Compound, intermediate, organic electroluminescent device and display device

Abstract

The invention provides a compound, an intermediate, an organic electroluminescent device and a display device. The compound has a structure as shown in a formula I; the organic light-emitting device comprises an anode, a cathode and an organic layer located between the anode and the cathode. The organic layer comprises a hole transport layer, an electron blocking layer, a light-emitting layer and an electron transport layer; the material of the light-emitting layer comprises a compound as shown in a formula I; and the material of the electron blocking layer comprises a compound shown as a formula A. The organic light-emitting device provided by the invention has relatively high current efficiency and relatively long service life.

Description

[0001] This application is a divisional application of the patent application with application number 202211259365.7 (the filing date of the original application is October 14, 2022, and the name of the invention is an organic electroluminescent device and display device). Technical Field

[0002] The invention belongs to the technical field of organic electroluminescence, and in particular relates to a compound, an intermediate, an organic electroluminescent device and a display device. Background Art

[0003] Electroluminescence, also known as electric field luminescence, or EL for short, is a luminescence phenomenon in which a solid directly converts electrical energy into light energy under the action of an electric field generated by a voltage applied to two electrodes. Among them, the electroluminescence of organic materials belongs to injection-type composite luminescence. Organic electroluminescent materials can be divided into hole injection layer, hole transport layer, electron blocking layer, luminescent layer, electron transport layer, electron injection layer and other materials according to their functions and device structures in organic electroluminescent (OLED) devices.

[0004] Currently, organic light emitting diodes (OLEDs) have become the mainstream display technology, and accordingly, various new OLED materials have been developed. However, their various performances need to be improved, especially in terms of efficiency, lifespan, voltage, etc. In order to meet people's higher requirements for OLED devices, the field urgently needs to develop more types of materials with higher performance, so as to prepare OLED devices with excellent performance. Summary of the invention

[0005] In view of the shortcomings of the prior art, the present invention aims to provide a compound, an intermediate, an organic electroluminescent device and a display device. In the present invention, by designing the material of the light-emitting layer and the material of the electron blocking layer, the prepared organic electroluminescent device has a higher current efficiency and a longer life.

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

[0007] In a first aspect, the present invention provides an organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode and an organic layer between the anode and the cathode;

[0008] The organic layer includes a hole transport layer, an electron blocking layer, a light emitting layer, and an electron transport layer;

[0009] The material of the light-emitting layer includes the compound shown in formula I;

[0010]

[0011] Among them, Ar 11is selected from C6-C40 aryl or C3-C30 heteroaryl;

[0012] L is selected from at least one of a single bond, a C6-C40 arylene group, or a C3-C30 heteroarylene group;

[0013] Ar 12 Having a structure as shown in Formula IA, the dotted line indicates the connection site;

[0014] The hydrogen atoms in the compound represented by Formula I can be independently replaced by deuterium atoms, -F, -CN, C1-C12 alkyl, C1-C12 alkoxy, C6-C20 aryl, or C3-C20 heteroaryl;

[0015] The material of the electron blocking layer includes the compound shown in formula A;

[0016]

[0017] wherein X is selected from O or S;

[0018] In formula A, R 11 , R 21 Each is independently selected from hydrogen, deuterium, fluorine, CN, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C40 aryl;

[0019] In formula A, Ar is selected from substituted or unsubstituted C6-C40 arylene groups;

[0020] In formula A, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C40 aryl group, a substituted or unsubstituted C12-C40 oxygen heteroaryl group, or a substituted or unsubstituted C12-C40 sulfur heteroaryl group, and at least one of Ar1 and Ar2 is selected from any one of phenyl, naphthyl, triphenylene or fluoranthenyl;

[0021] p is selected from 0 or 1;

[0022] m and n are each independently selected from integers of 0-4.

[0023] In the present invention, a compound with a specific structural formula is selected as the material of the light-emitting layer, and a compound with a specific structural formula is used as the material of the electron blocking layer. The prepared organic electroluminescent device has higher current efficiency and longer life.

[0024] In the present invention, the C6 to C40 may be selected from C6, C10, C12, C15, C18, C24, C30, C36 or C40, etc.

[0025] The C3-C30 can be selected from C3, C5, C6, C10, C12, C18, C20, C24 or C30, etc.

[0026] The C1-C12 can be selected from C1, C2, C4, C6, C8, C10 or C12, etc.

[0027] The C6-C40 can be selected from C6, C10, C12, C15, C18 or C20, etc.

[0028] The C3-C30 can be selected from C3, C5, C6, C10, C12, C18 or C20, etc.

[0029] The C1-C20 can be selected from C1, C2, C4, C6, C8, C10, C12, C14, C16, C18 or C20, etc.

[0030] The C6 to C40 may be selected from C12, C15, C18, C24, C30, C36 or C40, etc.

[0031] The m and n are each independently selected from 0, 1, 2, 3 or 4.

[0032] It should be noted that the oxygen heteroaryl group refers to a structure having an oxygen-containing five-membered heterocyclic ring formed by two aromatic rings connected by a single bond and bridged by an O atom. For example, two benzene rings are connected by a single bond to form biphenyl, and the carbon atoms on the two benzene rings constituting the biphenyl are simultaneously connected to O atoms to form dibenzofuran.

[0033] The sulfur heteroaryl group refers to a structure having a sulfur-containing five-membered heterocyclic ring formed by two aromatic rings connected by a single bond and bridged by an S atom. For example, two benzene rings are connected by a single bond to form biphenyl, and the carbon atoms on the two benzene rings constituting the biphenyl are simultaneously connected to S atoms to form dibenzothiophene.

[0034] The following are preferred technical solutions of the present invention, but are not intended to limit the technical solutions provided by the present invention. Through the following preferred technical solutions, the objectives and beneficial effects of the present invention can be better achieved and realized.

[0035] As a preferred technical solution of the present invention, the compound represented by formula I has the structure represented by the following formulas I-1 to I-4:

[0036]

[0037] Among them, Ar 11 , L, Ar 12 It has the same protection scope as claim 1.

[0038] Preferably, the compound represented by formula I has a structure represented by formula I-1 or I-4.

[0039] Preferably, the Ar 11 Any one or a combination of at least two selected from phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, fluorenyl, anthracenyl, phenanthryl, triphenylene, fluoranthenyl, benzofluorenyl, dibenzofluorenyl, indenofluorenyl, dibenzofuranyl, dibenzothienyl, naphthobenzofuranyl, naphthobenzothienyl, dinaphthofuranyl, and dinaphthothienyl.

[0040] Preferably, L is selected from any one of a single bond, a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a binaphthylene group, a fluorenylene group, anthracene group, a phenanthrylene group, a triphenylene group, a fluoranthenylene group, a dibenzofuranyl group, a dibenzothiophenylene group, a naphthobenzofuranyl group, a naphthobenzothiophenylene group, a dinaphthofuranyl group, a dinaphthothiophenylene group, a benzofluorenyl group, a dibenzofluorenyl group, and an indenofluorenyl group, or a combination of at least two of them.

[0041] Preferably, L is selected from any one of a single bond, a phenylene group, a biphenylene group, and a naphthylene group.

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

[0043]

[0044]

[0045]

[0046]

[0047] The substitution means that the hydrogen atoms in the above compounds can be independently replaced by deuterium atoms. Preferably, the compound represented by formula I is selected from any one of the following compounds:

[0048]

[0049] It should be noted that D in the above compounds is a deuterium atom (the same below).

[0050] As a preferred technical solution of the present invention, the compound represented by formula A is selected from the compound represented by formula A-1 or the compound represented by formula A-2:

[0051]

[0052] Wherein, X and X1 are each independently selected from O or S;

[0053] In the compound represented by formula A-1 or the compound represented by formula A-2, R 11 , R 21, Ar has the same protection scope as above;

[0054] In the compound represented by formula A-1 or the compound represented by formula A-2, Ar1 is selected from any one of phenyl, naphthyl, triphenylene or fluoranthenyl;

[0055] In the compound represented by formula A-1 or the compound represented by formula A-2, R 31 Selected from C1-C20 (for example, C1, C2, C4, C6, C8, C10, C12, C14, C16, C18 or C20, etc.) straight chain or branched alkyl, C1-C20 (for example, C1, C2, C4, C6, C8, C10, C12, C14, C16, C18 or C20, etc.) alkoxy, C6-C40 (for example, C6, C10, C12, C15, C18, C24, C30, C36 or C40, etc.) aryl;

[0056] In the compound represented by formula A-1 or the compound represented by formula A-2, R 41 , R 42 are each independently selected from C1-C20 (e.g., C1, C2, C4, C6, C8, C10, C12, C14, C16, C18, or C20, etc.) straight or branched alkyl, C6-C40 (e.g., C6, C10, C12, C15, C18, C24, C30, C36, or C40, etc.) aryl, and R 41 and R 42 They are independent of each other or connected to form a ring through single bonds.

[0057] As a preferred technical solution of the present invention, the compound represented by formula A is selected from any one of compounds 1 to 140 and compounds 1S to 140S:

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067] The compound 1S-140S is a compound 1-140 Replace with The dotted lines indicate the connection sites.

[0068] For example, the structure of compound 2 is Then the structure of compound 2S is:

[0069] As a preferred technical solution of the present invention, the material of the light-emitting layer further includes a compound represented by formula II and / or a compound represented by formula III:

[0070]

[0071] Among them, in the compound represented by formula II, Ar 21 ,Ar 22 Each is independently selected from any one of a substituted or unsubstituted C6-C40 (for example, C6, C10, C12, C15, C18, C24, C30, C36 or C40, etc.) aryl group, and a substituted or unsubstituted C3-C40 (for example, C3, C5, C6, C10, C12, C15, C18, C24, C30, C36 or C40, etc.) heteroaryl group;

[0072] In the compound represented by formula II, R 21 , R 22 and R 23 Each is independently selected from hydrogen or C1-C12 (e.g., C1, C2, C4, C6, C8, C10 or C12, etc.) alkyl;

[0073] In the compound represented by formula II, Ar 21 ,Ar 22 The substituents are independently selected from C1-C5 alkyl (e.g., methyl, ethyl, propyl, butyl or pentyl) or C6-C12 aryl (e.g., phenyl, naphthyl, biphenyl, etc.);

[0074] In the compound represented by formula III, Ar 31 ,Ar 32 ,Ar 33 and Ar 34 Each independently selected from substituted or unsubstituted C6 to C40

[0075] Any one of (for example, C6, C10, C12, C15, C18, C24, C30, C36 or C40, etc.) aryl, substituted or unsubstituted C12-C40 (for example, C12, C15, C18, C24, C30, C36 or C40, etc.) heteroaryl;

[0076] In the compound represented by formula III, R 31 Any one selected from phenyl, naphthyl or biphenyl;

[0077] a is selected from 0 or 1;

[0078] In the compound represented by formula III, Ar 31 ,Ar 32 ,Ar 33 ,Ar 34 The substituted substituents are each independently selected from C1-C5 alkyl (eg, methyl, ethyl, propyl, butyl or pentyl) or C6-C12 aryl (eg, phenyl, naphthyl, biphenyl, etc.).

[0079] As a preferred technical solution of the present invention, the C6-C40 aryl group is selected from any one or a combination of at least two of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthfluoroenyl, pyrenyl, peryl, spirofluorenyl, triphenylene, fluoranthenyl, hydrogenated benzanthryl, indenofluorenyl, benzoindenofluorenyl, dibenzoindenofluorenyl, naphthfluoroenyl or benzonaphthfluoroenyl.

[0080] Preferably, the C6-C40 aryl group is selected from any one of phenyl, biphenyl, fluorenyl, naphthyl, triphenylene, and fluoranthene, or a combination of at least two of them.

[0081] Preferably, the C3-C40 heteroaryl group is selected from any one of dibenzofuranyl, dibenzothiophenyl, benzodibenzofuranyl, benzodibenzothiophenyl, dinaphthofuranyl and dinaphthothiophenyl, or a combination of at least two of them.

[0082] Preferably, the C1-C12 alkyl group is selected from any one of methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl, and adamantyl.

[0083] Preferably, the compound represented by formula II is selected from any one of the following compounds:

[0084]

[0085]

[0086] Preferably, the compound represented by formula III is selected from any one of the following compounds:

[0087]

[0088]

[0089] In a second aspect, the present invention provides a display device, comprising the organic electroluminescent device as described in the first aspect.

[0090] In a third aspect, the present invention provides a compound, characterized in that the compound has a structure shown in Formula I:

[0091]

[0092] Among them, Ar 11 is selected from C6-C40 aryl or C3-C30 heteroaryl;

[0093] L is selected from at least one of a single bond, a C6-C40 arylene group, or a C3-C30 heteroarylene group;

[0094] Ar 12 Having a structure as shown in Formula IA, the dotted line indicates the connection site;

[0095] The hydrogen atoms in the compound represented by Formula I can be independently replaced by deuterium atoms, -F, -CN, C1-C12 alkyl, C1-C12 alkoxy, C6-C20 aryl, or C3-C20 heteroaryl;

[0096] The hydrogen atoms in the compound represented by Formula I can be independently replaced by deuterium atoms, -F, -CN, C1-C12-alkyl, C1-C12-alkoxy, C1-C20-aryl, or C3-C20-heteroaryl;

[0097] And the compound shown in formula I is not

[0098] The compound is used as a material for the light-emitting layer of the organic electroluminescent device according to the first aspect.

[0099] Preferably, the compound represented by formula I has the structure represented by the following formulas I-1 to I-4:

[0100]

[0101] Among them, Ar 11 , L, Ar 12 Has the same protection scope as above.

[0102] Preferably, the compound represented by formula I has a structure as shown in the following formula I-1 or I-4.

[0103] Preferably, the Ar 11Any one or a combination of at least two selected from phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, fluorenyl, anthracenyl, phenanthryl, triphenylene, fluoranthenyl, benzofluorenyl, dibenzofluorenyl, indenofluorenyl, dibenzofuranyl, dibenzothienyl, naphthobenzofuranyl, naphthobenzothienyl, dinaphthofuranyl, and dinaphthothienyl.

[0104] Preferably, L is selected from any one of a single bond, a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a binaphthylene group, a fluorenylene group, anthracene group, a phenanthrylene group, a triphenylene group, a fluoranthenylene group, a dibenzofuranyl group, a dibenzothiophenylene group, a naphthobenzofuranyl group, a naphthobenzothiophenylene group, a dinaphthofuranyl group, a dinaphthothiophenylene group, a benzofluorenyl group, a dibenzofluorenyl group, and an indenofluorenyl group, or a combination of at least two of them.

[0105] Preferably, L is selected from any one of a single bond, a phenylene group, a biphenylene group, and a naphthylene group.

[0106] Preferably, the compound is selected from the following substituted or unsubstituted compounds:

[0107]

[0108]

[0109]

[0110]

[0111] The substitution means that the hydrogen atoms in the above compounds can be independently replaced by deuterium atoms. Preferably, the compound represented by formula I is selected from any one of the following compounds:

[0112]

[0113] In a fourth aspect, the present invention provides an intermediate, wherein the intermediate comprises the following compound:

[0114]

[0115]

[0116] The intermediate is used to prepare the compound shown in formula I of the material of the light-emitting layer of the organic electroluminescent device as described in the first aspect, or is used to prepare the compound as described in the third aspect.

[0117] It should be noted that the present invention does not impose any special restrictions on the preparation methods of the compound represented by formula I, the compound represented by formula II, the compound represented by formula III, and the compound represented by formula A, and the preparation methods commonly used in the art can be adopted.

[0118] Compared with the prior art, the present invention has the following beneficial effects:

[0119] In the present invention, a compound with a specific structural formula is selected as the material of the light-emitting layer, and a compound with a specific structural formula is used as the material of the electron blocking layer. The prepared organic electroluminescent device has higher current efficiency and longer life. DETAILED DESCRIPTION

[0120] For the convenience of understanding the present invention, the present invention lists the following embodiments. It should be understood by those skilled in the art that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0121] Preparation Example 1

[0122] This preparation example provides an intermediate MA and a synthesis method thereof, and the synthesis method is as follows:

[0123]

[0124] (1) Synthesis of intermediate M1

[0125] In a 500mL three-necked flask, add 100mL of dichloromethane, iron powder (0.2g), ferrous chloride (0.1g), and the compound shown in M0 (4.7g), cool to 0°C, add 30mL of dichloromethane solution of iodine (5.2g) dropwise, keep at 0-5°C for 2 hours after the addition, slowly warm to room temperature for 4 hours, and then warm to reflux for 1 hour. Add water to split, wash with water, wash with 1% sodium bicarbonate solution, wash with sodium sulfite aqueous solution, and then wash with water until neutral, dry with magnesium sulfate, filter out magnesium sulfate, evaporate the solvent under reduced pressure, and crystallize 3 times with a mixed solvent of ethanol and petroleum ether to obtain intermediate M1 (1.3g).

[0126] The mass spectrometry of the intermediate M1 revealed a mass-to-charge ratio (m / z) of 359.96.

[0127] (2) Synthesis of intermediate MA-1

[0128] Under nitrogen protection, 50 mL of toluene, 10 mL of ethanol and 5 mL of water were added to a 250 mL three-necked flask in sequence, and then intermediate M1 (3.6 g), 2-fluoro-3-bromophenylboronic acid (2.2 g), anhydrous potassium phosphate (3.2 g) and tetrakistriphenylphosphine palladium (0.2 g) were added, and the temperature was slowly raised to 60 ° C for reaction for 12 h, and then cooled to room temperature, and water was added to separate. The organic layer was washed with water and dried with magnesium sulfate. After filtering to remove magnesium sulfate, the solvent was removed under reduced pressure, and crystallized twice with a mixed solvent of ethanol and petroleum ether to obtain intermediate MA-1 (2.1 g).

[0129] The intermediate MA-1 was subjected to mass spectrometry detection, and the two peaks with the largest mass-to-charge ratio (m / z) were measured to be 406.00 and 408.00, and their abundances were basically the same.

[0130] (3) Synthesis of intermediate MA

[0131] Under nitrogen protection, 600 mL of DMF, intermediate MA-1 (4.0 g), anhydrous potassium carbonate (1.4 g), cuprous iodide (0.02 g), and o-phenanthroline (0.3 g, CAS: 5144-89-8) were added to a 1000 mL three-necked flask, heated to 120 ° C for reaction for 60 h, cooled, water and dichloromethane were added for separation, the organic layer was washed with water until neutral, dried with magnesium sulfate, the desiccant was filtered out, concentrated to dryness, and crystallized with ethanol to obtain intermediate MA (1.2 g).

[0132] The intermediate MA was subjected to mass spectrometry detection, and the two peaks with the largest mass-to-charge ratio (m / z) were measured to be 385.99 and 387.99, and their abundances were basically the same.

[0133] The obtained intermediate MA was subjected to nuclear magnetic resonance detection: 1H-NMR (Bruker Company, Switzerland, AvanceⅡ400MHz nuclear magnetic resonance spectrometer, CDCl3), δ8.58 (m, 1H), δ8.00 (m, 1H), δ7.90 (m, 1H), δ7.81 (m, 1H), δ7.57 (m, 1H), δ7.56~7.52 (m, 2H), δ7.42 (m, 1H), δ7.33 (m, 1H), δ7.29 (m, 1H), δ7.02 (m, 1H).

[0134] Preparation Example 2

[0135] This preparation example provides an intermediate MB and a synthesis method thereof, and the synthesis method is as follows:

[0136]

[0137] For the specific synthesis method, refer to the synthesis method of intermediate MA in Preparation Example 1.

[0138] The intermediate MB-1 was subjected to mass spectrometry detection, and the two peaks with the largest mass-to-charge ratio (m / z) were measured to be 406.00 and 408.00, and their abundances were basically the same.

[0139] The intermediate MB was subjected to mass spectrometry detection, and the two peaks with the largest mass-to-charge ratio (m / z) were measured to be 385.99 and 387.99, and their abundances were basically the same.

[0140] Preparation Example 3

[0141] This preparation example provides an intermediate MC and a synthesis method thereof, and the synthesis method is as follows:

[0142]

[0143] For the specific synthesis method, refer to the synthesis method of intermediate MA in Preparation Example 1.

[0144] The intermediate MC-1 was subjected to mass spectrometry detection, and the two peaks with the largest mass-to-charge ratio (m / z) were measured to be 406.00 and 408.00, and their abundances were basically the same.

[0145] The intermediate MC was subjected to mass spectrometry detection, and the two peaks with the largest mass-to-charge ratio (m / z) were measured to be 385.99 and 387.99, and their abundances were basically the same.

[0146] Preparation Example 4

[0147] This preparation example provides an intermediate MD and a synthesis method thereof, and the synthesis method is as follows:

[0148]

[0149] For the specific synthesis method, refer to the synthesis method of intermediate MA in Preparation Example 1.

[0150] The intermediate MD-1 was subjected to mass spectrometry detection, and the two peaks with the largest mass-to-charge ratio (m / z) were measured to be 406.00 and 408.00, and their abundances were basically the same.

[0151] The intermediate MD was subjected to mass spectrometry detection, and the two peaks with the largest mass-to-charge ratio (m / z) were measured to be 385.99 and 387.99, and their abundances were basically the same.

[0152] Synthesis Example 1

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

[0154]

[0155] Under nitrogen protection, 100 mL of toluene, 30 mL of ethanol and 10 mL of water were added to a 250 mL three-necked flask in sequence, and then 9-phenylanthracene-10-boric acid (3.0 g), intermediate MA (3.9 g), anhydrous sodium carbonate (2.2 g) and tetrakistriphenylphosphine palladium (0.1 g) were added, and the temperature was slowly raised to reflux for 12 h, and the temperature was lowered to room temperature. Water was added to separate, the organic layer was washed with water, dried over magnesium sulfate, and the magnesium sulfate was removed by filtration. The solvent was removed under reduced pressure, and crystallization was performed with a mixed solvent of ethanol and toluene to obtain compound 1A (4.1 g).

[0156] The mass spectrometry of compound 1A showed that the mass-to-charge ratio (m / z) was 560.18.

[0157] Synthesis Example 2-24

[0158] Synthesis Examples 2-24 provide a compound, respectively, which is synthesized by the corresponding boronic acid compound and the corresponding bromine compound. The specific synthesis method refers to compound 1A in Synthesis Example 1. The specific structural formula of the synthesized compound is shown in Table 1 below. The compounds are respectively subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) results are shown in Table 1 below.

[0159] Table 1

[0160]

[0161]

[0162]

[0163]

[0164]

[0165] The specific structures of the compounds used in the following device application examples and device comparative examples are as follows:

[0166]

[0167] Device Example 1

[0168] The device embodiment provides an organic electroluminescent device, and the structure of the organic electroluminescent device is: ITO / HT (40nm) / electron blocking layer (10nm) / luminescent layer main material: BD-2 3% (30nm) / TPBI (30nm) / LiF (0.5nm) / Al (150nm).

[0169] The compound 1A of the present invention is selected as the main material of the light-emitting layer in the organic electroluminescent device. S-EB1 is selected as the electron blocking layer material. The preparation method of the organic electroluminescent device is as follows:

[0170] The material was placed in a vacuum chamber and evacuated to 1×10 -5 ~1×10 -6 Pa, and then vacuum evaporated onto the cleaned ITO substrate. Among them, the main material of the light-emitting layer: BD-2 3% (30nm) means that in the device, the main material of the light-emitting layer and BD-2 are co-evaporated in a volume ratio of 97:3 to form a light-emitting layer, and the thickness of the light-emitting layer is 30nm.

[0171] Device Examples 2-18

[0172] Device Examples 2-18 respectively provide an organic electroluminescent device, which differs from Device Example 1 in that the main material of the light-emitting layer and the material of the electron blocking layer are different (see Table 2 for details), and the other preparation steps and conditions are the same as those of Device Example 1.

[0173] Device Comparison Examples 1-7

[0174] Device Comparative Examples 1-7 respectively provide an organic electroluminescent device, which is different from Device Example 1 in that the main material of the light-emitting layer and the material of the electron blocking layer are different (see Table 2 for details), and the other preparation steps and conditions are the same as those of Device Example 1.

[0175] Performance Testing:

[0176] The OLED-1000 multi-channel accelerated aging life and light color performance analysis system produced by Hangzhou Yuanfang was used to test the driving voltage, current efficiency and life LT90 of the OLED devices provided above; LT90 refers to the time required for the brightness to drop to 90% of the original brightness while maintaining the current density unchanged at the initial brightness of 1000nit. The test items include the brightness, driving voltage, and current efficiency of the organic electroluminescent device. The driving voltage, current efficiency, and LT90 data are all based on a brightness of 1000cd / m 2 The test results are shown in Table 2 below.

[0177] Table 2

[0178]

[0179]

[0180] In device embodiment 6, 1A:1A-D1=1:1 means that in this device embodiment, the main material of the light-emitting layer is 1A:1A-D1, and the volume ratio of the two is 1:1.

[0181] It can be seen from the contents of Table 2 that in the present invention, by selecting a compound with a specific structure as the material of the light-emitting layer and selecting a compound with a specific structure as the material of the electron blocking layer, the organic electroluminescent device prepared has a lower driving voltage, a higher current efficiency and a longer life.

[0182] It can be seen from device embodiments 4, 5, 7 and device embodiments 1-3, 6, 8, 9, 10-15, 17, and 18 that compared with the organic electroluminescent devices prepared by using the compounds conforming to the structures shown in formulas I-2 and I-3 as the main materials of the light-emitting layer, the organic electroluminescent devices prepared by using the compounds conforming to the structures shown in formulas I-1 and I-4 as the main materials of the light-emitting layer have longer life.

[0183] It can be seen from device examples 1-18 and device comparison examples 1-2 and 4-7 that in the present invention, by selecting compounds with specific structures as the light-emitting layer material or selecting compounds with specific structures as the electron blocking layer material, an organic electroluminescent device with excellent comprehensive performance can be prepared.

[0184] It can be seen from device examples 1-18 and device comparative example 3 that the design of the electron blocking layer in the organic electroluminescent device can further reduce the driving voltage and improve the current efficiency and lifespan.

[0185] The applicant declares that the present invention illustrates the detailed process flow of the present invention through the above-mentioned embodiments, 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 of the present invention, equivalent replacement of various raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A compound, characterized in that The compound has a structure shown in Formula I: Among them, Ar 11 is selected from C6-C40 aryl or C3-C30 heteroaryl; L is selected from at least one of a single bond, a C6-C40 arylene group, or a C3-C30 heteroarylene group; Ar 12 Having a structure as shown in Formula IA, the dotted line indicates the connection site; The hydrogen atoms in the compound represented by Formula I can be independently replaced by deuterium atoms, -F, -CN, C1-C12 alkyl, C1-C12 alkoxy, C6-C20 aryl, or C3-C20 heteroaryl; The hydrogen atoms in the compound represented by Formula I can be independently replaced by deuterium atoms, -F, -CN, C1-C12-alkyl, C1-C12-alkoxy, C1-C20-aryl, or C3-C20-heteroaryl; And the compound shown in formula I is not The compound is used as a material for a light-emitting layer of an organic electroluminescent device.

2. The compound according to claim 1, characterized in that The compound represented by formula I has the structure represented by the following formulas I-1 to I-4: Among them, Ar 11 , L, Ar 12 It has the same protection scope as claim 1; Preferably, the compound represented by formula I has a structure as represented by formula I-1 or I-4.

3. The compound according to claim 1 or 2, characterized in that The Ar 11 Any one or a combination of at least two selected from phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, fluorenyl, anthracenyl, phenanthryl, triphenylene, fluoranthenyl, benzofluorenyl, dibenzofluorenyl, indenofluorenyl, dibenzofuranyl, dibenzothienyl, naphthobenzofuranyl, naphthobenzothienyl, dinaphthofuranyl, dinaphthothienyl; Preferably, L is selected from any one of a single bond, a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a binaphthylene group, a fluorenylene group, an anthrylene group, a phenanthrylene group, a triphenylene group, a fluoranthenylene group, a dibenzofuranyl group, a dibenzothiophenylene group, a naphthobenzofuranyl group, a naphthobenzothiophenylene group, a dinaphthofuranyl group, a dinaphthothiophenylene group, a benzofluorenyl group, a dibenzofluorenyl group, and an indenofluorenyl group, or a combination of at least two thereof; Preferably, L is selected from any one of a single bond, a phenylene group, a biphenylene group, and a naphthylene group; Preferably, the compound is selected from the following substituted or unsubstituted compounds: The substitution means that the hydrogen atoms in the above compounds can each be independently replaced by a deuterium atom.

4. An intermediate, characterized in that The intermediates include the following compounds: The intermediate is used to prepare the compound as claimed in any one of claims 1 to 3.

5. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises an anode, a cathode and an organic layer between the anode and the cathode; The organic layer includes a hole transport layer, an electron blocking layer, a light emitting layer, and an electron transport layer; The material of the light-emitting layer includes the compound shown in formula I; Among them, Ar 11 is selected from C6-C40 aryl or C3-C30 heteroaryl; L is selected from at least one of a single bond, a C6-C40 arylene group, or a C3-C30 heteroarylene group; Ar 12 Having a structure as shown in Formula IA, the dotted line indicates the connection site; The hydrogen atoms in the compound represented by Formula I can be independently replaced by deuterium atoms, -F, -CN, C1-C12 alkyl, C1-C12 alkoxy, C6-C20 aryl, or C3-C20 heteroaryl; The material of the electron blocking layer includes a compound represented by formula S-EB2 or formula S-EB1; 6. The organic electroluminescent device according to claim 5, characterized in that: The compound represented by formula I has the structure represented by the following formulas I-1 to I-4: Among them, Ar 11 , L, Ar 12 It has the same protection scope as claim 5; Preferably, the compound represented by formula I has a structure represented by formula I-1 or I-4; Preferably, the Ar 11 Any one or a combination of at least two selected from phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, fluorenyl, anthracenyl, phenanthryl, triphenylene, fluoranthenyl, benzofluorenyl, dibenzofluorenyl, indenofluorenyl, dibenzofuranyl, dibenzothienyl, naphthobenzofuranyl, naphthobenzothienyl, dinaphthofuranyl, dinaphthothienyl; Preferably, L is selected from any one of a single bond, a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a binaphthylene group, a fluorenylene group, an anthrylene group, a phenanthrylene group, a triphenylene group, a fluoranthenylene group, a dibenzofuranyl group, a dibenzothiophenylene group, a naphthobenzofuranyl group, a naphthobenzothiophenylene group, a dinaphthofuranyl group, a dinaphthothiophenylene group, a benzofluorenyl group, a dibenzofluorenyl group, and an indenofluorenyl group, or a combination of at least two thereof; Preferably, L is selected from any one of a single bond, a phenylene group, a biphenylene group, and a naphthylene group.

7. The organic electroluminescent device according to claim 5 or 6, characterized in that: The compound represented by formula I is selected from the following substituted or unsubstituted compounds: The substitution means that the hydrogen atoms in the above compounds can each be independently replaced by a deuterium atom.

8. The organic electroluminescent device according to any one of claims 5 to 7, characterized in that: The material of the light-emitting layer also includes a compound represented by formula II and / or a compound represented by formula III: Among them, in the compound represented by formula II, Ar 21 ,Ar 22 Each independently selected from substituted or unsubstituted C6-C40 aryl, Any one of substituted or unsubstituted C3-C40 heteroaryl; In the compound represented by formula II, R 21 , R 22 and R 23 Each is independently selected from hydrogen or C1-C12 alkyl; In the compound represented by formula II, Ar 21 ,Ar 22 The substituents in the substitution are each independently selected from C1-C5 alkyl or C6-C12 aryl; In the compound represented by formula III, Ar 31 ,Ar 32 ,Ar 33 and Ar 34 Each is independently selected from any one of a substituted or unsubstituted C6-C40 aryl group and a substituted or unsubstituted C12-C40 heteroaryl group; In the compound represented by formula III, R 31 Any one selected from phenyl, naphthyl or biphenyl; a is selected from 0 or 1; In the compound represented by formula III, Ar 31 ,Ar 32 ,Ar 33 ,Ar 34 The substituents in the substitution are each independently selected from C1-C5 alkyl or C6-C12 aryl; Preferably, the C6-C40 aryl group is selected from phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, Any one of benzofluorenyl, dibenzofluorenyl, naphthofluorenyl, pyrenyl, peryl, spirofluorenyl, triphenylene, fluoranthenyl, hydrogenated benzanthryl, indenofluorenyl, benzoindenofluorenyl, dibenzoindenofluorenyl, naphthofluorenyl or benzonaphthofluorenyl or a combination of at least two thereof; Preferably, the C6-C40 aryl group is selected from any one or a combination of at least two of phenyl, biphenyl, fluorenyl, naphthyl, triphenylene, and fluoranthene; Preferably, the C3-C40 heteroaryl group is selected from any one of dibenzofuranyl, dibenzothiophenyl, benzodibenzofuranyl, benzodibenzothiophenyl, dinaphthofuranyl, and dinaphthothiophenyl, or a combination of at least two thereof; Preferably, the C1-C12 alkyl group is selected from any one of methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl and adamantyl.

9. The organic electroluminescent device according to any one of claims 5 to 8, characterized in that: The compound represented by formula II is selected from any one of the following compounds: Preferably, the compound represented by formula III is selected from any one of the following compounds:

10. A display device, characterized in that: The display device comprises the organic electroluminescent device according to any one of claims 5 to 9.

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