CN116514778A - Organic electronic transmission material and organic electroluminescent device - Google Patents

Organic electronic transmission material and organic electroluminescent device Download PDF

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CN116514778A
CN116514778A CN202310757916.0A CN202310757916A CN116514778A CN 116514778 A CN116514778 A CN 116514778A CN 202310757916 A CN202310757916 A CN 202310757916A CN 116514778 A CN116514778 A CN 116514778A
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organic
layer
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electron transport
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王志恒
李雨康
梁洁
毕海
王悦
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Ji Hua Laboratory
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    • 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
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Abstract

The invention relates to the technical field of organic materials, and discloses an organic electronic transmission material and an organic electroluminescent device, wherein the organic electronic transmission material comprises an organic material layerThe molecular structural formula of the electron transport material is shown as follows:and. The organic electronic transmission material provided by the invention is a benzocinnamine organic compound, wherein the benzocinnamine is used as an electron-absorbing group with electron transmission property, and the electron-deficient group with electron transmission property is matched to construct the organic material with lower LUMO energy level, so that the energy level matching property between an electron injection layer and an electron transmission layer can be improved, and the driving voltage of an organic electroluminescent device is reduced; furthermore, the organic electronic transmission material can be matched with n-type dopants such as alkali metal or compounds thereof or air stability transition metal to form stable metal-organic complex, and the metal-organic complex can be used as an electronic transmission layer material to reduce the driving voltage of the organic electroluminescent device, enhance the luminous efficiency and prolong the service life of the organic electroluminescent device.

Description

Organic electronic transmission material and organic electroluminescent device
Technical Field
The invention relates to the technical field of organic materials, in particular to an organic electronic transmission material and an organic electroluminescent device.
Background
The structure of an Organic Light Emitting Diode (OLED) mainly comprises a glass substrate, positive and negative electrodes and a plurality of organic functional layers of stacked film structures sandwiched between the positive and negative electrodes. And applying proper voltage to the two ends of the electrode, generating holes and electrons at the two ends of the electrode, driving by an electric field to enable the holes and the electrons to be respectively injected into the organic functional layer from the two ends of the electrode, transmitting the holes and the electrons through the organic functional layer, enabling the holes and the electrons to reach the light-emitting layer, recombining the holes and the electrons into high-energy excitons, and then enabling the excitons to fade and radiate photons to emit light. The OLED is a semiconductor display device that generates electroluminescence by using a multi-film layer structure, and is characterized in that compared with the traditional display device, the OLED is light and thin in material, high in brightness, low in power consumption, high in definition, good in flexibility, and the like, the OLED can realize diversified device structural design, and most of the display elements are widely applied to information display, intelligent wearing, automobile electronics, and other devices.
The material properties determine the device performance, especially for organic transport functional layer materials in OLED devices, and it has been found that hole transport materials have three times their mobility for carriers compared to electron transport materials. In order to increase the electroluminescent efficiency of Organic Light Emitting Diodes (OLEDs), it is particularly important to find electron transport materials that are high mobility and stable. Accordingly, the prior art is still in need of improvement and development.
Disclosure of Invention
In view of the above-mentioned shortcomings of the prior art, the present invention aims to provide an organic electron transport material and an organic electroluminescent device, which aim to solve the problems of high driving voltage and low luminous efficiency of the organic electroluminescent device caused by poor electron mobility and stability of the existing electron transport material.
The technical scheme of the invention is as follows:
in a first aspect, an organic electronic transmission material is provided, wherein the molecular structural formula of the organic electronic transmission material is as follows:
and->Wherein m and n represent integers; l (L) 1 Is a linear bond or one of the following linking groups: a substituted or unsubstituted C6 to C60 arylene, a substituted or unsubstituted C2 to C60 heteroarylene, a substituted or unsubstituted C10 to C60 arylene fused ring, a substituted or unsubstituted C10 to C60 heteroarylene fused ring; z is Z 1 Is one of the following linking groups: deuterium, halo, cyano, substituted or unsubstituted C1 to C60 alkane, substituted or unsubstituted C1 to C60 aryl, substituted or unsubstituted C2 to C60 heteroaryl, substituted or unsubstituted C10 to C60 aryl fused rings, substituted or unsubstituted C10 to C60 heteroaryl fused rings, -SiRR ' R ', -P (=O) RR ', substituted or unsubstituted C2 to C20 alkyl, C6 to C60 aryl, and C2 to C60 heteroaryl substituted amine groups, wherein R, R ' and R ' are the same or different from each other, And each is independently selected from one of the following groups: hydrogen, halo, cyano, substituted or unsubstituted C1 to C60 alkane, substituted or unsubstituted C1 to C60 alkoxy, substituted or unsubstituted C1 to C60 aryl, substituted or unsubstituted C2 to C60 heteroaryl; r is R 1 To R 8 Identical to or different from each other, and each independently selects one of the following groups: hydrogen, halo, cyano, substituted or unsubstituted C1 to C60 alkane, substituted or unsubstituted C1 to C60 alkoxy, substituted or unsubstituted C1 to C60 aryl, or substituted or unsubstituted C2 to C60 heteroaryl, substituted or unsubstituted C10 to C60 aryl fused rings, substituted or unsubstituted C10 to C60 heteroaryl fused rings.
In a second aspect, an organic electroluminescent device is provided, which comprises a substrate, and an anode layer, an organic light-emitting functional layer and a cathode layer which are sequentially arranged on the substrate, wherein the organic light-emitting functional layer comprises an electron transport layer.
The beneficial effects are that: the organic electron transport material provided by the invention is a benzocinnamine organic compound, wherein benzocinnamine is used as an electron-absorbing group with electron transport property, and the electron-deficient group with electron transport property is matched to construct an organic material with a deeper LUMO energy level, and when the organic material is used as an electron transport layer material, the energy level matching property between an electron injection layer and the electron transport layer can be improved, so that the driving voltage of an organic electroluminescent device is reduced; furthermore, the organic electronic transmission material provided by the invention can be matched with n-type dopants such as alkali metal or compounds thereof or air stability transition metal to form stable metal-organic complex, when the metal-organic complex is used as an electron transmission layer, the electron mobility can be further promoted, the driving voltage of the organic electroluminescent device is reduced, the carrier balance of the luminescent layer is enhanced, so that the effects of improving the luminous efficiency and reducing the efficiency roll-off are achieved, and meanwhile, the benzocinnamine has better chemical stability and can enhance the service life of the organic electroluminescent device.
Drawings
Fig. 1 is a schematic structural diagram of an organic electroluminescent device of the present application.
The reference numerals in the figures illustrate: 10. an anode layer; 11. a hole injection layer; 12. a first hole transport layer; 13. a second hole transport layer; 14. a light emitting layer; 15. a second electron transport layer; 16. a first electron transport layer; 17. an electron injection layer; 18. and a cathode layer.
Detailed Description
For the purpose of making the objects, technical solutions and advantages of the embodiments of the present disclosure more apparent, the technical solutions of the embodiments of the present disclosure will be clearly and completely described below with reference to the accompanying drawings of the embodiments of the present disclosure. It will be apparent that the described embodiments are some, but not all, of the embodiments of the present disclosure. All other embodiments, which can be made by one of ordinary skill in the art without the benefit of the present disclosure, are intended to be within the scope of the present invention based on the described embodiments.
It is to be understood that any and all embodiments of the invention may be combined with any other embodiment or features of multiple other embodiments to yield yet further embodiments without conflict. The present invention includes such combinations resulting in additional embodiments.
In this specification, groups and substituents thereof can be selected by one skilled in the art to provide stable moieties and compounds. When substituents are described by conventional formulas written from left to right, the substituents also include chemically equivalent substituents obtained when writing formulas from right to left.
The section headings used in this specification are for organizational purposes only and are not to be construed as limiting the subject matter described. All documents or portions of documents cited in this disclosure, including but not limited to patents, patent applications, articles, books, operating manuals, and treatises, are hereby incorporated by reference in their entirety.
Unless otherwise specified, all technical and scientific terms used herein have the standard meaning of the art to which the claimed subject matter belongs. In case there are multiple definitions for a term, the definitions herein control.
As used herein, the singular forms "a", "an", and "the" are understood to include plural referents unless the context clearly dictates otherwise. Furthermore, the term "comprising" is an open-ended limitation and does not exclude other aspects, i.e. it includes the content indicated by the invention.
The invention provides an organic electronic transmission material, wherein the organic electronic transmission material is a benzocinnamine organic compound, and the molecular structural formula of the organic electronic transmission material is shown as follows:
and->Wherein m and n represent integers; l (L) 1 Is a linear bond or one of the following linking groups: a substituted or unsubstituted C6 to C60 arylene, a substituted or unsubstituted C2 to C60 heteroarylene, a substituted or unsubstituted C10 to C60 arylene fused ring, a substituted or unsubstituted C10 to C60 heteroarylene fused ring; z is Z 1 Is one of the following linking groups: deuterium, halo, cyano, substituted or unsubstituted C1 to C60 alkane, substituted or unsubstituted C1 to C60 aryl, substituted or unsubstituted C2 to C60 heteroaryl, substituted or unsubstituted C10 to C60 aryl fused rings, substituted or unsubstituted C10 to C60 heteroaryl fused rings, -SiRR ' R ', -P (=o) RR ', substituted or unsubstituted C2 to C20 alkyl, C6 to C60 aryl, and C2 to C60 heteroaryl substituted amine groups, wherein R, R ' and R ' are the same or different from each other and are each independently selected from one of the following groups: hydrogen, halo, cyano, substituted or unsubstituted C1 to C60 alkane, substituted or unsubstituted C1 to C60 alkoxy, substituted or unsubstituted C1 to C60 aryl, substituted or unsubstituted C2 to C60 heteroaryl; r is R 1 To R 8 Identical to or different from each other, and each independently selects one of the following groups: hydrogen, halo, cyano, substituted or unsubstituted C1 to C60 alkane, substitutedOr unsubstituted C1 to C60 alkoxy, substituted or unsubstituted C1 to C60 aryl, or substituted or unsubstituted C2 to C60 heteroaryl, substituted or unsubstituted C10 to C60 aryl fused rings, substituted or unsubstituted C10 to C60 heteroaryl fused rings.
In order to balance the recombination of holes and electrons as much as possible, it is necessary to find an electron transport material that has high mobility and is stable. The organic electron transport material provided by the invention is a benzocinnamine organic compound, wherein benzocinnamine is used as an electron-absorbing group with electron transport property, and the electron-deficient group with electron transport property is matched to construct an organic material with a deeper LUMO energy level, and when the organic material is used as an electron transport layer material, the energy level matching property between an electron injection layer and the electron transport layer can be improved, so that the driving voltage of an organic electroluminescent device is reduced; furthermore, the organic electronic transmission material provided by the invention can be matched with n-type dopants such as alkali metal or compounds thereof or air stability transition metal to form stable metal-organic complex, when the metal-organic complex is used as an electron transmission layer, the electron mobility can be further promoted, the driving voltage of the organic electroluminescent device is reduced, the carrier balance of the luminescent layer is enhanced, so that the effects of improving the luminous efficiency and reducing the efficiency roll-off are achieved, and meanwhile, the benzocinnamine has better chemical stability and can enhance the service life of the organic electroluminescent device.
In some embodiments, the L 1 Is one of the following structural formulas:
but is not limited thereto.
In some embodiments, the Z 1 Is one of the following structural formulas:
but is not limited thereto.
In some embodiments, the organic electron transport material is one of the following structural formulas:
in some embodiments, an organic electroluminescent device is further provided, including a substrate, and an anode layer, an organic light-emitting functional layer, and a cathode layer sequentially disposed on the substrate, where the organic light-emitting functional layer includes an electron transport layer, and a material of the electron transport layer includes the organic electron transport material of the present invention.
In this embodiment, the organic material is a benzocinnamine organic compound, where benzocinnamine is used as an electron-withdrawing group with electron-transporting property, and an organic material with a lower LUMO energy level is constructed by matching with an electron-withdrawing group with electron-transporting property, and when the organic material is used as an electron-transporting layer material, the energy level matching property between the electron-injecting layer and the electron-transporting layer can be improved, so that the driving voltage of the organic electroluminescent device is reduced.
In some embodiments, the material of the electron transport layer further comprises an n-type dopant, the n-type dopant being Li, rb, cs, mg, ba, liF, csF, baO, lithium 8-hydroxyquinolinate, sodium 8-hydroxyquinolinate, libpp, bepq2, bepp2, csCO 3 、ZnO、CsN 3 、Rb 2 CO 3 One or more of Yb, ag, cu and Au.
The n-type dopant and the electron transport material are doped to form an ohmic contact surface, so that the energy barrier of the high work function electrode can be overcome, the electron injection efficiency can be improved, and the service life of the device can be prolonged and the operation can be stable. Therefore, in this embodiment, the organic electron transport material may be further used with an n-type dopant such as an alkali metal or a compound thereof or an air-stable transition metal to form a stable metal-organic complex, and the metal-organic complex as an electron transport layer material may reduce the driving voltage of the organic electroluminescent device, enhance the light emitting efficiency, and enhance the service life of the organic electroluminescent device.
In some embodiments, the material of the electron transport layer is composed of an electron transport material and an n-type dopant, wherein the doping ratio of the n-type dopant is 0.1-50%, and as an example, the doping ratio of the n-type dopant may be 0.1%, 0.5%, 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, etc.
In some embodiments, there is also provided an organic electroluminescent device including a substrate, and an anode layer, an organic light-emitting functional layer, and a cathode layer sequentially disposed on the substrate, the organic light-emitting function The energy layer comprises an electron transport layer made of materialAnd Yb, wherein the doping mass ratio of Yb is 1%. In this example p-benzocinnamyl Compound +.>The organic electroluminescent device is matched with n-type dopant Yb as an electron transport layer material, the doping mass ratio of the metal Yb is 1.0%, and the prepared organic electroluminescent device is 10 mA/cm 2 The driving voltage at the current density was 3.8V, and the electron transport material Bphen +.>The turn-on voltage of the prepared organic electroluminescent device is 4.2V in combination with the Yb doping, which shows that the benzocinnamyl alkali compound of the embodiment can effectively reduce the turn-on voltage when being used as an electron transport body and doped with n-type dopants.
In some embodiments, the organic light-emitting functional layer further includes a light-emitting layer and a hole-functional layer disposed between the light-emitting layer and the anode layer. In this embodiment, the hole-functional layer includes one or more of a hole-injecting layer, a hole-transporting layer, and an electron-blocking layer; the organic light emitting functional layer further includes an electron injection layer disposed between the cathode layer and the electron transport layer.
Next, the organic electroluminescent device of the present application will be further described.
The application provides an organic electroluminescent device, as shown in fig. 1, which comprises a substrate, and an anode layer 10, an organic light-emitting functional layer and a cathode layer 18 which are sequentially arranged on the substrate, wherein the organic light-emitting functional layer comprises an electron transport layer, and the material of the electron transport layer comprises the organic electron transport material.
In the embodiment of the present application, the organic light emitting functional layer includes a hole injection layer 11, a hole transport layer, a light emitting layer 14, an electron transport layer, and an electron injection layer 17 sequentially formed on an anode layer 10 of a substrate.
Light emitting layer 14
In some embodiments, the light-emitting layer of the organic electroluminescent device determines the type of light-emitting color, and the film thickness of the light-emitting layer 14 is preferably 10-50-nm. The light-emitting layer of the organic electroluminescent device is preferably a binary system, that is, the light-emitting layer is composed of a host material and a guest material, and the host material and the guest material are GH-1 and Ir (mppy) 3, by way of example, wherein the mass doping ratio of the guest material Ir (mppy) 3 is preferably 1% -15%, and the GH-1 and Ir (mppy) 3 have the following structures:
anode layer 10
The anode layer 10 of the organic electroluminescent device mainly functions to inject holes into the hole injection layer 11, the hole transport layer or the light emitting layer 14, and preferably an anode layer material having a work function of 4.5. 4.5 eV or more is used. The anode layer material is preferably selected from one of Indium Tin Oxide (ITO), tin oxide (NESA), indium Gallium Zinc Oxide (IGZO), silver, and the like. The anode layer 10 may be formed as an anode layer film by a thermal vapor deposition method, a sputtering method, or the like. Preferably, the light transmittance of the visible region of the anode layer 10 is greater than 80%. In addition, the sheet resistance of the anode layer 10 is preferably 500 Ω/cm -1 Hereinafter, the film thickness is preferably selected in the range of 10 to 200. 200 nm.
Cathode layer 18
The cathode layer 18 of the organic electroluminescent device mainly functions to inject electrons into the electron injection layer 17, the electron transport layer or the light emitting layer 14, and preferably a material having a small work function is used. The cathode layer material is not particularly limited, and is preferably one selected from aluminum, magnesium, silver, a magnesium-silver alloy, a magnesium-aluminum alloy, an aluminum-lithium alloy, and the like. Similarly, the cathode layer 18 may be formed as a cathode layer thin film by a thermal vapor deposition method, a sputtering method, or the like, and the film thickness of the cathode layer 18 is preferably selected in the range of 10 to 200 nm. In addition, light may be extracted from the cathode side as needed.
Electron injection layer 17
In the organic electroluminescent device, it is preferable to provide the electron injection layer 17 at the interface region of the cathode layer 18 and the electron transport layer. The electron injection layer 17 mainly functions to promote electron injection from the cathode layer 18 to the electron transport layer, and to achieve an improvement in the light emission luminance and the device lifetime of the organic electroluminescent device. The electron injection layer material here means a material having a work function of 3.8 or less eV, and the electron injection layer material may preferably be at least one selected from lithium, sodium, potassium, rubidium, cesium, magnesium, calcium, gold, silver, copper, iron, nickel, platinum, palladium, ruthenium, ytterbium, molybdenum trioxide, vanadium pentoxide, tungsten trioxide, cesium fluoride, cesium carbonate, lithium fluoride, lithium carbonate, lithium 8-hydroxyquinolinate (Liq), and the like. The electron injection layer 17 may be formed into an electron injection layer film by a thermal vapor deposition method, and the vapor deposition rate is preferably 0.01 to 0.5 a/s, and the film thickness of the electron injection layer 17 thus produced is preferably selected within the range of 0.1 to 15 a nm.
Electron transport layer
The electron transport layer of the organic electroluminescent device is an organic layer formed between the light emitting layer 14 and the electron injection layer 17, and mainly functions to transport electrons from the cathode layer 18 to the light emitting layer 14. The electron transport layer may be composed of a layer of organic layer material, defined as the first electron transport layer 16; it is also possible to consist of two layers of organic layer material, the organic layer on the side close to the cathode layer 18 being defined as the first electron transport layer 16 and the organic layer on the side close to the light-emitting layer 14 being defined as the second electron transport layer 15.
In the present embodiment, when the electron transport layer is composed of the first electron transport layer 16 and the second electron transport layer 15, the film thickness of the first electron transport layer 16 is preferably 9 to 70 nm, and the film thickness of the second electron transport layer 15 is preferably 1 to 30 nm; when the electron transport layer is composed of only the second electron transport layer 15, the film thickness of the second electron transport layer 15 is preferably 10 to 100nm.
In this embodiment, the materials of the first electron transport layer 16 and the second electron transport layer 15 may be the organic electron transport materials according to the present invention; of course, the materials of the first electron transport layer 16 and the second electron transport layer 15 may be organic electron transport materials according to the present invention, for example, the materials of the first electron transport layer 16 are organic electron transport materials according to the present invention, and the materials of the second electron transport layer 15 may be SF3-TRZ with chemical structural formula。
Hole transport layer
The hole transport layer of the organic electroluminescent device is an organic layer formed between the light emitting layer 14 and the anode layer 10 (or the hole injection layer 11), and mainly functions to transport holes from the anode layer to the light emitting layer 14. The hole transport layer may be composed of a layer of organic layer material, defined as the first hole transport layer 12; it is also possible to consist of two layers of organic layer material, the organic layer on the side close to the anode layer 10 being defined as the first hole transport layer 12 and the organic layer on the side close to the light-emitting layer 14 being defined as the second hole transport layer 13.
The hole transport layer of the organic electroluminescent device of the present application may preferably be selected from aromatic amine compounds, preferably from compounds represented by the formulae (HT-1) - (HT-61), but is not limited to the following structures:
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the film thickness of the hole transport layer is not particularly limited, and is preferably 20 to 200 and nm. Wherein when the hole transport layer of the organic electroluminescent device is composed of the first hole transport layer, the film thickness of the first hole transport layer is preferably 20 to 200 nm; when the hole transport layer of the organic electroluminescent device is composed of a first hole transport layer and a second hole transport layer, the film thickness of the first hole transport layer is preferably 19 to 150 nm and the film thickness of the second hole transport layer is preferably 1 to 50 nm.
Hole injection layer 11
In the organic electroluminescent device of the present application, the hole injection layer 11 is preferably provided in the interface region between the anode layer 10 and the hole transport layer (or the light emitting layer 14). The hole injection layer 11 mainly functions to promote injection of holes from the anode layer 10 to the hole transport layer or the light emitting layer 14, realizing reduction in driving voltage of the organic electroluminescent device, and improvement in light emission luminance and device lifetime. The hole injection layer material here is an acceptor type organic material containing a deep LUMO level, and as a specific example thereof, one of HI-1-HI-20 is preferable, and the film thickness of the hole injection layer 11 is not particularly limited, and is preferably selected in the range of 1 to 50 nm.
Wherein, the structural formulas of HI-1 to HI-20 are as follows:
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n-type dopant and p-type dopant
In the organic electroluminescent device of the present application, it is preferable that an n-type dopant is doped in the electron transport layer, a p-type dopant is doped in the hole transport layer, the n-type dopant and the p-type dopant have the main functions of improving the transport properties of the electron transport layer and the hole transport layer,the driving voltage of the organic electroluminescent device is reduced. Here, as specific examples thereof, the n-type dopant may be preferably Li, cs, ba, yb, csF, baO, 8-hydroxyquinolinate lithium (Liq), naq, libpp, bepq2, bepp2, liF, csCO 3 One of ZnO, etc.; as specific examples thereof, one of HATCN, F4TCNQ, compound HI-3 and the like may be preferable.
When the hole transport layer contains a p-type dopant and a hole transport material, the doping concentration of the p-type dopant is preferably 0.1% to 50.0%; when the electron transport layer contains an n-type dopant and an electron transport layer material, the doping concentration of the n-type dopant is preferably 0.1% to 50.0%.
In the organic electroluminescent device, the structural formulas of Liq, naq, libpp, bepq and Bepp2 are as follows:
the present application is further illustrated by the following specific examples. Specific details of synthetic experiments are illustrated by examples 1-10. Specific details of the preparation of the organic electroluminescent device are described by taking examples 11 to 20 and examples 21 to 24 as examples. The organic electroluminescent devices of examples 31 to 32 and examples 41 to 43 were compared with those of examples 11 to 20 and examples 21 to 24, respectively, as comparative examples.
Example 1
Synthesis of Compound 5-2
To a 250mL round bottom flask under nitrogen was added 2-iodo-4-chloroaniline (2.52 g,10mmol,1 eq), 2-amino-5-chlorophenylboronic acid pinacol ester (2.62 g,12mmol,1.2 eq), tetrakis triphenylphosphine palladium Pd (PPh) 3 ) 4 (0.35 g,0.3mmol, 3M) and K 2 CO 3 (3.45 g,25mmol,2,5 eq) in ethylene glycol dimethyl ether (50 mL) With distilled water (50 mL). The round bottom flask with reflux condenser was then placed in a sand bath together and heated at 120 ℃ for 16 hours. The flask was cooled to room temperature, the reaction mixture was diluted with dichloromethane, and the aqueous phase was extracted with dichloromethane. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel to give the desired intermediate P-1 in a yield of 1.8g, 72%.
To a dried round bottom flask was added intermediate 1-1 (2.5 g,10mmol,1 eq) under nitrogen, tert-butyl nitrite (tBuONO, 3.09g,30mmol,3 eq) followed by the addition of solvent 2, 2-trifluoroethanol (TFE, 0.1 m,20 ml). The nitrogen was replaced, the reaction mixture was stirred at room temperature for 12-24 hours, after completion, the solid residue was removed by filtration through cotton, the mixture solution was concentrated using a rotary evaporator, and purified using silica gel flash column chromatography using hexane and ethyl acetate as eluent to give intermediate P-2 in a yield of 1.6g, yield 64%.
A mixture of intermediate 1-2 (2.50 g,10mmol,1 eq) in phosphorus tribromide (14.5 mL,154 mmol) was heated to 170℃and maintained under argon for 5.5 hours. After the reaction mixture was cooled to room temperature, it was quenched by addition of cold water and neutralized with sodium bicarbonate. The solid formed was collected by filtration and washed with water and methanol. The solid was purified by recrystallization from chloroform to give intermediate P-3 in a yield of 2.6g and a yield of 6.85%.
After compound P-3 (3.96 g,10mmol,1 eq) was dissolved in 50mL of toluene solution, 2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) pyrimidine (4.22 g,22mmol,2.3 eq), tetrakis triphenylphosphine palladium (0.693 g,0.6mmol,0.06 eq) and potassium carbonate (6.9 g, 50mmol,2.5 eq), 12mL ethanol and 12mL water were added thereto, and reacted at 100 ° for 12 hours. After the reaction was terminated, the resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to give the objective compound 5-2 in a yield of 2.3g and a yield of 69%.
Example 2
Synthesis of Compounds 5-8
Into a 250mL round bottom flask under nitrogen was added 2, 5-dibromoaniline (2.5 g,10mmol,1 eq), 2-aminophenylboronic acid pinacol ester (2.22 g,12mmol,1.3 eq), pd (PPh) 3 ) 4 (0.35 g,0.3mmol, 3M) and K 2 CO 3 (3.45 g,25mmol,2,5 eq) in ethylene glycol dimethyl ether (50 mL) with distilled water (50 mL). The round bottom flask with reflux condenser was then placed in a sand bath together and heated at 120 ℃ for 16 hours. The flask was cooled to room temperature, the reaction mixture was diluted with dichloromethane, and the aqueous phase was extracted with dichloromethane. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel to give the desired intermediate P-4 in a yield of 1.6g, 61%.
To a dried round bottom flask was added intermediate P-4 (2.7 g,10mmol,1 eq) under nitrogen, tert-butyl nitrite (tBuONO, 3.09g,30mmol,3 eq) followed by the addition of solvent 2, 2-trifluoroethanol (TFE, 0.1M, 20 mL). The nitrogen was replaced, the reaction mixture was stirred at room temperature for 12-24 hours, after completion, the solid residue was removed by filtration through cotton, the mixture solution was concentrated using a rotary evaporator, and purified using silica gel flash column chromatography using hexane and ethyl acetate as eluent to give intermediate P-5 in a yield of 1.5g, 59%.
After compound P-5 (2.66 g,10mmol,1 eq) was dissolved in 50mL of toluene solution, compound 2, 4-diphenyl-6-pinacol ester-1, 3, 5-triazine (3.71 g,14mmol,1.4 eq), tetrakis triphenylphosphine palladium (0.348 g,0.3mmol,0.03 eq) and potassium carbonate (3.5 g, 25mmol,2.5 eq), 12mL ethanol and 12mL water were added thereto, and reacted at 100 ° for 12 hours. After the reaction was terminated, the resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to give the objective compound 5-8 in a yield of 3.1g and a yield of 75%.
Example 3
Synthesis of Compounds 5-15
To a 250mL round bottom flask under nitrogen was added 2-iodo-4-chloroaniline (2.5 g,10mmol,1 eq), 2-aminophenylboronic acid pinacol ester (2.4 g,13mmol,1.3 eq), pd (PPh) 3 ) 4 (0.35 g,0.3mmol,0.03 eq) and K 2 CO 3 (3.45 g,25mmol,2,5 eq) in ethylene glycol dimethyl ether (50 mL) with distilled water (50 mL). The round bottom flask with reflux condenser was then placed in a sand bath together and heated at 120 ℃ for 16 hours. The flask was cooled to room temperature, the reaction mixture was diluted with dichloromethane, and the aqueous phase was extracted with dichloromethane. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel to give the desired intermediate P-6 in a yield of 1.2g, 52%.
To a dried round bottom flask was added intermediate P-6 (2.1 g,10mmol,1 eq) under nitrogen, tert-butyl nitrite (tBuONO, 3.09g,30mmol,3 eq) followed by the addition of solvent 2, 2-trifluoroethanol (TFE, 0.1M, 20 mL). The nitrogen was replaced, the reaction mixture was stirred at room temperature for 12-24 hours, after completion, the solid residue was removed by filtration through cotton, the mixture solution was concentrated using a rotary evaporator, and purified using silica gel flash column chromatography using hexane and ethyl acetate as eluent to give intermediate P-7 in a yield of 1.5g, yield 56%.
A mixture of intermediate P-7 (2.50 g,10mmol,1 eq) in phosphorus tribromide (14.5 mL,154 mmol) was heated to 170℃and maintained under argon for 5.5 hours. After the reaction mixture was cooled to room temperature, it was quenched by addition of cold water and neutralized with sodium bicarbonate. The solid formed was collected by filtration and washed with water and methanol. The solid was purified by recrystallization from chloroform to give intermediate P-8 in a yield of 1.6g and a yield of 64%.
After compound P-8 (2.66 g,10mmol,1 eq) was dissolved in 50mL of toluene, the compound 2, 4-diphenyl-6- [4- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl ] -1,3, 5-triazine (4.8 g,13mmol,1.3 eq), tetrakis triphenylphosphine palladium (0.348 g,0.3mmol, 0.03eq) and potassium carbonate (3.5 g, 25mmol,2.5 eq), 12mL of ethanol and 12mL of water were added thereto, and reacted at 100℃for 12 hours. After the reaction was terminated, the resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to give the objective compound 5-15 in a yield of 3.9g and a yield of 80%.
Example 4
5-18 Synthesis of Compounds
After the compound 2-bromo-1, 10-phenanthroline (2.6 g,10mmol,1 eq) was dissolved in 50mL of toluene solution, 4-bromophenylboronic acid pinacol ester (3.2 g,14mmol,1.4 eq), tetrakis triphenylphosphine palladium (0.348 g,0.3mmol,0.03 eq) and potassium carbonate (3.5 g,25mmol,2.5 eq), 12mL of ethanol and 12mL of water were added thereto, and reacted at 100 ° for 12 hours. After the reaction was terminated, the resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to give the objective compound P-9 in a yield of 2.3g and a yield of 71%.
Under nitrogen, intermediate P-9 (3.4 g,10mmol,1 eq), bis (pinacolato) diborane (3.75 g,15mmol,1.5 eq), potassium acetate (KOAC, 2.45g,25mmol,2.5 eq), DPPF palladium dichloride (Pd (DPPF) Cl2, 217mg,3mmol,0.03 eq) and 120mL dioxane were placed in a round bottom flask. The mixture was heated at 85 ℃ under nitrogen for 24 hours. After cooling to room temperature, the mixture was washed three times with 50mL of water and extracted with dichloromethane. The organic solution was treated with MgSO 4 Drying and then evaporating the solvent. The residue was purified by column chromatography using a petroleum ether/dichloromethane mixture to give intermediate P-10 as a white solid in a yield of 2.8g, 74%.
After compound P-10 (4.2 g,12mmol,1.2 eq) was dissolved in 50mL of toluene solution, intermediate P-8 (2.8 g,10mmol,1 eq), tetrakis triphenylphosphine palladium (0.348 g,0.3mmol,0.03 eq) and potassium carbonate (3.5 g,25mmol,2.5 eq), 12mL of ethanol and 12mL of water were added thereto, and reacted at 100℃for 12 hours. After the reaction was terminated, the resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to give the objective compound 5-18 in a yield of 3.3g and a yield of 78%.
Example 5
5-29 Synthesis of Compounds
To a 250mL round bottom flask was added a mixture of 2, 6-dibromoaniline (2.51 g,10mmol,1 eq), 2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) aniline (2.41 g,11mmol,1.1 eq), 3M% tetrakis triphenylphosphine palladium (Pd (PPh 3) 4) (346, 97mg,0.3mmol,0.03 eq) and K2CO3 (3.45 g,25mmol,2.5 eq) in ethylene glycol dimethyl ether (50 mL) with distilled water (50 mL) (DEM/H2O) under nitrogen. The round bottom flask with reflux condenser was then placed in a sand bath together and heated at 120 ℃ for 16 hours. The flask was cooled to room temperature, the reaction mixture was diluted with dichloromethane, and the aqueous phase was extracted with dichloromethane. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel to give the desired intermediate P-11. Yield 1.97g, 75%.
To a 250mL round bottom flask under nitrogen was added intermediate P-11 (4.04 g,20mmol,1 eq), tert-butyl nitrite (tBuONO, 6.18g,60mmol,3 eq), followed by the addition of solvent 2, 2-trifluoroethanol (TFE, 0.1M, 20 mL). The nitrogen was replaced, the reaction mixture was stirred at room temperature for 24 hours, after completion, the solid residue was removed by filtration through cotton, the mixture solution was concentrated using a rotary evaporator, and purified by flash column chromatography on silica gel using hexane and ethyl acetate as eluent, to give intermediate P-12 in a yield of 2.81g, 65%.
To a 250mL round bottom flask under nitrogen was added 4' - (4-bromophenyl) -2,2':6',2 "-terpyridine (3.8 g,10mmol,1 eq), bis (pinacolato) diborane (3.75 g,15mmol,1.5 eq), potassium acetate (KOAC, 2.45g,25mmol,2.5 eq), DPPF palladium dichloride (Pd (DPPF) Cl) 2 217mg,3mmol,0.03 eq) and 120mL dioxane were placed in a round bottom flask. The mixture was heated at 85 ℃ under nitrogen for 24 hours. After cooling to room temperature, the mixture was washed three times with 50mL of water and extracted with dichloromethane. The organic solution was treated with MgSO 4 Drying and then evaporating the solvent. The residue was purified by column chromatography using a petroleum ether/dichloromethane mixture to give intermediate P-13 as a white solid in a yield of 3.3g and 77%.
After compound P-12 (2.6 g,10mmol,1 eq) was dissolved in 50mL of toluene under nitrogen, intermediate P-13 (5.2 g,13mmol,1.3 eq), tetrakis triphenylphosphine palladium (0.348 g,0.3mmol,0.03 eq) and potassium carbonate (3.5 g, 25mmol,2.5 eq), 12mL of ethanol and 12mL of water were added thereto and reacted at 100℃for 12 hours. After the reaction was terminated, the resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to give the objective compound 29 in a yield of 3.9g and a yield of 80%.
Example 6
5-30 Synthesis of Compounds
A solution of 4,4' -dibromobiphenyl (4.48g,13.0 mmol,1eq) in 150 mL THF was cooled to-95℃with an acetone/liquid nitrogen bath under nitrogen. To the mixture was added dropwise a solution of n-butyllithium (n-BuLi) (2.5. 2.5M hexane solution, 5.2 mL,13.0 mmol). The resulting solution was stirred at-95 ℃ for 1 hour. To the mixture was added dropwise chlorodiphenylphosphine (2.9 g,13.0mmol,1 eq). The solution was warmed to room temperature over 3 hoursWhen (1). The solution was concentrated under vacuum. The residue was subjected to silica gel column chromatography (CH 2 Cl 2 Hexane, 1:5). The white solid was dissolved in a mixture of dichloromethane (60 mL) and methanol (60 mL). Hydrogen peroxide (30% solution, 3.5 mL) was slowly added to the solution. The resulting mixture was stirred at room temperature for 2 hours. With Na 2 SO 3 The reaction was quenched with aqueous solution. The mixture was extracted with dichloromethane. With anhydrous MgSO 4 The organic layer was dried. The organic layer was filtered. The organic layer was concentrated under vacuum. Intermediate P-14 was obtained in a yield of 2.3g and a yield of 53%.
To a 250mL round bottom flask under nitrogen was added intermediate P-14 (4.3 g,10mmol,1 eq), bis (pinacolato) diborane (3.75 g,15mmol,1.5 eq), potassium acetate (KOAC, 2.45g,25mmol,2.5 eq), DPPF palladium dichloride (Pd (DPPF) Cl) 2 217mg,3mmol,0.03 eq) and 120mL dioxane were placed in a round bottom flask. The mixture was heated at 85 ℃ under nitrogen for 24 hours. After cooling to room temperature, the mixture was washed three times with 50mL of water and extracted with dichloromethane. The organic solution was treated with MgSO 4 Drying and then evaporating the solvent. The residue was purified by column chromatography using a petroleum ether/dichloromethane mixture to give intermediate P-15 as a white solid in a yield of 3.8g and a yield of 79%.
After compound P-15 (5.5 g,1.2mmol,1.2 eq) was dissolved in 50mL of toluene under nitrogen, intermediate P-8 (2.6 g,10mmol,1 eq), tetrakis triphenylphosphine palladium (0.348 g,0.3mmol,0.03 eq) and potassium carbonate (3.5 g,25mmol,2.5 eq), 12mL of ethanol and 12mL of water were added thereto, and reacted at 100℃for 12 hours. After the reaction was terminated, the resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to give the objective compound 30 in a yield of 4.3g and a yield of 81%.
Example 7
5-34 Synthesis of Compounds
To a 250mL round bottom flask under nitrogen was added intermediate P-16 (2.8 g,10mmol,1 eq), bis (pinacolato) diborane (3.75 g,15mmol,1.5 eq), potassium acetate (KOAC, 2.45g,25mmol,2.5 eq), DPPF palladium dichloride (Pd (DPPF) Cl) 2 217mg,3mmol,0.03 eq) and 120mL dioxane were placed in a round bottom flask. The mixture was heated at 85 ℃ under nitrogen for 24 hours. After cooling to room temperature, the mixture was washed three times with 50mL of water and extracted with dichloromethane. The organic solution was treated with MgSO 4 Drying and then evaporating the solvent. The residue was purified by column chromatography using a petroleum ether/dichloromethane mixture to give intermediate P-16 as a white solid in a yield of 2.8g, 74%.
After the compound 2-bromo-1-phenyl-1H-benzimidazole (2.7 g,10mmol,1.2 eq) was dissolved in 50mL of toluene solution under nitrogen, intermediate P-16 (3.8 g,10mmol,1 eq), tetrakis triphenylphosphine palladium (0.348 g,0.3mmol,0.03 eq) and potassium carbonate (3.5 g, 25mmol,2.5 eq), 12mL of ethanol and 12mL of water were added thereto, and reacted at 100 ° for 12 hours. After the reaction was terminated, the resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to give the objective compound P-17 in a yield of 3.6g and a yield of 78%.
After compound P-17 (4.6 g,1.2mmol,1.2 eq) was dissolved in 50mL of toluene under nitrogen, intermediate P-8 (2.6 g,10mmol,1 eq), tetrakis triphenylphosphine palladium (0.348 g,0.3mmol,0.03 eq) and potassium carbonate (3.5 g, 25mmol,2.5 eq), 12mL of ethanol and 12mL of water were added thereto, and reacted at 100℃for 12 hours. After the reaction was terminated, the resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to give the objective compound 5-34 in a yield of 3.8g and a yield of 78%.
Example 8
5-35 Synthesis of Compounds
After the compound 2-bromo-1, 10-phenanthroline (2.6 g,10mmol,1 eq) was dissolved in 50mL of toluene solution, compound intermediate P-16 (4.2 g,12mmol,1.2 eq), tetrakis triphenylphosphine palladium (0.348 g,0.3mmol,0.03 eq) and potassium carbonate (3.5 g, 25mmol,2.5 eq), 12mL of ethanol and 12mL of water were added thereto, and reacted at 100 ° for 12 hours. After the reaction was terminated, the resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to give the objective compound P-18 in a yield of 3.3g and a yield of 77%.
After compound P-18 (4.5 g,12mmol,1.2 eq) was dissolved in 50mL of toluene solution, compound intermediate P-5 (2.6 g,10mmol,1 eq), tetrakis triphenylphosphine palladium (0.348 g,0.3mmol,0.03 eq) and potassium carbonate (3.5 g, 25mmol,2.5 eq), 12mL of ethanol and 12mL of water were added thereto, and reacted at 100℃for 12 hours. After the reaction was terminated, the resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to give the objective compound 5-35 in a yield of 3.8g and a yield of 80%.
Example 9
5-38 Synthesis of Compounds
After the compound 2, 4-diphenyl-6-pinacol ester-1, 3, 5-triazine (3.6 g,10mmol,1 eq) was dissolved in 50mL of toluene solution, the compound 9, 10-dibromoanthracene (3.5 g,12mmol,1.2 eq), tetrakis triphenylphosphine palladium (0.348 g,0.3mmol,0.03 eq) and potassium carbonate (3.5 g,25mmol,2.5 eq), 12mL of ethanol and 12mL of water were added thereto, and reacted at 100 ° for 12 hours. After the reaction was terminated, the resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to give the objective compound P-19 in a yield of 3.3g and a yield of 77%.
To a 250mL round bottom flask under nitrogen was added intermediate P-19 (4.3 g,10mmol,1 eq), bis (pinacolato) diborane (3.75 g,15mmol,1.5 eq), potassium acetate (KOAC, 2.45g,25mmol,2.5 eq), DPPF palladium dichloride (Pd (DPPF) Cl) 2 217mg,3mmol,0.03 eq) and 120mL dioxane were placed in a round bottom flask. The mixture was heated at 85 ℃ under nitrogen for 24 hours. After cooling to room temperature, the mixture was washed three times with 50mL of water and extracted with dichloromethane. The organic solution was treated with MgSO 4 Drying and then evaporating the solvent. The residue was purified by column chromatography using a petroleum ether/dichloromethane mixture to give intermediate P-20 as a white solid in a yield of 4.3g and 80%.
After intermediate P-20 (5.8 g,11mmol,1.1 eq) was dissolved in 50mL of toluene solution, compound intermediate P-5 (2.6 g,10mmol,1 eq), tetrakis triphenylphosphine palladium (0.348 g,0.3mmol,0.03 eq) and potassium carbonate (3.5 g, 25mmol,2.5 eq), 12mL of ethanol and 12mL of water were added thereto, and reacted at 100℃for 12 hours. After the reaction was terminated, the resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to give the objective compound 5-38 in a yield of 4.6g and a yield of 80%.
Example 10
5-41 Synthesis of Compounds
After the compound 4-pinacol borate-2, 2':6',2 "-terpyridine (3.6 g,10mmol,1 eq) was dissolved in 50mL of toluene solution, 12-dibromo dronate (4.2 g,11mmol,1.1 eq), tetrakis triphenylphosphine palladium (0.348 g,0.3mmol,0.03 eq) and potassium carbonate (3.5 g, 25mmol,2.5 eq), 12mL ethanol and 12mL water were added thereto, and reacted at 100℃for 12 hours. After the reaction was terminated, the resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to give the objective compound P-21 in a yield of 4.4g and a yield of 82%.
To a 250mL round bottom flask under nitrogen was added intermediate P-21 (5.4 g,10mmol,1 eq), bis (pinacolato) diborane (3.75 g,15mmol,1.5 eq), potassium acetate (KOAC, 2.45g,25mmol,2.5 eq), DPPF palladium dichloride (Pd (DPPF) Cl) 2 217mg,3mmol,0.03 eq) and 120mL dioxane were placed in a round bottom flask. The mixture was heated at 85 ℃ under nitrogen for 24 hours. After cooling to room temperature, the mixture was washed three times with 50mL of water and extracted with dichloromethane. The organic solution was treated with MgSO 4 Drying and then evaporating the solvent. The residue was purified by column chromatography using a petroleum ether/dichloromethane mixture to give intermediate P-22 as a white solid in a yield of 4.8g and a yield of 83%.
After intermediate P-22 (5.8 g,11mmol,1.1 eq) was dissolved in 50mL of toluene solution, compound intermediate P-8 (2.6 g,10mmol,1 eq), tetrakis triphenylphosphine palladium (0.348 g,0.3mmol,0.03 eq) and potassium carbonate (3.5 g,25mmol,2.5 eq), 12mL of ethanol and 12mL of water were added thereto, and reacted at 100℃for 12 hours. After the reaction was terminated, the resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to give the objective compound 5-41 in a yield of 4.7g and a yield of 73%.
Elemental analysis and molecular weights of the compounds prepared in examples 1 to 10 are shown in Table 1.
Elemental analysis and molecular weight results for the compounds of Table 1
Examples 11 to 20
The glass substrate with an ITO transparent electrode (anode layer, film thickness of ITO was 95 nm) of 30 mm ×30× 30 mm ×0.7 mm was subjected to ultrasonic cleaning in a washing liquid (1 time), acetone (1 time), ultrapure water (2 times), and isopropyl alcohol (1 time) in this order, and the ultrasonic cleaning time was 10 minutes for each step. And placing the cleaned ITO glass substrate in an oven at 80 ℃ for baking for 3 hours. The washing liquid is used for cleaning dirt and oil stains adhered to the surface of the glass substrate with the ITO transparent electrode, which is a commercially available product and is not described herein.
And carrying out vacuum plasma cleaning treatment on the baked glass substrate with the ITO transparent electrode for 10 minutes.
The glass substrate after plasma treatment was mounted on a substrate holder of a vacuum vapor deposition apparatus, and first, a compound HATCN (i.e., compound HI-3) was deposited on the surface of the substrate holder on the side where the ITO transparent electrode was formed so as to cover the ITO transparent electrode, thereby forming a hole injection layer having a film thickness of 10 nm a. The compound HT-10 was vapor deposited on the hole injection layer to form a first hole transport layer having a film thickness of 60 a nm a.
Then, a compound HT-61 was deposited on the first hole transport layer to form a second hole transport layer having a film thickness of 10 a nm a.
Then, a light-emitting layer having a film thickness of 30 a nm was formed by co-vapor deposition of light-emitting host GH-1 and light-emitting guest Ir (mppy) 3 on the second hole-transporting layer.
Then, SF3-TRZ was vapor deposited on the light-emitting layer to form a second electron transport layer having a film thickness of 10: 10 nm.
Then, an electron transport material was deposited on the second electron transport layer to form a first electron transport layer having a film thickness of 30 a nm a.
Examples 11 to 20, in which the electron transport material compound selected for the first electron transport layer was composed, are shown in table 2.
TABLE 2 first electron transport layer Material composition of examples 11-20
Then, liq was vapor deposited on the first electron transport layer to form an electron injection layer having a film thickness of 2 nm.
Then, metal Al was deposited on the electron injection layer to form a cathode layer having a film thickness of 100 a nm a.
Examples 21 to 24
The organic electroluminescent devices prepared in examples 21 to 24 were identical to examples 11 to 20, except that the first electron transport layer of examples 21 to 24 was a combined electron transport material layer formed by steaming the organic electron transport material (first compound) together with an n-type dopant (second compound) in the examples, wherein the n-type dopant was metal Yb, and the doping quality was preferably 1%. The first electron transport layer was formed by co-evaporation of the first compound and the n-type dopant, corresponding to examples 21-24 as shown in table 3.
TABLE 3 first electron transport layer material compositions of EXAMPLES 21-24
Comparative examples 31 to 33
The organic electroluminescent devices prepared in comparative examples 31 to 33 were identical to examples 11 to 20 except that the first electron transport layer, the first compounds of comparative examples 31 to 33 were commercially commonly used electron transport materials tmpb, TPBi and Bphen, and the electron transport layer compounds of comparative examples 31 to 32 are shown in table 4.
TABLE 4 comparative examples 31-33 first electron transport layer Material composition
The specific structural formulas of comparative compound 1, comparative compound 2 and comparative compound 3 are as follows:
comparative examples 41 to 43
The organic electroluminescent devices prepared in comparative examples 41 to 43 were identical to examples 21 to 24 except that the electron transport materials of the first electron transport layer were different, and comparative examples 41 to 43 are shown in Table 5.
TABLE 5 comparative examples 41-43 first electron transport layer Material composition
Evaluation of organic electroluminescent device Performance
Properties of the organic electroluminescent devices prepared in examples 11 to 20, examples 21 to 24, comparative examples 31 to 33 and comparative examples 41 to 43 were measured for CIE1931 chromaticity coordinates (x, y), and external quantum efficiency (unit: nm) of the prepared organic electroluminescent devices using a spectroradiometer CS-2000 (Konica Minolta) and a digital source table 2420 (Keithley).
The results of the properties of the organic electroluminescent devices prepared in examples 11 to 20, examples 21 to 30, comparative examples 31 to 32 and comparative examples 41 to 43 are shown in Table 6.
TABLE 6 comparison of performance results of organic electroluminescent devices
As can be seen from the device performance results of examples 11 to 20 and comparative examples 31 to 33 in table 6, compared with the comparative compound, the organic compound of benzocinnamine of the present application, under the same device preparation conditions, contains the heterocyclic electron-transport material of benzocinnamine structure, the driving voltage of the device is lower than that of the comparative example under the same conditions, the luminous efficiency is improved and the efficiency roll-off is suppressed, which means that the electron-transport material of the heterocyclic compound containing the benzocinnamine structure of the present application has better electron-transport and injection functions, reduces the voltage of the device, obtains better carrier balance, and is beneficial to improving the luminous efficiency and the efficiency roll-off of the device. In addition, the device performance results of comparative examples 21 to 24 and examples 11 to 20, and comparative examples 31 to 33 and comparative examples 41 to 43, revealed that n-type doping of the electron transport layer is a method for effectively improving electron mobility, more balanced hole and electron transport is achieved, and higher luminous efficiency and lower driving voltage are imparted to the device.
It is to be understood that the invention is not limited in its application to the examples described above, but is capable of modification and variation in light of the above teachings by those skilled in the art, and that all such modifications and variations are intended to be included within the scope of the appended claims.

Claims (10)

1. An organic electron transport material, characterized in that the molecular structural formula of the organic electron transport material is as follows:
and->Wherein m and n represent integers; l (L) 1 Is a linear bond or one of the following linking groups: a substituted or unsubstituted C6 to C60 arylene, a substituted or unsubstituted C2 to C60 heteroarylene, a substituted or unsubstituted C10 to C60 arylene fused ring, a substituted or unsubstituted C10 to C60 heteroarylene fused ring; z is Z 1 Is one of the following linking groups: deuterium, halo, cyano, substituted or unsubstituted C1 to C60 alkane, substituted or unsubstituted C1 to C60 aryl, substituted or unsubstituted C2 to C60 heteroaryl, substituted or unsubstituted C10 to C60 aryl fused rings, substituted or unsubstituted C10 to C60 heteroaryl fused rings, -SiRR ' R ', -P (=o) RR ', substituted or unsubstituted C2 to C20 alkyl, C6 to C60 aryl, and C2 to C60 heteroaryl substituted amine groups, wherein R, R ' and R ' are the same or different from each other and are each independently selected from one of the following groups: hydrogen, halo, cyano, substituted or unsubstituted C1 to C60 alkane, substituted or unsubstituted C1 to C60 alkoxy, substituted or unsubstituted C1 to C60 aryl, substituted or unsubstituted C2 to C60 heteroaryl; r is R 1 To R 8 Identical or different from each other and eachOne of the following groups is selected independently: hydrogen, halo, cyano, substituted or unsubstituted C1 to C60 alkane, substituted or unsubstituted C1 to C60 alkoxy, substituted or unsubstituted C1 to C60 aryl, or substituted or unsubstituted C2 to C60 heteroaryl, substituted or unsubstituted C10 to C60 aryl fused rings, substituted or unsubstituted C10 to C60 heteroaryl fused rings.
2. The organic electron transport material according to claim 1, wherein L 1 Is one of the following structural formulas:
。
3. the organic electron transport material according to claim 1, wherein Z 1 Is one of the following structural formulas:
。
4. the organic electron transport material according to claim 1, wherein the organic electron transport material is one of the following structural formulas:
。
5. an organic electroluminescent device comprising a substrate, and an anode layer, an organic luminescent functional layer and a cathode layer which are sequentially arranged on the substrate, wherein the organic luminescent functional layer comprises an electron transport layer, and the organic electroluminescent device is characterized in that the material of the electron transport layer comprises the organic electron transport material as claimed in any one of claims 1 to 4.
6. The organic electroluminescent device of claim 5, wherein the material of the electron transport layer further comprises an n-type dopant, the n-type dopant being Li, rb, cs, mg, ba, liF, csF, baO, lithium 8-hydroxyquinolinate, sodium 8-hydroxyquinolinate, libpp, bepq2, bepp2, csCO 3 、ZnO、CsN 3 、Rb 2 CO 3 One or more of Yb, ag, cu and Au.
7. The organic electroluminescent device of claim 5, wherein the material of the electron transport layer is composed of an organic electron transport material and an n-type dopant, wherein a doping ratio of the n-type dopant is 0.1-50%.
8. The organic electroluminescent device of claim 5, wherein the electron transport layer is made of a material consisting ofAnd Yb, wherein the doping mass ratio of Yb is 1%.
9. The organic electroluminescent device of claim 5, wherein the organic light-emitting functional layer further comprises a light-emitting layer and a hole-functional layer disposed between the light-emitting layer and the anode layer.
10. The organic electroluminescent device of claim 9, wherein the hole-functional layer comprises one or more of a hole-injecting layer, a hole-transporting layer, and an electron-blocking layer.
CN202310757916.0A 2023-06-26 2023-06-26 Organic electronic transmission material and organic electroluminescent device Pending CN116514778A (en)

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Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004026870A1 (en) * 2002-09-19 2004-04-01 Canon Kabushiki Kaisha Phenanthroline compound and organic light emitting device using same
CN102127073A (en) * 2010-11-26 2011-07-20 深圳大学 Star-shaped compound taking phenanthroline as core and luminescent device comprising same
JP2014123687A (en) * 2012-12-21 2014-07-03 Idemitsu Kosan Co Ltd Organic electroluminescent element and electronic device
WO2016017688A1 (en) * 2014-07-31 2016-02-04 コニカミノルタ株式会社 ORGANIC ELECTROLUMINESCENCE ELEMENT, DISPLAY DEVICE, ILLUMINATION DEVICE, π-CONJUGATED COMPOUND, AND LIGHT-EMITTING THIN FILM
CN105859714A (en) * 2016-05-09 2016-08-17 武汉大学 Thermal activation delayed fluorescence material containing 1, 10 phenanthroline unit and application of material
KR20170061603A (en) * 2015-11-26 2017-06-05 주식회사 엘지화학 Hetero-cyclic compound and organic light emitting device comprising the same
CN107531651A (en) * 2015-06-01 2018-01-02 株式会社Lg化学 Heterocyclic compound and the organic luminescent device for including it
CN107556307A (en) * 2016-06-30 2018-01-09 乐金显示有限公司 Organic compound and Organic Light Emitting Diode and organic light-emitting display device including the organic compound
CN108530443A (en) * 2018-05-18 2018-09-14 长春海谱润斯科技有限公司 A kind of phenanthroline derivative and its organic electroluminescence device
CN110698485A (en) * 2019-11-21 2020-01-17 北京鼎材科技有限公司 Compound and application thereof
CN111574505A (en) * 2020-05-22 2020-08-25 西安瑞联新材料股份有限公司 Compound with benzo [ c ] cinnoline as receptor and application thereof

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004026870A1 (en) * 2002-09-19 2004-04-01 Canon Kabushiki Kaisha Phenanthroline compound and organic light emitting device using same
CN102127073A (en) * 2010-11-26 2011-07-20 深圳大学 Star-shaped compound taking phenanthroline as core and luminescent device comprising same
JP2014123687A (en) * 2012-12-21 2014-07-03 Idemitsu Kosan Co Ltd Organic electroluminescent element and electronic device
WO2016017688A1 (en) * 2014-07-31 2016-02-04 コニカミノルタ株式会社 ORGANIC ELECTROLUMINESCENCE ELEMENT, DISPLAY DEVICE, ILLUMINATION DEVICE, π-CONJUGATED COMPOUND, AND LIGHT-EMITTING THIN FILM
CN107531651A (en) * 2015-06-01 2018-01-02 株式会社Lg化学 Heterocyclic compound and the organic luminescent device for including it
KR20170061603A (en) * 2015-11-26 2017-06-05 주식회사 엘지화학 Hetero-cyclic compound and organic light emitting device comprising the same
CN105859714A (en) * 2016-05-09 2016-08-17 武汉大学 Thermal activation delayed fluorescence material containing 1, 10 phenanthroline unit and application of material
CN107556307A (en) * 2016-06-30 2018-01-09 乐金显示有限公司 Organic compound and Organic Light Emitting Diode and organic light-emitting display device including the organic compound
CN108530443A (en) * 2018-05-18 2018-09-14 长春海谱润斯科技有限公司 A kind of phenanthroline derivative and its organic electroluminescence device
CN110698485A (en) * 2019-11-21 2020-01-17 北京鼎材科技有限公司 Compound and application thereof
CN111574505A (en) * 2020-05-22 2020-08-25 西安瑞联新材料股份有限公司 Compound with benzo [ c ] cinnoline as receptor and application thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
TENG-ZHOU YANG ET AL.: "Novel smectic liquid crystals based on benzo[c]cinnoline: their synthesis， mesomorphism， opto- and electro-chemical properties", TAYLOR & FRANCIS, vol. 44, no. 4, pages 666 - 673 *
YANG SHI ET AL.: "Structurally Nontraditional Benzo[c]cinnoline- Based Electron -Transporting Materials with 3D Molecular Interaction Architecture", ANGEW. CHEM., vol. 134, pages 202202898 - 1 *

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