Aromatic oxetane and application thereof in packaging composition

Abstract

The invention provides aromatic oxetane, and relates to the field of sealants, the aromatic oxetane has oxetane connecting R1 and R2, R2 is further connected with an aromatic ring through X and R3, and the aromatic ring is further connected with R4, R5 and R6; wherein R1 is selected from a substituted or unsubstituted aliphatic chain alkyl group with 1-6 hydrogen or carbon atoms, R2 is selected from an aliphatic chain alkyl group with 1-4 carbon atoms, X is selected from oxygen, sulfur or nitrogen, R3 is selected from a substituted or unsubstituted aliphatic chain alkyl group with 1-10 hydrogen or carbon atoms, and R4 is selected from a substituted or unsubstituted aliphatic chain alkyl group with 1-6 carbon atoms. R4, R5 and R6 are independently selected from hydrogen, a fluorine-containing group and substituted or unsubstituted aliphatic chain alkyl with the number of carbon atoms being 1-18, at least one of R4, R5 and R6 comprises the fluorine-containing group, and the fluorine-containing group comprises fluorine, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, fluorine-substituted aliphatic chain alkyl with the number of carbon atoms being 2-10 or fluorine-substituted aryl. According to the aromatic oxetane, the dielectric constant of the packaging composition is reduced, and the thermal stability and the spreading performance are improved.

Description

Technical Field

[0001] The present application relates to the field of sealants, and more particularly, to an aromatic oxetane and application thereof in a packaging composition. Background Art

[0002] Organic light-emitting diode (OLED) is a light-emitting electronic device using a sandwich structure. OLED devices have the characteristics of self-luminescence, high response, low power consumption, wide viewing angle, flexible display, etc., and have been widely used in recent years. When OLED devices are affected by water, oxygen, and outgassing from inside and outside, the organic layer and electrode layer of the OLED device will be oxidized, resulting in bad pixels and even causing a significant reduction in the life of the OLED device. Therefore, a packaging structure is needed to encapsulate the OLED.

[0003] The OLED device is encapsulated in a multi-layer structure, and the encapsulation layer includes an inorganic barrier layer and an organic barrier layer. Among them, the organic barrier layer can be prepared by inkjet printing using thin film encapsulation (TFE) ink.

[0004] TFE ink is a packaging composition. The performance of the packaging composition is very important to the stability and life of OLED devices. On the one hand, if the spreadability of the packaging composition is poor, the processing performance of the organic barrier layer will be reduced, resulting in uneven thickness of the prepared organic barrier layer, and ultimately reducing the imaging quality of the OLED device. On the other hand, after the packaging composition is cross-linked, an organic barrier layer will be formed, and the dielectric constant of the organic barrier layer is very important. A lower dielectric constant can effectively improve the signal-to-noise ratio of OLED devices and reduce signal delay. Therefore, the development of packaging compositions with low dielectric constants has also become a key point in OLED packaging technology.

[0005] Therefore, it is an urgent problem to be solved to enhance the spreading performance of the encapsulation composition on the basis of the low dielectric constant of the encapsulation composition after cross-linking. Summary of the invention

[0006] The present application provides an aromatic oxetane. When the aromatic oxetane is added to a packaging composition, not only the packaging composition has a low dielectric constant after cross-linking, but also the spreading performance of the packaging composition is enhanced.

[0007] In a first aspect, an aromatic oxetane is provided, wherein the aromatic oxetane has an oxetane, wherein the oxetane is connected to R 1 and R 2 , where R 2 Also through X, R3 is connected to an aromatic ring, wherein the aromatic ring is also connected to R 4 , R 5 and R 6 ; Among them, R 1 is selected from hydrogen atoms or substituted or unsubstituted fatty chain alkyl groups having 1 to 6 carbon atoms, R 2 is selected from aliphatic chain alkyl groups having 1 to 4 carbon atoms, X is selected from oxygen atoms, sulfur atoms or nitrogen atoms, R 3 is selected from hydrogen atoms or substituted or unsubstituted fatty chain alkyl groups having 1 to 10 carbon atoms, R 4 , R 5 and R 6 are independently selected from hydrogen atoms, fluorine-containing groups, substituted or unsubstituted fatty chain alkyl groups having 1 to 18 carbon atoms, and R 4 , R 5 and R 6 At least one of the fluorine-containing groups includes a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group, a trifluoromethylthio group, a fluorine-substituted aliphatic chain alkyl group having 2 to 10 carbon atoms, or a fluorine-substituted aryl group.

[0008] In combination with the first aspect, in certain implementations of the first aspect, the aromatic oxetane has Formula 1, which is as follows:

[0009]

[0010] After being added to the encapsulation composition, the aromatic oxetane provided in the present application can effectively reduce the dielectric constant of the encapsulation composition and effectively improve the thermal stability and spreading performance of the encapsulation composition.

[0011] In conjunction with the first aspect, in some implementations of the first aspect, R 1 Selected from methyl or ethyl.

[0012] In conjunction with the first aspect, in some implementations of the first aspect, R 2 Selected from methylene.

[0013] In conjunction with the first aspect, in certain implementations of the first aspect, X is selected from an oxygen atom.

[0014] In conjunction with the first aspect, in some implementations of the first aspect, R 3 Selected from methylene.

[0015] In combination with the first aspect, in certain implementations of the first aspect, the aromatic oxetane has Formula 2, Formula 3, Formula 4, or Formula 5, and Formula 2, Formula 3, Formula 4, and Formula 5 are as follows:

[0016]

[0017] In a second aspect, a packaging composition is provided, comprising: an aromatic oxetane according to the first aspect or any one of the implementations of the first aspect; a vinyl compound; and an initiator.

[0018] The encapsulation composition provided by the present application has a lower dielectric constant and higher thermal stability and spreading performance.

[0019] In combination with the second aspect, in certain implementations of the second aspect, the encapsulation composition further includes: an epoxy compound; and / or an alkyl-substituted oxetane compound.

[0020] In combination with the second aspect, in certain implementations of the second aspect, the alkyl-substituted oxetane compound includes: 3-ethyl-3-(pentyloxy)oxetane, and / or 3,3'-(oxybismethylene)bis(3-ethyl)oxetane.

[0021] In conjunction with the second aspect, in certain implementations of the second aspect, the vinyl compound includes benzyl vinyl ether and / or 1,4-cyclohexanedimethanol divinyl ether.

[0022] In conjunction with the second aspect, in certain implementations of the second aspect, the initiator includes triarylsulfonium pentafluorophenylborate and / or 9,10-dibutoxyanthracene.

[0023] In combination with the second aspect, in certain implementations of the second aspect, the weight fraction of the aromatic oxetane in the first aspect or any one of the implementations of the first aspect is 10% to 60% of the encapsulation composition.

[0024] In combination with the second aspect, in certain implementations of the second aspect, the weight fraction is 35% to 60%.

[0025] In combination with the second aspect, in certain implementations of the second aspect, the weight fraction is 35% to 45%.

[0026] In a third aspect, a use of an aromatic oxetane as in the first aspect or any one of the implementations of the first aspect in a packaging composition is provided. After being added to the packaging composition, the aromatic oxetane provided in the present application can effectively reduce the dielectric constant of the packaging composition and effectively improve the thermal stability and spreading performance of the packaging composition.

[0027] In a fourth aspect, a preparation method is provided, comprising: reacting an oxetane compound with an aromatic compound to generate an aromatic oxetane; wherein the oxetane compound comprises an oxetane connected to R 1 and R 2 , R 2Also connected to a hydroxyl group, a thiol group or an amino group; wherein the aromatic compound has an aromatic ring, and the aromatic ring is connected to R 3 , R 4 , R 5 and R 6 ; Among them, R 1 is selected from hydrogen atoms or substituted or unsubstituted fatty chain alkyl groups having 1 to 6 carbon atoms, R 2 is selected from aliphatic chain alkyl groups having 1 to 4 carbon atoms, R 3 is selected from hydrogen atoms or substituted or unsubstituted fatty chain alkyl groups having 1 to 10 carbon atoms, R 4 , R 5 and R 6 are independently selected from hydrogen atoms, fluorine-containing groups, substituted or unsubstituted fatty chain alkyl groups having 1 to 18 carbon atoms, and R 4 , R 5 and R 6 At least one of the fluorine-containing groups includes a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group, a trifluoromethylthio group, a fluorine-substituted aliphatic chain alkyl group having 2 to 10 carbon atoms, or a fluorine-substituted aryl group.

[0028] In combination with the fourth aspect, in certain implementations of the fourth aspect, an oxetane compound is reacted with an aromatic compound to generate an aromatic oxetane, comprising: adding the oxetane compound and the aromatic compound to a reaction container; adding an alkaline solution to the reaction container, and continuously stirring the alkaline solution, the oxetane compound and the aromatic compound to obtain a reaction product; extracting, washing, drying, concentrating, and purifying the reaction product to obtain the aromatic oxetane.

[0029] In combination with the fourth aspect, in certain implementations of the fourth aspect, the method further includes: using the tetrabutylammonium iodide as a phase transfer catalyst.

[0030] In combination with the fourth aspect, in certain implementations of the fourth aspect, the oxetane compound includes 3-methyl-3-hydroxymethyloxetane.

[0031] In combination with the fourth aspect, in certain implementations of the fourth aspect, the aromatic compound includes 3,5-bis(trifluoromethyl)benzyl bromide, 4-trifluoromethylbenzyl bromide, 4-trifluoromethoxybenzyl bromide or 1-bromo-4-fluoronaphthalene.

[0032] In a fifth aspect, an encapsulation layer is provided, comprising an inorganic barrier layer and an organic barrier layer, wherein the organic barrier layer is made of the encapsulation composition of the second aspect or any one of the implementations of the second aspect.

[0033] In a sixth aspect, an electronic device is provided, comprising an electrode layer and a packaging layer according to the fifth aspect or any one implementation of the fifth aspect.

[0034] In a seventh aspect, an electronic device is provided, comprising a processor and a display screen, wherein the display screen comprises the electronic device of the sixth aspect or any one implementation manner of the sixth aspect. BRIEF DESCRIPTION OF THE DRAWINGS

[0035] Figure 1 It is a schematic diagram of the encapsulation layer of an organic light-emitting diode. DETAILED DESCRIPTION

[0036] The technical solution in this application is described below.

[0037] In the embodiments of the present application, words such as "exemplary" and "for example" are used to indicate examples, illustrations or descriptions. Any embodiment or design described as "exemplary" in the present application should not be interpreted as being more preferred or more advantageous than other embodiments or designs. Specifically, the use of the word "exemplary" is intended to present concepts in a concrete way.

[0038] The business scenarios described in the embodiments of the present application are intended to more clearly illustrate the technical solutions of the embodiments of the present application, and do not constitute a limitation on the technical solutions provided in the embodiments of the present application. Ordinary technicians in this field can know that with the emergence of new business scenarios, the technical solutions provided in the embodiments of the present application are also applicable to similar technical problems.

[0039] References to "one embodiment" or "some embodiments" etc. described in this specification mean that a particular feature, structure or characteristic described in conjunction with the embodiment is included in one or more embodiments of the present application. Thus, the phrases "in one embodiment", "in some embodiments", "in some other embodiments", "in some other embodiments", etc. appearing in different places in this specification do not necessarily refer to the same embodiment, but mean "one or more but not all embodiments", unless otherwise specifically emphasized in other ways. The terms "including", "comprising", "having" and their variations all mean "including but not limited to", unless otherwise specifically emphasized in other ways.

[0040] Organic light-emitting diode (OLED) is a light-emitting electronic device using a sandwich structure. OLED devices have the characteristics of self-luminescence, high response, low power consumption, wide viewing angle, flexible display, etc., and have been widely used in recent years. When OLED devices are affected by water, oxygen, and outgassing from inside and outside, the organic layer and electrode layer of the OLED device will be oxidized, resulting in bad pixels and even causing a significant reduction in the life of the OLED device. Therefore, a packaging structure is needed to encapsulate the OLED.

[0041] Figure 1Schematic diagram of an encapsulation layer 100 of an organic light-emitting diode. The OLED device is encapsulated in a multi-layer structure, and the encapsulation layer 100 includes an inorganic barrier layer 110 and an organic barrier layer 120. The inorganic barrier layer 110 can be formed by plasma enhanced chemical vapor deposition (PECVD). The organic barrier layer 120 can be prepared by inkjet printing using thin film encapsulation (TFE) ink.

[0042] TFE ink is a packaging composition. The performance of the packaging composition is very important to the stability and life of the OLED device. On the one hand, if the spreadability of the packaging composition is poor, the processing performance of the organic barrier layer 120 will be reduced, resulting in uneven thickness of the prepared organic barrier layer 120, and ultimately reducing the imaging quality of the OLED device. On the other hand, after the packaging composition is cross-linked, an organic barrier layer 120 will be formed, and the dielectric constant of the organic barrier layer 120 is very important. A lower dielectric constant can effectively improve the signal-to-noise ratio of the OLED device and reduce signal delay. Therefore, the development of a packaging composition with a low dielectric constant has also become a key point in OLED packaging technology.

[0043] By introducing vinyl ether and oxetane substituted with fluorine-containing groups, the electronegativity of the encapsulation composition can be balanced, thereby achieving the purpose of reducing the dielectric constant, but the spreading performance is poor. Therefore, on the basis of the low dielectric constant of the encapsulation composition after cross-linking, enhancing the spreading performance of the encapsulation composition is an urgent problem to be solved.

[0044] Based on this, an embodiment of the present application provides an aromatic oxetane, which, after being added to the encapsulation composition, not only allows the encapsulation composition to have a low dielectric constant after cross-linking, but also enhances the spreading performance of the encapsulation composition.

[0045] The aromatic oxetane has an oxetane ring, and the oxetane ring is connected to R 1 and R 2 , where R 2 Also through X, R 3 is connected to an aromatic ring, wherein the aromatic ring is also connected to R 4 , R 5 and R 6 ; Among them, R 1 is selected from hydrogen atoms or substituted or unsubstituted fatty chain alkyl groups having 1 to 6 carbon atoms, R 2 is selected from aliphatic chain alkyl groups having 1 to 4 carbon atoms, X is selected from oxygen atoms, sulfur atoms or nitrogen atoms, R 3is selected from hydrogen atoms or substituted or unsubstituted fatty chain alkyl groups having 1 to 10 carbon atoms, R 4 , R 5 and R 6 are independently selected from hydrogen atoms, fluorine-containing groups, substituted or unsubstituted fatty chain alkyl groups having 1 to 18 carbon atoms, and R 4 , R 5 and R 6 At least one of the fluorine-containing groups includes a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group, a trifluoromethylthio group, a fluorine-substituted aliphatic chain alkyl group having 2 to 10 carbon atoms, or a fluorine-substituted aryl group.

[0046] In some embodiments, the aromatic oxetane has Formula 1, which is as follows:

[0047]

[0048] Among them, R 1 is selected from hydrogen atoms or substituted or unsubstituted fatty chain alkyl groups having 1 to 6 carbon atoms, R 2 is selected from aliphatic chain alkyl groups having 1 to 4 carbon atoms, X is selected from oxygen atoms, sulfur atoms or nitrogen atoms, R 3 is selected from hydrogen atoms or substituted or unsubstituted fatty chain alkyl groups having 1 to 10 carbon atoms, R 4 , R 5 and R 6 are independently selected from hydrogen atoms, fluorine-containing groups, substituted or unsubstituted fatty chain alkyl groups having 1 to 18 carbon atoms, and R 4 , R 5 and R 6 At least one of the fluorine-containing groups includes a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group, a trifluoromethylthio group, a fluorine-substituted aliphatic chain alkyl group having 2 to 10 carbon atoms, or a fluorine-substituted aryl group.

[0049] After being added to the encapsulation composition, the aromatic oxetane provided in the present application can effectively reduce the dielectric constant of the encapsulation composition and effectively improve the thermal stability and spreading performance of the encapsulation composition.

[0050] In some embodiments, R 1 Selected from methyl or ethyl.

[0051] In some embodiments, R 2 Selected from methylene.

[0052] In some embodiments, X is selected from oxygen atoms.

[0053] In some embodiments, R 3 Selected from methylene.

[0054] In some embodiments, the aromatic oxetane has Formula 2, Formula 3, Formula 4, or Formula 5, wherein Formula 2, Formula 3, Formula 4, and Formula 5 are

[0055] Formula 5 is as follows:

[0056]

[0057]

[0058] The present application also provides a packaging composition, comprising: the aforementioned aromatic oxetane; a vinyl compound; and an initiator.

[0059] The encapsulation composition provided by the present application has a lower dielectric constant and higher thermal stability and spreading performance.

[0060] In some embodiments, the encapsulation composition further comprises: an epoxy compound; and / or an alkyl-substituted oxetane compound.

[0061] In some embodiments, the alkyl-substituted oxetane compound includes: 3-ethyl-3-(pentyloxy)oxetane, and / or 3,3′-(oxybismethylene)bis(3-ethyl)oxetane.

[0062] In some embodiments, the vinyl compound includes benzyl vinyl ether and / or 1,4-cyclohexanedimethanol divinyl ether.

[0063] In some embodiments, the initiator includes triarylsulfonium pentafluorophenylborate and / or 9,10-dibutoxyanthracene.

[0064] In some embodiments, the weight fraction of the aromatic oxetane in the packaging composition is 10% to 60%.

[0065] In some embodiments, the weight fraction is 35% to 60%.

[0066] In some embodiments, the weight fraction is 35% to 45%.

[0067] The present application also provides a use of the aforementioned aromatic oxetane in a packaging composition.

[0068] After being added to the encapsulation composition, the aromatic oxetane provided in the present application can effectively reduce the dielectric constant of the encapsulation composition and effectively improve the thermal stability and spreading performance of the encapsulation composition.

[0069] The present application also provides a preparation method, comprising: reacting an oxetane compound with an aromatic compound to generate an aromatic oxetane; wherein the oxetane compound comprises an oxetane connected to R 1 and R 2 , R 2 Also connected to a hydroxyl group, a thiol group or an amino group; wherein the aromatic compound has an aromatic ring, and the aromatic ring is connected to R 3 , R 4 , R 5 and R 6 ; Among them, R 1 is selected from hydrogen atoms or substituted or unsubstituted fatty chain alkyl groups having 1 to 6 carbon atoms, R 2 is selected from aliphatic chain alkyl groups having 1 to 4 carbon atoms, R 3 is selected from hydrogen atoms or substituted or unsubstituted fatty chain alkyl groups having 1 to 10 carbon atoms, R 4 , R 5 and R 6 are independently selected from hydrogen atoms, fluorine-containing groups, substituted or unsubstituted fatty chain alkyl groups having 1 to 18 carbon atoms, and R 4 , R 5 and R 6 At least one of the fluorine-containing groups includes a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group, a trifluoromethylthio group, a fluorine-substituted aliphatic chain alkyl group having 2 to 10 carbon atoms, or a fluorine-substituted aryl group.

[0070] In some embodiments, an oxetane compound is reacted with an aromatic compound to generate an aromatic oxetane, comprising: adding the oxetane compound and the aromatic compound to a reaction container; adding an alkaline solution to the reaction container, and continuously stirring the alkaline solution, the oxetane compound, and the aromatic compound to obtain a reaction product; and extracting, washing, drying, concentrating, and purifying the reaction product to obtain the aromatic oxetane.

[0071] In some embodiments, the method further comprises: using the tetrabutylammonium iodide as a phase transfer catalyst.

[0072] In some embodiments, the oxetane compound includes 3-methyl 3-hydroxymethyloxetane.

[0073] In some embodiments, the aromatic compound includes 3,5-bis(trifluoromethyl)benzyl bromide, 4-trifluoromethylbenzyl bromide, 4-trifluoromethoxybenzyl bromide, or 1-bromo-4-fluoronaphthalene.

[0074] The present application also provides an encapsulation layer, including an inorganic barrier layer and an organic barrier layer, wherein the organic barrier layer is made of the aforementioned encapsulation composition. For example, the inorganic barrier layer and the organic barrier layer can be as follows Figure 1 Settings shown.

[0075] The present application also provides an electronic device, which includes an electrode layer and the aforementioned encapsulation layer. For example, the electronic device may be an OLED. The encapsulation layer 100 may be used to encapsulate the electrode layer of the OLED.

[0076] The present application also provides an electronic device, including a processor and a display screen, wherein the display screen includes the aforementioned electronic device. For example, the electronic device may be a mobile phone, a tablet computer, etc.

[0077] The synthesis method of the aromatic oxetane provided in the present application is described in detail below in conjunction with Examples C1 to C4.

[0078] [Example C1]

[0079] 100g (0.98mol) of 3-methyl-3-hydroxymethyloxetane, 315.6g (1.03mol) of 3,5-bis(trifluoromethyl)benzyl bromide and 0.36g of tetrabutylammonium iodide were added to a 1000mL three-necked reaction bottle equipped with a thermometer, a stirrer and a constant pressure dropping funnel, wherein tetrabutylammonium iodide was used as a phase transfer catalyst. 80g of a 50% sodium hydroxide aqueous solution was slowly dripped into the above three-necked reaction bottle and stirred continuously, and stirred at 25°C for 40 hours. Thin layer chromatography (TLC) technology was used to detect whether the chemical reaction was completed. After the reaction was completed, the product was extracted with ethyl acetate to obtain ethyl acetate containing the product. The ethyl acetate containing the product was washed with water, the washed ethyl acetate was dried, and the dried ethyl acetate was concentrated. The ethyl acetate containing the product was purified by column chromatography to obtain 201g of a colorless oil. Among them, the eluent for column chromatography purification includes petroleum ether and ethyl acetate with a mass fraction of 10 to 1.

[0080] The yield of Example C1 was 63%. The obtained product contained 99% of 3-methyl-3-(3,5-bis(trifluoromethyl)benzyloxymethyloxetane) (hereinafter referred to as Compound C1). Unless it is Example C1, Compound C1 mentioned below is Compound C1.

[0081] The structural formula of C1 is shown in the above formula 2.

[0082] [Example C2]

[0083] The process of Example C2 is similar to that of Example C1, except that, instead of adding 315.6 g (1.03 mol) of 3,5-bis(trifluoromethyl)benzyl bromide, 281 g (1.03 mol) of 4-trifluoromethylbenzyl bromide was added as a reactant in Example C2.

[0084] Example C2 obtained 201 g of a colorless oil, and the yield of Example C2 was 63%. The obtained product contained 99% of 3-methyl-3-(4-trifluoromethyl)benzyloxymethyloxetane (hereinafter referred to as compound C2). Unless it is emphasized that it is Example C2, C2 mentioned below is compound C2.

[0085] The structural formula of C2 is shown in the above formula 3.

[0086] [Example C3]

[0087] 100g (0.98mol) of 3-methyl-3-hydroxymethyloxetane, 300g (1.17mol) of 4-trifluoromethoxybenzyl bromide and 54g of tetrabutylammonium iodide were added to a 1000mL three-necked reaction bottle equipped with a thermometer, a stirrer and a constant pressure dropping funnel, wherein tetrabutylammonium iodide was used as a phase transfer catalyst. 580g of a 50% sodium hydroxide aqueous solution was slowly dripped into the three-necked reaction bottle and stirred continuously, and stirred at 25°C for 40 hours. TLC technology was used to detect whether the chemical reaction was completed. After the reaction was completed, the product was extracted with ethyl acetate to obtain ethyl acetate containing the product. The ethyl acetate containing the product was washed with water, the washed ethyl acetate was dried, and the dried ethyl acetate was concentrated. The ethyl acetate containing the product was purified by column chromatography to obtain 190g of a colorless oil. Among them, the eluent for column chromatography purification includes petroleum ether and ethyl acetate with a mass fraction of 10 to 1.

[0088] The yield of Example C3 was 70%. The obtained product contained 99% of 3-methyl-3-(4-trifluoromethoxy)benzyloxymethyloxetane (hereinafter referred to as Compound C3). Unless it is Example C3, all C3 mentioned below is Compound C3.

[0089] The structural formula of C3 is shown in the above formula 4.

[0090] [Example C4]

[0091] The process of Example C4 is similar to that of Example C3, except that, instead of adding 300 g (1.17 mol) of 4-trifluoromethoxybenzyl bromide, 264 g (1.17 mol) of 1-bromo-4-fluoronaphthalene is added as a reactant in Example C4.

[0092] Example C4 gave 160 g of a colorless oil, and the yield of Example C4 was 66%. The obtained product contained 99% of 3-methyl-3-(1-methoxy-4-fluoronaphthyl)oxetane (hereinafter referred to as Compound C4). Unless it is Example C4, all C4 mentioned below is Compound C4.

[0093] The structural formula of C2 is shown in the above formula 5.

[0094] The following is a detailed description of the synthesis methods of some components in the encapsulation composition provided by the present application in conjunction with Examples B1 and B2.

[0095] [Example B1]

[0096] 100g (0.86mol) of 3-ethyl-3-hydroxymethyloxetane and 0.28g of tetrabutylammonium iodide were added to a 1000mL three-necked reaction bottle equipped with a thermometer, a stirrer and a constant pressure dropping funnel, wherein tetrabutylammonium iodide was used as a phase transfer catalyst. 137g of a sodium hydroxide aqueous solution with a mass concentration of 50% was slowly dripped into the above three-necked reaction bottle and stirred continuously, and 136.5g (0.9mol) of 1-bromopentane was dripped at 25°C, and stirred for 40 hours after the dropwise addition was completed. TLC technology was used to detect whether the chemical reaction was completed. After the reaction was completed, the product was extracted with ethyl acetate to obtain ethyl acetate containing the product. The ethyl acetate containing the product was washed with water, the washed ethyl acetate was dried, and the dried ethyl acetate was concentrated. The ethyl acetate containing the product was purified by column chromatography to obtain 101g of colorless oil. Among them, the eluent for column chromatography purification includes petroleum ether and ethyl acetate with a mass fraction of 10 to 1.

[0097] The yield of Example B1 was 63%. The obtained product contained 99% of 3-ethyl-3-(pentyloxymethyl)oxetane (hereinafter referred to as Compound B1). Unless it is Example B1, Compound B1 mentioned below is Compound B1.

[0098] The structural formula of B1 is shown below:

[0099]

[0100] Compound B2 is a commercially available product with a product name of 3,3'-(oxybismethylene)bis(3-ethyl)oxetane and a CAS number of 18934-00-4.

[0101] The encapsulation composition provided in the present application is described in detail below in conjunction with Examples 1 to 9, and Comparative Examples 1 and 2.

[0102] For ease of description, the following compounds and their abbreviations are first introduced.

[0103] Epoxy compounds: aliphatic epoxy monomers (hereinafter referred to as A1), cyclohexene oxide monomers (hereinafter referred to as A2).

[0104] Among them, in the aliphatic epoxy monomer, the substituent other than the epoxy group is a non-cycloalkane aliphatic chain.

[0105] Vinyl ether monomers: benzyl vinyl ether (hereinafter referred to as D1), 1,4-cyclohexanedimethanol divinyl ether (hereinafter referred to as D2).

[0106] Initiator: triarylsulfonium pentafluorophenylborate (hereinafter referred to as E1), 9,10-dibutoxyanthracene (hereinafter referred to as E2).

[0107] [Example 1]

[0108] A1, C1, D1, E1 and E2 were placed in a 125 mL brown polypropylene bottle and mixed at room temperature for 6 hours using an oscillator. The weight ratio of A1, C1, D1, E1 and E2 was 30:35:35:0.5:1.5. The weight of the initiator is not included in the system, so the weight fractions mentioned in this application refer to the weight fractions of the compounds other than the initiator. For example, in Example 1, the weight fraction of C1 is 35%.

[0109] Similarly, Examples 2 to 9, and Comparative Examples 1 and 2 were also prepared using a method similar to that of Example 1. The difference from Example 1 is that the components and weight ratios included in the other examples are different, and Table 1 shows the weight ratios of the components of Examples 1 to 9, and Comparative Examples 1 and 2.

[0110] Table 1

[0111] A1 A2 B1 B2 C1 C2 C3 C4 D1 D2 E1 E2 Example 1 30 - - - 35 - - - 35 - 0.5 1.0 Example 2 30 - - - - 35 - - 35 - 0.5 1.0 Example 3 30 - - - - - 35 - 35 - 0.5 1.0 Example 4 30 - - - - - - 35 35 - 0.5 1.0 Example 5 30 - 35 - 35 - - - - - 0.5 1.0 Example 6 - 30 - 35 - 35 - - - - 0.5 1.0 Example 7 30 - - - 45 - - - 25 - 0.5 1.0 Example 8 - 30 - - - 35 - - - 35 0.5 1.0 Example 9 - - - - - 35 - - - 35 0.5 1.0 Comparative Example 1 30 - - 35 - - - - - 35 0.5 1.0 Comparative Example 2 30 - 35 - - - - - 35 - 0.5 1.0

[0112] In Table 1, “-” indicates that the corresponding component is not contained.

[0113] The encapsulation compositions obtained in the above examples and comparative examples were prepared into films with a thickness of 6 to 10 μm, and the following performance tests were performed on these films.

[0114] Photocuring rate: The infrared spectrum of a certain encapsulation composition in the embodiment and the comparative example, as well as the infrared spectrum of the film of the encapsulation composition after curing, is measured by Fourier infrared spectrometer, and the curing rate of the encapsulation composition is calculated by the ratio of the peak areas of the characteristic peaks of the encapsulation composition before and after curing.

[0115] Optical transmittance: The transmittance of the film at 300-800nm ​​is measured by a UV-visible spectrophotometer. The sample made of the film is placed on the light path of the light inlet. The test light emitted by the light emitter penetrates the sample and enters the integrating sphere from the light inlet. The detector is tested at the detection port to obtain the test light data. The sample without the film is placed on the light path of another light inlet. The test light emitted by the light emitter enters the integrating sphere from the other light inlet. The detector is tested at the detection port to obtain the reference light data. By comparing the measured test light data with the reference light data, the optical transmittance of the sample can be determined.

[0116] Dielectric constant: The encapsulation compositions prepared in the examples and comparative examples were coated on chrome plates, respectively. UV irradiation was performed at a wavelength of 395 nm and a flux of 100 mW / cm2 for 10 seconds to form a 6-10 μm film. Aluminum electrodes were deposited on the films, and the dielectric constants of the films were measured using an impedance meter at 200 kHz and 25°C.

[0117] Glass transition temperature: The glass transition temperatures of the encapsulating compositions prepared in Examples and Comparative Examples were measured by dynamic mechanical analysis (DMA).

[0118] Tension: Use a surface tension tester to measure the surface tension of the composition. For example, add the encapsulated composition to the sample dish, place the sample dish on the sample table, and reset it to zero; press the "up" key to automatically test the surface tension, and after the value on the display screen stabilizes, you can read the surface tension value on the liquid product display screen.

[0119] Viscosity: The viscosity of the encapsulation composition is measured using an EVO type rotational viscometer. For example, 7 mL of the encapsulation composition prepared in the examples and comparative examples is measured and poured into a test container, and the test container is placed on the instrument bracket. The rotor is connected to the nut with a hook, the rotor is placed in the test container, a certain speed is set for the rotor, the test is started, and the test is performed for about 20 minutes. After the data is stable, the viscosity of the encapsulation composition is read.

[0120] According to the above test, Table 2 is obtained. Table 2 shows some properties of the encapsulation composition provided by the embodiment of the present application and the comparative example.

[0121] Table 2

[0122]

[0123] According to Examples 1 to 9, the encapsulation composition provided in the embodiments of the present application has a good photocuring rate and optical transmittance, which is not much different from the photocuring rate and optical transmittance of Comparative Examples 1 and 2. Therefore, the encapsulation composition provided in the embodiments of the present application can be used to encapsulate OLEDs to form an organic barrier layer 120.

[0124] It can be seen from Examples 1 to 9 that the encapsulation composition provided in the present application has a relatively low dielectric constant, and the dielectric constants are all below 2.70.

[0125] It can be seen from Examples 1 to 9 that the encapsulation composition provided in the present application has a relatively high glass transition temperature, and therefore it can be shown that the encapsulation composition provided in the present application has good thermal stability.

[0126] According to Examples 1 to 9, the tension of the encapsulation composition provided in the present application is relatively low, so it can be shown that the encapsulation composition provided in the present application has good spreading performance. On the other hand, the viscosity of the encapsulation composition provided in the present application is relatively low, and low viscosity also corresponds to good spreading performance.

[0127] Therefore, by adding the aromatic oxetane provided in the present application, the dielectric constant of the encapsulation composition is effectively reduced, and the thermal stability and spreading performance of the encapsulation composition are effectively improved.

[0128] It should be noted that the use of the encapsulation composition provided in this application is not limited to encapsulating OLEDs. The encapsulation composition provided in this application has a low dielectric constant and a low surface tension, and can be applied to glue, coatings, inks, etc. in low dielectric constant scenarios or low surface tension scenarios. For example, it can be used as a thin film encapsulation material in the photovoltaic industry.

[0129] The above is only a specific implementation of the present application, but the protection scope of the present application is not limited thereto. Any person skilled in the art who is familiar with the present technical field can easily think of changes or substitutions within the technical scope disclosed in the present application, which should be included in the protection scope of the present application. Therefore, the protection scope of the present application should be based on the protection scope of the claims.

Claims

1. An aromatic oxetane, the aromatic oxetane having an oxetane, the oxetane being connected to R 1 and R 2 ,in, R 2 Also through X, R 3 connected to an aromatic ring, wherein the aromatic ring is also connected to R 4 , R 5 and R 6 ; Among them, R 1 is selected from hydrogen atoms or substituted or unsubstituted fatty chain alkyl groups having 1 to 6 carbon atoms, R 2 is selected from aliphatic chain alkyl groups having 1 to 4 carbon atoms, X is selected from oxygen atoms, sulfur atoms or nitrogen atoms, R 3 is selected from hydrogen atoms or substituted or unsubstituted fatty chain alkyl groups having 1 to 10 carbon atoms, R 4 , R 5 and R 6 are independently selected from hydrogen atoms, fluorine-containing groups, substituted or unsubstituted fatty chain alkyl groups having 1 to 18 carbon atoms, and R 4 , R 5 and R 6 At least one of the above mentioned fluorine-containing groups includes a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group, a trifluoromethylthio group, a fluorine-substituted aliphatic chain alkyl group having 2 to 10 carbon atoms, or a fluorine-substituted aryl group.

2. The aromatic oxetane according to claim 1, wherein the aromatic oxetane has Formula 1, which is as follows:

3. The aromatic oxetane according to claim 1 or 2, R 1 Selected from methyl or ethyl.

4. The aromatic oxetane according to any one of claims 1 to 3, wherein R 2 Selected from methylene.

5. The aromatic oxetane according to any one of claims 1 to 4, wherein X is selected from an oxygen atom.

6. The aromatic oxetane according to any one of claims 1 to 5, wherein R 3 Selected from methylene.

7. The aromatic oxetane according to any one of claims 1 to 6, wherein the aromatic oxetane has Formula 2, Formula 3, Formula 4 or Formula 5, wherein Formula 2, Formula 3, Formula 4 and Formula 5 are as follows:

8. A packaging composition, characterized in that include: The aromatic oxetane according to any one of claims 1 to 7; Vinyl compounds; Initiator.

9. The encapsulation composition according to claim 8, characterized in that Also includes: Epoxides; and / or Alkyl substituted oxetane compounds.

10. The encapsulation composition according to claim 9, characterized in that The alkyl-substituted oxetane compound includes: 3-ethyl-3-(pentyloxy)oxetane, and / or 3,3'-(oxybismethylene)bis(3-ethyl)oxetane.

11. The encapsulation composition according to any one of claims 8 to 10, characterized in that The vinyl compound includes benzyl vinyl ether and / or 1,4-cyclohexanedimethanol divinyl ether.

12. The encapsulation composition according to any one of claims 8 to 11, characterized in that The initiator includes triarylsulfonium pentafluorophenylborate and / or 9,10-dibutoxyanthracene.

13. The encapsulation composition according to any one of claims 8 to 12, characterized in that The weight fraction of the aromatic oxetane in the packaging composition is 10% to 60%.

14. The encapsulation composition according to claim 13, characterized in that The weight percentage is 35% to 60%.

15. The encapsulation composition according to claim 14, characterized in that The weight percentage is 35% to 45%.

16. Use of the aromatic oxetane according to any one of claims 1 to 7 in a packaging composition.

17. A preparation method, characterized in that: include: reacting an oxetane compound with an aromatic compound to produce an aromatic oxetane; Wherein, the oxetane compound has an oxetane, and the oxetane is connected to R 1 and R 2 , R 2 Also connected to hydroxyl, sulfhydryl or amino groups; The aromatic compound has an aromatic ring connected to R 3 , R 4 , R 5 and R 6 ; Among them, R 1 is selected from hydrogen atoms or substituted or unsubstituted fatty chain alkyl groups having 1 to 6 carbon atoms, R 2 is selected from aliphatic chain alkyl groups having 1 to 4 carbon atoms, R 3 is selected from hydrogen atoms or substituted or unsubstituted fatty chain alkyl groups having 1 to 10 carbon atoms, R 4 , R 5 and R 6 are independently selected from hydrogen atoms, fluorine-containing groups, substituted or unsubstituted fatty chain alkyl groups having 1 to 18 carbon atoms, and R 4 , R 5 and R 6 At least one of the above mentioned fluorine-containing groups includes a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group, a trifluoromethylthio group, a fluorine-substituted aliphatic chain alkyl group having 2 to 10 carbon atoms, or a fluorine-substituted aryl group.

18. The method according to claim 17, characterized in that The step of reacting an oxetane compound with an aromatic compound to generate an aromatic oxetane comprises: adding an oxetane compound and an aromatic compound into a reaction vessel; Adding an alkaline solution into the reaction container, and continuously stirring the alkaline solution, the oxetane compound and the aromatic compound to obtain a reaction product; The reaction product is extracted, washed, dried, concentrated and purified to obtain aromatic oxetane.

19. The method according to claim 17 or 18, characterized in that Also includes: Tetrabutylammonium iodide was used as a phase transfer catalyst.

20. The method according to any one of claims 17 to 19, characterized in that The oxetane compound includes 3-methyl-3-hydroxymethyloxetane.

21. The method according to any one of claims 17 to 20, characterized in that The aromatic compound includes 3,5-bis(trifluoromethyl)benzyl bromide, 4-trifluoromethylbenzyl bromide, 4-trifluoromethoxybenzyl bromide or 1-bromo-4-fluoronaphthalene.

22. A packaging layer, characterized in that: The invention comprises an inorganic barrier layer and an organic barrier layer, wherein the organic barrier layer is made of the encapsulation composition according to any one of claims 8 to 15.

23. An electronic device, characterized in that: Comprising an electrode layer and a packaging layer as claimed in claim 22.

24. An electronic device, characterized in that: It comprises a processor and a display screen, wherein the display screen comprises the electronic device as claimed in claim 23.

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