CN107857759A - Organic luminescent compounds and preparation method and organic luminescent device - Google Patents

Abstract

The present invention relates to a kind of organic luminescent compounds and preparation method and organic luminescent device, is related to organic field of light emitting materials.It is provided by the invention with it is more appropriate it is chromaticity coordinates, purity is high, the organic luminescent compounds of outstanding skeleton are as organic luminescent device electron transport layer materials, compared with other electron transport layer materials, the organic luminescent device prepared by the use of organic luminescent compounds provided by the invention as electron transport layer materials, its luminous efficiency significantly improves, the life-span is obviously improved.The preparation method of organic luminescent compounds provided by the invention, raw material are easy to get, and technique is simple, are suitable for industrialized production.

Description

Organic light-emitting compound and its preparation method and organic light-emitting device

technical field

The invention relates to the field of organic light-emitting materials, in particular to an organic light-emitting compound, a preparation method and an organic light-emitting device.

Background technique

OLEDs have attracted extensive attention due to their potential applications in display and lighting. Materials used in OLEDs include light-emitting materials, auxiliary materials, and electrode materials. The auxiliary materials mainly include carrier transport materials, carrier injection materials and carrier blocking materials. Carrier transport materials are hole transport materials and electron transport materials. The electron transport material mainly transports electrons, and is responsible for transferring electron carriers from the metal cathode to the light-emitting layer. The performance of the electron transport material has a great influence on the efficiency of the OLED device. Electron transport materials that can greatly improve the efficiency of OLED devices should generally have the following characteristics: (1) The electrochemical reduction of the material is reversible, because the process of electron conduction in organic thin films is a series of redox processes ; (2) The HOMO and LUMO energy levels of the material are suitable, so that the injection barrier of electrons is the smallest, with a lower turn-on and working voltage, and preferably has hole blocking ability; (3) The electron mobility of the material is higher , so as to ensure that electrons can recombine in the light-emitting layer, so that the rate of excitons is increased; (4) the glass transition temperature and thermal decomposition stability of the material are high, which can avoid the Joule generated by the device when it is working. The impact of heat on device life and efficiency; (5) The material should be in the form of an amorphous film to avoid light scattering or decay caused by crystals.

Electron transport materials currently available for organic electroluminescent devices include: metal complexes ALq3, Liq, TPBI, BCP, etc. Among them, Alq3 is an organometallic complex with luminescent function, which has been used as an electron transport material because of its excellent electron mobility. However, Alq3 has problems such as moving to other layers and reducing color purity when used in Blu-ray devices. Therefore, a new type of electron transport material is required to be available, which does not have the above-mentioned problems, has high electron affinity, and when used in organic electroluminescent devices, has fast electron movement characteristics to show high luminous efficiency.

Contents of the invention

The present invention aims to solve the technical problems in the prior art, and provides an organic light-emitting compound with a novel structure, a preparation method, and an organic light-emitting device. Life expectancy was significantly improved.

In order to solve the problems of the technologies described above, the technical solution of the present invention is specifically as follows:

An organic luminescent compound, its chemical structural formula is as shown in formula 1:

In the formula: X is O or S;

Ar ₁ is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted aromatic heterocyclic group;

Ar is hydrogen or benzene;

Z ₁ to Z ₅ are N or O, and at least one of Z ₁ to Z ₅ is C;

A phenyl group may be attached to the position indicated by the dotted line in the formula.

In the above technical scheme, the organic light-emitting compound is any one of the following structures:

In the above technical solution, Ar ₁ is a substituted or unsubstituted phenyl group with 6-16 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group with 5-11 carbon atoms.

In the above technical solution, Ar ₁ is a substituted or unsubstituted phenyl group with 11-16 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group with 6-10 carbon atoms.

In the above technical solution, Ar ₁ is a substituted or unsubstituted phenyl group with 11 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group with 7 carbon atoms.

In the above technical scheme, Ar is pyridyl, picoline, _lutyl , methylpyrimidinyl, dimethylpyrimidinyl, 4-pyridylphenyl, 4-(3-methylisoquinol linyl)phenyl, 2,3-dimethyl-1,4-quinoxalinyl, 2-methylisoquinolinyl or 2-methylbipyridyl.

In the above technical scheme, the organic light-emitting compound is any one of the structures shown below:

A method for preparing an organic luminescent compound, comprising the following steps:

Step 1. Put compound a, compound b, potassium carbonate, and tetrakistriphenylphosphine palladium into a round-bottomed flask, and pour tetrahydrofuran and H ₂ O into it, and reflux the mixture for 24 hours. After the reaction is completed, remove the water layer , the organic layer was dried with MgSO ₄ and distilled under reduced pressure, and the crude product was recrystallized to obtain compound c;

Step 2. Put compound c, compound d, and K ₃ PO ₄ in dimethyl sulfoxide, heat the mixture to 90°C for 1 hour, after the reaction is completed, add water to the reaction mixture, filter it to obtain light yellow Solid, then add 2,3-dichloro-5,6-dicyano-p-benzoquinone to the solution, stir at room temperature for 10 minutes, after the reaction is complete, filter, and distill under reduced pressure, the resulting crude product is passed through silica gel column chromatography Purify, using 0-10% ethyl acetate in hexane as eluent to obtain compound e;

Step 3. Put compound e, compound f, potassium carbonate, and tetrakistriphenylphosphine palladium into a round-bottomed flask, and pour tetrahydrofuran and H ₂ O into it, and reflux the mixture for 24 hours. After the reaction is completed, remove the water layer , the organic layer was dried with MgSO ₄ and distilled under reduced pressure, and the crude product was recrystallized to obtain compound g;

Step 4, compound g, two (pinacol) diboron, potassium acetate, two (dibenzylideneacetone) palladium, tricyclohexyl phosphine, placed in dioxane and refluxed for 12 hours, after the reaction was completed, the The mixture was cooled to room temperature, filtered to remove the salt, and the resulting liquid was distilled under reduced pressure to obtain a dark brown solid, which was recrystallized to obtain compound h;

Step 5. Dissolve compound h, compound i, tetrakistriphenylphosphine palladium and potassium carbonate in tetrahydrofuran and H ₂ O, and reflux for 12 hours. After the reaction is completed, cool the reaction mixture to room temperature, filter, and dissolve the obtained solid in In _CHCl3 , with _MgSO4Dry , filter through diatomaceous earth, recrystallize, obtain the compound shown in formula 1;

Its synthetic route is as follows:

In the formula: X is O or S; Ar ₁ is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted aromatic heterocyclic group; Ar is hydrogen or benzene; Z ₁ to Z ₅ are N or O, and Z At least one of ₁ to Z ₅ is C; the position indicated by the dotted line in the formula can be combined with a phenyl group.

An organic light-emitting device, the material of the electron transport layer is the organic light-emitting compound shown in formula 1.

The organic light-emitting compound can be applied to organic solar cells, electronic paper, organic photoreceptors, organic transistors or inkjet printing materials.

The beneficial effects of the present invention are:

The organic luminescent compound provided by the present invention has relatively appropriate color coordinates, high purity, and excellent skeleton as an electron transport layer material of an organic light-emitting device. Compared with other electron transport layer materials, the organic luminescent compound provided by the present invention is used as The organic light-emitting device prepared from the material of the electron transport layer has a significantly improved luminous efficiency and a significantly improved lifespan.

The preparation method of the organic light-emitting compound provided by the invention has easy-to-obtain raw materials and simple process, and is suitable for industrialized production.

Detailed ways

The present invention provides an organic luminescent compound, the chemical structural formula of which is shown in Formula 1:

In the formula: X is O or S; Ar ₁ is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted aromatic heterocyclic group; Ar is hydrogen or benzene; Z ₁ to Z ₅ are N or O, and Z At least one of ₁ to Z ₅ is C; the position indicated by the dotted line in the formula can be combined with a phenyl group.

Preferably, the organic light-emitting compound is any one of the following structures:

In the above structural formula, Ar ₁ is preferably a substituted or unsubstituted phenyl group with 6-16 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group with 5-11 carbon atoms. It is further preferred that Ar ₁ is a substituted or unsubstituted phenyl group having 11-16 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 6-10 carbon atoms. More preferably, Ar ₁ is a substituted or unsubstituted phenyl group having 11 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 7 carbon atoms. More preferably Ar is pyridyl, picoline, _lutyl , methylpyrimidinyl, dimethylpyrimidinyl, 4-pyridylphenyl, 4-(3-methylisoquinolinyl)benzene 2,3-dimethyl-1,4-quinoxalinyl, 2-methylisoquinolinyl or 2-methylbipyridyl.

Most preferably, the organic light-emitting compound is any one of the structures shown below:

The present invention also provides a method for preparing an organic luminescent compound, comprising the following steps:

Step 1. Put compound a, compound b, potassium carbonate, and tetrakistriphenylphosphine palladium into a round-bottomed flask, and pour tetrahydrofuran and H ₂ O into it, and reflux the mixture for 24 hours. After the reaction is completed, remove the water layer , the organic layer was dried with MgSO ₄ and distilled under reduced pressure, and the crude product was recrystallized to obtain compound c;

Step 2. Put compound c, compound d, and K ₃ PO ₄ in dimethyl sulfoxide, heat the mixture to 90°C for 1 hour, after the reaction is completed, add water to the reaction mixture, filter it to obtain light yellow Solid, then add 2,3-dichloro-5,6-dicyano-p-benzoquinone to the solution, stir at room temperature for 10 minutes, after the reaction is complete, filter, and distill under reduced pressure, the resulting crude product is passed through silica gel column chromatography Purify, using 0-10% ethyl acetate in hexane as eluent to obtain compound e;

Step 3. Put compound e, compound f, potassium carbonate, and tetrakistriphenylphosphine palladium into a round-bottomed flask, and pour tetrahydrofuran and H ₂ O into it, and reflux the mixture for 24 hours. After the reaction is completed, remove the water layer , the organic layer was dried with MgSO ₄ and distilled under reduced pressure, and the crude product was recrystallized to obtain compound g;

Step 4, compound g, two (pinacol) diboron, potassium acetate, two (dibenzylideneacetone) palladium, tricyclohexyl phosphine, placed in dioxane and refluxed for 12 hours, after the reaction was completed, the The mixture was cooled to room temperature, filtered to remove the salt, and the resulting liquid was distilled under reduced pressure to obtain a dark brown solid, which was recrystallized to obtain compound h;

Step 5. Dissolve compound h, compound i, tetrakistriphenylphosphine palladium and potassium carbonate in tetrahydrofuran and H ₂ O, and reflux for 12 hours. After the reaction is completed, cool the reaction mixture to room temperature, filter, and dissolve the obtained solid in In _CHCl3 , with _MgSO4Dry , filter through diatomaceous earth, recrystallize, obtain the compound shown in formula 1;

Its synthetic route is as follows:

In the formula: X is O or S; Ar ₁ is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted aromatic heterocyclic group; Ar is hydrogen or benzene; Z ₁ to Z ₅ are N or O, and Z At least one of ₁ to Z ₅ is C;; the position indicated by the dotted line in the formula can be combined with a phenyl group.

The present invention also provides an organic light-emitting device, the electron transport layer material of which is the organic light-emitting compound represented by Formula 1.

The organic light-emitting compound can be applied to organic solar cells, electronic paper, organic photoreceptors, organic transistors or inkjet printing materials.

Put 3-bromo-5-chlorobenzaldehyde (118.3mmol), (6-bromopyridin-2-yl)boronic acid (118.3mmol), potassium carbonate (354.9mmol), tetrakistriphenylphosphine palladium (2mol%) In a round-bottomed flask, tetrahydrofuran (THF) (500 mL) and H ₂ O (250 mL) were poured into it, and the mixture was refluxed for 24 hours. After the reaction was completed, the aqueous layer was removed, and the organic layer was dried with MgSO ₄ and distilled under reduced pressure. The crude product was recrystallized to give 3-(6-bromopyridin-2-yl)-5-chlorobenzaldehyde (73.35 mmol, 62% yield).

the intermediate replace with According to the preparation method of 3-(6-bromopyridin-2-yl)-5-chlorobenzaldehyde, use the same molar ratio and the same catalyst to obtain intermediates successively

Synthesis of 2-(3'-bromo-5-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine:

3-(6-Bromopyridin-2-yl)-5-chlorobenzaldehyde (136.7 mmol), benzamidine hydrochloride (273.4 mmol), K ₃ PO ₄ (273.4 mmol) were placed in dimethylsulfoxide (DMSO) , the mixture was heated to 90°C for 1 hour. After the reaction was completed, water was added to the reaction mixture, which was filtered to obtain a light yellow solid, and then 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) (136.7mmol) was added to the solution, Stir at room temperature for 10 minutes. After the reaction was completed, it was filtered and distilled under reduced pressure. The resulting crude product was purified by column chromatography on silica gel using 0-10% ethyl acetate in hexane as eluent to afford Intermediate 1-1 (118.9 mmol, 87% yield), theoretically 498.02, measured as 498.06.

the intermediate replace with According to the preparation method of intermediate 1-1, using the same molar ratio and the same catalyst, the intermediate is obtained in sequence

[Synthesis Example 1] Synthesis of Compound 001

Intermediate 1-1 (118.3mmol), benzo[b]naphtho[2,3-d]furan-2-ylboronic acid (118.3mmol), potassium carbonate (354.9mmol), tetrakistriphenylphosphine palladium ( 2mol%) into a round-bottomed flask, and tetrahydrofuran (THF) (500mL) and H ₂ O (250mL) were poured into it, and the mixture was refluxed for 24 hours. After the reaction was completed, the water layer was removed, and the organic layer was dried with MgSO ₄ And distilled under reduced pressure. The crude product was recrystallized to obtain intermediate 2-1 (107.65 mmol, 91% yield), theoretical value 636.17, measured value 636.20.

Intermediate 2-1 (106.6mmol), bis(pinacol) diboron (117.3mmol), potassium acetate (319.8mmol), bis(dibenzylideneacetone) palladium (3mol%), tricyclohexylphosphine ( 6mol%), placed in dioxane (500mL) and refluxed for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered to remove salt, and the resulting liquid was distilled under reduced pressure to obtain a dark brown solid, which was recrystallized to obtain Intermediate 3-1 (96.19 mmol, yield 82%), the theoretical value was 728.30 , which measures 728.25.

Intermediate 3-1 (22.1 mmol), 2-bromopyridine (22.1 mmol), tetrakistriphenylphosphine palladium (0.76 g, 3 mol%) and potassium carbonate (6.11 g, 44.2 mmol) were dissolved in THF (110 mL) and H ₂ O (55 mL), refluxed for 12 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and filtered. The resulting solid was dissolved in CHCl ₃ , dried with MgSO ₄ , filtered through celite, and recrystallized to give compound 001 (13.70 mmol, yield 62%), theoretical value 679.24, measured value 679.27.

[Synthesis Example 2] Synthesis of Compound 002

Intermediate 1-2 (118.3mmol), phenanthrene[9,10-b]benzofuran-12-ylboronic acid (118.3mmol), potassium carbonate (354.9mmol), tetrakistriphenylphosphine palladium (2mol%) Put into a round bottom flask, and pour tetrahydrofuran (THF) (500mL) and H ₂ O (250mL) into it, reflux the mixture for 24 hours, after the reaction is complete, remove the water layer, and the organic layer is dried with MgSO ₄ and reduced pressure Distillation and recrystallization of the crude product gave intermediate 2-2 (107.65 mmol, 91% yield), theoretical value 688.19, measured value 688.25.

Intermediate 2-2 (106.6mmol), bis(pinacol) diboron (117.3mmol), potassium acetate (319.8mmol), bis(dibenzylideneacetone)palladium (3mol%), tricyclohexylphosphine ( 6mol%), placed in dioxane (500mL) and refluxed for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered to remove salt, and the resulting liquid was distilled under reduced pressure to obtain a dark brown solid, which was recrystallized to obtain Intermediate 3-2 (96.19 mmol, yield 82%), the theoretical value was 779.31 , measured at 779.36.

Intermediate 3-2 (22.1 mmol), 3-bromopyridine (22.1 mmol), tetrakistriphenylphosphine palladium (0.76 g, 3 mol%) and potassium carbonate (6.11 g, 44.2 mmol) were dissolved in THF (110 mL) and H ₂ O (55 mL), refluxed for 12 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and filtered. The resulting solid was dissolved in CHCl ₃ , dried over MgSO ₄ , filtered through celite, and recrystallized to give compound 002 (13.70 mmol, yield 62%), theoretical value 730.25, measured value 730.31.

[Synthesis Example 3] Synthesis of Compound 003

Intermediate 1-3 (118.3mmol), benzo[b]phenanthrene[9,10-d]thiophen-12-ylboronic acid (118.3mmol), potassium carbonate (354.9mmol), tetrakistriphenylphosphine palladium ( 2mol%) into a round-bottomed flask, and tetrahydrofuran (THF) (500mL) and H ₂ O (250mL) were poured into it, and the mixture was refluxed for 24 hours. After the reaction was completed, the water layer was removed, and the organic layer was dried with MgSO ₄ And distilled under reduced pressure, the crude product was recrystallized to obtain intermediate 2-3 (107.65 mmol, yield 91%), the theoretical value was 703.16, and the measured value was 703.19.

Intermediate 2-3 (106.6mmol), bis(pinacol) diboron (117.3mmol), potassium acetate (319.8mmol), bis(dibenzylideneacetone)palladium (3mol%), tricyclohexylphosphine ( 6mol%), placed in dioxane (500mL) and refluxed for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to remove salt, and the resulting liquid was distilled under reduced pressure to obtain a dark brown solid, which was recrystallized to obtain intermediate Body 3-3 (96.19 mmol, 82% yield), theoretical value 780.26, measured value 780.31.

Intermediate 3-3 (22.1 mmol), 4-bromopyridine (22.1 mmol), tetrakistriphenylphosphine palladium (0.76 g, 3 mol%) and potassium carbonate (6.11 g, 44.2 mmol) were dissolved in THF (110 mL) and H ₂ O (55 mL), refluxed for 12 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and filtered. The resulting solid was dissolved in CHCl ₃ , dried over MgSO ₄ , filtered through celite, and recrystallized to give compound 003 (13.70 mmol, yield 62%), theoretical value 747.23, measured value 747.29.

[Synthesis Example 4] Synthesis of Compound 024

Intermediate 1-1 (118.3mmol), (3-(naphthol[2,1-b]benzene-10-yl)boronic acid (118.3mmol), potassium carbonate (354.9mmol), tetrakistriphenylphosphine palladium ( 2mol%) into a round-bottomed flask, and tetrahydrofuran (THF) (500mL) and H ₂ O (250mL) were poured into it, and the mixture was refluxed for 24 hours. After the reaction was completed, the water layer was removed, and the organic layer was dried with MgSO ₄ And distilled under reduced pressure, the crude product was recrystallized to obtain intermediate 2-24 (107.65 mmol, yield 91%), the theoretical value was 715.19, and the measured value was 715.20.

Intermediate 2-24 (106.6mmol), bis(pinacol)diboron (117.3mmol), potassium acetate (319.8mmol), bis(dibenzylideneacetone)palladium (3mol%), tricyclohexylphosphine ( 6mol%), placed in dioxane (500mL) and refluxed for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to remove salt, and the resulting liquid was distilled under reduced pressure to obtain a dark brown solid, which was recrystallized to obtain intermediate Body 3-24 (96.19 mmol, 82% yield), theoretical 806.32, measured 806.39.

Intermediate 3-24 (22.1 mmol), 2,6-dimethyl-3-bromopyridine (22.1 mmol), tetrakistriphenylphosphine palladium (0.76 g, 3 mol%) and potassium carbonate (6.11 g, 44.2 mmol) Dissolve in tetrahydrofuran THF (110 mL) and H ₂ O (55 mL), and reflux for 12 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and filtered. The resulting solid was dissolved in CHCl ₃ , dried with MgSO ₄ , filtered through celite, and recrystallized to give compound 024 (13.70 mmol, yield 62%), theoretical value 785.29, measured value 785.36.

[Synthesis Example 5-30]

According to the synthesis method of the above compound 001, compound 002 and compound 003, the intermediate 1-1, intermediate 1-2 and intermediate 1-3 in the general formula are replaced by In the general formula replace with Obtain the corresponding intermediate according to the same quantitative ratio;

According to the synthetic method of above-mentioned compound 001, compound 002 and compound 003, the Ar group in the ₂ -bromopyridine in the reaction formula is replaced by methylpyridyl, lutyl, methylpyrimidinyl, dimethyl Pyrimidinyl, 4-pyridylphenyl, 4-(3-methylisoquinolinyl)phenyl, 2,3-dimethyl-1,4-quinoxalinyl, 2-methylisoquinolinyl Or 2-methylbipyridyl, react with the corresponding intermediate to obtain the corresponding compound 004-023, 025-030.

Examples of Manufacturing of Organic Light Emitting Devices

[Experimental example] Green organic light-emitting device (electron transport layer)

First, 4,4',4"-tris[2-naphthylphenylamino]triphenylamine (hereinafter referred to as 2 -TNATA) to form a hole injection layer, and vacuum-evaporated N,N'-diphenyl-N,N'-(1-naphthyl)-1,1' with a thickness of 60 nm on the formed hole injection layer. -biphenyl-4,4'-diamine (hereinafter referred to as NPD) to form the hole transport layer. Then, a thickness of 30nm4,4'-two (9-carbazole) was vacuum evaporated on the above hole transport layer ) biphenyl as the main body (hereinafter referred to as CBP), the doped mixture is the light-emitting layer with three (2-phenylpyridine) iridium, and the weight ratio of the main material and the doping material is 95:5. Next, in the above Bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (hereinafter referred to as BAlq) with a thickness of 10 nm was vacuum-evaporated on the light-emitting layer to form a void. Hole blocking layer. On the above-mentioned hole blocking layer, the vacuum evaporation thickness is any one of the compounds 1-14 of the present invention of 40nm to form an electron transport layer. Subsequently, in the above-mentioned electron transport layer, a thickness of 40 nm is evaporated. Lithium fluoride of 0.2nm alkali metal halide forms an electron injection layer. Then aluminum with a thickness of 150nm is vapor-deposited to form a cathode, thereby completing the preparation of an organic light-emitting device.

[comparative example]

Comparative example (1)

An organic light-emitting device was prepared in the same manner as the above experimental example, except that the comparative compound 1 was used instead of the compound of the present invention as the substance of the electron transport layer.

<Comparative compound 1> Alq3

Comparative example (2)

Except that the compound of the present invention was replaced by comparative compound 2 as the substance of the electron transport layer, an organic light-emitting device was prepared in the same manner as the above experimental example.

<Comparative compound 2>

Comparative example (3)

The organic light-emitting device was prepared in the same way as the above experimental example, except that the comparative compound 3 was used as the substance of the electron transport layer instead of the compound represented by the present invention.

<Comparative compound 3>

Apply a forward DC bias voltage to the organic light-emitting device prepared above, use Photo Research's PR-650 photometric measurement equipment to measure the electroluminescence characteristics, and use the lifespan manufactured by ^McScience under the reference grayscale of 5000cd/m2 The measuring device measures the life of T95. The results are shown in Table 1.

[Table 1]

As can be seen from the above Table 1, the organic light-emitting device prepared by using the organic light-emitting compound of the present invention as the electron-transport layer, compared with the organic light-emitting device prepared by the comparative compound 1-3 as the electron-transport layer, is the same at 5000 cd/ Under the standard gray scale of m ² , it has lower driving voltage and current density, higher luminous efficiency, and higher lifetime.

The preferred specific embodiments of the present invention are described above. Those skilled in the art should understand that the present invention is not limited by the above embodiments, and the present invention also has various changes and changes without departing from the spirit and scope of the present invention. These changes and improvements all fall within the protection scope of the present invention. The protection scope of the present invention is defined by the appended claims and their equivalents.

Claims (10)

1. An organic luminescent compound, characterized in that its chemical structural formula is as shown in formula 1: In the formula: X is O or S; Ar ₁ is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted aromatic heterocyclic group; Ar is hydrogen or benzene; Z ₁ to Z ₅ are N or O, and at least one of Z ₁ to Z ₅ is C; A phenyl group may be attached to the position indicated by the dotted line in the formula. 2. The organic light-emitting compound according to claim 1, wherein the organic light-emitting compound is any one of the following structures: 3. The organic light-emitting compound according to claim ₁ or 2, wherein Ar is a substituted or unsubstituted phenyl group with 6-16 carbon atoms, or a substituted or unsubstituted phenyl group with 5-11 carbon atoms. aromatic heterocyclic group. 4. The organic light-emitting compound according to claim ₁ or 2, wherein Ar is a substituted or unsubstituted phenyl group with 11-16 carbon atoms, or a substituted or unsubstituted phenyl group with 6-10 carbon atoms. aromatic heterocyclic group. 5. The organic light-emitting compound according to claim ₁ or 2, wherein Ar is a substituted or unsubstituted phenyl group with 11 carbon atoms, or a substituted or unsubstituted aromatic hetero with 7 carbon atoms. Ring base. 6. The organic light-emitting compound according to claim ₁ or 2, wherein Ar is pyridyl, picoline, lutyl, methylpyrimidinyl, dimethylpyrimidinyl, 4-pyridine phenyl, 4-(3-methylisoquinolinyl)phenyl, 2,3-dimethyl-1,4-quinoxalinyl, 2-methylisoquinolinyl or 2-methylbis pyridyl. 7. The organic light-emitting compound according to claim 1, wherein the organic light-emitting compound is any one of the following structures: 8. The method for preparing an organic luminescent compound according to claim 1, comprising the following steps: Step 1. Put compound a, compound b, potassium carbonate, and tetrakistriphenylphosphine palladium into a round-bottomed flask, and pour tetrahydrofuran and H ₂ O into it, and reflux the mixture for 24 hours. After the reaction is completed, remove the water layer , the organic layer was dried with MgSO ₄ and distilled under reduced pressure, and the crude product was recrystallized to obtain compound c; Step 2. Put compound c, compound d, and K ₃ PO ₄ in dimethyl sulfoxide, heat the mixture to 90°C for 1 hour, after the reaction is completed, add water to the reaction mixture, filter it to obtain light yellow Solid, then add 2,3-dichloro-5,6-dicyano-p-benzoquinone to the solution, stir at room temperature for 10 minutes, after the reaction is complete, filter, and distill under reduced pressure, the resulting crude product is passed through silica gel column chromatography Purify, using 0-10% ethyl acetate in hexane as eluent to obtain compound e; Step 3. Put compound e, compound f, potassium carbonate, and tetrakistriphenylphosphine palladium into a round-bottomed flask, and pour tetrahydrofuran and H ₂ O into it, and reflux the mixture for 24 hours. After the reaction is completed, remove the water layer , the organic layer was dried with MgSO ₄ and distilled under reduced pressure, and the crude product was recrystallized to obtain compound g; Step 4, compound g, two (pinacol) diboron, potassium acetate, two (dibenzylideneacetone) palladium, tricyclohexyl phosphine, placed in dioxane and refluxed for 12 hours, after the reaction was completed, the The mixture was cooled to room temperature, filtered to remove the salt, and the resulting liquid was distilled under reduced pressure to obtain a dark brown solid, which was recrystallized to obtain compound h; Step 5. Dissolve compound h, compound i, tetrakistriphenylphosphine palladium and potassium carbonate in tetrahydrofuran and H ₂ O, and reflux for 12 hours. After the reaction is completed, cool the reaction mixture to room temperature, filter, and dissolve the obtained solid in In _CHCl3 , with _MgSO4Dry , filter through diatomaceous earth, recrystallize, obtain the compound shown in formula 1; Its synthetic route is as follows: In the formula: X is O or S; Ar ₁ is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted aromatic heterocyclic group; Ar is hydrogen or benzene; Z ₁ to Z ₅ are N or O, and Z At least one of ₁ to Z ₅ is C; the position indicated by the dotted line in the formula can be combined with a phenyl group. 9. An organic light-emitting device, characterized in that the electron transport layer material is an organic light-emitting compound represented by Formula 1. 10. The organic light-emitting compound according to claim 1 can be applied to organic solar cells, electronic paper, organic photoreceptors, organic transistors or inkjet printing materials.