Triazine compound, light extraction material and application thereof

Abstract

The invention discloses a triazine compound, a light extraction material and application thereof, and belongs to the technical field of display. The general formula of the triazine compound is as follows: # imgabs0, the triazine compound comprises a fluorene anthraquinone group, the fluorene anthraquinone group is a relatively large conjugated fused ring group and is relatively high in rigidity, a branched chain is a structure of a triazine group and a benzoheterocycle / aromatic ring, the branched chain has relatively many lone pair electrons, and the branched chain is matched with the fluorene anthraquinone group, so that a molecule can have relatively high polarizability, and the polarizability of the molecule is relatively high; and the refractive index is high. Therefore, when the triazine compound is used for the light extraction layer of the organic electroluminescent device, the light extraction layer can have high refractive index and high stability, so that high light extraction efficiency is obtained, the device efficiency of the organic electroluminescent device is improved, and the service life of the organic electroluminescent device is prolonged.

Description

Technical Field

[0001] The present application relates to the field of display technology, and in particular to a triazine compound, a light extraction material and applications thereof. Background Art

[0002] Organic Light Emission Diodes (OLED) are widely used in the field of lighting and display. OLED devices include a light-emitting functional layer and a cathode and an anode stacked on both sides of the light-emitting functional layer. By applying an electric field between the cathode and the anode, electrons are injected from the cathode and holes are injected from the anode. The electrons and holes recombine in the light-emitting functional layer and realize OLED electroluminescence.

[0003] Due to the difference in refractive index between different media, light is easily lost at the interface when it is transmitted between different media. Therefore, a light extraction (Capping Layer, CPL) layer is usually set on the side of the cathode away from the light-emitting functional layer. The CPL layer can allow the light confined inside the OLED device to be emitted to the outside, which is manifested as a higher light extraction efficiency.

[0004] However, the light extraction efficiency of the currently known light extraction layer still needs to be improved. Summary of the invention

[0005] The embodiment of the present application provides a triazine compound, a light extraction material and its application, which can improve the light extraction efficiency, thereby improving the efficiency and life of the device. The technical solution is as follows:

[0006] In one aspect, a triazine compound is provided, wherein the general formula of the triazine compound is as follows:

[0007]

[0008] Wherein, L1 and L2 are each independently selected from any one of a substituted or unsubstituted C6-C36 arylene group and a substituted or unsubstituted C2-C36 heteroarylene group;

[0009] m and n are each independently selected from 0, 1, 2, 3 or 4.

[0010] R1 and R2 are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C2-C36 heteroaryl, and any one of the formulas Ar1-Ar6;

[0011] Among them, the chemical formulas of Ar1, Ar2, Ar3, Ar4, Ar5 and Ar6 are as follows:

[0012]

[0013] Z is independently selected from C(R3) or N atoms;

[0014] R3 is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0015] X1 and Y are each independently selected from an O atom, a S atom, C(R4R5) or N(R6);

[0016] R4 and R5 are each independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atoms, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or R4 and R5 may be connected to form a substituted or unsubstituted ring;

[0017] R6 is selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0018] Ring A and Ring B are independently selected from any one of a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, and a substituted or unsubstituted phenanthrene ring.

[0019] In some possible implementations, the chemical formula of Ar1 is any of the following:

[0020]

[0021] In some possible implementations, the chemical formula of Ar2 is shown in any of the following:

[0022]

[0023] In some possible implementations, the chemical formula of Ar3 is shown in any of the following:

[0024]

[0025]

[0026] In some possible implementations, the chemical formula of Ar4 is shown in any of the following:

[0027]

[0028] In some possible implementations, the chemical formula of Ar5 is any of the following:

[0029]

[0030] In some possible implementations, the chemical formula of Ar6 is shown in any of the following:

[0031]

[0032]

[0033] On the other hand, a method for preparing the triazine compound described in any one of the above is provided, the preparation method comprising:

[0034] Providing reactant A1, reactant A2, reactant A3 and reactant A4;

[0035] Under the condition of protective atmosphere and the presence of a catalyst, reacting the reactant A1 with the reactant A2 to obtain a first intermediate;

[0036] Under the conditions of the protective atmosphere and the presence of the catalyst, the first intermediate and the reactant A3 react to obtain a second intermediate;

[0037] Under the conditions of the protective atmosphere and the presence of the catalyst, reacting the second intermediate with the reactant A4 to obtain the triazine compound;

[0038] The general formula of the reactant A1, the reactant A2, the reactant A3 and the reactant A4 is as follows:

[0039]

[0040] X represents a halogen.

[0041] On the other hand, a light extraction material is provided, wherein the light extraction material comprises any of the triazine compounds described above.

[0042] In some possible implementations, the mass percentage of the triazine compound is 100%.

[0043] In some possible implementations, the refractive index of the light extraction material within the wavelength range of 460 nm to 620 nm is greater than 2.

[0044] In some possible implementations, the glass transition temperature of the light extraction material is greater than or equal to 125°C.

[0045] On the other hand, an organic electroluminescent device is provided, comprising an anode, a light-emitting functional layer, a cathode and a light extraction layer which are sequentially stacked, wherein the light extraction layer adopts any of the light extraction materials described above.

[0046] In some possible implementations, the light-emitting functional layer includes a hole transport unit, a light-emitting functional layer and an electron transport unit, and the hole transport unit, the light-emitting functional layer and the electron transport unit are sequentially stacked in a direction from the anode to the cathode;

[0047] Wherein, the hole transport unit includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer;

[0048] The electron transport unit includes at least one of a hole blocking layer, an electron transport layer, and an electron injection layer.

[0049] In another aspect, a display device is provided, comprising any one of the organic electroluminescent devices described above.

[0050] The embodiment of the present application provides a triazine compound, which includes a fluorene anthraquinone group, which is a larger conjugated fused ring group with strong rigidity, and a side chain of a triazine group + a benzoheterocyclic ring / aromatic ring structure. Such side chains have more lone pairs of electrons, and in combination with the fluorene anthraquinone group, the molecule can have a larger polarizability and a higher refractive index. Therefore, when the triazine compound is used in the light extraction layer of an organic electroluminescent device, the light extraction layer can have a higher refractive index and stronger stability, thereby obtaining a higher light extraction efficiency, thereby improving the device efficiency and life of the organic electroluminescent device.

[0051] It is to be understood that the foregoing general description and the following detailed description are exemplary only and are not restrictive of the present disclosure. BRIEF DESCRIPTION OF THE DRAWINGS

[0052] Figure 1This is a schematic diagram of the absorption of the compounds provided in Examples 1 to 9 and the compounds provided in Comparative Examples 1 to 2 at different wavelengths provided in the examples of the present application. DETAILED DESCRIPTION

[0053] The technical solutions in the embodiments of the present application are described clearly and completely below. Obviously, the described embodiments are part of the embodiments of the present application, not all of the embodiments. Based on the embodiments in the present application, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present application.

[0054] On the one hand, the present invention provides a triazine compound, the general formula of which is as follows:

[0055]

[0056] Wherein, L1 and L2 are each independently selected from any one of a substituted or unsubstituted C6-C36 arylene group and a substituted or unsubstituted C2-C36 heteroarylene group;

[0057] m and n are each independently selected from 0, 1, 2, 3 or 4.

[0058] R1 and R2 are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C2-C36 heteroaryl, and any one of the formulas Ar1-Ar6;

[0059] Among them, the chemical formulas of Ar1, Ar2, Ar3, Ar4, Ar5 and Ar6 are as follows:

[0060]

[0061]

[0062] Z is independently selected from C(R3) or N atoms;

[0063] R3 is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0064] X1 and Y are each independently selected from an O atom, a S atom, C(R4R5) or N(R6);

[0065] R4 and R5 are each independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atoms, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or R4 and R5 may be connected to form a substituted or unsubstituted ring;

[0066] R6 is selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0067] Ring A and Ring B are independently selected from any one of a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, and a substituted or unsubstituted phenanthrene ring.

[0068] For the above-mentioned triazine compounds, the aryl groups involved can be subunits of the following aromatic groups: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, peryl, fluoranthenyl, triphenylene, phenanthrenyl, pyrenyl, tetraphenyl, pentaphenyl, fluorenyl, indenyl, acenaphthyl, benzofluorenyl, spirofluorenyl, etc.

[0069] Some examples of the aryl groups involved can be shown as follows: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, peryl, fluoranthenyl, triphenylene, phenanthrenyl, pyrenyl, tetracenyl, pentacene, fluorenyl, indenyl, acenaphthyl, benzofluorenyl, spirofluorenyl, etc.

[0070] The heteroatoms contained in the heteroaryl radical involved may be O, S, N, etc., and the heteroaryl radical may be a subunit of the following heteroaryl radicals: benzofuranyl, naphthofuranyl, phenanthrofuranyl, dibenzofuranyl, benzodibenzofuranyl, benzothiophenyl, naphthiophenyl, phenanthrothiophenyl, dibenzothiophenyl, benzodibenzothiophenyl, indolyl, naphthioindolyl, carbazolyl, benzocarbazolyl, benzodisulfide, dihydroisobenzofuranyl, dihydrobenzofuranyl, dihydrobenzothiophenyl, dihydroisobenzothiophenyl, phenoxazinyl, phenothiazinyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, etc.

[0071] Some examples of the heteroaryl groups involved can be shown as follows: benzofuranyl, naphthofuranyl, phenanthrofuranyl, dibenzofuranyl, benzodibenzofuranyl, benzothiophenyl, naphthiophenyl, phenanthrothiophenyl, dibenzothiophenyl, benzodibenzothiophenyl, indolyl, naphthioindolyl, carbazolyl, benzocarbazolyl, benzodisulfide, dihydroisobenzofuranyl, dihydrobenzofuranyl, dihydrobenzothiophenyl, dihydroisobenzothiophenyl, phenoxazinyl, phenothiazinyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, etc.

[0072] The alkyl group involved can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, n-pentyl, isopentyl, neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, octyl, etc.

[0073] The alkenyl group involved can be vinyl, propenyl-1-yl, propenyl-2-yl, propenyl-3-yl, buten-1-yl, buten-2-yl, buten-3-yl, buten-4-yl, 1-methylpropen-1-yl, 2-methylpropen-1-yl, 1-ethyl-ethen-1-yl, 2-methyl-propen-3-yl, buta-1,3-dienyl, buta-1,2-dienyl, buta-1,2-dien-4-yl, pentenyl, hexenyl, heptenyl, octenyl, etc.

[0074] The cycloalkyl group involved may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, etc.

[0075] The heterocycloalkyl involved refers to an alkyl skeleton containing one or more heteroatoms, and the heteroatoms may be oxygen atoms, nitrogen atoms, sulfur atoms, etc. Some examples of heterocycloalkyl may be methoxymethyl, ethoxyethyl, propoxypropyl, methoxyethyl, etc.

[0076] The alkoxy group referred to may be methoxy, ethoxy, propoxy, butoxy, pentoxy, or the like.

[0077] The embodiment of the present application provides a triazine compound, which includes a fluorene anthraquinone group, which is a larger conjugated fused ring group with strong rigidity, and a side chain of a triazine group + a benzoheterocyclic ring / aromatic ring structure. Such side chains have more lone pairs of electrons, and in combination with the fluorene anthraquinone group, the molecule can have a larger polarizability and a higher refractive index. Therefore, when the triazine compound is used in the light extraction layer of an organic electroluminescent device, the light extraction layer can have a higher refractive index and stronger stability, thereby obtaining a higher light extraction efficiency, thereby improving the device efficiency and life of the organic electroluminescent device.

[0078] In some examples, L1 and L2 are each independently selected from a single bond or a phenylene group, and the two may be the same or different. For example, both are single bonds or both are phenylene groups, or one is a single bond and the other is a phenylene group.

[0079] R1 and R2 are independently selected from any one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 to achieve the purpose of optimizing the above effects.

[0080] In some examples, R1 and R2 may be the same or different. For example, R1 and R2 are the same and are both selected from one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6, or R1 and R2 are different, that is, R1 is selected from one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6, and R2 is selected from another one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6.

[0081] In some possible implementations, the chemical formula of Ar1 is shown as any of the following:

[0082]

[0083] In some possible implementations, the chemical formula of Ar2 is shown as any of the following:

[0084]

[0085]

[0086] In some possible implementations, the chemical formula of Ar3 is shown as any of the following:

[0087]

[0088] In some possible implementations, the chemical formula of Ar4 is shown as any of the following:

[0089]

[0090] In some possible implementations, the chemical formula of Ar5 is shown as any of the following:

[0091]

[0092] In some possible implementations, the chemical formula of Ar6 is shown as any of the following:

[0093]

[0094]

[0095]

[0096] In combination with the above-mentioned schemes of triazine compounds, some examples of triazine compounds can be shown as follows:

[0097]

[0098]

[0099] On the other hand, an embodiment of the present application provides a method for preparing the above-mentioned triazine compound, the preparation method comprising:

[0100] Step 1: Provide reactant A1, reactant A2, reactant A3 and reactant A4.

[0101] Wherein, the general formula of reactant A1, reactant A2, reactant A3 and reactant A4 is as follows:

[0102]

[0103] Wherein, X represents a halogen. Specifically, X may be F, Cl, Br or I. In the embodiments of the present application, only X being Cl is used as an example for illustration.

[0104] Step 2: Under the conditions of protective atmosphere and the presence of a catalyst, reactant A1 and reactant A2 are reacted to obtain a first intermediate.

[0105] The protective atmosphere may be nitrogen, and the catalyst may be a palladium catalyst.

[0106] The palladium catalyst shows high selectivity, wide substrate adaptability, mild reaction conditions and efficient catalytic activity. By changing the reaction conditions such as the part, reaction solvent, temperature, alkali of the palladium catalyst, the activity, selectivity, etc. of the reaction can be finely regulated to meet different synthesis requirements. In the present application embodiment, only tetrakistriphenylphosphine palladium is used as the palladium catalyst for example to illustrate.

[0107] When X is Cl, the process of reactant A1 and reactant A2 reacting to form the first intermediate is as follows:

[0108]

[0109] Step 3: Under the conditions of protective atmosphere and the presence of a catalyst, the first intermediate and reactant A3 are reacted to obtain a second intermediate.

[0110] The process of the first intermediate and reactant A3 generating the second intermediate is as follows:

[0111]

[0112] Step 4: Under the condition of protective atmosphere and the presence of a catalyst, the second intermediate and reactant A4 are reacted to obtain a triazine compound.

[0113] The process of the second intermediate and reactant A4 generating a triazine compound is as follows:

[0114]

[0115] In the embodiment of the present application, reactants A3 and A4 can be designed according to the chemical structure of the triazine compound. Reactants A3 and A4 can be obtained by purchasing known compound products or prepared by themselves, which is not specifically limited.

[0116] On the other hand, the embodiment of the present application further provides a light extraction material, which includes any of the above-mentioned triazine compounds. The light extraction material provided by the embodiment of the present application has all the advantages of the triazine compound.

[0117] In some examples, the mass percentage of the triazine compound in the light extraction material is 100%.

[0118] In some examples, the light extraction material includes a triazine compound and an auxiliary agent, and the amount of the auxiliary agent added can be adaptively determined according to actual needs. For example, the mass percentage of the auxiliary agent in the light extraction material can be 0.5% to 5%.

[0119] The auxiliary agent may be selected from at least one of a material having a refractive index lower than that of a triazine compound, a scattering agent, and a light stabilizer, for example, nano silicon dioxide, nano titanium dioxide, nano zinc oxide, a hindered amine light stabilizer, and the like.

[0120] Based on the use of the triazine compound provided in the embodiment of the present application, the refractive index of the light extraction material in the wavelength range of 460nm to 620nm is greater than 2, showing an excellent light refraction effect. In addition, the glass transition temperature of the light extraction material is greater than or equal to 125°C, showing excellent thermal stability.

[0121] On the other hand, the embodiment of the present application also provides an organic electroluminescent device, wherein the organic electroluminescent device comprises an anode, a light-emitting functional layer, a cathode and a light extraction layer which are stacked in sequence, and the light extraction layer adopts any of the above-mentioned light extraction materials. The organic electroluminescent device provided by the embodiment of the present application has all the advantages of the triazine compound, so that it has higher light extraction efficiency and device stability.

[0122] For example, the light-emitting functional layer includes a hole transport unit, a light-emitting functional layer and an electron transport unit, and the hole transport unit, the light-emitting functional layer and the electron transport unit are stacked in sequence from the anode to the cathode. Among them, the hole transport unit includes at least one of a hole injection layer, a hole transport layer and an electron blocking layer; the electron transport unit includes at least one of a hole blocking layer, an electron transport layer and an electron injection layer.

[0123] In some examples (1), the hole transport unit includes a hole transport layer, wherein the anode, the hole transport layer, and the light-emitting functional layer are stacked in sequence.

[0124] In some examples (2), the hole transport unit includes a hole injection layer and a hole transport layer, wherein the anode, the hole injection layer, the hole transport layer, and the light-emitting functional layer are stacked in sequence.

[0125] In some examples (3), the hole transport unit includes a hole transport layer and an electron blocking layer, wherein the anode, the hole transport layer, the electron blocking layer, and the light-emitting functional layer are stacked in sequence.

[0126] In some examples (4), the hole transport region includes a hole transport layer, an electron blocking layer and a hole injection layer, wherein the anode, the hole injection layer, the hole transport layer, the electron blocking layer and the light-emitting functional layer are stacked in sequence.

[0127] In some examples (5), the electron transport region includes an electron transport layer, wherein the cathode, the electron transport layer, and the light-emitting functional layer are stacked in sequence.

[0128] In some examples (6), the electron transport region includes an electron transport layer and an electron injection layer, wherein the cathode, the electron injection layer, the electron transport layer, and the light-emitting functional layer are stacked in sequence.

[0129] In some examples (7), the electron transport region includes an electron transport layer and a hole blocking layer, wherein the cathode, the electron transport layer, the hole blocking layer, and the light-emitting functional layer are stacked in sequence.

[0130] In some examples (8), the electron transport region includes an electron transport layer, a hole blocking layer, and an electron injection layer, wherein the cathode, the electron injection layer, the electron transport layer, the hole blocking layer, and the light-emitting functional layer are stacked in sequence.

[0131] The hole transport unit, the electron transport unit, the anode and the cathode may all be made of currently known related materials, which will not be described in detail here.

[0132] For example, the hole injection layer includes but is not limited to: inorganic oxides, p-type dopants of strong electron-withdrawing systems and dopants of hole transport materials, such as hexacyanohexaazatriphenylene, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), 1,2,3-tris[(cyano)(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane, etc.

[0133] The hole transport material / electron blocking layer includes, but is not limited to, aromatic amines having hole transport properties and dimethylfluorene or carbazole materials and their derivatives.

[0134] The light-emitting layer is selected according to the actual light-emitting requirements. Taking the green light-emitting material as an example, it can be selected from but not limited to iridium complexes.

[0135] The hole blocking layer / electron transport layer includes but is not limited to: aromatic heterocyclic compounds, which can be selected from but not limited to at least one of benzimidazole, triazine, pyrimidine, pyridine, pyrazine, quinoxaline, quinoline, diazole, diazaphosphine, phosphine oxide, aromatic ketone, lactam, borane compounds and their derivatives.

[0136] The electron injection layer is generally an alkali metal or a metal, such as LiF, Yb, Mg, Ca, or a compound thereof.

[0137] On the other hand, an embodiment of the present application further provides a display device, which includes any one of the organic electroluminescent devices mentioned above.

[0138] The display device provided in the embodiment of the present application has all the advantages of an organic electroluminescent device. Exemplarily, the display device includes but is not limited to: OLED TVs, tablet computers, car displays, MP3 players, smart watches, fitness bracelets, virtual reality (VR) helmets, augmented reality (AR) glasses, etc.

[0139] The exemplary embodiments of the present application will be described in more detail below. Although the exemplary embodiments of the present application are described below, it should be understood that the present application can be implemented in various forms and should not be limited by the embodiments set forth herein. The specific techniques or conditions not specified in the embodiments are carried out according to the techniques or conditions described in the documents in this area or according to the product specification. The reagents used or the instruments not specified in the manufacturers are all conventional products that can be obtained commercially.

[0140] Example 1

[0141] This example synthesized a compound 1, and the synthesis route is as follows:

[0142]

[0143] Step 1: Add solvent DMF:H2O=3:1 to the bottle, then add 1eq of compound a and 1.1eq of compound b in turn, fill with nitrogen, and heat to reflux for 0.5h. Add 0.03eq of tetrakistriphenylphosphine palladium and 2eq of Na2CO3. Then fill with nitrogen and reflux at 110°C for 7h. After the reaction is completed, cool to room temperature, extract and evaporate, add dichloromethane to dissolve, and then separate by column chromatography. Then evaporate, add dichloromethane to dissolve, stand to room temperature for recrystallization twice, filter to obtain recrystallized solid, dry in a vacuum oven for 3h to obtain solid, and sublime the solid to obtain intermediate 1.

[0144] Step 2: Add solvent DMF:H2O=3:1 to the bottle, then add 1eq of intermediate 1 and 1.1eq of compound c in turn, fill with nitrogen, and heat to reflux for 0.5h. Add 0.03eq of tetrakistriphenylphosphine palladium and 2eq of Na2CO3. Fill with nitrogen again, and reflux at 110°C for 7h. After the reaction is completed, cool to room temperature, extract and evaporate, add dichloromethane to dissolve, and then separate by column chromatography. Then evaporate, add dichloromethane to dissolve, let stand to room temperature for recrystallization twice, filter to obtain recrystallized solid, dry in a vacuum oven for 3h to obtain solid, and sublime the solid to obtain intermediate 2.

[0145] Step 3: Add solvent THF:H2O=4:1 to the bottle, then add 1eq of intermediate 2 and 1.1eq of intermediate 3 in sequence, fill with nitrogen, and heat to reflux for 0.5h. Add 0.02eq of tetrakistriphenylphosphine palladium and 3eq of Na2CO3. Then fill with nitrogen and reflux at 75°C for 7h. After the reaction is completed, cool to room temperature, extract and evaporate, add dichloromethane to dissolve, and then separate by column chromatography. Then evaporate, add dichloromethane to dissolve, let stand to room temperature for recrystallization twice, filter to obtain recrystallized solid, dry in a vacuum oven for 3h to obtain solid, and sublime the solid to obtain compound 1.

[0146] Example 2

[0147] This example synthesized a compound 2, and the synthesis route is as follows:

[0148]

[0149] Step 1: Add solvent DMF:H2O=3:1 to the bottle, then add 1eq of intermediate 1 and 1.1eq of compound d in turn, fill with nitrogen, and heat to reflux for 0.5h. Add 0.03eq of tetrakistriphenylphosphine palladium and 2eq of Na2CO3. Then fill with nitrogen and reflux at 110°C for 7h. After the reaction is completed, cool to room temperature, extract and evaporate, add dichloromethane to dissolve, and then separate by column chromatography. Then evaporate, add dichloromethane to dissolve, stand to room temperature for recrystallization twice, filter to obtain recrystallized solid, dry in a vacuum oven for 3h to obtain solid, and sublime the solid to obtain intermediate 4.

[0150] Step 2: Add solvent THF:H2O=4:1 to the bottle, then add 1eq of intermediate 4 and 1.1eq of intermediate 3 in sequence, fill with nitrogen, and heat to reflux for 0.5h. Add 0.02eq of tetrakistriphenylphosphine palladium and 3eq of Na2CO3. Then fill with nitrogen and reflux at 75°C for 7h. After the reaction is completed, cool to room temperature, extract and evaporate, add dichloromethane to dissolve, and then separate by column chromatography. Then evaporate, add dichloromethane to dissolve, stand to room temperature for recrystallization twice, filter to obtain recrystallized solid, dry in a vacuum oven for 3h to obtain solid, and sublime the solid to obtain compound 2.

[0151] Example 3

[0152] This example synthesized a compound 3, and the synthesis route is as follows:

[0153]

[0154] Add solvent DMF:H2O=3:1 to the bottle, then add 1eq of intermediate 2 and 1.1eq of compound c in sequence, fill with nitrogen, and heat to reflux for 0.5h. Add 0.03eq of tetrakistriphenylphosphine palladium and 2eq of Na2CO3. Then fill with nitrogen and reflux at 110°C for 7h. After the reaction is completed, cool to room temperature, extract and evaporate, add dichloromethane to dissolve, and then separate by column chromatography. Then evaporate, add dichloromethane to dissolve, stand to room temperature for recrystallization twice, filter to obtain recrystallized solid, dry in a vacuum oven for 3h to obtain solid, and sublime the solid to obtain compound 3.

[0155] Example 4

[0156] This example synthesized a compound 4, and the synthesis route is as follows:

[0157]

[0158] Add solvent THF:H2O=4:1 to the bottle, then add 1eq of intermediate 1 and 1.1eq of intermediate 4 in sequence, fill with nitrogen, and heat to reflux for 0.5h. Add 0.02eq of tetrakistriphenylphosphine palladium and 3eq of Na2CO3. Then fill with nitrogen and reflux at 75°C for 7h. After the reaction is completed, cool to room temperature, extract and evaporate, add dichloromethane to dissolve, and then separate by column chromatography. Then evaporate, add dichloromethane to dissolve, let stand to room temperature for recrystallization twice, filter to obtain recrystallized solid, dry in a vacuum oven for 3h to obtain solid, and sublime the solid to obtain compound 4.

[0159] Example 5

[0160] This example synthesized a compound 5, and the synthesis route is as follows:

[0161]

[0162] Add solvent THF:H2O=4:1 to the bottle, then add 1eq of intermediate 1 and 1.1eq of intermediate 5 in sequence, fill with nitrogen, and heat to reflux for 0.5h. Add 0.02eq of tetrakistriphenylphosphine palladium and 3eq of Na2CO3. Then fill with nitrogen and reflux at 75°C for 7h. After the reaction is completed, cool to room temperature, extract and evaporate, add dichloromethane to dissolve, and then separate by column chromatography. Then evaporate, add dichloromethane to dissolve, let stand to room temperature for recrystallization twice, filter to obtain recrystallized solid, dry in a vacuum oven for 3h to obtain solid, and sublime the solid to obtain compound 5.

[0163] Example 6

[0164] This example synthesized a compound 6, and the synthesis route is as follows:

[0165]

[0166] Add solvent THF:H2O=4:1 to the bottle, then add 1eq of intermediate 1 and 1.1eq of intermediate 6 in turn, fill with nitrogen, and heat to reflux for 0.5h. Add 0.02eq of tetrakistriphenylphosphine palladium and 3eq of Na2CO3. Then fill with nitrogen and reflux at 75°C for 7h. After the reaction is completed, cool to room temperature, extract and evaporate, add dichloromethane to dissolve, and then separate by column chromatography. Then evaporate, add dichloromethane to dissolve, let stand to room temperature for recrystallization twice, filter to obtain recrystallized solid, dry in a vacuum oven for 3h to obtain solid, and sublime the solid to obtain compound 6.

[0167] Example 7

[0168] This example synthesized a compound 7, and the synthesis route is as follows:

[0169]

[0170] Add solvent THF:H2O=4:1 to the bottle, then add 1eq of intermediate 2 and 1.1eq of intermediate 4 in sequence, fill with nitrogen, and heat to reflux for 0.5h. Add 0.02eq of tetrakistriphenylphosphine palladium and 3eq of Na2CO3. Then fill with nitrogen and reflux at 75°C for 7h. After the reaction is completed, cool to room temperature, extract and evaporate, add dichloromethane to dissolve, and then separate by column chromatography. Then evaporate, add dichloromethane to dissolve, let stand to room temperature for recrystallization twice, filter to obtain recrystallized solid, dry in a vacuum oven for 3h to obtain solid, and sublime the solid to obtain compound 7.

[0171] Example 8

[0172] This example synthesized a compound 8, and the synthesis route is as follows:

[0173]

[0174] Add solvent THF:H2O=4:1 to the bottle, then add 1eq of intermediate 2 and 1.1eq of intermediate 5 in sequence, fill with nitrogen, and heat to reflux for 0.5h. Add 0.02eq of tetrakistriphenylphosphine palladium and 3eq of Na2CO3. Then fill with nitrogen and reflux at 75°C for 7h. After the reaction is completed, cool to room temperature, extract and evaporate, add dichloromethane to dissolve, and then separate by column chromatography. Then evaporate, add dichloromethane to dissolve, let stand to room temperature for recrystallization twice, filter to obtain recrystallized solid, dry in a vacuum oven for 3h to obtain solid, and sublime the solid to obtain compound 8.

[0175] Example 9

[0176] This example synthesized a compound 9, and the synthesis route is as follows:

[0177]

[0178]

[0179] Step 1: Add solvent THF:H2O=4:1 to the bottle, then add 1eq of intermediate 1 and 1.1eq of intermediate 5 in sequence, fill with nitrogen, and heat to reflux for 0.5h. Add 0.02eq of tetrakistriphenylphosphine palladium and 3eq of Na2CO3. Then fill with nitrogen and reflux at 75°C for 7h. After the reaction is completed, cool to room temperature, extract and evaporate, add dichloromethane to dissolve, and then separate by column chromatography. Then evaporate, add dichloromethane to dissolve, let stand to room temperature for recrystallization twice, filter to obtain recrystallized solid, dry in a vacuum oven for 3h to obtain solid, and sublime the solid to obtain intermediate 8.

[0180] Step 2: Add solvent THF:H2O=4:1 to the bottle, then add 1eq of intermediate 8 and 1.1eq of intermediate 7 in sequence, fill with nitrogen, and heat to reflux for 0.5h. Add 0.02eq of tetrakistriphenylphosphine palladium and 3eq of Na2CO3. Then fill with nitrogen and reflux at 75°C for 7h. After the reaction is completed, cool to room temperature, extract and evaporate, add dichloromethane to dissolve, and then separate by column chromatography. Then evaporate, add dichloromethane to dissolve, stand to room temperature for recrystallization twice, filter to obtain recrystallized solid, dry in a vacuum oven for 3h to obtain solid, and sublime the solid to obtain compound 9.

[0181] Comparative Example

[0182] Comparative Example 1 involves compound Ref1, and Comparative Example 2 involves compound Ref2, and the chemical structural formulas of the two are shown below:

[0183]

[0184] Test Example 1

[0185] The refractive index and glass transition temperature of the compounds 1 to 9 provided in the above examples and the compounds Ref1 and Ref2 provided in the comparative examples at different wavelengths were tested. The test results are shown in Table 1.

[0186] Table 1

[0187]

[0188] It can be seen from Table 1 that the refractive index of the triazine compounds provided in Examples 1 to 9 of the present application is greater than 2, which is conducive to improving the light extraction efficiency of the OLED device, obtaining a higher external quantum efficiency, reducing the loss of light inside the OLED device, and improving the device efficiency. At the same time, the glass transition temperature of the triazine compounds provided in Examples 1 to 9 of the present application is greater than or equal to 125° C., which is conducive to improving the thermal stability of the OLED device.

[0189] The absorbance of compounds 1 to 9 provided in the above examples and compounds Ref1 and Ref2 provided in the comparative examples at different wavelengths was also tested. The test results are shown in Figure 1 .

[0190] from Figure 1 It can be seen that compared with the compounds provided in the comparative example, the triazine compounds provided in Examples 1 to 9 of the present application lose absorption at 510 nm, which can significantly improve the light extraction efficiency of the device, obtain a higher external quantum efficiency, reduce the loss of light inside the device, and thus improve the efficiency of the green light device.

[0191] Test Example 2

[0192] A plurality of OLED devices are provided. The OLED devices respectively use the triazine compounds provided in the above-mentioned Examples 1 to 9 and the compounds provided in Comparative Examples 1 to 2 as light extraction layers.

[0193] OLED devices are top-emitting devices prepared by vacuum evaporation, which include an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (including host and guest doping), a hole blocking layer, an electron transport layer, an electron injection layer, a cathode, and a light extraction layer arranged in sequence.

[0194] Among them, the materials involved in each layer of the OLED device are as follows:

[0195]

[0196] The structure and layer thickness of the green OLED device are shown below:

[0197] ITO / m-MTDATA:F4TCNQ 3%10nm / m-MTDATA 110nm / CBP 5nm / GH:GD 10%40nm / TPBI 5nm / BCP:Liq 1:1 30nm / Yb 1nm / Mg:Ag 13nm / CPL 65nm

[0198] The green OLED device was subjected to performance testing, and the test results are shown in Table 2.

[0199] Table 2

[0200] Light extraction layer Voltage efficiency Lifespan (LT95@1000nit) Comparative Example 1 Compound Ref1 100％ 100％ 100％ Comparative Example 2 Compound Ref2 101％ 103％ 100％ Example 1 Compound 1 100％ 115％ 103％ Example 2 Compound 2 100％ 108％ 102％ Example 3 Compound 3 100％ 113％ 105％ Example 4 Compound 4 100％ 106％ 107％ Example 5 Compound 5 100％ 105％ 106％ Example 6 Compound 6 100％ 105％ 103％ Example 7 Compound 7 100％ 111％ 102％ Example 8 Compound 8 100％ 106％ 103％ Example 9 Compound 9 100％ 114％ 104％

[0201] It can be seen from Table 2 that compared with compounds Ref1 and Ref2, the green light OLED device prepared using the compounds provided in Examples 1 to 9 of the present application as the light extraction layer has higher light extraction efficiency, improved stability to a certain extent, and significantly improved green light efficiency and lifespan.

[0202] In summary, the present application uses fluorene anthraquinone and triazine as core compounds. When used in the light extraction layer, fluorene anthraquinone is a larger conjugated fused ring group with strong rigidity, and the side chain is a structure such as triazine + benzoheterocycle / aromatic ring. This type of side chain has more lone pairs of electrons, which, combined with the fluorene anthraquinone structure, improves the absorption at 510nm, making the molecule have a larger polarizability, a higher refractive index, and a lower green light absorption rate. When used in green light OLED devices, the light extraction efficiency can be improved. At the same time, the material structure has good rigidity and high thermal stability, which can also improve the device life problem, so that the green light device exhibits excellent performance.

[0203] The above description is only for the purpose of facilitating those skilled in the art to understand the technical solution of the present application and is not intended to limit the present application. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present application shall be included in the protection scope of the present application.

Claims

1. A triazine compound, characterized in that The general formula of the triazine compound is shown below: Wherein, L1 and L2 are each independently selected from any one of a substituted or unsubstituted C6-C36 arylene group and a substituted or unsubstituted C2-C36 heteroarylene group; m and n are each independently selected from 0, 1, 2, 3 or 4; R1 and R2 are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C2-C36 heteroaryl, and any one of the formulas Ar1-Ar6; Among them, the chemical formulas of Ar1, Ar2, Ar3, Ar4, Ar5 and Ar6 are as follows: Z is independently selected from C(R3) or N atoms; R3 is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; X1 and Y are each independently selected from an O atom, a S atom, C(R4R5) or N(R6); R4 and R5 are each independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atoms, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or R4 and R5 may be connected to form a substituted or unsubstituted ring; R6 is selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; Ring A and Ring B are independently selected from any one of a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, and a substituted or unsubstituted phenanthrene ring.

2. The triazine compound according to claim 1, characterized in that The chemical formula of Ar1 is shown in any of the following:

3. The triazine compound according to claim 1, characterized in that The chemical formula of Ar2 is shown in any of the following:

4. The triazine compound according to claim 1, characterized in that The chemical formula of Ar3 is shown in any of the following:

5. The triazine compound according to claim 1, characterized in that The chemical formula of Ar4 is shown in any of the following:

6. The triazine compound according to claim 1, characterized in that The chemical formula of Ar5 is shown in any of the following:

7. The triazine compound according to claim 1, characterized in that The chemical formula of Ar6 is shown in any of the following:

8. A method for preparing the triazine compound according to any one of claims 1 to 7, characterized in that: The preparation method comprises: Providing reactant A1, reactant A2, reactant A3 and reactant A4; Under the condition of protective atmosphere and the presence of a catalyst, reacting the reactant A1 with the reactant A2 to obtain a first intermediate; Under the conditions of the protective atmosphere and the presence of the catalyst, the first intermediate and the reactant A3 react to obtain a second intermediate; Under the conditions of the protective atmosphere and the presence of the catalyst, reacting the second intermediate with the reactant A4 to obtain the triazine compound; The general formula of the reactant A1, the reactant A2, the reactant A3 and the reactant A4 is as follows: X represents a halogen.

9. A light extraction material, characterized in that: The light extraction material includes the triazine compound according to any one of claims 1 to 7.

10. The light extraction material according to claim 9, characterized in that The mass percentage of the triazine compound is 100%.

11. The light extraction material according to any one of claims 9 to 10, characterized in that: The refractive index of the light extraction material in the wavelength range of 460 nm to 620 nm is greater than 2.

12. The light extraction material according to any one of claims 9 to 10, characterized in that: The glass transition temperature of the light extraction material is greater than or equal to 125°C.

13. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises an anode, a light-emitting functional layer, a cathode and a light extraction layer which are sequentially stacked, wherein the light extraction layer is made of the light extraction material according to any one of claims 9 to 12.

14. The organic electroluminescent device according to claim 13, characterized in that: The light-emitting functional layer comprises a hole transport unit, a light-emitting functional layer and an electron transport unit, and the hole transport unit, the light-emitting functional layer and the electron transport unit are sequentially stacked from the anode to the cathode; Wherein, the hole transport unit includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer; The electron transport unit includes at least one of a hole blocking layer, an electron transport layer, and an electron injection layer.

15. A display device, characterized in that: The display device comprises the organic electroluminescent device according to any one of claims 13 to 14.

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