CN116143781A - Organic electroluminescent compound and preparation method and application thereof - Google Patents
Organic electroluminescent compound and preparation method and application thereof Download PDFInfo
- Publication number
- CN116143781A CN116143781A CN202111356040.6A CN202111356040A CN116143781A CN 116143781 A CN116143781 A CN 116143781A CN 202111356040 A CN202111356040 A CN 202111356040A CN 116143781 A CN116143781 A CN 116143781A
- Authority
- CN
- China
- Prior art keywords
- unsubstituted
- organic electroluminescent
- substituted
- electroluminescent compound
- chemical formula
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 46
- 238000002360 preparation method Methods 0.000 title claims description 21
- 230000005525 hole transport Effects 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 239000002994 raw material Substances 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 14
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 12
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- 229910052763 palladium Inorganic materials 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 229960000583 acetic acid Drugs 0.000 claims description 7
- 239000012362 glacial acetic acid Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 5
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 claims description 4
- 239000011259 mixed solution Substances 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 3
- NJSUFZNXBBXAAC-UHFFFAOYSA-N ethanol;toluene Chemical compound CCO.CC1=CC=CC=C1 NJSUFZNXBBXAAC-UHFFFAOYSA-N 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 claims description 3
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 2
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 2
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Chemical group 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000005259 triarylamine group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 34
- 150000002894 organic compounds Chemical class 0.000 abstract description 5
- 239000010410 layer Substances 0.000 description 57
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 46
- 238000002347 injection Methods 0.000 description 14
- 239000007924 injection Substances 0.000 description 14
- 239000012153 distilled water Substances 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000000758 substrate Substances 0.000 description 8
- 238000009423 ventilation Methods 0.000 description 8
- 238000005406 washing Methods 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 5
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
- 238000010791 quenching Methods 0.000 description 5
- 230000005540 biological transmission Effects 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- -1 Bathocuproine (BCP) Chemical compound 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical compound C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 101100391182 Dictyostelium discoideum forI gene Proteins 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- HAQFCILFQVZOJC-UHFFFAOYSA-N anthracene-9,10-dione;methane Chemical compound C.C.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 HAQFCILFQVZOJC-UHFFFAOYSA-N 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- GIFAOSNIDJTPNL-UHFFFAOYSA-N n-phenyl-n-(2-phenylphenyl)naphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1C1=CC=CC=C1 GIFAOSNIDJTPNL-UHFFFAOYSA-N 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- 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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses an organic electroluminescent compound, which can reduce the initial voltage of the device, improve the efficiency of the organic electroluminescent device and prolong the service life well when being used as a hole transport material of an OLED luminescent device or other organic compound layers.
Description
Technical Field
The invention relates to the technical field of photoelectric materials, in particular to an organic electroluminescent compound, a preparation method and application thereof.
Background
In the arrival of the information age, the living standard of modern people is changed day by day, the requirements on display technology are continuously improved, and in the prior art, the OLED technology has the advantages of high contrast, flexibility, wide visual angle, high response speed and the like. This gives OLED technology the potential to replace conventional display technology well.
In general, an OLED light emitting device is a stacked structure, and is formed by sequentially stacking a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. The Hole Transport Layer (HTL) is responsible for adjusting the injection rate and injection amount of holes, and the hole transport material directly affects the efficiency and lifetime of the OLED. In the prior art, compounds commonly used in the hole transport region include copper phthalocyanine (CuPc), 4 '-bis [ N- (1-naphthyl) -N-phenylamino ] biphenyl (NPB), N' -diphenyl-N, N '-bis (3-methylphenyl) - (1, 1' -biphenyl) -4,4 '-diamine (TPD), 4',4 "-tris (3-methylphenyl-phenylamino) triphenylamine (MTDATA), and the like.
However, OLEDs using these materials have problems in terms of quantum efficiency and lifetime. This is because the hole transport material generally has a low Highest Occupied Molecular Orbital (HOMO) value, and excitons generated in the light emitting layer diffuse to the hole transport layer interface or the hole transport layer side, eventually causing light emission at the light emitting layer interface or charge imbalance in the light emitting layer, and thus light emission at the interface of the hole transport layer, making the color purity and efficiency of the organic electroluminescent device low.
Therefore, it is a technical problem that needs to be solved by those skilled in the art how to provide a hole transport material with high light emitting efficiency, better lifetime and low voltage.
Disclosure of Invention
The invention aims to provide an organic electroluminescent compound, a preparation method and application thereof, so as to solve the problems in the background art.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
an organic electroluminescent compound is characterized in that the structural general formula is shown in chemical formula 1:
wherein a and b are 0 or 1, respectively, and a and b cannot be 0 at the same time;
R 1 、R 4 and R is 5 Is at any position of the ring, and R 1 、R 4 And R is 5 The number of the substituents is an integer of 0 to 4;
R 2 and R is 3 Is at any position of the ring, and R 2 And R is 3 The number of the substituents is an integer of 0 to 3 respectively;
R 1 -R 5 each independently selected from the group consisting of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
or alternatively, the first and second heat exchangers may be,
is linked to adjacent substituents to form a single or multiple ring, in particular a C3-C30 cycloaliphatic or aromatic ring;
Ar 1 -Ar 4 each independently selected from the group consisting of substituted or unsubstituted C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted 3-to 30-membered heteroarylamino, substituted or unsubstituted C6-C60 arylamino, C1-C30 alkoxy, C6-C60 aryloxy;
or alternatively, the first and second heat exchangers may be,
and form a mono-or polycyclic C3-C30 aliphatic ring or a 3 to 30 membered aromatic ring with adjacent substituents, the carbon atoms of which may be replaced by at least one heteroatom selected from nitrogen, oxygen and sulfur;
L 1 and L 2 Each independently selected from a linkage or a substituted or unsubstituted C6-C30 aryl.
Preferably, said R 1 -R 5 0 to 1 substituents, respectively, and R is 1 -R 5 Each independently selected from a substituted or unsubstituted C1-C30 alkyl group or a substituted or unsubstituted C6-C30 aryl group.
Preferably, the Ar 1 -Ar 4 Each independently selected from a substituted or unsubstituted C6-C20 aryl, a substituted or unsubstituted C15-C26 heteroaryl, or a triarylamine group.
More preferablyIn the above-mentioned Ar 1 -Ar 4 Each independently selected from a substituted or unsubstituted C10-C14 aryl, a substituted or unsubstituted C18-C22 heteroaryl, or a triphenylamine group.
Preferably, the L 1 And L 2 Each independently selected from benzene or deuterated benzene.
Further, the organic electroluminescent compound is one of the formulas H001-H138:
the preparation method of the organic electroluminescent compound comprises the following synthesis routes:
in the above formula, R 1 ～R 5 、Ar 1 -Ar 4 、L 1 And L 2 And a and b are identical to the same parts of the chemical formula 1, and c is 1 or 2; wherein chemical formula 2 represents L in chemical formula 1 1 And L 2 Are all connecting keys;
the preparation method comprises the following steps:
step 1, preparation of intermediate 1
Dissolving the raw material 2 in THF, ventilating for 3 times, cooling to-78deg.C, adding N-BuLi, reacting for 2h, and then adding N 2 Adding the raw material 1 under protection, heating to 25 ℃, and stirring for 10 hours to prepare an intermediate 1;
step 2, preparation of intermediate 2
Adding the intermediate 1 into a reaction bottle, adding glacial acetic acid, heating to 80 ℃, and dropwise adding concentrated sulfuric acid to prepare an intermediate 2;
step 3, preparation of chemical formula 1
Adding the intermediate 2 and the raw material 3 into a mixed solution of toluene ethanol and water, then ventilating for 3 times, adding a palladium catalyst and potassium carbonate under the protection of nitrogen, uniformly stirring, heating to 95 ℃, and reacting for 10 hours to obtain a chemical formula 1;
or alternatively, the first and second heat exchangers may be,
preparation of chemical formula 2
And adding the intermediate 2 and the raw material 4 into toluene solution, then ventilating for 3 times, adding a palladium catalyst, tri-tert-butylphosphine and sodium tert-butoxide under the protection of nitrogen, stirring uniformly, heating to 110 ℃, and reacting for 8 hours to obtain the chemical formula 2.
Preferably, the step 1 specifically includes:
dissolving the raw material 2 in THF, ventilating for 3 times, cooling to-70 to-80 ℃, slowly adding n-BuLi, reacting for 1-3h, and N 2 Raw material 1 was added under protection, slowly warmed to 20-30 ℃, stirred for 8-10h, then distilled water was slowly added to the reaction solution to quench the reaction, and the reaction solution was extracted with DCM; the extracted organic layer was then dried using magnesium sulfate and the solvent was removed using a rotary evaporator; solid precipitated with DCM and PE (1:6) to afford intermediate 1.
Preferably, the step 2 specifically includes:
adding the intermediate 1 into a reaction bottle, adding glacial acetic acid with the volume of 10 times, heating to 80 ℃, slowly dropwise adding concentrated sulfuric acid (with the volume of 1 time), finishing the reaction after the dropwise adding, adding distilled water with the volume of 20 times of the concentrated sulfuric acid, and completely precipitating, filtering and drying solids to obtain the intermediate 2.
Preferably, the step 3 specifically includes:
preparation of chemical formula 1
Adding the intermediate 2 and the raw material 3 into a mixed solution of toluene ethanol and water, then ventilating for 3 times, adding a palladium catalyst and potassium carbonate under the protection of nitrogen, stirring uniformly, heating to 95 ℃, reacting for 10 hours, and then extracting the mixture with dichloromethane and water; the extracted organic layer was then dried over sodium sulfate and the solvent was removed using a rotary evaporator; the remaining material was purified by column chromatography to obtain a compound represented by chemical formula 1.
Or alternatively, the first and second heat exchangers may be,
preparation of chemical formula 2
Adding the intermediate 2 and the raw material 4 into toluene solution, then ventilating for 3 times, adding a palladium catalyst, tri-tert-butyl phosphine and sodium tert-butoxide under the protection of nitrogen, stirring uniformly, heating to 110 ℃, reacting for 10 hours, and then extracting the mixture with dichloromethane and water; the extracted organic layer was then dried over sodium sulfate and the solvent was removed using a rotary evaporator; the remaining material was purified by column chromatography to obtain a compound represented by chemical formula 2.
Another object of the present invention is to provide an organic electroluminescent device comprising the above organic electroluminescent compound, comprising: a first electrode, a second electrode, one or more organic compound layers interposed between the first electrode and the second electrode;
the organic compound layer includes a hole transport layer including the organic electroluminescent compound described above.
The hole transporting material is a material capable of receiving holes from the anode or the hole injection layer and transporting the holes to the light emitting layer, and has high hole mobility.
Preferably, one or more layers of a hole injection layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer are further included.
Preferably, the first electrode acts as an anode, which preferably comprises a material having a high work function. Such as Indium Tin Oxide (ITO) or Indium Zinc Oxide (IZO). Since the lifetime of the device of the invention is reduced in the presence of water and/or air, the device is properly (depending on the application) structured, provided with contacts and finally sealed.
The electron blocking layer may be disposed between the hole transport layer and the light emitting layer. As the electron blocking layer, materials known in the art, such as an arylamine-based organic material, may be used.
The material of the light emitting layer is a material capable of emitting visible light by receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and combining the received holes and electrons.
The light-emitting layer comprises a host material and a doping material;
the mass ratio of the main material to the doping material is 90-99.5:0.5-10;
the host material comprises a fluorescent host and a phosphorescent host;
doping materials include fluorescent doping and phosphorescent doping;
as the hole blocking layer material, a compound having a hole blocking effect known in the prior art, for example, a phenanthroline derivative such as Bathocuproine (BCP), an oxazole derivative, a triazole derivative, a triazine derivative, or the like can be used, but is not limited thereto.
The electron transport layer may function to facilitate electron transport. Compounds having an electron-transporting effect known in the art, for example, al complexes of 8-hydroxyquinoline; complexes comprising Alq 3; an organic radical compound; hydroxyflavone-metal complex, etc.
The electron injection layer may function to promote electron injection. Has an ability to transport electrons, and prevents excitons generated in the light emitting layer from migrating to the hole injection layer. The electron injecting material used in the present invention includes fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, oxazole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone and the like and derivatives thereof, metal complexes, nitrogen-containing five-membered ring derivatives and the like, but is not limited thereto.
The second electrode serves as a cathode, and a material having a small work function is generally preferable so that electrons are smoothly injected into the organic material layer. Such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof.
Compared with the prior art, the invention has the following beneficial effects:
the pi conjugation effect in the organic electroluminescent compound makes the compound have strong hole transmission capability; when the organic electroluminescent compound is used as a hole transport material or other organic compound layers of an OLED luminescent device, the high hole transport rate can reduce the starting voltage of the device, improve the efficiency of the organic electroluminescent device and prolong the service life well.
Detailed Description
The following description of the technical solutions in the embodiments of the present invention will be clear and complete, and it is obvious that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
The preparation method of the organic electroluminescent compound adopts the synthetic route and comprises the following steps:
raw material 2 (44.6 mmol) and 100ml THF were added to the reaction vessel, the temperature was lowered to-78℃by 3 times of ventilation, 2.5mol/L n-BuLi (17.8 ml,44.6 mmol) was added under nitrogen atmosphere and stirred for 2 hours, raw material 1 (37 mmol) was added and heated to 25℃and stirred for 10 hours, and the reaction was completed. Distilled water was then added to the reaction solution to quench the reaction, and the reaction solution was extracted with DCM. The extracted organic layer was then dried over magnesium sulfate and the solvent was removed using a rotary evaporator, and the solid was precipitated with DCM and PE (1:6) to afford intermediate 1 (12.8 g, 75.7% yield, MW: 457.91).
Intermediate 1 (26.2 mmol) was added to a reaction flask, 240ml of glacial acetic acid was added, the temperature was raised to 80 ℃, 12ml of concentrated sulfuric acid was added dropwise, the reaction was completed after the dropwise addition was completed, then 240ml of distilled water was added, solids were precipitated, and intermediate 2 (8.9 g, yield 77.23%, MW: 439.88) was obtained by drying.
Intermediate 2 (18.1 mmol) and raw material 3 (21.8 mmol) were added to 300ml of toluene solution, followed by ventilation 3 times, palladium catalyst (0.181 mmol), tri-tert-butylphosphine (0.905 mmol) and sodium tert-butoxide (36.2 mmol) were added under nitrogen protection, stirred well, warmed to 110 ℃, reacted for 10h, and the mixture was extracted with dichloromethane and water; the extracted organic layer was then dried over sodium sulfate and the solvent was removed using a rotary evaporator; the remaining material was purified by column chromatography (volume ratio of DCM to PE 1:11) to give an organic electroluminescent compound of formula H048 (9.88 g, 71.3% yield, MW: 764.97) as follows:
example 2
The preparation method of the organic electroluminescent compound adopts the synthetic route and comprises the following steps:
raw material 2 (44.6 mmol) and 100ml THF were added to the reaction vessel, the temperature was lowered to-78℃by 3 times of ventilation, 2.5mol/L n-BuLi (17.8 ml,44.6 mmol) was added under nitrogen atmosphere and stirred for 2 hours, raw material 1 (37 mmol) was added and heated to 25℃and stirred for 10 hours, and the reaction was completed. Distilled water was then added to the reaction solution to quench the reaction, and the reaction solution was extracted with DCM. The extracted organic layer was then dried over magnesium sulfate and the solvent was removed using a rotary evaporator, and the solid was precipitated with DCM and PE (1:6) to afford intermediate 1 (12.4 g, 73.4% yield, MW: 457.92).
Intermediate 1 (26.2 mmol) was added to a reaction flask, 240ml of glacial acetic acid was added, the temperature was raised to 80 ℃, 12ml of concentrated sulfuric acid was added dropwise, the reaction was completed after the dropwise addition was completed, then 240ml of distilled water was added, solids were precipitated, and intermediate 2 (8.4 g, yield 72.8%, MW: 439.89) was obtained by drying.
Intermediate 2 (18.1 mmol) and raw material 3 (21.8 mmol) were added to a mixed solution of toluene (180 ml), ethanol (60 ml) and water (60 ml), followed by ventilation for 3 times, palladium catalyst (0.181 mmol) and potassium carbonate (54.3 mmol), stirred well, warmed to 100 ℃, reacted for 10h, and then the mixture was extracted with dichloromethane and water; the extracted organic layer was then dried over sodium sulfate and the solvent was removed using a rotary evaporator; the remaining material was purified by column chromatography (volume ratio of DCM to PE 1:11) to give an organic electroluminescent compound of formula H033 (10.1 g, 69.8% yield, MW: 801.05), the reaction scheme being as follows:
example 3
The preparation method of the organic electroluminescent compound adopts the synthetic route and comprises the following steps:
raw material 2 (44.6 mmol) and 100ml THF were added to the reaction vessel, the temperature was lowered to-78℃by 3 times of ventilation, 2.5mol/L n-BuLi (17.8 ml,44.6 mmol) was added under nitrogen atmosphere and stirred for 2 hours, raw material 1 (37 mmol) was added and heated to 25℃and stirred for 10 hours, and the reaction was completed. Distilled water was then added to the reaction solution to quench the reaction, and the reaction solution was extracted with DCM. The extracted organic layer was then dried over magnesium sulfate and the solvent was removed using a rotary evaporator, and the solid was precipitated with DCM and PE (1:6) to afford intermediate 1 (14.3 g, 72.4% yield, MW: 536.11).
Intermediate 1 (26.2 mmol) was added to a reaction flask, 240ml of glacial acetic acid was added, the temperature was raised to 80 ℃, 12ml of concentrated sulfuric acid was added dropwise, the reaction was completed after the dropwise addition was completed, then 240ml of distilled water was added, solids were precipitated, and intermediate 2 (10.4 g, yield 76.5%, MW: 518.10) was obtained by drying.
Intermediate 2 (18.1 mmol) and raw material 3 (21.8 mmol) were added to 300ml of toluene solution, followed by ventilation 3 times, palladium catalyst (0.181 mmol), tri-tert-butylphosphine (0.905 mmol) and sodium tert-butoxide (36.2 mmol) were added under nitrogen protection, stirred well, warmed to 110 ℃, reacted for 10h, and the mixture was extracted with dichloromethane and water; the extracted organic layer was then dried over sodium sulfate and the solvent was removed using a rotary evaporator; the remaining material was purified by column chromatography (volume ratio of DCM to PE 1:11) to give an organic electroluminescent compound of formula H067 (11.2 g, 70.1% yield, MW: 883.18) as follows:
example 4
The preparation method of the organic electroluminescent compound adopts the synthetic route and comprises the following steps:
raw material 2 (44.6 mmol) and 100ml THF were added to the reaction vessel, the temperature was lowered to-78℃by 3 times of ventilation, 2.5mol/L n-BuLi (17.8 ml,44.6 mmol) was added under nitrogen atmosphere and stirred for 2 hours, raw material 1 (37 mmol) was added and heated to 25℃and stirred for 10 hours, and the reaction was completed. Distilled water was then added to the reaction solution to quench the reaction, and the reaction solution was extracted with DCM. The extracted organic layer was then dried over magnesium sulfate and the solvent was removed using a rotary evaporator, and the solid was precipitated with DCM and PE (1:6) to afford intermediate 1 (14.2 g, 75.5% yield, MW: 508.05).
Intermediate 1 (26.2 mmol) was added to a reaction flask, 240ml of glacial acetic acid was added, the temperature was raised to 80 ℃, 12ml of concentrated sulfuric acid was added dropwise, the reaction was completed after the dropwise addition was completed, then 240ml of distilled water was added, solids were precipitated, and intermediate 2 (9.8 g, yield 76.1%, MW: 490.08) was obtained by drying.
Intermediate 2 (18.1 mmol) and raw material 3 (21.8 mmol) were added to 300ml of toluene solution, followed by ventilation 3 times, palladium catalyst (0.181 mmol), tri-tert-butylphosphine (0.905 mmol) and sodium tert-butoxide (36.2 mmol) were added under nitrogen protection, stirred well, warmed to 110 ℃, reacted for 10h, and the mixture was extracted with dichloromethane and water; the extracted organic layer was then dried over sodium sulfate and the solvent was removed using a rotary evaporator; the remaining material was purified by column chromatography (volume ratio of DCM to PE 1:11) to give an organic electroluminescent compound of formula H093 (10.7 g, 71.1% yield, MW: 829.08) as follows:
examples 5 to 20
The synthesis of compounds 2,6, 11, 18, 26, 47, 60, 70, 76, 82, 85, 92, 95, 100, 105, 123 was accomplished by reference to the synthesis method of example 1, and the mass spectra and molecular formulas and yields of examples 5-20 are shown in table 1 below. In addition, other compounds of the present application can be obtained by referring to the synthetic methods of the examples listed above.
TABLE 1
Application example 1
An organic electroluminescent device is prepared by the following method:
a. ITO anode: the thickness of the coating is equal to
The ITO (indium tin oxide) -Ag-ITO (indium tin oxide) glass substrate is washed for 2 times in distilled water, ultrasonic wave is used for washing for 30min, then distilled water is used for repeatedly washing for 2 times, ultrasonic wave is used for washing for 10min, methanol, acetone and isopropanol are used for ultrasonic wave washing (5 min for washing each time) in sequence after washing is finished, drying is carried out, then the glass substrate is transferred into a plasma washer for washing for 5min, and then the glass substrate is sent into an evaporation machine, the substrate is used as an anode, and other functional layers are sequentially evaporated on the substrate.
b. HIL (hole injection layer): to be used for
Is evaporated at a vacuumPlating hole injection layer materials HT (compound provided in example 1 of the present invention) and P-dopant, wherein the evaporation rate ratio of HT and P-dopant is 98:2, the thickness is 10nm;
c. HTL (hole transport layer): to be used for
Vacuum evaporating 120nm of the compound provided in example 1 of the present invention as a hole transporting layer on top of the hole injecting layer; />
d. EML (light emitting layer): then on the hole transport layer to
The Host material (Host) and the Dopant material (Dopant) having a thickness of 25nm were vacuum-deposited as light-emitting layers, and the chemical formulas of Host and Dopant are shown below. Wherein the evaporation rate ratio of Host to Dopant is 97:3.
e. ETL (electron transport layer): to be used for
ET and Liq having a thickness of 35nm were vacuum-deposited as electron transport layers, and the chemical formula of ET is shown below. Wherein the evaporation rate ratio of ET to Liq is 50:50.
f. EIL (electron injection layer): to be used for
The vapor deposition rate of Yb film layer was 1.0nm to form an electron injection layer.
g. And (3) cathode: to be used for
The vapor deposition rate ratio of magnesium and silver is 18nm, and the vapor deposition rate ratio is 1:9, so that the OLED device is obtained.
h. Light extraction layer: to be used for
CPL with the thickness of 70nm is vacuum evaporated on the cathode,as a light extraction layer.
i. And packaging the substrate subjected to evaporation. Firstly, a gluing device is adopted to carry out a coating process on a cleaned cover plate by UV glue, then the coated cover plate is moved to a lamination working section, a substrate subjected to vapor deposition is placed at the upper end of the cover plate, and finally the substrate and the cover plate are bonded under the action of a bonding device, and meanwhile, the UV glue is cured by illumination.
Comparative example 1
According to the method of application example 1, the material of the hole transport layer is replaced by a chemical compound a in application example 1, and the structural formula of the compound a is as follows:
comparative example 2
According to the method of application example 1, the material of the hole transport layer is replaced by a chemical compound B in application example 1, and the structural formula of the compound B is as follows:
the organic electroluminescent devices obtained in the device comparative examples of the above device examples were characterized in terms of driving voltage, luminous efficiency, BI value and lifetime at a luminance of 1000 (nits), and the test results are shown in table 2 below:
TABLE 2
As can be seen from table 2, the pi conjugation effect in the organic electroluminescent compound provided by the invention makes the organic electroluminescent compound have strong hole transmission capability, the whole inter-structure of the compound is radial by introducing the aromatic amine side chain, so that the inter-molecule distance is increased, the intermolecular cohesive force is reduced, the crystallization possibility is reduced, and when the organic electroluminescent compound is used as a hole transmission material of an OLED light-emitting device or other organic compound layers, the high hole transmission rate can reduce the initial voltage of the device, improve the efficiency of the organic electroluminescent device, and prolong the service life well.
In the present specification, each embodiment is described in a progressive manner, and each embodiment is mainly described in a different point from other embodiments, and identical and similar parts between the embodiments are all enough to refer to each other. For the device disclosed in the embodiment, since it corresponds to the method disclosed in the embodiment, the description is relatively simple, and the relevant points refer to the description of the method section.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (7)
1. An organic electroluminescent compound is characterized in that the structural general formula is shown in chemical formula 1:
wherein a and b are 0 or 1, respectively, and a and b cannot be 0 at the same time;
R 1 、R 4 and R is 5 Is at any position of the ring andR 1 、R 4 and R is 5 The number of the substituents is an integer of 0 to 4;
R 2 and R is 3 Is at any position of the ring, and R 2 And R is 3 The number of the substituents is an integer of 0 to 3 respectively;
R 1 -R 5 each independently selected from the group consisting of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
or alternatively, the first and second heat exchangers may be,
to adjacent substituents to form a single or multiple ring;
Ar 1 -Ar 4 each independently selected from the group consisting of substituted or unsubstituted C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted 3-to 30-membered heteroarylamino, substituted or unsubstituted C6-C60 arylamino, C1-C30 alkoxy, C6-C60 aryloxy;
or alternatively, the first and second heat exchangers may be,
to adjacent substituents to form a single ring or multiple rings, and the carbon atom of which may be replaced with at least one heteroatom selected from nitrogen, oxygen and sulfur;
L 1 and L 2 Each independently selected from a linkage or a substituted or unsubstituted C6-C30 aryl.
2. An organic electroluminescent compound according to claim 1, wherein Ar 1 -Ar 4 Each independently selected from a substituted or unsubstituted C6-C20 aryl, a substituted or unsubstituted C15-C26 heteroaryl, or a triarylamine group.
3. An organic electroluminescent compound according to claim 1, wherein the L 1 And L 2 Each independently selected from benzene or deuterated benzene.
4. The organic electroluminescent compound according to claim 1, wherein the organic electroluminescent compound is one of the formulae H001-H138:
5. a method for preparing an organic electroluminescent compound as claimed in any one of claims 1 to 4, characterized in that the synthetic route is as follows:
in the above-mentioned description of the invention,R 1 ～R 5 、Ar 1 -Ar 4 、L 1 and L 2 And a, b are identical to the same moiety of formula 1 as described in any one of claims 1 to 3, c is 1 or 2; wherein chemical formula 2 represents L in chemical formula 1 1 And L 2 Are all connecting keys;
the preparation method comprises the following steps:
step 1, preparation of intermediate 1
Dissolving the raw material 2 in THF, ventilating for 3 times, cooling to-70 to-80 ℃, adding N-BuLi, reacting for 1-3h, and then adding N into the mixture 2 Adding the raw material 1 under protection, heating to 20-30 ℃, and stirring for 8-10h to obtain an intermediate 1;
step 2, preparation of intermediate 2
Adding the intermediate 1 into a reaction bottle, adding glacial acetic acid, heating to 60-80 ℃, and dropwise adding concentrated sulfuric acid to prepare an intermediate 2;
step 3, preparation of chemical formula 1
Adding the intermediate 2 and the raw material 3 into a mixed solution of toluene ethanol and water, then ventilating for 3 times, adding a palladium catalyst and potassium carbonate under the protection of nitrogen, uniformly stirring, heating to 90-100 ℃, and reacting for 8-10h to obtain a chemical formula 1;
or alternatively, the first and second heat exchangers may be,
preparation of chemical formula 2
Adding the intermediate 2 and the raw material 4 into toluene solution, then ventilating for 3 times, adding a palladium catalyst, tri-tert-butyl phosphine and sodium tert-butoxide under the protection of nitrogen, stirring uniformly, heating to 100-110 ℃, and reacting for 7-10 h to obtain the chemical formula 2.
6. A hole transport layer in an organic electroluminescent device, characterized in that the hole transport layer in the organic electroluminescent device comprises the organic electroluminescent compound according to any one of claims 1 to 4 or the organic electroluminescent compound produced by the production method according to claim 5.
7. An organic electroluminescent device comprising the hole transport layer of claim 6.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111356040.6A CN116143781A (en) | 2021-11-16 | 2021-11-16 | Organic electroluminescent compound and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111356040.6A CN116143781A (en) | 2021-11-16 | 2021-11-16 | Organic electroluminescent compound and preparation method and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116143781A true CN116143781A (en) | 2023-05-23 |
Family
ID=86339364
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111356040.6A Pending CN116143781A (en) | 2021-11-16 | 2021-11-16 | Organic electroluminescent compound and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116143781A (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112062765A (en) * | 2020-09-18 | 2020-12-11 | 吉林奥来德光电材料股份有限公司 | Organic photoelectric luminescent compound and preparation method thereof |
| CN112079806A (en) * | 2020-09-19 | 2020-12-15 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent compound, preparation method thereof and organic electroluminescent device |
| CN112079834A (en) * | 2020-09-18 | 2020-12-15 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent compound and application thereof |
| CN112500410A (en) * | 2020-11-30 | 2021-03-16 | 吉林奥来德光电材料股份有限公司 | Spiro nitrogen-containing organic luminescent compound, and preparation method and application thereof |
| CN113292481A (en) * | 2021-03-31 | 2021-08-24 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent compounds, preparation method and application thereof |
-
2021
- 2021-11-16 CN CN202111356040.6A patent/CN116143781A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112062765A (en) * | 2020-09-18 | 2020-12-11 | 吉林奥来德光电材料股份有限公司 | Organic photoelectric luminescent compound and preparation method thereof |
| CN112079834A (en) * | 2020-09-18 | 2020-12-15 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent compound and application thereof |
| CN112079806A (en) * | 2020-09-19 | 2020-12-15 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent compound, preparation method thereof and organic electroluminescent device |
| CN112500410A (en) * | 2020-11-30 | 2021-03-16 | 吉林奥来德光电材料股份有限公司 | Spiro nitrogen-containing organic luminescent compound, and preparation method and application thereof |
| CN113292481A (en) * | 2021-03-31 | 2021-08-24 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent compounds, preparation method and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101565200B1 (en) | New compound and organic light emitting device using the same | |
| CN113024529B (en) | Organic electroluminescent material and organic electroluminescent device | |
| KR101996649B1 (en) | Pyrene derivative compounds and organic light-emitting diode including the same | |
| CN115073305B (en) | Organic electroluminescent compound and preparation method and application thereof | |
| CN112079834B (en) | Organic electroluminescent compound and application thereof | |
| CN111116505B (en) | Amine compound and organic light-emitting device thereof | |
| CN114716330A (en) | Luminescent auxiliary material, preparation method and application thereof | |
| CN114957017B (en) | Organic electroluminescent compound and synthesis method and application thereof | |
| CN113816979B (en) | Organic compound and electroluminescent application thereof | |
| CN114262328B (en) | Organic electroluminescent compound, preparation method thereof and organic electroluminescent device | |
| CN115260042B (en) | Compound and preparation method thereof, organic electroluminescent device and organic photoelectric material | |
| CN112079876A (en) | Organic compound and organic electroluminescent device using same | |
| CN115304567A (en) | Organic compound, preparation method thereof and organic electroluminescent device | |
| CN112939990B (en) | Luminescent compound with organic condensed rings, preparation method thereof and organic electroluminescent device | |
| CN112574162A (en) | Dibenzo-pyranyl compound, preparation method thereof and organic electroluminescent device | |
| CN112480114A (en) | Organic electroluminescent compound, preparation method and application thereof | |
| CN115073307B (en) | Fluorene compound and application thereof in organic electroluminescent device | |
| CN115043739B (en) | Organic electroluminescent compound, preparation method thereof and organic electroluminescent device | |
| CN114605389B (en) | Thermal activation delay fluorescent material and device thereof | |
| CN115181074A (en) | Luminous auxiliary material, preparation method thereof and luminous device | |
| CN116143781A (en) | Organic electroluminescent compound and preparation method and application thereof | |
| CN112759571A (en) | Organic electroluminescent compound, preparation method thereof and organic electroluminescent device comprising organic electroluminescent compound | |
| CN115745900B (en) | Spirofluorene electron transport organic electroluminescent compound and organic electroluminescent device comprising same | |
| CN112661701B (en) | Pterenes electron transport material, preparation method thereof and organic electroluminescent device | |
| CN116041268B (en) | Organic compound and application thereof |
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 |