Deuterated composition, preparation method therefor, light-emitting layer and organic light-emitting device

Abstract

A deuterated composition, a preparation method therefor, a light-emitting layer, and an organic light-emitting device, relating to the field of organic light-emitting materials. The deuterated composition comprises different deuterated compounds of a compound represented by formula I, wherein in formula I, Ar1 is selected from phenyl or naphthyl. For the different deuterated compounds of the same compound, the average deuteration rate of deuterium-exchangeable hydrogen atoms on Ar1 and anthryl is greater than 98%, and the average deuteration rate of deuterium-exchangeable hydrogen atoms on phenanthryl is 96%-98%. When the deuterated composition is used as a light-emitting material of organic light-emitting devices, the service lifetime of the devices is significantly prolonged.

Description

Deuterated composition, preparation method thereof, light-emitting layer and organic light-emitting device TECHNICAL FIELD

[0001] The present application relates to the technical field of organic light-emitting materials, in particular to a deuterated composition, a preparation method thereof, a light-emitting layer and an organic light-emitting device. BACKGROUND

[0002] In an organic light-emitting device, the service life of a blue light-emitting device is generally lower than that of a red light-emitting device and a green light-emitting device, which becomes a short board of the service life of the organic light-emitting device. In order to improve the service life of the blue light-emitting device, one of the most effective ways is to improve the blue light-emitting host material.

[0003] A common blue light-emitting host material is an anthracene compound. If the anthracene compound is deuterated, the stability of the anthracene compound can be improved. Although the deuterated product of the anthracene compound can be used as a blue light-emitting host material to improve the service life of the blue light-emitting device, the service life of the device still needs to be further improved. SUMMARY

[0004] The technical problem solved by the present application is to improve the service life of a blue light-emitting device.

[0005] To solve the above technical problem, the first aspect of the present application provides a deuterated composition comprising different deuterated products of a compound as shown in formula I:

[0006] In formula I, Ar1 is selected from a phenyl group or a naphthyl group; in different deuterated products of the same compound, the average deuterium substitution rate of the deuterium-substitutable hydrogen of Ar1 and the anthracene group is greater than 98%, and the average deuterium substitution rate of the deuterium-substitutable hydrogen of the phenanthrene group is 96% to 98%.

[0007] The second aspect of the present application provides a deuterated composition, which is prepared by subjecting compound A1 to a first deuterium substitution reaction to obtain compound A2, then subjecting the compound A2 to a reaction with compound A3 to obtain compound A4, and then subjecting the compound A4 to a second deuterium substitution reaction.

[0008] The third aspect of the present application provides a preparation method of a deuterated composition, comprising the following steps: subjecting compound A1 to a first deuterium substitution reaction to obtain compound A2; subjecting the compound A2 to a reaction with compound A3 to obtain compound A4; and subjecting the compound A4 to a second deuterium substitution reaction to obtain a deuterated composition comprising different deuterated products, and the structure of the deuterated product is as shown in formula II:

[0009] D(n) represents that n deuterium pairs are substituted on the anthracene group, and n'≤n≤8, D(m) represents that m deuterium pairs are substituted on the deuterium-substitutable hydrogen of the phenanthrene group, and m≤9, and Ar1” is selected from a group consisting of a completely or partially deuterated phenyl group and a completely or partially deuterated naphthyl group, and the number of deuterium substitutions of Ar1” is greater than or equal to the number of deuterium substitutions of Ar1'.

[0010] In the above scheme, the compound A1 has the following structural formula: Ar1 is selected from a phenyl group or a naphthyl group; and the compound A2 has the following structural formula: D(n') represents that n' deuterium pairs are substituted on the deuterium-substitutable hydrogen of the anthracene group, and n'≤8, and Ar1' is selected from a group consisting of a completely or partially deuterated phenyl group and a completely or partially deuterated naphthyl group; and the compound A3 has the following structural formula: The compound A4 has the following structural formula:

[0011] The fourth aspect of the present application provides a light-emitting layer, which comprises the deuterated composition described above or the deuterated composition prepared by the preparation method of the deuterated composition described above.

[0012] The fifth aspect of the present application provides an organic light-emitting device, which comprises a first electrode and a second electrode arranged oppositely, and an organic layer located between the first electrode and the second electrode, wherein the organic layer comprises the light-emitting layer described above.

[0013] Through device testing verification, different deuterated compounds of formula I of the present application are used as light-emitting materials of an organic light-emitting device, and when the average deuterium substitution rate of the deuterium-substitutable hydrogen on Ar1 and the anthracene group is higher than the average deuterium substitution rate of the deuterium-substitutable hydrogen on the phenanthrene group, the device lifetime can be greatly improved. When the preparation method of the present application is used to deuterate anthracene compounds, the deuterium substitution cost can be greatly reduced, which is suitable for industrial production. BRIEF DESCRIPTION OF DRAWINGS

[0014] The following drawings in detail describe the exemplary embodiments disclosed in the present application. The same reference signs in the drawings represent similar structures in several views of the drawings. A person of ordinary skill in the art will understand that these embodiments are non-limiting, exemplary embodiments, and the drawings are only for the purpose of illustration and description, and are not intended to limit the scope of the present application, and other embodiments can also achieve the same purpose of the invention in the present application. It should be understood that the drawings are not drawn to scale. Among them:

[0015] FIG. 1 is a hydrogen nuclear magnetic spectrum of the deuterated composition prepared in Example 1 of the present application;

[0016] FIG. 2 is a hydrogen nuclear magnetic spectrum of the deuterated composition prepared in Comparative Example 1 of the present application;

[0017] Figure 3 is a hydrogen nuclear magnetic resonance spectrum of a deuterated composition prepared according to Comparative Example 2 of the present application;

[0018] Figure 4 is a hydrogen nuclear magnetic resonance spectrum of a deuterated composition prepared according to Comparative Example 3 of the present application;

[0019] Figure 5 is a hydrogen nuclear magnetic resonance spectrum of a deuterated composition prepared according to Example 2 of the present application;

[0020] Figure 6 is a hydrogen nuclear magnetic resonance spectrum of a deuterated composition prepared according to Example 3 of the present application. DETAILED DESCRIPTION

[0021] The following description provides specific applications and requirements of the present application, which is intended to enable those skilled in the art to make and use the contents of the present application. Various local modifications to the disclosed embodiments are apparent to those skilled in the art, and the general principles defined herein can be applied to other embodiments and applications without departing from the spirit and scope of the present application. Therefore, the present application is not limited to the embodiments shown, but is consistent with the widest scope of the claims.

[0022] The present application provides a deuterated composition, which includes different deuterated compounds of Formula I:

[0023] In Formula I, Ar1is selected from phenyl or naphthyl.

[0024] In Formula I, the connection site of phenanthryl and anthryl is not limited, thus, according to the connection site of phenanthryl and anthryl, Formula I represents a plurality of compounds. The following are examples of compounds represented by Formula I:

[0025] In the present application, the deuterated composition can include different deuterated compounds of only one compound of Formula I, or can include different deuterated compounds of two or more compounds of Formula I. For example, the deuterated composition can include different deuterated compounds of Formula I-1, or different deuterated compounds of Formula I-5, or different deuterated compounds of Formula I-6. For another example, the deuterated composition can include different deuterated compounds of two or three of Formula I-1, Formula I-5, and Formula I-6.

[0026] In the present application, different deuterated compounds of the compound refer to the number of deuterium-substituted deuterium of the compound. The deuterium-substitutable hydrogen refers to hydrogen that can be substituted by deuterium. In Formula I, the total number of deuterium-substitutable hydrogen on anthryl is 8, the total number of deuterium-substitutable hydrogen on phenanthryl is 9, the total number of deuterium-substitutable hydrogen when Ar1is phenyl is 5, and the total number of deuterium-substitutable hydrogen when Ar1is naphthyl is 7.

[0027] When deuterating anthracene compounds, the general consensus is that the higher the degree of deuteration, the better, ideally achieving complete deuteration. However, the inventors of this application unexpectedly discovered that closer to complete deuteration does not necessarily mean better performance. In anthracene compounds, the degree of deuteration of the anthracene group has a different impact on device lifetime than the degree of deuteration of other groups. When the degree of deuteration of the anthracene group is higher than that of other groups, the device exhibits a longer lifetime. The reason for this may be that when anthracene compounds are used as the main light-emitting material, the anthracene group contributes the most to the HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied Molecular Orbital) of the compound, and its stability is the most critical. Therefore, the requirement for the degree of deuteration of the anthracene group is higher than that of other groups.

[0028] Specifically, the inventors of this application have discovered that if, in different deuterated derivatives of the same compound, for example, in different deuterated derivatives of the compound shown in Formula I-1, or in different deuterated derivatives of the compound shown in Formula I-5, or in different deuterated derivatives of the compound shown in Formula I-6, the average deuteration rate of Ar1 and anthracene is greater than 98%, and the average deuteration rate of phenanthrene is 96% to 98%, then the deuterated composition containing these different deuterated derivatives can significantly improve the lifespan of the device when used as a luminescent material.

[0029] In this application, the average deuteration rate of the deuterable hydrogen refers to the average deuteration rate of the deuterable hydrogen. The average deuteration rate of the deuterable hydrogen will be explained below using the compound shown in Formula I-1 as an example.

[0030] In the above formula, d1 to d8 represent the deuterated hydrogen sites of the anthracene group, d9 to d13 represent the deuterated hydrogen sites of the phenyl group, and d14 to d22 represent the deuterated hydrogen sites of the phenanthrene group.

[0031] When deuterating the compound shown in Formula I-1, each deuteratable hydrogen may or may not be deuterated. Therefore, the deuteration rate of each deuteratable hydrogen can be calculated, which can represent the degree of deuteration. Since there are many deuteratable hydrogens, each deuteratable hydrogen corresponds to a deuteration rate, which cannot well reflect the overall degree of deuteration of a certain part. Therefore, this application introduces the average deuteration rate of deuteratable hydrogens to represent the degree of deuteration, and the higher the average deuteration rate of deuteratable hydrogens, the higher the degree of deuteration.

[0032] Theoretically, the deuteration rate of any deuteratizable hydrogen can be obtained in the following way: D di % = N Di / N T ×100%, D di% represents the deuterium substitution rate of the deuterium-substitutable hydrogen at the i-th site, N Di N represents the number of deuterated compounds in which the deuterium-substitutable hydrogen at the i-th site is replaced by deuterium, T N represents the number of deuterated compounds in which the deuterium-substitutable hydrogen at the i-th site is replaced by deuterium, N represents the number of deuterated compounds in which the deuterium-substitutable hydrogen at the i-th site is replaced by deuterium,

[0033] In actual quantitative analysis, the average deuterium substitution rate of the deuterium-substitutable hydrogen can be calculated by hydrogen nuclear magnetic test. Standard samples (such as mesitylene, 1,4-dioxane, etc.) are dissolved and diluted in a suitable deuterated reagent (such as deuterated DMSO, deuterated chloroform, etc.) to obtain a standard sample solution. The test sample is dissolved in the standard sample solution and subjected to hydrogen nuclear magnetic test. The molar mass of the standard sample and the test sample is calculated, and then the average deuterium substitution rate is calculated by combining the hydrogen nuclear magnetic spectrum analysis.

[0034] In some preferred embodiments, the different deuterated compounds of the compound of formula I are selected from the group consisting of:

[0035] wherein: D(n) represents that n deuteriums replace the deuterium-substitutable hydrogen of the anthracene group, and n≤8; D(m) represents that m deuteriums replace the deuterium-substitutable hydrogen of the phenanthrene group, and m≤9; when D(q1) appears, it represents that q1 deuteriums replace the deuterium-substitutable hydrogen of the phenyl group, and q1≤5; when D(q2) appears, it represents that q2 deuteriums replace the deuterium-substitutable hydrogen of the naphthyl group, and q2≤7.

[0036] In some preferred embodiments, the average deuterium substitution rate of the anthracene group is greater than the average deuterium substitution rate of the phenanthrene group, and the difference is p, and the value of p is 1% to 4%.

[0037] When anthracene compounds are deuterated, there is usually a problem of difficulty in deuterium substitution due to poor solubility of anthracene compounds. At present, in order to improve the deuterium substitution rate, the conventional method is to use a large amount of deuterated reagent for multiple deuterium substitution, but this method has problems of long deuterium substitution time and high deuterium substitution cost, which is not suitable for industrial production.

[0038] Therefore, the preparation method of the present application can obtain the deuterated composition with excellent application effect at a lower cost.

[0039] Specifically, the preparation method of the deuterated composition comprises the following steps:

[0040] S1: performing a first deuterium substitution reaction on compound A1 to obtain compound A2.

[0041] The structural formula of the compound A1 is: Ar1 is selected from phenyl and naphthyl.

[0042] The structural formula of the compound A2 is: D(n') represents that n' deuterium pairs are substituted for the deuterium-substitutable hydrogen of the anthracene group, and n' ≤ 8, and Ar1' is selected from a completely or partially deuterated phenyl group and a completely or partially deuterated naphthyl group.

[0043] In some embodiments, the method for performing the first deuterium substitution reaction comprises: placing the compound A1 in a first deuterium substitution reagent in the presence of a first catalyst to perform a deuterium substitution reaction.

[0044] In some preferred embodiments, the first catalyst comprises at least one of a protonic acid, a Lewis acid, and a high-molecular-weight bonded sulfonic acid. As an example, the protonic acid can be selected from trifluoroacetic acid, trifluoromethanesulfonic acid, perfluorobutylsulfonic acid, and the like. As an example, the Lewis acid can be selected from aluminum chloride, zinc chloride, molybdenum chloride, and the like.

[0045] In some preferred embodiments, the mass of the first catalyst is 3% to 20% of the mass of the compound A1.

[0046] In some preferred embodiments, the first deuterium substitution reagent comprises deuterated benzene or deuterated water.

[0047] In some preferred embodiments, the ratio of the volume of the first deuterium substitution reagent to the mass of the compound A1 (which can also be referred to as the volume-to-weight ratio) is (20-50) mL:1 g. Since the compound A1 has good solubility, a small amount of the first deuterium substitution reagent can achieve a high average deuterium substitution rate.

[0048] In some preferred embodiments, the reaction temperature of the first deuterium substitution reaction is reflux temperature, and the reaction time is 1-5 days.

[0049] S2: reacting the compound A2 with a compound A3 to obtain a compound A4.

[0050] The compound A3 has the following structural formula: The compound A4 has the following structural formula:

[0051] In some embodiments, the method for reacting the compound A2 with the compound A3 comprises: first brominating the compound A2 to obtain a bromide, and then coupling the bromide with the compound A3 to obtain the compound A4.

[0052] In some preferred embodiments, the method for brominating the compound A2 comprises: reacting the compound A2 with N-bromosuccinimide, using at least one solvent selected from N,N-dimethylformamide, toluene, chlorobenzene, at a reaction temperature of 0-40℃, and for a reaction time of 1-24 hours.

[0053] In some preferred embodiments, when the coupling reaction is performed, the catalyst is selected from platinum compounds and palladium compounds, such as Pd(dppf)Cl2, Pd2(dba)3, palladium acetate, etc., the auxiliary ligand is selected from phosphine ligands, such as 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, etc., the reaction system is basic, K2CO3 and Cs2CO3 can be used to adjust the pH value of the system, the solvent used is at least one selected from benzene, toluene, xylene, and chlorobenzene, the reaction temperature is room temperature to the boiling point of the solvent, and the reaction time is 1-24 hours.

[0054] S3: performing a second deuterium substitution reaction on the compound A4 to obtain a deuterium substitution composition comprising different deuterium substitution products, and the deuterium substitution products have the following structural formula:

[0055] D(n) represents that n deuterium pairs are substituted on the anthracene group, and n'≤n≤8, D(m) represents that m deuterium pairs are substituted on the deuterium-substitutable hydrogen of the phenanthrene group, and m≤9, and Ar1" is selected from phenyl groups that are fully or partially deuterated, and naphthyl groups that are fully or partially deuterated, and the number of deuterium substitutions of Ar1" is greater than or equal to the number of deuterium substitutions of Ar1'.

[0056] In some embodiments, the method for performing the second deuterium substitution reaction comprises: placing the compound A4 in a second deuterium substitution reagent in the presence of a second catalyst to perform a deuterium substitution reaction.

[0057] In some preferred embodiments, the second catalyst comprises at least one of a protic acid, a Lewis acid, a high molecular weight bonded sulfonic acid. As an example, the protic acid can be selected from trifluoroacetic acid, triflic acid, perfluorobutylsulfonic acid, etc. As an example, the Lewis acid can be selected from aluminum chloride, zinc chloride, molybdenum chloride, etc.

[0058] In some preferred embodiments, the second catalyst has a mass of 3% to 20% of the mass of the compound A4.

[0059] In some preferred embodiments, the second deuterating reagent comprises deuterated benzene or deuterated water.

[0060] In some preferred embodiments, the ratio of the volume of the second deuterating reagent to the mass of the compound A4 is (40 to 200) mL:1 g.

[0061] In the present application, the solubility of the compound A4 obtained after introducing the phenanthryl moiety is poor, and under the enlightenment of the generally accepted view that the higher the degree of deuteration is, the better it is, it is easy to think of using a large amount of deuterating reagent for multiple deuteration so that the phenanthryl moiety can also achieve a high degree of deuteration comparable to that of the anthryl moiety. However, based on the inventors' discovery, the average deuteration rate of the phenanthryl moiety is not the higher the better, and when there is a difference in the average deuteration rate between the phenanthryl moiety and the anthryl moiety, it is beneficial to the improvement of the device lifetime. Therefore, the present application can still use a small amount of deuterating reagent for the second deuteration. On the one hand, due to the solubility problem, the deuteration rate of the phenanthryl moiety will be less than that of the anthryl moiety; on the other hand, the second deuteration reaction will not only deuterate the phenanthryl moiety, but also deuterate the non-deuterated deuteratable hydrogens on the anthryl moiety (specifically Ar1' and anthryl), which comprehensively makes the average deuteration rate of the anthryl moiety greater than that of the phenanthryl moiety.

[0062] In some preferred embodiments, the reaction temperature of the second deuteration reaction is the reflux temperature, and the reaction time is 1 to 5 days.

[0063] The present application also provides a deuterated composition, which is prepared by subjecting compound A1 to a first deuteration reaction to obtain compound A2, then subjecting the compound A2 to a reaction with compound A3 to obtain compound A4, and then subjecting the compound A4 to a second deuteration reaction; wherein:

[0064] The structural formula of the compound A1 is: Ar1 is selected from phenyl or naphthyl; the structural formula of the compound A2 is: D(n') represents that n' deuterium pairs replace the deuteratable hydrogens of the anthryl moiety, and n'≤8, and Ar1' is selected from a fully or partially deuterated phenyl group or a fully or partially deuterated naphthyl group; the structural formula of the compound A3 is: The structural formula of compound A4 is:

[0065] In some embodiments, the first deuterium substitution reaction is carried out by placing compound A1 in a first deuterium substitution reagent in the presence of a first catalyst.

[0066] In some preferred embodiments, the conditions of the first deuterium substitution reaction satisfy at least one of the following conditions:

[0067] (a) the first catalyst comprises at least one of a protic acid, a Lewis acid, a high-molecular-weight bonded sulfonic acid; as an example, the protic acid can be selected from trifluoroacetic acid, triflic acid, perfluorobutylsulfonic acid, etc.; as an example, the Lewis acid can be selected from aluminum chloride, zinc chloride, molybdenum chloride, etc.;

[0068] (b) the mass of the first catalyst is 3% to 20% of the mass of compound A1;

[0069] (c) the first deuterium substitution reagent comprises deuterated benzene or deuterated water;

[0070] (d) the ratio of the volume of the first deuterium substitution reagent to the mass of compound A1 is (20-50) mL:1 g;

[0071] (e) the reaction temperature is reflux temperature, and the reaction time is 1-5 days.

[0072] In some embodiments, the second deuterium substitution reaction is carried out by placing compound A4 in a second deuterium substitution reagent in the presence of a second catalyst.

[0073] In some preferred embodiments, the conditions of the second deuterium substitution reaction satisfy at least one of the following conditions:

[0074] (a) the second catalyst comprises at least one of a protic acid, a Lewis acid, a high-molecular-weight bonded sulfonic acid; as an example, the protic acid can be selected from trifluoroacetic acid, triflic acid, perfluorobutylsulfonic acid, etc.; as an example, the Lewis acid can be selected from aluminum chloride, zinc chloride, molybdenum chloride, etc.;

[0075] (b) the mass of the second catalyst is 3% to 20% of the mass of compound A4;

[0076] (c) the second deuterium substitution reagent comprises deuterated benzene or deuterated water;

[0077] (d) the ratio of the volume of the second deuterium substitution reagent to the mass of compound A4 is (40-200) mL:1 g;

[0078] (e) the reaction temperature is reflux temperature, and the reaction time is 1-5 days.

[0079] The present application also provides a light-emitting layer comprising the deuterated composition described above or the deuterated composition prepared by the preparation method of the deuterated composition described above.

[0080] In some preferred embodiments, the light-emitting layer further comprises a compound as shown in Formula III:

[0081] wherein Q1, Q2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzo-cycloalkyl; and the substituents when substituted are selected from hydrogen, deuterium, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 6-30 carbon atoms, linear or branched alkyl or cycloalkyl having 1-10 carbon atoms; n is an integer from 0 to 3; R is selected from deuterium, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 6-30 carbon atoms, linear or branched alkyl or cycloalkyl having 1-10 carbon atoms; when n is 3 and R is linear or branched alkyl having 1-10 carbon atoms, the adjacent two alkyls are cyclized. Ar1 and Ar2 are independently selected from substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 6-30 carbon atoms, substituted or unsubstituted aryl-cycloalkyl having 6-30 carbon atoms, and the substituents are selected from aryl having 6-30 carbon atoms, heteroaryl having 6-30 carbon atoms, linear or branched alkyl or cycloalkyl having 1-10 carbon atoms.

[0082] In some more preferred embodiments, the compound as shown in Formula III is selected from the group consisting of:

[0083] In some preferred embodiments, the deuterated composition of the present application is a light-emitting host material, and the mass percentage is 95%-99%, and the compound as shown in Formula III is a light-emitting guest material, and the mass percentage is 1%-5%.

[0084] The present application also provides an organic light-emitting device comprising oppositely disposed first and second electrodes and an organic layer between the first and second electrodes, wherein the organic layer comprises the light-emitting layer described above. As an example, the first electrode is an anode, and the second electrode is a cathode. The cathode can be one or more layers. The organic layer can be a single-layer structure or a multi-layer series structure with two or more organic layers laminated. The organic layer can comprise at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0085] The specific configuration of the organic light-emitting device described in the present application can be referred to the priority document of the present application for incorporation or merger.

[0086] The technical solutions of the present application will be described clearly and completely in combination with the embodiments of the present application. If not otherwise specified, the reagents and raw materials used can be purchased through commercial channels. The experimental methods not specified in the following examples are generally determined according to the national standards. If there is no corresponding national standard, the international standard, the general method and condition, or the conditions suggested by the manufacturer, or the product instruction is selected.

[0087] The raw materials and solvents of the following examples are purchased from the National Medicine, and some commonly used OLED intermediates are purchased from domestic OLED intermediate manufacturers; the nuclear magnetic resonance data is measured by Varian 400-MR nuclear magnetic resonance spectrometer.

[0088] Deuterated composition: BH1

[0089] Example 1

[0090] The synthesis route of the deuterated composition of the present embodiment is as follows:

[0091] The specific preparation method is as follows:

[0092] 1) Preparation of compound A1:

[0093] In a clean 1000 mL three-necked flask, 9-bromoanthracene (30.3 g, 118.1 mmol), phenylboronic acid (14.4 g, 118.1 mmol), K2CO3(32.5 g, 236.2 mmol), Pd2(dba)3(0.54 g, 0.59 mmol), s-phos (0.45 g, 1.2 mmol) were added, and then 300 mL of toluene, 50 mL of ethanol and 100 mL of water were added. The system was replaced with nitrogen for 3 times, the reaction was heated to 95°C, and the reaction was stirred at reflux for 16 hours. The reaction was detected by TLC. The reaction liquid was cooled to room temperature, and the liquid was separated. The organic phase was passed through a silica gel column (200-300 mesh, 50 g, TOl), and the column liquid was concentrated to dryness. 200 mL of a mixed solvent of n-hexane and toluene with a volume ratio of 10:1 was added, and the mixture was stirred at room temperature for 2 hours. The filter cake was obtained by suction filtration, and the yield was 24 g of white solid, with a yield of 80%.

[0094] 2) Preparation of compound A2:

[0095] In a clean 1000 mL three-necked flask, add compound A1 (20 grams, 78 mmol), perfluorobutylsulfonic acid (4.4 grams, 7.8 mmol), and deuterobenzene 400 mL. The system is replaced with nitrogen three times, the reaction is heated to reflux, and the reaction is stirred for 4 days. The reaction is cooled to room temperature, and deuterobenzene is removed by rotary evaporation. 300 mL of dichloromethane and 100 mL of a 10% by mass sodium carbonate solution are added, the mixture is stirred for half an hour, and the mixture is separated. The aqueous phase is washed once more, and the organic phase is dried. The organic phase is passed through a silica gel column, and dichloromethane is used as the eluent. The organic phase is concentrated by rotary evaporation, 100 mL of ethanol is added, the mixture is filtered, and the filter cake is dried to obtain 19.5 grams of the product, with a yield of 97%.

[0096] 3) Preparation of compound A4:

[0097] In a 200 mL reaction flask, add the product of the previous step (15 grams, 56 mmol), NBS (10.5 grams, 59 mmol), and DMF (100 mL). The mixture is gradually heated to 50°C, and stirred for 2 hours. TLC shows that the reaction is complete. The reaction mixture is slowly added to 100 mL of water, and stirred for 1 hour. The mixture is filtered, and the filter cake is washed with 20 mL of ethanol, and then slurried with 30 mL of n-hexane for 2 hours. The mixture is filtered, and the filter cake is dried to obtain 17 grams of a yellow solid, with a yield of 87.7%.

[0098] In a clean 500 mL three-necked flask, add the product of the previous step (15 grams, 43 mmol), 9-phenanthrylboronic acid (9.5 grams, 43 mmol), K2CO3 (11.8 grams, 86 mmol), Pd2(dba)3 (0.19 grams, 0.21 mmol), s-phos (0.17 grams, 0.42 mmol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of water. The system is replaced with nitrogen three times, the reaction is heated to 95°C, and stirred for 10 hours. TLC shows that the reaction is complete. The reaction is cooled to room temperature, and the mixture is separated. The organic phase is passed through a silica gel column (200-300 mesh, 30 grams, TOL), and the column is concentrated. 200 mL of n-hexane and toluene (10:2 by volume) are added, the mixture is stirred for 4 hours at room temperature, and the mixture is filtered. The filter cake is dried to obtain 14 grams of a yellow-white solid, which is compound A4, with a yield of 73.6%.

[0099] 4) Preparation of deuterated composition BH1:

[0100] In a clean 1000 mL three-necked flask, compound A4 (12 g, 27.1 mmol), perfluorobutylsulfonic acid (1.5 g, 2.7 mmol), and 500 mL deuterated benzene were added. The system was replaced with nitrogen for 3 times, and the reaction was heated to reflux and stirred for 6 days. The reaction solution was cooled to room temperature, and deuterated benzene was removed by rotary evaporation. 500 mL dichloromethane and 300 mL 10% sodium carbonate solution were added, stirred for half an hour, and separated. It was washed with water once more and dried. The organic phase was passed through a silica gel column and eluted with dichloromethane. The organic phase was rotary evaporated, slurried with 500 mL ethanol, filtered, and dried to obtain 10.5 g of product with a yield of 86%.

[0101] The product was purified by vacuum sublimation, the vacuum degree was 3 x 10 -5 Pa, and the sublimation temperature was 245°C.

[0102] HNMR test: 65.2 mg of mesitylene was weighed and dissolved in 1487.48 mg of DMSO-D6 as a standard sample. After mixing 16.9 mg of the test sample and 18.91 mg of the standard sample, they were dissolved in DMSO-D6 for testing. The nuclear magnetic spectrum is shown in Figure 1.

[0103] According to the nuclear magnetic analysis, the peaks at 9.06 ppm, 8.09 ppm, 8.01 ppm, 7.76 ppm, 7.73 ppm, 7.68 ppm, 7.46 ppm, 7.42 ppm, and 7.32 ppm belong to the hydrogen on the phenanthryl group, and the remaining displacement peaks belong to the hydrogen on the anthryl and phenyl groups. The integral of the hydrogen on the phenanthryl group is 2.37, and the integral of the hydrogen on the anthryl and phenyl groups is 0.5. According to the calculation, the average deuterium substitution rate of the deuterium-substitutable hydrogen on the anthryl and phenyl groups is 99.5%, and the average deuterium substitution rate of the deuterium-substitutable hydrogen on the phenanthryl group is 96.5%.

[0104] The specific calculation method is as follows:

[0105] First, the molar mass of the standard sample in the test sample was calculated according to the weight of the standard sample, the dilution multiple, and the molecular weight of the standard sample: the molar mass of mesitylene = 18.91 x (65.2 ÷ 168.2 ÷ 1487.48) = 0.004928 mmol. Then the molar mass of the test sample was calculated as: 16.9 ÷ 452 = 0.037 mmol.

[0106] The standard sample has 9 hydrogens, and the test sample has 13 non-deuterated hydrogens on the phenyl and anthracenyl groups and 9 non-deuterated hydrogens on the phenanthrene group. With the hydrogen integration of the standard sample being 9, the hydrogen integration of the phenanthrene group when not deuterated is 0.037 ÷ 0.004928 x 9 = 68.28, and the hydrogen integration of the anthracenyl and phenyl groups when not deuterated is 98.6. According to the actual test nuclear magnetic hydrogen integration, the hydrogen integration of the methyl group of the standard sample is 9, the hydrogen integration of the phenanthrene group is 2.37, and the hydrogen integration of the anthracenyl and phenyl groups is 0.5.

[0107] The average deuterium degree of the phenanthrene group is 1 - (2.37 ÷ 68.28) x 100% = 96.5%, and the average deuterium degree of the anthracenyl and phenyl groups is 1 - (0.5 ÷ 218.29) x 100% = 99.5%.

[0108] Comparative Example 1

[0109] The synthetic route of the deuterated composition of the present comparative example is as follows:

[0110] The specific preparation method is as follows:

[0111] The steps are basically the same as in Example 1, except that the first deuterium substitution reaction is not performed on compound A1, but two deuterium substitution reactions are performed on compound A4-1, and the conditions of the two deuterium substitution reactions are the same as the second deuterium substitution reaction in Example 1. The yields of the two deuterium substitutions are 85% and 84%, respectively.

[0112] HNMR test: 15.76 mg of 1,4-dioxane was weighed and dissolved in 1386.2 mg of deuterated DMSO as a standard sample, ready for use. After mixing 15.1 mg of the test sample and 16.8 mg of the standard sample, they were dissolved in deuterated DMSO for testing, and the nuclear magnetic spectrum is shown in Figure 2.

[0113] As shown in Figure 2, the labeled peaks belong to the hydrogens on the phenanthrene group, and the remaining peaks belong to the hydrogens on the anthracenyl and phenyl groups. The hydrogen integration of the phenanthrene group is 46.53, and the hydrogen integration of the anthracenyl and phenyl groups is 73.23. According to the calculation, the average deuterium degree of the deuterium-substitutable hydrogens on the anthracenyl and phenyl groups is 97.08%, and the average deuterium degree of the deuterium-substitutable hydrogens on the phenanthrene group is 97.31%. The calculation method is the same as in Example 1.

[0114] Comparative Example 2

[0115] The synthetic route of the deuterated composition of the present comparative example is as follows:

[0116] The nuclear magnetic test method can refer to Comparative Example 1, and the nuclear magnetic spectrum is shown in Figure 3. Directly compare by hydrogen internal standard of phenanthrene, the hydrogen integral of non-deuterated phenanthrene group is 117.54. The theoretical integral of anthracene and benzene groups when non-deuterated is 117.54 x 13 / 9 = 169.78, the actual hydrogen integral of anthracene and benzene groups is 5.33, and the average deuterium substitution rate of deuterium-substitutable hydrogen of anthracene and benzene groups is calculated to be 1-(5.33 / 169.78) x 100% = 96.86%.

[0117] Comparative Example 3

[0118] The deuterium-substituted composition prepared in this comparative example is compound A4 in Example 1, which is only different from Comparative Example 2 in that the first deuterium substitution reaction is repeated twice.

[0119] The nuclear magnetic test method can refer to Comparative Example 1, and the nuclear magnetic spectrum is shown in Figure 4. Directly compare by hydrogen internal standard of phenanthrene, the hydrogen integral of non-deuterated phenanthrene group is 88.36, the theoretical integral of anthracene and benzene groups when non-deuterated is 88.36 x 13 / 9 = 127.63, the hydrogen integral of anthracene and benzene groups is 1.32, and the average deuterium substitution rate of deuterium-substitutable hydrogen of anthracene and benzene groups is calculated to be 1-(1.32 / 127.63) x 100% = 98.97%.

[0120] Deuterium-substituted composition: BH5

[0121] Example 2

[0122] The synthesis route of the deuterium-substituted composition of this example is as follows:

[0123] The preparation method can refer to Example 1:

[0124] 1) First coupling reaction: 1-naphthalene boronic acid is used instead of phenyl boronic acid in Example 1, and other conditions and molar equivalents are the same, and the yield is 81%.

[0125] 2) First deuterium substitution reaction: the same as Example 1, and the yield is 94%.

[0126] 3) Bromination reaction: the same as Example 1, and the yield is 92%.

[0127] 4) Second coupling reaction: 2-phenanthrene boronic acid is used instead of 9-phenanthrene boronic acid in Example 1, and the yield is 81%.

[0128] 5) Second deuterium substitution reaction: the same as Example 1, and the yield is 86%.

[0129] HNMR test: 45.5 mg of mesitylene was weighed and dissolved in 1321.5 mg of deuterated chloroform as a standard sample, ready for use. The test sample of 27.36 mg and the standard sample of 13.16 mg were mixed and dissolved in deuterated chloroform for testing, and the nuclear magnetic spectrum is shown in Figure 5. The hydrogen integral of phenanthryl is 5.53, and the hydrogen integral of anthryl and naphthyl is 4.94. According to the calculation, the average deuteration rate of the deuterium of the anthryl and naphthyl hydrogen is 98.36%, and the average deuteration rate of the deuterium of the phenanthryl hydrogen is 96.95%. The calculation method is the same as that of Example 1.

[0130] Comparative Example 4

[0131] The synthetic route of the deuterated composition of the present comparative example is as follows:

[0132] The specific preparation method is as follows:

[0133] The steps are basically the same as those of Example 2, except that the first deuteration reaction is not performed on compound A1, but two deuteration reactions are performed on compound A4-1, and the conditions of the two deuteration reactions are the same as those of the second deuteration reaction of Example 2. The yield of the two deuterations is 83% and 81%, respectively.

[0134] According to the nuclear magnetic test and calculation, the average deuteration rate of the deuterium of the anthryl and naphthyl hydrogen is 97.1%, and the average deuteration rate of the deuterium of the phenanthryl hydrogen is 96.5%.

[0135] Deuterated composition: BH6

[0136] Example 3

[0137] The difference between the preparation method of Example 2 is that compound A3 is replaced by

[0138] HNMR test: 45.5 mg of mesitylene was weighed and dissolved in 1321.5 mg of deuterated chloroform as a standard sample, ready for use. The test sample of 27.36 mg and the standard sample of 13.16 mg were mixed and dissolved in deuterated chloroform for testing, and the nuclear magnetic spectrum is shown in Figure 5. The hydrogen integral of phenanthryl is 5.53, and the hydrogen integral of anthryl and naphthyl is 4.94. According to the calculation, the average deuteration rate of the deuterium of the anthryl and naphthyl hydrogen is 98.36%, and the average deuteration rate of the deuterium of the phenanthryl hydrogen is 96.95%. The calculation method is the same as that of Example 1.

[0139] Comparative Example 5

[0140] The difference between the preparation method of Comparative Example 4 is that compound A3 is replaced by

[0141] ​​The average deuterium substitution rate of the anthracene group and naphthalene group is 96.8%, and the average deuterium substitution rate of the phenanthrene group is 96.2% through nuclear magnetic testing and calculation.

[0142] Organic light emitting device

[0143] Example 4

[0144] The present embodiment provides an organic light emitting device, and a preparation method thereof, which comprises the following steps:

[0145] (1) A mixed material of compound 1 and compound 2 is evaporated on the surface of the reflective anode as a hole injection layer, and the mixing ratio is 1:99 (mass ratio), and the thickness is 10 nm.

[0146] (2) Compound 2 is evaporated on the surface of the hole injection layer to obtain a first hole transport layer with a thickness of 100 nm.

[0147] (3) Compound 3 is evaporated on the surface of the first hole transport layer to obtain a second hole transport layer with a thickness of 5 nm.

[0148] (4) Compound 4, a light emitting host material, and compound 5, a light emitting guest material, are co-evaporated with a mass ratio of 99:1 to form an organic light emitting layer with a thickness of 25 nm on the surface of the second hole transport layer.

[0149] (5) Compound 6 is evaporated on the surface of the organic light emitting layer to form a hole blocking layer with a thickness of 5 nm, and then compound 7 and LiQ with a mixing ratio of 4:6 (mass ratio) are evaporated to form an electron transport layer with a thickness of 30 nm.

[0150] (6) Ytterbium (Yb) is evaporated on the surface of the electron transport layer to form an electron injection layer with a thickness of 5 nm, and magnesium (Mg) and silver (Ag) are mixed and deposited on the surface of the electron injection layer at a ratio of 1:9 to form a second electrode with a thickness of 14 nm as a cathode.

[0151] (7) Compound 8 is evaporated on the surface of the cathode to form a cover layer with a thickness of 60 nm.

[0152] The structural formula of the compounds involved in the above preparation process is shown in Table 1.

[0153] Table 1 Structural formula of compounds

[0154] Comparative Example 6

[0155] The difference from Example 4 is that compound 4 is replaced by the deuterated composition prepared in Comparative Example 1.

[0156] Comparative Example 7

[0157] The difference from Example 4 is that compound 4 is replaced by the deuterated composition prepared in Comparative Example 2.

[0158] Comparative Example 8

[0159] The difference from Example 4 is that compound 4 is replaced by the deuterated composition prepared in Comparative Example 3.

[0160] Example 5

[0161] The difference from Example 4 is that compound 4 is replaced by the deuterated composition prepared in Example 2.

[0162] Comparative Example 9

[0163] The difference from Example 4 is that compound 4 is replaced by the deuterated composition prepared in Comparative Example 4.

[0164] Example 6

[0165] The difference from Example 4 is that compound 4 is replaced by the deuterated composition prepared in Example 3.

[0166] Comparative Example 10

[0167] The difference from Example 4 is that compound 4 is replaced by the deuterated composition prepared in Comparative Example 5.

[0168] Device lifetime test

[0169] The organic light-emitting devices prepared in Examples 4-6 and Comparative Examples 6-10 were tested by a Fudan lifetime measurement system equipped with a power supply and a photodiode as a detection unit, and the test conditions were constant current 50 mA / cm 2 , to obtain the device lifetime under dark conditions, and the test results are shown in Table 2. LT95 refers to the time (hours) required for the luminance to decay to 95% from the initial luminance, and the longer the device lifetime, the more durable the device.

[0170] Table 2 Lifetime test results

[0171] As can be seen from Table 2, the deuterated composition of the present application can obtain an average deuterium substitution rate of anthryl and phenyl / naphthyl of more than 98%, and an average deuterium substitution rate of phenanthryl of less than 98%, and the use of the deuterated composition to prepare an organic light-emitting device can significantly improve the device lifetime.

[0172] At the same time, the preparation method of the present application can conveniently prepare the deuterated composition of the present application, greatly reduce the deuterium substitution cost, and is particularly suitable for industrial production, and the details are as follows:

[0173] In Example 1, although both Example 1 and Comparative Example 1 can achieve a high level of deuteration, because the solubility of the intermediate is much greater than that of the final product, the deuteration method of the present application can save deuterated reagents in the first deuteration, and is low in cost. For example, the volume weight ratio of deuterated benzene to the starting material to be deuterated used in the first deuteration of Example 1 is 20:1 (mL / g) (see the preparation of compound A2 in Example 1), and the volume weight ratio of deuterated benzene to the starting material to be deuterated in the second deuteration is 41.6:1 (mL / g), which can save the amount of deuterated benzene compared with two deuterations of the final product (Example 2), and is more economical.

[0174] Similarly, the products of Example 2 and Example 3 also have poor solubility, while the intermediate has good solubility, and the intermediate deuteration can save deuterated reagents.

[0175] The above description of the examples is to facilitate those of ordinary skill in the art to understand and apply the present application. Those skilled in the art can obviously make various modifications to these examples, and apply the general principles described herein to other examples without having to pay creative labor. Therefore, the present application is not limited to the examples herein, and improvements and modifications made by those skilled in the art based on the disclosure of the present application without departing from the scope and spirit of the present application are within the scope of the present application.

Claims

1. A deuterated composition characterized in that, Different deuterated versions of the compounds as shown in Formula I: In formula I, Ar1 is selected from phenyl or naphthyl; In different deuterium compounds, the average deuterium substitution rate of the deuterium-substitutable hydrogen of Ar1 and anthracene group is greater than 98%, and the average deuterium substitution rate of the deuterium-substitutable hydrogen of phenyl group is 96% to 98%.

2. The deuterated composition of claim 1, wherein different deuterated versions of the compound of Formula I are selected from the group consisting of: Wherein: D(n) represents that n deuteriums are substituted for the deuterium-substitutable hydrogen of anthracene group, and n≤8; D(m) represents that m deuteriums are substituted for the deuterium-substitutable hydrogen of phenyl group, and m≤9; When D(q1) appears, it represents that q1 deuteriums are substituted for the deuterium-substitutable hydrogen of phenyl group, and q1≤5; When D(q2) appears, it represents that q2 deuteriums are substituted for the deuterium-substitutable hydrogen of naphthyl group, and q2≤7.

3. The deuterated composition of claim 1, wherein The average deuterium substitution rate of the anthracene group is greater than the average deuterium substitution rate of the phenyl group, and the difference is p, and the value of p is 1% to 4%.

4. A deuterated composition characterized in that, The deuterium composition is prepared by subjecting compound A1 to a first deuterium substitution reaction to obtain compound A2, then subjecting the compound A2 to a reaction with compound A3 to obtain compound A4, and then subjecting the compound A4 to a second deuterium substitution reaction; Wherein: The structural formula of the compound A1 is: Ar1 is selected from phenyl or naphthyl; The structural formula of the compound A2 is: D(n') represents that n' deuteriums are substituted for the deuterium-substitutable hydrogen of anthracene group, and n'≤8, and Ar1' is selected from fully or partially deuterated phenyl group, fully or partially deuterated naphthyl group; The structural formula of the compound A3 is: The structural formula of compound A4 is:

5. The deuterated composition of claim 4, wherein The first deuterium substitution reaction is carried out by placing compound A1 in a first deuterium substitution reagent in the presence of a first catalyst, and the conditions of the first deuterium substitution reaction meet at least one of the following conditions: (a) the first catalyst comprises at least one of a protonic acid, a Lewis acid, and a high-molecular-weight sulfonic acid; (b) the mass of the first catalyst is 3% to 20% of the mass of the compound A1; (c) the first deuterium substitution reagent comprises deuterated benzene or deuterated water; (d) the ratio of the volume of the first deuterium substitution reagent to the mass of the compound A1 is (20-50) mL:1 g; (e) the reaction temperature is reflux temperature, and the reaction time is 1 to 5 days.

6. The deuterated composition of claim 4, wherein The second deuterium substitution reaction is carried out by placing the compound A4 in a second deuterium substitution reagent in the presence of a second catalyst, and the conditions of the second deuterium substitution reaction meet at least one of the following conditions: (a) the second catalyst comprises at least one of a protonic acid, a Lewis acid, and a high-molecular-weight sulfonic acid; (b) the mass of the second catalyst is 3% to 20% of the mass of the compound A4; (c) the second deuterium substitution reagent comprises deuterated benzene or deuterated water; (d) the ratio of the volume of the second deuterium substitution reagent to the mass of the compound A4 is (40-200) mL:1 g; (e) the reaction temperature is reflux temperature, and the reaction time is 1 to 5 days.

7. A method of producing a deuterated composition, characterized by, Comprising the following steps: carrying out a first deuterium substitution reaction on compound A1 to obtain compound A2; wherein, the structural formula of the compound A1 is: Ar1is selected from phenyl or naphthyl; the structural formula of the compound A2 is: D(n') represents that n' deuteriums are substituted for the deuterium-substitutable hydrogen of anthracene group, and n'≤8, and Ar1' is selected from fully or partially deuterated phenyl group, fully or partially deuterated naphthyl group; reacting the compound A2 with a compound A3 to obtain a compound A4; the structural formula of the compound A3 is: The structural formula of compound A4 is: Subjecting the compound A4 to a second deuterium substitution reaction to obtain a deuterium composition comprising different deuterium compounds, and the structure of the deuterium compounds is shown in formula II: D(n) represents that n deuterium pairs are substituted to anthracene group, and n'≤n≤8, D(m) represents that m deuterium pairs are substituted to deuterium-substitutable hydrogen of phenanthrene group, and m≤9, Ar1" is selected from phenyl group which is fully or partially deuterated, naphthyl group which is fully or partially deuterated, and the number of deuterium substitution of Ar1" is greater than or equal to the number of deuterium substitution of Ar1'.

8. The method of claim 7, wherein the deuterated composition is prepared by, The method for performing the first deuterium substitution reaction comprises: subjecting compound A1 to deuterium substitution reaction in a first deuterium substitution reagent in the presence of a first catalyst.

9. The method of claim 8, wherein the deuterated composition is prepared by, The conditions of the first deuterium substitution reaction satisfy at least one of the following conditions: (a) the first catalyst comprises at least one of a protic acid, a Lewis acid, and a high-molecular-weight bonded sulfonic acid; (b) the mass of the first catalyst is 3% to 20% of the mass of the compound A1; (c) the first deuterium substitution reagent comprises deuterated benzene or deuterated water; (d) the ratio of the volume of the first deuterium substitution reagent to the mass of the compound A1 is (20-50) mL:1 g; (e) the reaction temperature is reflux temperature, and the reaction time is 1-5 days.

10. The method of claim 7, wherein the deuterated composition is prepared by, The method for reacting the compound A2 with the compound A3 satisfies at least one of the following conditions:

11. The method of claim 10, wherein the deuterated composition is prepared by, (a1) the method for brominating the compound A2 comprises: reacting the compound A2 with N-bromosuccinimide, and the solvent used is selected from at least one of N,N-dimethylformamide, toluene, and chlorobenzene, the reaction temperature is 0-40℃, and the reaction time is 1-24 hours; (b1) when the coupling reaction is performed, the catalyst is selected from platinum compounds and palladium compounds, the auxiliary ligand is selected from phosphine ligands, the reaction system is alkaline, the solvent used is selected from at least one of benzene, toluene, xylene, and chlorobenzene, the reaction temperature is room temperature to the boiling point temperature of the solvent, and the reaction time is 1-24 hours. The method for performing the second deuterium substitution reaction comprises: subjecting the compound A4 to deuterium substitution reaction in a second deuterium substitution reagent in the presence of a second catalyst.

12. The method of claim 7, wherein the deuterated composition is prepared by, The conditions of the second deuterium substitution reaction satisfy at least one of the following conditions:

13. The method of claim 12, wherein the deuterated composition is prepared by, (a) the second catalyst comprises at least one of a protic acid, a Lewis acid, and a high-molecular-weight bonded sulfonic acid; (b) the mass of the second catalyst is 3% to 20% of the mass of the compound A4; (c) the second deuterium substitution reagent comprises deuterated benzene or deuterated water; (d) the ratio of the volume of the second deuterium substitution reagent to the mass of the compound A4 is (40-200) mL:1 g; (e) the reaction temperature is reflux temperature, and the reaction time is 1-5 days. The deuterium-substituted composition is prepared by the method for preparing the deuterium-substituted composition according to any one of claims 7 to 13.

14. A light emitting layer, characterized in that, ​ ​ 15. The light emitting layer of claim 14, wherein, The light-emitting layer also includes a compound as shown in Formula III: wherein Q1and Q2are each independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzo-cycloalkyl group, and substituents when substituted are selected from hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms, a linear or branched alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group; R is selected from deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms, a linear or branched alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group; n is an integer of 0 to 3; when n is 3 and R is a linear or branched alkyl group having 1 to 10 carbon atoms, the two adjacent alkyl groups are cyclized; Ar1and Ar2are independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl-cycloalkyl group having 6 to 30 carbon atoms, and substituents are selected from an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 6 to 30 carbon atoms, a linear or branched alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group.

16. An organic light-emitting device, characterized in that, An organic electroluminescence device comprising a first electrode and a second electrode disposed opposite each other and an organic layer between the first electrode and the second electrode, wherein the organic layer comprises the light-emitting layer according to claim 14 or 15.

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