CN116283725A - Aromatic amine substituted dibenzofive-membered ring compound and application thereof - Google Patents
Aromatic amine substituted dibenzofive-membered ring compound and application thereof Download PDFInfo
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- CN116283725A CN116283725A CN202310067325.0A CN202310067325A CN116283725A CN 116283725 A CN116283725 A CN 116283725A CN 202310067325 A CN202310067325 A CN 202310067325A CN 116283725 A CN116283725 A CN 116283725A
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- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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Abstract
The present application providesThe compound shown in the formula (I) can be used for light extraction materials, and the compound provided by the application has a high steric hindrance framework and can reduce the refractive index of the light extraction materials. The organic electroluminescent device comprises a first light extraction layer and a second light extraction layer, wherein a synergistic effect exists between the specific first light extraction layer and the second light extraction layer, and the light extraction efficiency of the light extraction layer can be improved. The first light extraction layer comprises the compound as a light extraction material, and the second light extraction layer can comprise a high-refraction material commonly used in the field as a light extraction material, so that the refractive index of the first light extraction layer is lower than that of the second light extraction layer, and the refractive index difference of the first light extraction layer and the second light extraction layer is more than 0.3, and light extraction can be effectively promoted, so that the luminous efficiency of the organic electroluminescent device is improved. The display device provided by the application has excellent display effect.
Description
Technical Field
The present application relates to the field of organic light emitting displays, and in particular to a compound, a light extraction material, an organic electroluminescent device and a display device.
Background
Electroluminescence (EL) refers to a phenomenon in which a light emitting material emits light when excited by current and voltage under the action of an electric field, and is a light emitting process in which electric energy is directly converted into light energy. The organic electroluminescent display has the advantages of self-luminescence, low voltage DC drive, full solidification, wide viewing angle, light weight, simple composition and process, etc., compared with the liquid crystal display, the organic electroluminescent display does not need a backlight source, has large viewing angle and low power, the response speed can reach 1000 times of the liquid crystal display, and the manufacturing cost is lower than that of the liquid crystal display with the same resolution. Therefore, the organic electroluminescent device has very wide application prospect.
An organic electroluminescent device is a multi-layered organic thin film structure that includes a light emitting layer and other functional layers between a cathode and an anode. Light emitted from the light-emitting layer after being energized is transmitted out from one side of the transparent electrode, and the light is lost due to waveguide effects such as total reflection occurring between the respective film layers. The light extraction material can improve the light extraction efficiency by forming a light extraction layer on a transparent metal electrode at the upper part of the organic electroluminescent device, thereby adjusting the optical interference distance, and inhibiting extinction and the like caused by external light reflection and surface plasma movement.
The refractive index is the most important index of the light extraction material, and in general, the higher the refractive index of the light extraction layer, the higher the light extraction efficiency from the electrode to the light extraction layer, and the higher the luminous efficiency of the organic electroluminescent device. At present, one proposal is to increase the light extraction efficiency by increasing the refractive index of the light extraction material with a single layer structure, but the range of increase in the refractive index of the light extraction material is limited, which limits the increase in the luminous efficiency of the organic electroluminescent device. Another solution is to improve light extraction efficiency by providing a bilayer structure, where the light extraction layer includes a high refractive layer and a low refractive layer disposed between the high refractive layer and the cathode, and when refractive indexes of the low refractive layer material and the high refractive layer material differ by a certain value, light emission efficiency can be further improved.
Aromatic compounds are generally used as low refractive layer materials in the prior art, however, the refractive index of such compounds is generally higher and slightly different from that of common high refractive layer materials. Carbazole derivatives, benzimidazole derivatives, triazole derivatives, diamine aromatic compounds, non-aromatic amine fluorine-containing compounds, fluorene-containing compounds and the like are also proposed in the prior art as low refractive layer materials. The refractive index of the low refractive layer material used in the prior art is higher, and the refractive index of the low refractive layer material is smaller than that of the high refractive layer material, so that the improvement of the luminous efficiency of the organic electroluminescent device is limited.
Disclosure of Invention
The object of the present application is to provide a compound which, when used as a light extraction material for a low refractive layer, can improve the luminous efficiency of an organic electroluminescent device. The specific technical scheme is as follows:
in a first aspect, the present application provides a compound having the structure shown in formula (I):
wherein,,
x is selected from O, S, NR or CRbRc, rb, rc, R are each independently selected from methyl and the following groups N-1 to N-10:
R 1 ～R 4 each independently selected from hydrogen, fluorine, C unsubstituted or substituted with Ra 6 ～C 15 C, unsubstituted or substituted by Ra 5 ～C 20 Heteroaryl, C which is unsubstituted or substituted by Ra 5 ～C 10 Cycloalkyl, unsubstituted or substituted C by Ra 1 ～C 10 C, unsubstituted or substituted by Ra 2 ～C 5 Cycloalkyl containing heteroatoms and R 1 ～R 4 Are not hydrogen at the same time;
the substituents Ra of the individual radicals are each independently selected from fluorine, trifluoromethyl, cyano, amino, C 1 ～C 4 Alkyl of (a);
heteroaryl or a heteroatom on the heteroatom-containing cycloalkyl is each independently selected from O, S or N.
A second aspect of the present application provides a light extraction material comprising at least one of the compounds described above.
A third aspect of the present application provides an organic electroluminescent device comprising a first light extraction layer and a second light extraction layer, the first light extraction layer having a refractive index that is less than the refractive index of the second light extraction layer, the first light extraction layer comprising at least one of the light extraction materials described above.
A fourth aspect of the present application provides a display device comprising the organic electroluminescent device described above.
The beneficial effects of the application are that:
the compound shown in the formula (I) can be used for light extraction materials. The compound provided by the application comprises a high-steric-hindrance aromatic amine-substituted dibenzofive-membered ring structure, the molar volume of molecules can be increased, the stacking density among the molecules is reduced, the propagation rate of light in a medium is improved, namely, the propagation rate ratio of light in vacuum and the medium can be reduced, and the refractive index of a light extraction material is reduced. The first light extraction layer obtained by using the compound as the light extraction material has good transparency.
The organic electroluminescent device provided by the application comprises a first light extraction layer and a second light extraction layer, wherein a synergistic effect exists between the specific first light extraction layer and the specific second light extraction layer, and the organic electroluminescent device can be specifically characterized in that the first light extraction layer is also called a low-refraction layer, the second light extraction layer is also called a high-refraction layer, the refractive index of the first light extraction layer is lower than that of the second light extraction layer, the transmittance of the light extraction layer can be improved, the reflection of the light extraction layer is reduced, and the light extraction efficiency of the light extraction layer can be improved. Wherein, the first light extraction layer contains the compound of this application as light extraction material, and the second light extraction layer can contain the high refractive material that is commonly used in the art as light extraction material for the refractive index of first light extraction layer is less than the second light extraction layer, and the refractive index difference of the light extraction material of first light extraction layer and the light extraction material of second light extraction layer is greater than more than 0.3, can promote light extraction effectively, thereby has improved the luminous efficacy of organic electroluminescent device. The display device provided by the application has excellent display effect.
Of course, not all of the above-described advantages need be achieved simultaneously in practicing any one of the products or methods of the present application.
Drawings
For a clearer description of the technical solutions of the present application or of the prior art, reference will be made below to the accompanying drawings used in the embodiments or in the description of the prior art, which are, obviously, only some embodiments of the present application, from which it is possible for a person skilled in the art to obtain other embodiments.
Fig. 1 is a schematic structural view of a typical organic electroluminescent device.
FIG. 2 is a High Performance Liquid Chromatography (HPLC) spectrum of compound A-35 synthesized in synthetic example 6 of the present application.
Detailed Description
The following description of the embodiments of the present application will be made clearly and fully with reference to the accompanying drawings, in which it is evident that the embodiments described are only some, but not all, of the embodiments of the present application. Based on the embodiments herein, a person of ordinary skill in the art would be able to obtain all other embodiments based on the disclosure herein, which are within the scope of the disclosure herein.
In a first aspect, the present application provides a compound having the structure shown in formula (I):
Wherein,,
x is selected from O, S, NR or CRbRc, rb, rc, R are each independently selected from methyl and the following groups N-1 to N-10:
R 1 ～R 4 each independently selected from hydrogen, fluorine, C unsubstituted or substituted with Ra 6 ～C 15 C, unsubstituted or substituted by Ra 5 ～C 20 Heteroaryl, C which is unsubstituted or substituted by Ra 5 ～C 10 Cycloalkyl, unsubstituted or substituted C by Ra 1 ～C 10 C, unsubstituted or substituted by Ra 2 ～C 5 Cycloalkyl containing heteroatoms and R 1 ～R 4 Are not hydrogen at the same time;
the substituents Ra of the individual radicals are each independently selected from fluorine, trifluoromethyl, cyano, amino, C 1 ～C 4 Alkyl of (a);
heteroaryl or a heteroatom on the heteroatom-containing cycloalkyl is each independently selected from O, S or N.
Preferably, rb, rc, R are selected from methyl and the following groups:
preferably, R 1 ～R 4 Each independently selected from the group consisting of hydrogen, fluorine, trifluoromethyl, methyl, t-butyl, and the groups represented by R-1 to R-48:
more preferably, R 1 ～R 4 Each independently selected from the group consisting of hydrogen, fluorine, trifluoromethyl, methyl, t-butyl, and the groups shown below:
for example, the aforementioned compounds are selected from the compounds shown in the following A-1 to A-43:
the compound provided in the first aspect of the application has a structure shown in a formula (I). The compound comprises a high-steric-hindrance aromatic amine-substituted dibenzofive-membered ring structure, at least one phenylene connected with N is ortho-position substituted, the molecular structure of the compound is high in steric hindrance, the space structure tends to be stereospecific, the stacking density among molecules of the compound can be reduced, the propagation rate of light in a medium is facilitated, namely, the propagation rate ratio of light in vacuum and the medium can be reduced, and therefore, the compound provided by the application has a lower refractive index when being used as a light extraction layer. In addition, the substituent group of the compound can also comprise a fluorine-containing substituent group, and the fluorine-containing substituent group has extremely high electron polarization rate and extremely high electronegativity, so that the bond energy of a C-F bond is extremely high, the fluorine-containing substituent group has larger volume, can cooperate with a high-steric-hindrance aromatic amine-substituted dibenzofive-membered ring structure, improves the steric hindrance of the compound, reduces the intermolecular packing density of the compound, and is beneficial to improving the propagation speed of light in a medium, thereby reducing the refractive index of the light extraction material. The first light extraction layer obtained by adopting the compound as the light extraction material has good transparency, lower dielectric constant and refractive index.
A second aspect of the present application provides a light extraction material comprising at least one of the compounds described above. The compounds provided herein have a lower refractive index when used in light extraction materials.
In some embodiments of the present application, the refractive index of the light extraction material is less than or equal to 1.59; preferably, the light extraction material has a red light refractive index of 1.50 or less, a green light refractive index of 1.55 or less, and a blue light refractive index of 1.59 or less.
A third aspect of the present application provides an organic electroluminescent device comprising a first light extraction layer and a second light extraction layer, the first light extraction layer having a refractive index that is less than the refractive index of the second light extraction layer, the first light extraction layer comprising at least one of the light extraction materials described above. Wherein the first light extraction layer has good transparency. The first light extraction layer and the second light extraction layer in the organic electroluminescent device have synergistic effect, and the light extraction efficiency of the light extraction layers can be improved. The first light extraction layer contains the compound as a light extraction material, and the second light extraction layer can contain a high-refraction material commonly used in the field as a light extraction material, so that the refractive index of the first light extraction layer is lower than that of the second light extraction layer, which is beneficial to promoting light extraction and improving the luminous efficiency of the organic electroluminescent device. The inventors found that when the refractive index difference between the light extraction material of the first light extraction layer and the light extraction material of the second light extraction layer is 0.3 or more, light extraction can be further effectively promoted, thereby further improving the light emission efficiency of the organic electroluminescent device.
In the present application, the kind and structure of the organic electroluminescent device are not particularly limited, and various types and structures of organic electroluminescent devices known in the art may be used as long as at least one of the light extraction materials provided in the present application can be used.
The organic electroluminescent device of the present application may be a light emitting device having a top emission structure, and examples thereof include an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a transparent or semitransparent cathode, a first light extraction layer, and a second light extraction layer, which are sequentially formed on a substrate.
The organic electroluminescent device of the present application may be a light emitting device having a bottom light emitting structure, and examples thereof include a substrate, a second light extraction layer, a first light extraction layer, a transparent or semitransparent anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode.
The organic electroluminescent device of the present application may be a light emitting device having a double-sided light emitting structure, and the substrate may include a second light extraction layer, a first light extraction layer, a transparent or semitransparent anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a transparent or semitransparent cathode, a first light extraction layer, and a second light extraction layer in this order.
In addition, an electron blocking layer may be provided between the hole transport layer and the light emitting layer, and a hole blocking layer may be provided between the light emitting layer and the electron transport layer. However, the structure of the organic electroluminescent device of the present application is not limited to the above-described specific structure, and each of the above-described layers may be omitted or added if necessary. The thickness of each layer is not particularly limited as long as the object of the present application can be achieved. For example, the organic electroluminescent device may include an anode (100 nm to 150 nm), a hole injection layer (5 nm to 20 nm), a hole transport layer (80 nm to 140 nm), an electron blocking layer (5 nm to 15 nm), a light emitting layer (20 nm to 45 nm), a hole blocking layer (5 nm to 15 nm), an electron transport layer (30 nm to 40 nm), an electron injection layer (0.3 nm to 1 nm), a cathode (10 nm to 16 nm), a first light extraction layer (5 nm to 50 nm), and a second light extraction layer (50 nm to 90 nm) made of a metal oxide or a metal, in this order, on a substrate.
The material of the substrate is not particularly limited, and conventional substrates used in the organic electroluminescent device in the related art, for example, glass, polymer materials, glass with Thin Film Transistor (TFT) elements, polymer materials, and the like can be used.
Fig. 1 shows a schematic view of a typical organic electroluminescent device 100, in which a substrate 10, an anode electrode 11, a hole injection layer 12, a hole transport layer 13, an electron blocking layer 14, a light emitting layer 15, a hole blocking layer 16, an electron transport layer 17, an electron injection layer 18, a cathode electrode 19, and a light extraction layer 21 are sequentially disposed from bottom to top, wherein the light extraction layer 21 includes a first light extraction layer 211 and a second light extraction layer 212.
It will be appreciated that fig. 1 schematically illustrates only one typical organic electroluminescent device structure, and the present application is not limited to this structure, and the light extraction material of the present application may be used in any type of organic electroluminescent device.
In the organic electroluminescent device of the present application, various materials used for the layers in the prior art may be used for the other layers, except that the light extraction layer contains the light extraction material provided in the present application.
For convenience, the organic electroluminescent device of the present application will be described below with reference to fig. 1, but this is not meant to limit the scope of protection of the present application in any way. It is understood that all organic electroluminescent devices capable of using the light extraction materials of the present application are within the scope of the present application.
In the present application, the material of the substrate 10 is not particularly limited, and conventional substrates used in the organic electroluminescent device in the related art, for example, glass, polymer materials, glass with Thin Film Transistor (TFT) elements, polymer materials, and the like can be used.
In the present application, the material of the anode electrode 11 is not particularly limited, and may be selected from anode electrodes known in the art. For example, a metal, an alloy, or a conductive compound having a high work function (. Gtoreq.4 eV) may be specifically selected from a transparent conductive material such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO 2), zinc oxide (ZnO), low Temperature Polysilicon (LTPS), or a metal material such as silver, an alloy thereof, aluminum, or an alloy thereof, or an organic conductive material such as poly (3, 4-ethylenedioxythiophene) (PEDOT), or an amorphous material such as In2O3-ZnO (IDIXO) that can form a transparent conductive film, or a multilayer structure In which the anode electrode is formed of the above materials. In the present application, the thickness of the anode electrode may vary depending on the materials used, as long as it is within the above-described range of the present application, and the object of the present application can be achieved.
In the present application, the material of the hole injection layer 12 is not particularly limited, and a hole injection layer material known in the art, for example, a Hole Transport Material (HTM) may be selected as the hole injection material.
In this application, the hole injection layer 12 may further include a p-type dopant, the kind of which is not particularly limited, and various p-type dopants known in the art may be used, for example, the following p-type dopants may be employed:
in the present application, the amount of the p-type dopant is not particularly limited, and may be an amount well known to those skilled in the art.
In the present application, the material of the hole transport layer 13 is not particularly limited, and may be made using a Hole Transport Material (HTM) known in the art. The number of layers of the hole transport layer 13 is not particularly limited and may be adjusted according to actual needs as long as the purpose of the present application is satisfied, for example, 1 layer, 2 layers, 3 layers, 4 layers, or more.
For example, the material for the hole injection layer and the material for the hole transport layer may each be independently selected from, but not limited to, at least one of the following HT-1 to HT-32 compounds:
alternatively, the organic electroluminescent device may include the electron blocking layer 14, and in this application, a material of the electron blocking layer 14 is not particularly limited, and an electron blocking layer material known in the art may be used. For example, it may be selected from, but not limited to, the following EB-1 to EB-5 compounds:
In the present application, the material of the light emitting layer 15 includes a light emitting layer host material and a light emitting layer guest material, wherein the amounts of the light emitting layer host material and the light emitting layer guest material are not particularly limited, and may be those known to those skilled in the art.
In the present application, the light emitting layer host material is not particularly limited, and at least one of red light emitting layer host materials known in the art may be used. For example, at least one of the following RH-1 to RH-14 compounds may be selected, but is not limited to:
the light emitting layer host material may also use at least one of green light emitting layer host materials known in the art. For example, at least one of the following GPH-1 to GPH-81 compounds may be selected, but is not limited to:
the light emitting layer host material may also use at least one of blue light emitting layer host materials known in the art. For example, at least one of the following BH-1 to BH-10 compounds may be selected, but not limited to:
the light emitting layer guest material may be a red light emitting layer guest material, for example, may be selected from, but not limited to, at least one of the following RPD-1 to RPD-28 compounds:
the light emitting layer guest material may be a green light emitting layer guest material, for example, may be selected from, but not limited to, at least one of the following GD01 to GD04 compounds:
The light emitting layer guest material may be a blue light emitting layer guest material, for example, may be selected from, but not limited to, at least one of the following BD-1 to BD-10 compounds:
alternatively, the organic electroluminescent device may include the hole blocking layer 16, and in this application, a material of the hole blocking layer 16 is not particularly limited, and a hole blocking layer material known in the art may be used. For example, known hole blocking layer materials may be selected from, but are not limited to, at least one of the following ET-1 to ET-63 compounds:
in the present application, the material of the electron transport layer 17 is not particularly limited, and electron transport materials known in the art may be used. For example, the known electron transport material may be selected from, but is not limited to, at least one of the above ET-1 to ET-61 compounds.
In this application, the electron transport layer 17 may further include n-type dopants, the kind of which is not particularly limited, and various n-type dopants known in the art may be employed, for example, the following n-type dopants may be employed:
in the present application, the amount of the n-type dopant is not particularly limited, and may be an amount well known to those skilled in the art.
In the present application, the material of the electron injection layer 18 is not particularly limited, and electron injection materials known in the art may be used, and may include, for example, but not limited to, lithium 8-hydroxyquinoline (LiQ), liF, naCl, csF, li 2 O、Cs 2 CO 3 At least one of materials such as BaO, yb, na, li, ca.
In the present application, the material of the cathode electrode 19 is not particularly limited, and may be selected from, but not limited to, magnesium silver mixture, magnesium aluminum mixture, liF/aluminum, ITO, aluminum or other metals, oxides, and the like.
In the present application, the light extraction layer 21 includes a first light extraction layer 211 and a second light extraction layer 212. The first light extraction layer 211 contains at least one of the light extraction materials of the present application, and the refractive index of the first light extraction layer is lower than that of the second light extraction layer, so that light extraction can be promoted. In order to improve the light extraction efficiency, the light extraction layer 21 of the present application is provided on the transparent electrode on the light extraction side, and the first light extraction layer is provided between the transparent electrode and the second light extraction layer.
In the present application, the second light extraction layer 212 may include a high refractive material known in the art as a light extraction material, and the refractive index of the high refractive material is selected to be different from that of the light extraction material of the present application by more than 0.3, for example, the known high refractive material may be selected from, but not limited to, at least one of the following C-1 to C-63 compounds:
the method for preparing the organic electroluminescent device is not particularly limited, and any method known in the art may be used, for example, the following steps may be included:
(1) Cleaning an anode electrode 11 on a substrate 10 of the top-emission organic electroluminescent device, respectively performing steps of medicine washing, water washing, hairbrush, high-pressure water washing, air knife and the like in a cleaning machine, and then performing heating treatment; the liquid medicine used in the medicine washing can be liquid medicine known in the field, and the application is not limited to the liquid medicine; the conditions of the steps of washing, hairbrush, high-pressure washing, air knife and the like can also be known in the art, and the application is not limited to the conditions;
(2) Vacuum evaporating a hole injection layer 12 on the anode electrode 11, wherein the hole injection layer 12 contains a hole injection material and a p-type dopant;
(3) Vacuum evaporating a hole transport material on the hole injection layer 12 as a hole transport layer 13;
(4) Vacuum evaporating an electron blocking material on the hole injection layer 13 as an electron blocking layer 14;
(5) Vacuum evaporating a light-emitting layer 15 on the electron blocking layer 14, wherein the light-emitting layer 15 comprises a host material and a guest material;
(6) Evaporating a hole blocking material on the light emitting layer 15 as a hole blocking layer 16;
(7) Vacuum evaporating an electron transport material on the hole blocking layer 16 as an electron transport layer 17, wherein the electron transport layer 17 comprises the electron transport material and an n-type dopant;
(8) Vacuum evaporating an electron injection material on the electron transport layer 17 as an electron injection layer 18;
(9) Vacuum evaporating a cathode material on the electron injection layer 18 as a cathode electrode 19;
(10) Evaporating a material of the first light extraction layer 211 on the cathode electrode 19 as the first light extraction layer 211;
(11) A material of the second light extraction layer 212 is vapor-deposited on the first light extraction layer 211 as the second light extraction layer 212.
A fourth aspect of the present application provides a display apparatus comprising the organic electroluminescent device described above. Therefore, the display device provided by the application has good display performance. The display device may include, but is not limited to, a display, a television, a tablet, a mobile communication terminal, and the like.
Test method and apparatus:
test of purity of the compound:
the High Performance Liquid Chromatography (HPLC) purity and HPLC profile of the compound was determined using an LC-20AXR high performance liquid chromatograph with detector A wavelength of 254nm.
Refractive index test:
the refractive index (n) of each of the compounds of examples and comparative examples was measured at different wavelengths using an EMA (effective dielectric modeling method) method using a Version-1.0.1.4 spectroscopic ellipsometer from Radiation technology company, wherein the material film was formed by vapor deposition of the compound of each of the examples or comparative examples on the glass substrate at a vapor deposition rate of 0.1nm/s and a vapor deposition film thickness of 80nm.
Performance detection of organic electroluminescent device:
a luminance-current density-voltage (BJV) test system was used to test the current efficiency and CIE color coordinates of the organic electroluminescent device.
For a blue light device, the luminous efficiency is examined by using a blue light index (BI), and when the luminous colors are the same or similar (namely, when CIE coordinates are the same or similar), the higher the BI value is, the better the luminous performance of the blue light device is; for a green organic electroluminescent device (green device) and a red organic electroluminescent device (red device), the luminous efficiency is mainly evaluated by current efficiency, and when the luminous colors are the same or similar (i.e., when CIE coordinates are the same or similar), the greater the current efficiency, the better the luminous performance of the green device and the red device.
The method for synthesizing the compound of the present application is not particularly limited, and may be synthesized by any method known to those skilled in the art. The following illustrates the synthesis of the compounds of the present application.
Synthetic examples
All raw materials used in the synthetic embodiment of the application belong to chemical raw materials well known to the person skilled in the chemical industry, and the raw material information is as follows:
f-0: chinese name, 2-aminophenylboronic acid; CAS No.5570-18-3.
F-1: chinese name, bromopentafluorobenzene; CAS No.344-04-7.
F-2: chinese name, 2-bromophenyl boronic acid; CAS No.244205-40-1.
F-3: chinese name, 2-chlorophenylboronic acid; CAS No.3900-89-8.
F-4: chinese name, 1-chlorodibenzofuran; CAS No.84761-86-4.
F-5: chinese name, 3, 5-bistrifluoromethyl bromobenzene; CAS No.328-70-1.
F-6: chinese name, 4-chlorobenzoic acid; CAS No.1679-18-1.
F-7: chinese name, 4-tert-butylbromobenzene; CAS No.3972-65-4.
F-8: chinese name, 4-aminophenylboronic acid; CAS No.89415-43-0.
F-9: chinese name, 1-chlorodibenzothiophene; CAS No.109014-36-0.
F-10: chinese name, 4-chlorocarbazole; CAS No.3652-88-8.
F-11: chinese name, bromocyclohexane; CAS No.108-85-0.
F-12: chinese name, 4-amino-9, 9-dimethylfluorene; CAS No.2249831-75-0.
F-13: chinese name, 2-chloroadamantane; CAS No.7346-41-0.
F-14: chinese name, 2-chlorophenylboronic acid; CAS No.3900-89-8.
F-15: chinese name, benzophenone; CAS No.119-61-9.
F-16: chinese name, 3', 5' -tetrafluoromethylbenzophenone; CAS No.175136-66-0.
F-17: chinese name, 2-bromo-2 '-chloro-1, 1' -biphenyl; CAS No.107208-70-8.
Synthesis example 1: synthesis of Compound A-3
< preparation of intermediate M0 >
Into a reaction flask were charged 100mmol of F-1, 100mmol of F-0, 41.4g (300 mmol) of potassium carbonate, 800ml of Tetrahydrofuran (THF), 200ml of water, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 ) The reaction was carried out at 120℃for 12h. After the reaction, the reaction was stopped, the reaction product was cooled to room temperature, water was added, the organic phase was concentrated to give a white solid, which was filtered and washed with water, and the obtained solid was purified by recrystallization with toluene to give white powder M0. Wherein Pd (PPh) 3 ) 4 The amount of (C) added was 1mol% based on F-1.
< preparation of intermediate M1 >
Into a reaction flask were charged 100mmol of F-1, 100mmol of F-2, 41.4g (300 mmol) of potassium carbonate, 800ml of THF, 200ml of water, and 1mol% of Pd (PPh) 3 ) 4 The reaction was carried out at 120℃for 12h. After the reaction, the reaction was stopped, the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to give a white solid, which was filtered and washed with water, and the obtained solid was purified by recrystallization with toluene to give white powder M1. Wherein Pd (PPh) 3 ) 4 The amount of (C) added was 1mol% based on F-1.
< preparation of intermediate M2 >
Into a reaction flask were charged 100mmol of M1, 100mmol of F-3, 41.4g (300 mm) ol), 800ml of THF, 200ml of water, and 1mol% of Pd (PPh) 3 ) 4 The reaction was carried out at 120℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M2. Wherein Pd (PPh) 3 ) 4 The amount of (C) added was 1mol% based on M1.
< preparation of intermediate M3 >
Into a reaction flask were charged 100mmol of M2, 100mmol of M0, 28.83g (300 mmol) of sodium t-butoxide, 800ml of xylene, and 1mol% of bis (benzalacetone) palladium (Pd (dba) 2 ) The reaction was carried out at 120℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, and washed with water, and the obtained solid was purified by recrystallization with toluene to obtain white powder M3. Wherein Pd (dba) 2 The amount of (2) added was 1mol% of M2.
< preparation of Compound A-3 >
Into a reaction flask were charged 100mmol of F-4, 100mmol of M3, 28.83g (300 mmol) of sodium tert-butoxide, 800ml of xylene, and 1mol% of Pd (dba) 2 The reaction was carried out at 120℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, and washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder of compound a-3. Wherein Pd (dba) 2 The amount of (C) added was 1mol% based on F-4.
The HPLC purity of the prepared compound A-3 was 99.9%.
1H NMR(300MHz,Chloroform-d)δ8.10-7.96(m,5H),7.60-7.54(m,3H),7.39-7.25(m,8H),7.14(m,2H),6.91(s,1H)。
Synthesis example 2: synthesis of Compound A-4
< preparation of intermediate M0 > was the same as in synthesis example 1.
< preparation of intermediate M1 >
Into a reaction flask were charged 100mmol of F-2, 100mmol of F-5, 41.4g (300 mmol) of potassium carbonate, 800ml of THF, 200ml of water, and 1mol% of Pd (PPh) 3 ) 4 The reaction was carried out at 120℃for 12h. After the reaction, the reaction was stopped, the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to give a white solid, which was filtered and washed with water, and the obtained solid was purified by recrystallization with toluene to give white powder M1. Wherein Pd (PPh) 3 ) 4 The amount of (C) added was 1mol% based on F-2.
< preparation of intermediate M2 >
Into a reaction flask were charged 100mmol of M1, 100mmol of F-3, 41.4g (300 mmol) of potassium carbonate, 800ml of THF, 200ml of water, and 1mol% of Pd (PPh) 3 ) 4 The reaction was carried out at 120℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M2. Wherein Pd (PPh) 3 ) 4 The amount of (C) added was 1mol% based on M1.
< preparation of intermediate M3 >
Into a reaction flask were charged 100mmol of M2, 100mmol of M0, 28.83g (300 mmol) of sodium tert-butoxide, 800ml of xylene, and 1mol% of Pd (dba) 2 The reaction was carried out at 120℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, and washed with water, and the obtained solid was purified by recrystallization with toluene to obtain white powder M3. Wherein Pd (dba) 2 The amount of (2) added was 1mol% of M2.
< preparation of Compound A-4 >
Into a reaction flask were charged 100mmol of F-4, 100mmol of M3, 28.83g (300 mmol) of sodium tert-butoxide, 800ml of xylene, and 1mol% of Pd (dba) 2 The reaction was carried out at 120℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, and washed with water, and the obtained solid was purified by recrystallization with toluene to obtain compound a-4 as a white powder. Wherein Pd (dba) 2 Is added in the amount of (2)1mol% of F-4.
The HPLC purity of the prepared compound A-4 was 99.9%.
1H NMR(300MHz,Chloroform-d)δ8.33(s,1H),8.10-7.96(m,7H),7.60-7.54(m,3H),7.39-7.25(m,8H),7.14(m,2H),6.91(s,1H)。
Synthesis example 3: synthesis of Compound A-6
< preparation of intermediate M0 >
Into a reaction flask were charged 100mmol of F-7, 100mmol of F-0, 41.4g (300 mmol) of potassium carbonate, 800ml of THF, 200ml of water, and 1mol% of (Pd (PPh) 3 ) 4 ) The reaction was carried out at 120℃for 12h. After the reaction, the reaction was stopped, the reaction product was cooled to room temperature, water was added, the organic phase was concentrated to give a white solid, which was filtered and washed with water, and the obtained solid was purified by recrystallization with toluene to give white powder M0. Wherein Pd (PPh) 3 ) 4 The amount of (C) added was 1mol% based on F-7.
< preparation of intermediate M1 >
Into a reaction flask were charged 100mmol of F-5, 100mmol of F-3, 41.4g (300 mmol) of potassium carbonate, 800ml of THF, 200ml of water, and 1mol% of Pd (PPh) 3 ) 4 The reaction was carried out at 120℃for 12h. After the reaction, the reaction was stopped, the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to give a white solid, which was filtered and washed with water, and the obtained solid was purified by recrystallization with toluene to give white powder M1. Wherein Pd (PPh) 3 ) 4 The amount of (C) added was 1mol% based on F-5.
< preparation of intermediate M2 >
Into a reaction flask were charged 100mmol of M1, 100mmol of M0, 28.83g (300 mmol) of sodium tert-butoxide, 800ml of xylene, and 1mol% of Pd (dba) 2 The reaction was carried out at 120℃for 12h. Stopping the reaction after the reaction is finished, cooling the reactant to room temperature, adding water, filtering, washing with water, and recrystallizing and purifying the obtained solid by using toluene White powder M2 was obtained. Wherein Pd (dba) 2 The amount of (C) added was 1mol% based on M1.
< preparation of Compound A-6 >
Into a reaction flask were charged 100mmol of F-4, 100mmol of M2, 28.83g (300 mmol) of sodium tert-butoxide, 800ml of xylene, and 1mol% of Pd (dba) 2 The reaction was carried out at 120℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, and washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder of compound a-6. Wherein Pd (dba) 2 The amount of (C) added was 1mol% based on F-4.
The HPLC purity of the prepared compound A-6 was 99.9%.
1H NMR(300MHz,Chloroform-d)δ8.33(s,1H),8.10-7.98(m,5H),7.54(s,1H),7.39-7.30(m,11H),7.25(s,1H),7.14(m,2H),6.91(s,1H),1.33(m,9H)。
Synthesis example 4: synthesis of Compound A-14
< preparation of intermediate M0 >
Into a reaction flask were charged 100mmol of F-1, 100mmol of F-8, 41.4g (300 mmol) of potassium carbonate, 800ml of THF, 200ml of water, and 1mol% of Pd (PPh) 3 ) 4 The reaction was carried out at 120℃for 12h. After the reaction, the reaction was stopped, the reaction product was cooled to room temperature, water was added, the organic phase was concentrated to give a white solid, which was filtered and washed with water, and the obtained solid was purified by recrystallization with toluene to give white powder M0. Wherein Pd (PPh) 3 ) 4 The amount of (C) added was 1mol% based on F-1.
< preparation of intermediate M1 >, < preparation of intermediate M2 > was the same as in synthesis example 2.
< preparation of intermediate M3 >
Into a reaction flask were charged 100mmol of M2, 100mmol of M0, 28.83g (300 mmol) of sodium tert-butoxide, 800ml of xylene, and 1mol% of Pd (dba) 2 At 120 DEG CThe reaction was carried out for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, and washed with water, and the obtained solid was purified by recrystallization with toluene to obtain white powder M3. Wherein Pd (dba) 2 The amount of (2) added was 1mol% of M2.
< preparation of Compound A-14 >
Into a reaction flask were charged 100mmol of F-9, 100mmol of M3, 28.83g (300 mmol) of sodium tert-butoxide, 800ml of xylene, and 1mol% of Pd (dba) 2 The reaction was carried out at 120℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, and washed with water, and the obtained solid was purified by recrystallization with toluene to obtain compound a-14 as a white powder. Wherein Pd (dba) 2 The amount of (C) added was 1mol% based on F-9.
The HPLC purity of the prepared compound A-14 was 99.9%.
1H NMR(300MHz,Chloroform-d)δ8.45-8.33(m,2H),8.10-7.93(m,6H),7.60-7.55(m,6H),7.49-7.37(m,7H),7.14(s,1H)。
Synthesis example 5: synthesis of Compound A-16
< preparation of intermediate M0 >, < preparation of intermediate M1 > and < preparation of intermediate M2 > were the same as in synthesis example 3.
< preparation of intermediate M3 >
Into the reaction flask were charged 100mmol of F-5, 120mmol of F-10, 1.9g (10 mmol) of cuprous iodide, 27.2g (200 mmol) of anhydrous potassium carbonate, 2.0g (10 mmol) of 1, 10-phenanthroline monohydrate, 730g (10 mol) of N, N-dimethylformamide, and reacted at 120℃under nitrogen atmosphere for 20 hours. Stopping the reaction after the reaction is finished, cooling the reactant to room temperature, adding water, concentrating the organic phase to obtain white solid, filtering, washing the white solid with water, and eluting and purifying the obtained solid with petroleum ether to obtain white powder M3.
< preparation of Compound A-16 >
In a reaction flask100mmol of M3, 100mmol of M2, 28.83g (300 mmol) of sodium tert-butoxide, 800ml of xylene and 1mol% of Pd (dba) are added 2 The reaction was carried out at 120℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, and washed with water, and the obtained solid was purified by recrystallization with toluene to obtain compound a-16 as a white powder. Wherein Pd (dba) 2 The amount of (2) added was 1mol% of M3.
The HPLC purity of the prepared compound A-16 was 99.9%.
1H NMR(300MHz,Chloroform-d)δ8.33-8.19(m,2H),8.10-8.07(m,6H),7.87(s,1H),7.60-7.50(m,3H),7.39-7.20(m,10H),7.14(m,2H),6.40(s,1H),1.33(m,9H)。
Synthesis example 6: synthesis of Compound A-33
< preparation of intermediate M1 >
Into a reaction flask were charged 100mmol of F-1, 100mmol of F-2, 41.4g (300 mmol) of potassium carbonate, 800ml of THF, 200ml of water, and 1mol% of Pd (PPh) 3 ) 4 The reaction was carried out at 120℃for 12h. After the reaction, the reaction was stopped, the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to give a white solid, which was filtered and washed with water, and the obtained solid was purified by recrystallization with toluene to give white powder M1. Wherein, the addition amount of Pd (PPh 3) 4 is 1mol% of F-1.
< preparation of intermediate M2 >
Into a reaction flask were charged 100mmol of F-2, 100mmol of M1, 41.4g (300 mmol) of potassium carbonate, 800ml of THF, 200ml of water, and 1mol% of Pd (PPh) 3 ) 4 The reaction was carried out at 120℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M2. Wherein Pd (PPh) 3 ) 4 The amount of (C) added was 1mol% based on F-2.
< preparation of Compound A-33 >
Into a reaction flask were charged 100mmol of F-12, 200mmol of M2, 19.22g (200 mmol) of sodium tert-butoxide, and 1mol% of tris (dibenzylideneacetone) dipalladium (Pd 2 (dba) 3 ) 4mol% of 2-cyclohexylphosphine-2, 4, 6-triisopropylbiphenyl (X-PHOS) and reacting at 110 ℃ for 12h. After the reaction, the reaction was stopped, the reaction product was cooled to room temperature, water was added, the organic phase was concentrated to give a white solid, which was filtered and washed with water, and the obtained solid was purified by recrystallization with toluene to give white powder A-33. Wherein Pd is 2 (dba) 3 The amount of the catalyst was 1mol% based on F-12, and the amount of the X-PHOS added was 4mol% based on F-12.
The HPLC purity of the prepared compound A-33 was 99.9%.
1H NMR(300MHz,Chloroform-d)δ8.10-7.90(m,7H),7.60-7.55(m,5H),7.39-7.37(m,5H),7.28-7.21(m，3H),7.16-7.14(m,3H),1.69(m,6H)。
Synthesis example 7: synthesis of Compound A-35
< preparation of intermediate M1 >
Into a reaction flask were charged 100mmol of F-11, 100mmol of F-2, 41.4g (300 mmol) of potassium carbonate, 800ml of THF, 200ml of water, and 1mol% of Pd (PPh) 3 ) 4 The reaction was carried out at 120℃for 12h. After the reaction, the reaction was stopped, the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to give a white solid, which was filtered and washed with water, and the obtained solid was purified by recrystallization with toluene to give white powder M1. Wherein Pd (PPh) 3 ) 4 The amount of (C) added was 1mol% based on F-11.
< preparation of intermediate M2 >
Into a reaction flask were charged 100mmol of F-2, 100mmol of M1, 41.4g (300 mmol) of potassium carbonate, 800ml of THF, 200ml of water, and 1mol% of Pd (PPh) 3 ) 4 The reaction was carried out at 120℃for 12h. Stopping the reaction after the reaction is completed, and reactingCooling to room temperature, adding water, concentrating the organic phase to obtain white solid, filtering, washing with water, and recrystallizing and purifying the obtained solid with toluene to obtain white powder M2. Wherein Pd (PPh) 3 ) 4 The amount of (C) added was 1mol% based on F-2.
< preparation of Compound A-35 >
Into a reaction flask were charged 100mmol of F-12, 200mmol of M2, 19.22g (200 mmol) of sodium tert-butoxide, and 1mol% of tris (dibenzylideneacetone) dipalladium (Pd 2 (dba) 3 ) 4mol% of 2-dicyclohexyl phosphorus-2, 4, 6-triisopropyl biphenyl (X-PHOS) and carrying out reflux reaction at 120 ℃ for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain the compound A-35 of white powder. Wherein Pd is 2 (dba) 3 The amount of the catalyst was 1mol% based on F-12, and the amount of the X-PHOS added was 4mol% based on F-12.
The HPLC purity of the prepared compound A-35 is 99.9%, and the HPLC spectrum is shown in FIG. 2.
1H NMR(300MHz,Chloroform-d)8.10-7.90(m,3H),7.77-7.51(m,5H),7.40-7.21(m,12H),7.16-7.14(m,3H),2.72(m,2H),1.86-1.43(m,26H)。
Synthesis example 8: synthesis of Compound A-40
< preparation of intermediate M3 > the same as in Synthesis example A-16
< preparation of intermediate M1 >
Into a reaction flask were charged 100mmol of F-6, 100mmol of M3, 41.4g (300 mmol) of potassium carbonate, 800ml of THF, 200ml of water, and 1mol% of Pd (PPh) 3 ) 4 The reaction was carried out at 120℃for 12h. After the reaction, the reaction was stopped, the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to give a white solid, which was filtered and washed with water, and the obtained solid was purified by recrystallization with toluene to give white powder M1. Wherein Pd (PPh) 3 ) 4 The amount of (C) added was 1mol% based on F-6.
< preparation of intermediate M2 >
Into a reaction flask were charged 100mmol of F-14, 100mmol of M1, 41.4g (300 mmol) of potassium carbonate, 800ml of THF, 200ml of water, and 1mol% of Pd (PPh) 3 ) 4 The reaction was carried out at 120℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M2. Wherein Pd (PPh) 3 ) 4 The amount of (C) added was 1mol% based on F-14.
< preparation of intermediate M4 >
Into a reaction flask were charged 100mmol of F-12, 100mmol of M2, 28.83g (300 mmol) of sodium tert-butoxide, 800ml of xylene, and 1mol% of Pd (dba) 2 The reaction was carried out at 120℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, and washed with water, and the obtained solid was purified by recrystallization with toluene to obtain white powder M4. Wherein Pd (dba) 2 The amount of (C) added was 1mol% based on F-12.
< preparation of intermediate M5 >
Into a reaction flask were charged 100mmol of F-3, 100mmol of F-13, 41.4g (300 mmol) of potassium carbonate, 800ml of THF, 200ml of water, and 1mol% of Pd (PPh) 3 ) 4 The reaction was carried out at 120℃for 12h. After the reaction, the reaction was stopped, the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to give a white solid, which was filtered and washed with water, and the obtained solid was purified by recrystallization with toluene to give white powder M5. Wherein Pd (PPh) 3 ) 4 The amount of (C) added was 1mol% based on F-3.
< preparation of Compound A-40 >
Into a reaction flask were charged 100mmol of M5, 100mmol of M4, 28.83g (300 mmol) of sodium tert-butoxide, 800ml of xylene, and 1mol% of Pd (dba) 2 The reaction was carried out at 120℃for 12h. Stopping the reaction after the reaction is completed, cooling the reactant to room temperature, adding water, filtering, washing the obtained solid with water Toluene was purified by recrystallization to give compound a-40 as a white powder. Wherein Pd (dba) 2 The amount of (2) added was 1mol% of M4.
The HPLC purity of the prepared compound A-40 was 99.9%.
1H NMR(300MHz,Chloroform-d)8.22-8.04(m,6H),7.90-7.87(m,2H),7.58-7.37(m,7H),7.28-6.96(m,14H),3.04(s,1H),2.25(m,2H),1.87-1.69(m,18H)。
Synthesis example 9: synthesis of Compound A-42
< preparation of intermediate M3 > the same as in synthesis example 1.
< preparation of intermediate M1 >
Under the protection of nitrogen, 100mmol of F-17, 250ml of THF and 115ml of sec-butyllithium are added to the reaction flask, the reaction flask is incubated at-70℃for 1 hour, 100mmol of F-15 is added, and the reaction is carried out at-70℃for 1 hour. After the reaction, the reaction was stopped, the reaction was warmed to-40℃and quenched with 120ml of diluted hydrochloric acid (1 mol/L concentration), filtered, washed with petroleum ether, and the obtained solid was recrystallized and purified with toluene to give white powder M1.
< preparation of intermediate M2 >
100mmol of M1, 270ml of glacial acetic acid and 70ml of hydrochloric acid are introduced into the reaction flask and reacted at 130℃for 1 hour. After the reaction, the reaction was stopped, and the reaction mixture was warmed to room temperature, filtered, washed with aqueous sodium carbonate, washed with n-hexane, and the obtained solid was purified by recrystallization with toluene to give compound M2 as a white powder.
< preparation of Compound A-40 >
Into a reaction flask were charged 100mmol of M2, 100mmol of M3, 28.83g (300 mmol) of sodium tert-butoxide, 800ml of xylene, and 1mol% of Pd (dba) 2 The reaction was carried out at 120℃for 12h. Stopping the reaction after the reaction is finished, cooling the reactant to room temperature, adding water, filtering, washing, and recrystallizing and purifying the obtained solid by toluene to obtain white powderArticle A-42. Wherein Pd (dba) 2 The amount of (2) added was 1mol% of M2.
The HPLC purity of the prepared compound A-42 is 99.9%.
1H NMR(300MHz,Chloroform-d)8.10-7.90(m,5H),7.60-7.37(m,8H),7.28-7.10(m,16H)。
Synthesis example 10: synthesis of Compound A-43
< preparation of intermediate M2 > was the same as in synthesis example 3.
< preparation of intermediate M1 >
Under the protection of nitrogen, 100mmol of F-17, 250ml of THF and 115ml of sec-butyllithium are added to the reaction flask, the reaction flask is incubated at-70℃for 1 hour, 100mmol of F-16 are added, and the reaction is carried out at-70℃for 1 hour. After the reaction, the reaction was stopped, the reaction was warmed to-40℃and quenched with 120ml of diluted hydrochloric acid (1 mol/L concentration), filtered, washed with petroleum ether, and the obtained solid was recrystallized and purified with toluene to give white powder M1.
< preparation of intermediate M3 >
100mmol of M1, 270ml of glacial acetic acid and 70ml of hydrochloric acid are introduced into the reaction flask and reacted at 130℃for 1 hour. After the reaction, the reaction was stopped, and the reaction mixture was warmed to room temperature, filtered, washed with aqueous sodium carbonate, washed with n-hexane, and the obtained solid was purified by recrystallization with toluene to give compound M3 as a white powder.
< preparation of Compound A-43 >
Into a reaction flask were charged 100mmol of M3, 100mmol of M2, 28.83g (300 mmol) of sodium tert-butoxide, 800ml of xylene, and 1mol% of Pd (dba) 2 The reaction was carried out at 120℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, and washed with water, and the obtained solid was purified by recrystallization with toluene to give compound a-43 as a white powder. Wherein Pd (dba) 2 The amount of (2) added was 1mol% of M3.
The HPLC purity of the prepared compound A-43 was 99.8%.
1H NMR(300MHz,Chloroform-d)8.33-7.81(m,5H),7.90-7.81(m,3H),7.55-7.37(m,12H),7.30-7.14(m,8H),1.33(m,9H)。
Other compounds of the present application can be synthesized by selecting appropriate raw materials according to the ideas of synthesis examples 1 to 8, or by selecting any other appropriate methods and raw materials.
Example 1
The glass substrate coated with the ITO transparent conductive layer with the thickness of 150nm is subjected to ultrasonic treatment in a commercial cleaning agent, washed in deionized water, subjected to ultrasonic degreasing in an acetone-ethanol mixed solvent, baked in a clean environment until water is completely removed, cleaned by ultraviolet light and ozone, and bombarded on the surface by a low-energy cation beam.
Then placing the above glass substrate with reflective anode into vacuum cavity, and vacuumizing to less than 10 -5 And (3) carrying out vacuum evaporation of a 10nm hole injection layer on the anode layer film, wherein the hole injection layer comprises a hole transport material HT-21 and a p-type dopant p-3, and the evaporation is carried out by utilizing a multi-source co-evaporation method, wherein the evaporation rate of the hole injection layer material HT-21 is regulated to be 0.1nm/s, and the evaporation rate of the p-type dopant p-3 is 3% of the evaporation rate of the hole injection layer material HT-11.
Then, a hole transport layer with a thickness of 140nm was vacuum-evaporated on top of the hole injection layer, wherein the hole transport material was HT-32, and the evaporation rate was 0.1nm/s.
Then, an electron blocking layer with the thickness of 5nm is vacuum evaporated on the hole injection layer, wherein the electron blocking layer is made of EB-1, and the evaporation rate is 0.1nm/s.
Then, a light-emitting layer of 20nm is vacuum-evaporated on the electron blocking layer, wherein the light-emitting layer comprises a host material BH-5 and a guest material BD-10, evaporation is performed by a multi-source co-evaporation method, the evaporation rate of the host material BH-5 is regulated to be 0.1nm/s, and the evaporation rate of the guest material BD-10 is 3% of the evaporation rate of the host material BH-5.
And then, vacuum evaporation is carried out on the light-emitting layer to form a hole blocking layer with the thickness of 5nm, wherein the hole blocking layer is made of ET-63, and the evaporation rate is 0.1nm/s.
Then, an electron transport layer having a thickness of 35nm, which contains an electron transport material ET-61 and an n-type dopant n-1, wherein the n-type dopant content is 50mol%, was vacuum-evaporated on the hole blocking layer.
Then, ytterbium (Yb) having a thickness of 1nm was vacuum-deposited as an electron injection layer on the electron transport layer at a deposition rate of 0.1nm/s.
Then, an aluminum layer having a thickness of 15nm was deposited on the electron injection layer as a cathode at a deposition rate of 1nm/s.
Then, a first light extraction layer having a thickness of 15nm was vacuum-deposited on the cathode electrode, the material of the first light extraction layer was A-3, and the deposition rate was 1nm/s.
Finally, a second light extraction layer with the thickness of 50nm is vacuum evaporated on the first light extraction layer, the material of the second light extraction layer is C-1, and the evaporation rate is 1nm/s.
The organic electroluminescent device of this embodiment is a blue organic electroluminescent device.
Examples 2 to 10
The procedure of example 1 was repeated except that the compounds A-4, A-6, A-14, A-16, A33, A-35, A40, A-42 and A-43 were used in the order mentioned in place of the compound A-3.
Example 11
The same procedure as in example 1 was repeated except that the light-emitting layer comprised host material GPH-81 and guest material GD01, and the organic electroluminescent device was a green organic electroluminescent device.
Example 12
The procedure of example 1 was repeated except that the light-emitting layer comprised host material RH-10 and guest material RPD-1, and the organic electroluminescent device was a red-light organic electroluminescent device.
Comparative examples 1 to 4
The procedure of example 1 was repeated except that the compounds D-1 to D-4 were used in place of the compound A-3 in this order.
Comparative example 5
The procedure of example 7 was repeated except that compound D-1 was used in place of compound A-3.
Comparative example 6
The procedure of example 8 was repeated except that compound D-1 was used in place of compound A-3.
Comparative example 7
The procedure of example 1 was repeated except that the first light extraction layer and the second light extraction layer were replaced with the light extraction layer prepared by the following < preparation of light extraction layer >.
< preparation of light extraction layer >
A light extraction layer with the thickness of 65nm is vacuum evaporated on the cathode electrode, the material of the light extraction layer is C-1, and the evaporation rate is 1nm/s.
Comparative example 8
The same as comparative example 7 was conducted except that the light-emitting layer included a host material GPH-81 and a guest material GD01, and the organic electroluminescent device was a green organic electroluminescent device.
Comparative example 9
The procedure of comparative example 7 was repeated except that the light-emitting layer comprised host material RH-10 and guest material RPD-1, and the organic electroluminescent device was a green organic electroluminescent device.
The performance parameters of each example and comparative example are shown in tables 1 and 2.
TABLE 1
Referring to table 1, the refractive index of the different light extraction materials at the same wavelength has a certain difference, and the compounds provided herein are used for the light extraction materials, and the refractive index of each of blue light, green light and red light is lower than that of the compound D-1, compound D-2, compound D-3 or compound D-4 in comparative examples 1 to 9, indicating that the compounds provided herein are used for the light extraction materials having lower refractive index than the low refractive layer materials in the related art, and are more suitable as the low refractive layer materials in the double layer structure. Among the compounds D-1 to D-4, at least one phenylene group connected with N is para-position substituted or meta-position substituted, the molecular structure of the compound has low steric hindrance, the space tends to be planar, and the stacking density among molecules of the compound is large, so that the refractive index of the compound is higher when the compound is used as a light extraction layer. In the compound provided by the application, at least one phenylene connected with N is ortho-substituted, the steric hindrance of the molecular structure of the compound is high, the compound has different space configurations from the compound D-1 to the compound D-4, the space structure tends to be stereospecific, the stacking density among molecules of the compound can be reduced, the propagation rate of light in a medium can be improved, namely, the propagation rate ratio of light in vacuum and the medium can be reduced, so that the compound provided by the application has lower refractive index when being used as a light extraction layer. In addition, the compounds provided herein are useful in light extraction materials having refractive indices for blue, green, and red light that are lower than the high refractive index material compound C-1 known in the art, and having refractive index differences of 0.3 or more.
TABLE 2
Note that: the "-" in table 2 indicates that this parameter is not present.
The organic electroluminescent devices of examples 1 to 12, comparative examples 1 to 6, including a first light extraction layer having a low refractive index and a second light extraction layer having a high refractive index, wherein the first light extraction layer of examples 1 to 12 includes the compound of the present application as a light extraction material, the first light extraction layer of comparative examples 1 to 6 includes compound D-1, compound D-2, compound D-3 or compound D-4 as a light extraction material, and the second light extraction layer of examples 1 to 12 and comparative examples 1 to 6 includes compound C-1 as a light extraction material. Referring to table 2, with the same second light extraction layer, the color coordinates (CIEx value and CIEy value) of the blue light device, the green light device, and the red light device are the same or similar, respectively, indicating that the emission colors thereof are the same or similar. The green organic electroluminescent device and the red organic electroluminescent device containing the compound have higher current efficiency, and the blue organic electroluminescent device containing the compound has higher blue index, which indicates that the organic electroluminescent device containing the compound provided by the application has better luminous performance.
Referring to table 2, when light extraction layers having the same thickness are provided, the organic electroluminescent device provided in the embodiment of the present application includes a first light extraction layer and a second light extraction layer, and the first light extraction layer includes the compound of the present application as a light extraction material, and the second light extraction layer includes the compound C-1 as a light extraction material; and the organic electroluminescent devices of comparative examples 7 to 9, the light extraction layer of which was a single layer structure, contained the compound C-1 as the light extraction material. The CIEx values and CIEy values of the blue light devices having the light extraction layers of the double layer structures containing the compounds of the present application obtained in examples 1 to 10 were the same as or similar to those of comparative examples 1 to 4, and the light emission colors thereof were the same as or similar to those of comparative examples 4; whereas the blue devices of examples 1 to 10 have a higher blue index. The CIEx and CIEy values of the green light device having a light extraction layer of a double structure containing the compound of the present application obtained in example 11 were the same as or similar to those of comparative example 5, indicating that the light emission colors thereof were similar; the CIEx and CIEy values of the red light device having a light extraction layer of a bilayer structure containing the compound of the present application obtained in example 12 were the same as or similar to those of comparative example 6, indicating that the light emission colors of the two were similar; the green light device obtained in example 11 and the red light device obtained in example 12 of the present application have higher current efficiency, which indicates that the organic electroluminescent device having the light extraction layer of the double-layer structure containing the compound of the present application has better light emitting performance.
It is noted that relational terms such as first and second, and the like are used solely to distinguish one entity or action from another entity or action without necessarily requiring or implying any actual such relationship or order between such entities or actions. Moreover, the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus.
In this specification, each embodiment is described in a related manner, and identical and similar parts of each embodiment are all referred to each other, and each embodiment mainly describes differences from other embodiments.
The foregoing description is only of the preferred embodiments of the present application and is not intended to limit the scope of the present application. Any modifications, equivalent substitutions, improvements, etc. that are within the spirit and principles of the present application are intended to be included within the scope of the present application.
Claims (10)
1. A compound has a structure shown in a formula (I):
wherein,,
x is selected from O, S, NR or CRbRc, rb, rc, R are each independently selected from methyl and the following groups N-1 to N-10:
R 1 ～R 4 each independently selected from hydrogen, fluorine, C unsubstituted or substituted with Ra 6 ～C 15 C, unsubstituted or substituted by Ra 5 ～C 20 Heteroaryl, C which is unsubstituted or substituted by Ra 5 ～C 10 Cycloalkyl, unsubstituted or substituted C by Ra 1 ～C 10 C, unsubstituted or substituted by Ra 2 ～C 5 Cycloalkyl containing heteroatoms and R 1 ～R 4 Are not hydrogen at the same time;
the substituents Ra of the individual radicals are each independently selected from fluorine, trifluoromethyl, cyano, amino, C 1 ～C 4 Alkyl of (a);
the heteroatoms on the heteroaryl or the heteroatom-containing cycloalkyl are each independently selected from O, S or N.
2. The compound of claim 1, wherein Rb, rc, R are each independently selected from methyl and the following groups:
3. the compound of claim 1, wherein R 1 ～R 4 Each independently selected from the group consisting of hydrogen, fluorine, trifluoromethyl, methyl, t-butyl, and the groups represented by R-1 to R-48:
4. the compound of claim 1, wherein R 1 ～R 4 Each independently selected from the group consisting of hydrogen, fluorine, trifluoromethyl, methyl, t-butyl, and the groups shown below:
5. The compound of claim 1, wherein the compound is selected from the group consisting of the compounds shown in a-1 to a-43:
6. a light extraction material comprising at least one of the compounds of any one of claims 1 to 5.
7. The light extraction material of claim 6, wherein the refractive index of the light extraction material is 1.56 or less.
8. The light extraction material of claim 6, wherein the light extraction material has a red light refractive index of 1.50 or less, a green light refractive index of 1.55 or less, and a blue light refractive index of 1.59 or less.
9. An organic electroluminescent device comprising a first light extraction layer and a second light extraction layer, the first light extraction layer having a refractive index that is less than the refractive index of the second light extraction layer, the first light extraction layer comprising at least one of the light extraction materials of any one of claims 6 to 8.
10. A display device comprising the organic electroluminescent device of claim 9.
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| CN117185990B (en) * | 2023-11-07 | 2024-01-30 | 烟台丰蓬液晶材料有限公司 | Compound and organic electroluminescent device comprising same |
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