CN106397406B - Aromatic heterocyclic derivative, preparation method thereof, and organic electroluminescence device - Google Patents

Abstract

The present invention provides an aromatic heterocyclic derivative having the structure represented by formula (I). Compared with the prior art, the aromatic heterocyclic derivative provided by the present invention is to introduce Q ₁ , Q ₂ , Ar ₁ , Ar ₂ , Ar ₃ and Ar into the pyrido[3,4-g] aromatic heterocyclic derivative ₄ groups, which can improve electron density and skills, and at the same time, R ₁ can improve the performance of aromatic heterocyclic derivatives, so that the organic electroluminescence device containing the aromatic heterocyclic derivatives represented by formula (I) has higher high brightness, good heat resistance, long life and high efficiency.

Description

Aromatic heterocyclic derivative, preparation method thereof, and organic electroluminescence device

This application is a divisional application with an application date of June 2, 2015, an application number of 201510295963.3, and an invention-creation title of "Aromatic Heterocyclic Derivative and its Preparation Method, and an Organic Electroluminescent Device".

technical field

The invention relates to the technical field of organic optoelectronic materials, in particular to an aromatic heterocyclic derivative and a preparation method thereof, and an organic electroluminescence device.

Background technique

An organic electroluminescent device (OLED) is a new type of flat display device, generally consisting of two opposite electrodes and at least one layer of an organic light-emitting compound interposed between the two electrodes. Charges are injected into the organic layer formed between the anode and cathode to form electron and hole pairs, resulting in light emission from organic compounds with fluorescent or phosphorescent properties.

Organic electroluminescent devices have the characteristics of energy saving, fast response, stable color, strong environmental adaptability, no radiation, light weight and thin thickness. With the rapid development of optoelectronic communication and multimedia fields in recent years, organic optoelectronic materials have been Become the core of modern social information and electronic industry. However, there are still some key problems in this field that have not been really solved, and the short device life and low luminous efficiency have become the bottlenecks restricting its wide application.

SUMMARY OF THE INVENTION

In view of this, the technical problem to be solved by the present invention is to provide an aromatic heterocyclic derivative, a preparation method thereof, and an organic electroluminescence device, and the organic electroluminescence device prepared from the aromatic heterocyclic derivative has a relatively high performance. High luminous efficiency and long life.

The present invention provides an aromatic heterocyclic derivative having the structure shown in formula (I):

in,

L ₁ , L ₂ , L ₃ , L ₄ are independently selected from 0 or 1;

Q ₁ and Q ₂ are independently selected from nitrogen, oxygen, sulfur, an aryl group with 6-30 carbon atoms or a heterocyclic group with 1-30 carbon atoms;

R ₁ is selected from a hydrogen atom, a cyano group, an alkyl group with 1 to 30 carbon atoms, a substituted or unsubstituted aryl group with 6 to 50 carbon atoms, and a substituted or unsubstituted heterocycle with 5 to 50 carbon atoms group, substituted or unsubstituted aromatic amine group with 7 to 30 carbon atoms, substituted or unsubstituted aralkoxy group with 7 to 30 carbon atoms, or substituted or unsubstituted aralkane with 7 to 30 carbon atoms Sulfhydryl;

Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ are independently selected from a hydrogen atom, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, and a substituted or unsubstituted aralkoxy group having 7 to 50 carbon atoms , substituted or unsubstituted aralkylmercapto group with 7 to 50 carbon atoms, aryl group with 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic group with 5 to 50 carbon atoms, substituted or unsubstituted carbon atoms Aromatic amine groups of 7 to 30.

Preferably, the aromatic heterocyclic derivative has the following structure:

in,

Z ₁ to Z ₁₆ are independently selected from CH, C or N;

L ₃ and L ₄ are independently selected from 0 or 1;

R ₁ is selected from a hydrogen atom, a cyano group, an alkyl group with 1 to 30 carbon atoms, a substituted or unsubstituted aryl group with 6 to 50 carbon atoms, and a substituted or unsubstituted heterocycle with 5 to 50 carbon atoms group, substituted or unsubstituted aromatic amine group with 7 to 30 carbon atoms, substituted or unsubstituted aralkoxy group with 7 to 30 carbon atoms, or substituted or unsubstituted aralkane with 7 to 30 carbon atoms Sulfhydryl;

Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ are independently selected from a hydrogen atom, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, and a substituted or unsubstituted aralkoxy group having 7 to 50 carbon atoms , substituted or unsubstituted aralkylmercapto group with 7 to 50 carbon atoms, aryl group with 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic group with 5 to 50 carbon atoms, substituted or unsubstituted carbon atoms Aromatic amine groups of 7 to 30.

Preferably, in the aromatic heterocyclic derivative, -R ₁ is selected from the following structures:

-OR ₁ '; -SR ₁ ';

in,

Z ₁ to Z ₈ are independently selected from CH, C or N;

R' ₁ and R' ₂ are independently selected from alkyl groups with 1 to 30 carbon atoms, aryl groups with 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic groups with 5 to 50 carbon atoms, or substituted or An unsubstituted aromatic amino group having 6 to 30 carbon atoms.

Preferably, in the aromatic heterocyclic derivative, -Ar ₁ , -Ar ₂ , -Ar ₃ , -Ar ₄ are independently selected from the structures represented by the following formulas (1) to (35):

in,

X and Y are independently selected from a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group Substituted alkenyl group with 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 30 carbon atoms, substituted or unsubstituted aralkoxy group with 7 to 30 carbon atoms, substituted or unsubstituted Aryl having 6 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted heterocyclic group having 5 to 30 carbon atoms, or substituted or unsubstituted carbon atoms 7-30 aromatic amine groups.

Preferably, when Q ₁ and Q ₂ are both phenyl and R ₁ is cyano or phenyl, Ar ₁ and Ar ₂ are independently selected from substituted or unsubstituted aryl groups with 7 to 50 carbon atoms, substituted or An unsubstituted heterocyclic group having 5 to 50 carbon atoms or a substituted or unsubstituted aromatic amino group having 7 to 30 carbon atoms.

Preferably, L ₁ and L ₂ are not 0 at the same time.

The present invention also provides a preparation method of aromatic heterocyclic derivatives, comprising:

The compound represented by the formula (III) is reacted with the compound represented by the formula (IV) and the compound represented by the formula (V) to obtain the aromatic heterocyclic derivative represented by the formula (I);

in,

X' is a halogen atom, and Y' and Y ₁ ' are independently selected from B(OH) ₂ or H;

L ₁ , L ₂ , L ₃ , L ₄ are independently selected from 0 or 1;

Q ₁ and Q ₂ are independently selected from nitrogen, oxygen, sulfur, an aryl group with 6-30 carbon atoms or a heterocyclic group with 1-30 carbon atoms;

R ₁ is selected from a hydrogen atom, a cyano group, an alkyl group with 1 to 30 carbon atoms, a substituted or unsubstituted aryl group with 6 to 50 carbon atoms, and a substituted or unsubstituted heterocycle with 5 to 50 carbon atoms group, substituted or unsubstituted aromatic amine group with 7 to 30 carbon atoms, substituted or unsubstituted aralkoxy group with 7 to 30 carbon atoms, or substituted or unsubstituted aralkane with 7 to 30 carbon atoms Sulfhydryl;

Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ are independently selected from a hydrogen atom, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, and a substituted or unsubstituted aralkoxy group having 7 to 50 carbon atoms , substituted or unsubstituted aralkylmercapto group with 7 to 50 carbon atoms, aryl group with 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic group with 5 to 50 carbon atoms, substituted or unsubstituted carbon atoms Aromatic amine groups of 7 to 30.

The present invention also provides an organic electroluminescence device, comprising the above aromatic heterocyclic derivative or the aromatic heterocyclic derivative prepared by the above preparation method.

Preferably, the organic electroluminescence device includes a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode; the organic layer includes the above-mentioned aromatic heterocyclic derivative or the above-mentioned preparation method Preparation of aromatic heterocyclic derivatives.

The present invention also provides an organic optoelectronic material, comprising the aromatic heterocyclic compound according to any one of claims 1 to 6 or the aromatic heterocyclic compound prepared by the preparation method according to claim 7; the organic optoelectronic material includes organic Solar cells, electronic paper, organic photoreceptors or organic transistors.

Compared with the prior art, the present invention provides an aromatic heterocyclic derivative having a structure represented by formula (I), wherein L ₁ , L ₂ , L ₃ and L ₄ are independently selected from 0 or 1; Q ₁ and Q ₂ are independently selected from nitrogen, oxygen, sulfur, an aryl group with 6 to 30 carbon atoms or a heterocyclic group with 1 to 30 carbon atoms; R ₁ is selected from hydrogen atom, cyano group, and a carbon number of 1 ~30 alkyl groups, substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic groups with 5 to 50 carbon atoms, substituted or unsubstituted aromatic groups with 7 to 30 carbon atoms amine group, substituted or unsubstituted aralkoxy group with 7-30 carbon atoms or substituted or unsubstituted aralkylmercapto group with 7-30 carbon atoms; Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ are independent selected from hydrogen atoms, substituted or unsubstituted aralkyl groups having 7 to 50 carbon atoms, substituted or unsubstituted aralkoxy groups having 7 to 50 carbon atoms, and substituted or unsubstituted aralkyl groups having 7 to 50 carbon atoms Aralkylmercapto group, aryl group having 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms, and substituted or unsubstituted aromatic amine group having 7 to 30 carbon atoms. Compared with the prior art, the aromatic heterocyclic derivative provided by the present invention is to introduce Q ₁ , Q ₂ , Ar ₁ , Ar ₂ , Ar ₃ and Ar into the pyrido[3,4-g] aromatic heterocyclic derivative ₄ groups, which can improve electron density and skills, and at the same time, R ₁ can improve the performance of aromatic heterocyclic derivatives, so that the organic electroluminescence device containing the aromatic heterocyclic derivatives represented by formula (I) has higher high brightness, good heat resistance, long life and high efficiency.

Detailed ways

The present invention provides an aromatic heterocyclic derivative having the structure shown in formula (I):

in,

L ₁ , L ₂ , L ₃ , L ₄ are independently selected from 0 or 1;

Q ₁ and Q ₂ are independently selected from nitrogen, oxygen, sulfur, an aryl group with 6-30 carbon atoms or a heterocyclic group with 1-30 carbon atoms;

R ₁ is selected from a hydrogen atom, a cyano group, an alkyl group with 1 to 30 carbon atoms, a substituted or unsubstituted aryl group with 6 to 50 carbon atoms, and a substituted or unsubstituted heterocycle with 5 to 50 carbon atoms group, substituted or unsubstituted aromatic amine group with 7 to 30 carbon atoms, substituted or unsubstituted aralkoxy group with 7 to 30 carbon atoms, or substituted or unsubstituted aralkane with 7 to 30 carbon atoms Sulfhydryl;

Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ are independently selected from a hydrogen atom, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, and a substituted or unsubstituted aralkoxy group having 7 to 50 carbon atoms , substituted or unsubstituted aralkylmercapto group with 7 to 50 carbon atoms, aryl group with 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic group with 5 to 50 carbon atoms, substituted or unsubstituted carbon atoms Aromatic amine groups of 7 to 30.

The aromatic heterocyclic derivatives provided by the present invention are the introduction of Q ₁ , Q ₂ , Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ groups into the pyrido[3,4-g] aromatic heterocyclic derivatives, which can increase the electron At the same time, R ₁ can improve the performance of aromatic heterocyclic derivatives, so that the organic electroluminescent device comprising the aromatic heterocyclic derivatives represented by formula (I) has higher brightness, better resistance Thermal properties, long life and high efficiency.

In the aromatic heterocyclic derivatives represented by formula (I) provided by the present invention, the L ₁ , L ₂ , L ₃ and L ₄ are independently selected from 0 or 1, preferably L ₁ , L ₂ , L ₃ and L ₄ is not 0 at the same time; more preferably, L ₁ and L ₂ are not 0 at the same time; in some specific embodiments of the present invention, L ₁ and L ₂ are both 1, and L ₃ and L ₄ are independently selected from 0 or 1.

Q ₁ and Q ₂ are independently selected from nitrogen, oxygen, sulfur, an aryl group with 6-30 carbon atoms or a heterocyclic group with 1-30 carbon atoms; preferably nitrogen, oxygen, sulfur, and 6-24 carbon atoms aryl or heterocyclic group with 1 to 24 carbon atoms; more preferably nitrogen, oxygen, sulfur, aryl group with 6 to 14 carbon atoms or heterocyclic group with 1 to 14 carbon atoms.

In the present invention, preferably when Q ₁ and Q ₂ are both phenyl and R ₁ is cyano or phenyl, Ar ₁ and Ar ₂ are independently selected from substituted or unsubstituted aryl groups having 7 to 50 carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms or a substituted or unsubstituted aromatic amino group having 7 to 30 carbon atoms.

Preferably in the present invention, the aromatic heterocyclic derivative has any of the following structures:

in,

Z ₁ to Z ₁₆ are independently selected from CH, C or N.

R ₁ is selected from a hydrogen atom, a cyano group, an alkyl group with 1 to 30 carbon atoms, a substituted or unsubstituted aryl group with 6 to 50 carbon atoms, and a substituted or unsubstituted heterocycle with 5 to 50 carbon atoms group, substituted or unsubstituted aromatic amine group with 7 to 30 carbon atoms, substituted or unsubstituted aralkoxy group with 7 to 30 carbon atoms, or substituted or unsubstituted aralkane with 7 to 30 carbon atoms A mercapto group; preferably a hydrogen atom, a cyano group, an alkyl group with 1 to 15 carbon atoms, a substituted or unsubstituted aryl group with 6 to 14 carbon atoms, and a substituted or unsubstituted heterocycle with 5 to 14 carbon atoms group, substituted or unsubstituted aromatic amine group with 7 to 14 carbon atoms, substituted or unsubstituted aralkoxy group with 7 to 14 carbon atoms, or substituted or unsubstituted aralkane with 7 to 14 carbon atoms Sulfhydryl.

In the present invention, R ₁ is more preferably H, that is, the heteroaromatic ring derivative has any of the following structures:

In the present invention, R ₁ is also preferably any of the following structures:

-OR ₁ '; -SR ₁ ';

That is, the aromatic heterocyclic derivative has any of the following structures:

in,

Z ₁ to Z ₈ are independently selected from CH, C or N;

R' ₁ and R' ₂ are independently selected from alkyl groups with 1 to 30 carbon atoms, aryl groups with 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic groups with 5 to 50 carbon atoms, or substituted or Unsubstituted aromatic amine group with 6 to 30 carbon atoms; more preferably an alkyl group with 1 to 15 carbon atoms, an aryl group with 6 to 30 carbon atoms, and a substituted or unsubstituted carbon number of 5 to 30 The heterocyclic group or substituted or unsubstituted aromatic amino group with 6-15 carbon atoms; in some specific embodiments of the present invention, R ₁ is selected from the following groups: phenyl, pyridyl, quinolinyl , o-phenanthroline, N,N-diphenylamino, pyridin-4-yloxy, pyridin-4-ylmercapto or C5-C15 alkyl.

L ₃ , L ₄ , R ₁ , Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ have the same ranges as the above-mentioned L ₃ , L ₄ , R ₁ , Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ , and are not repeated here. Repeat.

In the present invention, Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ are independently selected from hydrogen atoms, substituted or unsubstituted aralkyl groups having 7 to 50 carbon atoms, and substituted or unsubstituted aralkyl groups having 7 to 50 carbon atoms. Aralkoxy, substituted or unsubstituted aralkylmercapto group with 7 to 50 carbon atoms, aryl group with 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic group with 5 to 50 carbon atoms, substituted or unsubstituted A substituted aromatic amino group having 7 to 30 carbon atoms. More preferably a hydrogen atom, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aralkoxy group having 7 to 30 carbon atoms, and a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms aralkylmercapto group, aryl group with 6 to 30 carbon atoms, substituted or unsubstituted heterocyclic group with 5 to 30 carbon atoms, substituted or unsubstituted aromatic amine group with 7 to 14 carbon atoms. In some specific embodiments of the present invention, Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ are independently selected from the structures represented by the following formulas (1) to (35):

In the present invention, the above-mentioned substituted aryl group, substituted heterocyclic group, substituted aromatic amino group, substituted aralkoxy group, substituted aralkylmercapto group, substituted aralkyl group, substituted alkenyl group, substituted aryl group In the oxy group, the substituted refers to those containing a substituent, and the substituent is preferably selected from halogen, C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, hydroxyl, C1-C30 alkoxy, amino, nitro, mercapto, thioether, imino, cyano, amide, phosphonate, phosphine, carboxyl, thiocarbonyl, sulfonyl, sulfamoyl, carbonyl, aldehyde, ester group, acetyl, acetoxy, carbamoyl, oxo (=O), haloalkyl, substituted aminoacyl and aminoalkyl, cycloalkyl (which may be monocyclic, fused polycyclic or non-fused polycyclic), heterocyclic groups (which can be monocyclic, fused or non-fused polycyclic), monocyclic or fused or non-fused polycyclic aromatic groups (such as phenyl, naphthyl, pyrrolyl, indium dolyl, furanyl, thienyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, triazolyl, tetrazolyl, pyrazolyl, quinolinyl, isoquinolinyl, acridinyl, pyridine oxazinyl, pyridazinyl, pyrimidinyl, benzimidazolyl, benzothienyl or benzofuranyl), amino, -O-C1-C20 alkyl, O-aryl, aryl, aryl-C1 ~C20 alkyl, _-CO2CH3 , _-CONH2 , _-OCH2CONH2 , _-NH2 , _-SO2NH2 , _{-OCHF2 , -CF3 , -OCF3 .} These substituents may be optionally further substituted with substituents selected from the above-mentioned groups. In the present invention, the substituent is more preferably selected from any one of the following formulae 36 to 65:

The present invention also provides a preparation method of aromatic heterocyclic derivatives, comprising:

The compound represented by the formula (III) is reacted with the compound represented by the formula (IV) and the compound represented by the formula (V) to obtain the aromatic heterocyclic derivative represented by the formula (I);

in,

X' is a halogen atom, and Y' and Y ₁ ' are independently selected from B(OH) ₂ or H;

L ₁ , L ₂ , L ₃ , L ₄ are independently selected from 0 or 1;

Q ₁ and Q ₂ are independently selected from nitrogen, oxygen, sulfur, an aryl group with 6-30 carbon atoms or a heterocyclic group with 1-30 carbon atoms;

R ₁ is selected from a hydrogen atom, a cyano group, an alkyl group with 1 to 30 carbon atoms, a substituted or unsubstituted aryl group with 6 to 50 carbon atoms, and a substituted or unsubstituted heterocycle with 5 to 50 carbon atoms group, substituted or unsubstituted aromatic amine group with 7 to 30 carbon atoms, substituted or unsubstituted aralkoxy group with 7 to 30 carbon atoms, or substituted or unsubstituted aralkane with 7 to 30 carbon atoms Sulfhydryl;

Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ are independently selected from a hydrogen atom, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, and a substituted or unsubstituted aralkoxy group having 7 to 50 carbon atoms , substituted or unsubstituted aralkylmercapto group with 7 to 50 carbon atoms, aryl group with 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic group with 5 to 50 carbon atoms, substituted or unsubstituted carbon atoms Aromatic amine groups of 7 to 30.

Wherein, the L ₁ , L ₂ , L ₃ , L ₄ , Q ₁ , Q ₂ , Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ and R ₁ are the same as those described above, and will not be repeated here.

The present invention has no special limitation on the source of the above-mentioned reaction raw materials, which may be commercially available or prepared. The compound represented by the formula (III) in the present invention is preferably prepared according to the following method:

In the present invention, when Q ₁ or Q ₂ is a C6-C30 aryl group or a C1-C30 heterocyclic group, Y' or Y ₁ ' is B(OH) ₂ , and the compound represented by the formula (III) and the formula The compound represented by (IV) or the compound represented by formula (V) is subjected to a Suzuki coupling reaction under the action of a catalyst, and the reaction conditions may be those well known to those skilled in the art, and there are no special restrictions.

When the Q1 or Q2 is N, O or S, Y' or Y ₁ ' is H, in this case, the compound represented by the formula (III) and the compound represented by the formula (IV) or the compound represented by the formula (V) The compound is subjected to a substitution reaction; the conditions of the substitution reaction can be the substitution reaction conditions well known to those skilled in the art, and there are no special restrictions.

In the above reaction formula, the R ₁ and X' are the same as above, and are not repeated here.

In the present invention, when Y' is B(OH) ₂ , the compound represented by the formula (IV) is preferably prepared according to the following method:

X" is a halogen atom.

When Y ₁ ' is B(OH) ₂ , the compound represented by formula (V) is preferably prepared according to the following method:

X" is a halogen atom.

In the present invention, when both L ₁ and L ₂ are 0, the compound represented by the formula (III) can be obtained by reducing the compound represented by the formula (I).

The preparation method of the aromatic heterocyclic derivative provided by the invention is simple and easy to industrialize.

The present invention also provides an organic electroluminescent device comprising the above-mentioned aromatic heterocyclic derivative represented by formula (I).

The organic electroluminescence device may be an organic electroluminescence device well known to those skilled in the art. The present invention preferably includes a first electrode, a second electrode and an organic layer disposed between the first electrode and the second electrode. ; The organic layer contains the above-mentioned aromatic heterocyclic derivatives.

In the present invention, the organic layer refers to all layers between the first electrode and the second electrode of the organic electroluminescent device. At least one of the organic layers is a light-emitting layer.

According to the present invention, the organic layer preferably includes a hole injection layer, a hole transport layer, a layer with both hole injection and hole transport technology, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron One or more layers of the injection layer and the layer with both electron transport and electron injection skills, more preferably including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron The transport layer and the electron injection layer or a layer with both hole injection and hole transport technology, an electron blocking layer, a light-emitting layer, a hole blocking layer and a layer with both electron transport and electron injection technology are arranged in sequence.

When the organic substance layer of the present invention includes a hole injection layer, a hole transport layer or a layer with both hole injection and hole transport technology, preferably the hole injection layer, hole transport layer or both hole injection and hole transport layer At least one of the hole transport technology layers includes a hole injection material, a hole transport material, or a material with both hole injection and hole transport technology.

When the organic layer of the present invention has a single-layer structure, the organic layer is a light-emitting layer; when the organic layer has a multi-layer structure, the organic layer includes a light-emitting layer; the light-emitting layer preferably includes a phosphorescent host and a fluorescent host , one or more of a phosphorescent doping material and a fluorescent doping material; one or more of the phosphorescent host, the fluorescent host, the phosphorescent doping material and the fluorescent doping material are those shown in formula (I) Aromatic Heterocyclic Derivatives.

The light-emitting layer may also preferably be a red, yellow or cyan light-emitting layer, and the aromatic heterocyclic derivative is a host or dopant of the red, yellow or cyan light-emitting layer. For example, when the light-emitting layer is a cyan light-emitting layer, the aromatic heterocyclic derivative represented by the formula (I) can provide high efficiency, high brightness, high resolution and Long-life organic light-emitting devices.

When the organic substance layer includes an electron transport layer, the electron transport layer may include an aromatic heterocyclic derivative and/or a metal compound represented by formula (I). The metal compound may be a substance known to those skilled in the art for electron transport, and there is no special limitation.

When the organic layer includes both a light-emitting layer and an electron transport layer, the light-emitting layer and the electron transport layer may respectively include an aromatic heterocyclic derivative represented by formula (I) with the same or different structures.

The organic electroluminescent device provided by the present invention can be made of the aromatic heterocyclic derivative represented by the formula (I) and conventional materials. The present invention does not limit the preparation method of the organic electroluminescent device. Conventional methods are enough, the present invention preferably utilizes methods such as thin film evaporation, electron beam evaporation or physical vapor deposition to evaporate metals and conductive oxides and their alloys on the substrate to form an anode, and then form an organic layer and an anode thereon. The cathode is evaporated to obtain an organic electroluminescent device.

The organic layer may include the above-mentioned multilayer structure of hole injection layer, hole transport layer, light-emitting layer, hole blocking layer and electron transport layer, and these multilayer structures may be formed according to the above-mentioned thin film evaporation and electron beam evaporation. Or physical vapor deposition and other methods of evaporation, and various polymer material solvent engineering can also be used to replace evaporation methods, such as spin-coating, tape-casting, doctor-blading ), screen printing (Screen-Printing), inkjet printing or thermal imaging (Thermal-Imaging) and other methods to reduce the number of layers to manufacture.

The organic electroluminescent device provided by the present invention can also be classified into front light emitting, back light emitting or double-sided light emitting according to the materials used; and the organic electroluminescent device can be applied to organic light emitting devices (OLED), organic solar cells (OSC ), electronic paper (e-paper), organic photoreceptor (OPC) or organic thin film transistor (OTFT).

The aromatic heterocyclic derivatives represented by the formula (I) provided by the present invention can also be applied in organic devices such as organic solar cells, OLEDs for lighting, flexible OLEDs, organic photoreceptors and organic transistors according to the principle of applying organic light-emitting devices.

The present invention also provides an organic optoelectronic material, comprising the isoquinoline compound represented by the above formula (I); the organic optoelectronic material includes an organic solar cell, an electronic paper, an organic photoreceptor or an organic transistor.

In order to further illustrate the present invention, the aromatic heterocyclic derivatives and the preparation method thereof and the organic electroluminescent device provided by the present invention will be described in detail below with reference to the examples.

Example 1

Synthesis of intermediate 2-chloro-5-phenylpyrazine (A-1):

2-Bromo-5-chloropyrazine (21.3g, 0.11mol), phenylboronic acid (12.2g, 0.10mol), tetrakistriphenylphosphonium palladium 0.5g were added to a 1000mL reaction flask, toluene 400mL, sodium carbonate were added The aqueous solution (2N, 150 mL) was protected with nitrogen, and the reaction was carried out in an oil bath at 80°C for 24 hours. After-treatment process: the reaction system is cooled down, left to stand for 30 minutes to separate the liquid, the organic layer is retained, toluene is spin-dried, a small amount of dichloromethane is added to the solid to dissolve, the column is separated, and petroleum ether: dichloromethane=1:1 (volume ratio) The column was punched to obtain solid (A-1) (10.7 g, y=56%).

Example 2

Synthesis of Intermediates A-2 to A-5:

According to the synthesis method of the intermediate A-1 of Example 1, the compounds shown in Table 1 were prepared with the same molar ratio. Table 1 is a summary of the reaction substances, products and yields of Example 2 of the present invention.

Summary of Table 1 Example 2 Reaction Substances, Generated Substances and Yields

Example 3

Synthesis of intermediate 5-chloro-N,N-diphenylpyrazin-2-amine (A-6):

Diphenylamine (16.9 g, 0.10 mol), sodium tert-butoxide (28 g, 0.30 mol), and 400 mL of toluene were added to the reaction flask, stirred for 30 minutes, under nitrogen protection, and then added 2-bromo-5-chloropyrazine (23.2 g, 0.12mol), tris(dibenzylideneacetone)dipalladium 1.5g, finally added tri-tert-butylphosphine 4g, heated to 100 DEG C and reacted for 24 hours. Post-processing process: cooling the system, adding water to terminate the reaction, filtering, separating the filtrate, spin drying toluene, adding a small amount of dichloromethane to dissolve the solid, petroleum ether: dichloromethane=3:1 (volume ratio) and separating through a column to obtain a solid (A-6) (14.1 g, y=50%).

Example 4

According to the synthesis method of the intermediate A-6 in Example 3, the compounds shown in Table 2 were prepared with the same molar ratio. Table 2 is a summary of the reaction substances, generated substances and yields in Example 4 of the present invention.

Table 2 Summary of reaction substances, generated substances and yields in Example 4 of the present invention

Example 5

Synthesis of intermediate 5-chloro-2,3-diphenylpyrazine (A-9):

Phenylboronic acid (24.4g, 0.20mol), 2,3-dibromo-5-chloroquinoline (27.3g, 0.10mol), tetrakistriphenylphosphine palladium (7.0g, 3%) were added to the reaction flask, Toluene 600mL, sodium carbonate aqueous solution (2N, 250mL) nitrogen protection, oil bath 90 ℃ reaction, overnight. Post-processing process: cooling the system, separating liquids, spin-drying toluene, dissolving the residue in dichloromethane, adding an equal amount of petroleum ether, passing through a silica gel funnel, and using dichloromethane: petroleum ether=1:2 (volume ratio) Rinse until no point of product comes out, collect the filtrate, and spin dry the solvent to give a dark solid (A-9) (21.3 g, y=80%).

Example 6

According to the synthesis method of the intermediate A-9 in Example 5, the compounds shown in Table 3 were prepared with the same molar ratio. Table 3 is a summary of the reaction substances, generated substances and yields in Example 6 of the present invention.

Table 3 Summary of Example 6 Reaction Materials, Generated Materials and Yields of the Present Invention

Example 7

Synthesis of intermediate 5-(4-pyridyl)pyrimidin-2-ylboronic acid (A-13):

Take 5-(4-pyridyl)-2-bromopyrimidine (10g, 42.4mmol) into a three-necked flask, add 100mL of THF, under nitrogen protection, stir at -78°C for 30 minutes, then add n-butyllithium (2.5M) 21 mL, react for 1 hour, then add 14 g of triisopropyl borate, react at low temperature for 1 hour, and gradually return to room temperature. After treatment, 2M hydrochloric acid was added to the system to make the pH value of the solution 4-5, the solution was allowed to stand for separation, the aqueous layer was extracted once with ethyl acetate, the organic layers were combined, and spin-dried to obtain a white solid (A-13) (6.8g) , y=80%).

Example 8

According to the synthesis method of the intermediate A-13 of Example 7, the compounds shown in Table 4 were prepared with the same molar ratio. Table 4 is a summary of the reaction substances, products and yields of Example 8 of the present invention.

Table 4 Summary of reaction substances, generated substances and yields in Example 8 of the present invention

Example 9

Synthesis of the intermediate methyl 2-(pyridine-2-carbonyl)picolinate (B-1):

Dissolve 3-bromopyridine (15.9 g, 0.1 mol) in 300 mL of anhydrous ether, dry ice bath at -78 °C, nitrogen protection, add 44 mL of BuLi (2.5 M), stir for 1 hour, and then add 3,4-pyridine Diethyl diformate (19.5 g, 0.1 mol) was reacted for 2 hours, then gradually raised to room temperature, and water was added to terminate the reaction. Post-processing process: the system is liquid-separated, the water layer is separated, the water layer is extracted once with ethyl acetate, the organic layers are combined and the organic solvent is spin-dried, and the dichloromethane:petroleum ether=9:1 (volume ratio) is used for column separation, A white solid (B-1) (12.1 g, Y=50%) was obtained.

Example 10

According to the synthesis method of Intermediate B-1 in Example 9 above, the compounds shown in Table 5 were prepared with the same molar ratio. Table 5 is a summary of the reaction substances, products and yields in Example 10 of the present invention.

Table 5 Summary of Example 10 Reaction Substances, Generated Substances and Yields of the Present Invention

Example 11

Synthesis of intermediate pyrido[3,4-g]isoquinoline-5,10-dione (C-1):

The B-1 (10 g, 41.5 mmol) prepared in Example 9 was dissolved in 300 mL of THF, cooled to 0 °C, and the mixed solution LTMP was added (synthesis of LTMP: in 500 mL of THF, 0.13 mol BuLi was dissolved at 0 °C, 0.14 mol of 2,2,6,6-tetramethylpiperidine). The reaction was stirred at 0° C. for 2 hours, 200 mL of water was added to terminate the reaction, the aqueous layer was separated, the organic layer was spin-dried, and separated through a column with dichloromethane:petroleum ether=10:1 (volume ratio) to obtain solid (C-1) ( 3.5 g, y=44%).

Example 12

According to the synthesis method of the intermediate C-1 of Example 11, the compounds shown in Table 6 were prepared with the same molar ratio. Table 6 is a summary of the reaction substances, products and yields of Example 12 of the present invention.

Table 6 Summary of reaction substances, generated substances and yields in Example 12 of the present invention

Example 13

Synthesis of intermediate 5,10-dichloropyrido[3,4-g]isoquinoline (D-1):

Accurately weigh C-1 (10 g, 47.8 mmol) prepared in Example 11 and add it to the reaction flask, add 200 mL of acetonitrile, then weigh 30 g of phosphorus oxychloride and slowly add it dropwise to the reaction flask. 60°C, the reaction time was 5 hours. After the reaction is completed, add water to be carefully extracted and quenched, then add a large amount of saturated sodium carbonate solution to adjust the pH value to 7-8, then add dichloromethane, extract three times, spin dry to obtain solid (D-1) (7.5g, y= 63%).

Example 14

According to the synthesis method of the intermediate D-1 of Example 13 above, the compounds shown in Table 7 were prepared with the same molar ratio. Table 7 is a summary of the reaction substances, products and yields of Example 14 of the present invention.

Table 7 Summary of Reaction Substances, Generated Substances and Yields in Example 14 of the Present Invention

Example 15

Synthesis of 5,10-bis(4-pyridyl)pyrido[3,4-g]isoquinoline (E-1):

5,10-dichloro-pyrido[g]quinoline D-1 (14.8 g, 0.6 mmol) prepared in Example 13, 4-boronic acid pyridine (18 g, 0.146 mmol), and 4 g of tetrakistriphenylphosphine palladium were added Into the reaction flask, add a total of 600 mL of a 2:1:1 (volume ratio) mixture of toluene, ethanol and water, under nitrogen protection, stir and heat up to 110° C. to react for 24 hours. Post-processing process: cooling the system, separating liquids, and spin-drying toluene. Dichloromethane was added to dissolve the solid, passed through the column, and washed with petroleum ether:ethyl acetate=2:1 (volume ratio) to obtain solid (E-1) (13 g, y=65%).

The structure of the prepared compound was characterized by H NMR, and the results are as follows: ¹ H NMR (500MHz, Chloroform)δ9.29(s,2H), 8.71(s,4H), 8.52(s,2H), 7.90(s , 4H), 7.63(s, 2H). It can be seen that the above compound E-1 is prepared by the present invention.

Examples E-2 to E-23

According to the synthesis method of the intermediate E-1 of the above Example 15, the compounds shown in Table 8 were prepared with the same molar ratio. Table 8 is a summary of the reaction substances, generated substances and yields of Examples E-2 to E-23 of the present invention .

Table 8 Summary of Reaction Substances, Generated Substances and Yields in Examples E-2 to E-23 of the Present Invention

Embodiment F-1～F-9

According to the synthesis method of Example 15E-1 above, the compounds D2 to D9 prepared in Example 14 were used as raw materials, and the compounds shown in Table 9 were prepared with the same molar ratio. Table 9 is Examples F-1 to F- 9 Summary of reaction substances, product substances and yields.

Table 9 Summary of reaction substances, generated substances and yields of the embodiments F-1 to F-9 of the present invention

The structure of the prepared compound F-1 was characterized by hydrogen nuclear magnetic resonance spectroscopy, and the results were as follows: ¹ H NMR (500MHz, Chloroform)δ9.54(s,1H), 9.29(s,1H), 8.71(s,4H), 8.52(s, 1H), 8.33(s, 2H), 8.12(s, 1H), 7.90(s, 4H), 7.63(s, 1H), 7.52(d, J=30.0Hz, 3H). It can be seen that the above compound F-1 is prepared by the present invention.

The structure of the prepared compound F-9 was characterized by hydrogen nuclear magnetic resonance spectroscopy, and the results were as follows: ¹ H NMR (500MHz, Chloroform) δ9.23 (d, J=85.0 Hz, 2H), 8.32 (s, 1H), 7.65 ( d, J=5.0Hz, 5H), 7.55(s, 4H), 7.42(d, J=10.0Hz, 3H), 2.71(s, 2H), 1.63(s, 2H), 1.27(d, J=15.0 Hz, 12H), 0.89 (s, 3H). It can be seen that the above compound F-9 is prepared by the present invention.

Example 16

Synthesis of N,N-diphenyl-10-(pyridin-4-yloxy)pyrido[3,4-g]isoquinolin-5-amine (G-1):

1) Synthesis of 10-chloro-N,N-diphenylpyrido[3,4-g]isoquinolin-5-amine

According to the synthesis method of Example 3 Intermediate A-6, 5,10-dichloropyrido[3,4-g]isoquinoline (6.0 g, 24 mmol) and diphenylamine (4.4, 24 mmol) were used as raw materials for the reaction , the intermediate 10-chloro-N,N-diphenylpyrido[3,4-g]isoquinolin-5-amine (4.6g, y=50%) was obtained.

2) Synthesis of N,N-diphenyl-10-(pyridin-4-yloxy)pyrido[3,4-g]isoquinolin-5-amine (G-1)

Dissolve 4-hydroxypyridine (10g, 0.1mol) in 100mL of anhydrous tetrahydrofuran, stir, accurately weigh NaH (0.96g, 0.4mol) and add it to the reaction flask in batches, not too fast to prevent the generation of too many bubbles , the solution turned yellow after the addition, and then 10-chloro-N,N-diphenylpyrido[3,4-g]isoquinolin-5-amine (42.0g, 0.11mol) was added, which was also added in batches , and reacted overnight at room temperature. After-treatment process: filter, remove the solid matter, spin the filtrate to dryness, add dichloromethane to dissolve, pass through the column and flush the column with petroleum ether:ethyl acetate=1:5 (volume ratio) to obtain solid (G-1) (22.0g) , y=50%).

The structure of the prepared compound G-1 was characterized by hydrogen nuclear magnetic resonance spectroscopy, and the results are as follows: ¹ H NMR (500MHz, Chloroform)δ9.61(s,1H), 9.29(s,1H), 8.51(d,J=15.0 Hz, 2H), 8.39 (s, 2H), 7.65 (d, J=25.0 Hz, 2H), 7.24 (s, 4H), 7.14–6.93 (m, 8H). It can be seen that the compound represented by the above G-1 is prepared by the present invention.

Example 17

Synthesis of N,N-diphenyl-10-(pyridin-4-ylthio)pyrido[3,4-g]isoquinolin-5-amine (G-2):

4-Pyridinethiol (1.1 g, 10 mmol), 10-chloro-N,N-diphenylpyrido[3,4-g]isoquinolin-5-amine (3.8 g, 10 mmol), potassium hydroxide (840 mg, 15 mmol), mPANI/pFe3O4 (2.5 g, 5 mol%) H2O (30 mL) was mixed and heated for 8 hours. The organic phase was extracted with ethyl acetate, and separated by column using ethyl acetate: petroleum ether=4:1 (volume ratio) to obtain a white solid (G-2) (1.73 g, y=38%).

The structure of the prepared compound G-2 was characterized by hydrogen nuclear magnetic resonance spectroscopy, and the results were as follows: ¹ H NMR (500MHz, Chloroform)δ9.29(s,2H), 8.88(s,2H), 8.52(s,2H), 7.73(s, 1H), 7.63(s, 1H), 7.43(s, 2H), 7.24(s, 4H), 7.04(d, J=40.0Hz, 6H). It can be seen that the compound represented by the above G-2 is prepared by the present invention.

Example 18

Synthesis of 5,10-bis(pyridin-4-yloxy)pyrido[3,4-g]isoquinoline (G-3):

According to the synthesis method of G-1 in Example 16, D-1 (5.0 g, 20 mmol) and 4-hydroxypyridine (4.0 g, 42 mmol) were added to obtain solid (G-3) (3.4 g, y=46%) .

The structure of the prepared compound G-3 was characterized by hydrogen nuclear magnetic resonance spectroscopy, and the results were as follows: ¹ H NMR (500MHz, Chloroform)δ9.42(s,2H), 8.50(s,2H), 8.39(s,4H), 7.76(s, 2H), 6.98(s, 4H). It can be seen that the compound represented by G-3 above is prepared by the present invention.

Example 19

Synthesis of 5,10-bis(pyridin-4-ylthio)pyrido[3,4-g]isoquinoline (G-4):

According to the synthetic method of G-2 in Example 17, 4-pyridinethiol (2.2g, 20mmol) and 5,10-dichloropyridine[3,4-g]isoquinoline (2.5g, 10mmol) were added to obtain White solid (G-4) (1.4 g, y=35%).

The structure of the prepared compound G-4 was characterized by hydrogen nuclear magnetic resonance spectroscopy, and the results are as follows: ¹ H NMR (500MHz, Chloroform)δ9.29(s,1H), 8.88(s,2H), 8.52(s,1H), 7.63(s, 1H), 7.43(s, 2H). It can be seen that the compound represented by the above G-4 is prepared by the present invention.

Example 20

The Fisher Coating thickness is The ITO glass substrate was washed twice in distilled water, washed with ultrasonic waves for 30 minutes, then washed with isopropanol, acetone and methanol for 30 minutes in sequence, then repeatedly washed with distilled water for 2 times, washed with ultrasonic waves for 10 minutes, dried, and transferred to a plasma cleaning machine In the process, the above-mentioned substrate was washed for 5min and sent to the evaporation machine; the hole injection layer 2-TNATA was evaporated on the prepared ITO transparent electrode. Hole transport layer a-NPD evaporation Cyan host ADN/5% doped TPPDA evaporation The hole blocking layer and hole transport layer are evaporated as shown in Table 10 Cathode LiF Al The organic electroluminescent device is obtained; the organic matter evaporation rate in the above process is maintained LiF is Al is

Table 10 shows the electroluminescence properties of the organic light-emitting device obtained by the above method.

Table 10 The material types of the hole blocking layer and the hole transport layer and the electron emission characteristics of the organic electroluminescent device in Example 20

It can be seen from the above Table 10 that the luminous efficiency and lifetime characteristics of the organic electroluminescent device prepared by using the aromatic heterocyclic derivatives of the present invention are significantly improved.

The invention utilizes the novel aromatic heterocyclic derivatives to prepare the organic electroluminescent device, which has higher luminous efficiency and longer lifespan, and thus can be applied to the OLED industry with high practicability. The organic electroluminescent device of the present invention can be applied to flat panel display, flat light-emitting body, surface-emitting OLED light-emitting body for lighting, flexible light-emitting body, copiers, printers, LCD backlights or light sources of measuring machines, display panels, signs, etc. .

The descriptions of the above embodiments are only used to help understand the method and the core idea of the present invention. It should be pointed out that for those skilled in the art, without departing from the principle of the present invention, several improvements and modifications can also be made to the present invention, and these improvements and modifications also fall within the protection scope of the claims of the present invention.

Claims (9)

1. An aromatic heterocyclic derivative having the structure shown in formula (I): in, L ₁ , L ₂ , L ₃ , and L ₄ are independently selected from 0 or 1; and L ₁ , L ₂ are not 0 at the same time; Q ₁ and Q ₂ are independently selected from aryl groups having 6 to 30 carbon atoms; Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ are independently selected from substituted or unsubstituted heterocyclic groups having 5 to 50 carbon atoms; Or Q ₁ and Q ₂ are independently selected from heterocyclic groups with 1 to 30 carbon atoms; Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ are independently selected from a hydrogen atom, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, and a substituted or unsubstituted aralkoxy group having 7 to 50 carbon atoms , substituted or unsubstituted aralkylmercapto group with 7 to 50 carbon atoms, aryl group with 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic group with 5 to 50 carbon atoms, substituted or unsubstituted carbon atoms Aromatic amine groups of 7 to 30; R ₁ is selected from a hydrogen atom, a cyano group, an alkyl group with 1 to 30 carbon atoms, a substituted or unsubstituted aryl group with 6 to 50 carbon atoms, and a substituted or unsubstituted heterocycle with 5 to 50 carbon atoms group, substituted or unsubstituted aromatic amine group with 7 to 30 carbon atoms, substituted or unsubstituted aralkoxy group with 7 to 30 carbon atoms, or substituted or unsubstituted aralkane with 7 to 30 carbon atoms Sulfhydryl. 2. The aromatic heterocyclic derivative according to claim 1, wherein the aromatic heterocyclic derivative has the following structure: in, Z ₁ to Z ₁₆ are independently selected from CH, C or N; and Z ₁ to Z ₁₆ are not simultaneously CH or C; L ₃ and L ₄ are independently selected from 0 or 1; R ₁ is selected from a hydrogen atom, a cyano group, an alkyl group with 1 to 30 carbon atoms, a substituted or unsubstituted aryl group with 6 to 50 carbon atoms, and a substituted or unsubstituted heterocycle with 5 to 50 carbon atoms group, substituted or unsubstituted aromatic amine group with 7 to 30 carbon atoms, substituted or unsubstituted aralkoxy group with 7 to 30 carbon atoms, or substituted or unsubstituted aralkane with 7 to 30 carbon atoms thiol; Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ are independently selected from a hydrogen atom, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, and a substituted or unsubstituted aralkoxy group having 7 to 50 carbon atoms , substituted or unsubstituted aralkylmercapto group with 7 to 50 carbon atoms, aryl group with 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic group with 5 to 50 carbon atoms, substituted or unsubstituted carbon atoms Aromatic amine groups of 7 to 30; When Z ₁ to Z ₁₆ are both CH or C, Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ are independently selected from substituted or unsubstituted heterocyclic groups having 5 to 50 carbon atoms. 3. The aromatic heterocyclic derivative according to claim 1, wherein in the aromatic heterocyclic derivative, -R ₁ is selected from the following structures: in, Z ₁ to Z ₈ are independently selected from CH, C or N; R' ₁ and R' ₂ are independently selected from alkyl groups with 1 to 30 carbon atoms, aryl groups with 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic groups with 5 to 50 carbon atoms, or substituted or An unsubstituted aromatic amino group having 6 to 30 carbon atoms. The aromatic heterocyclic derivative according to any one of claims 1 to 3, wherein in the aromatic heterocyclic derivative, -Ar ₁ , -Ar ₂ , -Ar ₃ , -Ar ₄ are independent It is selected from the structures represented by the following formulas (1) to (35): in, X and Y are independently selected from a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group Substituted alkenyl group with 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 30 carbon atoms, substituted or unsubstituted aralkoxy group with 7 to 30 carbon atoms, substituted or unsubstituted Aryl having 6 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted heterocyclic group having 5 to 30 carbon atoms, or substituted or unsubstituted carbon atoms 7-30 aromatic amine groups. 5. The aromatic heterocyclic derivative according to claim 1, wherein when Q ₁ and Q ₂ are both phenyl and R ₁ is cyano or phenyl, Ar ₁ and Ar ₂ are independently selected from substituted or an unsubstituted heterocyclic group having 5 to 50 carbon atoms. 6. a preparation method of aromatic heterocyclic derivative, comprising: The compound represented by the formula (III) is reacted with the compound represented by the formula (IV) and the compound represented by the formula (V) to obtain the aromatic heterocyclic derivative represented by the formula (I); in, X' is a halogen atom, and Y' and Y ₁ ' are independently selected from B(OH) ₂ or H; L ₁ , L ₂ , L ₃ , L ₄ are independently selected from 0 or 1; And L ₁ and L ₂ are not 0 at the same time; Q ₁ and Q ₂ are independently selected from aryl groups having 6 to 30 carbon atoms; Ar ₁ , Ar ₂ , Ar ₃ and Ar ₄ are independently selected from substituted or unsubstituted heterocyclic groups having 5 to 50 carbon atoms; Or Q ₁ and Q ₂ are independently selected from heterocyclic groups with 1 to 30 carbon atoms; Ar ₁ , Ar ₂ , Ar ₃ , and Ar ₄ are independently selected from a hydrogen atom, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, and a substituted or unsubstituted aralkoxy group having 7 to 50 carbon atoms , substituted or unsubstituted aralkylmercapto group with 7 to 50 carbon atoms, aryl group with 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic group with 5 to 50 carbon atoms, substituted or unsubstituted carbon atoms Aromatic amine groups of 7 to 30; R ₁ is selected from a hydrogen atom, a cyano group, an alkyl group with 1 to 30 carbon atoms, a substituted or unsubstituted aryl group with 6 to 50 carbon atoms, and a substituted or unsubstituted heterocycle with 5 to 50 carbon atoms group, substituted or unsubstituted aromatic amine group with 7 to 30 carbon atoms, substituted or unsubstituted aralkoxy group with 7 to 30 carbon atoms, or substituted or unsubstituted aralkane with 7 to 30 carbon atoms Sulfhydryl. 7 . An organic electroluminescent device, comprising the aromatic heterocyclic derivative according to any one of claims 1 to 5 or the aromatic heterocyclic derivative prepared by the preparation method according to claim 6 . 8 . The organic electroluminescence device according to claim 7 , comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode; the organic layer comprises The aromatic heterocyclic derivative according to any one of claims 1 to 5 or the aromatic heterocyclic derivative prepared by the preparation method according to claim 6. 9 . An organic optoelectronic material, characterized in that it comprises the aromatic heterocyclic compound according to any one of claims 1 to 5 or the aromatic heterocyclic compound prepared by the preparation method according to claim 6 ; the organic optoelectronic material comprises Organic solar cells, electronic paper, organic photoreceptors or organic transistors.