CN111499650B - Charge transport material and preparation method and application thereof - Google Patents
Charge transport material and preparation method and application thereof Download PDFInfo
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- CN111499650B CN111499650B CN202010469670.3A CN202010469670A CN111499650B CN 111499650 B CN111499650 B CN 111499650B CN 202010469670 A CN202010469670 A CN 202010469670A CN 111499650 B CN111499650 B CN 111499650B
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- 239000000463 material Substances 0.000 title claims abstract description 102
- 238000002360 preparation method Methods 0.000 title abstract description 11
- 230000005525 hole transport Effects 0.000 claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 230000000903 blocking effect Effects 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims description 13
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 12
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical group 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- -1 diphenylamino Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 238000002347 injection Methods 0.000 claims description 5
- 239000007924 injection Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 230000009471 action Effects 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 230000009477 glass transition Effects 0.000 abstract description 10
- 238000012546 transfer Methods 0.000 abstract description 5
- 230000002035 prolonged effect Effects 0.000 abstract description 3
- 230000002195 synergetic effect Effects 0.000 abstract description 3
- 239000010410 layer Substances 0.000 description 30
- 125000001424 substituent group Chemical group 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 229940125904 compound 1 Drugs 0.000 description 9
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000011630 iodine Substances 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000005561 phenanthryl group Chemical group 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 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 2
- FZTLLUYFWAOGGB-UHFFFAOYSA-N 1,4-dioxane dioxane Chemical compound C1COCCO1.C1COCCO1 FZTLLUYFWAOGGB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical group C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 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 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
- 125000004957 naphthylene group Chemical group 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 125000006617 triphenylamine group Chemical group 0.000 description 2
- VIMMECPCYZXUCI-MIMFYIINSA-N (4s,6r)-6-[(1e)-4,4-bis(4-fluorophenyl)-3-(1-methyltetrazol-5-yl)buta-1,3-dienyl]-4-hydroxyoxan-2-one Chemical compound CN1N=NN=C1C(\C=C\[C@@H]1OC(=O)C[C@@H](O)C1)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 VIMMECPCYZXUCI-MIMFYIINSA-N 0.000 description 1
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000004653 anthracenylene group Chemical group 0.000 description 1
- 125000005264 aryl amine group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- LLCSWKVOHICRDD-UHFFFAOYSA-N buta-1,3-diyne Chemical group C#CC#C LLCSWKVOHICRDD-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000005567 fluorenylene group Chemical group 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- RWWYLEGWBNMMLJ-YSOARWBDSA-N remdesivir Chemical compound NC1=NC=NN2C1=CC=C2[C@]1([C@@H]([C@@H]([C@H](O1)CO[P@](=O)(OC1=CC=CC=C1)N[C@H](C(=O)OCC(CC)CC)C)O)O)C#N RWWYLEGWBNMMLJ-YSOARWBDSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- JLAVCPKULITDHO-UHFFFAOYSA-N tetraphenylsilane Chemical compound C1=CC=CC=C1[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 JLAVCPKULITDHO-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/20—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/20—Spiro-condensed systems
-
- 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
- H10K50/15—Hole transporting layers
-
- 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]
- H10K50/18—Carrier blocking layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides a charge transport material, a preparation method and application thereof, wherein the charge transport material has a structure shown in a formula I and is a compound with a spirofluorene condensed mother nucleus structure. The synergistic effect between the mother nucleus structure and the substituents endows the charge transport material with excellent charge transfer capability, higher glass transition temperature and thermal stability, so that the charge transport material is highly suitable for hole transport materials or electron blocking materials of electroluminescent devices, the luminous efficiency and the brightness of the devices can be effectively improved, the service life is prolonged, and the driving voltage is reduced. The charge transport material is used as a hole transport layer material of an OLED device, so that the luminous efficiency of the device reaches 80Cd/A, the driving voltage can be as low as 4.3V, the service life of the LT95 reaches 170A.U., and the luminous performance of the OLED device is remarkably improved.
Description
Technical Field
The invention belongs to the technical field of organic photoelectric materials, and particularly relates to a charge transport material, a preparation method and application thereof.
Background
The organic electroluminescent device (Organic Light Emission Diodes, OLED) is an active light emitting display device that emits light by recombination of electrons and holes in an organic layer when a current is applied to the organic layer. The organic electroluminescent device has advantages such as light weight, simple element constitution, excellent image quality, convenient manufacturing process, wide viewing angle, high color purity, low power consumption, and the like, and is very suitable for portable electronic devices.
In order to realize the excellent performance of the organic electroluminescent device, not only the structure and the manufacturing process of the electroluminescent device are required to be optimized, but also the organic layer material constituting the device is required to be continuously developed and innovated. In a high performance electroluminescent device, materials constituting the organic layer, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, etc., should be stable and have excellent efficiency. However, the development of organic layer materials currently applied to organic electroluminescent devices is still insufficient. Accordingly, there is a continuing need to develop new materials and apply them to the proper locations of the device.
When the organic electroluminescent device is manufactured by a vacuum deposition method, the operation or storage is in a high temperature environment, which may cause the emitted light to change, the luminous efficiency to decrease, the driving voltage to increase, and the lifetime to decrease. In order to prevent these problems, development of a novel charge transport material having a high glass transition temperature and capable of reducing a driving voltage is required.
CN105384764a discloses an organic charge transport material for OLED display and a preparation method thereof, wherein the organic charge transport material uses tetraphenyl silicon as a main body, and dibenzothiophene with hole transport capability is connected at the para position; to better adjust the HOMO energy level, a pentoxy group with electron donating ability is introduced on dibenzothiophene. The organic electron transport material is suitable for being used as a hole transport layer material in an OLED display device, and has higher glass transition temperature and triplet state energy level.
CN110437085a discloses a hole transport material based on an ether structure, and a preparation method and application thereof, wherein the hole transport material uses oxygen or sulfur-linked diphenylmethane as a core, uses alkoxy or alkylthio-substituted diphenylamine as a side group, and more triphenylamine structures can improve hole mobility, contain the ether or sulfur structure to enable the ether or sulfur structure to have good plane stacking effect, improve hole transport capacity, introduce alkoxy or alkylthio at the tail end to regulate and control the performance of the material, and can be used as a charge transport material for photoelectric devices such as solar cells, OLEDs, organic photosensitive drums and the like.
CN110563724a discloses a hole transporting material, a synthesis method thereof and a display panel, wherein the hole transporting material is a compound formed by combining planar diacetylene and an electron donating group, and the compound has a macrocyclic conjugated system with a rigid planar structure, so that molecules are orderly stacked in space, the hole transporting capability is enhanced, and the hole transporting rate is improved; meanwhile, electron donating groups are easy to migrate holes under the action of an electric field, so that the hole transport rate of the material is improved, and the hole transport material of the conventional OLED display panel is improved.
Although the charge transport materials and their application in OLED devices have been disclosed in the prior art, the charge transport materials still have few kinds, and have the problems of poor thermal stability, low transport efficiency, crystallization in the use process, influence on the service life of the device, and the like, and cannot meet the requirements of the device manufacturing process and the requirements of the device performance.
Therefore, development of a wider variety of charge transport materials having excellent stability and high-efficiency transport properties to meet the demands of low driving voltage, high efficiency, high brightness and long life OLED is an important research point in the art.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a charge transport material, a preparation method and application thereof, and the design of a compound mother core structure and the introduction of substituents on specific sites endow the charge transport material with excellent charge transfer capability and good thermal stability.
To achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the present invention provides a charge transport material having a structure according to formula I:
in the formula I, Z 1 、Z 2 Each independently selected from O or S.
In the formula I, X 1 、X 2 、X 3 、X 4 Each independently selected from C or N, and X 1 、X 2 、X 3 、X 4 At least 2 of them being C, e.g. X 1 、X 2 、X 3 、X 4 There are 2, 3 or 4C.
In the formula I, Y has the structure of
The dotted line represents the attachment site of the group.
L 1 、L 2 、L 3 Each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substitutedOr any one of unsubstituted C3 to C30 heteroarylene groups.
R 1 、R 2 、R 3 、R 4 、R 5 、R 6 Each independently selected from any of hydrogen, deuterium, halogen (e.g., fluorine, chlorine, bromine, or iodine), substituted or unsubstituted C1-C30 straight or branched alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and substituted or unsubstituted C6-C30 arylamine.
In Y, R 5 、R 6 Are not linked, or are linked by chemical bonds to form a ring or are fused to each other.
In the present invention, the "linked to form a ring through a chemical bond" means R 5 And R is 6 The two groups can be connected with each other through chemical bonds to form a ring, the formed ring can be a five-membered or six-membered nitrogen-containing heterocycle, and the specific connection ring forming mode is not limited; the term "fused to each other" means R 5 And R is 6 Can be mutually condensed to form a condensed ring structure, and the specific condensed mode is not limited in the invention. The following description refers to the same meaning when they are linked to form a ring or are fused to each other by chemical bonds.
The C6-C30 may be C6, C7, C8, C9, C10, C12, C15, C18, C20, C22, C24, C25, C27, C29, or the like.
The C3-C30 may be C4, C5, C6, C8, C10, C12, C15, C18, C20, C22, C24, C25, C27, C29, or the like.
The C1-C30 may be C2, C4, C5, C6, C8, C10, C13, C15, C18, C20, C23, C25, C27, C29, or the like.
The charge transport material provided by the invention is a compound with a spirofluorene condensed mother nucleus structure, the specific mother nucleus structure enables the charge transport material to have a macrocyclic conjugation effect, the introduction of N-containing substituent Y (such as aromatic amine or carbazole structure) further improves the charge transport efficiency of the material, and the synergistic effect between the mother nucleus structure and a plurality of substituents enables the charge transport material to have excellent charge transfer capability, higher glass transition temperature and higher thermal stability, so that the charge transport material is particularly suitable for hole transport materials or electron blocking materials of electroluminescent devices, the luminous performance and the service life of the devices can be effectively improved, and the driving voltage is reduced.
In the present invention, L 1 、L 2 、L 3 、R 1 、R 2 、R 3 、R 4 、R 5 、R 6 Each of the substituents of the substitution is independently selected from deuterium, a C1-C20 (e.g., C2, C4, C5, C6, C8, C10, C13, C15, C17, or C19, etc.) linear or branched alkyl group, a C3-C30 (e.g., C4, C5, C6, C8, C10, C13, C15, C18, C20, C23, C25, C27, or C29, etc.) cycloalkyl group, a C1-C20 (e.g., C2, C4, C5, C6, C8, C10, C13, C15, C17, or C19, etc.) alkoxy group, a C6-C30 (e.g., C6, C8, C10, C12, C15, C18, C20, C22, C24, C27, or C29, etc.) aryl group, a C3-C30 (e.g., C4, C5, C6, C8, C10, C13, C15, C18, C20, C23, C25, C27, or C29, etc.), a heteroaryl group, such as fluorine, iodine, or at least one of halogen.
Preferably, the X 1 、X 2 、X 3 、X 4 All are C.
Preferably, the X 1 、X 2 、X 3 、X 4 Each independently selected from C or N, and only 1 is N.
Preferably, the X 1 、X 2 、X 4 All are C, X 3 Is N.
Preferably, the L 1 Selected from single bonds or C6-C12 arylene groups, more preferably single bonds.
The C6-C12 arylene group may be a C6, C10, or C12 arylene group, and the like, and illustratively includes, but is not limited to, phenylene, biphenylene, naphthylene, and the like.
The "L" is 1 By "single bond" is meant that the N atom in substituent Y is connected to the parent nucleus structure in formula I by a single bond.
Preferably, the L 2 、L 3 Each independently selected from a single bond, a substituted or unsubstituted C6-C18 arylene group.
The "L" is 2 Selected from single bonds "means N-primary in substituent YSon and R 5 Is connected through single bond; the "L" is 3 Selected from single bonds "means that the N atom in substituent Y is bonded to R 6 Through single bond connection.
The C6-C18 arylene group may be a C6, C8, C9, C10, C12, C16, C18, etc., exemplary including but not limited to: phenylene, biphenylene, terphenylene, naphthylene, anthrylene, phenanthrylene, fluorenylene, and the like.
L 2 、L 3 Each of the substituents independently selected from at least one of deuterium, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9) straight or branched chain alkyl, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9) alkoxy, C6-C18 (e.g., C7, C9, C10, C12, C14, C16, or C18, etc.) aryl, C3-C20 (e.g., C4, C6, C7, C9, C10, C12, C14, C15, C17, or C19, etc.) heteroaryl, or halogen (e.g., fluorine, chlorine, bromine, or iodine).
Preferably, the L 2 、L 3 Each independently selected from a single bond, phenylene, or biphenylene.
Preferably, said R 5 、R 6 Each independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.
The C6-C30 aryl group may be an aryl group of C6, C7, C8, C9, C10, C12, C13, C15, C18, C20, C22, C24, C25, C27, C29, etc., exemplary including but not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, fluorenyl, spirofluorenyl, and the like.
The C3-C30 heteroaryl may be a C4, C5, C6, C7, C8, C9, C10, C13, C15, C18, C20, C23, C25, C27, or C29 heteroaryl, etc., the heteroatoms of which include N, O or S, etc., exemplary include but are not limited to: n-phenylcarbazolyl, furanyl, thienyl, pyrrolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, carbazolyl, acridinyl, imidazolyl, oxazolyl, thiazolyl, indolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzimidazolyl, quinolinyl, isoquinolinyl, and the like.
R 5 、R 6 Each of the substituents independently selected from at least one of deuterium, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9) straight or branched chain alkyl, C3-C20 (e.g., C4, C5, C6, C8, C10, C13, C15, C17, or C19, etc.) cycloalkyl, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9) alkoxy, C6-C20 (e.g., C7, C9, C10, C12, C14, C16, C18, or C20, etc.) aryl, C3-C20 (e.g., C4, C6, C7, C9, C10, C12, C14, C15, C17, or C19, etc.) heteroaryl, or halogen (e.g., fluorine, chlorine, bromine, or iodine).
Preferably, said R 5 、R 6 Each independently selected from any of hydrogen, deuterium, phenyl, biphenyl, fluorenyl, naphthyl, anthryl, phenanthryl, spirofluorenyl, carbazolyl, N-phenylcarbazolyl, acridinyl, furanyl, thienyl, pyrrolyl, pyridyl, imidazolyl, oxazolyl, thiazolyl, indolyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzimidazolyl, quinolinyl, or isoquinolinyl, or any of the foregoing substituted with a substituent; the R is 5 、R 6 Are not linked, or are linked by chemical bonds to form a ring or are fused to each other.
The substituents are each independently selected from at least one of deuterium, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9) straight or branched chain alkyl, C3-C20 (e.g., C4, C6, C7, C9, C10, C12, C14, C15, C17, or C19, etc.) cycloalkyl, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9) alkoxy, C6-C20 (e.g., C7, C9, C10, C12, C14, C16, C18, or C20, etc.) aryl, C3-C20 (e.g., C4, C6, C7, C9, C10, C12, C14, C15, C17, or C19, etc.) heteroaryl, or halogen (e.g., fluorine, chlorine, bromine, or iodine).
Preferably, Y is selected from any one of the following groups:
wherein the dotted line represents the attachment site of the group.
Preferably, said R 1 、R 2 、R 3 、R 4 Each independently selected from hydrogen, deuterium, halogen (e.g., fluorine, chlorine, bromine or iodine), substituted or unsubstituted C1-C10 straight or branched alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C6-C18 arylamine.
The C1-C10 linear or branched alkyl group may be a C1, C2, C3, C4, C5, C6, C7, C8, C9, or C10 linear or branched alkyl group, exemplary including but not limited to: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl or hexyl and the like.
The C6-C18 aryl group may be a C6, C8, C9, C10, C12, C13, C14, C16, or C18 aryl group, and the like, exemplary including but not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, and the like.
The C6-C18 arylamine group may be a C6, C12, C18, etc., exemplary including but not limited to: diphenylamino or triphenylamine groups, and the like.
The substituted substituents are each independently selected from at least one of deuterium, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9) straight or branched chain alkyl, C3-C20 (e.g., C4, C6, C7, C9, C10, C12, C14, C15, C17, or C19, etc.) cycloalkyl, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, or C9) alkoxy, C6-C20 (e.g., C7, C9, C10, C12, C14, C16, C18, or C20, etc.) aryl, C3-C20 (e.g., C4, C6, C7, C9, C10, C12, C14, C15, C17, or C19, etc.) heteroaryl, or halogen (e.g., fluorine, chlorine, bromine, or iodine).
Preferably, said R 1 、R 2 、R 3 、R 4 Each independently selected from hydrogen, deuterium, phenyl, triphenylamine, or diphenylamino.
Preferably, the charge transport material comprises any one or a combination of at least two of the following compounds 1 to 6:
in another aspect, the present invention provides a method for preparing a charge transport material as described above, the method comprising:
and->
And (3) performing a coupling reaction under the action of a catalyst to obtain the charge transport material.
Z 1 、Z 2 、X 1 、X 2 、X 3 、X 4 、L 1 、L 2 、L 3 、R 1 、R 2 、R 3 、R 4 、R 5 、R 6 Each independently has the same defined ranges as described above.
U is selected from halogen.
Preferably, said U is selected from chlorine or bromine.
Preferably, the catalyst is a palladium catalyst.
In another aspect, the present invention provides an OLED device comprising at least an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode, the material of the hole transport layer comprising a charge transport material as described above.
Preferably, the OLED device further comprises an electron blocking layer, the material of which comprises a charge transport material as described above.
In another aspect, the present invention provides an electronic device comprising an OLED device as described above.
Compared with the prior art, the invention has the following beneficial effects:
the charge transport material provided by the invention is a compound with a spirofluorene condensed mother nucleus structure, and the charge transport material is endowed with excellent charge transfer capability, higher glass transition temperature and thermal stability through the synergistic effect between the mother nucleus structure and a plurality of substituents, so that the charge transport material is highly suitable for hole transport materials or electron blocking materials of electroluminescent devices, the luminous efficiency and the brightness of the devices can be effectively improved, the service life is prolonged, and the driving voltage is reduced. The glass transition temperature of the charge transport material reaches above 110 ℃, and the charge transport material is used as a hole transport layer material of an OLED device, so that the luminous efficiency of the device reaches 62-80 Cd/A, the driving voltage can be as low as 4.3V, the service life of the LT95 reaches 170A.U., and the luminous performance of the OLED device is remarkably improved.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
The starting materials for the compounds in the following examples of the present invention (including compounds 1a, 2b, 3b, 4a, 4 b) are all commercially available.
Example 1
The present embodiment provides a charge transport material having the following structure:
the preparation method comprises the following steps:
4g of Compound 1a,3g of anhydrous cesium carbonate powder, 0.4g of dibenzylideneacetone dipalladium (Pd) 2 dba 3 ) Sequentially adding into 200mL three-necked flask, adding 100mL anhydrous 1,4-dioxane (1, 4-dioxane), stirring well, and processingVacuum was applied while replenishing nitrogen for at least 30min, and allowed to stand in a nitrogen atmosphere. Diphenylamine (2 g in total) is added dropwise under heating and maintaining the temperature at 100 ℃, the reaction is carried out for 24 hours under light-proof reflux, and the spot plate is tracked until the reaction is complete. After cooling and recrystallization, 2.7g of the target product compound 1 was obtained by chromatography on a chromatographic column, with a yield of 52%.
Structural test of target product: glass transition temperature T as measured by Differential Scanning Calorimetry (DSC) g 110 ℃; purity by High Performance Liquid Chromatography (HPLC) was 99.9%;
1 H NMR(400MHz，DMSO)：δ7.84(m,1H),7.55(m,1H),7.5(m,1H),7.48(m,2H),7.4(m,1H),7.38(m,1H),7.32(m,2H),7.28(m,1H),7.26(m,1H),7.22(m,1H),7.2(m,1H),7.1(m,1H),7.01(m,4H),6.9(m,1H),6.89(m,1H),6.7(m,1H),6.62(m,2H),6.61(m,1H),6.54(m,1H),6.46(m,4H)。
example 2
The present embodiment provides a charge transport material having the following structure:
the preparation differs from example 1 only in that the diphenylamine of example 1 is used in equimolar amounts as compound 2b
Alternatively, the desired product compound 2 was obtained in a total of 3.2g in 56% yield.
Structural test of target product: glass transition temperature T as measured by DSC g 113 ℃; purity by HPLC 99.9%;
1 H NMR(400MHz，DMSO)：δ7.84(m,1H),7.55(m,1H),7.5(m,1H),7.48(m,6H),7.4(m,1H),7.38(m,1H),7.32(m,6H),7.28(m,1H),7.23(m,4H),7.26(m,1H),7.22(m,3H),7.2(m,1H),7.1(m,1H),6.90(m,1H),6.89(m,1H),6.70(m,1H),6.61(m,1H),6.54(m,1H),6.52(m,4H)。
example 3
The present embodiment provides a charge transport material having the following structure:
the preparation differs from example 1 only in that the diphenylamine of example 1 is used in equimolar amounts as compound 3b
Alternatively, the desired product compound 3 was obtained in a total of 3.6g in 57% yield.
Structural test of target product: glass transition temperature T as measured by DSC g 114 ℃; purity by HPLC 99.9%;
1 H NMR(400MHz，DMSO)：δ7.84(m,2H),7.55(m,2H),7.59(m,1H),7.5(m,1H),7.48(m,2H),7.4(m,1H),7.38(m,2H),7.32(m,2H),7.28(m,2H),7.26(m,1H),7.22(m,1H),7.2(m,1H),7.1(m,1H),7.01(m,2H),6.90(m,1H),6.89(m,1H),6.75(m,1H),6.70(m,1H),6.62(m,1H),6.61(m,1H),6.58(m,1H),6.54(m,1H),6.46(m,2H),1.67(s,6H)。
example 4
The present embodiment provides a charge transport material having the following structure:
the preparation method comprises the following steps:
4g of the compound 4a,3g of anhydrous cesium carbonate powder, 0.4g of dibenzylideneacetone dipalladium (Pd) 2 dba 3 ) Sequentially adding into 200mL three-port bottles, adding 100mL anhydrous 1,4-dioxane (1, 4-dioxane), stirring uniformly, supplementing nitrogen in the process, vacuumizing for at least 30min, and keeping in nitrogen atmosphere. Heating and maintaining at 100deg.C, dropwise adding compound 4b (2.9 g), reflux-reacting for 24 hr under dark condition, and tracking the spot plate until the reaction is completedAll of them. After cooling and recrystallization, chromatography by a chromatographic column yields 4.2g of the objective compound 4 with a yield of 63%.
Structural test of target product: glass transition temperature T as measured by DSC g 120 ℃; purity by HPLC 99.9%; the method comprises the steps of carrying out a first treatment on the surface of the
1 H NMR(400MHz，DMSO)：δ8.59(m,2H),7.84(m,1H),7.55(m,1H),7.48(m,4H),7.38(m,2H),7.32(m,4H),7.28(m,1H),7.23(m,2H),7.26(m,1H),7.22(m,2H),7.01(m,2H),6.90(m,1H),6.89(m,1H),6.70(m,1H),6.62(m,1H),6.61(m,1H),6.54(m,1H),6.52(m,2H),6.46(d,2H)。
Application example 1
An OLED device comprising, in order: an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode; the material composition of each layer is specifically as follows:
anode: a thickness of 80nm, indium Tin Oxide (ITO);
hole injection layer: the thickness is 10nm; the host material is NPB, the guest material is F4-TCNQ, and the mass percentage of the guest material is 3%;
hole transport layer: a thickness of 100nm, the charge transport material (compound 1) provided in example 1 of the present invention;
light emitting layer: the thickness is 20nm; the host material is TCTA, and the guest material is Ir (ppy) 3 The mass percentage of the guest material is 5%;
electron transport layer: the thickness is 30nm; the host material is BPen, the guest material is LiQ, and the mass percentage of the guest material is 50%;
and (3) cathode: a Mg/Ag electrode with a thickness of 20nm;
the hole injection layer, the hole transport layer, the light-emitting layer, the electron transport layer and the cathode of the OLED device are prepared by an evaporation method.
Application example 2
An OLED device differing from application example 1 only in that compound 1 in the hole transport layer was replaced with the charge transport material (compound 2) provided in example 2 of the present invention.
Application example 3
An OLED device differing from application example 1 only in that compound 1 in the hole transport layer was replaced with the charge transport material (compound 3) provided in example 3 of the present invention.
Application example 4
An OLED device differing from application example 1 only in that compound 1 in the hole transport layer was replaced with the charge transport material (compound 4) provided in example 4 of the present invention.
Application example 5
An OLED device differing from application example 1 only in that Compound 1 in the hole-transporting layer was treated with Charge-transporting Material Compound 7 provided by the present invention
And (5) replacing.
Comparative example 1
An OLED device differing from application example 1 only in that Compound 1 in the hole-transporting layer was used as a comparative Compound NPB
And (5) replacing.
Comparative example 2
An OLED device differing from application example 1 only in that Compound 1 in the hole-transporting layer was used as comparative Compound 2
And (5) replacing.
Comparative example 3
An OLED device differing from application example 1 only in that Compound 1 in the hole-transporting layer was used as comparative Compound 3
And (5) replacing.
Performance test of OLED device:
the OLED devices provided in application examples 1 to 5 and comparative examples 1 to 3 were subjected to a test for luminous efficiency, and the test method was as follows: data of driving voltage V and luminous efficiency LE were measured at a luminance of 1000nits, LT95 lifetime data at a current density of 40mA/cm 2 Calculated under the condition.
The performance test results are shown in table 1:
TABLE 1
As can be seen from the data in Table 1, the charge transport material provided by the invention is suitable for being used as a hole transport layer material in an OLED device, and compared with a hole transport material NPB commonly used in the prior art, the OLED device using the charge transport material as a hole transport layer has the luminous efficiency reaching 62-80 Cd/A, the LT95 service life reaching 140-170 A.U., the driving voltage is reduced to 4.3-5.0V, the luminous efficiency of the device is effectively improved, the service life of the device is prolonged, and the driving voltage is reduced.
In the charge transport material provided by the invention, the specific parent nucleus structure and the substituent groups are mutually cooperated, so that the charge transport material has excellent charge transfer capability, and the change of the parent nucleus structure (comparative example 3) or the deletion of the substituent groups (comparative example 2) can lead to the reduction of the transport efficiency of the material and influence the performance of a device.
The applicant states that the present invention is described by way of the above examples as a charge transport material, and methods of making and using the same, but the present invention is not limited to, i.e., does not mean that the present invention must be practiced in dependence upon, the above examples. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of raw materials for the product of the present invention, addition of auxiliary components, selection of specific modes, etc., falls within the scope of the present invention and the scope of disclosure.
Claims (12)
1. A charge transport material, wherein the charge transport material has a structure according to formula I:
wherein Z is 1 、Z 2 Each independently selected from O or S;
X 1 、X 2 、X 3 、X 4 each independently selected from C or N, and X 1 、X 2 、X 3 、X 4 Wherein 3 or 4 of them are C;
y is selected from any one of the following groups:
the dotted line represents the attachment site of the group;
R 1 、R 2 、R 3 each independently selected from any one of hydrogen, deuterium, C6-C18 aryl and C6-C18 arylamine;
R 4 is hydrogen.
2. The charge transport material of claim 1, wherein X is 1 、X 2 、X 3 、X 4 All are C.
3. The charge transport material of claim 1, wherein X is 1 、X 2 、X 3 、X 4 Each independently selected from C or N, and only 1 is N.
4. The charge transport material of claim 1, wherein X is 1 、X 2 、X 4 All are C, X 3 Is N.
5. The charge transport material of claim 1, wherein R 1 、R 2 、R 3 Each independently selected from hydrogen, deuterium, phenyl, triphenylamine, or diphenylamino.
6. The charge transport material of claim 1, wherein the charge transport material comprises any one or a combination of at least two of the following compounds 1-14:
7. a method of producing the charge transport material according to any one of claims 1 to 6, comprising:
carrying out coupling reaction with Y-H under the action of a catalyst to obtain the charge transport material;
L 1 is a single bond, Y, Z 1 、Z 2 、X 1 、X 2 、X 3 、X 4 、R 1 、R 2 、R 3 、R 4 Having the same limitations as in claim 1;
u is selected from halogen.
8. The method of claim 7, wherein U is selected from chlorine or bromine.
9. The method of claim 7, wherein the catalyst is a palladium catalyst.
10. An OLED device comprising at least an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode, wherein the hole transport layer comprises a charge transport material according to any one of claims 1 to 6.
11. The OLED device of claim 10, further comprising an electron blocking layer, wherein the material of the electron blocking layer comprises the charge transport material of any one of claims 1-6.
12. An electronic device, characterized in that it comprises an OLED device as claimed in claim 10 or 11.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106255695A (en) * | 2014-04-29 | 2016-12-21 | 东进世美肯株式会社 | New compound and comprise its organic illuminating element |
| CN110818670A (en) * | 2018-08-07 | 2020-02-21 | 乐金显示有限公司 | Compound and organic light-emitting device |
| CN112321646A (en) * | 2020-10-21 | 2021-02-05 | 上海天马有机发光显示技术有限公司 | Organic compound, electroluminescent material and application thereof |
| CN112321587A (en) * | 2020-10-30 | 2021-02-05 | 上海天马有机发光显示技术有限公司 | Organic compound, electroluminescent material and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106255695A (en) * | 2014-04-29 | 2016-12-21 | 东进世美肯株式会社 | New compound and comprise its organic illuminating element |
| CN110818670A (en) * | 2018-08-07 | 2020-02-21 | 乐金显示有限公司 | Compound and organic light-emitting device |
| CN112321646A (en) * | 2020-10-21 | 2021-02-05 | 上海天马有机发光显示技术有限公司 | Organic compound, electroluminescent material and application thereof |
| CN112321587A (en) * | 2020-10-30 | 2021-02-05 | 上海天马有机发光显示技术有限公司 | Organic compound, electroluminescent material and application thereof |
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