CN114920748A - Organic compound and application thereof in OLED (organic light emitting diode) device - Google Patents
Organic compound and application thereof in OLED (organic light emitting diode) device Download PDFInfo
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- CN114920748A CN114920748A CN202210621667.8A CN202210621667A CN114920748A CN 114920748 A CN114920748 A CN 114920748A CN 202210621667 A CN202210621667 A CN 202210621667A CN 114920748 A CN114920748 A CN 114920748A
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Classifications
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/16—Peri-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/16—Peri-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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Abstract
The invention provides an organic compound and application thereof, wherein the organic compound has a structure shown in a formula I. According to the organic compound provided by the invention, a large conjugated structure containing heteroatoms is introduced, and lone-pair electrons in nitrogen atoms are conjugated to a benzene ring, so that the charge transfer balance of material molecules is improved, and the stability of the material is improved. The organic compound can be used as a luminescent layer material, and can improve the luminescent efficiency and the service life of the prepared electroluminescent device by matching with other proper materials, thereby providing a solution of the luminescent device with low manufacturing cost, high efficiency and long service life.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to an organic compound and application thereof in an OLED device.
Background
Organic semiconductor materials have structural diversity, low cost, and excellent optoelectronic properties, especially Organic Light Emitting Diodes (OLEDs) have great potential and space for applications in optoelectronic devices such as flat panel displays and lighting. At present, a mixed system of a host material/a dopant is generally used as a luminescent material in a luminescent layer of an organic electroluminescent device, so that color purity, luminous efficiency and stability can be improved. Generally, with a host material/dopant system, the choice of host material is critical because the host material greatly affects the efficiency and stability of the OLED device. The preferred host material should have a suitable molecular weight for deposition under vacuum, while also having a high glass transition temperature and thermal decomposition temperature to ensure thermal stability, high electrochemical stability to ensure long lifetime, easy formation of amorphous thin film, good interfacial effect with adjacent functional layer materials, and low tendency to molecular motion. Particularly, as a red light host material, the material is required to have good carrier transport capability and appropriate triplet state energy level, so that energy can be effectively transferred to a guest material in the light emitting process, and higher efficiency is realized.
The red host materials reported at present are generally aromatic rings with large conjugated systems, and generally show the problems of low device efficiency and poor stability in terms of devices. This is because the triplet level due to the larger conjugated structure is lower, and the exciton energy cannot be efficiently transferred to the guest, while the balance problem of carrier transport of the host material in the device is ignored.
Disclosure of Invention
In view of the above, the present invention provides an organic compound and an application thereof in an OLED device, which can effectively improve the efficiency and lifetime of the device.
The invention provides an organic compound, which has a structure shown in a formula I:
wherein A, B, C is independently selected from substituted or unsubstituted aryl of C6-C30, heteroaryl of C5-C30, and the C ring contains at least one electron-withdrawing group;
l is selected from single bond, substituted or unsubstituted arylene of C6-C30, heteroarylene of C2-C30, alicyclic ene of C3-C30 and combination of the above components;
R 1 selected from H, D, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, Cl, Br, F, I, substituted or unsubstituted straight chain alkyl, alkoxy, thioalkoxy, silyl or keto of C1-C20, substituted or unsubstituted branched alkyl, cycloalkyl of C3-C20, substituted or unsubstituted alkoxycarbonyl of C2-C20, substituted or unsubstituted aryloxycarbonyl of C7-C20, substituted or unsubstituted aromatic or heteroaromatic group having 5-60 ring atoms, aryloxy or heteroaryloxy group having 5-60 ring atoms or a combination thereof;
n is an integer of 0 to 6, and when n is 2 to 6, it represents that there may be a plurality of the same or different R 1 Exist and are adjacent to two R 1 May be fused to form a ring.
The invention provides an organic light-emitting device which comprises an anode, a cathode and an organic thin film layer positioned between the anode and the cathode, wherein the organic thin film layer comprises a light-emitting layer, and the light-emitting layer contains at least one organic compound.
The invention provides a display panel comprising the organic light-emitting device.
Compared with the prior art, the invention provides an organic compound with a structure shown in a formula I. According to the organic compound provided by the invention, a large conjugated structure containing heteroatoms is introduced, and lone-pair electrons in nitrogen atoms are conjugated to a benzene ring, so that the charge transfer balance of material molecules is improved, and the stability of the material is improved. The organic compound can be used as a luminescent layer material, and can improve the luminescent efficiency and the service life of the prepared electroluminescent device by matching with other proper materials, thereby providing a solution of the luminescent device with low manufacturing cost, high efficiency and long service life.
Drawings
FIG. 1 is a schematic structural diagram of an OLED device provided by the present invention;
wherein 110 is a glass substrate, 120 is an anode, 130 is a hole injection layer, 140 is a hole transport layer A, 150 is a hole transport layer B; 160 is a light emitting layer, 170 is an electron transport layer, and 180 is a cathode.
Detailed Description
The invention provides an organic compound, which has a structure shown in a formula I:
wherein A, B, C is independently selected from substituted or unsubstituted aryl of C6-C30, heteroaryl of C5-C30, and the C ring contains at least one electron-withdrawing group;
l is selected from single bond, substituted or unsubstituted arylene of C6-C30, heteroarylene of C2-C30, cycloaliphatic of C3-C30 and combination of the above;
R 1 selected from H, D, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, Cl, Br, F, I, substituted or unsubstituted straight chain alkyl, alkoxy, thioalkoxy, silyl or keto of C1-C20, substituted or unsubstituted branched alkyl, cycloalkyl of C3-C20, substituted or unsubstituted alkoxycarbonyl of C2-C20, substituted or unsubstituted aryloxycarbonyl of C7-C20, substituted or unsubstituted aromatic or heteroaromatic group having 5-60 ring atoms, aryloxy or heteroaryloxy group having 5-60 ring atoms or a combination thereof;
n is an integer of 0 to 6, and when n is 2 to 6, it represents that there may be a plurality of the same or different R 1 Exist and are adjacent to two R 1 May be fused to form a ring.
In the present invention, the aryl group having 6 to 30 includes monocyclic and fused ring aryl groups.
In the present invention, the above-mentioned heteroaryl group having C5 to C30 includes a monocyclic or fused ring heteroaryl group.
In the present invention, the above combination refers to a group in which groups are connected by a single bond, a C atom or a hetero atom (including but not limited to N, O, S, P, Si) or a group in which groups are fused.
In the present invention, C6-C30 each independently may be C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, or the like.
In the present invention, C5-C30 each independently may be C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, or the like.
In the present invention, C3 to C30 may each independently be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, or the like.
In the present invention, C2-C30 may each independently be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, or the like.
In the present invention, C1-C20 may each independently be C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20.
In the present invention, C3-C20 may each independently be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20.
In the present invention, C2-C20 may each independently be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20.
In the present invention, C7-C20 may each independently be C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20.
Optionally, said A, B, C, L, R 1 Wherein the substituents are independently selected from deuterium, halogen, cyano, C1-C10 linear or branched alkyl, C1-C10 alkoxy, C1-C10 alkylthio, C6-C20 aryl, C2-C20 heteroaryl or C3524 heteroaryl6-C18 arylamine group.
Optionally, said A, B, C, L, R 1 The substituent(s) in (b) is (are) independently one or more selected from deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, fluorenyl, 9 '-dimethylfluorenyl, 9' -diphenylfluorenyl, spirobifluorenyl, pyridyl, deuterated phenyl and cyanophenyl.
The above groups may be further substituted with one or more of deuterium, cyano, halogen.
Optionally, the aryl group of C6 to C30 is selected from any one of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, fluorenyl, 9 '-dimethylfluorenyl, 9' -diphenylfluorenyl, spirobifluorenyl, benzocyclopentenyl, and benzocyclohexenyl.
Optionally, the heteroaryl group of C5-C30 is selected from carbazolyl, triazinyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, imidazolyl, oxazolyl, thiazolyl, pyranyl, furanyl, pyrrolyl, thienyl, benzofuranyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzothienyl, dibenzothienyl, dibenzofuranyl, naphthopyridyl, naphthopyrazinyl, naphthoimidazolyl, naphthooxazolyl, naphthothiazolyl, phenanthropyridyl, phenanthropyrazinyl, phenanthroimidazolyl, phenanthrooxazolyl, phenanthrothiazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, 1, 5-naphthyridinyl, acridinyl, indolocarbazolyl, indolofluorenyl, benzothiophenopyrimidyl, benzofuropyrazinyl, benzofuropyrimidinyl, benzofurocarbazolyl carbazolyl, diazo, Any one of benzothienocarbazolyl, indolopyrazinyl, indolopyrimidinyl, indenopyrazinyl, or indenopyrimidinyl.
Optionally, the arylene group of C6 to C30 is selected from any one of phenylene, biphenylene, terphenylene, naphthylene, anthracenylene, phenanthrenylene, pyrenylene, fluorenylene, 9 '-dimethylfluorenyl, 9' -diphenylfluorenyl, spirobifluorenylene, benzocyclopentenylene, and benzocyclohexenylene.
Optionally, the heteroarylene group of C2-C30 is selected from the group consisting of carbazolyl, triazinylene, pyridinylene, pyrimidinylene, pyrazinylene, pyridazinylene, imidazolyl, oxazolylene, thiazolyl, pyranylene, furanylene, pyrrolylene, thiophenylene, benzofuranylene, benzimidazolylene, benzoxazolyl, benzothiazolyl, benzothiophenylene, dibenzothienyl, dibenzofuranylene, naphthopyridyl, naphthopyrazinylene, naphthoimidazolyl, naphthooxazolylene, naphthothiazolyl, phenanthropyridinylene, phenanthropyrazinylene, phenanthroimidazolylene, phenanthrooxazolyl, phenanthrothiazolylene, quinolinylene, isoquinolinyl, quinoxalylene, quinazolinylene, 1, 5-naphthyridine, acridinylene, indolocarbazolylene, indolofluorenyl, indolylenylene, phenanthrenefluorenyl, Any one of a benzothienopyrazinyl group, a benzothienopyrimidinyl group, a benzofuropyrazinyl group, a benzofuropyrimidinyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, an indolopyrazinyl group, an indolopyrimidinyl group, an indenopyrazinyl group, or an indenopyrimidinyl group.
Optionally, A, B, C is independently selected from Ry1 substituted or unsubstituted phenyl, pyrrolyl, furanyl, thienyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, quinoxalinyl, isoquinolinyl, quinazolinyl, 1, 5-naphthyridinyl, anthracyl, phenanthrenyl, pyrenyl, acridinyl, carbazolyl, fluorenyl, benzofuranyl, benzocyclopentenyl, benzocyclohexenyl, dibenzofuranyl, dibenzothienyl, or any of the following structures:
the Ry1 is one or more selected from deuterium, halogen, cyano, C6-C20 aryl or C2-C20 heteroaryl, and the C ring contains at least one electron-withdrawing group.
Optionally, A, B is independently selected from substituted or unsubstituted phenyl, naphthyl, pyrrolyl, furyl, thienyl, biphenyl, benzofuryl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzothienyl, benzocyclopentenyl, or benzocyclohexenyl;
the A, B substituents are independently selected from phenyl, naphthyl or biphenyl.
Optionally, the electron-withdrawing group in C is selected from one or more of F, Cl, Br, I, cyano.
Optionally, C has any one of the following structures:
wherein m is 1, 2 or 3; x 1 -X 8 Selected from the group consisting of CR 8 Or N, and at least one is N, while any two adjacent positions may form a mono-or polycyclic aliphatic or aromatic ring system; m 1 、M 2 、M 3 Each independently represents N (R) 9 )、C(R 10 ) 2 、Si(R 11 ) 2 、O、C＝N(R 12 )、C＝C(R 13 ) 2 、P(R 14 )、P(＝O)R 15 、S、S＝O、SO 2 Or a single bond;
R 2 ～R 15 independently selected from H, D, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, Cl, Br, F, I, substituted or unsubstituted C1-C20 straight chain alkyl, alkoxy, thioalkoxy, silyl or keto, substituted or unsubstituted C3-C20 branched chain alkyl, cycloalkyl, substituted or unsubstituted C2-C20 alkoxycarbonyl, substituted or unsubstituted C7-C20 aryloxycarbonyl, substituted or unsubstituted aromatic or heteroaromatic group having 5-60 ring atoms, aryloxy or heteroaryloxy group having 5-60 ring atoms or a combination thereof.
Optionally, L is selected from a single bond, a substituted or unsubstituted monocyclic aryl group, a monocyclic heteroaryl group, 2-3 ring-fused ring aryl groups, 2-3 ring-fused ring heteroaryl groups; optionally, the monocyclic aryl is selected from phenyl; optionally, the rings forming the fused ring aryl are phenyl; alternatively, the ring forming the fused ring heteroaryl includes at least one monocyclic heteroaryl group, including but not limited to pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, pyrrolyl, furanyl, thienyl, pyrazolyl, thiazolyl, oxazolyl; optionally, the ring forming the fused ring heteroaryl further comprises 1 or 2 phenyl groups.
Optionally, L is selected from a single bond, substituted or unsubstituted phenyl, triazinyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, imidazolyl, oxazolyl, thiazolyl, pyranyl, furanyl, pyrrolyl, thienyl, benzofuranyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzothienyl, dibenzothienyl, or dibenzofuranyl.
Optionally, the organic compound has any one of the following structures:
the invention provides an organic light-emitting device which comprises an anode, a cathode and an organic thin film layer positioned between the anode and the cathode, wherein the organic thin film layer comprises a light-emitting layer, and the light-emitting layer contains at least one organic compound.
Optionally, the organic compound is used as a red host material.
The invention provides a display panel comprising the organic light-emitting device.
The organic light-emitting device provided by the invention can be an organic light-emitting device well known to those skilled in the art, and optionally comprises a substrate, an ITO anode, a first hole transport layer, a second hole transport layer, an electron blocking layer, a light-emitting layer, a first electron transport layer, a second electron transport layer, a cathode (a magnesium-silver electrode, the mass ratio of magnesium to silver is 1:9) and a capping layer (CPL).
In the invention, the anode material of the organic light-emitting device can be selected from metal-copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum and the like and alloys thereof; such as metal oxide-indium oxide, zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), etc.; such as conductive polymers-polyaniline, polypyrrole, poly (3-methylthiophene), and the like, in addition to the above materials that facilitate hole injection and combinations thereof, include known materials suitable for use as anodes.
In the invention, the cathode material of the organic light-emitting device can be selected from metal-aluminum, magnesium, silver, indium, tin, titanium and the like and alloys thereof; such as multi-layer metal material-LiF/Al, LiO 2 /Al、BaF 2 Al, etc.; in addition to the above materials and combinations thereof that facilitate electron injection, known materials suitable for use as cathodes are also included.
In an alternative embodiment of the present invention, the organic optoelectronic device, for example, the organic thin film layer in the organic light emitting device, has at least one light emitting layer (EML), and may further include other functional layers, including a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), a Hole Blocking Layer (HBL), an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL).
In an alternative embodiment of the present invention, the organic light emitting device is prepared according to the following method:
an anode is formed on a transparent or opaque smooth substrate, an organic thin layer is formed on the anode, and a cathode is formed on the organic thin layer.
Alternatively, the organic thin layer may be formed by a known film forming method such as evaporation, sputtering, spin coating, dipping, ion plating, or the like.
The invention provides a display device which comprises the display panel.
In the present invention, an organic light emitting device (OLED device) may be used in a display device, wherein the organic light emitting display device may be a display screen of a mobile phone, a display screen of a computer, a display screen of a television, a display screen of a smart watch, a display panel of a smart car, a display screen of a VR or AR helmet, a display screen of various smart devices, and the like.
The following description will be clearly and completely described in conjunction with the technical solutions of the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without making any creative effort based on the embodiments in the present invention, belong to the protection scope of the present invention.
Example 1
Under nitrogen atmosphere, raw material A (18g), raw material B (25g), palladium chloride (0.5g), copper acetate (2.5g) and ferric trichloride (1.5g) are sequentially added into a 1000mL three-mouth reaction flask, then 500mL DMF is injected into the flask and vacuumized, nitrogen is replaced for three times, the flask is heated to 120 ℃ for reaction for 8 hours, after the reaction is finished, the solvent is removed by rotary evaporation and is extracted for three times by dichloromethane and deionized water, organic phases are combined, and separation and purification are carried out by silica gel column chromatography (eluent is petroleum ether), 30.7g of intermediate 1-1 is obtained, and the yield is 82.6%.
Under a nitrogen atmosphere, intermediate 1-1(29.8g), raw material C (15.2g), tetrakis (triphenylphosphine) palladium (0.8g) and X-phos (0.8) were sequentially added to a 1000mL three-necked flask, then 500mL of dried toluene was charged into the flask and evacuated, nitrogen was substituted three times, the flask was heated to 110 ℃ for reflux reaction for 12 hours, after completion of the reaction, the reaction mixture was poured into 500mL of deionized water and rapidly stirred while the product was continuously precipitated, after suction filtration, the product was dissolved again with dichloromethane and extracted three times with saturated brine, the organic phases were combined and subjected to silica gel column chromatography purification (eluent dichloromethane: petroleum ether 1:20) to obtain 28.4g of intermediate 1-2 with a yield of 81.2%.
Under a nitrogen environment, sequentially adding the intermediate 1-2(26.2g) and sodium tert-butoxide (44g) into a 500mL three-neck flask, then injecting 200mL of dry toluene into the flask, vacuumizing, replacing with nitrogen for three times, heating to 110 ℃, refluxing and reacting for 12 hours, pouring the reaction mixture into 500mL of deionized water after the reaction is finished, rapidly stirring while continuously precipitating the product, dissolving the product with dichloromethane again after suction filtration, extracting with saturated saline for three times, and separating and purifying the combined organic phases by silica gel column chromatography (eluent dichloromethane: petroleum ether is 1:20) to obtain 17.6g of the intermediate 1-3 with the yield of 70.3%.
Under the nitrogen environment, sequentially adding the intermediate 1-3(10.5g), the raw material D (9.7g), palladium trifluoroacetate (0.35g) and cesium carbonate (12g) into a 500mL three-neck flask, then injecting 200mL of dry toluene into the flask, vacuumizing and replacing with nitrogen for three times, heating to 110 ℃ for reflux reaction for 12 hours, pouring the reaction mixture into 500mL of deionized water after the reaction is finished, rapidly stirring while continuously precipitating the product, dissolving the product with dichloromethane after suction filtration, extracting with saturated saline for three times, combining organic phases, and separating and purifying by silica gel column chromatography (eluent dichloromethane: petroleum ether is 1:20) to obtain 13.3g of solid powder, namely the compound 1, wherein the yield is 73.4%. MS [ M + H ]] + calcd for C 53 H 32 N 4 :724.26,found:724.16.Elem.Anal.:C,87.82；H,4.43；N,7.72。
Example 2
Under nitrogen atmosphere, raw material A (18g), raw material B (25g), palladium chloride (0.5g), copper acetate (2.5g) and ferric trichloride (1.5g) are sequentially added into a 1000mL three-mouth reaction flask, then 500mL DMF is injected into the flask and vacuumized, nitrogen is replaced for three times, the flask is heated to 120 ℃ for reaction for 8 hours, after the reaction is finished, the solvent is removed by rotary evaporation and is extracted by dichloromethane and deionized water for three times, organic phases are combined, and separation and purification are carried out by silica gel column chromatography (eluent is petroleum ether), 31.3g of intermediate 2-1 is obtained, and the yield is 84.2%.
Intermediate 2-1(29.8g), raw material C (15.2g), tetrakis (triphenylphosphine) palladium (0.8g) and X-phos (0.8) were sequentially added to a 1000mL three-necked flask under a nitrogen atmosphere, then 500mL of dried toluene was charged into the flask and evacuated, nitrogen was substituted three times, the flask was heated to 110 ℃ for reflux reaction for 12 hours, after completion of the reaction, the reaction mixture was poured into 500mL of deionized water and stirred rapidly while the product was continuously precipitated, after suction filtration, the product was dissolved again with dichloromethane and extracted three times with saturated brine, the organic phases were combined and subjected to silica gel column chromatography purification (eluent dichloromethane: petroleum ether: 1:20) to obtain 27.9g of intermediate 2-2 with a yield of 79.8%.
Under nitrogen atmosphere, sequentially adding the intermediate 2-2(26.2g) and sodium tert-butoxide (44g) into a 500mL three-neck flask, then injecting 200mL of dry toluene into the flask and vacuumizing, replacing with nitrogen for three times, heating to 110 ℃ for reflux reaction for 12 hours, pouring the reaction mixture into 500mL of deionized water after the reaction is finished, rapidly stirring while continuously precipitating the product, dissolving the product with dichloromethane again after suction filtration and extracting with saturated saline for three times, and separating and purifying the combined organic phases by silica gel column chromatography (eluent dichloromethane: petroleum ether ═ 1:20) to obtain 18.6g of the intermediate 2-3 with the yield of 74.5%.
Under a nitrogen environment, sequentially adding the intermediate 2-3(10.5g), the raw material D (9.7g), palladium trifluoroacetate (0.35g) and cesium carbonate (12g) into a 500mL three-neck flask, then injecting 200mL of dry toluene into the flask, vacuumizing and replacing nitrogen for three times, heating to 110 ℃ for reflux reaction for 12 hours, pouring the reaction mixed solution into 500mL of deionized water after the reaction is finished, rapidly stirring while continuously precipitating the product, performing suction filtration, dissolving the product with dichloromethane again, extracting with saturated saline for three times, and performing silica gel column chromatography separation and purification on the combined organic phases (eluent dichloromethane, petroleum ether is 1:20) to obtain 12.7g of solid powder, namely the compound 2, wherein the yield is 70.1%. MS [ M + H ]] + calcd for C 53 H 32 N 4 :724.26,found:724.38.Elem.Anal.:C,87.82；H,4.45；N,7.72。
Example 3
Under a nitrogen environment, raw material A (18g), raw material B (25g), palladium chloride (0.5g), copper acetate (2.5g) and ferric trichloride (1.5g) are sequentially added into a 1000mL three-neck reaction flask, then 500mL DMF is injected into the flask and vacuumized, replaced by nitrogen for three times, heated to 120 ℃ for reaction for 8 hours, after the reaction is finished, the solvent is removed by rotary evaporation and extracted by dichloromethane and deionized water for three times, organic phases are combined, and separation and purification are carried out by silica gel column chromatography (an eluent is petroleum ether), so that 30.7g of intermediate 3-1 is obtained, and the yield is 82.6%.
Under a nitrogen atmosphere, intermediate 3-1(29.8g), raw material C (15.2g), tetrakis (triphenylphosphine) palladium (0.8g) and X-phos (0.8) were sequentially added to a 1000mL three-necked flask, then 500mL of dried toluene was charged into the flask and evacuated, nitrogen was substituted three times, the flask was heated to 110 ℃ for reflux reaction for 12 hours, after completion of the reaction, the reaction mixture was poured into 500mL of deionized water and rapidly stirred while the product was continuously precipitated, after suction filtration, the product was dissolved again with dichloromethane and extracted three times with saturated brine, the organic phases were combined and subjected to silica gel column chromatography purification (eluent dichloromethane: petroleum ether: 1:20) to obtain 28.4g of intermediate 3-2 with a yield of 81.2%.
Under nitrogen atmosphere, adding the intermediate 3-2(26.2g) and sodium tert-butoxide (44g) into a 500mL three-neck flask in turn, then injecting 200mL of dry toluene into the flask and vacuumizing, replacing with nitrogen for three times, heating to 110 ℃ for reflux reaction for 12 hours, pouring the reaction mixture into 500mL of deionized water after the reaction is finished, rapidly stirring, continuously separating out the product, dissolving the product with dichloromethane again after suction filtration and extracting with saturated saline for three times, and combining the organic phases and separating and purifying by silica gel column chromatography (eluent dichloromethane: petroleum ether ═ 1:20) to obtain 17.6g of the intermediate 3-3 with the yield of 70.3%.
Under nitrogenUnder the environment, sequentially adding the intermediate 3-3(10.5g), the raw material D (7.2g), palladium trifluoroacetate (0.35g) and cesium carbonate (12g) into a 500mL three-neck flask, then injecting 200mL of dry toluene into the flask, vacuumizing and replacing with nitrogen for three times, heating to 110 ℃ for reflux reaction for 12 hours, pouring the reaction mixed solution into 500mL of deionized water after the reaction is finished, rapidly stirring until a product is separated out continuously, performing suction filtration, dissolving the product with dichloromethane again, extracting with saturated saline for three times, and combining organic phases to perform silica gel column chromatography separation and purification (eluent dichloromethane: petroleum ether is 1:20) to obtain 11.7g of solid powder, namely the compound 3, wherein the yield is 75.6%. MS [ M + H ]] + calcd for C 46 H 27 N 3 :621.22,found:621.17.Elem.Anal.:C,87.83；H,4.38；N,6.78。
Comparative examples
(1) Preparation of Compound 4-3
Under the protection of nitrogen, sequentially adding compound 4-1(20.2g,50mmol), compound 4-2(17.2g,100mmol), tetrakis (triphenylphosphine) palladium (3.5g,3mmol), tetrabutylammonium bromide (8.1g,25mmol) and sodium hydroxide (4g,100mmol) into a 500mL three-neck flask, adding 200mL of toluene and 50mL of deionized water, vacuumizing, replacing with nitrogen for three times, heating to 110 ℃, and stirring for reaction for 24 hours; after the reaction was completed, the reaction solution was subjected to rotary evaporation to remove most of the solvent, washed three times with methylene chloride dissolved water, and the combined organic phases were separated and purified by silica gel column chromatography (eluent petroleum ether) to obtain 18.7g of compound 4-3 with a yield of 75%.
(2) Preparation of Compound 4-4
Adding the compound 4-3(14.9g,30mmol) and 100mL of N, N-dimethylformamide into a 250mL single-neck bottle, dropwise adding a N, N-dimethylformamide solution of 30mmol NBS under ice bath, stirring for reaction for 12h in a dark place, finishing the reaction, pouring the reaction solution into 300mL of water, performing suction filtration, and recrystallizing filter residues to obtain 17.3g of the compound 4-4 with the yield of 90%.
(3) Synthesis of Compound N1
Under the protection of nitrogen, compound 4-4(34.4g,20mmol), compound 4-5(11.5g,20mmol), tetrakis (triphenylphosphine) palladium (0.7g,0.6mmol), tetrabutylammonium bromide (3.2g,10mmol) and sodium hydroxide (1.6g,40mmol) were sequentially added to a 500mL three-necked flask, then 200mL of toluene and 50mL of deionized water were injected into the flask and evacuated, nitrogen was substituted three times, the mixture was heated to 110 ℃ for reflux reaction for 12 hours, after completion of the reaction, the solvent was removed by rotary evaporation, then the product was dissolved with dichloromethane, extracted three times with saturated saline, and the combined organic phases were separated and purified by silica gel column chromatography (eluent V dichloromethane: V petroleum ether ═ 1:10) to give 18.7g of comparative compound N1 (solid powder) with a yield of 85%.
Application example 1
The application example provides an OLED device ITO/HI/HI-1/HT-2/EML/ET Liq/Liq/Al, as shown in figure 1, the organic light-emitting device comprises a glass substrate 110, an anode 120, a hole injection layer 130, a hole transport layer A140, a hole transport layer B150, a light-emitting layer 160, an electron transport layer 170 and a cathode 180;
the preparation steps of the OLED device are as follows:
(1) cutting the glass substrate 110 into sizes of 50mm × 50mm × 0.7mm, performing ultrasonic treatment in isopropanol and deionized water for 30min, respectively, and then cleaning by exposure to ozone for about 10 min; mounting the resulting glass substrate with the ITO anode 120 on a vacuum deposition apparatus;
(2) vacuum evaporating a compound HI with the thickness of 30nm on the ITO anode 120 to form a hole injection layer 130;
(3) vacuum evaporating a compound HT-1 with the thickness of 60nm on the hole injection layer 130 to form a hole transport layer A140;
(4) a compound HT-2 is evaporated on the hole transport layer A140 in vacuum with the thickness of 10nm to form a hole transport layer B150;
(5) compound 1 (provided in example 1) and a red guest material RD in a weight ratio of 100:3 were vacuum evaporated on the hole transport layer B150 to a thickness of 40nm as a light emitting layer 160;
(6) vacuum evaporating compounds ET and Liq with the weight ratio of 50:50 on the light-emitting layer 160, wherein the thickness is 30nm, and the compounds ET and Liq are used as an electron transport layer 170;
(6) an aluminum electrode was vacuum-deposited on the electron transport layer 170 to a thickness of 100nm to form a cathode 180.
The structures of the compounds HI, HT-1, HT-2, red guest materials RD, ET and Liq are shown as follows:
application example 2
The present application example provides an OLED device, which differs from application example 1 only in that the organic compound 1 in step (5) is replaced with the organic compound 2 provided in example 2 of the same mass; the other preparation steps are the same.
Application example 3
The present application example provides an OLED device, which differs from application example 1 only in that the organic compound 1 in step (5) is replaced with the organic compound 3 provided in example 3 of the same quality; the other preparation steps are the same.
Comparative application example 1
The present application example provides an OLED device, which differs from application example 1 only in that the organic compound 1 in step (5) is replaced with the same mass of compound N1 provided in comparative example 1; the other preparation steps are the same.
Test example 1
Simulated calculation of Compounds
The simulation calculation method comprises the following steps: by using Density Functional Theory (DFT), aiming at the organic compound provided by the invention, the distribution and energy levels of the molecular front line orbitals HOMO and LUMO are obtained by optimizing and calculating through a Guassian 09 package (Guassian Inc.) under the calculation level of B3LYP/6-31G (d), and meanwhile, the lowest singlet state energy level S1 and the lowest triplet state energy level T1 of the compound molecules are calculated based on time-dependent density functional theory (TD-DFT) simulation, and the results are shown in Table 1:
TABLE 1
Test example 2
Evaluation of the Performance of OLED devices
The test method comprises the following steps: the life test method is used for testing the continuous working time of the device when the luminous brightness of the device is reduced to 95% of the initial value initially under the constant current density corresponding to 1000 nits.
The current efficiency testing method adopts I-V-L testing equipment to measure the current density corresponding to the brightness of 1000nits, and calculates to obtain the current efficiency.
The test results are shown in table 2.
TABLE 2
The above description of the embodiments is only intended to facilitate the understanding of the method of the invention and its core idea. It should be noted that, for those skilled in the art, it is possible to make various improvements and modifications to the present invention without departing from the principle of the present invention, and those improvements and modifications also fall within the scope of the claims of the present invention.
Claims (12)
1. An organic compound having the structure of formula i:
wherein A, B, C is independently selected from substituted or unsubstituted aryl of C6-C30, heteroaryl of C5-C30, and the C ring contains at least one electron-withdrawing group;
l is selected from single bond, substituted or unsubstituted arylene of C6-C30, heteroarylene of C2-C30, cycloaliphatic of C3-C30 and combination of the above;
R 1 selected from H, D, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, Cl, Br, F, I, substituted or unsubstituted straight chain alkyl, alkoxy, thioalkoxy, silyl or keto of C1-C20, substituted or unsubstituted branched alkyl, cycloalkyl of C3-C20, substituted or unsubstituted alkoxycarbonyl of C2-C20, substituted or unsubstituted aryloxycarbonyl of C7-C20, substituted or unsubstituted aromatic or heteroaromatic group having 5-60 ring atoms, aryloxy or heteroaryloxy group having 5-60 ring atoms or a combination thereof;
n is an integer of 0 to 6, and when n is 2 to 6, it represents that there may be a plurality of same or different R' s 1 Exist and are adjacent to two R 1 May be fused to form a ring.
2. The organic compound of claim 1, wherein A, B, C, L, R is the amino acid sequence of 1 The substituent in (A) is independently selected from one or more of deuterium, halogen, cyano, C1-C10 linear chain or branched chain alkyl, C1-C10 alkoxy, C1-C10 alkylthio, C6-C20 aryl, C2-C20 heteroaryl or C6-C18 arylamine.
3. The organic compound of claim 2Article, characterized in that said A, B, C, L, R 1 Wherein the substituents are independently selected from one or more of deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, dibenzofuranyl, dibenzothienyl, carbazolyl, fluorenyl, 9 '-dimethylfluorenyl, 9' -diphenylfluorenyl, spirobifluorenyl, pyridyl, deuterated phenyl and cyanophenyl.
4. The organic compound according to claim 1, wherein the aryl group having 6-30 is selected from any one of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, fluorenyl, 9 '-dimethylfluorenyl, 9' -diphenylfluorenyl, spirobifluorenyl, benzocyclopentenyl and benzocyclohexenyl;
the heteroaryl group of C5-C30 is selected from carbazolyl, triazinyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, imidazolyl, oxazolyl, thiazolyl, pyranyl, furyl, pyrrolyl, thienyl, benzofuranyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzothienyl, dibenzothienyl, dibenzofuranyl, naphthopyridyl, naphthopyrazinyl, naphthoimidazolyl, naphthooxazolyl, naphthothiazolyl, phenanthropyridyl, phenanthropyrazinyl, phenanthroimidazolyl, phenanthrooxazolyl, phenanthrothiazolyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, 1, 5-naphthyridinyl, acridinyl, indolocarbazolyl, indolofluorenyl, benzothiophenopyrazinyl, benzothienopyrimidinyl, benzofuropyrazinyl, benzofuropyrimidinyl, benzofurocarbazolyl, Benzothienocarbazolyl, indolopyrazinyl, indolopyrimidinyl, indenopyrazinyl or indenopyrimidinyl.
5. The organic compound of claim 4, wherein A, B, C is independently selected from Ry1 substituted or unsubstituted phenyl, pyrrolyl, furanyl, thienyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, quinoxalinyl, isoquinolinyl, quinazolinyl, 1, 5-naphthyridinyl, anthracyl, phenanthryl, pyrenyl, acridinyl, carbazolyl, fluorenyl, benzofuranyl, benzocyclopentenyl, benzocyclocyclohexenyl, dibenzofuranyl, dibenzothienyl, or any of the following structures:
the Ry1 is one or more selected from deuterium, halogen, cyano, C6-C20 aryl or C2-C20 heteroaryl, and the C ring contains at least one electron-withdrawing group.
6. The organic compound of claim 5, wherein A, B is independently selected from the group consisting of substituted or unsubstituted phenyl, naphthyl, pyrrolyl, furyl, thienyl, biphenyl, benzofuryl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzothienyl, benzocyclopentenyl, or benzocyclohexenyl;
the A, B substituents are independently selected from phenyl, naphthyl or biphenyl.
7. The organic compound of claim 1 or 5, wherein C has any one of the following structures:
wherein m is 1, 2 or 3; x 1 -X 8 Selected from the group consisting of CR 8 Or N, and at least one is N, while any two adjacent positions may form a mono-or polycyclic aliphatic or aromatic ring system; m 1 、M 2 、M 3 Each independently represents N (R) 9 )、C(R 10 ) 2 、Si(R 11 ) 2 、O、C＝N(R 12 )、C＝C(R 13 ) 2 、P(R 14 )、P(＝O)R 15 、S、S＝O、SO 2 Or a single bond;
R 2 ～R 15 independently selected from H, D, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, Cl, Br, F, I, substituted or unsubstituted C1-C20 straight chain alkyl, alkoxy, thioalkoxy, silyl or keto, substituted or unsubstituted C3-C20 branched chain alkyl, cycloalkyl, substituted or unsubstituted C2-C20 alkoxycarbonyl, substituted or unsubstituted C7-C20 aryloxycarbonyl, substituted or unsubstituted aromatic or heteroaromatic group having 5-60 ring atoms, aryloxy or heteroaryloxy group having 5-60 ring atoms or a combination thereof.
8. The organic compound of claim 1, wherein L is selected from the group consisting of a single bond, substituted or unsubstituted phenyl, triazinyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, imidazolyl, oxazolyl, thiazolyl, pyranyl, furyl, pyrrolyl, thienyl, benzofuranyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzothienyl, dibenzothienyl, or dibenzofuranyl.
9. The organic compound of claim 1, having any one of the following structures:
10. an organic light-emitting device comprising an anode, a cathode, and an organic thin film layer between the anode and the cathode, the organic thin film layer comprising a light-emitting layer containing at least one organic compound according to any one of claims 1 to 9.
11. The organic light-emitting device according to claim 10, wherein the organic compound is used as a red host material.
12. A display panel comprising the organic light emitting device according to any one of claims 10 to 11.
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