CN114933559A - Luminous auxiliary material and preparation method thereof, light-emitting device and light-emitting device - Google Patents

Luminous auxiliary material and preparation method thereof, light-emitting device and light-emitting device Download PDF

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CN114933559A
CN114933559A CN202210694403.5A CN202210694403A CN114933559A CN 114933559 A CN114933559 A CN 114933559A CN 202210694403 A CN202210694403 A CN 202210694403A CN 114933559 A CN114933559 A CN 114933559A
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汪康
贾宇
陈振生
王永光
唐志杰
白金凤
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

The luminescent auxiliary material is connected with an aromatic amine group by a phenyl carbazole skeleton through a phenyl group, adamantane is introduced, molecular conjugation is prolonged, electronic localization is avoided, electronic separation and transmission are facilitated, and the hole mobility, the spatial structure and the energy level of a compound are changed, so that the luminescent auxiliary material is more adaptive to the luminescent device, and the driving voltage can be reduced while the service life and the luminous efficiency of the luminescent device are effectively improved through structural optimization of the luminescent device; in addition, the asymmetry of the single triarylamine structure in the application can reduce the planarity of molecules and prevent the molecules from moving on a plane, and the triarylamine also has high hole transport rate, so that the driving voltage of a light-emitting device can be reduced, the efficiency of the light-emitting device can be further improved, and the service life of the light-emitting device can be further prolonged.

Description

Luminous auxiliary material and preparation method thereof, light-emitting device and light-emitting device
Technical Field
The application belongs to the technical field of materials, and particularly relates to a luminescent auxiliary material, a preparation method thereof, a luminescent device and a luminescent device.
Background
The organic electroluminescent (OLED) device technology can be used for manufacturing novel display products and novel lighting products, is expected to replace the existing liquid crystal display and fluorescent lamp lighting, and has wide application prospect. An organic electric element utilizing an organic light emitting phenomenon generally has an anode, a cathode, and a structure including an organic layer therebetween. In order to increase the efficiency and stability of organic electrical components, the organic layers are generally composed of multilayer structures of various substances.
The photoelectric functional materials of the OLED applied to the OLED device can be divided into two categories from the aspect of application, namely charge injection transmission materials and luminescent materials. Further, the charge injection transport material may be classified into an electron injection transport material, an electron blocking material, a hole injection transport material, and a hole blocking material, and the light emitting material may be classified into a host light emitting material and a doping material.
The Hole Transport Layer (HTL) is responsible for adjusting the injection speed and the injection amount of holes because thermal stress occurs between the anode and the hole injection layer when the OLED is driven at a high current, and the thermal stress may significantly reduce the lifespan of the device, which is problematic in terms of efficiency, voltage, and lifespan. Therefore, in order to solve the above problems, it is common to add a light-emission auxiliary layer between the hole transport layer and the light-emitting layer (i.e., to provide multiple hole transport layers) to improve device lifetime and efficiency. The light-emitting auxiliary layer can play a role in reducing potential barrier between the hole transport layer and the light-emitting layer, reducing the driving voltage of the organic electroluminescent device and further increasing the utilization rate of holes, thereby improving the luminous efficiency and the service life of the device and reducing the driving voltage. However, the number of functional materials that can form a light emission auxiliary layer is small.
The research on organic electroluminescent materials has been widely carried out in academia and industry, but the development of stable and efficient organic layer materials for organic electronic devices has not been fully developed so far, and the industrialization process of the technology still faces many key problems, so how to develop a new luminescent auxiliary material is a problem to be solved urgently by those skilled in the art.
Disclosure of Invention
An object of the embodiment of the present application is to provide a luminescent auxiliary material, which aims to solve the problem that the lifetime and the luminous efficiency of a device are not obviously improved by the existing luminescent auxiliary material.
The embodiment of the application is realized by the following steps that the structure general formula of the luminescence auxiliary material is shown as the general formula I:
Figure BDA0003700119890000021
wherein the content of the first and second substances,
L 1 、L 2 the two groups are the same or different and are respectively and independently one of a connecting bond, substituted or unsubstituted aryl of C6-C30 and substituted or unsubstituted heteroaryl of C6-C30, wherein hetero atoms are selected from oxygen, nitrogen and sulfur;
p and q independently represent 0 or 1 and are not 0 at the same time;
R 3 、R 4 one selected from hydrogen, deuterium, substituted or unsubstituted C1-C15 alkane, substituted or unsubstituted C1-C18 cycloalkane, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C6-C30 heteroaryl, which are the same or different from each other and are each independently, wherein the heteroatom is selected from oxygen, nitrogen and sulfur;
m and n are respectively independent and represent an integer of 0-4;
Ar 1 、Ar 2 identical or different from each other and each independently of the others, is one selected from the group consisting of substituted or unsubstituted 3-to 30-membered heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, wherein the heteroatom is selected from the group consisting of oxygen, nitrogen, sulfur.
Another object of the present application is to provide a method for preparing the above luminescent auxiliary material, comprising:
Figure BDA0003700119890000031
wherein, Hal 1 、Hal 2 、Hal 3 The same or different from each other and independent from each other, is selected from one of fluorine, chlorine, bromine and iodine;
dissolving the raw materials A and B in toluene, and reacting the solution in N 2 Adding Pd under atmosphere 2 (dba) 3 、P(t-Bu) 3 And t-BuONa, heating to 110-120 ℃, and stirring for reaction for 10-12h to obtain an intermediate 1;
in N 2 Under protection, the intermediate 1 and the raw material C, Pd are mixed 2 (dba) 3 、P(t-Bu) 3 And t-BuONa, heating to 110-120 ℃, and stirring for reaction for 12-14h to obtain an intermediate 2;
dissolving the intermediate 2 and the raw material D in a mixed solution of toluene, ethanol and water, adding potassium carbonate and a palladium catalyst under the protection of nitrogen, uniformly stirring, heating to 80-90 ℃, and carrying out reflux reaction for 6-8h to obtain the organic compound shown in the general formula 1.
Another object of the present application is the use of the above-mentioned luminescent auxiliary material in the field of optoelectronics.
Another object of the present application is a light emitting device comprising a luminescent auxiliary material as described above.
Another object of the present application is to provide a light emitting device including the above light emitting device.
According to the luminescent auxiliary material provided by the application, a phenylcarbazole skeleton is connected with an arylamine group through a phenyl group, adamantane is introduced, molecular conjugation is prolonged, electronic localization is avoided, electronic separation and transmission are facilitated, and the hole mobility, the space structure and the energy level of a compound are changed, so that the luminescent auxiliary material is more adaptive on a luminescent device, and through structural optimization of the luminescent device, the service life and the luminous efficiency of the luminescent device can be effectively prolonged, and meanwhile, the driving voltage is reduced; in addition, the asymmetry of the single triarylamine structure in the application can reduce the planarity of molecules and prevent the molecules from moving on a plane, and the triarylamine also has high hole transport rate, so that the driving voltage of a light-emitting device can be reduced, the efficiency of the light-emitting device can be further improved, and the service life of the light-emitting device can be further prolonged.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of a raw material D provided in an example of the present application;
fig. 2 is a nuclear magnetic resonance hydrogen spectrum of compound 1 provided in example 1 of the present application.
Detailed Description
In order to make the objects, technical solutions and advantages of the present application more apparent, the present application is described in further detail below with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the present application and are not intended to limit the present application.
The application provides a luminescent auxiliary material, which has a structural general formula shown as a general formula I:
Figure BDA0003700119890000051
substituent range:
in the above formula L 1 、L 2 The two groups are the same or different and are respectively and independently one of a connecting bond, substituted or unsubstituted aryl of C6-C30 and substituted or unsubstituted heteroaryl of C6-C30, wherein the heteroatom is selected from oxygen, nitrogen and sulfur.
p and q independently represent 0 or 1, and are not simultaneously 0.
R 3 、R 4 The same or different from each other and each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C15 alkane, substituted or unsubstitutedSubstituted C1-C18 cycloalkane, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, wherein the heteroatoms are selected from oxygen, nitrogen, sulfur. Wherein m and n are respectively independent integers from 0 to 4.
Ar 1 、Ar 2 Identical to or different from each other and each independently selected from substituted or unsubstituted 3-to 30-membered heterocycloalkyl, the heteroatoms of which are selected from oxygen, nitrogen, sulphur; substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, the heteroatoms of which are selected from oxygen, nitrogen, sulfur.
Preferably, said R is 3 、R 4 Identical or different from each other and independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C6 alkane, substituted or unsubstituted C1-C6 cycloalkane, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C6-C18 heteroaryl, wherein the heteroatoms are selected from nitrogen, oxygen, sulphur.
Preferably, Ar 1 、Ar 2 The following groups and any combination of the following groups:
Figure BDA0003700119890000061
wherein in the above formula is indicated as the point of attachment.
In the present specification, "substituted" means substituted with one, two or more substituents selected from: C1-C20 alkyl, C1-C20 alkoxy, C6-C30 aryl and C6-C30 heteroaryl, wherein the heteroatoms are selected from oxygen, nitrogen and sulfur.
Further, in the above-mentioned light-emitting auxiliary material, any one selected from compounds represented by the following structural formulae:
Figure BDA0003700119890000071
Figure BDA0003700119890000081
Figure BDA0003700119890000091
Figure BDA0003700119890000101
Figure BDA0003700119890000111
Figure BDA0003700119890000121
Figure BDA0003700119890000131
Figure BDA0003700119890000141
another objective of the present application is to provide a method for preparing the above luminescent auxiliary material, wherein the synthetic route of the compound represented by formula I is:
Figure BDA0003700119890000151
in the formula L 1 、L 2 、Ar 1 、Ar 2 、R 3 、R 4 M, n, p, q are as defined above; hal (halogen over glass) 1 、Hal 2 、Hal 3 The same or different from each other and independent from each other, is one selected from fluorine, chlorine, bromine and iodine;
dissolving the raw materials A and B in toluene, and reacting the solution in N 2 Adding Pd under atmosphere 2 (dba) 3 、P(t-Bu) 3 And t-BuONa, heating to 110-120 ℃, stirring and reacting for 10-12h, and after the reaction is finishedPerforming suction filtration by using diatomite while hot, removing salts and a catalyst, cooling the filtrate to room temperature, adding distilled water into the filtrate, washing, separating liquid, retaining an organic phase, extracting an aqueous phase by using ethyl acetate, drying a combined organic layer by using magnesium sulfate, removing the solvent by using a rotary evaporator, and finally purifying the rest substance by using a column chromatography by using a mixture of dichloromethane and petroleum ether as an eluent to obtain a compound shown as an intermediate 1;
in N 2 Under protection, the intermediate 1 and the raw material C, Pd are mixed 2 (dba) 3 、P(t-Bu) 3 And t-BuONa, heating to 110-120 ℃, stirring for reaction for 12-14h, performing suction filtration by using diatomite while hot after the reaction is finished, removing salts and a catalyst, cooling the filtrate to room temperature, adding distilled water into the filtrate for washing, separating liquid, retaining an organic phase, extracting an aqueous phase by using ethyl acetate, drying a combined organic layer by using magnesium sulfate, removing the solvent by using a rotary evaporator, and finally purifying the residual substance by using a column chromatography by using a mixture of dichloromethane and petroleum ether as an eluent to obtain a compound shown as an intermediate 2;
dissolving the intermediate 2 and the raw material D in a mixed solution of toluene ethanol and water, then ventilating for 3 times, adding potassium carbonate and a palladium catalyst under the protection of nitrogen, uniformly stirring, heating to 80-90 ℃, and performing reflux reaction for 6-8 hours; after the reaction is finished, slightly cooling, filtering by using kieselguhr, removing salt and a catalyst, cooling the filtrate to room temperature, washing with water for three times to keep an organic phase, and extracting an aqueous phase by using ethyl acetate; after the organic phases were combined, dried using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain a solid organic substance. And completely dissolving the solid organic matter by using a small amount of dichloromethane, slowly and dropwisely adding the dissolved solid organic matter into a petroleum ether solution, uniformly stirring, precipitating, carrying out suction filtration to obtain a solid, sequentially leaching by using absolute ethyl alcohol and petroleum ether, and drying to obtain the compound shown in the general formula I.
Through the technical scheme, compared with the prior art, the method has the following beneficial effects:
1. the organic electroluminescent compound with excellent performance for the blue light emitting auxiliary layer is obtained by connecting a phenylcarbazole skeleton with an arylamine group through phenyl, and the prepared device has the characteristics of high luminous efficiency, low driving voltage, long service life and the like.
2. The adamantane is introduced into the compound, so that electronic localization is avoided, electronic separation and transmission are facilitated, and the hole mobility, the space structure and the energy level of the compound are changed, so that the compound is more adaptive to devices, and the service life and the luminous efficiency of OLED devices can be effectively prolonged and the driving voltage can be reduced through structural optimization of the devices.
3. The asymmetry of the monotriarylamine structure in the compound can reduce the planarity of molecules and prevent the molecules from moving on a plane, and the triarylamine also has high hole transport rate, so that the driving voltage of the device can be reduced, the efficiency of the organic electroluminescent device can be further improved, and the service life of the organic electroluminescent device can be further prolonged.
The technical solutions in the embodiments of the present application will be described clearly and completely below with reference to the luminescent auxiliary material of the present application, and it is obvious that the described embodiments are only a part of the embodiments of the present application, and not all embodiments.
In addition, it should be noted that the numerical values given in the following examples are as precise as possible, but those skilled in the art understand that each numerical value should be understood as a divisor rather than an absolutely exact numerical value due to measurement errors and experimental operational problems that cannot be avoided.
The synthesis of starting material D in all the following examples is as follows:
Figure BDA0003700119890000171
in N 2 Dissolving a raw material D-1(40.00mmol) in a dichloromethane solution, adding a raw material D-2(40.00mmol), adding methanesulfonic acid (MSA) (160.00mmol), stirring at room temperature for 6h, finishing the reaction, adding distilled water into the reaction solution, washing, separating, retaining an organic phase, removing the solvent by using a rotary evaporator, and precipitating a solid to obtain a compound shown as an intermediate D-1(11.55g, yield: 69.25%);
intermediate D-1(27.68mmol) and starting material D-3(27.68mmol) were dissolved in toluene and the solution was filtered through a column of celite 2 Adding Pd under atmosphere 2 (dba) 3 (0.27mmol)、P(t-Bu) 3 (1.38mmol) and t-BuONa (55.36mmol), heating to 120 ℃ and stirring for reaction for 14h, after the reaction is finished, carrying out suction filtration by using diatomite while hot, removing salts and a catalyst, cooling the filtrate to room temperature, adding distilled water into the filtrate for washing, separating liquid, retaining an organic phase, extracting an aqueous phase by using ethyl acetate, drying a combined organic layer by using magnesium sulfate, removing the solvent by using a rotary evaporator, and finally purifying the remaining substance by using a column chromatography by using a mixture of dichloromethane and petroleum ether (V: V ═ 1:6) as an eluent to obtain a raw material D (7.21g, yield: 57.15%).
Nuclear magnetic resonance hydrogen spectrum: as shown in fig. 1.
Example 1
Figure BDA0003700119890000181
Starting materials A (40.00mmol) and B (40.00mmol) were dissolved in toluene and the solution was filtered through a column of toluene 2 Adding Pd under atmosphere 2 (dba) 3 (0.40mmol)、P(t-Bu) 3 (2.00mmol) and t-BuONa (80.00mmol), heating to 120 ℃ and stirring for reaction for 12h, after the reaction is finished, suction-filtering with diatomaceous earth while hot, removing salts and catalyst, cooling the filtrate to room temperature, adding distilled water to the filtrate for washing, separating the liquid, retaining the organic phase, extracting the aqueous phase with ethyl acetate, drying the combined organic layer with magnesium sulfate, removing the solvent with a rotary evaporator, and finally purifying the remaining substance with column chromatography using a mixture of dichloromethane and petroleum ether (V: V ═ 1:8) as an eluent to obtain the compound represented by intermediate 1 (10.42g, yield: 81.12%).
Intermediate 1(32.41mmol) and starting material C (32.41mmol) were dissolved in toluene and then purified by filtration under N 2 Adding Pd under atmosphere 2 (dba) 3 (0.32mmol)、P(t-Bu) 3 (1.62mmol) and t-BuONa (64.82mmol), heating to 120 ℃ and stirring for reaction for 14h,after the reaction was completed, suction filtration was performed using celite while hot to remove salts and a catalyst, the filtrate was cooled to room temperature, then distilled water was added to the filtrate to wash, the organic phase was retained after liquid separation, the aqueous phase was extracted with ethyl acetate, then the combined organic layer was dried with magnesium sulfate, and the solvent was removed using a rotary evaporator, and finally the remaining substance was purified by column chromatography using a mixture of dichloromethane and petroleum ether (V: V ═ 1:4) as an eluent, to obtain intermediate 2(10.93g, yield 76.48%).
Dissolving the intermediate 2(24.76mmol) and the raw material D (24.76mmol) in a mixed solution of toluene ethanol and water (volume ratio is 2:2:1), then ventilating for 3 times, adding potassium carbonate (49.52mmol) and tetrakistriphenylphosphine palladium (0.24mmol) under the protection of nitrogen, stirring uniformly, heating to 90 ℃, and carrying out reflux reaction for 8 hours; after the reaction is finished, slightly cooling, filtering by using kieselguhr, removing salt and a catalyst, cooling the filtrate to room temperature, washing with water for three times to keep an organic phase, and extracting an aqueous phase by using ethyl acetate; after the organic phases were combined, dried using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain a solid organic matter. And (2) completely dissolving the solid organic matter by using a small amount of dichloromethane, slowly and dropwise adding the dichloromethane into the petroleum ether solution, uniformly stirring, precipitating, carrying out suction filtration to obtain a solid, sequentially leaching by using absolute ethyl alcohol and petroleum ether, and drying to obtain a compound 1(14.77g, yield: 77.18%, Mw: 773.04).
Mass spectrometry test: a theoretical value of 773.04; the test value was 773.15.
Elemental analysis:
the calculated values are: c, 90.12; h, 6.26; and N, 3.62.
The test values are: c, 89.67; h, 6.55; and N, 3.81.
Nuclear magnetic resonance hydrogen spectrum: as shown in fig. 2.
Example 2
Figure BDA0003700119890000201
Starting materials A (40.00mmol) and B (40.00mmol) were dissolved in toluene and the solution was purified over N 2 In the atmosphereAdding Pd 2 (dba) 3 (0.40mmol)、P(t-Bu) 3 (2.00mmol) and t-BuONa (80.00mmol), heating to 120 ℃ and stirring for reaction for 12h, after the reaction is finished, suction-filtering with diatomaceous earth while hot, removing salts and catalyst, cooling the filtrate to room temperature, adding distilled water to the filtrate for washing, separating the liquid, retaining the organic phase, extracting the aqueous phase with ethyl acetate, drying the combined organic layer with magnesium sulfate, removing the solvent with a rotary evaporator, and finally purifying the remaining substance with column chromatography using a mixture of dichloromethane and petroleum ether (V: V ═ 1:8) as an eluent to obtain the compound represented by intermediate 1 (10.09g, yield: 78.59%).
Intermediate 1(31.39mmol) and starting material C (31.39mmol) were dissolved in toluene and then purified by filtration under N 2 Adding Pd under atmosphere 2 (dba) 3 (0.31mmol)、P(t-Bu) 3 (1.56mmol) and t-BuONa (62.78mmol), heating to 120 ℃ and stirring for 14h, after the reaction is finished, suction filtering with diatomaceous earth while hot, removing salts and catalyst, cooling the filtrate to room temperature, adding distilled water to the filtrate for washing, separating the liquid, retaining the organic phase, extracting the aqueous phase with ethyl acetate, drying the combined organic layers with magnesium sulfate, removing the solvent with a rotary evaporator, and finally purifying the remaining material by column chromatography with a mixture of dichloromethane and petroleum ether (V: V ═ 1:4) as eluent to give intermediate 2(13.27g, yield 73.48%).
Dissolving the intermediate 2(23.05mmol) and the raw material D (23.05mmol) in a mixed solution of toluene ethanol and water (volume ratio is 2:2:1), then ventilating for 3 times, adding potassium carbonate (46.10mmol) and tetrakistriphenylphosphine palladium (0.23mmol) under the protection of nitrogen, stirring uniformly, heating to 90 ℃, and carrying out reflux reaction for 8 hours; after the reaction is finished, slightly cooling, filtering by using kieselguhr, removing salt and a catalyst, cooling the filtrate to room temperature, washing with water for three times to keep an organic phase, and extracting an aqueous phase by using ethyl acetate; after the organic phases were combined, dried using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain a solid organic matter. And (3) completely dissolving the solid organic matter by using a small amount of dichloromethane, slowly dropwise adding the dissolved organic matter into a petroleum ether solution, uniformly stirring, precipitating, carrying out suction filtration to obtain a solid, sequentially leaching with absolute ethyl alcohol and petroleum ether, and drying to obtain a compound 61(13.63g, yield: 76.54%, Mw: 773.04).
Mass spectrum testing: a theoretical value of 773.04; the test value was 773.26.
Elemental analysis:
the calculated values are: c, 90.12; h, 6.26; and N, 3.62.
The test values are: c, 89.71; h, 6.52; and N, 3.86.
Example 3
Figure BDA0003700119890000221
Starting materials A (40.00mmol) and B (40.00mmol) were dissolved in toluene and the solution was purified over N 2 Adding Pd under atmosphere 2 (dba) 3 (0.40mmol)、P(t-Bu) 3 (2.00mmol) and t-BuONa (80.00mmol), heating to 120 ℃ and stirring for reaction for 12h, after the reaction is finished, carrying out suction filtration by using diatomite while hot, removing salts and a catalyst, cooling the filtrate to room temperature, adding distilled water into the filtrate for washing, separating liquid, retaining an organic phase, extracting an aqueous phase by using ethyl acetate, then drying a combined organic layer by using magnesium sulfate, removing the solvent by using a rotary evaporator, and finally purifying the remaining substance by using a column chromatography by using a mixture of dichloromethane and petroleum ether (V: V ═ 1:8) as an eluent to obtain a compound represented by an intermediate 1 (13.99g, yield: 78.19%).
Intermediate 1(31.25mmol) and starting material C (31.25mmol) were dissolved in toluene and the solution was purified by filtration under N 2 Adding Pd2(dba)3(0.31mmol), P (t-Bu)3(1.56mmol) and t-BuONa (62.50mmol) under atmosphere, heating to 120 ℃ and stirring for reaction for 14h, after the reaction is finished, using diatomite to perform suction filtration while hot, removing salts and a catalyst, after the filtrate is cooled to room temperature, adding distilled water into the filtrate for washing, after liquid separation, retaining an organic phase, extracting an aqueous phase with ethyl acetate, then using magnesium sulfate to dry a combined organic layer, using a rotary evaporator to remove a solvent, finally using a mixture of dichloromethane and petroleum ether (V: V ═ 1:4) as an eluent, and purifying the rest substance by column chromatography to obtain an intermediate substanceBody 2(13.22g, 74.58% yield).
Dissolving the intermediate 2(23.29mmol) and the raw material D (23.29mmol) in a mixed solution of toluol and water (volume ratio is 2:2:1), then ventilating for 3 times, adding potassium carbonate (46.58mmol) and tetrakistriphenylphosphine palladium (0.23mmol) under the protection of nitrogen, stirring uniformly, heating to 90 ℃, and carrying out reflux reaction for 8 hours; after the reaction is finished, slightly cooling, filtering by using kieselguhr, removing salt and a catalyst, cooling the filtrate to room temperature, washing with water for three times to keep an organic phase, and extracting an aqueous phase by using ethyl acetate; after the organic phases were combined, dried using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain a solid organic matter. And (2) completely dissolving the solid organic matter by using a small amount of dichloromethane, slowly dropwise adding the dissolved organic matter into a petroleum ether solution, uniformly stirring, precipitating, filtering to obtain a solid, sequentially leaching by using absolute ethyl alcohol and petroleum ether, and drying to obtain a compound 73(15.39g, yield: 73.54%, Mw: 899.19).
Mass spectrum testing: a theoretical value of 899.19; the test value was 899.32.
Elemental analysis:
the calculated values are: c, 90.83; h, 6.05; and N, 3.12.
The test values are: c, 90.41; h, 6.37; n, 3.44.
The general structural formula is formula 1 in the summary of the invention, and the synthetic routes and principles of other compounds are the same as those of the above-listed examples, so they are not exhaustive here. According to the preparation method, the luminescent auxiliary materials shown in the following table 1 can be obtained:
TABLE 1
Figure BDA0003700119890000231
Figure BDA0003700119890000241
When the organic layer includes the light-emitting auxiliary layer, the light-emitting auxiliary layer includes the light-emitting auxiliary material provided in the above embodiment.
Device embodiment
Organic electroluminescent devices were prepared as device examples 1 to 26, respectively, using the light-emitting auxiliary materials provided in table 1 above.
Specifically, the preparation of the organic electroluminescent device containing the luminescent auxiliary material comprises the following steps:
a. an ITO anode: washing an ITO (indium tin oxide) -Ag-ITO (indium tin oxide) glass substrate with the coating thickness of 150nm in distilled water for 2 times, ultrasonically washing for 30min, repeatedly washing for 2 times by using distilled water, ultrasonically washing for 10min, transferring to a spin dryer for spin-drying after washing is finished, baking for 2 hours at 220 ℃ by using a vacuum oven, and cooling after baking is finished. And (3) taking the substrate as an anode, performing a device evaporation process by using an evaporation machine, and sequentially evaporating other functional layers on the substrate.
b. HIL (hole injection layer): to be provided with
Figure BDA0003700119890000242
The evaporation rate per second, and the vacuum evaporation of hole injection layer materials HT and P-dots; wherein the evaporation rate ratio of HT to P-dopant is 97: 3, the thickness is 10 nm.
c. HTL (hole transport layer): to be provided with
Figure BDA0003700119890000243
The evaporation rate per second, 120nm HT was vacuum evaporated on top of the hole injection layer as a hole transport layer.
d. A light-emitting auxiliary layer: to be provided with
Figure BDA0003700119890000251
Vapor deposition Rate/s 10nm of the compound provided in the above example was vacuum deposited on top of the hole transport layer as a light-emitting auxiliary layer.
e. EML (light-emitting layer): then on the above-mentioned luminescence auxiliary layer so as to
Figure BDA0003700119890000252
Steam of/sPlating rate, namely vacuum evaporating a Host material (Host) and a doping material (span) with the thickness of 25nm as light-emitting layers, wherein the chemical formulas of the Host and the span are shown as follows; wherein, the evaporation rate ratio of Host to Dopant is 98: 2.
f. HBL (hole blocking layer): to be provided with
Figure BDA0003700119890000253
The structure of an HB layer having a vapor deposition rate/s and a vacuum deposition thickness of 5.0nm as a hole-blocking layer is shown below.
g. ETL (electron transport layer): to be provided with
Figure BDA0003700119890000254
The evaporation rate per second, ET and Liq with the thickness of 30nm are evaporated in vacuum to be used as electron transport layers, and the chemical formula of ET is shown as follows; wherein the evaporation rate ratio of ET to Liq is 50: 50.
h. EIL (electron injection layer): to be provided with
Figure BDA0003700119890000255
The evaporation rate of/s, evaporation of Yb film layer is 1.0nm, and the electron injection layer is formed.
i. Cathode: to be provided with
Figure BDA0003700119890000256
And (3) the evaporation rate ratio of/s, the evaporation rate ratio of magnesium to silver is 18nm, and the evaporation rate ratio is 1:9, so that the OLED device is obtained.
j. Light extraction layer: to be provided with
Figure BDA0003700119890000257
CPL was vacuum-deposited on the cathode at a deposition rate/s to form a light extraction layer, the thickness of which was 70 nm.
k. Packaging the evaporated substrate: firstly, coating the cleaned cover plate by using UV glue through gluing equipment, then moving the coated cover plate to a pressing working section, placing the evaporated substrate on the upper end of the cover plate, finally, attaching the substrate and the cover plate under the action of attaching equipment, and simultaneously, finishing the illumination and solidification of the UV glue.
The structural formula referred to above is as follows:
Figure BDA0003700119890000261
device comparative example:
the comparative device example provides an organic electroluminescent device, and the only difference between the preparation method of the organic electroluminescent device and the device example 1 is that the organic electroluminescent device is prepared by respectively adopting the existing comparative compounds a, b, c, d, e and f to replace the luminescent auxiliary material (compound 1) in the device example 1 for evaporation, and preparing the comparative device examples 1-6. Wherein the chemical structural formulas of the comparative compounds a, b, c, d, e and f are as follows:
Figure BDA0003700119890000271
the organic electroluminescent devices containing the light-emitting auxiliary materials obtained in the above-mentioned device application examples 1 to 26 and device comparative examples 1 to 6 were characterized in terms of driving voltage, light-emitting efficiency and lifetime at a luminance of 1000 (nits). The test results are shown in table 2.
TABLE 2 test results of luminescence characteristics (brightness 1000nits)
Figure BDA0003700119890000272
Figure BDA0003700119890000281
Note: in a blue top-emitting device, current efficiency is greatly affected by chromaticity, so that the influence factor of chromaticity on efficiency is taken into consideration, and the ratio of luminous efficiency to CIEy is defined as a BI value, i.e., (cd/a)/CIEy.
As can be seen from table 2, the organic electroluminescent devices prepared using the light-emitting auxiliary material provided in the present application, examples 1 to 26, compared to the conventional organic electroluminescent devices provided in comparative examples 1 to 6, have improved luminous efficiency and lifetime while reducing the driving voltage.
In the present specification, the embodiments are described in a progressive manner, each embodiment focuses on differences from other embodiments, and the same and similar parts among the embodiments are referred to each other. The device disclosed by the embodiment corresponds to the method disclosed by the embodiment, so that the description is simple, and the relevant points can be referred to the method part for description.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present application. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the application. Thus, the present application is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims (9)

1. A luminescence auxiliary material is characterized in that the structural general formula of the luminescence auxiliary material is shown as a general formula I:
Figure FDA0003700119880000011
wherein, the first and the second end of the pipe are connected with each other,
L 1 、L 2 the two groups are the same or different and are respectively and independently one of a connecting bond, substituted or unsubstituted aryl of C6-C30 and substituted or unsubstituted heteroaryl of C6-C30, wherein hetero atoms are selected from oxygen, nitrogen and sulfur;
p and q independently represent 0 or 1 and are not 0 at the same time;
R 3 、R 4 identical or different from each other and independently of each other, a mono-aryl group selected from hydrogen, deuterium, a substituted or unsubstituted C1-C15 alkane, a substituted or unsubstituted C1-C18 cycloalkane, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 heteroaryl groupWherein the heteroatom is selected from oxygen, nitrogen, sulfur;
m and n are respectively independent and represent an integer of 0-4;
Ar 1 、Ar 2 identical or different from each other and each independently of the others, is one selected from the group consisting of substituted or unsubstituted 3-to 30-membered heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, wherein the heteroatom is selected from the group consisting of oxygen, nitrogen, sulfur.
2. A luminescent support material as claimed in claim 1, wherein R is a group of atoms 3 、R 4 The same or different from each other and independent from each other, is one selected from hydrogen, deuterium, substituted or unsubstituted C1-C6 alkane, substituted or unsubstituted C1-C6 cycloalkane, substituted or unsubstituted C6-C18 aryl, and substituted or unsubstituted C6-C18 heteroaryl, wherein the heteroatom is selected from nitrogen, oxygen and sulfur.
3. The luminescent auxiliary material according to claim 1, wherein Ar is 1 、Ar 2 Is one of the following groups or the following groups in any combination:
Figure FDA0003700119880000021
where denotes the connection point.
4. The luminescent aid material according to claim 1, wherein the luminescent aid material is any one of the following structures:
Figure FDA0003700119880000031
Figure FDA0003700119880000041
Figure FDA0003700119880000051
Figure FDA0003700119880000061
Figure FDA0003700119880000071
Figure FDA0003700119880000081
Figure FDA0003700119880000091
Figure FDA0003700119880000101
5. a method for preparing a luminescent support material as claimed in any one of claims 1 to 4, comprising:
Figure FDA0003700119880000111
wherein Hal 1 、Hal 2 、Hal 3 The same or different from each other and independent from each other, is one selected from fluorine, chlorine, bromine and iodine;
dissolving the raw materials A and B in toluene, and reacting the solution in N 2 Adding Pd under atmosphere 2 (dba) 3 、P(t-Bu) 3 And t-BuONa, heating to 110-120 ℃ and stirring for reaction for 10-12h,obtaining an intermediate 1;
in N 2 Under protection, the intermediate 1 and the raw material C, Pd are mixed 2 (dba) 3 、P(t-Bu) 3 And t-BuONa, heating to 110-120 ℃, and stirring for reaction for 12-14h to obtain an intermediate 2;
dissolving the intermediate 2 and the raw material D in a mixed solution of toluene, ethanol and water, adding potassium carbonate and a palladium catalyst under the protection of nitrogen, uniformly stirring, heating to 80-90 ℃, and carrying out reflux reaction for 6-8h to obtain the organic compound shown in the general formula 1.
6. Use of a luminescent support material according to any one of claims 1 to 4 in the field of optoelectronics.
7. A light-emitting device characterized in that it comprises a luminescent support material as claimed in any one of claims 1 to 4.
8. The light-emitting device according to claim 7, wherein the light-emitting device comprises a light-emission auxiliary layer; the luminescent auxiliary layer comprises a luminescent auxiliary material according to any of claims 1 to 4.
9. A light-emitting apparatus characterized by comprising the light-emitting device according to claim 8.
CN202210694403.5A 2022-06-17 2022-06-17 Luminous auxiliary material and preparation method thereof, light-emitting device and light-emitting device Pending CN114933559A (en)

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CN115093402A (en) * 2022-08-29 2022-09-23 吉林奥来德光电材料股份有限公司 Organic compound and preparation method and application thereof
CN115557920A (en) * 2022-09-22 2023-01-03 吉林奥来德光电材料股份有限公司 Light-emitting auxiliary material, preparation method thereof and organic electroluminescent device
CN115626915A (en) * 2022-11-14 2023-01-20 吉林奥来德光电材料股份有限公司 Luminescence auxiliary material, preparation method thereof, luminescent device and luminescent device

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115093402A (en) * 2022-08-29 2022-09-23 吉林奥来德光电材料股份有限公司 Organic compound and preparation method and application thereof
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CN115557920A (en) * 2022-09-22 2023-01-03 吉林奥来德光电材料股份有限公司 Light-emitting auxiliary material, preparation method thereof and organic electroluminescent device
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