CN113620860A - Organic electroluminescent compound and preparation method and application thereof - Google Patents
Organic electroluminescent compound and preparation method and application thereof Download PDFInfo
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- CN113620860A CN113620860A CN202011475226.9A CN202011475226A CN113620860A CN 113620860 A CN113620860 A CN 113620860A CN 202011475226 A CN202011475226 A CN 202011475226A CN 113620860 A CN113620860 A CN 113620860A
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- Prior art keywords
- organic electroluminescent
- catalyst
- electroluminescent compound
- compound
- hole transport
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 61
- 238000002360 preparation method Methods 0.000 title abstract description 12
- 230000005525 hole transport Effects 0.000 claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 24
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 23
- 238000002347 injection Methods 0.000 claims description 9
- 239000007924 injection Substances 0.000 claims description 9
- 230000009471 action Effects 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 239000002994 raw material Substances 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- 230000000903 blocking effect Effects 0.000 claims description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- 239000010409 thin film Substances 0.000 claims description 4
- SFUIGUOONHIVLG-UHFFFAOYSA-N (2-nitrophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1[N+]([O-])=O SFUIGUOONHIVLG-UHFFFAOYSA-N 0.000 claims description 3
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 3
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 10
- 238000005137 deposition process Methods 0.000 abstract description 2
- 230000009477 glass transition Effects 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 230000015556 catabolic process Effects 0.000 abstract 1
- 238000006731 degradation reaction Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 75
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000001816 cooling Methods 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 10
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 238000003756 stirring 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
- 238000001514 detection method Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000005259 triarylamine group Chemical group 0.000 description 3
- UPJLZKCEPFAKSH-UHFFFAOYSA-N 2',7'-dibromo-9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC(Br)=CC=C1C1=CC=C(Br)C=C12 UPJLZKCEPFAKSH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000004986 diarylamino group Chemical group 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- FQHFBFXXYOQXMN-UHFFFAOYSA-M lithium;quinolin-8-olate Chemical compound [Li+].C1=CN=C2C([O-])=CC=CC2=C1 FQHFBFXXYOQXMN-UHFFFAOYSA-M 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- DKGYESBFCGKOJC-UHFFFAOYSA-N thiophen-3-amine Chemical compound NC=1C=CSC=1 DKGYESBFCGKOJC-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- JAUCIDPGGHZXRP-UHFFFAOYSA-N 4-phenyl-n-(4-phenylphenyl)aniline Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC(C=C1)=CC=C1C1=CC=CC=C1 JAUCIDPGGHZXRP-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
- GHQCIALFYKYZGS-UHFFFAOYSA-N dibenzofuran-3-amine Chemical compound C1=CC=C2C3=CC=C(N)C=C3OC2=C1 GHQCIALFYKYZGS-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000006617 triphenylamine group Chemical class 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
Classifications
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- 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
- C07D209/96—Spiro-condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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- 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
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
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- Y02E10/549—Organic PV cells
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- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to the technical field of organic electroluminescent materials, in particular to an organic electroluminescent compound and a preparation method and application thereof; the organic electroluminescent compound has a structure shown as a formula I, and the molecular structure and substituent groups are designedThe organic electroluminescent compound is endowed with higher glass transition temperature and good thermal stability, and the degradation of the organic electroluminescent compound in a high-temperature deposition process is avoided; and the hole transport performance and stability of the organic light emitting diode serving as a hole transport layer are remarkably improved, so that an OLED device containing the organic light emitting diode has high light emitting efficiency and long service life, and the power efficiency and the power consumption are improved.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to an organic electroluminescent compound and a preparation method and application thereof.
Background
An electroluminescent device (EL device) is a self-luminous device, which has advantages of a wider viewing angle, a larger contrast ratio, and a faster response time. Currently, the first organic EL device is manufactured by Eastman Kodak (Eastman Kodak) by using small aromatic diamine molecules and metal aluminum complexes as materials for forming a light emitting layer [ applied physics (appl. phys. lett.) 51,913,1987 ].
In the prior art, hole transport materials are usually used in the hole transport layer or hole injection layer and exciton blocking layer, and the hole transport materials which are frequently used are triarylamine derivatives which contain at least two triarylamine groups or at least one triarylamine group and at least one carbazole group; the above compounds are usually derived from diarylamino substituted triphenylamines (TPA type), diarylamino substituted biphenyl derivatives (TAD type) or combinations of these base compounds. The use of the above compounds in fluorescent OLEDs or phosphorescent OLEDs, in particular in organic electroluminescent devices, requires improvements in operating voltage, efficiency, lifetime and thermal stability during sublimation.
In view of the above, the present invention is particularly proposed.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides an organic electroluminescent compound and a preparation method and application thereof.
As a first object of the present invention, there is provided an organic electroluminescent compound intermediate; the intermediate can be used for synthesizing organic electroluminescent compounds.
Specifically, the organic electroluminescent compound has a structure shown as a formula M-1:
as a second object of the present invention, there is provided a method for preparing the above organic electroluminescent compound intermediate, the synthetic route being as follows:
the method specifically comprises the following steps:
(1) taking a compound IM-01 as a raw material, and carrying out a coupling reaction with o-nitrobenzeneboronic acid under the action of a catalyst to obtain a compound IM-02;
(2) performing a closed-loop reaction on the compound IM-02 under the action of a catalyst to obtain an organic electroluminescent compound intermediate with a structure shown as a formula M-1;
preferably, in step (1), the catalyst is a palladium catalyst;
preferably, in step (2), the catalyst is a phosphine catalyst;
further, in the step (1), the catalyst is palladium tetratriphenylphosphine;
further, in the step (2), the catalyst is triphenylphosphine.
The adoption of the palladium catalyst is more beneficial to the ring-closing reaction and improves the synthesis efficiency of the organic electroluminescent compound intermediate.
As a third object of the present invention, there is provided an organic electroluminescent compound; the organic electroluminescent compound has good hole transport performance and stability, and can be used for manufacturing OLED devices with long service life.
Specifically, the organic electroluminescent compound has a structure shown in a formula I:
wherein Ar is1、Ar2、Ar3Each independently represents a group having C6～C60Aromatic or C6～C60A heteroaromatic ring system of (a).
Preferably, Ar is1、Ar2、Ar3Each independently represents benzene, biphenyl, naphthalene, phenanthrene, fluorene, spirobifluorene, dibenzofuran or dibenzothiophene.
Preferably, the organic electroluminescent compound is selected from one or more of the formulae H1 to H20:
as a fourth object of the present invention, there is provided a method for preparing the above organic electroluminescent compound, comprising the steps of:
(1) to be provided with
As a raw material, with Ar1-X is subjected to a coupling reaction under the action of a catalyst to obtain
(2) To be provided with
As a raw material, with
Carrying out coupling reaction under the action of a catalyst to obtain
Wherein, X represents halogen;
Ar1、Ar2、Ar3each independently having the same limitations as claim 3.
Preferably, in step (1), the catalyst is a copper catalyst; preferably cuprous iodide;
preferably, in step (2), the catalyst is a palladium catalyst; preferably Pd2(dba)3；
Preferably, X represents I.
As a fifth object of the present invention, there is provided a hole transport layer for an OLED device, the hole transport layer comprising the above organic electroluminescent compound.
As a sixth object of the present invention, there is provided an OLED device comprising an anode, a cathode, and at least one organic thin film layer between the anode and the cathode; the organic thin film layer comprises a hole transport layer and any one or the combination of at least two of a hole injection layer, an electron blocking layer, a hole blocking layer, a light emitting layer, an electron transport layer and an electron injection layer;
the hole transport layer is the hole transport layer for the OLED device.
As a seventh object of the present invention, there is provided an electronic apparatus comprising the OLED device as described above.
The excellent effects of the present invention:
(1) the organic electroluminescent compound provided by the invention has a condensed ring structure, and the design of a molecular structure and a substituent endows the organic electroluminescent compound with higher glass transition temperature and good thermal stability, so that the organic electroluminescent compound is prevented from being degraded in a high-temperature deposition process; and the hole transport performance and stability of the organic light emitting diode serving as a hole transport layer are remarkably improved, so that an OLED device containing the organic light emitting diode has high light emitting efficiency and long service life, and the power efficiency and the power consumption are improved.
(2) The organic electroluminescent compound is suitable for fluorescent OLED devices and phosphorescent OLED devices, and is particularly suitable for phosphorescent OLED devices.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
The related compound has the following structure:
example 1
This example provides an organic electroluminescent compound intermediate M-1, which has the following structure:
the synthetic route of the M-1 is as follows:
the method specifically comprises the following steps:
(1) synthesis of IM-02:
adding 2, 7-dibromo-9, 9 '-spirobifluorene (47.4g and 0.1mol) and o-nitrobenzeneboronic acid (16.7g and 0.1mol) into a 1000ml three-neck flask, adding toluene 250ml, ethanol 125ml and water 125ml, adding sodium carbonate (13.8g and 0.13mol) under stirring, adding tetratriphenylphosphine palladium (0.12g and 0.00001mol), replacing nitrogen, starting heating, slowly heating to 80 ℃ (keeping nitrogen protection in the reaction process), reacting for 2 hours, detecting by HPLC (raw material 2, 7-dibromo-9, 9' -spirobifluorene < 1%), stopping the reaction, and cooling to room temperature. After the reaction is finished, cooling to 25 ℃, separating liquid, adding anhydrous sodium sulfate into the organic phase, and drying; performing column chromatography with toluene as eluent; concentration gave a crude product which was recrystallized from toluene and ethanol at 1: 2 to give 36.1g of intermediate IM-02 with a purity of > 98% and a yield of 70%.
(2) Synthesis of M-1:
to a 1000ml three-necked flask, IM-02(36.1g, 0.07mol), dichlorobenzene (500ml), triphenylphosphine (36.7g, 0.14mol) and nitrogen were added, the temperature was gradually raised to 170 ℃ to react for 10 hours, and the reaction was stopped by HPLC (IM-02< 1%). And (2) evaporating the solvent under reduced pressure, cooling to room temperature, adding ethyl acetate for dissolving, performing column chromatography separation, wherein an eluent is petroleum ether ethyl acetate to obtain a solid crude product, and adding toluene: ethanol ═ 1: 4, recrystallizing to obtain 23.7g of intermediate M-1 with the purity of 98 percent and the yield of 70 percent.
Example 2
This example provides an organic electroluminescent compound H1, which has the following structure:
the preparation method of the H1 comprises the following steps:
(1) synthesis of M-1-1:
m-1(23.7g, 0.049mol) and iodobenzene (10g, 0.049mol) were added to a 500ml three-necked flask, 200ml of DMF was added, potassium hydroxide (5.4g, 0.098mol) and cuprous iodide (9.3g, 0.049mol) were added with stirring, the mixture was heated to 150 ℃ for reaction for 3 hours, HPLC detection (M-1< 1%) was performed, the reaction was stopped, the reaction solution was cooled, 200ml of water was added, a solid was precipitated, and a crude product was obtained by filtration and recrystallized from toluene to obtain 22g of intermediate M-1-1, purity 98%, yield 80%.
(2) Synthesis H1:
to a 250ml three-necked flask, M-1-1(5.6g, 0.01mol) and bis (4-biphenylyl) amine (3.2g, 0.01mol) were added, 100ml of toluene was added, and sodium t-butoxide (1.2g, 0.013mol), Pd and the mixture were added under stirring2(dba)3(0.046g, 0.00005mol), replacing nitrogen, adding 0.2g of tri-tert-butylphosphine 10% toluene solution, starting heating, slowly heating to 80 ℃ (keeping nitrogen protection in the reaction process), reacting for 2 hours, and detecting by HPLC (M-1)<1 percent), stopping the reaction and cooling to room temperature. After the reaction is finished, cooling to 25 ℃, washing with salt water for 2 times, adding anhydrous sodium sulfate into the organic phase, and drying; performing column chromatography with toluene as eluent; concentrating to obtain crude product, recrystallizing with toluene to obtain product H1 6.4g with purity>99% and yield 80%.
The compound H1 was subjected to nuclear magnetic detection and the data was resolved as follows:
1HNMR(300MHz，CDCl3)δ8.55(d，1H)，δ8.22(s，1H)δ8.20(d，1H)，δ7.94～7.89(m，3H)，δ7.75～7.73(m，5H)，δ7.62～7.28(m，28H)，δ7.16(t，1H)。
example 3
This example provides an organic electroluminescent compound H2, which has the following structure:
the preparation method of the H2 comprises the following steps:
(1) synthesis of M-1-1:
the same as in example 2.
(2) Synthesis H2:
to a 250ml three-necked flask, M-1-1(5.6g, 0.01mol) and N- [1,1' -biphenyl-4-yl were added]-9, 9-dimethyl-9H-fluoren-2-amine (3.6g, 0.01mol), 100ml of toluene was added, and sodium t-butoxide (1.2g, 0.013mol), Pd were added with stirring2(dba)3(0.046g, 0.00005mol), replacing nitrogen, adding 0.2g of tri-tert-butylphosphine 10% toluene solution, starting heating, slowly heating to 80 ℃ (keeping nitrogen protection in the reaction process), reacting for 2 hours, and detecting by HPLC (M-1)<1 percent), stopping the reaction and cooling to room temperature. After the reaction is finished, cooling to 25 ℃, washing with salt water for 2 times, adding anhydrous sodium sulfate into the organic phase, and drying; performing column chromatography with toluene as eluent; concentrating to obtain crude product, recrystallizing with toluene to obtain product H2 (6.7 g) with purity>99% and yield 80%.
The compound H2 was subjected to nuclear magnetic detection and the data was resolved as follows:
1HNMR(300MHz，CDCl3)δ8.55(d，1H)，δ8.22(s，1H)δ8.20(d，1H)，δ7.94～7.86(m，5H)，δ7.75～7.73(m，3H)，δ7.62～7.28(m，25H)，δ7.16(m，2H),δ1.69(s，6H)。
example 4
This example provides an organic electroluminescent compound H5, which has the following structure:
the preparation method of the H5 comprises the following steps:
(1) synthesis of M-1-1:
the same as in example 2.
(2) Synthesis H5:
to a 50ml three-necked flask, M-1-1(5.6g, 0.01mol) and N- [1,1' -biphenyl-4-yl were added]-dibenzo [ b, d ]]Thiophene-3-amine (3.5g, 0.01mol), toluene (100 ml) was added, and sodium tert-butoxide (1.2g, 0.013mol), Pd were added with stirring2(dba)3(0.046g, 0.00005mol), replacing nitrogen, adding 0.2g of tri-tert-butylphosphine 10% toluene solution, starting heating, slowly heating to 80 ℃ (keeping nitrogen protection in the reaction process), reacting for 2 hours, and detecting by HPLC (M-1)<1 percent), stopping the reaction and cooling to room temperature. After the reaction is finished, cooling to 25 ℃, washing with salt water for 2 times, adding anhydrous sodium sulfate into the organic phase, and drying; performing column chromatography with toluene as eluent; concentrating to obtain crude product, recrystallizing with toluene to obtain product H5 6.6g with purity>99% and yield 80%.
The compound H5 was subjected to nuclear magnetic detection and the data was resolved as follows:
1HNMR(300MHz，CDCl3)δ8.55(d，1H)，δ8.45(d，1H),δ8.22(s，1H)δ8.20(d，1H)，δ8.01(d，1H),δ7.94～7.89(m，4H)，δ7.75～7.73(m，3H)，δ7.62～7.28(m，25H)，δ7.16(t，1H)。
example 5
This example provides an organic electroluminescent compound H8, which has the following structure:
the preparation method of the H8 comprises the following steps:
(1) synthesis of M-1-1:
the same as in example 2.
(2) Synthesis H8:
to 250ml of threeInto a mouth bottle, M-1-1(5.6g, 0.01mol) and N- (dibenzo [ b, d ] were added]Thien-3 yl) dibenzo [ b, d]Furan-3-amine (3.65g, 0.01mol), toluene (100 ml) and sodium tert-butoxide (1.2g, 0.013mol), Pd were added with stirring2(dba)3(0.046g, 0.00005mol), replacing nitrogen, adding 0.2g of tri-tert-butylphosphine 10% toluene solution, starting heating, slowly heating to 80 ℃ (keeping nitrogen protection in the reaction process), reacting for 2 hours, and detecting by HPLC (M-1)<1 percent), stopping the reaction and cooling to room temperature. After the reaction is finished, cooling to 25 ℃, washing with salt water for 2 times, adding anhydrous sodium sulfate into the organic phase, and drying; performing column chromatography with toluene as eluent; concentrating to obtain crude product, recrystallizing with toluene to obtain product H8 6.6g with purity>99%, yield: 80 percent.
The compound H8 was subjected to nuclear magnetic detection and the data was resolved as follows:
1HNMR(300MHz，CDCl3)δ8.55(d，1H)，δ8.22(s，1H)δ8.20(d，1H)，δ8.01～7.80(m，9H),δ7.73(s，1H)，δ7.62～7.28(m，20H)，δ7.16(t，1H),δ6.91(d，2H)。
example 6
This example provides an organic electroluminescent compound H17, which has the following structure:
the preparation method of the H17 comprises the following steps:
(1) synthesis of M-1-1:
the same as in example 2.
(2) Synthesis H17:
to a 250ml three-necked flask, M-1-1(5.6g, 0.01mol) and N- [1,1' -biphenyl-2-yl ] were added]-dibenzo [ b, d ]]Thiophene-3-amine (3.5g, 0.01mol), toluene (100 ml) was added, and sodium tert-butoxide (1.2g, 0.013mol), Pd were added with stirring2(dba)3(0.046g、000005mol), replacing nitrogen, adding 0.2g of tri-tert-butylphosphine 10% toluene solution, starting heating, slowly heating to 80 ℃ (keeping nitrogen protection in the reaction process), reacting for 2 hours, and detecting by HPLC (M-1)<1 percent), stopping the reaction and cooling to room temperature. After the reaction is finished, cooling to 25 ℃, washing with salt water for 2 times, adding anhydrous sodium sulfate into the organic phase, and drying; performing column chromatography with toluene as eluent; concentrating to obtain crude product, recrystallizing with toluene to obtain product H17 6.6g with purity>99% and yield 80%.
The compound H17 was subjected to nuclear magnetic detection and the data was resolved as follows:
1HNMR(300MHz，CDCl3)δ8.55(d，1H)，δ8.45(d，1H),δ8.22(s，1H)δ8.20(d，1H)，δ8.10(d，1H),δ8.01(d，1H),δ7.94～7.89(m，4H)，δ7.73(s，1H)，δ7.62～7.27(m，23H)，δ7.35～7.08(m，4H)。
application example 1
The application example provides an OLED device, and the preparation method of the OLED device comprises the following steps:
(1) a transparent electrode Indium Tin Oxide (ITO) film (15 Ω/sq, Samsung Corning, Samsung) on a glass substrate for an Organic Light Emitting Diode (OLED) device was sequentially ultrasonically cleaned with trichloroethylene, acetone, ethanol, and distilled water, and then stored in isopropyl alcohol; and mounting the ITO substrate on a substrate clamp of vacuum vapor deposition equipment.
(2) The compound HIL was introduced into the chamber of a vacuum vapor deposition apparatus, and then the chamber pressure of the apparatus was controlled to reach 10 deg.C-6And applying a current to the chamber to evaporate the introduced substances, thereby forming a hole injection layer having a thickness of 60nm on the ITO substrate.
(3) The organic electroluminescent compound H1 provided by the present invention was introduced into another chamber of a vacuum vapor deposition apparatus, and evaporation was performed by applying a current to the chamber, thereby forming a hole transport layer having a thickness of 20nm on the hole injection layer.
(4) Introducing compound CBP into one chamber of a vacuum vapor deposition apparatus as a host material and compound D-1 into the other chamber as a dopant; the two materials were evaporated at different rates and deposited at a doping amount of 15 wt% (based on the total weight of the host material and the dopant) to form a light-emitting layer having a thickness of 30nm on the hole transport layer.
(5) Introducing compound ETL into one chamber and 8-hydroxyquinolinolato lithium (lithium quinolate) into the other chamber; both materials were evaporated at the same rate and deposited at doping amounts of 50 wt%, respectively, to form an electron transport layer having a thickness of 30nm on the light emitting layer.
(6) 8-hydroxyquinolinolato lithium with a thickness of 2nm was deposited on the electron transport layer as an electron injection layer EIL.
(7) Depositing an Al cathode with the thickness of 150nm on the electron injection layer by another vacuum vapor deposition device; and obtaining the OLED device.
All materials described above for the preparation of OLED devices were used by placing 10 a-6Purification was performed by vacuum sublimation under torr conditions.
Application example 2
The present application example provides an OLED device, which is different from application example 1 in that: h1 in step (3) is replaced by H2.
Application example 3
The present application example provides an OLED device, which is different from application example 1 in that: h1 in step (3) is replaced by H4.
Application example 4
The present application example provides an OLED device, which is different from application example 1 in that: h1 in step (3) is replaced by H5.
Application example 5
The present application example provides an OLED device, which is different from application example 1 in that: h1 in step (3) is replaced by H7.
Application example 6
The present application example provides an OLED device, which is different from application example 1 in that: h1 in step (3) is replaced by H8.
Application example 7
The present application example provides an OLED device, which is different from application example 1 in that: h1 in step (3) is replaced by H13.
Application example 8
The present application example provides an OLED device, which is different from application example 1 in that: h1 in step (3) is replaced by H20.
Comparative example 1
The present comparative example provides an OLED device, which is different from application example 1 in that: h1 in step (3) was replaced with HTL.
Performance testing of OLED devices
The OLED-1000 multichannel accelerated aging life and light color performance analysis system produced in Hangzhou distance is used for testing the LT90 of the driving voltage, the current efficiency and the life of the OLED device provided in application examples 1-8 and comparative example 1; here, LT90 indicates the time required for the luminance to decrease to 90% of the original luminance with the current density kept constant.
The specific test results are shown in table 1:
TABLE 1
As can be seen from table 1, the organic electroluminescent compounds according to the present invention have superior properties compared to the organic electroluminescent compounds of the prior art, and thus the organic electroluminescent device provided by the present invention has high luminous efficiency and long operating life; also, the organic electroluminescent device requires a low driving voltage, thereby improving power efficiency and power consumption.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (10)
1. An organic electroluminescent compound intermediate characterized by having a structure represented by the formula M-1:
2. the method for preparing an organic electroluminescent compound intermediate according to claim 1, wherein the synthetic route is as follows:
the method specifically comprises the following steps:
(1) taking a compound IM-01 as a raw material, and carrying out a coupling reaction with o-nitrobenzeneboronic acid under the action of a catalyst to obtain a compound IM-02;
(2) performing a closed-loop reaction on the compound IM-02 under the action of a catalyst to obtain an organic electroluminescent compound intermediate with a structure shown as a formula M-1;
preferably, in step (1), the catalyst is a palladium catalyst; and/or, in step (2), the catalyst is a phosphine catalyst;
more preferably, in step (1), the catalyst is palladium tetratriphenylphosphine; and/or, in the step (2), the catalyst is triphenylphosphine.
3. An organic electroluminescent compound having a structure represented by formula I:
wherein Ar is1、Ar2、Ar3Each independently represents a group having C6～C60Aromatic or C6～C60Of (a) a heteroaromatic compoundAn aromatic ring system.
4. The organic electroluminescent compound according to claim 3, wherein Ar is Ar1、Ar2、Ar3Each independently represents benzene, biphenyl, naphthalene, phenanthrene, fluorene, spirobifluorene, dibenzofuran or dibenzothiophene.
5. The organic electroluminescent compound of claim 3 or 4, wherein the organic electroluminescent compound is selected from one or more of the formulae H1 to H20:
6. the method for producing an organic electroluminescent compound according to any one of claims 3 to 5, comprising the steps of:
(1) to be provided with
As a raw material, with Ar1-X is subjected to a coupling reaction under the action of a catalyst to obtain
(2) To be provided with
As a raw material, with
Carrying out coupling reaction under the action of a catalyst to obtain
Wherein, X represents halogen;
Ar1、Ar2、Ar3each independently having the same limitations as claim 3.
7. The production method according to claim 6, wherein in the step (1), the catalyst is a copper catalyst; preferably cuprous iodide;
and/or, in the step (2), the catalyst is a palladium catalyst; preferably Pd2(dba)3；
And/or, X represents I.
8. A hole transport layer for an OLED device, comprising the organic electroluminescent compound according to any one of claims 3 to 5.
9. An OLED device comprising an anode, a cathode, and at least one organic thin film layer between the anode and the cathode; the organic thin film layer comprises a hole transport layer and any one or the combination of at least two of a hole injection layer, an electron blocking layer, a hole blocking layer, a light emitting layer, an electron transport layer and an electron injection layer;
the hole transport layer is the hole transport layer for the OLED device of claim 8.
10. An electronic device, characterized in that it comprises an OLED device as claimed in claim 9.
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