CN112759584A - Organic electroluminescent material and synthetic method thereof - Google Patents
Organic electroluminescent material and synthetic method thereof Download PDFInfo
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- 125000003118 aryl group Chemical group 0.000 claims description 8
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- QTPLEVOKSWEYAC-UHFFFAOYSA-N 1,2-diphenyl-9h-fluorene Chemical class C=1C=CC=CC=1C1=C2CC3=CC=CC=C3C2=CC=C1C1=CC=CC=C1 QTPLEVOKSWEYAC-UHFFFAOYSA-N 0.000 claims description 4
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 2
- 238000005401 electroluminescence Methods 0.000 claims 2
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- INJYATWDDJSOIP-UHFFFAOYSA-N 2-bromo-4,6-diphenylpyridine Chemical group N=1C(Br)=CC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 INJYATWDDJSOIP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
本发明提供一种有机电致发光材料及其合成方法，属于有机光电材料技术领域。提供的光电材料中含有吡啶的结构，电子载流子传输能力更强，同时结构中引入螺原子，使得材料的玻璃化转化温度更高，同时使得三线态能级更高。同时用正交实验的方法，考察确定了关键步骤的合成参数。本发明提供的化合物可以作为发光层材料或电子传输层材料应用于有机发光器件中，具有更高的发光效率和更低的驱动电压。The invention provides an organic electroluminescent material and a synthesis method thereof, belonging to the technical field of organic optoelectronic materials. The provided optoelectronic material contains a pyridine structure, and the electron carrier transport capability is stronger, and at the same time, spiro atoms are introduced into the structure, so that the glass transition temperature of the material is higher, and the triplet energy level is higher at the same time. At the same time, the method of orthogonal experiment was used to investigate and determine the synthesis parameters of the key steps. The compounds provided by the present invention can be used as light-emitting layer materials or electron transport layer materials in organic light-emitting devices, and have higher light-emitting efficiency and lower driving voltage.
Description
Technical Field
The invention relates to the technical field of organic photoelectric materials, in particular to an organic electroluminescent material and an organic light-emitting device thereof.
Background
Since the Organic Light Emitting Diode (OLED) has excellent characteristics of self-luminescence, no need of a backlight source, high contrast, thin thickness, wide viewing angle, high reaction speed, applicability to a flexible panel, wide use temperature range, simple structure and manufacture, and the like, the technology has been gradually applied to smart phones, flat-panel televisions, virtual reality commodities after continuous research and development for more than twenty years.
To increase the lifetime of OLEDs, increasing the luminous efficiency is key to the industrialization of OLED displays, and to improve the brightness, efficiency and lifetime of organic electroluminescent devices, multilayer structures are generally used in the devices. A hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, and the like.
In the OLED material, the mobility of electrons is 2-3 orders of magnitude lower than that of holes, so that the quantity of electrons and holes in the OLED is far greater than that of electrons.
Disclosure of Invention
In view of the above, the present invention provides an organic electroluminescent material and an organic light emitting device thereof, and the organic light emitting device prepared by using the organic electroluminescent material has higher light emitting efficiency and lower driving voltage.
The invention firstly provides an organic electroluminescent material, which has a structural general formula shown as I:
wherein X is selected from O, S, C (CH)3)2Or CPh2；
E is selected from substituted or unsubstituted phenyl, substituted or unsubstituted polycyclic aromatic hydrocarbon, substituted or unsubstituted biaryl, substituted or unsubstituted dimethyl fluorene, substituted or unsubstituted diphenyl fluorene and substituted or unsubstituted carbazole; substituted or unsubstituted indoles; substituted or unsubstituted benzofuran, substituted or unsubstituted benzothiophene;
l is selected from a single bond, a substituted or unsubstituted divalent aryl group, and an unsubstituted divalent biaryl group;
a is selected from structural formula II;
y1 to Y13 are independently selected from C or N; wherein Y1 is selected from N; at most one of Y4 to Y8 is selected from N; at most one of Y9 to Y13 is selected from N;
m and n are independently selected from an integer of 0 or 1.
Preferably, X is selected from O or C (CH)3)2；
E is selected from substituted or unsubstituted phenyl, substituted or unsubstituted polycyclic aromatic hydrocarbon, substituted or unsubstituted biaryl;
l is selected from single bond, substituted or unsubstituted divalent aryl;
a is selected from structural formula II;
y1 to Y13 are independently selected from C or N; wherein Y1 to Y3 have and only one is selected from N; at most one of Y4 to Y8 is selected from N; at most one of Y9 to Y13 is selected from N;
m and n are independently selected from an integer of 0 or 1.
Preferably, the organic electroluminescent material is selected from any one of the following structures:
the invention also provides a synthesis method of the organic luminescent compound, wherein the Suzuki reaction catalyzed by the noble metal is designed in at least one step of reaction.
Preferably, the parameters of the Suzuki method are selected and optimized by adopting a statistical method.
Preferably, the statistical method is an orthogonal test method.
Preferably, the orthogonal assay uses a three-factor four-level analysis.
The invention also provides an organic light-emitting device comprising a first electrode, a second electrode and one or more organic compound layers disposed between the two electrodes, at least one organic compound layer comprising the organic electroluminescent material of the invention.
Preferably, the organic compound layer includes a light-emitting layer containing the organic electroluminescent material.
Preferably, the organic compound layer includes an electron transport layer containing the organic electroluminescent material.
The invention has the beneficial effects that:
the organic electroluminescent material provided by the invention contains a pyridine structure, the electron carrier transmission capability is stronger, and meanwhile, the structure is introduced with spiro atoms, so that the glass transition temperature of the structure is higher, and the triplet state energy level is higher.
Detailed Description
The present invention will be described in detail with reference to the following embodiments, which are intended to cover all the embodiments of the invention, and not all the embodiments of the invention.
The invention firstly provides an organic electroluminescent material, which has the following structural general formula:
wherein X is selected from O, S, C (CH)3)2Or CPh2；
E is selected from substituted or unsubstituted phenyl, substituted or unsubstituted polycyclic aromatic hydrocarbon, substituted or unsubstituted biaryl, substituted or unsubstituted dimethyl fluorene, substituted or unsubstituted diphenyl fluorene and substituted or unsubstituted carbazole; substituted or unsubstituted indoles; substituted or unsubstituted benzofuran, substituted or unsubstituted benzothiophene;
l is selected from a single bond, a substituted or unsubstituted divalent aryl group, and an unsubstituted divalent biaryl group;
a is selected from structural formula II;
y1 to Y13 are independently selected from C or N; wherein Y1 is selected from N; at most one of Y4 to Y8 is selected from N; at most one of Y9 to Y13 is selected from N;
m and n are independently selected from an integer of 0 or 1.
Preferably, X is selected from O or C (CH)3)2；
E is selected from substituted or unsubstituted phenyl, substituted or unsubstituted polycyclic aromatic hydrocarbon, substituted or unsubstituted biaryl;
l is selected from single bond, substituted or unsubstituted divalent aryl;
a is selected from structural formula II;
y1 to Y13 are independently selected from C or N; wherein Y1 to Y3 have and only one is selected from N; at most one of Y4 to Y8 is selected from N; at most one of Y9 to Y13 is selected from N;
m and n are independently selected from an integer of 0 or 1.
More preferably, X is selected from O or C (CH)3)2；
E is selected from substituted or unsubstituted phenyl;
l is selected from single bond, substituted or unsubstituted divalent aryl;
a is selected from structural formula II;
y1 is selected from N; y4 is selected from N; y9 is selected from N;
m and n are independently selected from an integer of 0 or 1.
Most preferably, X is selected from O;
e is selected from unsubstituted phenyl;
l is selected from single bonds;
a is selected from structural formula II;
y1 to Y13 are independently selected from C or N; wherein Y1 is selected from N; y4 is selected from N; y9 is selected from N;
m and n are independently selected from an integer 1.
More preferably, the organic electroluminescent material is selected from any one of the following structures:
the invention also provides a synthesis method of the organic luminescent compound, wherein at least one step of reaction involves a Suzuki reaction catalyzed by noble metal.
Reaction scheme a:
wherein X is selected from O, S, C (CH)3)2Or CPh2；
E is selected from substituted or unsubstituted phenyl, substituted or unsubstituted polycyclic aromatic hydrocarbon, substituted or unsubstituted biaryl, substituted or unsubstituted dimethyl fluorene, substituted or unsubstituted diphenyl fluorene and substituted or unsubstituted carbazole; substituted or unsubstituted indoles; substituted or unsubstituted benzofuran, substituted or unsubstituted benzothiophene;
l is selected from a single bond, a substituted or unsubstituted divalent aryl group, and an unsubstituted divalent biaryl group;
a is selected from structural formula II;
y1 to Y13 are independently selected from C or N; wherein Y1 is selected from N; at most one of Y4 to Y8 is selected from N; at most one of Y9 to Y13 is selected from N;
m and n are independently selected from an integer of 0 or 1.
The noble metal in the invention refers to a metal complex containing palladium, rhodium, platinum and nickel, such as Pd (PPh)3)4，Pd2(dba)3But is not limited thereto.
The solvent of the noble metal catalyzed Suzuki reaction is toluene, xylene, trimethylbenzene, tetramethylbenzene, DMF, DMSO, and dimethyl pyrrolidone, but is not limited thereto.
The parameters of the Suzuki method are selected and optimized by an orthogonal experiment method in a statistical method.
The orthogonal experimental method is an important method in the mathematical discipline, mainly adopts an experimental method of carrying out multi-factor and multi-level analysis by a mathematical statistical method, selects part of combinations with typical characteristics in all experimental groups to carry out the experiment according to the Galois theory, adopts a few experiments to represent all the experiments, and considers finding part of the representative combinations from multiple experimental horizontal combinations to carry out the experiment according to the factorial design, namely the factorial design.
The orthogonal table of the invention is composed of row number, column number and horizontal numberA form formed, usually by Ln(mk) Expressing that L is an orthogonal table, and n is the row number of the orthogonal table and represents the test times; k is the column number of the orthogonal table and represents the number of the most variables of the influencing factors; m is the horizontal number, also called the value of each variable; the following quantitative relationships exist between n, m, k: n ═ k (m-1) +1. the orthogonal table must have the characteristics of "uniform distribution, uniformity and comparability", the experimental range of "uniform distribution" includes all experimental points, and the experimental points should be uniformly distributed, so that each point is randomly extracted and has the representativeness of "uniformity and comparability", so that the researcher can clearly and conveniently obtain the analysis result, and can make analysis estimation on all the factors by means of result, and can further find out core factor from several factors to ensure that the interference is eliminated in all levels, and can effectively compare the experimental results to obtain optimum experimental conditions.
The orthogonal experimental steps of the invention are analyzed as follows: specifically, the method comprises the steps of finding out nearly optimal data from all experimental data in the first step, carrying out multi-factor analysis in the second step, summing experimental values in all factors to obtain an experimental result, obtaining the optimal factor, then comparing the experimental result to obtain a variation trend, wherein the variation trend plays a role in guiding the next step of experiment; the influence of the factors is contrasted and analyzed through concepts and principles such as variance, standard deviation, range difference and the like in statistics; then, the test range is narrowed, and the next experiment is carried out, so that the optimal value can be obtained; according to the experimental result, the core is to find out the optimal combination.
The application range of the orthogonal experimental method is as follows: the experimental design and analysis of single-factor analysis and double-factor analysis are often simpler, but more influencing factors exist in the specific problem, so that the single-factor analysis and double-factor analysis are less in application; when multiple influencing factors are considered, if multiple experiments are needed, the workload is large, time and labor are consumed, so that a specific problem is solved, and due to the influence of multiple factors, comprehensive experiments cannot be performed; however, at the present stage, under the guidance of the "innovation" concept, we should find the optimal method theoretically, and then find the optimal experimental combination, and strive for more time for our research and product design, so that the work efficiency is higher.
The orthogonal experimental method of the invention comprises the following evaluation: the orthogonal experimental method is widely applied to the fields of science and technology, agricultural production and the like; in the process of researching the multi-factor problem, the orthogonal experimental design method reduces the experimental times, saves time for each department in the production stage, improves the working efficiency, is a high-efficiency experimental method, provides theoretical basis and analysis thought for 'innovative development' and 'coordinated development' of production departments in the related field, and has good effect on the application of related multi-factor analysis.
The meaning of the factors and levels in the three-factor four-level orthogonal experimental method is well known to those skilled in the art, and the three factors refer to the reaction temperature, the reaction time and the catalyst adding amount.
The organic light emitting device comprises a first electrode, a second electrode and one or more organic compound layers arranged between the two electrodes, wherein at least one organic compound layer comprises the organic light emitting material.
Example 1: preparation of Compound 1
Step1. in a three-necked flask equipped with addition funnel, condenser and glass stopper, magnesium turnings (10.9g, 450mmol, 3 equiv.) and iodine (381mg, 1.50mmol, 0.01 equiv.) are added p-chlorobromobenzene (86g, 450mmol, 3 equiv.) dissolved in THF (210 mL) and 25 mL of this solution is added, stirring is carried out for 5 minutes until gentle reflux is achieved, then the remaining solution is added dropwise over 1 hour, after addition is complete, the reaction is refluxed for 1 hour until all magnesium has reacted, then cooling is carried out to 0 deg.C, xanthone (29.4g, 150mmol, 1 equiv.) is dissolved in THF (120mL) and added dropwise over 1 hour, after addition is complete, the reaction is allowed to warm to rt and stirred to completion (30 minutes), the mixture is poured into 1L of ice/saturated ammonium chloride and the combined organic layers are extracted with dichloromethane (3X 500mL) and water (1L) and the organic layers are extracted with TLC (5% ethyl acetate in hexane) Brine (1L) was washed, then dried over magnesium sulfate, filtered and concentrated to give b, 30.8g as a white solid.
Step2. mixing BF3-Et2A solution of O complex (4.39mL, 34.6mmol) in the appropriate dichloromethane (200mL) was added dropwise to a mixed solution of b (10.47g, 34.1mmol, 2.1 equiv.) and dibenzofuran (2.69, 16mmol) in the appropriate dichloromethane (1L.) the reaction mixture was stirred at rt (25 deg.C) under nitrogen until the starting material could no longer be detected by TLC.ethanol (500mL) and water (1.5L) were added successively to quench the reaction then the phases were separated and the aqueous phase was extracted with dichloromethane after the combined dichloromethane layers were washed and dried (MgSO4) to remove solvent, the crude product remaining was purified by silica gel chromatography (petroleum ether-dichloromethane) to give the product in 70% yield of c (5.14, 11.2 mmol).
Step3. 1L of absolute dry THF was cooled to-78 deg.C by a dry ice-acetone bath, a solution of n-butyllithium in n-hexane (containing 22.4mmol, 2 equiv. of n-butyllithium) was added, stirred for 1 hour, reactant c (5.14g, 11.2mmol, 1 equiv.) was slowly added, stirred until dissolved and gradually warmed to room temperature, reacted overnight the next day, saturated aqueous ammonium chloride was added to the reaction solution, followed by extraction with dichloromethane (3X 500mL), the combined organic layers were washed with water (1L) and brine (1L), then dried over magnesium sulfate, and after removal of the solvent, the remaining crude product was purified by silica gel chromatography (petroleum ether-dichloromethane) to give product d (4.93g, 8.96mmol) in 80% yield.
In the process of the Suzuki reaction in the fourth step, the influence of the addition amount, the reaction temperature and the reaction time of the tetratriphenylphosphine palladium on the Suzuki coupling reaction is screened through a three-factor four-level orthogonal experiment, and the optimal preparation condition is determined.
Factor-level table of the conditions was examined as shown in table I.
Table I factor level table
L16(43) The results of the orthogonality experiment are shown in table II.
TABLE II L16 (4)3) Results of orthogonal experiments
As can be seen from table II, experiment 16 reflects the best experimental results, and the best reaction conditions are that the catalyst addition amount is 2%, the reaction temperature is strong reflux, and the reaction time is 10h, but considering the principle of the lowest cost of the actual production link, experiment 11 reflects the best experimental results that can be actually produced, the catalyst addition amount is 1%, the reaction temperature is 110 ℃, and the reaction time is 2h.
Step4. to 500ml of a toluene solution of the raw material d (4.93g, 8.96mmol) and the raw material e (2.79g, 8.96mmol) in a degassed reaction system under the protection of nitrogen, tetratriphenylphosphine palladium (0.1g, 0.09mmol) is added, a 2M aqueous solution of sodium carbonate (2.85, 26.88mmol) and 50ml of absolute ethanol are added to the reaction solution, the reaction solution is reacted at 110 ℃ for 2 hours, after the reaction is completed, the reaction solution passes through a silica gel funnel, the filtrate is evaporated to dryness in a rotating manner, and the obtained solid product is recrystallized by ethanol to obtain a white product (4.63g, 7.06mmol) with the yield of 78.8%.
Example 2: preparation of Compound 2
The fourth step in example 1 was replaced with 2, 6-diphenyl-4-bromopyridine and the rest of the procedure was the same as in example 1.
EXAMPLE 3 preparation of Compound 3
The fourth step in example 1 was replaced with 4- (4-bromophenyl) -2, 6-diphenylpyridine and the remaining steps were the same as in example 1.
EXAMPLE 4 preparation of Compound 6
The fourth step in example 1 was replaced with 2-bromo-4, 6-diphenylpyridine and the rest of the procedure was the same as in example 1.
EXAMPLE 5 preparation of Compound 7
The first step of example 1 was replaced with para-chlorobromobenzene the rest of the procedure was the same as in example 1.
FD-MS values of the Compounds prepared in the examples of the invention
| Compound (I) | FD-MS |
| 1 | M/z：655.76，C46H29N3O2(655.78) |
| 2 | M/z：653.24，C48H31NO2(653.59) |
| 3 | M/z：729.27，C54H35NO2(729.77) |
| 6 | M/z：653.24，C48H31NO2(653.57) |
| 7 | M/z：655.76，C46H29N3O2(655.90) |
Comparative application example 1:
the ITO glass substrate is placed in distilled water for cleaning for 2 times, ultrasonic cleaning is carried out for 30 minutes, after the cleaning of the distilled water is finished, solvents such as isopropanol, acetone, methanol and the like are sequentially subjected to ultrasonic cleaning and then dried, the substrate is transferred into a plasma cleaning machine, the substrate is cleaned for 5 minutes, and the substrate is sent to an evaporation machine.
Depositing hole injection layer on prepared ITO transparent electrode
Vapor deposition of hole transport layer
Vapor deposition of luminescent layer material
Then evaporating the electron transport layer
Cathode electrode
The organic evaporation speed is maintained in the above process
LiF is
Al is
Application example 1:
depositing hole injection layer on prepared ITO transparent electrode
Vapor deposition of hole transport layer
Evaporation coating luminescent layer material compound
Then evaporating the electron transport layer
Cathode electrode
The organic evaporation speed is maintained in the above process
LiF is
Al is
Application example 2:
compound 1 in example 1 was changed to compound 2.
Application example 3:
compound 1 in example 1 was changed to compound 3.
Application example 4:
compound 1 in example 1 was changed to compound 6.
Application example 5:
compound 1 in example 1 was changed to compound 7.
Measurement example 1: comparative sample and luminescent properties of sample
Comparative samples and samples were evaluated for luminous efficiency and driving voltage using Keithley SMU235, PR650, and the results are shown in table 1:
table 1 luminescence characteristics of light emitting devices prepared according to examples of the present invention
Comparative application example 2:
the ITO glass substrate is placed in distilled water for cleaning for 2 times, ultrasonic cleaning is carried out for 30 minutes, after the cleaning of the distilled water is finished, solvents such as isopropanol, acetone, methanol and the like are sequentially subjected to ultrasonic cleaning and then dried, the substrate is transferred into a plasma cleaning machine, the substrate is cleaned for 5 minutes, and the substrate is sent to an evaporation machine.
Depositing hole injection layer on prepared ITO transparent electrode
Vapor deposition of hole transport layer
Vapor deposition of luminescent layer material
Then evaporating the electron transport layer
Cathode LiF
Al
The organic evaporation speed is maintained in the above process
LiF is
Al is
Application example 6:
depositing hole injection layer on prepared ITO transparent electrode
Vapor deposition of hole transport layer
Vapor deposition of luminescent layer material
Then evaporating electron transport layer compound
Cathode LiF
Al
The organic evaporation speed is maintained in the above process
LiF is
Al is
Application example 7:
compound 1 in example 6 was changed to compound 7.
Measurement example 2: comparative sample and luminescent properties of sample
Comparative samples and samples were evaluated for luminous efficiency and driving voltage using Keithley SMU235, PR650, and the results are shown in table 2:
table 2 luminescence characteristics of light emitting devices prepared according to examples of the present invention
While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present invention as defined by the following claims.
Claims (10)
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| US20180013074A1 (en) * | 2016-07-11 | 2018-01-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
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