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 invention belongs to the technical field of organic electroluminescent materials, and in particular relates to an indolecarbazole deuterated compound, an intermediate and an organic electroluminescent device. Background Art

[0002] Displays integrate electronics, communications and information processing technologies, and are considered another major development opportunity for the electronics industry after electronics and computers. Display technology and displays occupy a very important position in the development of information technology. Displays on televisions, computers, telephones and various instruments provide a large amount of information for people's daily lives and work. In recent years, new display technologies have become the focus of research, among which flat-panel displays have the advantages of light weight, low power consumption and easy portability, and have become a research hotspot.

[0003] Among the various flat panel displays currently available, liquid crystal displays (LCDs) play an important role. However, liquid crystal displays (LCDs) have many shortcomings: they do not emit light by themselves, but need to rely on light sources or ambient light, have viewing angle problems, have slow response speeds, and have 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 people's attention at the time. It was not until 1987 that the Tang research team of Kodak published a high-brightness, high-efficiency thin-film organic electroluminescent device (OLED) made of organic fluorescent materials and hole materials and driven by low DC voltage that the technology regained attention and opened up a new research field.

[0004] OLED has outstanding advantages, such as low power consumption, fast response speed, easy bending, wide viewing angle, large area display, full luminous colors, etc. It 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, OLED, as a new display technology, has made great progress and has been widely used in the fields of flat panel displays, flexible displays, solid-state lighting and vehicle displays.

[0005] Therefore, developing more types of OLED materials with better performance to meet the needs of their use in high-performance OLED devices is a research focus in this field. Summary of the invention

[0006] In view of the shortcomings of the prior art, the present invention aims to provide an indolecarbazole deuterated compound, an intermediate and an organic electroluminescent device. In the present invention, the structure of the indolecarbazole deuterated compound is designed, so that the indolecarbazole deuterated compound is used as the main 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 life.

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

[0008] In a first aspect, the present invention provides an indolecarbazole deuterated compound, wherein the indolecarbazole deuterated compound has a structure as shown in the following formula I:

[0009]

[0010] Among them, Ar 11 Selected from biphenyl or carbazolyl;

[0011] Ar 12 Selected from C8-C40 aryl or carbazole;

[0012] Ar 11 ,Ar 12 The hydrogen atoms in can be replaced by deuterium atoms (D) independently;

[0013] The hydrogen atoms in the compound of formula I may be independently substituted by at least one of -F, -CN, C6-C20 aryl, C6-C30 heteroaryl, triphenylmethyl, triphenylsilyl, C1-C12 alkyl or C1-C12 alkoxy.

[0014] In the present invention, the structure of the deuterated indolecarbazole compound is designed so that the deuterated indolecarbazole compound is used as the main 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.

[0015] In the present invention, C6-C40 can be C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.

[0016] C6-C30 can be C6, C8, C10, C12, C16, C20, C24, C28 or C30, etc.

[0017] C6-C20 can be C6, C8, C10, C12, C16 or C20, etc.

[0018] C1-C12 can be C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11 or C12.

[0019] It should be noted that, in the present invention, "D" represents a deuterium atom, and unless otherwise indicated in the present invention, H and hydrogen therein all represent "protium", and the same shall apply hereinafter.

[0020] 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.

[0021] As a preferred technical solution of the present invention, the C8-C40 aromatic group is selected from any one or a combination of at least two of biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthanofluorenyl, pyrene, peryl, spirofluorenyl, triphenylene, fluoranthenyl, hydrogenated benzanthryl, indenofluorenyl, benzoindenofluorenyl, dibenzoindenofluorenyl, naphthanofluorenyl, triphenylmethane, triphenylsilanyl or benzonaphthofluorenyl.

[0022] As a preferred technical solution of the present invention, the C6-C30 heteroaryl group is selected from any one of carbazolyl, dibenzothiophenyl, dibenzofuranyl, naphthiobenzofuranyl, naphthiobenzothiophenyl, dinaphthofuranyl, and dinaphthothiophenyl, or a combination of at least two thereof.

[0023] Preferably, the C6-C20 aryl group is selected from any one of phenyl, naphthyl, biphenyl, anthracenyl, phenanthryl, fluorenyl, triphenylene or fluoranthene.

[0024] Preferably, the C1-C12 alkyl group is selected from any one of methyl, ethyl, propyl, n-butyl, tert-butyl, cyclopentyl, cyclohexyl, octyl and adamantyl.

[0025] Preferably, the C1-C12 alkoxy group is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy and octyloxy.

[0026] As a preferred technical solution of the present invention, the Ar 12 At least one selected from the group consisting of biphenyl, terphenyl, naphthyl, triphenylene, fluoranthene, anthracene, phenanthryl, 9,9-dimethylfluorenyl and carbazolyl.

[0027] Preferably, the Ar 12 Any one selected from biphenyl, terphenyl or naphthyl.

[0028] Preferably, the Ar 11 Selected from p-biphenyl groups.

[0029] Preferably, the Ar 11 Selected from meta-biphenyl groups.

[0030] Preferably, the Ar 11 Selected from carbazolyl.

[0031] Preferably, the hydrogen atoms in the compound of formula I can be independently substituted by at least one of -F, -CN, phenyl, naphthyl, methyl, ethyl, propyl, tert-butyl, methoxy, ethoxy, propoxy, triphenylmethyl, triphenylsilyl, and carbazolyl.

[0032] As a preferred technical solution of the present invention, the indolecarbazole deuterated compound is selected from any one of the following substituted or unsubstituted compounds:

[0033]

[0034]

[0035] The substitution refers to the Ar in the above-mentioned indole carbazole deuterated compound. 11 ,Ar 12 The hydrogen atoms at the corresponding positions in the groups can each independently be replaced by a deuterium atom.

[0036] like in Ar 11 The group at the corresponding position is p-biphenyl, Ar 11 When all hydrogen atoms in the corresponding position groups are replaced by deuterium atoms, we get Ar 12 The group at the corresponding position is biphenyl, Ar 12 When all hydrogen atoms in the corresponding position groups are replaced by deuterium atoms, we get

[0037] Preferably, the indolecarbazole deuterated compound includes the following compounds:

[0038]

[0039] It should be noted that the present invention does not impose any special limitation on the preparation method of the deuterated indolecarbazole compounds, and all commonly used preparation methods in the art are applicable.

[0040] The synthesis method of the deuterated indolecarbazole compound provided by the present invention includes the following steps:

[0041]

[0042] Among them, X 1 , X 2 Each independently selected from any one of -F, -Cl, -Br or -I;

[0043] Ar 11 ,Ar 12Has the same definition as above.

[0044] In a second aspect, the present invention provides an intermediate having a structure as shown in the following formula MA:

[0045]

[0046] Among them, Ar 12 has the same definition as above;

[0047] The hydrogen atoms in the formula MA may be independently substituted by at least one of -F, -CN, C6-C20 aryl, C6-C30 heteroaryl, triphenylmethyl, triphenylsilyl, C1-C12 alkyl or C1-C12 alkoxy;

[0048] Ar 12 The hydrogen atoms in can be replaced by deuterium atoms;

[0049] The intermediates do not include the following compounds:

[0050]

[0051] The intermediate is used to prepare the indolecarbazole deuterated compound as described in the first aspect.

[0052] As a preferred technical solution of the present invention, the intermediate includes the following compounds:

[0053]

[0054] In a third aspect, the present invention provides an organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode and an organic thin film layer disposed between the anode and the cathode;

[0055] The material of the organic thin film layer includes the deuterated indolecarbazole compound as described in the first aspect.

[0056] Preferably, the organic thin film layer includes a light-emitting layer;

[0057] The host material of the light-emitting layer includes the indolecarbazole deuterated compound described in the first aspect.

[0058] As a preferred technical solution of the present invention, the organic electroluminescent device is a green organic electroluminescent device.

[0059] The luminescent layer in the present invention includes a luminescent layer main material and a doping material, wherein the doping material is also called a dye or a phosphorescent luminescent material. The luminescent layer main material can be a single compound or a mixture of two or more compounds.

[0060] Preferably, the light-emitting layer comprises a phosphorescent light-emitting layer, and the phosphorescent light-emitting layer comprises a green phosphorescent light-emitting layer, a red phosphorescent light-emitting layer, and a blue phosphorescent light-emitting layer.

[0061] The volume percentage of the main material in the phosphorescent 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 more preferably 85% to 95%.

[0062] In the present invention, the doping material of the light-emitting layer may be a phosphorescent material, which is also called a triplet light-emitting material, and refers to the light emitted from a triplet excited state. The specific selection of the phosphorescent material in the present invention is not particularly limited, and the doping materials of the light-emitting layer commonly used in the art are applicable, including but not limited to: a compound having a structure shown in Formula PD:

[0063]

[0064] Wherein, M is selected from any one of Ir, Pt, Pd, Os, Ti, Zr, Hf, Eu, Tb, Tm, Cu or Au;

[0065] Y 1 -Y 4 are each independently selected from carbon or nitrogen;

[0066] Y 1 and Y 2 They can be connected by single or double bonds. 3 and Y 4 They can be connected by single or double bonds;

[0067] Cy 1 and Cy 2 are each independently selected from any one of phenyl, naphthyl, fluorenyl, spirofluorenyl, indenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothienyl, benzimidazolyl, benzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, N-heterocarbazolyl, N-heterodibenzofuranyl, wherein Cy is 1 and Cy 2 may optionally be linked to each other via a single bond or an organic linking group;

[0068] Any two ligands of M, or more than two ligands, may be connected by a single bond or a double bond, or may be bridged by O or S, or may be connected by any chemical group or chemical structure to form a structural form that conforms to chemical principles;

[0069] R 91 and R 92 Each is independently selected from -H, -D, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid, carboxylate, sulfonic acid, sulfonate, phosphoric acid, phosphate, -SF 5 , substituted or unsubstituted C1-C60 (for example, C1, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkyl, substituted or unsubstituted C2-C60 (for example, C2, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkenyl, substituted or unsubstituted C2-C60 (e.g., C2, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55, or C60, etc.) alkynyl, substituted or unsubstituted C1-C60 (e.g., C1, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55, or C60, etc.) alkoxy, substituted or unsubstituted C2-C10 (for example, C2, C3, C4, C5, C6, C7, C8, C9 or C10) heterocycloalkyl, substituted or unsubstituted C6-C60 (for example, C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60, etc.) aryl, substituted or unsubstituted C6-C60 (for example, C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60, etc.) any one of a C24, C30, C32, C36, C40, C42, C54 or C60 (e.g., C24, C30, C32, C36, C40, C42, C54 or C60, etc.) aryloxy group, a substituted or unsubstituted C6-C60 (e.g., C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60, etc.) arylthio group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.

[0070] a 1 and a 2 Each is independently an integer selected from 1-5, for example, 1, 2, 3, 4 or 5; b is an integer selected from 0-4, for example, 0, 1, 2, 3 or 4;

[0071] a is selected from 1, 2 or 3;

[0072] L1 It is a monovalent organic ligand, a divalent organic ligand or a trivalent organic ligand.

[0073] Preferably, the compound of formula PD is selected from any one of the following compounds:

[0074]

[0075]

[0076]

[0077]

[0078] In a fourth aspect, the present invention provides a display device, comprising the organic electroluminescent device as described in the third aspect.

[0079] Compared with the prior art, the present invention has the following beneficial effects:

[0080] In the present invention, the structure of the deuterated indolecarbazole compound is designed so that the deuterated indolecarbazole compound is used as the main 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. DETAILED DESCRIPTION

[0081] 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.

[0082] Preparation Example 1 Synthesis of Intermediate M1

[0083] This preparation example provides an intermediate MA and a synthesis method thereof, and the synthesis method is as follows:

[0084]

[0085] (1) Synthesis of intermediate M5-1

[0086] Under nitrogen, add 60 mL of toluene, 30 mL of ethanol, and 10 mL of water into a three-necked flask, then add 1.2 g of deuterated o-dibromobenzene, 1.8 g of o-nitrobenzene boric acid, 2.12 g of sodium carbonate, and 0.46 g of tetrakistriphenylphosphine palladium. Slowly raise the temperature to reflux for 10 hours, cool to room temperature, add water to separate, wash the organic layer with water, dry it with magnesium sulfate, remove the desiccant, and concentrate to dryness. Crystallize it with a mixed solvent of toluene and methanol to obtain intermediate M5-1 (0.56 g).

[0087] The obtained intermediate M5-1 was subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) was measured to be 324.10.

[0088] (2) Synthesis of intermediate M5-2

[0089] Under nitrogen, add 0.5 g of intermediate M5-1, 4 g of triethyl phosphite and 20 mL of o-dichlorobenzene to a three-necked flask, heat to reflux for 24 hours, cool, add 20 mL of 5% sodium carbonate solution, stir for 2 hours, separate the liquids, concentrate the organic layer to dryness under reduced pressure, separate by silica gel column chromatography, and elute with petroleum ether to obtain intermediate M5-2 (0.16 g).

[0090] The obtained intermediate M5-2 was subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) was measured to be 258.11.

[0091] (3) Synthesis of intermediate M1

[0092] Under nitrogen protection, dry toluene (70 mL), compound M5-2 (2.6 g), 2'-bromo-1,1':3',1"-terphenyl (3.1 g), Pd(dba) were added to a three-necked flask. 2 (bis(dibenzylideneacetonepalladium, 0.0575g), 10% tri-tert-butylphosphine toluene solution (the mass of tri-tert-butylphosphine solution is 0.4g, and the amount of tri-tert-butylphosphine is 0.0002mol) and sodium tert-butoxide (1.44g), heated to reflux, reacted for 8h, cooled to room temperature, added water to separate, and then the organic layer was washed with water until neutral, dried with magnesium sulfate, filtered to remove magnesium sulfate, concentrated to dryness, separated by silica gel column chromatography, eluted with a solvent of petroleum ether: ethyl acetate = 20:1 (volume ratio), to obtain intermediate M1 (2.2g).

[0093] The intermediate M1 was subjected to mass spectrometry detection: the mass-to-charge ratio (m / z) was measured to be 486.21.

[0094] Preparation Example 2-9

[0095] Preparation Examples 2-9 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 compounds (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.

[0096] Table 1

[0097]

[0098]

[0099]

[0100] Synthesis Example 1

[0101] This synthesis example provides compound P1 and its synthesis method, and its synthesis method is as follows:

[0102]

[0103] Under nitrogen protection, dry toluene (110 mL), intermediate M1 (4.9 g), 4-bromobiphenyl (2.3 g), Pd (dba) were added to a three-necked flask. 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), heat to reflux reaction for 6 hours, cool to room temperature, add water to separate, then wash the organic layer with water until neutral, dry with magnesium sulfate, filter to remove magnesium sulfate, concentrate to dryness, separate by silica gel column chromatography, elute with petroleum ether to obtain compound P1 (5.1 g).

[0104] The mass spectrometry detection of compound P1: the mass-to-charge ratio (m / z) was measured to be 638.27.

[0105] Synthesis Example 2-9

[0106] 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.

[0107] Table 2

[0108]

[0109]

[0110] 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.

[0111] The specific structures of the compounds used in the following device examples and device comparative examples are as follows:

[0112]

[0113]

[0114] Wherein, the synthesis method of compound D4 is as follows:

[0115]

[0116] Compound D4 was synthesized by referring to the synthesis method of compound P1.

[0117] The obtained compound D4 was subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) was measured to be 646.32.

[0118] Device Example 1

[0119] The device embodiment provides an organic electroluminescent device, and the compound provided by the present invention is selected as a green light host material in the organic electroluminescent device.

[0120] 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).

[0121] The preparation process of organic electroluminescent device is as follows:

[0122] The preparation method of the green organic electroluminescent device is as follows:

[0123] The material was placed in a vacuum chamber and evacuated to 1×10 -5 ~1×10 -6 Pa was vacuum evaporated onto the cleaned ITO substrate in sequence to prepare an OLED device.

[0124] PGD-1[10%] refers to the doping ratio of the dye, that is, the volume ratio of the main material to the dye PGD-1 is 90:10; HT-1 is a hole transport material, and ETL-1 is an electron transport material.

[0125] The green light host material of the green light organic electroluminescent device provided in this application example is compound P1.

[0126] Device Examples 2-6, Device Comparative Example 1

[0127] Device Examples 2-6 and Device Comparative Example 1 respectively provide an organic electroluminescent device, which differs from Device Example 1 only in that the green light host material is different (see Table 3 below for details), and the other preparation steps and conditions are the same as those of Device Example 1.

[0128] Performance Testing:

[0129] The test measured the brightness, driving voltage, current efficiency, and life test LT90 of the prepared organic electroluminescent device. Among them, the life test LT90 refers to the current density at room temperature (25-27°C) at the initial brightness (here 1000cd / m 2The time required for the brightness to decrease to 90% of the initial brightness is calculated based on the current density at the time of the test. The driving voltage, current efficiency, and LT90 life are all relative values. The test results are detailed in Table 3 below.

[0130] Table 3

[0131] Green light main material <![CDATA[Required brightness / (cd / m 2 )]]> Driving voltage Current efficiency LT90 Life Device Example 1 P1 1000 0.97 1.04 1.02 Device Example 2 P2 1000 0.90 0.99 1.07 Device Example 3 P6 1000 0.89 1.23 1.02 Device Example 4 P7 1000 1.02 1.31 1.01 Device Example 5 P8 1000 0.76 1.02 0.98 Device Example 6 P9 1000 0.92 1.11 1.05 Device Comparison Example 1 D4 1000 1 1 1

[0132] Generally, when a specific compound is used as a green light host material, the device life will be improved by replacing the H atoms in the specific compound with D atoms. However, when H atoms at different positions of the specific compound are replaced with D atoms, the performance of the obtained compounds will be different.

[0133] The benzene ring in the middle of the indolecarbazole group in the indolecarbazole deuterated compound provided by the present invention is affected by the conjugation of the two benzene rings on the left and right sides, and the benzene ring in the middle of the indolecarbazole group is connected to two N atoms, so that the electron cloud density of the middle benzene ring is larger. If the benzene ring in the middle is connected to two H atoms, the bond is easily broken, which affects the life of the device.

[0134] The present invention designs the structure of the indolecarbazole deuterated compound, and only replaces two hydrogen atoms in the middle benzene ring of the indolecarbazole group with deuterium atoms, and the life improvement is consistent with the effect of replacing all hydrogen atoms in the indolecarbazole group with deuterium atoms. Because the cost of materials will increase after the deuteration rate is increased, the indolecarbazole deuterated compound provided by the present invention uses a lower deuteration rate and obtains the same life improvement.

[0135] At the same time, in the compound D1 used in the device comparison example, all H atoms in the indolecarbazole group are replaced by deuterium atoms, which affects the electron cloud distribution on the indolecarbazole group and also has an adverse effect on the film-forming property of the material, resulting in that the voltage and efficiency of the OLED device prepared using the compound D1 are worse than those of the OLED device prepared using the compound P1 provided by the present invention.

[0136] Device Examples 7-9, Device Comparative Examples 2-4

[0137] Device Examples 7-9 and Device Comparative Examples 2-4 respectively provide an organic electroluminescent device, which differs from Device Example 1 only in that the green light host material is different (see Table 4 below for details), and the other preparation steps and conditions are the same as those of Device Example 1.

[0138] Performance Testing:

[0139] The test measured the brightness, driving voltage, current efficiency, and life test LT90 of the prepared organic electroluminescent device. Among them, the life test LT90 refers to the current density at room temperature (25-27°C) at the initial brightness (here 1000cd / m 2 The time required for the brightness to decrease to 90% of the initial brightness is calculated based on the current density at the time of the test. The driving voltage, current efficiency, and LT90 life are all relative values. The test results are detailed in Table 4 below.

[0140] Table 4

[0141] Green light main material <![CDATA[Required brightness / (cd / m 2 )]]> Driving voltage Current efficiency LT90 Life Device Example 7 P3 1000 0.94 1.09 1.15 Device Example 8 P4 1000 0.93 1.22 1.21 Device Example 9 P5 1000 0.87 1.12 1.78 Device Comparison Example 2 D1 1000 1 1 1 Device Comparison Example 3 D2 1000 0.98 1.04 0.89 Device Comparison Example 4 D3 1000 0.96 1.07 1.12

[0142] By comparing device examples 2-3 with device example 4, it can be seen that compound D3 in device example 4, in which two substituents (biphenyl and carbazole) on the indolecarbazole ring act synergistically, improves the device voltage, efficiency and life.

[0143] From the comparison between device example 7 and device comparative examples 2-3, it can be seen that in the present invention, by designing the structure of the indolecarbazole deuterated compound, the indolecarbazole deuterated compound is used as the main 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 life.

[0144] 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. An indolecarbazole deuterated compound, characterized in that: The indolecarbazole deuterated compound has a structure shown in the following formula I: Among them, Ar 11 Selected from biphenyl or carbazolyl; Ar 12 Selected from C8-C40 aryl or carbazole; Ar 11 ,Ar 12 The hydrogen atoms in can each be replaced by deuterium atoms independently; The hydrogen atoms in the compound of formula I may be independently substituted by at least one of -F, -CN, C6-C20 aryl, C6-C30 heteroaryl, triphenylmethyl, triphenylsilyl, C1-C12 alkyl or C1-C12 alkoxy.

2. The indolecarbazole deuterated compound according to claim 1, characterized in that: The C8-C40 aryl group is selected from any one or a combination of at least two of biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthofluorenyl, pyrenyl, peryl, spirofluorenyl, triphenylene, fluoranthenyl, hydrogenated benzanthryl, indenofluorenyl, benzoindenofluorenyl, dibenzoindenofluorenyl, naphthofluorenyl, 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 the group consisting of biphenyl, terphenyl, naphthyl, triphenylene, fluoranthene, anthracene, phenanthryl, 9,9-dimethylfluorenyl, and carbazole; The Ar 12 The hydrogen atoms in can each be replaced by deuterium atoms independently; Preferably, the Ar 12 Any one selected from biphenyl, terphenyl or naphthyl; The Ar 12 The hydrogen atoms in the ion can be replaced by deuterium atoms independently.

4. The indolecarbazole deuterated compound according to any one of claims 1 to 3, characterized in that: The Ar 11 Selected from p-biphenyl; The Ar 11 The hydrogen atoms in can each be replaced by deuterium atoms independently; Preferably, the Ar 11 Selected from meta-biphenyl; The Ar 11 The hydrogen atoms in can each be replaced by deuterium atoms independently; Preferably, the Ar 11 is selected from carbazolyl; The Ar 11 The hydrogen atoms in the ion can be replaced by deuterium atoms independently.

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

6. The indolecarbazole deuterated compound according to any one of claims 1 to 5, 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. 11 ,Ar 12 The hydrogen atoms at the corresponding positions of the groups can be replaced by deuterium atoms independently.

7. 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; The hydrogen atoms in the formula MA may be independently substituted by at least one of -F, -CN, C6-C20 aryl, C6-C30 heteroaryl, triphenylmethyl, triphenylsilyl, C1-C12 alkyl or C1-C12 alkoxy; Ar 12 The hydrogen atoms in can be replaced by deuterium atoms; 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 6.

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

9. 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 6.

10. The organic electroluminescent device according to claim 9, characterized in that: The organic thin film layer includes a light-emitting layer; The main material of the light-emitting layer comprises the deuterated indolecarbazole compound according to any one of claims 1 to 6; Preferably, the organic electroluminescent device is a green organic electroluminescent device.

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