Phenyl naphthyl anthracene compound and deuterated composition thereof

Abstract

The invention provides a phenyl naphthyl anthracene compound and a deuterated composition thereof. The phenyl naphthyl anthracene compound has a structure as shown in the following formula (I). The phenyl naphthyl anthracene compound and the deuterated composition thereof provided by the invention can be used as a main body material of a luminescent layer of an OLED luminescent device, so that the OLED luminescent device has relatively low driving voltage, relatively high current efficiency and relatively long service life.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic electroluminescent materials, and particularly relates to a phenylnaphthylanthracene compound and its deuterated composition. Background Art

[0002] An organic electroluminescent device is a device prepared by depositing one or more organic materials between two metal electrodes by spin coating or vacuum evaporation. A classic three-layer organic electroluminescent device includes a hole transport layer, a light-emitting layer, and an electron transport layer. Holes generated from the anode pass through the hole transport layer and electrons generated from the cathode pass through the electron transport layer and combine in the light-emitting layer to form excitons, and then emit light. The organic electroluminescent device can adjust the emission of various required lights by changing the material of the light-emitting layer as needed.

[0003] As a new type of display technology, organic electroluminescent devices have unique advantages such as self-luminescence, wide viewing angle, low energy consumption, high efficiency, thinness, rich colors, fast response speed, wide applicable temperature range, low driving voltage, and can be used to manufacture flexible, bendable and transparent display panels as well as environmental friendliness. They can be applied to flat panel displays and new generation lighting, and can also be used as the backlight of LCDs.

[0004] Since its invention in the late 1980s, organic electroluminescent devices have been industrially applied, such as being used as the screens of cameras and mobile phones, etc. However, the current OLED devices are restricted from wider applications due to factors such as low efficiency and short service life, especially for large screen displays. Therefore, it is necessary to improve the efficiency of the devices. And an important factor restricting this is the performance of the organic electroluminescent materials in the organic electroluminescent devices. Therefore, it is necessary to develop stable and efficient organic electroluminescent materials to improve the current efficiency and service life of OLED devices. Summary of the Invention

[0005] Aiming at the deficiencies of the prior art, the purpose of the present invention is to provide a phenylnaphthylanthracene compound and its deuterated composition, intermediate, organic electroluminescent device and display device. The phenylnaphthylanthracene compound and deuterated composition provided by the present invention can be used as the host material of the light-emitting layer of the OLED light-emitting device, so that the OLED light-emitting device has a lower driving voltage, a higher current efficiency and a longer life.

[0006] To achieve this purpose, the present invention adopts the following technical solutions:

[0007] In a first aspect, the present invention provides a phenylnaphthylanthracene compound, and the phenylnaphthylanthracene compound is a compound represented by formula (I):

[0008]

[0009] Among them, Ar1 is selected from phenyl, naphthyl, biphenyl or naphthyl-substituted phenyl;

[0010] The H atom in Ar1 can be replaced by a D atom;

[0011] D in formula (I) represents a deuterium atom.

[0012] Preferably, the compound represented by formula (I) includes the compounds represented by the following formula (I-A) and formula (I-B):

[0013]

[0014] Furthermore, the compound represented by formula (I) includes the compounds represented by the following formula (I-A-1) to formula (I-A-4) or formula (I-B-5) to formula (I-B-8):

[0015]

[0016] As a preferred technical solution of the present invention, the compound represented by formula (I) is selected from any one of the following substituted or unsubstituted compounds:

[0017]

[0018]

[0019]

[0020]

[0021]

[0022] The substitution means that in the structure of the corresponding Ar1 part in the structure of formula (I), some or all of the H atoms are replaced by D atoms.

[0023] Illustrations are as follows:

[0024] The structure of Compound 1 is as follows:

[0025]

[0026] The substituted Compound 1 includes, but is not limited to, the following structures:

[0027]

[0028] Preferably, the compound represented by formula (I) is selected from the following structures:

[0029]

[0030] Second aspect, the present invention provides a deuterated composition, the deuterated composition at least comprises a first component and a second component, the first component is selected from any one of the compounds shown by formula (I), the second component has a different structure from the first component, and can be selected from any one of the compounds shown by formula (I), or can be selected from any one of the compounds shown by formula A.

[0031] Preferably, the second component is selected from any one of the compounds shown by formula (I).

[0032] The compound shown by formula A is as follows:

[0033]

[0034] Wherein, Ar 11 , Ar 12 each independently selected from any one of substituted or unsubstituted phenyl, naphthyl or biphenyl;

[0035] X is selected from O or S;

[0036] Ar 11 , Ar 12 the substituents in the substituted ones are each independently selected from at least one of -F, -CN, C1-C12 alkyl, C1-C12 alkoxy, phenyl, naphthyl, biphenyl, binaphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl;

[0037] As a preferred technical solution of the present invention, one of the Ar 11 , Ar 12 is selected from phenyl.

[0038] Preferably, one of the Ar 11 , Ar 12 is biphenyl.

[0039] Preferably, both of the Ar 11 , Ar 12 are selected from phenyl.

[0040] Preferably, both of the Ar 11 , Ar 12 are selected from biphenyl.

[0041] Preferably, the substituents in the Ar 11 , Ar 12 are each independently selected from at least one of -F, -CN, methyl, ethyl, tert-butyl, adamantyl, cyclohexyl, cyclopentyl, 1-methylcyclopentyl, 1-methylcyclohexyl, methoxy, phenyl, biphenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl or naphthyl.

[0042] As a preferred technical solution of the present invention, the compound shown by formula A is selected from any one of the following substituted or unsubstituted compounds:

[0043]

[0044]

[0045]

[0046]

[0047] Wherein, the substitution means that the hydrogen atoms in the above compounds can be independently replaced by deuterium atoms. It should be noted that D in the above compounds is a deuterium atom (the same below).

[0048] Preferably, the compound shown by formula A is selected from the following compounds:

[0049]

[0050] Preferably, the first component of the deuterated composition is compound 3,

[0051]

[0052] Preferably, the first component of the deuterated composition is compound 3, and the second component is compound 6,

[0053]

[0054] In the third aspect, the present invention provides an intermediate, and the intermediate includes compounds shown by M0-1, M0-2, M1, M2, M2BE:

[0055]

[0056] And the intermediate does not include M0-01,

[0057]

[0058] The intermediate is used for preparing the phenylnaphthylanthracene compound as described in the first aspect.

[0059] Preferably, the intermediate includes:

[0060]

[0061]

[0062]

[0063] The synthesis method of the compound of formula (I) can adopt the following three routes:

[0064] Route 1:

[0065]

[0066] wherein X1, X3, and X4 are each independently selected from F, Cl, Br, and I; and those skilled in the art can specifically select the types of X3 and X4 according to the reaction principle to obtain the target product. For example, when X4 is selected from Cl, X3 can be selected from Br and I; when X4 is selected from Br, X3 can be selected from I; when The specific structure is X3 and X4 can be the same.

[0067] Ar1 has the same scope of protection as described above.

[0068] Route 2:

[0069]

[0070] wherein X1 and X2 are each independently selected from F, Cl, Br, and I;

[0071] Ar1 has the same scope of protection as described above.

[0072] Route 3:

[0073]

[0074]

[0075] Ar1 has the same scope of protection as described above.

[0076] Fourthly, the present invention provides an organic electroluminescent device, which includes an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode. The organic thin film layer includes the compound of formula (I) described in the first aspect or the deuterated composition described in the second aspect.

[0077] Preferably, the organic thin film layer includes a light-emitting layer, and the material of the light-emitting layer includes the compound described in the first aspect or the deuterated composition described in the second aspect..

[0078] Preferably, the host material of the material of the light-emitting layer includes the compound described in the first aspect or the deuterated composition described in the second aspect..

[0079] In the present invention, the material of the light-emitting layer further includes a compound having the structure shown in formula II and / or a compound having the structure shown in formula III:

[0080]

[0081] Among them, Ar 21 and Ar 22 are each independently selected from any one of substituted or unsubstituted C6-C20 (such as C6, C8, C10, C12, C16 or C20, etc.) aryl groups and substituted or unsubstituted C3-C20 (such as C3, C6, C8, C10, C12, C16 or C20, etc.) heteroaryl groups;

[0082] R 21 and R 22 and R 23 are each independently selected from any one of hydrogen, C1-C12 (such as C1, C2, C4, C6, C8, C10 or C12, etc.) straight-chain or branched-chain alkyl groups, and C6-C12 (such as C6, C8, C10 or C12, etc.) cycloalkyl groups;

[0083] The substituents of the substituted groups in Ar 21 and Ar 22 are each independently selected from C1-C5 (such as methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, etc.) straight-chain or branched-chain alkyl groups or C6-C12 (such as phenyl, biphenyl, naphthyl, etc.) aryl groups;

[0084] Ar 31 and Ar 32 and Ar 33 and Ar 34 are each independently selected from any one of substituted or unsubstituted C6-C22 (such as C6, C8, C10, C16, C18 or C22, etc.) aryl groups and substituted or unsubstituted C12-C40 (such as C12, C18, C20, C24, C30, C36 or C40, etc.) heteroaryl groups;

[0085] R 31 is selected from any one of phenyl, naphthyl or biphenyl;

[0086] a is selected from 0 or 1;

[0087] The substituents of the substituted groups in Ar 31 and Ar 32 and Ar 33 and Ar 34 are each independently selected from C1-C5 straight-chain or branched-chain alkyl groups (such as methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, etc.) or C6-C12 (such as C6, C8, C10 or C12, etc.) aryl groups.

[0088] As a preferred technical solution of the present invention, the Ar 21 and Ar 22 are each independently selected from Any one of the following.

[0089] Preferably, the R 21 , R 22 and R 23 are each independently selected from any one of hydrogen, methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl or adamantyl.

[0090] Preferably, the Ar 31 , Ar 32 , Ar 33 and Ar 34 are each independently selected from any one or a combination of at least two of the following.

[0091] As a preferred technical solution of the present invention, the compound having the structure shown in Formula II is selected from any one of the following compounds:

[0092]

[0093]

[0094] As a preferred technical solution of the present invention, the compound having the structure shown in Formula III is selected from any one of the following compounds:

[0095]

[0096]

[0097] Preferably, the organic thin film layer further includes a hole layer, and the hole layer includes a hole transport layer, a hole injection layer and an electron blocking layer.

[0098] Fifthly, the present invention provides a display device, and the display device includes the organic electroluminescent device as described in the third aspect.

[0099] Compared with the prior art, the present invention has the following beneficial effects:

[0100] By designing the structure of the anthracene compound substituted with phenylnaphthyl and using it as the host material of the light-emitting layer of the OLED light-emitting device, or using the deuterated composition containing the compound of Formula (I) of the present invention as the host material of the light-emitting layer of the OLED light-emitting device, the OLED light-emitting device has a lower driving voltage, a higher current efficiency and a longer lifespan. Detailed embodiments

[0101] To facilitate the understanding of the present invention, the following examples are listed. Those skilled in the art should understand that the said examples are only for helping to understand the present invention and should not be regarded as specific limitations on the present invention.

[0102] Preparation of Intermediate

[0103] Synthesis of Intermediate M0-01 in Preparation Example 1

[0104] This preparation example provides intermediate M0-01 and its synthesis method, and the said synthesis method is as follows:

[0105]

[0106] Under the protection of nitrogen, 80 mL of toluene, 10 mL of ethanol and 10 mL of water were successively added into a 250 mL three-necked flask, and then 3.3 g of 2-bromo-6-iodonaphthalene, 1.3 g of deuterated phenylboronic acid, 2.12 g (0.02 mol) of sodium carbonate and 0.23 g (0.0002 mol) of tetrakis(triphenylphosphine)palladium were added thereto. The temperature was slowly raised to 50 °C and reacted for 2 h, then raised to reflux and reacted for 4 h. After cooling to room temperature, water was added for liquid separation. After the organic layer was washed with water, it was dried with magnesium sulfate. After removing the desiccant, it was concentrated to dryness and crystallized with a mixed solvent of methanol and toluene to obtain 2.1 g of intermediate M0-01.

[0107] The obtained intermediate M0-01 was subjected to mass spectrometry detection, and the two peaks with the largest mass-to-charge ratio (m / z) were 287.04 and 289.03.

[0108] Preparation Examples 2-8

[0109] Referring to the synthesis method of intermediate M0-01 in Preparation Example 1, the corresponding bromide and boronic acid compound were reacted to synthesize the following intermediates, and the mass spectrometry of the obtained intermediates was tested. The structural formulas of the corresponding bromide and boronic acid compounds, as well as the structural formulas and mass spectrometry data of the prepared intermediates, are shown in Table 1 below.

[0110] Table 1

[0111]

[0112]

[0113] Synthesis of Intermediate MD-1 in Preparation Example 9

[0114] This preparation example provides intermediate MD-1 and its synthesis method, and the said synthesis method is as follows:

[0115]

[0116] Under nitrogen protection, 80 mL of dioxane and 15 mL of water were successively added to a 250 mL three-necked flask. Then, 2.9 g of intermediate M0-01, 2.3 g of deuterated anthracene boronic acid, 2.12 g (0.02 mol) of sodium carbonate, and 0.23 g (0.0002 mol) of tetrakis(triphenylphosphine)palladium were added thereto. The temperature was slowly raised to reflux for 12 h, and then cooled to room temperature. Toluene and water were added for liquid separation. After washing the organic layer with water, it was dried with magnesium sulfate. After removing the desiccant, it was concentrated to dryness, and crystallized with a mixed solvent of toluene and ethanol to obtain 3.1 g of intermediate MD-1.

[0117] MD-1 was detected by mass spectrometry, and the measured mass-to-charge ratio (m / z) was 394.24.

[0118] Preparation Examples 10-16

[0119] Referring to the synthesis method of intermediate MD-1 in Preparation Example 9, the corresponding bromide was reacted with a boronic acid compound to synthesize the following intermediates, and the mass spectrometry of the prepared intermediates was tested. The structural formulas of the corresponding bromide and boronic acid compound, as well as the structural formulas and mass spectrometry data of the prepared intermediates, are shown in Table 2 below.

[0120] Table 2

[0121]

[0122]

[0123]

[0124] Synthesis of Intermediate M1-1 in Preparation Example 17

[0125] This preparation example provides intermediate M1-1 and its synthesis method. The synthesis method is as follows:

[0126]

[0127] In a 500 mL three-necked flask, 4.0 g of the intermediate shown in MD-1 and 100 mL of DMF were added. While maintaining the temperature at 25-30 °C, 1.9 g of solid NBS (N-bromosuccinimide) was added in portions. After the addition, the reaction was carried out at 25-30 °C for 22 h. Then, it was poured into water, and the obtained solid was filtered, dried, boiled and washed with acetone for 2 h, cooled, and filtered to obtain 3.9 g of intermediate M1-1.

[0128] M1-1 was detected by mass spectrometry, and the two peaks with the largest mass-to-charge ratio (m / z) were 471.15 and 473.15.

[0129] Preparation Examples 18-24

[0130] Referring to the synthesis method of intermediate M1-1 in Preparation Example 17, only replace MD-1 with the corresponding brominated raw material, and carry out bromination reaction with NBS. The structural formula and mass spectrometry data of the prepared intermediate are shown in Table 3 below.

[0131] Table 3

[0132]

[0133]

[0134] Synthesis of Intermediate M1-1BA in Preparation Example 25

[0135] This preparation example provides intermediate M1-1BA and its synthesis method. The synthesis method is as follows:

[0136]

[0137] In a 250 mL three-necked flask, under nitrogen protection, add 4.7 g of intermediate M1-1 and 100 mL of tetrahydrofuran. Cool the temperature to -78 °C, and slowly dropwise add 0.012 mol of butyllithium (7.5 mL of a 1.6 M n-hexane solution). After addition, maintain at -78 °C to -65 °C for 30 minutes. Add 0.015 mol of trimethyl borate at one time, then slowly raise the temperature to room temperature. Add ammonium chloride aqueous solution and ethyl acetate for liquid separation. Wash the organic layer with saturated sodium chloride aqueous solution, then concentrate to dryness. Add petroleum ether, stir, precipitate solids, filter, and dry under reduced pressure to obtain 3.6 g of intermediate M1-1BA.

[0138] Preparation Examples 26 - 32

[0139] Referring to the synthesis method of intermediate M1-1BA in Preparation Example 25, only replace M1-1 with the corresponding brominated raw material to prepare the corresponding boric acid compounds. See Table 4 below for details.

[0140] Table 4

[0141]

[0142]

[0143] Synthesis of Intermediate M1-1BE in Preparation Example 33

[0144] This preparation example provides intermediate M1-1BE and its synthesis method. The synthesis method is as follows:

[0145]

[0146] In a 250 mL three-necked flask, add 0.5 g of intermediate M1-1BA, 0.12 g of pinacol, and 60 mL of petroleum ether. Reflux for 4 hours, filter and cool to precipitate crystals, which are M1-1BE. Perform mass spectrometry on M1-1BE, and the measured mass-to-charge ratio (m / z) is 519.32.

[0147] Preparation Examples 34 - 40

[0148] Referring to the synthesis method of intermediate M1-1BAE in Preparation Example 33, only replace M1-1BA with the corresponding boric acid raw material to prepare the corresponding borate compound, and measure the mass spectrometry (m / z) of the prepared borate compound. See Table 5 below.

[0149] Table 5

[0150]

[0151]

[0152] Synthesis of Compound 1 in Synthesis Example 1

[0153] This synthesis example provides Compound 1 and its synthesis method, and the synthesis method is as follows:

[0154]

[0155] Under nitrogen protection, add 100 mL of toluene, 40 mL of ethanol, and 15 mL of water to a 250 mL three-necked flask in sequence. Then add 4.8 g of intermediate M1-1, 2.0 g of biphenylboronic acid, 2.12 g (0.02 mol) of sodium carbonate, and 0.23 g (0.0002 mol) of tetrakis(triphenylphosphine)palladium. Slowly heat to reflux for 10 h, cool to room temperature, add water and separate the layers. After washing the organic layer with water, dry it with magnesium sulfate. After removing the desiccant, concentrate to dryness and crystallize with toluene twice to obtain 4.3 g of Compound 1.

[0156] Perform mass spectrometry on the obtained Compound 1, and the measured mass-to-charge ratio (m / z) is 545.30.

[0157] Synthesis of Compound 1 in Synthesis Example 1-1

[0158] This synthesis example provides another synthesis method of Compound 1, and the synthesis method is as follows:

[0159]

[0160] Referring to the synthesis of Compound 1 in Synthesis Example 1, only change the reaction raw materials to obtain Compound 1.

[0161] The obtained compound 1 was subjected to mass spectrometry, and the measured mass-to-charge ratio (m / z) was 545.30.

[0162] Synthesis of Compound 1 in Synthesis Example 1-2

[0163] This synthesis example provides another synthesis method for the compound. The synthesis method is as follows:

[0164]

[0165] Referring to the synthesis of compound 1 in Synthesis Example 1, only changing the reaction raw materials, compound 1 was obtained.

[0166] The obtained compound 1 was subjected to mass spectrometry, and the measured mass-to-charge ratio (m / z) was 545.30.

[0167] Synthesis Examples 2-15

[0168] Referring to the synthesis of compound 1 in Synthesis Example 1 and Synthesis Example 1-1, the corresponding bromide and boronic acid compound were reacted to synthesize the following compounds, and the mass spectra of the prepared compounds were tested. The structural formulas of the corresponding bromide and boronic acid compounds, as well as the structural formulas and mass spectrometry data of the prepared compounds, are shown in Table 6 below.

[0169] Table 6

[0170]

[0171]

[0172]

[0173]

[0174] For other compounds whose specific synthesis steps are not listed, they can be prepared by combining the above synthesis examples with common general knowledge in the art.

[0175] The specific structures of the compounds used in the following application examples and comparative application examples are shown as follows:

[0176]

[0177]

[0178] Application Example 1

[0179] This application example provides a blue organic electroluminescent device. The structure of the organic electroluminescent device is: ITO / HTL:HI-2(5%)(20nm) / HTL(50nm) / BH:BD-1(5%)(30nm) / TPBI(30nm) / Al(150nm);

[0180] The preparation method of the above organic electroluminescent device is as follows:

[0181] Place each layer of material in a vacuum chamber, evacuate to 1×10 -5 ~1×10 -6 Pa, and vacuum deposit them onto the cleaned ITO substrate in sequence. Among them, HTL:HI-2(5%)(20nm) means that in this device, HTL and HI-2 are co-evaporated to form a hole injection layer in a volume ratio of 95:5, and its thickness is 20nm. BH:BD-1(5%)(30nm) means that BH and BD-1 are co-evaporated to form a light-emitting layer in a volume ratio of 95:5, and its thickness is 30nm.

[0182] BH is a blue light host material (also called BH material). In this application example, BH is Compound 1.

[0183] In the device provided by this application example, HTL:HI-2(5%)(20nm) is the hole injection layer, and HTL(50nm) is the hole transport layer.

[0184] Application Examples 2-8

[0185] Application Examples 2-8 respectively provide an organic electroluminescent device. The difference from Application Example 1 is only that the BH material is different (the specific composition is as described in the following table), and other preparation steps are the same as those in Application Example 1.

[0186] Comparative Application Examples 1-5

[0187] Comparative Application Examples 1-5 respectively provide an organic electroluminescent device. The difference from Application Example 1 is only that the BH material is different (as described below), and other preparation steps are the same as those in Application Example 1.

[0188] Performance Test

[0189] Test method: Use the OLED-1000 multi-channel accelerated aging life and optical color performance analysis system produced by Hangzhou Yuanfang for testing. The test items include the brightness, driving voltage, current efficiency, and LT80 of the organic electroluminescent device; among them, LT80 refers to the time required for the device efficiency to drop to 80% of the efficiency corresponding to the initial brightness of 1000 cd / m 2 while keeping the current density of the initial brightness of 1000 cd / m 2 constant. Among them, the driving voltage, current efficiency, and LT80 are all relative values.

[0190] The specific test results are shown in Table 7 below:

[0191] Table 7

[0192]

[0193] From the comparison of Comparative Application Examples 4-5 and Application Examples 1-2 in the above table, it can be seen that in Comparative Application Example 4, the BH material is compound BH6, and only the anthracene ring is deuterated; in Comparative Application Example 5, the BH material is compound BH7, and all groups are deuterated, resulting in an improvement in the device lifetime, but a decrease in efficiency and an increase in voltage. In Application Example 1, the compound of the present invention is used, and its voltage, efficiency, and lifetime are all improved. The reason is that compared with BH7 and BH6, the deuteration rate is increased and the lifetime is improved. However, because the diameter of the deuterium nucleus is larger than that of the hydrogen nucleus, the electron cloud density outside the deuterium nucleus decreases, the intermolecular force of the material decreases, the film-forming property becomes poor, and the charge transfer ability becomes poor, thus affecting the efficiency and lifetime. The compound of the present invention uses a non-deuterated naphthalene ring substituted with deuterated benzene on the deuterated anthracene ring ( ), appropriately increasing the deuteration rate of the material, taking into account the electron cloud density outside the molecule, having a relatively large intermolecular force of the material, good film-forming property, so the lifetime is improved, and the efficiency and voltage are also improved.

[0194] Comparing Comparative Application Example 2 and Application Example 3, in Comparative Application Example 2, BH2 is used as the BH material, with a symmetric structure and good crystallization performance, resulting in a poor lifetime; and BH2 contains one anthracene ring, two naphthalene rings, and two benzene rings, and the two naphthalene rings are directly connected to the anthracene ring, making the electron cloud density around the anthracene ring in the material molecule relatively large and the material unstable. In Application Example 3, compound 7 is used as the BH material. Although BH7 also contains one anthracene ring, two naphthalene rings, and two benzene rings, only one naphthalene ring is directly connected to the anthracene ring, thus improving the material performance.

[0195] Application Examples 9-11

[0196] Application Examples 9-11 respectively provide an organic electroluminescent device, which is different from Application Example 1 only in that BD-1 is replaced with BD-3 therein, and the BH material is different (the specific composition is as described in the following table), and other preparation steps are the same as those in Application Example 1.

[0197] Comparative Application Examples 6-8

[0198] Comparative Application Examples 6-8 respectively provide an organic electroluminescent device, which is different from Application Example 1 only in that BD-1 is replaced with BD-3 therein, and the BH material is different (the specific composition is as described in the following table), and other preparation steps are the same as those in Application Example 1.

[0199] Performance Test

[0200] Test method: Test using the OLED-1000 multi-channel accelerated aging life and light color performance analysis system produced by Hangzhou Yuanfang. The test items include the brightness, driving voltage, current efficiency, and LT80 of the organic electroluminescent device; among them, LT80 refers to maintaining the initial brightness of the device at 1000 cd / m 2 while keeping the current density unchanged, and the device efficiency drops to 80% of the efficiency corresponding to the initial brightness of 1000 cd / m 2 The required time. Among them, the driving voltage, current efficiency, and LT80 are all relative values.

[0201] The specific test results are shown in Table 8 below:

[0202] Table 8

[0203]

[0204] From the comparison between Comparative Application Example 6 (using BH5 as the BH material) and Application Example 9 (using Compound 12 as the BH material), it can be seen that the performance of the device prepared with the fully deuterated compound is inferior to that of the compound of the present invention.

[0205] From the comparison between Comparative Application Example 7 (using BH9 as the BH material) and Application Example 9 (using Compound 12 as the BH material), it can be seen that replacing the deuterated benzene ring of the compound of the present invention with a deuterated naphthalene ring results in a device with performance inferior to that of the compound of the present invention.

[0206] Application Examples 12 - 15

[0207] Application Examples 12 - 15 respectively provide an organic electroluminescent device, which is different from Application Example 1 only in that the BH material therein is two compounds (Host 1 (the first component) and Host 2 (the second component)). When preparing the device, the two compounds are respectively placed in different evaporation sources, and the heating temperature is controlled so that the ratio of the two compounds evaporated onto the substrate is 1:1 (volume ratio), and other preparation steps are the same as those in Application Example 1.

[0208] Comparative Application Examples 9 - 12

[0209] Comparative Application Examples 9 - 12 respectively provide an organic electroluminescent device, which is different from Application Example 1 only in that the BH material therein is two compounds (Host 1 and Host 2). When preparing the device, the two compounds are respectively placed in different evaporation sources, and the heating temperature is controlled so that the ratio of the two compounds evaporated onto the substrate is 1:1 (volume ratio), and other preparation steps are the same as those in Application Example 1.

[0210] Performance Test

[0211] Test method: Test using the OLED-1000 multi-channel accelerated aging life and optical color performance analysis system produced by Hangzhou Yuanfang. The test items include the brightness, driving voltage, current efficiency, and LT80 of the organic electroluminescent device. Among them, LT80 refers to the time required for the device efficiency to drop to 80% of the efficiency corresponding to the initial brightness of 1000 cd / m 2 while keeping the current density unchanged, and the initial brightness of the device is 1000 cd / m 2 . The driving voltage, current efficiency, and LT80 are all relative values.

[0212] The specific test results are shown in Table 9 below:

[0213] Table 9

[0214]

[0215] According to the data in the above table, it can be seen that the performance of the OLED device prepared using the deuterated composition of the present invention is relatively good.

[0216] When the compound shown in formula (I) of the present invention is used as the first component and the compound having the structure shown in formula A is used as the second component as the BH material, the device performance is better than that of the comparative application example.

[0217] Moreover, by comparing Application Example 15 with Application Examples 12-14, it can be seen that when both the first component and the second component of the deuterated composition of the present invention are selected from the compounds shown in formula (I), the device performance is further improved.

[0218] The applicant declares that the present invention uses the above embodiments to illustrate the detailed process flow of the present invention, but the present invention is not limited to the above detailed process flow, that is, it does not mean that the present invention must rely on the above detailed process flow to be implemented. Those skilled in the art should understand that any improvement to the present invention, the equivalent substitution of each raw material of the product of the present invention, the addition of auxiliary components, the selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A phenylnaphthylanthracene compound, characterized in that, The phenylnaphthylanthracene compound is a compound represented by formula (I): Wherein, Ar1 is selected from phenyl, naphthyl, biphenyl or naphthyl-substituted phenyl; The H atom in Ar1 can be replaced by a D atom.

2. The phenylnaphthylanthracene compound according to claim 1, wherein The compound represented by formula (I) includes the compounds represented by the following formula (I-A) and formula (I-B): Preferably, the compound represented by formula (I) includes the compounds represented by the following formula (I-A-1) to formula (I-A-4) or formula (I-B-5) to formula (I-B-8): More preferably, the compound represented by formula (I) is selected from any one of the following substituted or unsubstituted compounds: The substitution means that in the structure of the corresponding Ar1 part in the structure of formula (I), part or all of the H atoms are replaced by D atoms; More preferably, the compound represented by formula (I) is selected from the following structures:

3. A deuterated composition, characterized in that, The deuterated composition includes at least a first component and a second component. The first component is selected from any one of the compounds represented by formula (I) as claimed in claim 1 or 2, and the second component is selected from any one of the compounds represented by formula A; Among them, Ar 11 and Ar 12 are each independently selected from any one of substituted or unsubstituted phenyl, naphthyl or biphenyl; X is selected from O or S; Ar 11 、Ar 12 The substituents described in 11 and 12 are each independently selected from at least one of -F, -CN, C1-C12 alkyl, C1-C12 alkoxy, phenyl, naphthyl, biphenyl, binaphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, and dibenzothiophenyl; Or the second component is selected from any one of the compounds represented by formula (I) as claimed in claim 1 or 2, and the second component is different from the first component; Preferably, the second component of the deuterated composition is selected from the compounds represented by formula (I).

4. The deuterated composition according to claim 3, wherein Among the compounds represented by Formula A, Ar 11 and Ar 12 one of which is selected from phenyl; Preferably, the Ar 11 and Ar 12 one of which is a biphenyl group; Preferably, the Ar 11 and Ar 12 are both selected from phenyl; Preferably, the Ar 11 and Ar 12 are both selected from biphenyl groups; Preferably, the Ar 11 , Ar 12 the substituents in are each independently selected from at least one of -F, -CN, methyl, ethyl, tert-butyl, adamantyl, cyclohexyl, cyclopentyl, 1-methylcyclopentyl, 1-methylcyclohexyl, methoxy, phenyl, biphenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl or naphthyl; Preferably, the compound represented by formula A is selected from any one of the following substituted or unsubstituted compounds: Preferably, the compound represented by formula A is selected from the following compounds:

5. The deuterated composition according to claim 3, characterized in that, The first component of the deuterated composition is compound 3, Preferably, the first component of the deuterated composition is compound 3, and the second component is compound 6, 6. An intermediate, the intermediate includes compounds M0-1, M0-2, M1, M2, M2BE: And the intermediate does not include M0-01, The intermediate is used for preparing the phenylnaphthylanthracene compound as claimed in claim 1; Preferably, the intermediate includes:

7. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode. The organic thin film layer includes the phenylnaphthylanthracene compound as claimed in claim 1 or 2 or the deuterated composition as claimed in any one of claims 3-5; Preferably, the organic thin film layer includes a light-emitting layer, and the material of the light-emitting layer includes the phenylnaphthylanthracene compound as claimed in claim 1 or 2 or the deuterated composition as claimed in any one of claims 3-5; Preferably, the light-emitting layer material further includes a compound having a structure represented by formula II and / or a compound having a structure represented by formula III: Among them, Ar 21 and Ar 22 are each independently selected from any one of substituted or unsubstituted C6-C20 aryl and substituted or unsubstituted C3-C20 heteroaryl; R 21 、R 22 and R 23 each independently selected from any one of hydrogen, C1-C12 linear or branched alkyl, and C6-C12 cycloalkyl; Ar 21 、Ar 22 The substituents in 21 and 22 are each independently selected from C1-C5 straight-chain or branched-chain alkyl groups or C6-C12 aryl groups; Ar 31 、 Ar 32 、 Ar 33 and Ar 34 each independently selected from any one of substituted or unsubstituted C6-C22 aryl, substituted or unsubstituted C12-C40 heteroaryl; R 31 Selected from any one of phenyl, naphthyl or biphenyl; a is selected from 0 or 1; Ar 31 、 Ar 32 、 Ar 33 、 Ar 34 The substituents described in each of them are independently selected from C1-C5 straight-chain or branched-chain alkyl groups or C6-C12 aryl groups.

8. The organic electroluminescent device according to claim 7, wherein The Ar 21 and Ar 22 are each independently selected from any one of; Preferably, the R 21 , R 22 and R 23 are each independently selected from any one of hydrogen, methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl or adamantyl; Preferably, the Ar 31 , Ar 32 , Ar 33 and Ar 34 are each independently selected from any one or a combination of at least two thereof.

9. The organic electroluminescent device according to claim 7 or 8, characterized in that, The compound having a structure represented by formula II is selected from any one of the following compounds: Preferably, the compound having a structure represented by formula III is selected from any one of the following compounds:

10. A display device, characterized in that, The display device includes the organic electroluminescent device as claimed in any one of claims 7-9.

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