CN117185894A - Organic electroluminescent material and application thereof - Google Patents

Organic electroluminescent material and application thereof Download PDF

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CN117185894A
CN117185894A CN202311152635.9A CN202311152635A CN117185894A CN 117185894 A CN117185894 A CN 117185894A CN 202311152635 A CN202311152635 A CN 202311152635A CN 117185894 A CN117185894 A CN 117185894A
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organic electroluminescent
layer
compound
organic
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黄鑫鑫
李之洋
曾礼昌
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Beijing Eternal Material Technology Co Ltd
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Beijing Eternal Material Technology Co Ltd
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Abstract

The application provides a compound which has a structure shown in a general formula (1), wherein each group is defined in the specification. Also provided are organic electroluminescent devices comprising the compounds.

Description

Organic electroluminescent material and application thereof
The application is a divisional application of Chinese patent application (application day: 2021, 02, 26, title of application: organic electroluminescent material and application thereof) with application number 201910767252. X.
Technical Field
The present application relates to an organic compound which can be used in an organic electroluminescent device, in particular, a light-emitting layer host material or a hole blocking layer material; the application also relates to application of the compound in an organic electroluminescent device and the organic electroluminescent device containing the compound.
Background
Optoelectronic devices based on organic materials have become increasingly popular in recent years. The inherent flexibility of organic materials makes them very suitable for fabrication on flexible substrates, which can be designed to produce aesthetically pleasing and cool optoelectronic products, as desired, with no comparable advantages over inorganic materials. Examples of such organic optoelectronic devices include Organic Light Emitting Diodes (OLEDs), organic field effect transistors, organic photovoltaic cells, organic sensors, and the like. Among them, OLED has been developed particularly rapidly, and has been commercially successful in the field of information display. OLED can provide three colors of red, green and blue with high saturation, and the full-color display device manufactured by the OLED does not need extra backlight source, and has the advantages of colorful, light, thin, soft and the like.
The OLED device core is a thin film structure containing a plurality of organic functional materials. Common functionalized organic materials are: a hole injecting material, a hole transporting material, a hole blocking material, an electron injecting material, an electron transporting material, an electron blocking material, a light emitting host material, a light emitting guest (dye), and the like. When energized, electrons and holes are injected, transported to the light emitting region, respectively, and recombined therein, thereby generating excitons and emitting light.
Various organic materials have been developed, and various peculiar device structures are combined, so that carrier mobility can be improved, carrier balance can be regulated, electroluminescent efficiency can be broken through, and device attenuation can be delayed. For quantum mechanical reasons, common fluorescent emitters emit light mainly using singlet excitons generated when electrons and holes are combined, and are still widely used in various OLED products. Some metal complexes, such as iridium complexes, can emit light using both triplet and singlet excitons, known as phosphorescent emitters, and can have energy conversion efficiencies up to four times greater than conventional fluorescent emitters. The thermal excitation delayed fluorescence (TADF) technique can achieve higher luminous efficiency by promoting transition of triplet excitons to singlet excitons, and still effectively utilizing triplet excitons without using a metal complex.
As OLED products continue to enter the market, there is an increasing demand for the performance of such products. The currently used OLED materials and device structures cannot completely solve the problems of OLED product efficiency, lifetime, cost, etc. The researchers of the present application have discovered a smart molecular design through careful thought and continuous experimentation and are described in detail below. Surprisingly, the disclosed compounds are well suited for application to OLEDs and to enhance the performance of the device.
Disclosure of Invention
The application discloses a compound with a large conjugated system structure containing seven-membered rings, which can improve the charge transmission performance of materials, and simultaneously adjust HOMO/LUMO energy level so as to balance carrier transmission and achieve the aim of improving the performance of OLED devices.
In one aspect, the present application provides a compound having a structure of formula (1):
wherein,
x and Y are independently selected from oxygen, sulfur, selenium, BR a ，NR b ，CR c R d ，SiR e R f ，CR g R h -CR i R j ；
Z 1 -Z 10 Each independently is CR z Or N;
R 1 represents 0 to 2 identical or different substituents; r is R 2 Represents 0 to 2 identical or different substituents;
R 3 represents 0 to 3 identical or different substituents; r is R 4 Represents 0 to 3 identical or different substituents;
R a ，R c ，R d ，R e ，R f ，R g ，R h ，R i ，R j ，R z ，R 1 ，R 2 ，R e and R is 4 Independently selected from hydrogen, halogen, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy, C2-C12 cycloalkoxy, silyl, carbonyl, acyl, ester, cyano, amine, C6-C30 aryl, C3-C30 heteroaryl, or a combination thereof;
R b selected from halogen, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy, C2-C12 cycloalkoxy, silyl, carbonyl, acyl, ester, cyano, amine, C6-C30 aryl, C3-C30 heteroaryl, or combinations thereof;
any two adjacent substituents may be linked to each other to form a ring, for example, a five-membered aromatic ring or a six-membered aromatic ring;
when R is a ，R b ，R c ，R d ，R e ，R f ，R g ，R h ，R i ，R j Or R is z When there are a plurality of any one of them, they are each the same or different.
In some embodiments, the compound has the following structure:
wherein each group is defined as in the general formula (1).
In some embodiments, R b A group selected from the group consisting of:
in some embodiments, the compound has a structure selected from those shown by P1-P236:
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as another aspect of the present application, the present application also provides the use of a compound as described above in an organic electroluminescent device.
As still another aspect of the present application, there is also provided an organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic material layers interposed between the first electrode and the second electrode, wherein at least one of the organic material layers contains the compound of the present application.
In some embodiments, the compounds of the present application are included in the light-emitting layer and/or hole blocking layer of an organic electroluminescent device.
In some embodiments, the compounds of the present application are used as light-emitting hosts in light-emitting layers.
In some embodiments, the compounds of the present application are useful as hole blocking layers.
Detailed Description
In order that those skilled in the art will better understand the present application, the present application will be described in further detail with reference to specific embodiments.
In the present specification, alkyl, alkoxy, and silyl groups may contain 1 to 12 carbon atoms, cycloalkyl and cycloalkoxy groups may contain 3 to 12 carbon atoms, aryl groups may contain 6 to 30 carbon atoms, and heteroaryl groups may contain 3 to 30 carbon atoms.
None of the compounds of the synthetic methods mentioned in the present application are commercially available starting products. The solvents and reagents used in the present application, such as methylene chloride, petroleum ether, ethanol, tetrahydrofuran, N-dimethylacetamide, anhydrous magnesium sulfate, carbazole, benzimidazole, and the like, may be purchased from domestic chemical product markets, such as from the national pharmaceutical group reagent company, TCI company, shanghai Pichia pharmaceutical company, carboline reagent company, and the like.
The present application will be described in detail below by way of examples, and the compounds according to the examples of the present application can be synthesized by referring to the examples shown below, but it should be noted that the method and raw materials for obtaining the compounds are not limited to the synthetic methods and materials used in the present application, and those skilled in the art can choose other methods or routes to obtain the novel compounds according to the present application. The compounds for which no synthetic method is mentioned in the present application are all commercially available starting products or are prepared by these starting products according to known methods.
Analytical detection of intermediates and compounds in the present application was carried out using mass spectrometry (ZAB-HS type mass spectrometer assay, manufactured by Micromass Co., UK).
Synthetic examples
Representative synthetic pathway 1:
representative synthetic pathway 1-1:
representative synthetic pathways 1-2:
representative synthetic pathways 1-3:
representative synthetic pathway 2:
representative synthetic pathway 3:
synthesis of M1
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1-bromo-8-iodonaphthalene (66.60 g,200 mmol), 2- (methoxycarbonyl) phenylboronic acid (36.00 g,200 mmol), tetrakis (triphenylphosphine) palladium (2.30 g,2 mmol), potassium carbonate (55.2 g,400 mmol), 1, 4-dioxane 1200ml, and distilled water 400ml were placed in a 3L reaction vessel under nitrogen atmosphere and reacted at 100℃under reflux for 12h. Cooled to room temperature and the concentrated organic phases were combined. Separation by column chromatography gave intermediate M1-1.75 g. Calculated molecular weight: 314.20, found C/Z:314.2.
under nitrogen atmosphere, M1-1 (47.13 g,150 mmol) and tetrahydrofuran (500 ml) were placed in a 2L reaction vessel, cooled to 0℃and methyl magnesium bromide (110.48 g,600 mmol) was slowly added. Returning to room temperature for reaction for 12h, adding saturatedNH 4 The aqueous Cl solution was stirred for 15min, extracted with ethyl acetate, and the concentrated organic phases were combined. Separation by column chromatography gave intermediate M1-2.68 g. Calculated molecular weight: 341.25, found C/Z:341.2.
m1-2 (40.95 g,120 mmol) and 400ml of methylene chloride were placed in a 1L reaction vessel under nitrogen atmosphere, cooled to 0℃and then methanesulfonic acid (11.52 g,120 mmol) was added to the vessel and reacted for 12 hours. Water was added and stirred for 1h, the extracts were combined and the organic phases were concentrated. Isolation by column chromatography gave intermediate M1.54 g. Calculated molecular weight: 323.23, found C/Z:323.2.
synthesis example 1:
synthesis of P16
Under nitrogen atmosphere, M1 (16.16 g,50 mmol), 2- (methoxycarbonyl) phenylboronic acid (9.00 g,50 mmol), tetrakis (triphenylphosphine) palladium (1.15 g,1 mmol), potassium carbonate (13.8 g,100 mmol), 1, 4-dioxane (300 ml) and distilled water (100 ml) were placed in a 1L reaction vessel and reacted at 100℃under reflux for 12h. Cooled to room temperature and the concentrated organic phases were combined. Separation by column chromatography gave intermediate P16-1.78 g. Calculated molecular weight: 378.47, found C/Z:378.5.
p16-1 (15.14 g,40 mmol) and 200ml of tetrahydrofuran were placed in a 2L reaction vessel under nitrogen atmosphere, cooled to 0℃and methyl magnesium bromide (29.46 g,160 mmol) was slowly added. Returning to room temperature for reaction for 12h, adding saturated NH 4 The aqueous Cl solution was stirred for 15min, extracted with ethyl acetate, and the concentrated organic phases were combined. Separation by column chromatography to give intermediate P16-2.78 g. Calculated molecular weight: 378.52, found C/Z:378.5.
p16-2 (11.36 g,30 mmol) and 150ml of methylene chloride were placed in a 1L reaction vessel under nitrogen atmosphere, cooled to 0℃and then methanesulfonic acid (2.88 g,30 mmol) was added to the vessel for reaction for 12 hours. Water was added and stirred for 1h, the extracts were combined and the organic phases were concentrated. Separation by column chromatography gave intermediate P16-3.29 g. Calculated molecular weight: 360.50, found C/Z:360.5.
p16-3 (7.21 g,20 mmol), sodium chloride (23.38 g,400 mmol), aluminum trichloride (193.14 g,800 mmol) and benzene 500ml were placed in a 2L reaction vessel under nitrogen atmosphere and reacted under reflux for 12 hours. Cooled to room temperature, and treated with NaHCO 3 The saturated aqueous solution is used for removing excessive AlCl 3 The organic phases were combined and concentrated. Separation by column chromatography gave 163.04g of compound p. Calculated molecular weight: 358.48, found C/Z:358.5.
synthesis example 2:
synthesis of P18
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Under a nitrogen atmosphere, M1 (32.32 g,100 mmol), 2-methylthiophenylboronic acid (16.80 g,100 mmol), tetrakis (triphenylphosphine) palladium (1.15 g,1 mmol), potassium carbonate (27.6 g,200 mmol), 1, 4-dioxane (600 ml) and distilled water (200 ml) were placed in a 1L reaction vessel and reacted at 100℃under reflux for 12 hours. Cooled to room temperature and the concentrated organic phases were combined. Separation by column chromatography gave intermediate P18-1.55 g. Calculated molecular weight: 366.52, found C/Z:366.5.
under nitrogen atmosphere, P18-1 (29.32 g,80 mmol) and 300ml of acetic acid were placed in a 1L reaction vessel, and H was introduced 2 O 2 (8.16 g,240 mmol) was dissolved in 50ml acetic acid and the solution was slowly added dropwise and reacted at room temperature for 8h. After the reaction, the acetic acid was removed by concentration. Separation by column chromatography gave intermediate P18-2.41 g. Calculated molecular weight: 382.52, found C/Z:382.5.
p18-2 (19.13 g,50 mmol) and 75ml of trifluoromethanesulfonic acid were put into a 500ml reaction vessel under nitrogen atmosphere, stirred at room temperature for 24 hours, added with 40ml of pyridine and 5ml of water, and reacted under reflux for 30 minutes. The temperature was returned to room temperature, extracted with dichloromethane and the concentrated organic phases combined. Separation by column chromatography gave intermediate P18-3.22 g. Calculated molecular weight: 350.48, found C/Z:350.5.
under nitrogen atmosphere, P18-3 (10.52 g,30 mmol), sodium chloride (35.06 g,600 mmol), aluminum trichloride (289.68 g,1200 mmol) and benzene 1000ml were placed in a 2L reaction vessel and reacted under reflux for 12h. Cooled to room temperature, and treated with NaHCO 3 The saturated aqueous solution is used for removing excessive AlCl 3 The organic phases were combined and concentrated. The separation was carried out by column chromatography to obtain 4.25g of P18. Calculated molecular weight: 348.46, found C/Z:348.5.
synthesis example 3:
synthesis of P174
Under a nitrogen atmosphere, M1 (32.32 g,100 mmol), 2-nitrophenylboronic acid (16.70 g,100 mmol), tetrakis (triphenylphosphine) palladium (1.15 g,1 mmol), potassium carbonate (27.6 g,200 mmol), and 600ml of 1, 4-dioxane were placed in a 1L reaction vessel, and 200ml of distilled water was reacted at 100℃under reflux for 12 hours. Cooled to room temperature and the concentrated organic phases were combined. Separation by column chromatography gave intermediate P174-1.38 g. Calculated molecular weight: 366.52, found C/Z:366.5.
p174-1 (29.32 g,80 mmol), triphenylphosphine (52.46 g,200 mmol) and 300ml o-dichlorobenzene were placed in a 1L reaction vessel under nitrogen atmosphere and reacted at 180℃under reflux for 12h. Cooled to room temperature and the concentrated organic phases were combined. Separation by column chromatography gave intermediate P174-2.68 g. Calculated molecular weight: 333.43, found C/Z:333.4.
under nitrogen atmosphere, P174-2 (20.00 g,60 mmol), sodium chloride (70.13 g,1200 mmol), aluminum trichloride (579.43 g,2400 mmol) and benzene 1500ml were placed in a 3L reaction vessel and reacted under reflux for 12h. Cooled to room temperature, and treated with NaHCO 3 The saturated aqueous solution is used for removing excessive AlCl 3 The organic phases were combined and concentrated. Separation by column chromatography gave intermediate P174-3.76 g. Calculated molecular weight: 331.42, found C/Z:331.4.
under nitrogen atmosphere, M1 (6.63 g,20 mmol), 2-chloro-4-phenylquinazoline (4.81 g,20 mmol), cesium carbonate (13.04 g,40 mmol) and DMF (100 ml) were placed in a 250ml reaction vessel and reacted under reflux for 12h. Cooled to room temperature and the concentrated organic phases were combined. The separation was carried out by column chromatography to obtain 4.77g of P174. Calculated molecular weight: 535.65, found C/Z:535.6.
synthesis of M2
1-bromo-8-iodonaphthalene (66.60 g,200 mmol), 2-methylthiophenylboronic acid (33.60 g,200 mmol), tetrakis (triphenylphosphine) palladium (2.30 g,2 mmol), potassium carbonate (55.2 g,400 mmol), 1, 4-dioxane 1200ml and distilled water 400ml were placed in a 3L reaction vessel under nitrogen atmosphere, and reacted at 100℃under reflux for 12 hours. Cooled to room temperature and the concentrated organic phases were combined. Separation by column chromatography gave intermediate M2-1.12 g. Calculated molecular weight: 329.26, found C/Z:329.3.
m2-1 (47.74 g,145 mmol) and 600ml of acetic acid were placed in a 2L reaction vessel under nitrogen atmosphere, and H was introduced 2 O 2 (14.79 g,435 mmol) in 150ml acetic acid, the above solution was slowly added dropwise and reacted at room temperature for 8 hours. After the reaction, the acetic acid was removed by concentration. Separation by column chromatography gave intermediate M2-2.36.21 g. Calculated molecular weight: 345.25, found C/Z:345.2.
under nitrogen atmosphere, M2-2 (34.52 g,100 mmol) and 150ml of trifluoromethanesulfonic acid were placed in a 1L reaction vessel, stirred at room temperature for 24 hours, 80ml of pyridine and 10ml of water were added, and the mixture was refluxed for 30 minutes. The temperature was returned to room temperature, extracted with dichloromethane and the concentrated organic phases combined. Isolation by column chromatography gives 14.38g of intermediate M2. Calculated molecular weight: 313.21, found C/Z:313.2.
synthesis example 4:
synthesis of P90
M1 in Synthesis example 3 was replaced with M2, and P90 was obtained without any change. Calculated molecular weight: 525.63, found C/Z:525.6.
synthesis of M3
1-bromo-8-iodonaphthalene (66.60 g,200 mmol), 2-nitrophenylboronic acid (33.40 g,200 mmol), tetrakis (triphenylphosphine) palladium (2.30 g,2 mmol), potassium carbonate (55.2 g,400 mmol), 1, 4-dioxane 1200ml, and distilled water 400ml were placed in a 3L reaction vessel under nitrogen atmosphere, and reacted at 100℃under reflux for 12 hours. Cooled to room temperature and the concentrated organic phases were combined. Separation by column chromatography gave intermediate M3-1.04 g. Calculated molecular weight: 328.17, found C/Z:328.2.
m3-1 (52.51 g,160 mmol), triphenylphosphine (104.92 g,400 mmol) and o-dichlorobenzene 600ml were placed in a 2L reaction vessel under nitrogen atmosphere and reacted at 180℃under reflux for 12h. Cooled to room temperature and the concentrated organic phases were combined. Separation by column chromatography gave intermediate M3-2.57 g. Calculated molecular weight: 296.17, found C/Z:296.2.
m3-2 (32.58 g,110 mmol), iodobenzene (22.44 g,110 mmol), cuprous iodide (20.95 g,110 mmol), phenanthroline (19.82 g,110 mmol), potassium phosphate (46.64 g,220 mmol), and xylene (500 ml) were placed in a 2L reaction vessel under nitrogen atmosphere, and reacted under reflux for 12 hours. Cooled to room temperature and the concentrated organic phases were combined. Separation by column chromatography gave 33.91g of intermediate M3. Calculated molecular weight: 372.27, found C/Z:372.3.
synthesis example 5:
synthesis of P204
The synthesis of example 3 in which M1 is replaced by M3, 2-chloro-4-phenyl quinazoline is replaced by 2-chloro-4, 6-diphenyltriazine, and the other is unchanged, P204. Calculated molecular weight: 611.71, found C/Z:611.7.
synthesis example 6:
synthesis of P208
M1 in Synthesis example 3 was replaced with M3, and P208 was obtained without any change. Calculated molecular weight: 584.68, found C/Z:584.7.
synthesis example 7:
synthesis of P213
2-chloro-4-phenylquinazoline (7.22 g,30 mmol), 4-fluorobenzeneboronic acid (4.20 g,30 mmol), tetrakis (triphenylphosphine) palladium (0.69 g,0.6 mmol), potassium carbonate (16.56 g,60 mmol), dioxane (100 ml) and distilled water (30 ml) were placed in a 500ml reaction vessel under nitrogen atmosphere, and reacted at 100℃under reflux for 12 hours. Cooled to room temperature and the concentrated organic phases were combined. Isolation by column chromatography gave intermediate P213-1.04 g. M:300.3.
the M1 in Synthesis example 3 was replaced with M3, and the 2-chloro-4-phenylquinazoline was replaced with P213-1, and the other was unchanged, to give P213. Calculated molecular weight: 660.78, found C/Z:660.8.
synthesis of comparative example 1:
synthesis of D2
Under a nitrogen atmosphere, M1 (32.32 g,100 mmol), 2-methylthiophenylboronic acid (16.80 g,100 mmol), tetrakis (triphenylphosphine) palladium (1.15 g,1 mmol), potassium carbonate (27.6 g,200 mmol), 1, 4-dioxane (600 ml) and distilled water (200 ml) were placed in a 1L reaction vessel and reacted at 100℃under reflux for 12 hours. Cooled to room temperature and the concentrated organic phases were combined. Separation by column chromatography gave intermediate D2-1.55 g. Calculated molecular weight: 366.52, found C/Z:366.5.
under nitrogen atmosphere, D2-1 (29.32 g,80 mmol) and 300ml of acetic acid were placed in a 1L reaction vessel, and H was introduced 2 O 2 (8.16 g,240 mmol) was dissolved in 50ml acetic acid and the solution was slowly added dropwise and reacted at room temperature for 8h. After the reaction, the acetic acid was removed by concentration. Separation by column chromatography gave intermediate D2-2.41 g. Calculated molecular weight: 382.52, found C/Z:382.5.
under nitrogen atmosphere, D2-2 (19.13 g,50 mmol) and 75ml of trifluoromethanesulfonic acid were put into a 500ml reaction vessel, stirred at room temperature for 24 hours, added with 40ml of pyridine and 5ml of water, and reacted under reflux for 30 minutes. The temperature was returned to room temperature, extracted with dichloromethane and the concentrated organic phases combined. Isolation by column chromatography gives 11.22g of intermediate D2. Calculated molecular weight: 350.48, found C/Z:350.5.
device embodiment
Description of the embodiments
The OLED includes a first electrode and a second electrode, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In particular embodiments, a substrate may be used below the first electrode or above the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, water resistance and transparency. A Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material serving as the first electrode on the substrate. When the first electrode is used as the anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO 2), zinc oxide (ZnO), or the like, and any combination thereof may be used. When the first electrode is used as the cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) and any combination thereof can be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compounds used as the organic material layer may be small organic molecules, large organic molecules and polymers, and combinations thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer hole transport layer containing only one compound and a single layer hole transport layer containing a plurality of compounds. The hole transport region may have a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or conductive dopant containing polymers such as polystyrene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as the compounds shown below HT-1 to HT-34; or any combination thereof.
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The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more of the compounds HT-1 through HT-34 described above, or one or more of the compounds HI1 through HI3 described below; one or more of the compounds HT-1 to HT-34 may also be used to dope one or more of the compounds HI1 to HI3 described below.
The luminescent layer comprises luminescent dyes (i.e. dopants) that can emit different wavelength spectra, and may also comprise Host materials (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The plurality of monochromatic light emitting layers with different colors can be arranged in a plane according to the pixel pattern, or can be stacked together to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light emitting layer may be a single color light emitting layer capable of simultaneously emitting different colors such as red, green, and blue.
According to different technologies, the luminescent layer material can be made of different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescence luminescent material and the like. In an OLED device, a single light emitting technology may be used, or a combination of different light emitting technologies may be used. The different luminescent materials classified by the technology can emit light of the same color, and can also emit light of different colors.
In one aspect of the application, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer host material is selected from, but not limited to, one or more of GPH-1 to GPH-80.
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In one aspect of the application, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of GPD-1 to GPD-47 listed below.
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In one aspect of the application, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of the RPD-1 through RPD-28 listed below.
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In one aspect of the application, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of YPD-1-YPD-11 listed below.
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The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single layer structure including a single layer electron transport layer containing only one compound and a single layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
In one aspect of the application, the electron transport layer material may be selected from, but is not limited to, combinations of one or more of ET-1 through ET-57 listed below.
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An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, a combination of one or more of the following.
LiQ，LiF，NaCl，CsF，Li 2 O，Cs 2 CO 3 ，BaO，Na，Li，Ca。
The preparation process of the organic electroluminescent device in this embodiment is as follows:
example 1
The glass plate coated with the ITO transparent conductive layer was sonicated in commercial cleaners, rinsed in deionized water, and rinsed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding surface with low-energy cation beam.
Placing the above glass substrate with anode in vacuum chamber, and vacuumizing to less than 1×10 -5 Pa, vacuum thermal evaporation of 10nm HT-4 on the anode layer film in sequence: HI-3 (97/3,w/w) mixture as hole injection layer, 60nm compound HT-4 as hole transport layer, 40nm compound P174: RPD-8 (100:3, w/w) binary mixture as light-emitting layer, 25nm compound ET-46: ET-57 (50/50, w/w) mixture as electron transport layer, liF of 1nm as electron injection layer, metallic aluminum of 150nm as cathode. The total evaporation rate of all organic layers and LiF was controlled at 0.1 nm/sec, and the evaporation rate of the metal electrode was controlled at 1 nm/sec.
Examples 2 to 5
An organic electroluminescent device was prepared according to the method described in example 1, except that P174 was replaced with P90, P204, P208 and P213, respectively.
Comparative example 1
An organic electroluminescent device was prepared as described in example 1, except that P174 was replaced with a compound as shown below:
the organic electroluminescent device prepared by the above procedure was subjected to the following performance measurement:
the driving voltage and current efficiency and the lifetime of the organic electroluminescent devices manufactured in examples 1 to 5 and comparative example 1 were measured using a digital source meter and a luminance meter at the same luminance. Specifically, the luminance of the organic electroluminescent device was measured to reach 3000cd/m by increasing the voltage at a rate of 0.1V per second 2 The voltage at the time is the driving voltage, and the current density at the time is measured; the ratio of brightness to current density is the current efficiency; the lifetime test of LT95 is as follows: using a luminance meter at 10000cd/m 2 Under the condition of brightness, constant current is kept, and the brightness of the organic electroluminescent device is measured to be reduced to 9500cd/m 2 Time in hours.
The organic electroluminescent device performance is shown in table 1 below:
TABLE 1 organic electroluminescent device Properties of examples 1 to 5 and comparative example 1
The result shows that the novel organic material is used for an organic electroluminescent device, can effectively reduce the voltage at the start and the stop, simultaneously keeps good efficiency, prolongs the service life of the material, and is a red light main body material with good performance.
Example 6
The glass plate coated with the ITO transparent conductive layer was sonicated in commercial cleaners, rinsed in deionized water, and rinsed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding surface with low-energy cation beam.
Placing the above glass substrate with anode in vacuum chamber, and vacuumizing to less than 1×10 -5 Pa, vacuum thermal evaporation of 10nm HT-4 on the anode layer film in sequence: HIL-3 (97/3,w/w) mixture as hole injection layer, 60nm compound HT-4 as hole transport layer, 40nm compound GPH-62: RPD-8 (100:3, w/w) binary mixture as light emitting layer, 5nm compound P204 as hole blocking layer, 25nm compound ET-46: ET-57 (50/50, w/w) mixture as electron transport layer, liF of 1nm as electron injection layer, metallic aluminum of 150nm as cathode. The total evaporation rate of all organic layers and LiF was controlled at 0.1 nm/sec, and the evaporation rate of the metal electrode was controlled at 1 nm/sec.
Examples 7 to 8
An organic electroluminescent device was prepared according to the method described in example 6, except that P204 was replaced with P208 or P213, respectively.
Comparative example 2
An organic electroluminescent device was prepared according to the method described in example 6, except that P204 was replaced with a compound as shown below:
the organic electroluminescent device prepared by the above procedure was subjected to the following performance measurement:
the driving voltage and current efficiency and the lifetime of the organic electroluminescent devices manufactured in examples 6 to 8 and comparative example 2 were measured using a digital source meter and a luminance meter at the same luminance. Specifically, the luminance of the organic electroluminescent device was measured to reach 3000cd/m by increasing the voltage at a rate of 0.1V per second 2 The voltage at the time is the driving voltage, and the current density at the time is measured; the ratio of brightness to current density is the current efficiency; the lifetime test of LT95 is as follows: using a luminance meter at 10000cd/m 2 Under the condition of brightness, constant current is kept, and the brightness of the organic electroluminescent device is measured to be reduced to 9500cd/m 2 Time in hours.
The organic electroluminescent device performance is shown in table 2 below:
TABLE 2 organic electroluminescent device Properties of examples 6-8 and comparative example 2
The result shows that the novel organic material can be used for a hole blocking layer material, and can improve the current efficiency and the service life of a device while keeping good reduction of the landing voltage.
Examples 9 to 10
An organic electroluminescent device was prepared according to the method described in example 6, except that P204 was replaced with P16 or P18, respectively.
Comparative example 3
An organic electroluminescent device was prepared according to the method described in example 6, except that P204 was replaced with the compound shown below prepared in synthetic comparative example 1:
the organic electroluminescent device properties are shown in table 3 below.
TABLE 3 organic electroluminescent device Properties of examples 9 and 10 and comparative example 3
The results show that materials without electron withdrawing groups such as P16 and P18 can also be used as hole blocking layer materials, and compared with D2, the compound with the seven-membered ring-containing large conjugated architecture can improve the service life of the device while maintaining good voltage and current rising and falling efficiency.
While the application has been described in connection with the embodiments, it is not limited to the above embodiments, but it should be understood that various modifications and improvements can be made by those skilled in the art under the guidance of the inventive concept, and the scope of the application is outlined in the appended claims.

Claims (8)

1. A compound having a structure represented by the general formula (1):
wherein X is independently selected from sulfur, CR c R d Y is independently selected from NR b 、CR c R d ；
Z 1 -Z 10 Each independently is CR z ，R z Is hydrogen;
R c ，R d ，R 1 ，R 2 ，R 3 and R is 4 Independently selected from hydrogen, halogen, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy, C2-C12 cycloalkoxy, silyl, carbonyl, acyl, ester, cyano, amine, C6-C30 aryl, C3-C30 heteroaryl, or a combination thereof;
R b selected from halogen, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy,C2-C12 cycloalkoxy, silyl, carbonyl, acyl, ester, cyano, amine, C6-C30 aryl, C3-C30 heteroaryl, or a combination thereof;
any two adjacent substituents may be linked to each other to form a ring;
when R is c ，R d When there are a plurality of any one, they are the same or different from each other.
2. The compound of claim 1, having the structure shown below:
wherein R is 1 、R 2 、R 3 、R 4 、R b 、R c 、R d As defined in claim 1.
3. The compound according to claim 1 or 2, wherein R b A group selected from the group consisting of:
4. the compound of claim 1 having a structure selected from the group consisting of:
5. use of a compound according to any one of claims 1 to 4 in an organic electroluminescent device.
6. An organic electroluminescent device comprising a first electrode, a second electrode and one or more organic material layers interposed between the first and second electrodes, wherein at least one of the organic material layers comprises the compound according to any one of claims 1 to 4.
7. The organic electroluminescent device according to claim 6, wherein the organic material layer comprising the compound according to any one of claims 1 to 4 is a light emitting layer and/or a hole blocking layer.
8. The organic electroluminescent device according to claim 6 or 7, wherein the compound according to any one of claims 1 to 4 is used as a light-emitting host in a light-emitting layer.
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