CN113461593B - Biphenyl amine derivative and application thereof - Google Patents
Biphenyl amine derivative and application thereof Download PDFInfo
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- CN113461593B CN113461593B CN202110029258.4A CN202110029258A CN113461593B CN 113461593 B CN113461593 B CN 113461593B CN 202110029258 A CN202110029258 A CN 202110029258A CN 113461593 B CN113461593 B CN 113461593B
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- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical class C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 title abstract description 8
- 239000010410 layer Substances 0.000 claims abstract description 162
- 239000000463 material Substances 0.000 claims abstract description 67
- 238000002347 injection Methods 0.000 claims abstract description 35
- 239000007924 injection Substances 0.000 claims abstract description 35
- 230000000903 blocking effect Effects 0.000 claims abstract description 30
- TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical class NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000002346 layers by function Substances 0.000 claims abstract description 9
- 230000005525 hole transport Effects 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- -1 dibenzofuranyl Chemical group 0.000 claims description 8
- 239000011368 organic material Substances 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 3
- 241000720974 Protium Species 0.000 claims description 3
- 125000006267 biphenyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims 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 claims description 2
- 150000001975 deuterium Chemical group 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 11
- 230000005540 biological transmission Effects 0.000 abstract description 9
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 abstract description 3
- 230000006798 recombination Effects 0.000 abstract description 3
- 238000005215 recombination Methods 0.000 abstract description 3
- 239000004065 semiconductor Substances 0.000 abstract description 2
- 230000005855 radiation Effects 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 description 56
- 150000001875 compounds Chemical class 0.000 description 42
- 239000010408 film Substances 0.000 description 33
- 230000000052 comparative effect Effects 0.000 description 15
- 230000008025 crystallization Effects 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- 238000007740 vapor deposition Methods 0.000 description 10
- 239000000376 reactant Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000008204 material by function Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000007738 vacuum evaporation Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007772 electrode material Substances 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000010025 steaming Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 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
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229910052722 tritium Inorganic materials 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 1
- PAYROHWFGZADBR-UHFFFAOYSA-N 2-[[4-amino-5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidin-2-yl]amino]propane-1,3-diol Chemical compound C1=C(I)C(OC)=CC(C(C)C)=C1OC1=CN=C(NC(CO)CO)N=C1N PAYROHWFGZADBR-UHFFFAOYSA-N 0.000 description 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
- VKLKXFOZNHEBSW-UHFFFAOYSA-N 5-[[3-[(4-morpholin-4-ylbenzoyl)amino]phenyl]methoxy]pyridine-3-carboxamide Chemical compound O1CCN(CC1)C1=CC=C(C(=O)NC=2C=C(COC=3C=NC=C(C(=O)N)C=3)C=CC=2)C=C1 VKLKXFOZNHEBSW-UHFFFAOYSA-N 0.000 description 1
- XASOHFCUIQARJT-UHFFFAOYSA-N 8-methoxy-6-[7-(2-morpholin-4-ylethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C(N1C(=O)C2=C(OC)C=C(C=3N4C(=NC=3)C=C(C=C4)OCCN3CCOCC3)C=C2CC1)C(F)(F)F XASOHFCUIQARJT-UHFFFAOYSA-N 0.000 description 1
- KCBAMQOKOLXLOX-BSZYMOERSA-N CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O Chemical compound CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O KCBAMQOKOLXLOX-BSZYMOERSA-N 0.000 description 1
- SCJNYBYSTCRPAO-LXBQGUBHSA-N CN(C)C\C=C\C(=O)NC1=CC=C(N=C1)C(=O)N[C@@]1(C)CCC[C@H](C1)NC1=NC(C2=CNC3=CC=CC=C23)=C(Cl)C=N1 Chemical compound CN(C)C\C=C\C(=O)NC1=CC=C(N=C1)C(=O)N[C@@]1(C)CCC[C@H](C1)NC1=NC(C2=CNC3=CC=CC=C23)=C(Cl)C=N1 SCJNYBYSTCRPAO-LXBQGUBHSA-N 0.000 description 1
- 101100412446 Caenorhabditis elegans rer-1 gene Proteins 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 238000011982 device technology Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000012994 industrial processing Methods 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 238000005036 potential barrier Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001894 space-charge-limited current method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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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
- H10K85/649—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
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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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- Chemical & Material Sciences (AREA)
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- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to a biphenylamine derivative and application thereof, belonging to the technical field of semiconductors, and the structure of the biphenylamine derivative is shown as a general formula (1): The invention also discloses application of the biphenyl amine derivative. The biphenylamine derivative provided by the invention has stronger hole transmission capability, and improves hole injection and transmission performance under proper HOMO energy level; under the proper LUMO energy level, the electron blocking function is also realized, and the recombination efficiency of excitons in the light-emitting layer is improved; when the organic light-emitting diode is used as a light-emitting functional layer material of an OLED light-emitting device, the exciton utilization rate and the radiation efficiency can be effectively improved.
Description
Technical Field
The invention relates to the technical field of semiconductors, in particular to a biphenyl amine derivative and application thereof.
Background
The organic electroluminescent (OLED: organic Light Emission Diodes) device technology can be used for manufacturing novel display products and novel illumination products, is hopeful to replace the existing liquid crystal display and fluorescent lamp illumination, and has wide application prospect. The OLED light-emitting device is like a sandwich structure and comprises electrode material film layers and organic functional materials clamped between different electrode film layers, wherein various functional materials are mutually overlapped together according to purposes to jointly form the OLED light-emitting device. When voltage is applied to two end electrodes of the OLED light-emitting device as a current device, positive and negative charges in the organic layer functional material film layer act through an electric field, and the positive and negative charges are further compounded in the light-emitting layer, so that OLED electroluminescence is generated.
At present, the OLED display technology has been applied to the fields of smart phones, tablet computers and the like, and further expands to the large-size application fields of televisions and the like, but compared with the actual product application requirements, the OLED display technology has the advantages that the luminous efficiency, the service life and the like of OLED devices are further improved. The studies on the improvement of the performance of the OLED light emitting device include: the driving voltage of the device is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the like. In order to realize the continuous improvement of the performance of the OLED device, not only is the innovation of the structure and the manufacturing process of the OLED device needed, but also the continuous research and innovation of the OLED photoelectric functional material are needed, and the functional material of the OLED with higher performance is created.
The OLED photoelectric functional materials applied to the OLED device can be classified into two major categories in terms of use, namely, charge injection transport materials and light emitting materials, and further, the charge injection transport materials can be further classified into electron injection transport materials, electron blocking materials, hole injection transport materials and hole blocking materials, and the light emitting materials can be further classified into host light emitting materials and doping materials.
In order to manufacture high-performance OLED light emitting devices, various organic functional materials are required to have good photoelectric properties, for example, as a charge transport material, good carrier mobility, high glass transition temperature, and the like, and as a host material of a light emitting layer, a material having good bipolar properties, appropriate HOMO/LUMO energy levels, and the like are required.
When the organic OLED device is applied to a display apparatus, the organic OLED device is required to have a long life and high efficiency, particularly, a blue light device (compared to red and green light emitting devices) of a blue pixel region, a driving voltage is high, and a lifetime is short. In order to prolong the service life of blue pixels and reduce driving voltage, the requirements on the film phase stability and the thermal stability of the hole transport materials are enhanced at present.
At present, the hole transmission side is mainly made of aromatic amine compounds, but devices prepared from the materials still have the problems of higher voltage and shorter service life, so that the service life of blue light devices is prolonged, and the problem that the voltage of the devices is reduced is still needed to be overcome.
Disclosure of Invention
In view of the above problems in the prior art, the applicant provides a biphenylamine derivative and application thereof. The compound has higher hole mobility and proper HOMO energy level, and has stronger film phase stability and molecular thermal stability, so that the service life of an OLED device can be effectively prolonged, and the device voltage can be reduced.
The invention provides a specific technical scheme as follows: a biphenylamine derivative has a structure shown in a general formula (1):
In the general formula (1), each R 1-R3 is independently represented by a substituted or unsubstituted C 6-30 aryl group, a substituted or unsubstituted C 2-30 heteroaryl group containing one or more heteroatoms;
Ar is a substituted or unsubstituted C 6-30 arylene group, a substituted or unsubstituted C 2-30 heteroarylene group containing one or more heteroatoms;
r 4 is represented by a structure shown in a general formula (2);
The Ra represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted dibenzofuranyl group;
In the general formula (2), rb and Rc are respectively and independently protium, deuterium, tritium, methoxy, alkyl of C 1-20, cycloalkyl of C 3-20, substituted or unsubstituted C 6-30 aryl and substituted or unsubstituted C 2-30 heteroaryl containing one or more hetero atoms; the Rb and Rc may be the same or different;
m=1 or 2; said n, o=0, 1 or 2;
The substituents of the substitutable group are optionally one or more from the group consisting of deuterium atoms, methoxy groups, alkyl groups of C 1-20, cycloalkyl groups of C 3-20, C 6-30 aryl groups, substituted or unsubstituted C 2-30 heteroaryl groups containing one or more heteroatoms;
the heteroatom is any one or more selected from oxygen atoms, sulfur atoms or nitrogen atoms.
Further, ra is represented as phenyl.
Further, each of the R 1-R3 is independently represented as one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted fluorenyl group, and a substituted or unsubstituted carbazolyl group;
Ar represents one of a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrylene group-substituted or unsubstituted benzophenanthrene group;
Each of Rb, rc is independently represented by one of protium, deuterium, tritium, methoxy, methyl, ethyl, propyl, isopropyl, t-butyl, pentyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted furyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl; the Rb and Rc may be the same or different;
The substituents of the substitutable group are optionally selected from one or more of deuterium atom, methoxy, methyl, ethyl, propyl, adamantyl, isopropyl, tert-butyl, pentyl, phenyl, naphthyl or biphenyl.
Further, the general formula (1) can be represented by a structure represented by general formula (III-1) -general formula (III-3);
the symbols in the general formulae (III-1) - (III-3) have the meanings defined in claim 1.
Further, the specific structure of the derivative is as follows:
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the second aspect of the invention provides application of the biphenyl amine derivative in preparing an organic electroluminescent device.
In a third aspect, the present invention provides an organic electroluminescent device, which has the characteristics of comprising a cathode, an anode and a functional layer, wherein the functional layer is located between the anode and the cathode, and at least one functional layer of the organic electroluminescent device contains the biphenylamine derivative.
A fourth aspect of the present invention is to provide an organic electroluminescent device comprising a hole transport layer having such a feature that the hole transport layer contains the biphenylamine derivative.
A fifth aspect of the present invention is to provide an organic electroluminescent device comprising an electron blocking layer having such a feature that the electron blocking layer contains the biphenylamine derivative.
A sixth aspect of the present invention is to provide an organic electroluminescent device having such a feature that the above-mentioned organic electroluminescent device comprises a hole injection layer, a hole transport auxiliary layer, a light emitting layer and an electron transport region, the hole transport auxiliary layer being adjacent to the light emitting layer, the hole injection layer comprising a P-doped material and the above-mentioned biphenylamine derivative, the hole transport layer comprising the same organic material as the hole injection layer.
A seventh aspect of the present invention is to provide an organic electroluminescent device having such a feature that the above-mentioned organic electroluminescent device comprises a hole injection layer, a hole transport auxiliary layer, a light emitting layer and an electron transport region, the hole transport auxiliary layer being adjacent to the light emitting layer, the hole injection layer comprising a P-doped material and an organic material, the hole transport layer comprising the same organic material as the hole injection layer, the hole transport auxiliary layer comprising the above-mentioned biphenylamine derivative, the hole auxiliary layer comprising one or two materials.
An eighth aspect of the present invention provides a full-color display device, which includes, in order from bottom to top, a substrate, a first electrode, an organic functional material layer, and a second electrode, the organic functional material layer including: a hole transport region located over the first electrode; a light emitting layer on the hole transporting region, the light emitting layer having a red light emitting layer, a green light emitting layer and a blue light emitting layer patterned in a red pixel region, a green pixel region and a blue pixel region, respectively; an electron transport region located over the light emitting layer; the hole transport region comprises a hole injection layer, a hole transport layer and a hole transport auxiliary layer from bottom to top in sequence, the hole injection layer comprises a P-type doping material, the red pixel unit, the green pixel unit and the blue pixel unit have a common hole injection layer and a hole transport layer, and the hole transport region comprises respective hole transport auxiliary layers, and the hole transport region comprises the biphenyl amine derivative shown in the general formula (1).
A ninth aspect of the present invention is to provide an illumination or display element having such features, including the organic electroluminescent device described above.
Compared with the prior art, the invention has the beneficial technical effects that:
(1) In the device driving process, if crystallization occurs in the HT material film layer, the service life of the device is shorter, compared with the structure disclosed in patent CN1984874A, the compound has more excellent film crystallization stability because of taking the biphenylamine derivative and carbazole as the core, and the hole transport material has a thickness of 120nm in the TOP device structure and is a common layer of red, green and blue pixels, so that the hole transport material is required to have excellent film crystallization stability (film crystallization stability standard is that the crystallization is not performed at 85 ℃ for 1000 hours and the crystallization is not performed at 115 ℃ for 200 hours);
(2) The compound has smaller reforming energy (energy generated by molecular configuration change and environmental polarization caused by electronic state change), so that the compound has higher mobility, has excellent hole transport performance, and can obviously reduce the voltage of an OLED device when applied to the device;
(3) The compound takes the biphenylamine derivative as a core, has higher hole mobility, can be used as a material of a hole transmission layer of an OLED luminescent device, can improve the recombination efficiency of excitons in the luminescent layer and improve the energy utilization rate, so that the luminescent efficiency of the device is improved, and the compound taking the biphenylamine derivative as the core can reduce the potential barrier of an anode interface due to proper HOMO energy level, is beneficial to the injection of holes, and can form a stable CT complex with P doping under low concentration, so that the injection of holes is enhanced;
(4) The compound has excellent hole injection capability and excellent hole transmission performance, so that the compound can be applied as a hole transmission material, more holes can be injected into the light-emitting layer, a composite region of the light-emitting layer is far away from the EB side, and long service life of the device is facilitated;
(5) The compound provided by the invention has a proper HOMO energy level, can form a stable CT complex with a P doped material under a low doping proportion, further improves hole injection efficiency, and reduces risk of Cross-talk (red, green and blue pixels Cross color due to different starting voltages of the red, green and blue pixels, wherein the starting voltage of the blue pixel is highest, and the risk of starting an adjacent pixel point is caused when a blue light pixel is started.
(6) The biphenylamine derivative of the invention enables the distribution of electrons and holes in the light-emitting layer to be more balanced, and improves the hole injection and transmission performance under the proper HOMO energy level; under the proper LUMO energy level, the electron blocking function is also realized, and the recombination efficiency of excitons in the light-emitting layer is improved; the exciton utilization rate can be effectively improved, the device voltage can be reduced, and the current efficiency and the service life of the device can be improved. The biphenylamine derivative has good application effect in OLED luminescent devices and has good industrialization prospect.
(7) The structure of the compound biphenyl amine derivative of the invention has an amino structure, so that the biphenyl amine derivative of the invention has higher mobility and wider band gap, thereby ensuring that the biphenyl amine derivative of the invention has no absorption in the visible light field; in addition, the intermolecular distance is increased, and the intermolecular interaction force is weakened, so that the vapor deposition temperature is low, and the industrial processing window of the material is widened.
(8) The material with deep HOMO energy level and wider band gap can be used as a green light and red light electron blocking layer, the wider band gap can effectively block electrons from being transmitted to one side of the hole transmission layer, the degradation of electrons to the hole transmission material is effectively prevented, and the material has excellent film phase stability and mobility, so that the material can effectively prolong the service life of the device when being used as the green light and red light electron blocking layer.
Drawings
FIG. 1 is a schematic diagram of the structure of an OLED device using the materials of the present invention;
Wherein 1 is a transparent substrate layer, 2 is an ITO anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is an electron transport or hole blocking layer, 8 is an electron injection layer, 9 is a cathode layer, and 10 is a CPL layer.
FIG. 2 shows the results of film crystallization experiments of the compound 4 of the present application and a comparative compound.
Detailed Description
The principles and features of the present invention are described below with reference to the drawings, the illustrated embodiments are provided for illustration only and are not intended to limit the scope of the present invention.
All materials in the examples described below were purchased from tobacco stand Mo Run fine chemicals Co., ltd.
Preparation of reactant A-1
Adding 0.01mol of raw material X-1,0.01mol of raw material X-2 and 150ml of toluene into a 250ml three-port bottle under the protection of nitrogen, stirring and mixing, then adding 5X 10 -5mol Pd2(dba)3,5×10-5mol P(t-Bu)3 and 0.03mol of sodium tert-butoxide, heating to 105 ℃, carrying out reflux reaction for 24 hours, sampling a dot plate, and displaying no bromide residue, wherein the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction exists, and passing through a neutral silica gel column to obtain a reactant A-1, wherein the purity of HPLC is 99.06%, and the yield is 82.65%;
theoretical value of elemental analysis structure (C 36H26N2): c,88.86; h,5.39; n,5.76; test value: c,88.88; h,5.38; n,5.75.LC-MS: theoretical value 486.21, found 486.25.
The preparation of the other reactant A was similar to that of reactant A-1, except for the different starting materials used.
Example 1 preparation of Compound 4
(1) Adding 0.01mol of reactant A-2 and 0.01mol of reactant B-1 into a 250ml three-port bottle under the protection of nitrogen, stirring and mixing 150ml of toluene, then adding 5X 10 -5mol Pd2(dba)3,5×10-5mol P(t-Bu)3 and 0.03mol of sodium tert-butoxide, heating to 105 ℃, carrying out reflux reaction for 24 hours, sampling a dot plate, and displaying no bromide residue, wherein the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction is present, and passing through a neutral silica gel column to obtain an intermediate C-1;
(2) Adding 0.01mol of intermediate C-1 and 0.01mol of reactant A-1 into a 250ml three-port bottle under the protection of nitrogen, stirring and mixing 150ml of toluene, then adding 5X 10 -5mol Pd2(dba)3,5×10-5mol P(t-Bu)3 and 0.03mol of sodium tert-butoxide, heating to 105 ℃, carrying out reflux reaction for 24 hours, sampling a dot plate, and displaying no bromide residue, wherein the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction exists, and passing through a neutral silica gel column to obtain the compound 4.
The procedure of example 1 was repeated to synthesize the following compounds, except that reactant A and reactant B, as set forth in Table 1-1 below, were used, and the test results are also set forth in the following Table.
TABLE 1-1
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The compound of the invention is used in a light-emitting device, can be used as a hole transport layer material and also can be used as an electron blocking layer material. The compounds prepared in the above examples of the present invention were tested for thermal properties, T1 energy level, HOMO energy level and hole mobility, respectively, and the test results are shown in table 2:
TABLE 2
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Note that: the triplet state energy level T1 is tested by a fluorescent-3 series fluorescence spectrometer of Horiba, and the test condition of the material is toluene solution of 2 x10 -5 mol/L; the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, german fast Co., DSC204F1 differential scanning calorimeter) at a heating rate of 10 ℃/min; the thermal weight loss temperature Td is a temperature at which the weight loss is 1% in a nitrogen atmosphere, and is measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation, the nitrogen flow rate is 20mL/min; the highest occupied molecular orbital HOMO energy level was tested by the ionization energy measurement system (IPS-3), tested as an atmospheric environment; eg was tested by a dual beam UV-Vis spectrophotometer (model: TU-1901); hole mobility test the materials of the present invention were fabricated into single charge devices and tested using the SCLC method.
As can be seen from the data in the table, the organic compound of the invention has a more suitable HOMO energy level, can be applied to a hole transport layer or an electron blocking layer, has higher hole mobility and higher thermal stability, and improves the efficiency and the service life of the manufactured OLED device containing the organic compound of the invention.
The effect of the OLED materials synthesized according to the present invention in the application to devices will be described in detail below with reference to device examples 1 to 50 and device comparative examples 1 to 5. The device examples 1-50 of the present invention were identical in device fabrication process to the device comparative examples 1-5, and the same substrate materials and electrode materials were used, and the film thickness of the electrode materials was also kept uniform, except that the hole injection layer and hole transport layer materials or electron blocking layer materials in the device were replaced.
Device comparative example 1 (Blue)
The preparation process comprises the following steps:
As shown in fig. 1, the transparent substrate layer 1 is washed with an anode layer 2 (ITO (15 nm)/Ag (150 nm)/ITO (15 nm)), that is, alkali washing, pure water washing, drying, and ultraviolet-ozone washing in order to remove organic residues on the surface of the anode layer. On the anode layer 2 after the above washing, HT-1 and P-1 having film thicknesses of 10nm were vapor deposited as hole injection layers 3 by a vacuum vapor deposition apparatus, and the mass ratio of HT-1 and P-1 was 97:3. Next, HT-1 was evaporated to a thickness of 120nm as a hole transport layer 4. Subsequently EB-1 was evaporated to a thickness of 10nm as an electron blocking layer 5. After the evaporation of the electron blocking material is completed, a light emitting layer 6 of the OLED light emitting device is manufactured, and the structure of the light emitting layer comprises BH-1 used by the OLED light emitting layer 6 as a main material, BD-1 as a doping material, the doping material doping ratio is 3% by weight, and the film thickness of the light emitting layer is 20nm. After the luminescent layer 6, the ET-1 and the Liq are continuously evaporated, and the mass ratio of the ET-1 to the Liq is 1:1. The vacuum evaporation film thickness of the material is 30nm, and the layer is a hole blocking/electron transport layer 7. On the hole blocking/electron transporting layer 7, a LiF layer having a film thickness of 1nm, which is an electron injecting layer 8, was produced by a vacuum vapor deposition apparatus. On the electron injection layer 8, mg having a film thickness of 16nm was produced by a vacuum vapor deposition apparatus: the mass ratio of Mg to Ag in the Ag electrode layer is 1:9, and the Ag electrode layer is used as a cathode layer 9. On the cathode layer 9, 70nm of CP-1 was vacuum-deposited as CPL layer 10.
Device comparative example 2 (Green)
As shown in fig. 1, the transparent substrate layer 1 is washed with an anode layer 2 (ITO (15 nm)/Ag (150 nm)/ITO (15 nm)), that is, alkali washing, pure water washing, drying, and ultraviolet-ozone washing in order to remove organic residues on the surface of the anode layer. On the anode layer 2 after the above washing, HT-2 and P-1 having film thicknesses of 10nm were vapor deposited as hole injection layers 3 by a vacuum vapor deposition apparatus, and the mass ratio of HT-2 to P-1 was 97:3. Next, HT-2 having a thickness of 120nm was evaporated as a hole transport layer 4. EB-2 was then evaporated to a thickness of 30nm as an electron blocking layer 5. After the evaporation of the electron blocking material is finished, the luminescent layer 6 of the OLED luminescent device is manufactured, the structure of the luminescent layer comprises GH-1 and GH-2 used by the OLED luminescent layer 6 as main materials, GD-1 as doping materials, the mass ratio of the GH-1, the GH-2 and the GD-1 is 47:47:6, and the thickness of the luminescent layer is 30nm. After the luminescent layer 6, the ET-1 and the Liq are continuously evaporated, and the mass ratio of the ET-1 to the Liq is 1:1. The vacuum evaporation film thickness of the material is 30nm, and the layer is a hole blocking/electron transport layer 7. On the hole blocking/electron transporting layer 7, a LiF layer having a film thickness of 1nm, which is an electron injecting layer 8, was produced by a vacuum vapor deposition apparatus. On the electron injection layer 8, mg having a film thickness of 16nm was produced by a vacuum vapor deposition apparatus: the mass ratio of Mg to Ag in the Ag electrode layer is 1:9, and the Ag electrode layer is used as a cathode layer 9. On the cathode layer 9, 70nm of CP-1 was vacuum-deposited as CPL layer 10.
Device comparative example 3 (Red)
As shown in fig. 1, the transparent substrate layer 1 is washed with an anode layer 2 (ITO (15 nm)/Ag (150 nm)/ITO (15 nm)), that is, alkali washing, pure water washing, drying, and ultraviolet-ozone washing in order to remove organic residues on the surface of the anode layer. On the anode layer 2 after the above washing, HT-2 and P-1 having film thicknesses of 10nm were vapor deposited as hole injection layers 3 by a vacuum vapor deposition apparatus, and the mass ratio of HT-2 to P-1 was 97:3. Next, HT-2 having a thickness of 120nm was evaporated as a hole transport layer 4. Subsequently EB-3 was evaporated to a thickness of 80nm as electron blocking layer 5. After the evaporation of the electron blocking material is finished, the light emitting layer 6 of the OLED light emitting device is manufactured, and the structure of the light emitting layer comprises RH-1 used by the OLED light emitting layer 6 as a main material, RD-1 as a doping material, the mass ratio of the RH-1 to the RD-1 is 97:3, and the film thickness of the light emitting layer is 30nm. After the luminescent layer 6, the ET-1 and the Liq are continuously evaporated, and the mass ratio of the ET-1 to the Liq is 1:1. The vacuum evaporation film thickness of the material is 30nm, and the layer is a hole blocking/electron transport layer 7. On the hole blocking/electron transporting layer 7, a LiF layer having a film thickness of 1nm, which is an electron injecting layer 8, was produced by a vacuum vapor deposition apparatus. On the electron injection layer 8, mg having a film thickness of 16nm was produced by a vacuum vapor deposition apparatus: the mass ratio of Mg to Ag in the Ag electrode layer is 1:9, and the Ag electrode layer is used as a cathode layer 9. On the cathode layer 9, 70nm of CP-1 was vacuum-deposited as CPL layer 10.
Device examples 1-22: device examples 1-22 were prepared in the same manner as device comparative example 1, except that the organic materials of the hole injection layer and the hole transport layer material or the electron blocking layer were used with the organic compounds of the present application.
Device examples 23-37: device examples 23-37 were prepared in the same manner as device comparative example 2, except that the organic materials of the hole injection layer and the hole transport layer material or the electron blocking layer were used with the organic compounds of the present application.
Device examples 38-52: device examples 38-52 were prepared in the same manner as device comparative example 3, except that the organic materials of the hole injection layer and the hole transport layer material or the electron blocking layer were used with the organic compounds of the present application.
Device comparative examples 4, 5: the device comparative examples 4 and 5 were prepared in the same manner as in the device comparative example 1, except that the hole injection layer was made of the organic material rer-1 or ref-2.
The molecular structural formula of the related material is shown as follows:
After completing the OLED light emitting device as described above, the anode and cathode were connected by a well-known driving circuit, and the current efficiency of the device, the light emission spectrum, and the lifetime of the device were measured. Specific structures of device examples 1-50 are shown in Table 3; the results of the tests for current efficiency, color and lifetime of the obtained devices are shown in tables 4 to 6.
TABLE 3 Table 3
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TABLE 4 Table 4
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TABLE 5
TABLE 6
Note that: the voltage, current efficiency and color coordinates were tested using an IVL (Current-Voltage-Brightness) test system (Freund's scientific instruments, st., inc.), with a current density of 10mA/cm 2 at the time of testing; the life test system is an EAS-62C OLED device life tester of Japanese system technical research company; LT95 refers to the time taken for the device brightness to decay to 95% at a particular brightness (blue light: 1000nits; green light: 10000nits; red light: 8000 nits).
As can be seen from the device data results, the organic light emitting device of the present invention achieves a greater improvement in both efficiency and lifetime over the OLED devices of known materials, as compared to the device comparative examples.
To illustrate the stable phase of the film phase of the inventive subject matter, film-accelerated crystallization experiments were performed on the inventive subject matter with a comparative compound: evaporating different materials on alkali-free glass by adopting a vacuum evaporation mode, packaging in a glove box (the water oxygen content is less than 0.1 ppm), placing a packaged sample under the condition of (the temperature is 85 ℃ and 115 ℃), and observing the surface morphology of the film by using a microscope (LEICA, DM8000M and 5 x 10 multiplying power) periodically, wherein the surface morphology results of the materials are shown in table 7 and figure 2;
TABLE 7
| Compounds of formula (I) | 85℃(1000h) | 115℃(200h) |
| Compound 4 | Non-crystallization | Non-crystallization |
| Compound 7 | Non-crystallization | Non-crystallization |
| Compound 23 | Non-crystallization | Non-crystallization |
| Compound 26 | Non-crystallization | Non-crystallization |
| Compound 44 | Non-crystallization | Non-crystallization |
| Compound 75 | Non-crystallization | Non-crystallization |
| Compound 85 | Non-crystallization | Non-crystallization |
| Compound 86 | Non-crystallization | Non-crystallization |
| Compound 88 | Non-crystallization | Non-crystallization |
| Compound 128 | Non-crystallization | Non-crystallization |
| Compound 189 | Non-crystallization | Non-crystallization |
| Compound 213 | Non-crystallization | Non-crystallization |
| Compound 223 | Non-crystallization | Non-crystallization |
| Compound 240 | Non-crystallization | Non-crystallization |
| Compound 243 | Non-crystallization | Non-crystallization |
| Compound 251 | Non-crystallization | Non-crystallization |
| Compound 261 | Non-crystallization | Non-crystallization |
| Compound 264 | Non-crystallization | Non-crystallization |
| Compound 266 | Non-crystallization | Non-crystallization |
| Compound 268 | Non-crystallization | Non-crystallization |
| Compound 271 | Non-crystallization | Non-crystallization |
| ref-1 | Crystallization | Crystallization |
| ref-2 | Darkening of color | Completely darken |
As can be seen from the results of the crystallization experiments of comparative compounds ref-1 and ref-2 of the compound 4 of the present application in FIG. 2, the surface morphology of the thin film of the compound 4 of the present application is unchanged no matter the compound 4 of the present application is subjected to the standing experiment at 85 ℃ or 115 ℃, which indicates that the compound of the present application has excellent film phase stability; after the ref-1 compound is placed at 85 ℃ for experiment, crystallization starts to appear, but crystallization appears on a large area of the surface after the compound is placed at 115 ℃; the ref-2 compound has a darkening film color at 85 ℃ and a completely darkening surface after being placed at 115 ℃; the ref-2 compound film has the worst crystallization stability; from this, it was confirmed that Compound 4 of the present invention had more excellent film phase stability than ref-1 and ref-2.
Claims (8)
1. The biphenylamine derivative is characterized in that the structure of the derivative is shown as a general formula (1):
In the general formula (1), each R 1-R3 is independently represented as one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, and a substituted or unsubstituted naphthyl group;
Ar is one of phenylene, bivalent phenyl and naphthylene;
r 4 is represented by a structure shown in a general formula (2);
the Ra represents phenyl and dibenzofuranyl;
In the general formula (2), rb and Rc are respectively and independently one of protium, deuterium and tert-butyl; the Rb and Rc may be the same or different;
M=1; said n, o=0 or 1;
The substituents of the substitutable group are optionally selected from one or more of deuterium atom, tert-butyl, phenyl or naphthyl.
2. The biphenylamine derivative according to claim 1, wherein the general formula (1) is represented by a structure represented by general formula (iii-1) -general formula (iii-3);
the symbols in the general formulae (III-1) - (III-3) have the meanings defined in claim 1.
3. The biphenylamine derivative according to claim 1, wherein the specific structure of the derivative is:
4. The biphenylamine derivative is characterized by comprising the following specific structure:
5. An organic electroluminescent device comprising a cathode, an anode and a functional layer, the functional layer being located between the anode and the cathode, characterized in that at least one functional layer of the organic electroluminescent device comprises the biphenylamine derivative according to any one of claims 1 to 4.
6. The organic electroluminescent device according to claim 5, wherein the functional layer comprises a hole transporting layer or an electron blocking layer, wherein the hole transporting layer or the electron blocking layer contains the biphenylamine derivative according to any one of claims 1 to 4.
7. The organic electroluminescent device according to claim 5, wherein the organic functional layer comprises a hole injection layer, a hole transport auxiliary layer, a light emitting layer, and an electron transport region, the hole transport auxiliary layer being adjacent to the light emitting layer, the hole injection layer comprising a P-doped material and the biphenylamine derivative according to any one of claims 1 to 4, the hole transport layer comprising the same organic material as the hole injection layer.
8. A lighting or display element comprising the organic electroluminescent device as claimed in any one of claims 5, 6, 7.
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| Title |
|---|
| 基于咔唑、联苯、蒽的有机小分子半导体材料的合成与光电性能研究;李景通;山东理工大学硕士学位论文;1-52 * |
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