阅读说明：本技术 一种芳胺类化合物及其制备方法和应用 (Arylamine compound and preparation method and application thereof ) 是由 金成寿 马晓宇 张鹤 王进政 黄悦 张雪 汪康 于 2020-11-24 设计创作，主要内容包括：本发明公开了一种芳胺类化合物及其制备方法和应用,芳胺类化合物的结构通式如化学式1所示：本发明中的芳胺类化合物作为新的芳胺类CPL材料,能够提高在各个波长下的折射率,从而来提高对各种不同颜色的光的提取效率,且含有该材料的有机EL器件的发光效率、热稳定性、寿命、启动电压等性能得到极大的改善。(The invention discloses an arylamine compound and a preparation method and application thereof, wherein the structural general formula of the arylamine compound is shown as a chemical formula 1:)

1. An arylamine compound is characterized in that the structural general formula of the arylamine compound is shown as chemical formula 1:

wherein Ar is₁-Ar₂Each independently represents: hydrogen, isotopes of hydrogen, substituted or unsubstituted C1-C60 alkyl, C3-C60 cycloalkyl, substituted or unsubstituted C2-C60 alkenyl, C3-C60 cycloalkenyl, substituted or unsubstituted C3-C60 alkynyl, C3-C60 cycloalkynyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted 6-30 membered heterocyclyl;

or, each is linked to an adjacent substituent to form a substituted or unsubstituted monocyclic or polycyclic ring;

x is an oxygen or sulfur atom;

l is a connecting bond, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-10 member heterocyclyl, substituted or unsubstituted C6-C30 condensed ring group;

or, taken together with an adjacent substituent to form a substituted or unsubstituted monocyclic or polycyclic ring;

R₁-R₄each independently represents: hydrogen, isotopes of hydrogen, substituted or unsubstituted C1-C60 alkyl, C3-C60 cycloalkyl, substituted or unsubstituted C2-C60 alkenyl, C3-C60 cycloalkenyl, substituted or unsubstituted C3-C60 alkynyl, C3-C60 cycloalkynyl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C1-C20 alkylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted 3-10 membered heterocyclyl;

or, each is linked to an adjacent substituent to form a substituted or unsubstituted monocyclic or polycyclic ring.

2. An arylamine compound according to claim 1, wherein the substituted or unsubstituted monocyclic or polycyclic ring is a C3-C30 aliphatic ring or a 3-10 membered aromatic ring;

wherein at least one of the carbon atoms in the aliphatic ring or the aromatic ring is replaced by one of nitrogen, oxygen, silicon and sulfur.

3. The aromatic amine compound of claim 1, wherein L is one of phenyl, biphenylyl, terphenylyl, naphthyl, isopropyl, and cyclohexyl.

4. An arylamine compound according to claim 1, wherein Ar is selected from the group consisting of₁And Ar₂Independently selected from any one of the following structures:

wherein R is selected from hydrogen, halogen, cyano, C1-C30 alkyl, C6-C50 aryl, C7-C50 aralkyl, C7-C50 arylalkoxy, C7-C50 arylalkylmercapto or C5-C50 heteroaryl;

and said-R represents any position on the phenyl ring on which it is located, "+" is the linking position.

5. A process for the preparation of an aromatic amine compound according to any one of claims 1 to 4, comprising the steps of:

the synthesis method of the chemical formula 1 is as follows:

the method comprises the following specific steps:

(1) under the protection of nitrogen, adding I-1 and I-2 into a toluene solvent, heating to 50 ℃, stirring for 15min, sequentially adding sodium tert-butoxide, tri-tert-butylphosphine and tris (dibenzylideneacetone) dipalladium, continuously heating to 65 ℃ for reaction, cooling to room temperature after the reaction is finished, extracting, drying, filtering, concentrating and purifying to obtain an intermediate I-3;

(2) under the protection of nitrogen, adding the intermediates I-4 and I-5 into toluene, heating to 50 ℃, stirring for 15min, sequentially adding potassium carbonate and tetratriphenylphosphine palladium, continuously heating to 65 ℃ for reaction, cooling to room temperature after the reaction is finished, extracting, drying, filtering, concentrating and purifying to obtain an intermediate I-6.

(3) Under the protection of nitrogen, adding the intermediates I-3 and I-6 into toluene, heating to 50 ℃, stirring for 15min, sequentially adding sodium tert-butoxide, tri-tert-butylphosphine and tris (dibenzylideneacetone) dipalladium, continuously heating to 65 ℃ for reflux reaction, cooling to room temperature after the reaction is finished, extracting, drying, filtering, concentrating and purifying to obtain the chemical formula I.

6. A process for the preparation of an aromatic amine compound according to claim 5, wherein in step (1), the molar ratio of I-1, I-2, sodium tert-butoxide, tri-tert-butylphosphine and tris (dibenzylideneacetone) dipalladium is 100: 100: 200: 2: 1.

7. a method for preparing an aromatic amine compound according to claim 5, wherein in the step (2), the molar ratio of I-4, I-5, potassium carbonate and palladium tetratriphenylphosphine is 100: 100: 20: 1.

8. a process for the preparation of an aromatic amine compound according to claim 5, wherein in step (3), the molar ratio of the intermediates I-3, I-6, sodium tert-butoxide, tri-tert-butylphosphine and tris (dibenzylideneacetone) dipalladium is 76.68: 76.68: 153.36: 1.53: 0.77.

9. use of an aromatic amine compound according to any one of claims 1 to 4 or prepared by a process according to any one of claims 5 to 8 for the preparation of an organic electroluminescent device.

10. An organic electroluminescent device as claimed in claim 9, comprising: the ITO anode comprises a substrate, an ITO anode, a hole injection layer, a hole transport layer, a light emitting layer, a first electron transport layer and a second electron transport layer; the light-emitting layer includes the arylamine compound.

Technical Field

The invention relates to the technical field of organic electroluminescent materials, in particular to an arylamine compound and a preparation method and application thereof.

Background

OLED displays may be classified into bottom-emitting OLED displays and top-emitting OLED displays according to the direction in which light is emitted from an organic light emitting layer. In the bottom-emitting OLED display, light is emitted toward the substrate, and the thin film transistor portion formed therein does not transmit light, resulting in a reduction in light emitting area. In the top emission OLED display, the transparent electrode is formed above the organic light emitting layer and the reflective electrode is formed below the organic light emitting layer, so that light is emitted in the opposite direction to the substrate, thereby increasing the light transmission area and improving the brightness. Aiming at the current situation that the light extraction efficiency of the OLED device is low at present, the surface covering layer is used on the light-emitting surface of the substrate, the process is simple, the light-emitting efficiency is remarkably improved, and people pay attention to the method.

The surface of the cathode in the top-emitting device structure is covered with a cap layer (CPL, also called as cathode covering layer), namely a light extraction material, so as to adjust the optical interference distance, inhibit external light emission and inhibit extinction caused by the movement of surface plasma. The material of the surface covering layer should have a higher refractive index as good as possible, according to the principles of optical absorption and refraction.

Problems with existing CPL materials include: (1) the refractive index is not high enough, and the light extraction effect is not good enough; (2) the difference in refractive index measured in each wavelength region of blue light, green light, and red light is large. Therefore, high light extraction efficiency cannot be simultaneously obtained for all the lights in the light emitting device emitting blue, green, and red lights.

Therefore, it is an urgent problem to be solved by those skilled in the art to provide an arylamine compound capable of increasing the refractive index at each wavelength to improve the extraction efficiency of light of different colors.

Disclosure of Invention

In view of the above, the present invention provides an arylamine compound capable of increasing a refractive index at each wavelength to improve extraction efficiency of light of various colors.

In order to achieve the purpose, the invention adopts the following technical scheme: an arylamine compound, the structural general formula of which is shown in chemical formula 1:

wherein Ar is₁-Ar₂Each independently represents: hydrogen, isotopes of hydrogen, substituted or unsubstituted C1-C60 alkyl, C3-C60 cycloalkyl, substituted or unsubstituted C2-C60 alkenyl, C3-C60 cycloalkenyl, substituted or unsubstituted C3-C60 alkynyl, C3-C60 cycloalkynyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted 6-30 membered heterocyclyl;

or, each is linked to an adjacent substituent to form a substituted or unsubstituted monocyclic or polycyclic ring;

x is an oxygen or sulfur atom;

l is a connecting bond, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-10 member heterocyclyl, substituted or unsubstituted C6-C30 condensed ring group;

or, taken together with an adjacent substituent to form a substituted or unsubstituted monocyclic or polycyclic ring;

R₁-R₄each independently represents: hydrogen, isotopes of hydrogen, substituted or unsubstituted C1-C60 alkyl, C3-C60 cycloalkyl, substituted or unsubstituted C2-C60 alkenyl, C3-C60 cycloalkenyl, substituted or unsubstituted C3-C60 alkynyl, C3-C60 cycloalkynyl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C1-C20 alkylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted CSubstituted 3-10 membered heterocyclic group.

Or, each is linked to an adjacent substituent to form a substituted or unsubstituted monocyclic or polycyclic ring.

The invention has the beneficial effects that: the arylamine CPL material has the refractive index at each wavelength, so that the extraction efficiency of light with different colors is improved.

Preferably, Ar is₁-Ar₄L and R₁-R₄Each linked to an adjacent substituent to form a mono-or polycyclic ring, each of which is a C3-C30 aliphatic ring or a 3-10 membered aromatic ring;

wherein at least one of the carbon atoms in the aliphatic ring or the aromatic ring is replaced by one of nitrogen, oxygen, silicon and sulfur.

Preferably, the L is one of phenyl, biphenylyl, terphenylyl, naphthyl, isopropyl, and cyclohexyl.

Preferably, Ar is₁And Ar₂Any one selected from the following structures:

wherein R is selected from hydrogen, halogen, cyano, C1-C30 alkyl, C6-C50 aryl, C7-C50 aralkyl, C7-C50 arylalkoxy, C7-C50 arylalkylmercapto and C5-C50 heteroaryl; and said-R represents any position on the phenyl ring on which it is located, "+" is the linking position.

The aromatic compound of chemical formula 1 in the present invention may be preferably selected from one of the following specific structures, but is not limited thereto:

the invention also provides a preparation method of the arylamine compound, which comprises the following steps:

the synthesis method of the chemical formula 1 is as follows:

the method comprises the following specific steps:

(1) under the protection of nitrogen, adding I-1 and I-2 into a toluene solvent, heating to 50 ℃, stirring for 15min, sequentially adding sodium tert-butoxide, tri-tert-butylphosphine and tris (dibenzylideneacetone) dipalladium, continuously heating to 65 ℃ for reaction, cooling to room temperature after the reaction is finished, extracting, drying, filtering, concentrating and purifying to obtain an intermediate I-3;

(2) under the protection of nitrogen, adding the intermediates I-4 and I-5 into toluene, heating to 50 ℃, stirring for 15min, sequentially adding potassium carbonate and tetratriphenylphosphine palladium, continuously heating to 65 ℃ for reaction, cooling to room temperature after the reaction is finished, extracting, drying, filtering, concentrating and purifying to obtain an intermediate I-6.

(3) Under the protection of nitrogen, adding the intermediates I-3 and I-6 into toluene, heating to 50 ℃, stirring for 15min, sequentially adding sodium tert-butoxide, tri-tert-butylphosphine and tris (dibenzylideneacetone) dipalladium, heating to 65 ℃ for reflux reaction, cooling to room temperature after the reaction is finished, extracting, drying, filtering, concentrating and purifying to obtain the chemical formula I.

Preferably, in the step (1), the molar ratio of the I-1, the I-2, the sodium tert-butoxide, the tri-tert-butylphosphine and the tris (dibenzylideneacetone) dipalladium is 100: 100: 20: 1: 1.

preferably, in the step (2), the molar ratio of the I-4 to the I-5 to the potassium carbonate to the palladium tetratriphenylphosphine is 100: 100: 200: 2: 1.

preferably, in step (3), the molar ratio of the intermediate I-3, I-6, sodium tert-butoxide, tri-tert-butylphosphine and tris (dibenzylideneacetone) dipalladium is 76.68: 76.68: 153.36: 1.53: 0.77.

the invention also provides application of the arylamine compound in an organic electroluminescent device.

The present invention also provides an organic electroluminescent device comprising: the ITO anode comprises a substrate, an ITO anode, a hole injection layer, a hole transport layer, a light emitting layer, a first electron transport layer and a second electron transport layer; the light-emitting layer includes the arylamine compound.

According to the technical scheme, compared with the prior art, the arylamine compound and the preparation method and application thereof are disclosed, the arylamine compound is used as a novel arylamine CPL material, and the refractive index of the CPL material under each wavelength can be improved, so that the extraction efficiency of light with different colors is improved. The organic EL device containing the material has greatly improved performances of luminous efficiency, thermal stability, service life, starting voltage and the like.

Detailed Description

The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.

Example 1: synthesis of Compound 1

(1) Under the protection of nitrogen, adding 1-4(18g, 100mmol) and 1-5(34.36g, 100mmol) into a toluene/water mixed solvent, heating to 50 ℃, stirring for 15min, sequentially adding potassium carbonate (27.6g, 200mmol) and tetratriphenylphosphine palladium (1.15g, 1mmol), heating to 65 ℃ for reaction after the addition is finished, monitoring the reaction process by TLC, and cooling to room temperature after the reaction is finished; after transferring to a separatory funnel and extracting with ethyl acetate and water, the extract was dried over anhydrous magnesium sulfate, filtered and concentrated, and then the sample was purified by silica gel column chromatography to obtain 1-6-333.36g of intermediate (yield: 83.63%).

(2) Under the protection of nitrogen, adding 1-1(100mmol) and 1-2(100mmol) into toluene, heating to 50 ℃, stirring for 15min, sequentially adding sodium tert-butoxide (200mmol), tri-tert-butylphosphine (2mmol) and tris (dibenzylideneacetone) dipalladium (1mmol), heating to 65 ℃ for reaction after the addition is finished, monitoring the reaction process by TLC, and cooling to room temperature after the reaction is finished; after transferring to a separatory funnel and extracting with ethyl acetate and water, the extract was dried over anhydrous magnesium sulfate, filtered and concentrated, and then the sample was purified by silica gel column chromatography to obtain 1 to 3 of intermediate, 26.39g (yield: 82.11%).

(3) Under the protection of nitrogen, adding the intermediates 1-3(83.63mmol) and 1-6(83.63mmol) into toluene, heating to 50 ℃, stirring for 15min, sequentially adding sodium tert-butoxide (167.26mmol), tri-tert-butylphosphine (1.67mmol) and tris (dibenzylideneacetone) dipalladium (0.84mmol), and heating to reflux reaction after the addition is finished; the progress of the reaction was monitored by TLC, and after completion of the reaction, the reaction mixture was cooled to room temperature, and then transferred to a separatory funnel, extracted with ethyl acetate and water, and the extract was dried over anhydrous magnesium sulfate, filtered and concentrated, and then the sample was purified by silica gel column chromatography and recrystallized from toluene to obtain 148.36g of the compound (yield: 84.55%).

Example 2: synthesis of Compound 13

(1) Under the protection of nitrogen, adding 13-4(100mmol) and 13-5(100mmol) into a toluene/water mixed solvent, heating to 50 ℃, stirring for 15min, sequentially adding potassium carbonate (200mmol) and tetratriphenylphosphine palladium (1mmol), heating to 65 ℃ for reaction after the addition is finished, monitoring the reaction process by TLC, and cooling to room temperature after the reaction is finished; after transferring to a separatory funnel and extracting with ethyl acetate and water, the extract was dried over anhydrous magnesium sulfate, filtered and concentrated, and then the sample was purified by silica gel column chromatography to obtain intermediate 13 to 621.06g (yield: 85.33%).

(2) Under the protection of nitrogen, adding 13-1(100mmol) and 13-2(100mmol) into toluene, heating to 50 ℃, stirring for 15min, sequentially adding sodium tert-butoxide (200mmol), tri-tert-butylphosphine (2mmol) and tris (dibenzylideneacetone) dipalladium (1mmol), heating to 65 ℃ for reaction after the addition is finished, monitoring the reaction process by TLC, and cooling to room temperature after the reaction is finished; after transferring to a separatory funnel and extracting with ethyl acetate and water, the extract was dried over anhydrous magnesium sulfate, filtered and concentrated, and then the sample was purified by silica gel column chromatography to obtain intermediate 13 to 329.56g (yield: 76.68%).

(3) Under the protection of nitrogen, adding the intermediate 13-3(76.68mmol) and 13-6(76.68mmol) into toluene, heating to 50 ℃, stirring for 15min, sequentially adding sodium tert-butoxide (153.36mmol), tri-tert-butylphosphine (1.53mmol) and tris (dibenzylideneacetone) dipalladium (0.77mmol), and heating to reflux reaction after the addition is finished; the progress of the reaction was monitored by TLC and, after completion of the reaction, the temperature was lowered to room temperature. Transferred to a separatory funnel and extracted with ethyl acetate and water. The extract was dried over anhydrous magnesium sulfate, filtered and concentrated, and then the sample was purified by silica gel column chromatography. Further, by slurrying with toluene, the compound 1338.32g (yield: 83.87%) was obtained.

Example 3: synthesis of Compound 15

(1) Under the protection of nitrogen, adding 15-4(100mmol) and 15-5(100mmol) into a toluene/water mixed solvent, heating to 50 ℃, stirring for 15min, sequentially adding potassium carbonate (200mmol) and tetratriphenylphosphine palladium (1mmol), heating to 65 ℃ for reaction after the addition is finished, monitoring the reaction process by TLC, and cooling to room temperature after the reaction is finished; after transferring to a separatory funnel and extracting with ethyl acetate and water, the extract was dried over anhydrous magnesium sulfate, filtered and concentrated, and then the sample was purified by silica gel column chromatography to obtain 15 to 619.30g of intermediate (yield: 78.14%).

(2) Under the protection of nitrogen, adding 15-1(100mmol) and 15-2(100mmol) into toluene, stirring, heating to 50 ℃, stirring for 15min, sequentially adding sodium tert-butoxide (200mmol), tri-tert-butylphosphine (2mmol) and tris (dibenzylideneacetone) dipalladium (1mmol), heating to 65 ℃ for reaction after the addition is finished, monitoring the reaction process by TLC, and cooling to room temperature after the reaction is finished; transferred to a separatory funnel and extracted with ethyl acetate and water. The extract was dried over anhydrous magnesium sulfate, filtered and concentrated, and then the sample was purified by silica gel column chromatography to obtain intermediate 15 to 337.81g (yield: 79.77%).

(3) Under the protection of nitrogen, adding the intermediate 15-3(76.68mmol) and 15-6(76.68mmol) into toluene, heating to 50 ℃, stirring for 15min, sequentially adding sodium tert-butoxide (153.36mmol), tri-tert-butylphosphine (1.53mmol) and tris (dibenzylideneacetone) dipalladium (0.77mmol), heating to reflux reaction after the addition is finished, monitoring the reaction process by TLC, and cooling to room temperature after the reaction is finished; after transferring to a separatory funnel and extracting with ethyl acetate and water, the extract was dried over anhydrous magnesium sulfate, filtered and concentrated, and then the sample was purified by silica gel column chromatography and further purified by beating with toluene to obtain 1543.53g of compound (yield: 83.23%).

Example 4: synthesis of Compound 26

(1) Under the protection of nitrogen, adding 26-4(100mmol) and 26-5(100mmol) into a toluene/water mixed solvent, heating to 50 ℃, stirring for 15min, sequentially adding potassium carbonate (200mmol) and tetratriphenylphosphine palladium (1mmol), monitoring the reaction process by TLC after the addition is finished, heating to 65 ℃ for reaction, and cooling to room temperature after the reaction is finished; after transferring to a separatory funnel and extracting with ethyl acetate and water, the extract was dried over anhydrous magnesium sulfate, filtered and concentrated, and then the sample was purified by silica gel column chromatography to obtain intermediate 26 to 621.15g (yield: 86.33%).

(2) Under the protection of nitrogen, adding 26-1(100mmol) and 26-2(100mmol) into toluene, stirring, heating to 50 ℃, stirring for 15min, sequentially adding sodium tert-butoxide (200mmol), tri-tert-butylphosphine (2mmol) and tris (dibenzylideneacetone) dipalladium (1mmol), heating to 65 ℃ for reaction after the addition is finished, monitoring the reaction process by TLC, and cooling to room temperature after the reaction is finished; after transferring to a separatory funnel and extracting with ethyl acetate and water, the extract was dried over anhydrous magnesium sulfate, filtered and concentrated, and then the sample was purified by silica gel column chromatography to obtain intermediate 26 to 337.21g (yield: 78.50%).

(3) Under the protection of nitrogen, adding the intermediate 26-3(76.68mmol) and 26-6(76.68mmol) into toluene, heating to 50 ℃, stirring for 15min, sequentially adding sodium tert-butoxide (153.36mmol), tri-tert-butylphosphine (1.53mmol) and tris (dibenzylideneacetone) dipalladium (0.77mmol), and heating to reflux reaction after the addition is finished; the progress of the reaction was monitored by TLC, and after completion of the reaction, the reaction was cooled to room temperature, transferred to a separatory funnel, extracted with ethyl acetate and water, the extract was dried over anhydrous magnesium sulfate, filtered and concentrated, and then the sample was purified by silica gel column chromatography and further purified by toluene beating to obtain 2646.31g of compound (yield: 88.55%).

The synthesis of the other compounds is the same as the above-listed examples, and therefore, they are not illustrated here, and some of the mass spectra and molecular formulae are shown in table 1 below:

	compound (I)	Molecular formula	Theoretical value of mass spectrum	Mass spectrometric test values
					Example 5	Compound 8	C39H24N2S3	618.82	618.73
Example 6	Compound 18	C45H30N2S	630.81	630.77
					Example 7	Compound 24	C55H37N2S	743.97	743.91
Example 8	Compound 31	C44H27NS3	665.89	665.83
					Example 9	Compound 44	C41H31NOS	585.77	585.69

Using the compound of the present invention, a vapor deposited film having a film thickness of 80nm was formed on a substrate, and refractive indices of 450nm, 530nm and 635nm were measured using a spectrometer, and for comparison, Alq was measured³(note as comparative example 1) was also measured.

The aromatic amine compounds of the invention and the comparative compound Alq are listed in the following table₃The thermal and refractive index test results of (a) are given in table 2 below:

from the above table 2, for visible light with wavelength of 450-635nm, the refractive indexes of the compounds of the present invention are all greater than 2.0, which meets the refractive index requirement of the light emitting device for CPL, and the extinction coefficient k value is almost 0 after the blue light wavelength of 430nm, which does not affect the light emission of the light emitting layer material in the blue region. And therefore can bring about higher light emission efficiency. In addition, the glass transition temperature of the compounds of the present invention is higher than 155 ℃, thus showing that the aromatic compounds have high stability in a thin film state when applied to a light emitting device.

The following example provides an illustrative example to illustrate the technical effect of the compounds of the present invention in practical application by their use in organic light emitting devices.

Device example 1

An embodiment provides an organic light emitting device including: the structure comprises a substrate, an ITO anode, a hole injection layer, a hole transport layer, a light-emitting layer, a first electron transport layer, a second electron transport layer, a cathode (a magnesium-silver electrode, the mass ratio of magnesium to silver is 9:1) and a cap layer (CPL), wherein the thickness of the ITO anode is 15nm, the thickness of the hole injection layer is 5nm, the thickness of the hole transport layer is 70nm, the thickness of the light-emitting layer is 25nm, the thickness of the first electron transport layer is 30nm, the thickness of the second electron transport layer is 5nm, the thickness of the magnesium-silver electrode is 14nm and the thickness of the cap layer (CPL) is 100 nm.

The organic light-emitting device of the present invention is prepared by the following steps:

the glass substrate was cleaned by sonication in isopropanol and deionized water, respectively, for 30 minutes followed by exposure to ozone for about 10 minutes; mounting the obtained glass substrate with the ITO anode on a vacuum deposition device; on the ITO anode layer, vacuum evaporation is carried outPlating a hole injection layer material HAT-CN in a vapor deposition mode, wherein the thickness of the hole injection layer material HAT-CN is 5nm, and the hole injection layer material HAT-CN is used as a hole injection layer; vacuum evaporating a hole transport layer material TAPC with the thickness of 70nm on the hole injection layer to be used as a hole transport layer; co-depositing a light-emitting layer on the hole transport layer, wherein CBP (arylamine compound) is used as a main material, and Ir (ppy)₃As doping material, Ir (ppy)₃The mass ratio of CBP to CBP is 0.2:9.8, and the thickness is 25 nm; vacuum evaporating a first electron transport layer on the light-emitting layer, wherein the material of the first electron transport layer is TPBI, and the thickness of the first electron transport layer is 30 nm; vacuum evaporating a second electron transport layer on the first electron transport layer, wherein the second electron transport layer is made of Alq³The thickness is 5 nm; a magnesium-silver electrode is evaporated on the second electron transport layer in vacuum, wherein the mass ratio of Mg to Ag is 9:1, the thickness is 14nm, and the magnesium-silver electrode is used as a cathode; the compound 1 designed in the scheme is vacuum evaporated on a cathode, the thickness is 100nm, and the compound is used as a cathode cap layer.

Organic light emitting device examples 2 to 9

Organic light-emitting devices 2 to 9 were prepared in the same manner as in organic light-emitting device example 1. Except that the CPL layer material compound 1 was changed to compounds 8, 13, 15, 18, 24, 26, 31, 44, respectively, and the materials of the other materials such as the light-emitting layer and the auxiliary layer were the same.

Comparative device example 1

Comparative organic light-emitting device 1 was prepared according to the method of device example 1. Except that the CPL layer material compound 1 was changed to CBP, and the materials of the other layers, such as the light-emitting layer and the auxiliary layer, were the same.

The light emitting properties of the organic light emitting devices 1 to 9 and the comparative device 1 were tested, and the test results are shown in table 3 below:

current density: 10mA/cm²

As can be seen from table 3 above, the devices using the compound of the present invention as the CPL material all had lower driving voltages than the comparative device 1. Compared with the comparison device 1, the brightness and the service life of the device adopting the compound of the invention as the CPL material are both obviously improved. Therefore, the arylamine compound can improve the luminous efficiency of a luminescent device and prolong the service life of the device, and is an ideal CPL material.

Another aspect of the present invention also provides a display apparatus including the display panel of the organic light emitting device as described above.

The embodiments in the present description are described in a progressive manner, each embodiment focuses on differences from other embodiments, and the same and similar parts among the embodiments are referred to each other. The device disclosed by the embodiment corresponds to the method disclosed by the embodiment, so that the description is simple, and the relevant points can be referred to the method part for description.

The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.