Phenyl naphthyl anthracene compound-containing deuterated composition and phenyl naphthyl anthracene compound

Abstract

The invention provides a deuterated composition containing a phenyl naphthyl anthracene compound and the phenyl naphthyl anthracene compound. The phenyl naphthyl anthracene compound has a structure as shown in the following formula (I). The deuterated composition containing the phenyl naphthyl anthracene compound and the phenyl naphthyl anthracene compound 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 deuterated composition containing phenylnaphthylanthracene compounds and phenylnaphthylanthracene compounds. Background Art

[0002] An organic electroluminescent device is a device prepared by depositing one or more layers of 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 to combine in the light-emitting layer to form excitons, and then emit light. The organic electroluminescent device can emit 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 fabricate flexible, bendable, and transparent display panels, as well as being environmentally friendly. They can be applied in flat panel displays and new generation lighting, and can also be used as the backlight of LCDs.

[0004] Since its invention at the end of the 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 deuterated composition containing phenylnaphthyl-substituted anthracene compounds and phenylnaphthyl-substituted anthracene compounds. The deuterated composition containing phenylnaphthyl-substituted anthracene compounds and phenylnaphthyl-substituted anthracene compounds provided by the present invention can be used as the host material of the light-emitting layer of an OLED light-emitting device, making the OLED light-emitting device have 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 deuterated composition containing a phenylnaphthylanthracene compound. 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), and the second component has a different structure from the first component. It can be selected from any one of the compounds represented by formula (I) or any one of the compounds having the structure represented by formula A.

[0008] The structure represented by formula (I) is as follows:

[0009]

[0010] Wherein, Ar1 is selected from a single bond, a phenylene group, a naphthylene group or a biphenylene group, and Ar2 is selected from H, a phenyl group, a naphthyl group or a biphenyl group;

[0011] The H atoms on Ar1, Ar2 and the dibenzofuran ring can be replaced by D atoms;

[0012] D in formula (I) represents a deuterium atom;

[0013] The compound having the structure represented by formula A is as follows:

[0014]

[0015] Wherein, Ar 301 , Ar 302 , Ar 401 , Ar 402 are each independently selected from a phenyl group, a naphthyl group, a phenanthryl group, a phenylene group, a naphthylene group or a phenanthrylene group, and Ar 301 , Ar 302 , Ar 401 , Ar 402 are not simultaneously a phenanthryl group; the structure represented by formula A contains at most one phenanthryl group;

[0016] The o and p are each independently selected from 0 or 1;

[0017] The H atoms in the compound represented by formula A can be replaced by D atoms.

[0018] In the deuterated composition provided by the present invention, preferably, the second component is selected from any one of the compounds represented by formula (I).

[0019] As a preferred technical solution of the present invention, the compound represented by formula A is selected from any one of the following compounds:

[0020]

[0021]

[0022] Preferably, the compound represented by formula A is selected from the following structures:

[0023]

[0024] Preferably, the first component of the deuterated composition is the following compound:

[0025]

[0026]

[0027] Preferably, the first component of the deuterated composition is Compound 15, and the second component is Compound C-3; or the first component is Compound 24, and the second component is Compound C-1; or the first component is Compound 24, and the second component is Compound BH1;

[0028] or the first component is Compound 15, and the second component is Compound 14:

[0029]

[0030] In a second aspect, the present invention provides a compound represented by formula (I):

[0031]

[0032] wherein, Ar1 is selected from a single bond, a phenylene group, a naphthylene group or a biphenylene group, and Ar2 is selected from H, a phenyl group, a naphthyl group or a biphenyl group;

[0033] The H atoms on Ar1, Ar2 and the dibenzofuran ring can be replaced by D atoms;

[0034] D in formula (I) represents a deuterium atom;

[0035] and the compound represented by formula (I) does not include BH1:

[0036]

[0037] The compound represented by formula (I) is used to prepare the deuterated composition described in the first aspect.

[0038] Preferably, the compound represented by formula (I) includes the compounds represented by the following formula (I-A) and formula (I-B):

[0039]

[0040] Furthermore, the compound represented by formula (I) includes the compounds represented by the following formula (I-A-1) to formula (I-A-4), and the compounds represented by formula (I-B-5) to formula (I-B-8):

[0041]

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

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050] The substitution means that the H atoms on the corresponding Ar1, Ar2, and dibenzofuran ring in the structure of formula (I) are partially or completely replaced by D atoms, and examples are as follows:

[0051] The structure of Compound 1 is as follows:

[0052]

[0053] The substituted Compound 1 includes, but is not limited to, the following structures:

[0054]

[0055] The structure of Compound 2 is as follows:

[0056]

[0057] The substituted Compound 2 includes, but is not limited to, the following structures:

[0058] Preferably, the compound represented by the formula (I) is selected from the following structures:

[0059]

[0060]

[0061] In a third aspect, 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, and the organic thin film layer includes the deuterated composition as described in the first aspect or the compound of formula (I) as described in the second aspect.

[0062] Preferably, the organic thin film layer includes a light-emitting layer, and the material of the light-emitting layer includes the deuterated composition described in the first aspect or the compound of formula (I) described in the second aspect.

[0063] Preferably, the host material of the material of the light-emitting layer includes the deuterated composition described in the first aspect or the compound of formula (I) described in the second aspect.

[0064] In the present invention, the light-emitting layer material further includes a compound having the structure shown in formula II and / or a compound having the structure shown in formula III:

[0065]

[0066] wherein, Ar 21 and Ar 22 each independently selected from substituted or unsubstituted C6-C20 (such as C6, C8, C10, C12, C16 or C20, etc.) aryl, substituted or unsubstituted C3-C20 (such as C3, C6, C8, C10, C12, C16 or C20, etc.) heteroaryl;

[0067] R 21 、R 22 and R 23 each independently selected from hydrogen, C1-C12 (such as C1, C2, C4, C6, C8, C10 or C12, etc.) linear or branched alkyl, C6-C12 (such as C6, C8, C10 or C12, etc.) cycloalkyl;

[0068] Ar 21 、Ar 22 the substituents in the substituted ones are each independently selected from C1-C5 (such as methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, etc.) linear or branched alkyl or C6-C12 (such as phenyl, biphenyl, naphthyl, etc.) aryl;

[0069] Ar 31 、Ar 32 、Ar 33 and Ar 34 each independently selected from substituted or unsubstituted C6-C22 (such as C6, C8, C10, C16, C18 or C22, etc.) aryl, substituted or unsubstituted C12-C40 (such as C12, C18, C20, C24, C30, C36 or C40, etc.) heteroaryl;

[0070] R 31 is selected from any one of phenyl, naphthyl or biphenyl;

[0071] a is selected from 0 or 1;

[0072] Ar 31 、Ar 32 、Ar 33 、Ar 34 The substituents in the above-mentioned substitution are each independently selected from C1-C5 linear or branched alkyl groups (such as methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, etc.) or C6-C12 aryl groups (such as C6, C8, C10, or C12, etc.).

[0073] As a preferred technical solution of the present invention, the said Ar 21 、Ar 22 are each independently selected from

[0074] any one of those in

[0075] Preferably, the said 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.

[0076] Preferably, the said Ar 31 、Ar 32 、Ar 33 and Ar 34 are each independently selected from any one of those in or a combination of at least two of them.

[0077] 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:

[0078]

[0079]

[0080] 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:

[0081]

[0082]

[0083] In the present invention, the light-emitting layer material further includes a compound having the structure shown in Formula BDI:

[0084]

[0085] Among them, Ar 101 , Ar 102 , Ar 201 , Ar 202 are each independently selected from any one of substituted or unsubstituted C6 - C40 (such as C6, C10, C12, C15, C18, C24, C30, C36 or C40, etc.) aryl groups, and substituted or unsubstituted C12 - C20 (such as C12, C13, C14, C15, C16, C17, C18, C19 or C20) heteroaryl groups;

[0086] R 101 and R 102 are each independently selected from any one of substituted or unsubstituted C1 - C12 (such as C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11 or C12) alkyl groups, substituted or unsubstituted C6 - C40 (such as C6, C10, C12, C15, C18, C24, C30, C36 or C40, etc.) aryl groups, and substituted or unsubstituted C12 - C20 (such as C12, C13, C14, C15, C16, C17, C18, C19 or C20) heteroaryl groups;

[0087] R 101 and R 102 can be connected into a ring through a single bond;

[0088] m and n are each independently selected from 0 or 1, and m and n are not both 0 at the same time;

[0089] Ar 101 , Ar 102 , Ar 201 , Ar 202 , R 101 and R 102 the substituents in the above - mentioned substitution are each independently selected from any one or a combination of at least two of - D, - F, - CN, C1 - C12 (such as C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11 or C12) alkyl groups, C1 - C6 (such as C1, C2, C3, C4, C5 or C6) alkoxy groups, C2 - C8 (such as C2, C3, C4, C5, C6, C7 or C8) alkenyl groups, C6 - C15 (such as C6, C7, C8, C10, C12 or C15, etc.) aryl groups, and C12 - C20 (such as C12, C15, C18 or C20, etc.) heteroaryl groups.

[0090] As a preferred technical solution of the present invention, the C6-C40 aryl is selected from any one of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, benzofluorenyl, 9,10-diphenylanthryl, dibenzofluorenyl, naphthofluorenyl, pyrenyl, perylenyl, spirofluorene, triphenylene, fluoranthenyl, hydrobenzanthryl, indeno[1,2-b]fluorene, benzo[1,2,3-cd]indeno[1,2-b]fluorene, dibenzo[1,2,3-cd]indeno[1,2-b]fluorene, naphthofluorenyl or benzonaphthofluorenyl, preferably any one of phenyl, naphthyl, biphenyl, terphenyl, fluoranthenyl, fluorenyl, 9,10-diphenylanthryl or benzofluorenyl.

[0091] Preferably, the C12-C20 heteroaryl is selected from any one of dibenzofuranyl, dibenzothiophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, dinaphthofuranyl or dinaphthothiophenyl.

[0092] Preferably, the C1-C12 alkyl is selected from any one of methyl, ethyl, propyl, butyl, adamantyl, 1-methylcyclohexyl, 1-methylcyclopentyl, cyclopentyl or cyclohexyl.

[0093] Preferably, the C1-C6 alkoxy is selected from any one of methoxy, ethoxy, propoxy, butoxy or any one of them, and the dotted line indicates the connection site.

[0094] Preferably, the C6-C15 aryl is selected from any one of phenyl, naphthyl or biphenyl.

[0095] As a preferred technical solution of the present invention, the Ar 101 and Ar 102 each independently is selected from any one of the following substituted or unsubstituted groups: phenyl, naphthyl, biphenyl, terphenyl, fluoranthenyl, fluorenyl, 9,10-diphenylanthryl, benzofluorenyl, dibenzofuranyl, dibenzothiophenyl, naphthobenzofuranyl or naphthobenzothiophenyl;

[0096] The substituents of the substitution are selected from any one or a combination of at least two of -D (deuterium atom), -F, -CN, phenyl, biphenyl, dibenzofuranyl, methyl, deuterated methyl, adamantyl, tert-butyl, 1-methylcyclopentyl, cyclohexyl, cyclopentyl, methoxy, naphthyl, dibenzothiophenyl, naphthobenzothiophenyl, and the dotted line indicates the connection site.

[0097] Preferably, the Ar 201 and Ar 202 each independently is selected from any one of the following substituted or unsubstituted groups: phenyl, naphthyl, dibenzofuranyl or biphenyl;

[0098] The substituted substituent is selected from any one or a combination of at least two of methyl, methoxy, phenyl or dibenzofuranyl.

[0099] Preferably, R 101 and R 102 are each independently selected from any one of methyl, ethyl, propyl or phenyl.

[0100] Preferably, R 101 and R 102 are the same.

[0101] As a preferred technical solution of the present invention, the compound having the structure shown in formula BDI is selected from any one of the following compounds:

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110] 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.

[0111] Fourthly, the present invention provides a display device, and the display device includes the organic electroluminescent device as described in the third aspect.

[0112] Fifthly, the present invention provides intermediate X1-3 for preparing the compound shown in formula (I) of the present invention,

[0113]

[0114] Compared with the prior art, the present invention has the following beneficial effects:

[0115] The present invention designs through the composition of deuterium substitution combinations, and uses this as the host material of the light-emitting layer of the OLED light-emitting device, or uses the compound shown in formula (I) of the present invention 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 lifespan. Detailed implementation mode

[0116] To facilitate the understanding of the present invention, the following examples are listed for the present invention. 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.

[0117] Preparation of intermediate

[0118] Synthesis of intermediate M0-01 in Preparation Example 1

[0119] This preparation example provides intermediate M0-01 and its synthesis method, and the said synthesis method is as follows:

[0120]

[0121] Under the condition of nitrogen protection, 80 mL of toluene, 10 mL of ethanol and 10 mL of water are 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 are added thereto. The temperature is 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 is added for liquid separation. After the organic layer is washed with water, it is dried with magnesium sulfate. After removing the desiccant, it is concentrated to dryness, and crystallized with a mixed solvent of methanol and toluene to obtain 2.1 g of intermediate M0-01.

[0122] 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.

[0123] Preparation Examples 2-8, Preparation Example 8-1

[0124] Referring to the synthesis method of intermediate M0-01 in Preparation Example 1, the corresponding bromide and boronic acid compound are reacted to synthesize the following intermediates, and the mass spectrometry of the obtained intermediates is tested. The structural formulas of the corresponding bromide and boronic acid compound and the structural formulas and mass spectrometry data of the prepared intermediates are shown in Table 1 below.

[0125] Table 1

[0126]

[0127]

[0128] Synthesis of intermediate MD-1 in Preparation Example 9

[0129] This preparation example provides intermediate MD-1 and its synthesis method, and the said synthesis method is as follows:

[0130]

[0131] 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 reaction for 12 h, and then cooled to room temperature. Toluene and water were 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 toluene and ethanol to obtain 3.1 g of intermediate MD-1.

[0132] MD-1 was subjected to mass spectrometry detection, and the measured mass-to-charge ratio (m / z) was 394.24.

[0133] Preparation Examples 10-16

[0134] Referring to the synthesis method of intermediate MD-1 in Preparation Example 9, the corresponding bromide and boronic acid compound were reacted 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 compounds, as well as the structural formulas and mass spectrometry data of the prepared intermediates, are shown in Table 2 below.

[0135] Table 2

[0136]

[0137]

[0138] Synthesis of Intermediate M1-1 in Preparation Example 17

[0139] This preparation example provides intermediate M1-1 and its synthesis method, and the synthesis method is as follows:

[0140]

[0141] In a 500 mL three-necked flask, 4.0 g of the intermediate shown in MD-1 and 100 mL of DMF were added, and the temperature was maintained at 25-30 °C. 1.9 g of solid NBS (N-bromosuccinimide) was added in batches. After the addition, the reaction was carried out at 25-30 °C for 22 h, poured into water, and the obtained solid was filtered, dried, boiled and washed with acetone for 2 h, cooled, and filtered to obtain intermediate M1-1 with a mass of 3.9 g.

[0142] M1-1 was subjected to mass spectrometry detection, and the two peaks with the largest mass-to-charge ratio (m / z) were 471.15 and 473.15.

[0143] Preparation Examples 18-24

[0144] Referring to the synthesis method of intermediate M1-1 in Preparation Example 17, only replacing MD-1 with the corresponding brominated raw material and performing a bromination reaction with NBS, the structural formula and mass spectrometry data of the prepared intermediate are shown in Table 3 below.

[0145] Table 3

[0146]

[0147]

[0148] Synthesis of Intermediate M1-1BA in Preparation Example 25

[0149] This preparation example provides intermediate M1-1BA and its synthesis method. The synthesis method is as follows:

[0150]

[0151] 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 add dropwise 0.012 mol of butyllithium (7.5 mL of a 1.6 M n-hexane solution). After addition, maintain the temperature at -78 °C to -65 °C for 30 minutes. Add 0.015 mol of trimethyl borate all at once, then slowly raise the temperature to room temperature. Add aqueous ammonium chloride solution and ethyl acetate for liquid separation. Wash the organic layer with saturated aqueous sodium chloride solution, then concentrate to dryness. Add petroleum ether, stir, precipitate a solid, filter, and dry under reduced pressure to obtain 3.6 g of intermediate M1-1BA.

[0152] Preparation Examples 26 - 32

[0153] Referring to the synthesis method of intermediate M1-1BA in Preparation Example 25, only replacing M1-1 with the corresponding brominated raw material to prepare the corresponding boric acid compounds, which are shown in Table 4 below.

[0154] Table 4

[0155]

[0156]

[0157] Synthesis of Compound 1 in Synthesis Example 1

[0158] This synthesis example provides compound 1 and its synthesis method. The synthesis method is as follows:

[0159]

[0160] Under nitrogen protection, 100 mL of dioxane and 35 mL of water were successively added to a 250 mL three-necked flask. Then, 4.4 g of intermediate M1-2BA, 3.3 g of intermediate M1, 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 15 h, cooled to room temperature, water and toluene were added and separated by liquid-liquid extraction. After washing the organic layer with water, it was dried with magnesium sulfate. After removing the desiccant, it was concentrated to dryness and crystallized twice with toluene to obtain 4.7 g of compound 1.

[0161] The obtained compound 1 was subjected to mass spectrometry, and the measured mass-to-charge ratio (m / z) was 635.31.

[0162] Synthesis Example 2-13

[0163] Referring to the synthesis of compound 1 in Synthesis Example 1, the corresponding bromide and boronic acid compound were reacted to synthesize the following compounds, and the mass spectrometry of the obtained compounds 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 obtained compounds, are shown in Table 5.

[0164] Table 5

[0165]

[0166]

[0167]

[0168]

[0169]

[0170] Other compounds for which the specific synthesis steps are not listed can be prepared by combining the above synthesis examples with common general knowledge in the art.

[0171] The specific structures of the compounds used in the following Application Examples and Comparative Application Examples are shown below:

[0172]

[0173]

[0174] Application Example 1

[0175] This application example provides a blue organic electroluminescent device, and the structure of the organic electroluminescent device is: ITO / HTL:HI-2(5%)(20 nm) / HTL(50 nm) / BH:BD-1(5%)(30 nm) / TPBI(30 nm) / Al(150 nm);

[0176] The preparation method of the above-mentioned organic electroluminescent device is as follows:

[0177] Place each layer of material in a vacuum chamber, evacuate to 1×10 -5 ~1×10 -6 Pa, and then vacuum-evaporate 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 at a volume ratio of 95:5 to form a hole injection layer with a thickness of 20nm. In this embodiment, HTL is compound 47.

[0178] BH:BD-1(5%)(30nm) means that BH and BD-1 are co-evaporated at a volume ratio of 95:5 to form a light-emitting layer with a thickness of 30nm.

[0179] BH is a blue light host material (also called BH material). In this application example, the BH material is two compounds (host 1 (the first component) and host 2 (the second component)). When preparing the device, place the two compounds in different evaporation sources respectively, control the heating temperature, so that the ratio of the two compounds evaporated onto the substrate is 1:1 (volume ratio). In this embodiment, host 1 is compound 1 and host 2 is compound C-1.

[0180] In the device provided in this application example, HTL:HI-2(5%)(20nm) is the hole injection layer, and HTL(50nm) is the hole transport layer. HTL is compound 47.

[0181] Application examples 2-8, 6-1, 7-1

[0182] Application examples 2-8, 6-1, and 7-1 respectively provide an organic electroluminescent device. The difference from application example 1 is only that the BH materials are different (the specific compositions are as described in the following table), and the other preparation steps are the same as those in application example 1.

[0183] Comparative application examples 1-5

[0184] Comparative application examples 1-5 respectively provide an organic electroluminescent device. The difference from application example 1 is only that the BH materials are different (as described below), and the other preparation steps are the same as those in application example 1.

[0185] Performance test

[0186] Test method: Use the OLED-1000 multi-channel accelerated aging life and light 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 maintaining the initial brightness of the device at 1000cd / m 2The current density remains unchanged, and the device efficiency drops to 80% of the initial luminance of 1000 cd / m 2 The time required for this corresponding efficiency. Among them, the driving voltage, current efficiency, and LT80 are all relative values.

[0187] The specific test results are shown in Table 6.

[0188] Table 6

[0189]

[0190] According to the above table, the device prepared from the deuterated composition provided by the present invention has excellent performance. Moreover, according to Application Examples 6-1 and 7-1, when both components constituting the deuterated composition of the present invention conform to the structure shown in Formula (I), the device performance is further improved.

[0191] Application Example 9

[0192] This application example provides a blue organic electroluminescent device. The structure of the organic electroluminescent device is: ITO / HTL:HI-2(5%)(20 nm) / HTL(50 nm) / BH:BD-4(5%)(30 nm) / TPBI(30 nm) / Al(150 nm);

[0193] The preparation method of the above organic electroluminescent device is as follows:

[0194] Place each layer of material in a vacuum chamber, evacuate to 1×10 -5 ~1×10 -6 Pa, and sequentially vacuum deposit onto the cleaned ITO substrate. Among them, HTL:HI-2(5%)(20 nm) means that in this device, HTL and HI-2 are co-evaporated at a volume ratio of 95:5 to form a hole injection layer with a thickness of 20 nm. In this embodiment, HTL is Compound 47.

[0195] BH:BD-4(5%)(30 nm) means that BH and BD-4 are co-evaporated at a volume ratio of 95:5 to form a light-emitting layer with a thickness of 30 nm.

[0196] BH is a blue light host material (also called BH material). In this application example, BH is Compound 1-3.

[0197] In the device provided by this application example, HTL:HI-2(5%)(20 nm) is the hole injection layer, and HTL(50 nm) is the hole transport layer. HTL is Compound 47.

[0198] Application Examples 10-16

[0199] Application Examples 10-16 each provide an organic electroluminescent device, which is only different from Application Example 1 in 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.

[0200] Comparative Application Examples 6-7

[0201] Comparative Application Examples 6-7 each provide an organic electroluminescent device, which is only different from Application Example 1 in that the BH material is different (as described in the following table), and other preparation steps are the same as those in Application Example 1.

[0202] Performance Test

[0203] 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 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 at the initial brightness of 1000 cd / m 2 unchanged. Among them, the driving voltage, current efficiency, and LT80 are all relative values.

[0204] The specific test results are shown in Table 7:

[0205] Table 7

[0206]

[0207] The applicant declares that the present invention uses the above-mentioned embodiments to illustrate the detailed process flow of the present invention, but the present invention is not limited to the above-mentioned detailed process flow, that is, it does not mean that the present invention must rely on the above-mentioned 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 deuterated composition containing a phenylnaphthylanthracene compound, the deuterated composition comprising at least a first component and a second component, the first component being selected from any one of the compounds represented by formula (I), and the second component being selected from any one of the compounds having the structure represented by formula A; In formula (I), Ar1 is selected from a single bond, a phenylene group, a naphthylene group or a biphenylene group, and Ar2 is selected from H, a phenyl group, a naphthyl group or a biphenyl group; The H atoms on Ar1, Ar2 and the dibenzofuran ring can be replaced by D atoms; In formula A, Ar 301 , Ar 302 , Ar 401 , Ar 402 are each independently selected from one of phenyl, naphthyl, phenanthryl, phenylene, naphthylene or phenanthrylene, and Ar 301 , Ar 302 , Ar 401 , Ar 402 are not simultaneously phenanthryl; the structure shown in formula A contains at most one phenanthryl; Each of o and p independently is selected from 0 or 1; The H atoms in the compound represented by formula A can be replaced by D atoms.

2. A deuterated composition containing a phenylnaphthylanthracene compound, the deuterated composition comprising at least a first component and a second component, the first component being selected from any one of the compounds represented by formula (I), and the second component being selected from any one of the compounds represented by formula (I), and the first component and the second component are different; In formula (I), Ar1 is selected from a single bond, a phenylene group, a naphthylene group or a biphenylene group, and Ar2 is selected from H, a phenyl group, a naphthyl group or a biphenyl group; The H atoms on Ar1, Ar2 and the dibenzofuran ring can be replaced by D atoms.

3. A phenylnaphthylanthracene compound, characterized in that, The structural formula is as shown in formula (I): Wherein, Ar1 is selected from a single bond, a phenylene group, a naphthylene group or a biphenylene group, and Ar2 is selected from H, a phenyl group, a naphthyl group or a biphenyl group; The H atoms on Ar1, Ar2 and the dibenzofuran ring can be replaced by D atoms; And the phenylnaphthylanthracene compound does not include BH1: The phenylnaphthylanthracene compound is used to prepare the deuterated composition according to claim 1 or 2; Preferably, the compound represented by formula (I) includes the compounds represented by formula (I-A) and formula (I-B) as follows: Preferably, the compound represented by formula (I) includes the compounds represented by formula (I-A-1) to formula (I-A-4) and the compounds represented by formula (I-B-5) to formula (I-B-8) as follows: Preferably, the compound represented by formula (I) is selected from any one of the following substituted or unsubstituted compounds: Preferably, the compound represented by formula (I) is selected from the following structures:

4. The deuterated composition according to claim 1, wherein The compound represented by formula A is selected from any one of the following compounds: Preferably, the compound represented by formula A is selected from the following compounds: Preferably, the first component of the deuterated composition is any one of the following compounds:

5. A deuterated composition, characterized in that, Comprising a first component and a second component; the first component is compound 15 and the second component is compound C-3; Or the first component is compound 24 and the second component is compound C-1; Or the first component is compound 24 and the second component is compound BH1; Or the first component is compound 15 and the second component is compound 14:

6. An intermediate, characterized in that, The intermediate is the compound shown as X1-3: The intermediate is used to prepare the phenylnaphthylanthracene compound according to claim 3.

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, and the organic thin film layer includes the deuterated composition according to claims 1-2, claims 4-5 or the phenylnaphthylanthracene compound according to claim 3; Preferably, the organic thin film layer includes a light-emitting layer, and the material of the light-emitting layer includes the deuterated composition as described in Claims 1-2, Claims 4-5 or the phenylnaphthylanthracene compound as described in Claim 3; Preferably, 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: Among them, Ar 21 and Ar 22 are each independently selected from any one of substituted or unsubstituted C6-C 20 aryl, substituted or unsubstituted C3-C 20 heteroaryl; R 21 、R 22 and R 23 each independently selected from any one of hydrogen, C1-C12 straight-chain or branched-chain alkyl, and C6-C12 cycloalkyl; Ar 21 、Ar 22 The substituents described 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 are independently selected from C1-C5 straight-chain or branched-chain alkyl groups or C6-C12 aryl groups; Preferably, the material of the light-emitting layer further includes a compound having the structure shown in Formula BDI: Among them, Ar 101 、Ar 102 、Ar 201 、Ar 202 are each independently selected from any one of substituted or unsubstituted C6-C40 aryl groups and substituted or unsubstituted C12-C20 heteroaryl groups; R 101 and R 102 each independently selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C40 aryl, and substituted or unsubstituted C12-C20 heteroaryl; R 101 and R 102 can be connected into a ring through a single bond; m and n are each independently selected from 0 or 1, and m and n are not both 0 at the same time; Ar 101 、Ar 102 、Ar 201 、Ar 202 、R 101 and R 102 The substituents described in each of them are independently selected from any one or a combination of at least two of -D, -F, -CN, alkyl groups having 1 to 12 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, alkenyl groups having 2 to 8 carbon atoms, aryl groups having 6 to 15 carbon atoms, and heteroaryl groups having 12 to 20 carbon atoms; Preferably, the C6-C40 aryl group is selected from any one of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, benzofluorenyl, 9,10-diphenylanthryl, dibenzofluorenyl, naphthofluorenyl, pyrenyl, perylenyl, spirofluorene, triphenylene, fluoranthenyl, hydrobenzanthryl, indeno-fluorenyl, benzindeno-fluorenyl, dibenzindeno-fluorenyl, naphthofluorenyl or benzonaphthofluorenyl, and is preferably any one of phenyl, naphthyl, biphenyl, terphenyl, fluoranthenyl, fluorenyl, 9,10-diphenylanthryl or benzofluorenyl; Preferably, the C12-C20 heteroaryl group is selected from any one of dibenzofuranyl, dibenzothiophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, dinaphthofuranyl, dinaphthothiophenyl; Preferably, the C1-C12 alkyl group is selected from any one of methyl, ethyl, propyl, butyl, adamantyl, 1-methylcyclohexyl, 1-methylcyclopentyl, cyclopentyl or cyclohexyl; Preferably, the C1-C6 alkoxy group is selected from any one of methoxy, ethoxy, propoxy, butoxy or as shown in the figure, and the dotted line indicates the connection site; Preferably, the C6-C15 aryl group is selected from any one of phenyl, naphthyl or biphenyl; Preferably, the Ar 101 and Ar 102 are each independently selected from any one of the following substituted or unsubstituted groups: phenyl, naphthyl, biphenyl, terphenyl, fluoranthenyl, fluorenyl, 9,10-diphenylanthryl, benzofluorenyl, dibenzofuranyl, dibenzothiophenyl, naphthobenzofuranyl or naphthobenzothiophenyl; the substituent of the substitution is selected from -D (deuterium atom), -F, -CN, phenyl, biphenyl, dibenzofuranyl, methyl, deuterated methyl, adamantyl, tert-butyl, 1-methylcyclopentyl, cyclohexyl, cyclopentyl, methoxy any one or a combination of at least two of naphthyl, dibenzothiophenyl, naphthobenzothiophenyl, and the dotted line indicates the connection site; Preferably, the Ar 201 and Ar 202 are each independently selected from any one of the following substituted or unsubstituted groups: phenyl, naphthyl, dibenzofuranyl or biphenyl; The substituents of the substitution are selected from any one or a combination of at least two of methyl, methoxy, phenyl or dibenzofuranyl; Preferably, R 101 and R 102 are each independently selected from any one of methyl, ethyl, propyl or phenyl; Preferably, R 101 and R 102 are the same.

8. The organic electroluminescent device according to claim 7, characterized in that, The Ar 21 and Ar 22 are each independently selected from any one of; Preferably, said 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 the structure shown in Formula II is selected from any one of the following compounds: Preferably, the compound having the structure shown in Formula III is selected from any one of the following compounds: Preferably, the compound having the structure shown in Formula BDI 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 described in any one of Claims 7-9.

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