CN111777714A - Thin film packaging material, manufacturing method thereof, thin film packaging structure and electronic device - Google Patents
Thin film packaging material, manufacturing method thereof, thin film packaging structure and electronic device Download PDFInfo
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- CN111777714A CN111777714A CN201910270781.9A CN201910270781A CN111777714A CN 111777714 A CN111777714 A CN 111777714A CN 201910270781 A CN201910270781 A CN 201910270781A CN 111777714 A CN111777714 A CN 111777714A
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- ferrocene
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- adamantyl
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- 238000004806 packaging method and process Methods 0.000 title claims abstract description 21
- 239000005022 packaging material Substances 0.000 title claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 13
- 239000010409 thin film Substances 0.000 title claims description 40
- OVMIKLUPRSNKND-UHFFFAOYSA-N cyclopenta-1,3-diene 1-cyclopenta-2,4-dien-1-yladamantane iron(2+) Chemical group [Fe++].c1cc[cH-]c1.C1C2CC3CC1CC(C2)(C3)[c-]1cccc1 OVMIKLUPRSNKND-UHFFFAOYSA-N 0.000 claims abstract description 39
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 23
- -1 adamantyl ferrocene compound Chemical class 0.000 claims abstract description 19
- 239000012044 organic layer Substances 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims description 49
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 36
- 239000010408 film Substances 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 238000005538 encapsulation Methods 0.000 claims description 25
- 239000011259 mixed solution Substances 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 claims description 22
- 239000000758 substrate Substances 0.000 claims description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 17
- 150000001263 acyl chlorides Chemical class 0.000 claims description 12
- 239000012043 crude product Substances 0.000 claims description 12
- 238000005886 esterification reaction Methods 0.000 claims description 12
- 230000002194 synthesizing effect Effects 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 6
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 239000000741 silica gel Substances 0.000 claims description 6
- 229910002027 silica gel Inorganic materials 0.000 claims description 6
- 238000000967 suction filtration Methods 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000001033 ether group Chemical group 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 244000028419 Styrax benzoin Species 0.000 claims description 3
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 3
- 229960002130 benzoin Drugs 0.000 claims description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 3
- 239000012965 benzophenone Substances 0.000 claims description 3
- 235000019382 gum benzoic Nutrition 0.000 claims description 3
- 239000003999 initiator Substances 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 238000010030 laminating Methods 0.000 claims description 2
- 239000003566 sealing material Substances 0.000 claims 3
- 239000008393 encapsulating agent Substances 0.000 claims 1
- 238000002834 transmittance Methods 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 5
- 239000000178 monomer Substances 0.000 abstract description 5
- 229920006254 polymer film Polymers 0.000 abstract description 4
- 239000010410 layer Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 3
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920006280 packaging film Polymers 0.000 description 1
- 239000012785 packaging film Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2343/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium or a metal; Derivatives of such polymers
Abstract
In the film packaging material, the manufacturing method thereof, the film packaging structure and the electronic device, the adamantyl ferrocene unit is introduced into the main chain or the side group of the acrylate monomer, the thermal stability and the light transmittance of the organic layer are improved by utilizing the structural characteristics of the adamantyl ferrocene compound, and meanwhile, the finally formed polymer film has good film forming property, so that the film packaging effect is improved.
Description
Technical Field
The present disclosure relates to the field of display technologies, and in particular, to a thin film encapsulation material, a method for manufacturing the thin film encapsulation material, a thin film encapsulation structure, and an electronic device.
Background
The organic electroluminescent device (OLED) is called a display device with the greatest application prospect because it has the characteristics of self-luminescence, high brightness, high contrast, low operating voltage, flexible display and the like. In recent years, with the development of curved panels and foldable display devices, various flexible OLED display devices having bendability have been developed.
A flexible OLED display device generally includes a substrate, an electroluminescent element on the substrate, and a thin film encapsulation structure on the electroluminescent element. For a flexible OLED device, the encapsulation effect of the thin film encapsulation structure directly affects the reliability and the service life of the flexible OLED device, and therefore, how to efficiently encapsulate the flexible OLED device to prolong the service life of the device is an important issue facing those skilled in the art.
The existing film packaging structure is generally formed by overlapping an inorganic packaging layer and an organic packaging layer, wherein the inorganic packaging layer can block external water vapor and oxygen, and the organic packaging layer can ensure the planarization of the surface of a packaging film and release stress. Meanwhile, the organic packaging layer has the function of coating particles, and defects in the inorganic layer are prevented from diffusing.
Currently, the organic layer is generally formed of an acrylic material or an epoxy material. However, these polymeric materials generally exhibit the characteristic of poor thermal stability. Therefore, the existing film packaging material generally has the problem of poor thermal stability, and the film packaging effect is seriously influenced.
Therefore, how to solve the problem of poor thermal stability of the existing film packaging material becomes a technical problem to be solved urgently by the technical personnel in the field.
Disclosure of Invention
In view of the above, the present application provides a film packaging material to solve the problem of poor thermal stability of the existing film packaging material.
In order to solve the above technical problem, the present invention provides a film packaging material, including: a photoinitiator and a compound synthesized from an adamantyl ferrocene unit and an acrylate functional group;
the structure of the compound is shown as a formula I or a formula II:
wherein n is an integer of 1 to 30, m is an integer of 0 to 30, R1, R2 are hydrogen, alkyl or cycloalkyl; l1 to L3 are alkylene groups, alkylene ether groups, carbonyl groups or amic acid groups.
Optionally, in the thin film encapsulation material, the structural formula of the compound is:
optionally, in the thin film encapsulation material, the structural formula of the compound is:
optionally, in the film encapsulating material, the photoinitiator includes any one of acetophenone, benzophenone, benzoin, and phosphorus initiators, or any combination thereof.
The invention also provides a manufacturing method of the film packaging material, which comprises the following steps:
providing methacryloyl chloride and adamantyl ferrocene having a hydroxyl group;
synthesizing methacryloyl chloride and adamantyl ferrocene into a compound through esterification reaction of acyl chloride and hydroxyl, wherein the compound is synthesized from adamantyl ferrocene units and acrylate functional groups; and
a photoinitiator is provided and the compound is mixed with the photoinitiator.
Optionally, in the method for manufacturing a thin film encapsulation material, the adamantyl ferrocene having a hydroxyl group is monohydroxyadamantyl ferrocene;
the process for synthesizing the methacryloyl chloride and the monohydroxyadamantyl ferrocene into the compound through the esterification reaction of the acyl chloride and the hydroxyl comprises the following steps:
placing triethylamine and the monohydroxyadamantyl ferrocene in the same reaction vessel;
adding dichloromethane to the reaction vessel to form a first mixed solution;
dissolving the methacryloyl chloride in methylene chloride to form a second mixed solution;
dropwise adding the second mixed solution into the first mixed solution to perform reaction;
carrying out suction filtration and concentration to obtain a crude product of the target compound; and
and purifying the crude product by a 200-300-mesh silica gel column.
Optionally, in the manufacturing method of the thin film encapsulation material, the adamantyl ferrocene having hydroxyl group is dihydroxyadamantyl ferrocene;
the process for synthesizing the compound by the esterification reaction of acyl chloride and hydroxyl, wherein the methyl acryloyl chloride and the dihydroxy adamantyl ferrocene comprise the following steps:
placing triethylamine and the dihydroxy adamantyl ferrocene in the same reaction vessel;
adding dichloromethane to the reaction vessel to form a first mixed solution;
dissolving the methacryloyl chloride in methylene chloride to form a second mixed solution;
dropwise adding the second mixed solution into the first mixed solution to perform reaction;
carrying out suction filtration and concentration to obtain a crude product of the target compound; and
and purifying the crude product by a 200-300-mesh silica gel column.
The present invention also provides a thin film encapsulation structure, including: laminating alternating inorganic and organic layers;
wherein, the organic layer adopts the thin film packaging material.
The present invention also provides an electronic device comprising: a substrate, a functional device and a thin film encapsulation structure as described above;
the functional device and the film packaging structure are sequentially formed on the substrate, and the film packaging structure is used for packaging the functional device.
According to the film packaging material, the manufacturing method thereof, the film packaging structure and the electronic device, the adamantyl ferrocene unit is introduced into the main chain or the side group of the acrylate monomer, the thermal stability and the light transmittance of the organic layer are improved by utilizing the structural characteristics of the adamantyl ferrocene compound, and meanwhile, the finally formed polymer film has good film forming property, so that the film packaging effect is improved.
Drawings
The technical solutions of the present invention will be described in detail below with reference to the accompanying drawings and specific embodiments so that the features and advantages of the present invention will be more apparent.
FIG. 1 is a schematic structural diagram of a thin film package structure according to an embodiment of the present invention;
fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present invention.
Detailed Description
Example embodiments will now be described more fully with reference to the accompanying drawings. Example embodiments may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of example embodiments to those skilled in the art. The same reference numerals in the drawings denote the same or similar structures, and thus their repetitive description will be omitted.
The present invention provides a novel thin film encapsulation material, comprising:
a photoinitiator and a compound synthesized from an adamantyl ferrocene unit and an acrylate functional group; the structure of the compound is shown as a formula I or a formula II:
wherein n is an integer of 1 to 30, m is an integer of 0 to 30, R1, R2 are hydrogen, alkyl or cycloalkyl; l1 to L3 are alkylene groups, alkylene ether groups, carbonyl groups or amic acid groups.
Specifically, ferrocene is also called "IICyclopentadienyl iron, with the molecular formula Fe (C)5H5)2An organometallic compound of (2). Adamantane is a tricyclic aliphatic hydrocarbon, belongs to a cluster compound, is a cyclic tetrahedron which is obtained by reacting dicyclopentadiene with hydrogen under the combined action of a nickel catalyst and an aluminum trichloride catalyst and consists of 10 carbon atoms and 16 hydrogen atoms, is a highly symmetrical cage compound and has a molecular formula of C10H16The structure can be seen as a spatial configuration consisting of four equivalent six-membered rings.
The adamantyl ferrocene unit is formed by combining an adamantine unit and a ferrocene unit, wherein the adamantine unit and the ferrocene unit are connected through L2. The adamantyl ferrocene unit is combined with the acrylate functional group to form a compound in which the adamantyl ferrocene unit is attached to the acrylate functional group through either L1 or L2.
In the compound of formula one, one side of the adamantyl ferrocene unit is attached to an acrylate functional group through L1. R1 on the acrylate functional group is hydrogen, alkyl or cycloalkyl, the alkyl group has 1-10 carbon atoms, and the cycloalkyl group has 3-30 carbon atoms. L1 to L2 are alkylene groups having 1 to 30 carbon atoms, alkylene ether groups having 1 to 50 carbon atoms, carbonyl groups or amic acid groups. Wherein, L1 and L2 may be the same or different.
In the compound of formula two, the adamantyl ferrocene unit is flanked on both sides by an acrylate functional group via L1 and L2, respectively. R1 and R2 on the acrylate functional group are hydrogen, alkyl or cycloalkyl, the alkyl has 1-10 carbon atoms, and the cycloalkyl has 3-30 carbon atoms. L1 to L3 are alkylene groups having 1 to 30 carbon atoms, alkylene ether groups having 1 to 50 carbon atoms, carbonyl groups or amic acid groups. Wherein, L1, L2 and L3 may be the same or different.
The acrylate is a generic term for esters of acrylic acid and its homologues, including methyl acrylate, ethyl acrylate, 2-methyl methacrylate, 2-ethyl methacrylate, and the like. The acrylate functionality includes methyl acrylate functionality, ethyl acrylate functionality, methyl 2-methacrylate functionality, ethyl 2-methacrylate functionality, and the like. The structural formula of the acrylate functional group is as follows:
wherein x represents a position binding to L1 or L3, and Y is R1 or R2.
The compound is mixed with a photoinitiator, wherein the photoinitiator comprises any one or any combination of acetophenone, benzophenone, benzoin and phosphorus initiators and is used for causing photocuring reaction.
In the film packaging material, the adamantyl ferrocene unit and the acrylate functional group have synergistic effect, so that the film packaging material is not only beneficial to light transmission, but also has higher bond energy, and therefore, the compound has good light transmittance and thermal stability, and simultaneously has good film forming property. Therefore, the film packaging material is used as the organic layer for film packaging, so that the thermal stability and the light transmittance of the organic layer can be improved, and the film forming quality of the finally formed polymer film is better.
Correspondingly, the invention also provides a manufacturing method of the film packaging material, which comprises the following steps:
the method comprises the following steps: providing methacryloyl chloride and adamantyl ferrocene having a hydroxyl group (-OH);
step two: synthesizing methacryloyl chloride and adamantyl ferrocene into a compound through esterification reaction of acyl chloride and hydroxyl, wherein the compound is synthesized from adamantyl ferrocene units and acrylate functional groups;
step three: a photoinitiator is provided and the compound is mixed with the photoinitiator.
Specifically, methacryloyl chloride and adamantyl ferrocene with hydroxyl are intermediate products and can be directly purchased from the market. Wherein, the structural formula of the methacryloyl chloride is as follows:
in this embodiment, the hydroxyl-containing adamantyl ferrocene is monohydroxyadamantyl ferrocene, and the structural formula of the monohydroxyadamantyl ferrocene is:
the reaction equation for synthesizing methacryloyl chloride and monohydroxyadamantyl ferrocene into a compound through the esterification reaction of acyl chloride and hydroxyl is as follows:
specifically, the process for synthesizing the methacryloyl chloride and the monohydroxyadamantyl ferrocene into the compound through the esterification reaction of the acyl chloride and the hydroxyl comprises the following steps:
firstly, triethylamine (0.15g, 1.5mmol) and the monohydroxyadamantyl ferrocene (0.36g, 1mmol) are placed in the same reaction vessel;
next, dichloromethane (10mL) was added to the reaction vessel to form a first mixed solution;
thereafter, methacryloyl chloride (0.15g, 1.5mmol) was dissolved in dichloromethane to form a second mixed solution;
then, the second mixed solution was added dropwise to the first mixed solution to carry out a reaction, ice bath control was carried out for 30 minutes at the beginning of the reaction, and then a room-temperature reaction was carried out for 24 hours;
then, obtaining a crude product of the target compound through suction filtration and concentration;
and finally, purifying the crude product through a 200-300-mesh silica gel column to obtain a target compound, wherein the target compound introduces adamantyl ferrocene units into a main chain or a side group of the acrylate monomer.
In another embodiment of the present invention, the adamantyl ferrocene having a hydroxyl group is dihydroxyadamantyl ferrocene, and the structural formula of the dihydroxyadamantyl ferrocene is:
the reaction equation for synthesizing methacryloyl chloride and bis-hydroxyadamantyl ferrocene into a compound through the esterification reaction of acyl chloride and hydroxyl is as follows:
specifically, the process for synthesizing the compound from the methacryloyl chloride and the dihydroxy adamantyl ferrocene through the esterification reaction of the acyl chloride and the hydroxyl comprises the following steps:
firstly, triethylamine (0.30g, 3mmol) and the dihydroxyadamantyl ferrocene (0.41g, 1mmol) are placed in the same reaction vessel;
next, dichloromethane (10mL) was added to the reaction vessel to form a first mixed solution;
thereafter, methacryloyl chloride (0.30g, 3mmol) was dissolved in dichloromethane to form a second mixed solution;
then, the second mixed solution was added dropwise to the first mixed solution to carry out a reaction, ice bath control was carried out for 30 minutes at the beginning of the reaction, and then a room-temperature reaction was carried out for 24 hours;
then, obtaining a crude product of the target compound through suction filtration and concentration;
and finally, purifying the crude product through a 200-300-mesh silica gel column to obtain a target compound, wherein the target compound introduces adamantyl ferrocene units into a main chain or a side group of the acrylate monomer.
It should be noted that the above compounds and their preparation methods are only examples and not limitations, and in other embodiments of the present invention, different types of adamantyl ferrocene and corresponding processes can be used, as long as the compounds synthesized from adamantyl ferrocene units and acrylate functional groups can be synthesized by esterification reaction of acyl chloride and hydroxyl group.
After the target compound is formed, the target compound is mixed with a photoinitiator, whereby the thin film encapsulation material is obtained. The film packaging material not only has better thermal stability and light transmittance, but also has better film forming property.
Correspondingly, the invention also provides a film packaging structure. Fig. 1 is a schematic structural diagram of a thin film package structure according to an embodiment of the invention. As shown in fig. 1, the thin film encapsulation structure 30 includes: alternating inorganic layers 31 and organic layers 32 are stacked, and the organic layers 32 employ a thin film encapsulation material as described above.
Correspondingly, the invention also provides an electronic device. Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the invention. As shown in fig. 2, the electronic device 1 includes a substrate 10, a functional device 20, and a thin film encapsulation structure 30 as described above; the functional device 20 and the thin film encapsulation structure 30 are sequentially formed on the substrate 10, and the thin film encapsulation structure 30 is used for encapsulating the functional device 20.
Specifically, the substrate 10 may be a rigid substrate, or may be a flexible substrate, preferably a flexible substrate, so as to implement a flexible display function. The rigid substrate may be, for example, a glass substrate or a quartz substrate. The flexible substrate may be an organic polymer substrate such as a polyimide substrate (PI substrate), a polyamide substrate, a polycarbonate substrate, or a polyether sulfone substrate.
The functional device 20 includes, but is not limited to, an electroluminescent element (e.g., OLED), a liquid crystal display device, a solar cell, a thin film battery, an organic sensor, and other electronic devices.
The thin film encapsulation structure 30 includes organic layers and inorganic layers alternately stacked, and the thin film positioned at the lowermost layer and/or the uppermost layer may be either an organic layer or an inorganic layer. The organic layer is made of the thin film packaging material, and the thin film packaging material contains a compound synthesized by adamantyl ferrocene units and acrylate functional groups, so that the organic layer has good thermal stability and light transmittance, and the finally formed polymer thin film has good film forming property.
In summary, according to the film encapsulating material, the manufacturing method thereof, the film encapsulating structure and the electronic device provided by the invention, the adamantyl ferrocene unit is introduced into the main chain or the side group of the acrylate monomer, the structural characteristics of the adamantyl ferrocene compound are utilized to improve the thermal stability and the light transmittance of the organic layer, and meanwhile, the finally formed polymer film has good film forming property, so that the film encapsulating effect is improved.
The foregoing is a more detailed description of the present application in connection with specific preferred embodiments and it is not intended that the present application be limited to these specific details. For those skilled in the art to which the present application pertains, several simple deductions or substitutions may be made without departing from the concept of the present application, and all should be considered as belonging to the protection scope of the present application.
Claims (9)
1. A thin film encapsulation material, comprising: a photoinitiator and a compound synthesized from an adamantyl ferrocene unit and an acrylate functional group;
the structure of the compound is shown as a formula I or a formula II:
wherein n is an integer of 1 to 30, m is an integer of 0 to 30, R1, R2 are hydrogen, alkyl or cycloalkyl; l1 to L3 are alkylene groups, alkylene ether groups, carbonyl groups or amic acid groups.
2. The thin film encapsulant of claim 1 wherein the compound has the formula:
3. the thin film sealing material according to claim 1, wherein the compound has a formula of:
4. the film encapsulation material according to claim 1, wherein the photoinitiator comprises any one or any combination of acetophenone, benzophenone, benzoin, and phosphorus initiators.
5. A method of manufacturing a thin film encapsulation material, comprising:
providing methacryloyl chloride and adamantyl ferrocene having a hydroxyl group;
synthesizing methacryloyl chloride and adamantyl ferrocene into a compound through esterification reaction of acyl chloride and hydroxyl, wherein the compound is synthesized from adamantyl ferrocene units and acrylate functional groups; and
a photoinitiator is provided and the compound is mixed with the photoinitiator.
6. The method for producing a thin film sealing material according to claim 5, wherein the adamantyl ferrocene having a hydroxyl group is monohydroxyadamantyl ferrocene;
the process for synthesizing the methacryloyl chloride and the monohydroxyadamantyl ferrocene into the compound through the esterification reaction of the acyl chloride and the hydroxyl comprises the following steps:
placing triethylamine and the monohydroxyadamantyl ferrocene in the same reaction vessel;
adding dichloromethane to the reaction vessel to form a first mixed solution;
dissolving the methacryloyl chloride in methylene chloride to form a second mixed solution;
dropwise adding the second mixed solution into the first mixed solution to perform reaction;
carrying out suction filtration and concentration to obtain a crude product of the target compound; and
and purifying the crude product by a 200-300-mesh silica gel column.
7. The method for producing a thin film sealing material according to claim 5, wherein the hydroxyl group-containing adamantyl ferrocene is bishydroxy adamantyl ferrocene;
the process for synthesizing the compound by the esterification reaction of acyl chloride and hydroxyl, wherein the methyl acryloyl chloride and the dihydroxy adamantyl ferrocene comprise the following steps:
placing triethylamine and the dihydroxy adamantyl ferrocene in the same reaction vessel;
adding dichloromethane to the reaction vessel to form a first mixed solution;
dissolving the methacryloyl chloride in methylene chloride to form a second mixed solution;
dropwise adding the second mixed solution into the first mixed solution to perform reaction;
carrying out suction filtration and concentration to obtain a crude product of the target compound; and
and purifying the crude product by a 200-300-mesh silica gel column.
8. A thin film encapsulation structure, comprising: laminating alternating inorganic and organic layers; wherein the organic layer adopts the thin film packaging material as claimed in any one of claims 1 to 4.
9. An electronic device, comprising: a substrate, a functional device and the thin film encapsulation structure of claim 8;
the functional device and the film packaging structure are sequentially formed on the substrate, and the film packaging structure is used for packaging the functional device.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020077499A1 (en) * | 2000-12-15 | 2002-06-20 | Minoru Kakuda | Production of 2-hydrocarbyl-2-adamantyl acrylate compounds |
| CN101602832A (en) * | 2009-06-09 | 2009-12-16 | 苏州大学 | A kind of ferrocenyl graft polymer and preparation method thereof |
| CN103910764A (en) * | 2014-04-03 | 2014-07-09 | 黎明职业大学 | Polymerizable ferrocenyl derivative and preparation method thereof |
| CN104004195A (en) * | 2014-05-09 | 2014-08-27 | 中南大学 | Ferrocenyl polymer and porous material thereof, and preparation methods and application thereof |
| CN106299149A (en) * | 2015-06-12 | 2017-01-04 | 上海和辉光电有限公司 | Thin-film packing structure, preparation method and there is the organic light emitting apparatus of this structure |
| CN106967125A (en) * | 2017-05-05 | 2017-07-21 | 苏州大学 | Glycol containing ferrocene and preparation method thereof |
-
2019
- 2019-04-04 CN CN201910270781.9A patent/CN111777714A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020077499A1 (en) * | 2000-12-15 | 2002-06-20 | Minoru Kakuda | Production of 2-hydrocarbyl-2-adamantyl acrylate compounds |
| CN101602832A (en) * | 2009-06-09 | 2009-12-16 | 苏州大学 | A kind of ferrocenyl graft polymer and preparation method thereof |
| CN103910764A (en) * | 2014-04-03 | 2014-07-09 | 黎明职业大学 | Polymerizable ferrocenyl derivative and preparation method thereof |
| CN104004195A (en) * | 2014-05-09 | 2014-08-27 | 中南大学 | Ferrocenyl polymer and porous material thereof, and preparation methods and application thereof |
| CN106299149A (en) * | 2015-06-12 | 2017-01-04 | 上海和辉光电有限公司 | Thin-film packing structure, preparation method and there is the organic light emitting apparatus of this structure |
| CN106967125A (en) * | 2017-05-05 | 2017-07-21 | 苏州大学 | Glycol containing ferrocene and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 刘卅等: ""含金刚烷聚合物的研究进展"", 《高分子材料科学与工程》 * |
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Application publication date: 20201016 |