CN110590846A - Light coupling-out material, preparation method thereof and organic electroluminescent device - Google Patents
Light coupling-out material, preparation method thereof and organic electroluminescent device Download PDFInfo
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- CN110590846A CN110590846A CN201910807772.9A CN201910807772A CN110590846A CN 110590846 A CN110590846 A CN 110590846A CN 201910807772 A CN201910807772 A CN 201910807772A CN 110590846 A CN110590846 A CN 110590846A
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- 239000000463 material Substances 0.000 title claims abstract description 52
- 238000002360 preparation method Methods 0.000 title description 6
- 238000000034 method Methods 0.000 claims abstract description 26
- 230000008569 process Effects 0.000 claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 239000000376 reactant Substances 0.000 claims description 47
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000012295 chemical reaction liquid Substances 0.000 claims description 17
- 235000011056 potassium acetate Nutrition 0.000 claims description 15
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical group [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 claims description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 238000010168 coupling process Methods 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 7
- 239000011261 inert gas Substances 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- IFGLECYAEGYLSJ-UHFFFAOYSA-N 2-bromo-3-fluoropyridine Chemical compound FC1=CC=CN=C1Br IFGLECYAEGYLSJ-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 239000004327 boric acid Substances 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- IMDXZWRLUZPMDH-UHFFFAOYSA-N dichlorophenylphosphine Chemical compound ClP(Cl)C1=CC=CC=C1 IMDXZWRLUZPMDH-UHFFFAOYSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 abstract description 6
- 238000001704 evaporation Methods 0.000 abstract description 6
- 230000008020 evaporation Effects 0.000 abstract description 5
- 230000007935 neutral effect Effects 0.000 abstract description 3
- 229910001392 phosphorus oxide Inorganic materials 0.000 abstract description 3
- 230000002194 synthesizing effect Effects 0.000 abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 239000005457 ice water Substances 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 238000009987 spinning Methods 0.000 description 8
- 239000012300 argon atmosphere Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000004949 mass spectrometry Methods 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 229940125898 compound 5 Drugs 0.000 description 6
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
- 229940125782 compound 2 Drugs 0.000 description 5
- 229940126214 compound 3 Drugs 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 2
- HYGLETVERPVXOS-UHFFFAOYSA-N 1-bromopyrene Chemical compound C1=C2C(Br)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 HYGLETVERPVXOS-UHFFFAOYSA-N 0.000 description 2
- AVESHYKDJMFQGJ-UHFFFAOYSA-N 4-bromo-2,6-diphenylpyridine Chemical compound C=1C(Br)=CC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 AVESHYKDJMFQGJ-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- -1 Bromo Chemical group 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
- C07F9/65685—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine oxide or thioxide
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Abstract
A light coupling-out material has a general structural formula ofThe R1 group and the R2 group are independently selected from an electron-withdrawing aromatic structure of a neutral aromatic structure or a nitrogen-containing heterocyclic ring. Through synthesizing N-doped phosphorus oxide aromatic group rodlike CPL material molecules, the CPL materials can be arranged more regularly and tightly in the evaporation process, the CPL has higher refractive index, so that a top-emitting electroluminescent device based on the CPL materials has higher luminous efficiency, the thickness of the CPL in the device can be reduced from 85 nanometers to 65 nanometers, and the production time and the capital cost can be saved.
Description
Technical Field
The invention relates to the technical field of semiconductors, in particular to a light coupling-out material, a preparation method thereof and an organic electroluminescent device.
Background
Organic Light-Emitting diodes (OLEDs) have attracted the attention of many researchers due to their advantages of active Light emission, large viewing angle, fast response speed, wide temperature application range, low driving voltage, low energy consumption, lighter weight, flexible display, and the like, as well as huge application prospects.
The OLED display device comprises a top emission device and a bottom emission device, and for the currently used top emission device structure, the microcavity effect of the OLED display device can greatly improve the efficiency of the device, narrow the spectrum and widen the color gamut. In the device structure, the light Coupling output Layer material (CPL) plays a great role, and the material with high refractive index can not only improve the device efficiency, but also reduce the thickness of the material, thereby achieving the purposes of saving the material and reducing the cost.
However, the refractive index of the CPL material is low, and the thickness of the light coupling-out layer formed by the CPL material in the evaporation process often exceeds 80nm, which results in a large thickness of the light emitting device, and is not favorable for the development of light and thin light emitting devices. In addition, the industry lacks a CPL material with a high refractive index, and even if the CPL material with a high refractive index can be synthesized, the reasonable route design is long and the synthesis efficiency is low.
Disclosure of Invention
The invention provides a light coupling-out material, a preparation method thereof and an organic electroluminescent device, and aims to solve the technical problems that the existing light coupling-out material is low in refractive index, and the thickness of a light coupling-out layer formed by a CPL material in an evaporation process is often more than 80nm, so that the thickness of the luminescent device is large, and the development of the luminescent device in a light and thin mode is not facilitated.
In order to solve the above problems, the technical scheme provided by the invention is as follows:
the invention provides a light coupling-out material, which is characterized in that the structural general formula is as follows:
wherein R is1Group and R2The groups are respectively and independently selected from any one of the following structural formulas:
the invention also provides a preparation method of the light coupling-out material, which comprises the following steps:
s10, mixing the first reactant, the second reactant, the catalyst and the solvent, and reacting to obtain a first intermediate;
s20, mixing the first intermediate with a third reactant, the catalyst and a solvent, and reacting to obtain the light coupling-out material, wherein the general structural formula of the light coupling-out material isR1Group and R2The groups are respectively and independently selected from any one of the following structural formulas:
in at least one embodiment of the present invention, the first reactant has the general structural formula:
in at least one embodiment of the present invention, the process for preparing the first reactant comprises:
reacting 2-bromo-3-fluoropyridine with pyridine-3-boric acid to obtain a second intermediate, wherein the structural formula of the second intermediate is shown in the specification
Reacting the second intermediate with phenyl phosphorus dichloride to obtain a third intermediate, wherein the structural formula of the third intermediate is shown in the specification
Reacting the third intermediate with liquid bromine and hydrogen peroxide to obtain a fourth intermediateThe structural formula of the fourth intermediate is
Reacting the fourth intermediate with a bis (pinacolato) diboron reagent to obtain the first reactant, wherein the structural formula of the first reactant is shown in the specification
In at least one embodiment of the present invention, the second reactant and the third reactant are each independently selected from one of the following structural formulas:
in at least one embodiment of the present invention, the catalyst is [1,1 '-bis (diphenylphosphino) ferrocene ] palladium dichloride and potassium acetate, and the solvent is N, N' -dimethylformamide.
In at least one embodiment of the present invention, the S10 includes:
s101, adding the first reactant, the second reactant, [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium, and potassium acetate to a first vessel;
s102, vacuumizing the container, introducing inert gas, and introducing deoxygenated N, N' -dimethylformamide into the container;
s103, reacting for 20-28 hours at 70-90 ℃ to obtain a first reaction liquid, and extracting and purifying the first reaction liquid to obtain the first intermediate.
In at least one embodiment of the present invention, the reaction temperature is 80 degrees Celsius and the reaction time is 24 hours.
In at least one embodiment of the present invention, the S20 includes:
s201, adding the first intermediate, the third reactant, [1,1' -bis (diphenylphosphino) ferrocene ] palladium dichloride, and potassium acetate to a second vessel;
s202, vacuumizing the second container, introducing inert gas, and introducing deoxygenated N, N' -dimethylformamide into the second container;
s203, reacting for 20-28 hours at 70-90 ℃ to obtain a second reaction solution, and extracting and purifying the second reaction solution to obtain the optical coupling-out material.
The invention also provides an organic electroluminescent device which comprises a light coupling-out layer, wherein the light coupling-out layer is made of the light coupling-out material or the light coupling-out material prepared by the method.
The invention has the beneficial effects that: through synthesizing N-doped phosphorus oxide aromatic group rodlike CPL material molecules, the CPL materials can be arranged more regularly and tightly in the evaporation process, the CPL has higher refractive index, so that a top-emitting electroluminescent device based on the CPL materials has higher luminous efficiency, the thickness of the CPL in the device can be reduced from 85 nanometers to 65 nanometers, and the production time and the capital cost can be saved.
Drawings
In order to illustrate the embodiments or the technical solutions in the prior art more clearly, the drawings needed to be used in the description of the embodiments or the prior art will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments of the invention, and it is obvious for a person skilled in the art that other drawings can be obtained according to these drawings without creative efforts.
FIG. 1 is a flow chart illustrating steps in a method for making a light outcoupling material according to an embodiment of the present invention;
FIG. 2 is a graph of photophysical properties of a synthetic target compound of an embodiment of the invention;
fig. 3 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present invention.
Detailed Description
The following description of the various embodiments refers to the accompanying drawings that illustrate specific embodiments in which the invention may be practiced. The directional terms mentioned in the present invention, such as [ upper ], [ lower ], [ front ], [ rear ], [ left ], [ right ], [ inner ], [ outer ], [ side ], are only referring to the directions of the attached drawings. Accordingly, the directional terms used are used for explanation and understanding of the present invention, and are not used for limiting the present invention. In the drawings, elements having similar structures are denoted by the same reference numerals.
The invention aims at the technical problems that the prior optical coupling output material has low refractive index, and when the material is applied to a CPL layer in an electroluminescent device, the thickness of the CPL layer often exceeds 80 nanometers, so that the thickness of the luminescent device is large, the development of the luminescent device is not facilitated, and the display is influenced.
The embodiment of the invention provides a light coupling-out material, which has a structural general formula ofWherein, R is1Group and R2The radicals R being identical or different1Group and R2The group is selected from electrically neutral aromatic structure or nitrogen heterocyclic ring electron-withdrawing aromatic structure.
Specifically, the electrically neutral aromatic structure is one of the following structural formulas, but is not limited to the following structural formula:
the electron-withdrawing aromatic structure of the nitrogen-containing heterocycle is selected from one of the following structural formulas, but is not limited to the following structural formula:
the light coupling-out material is of a N-doped phosphorus oxygen aromatic group rod-shaped molecular structure, so that the molecular arrangement is more regular and compact in the process of evaporating a light coupling-out layer, and the light coupling-out material has a very high refractive index.
As shown in fig. 1, an embodiment of the present invention further provides a method for preparing the light out-coupling material, including: s10, mixing the first reactant, the second reactant, the catalyst and the solvent, and reacting to obtain a first intermediate; and S20, mixing the first intermediate with a third reactant, the catalyst and a solvent, and reacting to obtain the light coupling-out material.
Specifically, the catalyst is [1,1 '-bis (diphenylphosphino) ferrocene ] palladium dichloride and potassium acetate, and the solvent is N, N' -dimethylformamide.
The S10 includes: first charging a first vessel with the first reactant, the second reactant, [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium, and potassium acetate; vacuumizing the container and introducing inert gas, and introducing deoxygenated N, N' -dimethylformamide into the container; and then reacting for 20-28 hours at 70-90 ℃ to obtain a first reaction liquid, and extracting and purifying the first reaction liquid to obtain the first intermediate.
The S20 includes: first charging a second vessel with the first intermediate, the third reactant, [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium, and potassium acetate; vacuumizing the second container, introducing inert gas, and introducing deoxygenated N, N' -dimethylformamide into the second container; and finally, reacting for 20-28 hours at 70-90 ℃ to obtain a second reaction solution, and extracting and purifying the second reaction solution to obtain the optical coupling-out material.
Wherein the structural formula of the first reactant isThe second reactant and the third reactant are respectively the same as R1Radical, R2Bromo corresponding to the radicalOne of the substances.
It will be understood that when R in the structural formula of the light outcoupling material is used1Group and R2When the groups are the same, the structural formulas of the third reactant and the second reactant are the same, that is, the same substance is obtained, when the optical coupling-out material is prepared, the two-step reaction in the preparation method can be combined into one-step reaction, the first reactant, the second reactant and the third reactant are mixed and then react, and the optical coupling-out material is obtained through extraction and purification.
The raw material of the first reactant can be 2-bromo-3-fluoropyridine, pyridine-3-boric acid, bromine simple substance and hydrogen peroxide, the 2-bromo-3-fluoropyridine is firstly reacted with the pyridine-3-boric acid to obtain a second intermediate, and the structural formula of the second intermediate is shown in the specificationThen reacting the second intermediate with phenyl phosphorus dichloride to obtain a third intermediate, wherein the structural formula of the third intermediate is shown in the specificationThen reacting the third intermediate with liquid bromine and hydrogen peroxide to obtain a fourth intermediate, wherein the structural formula of the fourth intermediate is shown in the specificationFinally, reacting the fourth intermediate with a bis (pinacolato) diboron reagent to obtain the first reactant. The process of the first reactant synthesis step is shown as the formula:
specifically, 2-bromo-3-fluoropyridine (1.75g, 10mmol), pyridine-3-boronic acid (1.48g, 12mmol), [1,1 '-bis (diphenylphosphino) ferrocene ] dichloropalladium (0.36g, 0.4mmol), and potassium acetate (0.12g, 1.2mmol) were added to a 250-mL two-neck flask, the two-neck flask containing the above-mentioned compounds was evacuated three times and filled with an inert gas such as nitrogen, argon, etc., then 100mL of N, N' -dimethylformamide, which had been previously deaerated, was charged to the two-neck flask, reacted at 80 ℃ for 24 hours and cooled to room temperature to obtain a reaction solution, the reaction solution was poured into 200mL of ice water, dichloromethane was extracted three times, the organic phases were combined, silica gel was spun, column chromatography (dichloromethane: N-hexane, v: v, 1:1) was separated and purified to obtain 1.62g of a second intermediate, which was white powder, the yield was 93%, and mass spectrometry gave an actual relative molecular mass of 174.00 for the second intermediate, which was 174.06 for the theoretical molecular mass.
Then, the second intermediate (1.74g, 10mmol) and phenylphosphorus dichloride (2.13g, 12mmol) were added to a 250mL two-necked flask, vacuum was applied three times, argon gas was introduced, 100mL of N, N' -dimethylformamide, which had been previously deoxygenated, was added to the two-necked flask, and the reaction was carried out at 120 ℃ for 24 hours. And cooling to room temperature, pouring the reaction liquid into 200mL of ice water, extracting with dichloromethane for three times, combining organic phases, spinning into silica gel, separating and purifying by column chromatography (dichloromethane: n-hexane, v: v, 3:1) to obtain 2.91g of a second intermediate, wherein the second intermediate is white powder, the yield is 67%, and the actual relative molecular mass of the third intermediate is 433.78 and the theoretical relative molecular mass is 433.88 through mass spectrometry.
Then, the third intermediate (2.62g, 10mmol) and 100mL of nitric acid were added to a 250mL two-necked flask, 10mL of liquid bromine was added dropwise with stirring, and the reaction solution was reacted at room temperature for 24 hours to obtain a reaction solution, the reaction solution was cooled to room temperature and poured into 200mL of ice water to precipitate a white solid, the white solid was dissolved with dichloromethane, 20mL of hydrogen peroxide was added, and the reaction solution was reacted at room temperature for 24 hours, and the reaction solution was poured into 200mL of ice water to precipitate a white solid (fourth intermediate) with a yield of 46%. The actual relative molecular mass of the fourth intermediate was 262.03 by apodisation, and the theoretical relative molecular mass was 206.07.
Finally, adding the fourth intermediate (4.34g, 10mmol), the diboron reagent (6.09g, 24mmol), the palladium acetate (90mg, 0.4mmol) and the potassium carbonate (1.66g, 12mmol) into a 250mL two-neck flask, vacuumizing three times and introducing argon, adding 100mL of N, N' -dimethylformamide which is deoxidized in advance into the two-neck flask, reacting at 100 ℃ for 24 hours, cooling to room temperature, pouring the reaction liquid into 200mL of ice water, extracting dichloromethane three times, combining organic phases, spinning into silica gel, and separating and purifying by column chromatography (dichloromethane: N-hexane, v: v, 1:1) to obtain 1.62g of white powder, namely the first reactant, wherein the yield is 93%, and the actual relative molecular mass of the first reactant is 530.20 and the theoretical relative molecular mass is 520.23 through mass spectrometry.
The production process of the present invention will be described in detail with reference to specific examples.
Example one
To a 250mL two-necked flask was added the first reactant (2.65g, 5mmol), 1-bromonaphthalene (2.47g, 12mmol), [1,1' -bis (diphenylphosphino) ferrocene]Vacuumizing three times, adding 100mL of N, N' -dimethylformamide which is deoxidized in advance into the palladium dichloride (0.36g, 0.4mmol) and potassium acetate (0.12g, 1.2mmol) under the argon atmosphere, reacting at 80 ℃ for 24 hours, cooling to room temperature, pouring the reaction liquid into 200mL of ice water, extracting three times by using dichloromethane, combining organic phases, spinning into silica gel, separating and purifying by column chromatography (dichloromethane: N-hexane, v: v, 1:1) to obtain a target compound 1, wherein the yield is 66%, the actual relative molecular mass of the target compound 1 is 530.10, the theoretical relative molecular mass is 530.15, and the structural formula of the target compound 1 is 530.15
The synthesis process of the target compound 1 is shown as the following formula:
example two
A250 mL two-necked flask was charged with the first reactant (2.65g, 5mmol), 1-bromopyrene, (3.36g, 12mmol) and [1,1' -bis (diphenylphosphino) ferrocene]Palladium dichloride (0.36g, 0.4mmol) and potassium acetate (0.12g, 1.2mmol) were evacuated three times, 100mL of N, N' -dimethylformamide, which had been previously deoxygenated, were added under an argon atmosphere, reacted at 80 ℃ for 24 hours, and cooledCooling to room temperature, pouring the reaction liquid into 200mL of ice water, extracting with dichloromethane for three times, combining organic phases, spinning into silica gel, separating and purifying by column chromatography (dichloromethane: n-hexane, v: v, 1:1) to obtain a target compound 2, wherein the yield is 71%, the actual relative molecular mass of the target compound 2 is 678.11, the theoretical relative molecular mass is 678.19, and the structural formula of the target compound 2 is shown in the specification
The synthesis process of the target compound 2 is shown as the following formula:
EXAMPLE III
To a 250mL two-necked flask were added the first reactant (2.65g, 5mmol), 4-bromo-2, 6-diphenylpyridine (3.71g, 12mmol), and [1,1' -bis (diphenylphosphino) ferrocene]Vacuumizing three times, adding 100mL of N, N' -dimethylformamide which is deoxidized in advance into the palladium dichloride (0.36g, 0.4mmol) and potassium acetate (0.12g, 1.2mmol) under the argon atmosphere, reacting for 24 hours at the temperature of 80 ℃, cooling to room temperature, pouring the reaction liquid into 200mL of ice water, extracting the dichloromethane for three times, combining organic phases, spinning into silica gel, separating and purifying by column chromatography (dichloromethane: N-hexane, v: v, 1:1) to obtain a target compound 3, wherein the yield is 58%, the actual relative molecular mass of the target compound 3 is 736.09, the theoretical relative molecular mass is 736.24, and the structural formula of the target compound 3 is 736.24
The synthesis process of the target compound 3 is shown as the following formula:
example four
First, a 250mL two-necked flask was charged with 1(2.65g, 5mmol) as a starting material, 1-bromonaphthalene (1.24g, 6mmol) and [1,1' -bis (diphenylphosphino) ferrocene]Pumping palladium dichloride (0.36g, 0.4mmol) and potassium acetate (0.12g, 1.2mmol) for three times, adding 100mL of N, N' -dimethylformamide which is deoxidized in advance under the argon atmosphere, reacting for 24 hours at 80 ℃ to obtain a first reaction liquid, cooling to room temperature, pouring the first reaction liquid into 200mL of ice water, extracting for three times by using dichloromethane, combining organic phases, spinning into silica gel, separating and purifying column chromatography (dichloromethane: N-hexane, v: v, 1:1) to obtain a first intermediate, wherein 1.93g of white powder is obtained, the yield is 73%, mass spectrometry is carried out to obtain the first intermediate, the actual relative molecular mass is 530.08, the theoretical relative molecular mass is 530.19, and the structural formula of the first intermediate is represented by
The synthesis process of the first intermediate is shown as the following formula:
then the first intermediate (2.65g, 5mmol), 1-bromopyrene (1.68g, 6mmol) and [1,1' -bis (diphenylphosphino) ferrocene were added to a 250mL two-necked flask]Vacuumizing three times, adding 100mL of N, N' -dimethylformamide which is deoxidized in advance into the mixture under the argon atmosphere, reacting at 80 ℃ for 24 hours to obtain a second reaction liquid, cooling to room temperature, pouring the second reaction liquid into 200mL of ice water, extracting three times by using dichloromethane, combining organic phases, carrying out spinning to obtain silica gel, and carrying out column chromatography (dichloromethane: N-hexane, v: v, 1:1) to obtain a target compound 4, wherein the yield is 70% and 2.11g of white powder is obtained through separation and purification, mass spectrometry is carried out to obtain the target compound 4, the actual relative molecular mass is 604.01, the theoretical relative molecular mass is 604.17, and the structural formula of the target compound 4 is 604.17
The synthesis process of the target compound 4 is shown as the following formula:
EXAMPLE five
On the basis of the synthesis of the first intermediate in example four, a target compound 5 is synthesized, and the synthesis process of the target compound 5 is shown as the following formula:
to a 250mL two-necked flask was added the first intermediate (2.65g, 5mmol), 4-bromo-2, 6-diphenylpyridine (1.85g, 6mmol), [1,1' -bis (diphenylphosphino) ferrocene]Vacuumizing three times, adding 100mL of N, N' -dimethylformamide which is deoxidized in advance into the mixture under the argon atmosphere, reacting at 80 ℃ for 24 hours to obtain a second reaction liquid, cooling to room temperature, pouring the second reaction liquid into 200mL of ice water, extracting three times by using dichloromethane, combining organic phases, spinning into silica gel, separating and purifying by column chromatography (dichloromethane: N-hexane, v: v, 1:1) to obtain the target compound 5, wherein the yield of the white powder is 2.47g, the actual relative molecular mass of the target compound 5 is 633.12%, the theoretical relative molecular mass is 633.20, and the structural formula of the target compound 5 is 633.20% by mass spectrometry
EXAMPLE six
To a 250mL two-necked flask was added the first reactant (2.65g, 5mmol), 2-bromo-4, 6-di-p-tolyl- [1,3, 5%]Triazine (4.07g, 12mmol), [1,1' -bis (diphenylphosphino) ferrocene]Palladium dichloride (0.36g, 0.4mmol) and potassium acetate (0.12g, 1.2mmol) were evacuated three times, 100mL of N, N' -dimethylformamide, which had been previously deoxygenated, were added under an argon atmosphere, reacted at 80 ℃ for 24 hours, cooled to room temperature, the reaction solution was poured into 200mL of ice water, and dichloromethane was addedThe mixture was extracted with hexane three times, the organic phases were combined, spun into silica gel, and subjected to column chromatography (dichloromethane: n-hexane, v: v, 1:1) for separation and purification to give the objective compound 6 as a white powder 5.66g, in 67% yield. The actual relative molecular mass of the target compound 6 obtained by mass spectrometry is 796.18, and the structural formula of the target compound 6 is shown in the specification
The synthesis process of the target compound 6 is shown as the following formula:
as shown in fig. 2, fig. 2 is a graph of photophysical properties of target compounds 1 to 5 synthesized in the embodiment of the present invention, the abscissa is a wavelength λ (nm), and the ordinate is a refractive index n, and it can be seen from fig. 2 that the target compound provided in the embodiment of the present invention has a refractive index greater than 1.70 in a light wavelength range of 380 to 780nm, and has a higher refractive index.
Based on the application of the light coupling-out material, as shown in fig. 3, an embodiment of the present invention further provides an organic electroluminescent device 100, where in the embodiment of the present invention, a top emission device is taken as an example, the organic electroluminescent device 100 includes a substrate 10, a reflective electrode layer 20, a hole injection layer 30, a hole transport layer 40, an electron blocking layer 50, a light emitting layer 60, a hole blocking layer 70, an electron transport layer 80, an electron injection layer 90, a semitransparent electrode layer 10 ', and a light coupling-out layer 20 ' that are sequentially stacked, where the light coupling-out layer 20 ' adopts the light coupling-out material prepared by the above method. Compared with the thickness of the existing light coupling-out layer, the light coupling-out layer 20 provided by the embodiment of the invention has the advantages that the refractive index is improved, the thickness of the film layer can be reduced from 85 nanometers to about 65 nanometers, and the light and thin development of a light-emitting device is facilitated.
As shown in table 1 below, table 1 shows performance data of the organic electroluminescent device corresponding to each example.
TABLE 1
| Device with a metal layer | Light out-coupling material | Maximum current efficiency (cd/A) | (CIEx,CIEy) | Maximum external quantum efficiency (%) |
| Device 1 | Object Compound 1 | 6.1 | (0.13,0.045) | 13.8％ |
| Device 2 | Target Compound 2 | 5.8 | (0.13,0.046) | 12.6％ |
| Device 3 | Target Compound 3 | 6.6 | (0.13,0.045) | 14.9％ |
| Device 4 | Target Compound 4 | 6.3 | (0.13,0.046) | 14.3％ |
| Device 5 | Target Compound 5 | 6.0 | (0.13,0.045) | 13.2％ |
| Device 6 | Target Compound 6 | 6.1 | (0.13,0.045) | 13.8％ |
Has the advantages that: through synthesizing N-doped phosphorus oxide aromatic group rodlike CPL material molecules, the CPL materials can be arranged more regularly and tightly in the evaporation process, the CPL has higher refractive index, so that a top-emitting electroluminescent device based on the CPL materials has higher luminous efficiency, the thickness of the CPL in the device can be reduced from 85 nanometers to 65 nanometers, and the production time and the capital cost can be saved.
In summary, although the present invention has been described with reference to the preferred embodiments, the above-described preferred embodiments are not intended to limit the present invention, and those skilled in the art can make various changes and modifications without departing from the spirit and scope of the present invention, therefore, the scope of the present invention shall be determined by the appended claims.
Claims (10)
1. A light outcoupling material, characterized by the general structural formula:
wherein the content of the first and second substances,
R1group and R2Each radical is independently selected fromAny one of the following structural formulas:
2. a method of making a light out-coupling material, comprising:
s10, mixing the first reactant, the second reactant, the catalyst and the solvent, and reacting to obtain a first intermediate;
s20, mixing the first intermediate with a third reactant, the catalyst and the solvent, and reacting to obtain the light coupling-out material, wherein the general structural formula of the light coupling-out material isR1Group and R2The groups are respectively and independently selected from any one of the following structural formulas:
3. the method of claim 2, wherein the first reactant has the general structural formula:
4. the method of claim 3, wherein the first reactant is prepared by a process comprising:
reacting 2-bromo-3-fluoropyridine with pyridine-3-boric acid to obtain a second intermediate, wherein the structural formula of the second intermediate is shown in the specification
Reacting the second intermediate with phenyl phosphorus dichloride to obtain a third intermediate, wherein the structural formula of the third intermediate is shown in the specification
Reacting the third intermediate with liquid bromine and hydrogen peroxide to obtain a fourth intermediate, wherein the structural formula of the fourth intermediate is shown in the specification
Reacting the fourth intermediate with a bis (pinacolato) diboron reagent to obtain the first reactant, wherein the structural formula of the first reactant is shown in the specification
5. The method of claim 2, wherein the second reactant and the third reactant are each independently selected from one of the following structural formulas:
6. the method according to claim 2, wherein the catalyst is [1,1 '-bis (diphenylphosphino) ferrocene ] dichloropalladium and potassium acetate, and the solvent is N, N' -dimethylformamide.
7. The method according to claim 6, wherein the S10 includes:
s101, adding the first reactant, the second reactant, [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium, and potassium acetate to a first vessel;
s102, vacuumizing the container, introducing inert gas, and introducing deoxygenated N, N' -dimethylformamide into the container;
s103, reacting for 20-28 hours at 70-90 ℃ to obtain a first reaction liquid, and extracting and purifying the first reaction liquid to obtain the first intermediate.
8. The method according to claim 7, wherein the reaction temperature is 80 ℃ and the reaction time is 24 hours.
9. The method according to claim 7, wherein the S20 includes:
s201, adding the first intermediate, the third reactant, [1,1' -bis (diphenylphosphino) ferrocene ] palladium dichloride, and potassium acetate to a second vessel;
s202, vacuumizing the second container, introducing inert gas, and introducing deoxygenated N, N' -dimethylformamide into the second container;
s203, reacting for 20-28 hours at 70-90 ℃ to obtain a second reaction solution, and extracting and purifying the second reaction solution to obtain the optical coupling-out material.
10. An organic electroluminescent device comprising a light out-coupling layer of the light out-coupling material of claim 1.
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| CN111100126A (en) * | 2019-12-31 | 2020-05-05 | 厦门天马微电子有限公司 | Compound, display panel and display device |
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| CN110950858A (en) * | 2019-10-31 | 2020-04-03 | 武汉华星光电半导体显示技术有限公司 | Coupling light-emitting material and preparation method thereof |
| CN111100126A (en) * | 2019-12-31 | 2020-05-05 | 厦门天马微电子有限公司 | Compound, display panel and display device |
| CN111100126B (en) * | 2019-12-31 | 2021-06-01 | 厦门天马微电子有限公司 | Compound, display panel and display device |
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