CN113563315A - Compound, organic electroluminescent device and display device - Google Patents

Compound, organic electroluminescent device and display device Download PDF

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CN113563315A
CN113563315A CN202110807129.3A CN202110807129A CN113563315A CN 113563315 A CN113563315 A CN 113563315A CN 202110807129 A CN202110807129 A CN 202110807129A CN 113563315 A CN113563315 A CN 113563315A
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compound
carbon atoms
formula
organic electroluminescent
synthesis
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CN113563315B (en
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王占奇
郭林林
李志强
陆金波
丁言苏
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Beijing Xinyihua Material Technology Co ltd
Fuyang Sineva Material Technology Co Ltd
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Beijing Xinyihua Material Technology Co ltd
Fuyang Sineva Material Technology Co Ltd
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Abstract

The present application relates to electroluminescent collarsDisclosed are a compound, an organic electroluminescent device and a display device. The structural formula of the compound is shown as the formula (I):

Description

Compound, organic electroluminescent device and display device
Technical Field
The application relates to the field of electroluminescence, in particular to a compound, an organic electroluminescent device and a display device.
Background
Currently, organic electroluminescent (OLED) display technology has been applied in the fields of smart phones, tablet computers, and the like, and further will be expanded to large-size application fields such as televisions. In the development process of the last 30 years, various OLED materials with excellent performance are developed, and the commercialization process of the OLED is accelerated by different designs of the device structure and optimization of the device life, efficiency and other properties, so that the OLED is widely applied in the fields of display and illumination.
The selection of the hole layer, the light-emitting layer and other organic functional layer materials also has a great influence on the current efficiency, the driving voltage and the lifetime of the device, and functional layer materials with higher performance are still being explored.
Therefore, in order to meet the higher requirements of people for OLED devices, the development of more various and higher-performance OLED materials is urgently needed in the art.
Disclosure of Invention
The compound can be used as a main body material and an electron transmission material of an OLED (organic light emitting diode) light emitting device, and the obtained organic electroluminescent device has lower driving voltage and higher current efficiency, is particularly suitable for a red light emitting device or a green light emitting device, is used for reducing the driving voltage of the red light emitting device or the green light emitting device, and improves the light emitting efficiency of the two devices.
In order to achieve the purpose, the application provides the following technical scheme:
the application provides a compound, which has a structure shown in a formula (I),
Figure BDA0003167026290000011
wherein X is selected from O or S;
R11、R21independently selected from deuterium, F, CN, alkyl group containing 1-20 carbon atoms, alkoxy group containing 1-20 carbon atoms, aryl group containing 6-40 carbon atoms;
Ar、Ar1、Ar2each independently selected from aromatic groups having 6 to 40 carbon atoms;
Ar3selected from aromatic group containing 6-40 carbon atoms or one of C-1-C-7,
Figure BDA0003167026290000021
wherein X1～X12Each independently selected from NR1、O、S、CR2R3And X1And X2At least one selected from NR1，X3And X4At least one selected from NR1，X5And X6At least one selected from NR1，X7And X8At least one selected from NR1，X9And X10At least one selected from NR1，X11And X12At least one selected from NR1；R1Selected from alkyl containing 1-20 carbon atoms or aryl containing 6-40 carbon atoms; r2、R3Each independently selected from an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, and R2And R3The carbon atoms on the above may be linked to form a ring; c-1 to C-7 participate in connection through SP2 hybridized carbon atoms;
Z1、Z2、Z3each independently selected from N or CR, wherein R is selected fromFrom hydrogen, deuterium, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, and Z1、Z2、Z3At least one is selected from N;
p is selected from 0 and 1;
m and n are selected from 0, 1, 2, 3 and 4;
the hydrogen in the compound represented by formula (I) may be substituted by an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, benzene, biphenyl, naphthalene, phenanthrene, anthracene, fluorene, benzofluorene, dibenzofluorene, triphenylene, fluoranthene, pyrene, perylene, spirofluorene, indenofluorene or hydrogenated benzanthracene.
Further, Ar1、Ar2Independently selected from one or the combination of more than two groups of benzene, biphenyl, naphthalene, phenanthrene, anthracene, fluorene, benzofluorene, dibenzofluorene, triphenylene, fluoranthene, pyrene, perylene, spirofluorene, indenofluorene or hydrogenated benzanthracene.
Further, R11、R21Each independently selected from one of hydrogen, deuterium, F, CN, alkyl containing 1-6 carbon atoms, alkoxy containing 1-6 carbon atoms, benzene, biphenyl, naphthalene, phenanthrene, anthracene, fluorene, benzofluorene, dibenzofluorene, triphenylene, fluoranthene, pyrene, perylene, spirofluorene, indenofluorene or hydrogenated benzanthracene.
Further, Z1、Z2And Z3At least two of which are selected from N.
Further, Z1、Z2And Z3Are all selected from N.
Further, Ar1、Ar2One of which is selected from benzene or biphenyl.
Further, Ar is selected from benzene, and p is selected from 1.
Further, in the formula (1), X is selected from O or S, Ar3Selected from benzene, biphenyl, or one of the following structures:
Figure BDA0003167026290000031
further, the compound is selected from the following compounds in tables 1 to 8:
TABLE 1
Figure BDA0003167026290000032
Figure BDA0003167026290000041
Figure BDA0003167026290000051
Figure BDA0003167026290000061
TABLE 2
Figure BDA0003167026290000071
Figure BDA0003167026290000081
Figure BDA0003167026290000091
Figure BDA0003167026290000101
TABLE 3
Figure BDA0003167026290000102
Figure BDA0003167026290000111
Figure BDA0003167026290000121
Figure BDA0003167026290000131
Figure BDA0003167026290000141
TABLE 4
Figure BDA0003167026290000142
Figure BDA0003167026290000151
Figure BDA0003167026290000161
Figure BDA0003167026290000171
Figure BDA0003167026290000181
TABLE 5
Figure BDA0003167026290000182
Figure BDA0003167026290000191
Figure BDA0003167026290000201
Figure BDA0003167026290000211
Figure BDA0003167026290000221
TABLE 6
Figure BDA0003167026290000222
Figure BDA0003167026290000231
Figure BDA0003167026290000241
Figure BDA0003167026290000251
Figure BDA0003167026290000261
TABLE 7
Figure BDA0003167026290000262
Figure BDA0003167026290000271
Figure BDA0003167026290000281
Figure BDA0003167026290000291
Figure BDA0003167026290000301
TABLE 8
Figure BDA0003167026290000302
Figure BDA0003167026290000311
Figure BDA0003167026290000321
Figure BDA0003167026290000331
Figure BDA0003167026290000341
Wherein, in the compounds listed in tables 1 to 8, X is selected from O or S, Ar3Selected from benzene, biphenyl, or the following structure:
Figure BDA0003167026290000351
further, the structure of formula (I) also includes compounds of the following structures:
Figure BDA0003167026290000352
Figure BDA0003167026290000361
Figure BDA0003167026290000371
Figure BDA0003167026290000381
Figure BDA0003167026290000391
Figure BDA0003167026290000401
Figure BDA0003167026290000411
the present application also provides an organic electroluminescent device comprising a compound of the present application.
Further, the material of the electron transport layer of the organic electroluminescent device is the compound of the application.
Further, the host material of the light-emitting layer of the organic electroluminescent device is the compound.
Further, the organic electroluminescent device is a red device.
Further, the organic electroluminescent device is a red phosphorescent device.
The application also provides a display device which comprises the organic electroluminescent device provided by the application.
By adopting the technical scheme of the application, the beneficial effects are as follows:
the application provides a compound shown in formula (I), wherein spirofluorene xanthene or spirofluorene thiaanthracene is used as a mother nucleus, the substitution position of each substituent group in the mother nucleus is defined, and a specific substituent group is defined at the same time, so that the material performance is improved, and an organic electroluminescent device prepared by using the compound has high luminous efficiency, low driving voltage and long service life.
Detailed Description
The technical solutions in the embodiments of the present application will be clearly and completely described below with reference to the embodiments 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 of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present application.
It should be noted that: in the present application, all embodiments and preferred methods mentioned herein can be combined with each other to form new solutions, if not specifically stated. In the present application, all the technical features mentioned herein as well as preferred features may be combined with each other to form new technical solutions, if not specifically stated. In the present application, percentages (%) or parts refer to percent by weight or parts by weight relative to the composition, unless otherwise specified. In the present application, the components referred to or the preferred components thereof may be combined with each other to form new embodiments, if not specifically stated. In this application, unless otherwise stated, the numerical range "a-b" represents a shorthand representation of any combination of real numbers between a and b, where a and b are both real numbers. For example, a numerical range of "6 to 22" means that all real numbers between "6 to 22" have been listed herein, and "6 to 22" is simply a shorthand representation of the combination of these values. The "ranges" disclosed herein may be in the form of lower limits and upper limits, and may be one or more lower limits and one or more upper limits, respectively. In the present application, unless otherwise indicated, the individual reactions or process steps may or may not be performed in sequence. Preferably, the reaction processes herein are carried out sequentially.
Unless otherwise defined, technical and scientific terms used herein have the same meaning as is familiar to those skilled in the art. In addition, any methods or materials similar or equivalent to those described herein can also be used in the present application.
And (3) synthesis of an intermediate:
(1) synthesis of intermediate M-1:
Figure BDA0003167026290000421
adding 5.5 g of a compound shown by M-0 and 200 ml of dried tetrahydrofuran in a 500 ml three-necked bottle under the protection of nitrogen, cooling to-78 ℃, controlling the temperature to be below-70-78 ℃, dropwise adding 6.25 ml of a 1.6M n-hexane solution of butyllithium, controlling the temperature to be-70-78 ℃ after adding, keeping for 1 hour, adding 2.54 g of iodine at one time, slowly heating to 20 ℃, keeping for 2 hours at the temperature of 20-25 ℃, adding water and dichloromethane for separating liquid, washing a dichloromethane layer with water, washing with a 1% sodium bisulfite solution, concentrating to dryness, and crystallizing for 3 times by using a mixed solvent of chlorobenzene and ethanol to obtain 3.8 g of the compound shown by M-1.
Performing mass spectrometric detection on the compound shown as M-1, wherein the maximum two peaks are 538 and 536, and determining that the molecular formula of M-1 is C25H14BrIO。
Synthesis example 1-synthesis of compound 1:
Figure BDA0003167026290000431
(1) synthesis of M-2
A250 ml three-neck flask is put into a nitrogen protection bottle, 80 ml of dioxane and 20 ml of water are added, 5.37 g (0.01mol) of a compound shown as M1-1, 1.22 g (0.01mol) of phenylboronic acid, 2.12 g (0.02mol) of sodium carbonate and 0.115 g (0.0001mol) of tetrakistriphenylphosphine palladium are added, the temperature is slowly increased to 60 ℃ for reaction for 6 hours, the temperature is reduced, water and toluene are added for liquid separation, an organic layer is washed by water, magnesium sulfate is dried, the magnesium sulfate is filtered and removed, the solvent is reduced under reduced pressure, the obtained solid is recrystallized by using a mixed solvent of ethanol and chlorobenzene, and 3.9 g of the compound shown as a formula M-2 is obtained.
Performing mass spectrum detection on the compound shown in the formula M-2, determining that the molecular formula of M-2 is C, wherein the largest two peaks are 486 and 48831H19BrO。
(2) Synthesis of M-3
Adding 4.87 g of a compound shown as M-2 and 300 ml of dried tetrahydrofuran in a 500 ml three-neck flask under the protection of nitrogen, cooling to-78 ℃, controlling the temperature to be below-70-78 ℃, dropwise adding 8 ml of a 1.6M n-hexane solution of butyllithium, controlling the temperature to be below-70-78 ℃, keeping the temperature for 1 hour at the temperature of-70-78 ℃, adding 1.8 g of trimethyl borate at one time, slowly heating to 20 ℃, keeping the temperature for 4 hours at the temperature of 20-25 ℃, adding water and ethyl acetate for separating liquid, washing an organic layer with water, concentrating to dryness, obtaining a compound shown as M-3, and directly carrying out the next reaction without further purification.
(3) Synthesis of Compound 1
A 500 ml three-neck flask, under the protection of nitrogen, adding 300 ml of dioxane and 60 ml of water, adding the unpurified compound shown as M-3 obtained in the previous step, 3.88 g of 2- (4-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine, 2.12 g of sodium carbonate and 0.115 g of palladium tetratriphenylphosphine, slowly heating to reflux reaction for 8 hours, cooling, adding water and toluene for separating liquid, washing an organic layer with water, drying magnesium sulfate, filtering to remove the magnesium sulfate, removing the solvent under reduced pressure, and boiling and washing the obtained solid with hot acetone to obtain 6.1 g of the compound shown as formula 1.
The compound shown in the formula 1 is subjected to mass spectrometric detection, and the m/z is 715.
Synthesis example 2-synthesis of compound 2:
Figure BDA0003167026290000441
referring to the synthesis of Compound 1, except that in step (3), 2- (4-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine is replaced with 2- ([1,1' -biphenyl ] -4-yl) -4- (4-bromophenyl) -6-phenyl-1, 3, 5-triazine to give the compound of formula 2.
The compound shown in the formula 2 is subjected to mass spectrometric detection, and the m/z is 791.
Synthesis example 3-synthesis of compound 3:
Figure BDA0003167026290000442
referring to the synthesis of compound 1, except that in step (3), 2- (4-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine therein is replaced with 2- (4-bromophenyl) -4- (9, 9-dimethyl-9H-fluoren-2-yl) -6-phenyl-1, 3, 5-triazine to obtain the compound represented by formula 3.
The compound shown in the formula 3 is subjected to mass spectrometric detection, and the m/z is 831.
Synthesis example 4-synthesis of compound 4:
Figure BDA0003167026290000443
referring to the synthesis of Compound 1, except that in step (3), 2- (4-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine is replaced with 2, 4-bis ([1,1' -biphenyl ] -4-yl) -6- (4-bromophenyl) -1,3, 5-triazine to give the compound of formula 4.
The compound shown in the formula 4 is subjected to mass spectrometric detection, and the m/z is 867.
Synthesis example 5-synthesis of compounds 5-8:
Figure BDA0003167026290000451
referring to the syntheses of compounds 1-4, respectively, except that in step (1), phenylboronic acid therein is replaced with 3-phenylboronic acid to give compounds 5-8.
The compound shown as the formula 5 is subjected to mass spectrometric detection, and the m/z is 791.
The compound shown as the formula 6 is subjected to mass spectrometric detection, and the m/z is 867.
The compound shown in the formula 7 is subjected to mass spectrometric detection, and the m/z is 907.
The compound shown in the formula 8 is subjected to mass spectrometric detection, and the m/z is 943.
Synthesis example 6 Synthesis of Compounds 9-12:
Figure BDA0003167026290000452
referring to the synthesis of compounds 1-4, respectively, except that in step (1), phenylboronic acid therein is replaced with N-phenylcarbazole-3-boronic acid to give compounds 9-12.
The compound shown as the formula 9 is subjected to mass spectrometric detection, and the m/z is 880.
Mass spectrometric detection of a compound of formula 10 was carried out at m/z 956.
The compound shown in the formula 11 is subjected to mass spectrometric detection, and the m/z is 996.
The compound shown in the formula 12 is subjected to mass spectrometric detection, and the m/z is 1032.
Synthesis example 7 Synthesis of Compounds 13 to 16:
Figure BDA0003167026290000461
referring to the synthesis of Compound 1, except that in step (3), 2- (4-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine is replaced with 2-bromo-4, 6-diphenyl-1, 3, 5-triazine to give the compound of formula 13.
The compound shown as the formula 13 is subjected to mass spectrometric detection, and m/z is 639.
Referring to the synthesis of Compound 1, except that in step (3), 2- (4-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine is replaced with 2-bromo-4-phenyl-6- (4-biphenyl) -1,3, 5-triazine to give the compound of formula 14.
The compound shown in the formula 14 is subjected to mass spectrometric detection, and the m/z is 715.
Referring to the synthesis of Compound 1, except that in step (3), 2- (4-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine is replaced with 2-bromo-4-2-naphthyl-6-phenyl-1, 3, 5-triazine to give the compound of formula 15.
The compound shown in the formula 15 is subjected to mass spectrometric detection, and m/z is 689.
Referring to the synthesis of Compound 1, except that in step (3), 2- (4-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine is replaced with 2, 4-bis ([1,1' biphenyl ] -4-yl) -6-bromo-1, 3, 5-triazine to give the compound of formula 16.
The compound shown in the formula 16 is subjected to mass spectrometric detection, and the m/z is 791.
Synthesis example 8-synthesis of compound 21:
Figure BDA0003167026290000462
referring to the synthesis of compound 13, except for the step (1), the phenylboronic acid therein is replaced with N-phenylcarbazole-3-boronic acid to obtain the compound represented by formula 21.
The compound shown in the formula 21 is subjected to mass spectrometric detection, and the m/z is 804.
Synthesis example 9-synthesis of compound 25:
Figure BDA0003167026290000471
referring to the synthesis of compound 13, except for the step (1), the phenylboronic acid therein is replaced with 4- (N-carbazolyl) phenylboronic acid to obtain the compound represented by formula 25.
The compound shown in the formula 25 is subjected to mass spectrometric detection, and the m/z is 804.
Synthesis example 10 Synthesis of Compound P-1:
(1) synthesis of (7, 7-dimethyl-5-phenyl-5, 7-indolino [2,1-b ] carbazol-9-yl) boronic acid
Figure BDA0003167026290000472
Referring to the synthesis of M-3, the corresponding bromide was reacted with butyllithium and trimethyl borate in this order, followed by hydrolysis to give (7, 7-dimethyl-5-phenyl-5, 7-indolino [2,1-b ] carbazol-9-yl) boronic acid.
(2) Synthesis of Compound P-1
Figure BDA0003167026290000473
With reference to the synthesis of compound 1, except that phenylboronic acid therein was replaced with the (7, 7-dimethyl-5-phenyl-5, 7-indolino [2,1-b ] carbazol-9-yl) boronic acid prepared in the previous step to give compound P-1.
The compound shown as the P-1 is subjected to mass spectrometric detection, and the m/z is 996.
Synthesis example 11 Synthesis of Compound P-10:
(1) synthesis of (12, 12-dimethyl-11-phenyl-11, 12-indolino [2,1-a ] carbazol-8-yl) boronic acid
Figure BDA0003167026290000481
Referring to the synthesis of M-3, the corresponding bromide was reacted with butyllithium and trimethyl borate in this order, followed by hydrolysis to give (12, 12-dimethyl-11-phenyl-11, 12-indolino [2,1-a ] carbazol-8-yl) boronic acid.
(2) Synthesis of Compound P-10
Figure BDA0003167026290000482
With reference to the synthesis of compound 1, except that phenylboronic acid therein was replaced with the (12, 12-dimethyl-11-phenyl-11, 12-indolino [2,1-a ] carbazol-8-yl) boronic acid prepared in the previous step to give compound P-10.
The compound shown as the P-10 is subjected to mass spectrometric detection, and the m/z is 996.
Synthesis example 12 Synthesis of Compound P-19:
Figure BDA0003167026290000483
referring to the synthesis of compound P-1, except that 2- (4-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine therein was changed to 2-bromo-4, 6-diphenyl-1, 3, 5-triazine, compound P-19 was obtained.
The compound shown as P-19 is subjected to mass spectrometric detection, and the m/z is 920.
Other compounds, for which synthetic methods are not specifically described, can be synthesized by conventional reactions using methods well known in the art.
Materials used in device examples:
Figure BDA0003167026290000491
device example 1
The compound of the application is selected as an electron transport material in an organic electroluminescent device in the examples, and H-1, H-3 and H-6 are selected as electron transport materials in the organic electroluminescent device in the comparative examples.
The organic electroluminescent device has the following structure: ITO/HIL02(100nm)/NPB (40nm)/EM1(30 nm)/electron transport material (30nm)/LiF (0.5nm)/Al (150 nm).
The preparation process of the organic electroluminescent device is as follows:
carrying out ultrasonic treatment on the glass substrate coated with the ITO transparent conductive layer (serving as an anode) in a cleaning agent, then washing the glass substrate in deionized water, ultrasonically removing oil in a mixed solvent of acetone and ethanol, baking the glass substrate in a clean environment until the water is completely removed, cleaning the glass substrate by using ultraviolet light and ozone, and bombarding the surface by using low-energy cation beams to improve the surface property and improve the binding capacity with a hole injection layer;
placing the glass substrate in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, performing vacuum evaporation on the anode to form HIL02 as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 100 nm;
carrying out vacuum evaporation on NPB (N-propyl bromide) on the hole injection layer to form a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 40 nm;
vacuum evaporating EM1 on the hole transport layer to serve as an organic light emitting layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness is 30 nm;
respectively carrying out vacuum evaporation on the organic light-emitting layer to form a comparison compound and the compound of the invention as an electron transport layer of an organic electroluminescent device; the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30 nm;
LiF with the thickness of 0.5nm and Al with the thickness of 150nm are evaporated on the electron transport layer in vacuum to be used as an electron injection layer and a cathode.
The luminance, driving voltage, and current efficiency of the prepared organic electroluminescent device were measured.
The organic electroluminescent device properties are shown in table 9 below. And testing by using an OLED-1000 multichannel accelerated aging life and light color performance analysis system produced in Hangzhou distance.
TABLE 9
Electron transport material Required luminance cd/m2 Drive voltage V Current efficiency cd/A
HT-1 1000 5.08 1.62
HT-3 1000 4.88 1.05
HT-6 1000 5.01 1.77
Compound 1 1000 4.56 1.90
Compound 2 1000 4.61 2.01
Compound 4 1000 4.49 1.96
Compound 15 1000 4.55 1.89
Compound 30 1000 4.60 1.99
Compound 37 1000 3.88 2.01
Compound 40 1000 4.71 2.24
Compound 41 1000 4.69 2.33
Compound 42 1000 4.86 2.19
As can be seen from the data in table 9, compared with the comparative example, the organic electroluminescent device prepared by using the compound of the embodiment of the present application has the advantages of significantly reduced driving voltage, significantly improved current efficiency, more significantly reduced voltage of the compound 37, and better efficiency improvement effect of the compounds 40 to 42.
Device example 2
The compound of the application is selected as the red light main body material in the organic electroluminescent device in the embodiment, and H-2, H-4 and H-5 are selected as the red light main body material in the organic electroluminescent device in the comparative embodiment.
The structure of the organic electroluminescent device is as follows: ITO/NPB (40 nm)/Red host Material (35 nm): ir (piq)3[ 10% ]/TPBI (10nm)/Alq3(15nm)/LiF (0.5nm)/Al (150 nm). Wherein "Ir (piq)3[ 10% ]" refers to the doping ratio of the red dye, i.e. the weight portion ratio of the red host material to Ir (piq)3 is 100: 10.
The preparation process of the organic electroluminescent device is as follows: the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, vacuum evaporating air on the anode layer filmThe evaporation rate of the hole transmission layer NPB is 0.1nm/s, and the thickness of the evaporation film is 40 nm;
vacuum evaporating a red light main material and a dye Ir (piq)3 on the hole transport layer to be used as a light emitting layer of the organic electroluminescent device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 35 nm; (ii) a
Sequentially vacuum evaporating an electron transport layer TPBI and an electron transport layer Alq3 on the light-emitting layer, wherein the evaporation rates are both 0.1nm/s, and the evaporation film thicknesses are respectively 10nm and 15 nm;
and (3) evaporating LiF with the thickness of 0.5nm and Al with the thickness of 150nm on the electron transport layer in vacuum to be used as an electron injection layer and a cathode.
All the organic electroluminescent devices are prepared by the method, and the differences only lie in the selection of the red light main body material, and the details are shown in the following table 10.
And (3) performance testing:
the brightness, the driving voltage and the current efficiency of the prepared organic electroluminescent device are measured by using a Hangzhou remote production OLED-1000 multichannel accelerated aging life and photochromic performance analysis system test, and the test results are shown in the following table.
Watch 10
Figure BDA0003167026290000511
Figure BDA0003167026290000521
As can be seen from the above table, compared to the comparative compound, the compound provided by the present application as the red host material of the organic electroluminescent device can improve the light emitting efficiency and reduce the driving voltage, and the voltage reduction is significant for the compounds P-40 to P-43, although the efficiency is not improved.
It will be apparent to those skilled in the art that various changes and modifications may be made in the embodiments of the present application without departing from the spirit and scope of the application. Thus, if such modifications and variations of the present application fall within the scope of the claims of the present application and their equivalents, the present application is intended to include such modifications and variations as well.

Claims (10)

1. A compound having the structure of formula (i):
Figure FDA0003167026280000011
wherein X is selected from O or S;
R11、R21independently selected from deuterium, F, CN, alkyl group containing 1-20 carbon atoms, alkoxy group containing 1-20 carbon atoms, aryl group containing 6-40 carbon atoms;
Ar、Ar1、Ar2each independently selected from aromatic groups having 6 to 40 carbon atoms;
Ar3selected from aromatic group containing 6-40 carbon atoms or one of C-1-C-7,
Figure FDA0003167026280000012
wherein X1～X12Each independently selected from NR1、O、S、CR2R3And X1And X2At least one selected from NR1，X3And X4At least one selected from NR1，X5And X6At least one selected from NR1，X7And X8At least one selected from NR1，X9And X10At least one selected from NR1，X11And X12At least one selected from NR1；R1Selected from alkyl containing 1-20 carbon atoms or aryl containing 6-40 carbon atoms; r2、R3Each independently selected from an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, and R2And R3The carbon atoms on the above may be linked to form a ring; c-1 to C-7 participate in connection through SP2 hybridized carbon atoms;
Z1、Z2、Z3each independently selected from N or CR, wherein R is selected from hydrogen, deuterium, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, and Z1、Z2、Z3At least one is selected from N;
p is selected from 0 and 1;
m and n are selected from 0, 1, 2, 3 and 4;
the hydrogen in the compound represented by formula (I) may be substituted by an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, benzene, biphenyl, naphthalene, phenanthrene, anthracene, fluorene, benzofluorene, dibenzofluorene, triphenylene, fluoranthene, pyrene, perylene, spirofluorene, indenofluorene or hydrogenated benzanthracene.
2. The compound of claim 1, wherein Ar, Ar1、Ar2Independently selected from one or a combination of two of benzene, biphenyl, naphthalene, phenanthrene, anthracene, fluorene, benzofluorene, dibenzofluorene, triphenylene, fluoranthene, pyrene, perylene, spirofluorene, indenofluorene or hydrogenated benzanthracene.
3. A compound of claim 1, wherein R is11、R21Each independently selected from one of hydrogen, deuterium, F, CN, alkyl containing 1-6 carbon atoms, alkoxy containing 1-6 carbon atoms, benzene, biphenyl, naphthalene, phenanthrene, anthracene, fluorene, benzofluorene, dibenzofluorene, triphenylene, fluoranthene, pyrene, perylene, spirofluorene, indenofluorene or hydrogenated benzanthracene.
4. The compound of claim 1, wherein Z is1、Z2And Z3At least two of which are selected from N.
5. The compound of claim 1, wherein Z is1、Z2And Z3Are all selected from N.
6. According to the rightThe compound of claim 1, wherein Ar is Ar1、Ar2One of which is selected from benzene or biphenyl.
7. The compound of claim 1, wherein Ar is selected from benzene and p is selected from 1.
8. The compound according to claim 1, wherein in the formula (1), X is selected from O or S, Ar3Selected from benzene, biphenyl, or one of the following structures:
Figure FDA0003167026280000021
9. an organic electroluminescent device, characterized in that it comprises a compound according to any one of claims 1 to 8.
10. A display device comprising the organic electroluminescent device according to claim 9.
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