CN115583888A - Naphthyl substituted arylamine compound and application thereof - Google Patents
Naphthyl substituted arylamine compound and application thereof Download PDFInfo
- Publication number
- CN115583888A CN115583888A CN202211587275.0A CN202211587275A CN115583888A CN 115583888 A CN115583888 A CN 115583888A CN 202211587275 A CN202211587275 A CN 202211587275A CN 115583888 A CN115583888 A CN 115583888A
- Authority
- CN
- China
- Prior art keywords
- reaction
- added
- water
- 100mmol
- 1mol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 arylamine compound Chemical class 0.000 title claims abstract description 11
- 125000001624 naphthyl group Chemical group 0.000 title abstract description 12
- 239000000463 material Substances 0.000 claims abstract description 71
- 230000005525 hole transport Effects 0.000 claims abstract description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 239000007787 solid Substances 0.000 abstract description 40
- 238000009825 accumulation Methods 0.000 abstract description 3
- 150000004982 aromatic amines Chemical class 0.000 abstract description 3
- 230000002349 favourable effect Effects 0.000 abstract description 2
- 230000007704 transition Effects 0.000 abstract description 2
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 121
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 87
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 87
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 73
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 40
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- 238000002347 injection Methods 0.000 description 29
- 239000007924 injection Substances 0.000 description 29
- 239000000843 powder Substances 0.000 description 29
- 238000001704 evaporation Methods 0.000 description 22
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 20
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 20
- 239000007795 chemical reaction product Substances 0.000 description 20
- 229910052763 palladium Inorganic materials 0.000 description 20
- 239000008096 xylene Substances 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 230000008020 evaporation Effects 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 14
- 239000001257 hydrogen Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 14
- PJZDEYKZSZWFPX-UHFFFAOYSA-N 2,6-dibromonaphthalene Chemical compound C1=C(Br)C=CC2=CC(Br)=CC=C21 PJZDEYKZSZWFPX-UHFFFAOYSA-N 0.000 description 12
- 239000002019 doping agent Substances 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 6
- HKRVHTFXSUGWIV-UHFFFAOYSA-N 1,1'-spirobi[fluorene]-2'-amine Chemical compound C12=CC3=CC=CC=C3C1=CC=CC12C2=CC3=CC=CC=C3C2=CC=C1N HKRVHTFXSUGWIV-UHFFFAOYSA-N 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 238000012512 characterization method Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000005406 washing Methods 0.000 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 description 3
- ODJZWBLNJKNOJK-UHFFFAOYSA-N 2,7-dibromonaphthalene Chemical compound C1=CC(Br)=CC2=CC(Br)=CC=C21 ODJZWBLNJKNOJK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 125000005561 phenanthryl group Chemical group 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000005580 triphenylene group Chemical group 0.000 description 3
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 2
- IBGUDZMIAZLJNY-UHFFFAOYSA-N 1,4-dibromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=C(Br)C2=C1 IBGUDZMIAZLJNY-UHFFFAOYSA-N 0.000 description 2
- ONCCVJKFWKAZAE-UHFFFAOYSA-N 2-bromo-9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=C(Br)C=C12 ONCCVJKFWKAZAE-UHFFFAOYSA-N 0.000 description 2
- QFUPJXCUNNWZJQ-UHFFFAOYSA-N 2-bromofluoren-1-one Chemical compound C1=CC=C2C3=CC=C(Br)C(=O)C3=CC2=C1 QFUPJXCUNNWZJQ-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 101000766357 Ruditapes philippinarum Big defensin Proteins 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 1
- XHCAGOVGSDHHNP-UHFFFAOYSA-N 1-bromo-4-tert-butylbenzene Chemical compound CC(C)(C)C1=CC=C(Br)C=C1 XHCAGOVGSDHHNP-UHFFFAOYSA-N 0.000 description 1
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 1
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 description 1
- APSMUYYLXZULMS-UHFFFAOYSA-N 2-bromonaphthalene Chemical compound C1=CC=CC2=CC(Br)=CC=C21 APSMUYYLXZULMS-UHFFFAOYSA-N 0.000 description 1
- KDVYCTOWXSLNNI-UHFFFAOYSA-N 4-t-Butylbenzoic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C=C1 KDVYCTOWXSLNNI-UHFFFAOYSA-N 0.000 description 1
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- 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
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/93—Spiro compounds
- C07C2603/94—Spiro compounds containing "free" spiro atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention belongs to the technical field of organic light-emitting display, and particularly relates to a naphthyl substituted arylamine compound and application thereof. The organic compound has a structure shown as a general formula (I), and can be used for a hole transport material. The compound has mother structure of naphthyl substituted arylamine, high bond energy between atoms, high heat stability, and favorable intermolecular solid accumulation and holeThe material has strong transition capability, and can effectively reduce the voltage of a device and prolong the service life of the material when used as a hole transport material. The invention also provides an organic electroluminescent device and a display device comprising the compound of formula (I).
(Ⅰ)。
Description
Technical Field
The invention belongs to the technical field of organic light-emitting display, and particularly relates to a naphthyl substituted arylamine compound and application thereof.
Background
Electroluminescence (EL) refers to a phenomenon in which a light emitting material emits light when excited by a current and an electric field under the action of an electric field, and is a light emitting process in which electric energy is directly converted into light energy. The organic electroluminescent display (hereinafter referred to as OLED) has a series of advantages of self-luminescence, low-voltage dc driving, full curing, wide viewing angle, light weight, simple composition and process, etc., and compared with the liquid crystal display, the organic electroluminescent display does not need a backlight source, and has a large viewing angle, low power, a response speed 1000 times that of the liquid crystal display, and a manufacturing cost lower than that of the liquid crystal display with the same resolution. Therefore, the organic electroluminescent device has very wide application prospect.
With the continuous advance of the OLED technology in the two fields of lighting and display, people pay more attention to the research on efficient organic materials affecting the performance of OLED devices, and an organic electroluminescent device with good efficiency and long service life is generally the result of the optimized matching of device structures and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures.
Organic electroluminescent materials have many advantages over inorganic luminescent materials, such as: the processing performance is good, a film can be formed on any substrate by an evaporation or spin coating method, and flexible display and large-area display can be realized; the optical property, the electrical property, the stability and the like of the material can be adjusted by changing the structure of the molecule, and the material has a large space for selection. In the most common OLED device structures, the following classes of organic materials are typically included: a hole injection material, a hole transport material, an electron transport material, and light emitting materials (dyes or doped guest materials) and corresponding host materials of each color. The hole transport material, as an important functional material, has a direct influence on the mobility of holes, and ultimately influences the light emitting efficiency of the OLED. However, the hole transport materials currently used in OLEDs have low hole transport rates, poor energy level matching with adjacent layers, and no consideration for efficiency and lifetime, which severely restricts the display function and development of OLED display devices.
Disclosure of Invention
The invention aims to provide a naphthyl substituted arylamine compound and application thereof, and provides a hole transport material to improve the working efficiency and prolong the service life of an organic electroluminescent device.
It is an object of a first aspect of the present invention to provide a naphthyl substituted arylamine compound having a structure represented by formula (I):
(Ⅰ)
wherein the content of the first and second substances,
R 1 -R 2 independently of one another, from C 6 -C 30 Aryl or C 3 -C 30 Heteroaryl of (a), R 1 ,R 2 Can be connected into a ring;
R 3 -R 7 independently of one another, from hydrogen, C 6 -C 30 Aryl or C 3 -C 30 The adjacent substituents of the heteroaryl group can be connected to form a ring;
R 8 -R 9 independently of one another, from hydrogen, C 6 -C 30 Aryl or C 3 -C 30 And at least one is not H;
each heteroatom on the heteroaryl group is independently selected from O, S or N;
the hydrogen atoms on the aryl and heteroaryl groups may each independently be substituted by Ra, which is independently selected from deuterium, halogen, nitro, cyano, C 1 -C 4 Alkyl of (C) 5 -C 20 Cycloalkyl, phenyl, biphenyl, terphenyl, or naphthyl.
Preferably, said R is 1 -R 2 Independently of one another, from C 6 -C 30 Aryl or C 3 -C 30 Heteroaryl of (A), R 1 ,R 2 Can be connected into a ring; r 3 -R 7 Independently of one another, from hydrogen, C 6 -C 30 Aryl or C 3 -C 30 The adjacent substituents can be connected to form a ring, and hydrogen atoms on the aryl and heteroaryl can be independently substituted by Ra; r 8 -R 9 Independently of one another, from hydrogen, C 6 -C 30 Aryl or C 3 -C 30 And at least one is not H, the hydrogen atoms on the aryl and heteroaryl groups each independently may be substituted with Ra.
Preferably, said R is 1 -R 2 Independently of one another, from the following groups which are unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamino, carbazolyl.
Preferably, said R is 3 -R 7 Independently of one another, from hydrogen, the following groups which are unsubstituted or substituted by Ra: phenyl, biphenyl, terphenylPhenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothiophenyl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, carbazolyl.
Preferably, said R is 8 -R 9 Independently of one another, from hydrogen, the following groups unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamino, carbazolyl.
Preferably, the compound of formula (I) may be selected from the following compounds represented by A1 to a 25:
it is an object of the second aspect of the present invention to provide a hole transport material comprising at least one of the compounds provided by the first aspect of the present invention.
It is an object of a third aspect of the present invention to provide an organic electroluminescent device comprising at least one of the hole transport materials provided by the second aspect of the present invention.
It is an object of a fourth aspect of the present invention to provide a display apparatus including the organic electroluminescent device provided by the third aspect of the present invention.
Compared with the prior art, the invention has the beneficial effects that:
the compound disclosed by the invention has a parent structure of naphthyl substituted arylamine, has high bond energy among atoms, good thermal stability, strong hole transition capability and capability of being used as a hole transport layer material, is favorable for solid-state accumulation among molecules, and can effectively reduce the voltage of a device and prolong the service life of the material.
The compound provided by the invention is applied to a hole transport layer, has a proper energy level with an adjacent layer, is beneficial to injection and migration of holes, can effectively reduce the driving voltage, has a high hole migration rate, and can realize good luminous efficiency in a device. The compound has a larger conjugated plane, is beneficial to molecular accumulation, shows good thermodynamic stability and shows long service life in a device.
Meanwhile, the preparation process of the compound is simple and feasible, the raw materials are easy to obtain, and the compound is suitable for industrial production.
Drawings
In order to more clearly illustrate the technical solution of the present invention, the drawings will be briefly introduced, and it is apparent that the drawings in the following description are only one embodiment of the present invention, and it is obvious to those skilled in the art that other embodiments can be obtained according to the drawings.
Fig. 1 is a schematic structural view of a typical organic electroluminescent device. Each part is as follows:
1. a substrate; 2. a reflective anode electrode; 3. a hole injection layer; 4. a hole transport layer; 5. a light emitting layer; 6. an electron transport layer; 7. an electron injection layer; 8. and a cathode electrode.
Detailed Description
The technical solutions in the present invention will be described clearly and completely with reference to the following examples, and it should be understood that the described examples are only a part of the examples, but not all of the examples. All other embodiments obtained by a person skilled in the art based on the embodiments of the present invention are within the scope of protection of the present invention.
In the present invention, there is no particular limitation on the kind and structure of the organic electroluminescent device as long as the hole transport material provided by the present invention can be used.
The organic electroluminescent device of the present invention may be a light-emitting device of a top emission structure, for example, comprising an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a transparent or semitransparent cathode in this order on a substrate.
The organic electroluminescent device of the present invention may be a light-emitting device having a bottom emission structure, for example, a structure comprising a transparent or translucent anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode in this order on a substrate.
The organic electroluminescent device of the present invention may also be a light-emitting device of a double-sided light-emitting structure, for example, a structure comprising a transparent or semitransparent anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a transparent or semitransparent cathode on a substrate in this order.
In the organic electroluminescent device of the present invention, any material used for the layer in the prior art may be used for the layer except that the hole transport layer comprises the hole transport material provided by the present invention.
For convenience, the organic electroluminescent device of the present invention will be described below with reference to fig. 1, but this is not meant to limit the scope of the present invention in any way. It is understood that all organic electroluminescent devices capable of using the hole transport material of the present invention are within the scope of the present invention.
Fig. 1 shows a schematic diagram of a typical organic electroluminescent device, in which a substrate 1, a reflective anode electrode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode electrode 8 are sequentially disposed from bottom to top.
It is to be understood that fig. 1 schematically shows the structure of a typical organic electroluminescent device, and the present invention is not limited to this structure, and the hole transport material of the present invention may be used in any type of organic electroluminescent device. For example, the organic electroluminescent device may further include an electron blocking layer, a hole blocking layer, a light extraction layer, etc., and these layers may be added or omitted as the case may be, in actual application.
In the present invention, the substrate 1 is not particularly limited, and conventional substrates used in the organic electroluminescent device in the related art, for example, glass, polymer materials, and glass and polymer materials with TFT components, etc. may be used.
In the present invention, the material of the reflective anode electrode 2 is not particularly limited, and may be selected from Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO) known in the art 2 ) Transparent conductive materials such as zinc oxide (ZnO) and Low Temperature Polysilicon (LTPS), metal materials such as silver and its alloys, aluminum and its alloys, organic conductive materials such as PEDOT (poly 3, 4-ethylenedioxythiophene), and multilayer structures of these materials.
In the present invention, the material of the hole injection layer 3 is not particularly limited, and a hole injection material known in the art or a hole transport material provided by the present invention may be selected as the hole injection material.
For example, the material of the hole injection layer may be selected from at least one of the following HT-1 to HT-31 compounds:
in the present invention, the hole injection layer 3 may further include a p-type dopant, the kind of which is not particularly limited, and various p-type dopants known in the art may be used, for example, the p-type dopant may be selected from at least one of the following compounds:
in the present invention, the amount of the p-type dopant is not particularly limited, and may be an amount well known to those skilled in the art.
In the present invention, the hole transport layer 4 contains at least one of the hole transport materials of the present invention. The hole transport layer 4 may also comprise any combination of at least one of the hole transport materials of the invention with known hole transport materials. The currently known hole transport material may be selected from at least one of the above-mentioned HT-1 to HT-31 compounds, but is not limited to the above-mentioned compounds.
In the present invention, the light emitting material of the light emitting layer 5 is not particularly limited, and any light emitting material known to those skilled in the art may be used, and for example, the light emitting material may include a host material and a guest material. For example, known light emitting layer host materials may be selected from at least one of the following GPH-1 to GPH-80 compounds:
in a preferred embodiment of the invention, the light-emitting layer 5 employs the technique of phosphorescent electroluminescence. The guest material in the light-emitting layer 5 thereof is a phosphorescent dopant, which may be selected from, but not limited to, a combination of one or more of the following compounds PRD-1 to PRD-28. The amount of the phosphorescent dopant is not particularly limited and may be an amount known in the art.
In the present invention, the material of the electron transport layer 6 is not particularly limited, and may be made of an electron transport material known in the art. For example, the electron transport layer material may be selected from at least one of the following ET-1 to ET-57 compounds:
in the present invention, the electron transport layer 6 may further include an n-type dopant, the kind of which is not particularly limited, and various n-type dopants known in the art may be employed. For example, the n-type dopant may be a compound represented by the following formula:
in the present invention, the amount of the n-type dopant is not particularly limited, and may be an amount well known to those skilled in the art.
In the present invention, the material of the electron injection layer 7 is not particularly limited, and electron injection materials known in the art may be used, and for example, may include, but are not limited to, liQ, liF, naCl, csF, li in the prior art 2 O、Cs 2 CO 3 And at least one of BaO, na, li, ca and the like.
In the present invention, the material of the cathode electrode 8 is not particularly limited, and may be selected from, but not limited to, magnesium silver mixture, metal such as LiF/Al, ITO, al, etc., metal mixture, oxide, etc.
In the present invention, the display device includes, but is not limited to, a display, a television, a tablet computer, a mobile communication terminal, and the like.
The method of preparing the organic electroluminescent device of the present invention is not particularly limited, and any method known in the art may be employed, and for example, the present invention may be prepared by the following preparation method:
(1) Cleaning a reflective anode electrode 2 on an OLED device substrate 1 for top emission, respectively performing steps of medicine washing, water washing, hair brushing, high-pressure water washing, air knife and the like in a cleaning machine, and then performing heat treatment;
(2) Vacuum evaporating a hole injection material on the reflective anode electrode 2 to form a hole injection layer 3;
(3) Vacuum evaporating a hole transport material on the hole injection layer 3 to form a hole transport layer 4;
(4) A luminescent layer 5 is evaporated on the hole transport layer 4 in vacuum, and the luminescent layer 5 comprises a host material and a guest material;
(5) Vacuum evaporating an electron transport material on the luminescent layer 5 to form an electron transport layer 6;
(6) Vacuum evaporating electron injection material selected from LiQ, liF, naCl, csF, and Li on the electron transport layer 6 as electron injection layer 7 2 O、Cs 2 CO 3 One or a combination of more of materials such as BaO, na, li, ca and the like;
(7) A cathode material is vacuum-deposited on the electron injection layer 7 as a cathode electrode 8.
The above description has been made of only a structure of a typical organic electroluminescent device and a method for fabricating the same, and it is to be understood that the present invention is not limited to this structure. The hole transport material of the present invention can be used for an organic electroluminescent device of any structure, and the organic electroluminescent device can be prepared by any preparation method known in the art.
The method for synthesizing the compound of the present invention is not particularly limited, and the synthesis can be carried out by any method known to those skilled in the art. The following illustrates the synthesis of the compounds of the present invention.
Synthesis example 1: synthesis of Compound A2
Into a reaction flask were charged 100mmol of 2, 6-dibromonaphthalene, 100mmol of phenylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) was added 3 ) 4 ). The reaction was carried out at 60 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reactant was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M1. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on the amount of 2, 6-dibromonaphthalene.
100mmol of aniline, 100mmol of 2-bromo-spirobifluorene, 28.83g of sodium tert-butoxide (300 mmol), 800ml of xylene and 1mol% of palladium bis-dibenzylideneacetone (Pd (dba)) were charged into a reaction flask. The reaction was carried out at 120 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was recrystallized and purified with toluene to obtain white powder M2. Wherein the addition amount of Pd (dba) is 1mol percent of the aniline.
To a reaction flask were added 100mmol of M1, 100mmol of M2, 28.83g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of palladium bis-dibenzylideneacetone (Pd (dba)). The reaction was carried out at 120 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain a white powder A2. Wherein Pd (dba) is added in an amount of 1mol% based on M1.
The hydrogen spectrum characterization of A2 resulted in:
1 H NMR (400 MHz, CDCl 3 ) δ7.96-7.61 (m, 4H), 7.55 (t, J = 8.4 Hz, 4H), 7.49 (s, 1H), 7.43-7.30 (m, 8H), 7.22 (d, J = 10.0 Hz, 6H), 7.13 (s, 1H), 7.10 (d, J = 8.0 Hz, 8H), 7.00 (s, 1H).
M/Z: experimental value, 611.1; theoretical, 611.3.
Synthesis example 2: synthesis of Compound A7
Into a reaction flask were charged 100mmol of 2, 6-dibromonaphthalene, 100mmol of phenylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF), and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) was added 3 ) 4 ). The reaction was carried out at 60 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M1. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on the amount of 2, 6-dibromonaphthalene.
To a reaction flask were added 200mmol of M1, 100mmol of 2-amino-spirobifluorene, 28.83g of sodium tert-butoxide (300 mmol), 800ml of xylene, and 2mol% of palladium bis-dibenzylideneacetone (Pd (dba)). The reaction was carried out at 120 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was recrystallized from toluene to purify it to obtain white powder A7. Wherein Pd (dba) is added in an amount of 2mol% based on M1.
The hydrogen spectrum characterization of A7 resulted in:
1 H NMR (400 MHz, CDCl 3 ) δ8.00-7.70 (m, 4H), 7.71 (t, J = 8.0 Hz, 2H), 7.69 (s, 1H), 7.57 (t, J = 8.4 Hz, 2H), 7.49 (s, 1H), 7.43-7.39 (m, 6H), 7.33 (d, J = 11.2Hz, 6H), 7.24 (d, J = 8.0 Hz, 6H), 7.17 -7.08 (m, 9H).
M/Z: experimental value, 735.2; theoretical value, 735.3.
Synthesis example 3: synthesis of Compound A8
Into a reaction flask were charged 100mmol of 2, 6-dibromonaphthalene, 100mmol of phenylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF), and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) was added 3 ) 4 ). The reaction was carried out at 60 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M1. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on the amount of 2, 6-dibromonaphthalene.
To a reaction flask were added 100mmol of M1, 100mmol of 2-amino-spirobifluorene, 28.83g of sodium tert-butoxide (300 mmol), 800ml of xylene, and 2mol% of palladium bis-dibenzylideneacetone (Pd (dba)). The reaction was carried out at 120 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was recrystallized and purified with toluene to obtain white powder M2. Wherein Pd (dba) is added in an amount of 1mol% based on M1.
Into a reaction flask were charged 100mmol of 1, 4-dibromonaphthalene, 100mmol of phenylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) was added 3 ) 4 ). The reaction was carried out at 60 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M3. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on 1, 4-dibromonaphthalene.
To a reaction flask were added 100mmol of M2, 100mmol of M3, 28.83g of sodium t-butoxide (300 mmol), 800ml of xylene, and 2mol% of palladium bis-dibenzylideneacetone (Pd (dba)). The reaction was carried out at 120 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was recrystallized with toluene to obtain a white powder A8. Wherein the amount of Pd (dba) added is 1mol% of M2.
The hydrogen spectrum of A8 is characterized as follows:
1 H NMR (400 MHz, CDCl 3 ) δ8.00-7.82 (m, 4H), 7.79 -7.71 (m, 3H), 7.64 (s, 1H), 7.60-7.52 (m, 4H), 7.47 (d, J = 10.0 Hz, 4H), 7.43-7.34 (m, 6H), 7.33 (d, J = 8.0 Hz, 4H), 7.27-7.16 (m, 5H), 7.04-6.92 (m, 6H).
M/Z: experimental value, 735.1; theoretical value, 735.3.
Synthesis example 4: synthesis of Compound A11
Into a reaction flask were charged 100mmol of 2, 6-dibromonaphthalene, 100mmol of phenylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) was added 3 ) 4 ). The reaction was carried out at 60 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M1. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on the amount of 2, 6-dibromonaphthalene.
Into a reaction flask were charged 100mmol of aniline, 100mmol of M1, 28.83g of sodium tert-butoxide (300 mmol), 800ml of xylene, and 1mol% of palladium bis-dibenzylideneacetone (Pd (dba)) were added. The reaction was carried out at 120 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M2. Wherein the addition amount of Pd (dba) is 1mol percent of the aniline.
100mmol of 2-bromofluorenone and 1000mmol of phenol were charged into a reaction flask. The reaction was heated to reflux for 12h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M3.
Into a reaction flask were charged 100mmol of M2, 100mmol of M3, 28.83g of sodium tert-butoxide (300 mmol), 800ml of xylene, and 1mol% of palladium bis-dibenzylideneacetone (Pd (dba)) was added. The reaction was carried out at 120 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was recrystallized from toluene to purify it to obtain white powder a11. Wherein Pd (dba) is added in an amount of 1mol% based on M1.
The hydrogen spectrum characterization results for a11 are as follows:
1 H NMR (400 MHz, CDCl 3 ) δ7.92 (d, J = 7.2 Hz, 2H), 7.86-7.75 (m, 3H), 7.74 (t, J = 8.4 Hz, 2H), 7.73 (d, J = 8.0 Hz, 4H), 7.59 (s, 1H), 7.55 (d, J= 8.4 Hz, 6H), 7.42-7.28 (m, 4H), 7.22-7.06 (m, 8H), 7.00 (s, 1H).
M/Z: experimental value, 625.2; theoretical value, 625.2.
Synthesis example 5: synthesis of Compound A17
A reaction flask was charged with 100mmol of 2, 6-dibromonaphthalene, 100mmol of diphenylamine, 28.83g of sodium tert-butoxide (300 mmol), 800ml of xylene, and 1mol% of palladium bis-dibenzylideneacetone (Pd (dba)) was added. The reaction was carried out at 120 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M1. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on the amount of 2, 6-dibromonaphthalene.
100mmol of aniline, 100mmol of 2-bromo-spirobifluorene, 28.83g of sodium tert-butoxide (300 mmol), 800ml of xylene and 1mol% of palladium bis-dibenzylideneacetone (Pd (dba)) were charged into a reaction flask. The reaction was carried out at 120 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was recrystallized and purified with toluene to obtain white powder M2. Wherein the addition amount of Pd (dba) is 1mol percent of the aniline.
Into a reaction flask were charged 100mmol of M1, 100mmol of M2, 28.83g of sodium tert-butoxide (300 mmol), 800ml of xylene, and 1mol% of palladium bis-dibenzylideneacetone (Pd (dba)) was added. The reaction was carried out at 120 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was recrystallized from toluene to purify it to obtain white powder a17. Wherein Pd (dba) is added in an amount of 1mol% based on M1.
The hydrogen spectrum of a17 is characterized as follows:
1 H NMR (400 MHz, CDCl 3 ) δ7.88 (t, J = 10.0 Hz, 4H), 7.63 (s, 1H), 7.55 (d, J = 7.2 Hz, 4H), 7.35 (d, J = 8.0 Hz, 8H), 7.25 (d, J = 10.0Hz, 8H), 7.12-7.00 (m, 10H), 6.88 (s, 1H).
M/Z: experimental value, 700.8; theoretical value, 700.3.
Synthesis example 6: synthesis of Compound A18
Into a reaction flask were charged 100mmol of 2, 6-dibromonaphthalene, 100mmol of phenylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) was added 3 ) 4 ). The reaction was carried out at 60 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M1. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on the amount of 2, 6-dibromonaphthalene.
100mmol of M1, 100mmol of 2-amino-spirobifluorene, 28.83g of sodium tert-butoxide (300 mmol), 800ml of xylene and 2mol% of palladium bis-dibenzylideneacetone (Pd (dba)) are added to a reaction flask. The reaction was carried out at 120 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was recrystallized and purified with toluene to obtain white powder M2. Wherein Pd (dba) is added in an amount of 1mol% based on M1.
A reaction flask was charged with 100mmol of aniline, 100mmol of 1-bromonaphthalene, 28.83g of sodium tert-butoxide (300 mmol), 800ml of xylene, and 2mol% of palladium bis-dibenzylideneacetone (Pd (dba)) was added. The reaction was carried out at 120 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M3. Wherein the addition amount of Pd (dba) is 1mol percent of the aniline.
100mmol of M3, 100mmol of p-dibromobenzene, 28.83g of sodium tert-butoxide (300 mmol), 800ml of xylene and 2mol% of palladium bis-dibenzylideneacetone (Pd (dba)) are added to a reaction flask. The reaction was carried out at 120 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain a white powder M4. Wherein the amount of Pd (dba) added is 1mol% based on M3.
Into a reaction flask were charged 100mmol of M2, 100mmol of M4, 28.83g of sodium tert-butoxide (300 mmol), 800ml of xylene, and 2mol% of palladium bis-dibenzylideneacetone (Pd (dba)) were added. The reaction was carried out at 120 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder a18. Wherein Pd (dba) is added in an amount of 1mol% based on M2.
The hydrogen spectrum of a18 is characterized as follows:
1 H NMR (400 MHz, CDCl 3 ) δ8.22 (s, 1H), 8.00-7.73 (m, 5H), 7.72-7.64 (m, 4H), 7.63 (d, J = 8.0 Hz, 4H), 7.57 (d, J = 8.4 Hz, 4H), 7.47-7.38 (m, 6H), 7.33 (d, J = 11.2 Hz, 4H), 7.28-7.13 (m, 7H), 7.10 (d, J = 10.0 Hz, 6H), 7.00 (s, 1H).
M/Z: experimental value, 826.1; theoretical value, 826.3.
Synthesis example 7: synthesis of Compound A20
Into a reaction flask were charged 100mmol of 2,7 dibromonaphthalene, 100mmol of phenylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF), and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) was added 3 ) 4 ). The reaction was carried out at 60 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M1. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on the amount of 2, 7-dibromonaphthalene.
To a reaction flask were added 100mmol of M1, 100mmol of 2-amino-spirobifluorene, 28.83g of sodium tert-butoxide (300 mmol), 800ml of xylene, and 2mol% of palladium bis-dibenzylideneacetone (Pd (dba)). The reaction was carried out at 120 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was recrystallized and purified with toluene to obtain white powder M2. Wherein Pd (dba) is added in an amount of 1mol% based on M1.
To a reaction flask were added 100mmol of p-dibromobenzene, 100mmol of p-tert-butylbenzoic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF), and 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) was added 3 ) 4 ). The reaction was carried out at 60 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M3. Wherein, pd (PPh) 3 ) 4 Is added in an amount of 1mol% to dibromobenzene.
To a reaction flask were added 100mmol of M2, 100mmol of M3, 28.83g of sodium t-butoxide (300 mmol), 800ml of xylene, and 2mol% of palladium bis-dibenzylideneacetone (Pd (dba)). The reaction was carried out at 120 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was recrystallized from toluene to purify it to obtain white powder a20. Wherein the amount of Pd (dba) added is 1mol% of M2.
The hydrogen spectrum characterization of a20 resulted in:
1 H NMR (400 MHz, CDCl 3 ) δ8.00-7.81 (m, 4H), 7.75 (d, J = 8.0 Hz, 4H), 7.63 (s, 1H), 7.60-7.53 (m, 6H), 7.50-7.44 (m, 5H), 7.43-7.30 (m, 4H), 7.24 (d, J = 8.0 Hz, 6H), 7.14 (d, J = 10.0 Hz, 4H), 1.33 (s, 9H).
M/Z: experimental value, 741.2; theoretical value, 741.3.
Synthesis example 8: synthesis of Compound A22
A reaction flask was charged with 100mmol of aniline, 100mmol of 2-bromonaphthalene, 28.83g of sodium tert-butoxide (300 mmol), 800ml of xylene, and 2mol% of palladium bis-dibenzylideneacetone (Pd (dba)) were added. The reaction was carried out at 120 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was recrystallized and purified with toluene to obtain white powder M2. Wherein Pd (dba) is added in an amount of 1mol% based on M1.
Into a reaction flask were charged 100mmol of M1, 100mmol of 2,7 dibromonaphthalene, 28.83g of sodium tert-butoxide (300 mmol), 800ml of xylene, and 2mol% of palladium bis-dibenzylideneacetone (Pd (dba)) were added. The reaction was carried out at 120 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was recrystallized and purified with toluene to obtain white powder M2. Wherein Pd (dba) is added in an amount of 1mol% based on M1.
Into a reaction flask were charged 100mmol of M2, 100mmol of aniline, 28.83g of sodium tert-butoxide (300 mmol), 800ml of xylene, and 2mol% of palladium bis-dibenzylideneacetone (Pd (dba)) were added. The reaction was carried out at 120 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M3. Wherein Pd (dba) is added in an amount of 1mol% based on M2.
Adding 100mmol of p-tert-butylbromobenzene and 200ml of THF into a reaction bottle, dropwise adding 100mmol of butyl lithium at 0 ℃, controlling the temperature to react for 1h after the dropwise adding is finished, dissolving 100mmol of 2-bromofluorenone in 200ml of THF, dropwise adding the solution into the reaction bottle, heating to room temperature to react for 12h after the dropwise adding is finished. After the reaction, water is added, the organic phase is separated and concentrated to obtain an intermediate M4.
100mmol of M4, 200ml of benzene and 10ml of trifluoromethanesulfonic acid are added into a reaction flask, heated to reflux for water diversion, and reacted for 12 hours. After the reaction is finished, water is added, solid is separated out, and the intermediate M5 is obtained after filtration and drying.
100mmol of M3, 100mmol of M5, 28.83g of sodium tert-butoxide (300 mmol), 800ml of xylene and 2mol% of palladium bis-dibenzylideneacetone (Pd (dba)) are added to the reaction vessel. The reaction was carried out at 120 ℃ for 12h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain a white powder a22. Wherein the amount of Pd (dba) added is 1mol% of M3.
The hydrogen spectrum of a22 is characterized as follows:
1 H NMR (400 MHz, CDCl 3 ) δ8.10-7.95 (m, 5H), 7.82 (d, J = 12.4 Hz, 2H), 7.74 (d, J = 9.6 Hz, 2H), 7.62 (s, 1H), 7.54 (s, 1H), 7.44 (d, J = 10.0 Hz, 2H), 7.41-7.31 (m, 7H), 7.26 (t, J = 8.0 Hz, 3H), 7.21-7.14 (m, 5H), 7.13-7.06 (m, 7H), 6.98 (d, J = 10.0 Hz, 4H), 1.33 (s, 9H).
M/Z: experimental value, 808.2; theoretical, 808.4.
The other compounds of the present invention can be synthesized by selecting suitable raw materials according to the concept of the above synthesis examples 1 to 8, and also can be synthesized by selecting any other suitable methods and raw materials.
Example 1
Carrying out ultrasonic treatment on the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, washing in deionized water, carrying out ultrasonic degreasing in an acetone-ethanol mixed solvent, baking in a clean environment until water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy solar ion beams;
the above-mentioned belt is provided with an anodeThe glass substrate is placed in a vacuum chamber and is vacuumized to be less than 10 DEG -5 Performing vacuum evaporation on the anode layer film to form HT-11 as a hole injection layer at the following step, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10nm;
vacuum evaporating an A2 material on the hole injection layer to form a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 80nm;
a luminescent layer is evaporated on the hole transport layer in vacuum, the luminescent layer comprises a main material GHP-16 and a dye material RPD-1, evaporation is carried out by a multi-source co-evaporation method, the evaporation rate of the main material GHP-16 is adjusted to be 0.1nm/s, the evaporation rate of the dye RPD-1 is 3% of the evaporation rate of the main material, and the total thickness of the evaporation film is 30nm;
vacuum evaporating an electron transport layer on the light emitting layer, wherein an ET-42 material is selected as an electron transport material, the evaporation rate is 0.1nm/s, and the evaporation film thickness is 30nm;
vacuum evaporating LiF with the thickness of 0.5nm on the Electron Transport Layer (ETL) to be used as an electron injection layer, wherein the evaporation rate is 0.1nm/s;
and finally, evaporating an aluminum layer with the thickness of 150 nm on the electron injection layer to be used as a cathode of the organic electroluminescent device, wherein the evaporation rate is 0.1nm/s.
Examples 2 to 8
The procedure was as in example 1 except that A2 was replaced with A7, A8, A11, A17, A18, A20 and A22, respectively.
Comparative example 1
The procedure was as in example 1, except that HT-27 was used in place of A2.
The organic electroluminescent device prepared by the above process was subjected to the following performance measurement:
the driving voltage and current efficiency of the organic electroluminescent device prepared in examples and comparative examples and the lifetime of the device were measured at the same luminance using a digital source meter and a luminance meter, and specifically, the luminance of the organic electroluminescent device reached 5000cd/m as measured by increasing the voltage at a rate of 0.1V per second 2 The current voltage is the driving voltage, and the current density at the moment is measured; the ratio of the brightness to the current density is the current efficiency; the life test of LT95 is as follows: using a luminance meter at 5000cd/m 2 At luminance, the luminance drop of the organic electroluminescent device was measured to be 4750cd/m while maintaining a constant current 2 Time in hours, the test results are shown in table 1.
TABLE 1 organic electroluminescent device Performance results
The data in the table show that the compound prepared by the invention is used for the hole transport material of the organic electroluminescent device, can effectively reduce the driving voltage, improve the current efficiency and prolong the service life of the device, and is a hole transport material with good performance.
The above description is only for the preferred embodiment of the present invention, and is not intended to limit the scope of the present invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention shall fall within the protection scope of the present invention.
Claims (4)
1. A naphthyl-substituted arylamine compound, characterized by being selected from the following compounds represented by A1 to a 25:
2. a hole transport material comprising at least one compound of claim 1.
3. An organic electroluminescent device, characterized in that it comprises at least one of the hole transport materials of claim 2.
4. A display device comprising the organic electroluminescent element according to claim 3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211587275.0A CN115583888A (en) | 2022-12-12 | 2022-12-12 | Naphthyl substituted arylamine compound and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211587275.0A CN115583888A (en) | 2022-12-12 | 2022-12-12 | Naphthyl substituted arylamine compound and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN115583888A true CN115583888A (en) | 2023-01-10 |
Family
ID=84783121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211587275.0A Pending CN115583888A (en) | 2022-12-12 | 2022-12-12 | Naphthyl substituted arylamine compound and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115583888A (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103666455A (en) * | 2013-12-03 | 2014-03-26 | 方圆环球光电技术盐城有限公司 | Novel spirofluorene xanthene organic electroluminescent material and preparation method thereof |
| CN108117491A (en) * | 2016-11-30 | 2018-06-05 | 武汉尚赛光电科技有限公司 | 9,9 '-spiral shell, two fluorenes and amine derivant, its preparation method, application and device |
| KR20190118137A (en) * | 2018-04-09 | 2019-10-17 | 주식회사 엘지화학 | Compound and organic light emitting device comprising same |
| CN113773209A (en) * | 2021-09-28 | 2021-12-10 | 长春海谱润斯科技股份有限公司 | Triarylamine derivative and organic electroluminescent device thereof |
| CN113801655A (en) * | 2020-06-11 | 2021-12-17 | 三星显示有限公司 | Organic electroluminescent device |
| CN114195653A (en) * | 2020-09-18 | 2022-03-18 | 广州华睿光电材料有限公司 | Organic compound, mixture, composition and organic electronic device |
-
2022
- 2022-12-12 CN CN202211587275.0A patent/CN115583888A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103666455A (en) * | 2013-12-03 | 2014-03-26 | 方圆环球光电技术盐城有限公司 | Novel spirofluorene xanthene organic electroluminescent material and preparation method thereof |
| CN108117491A (en) * | 2016-11-30 | 2018-06-05 | 武汉尚赛光电科技有限公司 | 9,9 '-spiral shell, two fluorenes and amine derivant, its preparation method, application and device |
| KR20190118137A (en) * | 2018-04-09 | 2019-10-17 | 주식회사 엘지화학 | Compound and organic light emitting device comprising same |
| CN113801655A (en) * | 2020-06-11 | 2021-12-17 | 三星显示有限公司 | Organic electroluminescent device |
| CN114195653A (en) * | 2020-09-18 | 2022-03-18 | 广州华睿光电材料有限公司 | Organic compound, mixture, composition and organic electronic device |
| CN113773209A (en) * | 2021-09-28 | 2021-12-10 | 长春海谱润斯科技股份有限公司 | Triarylamine derivative and organic electroluminescent device thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN113816898A (en) | Compound, electron transport material, organic electroluminescent device and display device | |
| CN110734446A (en) | organic compound and application thereof | |
| CN111233764B (en) | Organic compound with acridine derived triarylamine structure and application thereof | |
| CN112125813B (en) | Compound, hole transport material and organic electroluminescent device | |
| CN112174918B (en) | Compound, hole transport material, organic electroluminescent device and display device | |
| CN112125892B (en) | Compound, electron transport material and organic electroluminescent device | |
| CN112159361A (en) | Electron transport material, organic electroluminescent device and display device | |
| CN112159326A (en) | Compound, luminescent layer dye material and organic electroluminescent device | |
| CN115636755A (en) | Naphthyl substituted diarylamine compound and application thereof | |
| CN113321649B (en) | Compound, electron transport material and organic electroluminescent device | |
| CN112110885B (en) | Hole transport material, organic electroluminescent device and display device | |
| CN112341470B (en) | Electron transport material, organic electroluminescent device and display device | |
| CN112125861B (en) | Compound, electron transport material and organic electroluminescent device | |
| CN115991699A (en) | Naphthalene bridging double-suction fragment compound | |
| CN113045553A (en) | Aza-aromatic compound used as electron transport material and application thereof | |
| CN113024512A (en) | Aromatic heterocyclic compound used as electron transport material and application thereof | |
| CN115594599B (en) | Bis-naphthalene compound and application thereof | |
| CN115583888A (en) | Naphthyl substituted arylamine compound and application thereof | |
| CN115521253B (en) | Bibiquinoline derivative compound and application thereof | |
| CN113307764B (en) | Compound, electron transport material, organic electroluminescent device and display device | |
| CN115521292B (en) | Quinoline substituted pyridine compound and application thereof | |
| CN117069597B (en) | Compound and application thereof | |
| CN115611891B (en) | Quinoline-substituted phenanthroline compound and application thereof | |
| CN111635355B (en) | Compound, hole transport material and organic electroluminescent device | |
| CN113321641B (en) | Compound, electron transport material, organic electroluminescent device and display device |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20230110 |
|
| RJ01 | Rejection of invention patent application after publication |