C1-C20 alkyl, C3-C21 cycloalkyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
in the formula (1), n is an integer of 0-7, such as 1, 2, 3,4, 5, 6, etc., preferably n is 0 or 1, and m is an integer of 0 or 1;
in the formula (1), Y represents a single bond; when m is 0, R1And R2Are two independent substituents which are not linked, R is R when m is 11And R2By a single bond Y, when R is present in accordance with the common general knowledge in the art1Or R2When any one is selected from hydrogen, deuterium, halogen, cyano or nitro, the two cannot be connected, namely m is only 0;
Ar、L、R1、R2and in R, the substituted groups are respectively and independently selected from one or the combination of at least two of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C6-C30 condensed ring heteroaryl. "monocyclic aryl" refers to aryl groups that do not contain fused groups, e.g., phenyl, biphenyl, terphenyl, are monocyclic aryl groups, "fused aryl" refers to fused aryl groups, e.g., naphthyl, anthryl, phenanthryl, and the like, monocyclic heteroaryl and fused ring heteroaryl are synonymous.
Ar、L、R1、R2In the R, the number of the substituted groups is 1 to the maximum number of the substitutable groups, the groups listed in the upper paragraph refer to the selection range of the substituent when the substituent exists in the substituted or unsubstituted group, one substituent can be substituted on the substituted or unsubstituted group, and a plurality of substituents can be substituted on the substituted or unsubstituted group.
In a preferred embodiment of the present invention, Ar, L, R1、R2And in R, the substituted groups are respectively and independently selected from any one or at least two of cyano, phenyl, methyl or pyridyl.
In the present invention, the heteroatom of heteroaryl is generally referred to as N, O, S.
In the present invention, the expression of the "-" underlined loop structure indicates that the linking site is located at an arbitrary position on the loop structure where the linkage can be formed.
In the present invention, the carbon number of the C8-C60 aryl group, C6-C60 (arylene) group may be C8, C10, C12, C14, C16, C18, C20, C26, C28, C30, C32, C34, C36, C38, C40, C42, C46, C48, C50, C52, C54, C56, C58, etc.;
in the present invention, the carbon number of the C3-C60 (arylene) heteroaryl group may be C4, C5, C6, C7, C8, C10, C12, C14, C16, C18, C20, C26, C28, C30, C32, C34, C36, C38, C40, C42, C46, C48, C50, C52, C54, C56, C58, etc.;
in the invention, the carbon number of the C2-C20 alkenyl, C2-C20 alkynyl and C1-C20 alkyl can be C2, C3, C4, C5, C6, C7, C8, C9, C10, C12, C14, C16, C18 and the like;
in the present invention, the carbon number of the C3-C21 cycloalkyl group may be C4, C5, C6, C7, C8, C9, C10, C12, C14, C16, C18, C19, C20, etc.;
in the present invention, the carbon number of the C1-C10 chain alkyl group, C1-C10 alkoxy group, and C1-C10 thioalkoxy group may be C2, C3, C4, C5, C6, C7, C8, C9, C10, or the like;
in the invention, the number of carbons of the C3-C10 cycloalkyl group can be C4, C5, C6, C7, C8, C9 and the like;
in the invention, the carbon number of the C6-C30 arylamino can be C8, C10, C12, C14, C16, C18, C20, C26, C28 and the like;
in the invention, the number of carbons of the C3-C30 heteroaryl amino group can be C3, C4, C6, C8, C10, C12, C14, C16, C18, C20, C26, C28 and the like;
in the invention, the number of carbons in the C6-C30 monocyclic aryl group can be C8, C10, C12, C14, C16, C18, C20, C26, C28, and the like; the number of carbons of the C10-C30 condensed ring aryl can be C12, C14, C16, C18, C20, C26, C28 and the like; the C3-C30 monocyclic heteroaryl can have the carbon number of C3, C4, C6, C8, C10, C12, C14, C16, C18, C20, C26, C28 and the like; the number of carbons of the C6-C30 fused ring heteroaryl can be C8, C10, C12, C14, C16, C18, C20, C26, C28 and the like.
The number of carbons is merely an example and is not limited to the above.
The compound provided by the invention is an imidazonitrogen sulfur (oxygen) hetero seven-membered ring dibenzo-p-phenylene
The electron-deficient large conjugated structure is a mother nucleus and is connected with an Ar group, the compound structure has strong electron-deficiency property and is beneficial to the injection of electrons, and meanwhile, the electron-deficient group of the large conjugated structure enables molecules to have good plane conjugation, so that the mobility of electrons is improved.
The characteristics of the compound can enable molecules to show good electron injection and migration performance, so when the compound is used in an organic electroluminescent device, particularly as an electron transport material, the electron injection and migration efficiency in the device can be effectively improved, and the excellent effects of high luminous efficiency and low starting voltage of the device are ensured.
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.
Preferably, m is 0, i.e. the structure of formula (1) is as follows:
Preferably, the compound has a structure represented by formula (1-1) or formula (1-2);
ar, L and R1、R2R and n all have the same meanings as in formula (1).
Preferably, the compound has any one of the structures shown in formula (a) to formula (h);
the R is3-R9Each independently selected from any one of hydrogen, deuterium, halogen, cyano, C2-C20 alkenyl, C2-C20 alkynyl, nitro, C1-C20 alkyl, C3-C21 cycloalkyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
R3-R9wherein the substituted groups are independently selected from one or a combination of at least two of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 fused ring aryl, C3-C30 monocyclic heteroaryl and C6-C30 fused ring heteroaryl;
ar, L and R1、R2All have the same meaning as in formula (1).
In the present invention, a compound having an imidazonitrogen-sulfur-hetero seven-membered ring dibenzoyl as a core (i.e., X is S) is preferable, and since the compound has a higher conjugated electron cloud density than a compound having an imidazonitrogen-oxygen-hetero seven-membered ring dibenzoyl as a core (i.e., X is O), the current efficiency of the device can be further improved.
Preferably, Ar is selected from any one of substituted or unsubstituted C8-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl and cyano, and is preferably substituted or unsubstituted C3-C30 electron-deficient heteroaryl or cyano.
The invention preferably substitutes electron-deficient group Ar on the imidazo nitrogen sulfur (oxygen) hetero seven-membered ring dibenzo-p-phenylene nucleus, and compared with a group without electron-deficient property, the invention can further improve the electron-deficient property of the structure, thereby being more beneficial to the injection of electrons, further improving the electron injection and migration performance of the compound, and when the compound is used as an electron transport material of an organic electroluminescent device, the compound can further improve the luminous efficiency of the device and reduce the driving voltage.
Compared with the single structures of oxazole, thiazole, imidazole, triazole or triazine in the prior art, the structure of the invention, which replaces electron-deficient group Ar on the imidazo nitrogen sulfur (oxygen) hetero seven-membered ring dibenzo-nucleus, has relatively stronger electron-deficient performance, thereby being more beneficial to the injection of electrons, and the molecules have good plane conjugation by matching with the large conjugated electron-deficient nucleus, thereby being beneficial to improving the mobility of electrons and further being more beneficial to improving the performance of devices.
In the present invention, "electron deficient heteroaryl" refers to a group in which the electron cloud density on the aromatic ring is reduced after the group replaces a hydrogen on the aromatic ring, and generally such a group has a Hammett value of more than 0.6. The Hammett value is a representation of the charge affinity for a particular group and is a measure of the electron withdrawing group (positive Hammett value) or electron donating group (negative Hammett value). The Hammett equation is described In more detail In Thomas H.Lowry and Kathelen Schueler Richardson, "mechanics and Theory In Organic Chemistry", New York,1987, 143-. Such groups may be listed but are not limited to: triazinyl, pyrimidinyl, benzopyrimidinyl, benzopyridyl, naphthyridinyl, phenanthridinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, pyridazinyl, and alkyl-or aryl-substituted ones of the foregoing. The meaning of "electron deficient heteroaryl" in the context of the present invention is consistent with the meaning of "electron deficient group" herein.
Preferably, Ar is selected from cyano or any one of the following substituted or unsubstituted groups:
wherein the wavy line indicates the bond of the group.
Preferably, Ar is selected from cyano or any one of the following substituted or unsubstituted groups:
wherein the wavy line indicates the bond of the group.
Preferably, said Ar is selected from substituted or unsubstituted triazinyl.
According to the invention, Ar is further preferably a triazine group which has lower electron density and can be matched with an imidazo nitrogen sulfur (oxygen) hetero seven-membered ring dibenzo-p-phenylene nucleus to further improve the electron injection and migration performance; thereby further improving the luminous efficiency of the device and reducing the driving voltage.
Preferably, the L is selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group, preferably a single bond, or a substituted or unsubstituted C6-C30 arylene group, and further preferably a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted biphenylene group, and a substituted or unsubstituted naphthylene group.
Preferably, the L is a substituted or unsubstituted phenylene group and the Ar is a cyano group.
Preferably, said R is1And R2Each independently selected from any one of hydrogen, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.
Preferably, R1And R2The substituted or unsubstituted C6-C30 aryl group is a cyano-substituted C6-C30 aryl group, preferably a cyano-substituted phenyl group.
Further preferred according to the invention is R1And R2Are all selected from cyano-substituted aryl, R1And R2The single bond connection with the mother nucleus enables the whole to have a symmetrical linear structure, and compared with aryl which is not substituted by cyano, the electron injection and migration efficiency is further improved.
Preferably, said R is1And R2Each independently selected from hydrogen or any one of the following substituted or unsubstituted groups:
wherein the wavy line indicates the bond of the group.
Preference is given toEarth, the R1And R2Each independently selected from hydrogen, cyano-substituted phenyl, or any one of the following substituted or unsubstituted groups:
wherein the wavy line indicates the bond of the group.
Preferably, R is selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl, preferably any one of the following substituted or unsubstituted groups:
wherein the wavy line indicates the bond of the group.
Preferably, said R is3-R9Each independently selected from any one of hydrogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, preferably hydrogen or any one of the following substituted or unsubstituted groups:
wherein the wavy line indicates the bond of the group.
Preferably, the compound has any one of the following structures shown as C1 to C75:
it is a second object of the present invention to provide the use of the compounds according to the first object for organic electronic devices.
The organic electronic device includes an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet type scanner, or electronic paper, and is preferably an organic electroluminescent device.
Preferably, the compound is used as an electron transport material in the organic electroluminescent device.
The invention also provides an organic electroluminescent device which comprises a substrate, a first electrode, a second electrode and at least one organic layer positioned between the first electrode and the second electrode, wherein the organic layer contains at least one compound for one purpose.
Preferably, the organic layer comprises an electron transport layer comprising at least one compound according to one of the objects.
Specifically, one embodiment of the present invention provides an organic electroluminescent device including a substrate, and an anode layer, a plurality of light emitting functional layers, and a cathode layer sequentially formed on the substrate; the light-emitting functional layer comprises a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is arranged between the hole transport layer and the electron transport layer; wherein the electron transport layer contains the compound of the general formula of the present invention represented by the above formula (1).
More specifically, the organic electroluminescent device will be described in detail.
The OLED device 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, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO) may be used2) And transparent conductive oxide materials such as zinc oxide (ZnO), and any combination thereof. 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), and aromatic amine derivatives as 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 HI-1 to HI-3 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 HI-1 to HI-3 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 accordance with 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 a fluorescent electroluminescence technique. The luminescent layer fluorescent host material may be selected from, but not limited to, the combination of one or more of BFH-1 through BFH-17 listed below.
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent dopant may be selected from, but is not limited to, combinations of one or more of BFD-1 through BFD-12 listed below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The host material of the light emitting layer is selected from, but not limited to, one or more of GPH-1 to GPH-80.
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.
Wherein D is deuterium.
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.
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 YPD-1 to YPD-11 listed below.
The organic electroluminescent device of the present invention includes 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).
The electron transport region may also be formed using the compound of the present invention for a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL), although the material of the electron transport region may also be combined with one or more of ET-1 to 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 material including, but not limited to, combinations of one or more of the following:
Liq、LiF、NaCl、CsF、Li2O、Cs2CO3、BaO、Na、Li、Ca。
compared with the prior art, the invention has the following beneficial effects:
the compound provided by the invention takes an electron-deficient large conjugated structure of the imidazo nitrogen sulfur (oxygen) hetero seven-membered ring dibenzo-benzene as a mother nucleus and is connected with an Ar group, the compound structure has stronger electron-deficient performance and is favorable for electron injection, and meanwhile, the electron-deficient group of the large conjugated structure enables molecules to have good plane conjugation, thereby being favorable for improving the mobility of electrons. The aforementioned characteristics can enable molecules to show good electron injection and migration performance, so when the compound provided by the invention is used in an organic electroluminescent device, particularly as an electron transport material, the electron injection and migration efficiency in the device can be effectively improved, and the excellent effects of high luminous efficiency and low starting voltage of the device are ensured.
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 technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
The synthetic route of the compound shown in the invention is as follows:
in the first step of reaction, substituted o-bromobenzaldehyde and substituted o-diketone are subjected to an aldehyde-amine condensation reaction in a glacial acetic acid solution containing ammonium acetate, and then an intermediate M1 with an imidazole ring structure is formed in a closed ring mode; in the second step of reaction, the intermediate M1 and substituted o-bromophenol or o-bromophenylthiophenol are catalytically coupled with cuprous iodide to obtain the target compound with seven-membered ring. Wherein X is O or S, R1、R2R, n, L and Ar all have the same meaning as in the general formula (1), NH4OAc is ammonium acetate, AcOH is glacial acetic acid, o-phen is phenanthroline, and DMF is N, N-dimethylformamide.
Basic chemical materials such as ethanol, ethyl acetate, sodium sulfate, toluene, tetrahydrofuran, dichloromethane, 1, 4-dioxane, N-dimethylformamide, potassium carbonate, potassium acetate, and cuprous iodide used in the synthesis method of the specific compound provided in the following synthesis examples were purchased from shanghai tatatake gmbh and silong chemical gmbh. The mass spectrometer used for determining the following compounds was a ZAB-HS type mass spectrometer measurement (manufactured by Micromass, UK).
Synthesis example 1:
synthesis of Compound C1
(1) Preparation of Compound 1-1
The compound 2-bromo-4-chlorobenzaldehyde (218g, 1.0mol) was added to a 5L flask containing 2L of glacial acetic acid, ammonium acetate (154g, 2.0mol) and benzil (210g, 1.0mol) were added slowly in portions with stirring at room temperature, and after the addition, the reaction was stirred at 120 ℃ for reflux for 4 hours, and TLC monitoring indicated completion of the reaction. After the reaction solution was cooled to room temperature, it was slowly poured into 4L of water to precipitate a large amount of solid, which was then filtered off with suction and purified by column chromatography to obtain compound 1-1(381g, yield 93%).
(2) Preparation of Compounds 1-2
Adding a compound 1-1(40.8g, 100mmol), o-bromophenylthiol (18.8g, 100mmol) and 300mL of N, N-dimethylformamide into a 1L flask, replacing nitrogen, respectively adding cuprous iodide (0.38g, 2.0mmol) and o-phenanthroline (0.79g, 4.0mol), replacing nitrogen for 4 times, carrying out reflux reaction for 12 hours under stirring at 110 ℃, and monitoring the reaction end point by TLC. And cooling the reaction to room temperature, slowly pouring the cooled reaction product into 2L of cold water, precipitating a large amount of solid, leaching the filtered solid with water and ethanol for three times respectively, drying the solid, and performing column chromatography separation and purification to obtain the compound 1-2(31g, yield 71%).
(3) Preparation of Compounds 1-3
Compound 1-2(30g, 69mmol), pinacol diboron diboronate (26.3g, 104mmol) and potassium acetate (13.5g, 138mmol) were charged into a 1L flask containing 300mL of 1, 4-dioxane, and after nitrogen gas was replaced with stirring at room temperature, palladium acetate (0.35g, 1.38mmol) and 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (1.13g, 2.76mmol) were added. After the addition was completed, nitrogen was replaced four times, the reaction was refluxed with stirring for 12 hours, and the end of the reaction was monitored by TLC. The 1, 4-dioxane was removed by rotary evaporation, and the mixture was separated with water and dichloromethane, and the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and purified by column chromatography to give compounds 1 to 3(32g, yield 88%).
(4) Preparation of Compound C1
Compound 1-3(10g, 19mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (5.3g, 19mmol), potassium carbonate (5.4g, 38mmol), [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium (146mg, 0.2mmol) was added to a flask containing 100mL of tetrahydrofuran and 25mL of water, the nitrogen was replaced and the reaction was refluxed under nitrogen for 4 hours, and TLC showed completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, respectively, dried and purified by column chromatography to obtain compound C1(9.6g, yield 80%). Calculated molecular weight: 633.20, found C/Z: 633.2.
synthesis example 2:
synthesis of Compound C20
(1) Preparation of Compound 2-1
The compound 4,4' -dibromodiphenylethanone (36.6g, 100mmol), 4-pyridineboronic acid (24.6g, 200mmol), potassium carbonate (27.6g, 200mmol), tetratriphenylphosphonium palladium (1.0g, 0.87mol) were added to a 2L flask containing 500L toluene, 100mL ethanol, and 100mL water, the reaction was refluxed under nitrogen atmosphere for 4 hours, and TLC showed completion of the reaction. Cooling to room temperature, separating, extracting water phase with ethyl acetate, combining organic phases, drying with anhydrous sodium sulfate, and purifying by column chromatography to obtain compound 2-1(29.2g, yield 80%).
(2) Preparation of Compound 2-2
Compound 2-1(29g, 79.7mmol) was added to a 500mL flask containing 200mL glacial acetic acid, ammonium acetate (12.3g, 159.4mmol) was added slowly in portions with stirring at room temperature, and upon completion the reaction was stirred at 120 ℃ for 4 hours under reflux and TLC monitoring indicated complete reaction. After the reaction solution is cooled to room temperature, the reaction solution is slowly poured into 1L of water, a large amount of solid is separated out, and after suction filtration, the solid is separated and purified by column chromatography to obtain the compound 2-2(40.3g, yield 90%).
(3) Preparation of Compounds 2-3
Adding the compound 2-2(40.0g, 71.2mmol), o-bromophenylthiol (12.2g, 71.2mmol) and 300mL of N, N-dimethylformamide into a 1L flask, replacing nitrogen, respectively adding cuprous iodide (0.27g, 1.4mmol) and o-phenanthroline (0.56g, 2.8mol), replacing nitrogen for 4 times, stirring at 110 ℃, refluxing for 8 hours, and monitoring the reaction endpoint by TLC. And cooling the reaction to room temperature, slowly pouring the cooled reaction product into 2L of cold water, precipitating a large amount of solid, leaching the filtered solid with water and ethanol for three times respectively, drying the solid, and performing column chromatography separation and purification to obtain the compound 2-3(26g, yield 62%).
(4) Preparation of Compound C20
Compound 2-3(15g, 26.7mmol), 4-pyridineboronic acid (3.3g, 26.7mmol), potassium carbonate (7.4g, 54.3mmol), dibenzylideneacetone dipalladium (0.22g, 0.3mmol), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (0.24g, 0.6mmol) were added to a 1L flask containing 200mL of 1, 4-dioxane and 20mL of water, the nitrogen was replaced and the reaction was heated under reflux under nitrogen atmosphere for 4 hours, and TLC showed completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, respectively, dried and purified by column chromatography to obtain compound C20(12.1g, yield 72%). Calculated molecular weight: 633.20, found C/Z: 633.2.
synthesis example 3:
synthesis of Compound C42
(1) Preparation of Compound 3-1
The compound 2-bromo-4-chlorobenzaldehyde (218g, 1.0mol) was added to a 5L flask containing 2L of glacial acetic acid, ammonium acetate (154g, 2.0mol) and benzil (210g, 1.0mol) were added slowly in portions with stirring at room temperature, and after the addition, the reaction was stirred at 120 ℃ for reflux for 4 hours, and TLC monitoring indicated completion of the reaction. After the reaction solution was cooled to room temperature, it was slowly poured into 4L of water to precipitate a large amount of solid, which was then filtered off with suction and purified by column chromatography to obtain compound 3-1(381g, yield 93%).
(2) Preparation of Compound 3-2
Adding a compound 3-1(40.8g, 100mmol), o-bromophenol (17.2g, 100mmol) and 300mL of N, N-dimethylformamide into a 1L flask, replacing nitrogen, respectively adding cuprous iodide (0.38g, 2.0mmol) and o-phenanthroline (0.79g, 4.0mol), replacing nitrogen for 4 times, carrying out stirring reflux reaction at 110 ℃ for 12 hours, and monitoring the reaction endpoint by TLC. And cooling the reaction to room temperature, slowly pouring the cooled reaction product into 2L of cold water, precipitating a large amount of solid, leaching the filtered solid with water and ethanol for three times respectively, drying the solid, and performing column chromatography separation and purification to obtain the compound 3-2(24g, yield 57%).
(3) Preparation of Compound 3-3
4-bromo-4 ' -cyanobiphenyl (25.7g, 100mmol), pinacol diboron diborate (38.1g, 150mmol), and potassium acetate (19.6g, 200mmol) were charged into a 1L flask containing 400mL of 1, 4-dioxane, and after replacing nitrogen with nitrogen at room temperature, palladium acetate (0.45g, 2.0mmol) and 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (1.6g, 4.0mmol) were added thereto with stirring. After the addition was completed, nitrogen was replaced four times, the reaction was refluxed with stirring for 12 hours, and the end of the reaction was monitored by TLC. The 1, 4-dioxane was removed by rotary evaporation, and the mixture was separated with water and dichloromethane, and the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and purified by column chromatography to give compound 3-3(22.2g, yield 73%).
(4) Preparation of Compound C42
Compound 3-2(15g, 35.7mmol), compound 3-3(10.9g, 35.7mmol), potassium carbonate (9.9g, 71.4mmol), dibenzylideneacetone dipalladium (0.26g, 0.36mmol), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (0.3g, 0.72mmol) were added to a 1L flask containing 200mL of 1, 4-dioxane and 20mL of water, the nitrogen was replaced and the reaction was heated under reflux under nitrogen atmosphere for 4 hours, and TLC showed completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, respectively, dried and purified by column chromatography to give compound C42(15.4g, yield 77%). Calculated molecular weight: 563.20, found C/Z: 563.2.
synthesis example 4:
synthesis of Compound C64
(1) Preparation of Compound 4-1
After 2-amino-4, 6-diphenylpyrazine (24.7g, 100mmol) was dissolved in 250mL dioxane, the solution was added to a 500mL three-necked flask, and ethoxycarbonyl isothiocyanate (15.8g, 120mmol) was gradually added dropwise while maintaining the temperature at not higher than 15 ℃ and the mixture was stirred at room temperature overnight. TLC detection reaction is complete, dioxane is concentrated, ethanol is stirred and washed, and after filtration, column chromatography separation and purification are carried out to obtain the compound 4-1(29.1g, yield 77%).
(2) Preparation of Compound 4-2
A500 mL three-necked flask was charged with hydroxylamine hydrochloride (19.2g, 288mmol), 150mL of ethanol and 150mL of methanol were further added, and then triethylamine (19.2g, 288mmol) was added in portions, and the mixture was stirred at room temperature for one hour. Then compound 4-1(24g, 64mmol) is added, the mixture is heated to reflux and reacted for about 4h, the TLC detection reaction is finished, and the mixture is cooled to room temperature. Filtering, rinsing with water, rinsing with ethanol, drying, and purifying by column chromatography to obtain compound 4-2(15.2g, 93%).
(3) Preparation of Compound 4-3
Reacting CuBr2(23.4g, 106mmol) and acetonitrile (MeCN)200mL were added to a 500mL single neck flask, then tert-butyl nitrite (11g, 106mmol) was slowly added dropwise and heated at 50 ℃ with stirring for one hour, then Compound 4-2(15.2g, 53mmol) was added in portions and stirring continued at 50 ℃. Reacting for 3h, detecting by TLC, enabling the compound 4-2 to completely react, cooling the reaction liquid, pouring the cooled reaction liquid into 1L of water, separating out a large amount of yellow-green solid, filtering, leaching with ethanol, drying, extracting and separating with DCM, drying with organic phase anhydrous sodium sulfate, and purifying by column chromatography to obtain the compound 4-3(15g, yield 81%).
(4) Preparation of Compound 4-4
The compound 2-bromo-4-chlorobenzaldehyde (21.8g, 100mol) was added to a 500mL flask containing 200mL glacial acetic acid, ammonium acetate (15.4g, 200mmol) and phenanthrenequinone (20.8g, 100mmol) were added slowly in portions with stirring at room temperature, and after addition the reaction was stirred at 120 ℃ for 4 hours under reflux, and TLC monitoring indicated completion of the reaction. After the reaction solution was cooled to room temperature, it was slowly poured into 4L of water to precipitate a large amount of solid, which was then filtered off with suction and purified by column chromatography to obtain compound 4-4(33.2g, yield 82%).
(5) Preparation of Compounds 4-5
Adding compounds 4-4(33g, 76mmol), o-bromophenylthiol (14.3g, 76mmol) and 300mL of N, N-dimethylformamide into a 1L flask, replacing nitrogen, respectively adding cuprous iodide (0.29g, 1.5mmol) and o-phenanthroline (0.6g, 3.0mol), replacing nitrogen for 4 times, stirring at 110 ℃, carrying out reflux reaction for 12 hours, and monitoring the reaction end point by TLC. And cooling the reaction to room temperature, slowly pouring the cooled reaction product into 2L of cold water, precipitating a large amount of solid, leaching the filtered solid with water and ethanol for three times respectively, drying the solid, and performing column chromatography separation and purification to obtain the compound 4-5(24.4g, yield 74%).
(6) Preparation of Compounds 4-6
Compound 4-5(24g, 55.3mmol), pinacol diboron ester (21g, 83mmol) and potassium acetate (10.8g, 110.6mmol) were charged into a 1L flask containing 300mL of 1, 4-dioxane, and after nitrogen exchange at room temperature with stirring, palladium acetate (0.25g, 1.1mmol) and 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (0.9g, 2.2mmol) were added. After the addition was completed, nitrogen was replaced four times, the reaction was refluxed with stirring for 12 hours, and the end of the reaction was monitored by TLC. The 1, 4-dioxane was removed by rotary evaporation, the mixture was separated with water and dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and purified by column chromatography to give compound 4-6(21g, yield 76%).
(7) Preparation of Compound C64
Compound 4-3(10g, 28.6mmol), compound 4-6(15g, 28.6mmol), potassium carbonate (7.9g, 57.2mmol), tetrakistriphenylphosphine palladium (0.34g, 0.29mmol) were added to a flask containing 100mL of toluene, 20mL of ethanol, and 20mL of water, the reaction was refluxed for 4 hours under nitrogen atmosphere, and TLC showed completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, respectively, dried and purified by column chromatography to obtain compound C64(16.3g, yield 85%). Calculated molecular weight: 670.19, found C/Z: 670.2.
synthesis example 5:
synthesis of Compound C67
(1) Preparation of Compound 5-1
Adding 50g (256mmol, 1.0eq) of 2, 4-dichloroquinazoline into a 1L single-neck bottle, adding 400mL of dichloromethane, cooling to 0 ℃ in an ice bath, adding 64g (632mmol, 3.0eq) of triethylamine, stirring until a reaction solution is clear, dropwise adding 18.6g (316mmol, 1.5eq) of hydrazine hydrate in the ice bath, gradually precipitating solids in the reaction process, stirring for 3 hours, monitoring the reaction by TLC, allowing the raw materials to disappear, adding 4.0L of water, and continuing stirring for 1 hour. Filtration and drying were carried out to obtain Compound 5-1(33g, yield: 81%).
(2) Preparation of Compound 5-2
33g of compound 5-1(170mmol, 1.0eq), 19.8g of benzaldehyde (187mmol, 1.1eq) and 500mL of ethanol were added to a 1.0L single-neck flask, and stirring was continued for 30 minutes after the solution was clear, and disappearance of the starting material was monitored by TLC. 60g (187mmol, 1.1eq) iodobenzene diacetic acid were added portionwise (temperature controlled below 20 ℃ C. for the addition). After the addition was completed, stirring was carried out overnight, a solid was gradually precipitated, TLC monitored reaction was completed, filtration was carried out, the filter cake was rinsed with ethanol until the filtrate was a colorless clear liquid, rinsed with Petroleum Ether (PE) for 2 to 3 times, and dried to obtain compound 5-2(39g, yield: 82%).
(3) Preparation of Compound 5-3
The compound 2-bromo-4-chlorobenzaldehyde (21.8g, 100mmol) was added to a 500mL flask containing 200mL glacial acetic acid, ammonium acetate (15.4g, 200mmol) and diethyl oxalate (14.6g, 100mmol) were added slowly in portions with stirring at room temperature, and after addition the reaction was stirred at 120 ℃ for 4 hours under reflux, and TLC monitoring indicated completion of the reaction. After the reaction solution was cooled to room temperature, it was slowly poured into 4L of water to precipitate a large amount of solid, which was then filtered off with suction and purified by column chromatography to obtain compound 5-3(22.5g, yield 88%).
(4) Preparation of Compounds 5-4
Adding a compound 5-3(22g, 86mmol), 4-chloro-2-bromophenylthiophenol (18.9g, 86mmol) and 300mL of N, N-dimethylformamide into a 1L flask, replacing nitrogen, respectively adding cuprous iodide (0.33g, 1.7mmol) and phenanthroline (0.67g, 3.4mol), replacing nitrogen for 4 times, stirring at 110 ℃, carrying out reflux reaction for 12 hours, and monitoring the reaction end point by TLC. And cooling the reaction to room temperature, slowly pouring the cooled reaction product into 2L of cold water, precipitating a large amount of solid, leaching the filtered solid with water and ethanol for three times respectively, drying the solid, and performing column chromatography separation and purification to obtain the compound 5-4(21g, yield 77%).
(5) Preparation of Compounds 5-5
Compound 5-4(20.6g, 80mmol), pinacol diboron ester (50.8g, 200mmol) and potassium acetate (15.7g, 160mmol) were charged into a 1L flask containing 500mL of 1, 4-dioxane, and after nitrogen exchange at room temperature with stirring, palladium acetate (0.36g, 1.6mmol) and 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (1.3g, 3.2mmol) were added. After the addition was completed, nitrogen was replaced four times, the reaction was refluxed with stirring for 12 hours, and the end of the reaction was monitored by TLC. The 1, 4-dioxane was removed by rotary evaporation, the mixture was separated with water and dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and purified by column chromatography to give compound 5-5(30.5g, yield 76%).
(6) Preparation of Compound C67
Compound 5-2(10g, 35.7mmol), compound 5-5(8.5g, 17mmol), potassium carbonate (9.9g, 71.4mmol), dibenzylideneacetone dipalladium (0.22g, 0.3mmol), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (0.24g, 0.6mmol) were added to a 1L flask containing 200mL of 1, 4-dioxane and 20mL of water, the nitrogen was replaced and the reaction was heated under reflux under nitrogen for 4 hours, and TLC showed completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, respectively, dried and purified by column chromatography to give compound C67(9.8g, yield 78%). Calculated molecular weight: 738.21, found C/Z: 738.2.
comparative Synthesis example 1
Synthesis of compound D1:
(1) preparation of Compound D1-1
The compound, diphenylethanone (21g, 100mmol), was added to a 500mL flask containing 200mL glacial acetic acid, ammonium acetate (15.5g, 200mmol) was added slowly in portions with stirring at room temperature, and after the addition the reaction was stirred at 120 ℃ for 4 hours under reflux and the reaction was complete as monitored by TLC. After the reaction solution was cooled to room temperature, it was slowly poured into 1L of water to precipitate a large amount of solid, which was then filtered off with suction and purified by column chromatography to obtain compound D1-1(37.5g, yield 92%).
(2) Preparation of Compound D1-2
Adding a compound D1-1(35g, 85.8mmol), o-bromophenol (14.7g, 85.8mmol) and 300mL of N, N-dimethylformamide into a 1L flask, replacing nitrogen, respectively adding cuprous iodide (0.33g, 1.7mmol) and o-phenanthroline (0.68g, 3.4mol), replacing nitrogen for 4 times, stirring at 110 ℃, carrying out reflux reaction for 8 hours, and monitoring the reaction end point by TLC. And cooling the reaction to room temperature, slowly pouring the cooled reaction product into 2L of cold water, precipitating a large amount of solid, leaching the filtered solid with water and ethanol for three times respectively, drying the solid, and performing column chromatography separation and purification to obtain the compound D1-2(25.4g, yield 68%).
(3) Preparation of Compound D1
Compound D1-2(15g, 34.4mmol), phenylboronic acid (5.0g, 41.2mmol), potassium carbonate (9.5g, 68.8mmol), dibenzylideneacetone dipalladium (0.62g, 0.68mmol), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (0.53g, 1.3mmol) was added to a 1L flask containing 200mL of 1, 4-dioxane and 20mL of water, the nitrogen was replaced and the reaction was heated under reflux under nitrogen for 4 hours, and TLC showed completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, respectively, dried and purified by column chromatography to give compound D1(12.3g, yield 75%). Calculated molecular weight: 478.15, found C/Z: 478.2.
comparative Synthesis example 2
Synthesis of compound D2:
(1) preparation of Compound D2-1
Adding a compound 4-chloro-2-bromoaniline (20.5g, 100mmol), o-bromophenol (17.1g, 100mmol) and 300mL of N, N-dimethylformamide into a 1L flask, replacing nitrogen, respectively adding cuprous iodide (0.39g, 2.0mmol) and o-phenanthroline (0.80g, 4.0mol), replacing nitrogen for 4 times, stirring at 110 ℃, carrying out reflux reaction for 6 hours, and monitoring the reaction endpoint by TLC. After the reaction is cooled to room temperature, slowly pouring the reaction product into 2L of cold water to precipitate a large amount of solid, leaching the filtered solid with water and ethanol for three times respectively, drying the solid, and performing column chromatography separation and purification to obtain a compound D2-1(18.3g, yield 79%).
(2) Preparation of Compound D2-2
Compound D2-1(18g, 78mmol), pinacol diboron (29.7g, 117mmol) and potassium acetate (21.5g, 156mmol) were charged into a 1L flask containing 300mL of 1, 4-dioxane, and after nitrogen exchange at room temperature with stirring, palladium acetate (0.36g, 1.6mmol) and 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (1.3g, 3.2mmol) were added. After the addition was completed, nitrogen was replaced four times, the reaction was refluxed with stirring for 8 hours, and the end of the reaction was monitored by TLC. The 1, 4-dioxane was removed by rotary evaporation, and the mixture was separated with water and dichloromethane, and the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and purified by column chromatography to give compound D2-2(19.4g, yield 77%).
(3) Preparation of Compound D2
Compound D2-2(15g, 46.3mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (12.3g, 46.3mmol), potassium carbonate (12.7g, 92.6mmol), [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium (366mg, 0.5mmol) was added to a flask containing 200mL tetrahydrofuran and 50mL water, the nitrogen was replaced and the reaction was heated to reflux under nitrogen for 4 hours and TLC indicated completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, respectively, dried and purified by column chromatography to give compound D2(16.3g, yield 82%). Calculated molecular weight: 429.12, found C/Z: 429.1.
comparative Synthesis example 3
Synthesis of compound D3:
the compounds 4-spirobifluoreneboronic acid (15g, 41.6mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (11.1g, 41.6mmol), potassium carbonate (11.4g, 83mmol), [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium (292mg, 0.4mmol) were added to a flask containing 200mL of tetrahydrofuran and 50mL of water, the nitrogen was replaced and the reaction was heated under reflux under nitrogen for 6 hours, TLC indicated completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, respectively, dried and purified by column chromatography to give compound D3(17.8g, yield 78%). Calculated molecular weight: 549.22, found C/Z: 549.2.
example 1
The embodiment provides a preparation method of an organic electroluminescent device, which comprises the following specific steps:
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 until the pressure is less than 10-5Pa, performing vacuum evaporation on the anode layer film by using a multisource co-evaporation method to obtain HI-3 serving as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
evaporating HT-4 on the hole injection layer in vacuum to serve as a first hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 40 nm;
evaporating HT-14 on the first hole transport layer in vacuum to serve as a second hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 10 nm;
a luminescent layer of the device is vacuum evaporated on the second hole transport layer, the luminescent layer comprises a main material and a dye material, the evaporation rate of the main material BFH-4 is adjusted to be 0.1nm/s, the evaporation rate of the dye BFD-6 is set in a proportion of 5%, and the total film thickness of evaporation is 20nm by using a multi-source co-evaporation method;
vacuum evaporating ET-17 on the luminescent layer to be used as a hole blocking layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness is 5 nm;
evaporating the compounds C1 and ET-57 of the invention on the hole blocking layer by a multi-source co-evaporation method to be used as an electron transport layer, adjusting the evaporation rate of the compound C1 to be 0.1nm/s, setting the ratio of the evaporation rate of the compound C1 to the evaporation rate of the ET-57 to be 100% (the ratio of the evaporation rates of C1 and ET-57 is 1:1), and setting the total thickness of the evaporated film to be 23 nm;
LiF with the thickness of 1nm 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 80nm is used as a cathode of the device.
Examples 2 to 15, comparative examples 1 to 3 and example 1 differ only in that compound C1 was replaced by another compound, as specified in table 1.
And (3) performance testing:
the driving voltage and current efficiency of the organic electroluminescent devices prepared in examples and comparative examples were measured at the same brightness using a PR 750 type photoradiometer of Photo Research, a ST-86LA type brightness meter (photoelectric instrument factory of university of beijing) and a Keithley4200 test system. 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 1000cd/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;
the results of the performance tests are shown in table 1.
TABLE 1
As can be seen from table 1, under the condition that other materials in the organic electroluminescent device structure are the same, the organic electroluminescent device provided by the embodiment of the present invention has high current efficiency and low driving voltage, wherein the current efficiency is 6.42 to 7.22cd/a, and the driving voltage is 3.81 to 4.38V.
The parent nucleus of the compound is an electron-deficient large conjugated structure of imidazo nitrogen sulfur (oxygen) heteroheptatomic ring dibenzo, Ar is connected with the parent nucleus through a single bond or L, so that the whole compound has higher electron injection and migration performance, a device has higher current efficiency and lower driving voltage, and the technical effect of the invention can not be realized by replacing the parent nucleus or Ar with other structures (comparative examples 1-3).
It can be seen from the comparison between example 1 and examples 2 and 5 that the electron-deficient large conjugated structure of the parent core imidazo diazo thio (oxy) hetero seven-membered ring dibenzo is connected with the triazine electron-deficient group (Ar), the voltage of the device is low, and the current efficiency is high, while the voltage is increased and the current efficiency is reduced by changing the substituent group (Ar) into phenanthrene and cyano-substituted phenyl in examples 2 and 5, because the triazine group with lower electron density is more obvious in improving the electron injection and mobility in the specific electron-deficient large conjugated structure of the imidazo diazo thio (oxy) hetero seven-membered ring dibenzo.
Comparing example 1 with example 3, it can be seen that the parent imidazole has no substituent R1And R2In the case (example 3), the current efficiency was decreased by 0.12cd/a, but the voltage was greatly decreased by 0.2V, because the whole molecule had better electron deficiency and plane conjugation, and the molecular weight was smaller to make the electron transport resistance smaller and the voltage lower on the premise of ensuring the electron injection and migration performance.
It is understood from the comparison of example 1 with example 6 that, although the voltage is substantially the same when X is O (example 6) as compared with the electron transport material in which X is S (example 1), the current efficiency of example 1 is higher than that of example 6 because the azasulfur seven-membered ring has a higher conjugated electron cloud density than the nitroxide seven-membered ring.
Comparing example 5 with example 7, it can be seen that the substituent R on the parent imidazole1And R2After the phenyl group is changed into the 4-cyanophenyl group (example 7), the driving voltage of the device is reduced, and the current efficiency is higher, because the 4-cyanophenyl group of the linear three-dimensional structure is connected with the single bond of the mother nucleus, so that the whole has a symmetrical linear structure, the electron injection and migration efficiency is further improved, and the driving voltage is reduced, and the current efficiency is also improved by 10 percent.
The experimental data show that the novel organic material is an organic luminescent functional material with good performance as an electron transport material of an organic electroluminescent device, and has wide application prospect.
The present invention is illustrated in detail by the examples described above, but the present invention is not limited to the details described above, i.e., it is not intended that the present invention be implemented by relying on the details described above. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (12)
1. A compound having a structure represented by formula (1);
in the formula (1), X is S or O;
in the formula (1), Ar is any one selected from substituted or unsubstituted C8-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl and cyano;
in the formula (1), L is selected from any one of single bond, substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene;
in the formula (1), R is1And R2Each independently selected from any one of hydrogen, deuterium, halogen, cyano, C2-C20 alkenyl, C2-C20 alkynyl, nitro, C1-C20 chain alkyl, C3-C21 cycloalkyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
in the formula (1), R is selected from any one of deuterium, halogen, cyano, C2-C20 alkenyl, C2-C20 alkynyl, nitro, C1-C20 chain alkyl, C3-C21 cycloalkyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
in the formula (1), n is an integer of 0-7, and m is an integer of 0 or 1;
in the formula (1), Y represents a single bond;
Ar、L、R1、R2and in R, the substituted groups are respectively and independently selected from one or the combination of at least two of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 condensed ring aryl, C3-C30 monocyclic heteroaryl and C6-C30 condensed ring heteroaryl.
2. The compound of claim 1, wherein the compound has any one of the structures shown by formula (a) to formula (h);
the R is3-R9Each independently selected from any one of hydrogen, deuterium, halogen, cyano, C2-C20 alkenyl, C2-C20 alkynyl, nitro, C1-C20 alkyl, C3-C21 cycloalkyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
R3-R9wherein the substituted groups are independently selected from one or a combination of at least two of halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 fused ring aryl, C3-C30 monocyclic heteroaryl and C6-C30 fused ring heteroaryl;
ar, L and R1、R2All having the same limitations as defined in claim 1.
3. A compound according to claim 1 or 2, wherein Ar is selected from any one of substituted or unsubstituted C8-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, cyano, preferably substituted or unsubstituted C3-C30 electron deficient heteroaryl or cyano.
4. A compound according to claim 1 or 2, wherein Ar is selected from cyano or any one of the following substituted or unsubstituted groups:
wherein the wavy line indicates the bond of the group.
5. A compound according to claim 1 or 2, wherein Ar is selected from cyano or any one of the following substituted or unsubstituted groups:
wherein the wavy line indicates the bond of the group;
preferably, said Ar is selected from substituted or unsubstituted triazinyl.
6. A compound according to claim 1 or 2, wherein L is selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group, preferably a single bond, or a substituted or unsubstituted C6-C30 arylene group, further preferably a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group;
preferably, the L is a substituted or unsubstituted phenylene group and the Ar is a cyano group.
7. A compound according to claim 1 or 2, wherein R is1And R2Each independently selected from any one of hydrogen, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
preferably, R1And R2Wherein said substituted or unsubstituted C6-C30 aryl is cyano-substituted C6-C30 aryl, preferably cyano-substituted phenyl;
preferably, said R is1And R2Each independently selected from hydrogen or any one of the following substituted or unsubstituted groups:
preferably, said R is1And R2Each independently selected from hydrogen, cyano-substituted phenyl, or any one of the following substituted or unsubstituted groups:
wherein the wavy line indicates the bond of the group.
8. The compound of claim 1, wherein R is selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl, preferably any one of the following substituted or unsubstituted:
wherein the wavy line indicates the bond of the group.
9. A compound of claim 2, wherein R is3-R9Each independently selected from any one of hydrogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, preferably hydrogen or any one of the following substituted or unsubstituted groups:
wherein the wavy line indicates the bond of the group.
10. The compound of claim 1, wherein the compound has any one of the following structures C1-C75:
11. use of a compound according to any one of claims 1 to 10 for an organic electronic device;
the organic electronic device comprises an organic electroluminescent device, an optical sensor, a solar cell, an illuminating element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet type scanner or electronic paper, preferably the organic electroluminescent device;
preferably, the compound is used as an electron transport material in the organic electroluminescent device.
12. An organic electroluminescent device, characterized in that it comprises a substrate, a first electrode, a second electrode and, between said first and second electrodes, at least one organic layer comprising at least one compound according to any one of claims 1 to 10;
preferably, the organic layer comprises an electron transport layer comprising at least one compound according to any one of claims 1 to 10.
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