CN113461593A - Biphenylamine derivative and application thereof - Google Patents
Biphenylamine derivative and application thereof Download PDFInfo
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- CN113461593A CN113461593A CN202110029258.4A CN202110029258A CN113461593A CN 113461593 A CN113461593 A CN 113461593A CN 202110029258 A CN202110029258 A CN 202110029258A CN 113461593 A CN113461593 A CN 113461593A
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- TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical class NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 title description 2
- 239000010410 layer Substances 0.000 claims abstract description 156
- 239000000463 material Substances 0.000 claims abstract description 65
- 238000002347 injection Methods 0.000 claims abstract description 33
- 239000007924 injection Substances 0.000 claims abstract description 33
- 230000000903 blocking effect Effects 0.000 claims abstract description 24
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000002346 layers by function Substances 0.000 claims abstract description 8
- 230000005525 hole transport Effects 0.000 claims description 36
- -1 biphenylyl group Chemical group 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 239000011368 organic material Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 4
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 4
- 241000720974 Protium Species 0.000 claims description 4
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 150000001975 deuterium Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 229910052722 tritium Inorganic materials 0.000 claims description 4
- 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
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000005562 phenanthrylene group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000006836 terphenylene group Chemical group 0.000 claims description 2
- QGMGHALXLXKCBD-UHFFFAOYSA-N 4-amino-n-(2-aminophenyl)benzamide Chemical class C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1N QGMGHALXLXKCBD-UHFFFAOYSA-N 0.000 claims 1
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 10
- 230000005540 biological transmission Effects 0.000 abstract description 7
- 230000006798 recombination Effects 0.000 abstract description 4
- 238000005215 recombination Methods 0.000 abstract description 4
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical class C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 abstract description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 abstract description 3
- 239000004065 semiconductor Substances 0.000 abstract description 2
- 230000005855 radiation Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 44
- 239000010408 film Substances 0.000 description 28
- 230000000052 comparative effect Effects 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000002425 crystallisation Methods 0.000 description 12
- 230000008025 crystallization Effects 0.000 description 12
- 238000012360 testing method Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 238000007738 vacuum evaporation Methods 0.000 description 7
- 238000001704 evaporation 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
- 238000001771 vacuum deposition Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000008204 material by function Substances 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
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- 239000000758 substrate Substances 0.000 description 3
- 238000005406 washing 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
- 241001597008 Nomeidae Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000010409 thin film Substances 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
- 206010041067 Small cell lung cancer Diseases 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
- 235000019504 cigarettes Nutrition 0.000 description 1
- 229940125833 compound 23 Drugs 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
- 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
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
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- 230000003993 interaction Effects 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 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
- 230000010287 polarization Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
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- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
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- 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
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- 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
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- 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
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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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Abstract
The invention relates to a biphenyl amine derivative and application thereof, belongs to the technical field of semiconductors, and provides a biphenyl amine derivative with a structure shown as a general formula (1):
the invention also discloses application of the benzidine derivative. The benzidine derivative provided by the invention has stronger hole transmission capability, and promotes the hole transmission capability under the appropriate HOMO energy levelHole injection and transport properties; under a proper LUMO energy level, the organic electroluminescent material plays a role in blocking electrons, and improves the recombination efficiency of excitons in the luminescent layer; when the material 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 Light Emission Diodes (OLED) device technology can be used for manufacturing novel display products and novel lighting products, is expected to replace the existing liquid crystal display and fluorescent lamp lighting, and has wide application prospect. The OLED light-emitting device is of a sandwich structure and comprises electrode material film layers and organic functional materials clamped between different electrode film layers, and the various different functional materials are mutually overlapped together according to the application to 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 are acted through an electric field, and the positive and negative charges are further compounded in the light-emitting layer, namely OLED electroluminescence is generated.
At present, the OLED display technology has been applied in the fields of smart phones, tablet computers, and the like, and will further expand to large-size application fields such as televisions, but compared with actual product application requirements, the light emitting efficiency, the service life, and other performances of the OLED device need to be further improved. The research on the improvement of the performance of the OLED light emitting device includes: 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 the innovation of the structure and the manufacturing process of the OLED device but also the continuous research and innovation of the OLED photoelectric functional material are needed to create the functional material of the OLED with higher performance.
The photoelectric functional materials of the OLED applied to the OLED device can be divided into two broad categories from the application, i.e., charge injection transport materials and light emitting materials, and further, the charge injection transport materials can be further divided into electron injection transport materials, electron blocking materials, hole injection transport materials and hole blocking materials, and the light emitting materials can be further divided into main light emitting materials and doping materials.
In order to fabricate a high-performance OLED light-emitting device, 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, etc. are required, and as a host material of a light-emitting layer, a material having good bipolar property, appropriate HOMO/LUMO energy level, etc. is required.
When the organic OLED device is applied to a display device, the organic OLED device is required to have a long life and a high efficiency, and particularly, a blue device (compared to red and green light emitting devices) of a blue pixel region has a high driving voltage and a short life. In order to prolong the service life of the blue pixel and reduce the driving voltage, the requirements on the film phase stability and the thermal stability of the hole transport material are enhanced at present.
At present, arylamine compounds are mostly adopted at the hole transport side, but the devices prepared by the materials still have the problems of high voltage and short service life, so that the service life of a blue light device is prolonged, and the problem of reducing the voltage of the device still needs to be overcome.
Disclosure of Invention
In order to solve the problems in the prior art, the applicant of the present invention provides a biphenyl derivative and applications thereof. The compound has higher hole mobility, proper HOMO energy level, stronger film phase state stability and molecular thermal stability, can effectively prolong the service life of an OLED device, and reduces the voltage of the device.
The invention provides a specific technical scheme as follows: a kind of bianiline derivant, the structure of this derivant is shown as general formula (1):
in the general formula (1), R is1-R3Each independently represents substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C containing one or more hetero atoms2-30A heteroaryl group;
ar represents substituted or unsubstitutedSubstituted C6-30Arylene radical, substituted or unsubstituted C containing one or more hetero atoms2-30A heteroarylene group;
the R is4Represented by a structure represented by the general formula (2);
the Ra represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group;
in the general formula (2), Rb and Rc are independently protium, deuterium, tritium, methoxy and C1-20Alkyl of (C)3-20Cycloalkyl, substituted or unsubstituted C6-30Aryl, C substituted or unsubstituted with one or more hetero atoms2-30A heteroaryl group; the Rb and the Rc can be the same or different;
wherein m is 1 or 2; n, o ═ 0, 1 or 2;
the substituent of the substitutable group is selected from deuterium atom, methoxyl group, C1-20Alkyl of (C)3-20Cycloalkyl of, C6-30Aryl, substituted or unsubstituted C containing one or more hetero atoms2-30One or more of heteroaryl;
the heteroatom is one or more selected from oxygen atom, sulfur atom or nitrogen atom.
Further, Ra represents phenyl.
Further, R is1-R3Each independently represents one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl and substituted or unsubstituted carbazolyl;
ar represents one of substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene and substituted or unsubstituted phenanthrylene substituted or unsubstituted benzophenanthrylene;
rb and Rc are respectively and independently represented by protium, deuterium, tritium, methoxy, methyl, ethyl, propyl, isopropyl, tert-butyl, amyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted furyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted fluorenyl and substituted or unsubstituted carbazolyl; the Rb and the Rc can be the same or different;
the substituent of the substitutable group is one or more selected from deuterium atom, methoxy group, methyl group, ethyl group, propyl group, adamantyl group, isopropyl group, tert-butyl group, pentyl group, phenyl group, naphthyl group or biphenyl group.
Further, the general formula (1) can be represented by a structure represented by general formula (III-1) to general formula (III-3);
the symbols in the general formula (III-1) to the general formula (III-3) have the meanings defined in claim 1.
Further, the specific structure of the derivative is as follows:
the second aspect of the present invention is to provide the use of the above benzidine derivative in the preparation of an organic electroluminescent device.
A third aspect of the present invention is to provide an organic electroluminescent device having such features comprising a cathode, an anode and functional layers disposed between the anode and the cathode, at least one of the functional layers of the organic electroluminescent device containing the benzidine derivative.
A fourth aspect of the present invention is to provide an organic electroluminescent device comprising a hole transporting layer having such a feature that the above hole transporting layer contains the benzidine 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 above electron blocking layer contains the benzidine derivative.
A sixth aspect of the present invention is to provide an organic electroluminescent device having such features, that the above 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 benzidine derivative, and 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 features, that the above 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 is adjacent to the light-emitting layer, the hole injection layer comprises a P-doped material and an organic material, the hole transport layer comprises the same organic material as the hole injection layer, the hole transport auxiliary layer comprises the above benzidine derivative, and the hole auxiliary layer comprises one or two materials.
An eighth aspect of the present invention provides a full-color display device including, 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 over the first electrode; a light emitting layer on the hole transport 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 over the light emitting layer; the hole transport region sequentially comprises a hole injection layer, a hole transport layer and a hole transport auxiliary layer from bottom to top, the hole injection layer comprises a P-type doping material, the red pixel unit, the green pixel unit and the blue pixel unit share the hole injection layer and the hole transport layer and respectively comprise the hole transport auxiliary layer, and the hole transport region comprises the benzidine derivative shown in the general formula (1).
A ninth aspect of the present invention is to provide a lighting or display element having such a feature, including the organic electroluminescent device described above.
Compared with the prior art, the invention has the beneficial technical effects that:
(1) compared with the structure disclosed in patent CN1984874A, the compound of the invention has more excellent film crystallization stability because benzidine derivatives and carbazole are taken as cores, 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 (the film crystallization stability is standard 85 ℃, 1000h does not crystallize, 115 ℃, 200h does not crystallize);
(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, thereby having excellent hole transport performance, and can obviously reduce the voltage of the device when being applied to an OLED device;
(3) the compound takes benzidine derivatives as the core, has higher hole mobility, can improve the recombination efficiency of excitons in a luminescent layer and improve the energy utilization rate as the material of a hole transport layer of an OLED luminescent device, thereby improving the luminescent efficiency of the device;
(4) the compound has excellent hole injection capability and hole transmission performance, so that the compound can be applied as a hole transmission material, more holes can be injected into a light-emitting layer, a light-emitting layer recombination region is far away from an EB (electron beam) side, and the long service life of a 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 doping material under a low doping proportion, further improves the hole injection efficiency, and reduces the risk of Cross-talk (red, green and blue pixels are subjected to color crosstalk due to different starting voltages of the red, green and blue pixels, wherein the starting voltage of the blue pixel is highest, and when the blue pixel is lighted, the risk of lighting an adjacent pixel point is caused).
(6) The benzidine derivative provided by the invention enables the distribution of electrons and holes in the luminescent layer to be more balanced, and under the appropriate HOMO energy level, the hole injection and transmission performances are improved; under a proper LUMO energy level, the organic electroluminescent material plays a role in blocking electrons, and improves the recombination efficiency of excitons in the luminescent layer; can effectively improve the exciton utilization rate, reduce the voltage of the device, improve the current efficiency of the device and prolong the service life of the device. The benzidine derivative has good application effect in OLED luminescent devices and good industrialization prospect.
(7) The benzidine derivative structure of the compound has an amino structure, so that the benzidine derivative has higher mobility and wider band gap, and the benzidine derivative is ensured not to be absorbed in the field of visible light; in addition, the distance between molecules is increased, the interaction force between molecules is weakened, so that the evaporation temperature is low, and the industrial processing window of the material is widened.
(8) The compound provided by the invention has a deep HOMO energy level, can be used as a green light and red light electron blocking layer, can effectively block electrons from being transmitted to one side of a hole transmission layer, effectively prevents the hole transmission material from being degraded by the electrons, and can effectively prolong the service life of a device when being used as the green light and red light electron blocking layer due to excellent film phase stability and mobility.
Drawings
FIG. 1 is a schematic structural diagram of an OLED device using the materials listed in 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 for compound 4 of the present invention and a comparative compound.
Detailed Description
The principles and features of this invention are described below in conjunction with the following drawings, which are set forth to illustrate, but are not to be construed to limit the scope of the invention.
All the raw materials in the following examples were purchased from cigarette Taiwangrun Fine chemical 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-neck bottle under the protection of nitrogen, stirring and mixing, and then adding 5 multiplied by 10-5mol Pd2(dba)3，5×10-5mol P(t-Bu)3Heating 0.03mol of sodium tert-butoxide to 105 ℃, carrying out reflux reaction for 24 hours, and sampling a point plate to show that no bromide is left and the reaction is complete; naturally cooling to room temperature, filtering, carrying out rotary evaporation on the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain a reactant A-1, wherein the HPLC purity is 99.06%, and the yield is 82.65%;
elemental analysis Structure (C)36H26N2) Theoretical value: c, 88.86; h, 5.39; n, 5.76; test values are: c, 88.88; h, 5.38; and N, 5.75. LC-MS: theoretical value is 486.21, found 486.25.
The other reactant A was prepared similarly to the reactant A-1 except for the difference in the starting materials used.
EXAMPLE 1 preparation of Compound 4
(1) Adding 0.01mol of reactant A-2, 0.01mol of reactant B-1 and 150ml of toluene into a 250ml three-neck flask under the protection of nitrogen, stirring and mixing, and then adding 5X 10-5mol Pd2(dba)3，5×10-5mol P(t-Bu)3Heating 0.03mol of sodium tert-butoxide to 105 ℃, carrying out reflux reaction for 24 hours, and sampling a point plate to show that no bromide is left and the reaction is complete; naturally cooling to room temperature, filtering, rotary evaporating the filtrate until no fraction is obtained, and passing through neutral siliconCarrying out gel column to obtain an intermediate C-1;
(2) adding 0.01mol of intermediate C-1, 0.01mol of reactant A-1 and 150ml of toluene into a 250ml three-neck flask under the protection of nitrogen, stirring and mixing, and then adding 5X 10-5mol Pd2(dba)3，5×10-5mol P(t-Bu)3Heating 0.03mol of sodium tert-butoxide to 105 ℃, carrying out reflux reaction for 24 hours, and sampling a point plate to show that no bromide is left and the reaction is complete; naturally cooling to room temperature, filtering, rotatably evaporating the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain a compound 4.
The procedure of example 1 was repeated to synthesize the following compounds, except that the reactants a and B listed in the following table 1-1 were used, and the test results were also listed in the following table.
TABLE 1-1
The compound of the invention is used in a luminescent device, can be used as a hole transport layer material, and can also be used as an electron blocking layer material. The compounds prepared in the above examples of the present invention were tested for thermal performance, T1 energy level, HOMO energy level and hole mobility, respectively, and the test results are shown in table 2:
TABLE 2
Note: the triplet energy level T1 was measured by Fluorolog-3 series fluorescence spectrometer from Horiba under the conditions of 2 x 10-5A toluene solution of mol/L; the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 DSC, Germany Chi corporation), the heating rate is 10 ℃/min; the thermogravimetric temperature Td is a temperature at which 1% of the weight loss is observed in a nitrogen atmosphere, and is measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation, Japan, and the nitrogen flow rate is 20 mL/min; the highest occupied molecular orbital HOMO energy level is tested by an ionization energy testing system (IPS-3), and the test is in an atmospheric environment; eg is tested by a double-beam ultraviolet-visible spectrophotometer (model: TU-1901); and (3) testing hole mobility, namely preparing the material into a single-charge device and measuring by using an SCLC (liquid crystal display cell) method.
The data in the table show that the organic compound has a suitable HOMO energy level, and can be applied to a hole transport layer or an electron blocking layer.
The application effect of the synthesized OLED material of the present invention in the device is detailed by device examples 1-50 and device comparative examples 1-5. Compared with the device comparative examples 1 to 5, the device examples 1 to 50 of the present invention have the same manufacturing process, and the same substrate material and electrode material are used, and the film thickness of the electrode material is also kept consistent, except that the hole injection layer and the hole transport layer material or the electron blocking layer material in the device is replaced.
Device comparative example 1(Blue)
The preparation process comprises the following steps:
as shown in fig. 1, the anode layer 2(ITO (15nm)/Ag (150nm)/ITO (15nm)) is washed, that is, washed with alkali, washed with pure water, dried, and then washed with ultraviolet rays and ozone to remove organic residues on the surface of the anode layer 1. HT-1 and P-1 having a film thickness of 10nm were deposited on the anode layer 2 after the above washing as the hole injection layer 3 by a vacuum deposition apparatus, and the mass ratio of HT-1 to P-1 was 97: 3. HT-1 was then evaporated to a thickness of 120nm as the hole transport layer 4. EB-1 was then evaporated to a thickness of 10nm as an 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 OLED light emitting device comprises that BH-1 used by the OLED light emitting layer 6 is used as a main material, BD-1 is used as a doping material, the doping proportion of the doping material is 3% by weight, and the thickness of the light emitting layer is 20 nm. After the light-emitting layer 6, ET-1 and Liq are continuously evaporated, wherein the mass ratio of ET-1 to Liq is 1: 1. The vacuum evaporation film thickness of the material was 30nm, and this layer was a hole-blocking/electron-transporting layer 7. On the hole-blocking/electron-transporting layer 7, a LiF layer having a film thickness of 1nm was formed by a vacuum evaporation apparatus, and this layer was an electron-injecting layer 8. On the electron injection layer 8, a vacuum deposition apparatus was used to produce a 16 nm-thick Mg: the Ag electrode layer has a Mg/Ag mass ratio of 1:9, and is used as the cathode layer 9. On the cathode layer 9, 70nm of CP-1 was vacuum-deposited as a CPL layer 10.
Comparative device example 2(Green)
As shown in fig. 1, the anode layer 2(ITO (15nm)/Ag (150nm)/ITO (15nm)) is washed, that is, washed with alkali, washed with pure water, dried, and then washed with ultraviolet rays and ozone to remove organic residues on the surface of the anode layer 1. HT-2 and P-1 having a film thickness of 10nm were deposited on the anode layer 2 after the above washing as the hole injection layer 3 by a vacuum deposition apparatus, and the mass ratio of HT-2 to P-1 was 97: 3. HT-2 was then evaporated to a thickness of 120nm as the 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, a light emitting layer 6 of the OLED light emitting device is manufactured, and the structure of the light emitting layer 6 comprises GH-1 and GH-2 used as main materials of the OLED light emitting layer 6, GD-1 used as a doping material, the mass ratio of GH-1 to GH-2 to GD-1 is 47:47:6, and the thickness of the light emitting layer is 30 nm. After the light-emitting layer 6, ET-1 and Liq are continuously evaporated, wherein the mass ratio of ET-1 to Liq is 1: 1. The vacuum evaporation film thickness of the material was 30nm, and this layer was a hole-blocking/electron-transporting layer 7. On the hole-blocking/electron-transporting layer 7, a LiF layer having a film thickness of 1nm was formed by a vacuum evaporation apparatus, and this layer was an electron-injecting layer 8. On the electron injection layer 8, a vacuum deposition apparatus was used to produce a 16 nm-thick Mg: the Ag electrode layer has a Mg/Ag mass ratio of 1:9, and is used as the cathode layer 9. On the cathode layer 9, 70nm of CP-1 was vacuum-deposited as a CPL layer 10.
Comparative device example 3(Red)
As shown in fig. 1, the anode layer 2(ITO (15nm)/Ag (150nm)/ITO (15nm)) is washed, that is, washed with alkali, washed with pure water, dried, and then washed with ultraviolet rays and ozone to remove organic residues on the surface of the anode layer 1. HT-2 and P-1 having a film thickness of 10nm were deposited on the anode layer 2 after the above washing as the hole injection layer 3 by a vacuum deposition apparatus, and the mass ratio of HT-2 to P-1 was 97: 3. HT-2 was then evaporated to a thickness of 120nm as the hole transport layer 4. EB-3 was then evaporated to a thickness of 80nm as an electron blocking layer 5. And after the evaporation of the electron blocking material is finished, a light emitting layer 6 of the OLED light emitting device is manufactured, and the structure of the OLED light emitting device comprises RH-1 used as a main material of the OLED light emitting layer 6, RD-1 used as a doping material, the mass ratio of RH-1 to RD-1 is 97:3, and the thickness of the light emitting layer is 30 nm. After the light-emitting layer 6, ET-1 and Liq are continuously evaporated, wherein the mass ratio of ET-1 to Liq is 1: 1. The vacuum evaporation film thickness of the material was 30nm, and this layer was a hole-blocking/electron-transporting layer 7. On the hole-blocking/electron-transporting layer 7, a LiF layer having a film thickness of 1nm was formed by a vacuum evaporation apparatus, and this layer was an electron-injecting layer 8. On the electron injection layer 8, a vacuum deposition apparatus was used to produce a 16 nm-thick Mg: the Ag electrode layer has a Mg/Ag mass ratio of 1:9, and is used as the cathode layer 9. On the cathode layer 9, 70nm of CP-1 was vacuum-deposited as a CPL layer 10.
Device examples 1-22: device examples 1 to 22 were prepared in the same manner as in device comparative example 1, except that the organic compound of the present invention was used as the hole injection layer and the hole transport layer material or the organic material of the electron blocking layer.
Device examples 23-37: device examples 23 to 37 were prepared in the same manner as in device comparative example 2 except that the organic compound of the present invention was used as the hole injection layer and the hole transport layer material or the organic material of the electron blocking layer.
Device examples 38-52: device examples 38 to 52 were prepared in the same manner as in device comparative example 3, except that the organic compound of the present invention was used as the hole injection layer and the hole transport layer material or the organic material of the electron blocking layer.
Device comparative examples 4, 5: device comparative examples 4 and 5 were prepared in the same manner as in device comparative example 1, except that the hole injection layer used the organic material rer-1 or ref-2.
The molecular structural formula of the related material is shown as follows:
after the OLED light emitting device was completed as described above, the anode and cathode were connected by a known driving circuit, and the current efficiency, 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 current efficiency, color and lifetime tests of the resulting devices are shown in tables 4-6.
TABLE 3
TABLE 4
TABLE 5
TABLE 6
Note: voltage, current efficiency and color coordinates were measured using an IVL (Current-Voltage-Brightness) test System (Fushda scientific instruments, Suzhou) at a current density of 10mA/cm2(ii) a The life test system is an EAS-62C type OLED device life tester of Japan System research company; LT95 refers to the time it takes for the device luminance to decay to 95% at a particular luminance (blue: 1000 nits; green: 10000 nits; red: 8000 nits).
It can be seen from the device data results that the organic light emitting device of the present invention achieves a greater improvement in both efficiency and lifetime compared to the device comparative example over the OLED device of known materials.
To illustrate the stable phase of the phase state of the material film of the present application, the compound of the present application and the comparative compound were subjected to a film accelerated crystallization experiment: different materials are evaporated on alkali-free glass in a vacuum evaporation mode, the alkali-free glass is packaged in a glove box (the water oxygen content is less than 0.1ppm), the packaged sample is placed at the temperature of 85 ℃ and 115 ℃, the surface morphology of the thin film is observed by a microscope (LEICA, DM8000M, 5 x 10 multiplying power) periodically, and the surface morphology results of the materials are shown in Table 7 and FIG. 2;
TABLE 7
| Compound (I) | 85℃(1000h) | 115℃(200h) |
| Compound 4 | Does not crystallize | Does not crystallize |
| |
Does not crystallize | Does not crystallize |
| Compound 23 | Does not crystallize | Does not crystallize |
| Compound 26 | Does not crystallize | Does not crystallize |
| Compound 44 | Does not crystallize | Does not crystallize |
| Compound 75 | Does not crystallize | Does not crystallize |
| Compound 85 | Does not crystallize | Does not crystallize |
| Compound 86 | Does not crystallize | Does not crystallize |
| Compound 88 | Does not crystallize | Does not crystallize |
| Compound 128 | Does not crystallize | Does not crystallize |
| Compound 189 | Does not crystallize | Does not crystallize |
| Compound 213 | Does not crystallize | Does not crystallize |
| Compound 223 | Does not crystallize | Does not crystallize |
| Compound 240 | Does not crystallize | Does not crystallize |
| Compound 243 | Does not crystallize | Does not crystallize |
| Compound 251 | Does not crystallize | Does not crystallize |
| Compound 261 | Does not crystallize | Does not crystallize |
| Compound 264 | Does not crystallize | Does not crystallize |
| Compound 266 | Does not crystallize | Does not crystallize |
| Compound 268 | Does not crystallize | Does not crystallize |
| Compound 271 | Does not crystallize | Does not crystallize |
| ref-1 | Crystallization of | Crystallization of |
| ref-2 | Darkening of color | Completely blackened |
As can be seen from the crystallization experiment results of compound 4 of the present invention in comparison with the crystallization experiments of compounds ref-1 and ref-2 in FIG. 2, the surface morphology of the compound 4 thin film of the present invention is not changed no matter the compound 4 of the present invention is placed at 85 ℃ or 115 ℃, which indicates that the compound of the present invention has excellent film phase stability; after a ref-1 compound is placed at 85 ℃ for an experiment, crystallization starts to occur, but after the compound is placed at 115 ℃, the crystallization occurs on a large surface area; the color of the ref-2 compound film at 85 ℃ is darkened, and the surface of the film is completely blackened after the film is placed at 115 ℃; the ref-2 compound film has the worst crystallization stability; therefore, the compound 4 of the present invention is judged to have more excellent film phase stability than ref-1 and ref-2.
Claims (9)
1. The dianiline derivative is characterized by having a structure shown as a general formula (1):
in the general formula (1), R is1-R3Each independently represents substituted or unsubstituted C6-30Aryl, substituted or unsubstituted C containing one or more hetero atoms2-30A heteroaryl group;
ar represents substituted or unsubstituted C6-30Arylene radical, substituted or unsubstituted C containing one or more hetero atoms2-30A heteroarylene group;
the R is4Represented by a structure represented by the general formula (2);
the Ra represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group;
in the general formula (2), Rb and Rc are independently protium, deuterium, tritium, methoxy and C1-20Alkyl of (C)3-20A cycloalkyl group of,Substituted or unsubstituted C6-30Aryl, C substituted or unsubstituted with one or more hetero atoms2-30A heteroaryl group; the Rb and the Rc can be the same or different;
wherein m is 1 or 2; n, o ═ 0, 1 or 2;
the substituent of the substitutable group is selected from deuterium atom, methoxyl group, C1-20Alkyl of (C)3-20Cycloalkyl of, C6-30Aryl, substituted or unsubstituted C containing one or more hetero atoms2-30One or more of heteroaryl;
the heteroatom is one or more selected from oxygen atom, sulfur atom or nitrogen atom.
2. The benzidine derivative of claim 1, wherein Ra represents a phenyl group.
3. The benzidine derivative of claim 1, wherein R is1-R3Each independently represents one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl and substituted or unsubstituted carbazolyl;
ar represents one of substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene and substituted or unsubstituted phenanthrylene;
rb and Rc are respectively and independently represented by protium, deuterium, tritium, methoxy, methyl, ethyl, propyl, isopropyl, tert-butyl, amyl, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted furyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted fluorenyl and substituted or unsubstituted carbazolyl; the Rb and the Rc can be the same or different;
the substituent of the substitutable group is one or more selected from deuterium atom, methoxy group, methyl group, ethyl group, propyl group, adamantyl group, isopropyl group, tert-butyl group, pentyl group, phenyl group, naphthyl group or biphenyl group.
4. The benzidine derivative according to claim 1, wherein the general formula (1) is represented by a structure represented by general formula (iii-1) to general formula (iii-3);
the symbols in the general formula (III-1) to the general formula (III-3) have the meanings defined in claim 1.
5. The benzidine derivative of claim 1, having the specific structure:
6. an organic electroluminescent device comprising a cathode, an anode and functional layers, the functional layers being located between the anode and the cathode, characterized in that at least one of the functional layers of the organic electroluminescent device comprises a benzidine derivative according to any one of claims 1 to 5.
7. The organic electroluminescent device according to claim 6, wherein the functional layer comprises a hole transport layer or an electron blocking layer, wherein the hole transport layer or the electron blocking layer contains the benzidine derivative according to any one of claims 1 to 5.
8. The organic electroluminescent device according to claim 7, 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 is adjacent to the light emitting layer, the hole injection layer comprises a P-doped material and the benzidine derivative according to any one of claims 1 to 5, and the hole transport layer comprises the same organic material as the hole injection layer.
9. A lighting or display element comprising the organic electroluminescent device according to any one of claims 6, 7 and 8.
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