Quinazoline compound, intermediate and organic electroluminescent device

Abstract

The invention provides a quinazoline compound, an intermediate and an organic electroluminescent device. The compound has a structure as shown in a formula I, a formula II, a formula III or a formula IV. The structure of the quinazoline compound is designed, so that the quinazoline compound is suitable for being used as a main body material of a luminescent layer of the organic electroluminescent device, and the organic electroluminescent 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 particularly relates to a quinazoline compound, an intermediate and an organic electroluminescent device. Background Art

[0002] The structure of an organic electroluminescent device specifically consists of an anode, a cathode, and an organic layer between them. To improve the efficiency and stability of organic electroluminescent elements, the organic material layer includes multiple layers made of different materials, such as a hole injection layer (HIL), a hole transport layer (HTL), a hole blocking layer, a light-emitting layer, an electron transport layer (ETL), and an electron injection layer (EIL). Currently, organic electroluminescence has become a mainstream display technology, and accordingly, various new OLED materials have also been developed.

[0003] In order to meet people's higher requirements for OLED devices, the field urgently needs to develop more types of materials to improve the performance of OLED devices in terms of current efficiency, lifespan, etc. Summary of the Invention

[0004] In view of the shortcomings of the prior art, the present invention provides a quinazoline compound, an intermediate, and an organic electroluminescent device. The present invention designs the structure of the quinazoline compound so that it is suitable as a host material for the light-emitting layer of the organic electroluminescent device, thereby enabling the organic electroluminescent device to have a lower driving voltage, higher current efficiency, and longer life.

[0005] To achieve this object, the present invention adopts the following technical solutions:

[0006] In a first aspect, the present invention provides a quinazoline compound having a structure shown in Formula I, Formula II, Formula III or Formula IV:

[0007]

[0008] Ar 11 Any one selected from a single bond, a C6-C30 arylene group or a C6-C20 heteroarylene group;

[0009] R 101 Any one selected from H, cyano (-CN), C1-C12 alkyl, C6-C30 aryl or C6-C20 heteroaryl;

[0010] R1, R2, and R3 are each independently selected from any one of H, C6-C40 aryl, C6-C30 heteroaryl, or C1-C12 alkyl;

[0011] The hydrogen atoms in the quinazoline compound can each independently be substituted by at least one of a deuterium atom (D), -CN, -F, a C6-C20 aryl group, a C6-C20 heteroaryl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a triphenylsilyl group or a triphenylmethyl group.

[0012] The present invention obtains a compound suitable for use as a main material of a light-emitting layer by designing the structure of a quinazoline compound. The organic electroluminescent device prepared thereby has a lower driving voltage, a higher current efficiency and a longer service life.

[0013] In the present invention, the C6-C40 can be selected from C6, C10, C12, C18, C24, C30, C36 or C40.

[0014] The C6-C30 can be selected from C6, C10, C12, C18, C24 or C30, etc.

[0015] The C6-C20 can be selected from C6, C10, C12, C18 or C20, etc.

[0016] The C1-C12 may be selected from C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11 or C12.

[0017] The C1-C6 may be selected from C1, C2, C3, C4, C5 or C6.

[0018] In the present invention, "D" represents a deuterium atom, and the same shall apply hereinafter.

[0019] 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.

[0020] As a preferred technical solution of the present invention, the C6-C30 arylene group is selected from phenylene, biphenylene, terphenylene, naphthylene, anthrylene, phenanthrenyl, fluorenylene, benzofluorenylene, dibenzofluorenylene, naphthofluorenylene, pyrenylene, perylene, spirofluorenylene, triphenylene, fluoranthenylene, hydrogenated benzanthrylene, naphthofluorenylene, tetraphenylmethane or any one or a combination of at least two of benzonaphthofluorenyl.

[0021] As a preferred technical solution of the present invention, the C6-C20 heteroaryl group is selected from any one of a carbazolyl group, a dibenzothiophenyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group or a carbazolyl group.

[0022] As a preferred technical solution of the present invention, the C6-C30 aryl group is selected from any one or a combination of at least two of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthacenyl, pyrenyl, peryl, spirofluorenyl, triphenylene, fluoranthenyl, hydrogenated benzoanthryl, indenofluorenyl, benzoindenofluorenyl, dibenzoindenofluorenyl, naphthacenyl, tetraphenylmethane or benzonaphthofluorenyl.

[0023] As a preferred technical solution of the present invention, the C6-C20 heteroaryl group is selected from any one of carbazolyl, dibenzothiophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, dinaphthofuranyl, dinaphthothiophenyl or carbazolyl.

[0024] 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, phenanthrenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthacenyl, pyrenyl, peryl, spirofluorenyl, triphenylene, fluoranthenyl, hydrogenated benzoanthryl, indenofluorenyl, benzoindenofluorenyl, dibenzoindenofluorenyl, naphthacenyl, tetraphenylmethane or benzonaphthofluorenyl.

[0025] As a preferred technical solution of the present invention, the C6-C30 heteroaryl group is selected from any one of carbazolyl, dibenzothiophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, dinaphthofuranyl, dinaphthothiophenyl or carbazolyl.

[0026] As a preferred technical solution of the present invention, the C1-C12 alkyl group is selected from any one of methyl, ethyl, propyl, n-butyl, tert-butyl, cyclopentyl, cyclohexyl, octyl and adamantyl.

[0027] As a preferred technical solution of the present invention, the C6-C20 aryl group is selected from any one of phenyl, naphthyl, biphenyl, anthracenyl, phenanthrenyl, fluorenyl, triphenylene or fluoranthenyl.

[0028] As a preferred technical solution of the present invention, the C6-C20 heteroaryl group is selected from any one of a carbazolyl group, a dibenzothiophenyl group, a dinaphthofuranyl group or a carbazolyl group.

[0029] As a preferred technical solution of the present invention, the C1-C6 alkyl group is selected from any one of methyl, ethyl, propyl, n-butyl, tert-butyl, cyclopentyl or cyclohexyl.

[0030] As a preferred technical solution of the present invention, the C1-C6 alkoxy group is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentyloxy or hexyloxy.

[0031] As a preferred technical solution of the present invention, the Ar 11Any one or a combination of at least two selected from the group consisting of a single bond, a phenylene group, a naphthylene group, a triphenylene group, a fluoranthenylene group, a fluorenylene group, an anthrylene group, a phenanthrenyl group, a biphenylene group, a dibenzofuranyl group, and a dibenzothiophenylene group.

[0032] Preferably, the Ar 11 Any one selected from a single bond, phenylene, naphthylene, triphenylene, fluoranthenylene, fluorenylene, anthracenylene, biphenylene, dibenzofuranylene, and dibenzothiophenylene.

[0033] Preferably, the Ar 11 Any one selected from a single bond, a phenylene group, a naphthylene group, a biphenylene group or a carbazolylene group.

[0034] As a preferred technical solution of the present invention, the R 101 Any one or a combination of at least two selected from H, cyano, phenyl, naphthyl, triphenylene, fluoranthenyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

[0035] Preferably, the R 101 Any one or a combination of at least two selected from phenyl, naphthyl, biphenyl, triphenylene, fluoranthene, anthracenyl, phenanthryl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, methyl, ethyl, propyl, propyl, butyl, pentyl, and hexyl.

[0036] Preferably, the R 101 Any one selected from the group consisting of methyl, ethyl, phenyl, naphthyl, biphenyl, benzofuranyl, dibenzothiophenyl, and carbazolyl.

[0037] As a preferred technical solution of the present invention, R1, R2, and R3 are each independently selected from H, methyl, ethyl, propyl, butyl, pentyl, hexyl, H atom, cyano, phenyl, naphthyl, triphenylene, fluoranthene, fluorenyl, anthracene, phenanthrenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, or any one or a combination of at least two of carbazolyl.

[0038] As a preferred technical solution of the present invention, R1, R2, and R3 are each independently selected from any one of H, tert-butyl, phenyl, naphthyl, or carbazolyl.

[0039] Preferably, the hydrogen atoms in the quinazoline compound can be independently substituted by at least one of a deuterium atom, -CN, -F, phenyl, phenyl, naphthyl, triphenylene, fluoranthene, fluorenyl, anthracene, phenanthrenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, triphenylsilyl, and triphenylmethyl.

[0040] Preferably, the hydrogen atoms in the quinazoline compound can each independently be substituted by at least one of a deuterium atom, -CN, -F, a methyl group, an ethyl group, a tert-butyl group, a methoxy group, a phenyl group or a naphthyl group.

[0041] As a preferred technical solution of the present invention, the quinazoline compound is selected from any one of the following compounds:

[0042]

[0043]

[0044] The substitution means that the hydrogen atoms in the above quinazoline compounds can be independently replaced by deuterium atoms.

[0045] Preferably, the quinazoline compound is selected from any one of the following compounds:

[0046]

[0047] It should be noted that the present invention does not have any special restrictions on the preparation method of the above-mentioned triphenylene compounds, and the preparation methods commonly used in the art are applicable. The preparation method of the compound of formula I provided by the present invention is illustrated by way of example:

[0048]

[0049] Wherein, X and Y are each independently selected from any one of fluorine, chlorine, bromine and iodine;

[0050] Ar 11 , R1, R2, R 101 Has the same definition as above.

[0051] The preparation method of the compound of formula II provided by the present invention is illustrated as follows:

[0052]

[0053] Wherein, X and Y are each independently selected from any one of fluorine, chlorine, bromine and iodine;

[0054] Ar 11 , R1, R2, R 101 Has the same definition as above.

[0055] In a second aspect, the present invention provides an intermediate, comprising a compound having a structure represented by the following formula M1 or M2:

[0056]

[0057] Wherein, X is selected from any one of fluorine, chlorine, bromine and iodine;

[0058] Ar 11 、R 101 Has the same definition as above;

[0059] The intermediate is used to prepare the quinazoline compound as described in the first aspect.

[0060] Preferably, the intermediate includes the following compounds:

[0061]

[0062] In a third aspect, the present invention provides an organic electroluminescent device, comprising an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode;

[0063] The organic thin film layer material includes the quinazoline compound as described in the first aspect.

[0064] As a preferred technical solution of the present invention, the organic thin film layer includes a light-emitting layer, and the main material of the light-emitting layer includes the quinazoline compound as described in the first aspect.

[0065] Preferably, the light-emitting layer is a phosphorescent light-emitting layer.

[0066] Preferably, the light-emitting layer is a red phosphorescent light-emitting layer.

[0067] In the present invention, the structure of the quinazoline compound is designed to make it suitable as the main material of the light-emitting layer of the organic electroluminescent device, so that the organic electroluminescent device has a lower driving voltage, higher current efficiency and longer life. DETAILED DESCRIPTION

[0068] For the convenience of understanding the present invention, the present invention is given below with examples. It should be understood by those skilled in the art that the examples are only for the purpose of helping to understand the present invention and should not be regarded as specific limitations of the present invention.

[0069] Synthesis Example 1

[0070] This synthesis example provides compound P1, and its synthesis method is as follows:

[0071]

[0072] (1) Synthesis of intermediate P1-1

[0073] Under nitrogen protection, 60 mL of dioxane was added to a 250 mL three-necked flask in sequence, followed by 2.4 g of compound M1-0, 3.9 g of compound M1-1, 2.12 g (0.02 mol) of sodium carbonate and 0.23 g (0.0002 mol) of tetrakistriphenylphosphine palladium. The temperature was slowly raised to 40 ° C. for reaction for 2 hours, then raised to 60 ° C. for reaction for 4 hours, then raised to reflux for reaction for 2 hours, cooled to room temperature, added with water and dichloromethane for separation, the organic layer was washed with water, dried with magnesium sulfate, the desiccant was removed, concentrated to dryness, and crystallized from toluene to obtain 2.9 g of intermediate P1-1.

[0074] The obtained intermediate P1-1 was subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) was measured to be 466.12.

[0075] (2) Synthesis of compound P1

[0076] Under a nitrogen atmosphere, 100 mL of dry xylene, 4.7 g of intermediate P1-1, 1.9 g of carbazole, Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 g), a 10% mass percentage of tri-tert-butylphosphine toluene solution (the mass of tri-tert-butylphosphine solution is 0.8 g) and 1.2 g of sodium tert-butoxide were added to a 250 mL three-necked flask, heated to reflux temperature, reacted for 8 h, cooled to room temperature, and separated by adding water. The organic layer was then washed with water until neutral, dried over magnesium sulfate, filtered to remove magnesium sulfate, concentrated to dryness, and crystallized from a mixed solvent of toluene and ethanol to obtain 4.9 g of compound P1.

[0077] Compound P1 was detected by mass spectrometry: the mass-to-charge ratio (m / z) was measured to be 597.22.

[0078] Synthesis Examples 2-8

[0079] Synthesis Examples 2-8 respectively provide a compound. The specific structure of the compound is shown in Table 1 below. The synthesis method of the compound refers to the synthesis method in Synthesis Example 1. The intermediate is first synthesized using raw material 1 (chloride or bromide) and M1-1, and the mass spectrum of the intermediate is measured. The mass-to-charge ratio (m / z) is recorded. The intermediate is then reacted with raw material 2 to prepare the compound, and the obtained compound is subjected to mass spectrometry detection. The measured mass-to-charge ratio (m / z) is shown in Table 1 below.

[0080] Table 1

[0081]

[0082]

[0083] Synthesis Example 8

[0084] This synthesis example provides compound P12, and its synthesis method is as follows:

[0085]

[0086] Under a nitrogen atmosphere, 5.5 g of P9-1 intermediate, 3.0 g of N-phenylcarbazole-3-boric acid, 200 mL of DMF, 2.2 g of triethylamine, 0.1 g of bis(1,5-cyclooctadiene)nickel(0), and 0.18 g of triphenylphosphine were added to a 500 mL three-necked flask, and the temperature was raised to 65°C for reaction for 4 hours. Water and ethyl acetate were added for separation, and the organic layer was washed with water until neutral, dried over anhydrous magnesium sulfate, filtered to remove the desiccant, and concentrated to dryness. The mixture was separated by silica gel column chromatography with petroleum ether:ethyl acetate = 10:1 (volume ratio) to obtain 5.8 g of compound P12.

[0087] The obtained compound P12 was detected by mass spectrometry, and the m / z was 749.28.

[0088] Synthesis Example 9

[0089] This synthesis example provides compound P14, the synthesis method of which is as follows:

[0090]

[0091] Referring to the synthesis method of compound P12 in Synthesis Example 9, only the corresponding raw materials were changed to obtain compound P14.

[0092] The obtained compound P14 was detected by mass spectrometry, and the m / z was 673.25.

[0093] Other compounds for which the specific synthesis methods are not listed can be synthesized by referring to the above examples in combination with common knowledge in the art.

[0094] The present invention also provides compound D2, the synthesis method of which is as follows:

[0095]

[0096] Compound D2 was synthesized by referring to the synthesis method of compound P1 in Synthesis Example 1.

[0097] Compound D2 was detected by mass spectrometry: the mass-to-charge ratio (m / z) was measured to be 597.22.

[0098] The present invention also provides compound D3, the synthesis method of which is as follows:

[0099]

[0100] Compound D3 was synthesized by referring to the synthesis method of compound P1 in Synthesis Example 1.

[0101] The mass spectrometry of compound D3 was performed: the mass-to-charge ratio (m / z) was 762.28

[0102] The specific structures of some of the compounds used in the following application examples and comparative application examples of the present invention are as follows:

[0103]

[0104] Application Example 1

[0105] This application example provides a red organic electroluminescent device, using the compound provided by the present invention as a main material of the light-emitting layer. The structure of the red organic electroluminescent device is:

[0106] ITO / HT-1: HI-2[5%](80nm) / HT-1(30nm) / EB-1(20nm) / host material: PRD-1[5%](35nm) / ETL-1(25nm) / LiF(0.5nm) / Al(150nm).

[0107] The preparation method of the red organic electroluminescent device is as follows:

[0108] 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 to prepare OLED devices.

[0109] PRD-1[5%] refers to the dye doping ratio, meaning the volume ratio of the host material to the dye PRD-1 is 95:5. HT-1:HI-2[5%] refers to the p-type dopant ratio, meaning the volume ratio of the hole-transporting material HT-1 to the p-type dopant HI-2 is 95:5. HT-1 is a hole-transporting material; HT-1:HI-2[5%] serves as the hole-injection layer, and EB-1 is the electron-blocking layer.

[0110] The main material of the light-emitting layer of the red organic electroluminescent device provided in this application example is compound P1.

[0111] Application Example 2-16, Comparative Application Example 1-4

[0112] Application Examples 2-16 and Comparative Application Examples 1-4 respectively provide a red organic electroluminescent device, which differs from Application Example 1 only in that the main material of the light-emitting layer is replaced with other compounds (see Table 2 below for details). Other preparation steps and conditions are the same as those of Application Example 1.

[0113] Performance Testing

[0114] The brightness, driving voltage, current efficiency and LT95 of the organic electroluminescent device provided above were tested, wherein the current efficiency is the brightness of 1000cd / m 2 The corresponding value, LT95, refers to maintaining the initial current density of the device at 10mA / cm 2 The time required for the device efficiency to drop to 95% of the efficiency corresponding to the initial current density remains unchanged. The driving voltage, current efficiency and LT95 are relative values. The specific test results are shown in Table 2 below:

[0115] Table 2

[0116]

[0117]

[0118] It can be seen from Application Examples 4-6 and Application Example 14 that R 101 When the carbazole group is included, the compound is used as the main material of the OLED device, and the OLED device prepared has high current efficiency.

[0119] As can be seen from Application Examples 9-10, Ar in the compounds of Formula I to Formula IV 11 When it is not a single bond, the compound is used as the main material of an OLED device, and the OLED device prepared has a longer life.

[0120] It can be seen from Application Examples 8 and 12 that when one of R1 and R2 in the compound of Formula I or Formula II is H and the other is a carbazole group, the OLED device prepared using this compound as the main material of the OLED device has a lower driving voltage.

[0121] It can be seen from Application Examples 1-16 and Comparative Application Examples 1-3 that the present invention designs the structure of quinazoline compounds to make them suitable as the main material of the light-emitting layer of organic electroluminescent devices, so that the organic electroluminescent devices have lower driving voltage, higher current efficiency and longer life.

[0122] In summary, the present invention designs the structure of quinazoline compounds to make them suitable as the host material of the light-emitting layer of an organic electroluminescent device, so that the organic electroluminescent device has better comprehensive performance.

[0123] The applicant declares that the present invention uses the above-described embodiments to illustrate the detailed process flow of the present invention, but the present invention is not limited to the above-described detailed process flow, that is, it does not mean that the present invention must rely on the above-described detailed process flow to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent replacements for various raw materials in the products of the present invention, addition of auxiliary ingredients, and selection of specific methods, etc., are all within the scope of protection and disclosure of the present invention.

Claims

1. A quinazoline compound, characterized in that The compound has a structure shown in the following formula I, formula II, formula III or formula IV: Ar 11 Any one selected from a single bond, a C6-C30 arylene group or a C6-C20 heteroarylene group; R 101 Any one selected from H, cyano, C1-C12 alkyl, C6-C30 aryl or C6-C20 heteroaryl; R1, R2, and R3 are each independently selected from any one of H, C6-C40 aryl, C6-C30 heteroaryl, or C1-C12 alkyl; The hydrogen atoms in the quinazoline compound can each independently be substituted by at least one of a deuterium atom, -CN, -F, a C6-C20 aryl group, a C6-C20 heteroaryl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a triphenylsilyl group or a triphenylmethyl group.

2. The quinazoline compound according to claim 1, wherein The C6-C30 arylene group is selected from any one or a combination of at least two of phenylene, biphenylene, terphenylene, naphthylene, anthrylene, phenanthrenyl, fluorenylene, benzofluorenylene, dibenzofluorenylene, naphthofluorenylene, pyrenylene, perylene, spirofluorenylene, triphenylene, fluoranthenylene, hydrobenzoanthrylene, naphthylene fluorenylene, tetraphenylmethane or benzonaphthofluorenylene; Preferably, the C6-C20 heteroarylene group is selected from any one of a carbazolylene group, a dibenzothiophenylene group, a naphthobenzofuranyl group, a naphthobenzothiophenylene group, a dinaphthofuranyl group, a dinaphthothiophenylene group or a carbazolylene group; Preferably, the C6-C30 aryl group is selected from any one or a combination of at least two of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthrofluorenyl, pyrenyl, peryl, spirofluorenyl, triphenylene, fluoranthenyl, hydrogenated benzanthryl, indenofluorenyl, benzoindenofluorenyl, dibenzoindenofluorenyl, naphthrofluorenyl, tetraphenylmethane or benzonaphthofluorenyl; Preferably, the C6-C20 heteroaryl group is selected from any one of carbazolyl, dibenzothiophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, dinaphthofuranyl, dinaphthothiophenyl or carbazolyl; Preferably, the C6-C40 aryl group is selected from any one or a combination of at least two of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthrofluorenyl, pyrenyl, peryl, spirofluorenyl, triphenylene, fluoranthenyl, hydrogenated benzanthryl, indenofluorenyl, benzoindenofluorenyl, dibenzoindenofluorenyl, naphthrofluorenyl, tetraphenylmethane or benzonaphthofluorenyl; Preferably, the C6-C30 heteroaryl group is selected from any one of carbazolyl, dibenzothiophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, dinaphthofuranyl, dinaphthothiophenyl or carbazolyl; 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 C6-C20 aryl group is selected from any one of phenyl, naphthyl, biphenyl, anthracenyl, phenanthrenyl, fluorenyl, triphenylene or fluoranthenyl; Preferably, the C6-C20 heteroaryl group is selected from any one of carbazolyl, dibenzothiophenyl, dinaphthofuranyl or carbazolyl; Preferably, the C1-C6 alkyl group is selected from any one of methyl, ethyl, propyl, n-butyl, tert-butyl, cyclopentyl or cyclohexyl; As a preferred technical solution of the present invention, the C1-C6 alkoxy group is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentyloxy or hexyloxy.

3. The quinazoline compound according to claim 1 or 2, wherein The Ar 11 Any one or a combination of at least two selected from the group consisting of a single bond, a phenylene group, a naphthylene group, a triphenylene group, a fluoranthenylene group, a fluorenylene group, an anthrylene group, a phenanthrenyl group, a biphenylene group, a dibenzofuranyl group, and a dibenzothiophenylene group; Preferably, the Ar 11 Any one selected from a single bond, phenylene, naphthylene, triphenylene, fluoranthenylene, fluorenylene, anthracenylene, biphenylene, dibenzofuranylene, and dibenzothiophenylene; Preferably, the Ar 11 Any one selected from a single bond, a phenylene group, a naphthylene group, a biphenylene group or a carbazolylene group; Preferably, the R 101 Any one or a combination of at least two selected from H, cyano, phenyl, naphthyl, triphenylene, fluoranthene, fluorenyl, anthracenyl, phenanthrenyl, diphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl; Preferably, the R 101 Any one or a combination of at least two selected from phenyl, naphthyl, biphenyl, triphenylene, fluoranthene, anthracenyl, phenanthrenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, methyl, ethyl, propyl, propyl, butyl, pentyl, and hexyl; Preferably, the R 101 Any one selected from methyl, ethyl, phenyl, naphthyl, biphenyl, benzofuranyl, dibenzothiophenyl, and carbazolyl; Preferably, R1, R2, and R3 are each independently selected from any one or a combination of at least two of H, methyl, ethyl, propyl, butyl, pentyl, hexyl, H atom, cyano, phenyl, naphthyl, triphenylene, fluoranthene, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, and carbazolyl; Preferably, R1, R2, and R3 are each independently selected from any one of H, tert-butyl, phenyl, naphthyl, or carbazolyl.

4. The quinazoline compound according to any one of claims 1 to 3, wherein The hydrogen atoms in the quinazoline compound can each independently be substituted by at least one of a deuterium atom, -CN, -F, a phenyl group, a phenyl group, a naphthyl group, a triphenylene group, a fluoranthene group, a fluorenyl group, an anthracene group, a phenanthrenyl group, a biphenyl group, a dibenzofuranyl group, a dibenzothienyl group, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a triphenylsilyl group, and a triphenylmethyl group; Preferably, the hydrogen atoms in the quinazoline compound can each independently be substituted by at least one of a deuterium atom, -CN, -F, a methyl group, an ethyl group, a tert-butyl group, a methoxy group, a phenyl group or a naphthyl group.

5. The quinazoline compound according to any one of claims 1 to 4, wherein The quinazoline compound is selected from any one of the following compounds: The substitution means that the hydrogen atoms in the above quinazoline compounds can be independently replaced by deuterium atoms.

6. The quinazoline compound according to any one of claims 1 to 5, wherein The quinazoline compound is selected from any one of the following compounds:

7. An intermediate, characterized in that The intermediate includes a compound having a structure shown in the following formula M1 or M2: Wherein, X is selected from any one of fluorine, chlorine, bromine and iodine; Ar 11 、R 101 has the same definition as in claim 1; The intermediate is used to prepare the quinazoline compound according to 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 organic thin film layer material comprises the quinazoline 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, and a main material of the light-emitting layer includes the quinazoline compound according to any one of claims 1 to 6.

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