CN115232303B - Polymer for black matrix, preparation method and application thereof - Google Patents
Polymer for black matrix, preparation method and application thereof Download PDFInfo
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- CN115232303B CN115232303B CN202210447167.7A CN202210447167A CN115232303B CN 115232303 B CN115232303 B CN 115232303B CN 202210447167 A CN202210447167 A CN 202210447167A CN 115232303 B CN115232303 B CN 115232303B
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- polymer
- bis
- dianhydride
- black matrix
- dihydroxy
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- 229920000642 polymer Polymers 0.000 title claims abstract description 113
- 239000011159 matrix material Substances 0.000 title claims abstract description 45
- 238000002360 preparation method Methods 0.000 title claims abstract description 26
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims abstract description 43
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 42
- GUAACGKXPUGLAQ-UHFFFAOYSA-N 2,4,5,7-tetraamino-1,8-dihydroxyanthracene-9,10-dione Chemical compound NC1=C(C=2C(C3=C(C(=CC(=C3C(C=2C(=C1)N)=O)N)N)O)=O)O GUAACGKXPUGLAQ-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000000178 monomer Substances 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 27
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims abstract description 16
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000004985 diamines Chemical class 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims description 16
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical group NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 8
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 8
- 229940018564 m-phenylenediamine Drugs 0.000 claims description 8
- 150000007530 organic bases Chemical class 0.000 claims description 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 6
- IAWQUHCVFXQBMC-UHFFFAOYSA-N 1,3-benzoxazol-5-amine Chemical compound NC1=CC=C2OC=NC2=C1 IAWQUHCVFXQBMC-UHFFFAOYSA-N 0.000 claims description 5
- LBPVOEHZEWAJKQ-UHFFFAOYSA-N 3-[4-(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 LBPVOEHZEWAJKQ-UHFFFAOYSA-N 0.000 claims description 5
- JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 claims description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 5
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 4
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims description 4
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 claims description 4
- ZJYIRVSPPOOPCL-UHFFFAOYSA-N 1,3-benzoxazol-6-amine Chemical compound NC1=CC=C2N=COC2=C1 ZJYIRVSPPOOPCL-UHFFFAOYSA-N 0.000 claims description 3
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 claims description 3
- UMGYJGHIMRFYSP-UHFFFAOYSA-N 2-(4-aminophenyl)-1,3-benzoxazol-5-amine Chemical compound C1=CC(N)=CC=C1C1=NC2=CC(N)=CC=C2O1 UMGYJGHIMRFYSP-UHFFFAOYSA-N 0.000 claims description 3
- IBKFNGCWUPNUHY-UHFFFAOYSA-N 2-(4-aminophenyl)-1,3-benzoxazol-6-amine Chemical compound C1=CC(N)=CC=C1C1=NC2=CC=C(N)C=C2O1 IBKFNGCWUPNUHY-UHFFFAOYSA-N 0.000 claims description 3
- XAFOTXWPFVZQAZ-UHFFFAOYSA-N 2-(4-aminophenyl)-3h-benzimidazol-5-amine Chemical compound C1=CC(N)=CC=C1C1=NC2=CC=C(N)C=C2N1 XAFOTXWPFVZQAZ-UHFFFAOYSA-N 0.000 claims description 3
- MESFSCWCECYZNL-UHFFFAOYSA-N 2-amino-5-[3-(4-amino-3-hydroxyphenoxy)phenoxy]phenol Chemical compound C1=C(O)C(N)=CC=C1OC1=CC=CC(OC=2C=C(O)C(N)=CC=2)=C1 MESFSCWCECYZNL-UHFFFAOYSA-N 0.000 claims description 3
- ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-UHFFFAOYSA-N 0.000 claims description 3
- WUPRYUDHUFLKFL-UHFFFAOYSA-N 4-[3-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(OC=2C=CC(N)=CC=2)=C1 WUPRYUDHUFLKFL-UHFFFAOYSA-N 0.000 claims description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 238000001259 photo etching Methods 0.000 abstract description 4
- 239000011342 resin composition Substances 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 239000003431 cross linking reagent Substances 0.000 description 8
- 239000011651 chromium Substances 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 6
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 5
- 229910052804 chromium Inorganic materials 0.000 description 5
- YYOOOMNEONKALI-UHFFFAOYSA-N 1,8-dihydroxy-2,4,5,7-tetranitroanthracene-9,10-dione Chemical compound O=C1C2=C([N+]([O-])=O)C=C([N+]([O-])=O)C(O)=C2C(=O)C2=C1C([N+]([O-])=O)=CC([N+]([O-])=O)=C2O YYOOOMNEONKALI-UHFFFAOYSA-N 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- QBPFLULOKWLNNW-UHFFFAOYSA-N chrysazin Chemical compound O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O QBPFLULOKWLNNW-UHFFFAOYSA-N 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- 230000001546 nitrifying effect Effects 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 238000011056 performance test Methods 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- GJCHQJDEYFYWER-UHFFFAOYSA-N 1,8-dihydroxy-4,5-dinitroanthracene-9,10-dione Chemical compound O=C1C2=C([N+]([O-])=O)C=CC(O)=C2C(=O)C2=C1C([N+]([O-])=O)=CC=C2O GJCHQJDEYFYWER-UHFFFAOYSA-N 0.000 description 2
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 230000002744 anti-aggregatory effect Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000001459 lithography Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- -1 oxime ester Chemical class 0.000 description 2
- 238000002310 reflectometry Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- CQMIJLIXKMKFQW-UHFFFAOYSA-N 4-phenylbenzene-1,2,3,5-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C(O)=O)=C1C1=CC=CC=C1 CQMIJLIXKMKFQW-UHFFFAOYSA-N 0.000 description 1
- 229940076442 9,10-anthraquinone Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/32—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from aromatic diamines and aromatic dicarboxylic acids with both amino and carboxylic groups aromatically bound
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/265—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from at least two different diamines or at least two different dicarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/28—Preparatory processes
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
The invention discloses a polymer for a black matrix, which is prepared by reacting dianhydride monomer with hydroxyethyl methacrylate to obtain an intermediate, and then reacting the intermediate, diamine monomer, triethylamine and 1, 8-dihydroxy-2, 4,5, 7-tetramino-9, 10-anthraquinone under the action of a catalyst. The polymer provided by the invention has unique structural characteristics, has good mechanical and thermal properties and photoetching properties, and can better meet the requirements of the current industry on the performance of a black matrix when being applied to the black matrix. Meanwhile, the invention also discloses a preparation method and application of the polymer, wherein the preparation method has simple process and is convenient for industrialized popularization and application. The application of the polymer not only provides a new polymer choice for the black matrix, but also can obviously improve the mechanical and thermal properties of the black matrix.
Description
Technical Field
The invention relates to a polymer for a black matrix, in particular to a polymer for an intrinsic resin black matrix, a preparation method and application thereof.
Background
A Black Matrix (Black Matrix) is a negative photoresist of Black dispersed pigment, and currently, a Black Matrix containing carbon Black is widely used in flat panel displays, and is generally disposed at the gaps between the stripes and the dots of a color filter, and the Black Matrix mainly has the following functions: 1. the black matrix resist must have a high Optical Density (Optical Density) to prevent light leakage; 2. the color pixels are separated, so that mutual interference among the color pixels is prevented, and the image contrast is improved; 3. preventing generation of light leakage current; 4. preventing the writing of background light from causing low contrast.
With the rapid development of the LCD industry, the requirements of black matrixes are also increasing. In the color filter, the black matrix plays a role of shielding light and constructing a frame for the red, green and blue three primary color resists to be coated later, so that higher requirements are placed on the performance of the black matrix.
Early black matrices were based on inorganic chromium (Cr), and the benefits of using a chromium-based black matrix were higher optical density and greater material stability. Chromium-based black matrices have many disadvantages such as high cost, complex manufacturing process, poor adhesion, high reflectivity, and complex manufacturing process and potential environmental problems. To solve these problems caused by chromium, the black matrix is shifted from chromium-based to a resin-based doped with a black dye. The film made of the resin-based black matrix is applied to a color filter of a liquid crystal display, has the characteristics of lower reflectivity than that of chromium oxide and lower environmental pressure of a process developer, but the introduction of a carbon material and an organic dye obviously reduces the electrical insulation performance of the black matrix, and the mechanical performance of the black matrix can be inevitably damaged due to uneven distribution, and the heat resistance of the black matrix can be obviously reduced due to poor heat resistance of the organic dye.
Therefore, developing an intrinsic resin black matrix to avoid the above-mentioned drawbacks and to meet the current requirements of the industry for black matrices is a highly desirable goal for those skilled in the art.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a polymer for a black matrix, which has better mechanical and thermal properties and photoetching properties. Meanwhile, the invention also provides a preparation method and application of the polymer.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows: a polymer is prepared by reacting dianhydride monomer with hydroxyethyl methacrylate to obtain an intermediate, and then reacting the intermediate, organic base, diamine monomer and 1, 8-dihydroxy-2, 4,5, 7-tetramino-9, 10-anthraquinone under the action of a catalyst.
The polymer is prepared by reacting dianhydride monomer and hydroxyethyl methacrylate in a solvent to obtain an intermediate, and then reacting the obtained intermediate with diamine monomer and 1, 8-dihydroxy-2, 4,5, 7-tetraamino-9, 10-anthraquinone under the action of a catalyst.
As a preferred embodiment of the polymer according to the invention, the dianhydride monomer is 3,4' -diphenyl ether tetracarboxylic dianhydride, 4' -biphenyl tetracarboxylic dianhydride, 3', at least one of 4,4' -benzophenone tetracarboxylic dianhydride, 2' -bis (3, 4-dicarboxylic acid) hexafluoropropane dianhydride, 2, 3',4' -biphenyl tetracarboxylic dianhydride, 3',4' -diphenyl sulfone tetracarboxylic dianhydride, naphthalene-1, 4,5, 8-tetracarboxylic dianhydride, and diphenyl sulfide dianhydride. As a more preferred embodiment of the polymer of the present invention, the dianhydride monomer is 3,4' -diphenyl ether tetracarboxylic dianhydride.
As a preferred embodiment of the polymer according to the invention, the intermediate has the formula:
as a preferred embodiment of the polymer of the present invention, the organic base is at least one of triethylamine, methylamine, ethylamine, dimethylamine, and diethylamine. As a more preferred embodiment of the polymer according to the present invention, the organic base is triethylamine.
As a preferred embodiment of the polymer according to the invention, the diamine monomer is m-phenylenediamine, p-phenylenediamine, 4 '-diaminodiphenyl ether, 4' -diaminodiphenyl ether, 3,4 '-diaminodiphenyl ether, 4' -diaminodiphenyl ketone, 4 '-diaminodiphenyl methane, 1, 3-bis (4-aminophenoxy) benzene, 1, 4-bis (4-aminophenoxy) benzene, 4' -diamino-2, 2 '-dimethylbiphenyl at least one of 2- (4-aminophenyl) -5-aminobenzoxazole, 2- (4-aminophenyl) -5-aminobenzimidazole, 1, 4-bis (3-aminophenoxy) benzene, 1, 3-bis (3-hydroxy-4-aminophenoxy) benzene, 2- (4-aminophenyl) -6-aminobenzoxazole, 2-p-phenyl-bis (5-aminobenzoxazole), 2' -p-phenyl-bis (6-aminobenzoxazole). As a more preferred embodiment of the polymer of the present invention, the diamine monomer is m-phenylenediamine.
As a preferred embodiment of the polymer according to the invention, the catalyst is SOCl 2 、AlCl 3 、BF 3 、SbCl 5 、FeBr 3 、FeCl 3 、SnCl 4 、TiCl 4 、ZnCl 2 At least one of them. As a more preferred embodiment of the polymer of this method, the catalyst is SOCl 2 。
As a preferred embodiment of the polymer of the present invention, the dianhydride monomer is 3,4' -diphenyl ether tetracarboxylic dianhydride and the diamine monomer is m-phenylenediamine.
The structural formula of the 1,8 dihydroxy-2, 4,5,7 tetramino-9, 10-anthraquinone is as follows:
as a preferred embodiment of the polymer according to the invention, the polymer has the formula:
wherein n is an integer of 10 to 50.
As a more preferable embodiment of the polymer of the present invention, in the structural formula of the polymer, n is an integer of 20 to 40.
Meanwhile, another object of the present invention is to provide a method for preparing the polymer as described above, which has simple process steps and is convenient for industrial application, and in order to achieve the purpose, the present invention adopts the following technical scheme: a method of preparing a polymer, the method comprising the steps of:
(1) Taking dianhydride monomer and hydroxyethyl methacrylate to react in a solvent 1 to obtain an intermediate;
(2) And (2) adding diamine monomer, organic alkali 1,8 dihydroxy-2, 4,5,7 tetraamino-9, 10-anthraquinone and the intermediate obtained in the step (1) into a solvent 2, and then adding a catalyst for reaction to obtain the polymer.
As a preferred embodiment of the method for preparing a polymer according to the present invention, the molar ratio of the dianhydride monomer to the hydroxyethyl methacrylate in the step (1) is 1:2, and the reaction temperature is 40 to 80 ℃.
As a preferred embodiment of the process for the preparation of a polymer according to the invention, the reaction temperature in step (1) is 70 ℃.
As a preferred embodiment of the method for producing a polymer according to the present invention, the reaction conditions in the step (1) are: oil bath at 70 ℃ under nitrogen atmosphere.
As a preferred embodiment of the method for producing a polymer according to the present invention, the dianhydride monomer in the step (1) is 3,4' -diphenyl ether tetracarboxylic dianhydride, 4' -biphenyl tetracarboxylic dianhydride, 3', at least one of 4,4' -benzophenone tetracarboxylic dianhydride, 2' -bis (3, 4-dicarboxylic acid) hexafluoropropane dianhydride, 2, 3',4' -biphenyl tetracarboxylic dianhydride, 3',4' -diphenyl sulfone tetracarboxylic dianhydride, naphthalene-1, 4,5, 8-tetracarboxylic dianhydride, and diphenyl sulfide dianhydride. As a more preferable embodiment of the method for producing a polymer according to the present method, the dianhydride monomer in the step (1) is 3,4' -diphenyl ether tetracarboxylic dianhydride.
As a preferred embodiment of the method for preparing a polymer according to the present invention, the molar ratio of diamine monomer, 1,8 dihydroxy-2, 4,5,7 tetramino-9, 10-anthraquinone and intermediate in the step (2) is 1:1:1, and the reaction temperature is 0 to 5 ℃.
As a preferred embodiment of the method for producing a polymer according to the present invention, the diamine monomer in the step (2) is m-phenylenediamine, p-phenylenediamine, 4 '-diaminobiphenyl, 4' -diaminodiphenyl ether, 3,4 '-diaminodiphenyl ether, 4' -diaminodiphenyl ketone, 4 '-diaminodiphenyl methane, 1, 3-bis (4-aminophenoxy) benzene, 1, 4-bis (4-aminophenoxy) benzene, 4' -diamino-2, 2 '-dimethylbiphenyl at least one of 2- (4-aminophenyl) -5-aminobenzoxazole, 2- (4-aminophenyl) -5-aminobenzimidazole, 1, 4-bis (3-aminophenoxy) benzene, 1, 3-bis (3-hydroxy-4-aminophenoxy) benzene, 2- (4-aminophenyl) -6-aminobenzoxazole, 2-p-phenyl-bis (5-aminobenzoxazole), 2' -p-phenyl-bis (6-aminobenzoxazole). As a more preferable embodiment of the method for producing a polymer of the present invention, the diamine monomer in the step (2) is m-phenylenediamine.
As a preferred embodiment of the method for preparing a polymer according to the present invention, the dianhydride monomer in the step (1) is 3,4' -diphenyl ether tetracarboxylic dianhydride; the diamine monomer in the step (2) is p-phenylenediamine.
As a preferred embodiment of the method for preparing a polymer according to the present invention, the intermediate obtained in the step (1) has a structural formula:
as a preferred embodiment of the method for preparing the polymer of the present invention, the 1, 8-dihydroxy-2, 4,5, 7-tetramino-9, 10-anthraquinone in the step (2) is prepared by the following method: nitrifying 1, 8-dihydroxy-9, 10-anthraquinone to 1, 8-dihydroxy-2, 4,5, 7-tetranitro-9, 10-anthraquinone in the presence of concentrated sulfuric acid and concentrated nitric acid, and then reducing the nitro group to amino group to obtain 1, 8-dihydroxy-2, 4,5, 7-tetraamino-9, 10-anthraquinone.
As a preferred embodiment of the method for preparing the polymer of the present invention, the 1, 8-dihydroxy-2, 4,5, 7-tetramino-9, 10-anthraquinone in the step (2) is prepared by the following method: nitrifying 1, 8-dihydroxy-4, 5-dinitro-9, 10-anthraquinone to 1, 8-dihydroxy-2, 4,5, 7-tetranitro-9, 10-anthraquinone in the presence of concentrated sulfuric acid and concentrated nitric acid, and then reducing the nitro group to amino group to obtain 1, 8-dihydroxy-2, 4,5, 7-tetraamino-9, 10-anthraquinone.
As a preferred embodiment of the method for producing a polymer of the present invention, the solvent 1 and the solvent 2 are each independently selected from at least one of N-methylpyrrolidone, N-dimethylformamide, N-dimethylacetamide, dimethylsulfoxide, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, tetrahydrofuran; the organic base in the step (2) is at least one of triethylamine, methylamine, ethylamine, dimethylamine and diethylamine; the catalyst in the step (2) is SOCl 2 、AlCl 3 、BF 3 、SbCl 5 、FeBr 3 、FeCl 3 、SnCl 4 、TiCl 4 、ZnCl 2 At least one of them.
As a preferred embodiment of the method for producing a polymer according to the present invention, the solvent 1 and the solvent 2 are both N-methylpyrrolidone.
As a preferred embodiment of the method for producing a polymer according to the present invention, the organic base in the step (2) is triethylamine and the catalyst is SOCl 2 。
Finally, the invention also provides the use of a polymer as described above for the preparation of a black matrix.
When the polymer is used for preparing the black matrix, the black photosensitive resin composition is prepared by mixing the polymer with substances including but not limited to a photoinitiator, a cross-linking agent, a solvent and the like and uniformly stirring. The photoinitiator in the black photosensitive resin composition comprises, but is not limited to, oxime ester photoinitiators such as oxe-01, oxe-02, pbg-304, pbg and the like, the crosslinking agent is preferably acrylic acid system photosensitive crosslinking agent such as tetraethyleneglycol dimethacrylate and the solvent is an organic solvent. In the black photosensitive resin composition, the mass ratio of the polymer, the photoinitiator and the crosslinking agent is preferably as follows: and (2) polymer: and (3) a photoinitiator: crosslinking agent=100 (3 to 5): (5-10). In the black photosensitive resin composition, the solvent is added in an amount of 150 to 300ml per 100g of polymer.
The black photosensitive resin composition may further contain, if necessary, at least one of additives such as a surfactant, a filler, an adhesion promoter, a bridging agent, an antioxidant, and an anti-aggregation agent.
When the black photosensitive resin composition is prepared, the polymer is mixed with other components contained in the black photosensitive resin composition, and then stirred, for example, in a planetary gravity stirrer (Mianyang Shinuo technology Co., ltd.) to be in a solution state after being uniformly stirred and mixed, thereby obtaining the black photosensitive resin composition.
In preparing the black matrix, the polymer of the present invention may be prepared, for example, by the following method: the black photosensitive resin composition is coated on a substrate, then prebaked, exposed on photoetching equipment, developed and then post-baked to obtain a black matrix.
In the preparation process of the black matrix, the used equipment is, for example: spin coating on a substrate on an RC-150 spin coater (Suzhou Mei semiconductor technology Co., ltd.), pre-baking on a PHP-8 hotplate (Suzhou Mei semiconductor technology Co., ltd.), exposing on URE-2000/35 lithography equipment (institute of photoelectric technology, china academy of sciences), developing, and post-baking on a PHP-8 hotplate (Suzhou Mei semiconductor technology Co., ltd.).
The above-mentioned pre-baking treatment is performed at a temperature of 70 ℃ to 110 ℃ for 1 minute to 15 minutes. After the pre-baking, the above-mentioned coating film is exposed to light under a prescribed reticle, and then immersed in a developer at a temperature of 23.+ -. 2 ℃ for 1 second to 5 minutes to remove unnecessary portions to form a specific pattern. The light used for exposure is preferably ultraviolet rays such as g-line, h-line or i-line, and the ultraviolet irradiation device may be a (ultra) high pressure mercury lamp or a metal halogen lamp.
The polymer provided by the invention has unique structural characteristics, has good mechanical and thermal properties and photoetching properties, and can better meet the requirements of the current industry on the performance of a black matrix when being applied to the black matrix.
In the preparation method of the polymer, the raw materials are convenient and easy to obtain, the preparation steps and the process conditions are simple, and the industrialized popularization is convenient.
The application of the polymer in preparing the black matrix not only provides a new polymer choice for the black matrix, but also can obviously improve the mechanical and thermal properties of the black matrix.
Drawings
FIG. 1 is a structural formula of one embodiment of a polymer according to the present invention;
FIG. 2 is a structural reaction scheme of one embodiment of a method of preparing a polymer according to the present invention;
FIG. 3 is a graph of the thermal performance test results of one embodiment of the polymer of the present invention;
FIG. 4 is a graph of lithographic performance testing for one embodiment of the polymer of the present invention;
FIG. 5 is a graph of a lithographic performance test of another embodiment of a polymer according to the present invention;
FIG. 6 is a graph of a lithographic performance test of another embodiment of the polymer of the present invention.
Detailed Description
For a better description of the objects, technical solutions and advantages of the present invention, the present invention will be further described with reference to the accompanying drawings and specific embodiments.
The structural formula of 1,8 dihydroxy-2, 4,5,7 tetramino-9, 10-anthraquinone described in the examples below is:
the 1,8 dihydroxy-2, 4,5,7 tetramino-9, 10-anthraquinone is prepared by the following method: nitrifying 1, 8-dihydroxy-9, 10-anthraquinone to 1, 8-dihydroxy-2, 4,5,7 tetranitro-9, 10-anthraquinone in the presence of concentrated sulfuric acid and concentrated nitric acid, and then reducing the nitro to amino to obtain 1, 8-dihydroxy-2, 4,5,7 tetraamino-9, 10-anthraquinone; or is prepared by the following method: nitrifying 1, 8-dihydroxy-4, 5-dinitro-9, 10-anthraquinone to 1, 8-dihydroxy-2, 4,5, 7-tetranitro-9, 10-anthraquinone in the presence of concentrated sulfuric acid and concentrated nitric acid, and then reducing the nitro group to amino group to obtain 1, 8-dihydroxy-2, 4,5, 7-tetraamino-9, 10-anthraquinone.
Example 1
An embodiment of the polymer of the present invention, the structural formula of the polymer is shown in fig. 1, and the preparation method of the polymer of the present embodiment includes the following steps:
(1) Taking a molar ratio of 1:2, adding 3,4' -diphenyl ether tetracarboxylic dianhydride and hydroxyethyl methacrylate into N-methyl pyrrolidone, and carrying out oil bath reaction at 70 ℃ under nitrogen atmosphere to obtain an intermediate;
(2) Adding p-phenylenediamine, triethylamine and 1, 8-dihydroxy-2, 4,5, 7-tetramino-9, 10-anthraquinone to the intermediate in step (1), followed by adding SOCl 2 Reacting at 0 ℃ to obtain the polymer of the embodiment; the molar ratio of the intermediate, the p-phenylenediamine and the 1,8 dihydroxy-2, 4,5,7 tetramino-9, 10-anthraquinone is 1:1:1.
The structural reaction formula of the polymer in this example is shown in fig. 2.
Example 2
An embodiment of the polymer of the present invention, the preparation method of the polymer of the present embodiment includes the following steps:
(1) Taking a molar ratio of 1:2, adding the 4,4' -biphenyl tetracarboxylic dianhydride and hydroxyethyl methacrylate into N, N-dimethylformamide, and carrying out oil bath reaction at 60 ℃ under nitrogen atmosphere to obtain an intermediate;
(2) Adding m-phenylenediamine, triethylamine and 1, 8-dihydroxy-2, 4,5, 7-tetramino-9, 10-anthraquinone to the intermediate in the step (1), and then adding SOCl 2 Reacting at 1 ℃ to obtain the polymer of the embodiment; the molar ratio of the intermediate to the m-phenylenediamine to the 1,8 dihydroxy-2, 4,5,7 tetramino-9, 10-anthraquinone is 1:1:1.
Example 3
An embodiment of the polymer of the present invention, the preparation method of the polymer of the present embodiment includes the following steps:
(1) Taking a molar ratio of 1:2 naphthalene-1, 4,5, 8-tetracarboxylic dianhydride and hydroxyethyl methacrylate are added into N, N-dimethylacetamide to react in an oil bath at 80 ℃ under the nitrogen atmosphere to obtain an intermediate;
(2) Adding 4,4' -diaminobiphenyl, triethylamine and 1, 8-dihydroxy-2, 4,5, 7-tetramino-9, 10-anthraquinone to the intermediate in step (1), and then adding SOCl 2 Reacting at 0 ℃ to obtain the polymer of the embodiment; the molar ratio of the intermediate, 4' -diaminobiphenyl and 1,8 dihydroxy-2, 4,5,7 tetramino-9, 10-anthraquinone is 1:1:1.
Example 4
An embodiment of the polymer of the present invention, the preparation method of the polymer of the present embodiment includes the following steps:
(1) Taking a molar ratio of 1:2 diphenyl sulfide dianhydride and hydroxyethyl methacrylate are added into dimethyl sulfoxide, and are subjected to oil bath reaction at 50 ℃ under nitrogen atmosphere to obtain an intermediate;
(2) Adding 1, 4-bis (4-aminophenoxy) benzene, triethylamine and 1, 8-dihydroxy-2, 4,5, 7-tetramino-9, 10-anthraquinone to the intermediate in step (1), followed by adding SOCl 2 Reacting at 2 ℃ to obtain the polymer of the embodiment; the molar ratio of the intermediate, 1, 4-bis (4-aminophenoxy) benzene and 1, 8-dihydroxy-2, 4,5, 7-tetramino-9, 10-anthraquinone is 1:1:1.
Example 5
An embodiment of the polymer of the present invention, the preparation method of the polymer of the present embodiment includes the following steps:
(1) Taking a molar ratio of 1:2, 3',4' -biphenyl tetracarboxylic dianhydride and hydroxyethyl methacrylate are added into N-ethyl-2-pyrrolidone, and are subjected to oil bath reaction at 55 ℃ under nitrogen atmosphere to obtain an intermediate;
(2) Adding 2, 2-p-phenyl-bis (5-aminobenzoxazole), triethylamine and 1, 8-dihydroxy-2, 4,5, 7-tetramino-9, 10-anthraquinone to the intermediate of step (1), and then adding SOCl 2 Reacting at 0 ℃ to obtain the polymer of the embodiment; the molar ratio of the intermediate, the 2, 2-p-phenyl-bis (5-aminobenzoxazole) and the 1,8 dihydroxy-2, 4,5,7 tetramino-9, 10-anthraquinone is 1:1:1.
Example 6
An embodiment of the polymer of the present invention, the preparation method of the polymer of the present embodiment includes the following steps:
(1) Taking a molar ratio of 1:2, 2' -bis (3, 4-dicarboxylic acid) hexafluoropropane dianhydride and hydroxyethyl methacrylate are added into tetrahydrofuran to react in an oil bath at 75 ℃ under nitrogen atmosphere to obtain an intermediate;
(2) Adding 4,4' -diaminodiphenyl ether, triethylamine and 1, 8-dihydroxy-2, 4,5, 7-tetramino-9, 10-anthraquinone to the intermediate in the step (1), and then adding SOCl 2 Reacting at 4 ℃ to obtain the polymer of the embodiment; the molar ratio of the intermediate, 4' -diaminodiphenyl ether and 1,8 dihydroxy-2, 4,5,7 tetramino-9, 10-anthraquinone is 1:1:1.
Example 7
An embodiment of the polymer of the present invention, the preparation method of the polymer of the present embodiment includes the following steps:
(1) Taking a molar ratio of 1:2, adding 3,4' -diphenyl ether tetracarboxylic dianhydride and hydroxyethyl methacrylate into N-methyl-2-pyrrolidone, and carrying out oil bath reaction at 60 ℃ under nitrogen atmosphere to obtain an intermediate;
(2) Adding 1, 4-bis (3-aminophenoxy) benzene, triethylamine and 1,8 dihydroxy-2, 4,5,7 tetramino to the intermediate of step (1)-9, 10-anthraquinone and then SOCl is added 2 Reacting at 5 ℃ to obtain the polymer of the embodiment; the molar ratio of the intermediate, 1, 4-bis (3-aminophenoxy) benzene and 1, 8-dihydroxy-2, 4,5, 7-tetramino-9, 10-anthraquinone is 1:1:1.
Example 8
An embodiment of the polymer of the present invention, the preparation method of the polymer of the present embodiment includes the following steps:
(1) Taking a molar ratio of 1:2, adding 3,3',4' -benzophenone tetracarboxylic dianhydride and hydroxyethyl methacrylate into N-methyl pyrrolidone, and carrying out oil bath reaction at 70 ℃ under nitrogen atmosphere to obtain an intermediate;
(2) Adding p-phenylenediamine, triethylamine and 1, 8-dihydroxy-2, 4,5, 7-tetramino-9, 10-anthraquinone to the intermediate in step (1), followed by adding SOCl 2 Reacting at 3 ℃ to obtain the polymer of the embodiment; the molar ratio of the intermediate, the p-phenylenediamine and the 1,8 dihydroxy-2, 4,5,7 tetramino-9, 10-anthraquinone is 1:1:1.
Example 9
One example of a black matrix prepared using the polymers of the present invention
1. Preparation of black photosensitive resin composition
The black photosensitive resin composition of this example comprises the following components by weight: 100g of the polymer in the embodiment 1, 3-5 g of a photoinitiator, 5-10 g of a crosslinking agent and 150-300 ml of a solvent.
In this embodiment, the photoinitiator is an oxime ester photoinitiator, such as oxe-01, oxe-02, pbg-304, pbg, 314, etc., the crosslinking agent is an acrylic photosensitive crosslinking agent, such as tetraethyleneglycol dimethacrylate, and the solvent is an organic solvent.
In the preparation of the black photosensitive resin composition of this example, the polymer and other components are mixed and stirred, for example, in a planetary gravity stirrer (Mianyang Shino technology Co., ltd.) and then stirred and mixed uniformly to form a solution, thereby obtaining the black photosensitive resin composition.
The black photosensitive resin composition may further contain, if necessary, at least one of additives such as a surfactant, a filler, an adhesion promoter, a bridging agent, an antioxidant, and an anti-aggregation agent, and may be selected by those skilled in the art according to actual needs.
2. Preparation of black matrix
The black matrix of the embodiment is prepared by the following method:
the black photosensitive resin composition of example 9 was spin-coated on a substrate on an RC-150 spin coater (Suzhou Mei-FIG. semiconductor technology Co., ltd.), pre-baked on a PHP-8 hotplate (Suzhou Mei-FIG. semiconductor technology Co., ltd.), exposed on a URE-2000/35 lithography apparatus (institute of photoelectric technology, china academy of sciences), developed, and post-baked on a PHP-8 hotplate (Suzhou Mei-FIG. semiconductor technology Co., ltd.) to obtain the black matrix of this example.
In this embodiment, the pre-baking treatment is performed at a temperature of 70 ℃ to 110 ℃ for 1 minute to 15 minutes. After the pre-baking, the above-mentioned coating film is exposed to light under a prescribed reticle, and then immersed in a developer at a temperature of 23.+ -. 2 ℃ for 1 second to 5 minutes to remove unnecessary portions to form a specific pattern. The light used for exposure is preferably ultraviolet rays such as g-line, h-line or i-line, and the ultraviolet irradiation device may be a (ultra) high pressure mercury lamp or a metal halogen lamp.
Example 11
Performance test of the polymers of the invention.
1. Mechanical and thermal properties of black matrix prepared by the polymer
1. Mechanical properties of the black matrix obtained by the polymer
The black matrices were prepared as test groups 1 to 8 using the polymers described in examples 1 to 8, respectively, according to the method of example 9, and the content of the remaining components and the preparation process were the same except for the different polymers in the preparation process of the black matrices of test groups 1 to 8. The black matrixes prepared in the test groups 1 to 8 are used as test objects, and the mechanical properties of the black matrixes obtained in each group are tested by the specific test method: the test was performed using a DMA tester (model: TA Q800), and the sample film was stretched from 0N at 25℃to obtain elongation at break (. Epsilon.) and tensile strength (. Sigma.).
The test results are shown in Table 1.
Table 1 mechanical test results of the black matrices described in test groups 1 to 8
As can be seen from the results in Table 1, the black matrices prepared from the polymers according to examples 1 to 8 of the present invention all have good mechanical properties.
2. Thermal properties of black matrices prepared from the polymers of the present invention
The black matrix (example 9) prepared from the polymer described in example 1 was used as a test object to test its thermal properties by the following specific test method: using a TMA tester (model: TA Q400) to test, heating the sample film from 25 ℃ to 400 ℃, and taking CTE in the range of 50-150 ℃; taking the temperature corresponding to the inflection point on the curve as Tg. The test results are shown in FIG. 3.
As can be seen from fig. 3, the black matrix prepared from the polymer of the present invention has good thermal properties.
2. Lithographic properties of the polymers of the invention
The polymer of the present invention was tested for its lithographic properties using the polymer of example 1 as a test object. The specific test procedure is as described in example 10.
The test results are shown in figures 4-6.
Fig. 4-6 show the developed images of the black matrix of the present invention, and it can be seen from fig. 4-6 that the black matrix exhibits good patterning performance in the 15nm-25nm range.
Finally, it should be noted that the above embodiments are only for illustrating the technical solution of the present invention and not for limiting the scope of the present invention, and although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that the technical solution of the present invention may be modified or substituted equally without departing from the spirit and scope of the technical solution of the present invention.
Claims (7)
1. A polymer is characterized in that the polymer is prepared by reacting dianhydride monomer with hydroxyethyl methacrylate to obtain an intermediate, and then reacting the intermediate, organic base, diamine monomer and 1, 8-dihydroxy-2, 4,5, 7-tetramino-9, 10-anthraquinone under the action of a catalyst;
wherein, the structural formula of the intermediate is:
；
wherein the dianhydride monomer is 3,4' -diphenyl ether tetracarboxylic dianhydride, 4' -biphenyl tetracarboxylic dianhydride, 3',4,4' -benzophenone tetracarboxylic dianhydride, 2' -bis (3, 4-dicarboxylic acid) hexafluoropropane dianhydride, 2, 3', at least one of 4' -biphenyl tetracarboxylic dianhydride, 3',4' -diphenyl sulfone tetracarboxylic dianhydride, naphthalene-1, 4,5, 8-tetracarboxylic dianhydride and diphenyl sulfide dianhydride;
wherein, the diamine monomer is m-phenylenediamine, p-phenylenediamine, 4 '-diaminodiphenyl ether, 4' -diaminodiphenyl ether, 3,4 '-diaminodiphenyl ether, 4' -diaminodiphenyl ketone, 4 '-diaminodiphenyl methane, 1, 3-bis (4-aminophenoxy) benzene, 1, 4-bis (4-aminophenoxy) benzene, 4' -diamino-2, 2 '-dimethylbiphenyl at least one of 2- (4-aminophenyl) -5-aminobenzoxazole, 2- (4-aminophenyl) -5-aminobenzimidazole, 1, 4-bis (3-aminophenoxy) benzene, 1, 3-bis (3-hydroxy-4-aminophenoxy) benzene, 2- (4-aminophenyl) -6-aminobenzoxazole, 2-p-phenyl-bis (5-aminobenzoxazole), 2' -p-phenyl-bis (6-aminobenzoxazole);
wherein, the mol ratio of the dianhydride monomer to the hydroxyethyl methacrylate is 1:2;
wherein the molar ratio of diamine monomer, 1,8 dihydroxy-2, 4,5,7 tetraamino-9, 10-anthraquinone and intermediate is 1:1:1.
2. The polymer of claim 1, wherein the polymer has the formula:
；
wherein n is an integer of 10 to 50.
3. A process for the preparation of a polymer as claimed in claim 1 or 2, comprising the steps of:
taking dianhydride monomer and hydroxyethyl methacrylate to react in a solvent 1 to obtain an intermediate;
(2) And (2) adding diamine monomer, organic base, 1,8 dihydroxy-2, 4,5,7 tetraamino-9, 10-anthraquinone and the intermediate obtained in the step (1) into a solvent 2, and then adding a catalyst for reaction to obtain the polymer.
4. The method of producing a polymer according to claim 3, wherein in the step (1), the reaction temperature is 40 to 80 ℃.
5. The method of claim 3, wherein in the step (2), the reaction temperature is 0 to 5 ℃.
6. A method for producing a polymer according to claim 3, wherein the solvent 1 and the solvent 2 are each independently selected from at least one of N-methylpyrrolidone, N-dimethylformamide, N-dimethylacetamide, dimethylsulfoxide, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, tetrahydrofuran; the organic base in the step (2) is at least one of triethylamine, methylamine, ethylamine, dimethylamine and diethylamine; the catalyst in the step (2) is SOCl 2 、AlCl 3 、BF 3 、 SbCl 5 、FeBr 3 、FeCl 3 、SnCl 4 、TiCl 4 、ZnCl 2 At least one of them.
7. Use of a polymer according to claim 1 or 2 for the preparation of a black matrix.
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| JP2010515098A (en) * | 2006-12-26 | 2010-05-06 | エルジー・ケム・リミテッド | Black matrix high-sensitivity photosensitive resin composition for liquid crystal display and black matrix produced using the same |
| CN109867786A (en) * | 2019-02-28 | 2019-06-11 | 常州市尚科新材料有限公司 | Black polyamide thin film and its preparation method and application |
| CN113563212A (en) * | 2021-06-25 | 2021-10-29 | 同济大学 | Anthraquinone derivative tetramine monomer, black intrinsic polyimide derived from anthraquinone derivative tetramine monomer and preparation method of black intrinsic polyimide |
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| CN109988312B (en) * | 2019-04-09 | 2023-04-11 | 深圳先进技术研究院 | Polyamide acid ester, preparation method, negative polyimide composition and application |
| CN115232303B (en) * | 2022-04-19 | 2023-09-15 | 上海交通大学 | Polymer for black matrix, preparation method and application thereof |
| CN116482933A (en) * | 2023-03-31 | 2023-07-25 | 深圳先进电子材料国际创新研究院 | Negative photosensitive polyimide precursor resin composition |
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| JP2010515098A (en) * | 2006-12-26 | 2010-05-06 | エルジー・ケム・リミテッド | Black matrix high-sensitivity photosensitive resin composition for liquid crystal display and black matrix produced using the same |
| CN109867786A (en) * | 2019-02-28 | 2019-06-11 | 常州市尚科新材料有限公司 | Black polyamide thin film and its preparation method and application |
| CN113563212A (en) * | 2021-06-25 | 2021-10-29 | 同济大学 | Anthraquinone derivative tetramine monomer, black intrinsic polyimide derived from anthraquinone derivative tetramine monomer and preparation method of black intrinsic polyimide |
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