Indolocarbazole deuterated compound, intermediate and organic electroluminescent device

Abstract

The invention provides an indolocarbazole deuterated compound, an intermediate and an organic electroluminescent device. The indolocarbazole deuterated compound has a structure as shown in a formula I. The structure of the indolocarbazole deuterated compound is designed, the indolocarbazole deuterated compound is used as a main body material of a light-emitting layer of an OLED device, and the prepared OLED 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 an indolocarbazole-based deuterated compound, an intermediate, and an organic electroluminescent device. Background Art

[0002] A display integrates electronics, communication, and information processing technologies, and is regarded as another major development opportunity for the electronics industry after electronics and computers. Display technology and displays have occupied a very important position in the development process of information technology. Displays on televisions, computers, telephones, and various instruments and meters provide people with a large amount of information in daily life and work. In recent years, new display technologies have become the focus of research. Among them, flat panel displays have the advantages of small weight, low power consumption, and easy portability, and have become a research hotspot.

[0003] Among various current flat panel displays, liquid crystal displays (LCDs) have an important position. However, LCDs have many deficiencies: they do not emit light by themselves, rely on light sources or ambient light, have viewing angle problems, slow response speeds, and low resolutions. Therefore, people have been looking for new flat panel display technologies. The phenomenon of organic electroluminescence was discovered as early as 1963, but it did not attract much attention at that time; until 1987, the research group of Tang from Eastman Kodak Company in the United States published a high-brightness, high-efficiency thin-film organic electroluminescent device (OLED) made of organic fluorescent materials and hole materials driven by a direct current low voltage, this technology has regained attention and created a brand-new research field.

[0004] OLEDs have prominent advantages, such as low power consumption, fast response speed, easy bending, wide viewing angle, large-area display, and full-color emission, and can be compatible with various existing standards and technologies to make low-cost light-emitting devices, showing broad application prospects in realizing color flat panel displays. In the past few decades, OLEDs, as a new display technology, have achieved great development and have been widely used in the fields of flat panel display, flexible display, solid-state lighting, and vehicle-mounted display.

[0005] Therefore, developing more types of OLED materials with more perfect performance to meet the usage requirements of high-performance OLED devices is the research focus in this field. Summary of the Invention

[0006] Aiming at the deficiencies of the prior art, the purpose of the present invention is to provide an indolocarbazole-based deuterated compound, an intermediate, and an organic electroluminescent device. In the present invention, by designing the structure of the indolocarbazole-based deuterated compound, the indolocarbazole-based deuterated compound is used as the host material of the light-emitting layer of the OLED device, and the prepared OLED device has a lower driving voltage, a higher current efficiency, and a longer lifespan.

[0007] To achieve this purpose, the present invention adopts the following technical solutions:

[0008] In the first aspect, the present invention provides an indolocarbazole-based deuterated compound, and the indolocarbazole-based deuterated compound has the structure shown in the following formula I:

[0009]

[0010] Ar 12 is selected from any one of C6-C40 aryl and C6-C30 heteroaryl;

[0011] m is an integer between 0 and 5, and n is an integer between 0 and 4;

[0012] Ar 12 The hydrogen atoms in can be independently replaced by at least one of -D, -F, -CN, C6-C20 aryl, trityl, triphenylsilyl, C1-C12 alkyl, or C1-C12 alkoxy.

[0013] In the present invention, by designing the structure of the indolocarbazole-based deuterated compound, the indolocarbazole-based deuterated compound is used as the host material of the light-emitting layer of the OLED device, and the prepared OLED device has a lower driving voltage, a higher current efficiency, and a longer lifespan.

[0014] In the present invention, C6-C40 can be C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.

[0015] C6-C30 can be C6, C8, C10, C12, C16, C20, C24, C28, or C30, etc.

[0016] C6-C20 can be C6, C8, C10, C12, C16, or C20, etc.

[0017] C1-C12 can be C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, or C12.

[0018] It should be noted that in the present invention, "D" represents a deuterium atom. Where not separately indicated in the present invention, H and hydrogen therein both represent "protium", and the same applies hereinafter.

[0019] The following are the preferred technical solutions of the present invention, but do not 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.

[0020] 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, anthryl, phenanthryl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthofluorenyl, pyrenyl, perylenyl, spirofluorene, triphenylene, fluoranthenyl, hydrobenzanthryl, indeno[1,2-b]fluorene, benzo[ghi]fluorene, dibenzo[ghi]fluorene, naphthofluorenyl, triphenylmethyl, triphenylsilyl or benzo[naphtho[2,1,8,7-defg]fluorene.

[0021] As a preferred technical solution of the present invention, the C6-C30 heteroaryl group is selected from any one or a combination of at least two of carbazolyl, dibenzothiophenyl, dibenzofuranyl, naphtho[2,1-b]benzofuranyl, naphtho[2,1-b]benzothiophenyl, dinaphtho[2,1-b:1',2'-d]furanyl, dinaphtho[2,1-b:1',2'-d]thiophenyl.

[0022] Preferably, the C6-C20 aryl group is selected from any one of phenyl, naphthyl, biphenyl, anthryl, phenanthryl, fluorenyl, triphenylene or fluoranthenyl.

[0023] Preferably, the C1-C12 alkyl group is selected from any one of methyl, ethyl, propyl, n-butyl, tert-butyl, cyclopentyl, cyclohexyl, octyl, adamantyl.

[0024] Preferably, the C1-C12 alkoxy group is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, octyloxy.

[0025] As a preferred technical solution of the present invention, the Ar 12 is selected from at least one of phenyl, biphenyl, terphenyl, naphthyl, triphenylene, fluoranthenyl, anthryl, phenanthryl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl or dibenzothiophenyl.

[0026] Preferably, the Ar 12 is selected from any one of phenyl, biphenyl, terphenyl or naphthyl.

[0027] Preferably, the hydrogen atoms in the Ar 12 can each independently be substituted by at least one of -D, -F, -CN, phenyl, naphthyl, methyl, ethyl, propyl, tert-butyl, methoxy, ethoxy, propoxy, triphenylmethyl, triphenylsilyl, carbazolyl.

[0028] As a preferred technical solution of the present invention, the indolocarbazole-based deuterated compound is selected from any one of the following substituted or unsubstituted compounds:

[0029]

[0030]

[0031] The substitution means that the hydrogen atoms on the corresponding position groups of the above indolocarbazole-based deuterated compounds can be independently replaced by deuterium atoms. 12 For example, in

[0032] where Ar at the corresponding position group is a phenyl group, after all the hydrogen atoms on the corresponding position group of Ar 12 are replaced by deuterium atoms, 12 the following are obtained

[0033] Preferably, the indolocarbazole-based deuterated compound includes the following compounds:

[0034]

[0035] It should be noted that the preparation method of the indolocarbazole-based deuterated compound of the present invention is not specifically limited, and any commonly used preparation method in the art is applicable.

[0036] Illustrative examples of the synthesis method of the indolocarbazole-based deuterated compound of the present invention include the following steps:

[0037]

[0038] Among them, X1 is selected from any one of -F, -Cl, -Br or -I;

[0039] Ar 12 , m, and n have the same definitions as above;

[0040] Ar 12 the hydrogen atoms in can be independently replaced by at least one of -D, -F, -CN, C6-C20 aryl, trityl, triphenylsilyl, C1-C12 alkyl or C1-C12 alkoxy.

[0041] In a second aspect, the present invention provides an intermediate, and the intermediate has a structure shown in Formula MA below;

[0042]

[0043] Among them, Ar 12 has the same definition as above;

[0044] Ar 12 Each hydrogen atom in it can be independently substituted by at least one of -D, -F, -CN, C6-C20 aryl, triphenylmethyl, triphenylsilyl, C1-C12 alkyl or C1-C12 alkoxy;

[0045] The intermediate does not include the following compounds:

[0046]

[0047]

[0048] The intermediate is used to prepare the indolocarbazole-based deuterated compound as described in the first aspect.

[0049] As a preferred technical solution of the present invention, the intermediate includes the following compounds:

[0050]

[0051] In the 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;

[0052] The material of the organic thin film layer includes the indolocarbazole-based deuterated compound as described in the first aspect.

[0053] Preferably, the organic thin film layer includes a light-emitting layer;

[0054] The host material of the light-emitting layer includes the indolocarbazole-based deuterated compound as described in the first aspect.

[0055] As a preferred technical solution of the present invention, the organic electroluminescent device is a green organic electroluminescent device.

[0056] In the present invention, the light-emitting layer includes a light-emitting layer host material and a doping material, where the doping material is also called a dye or a phosphorescent light-emitting material. The light-emitting layer host material can be a single compound or a mixture formed by two or more compounds.

[0057] Preferably, the light-emitting layer includes a phosphorescent light-emitting layer, and the phosphorescent light-emitting layer includes a green phosphorescent light-emitting layer, a red phosphorescent light-emitting layer, and a blue phosphorescent light-emitting layer.

[0058] The volume percentage content of the host material in the phosphorescent light-emitting layer is 60% to 99.9% (for example, it can be 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 98% or 99.9%, etc.), preferably 70% to 99.5%, and further preferably 85% to 95%.

[0059] In the present invention, the doping material of the light-emitting layer can be selected from phosphorescent materials, which are also known as triplet light-emitting materials and refer to the light emitted by substances from the triplet excited state. In the present invention, the specific selection of the phosphorescent material is not particularly limited, and the doping materials of the light-emitting layer commonly used in the art are applicable. Exemplarily, but not limited to, compounds having the structure shown by formula PD:

[0060]

[0061] wherein M is selected from any one of Ir, Pt, Pd, Os, Ti, Zr, Hf, Eu, Tb, Tm, Cu or Au;

[0062] Y1 - Y4 are each independently selected from carbon or nitrogen;

[0063] Y1 and Y2 can be connected by a single bond or a double bond, and Y3 and Y4 can be connected by a single bond or a double bond;

[0064] Cy1 and Cy2 are each independently selected from phenyl, naphthyl, fluorenyl, spirofluorenyl, indenyl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl, benzimidazolyl, benzofuryl, benzothienyl, isobenzothienyl, benzimidazazolyl, benzazolyl, triazolyl, tetrazolyl, dioxazolyl, triazinyl, dibenzofuryl, dibenzothienyl, N-heterocarbazolyl, N-heterodibenzofuryl, and Cy1 and Cy2 can optionally be connected to each other via a single bond or an organic linking group;

[0065] Between any two ligands of M, between two or more ligands, they can be connected by a single bond, a double bond, or can be bridged by O, S, or can be connected by any chemical group or chemical structure to form a structural form that conforms to chemical principles;

[0066] R 91 and R 92Each independently selected from -H, -D, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazone group, carboxylic acid group, carboxylate group, sulfonic acid group, sulfonate group, phosphoric acid group, phosphate group, -SF5, substituted or unsubstituted C1-C60 (such as C1, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkyl group, substituted or unsubstituted C2-C60 (such as C2, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkenyl group, substituted or unsubstituted C2-C60 (such as C2, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkynyl group, substituted or unsubstituted C1-C60 (such as C1, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkoxy group, substituted or unsubstituted C2-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9 or C10) heterocycloalkyl group, substituted or unsubstituted C6-C60 (such as C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60, etc.) aryl group, substituted or unsubstituted C6-C60 (such as C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60, etc.) aryloxy group, substituted or unsubstituted C6-C60 (such as C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60, etc.) arylthio group, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.

[0067] a1 and a2 are each independently an integer selected from 1-5, such as 1, 2, 3, 4 or 5;

[0068] b is an integer selected from 0-4, such as 0, 1, 2, 3 or 4;

[0069] a is selected from 1, 2 or 3;

[0070] L1 is a monovalent organic ligand, divalent organic ligand or trivalent organic ligand.

[0071] Preferably, the PD compound of the formula is selected from any one of the following compounds:

[0072]

[0073]

[0074]

[0075]

[0076] Fourthly, the present invention provides a display device, and the display device includes the organic electroluminescent device as described in the third aspect.

[0077] Compared with the prior art, the present invention has the following beneficial effects:

[0078] In the present invention, by designing the structure of the indolo[3,2-b]carbazole-based deuterated compound, the indolo[3,2-b]carbazole-based deuterated compound is used as the host material of the light-emitting layer of the OLED device, and the prepared OLED device has a lower driving voltage, a higher current efficiency, and a longer lifespan. Specific Embodiments

[0079] 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 examples are only for helping to understand the present invention and should not be regarded as specific limitations on the present invention.

[0080] Preparation Example 1 Synthesis of Intermediate M1

[0081] This preparation example provides intermediate M1 and its synthesis method, and the synthesis method is as follows:

[0082]

[0083] Under nitrogen protection, dry toluene (60 mL), compound M0 (2.6 g), deuterated 4-bromobiphenyl (2.5 g), tritert-butylphosphine toluene solution (the mass of the tritert-butylphosphine solution is 0.4 g, and the amount of substance of tritert-butylphosphine is 0.0002 mol), and sodium tert-butoxide (1.44 g) are added to a three-necked flask, heated to reflux, after reacting for 8 h, cooled to room temperature, water is added for liquid separation, then the organic layer is washed with water until neutral, dried with magnesium sulfate, magnesium sulfate is filtered off, concentrated to dryness, separated by silica gel column chromatography, and eluted with a solvent of petroleum ether:ethyl acetate = 20:1 (volume ratio) to obtain intermediate M1 (2.9 g).

[0084] Mass spectrometry detection was performed on intermediate M1: the measured mass-to-charge ratio (m / z) was 419.23.

[0085] Preparation Examples 2-7

[0086] Preparation Examples 2-7 respectively provide an intermediate compound and a synthesis method thereof. The corresponding intermediate compound refers to the synthesis method of intermediate M1, and compound M0 is reacted with different brominated substances (as shown in Table 1 below) to prepare the corresponding intermediates, as shown in Table 1 below. The mass spectrum of the prepared intermediate is characterized, and its (m / z) value is recorded. See Table 1 below for details.

[0087] Table 1

[0088]

[0089]

[0090] Synthesis Example 1

[0091] This synthesis example provides compound P1 and its synthesis method, and its synthesis method is as follows:

[0092]

[0093] Under nitrogen protection, dry toluene (110 mL), intermediate M1 (4.2 g), 3-bromobiphenyl (2.3 g), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.0575 g), 10% tri-tert-butylphosphine toluene solution (the mass of tri-tert-butylphosphine solution is 0.4 g, and the amount of tri-tert-butylphosphine is 0.0002 mol) and sodium tert-butoxide (1.44 g) were added to a three-necked flask. The mixture was heated to reflux for 6 h, cooled to room temperature, and separated by adding water. The organic layer was then washed with water until neutral, dried with magnesium sulfate, filtered to remove the magnesium sulfate, concentrated to dryness, separated by silica gel column chromatography, and eluted with petroleum ether to obtain compound P1 (5.0 g).

[0094] The mass spectrometry detection of compound P1: the mass-to-charge ratio (m / z) was measured to be 571.29.

[0095] Synthesis Example 2-7

[0096] The synthesis examples are respectively a compound and a synthesis method thereof. The corresponding compounds refer to the synthesis method of compound P1, and different raw materials are used to react to prepare the following compounds (see Table 2 below for details). The mass spectra of the prepared compounds are measured and the (m / z) values ​​are recorded. See Table 2 below for details.

[0097] Table 2

[0098]

[0099]

[0100] The synthesis of other compounds not listed can be carried out by referring to the above embodiments in combination with common knowledge in the art.

[0101] The specific structures of the partial compounds used in the following device examples and device comparative examples are as follows:

[0102]

[0103] Among them, the synthesis method of compound D1 is as follows:

[0104]

[0105] Referring to the synthesis method of intermediate M1, increase the proportion of the bromide, so that the amount of 4-bromobiphenyl is

[0106] 2 times the amount of substance, and the reaction time is extended to 12 hours, and the others remain unchanged, to synthesize compound D1.

[0107] The obtained compound D1 was subjected to mass spectrometry detection, and the measured mass-to-charge ratio (m / z) was: 562.24.

[0108] Among them, the synthesis method of compound D3 is as follows:

[0109]

[0110] Referring to the synthesis method of compound P1, compound D3 was synthesized.

[0111] The obtained compound D3 was subjected to mass spectrometry detection, and the measured mass-to-charge ratio (m / z) was: 570.29.

[0112] Device Example 1

[0113] This device example provides an organic electroluminescent device, and the compound provided by the present invention is selected as the green light host material in the organic electroluminescent device.

[0114] The structure of the organic electroluminescent device is: ITO / HT-1(40nm) / green light host material(35nm): PGD-1[10%] / ETL-1(25nm) / LiF(0.5nm) / Al(150nm).

[0115] The preparation process of the organic electroluminescent device is as follows:

[0116] The preparation method of the green light organic electroluminescent device is as follows:

[0117] Place the materials in a vacuum chamber, evacuate to 1×10 -5 ~1×10 -6 Pa, and vacuum deposit them onto the cleaned ITO substrate in sequence to prepare an OLED device.

[0118] Among them, PGD-1 [10%] refers to the doping ratio of the dye, that is, the volume ratio of the host material to the dye PGD-1 is 90:10; HT-1 is a hole transport material, and ETL-1 is an electron transport material.

[0119] The green host material of the green organic electroluminescent device provided in this application example is compound P1.

[0120] Device Examples 2-6, Device Comparative Examples 1-3

[0121] Device Examples 2-6 and Device Comparative Examples 1-3 respectively provide an organic electroluminescent device, which is only different from Device Example 1 in that the green host material is different (see Table 3 below), and other preparation steps and conditions are the same as those in Device Example 1.

[0122] Performance test:

[0123] The brightness, driving voltage, current efficiency of the prepared organic electroluminescent device were measured, and the lifetime test LT90 was also carried out. Among them, the lifetime test LT90 refers to the time required for the brightness to decrease to 90% of the initial brightness at room temperature (25-27 °C) while keeping the current density at the initial brightness unchanged (here it is the current density at 1000 cd / m 2 . The driving voltage, current efficiency, and LT90 lifetime are all relative values. The test results are shown in Table 3 below.

[0124] Table 3

[0125]

[0126]

[0127] Among them, " / " means that this data is not available.

[0128] Generally, when a specific compound is used as a green host material, replacing the H atoms in the specific compound with D atoms can improve the device lifetime. However, when the H atoms at different positions of the specific compound are replaced with D atoms, the resulting different compounds will have different performances.

[0129] Comparing Device Example 1 and Device Comparative Example 3, it can be analyzed that the middle benzene ring in the indolocarbazole group of the indolocarbazole-based deuterated compound provided by the present invention is affected by the conjugation of the two benzene rings on the left and right, and there are two N atoms connected to the middle benzene ring in the indolocarbazole group, making the electron cloud density of the middle benzene ring larger. If two H atoms are connected to the middle benzene ring, the bond is more likely to break, which affects the device lifetime.

[0130] The applicant has found that by designing the structure of the indolocarbazole-based deuterated compound, only two hydrogen atoms of the middle benzene ring in the indolocarbazole group are replaced with deuterium atoms, and the improvement in lifetime is the same as or better than that when all hydrogen atoms in the indolocarbazole group are replaced with deuterium atoms.

[0131] Meanwhile, in compound D3 used in device comparative example 3, all H atoms in the indolocarbazole group are replaced by deuterium atoms, which affects the electron cloud distribution on the indolocarbazole group and also has an adverse effect on the film-forming property of the material. As a result, compared with the OLED device prepared using compound P1 provided by the present invention, the voltage and efficiency of the OLED device prepared using compound D3 become worse.

[0132] Device example 7, device comparative example 4

[0133] Device example 7 and device comparative example 4 respectively provide an organic electroluminescent device, which is different from device example 1 only in that the green light host material is different (see Table 4 below), and other preparation steps and conditions are the same as those in device example 1.

[0134] Performance test:

[0135] The brightness, driving voltage, current efficiency of the prepared organic electroluminescent device were measured, and the lifetime test LT90 was also carried out. Among them, the lifetime test LT90 refers to the time required for the brightness to decrease to 90% of the initial brightness at room temperature (25 - 27 °C) while keeping the current density at the initial brightness unchanged (here it is the current density at 1000 cd / m 2 . The driving voltage, current efficiency, and LT90 lifetime are all relative values. The test results are shown in Table 4 below.

[0136] Table 4

[0137] Green light host material <![CDATA[Required luminance / (cd / m 2 )]]> Driving voltage Current efficiency LT90 lifetime Device Example 7 P5 1000 0.96 1.05 1.66 Device Comparative Example 4 D4 1000 1 1 1

[0138] As can be seen from the above, in the present invention, by designing the structure of the indolocarbazole-based deuterated compound, the indolocarbazole-based deuterated compound is used as the host material of the light-emitting layer of the OLED device, and the prepared OLED device has a lower driving voltage, a higher current efficiency, and a longer lifetime.

[0139] 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 replacement of each raw material of the product of the present invention, the addition of auxiliary components, and the selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An indolecarbazole deuterated compound, characterized in that: The indolecarbazole deuterated compound has a structure shown in the following formula I: Ar 12 Any one selected from C6-C40 aryl and C6-C30 heteroaryl; m is selected from an integer between 0 and 5, and n is selected from an integer between 0 and 4; Ar 12 The hydrogen atoms in the alkyl group may be independently substituted by at least one of -D, -F, -CN, a C6-C20 aryl group, a triphenylmethyl group, a triphenylsilyl group, a C1-C12 alkyl group or a C1-C12 alkoxy group.

2. The indolecarbazole deuterated compound according to claim 1, characterized in that: 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, triphenylmethane, triphenylsilyl or benzonaphthofluorenyl; Preferably, the C6-C30 heteroaryl group is selected from any one or a combination of at least two of carbazolyl, dibenzothiophenyl, dibenzofuranyl, naphthobenzofuranyl, naphthobenzothiophenyl, dinaphthofuranyl and dinaphthothiophenyl; Preferably, the C6-C20 aryl group is selected from any one of phenyl, naphthyl, biphenyl, anthracenyl, phenanthryl, fluorenyl, triphenylene or fluoranthenyl; Preferably, the C1-C12 alkyl group is selected from any one of methyl, ethyl, propyl, n-butyl, tert-butyl, cyclopentyl, cyclohexyl, octyl and adamantyl; Preferably, the C1-C12 alkoxy group is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy and octyloxy.

3. The indolecarbazole deuterated compound according to claim 1 or 2, characterized in that: The Ar 12 At least one selected from phenyl, biphenyl, terphenyl, naphthyl, triphenylene, fluoranthene, anthracene, phenanthryl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl or dibenzothiophenyl; Preferably, the Ar 12 Any one selected from phenyl, biphenyl, terphenyl or naphthyl.

4. The indolecarbazole deuterated compound according to any one of claims 1 to 3, characterized in that: The Ar 12 The hydrogen atoms in the group may be independently substituted by at least one of -D, -F, -CN, phenyl, naphthyl, methyl, ethyl, propyl, tert-butyl, methoxy, ethoxy, propoxy, triphenylmethyl, triphenylsilyl, and carbazolyl.

5. The deuterated indolecarbazole compound according to any one of claims 1 to 4, characterized in that: The indolecarbazole deuterated compound is selected from any one of the following substituted or unsubstituted compounds: The substitution refers to the Ar in the above-mentioned indole carbazole deuterated compound. 12 The hydrogen atoms at the corresponding positions of the groups can each independently be replaced by a deuterium atom.

6. An intermediate, characterized in that The intermediate has a structure shown in the following formula MA: Among them, Ar 12 has the same definition as in claim 1; Ar 12 The hydrogen atoms in the may be independently substituted by at least one of -D, -F, -CN, C6-C20 aryl, triphenylmethyl, triphenylsilyl, C1-C12 alkyl or C1-C12 alkoxy; The intermediates do not include the following compounds: The intermediate is used to prepare the indolecarbazole deuterated compound as claimed in any one of claims 1 to 5.

7. The intermediate according to claim 6, characterized in that The intermediates include the following compounds:

8. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises an anode, a cathode and an organic thin film layer arranged between the anode and the cathode; The material of the organic thin film layer includes the deuterated indolecarbazole compound according to any one of claims 1 to 5.

9. The organic electroluminescent device according to claim 8, characterized in that: The organic thin film layer includes a light-emitting layer; The host material of the light-emitting layer includes the indolecarbazole deuterated compound according to any one of claims 1 to 5.

10. The organic electroluminescent device according to claim 8 or 9, characterized in that: The organic electroluminescent device is a green organic electroluminescent device.

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