WO2023202390A1 - Composition de résine photosensible et procédé de formation de motifs - Google Patents
Composition de résine photosensible et procédé de formation de motifs Download PDFInfo
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- WO2023202390A1 WO2023202390A1 PCT/CN2023/086787 CN2023086787W WO2023202390A1 WO 2023202390 A1 WO2023202390 A1 WO 2023202390A1 CN 2023086787 W CN2023086787 W CN 2023086787W WO 2023202390 A1 WO2023202390 A1 WO 2023202390A1
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- 239000000203 mixture Substances 0.000 title claims abstract description 92
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 92
- 238000000034 method Methods 0.000 title claims abstract description 40
- 238000000059 patterning Methods 0.000 title claims abstract description 12
- 239000000178 monomer Substances 0.000 claims abstract description 92
- 239000002904 solvent Substances 0.000 claims abstract description 29
- 239000000758 substrate Substances 0.000 claims abstract description 29
- 239000002253 acid Substances 0.000 claims abstract description 24
- 229920000642 polymer Polymers 0.000 claims abstract description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 13
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 11
- 239000011737 fluorine Substances 0.000 claims abstract description 11
- 230000005855 radiation Effects 0.000 claims abstract description 5
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 3
- 239000011368 organic material Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 230000008859 change Effects 0.000 claims description 5
- 238000010526 radical polymerization reaction Methods 0.000 claims description 5
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 claims description 4
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 claims description 4
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000002015 acyclic group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 3
- 238000002347 injection Methods 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- 230000008569 process Effects 0.000 description 11
- 239000004020 conductor Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000003086 colorant Substances 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- -1 nonafluorobutyl ether Chemical compound 0.000 description 3
- NOPJRYAFUXTDLX-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-methoxypropane Chemical compound COC(F)(F)C(F)(F)C(F)(F)F NOPJRYAFUXTDLX-UHFFFAOYSA-N 0.000 description 2
- WVRJJXQSRCWPNS-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-1-[2-(1,1,2,2-tetrafluoroethoxy)ethoxy]ethane Chemical compound FC(F)C(F)(F)OCCOC(F)(F)C(F)F WVRJJXQSRCWPNS-UHFFFAOYSA-N 0.000 description 2
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
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- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
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- 150000002894 organic compounds Chemical class 0.000 description 2
- 238000000206 photolithography Methods 0.000 description 2
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- 239000010703 silicon Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 2
- OBQBCHMEIBSHBO-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-propoxyoctane Chemical compound CCCOCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F OBQBCHMEIBSHBO-UHFFFAOYSA-N 0.000 description 1
- QKAGYSDHEJITFV-UHFFFAOYSA-N 1,1,1,2,2,3,4,5,5,5-decafluoro-3-methoxy-4-(trifluoromethyl)pentane Chemical compound FC(F)(F)C(F)(F)C(F)(OC)C(F)(C(F)(F)F)C(F)(F)F QKAGYSDHEJITFV-UHFFFAOYSA-N 0.000 description 1
- TZMQCOROQZMJIS-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)pentane Chemical compound FC(F)(F)C(F)C(F)(F)C(C)OC(F)(F)C(F)C(F)(F)F TZMQCOROQZMJIS-UHFFFAOYSA-N 0.000 description 1
- SQEGLLMNIBLLNQ-UHFFFAOYSA-N 1-ethoxy-1,1,2,3,3,3-hexafluoro-2-(trifluoromethyl)propane Chemical compound CCOC(F)(F)C(F)(C(F)(F)F)C(F)(F)F SQEGLLMNIBLLNQ-UHFFFAOYSA-N 0.000 description 1
- YRGYOFYTTFLPQM-UHFFFAOYSA-N 2,3,3,4,4-pentafluoro-2,5-bis(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-5-methoxyoxolane Chemical compound COC1(OC(F)(C(F)(C(F)(F)F)C(F)(F)F)C(F)(F)C1(F)F)C(F)(C(F)(F)F)C(F)(F)F YRGYOFYTTFLPQM-UHFFFAOYSA-N 0.000 description 1
- DJXNLVJQMJNEMN-UHFFFAOYSA-N 2-[difluoro(methoxy)methyl]-1,1,1,2,3,3,3-heptafluoropropane Chemical compound COC(F)(F)C(F)(C(F)(F)F)C(F)(F)F DJXNLVJQMJNEMN-UHFFFAOYSA-N 0.000 description 1
- FNUBKINEQIEODM-UHFFFAOYSA-N 3,3,4,4,5,5,5-heptafluoropentanal Chemical compound FC(F)(F)C(F)(F)C(F)(F)CC=O FNUBKINEQIEODM-UHFFFAOYSA-N 0.000 description 1
- CDXFIRXEAJABAZ-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CDXFIRXEAJABAZ-UHFFFAOYSA-N 0.000 description 1
- HHBBIOLEJRWIGU-UHFFFAOYSA-N 4-ethoxy-1,1,1,2,2,3,3,4,5,6,6,6-dodecafluoro-5-(trifluoromethyl)hexane Chemical compound CCOC(F)(C(F)(C(F)(F)F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)F HHBBIOLEJRWIGU-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910018286 SbF 6 Inorganic materials 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- VZPPHXVFMVZRTE-UHFFFAOYSA-N [Kr]F Chemical compound [Kr]F VZPPHXVFMVZRTE-UHFFFAOYSA-N 0.000 description 1
- 239000011358 absorbing material Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- ISQINHMJILFLAQ-UHFFFAOYSA-N argon hydrofluoride Chemical compound F.[Ar] ISQINHMJILFLAQ-UHFFFAOYSA-N 0.000 description 1
- 238000003491 array Methods 0.000 description 1
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- CXKCTMHTOKXKQT-UHFFFAOYSA-N cadmium oxide Inorganic materials [Cd]=O CXKCTMHTOKXKQT-UHFFFAOYSA-N 0.000 description 1
- CFEAAQFZALKQPA-UHFFFAOYSA-N cadmium(2+);oxygen(2-) Chemical compound [O-2].[Cd+2] CFEAAQFZALKQPA-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
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- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910021389 graphene Inorganic materials 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000011165 process development Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
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- 230000004044 response Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000004984 smart glass Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- ZDCRNXMZSKCKRF-UHFFFAOYSA-N tert-butyl 4-(4-bromoanilino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=CC=C(Br)C=C1 ZDCRNXMZSKCKRF-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
Definitions
- the present disclosure relates to a photoresist composition and a method of patterning a device using the photoresist composition.
- OLED organic light-emitting diode
- LCD organic light-emitting diode
- OLED light-emitting diode
- OLED can be used in display devices, such as TV screens, computer screens, mobile phones, tablets, smart watches and smart glasses.
- OLED devices are self-illuminating devices and have been widely discussed due to their brightness, better visibility, and ability to display clearer images than LCD devices.
- a photoresist composition includes: a polymer composed of a first monomer and a first Polymerized from two monomers, the first monomer is an acrylic monomer containing a polymerizable group and a fluorine-containing group, and the second monomer is an acrylic monomer containing a polymerizable group and a reactive group that can change the solubility.
- a group of monomers a photobase generator; a thermal acid generator; and a fluorinated solvent.
- a method of patterning a device includes forming a photoresist composition layer on a substrate of a device, the photoresist composition layer including a photoresist composition, the The photoresist composition includes a polymer polymerized from a first monomer and a second monomer, wherein the first monomer is an acrylic monomer containing a polymerizable group and a fluorine-containing group.
- the second monomer is a monomer containing a polymerizable group and a solubility-changing reactive group, a photobase generator, a thermal acid generator, and a first fluorinated solvent; exposing the photoresist composition subjecting the photoresist composition layer to patterned radiation to form an exposed area and an unexposed area; baking the exposed area and the unexposed area; and removing the photoresist composition layer
- the exposure area forms a development structure.
- Figure 1 is a flowchart of a method of patterning a device in accordance with certain embodiments of the present disclosure.
- Figure 2 is a top view of a device according to a method of patterning a device in accordance with certain embodiments of the present disclosure.
- 3-10 are cross-sectional views of a device structure during various stages according to certain embodiments of the present disclosure.
- a key challenge in OLED devices is to pattern arrays of red, green, and blue pixels, and each pixel contains easily damaged and sensitive organic compound materials. Therefore, the art needs to come up with an effective and non-damaging OLED A method of patterning a device.
- the present disclosure provides a photoresist composition, including: a polymer polymerized from a first monomer and a second monomer, wherein the first monomer contains a polymerizable group An acrylic monomer with a group and a fluorine-containing group, the second monomer is a monomer containing a polymerizable group and a reactive group that can change the solubility; Photo base generator (PBG); A thermal acid generator (TAG); and a fluorinated solvent.
- the photoresist composition is a positive photoresist.
- the polymer is formed by free radical polymerization of a first monomer and a second monomer, and the first monomer is a monomer represented by formula (I):
- R 1 represents a hydrogen atom, a cyano group, a methyl group or an ethyl group
- R 2 represents a substituted or unsubstituted alkyl group having at least 5 fluorine atoms.
- R is a substituted or unsubstituted alkyl group of at least 10 fluorine atoms.
- the alkyl group of R2 is a cyclic or acyclic hydrofluorocarbon or hydrofluoroether having at least as many fluorine atoms as carbon atoms.
- R represents a perfluoroalkyl group having at least 4 carbon atoms or a 1H, 1H, 2H, 2H-perfluoroalkyl group.
- the 1H, 1H, 2H, 2H-perfluoroalkyl group may be, for example, but not limited to, 1H, 1H, 2H, 2H-perfluorooctyl methacrylate (FOMA for short).
- the first monomer is a monomer represented by formula (I-1):
- the second monomer is a monomer represented by formula (II):
- R 3 represents a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms. In certain embodiments, R3 is tertiary alkyl. In certain embodiments, the monomer represented by formula (II) is selected from the group consisting of: formula (II-1), formula (II-2), formula (II-3), formula (II-4) ), or formula (II-5)
- the second monomer is a monomer represented by formula (II-2).
- the polymer is formed through free radical polymerization.
- a thermal initiator that can undergo pyrolysis to generate free radicals, and performing free radical polymerization under certain polymerization conditions.
- the thermal initiator may be, for example, but not limited to, 2,2'-Azobis (isobutyronitrile), AIBN for short.
- the polymer is formed by reacting the monomer represented by formula (I-1) and the monomer represented by formula (II-2) as follows, so that the polymer contains the structure shown below:
- the thermal acid generator is selected from the group consisting of: Para-Toluene-Sulfonic Acid (pTSA for short), Dodecyl Benzene Sulfonic Acid (Dodecyl Benzene Sulfonic Acid for short) DDBSA), Fluoroantimonic acid (SbF 6 ), Triflate group (-OTf), and Tris(pentafluorophenyl)borane (TPFB) ).
- pTSA Para-Toluene-Sulfonic Acid
- Dodecyl Benzene Sulfonic Acid Dodecyl Benzene Sulfonic Acid for short
- DDBSA Dodecyl Benzene Sulfonic Acid
- SbF 6 Fluoroantimonic acid
- -OTf Triflate group
- TPFB Tris(pentafluorophenyl)borane
- the photobase generator is selected from the group consisting of: formula (III-1), formula (III-2), formula (III-3), formula (III-4), or Formula (III-5)
- the photoresist composition does not include a photoacid generator.
- fluorinated solvents include room temperature perfluorinated or highly fluorinated solvents that are immiscible with water and most organic solvents.
- the fluorinated solvent may be, for example, but not limited to, hydrofluoroether (HFE), which is highly environmentally friendly and has the title of "green” solvent.
- HFE hydrofluoroether
- HFE including isolated HFE is non-flammable, has zero ozone depletion potential, and has been shown to have very low toxicity to humans.
- HFE and isomeric mixtures of HFE may be, for example, but not limited to, methyl nonafluorobutyl ether and methyl nonafluoroisobutyl ether (HFE-7100), ethanol.
- Isomeric mixture of nonafluorobutyl ether and ethyl nonafluoroisobutyl ether HFE-7200aka Novec TM 7200
- 3-ethoxy-1,1,1,2,3,4,4, 5,5,6,6,6-dodecafluoro-2-trifluoromethyl-hexane HFE-7500aka Novec TM 7500
- 1,1,1,2,3,3-hexafluoro-4-( 1,1,2,3,3,3-Hexafluoropropoxy)-pentane HFE-7600aka Novec TM 7600
- 1-methoxyheptafluoropropane HFE-7000
- the content of the polymer ranges from The content of the photobase generator ranges from 1 to 50wt%, the content of the photobase generator ranges from 0.1 to 20wt%, the content of the thermal acid generator ranges from 0.1 to 20wt%, and the content of the fluorinated solvent ranges from 1 to 99wt%.
- Figure 1 is a flowchart of a method of patterning a device in accordance with certain embodiments of the present disclosure.
- the method 100 includes several operations: (101) Forming a photoresist composition layer on a substrate of a device, the photoresist composition layer includes a photoresist composition, a photoresist
- the composition includes a polymer polymerized from a first monomer and a second monomer, wherein the first monomer is an acrylic monomer containing a polymerizable group and a fluorine-containing group, and the second monomer
- the body is a monomer containing a polymerizable group and a solubility-changing reactive group, a photobase generator, a thermal acid generator, and a first fluorinated solvent; (102) Exposing the photoresist composition layer to Patterned radiation to form an exposed area and an unexposed area in the photoresist composition layer; (103) baking the exposed area and the unexposed area; and (104) removing the exposure of the photore
- Figure 2 is a top view of a device processed by a method of patterning a device in accordance with certain embodiments of the present disclosure. As shown in Figure 2, a substrate 10 is provided.
- the device processed by method 100 is an electroluminescent device. In some embodiments, the device processed by method 100 is an OLED device.
- device substrate 10 includes display area 10D and peripheral area 10P.
- the substrate 10 also includes a plurality of pixels 12 located in the display area 10D. Pixels 12 may be arranged in an array. Each individual pixel 12 is separated from other adjacent pixels 12 .
- each pixel 12 includes a first sub-pixel 12A and a second sub-pixel 12B.
- each pixel 12 includes a first sub-pixel 12A, a second sub-pixel 12B, and a third sub-pixel 12C.
- a sub-pixel may also be referred to as a sub-pixel region or pixel.
- the first sub-pixel 12A, the second sub-pixel 12B and the third sub-pixel 12B can be used to display different colors.
- the first sub-pixel 12A, the second sub-pixel 12B and the third sub-pixel 12C can respectively emit a first color image, a second color image and a third color image.
- the first sub-pixel 12A can be used to display green
- the second sub-pixel 12B can be used to display red
- the third sub-pixel 12C can be used to display red. Shows blue.
- the arrangement of the sub-pixels includes, from left to right, the first sub-pixel 12A, the second sub-pixel 12B and then the third sub-pixel 12C, but is not limited thereto.
- the arrangement of sub-pixels can also be changed based on design or other considerations.
- the sub-pixel shape shown in FIG. 2 is square, the sub-pixels can also adopt other shapes.
- the number of sub-pixels in the pixel 12 may be, but is not limited to, three sub-pixels; the number of sub-pixels may be changed, and other appropriate sub-pixels may be used to display different colors, such as yellow, white or other colors.
- substrate 10 may be a rigid or flexible substrate. Furthermore, substrate 10 may be an opaque or transparent substrate. Substrate 10 may include glass, quartz, semiconductor materials (such as silicon, III-V elements), or other suitable materials. In certain embodiments, substrate 10 includes graphene. In certain embodiments, substrate 10 may be formed utilizing a polymeric matrix material. A dielectric layer (not shown in the figure) may optionally be provided on the substrate 10 . In certain embodiments, the dielectric layer may be made of silicon oxide, silicon nitride, silicon oxynitride, or other suitable materials.
- FIG. 3-10 are cross-sectional views of a device structure during various stages according to certain embodiments of the present disclosure.
- FIG. 3 is a schematic cross-sectional view of a pixel along line segment A-A in FIG. 2 .
- method 100 uses the photoresist composition of the present disclosure.
- electrode 14 is formed on substrate 10 .
- a plurality of sub-pixels share an electrode 14 .
- Electrode 14 may include opaque conductive material or transparent conductive material. Examples of opaque conductive materials may include a metal such as aluminum (Al), copper (Cu), silver (Ag), gold (Au), tungsten (W), another metal, or a metal alloy. Examples of transparent conductive materials may include indium tin oxide (ITO), indium zinc oxide (IZO), aluminum-doped zinc oxide (AZO) and indium-doped cadmium oxide, or other similar materials.
- electrode 14 is the anode of the device. In some embodiments, a plurality of electrodes 14 are formed separately on the substrate 10 , and the first sub-pixel 12A and the second sub-pixel 12B respectively have different electrodes 14 . In some embodiments, each sub-image The element includes an electrode 14.
- the substrate 10 includes a driving circuit, such as a thin film transistor (TFT) array.
- the pattern of the electrode 14 can be designed according to the desired pixel arrangement.
- the electrode 14 can be electrically connected to a driving circuit in the substrate 10 to receive a driving signal for driving the electroluminescent device.
- the disclosed method of patterning a device can process multiple pixels 12 .
- a pixel defining layer (also referred to as PDL) 16 is formed on the substrate 10 to separate the first sub-pixel 12A and the second sub-pixel 12B.
- pixel defining layer 16 partially covers electrode 14 and leaves a portion of electrode 14 open to receive the light emitting layer.
- the pixel defining layer 16 separates the plurality of electrodes 14 from each other when viewed through the thickness of the device.
- Pixel defining layers 16 may have the same or different shapes. As shown in FIG. 3 , the cross-section of the pixel defining layer 16 may have a curved surface. In some embodiments, the shape of the pixel defining layer 16 may be a trapezoid, an inverted ladder, or a square. Viewed through the thickness of the device, the pixel defining layers 16 may be arranged in a grid. The pattern of the pixel defining layer 16 can be designed according to the desired pixel arrangement.
- the pixel defining layer 16 includes a polymer material, a photosensitive material or a light-absorbing material, and its color is not particularly limited. In some embodiments, the pixel defining layer 16 is formed through a photolithography process.
- an organic material layer 18 is formed over the pixel defining layer 16 and the electrode 14 exposed through the pixel defining layer 16 .
- the organic material layer 18 is a first carrier injection layer, a first carrier transport layer, or a combination of the above.
- the first carrier injection layer can be used for hole injection or electron injection.
- the first carrier transport layer can be used for hole transport or electron transport.
- the first carriers are holes, and the organic material layer 18 includes a hole injection layer (HIL) formed on the electrode 14 and a hole transport layer (HTL) formed on the HIL.
- the first sub-pixel 12A includes a first light-emitting layer 13A. In some embodiments, the first light-emitting layer 13A can be used to display green.
- the organic material layer 18 is disposed on the electrode 14 and the pixel defining layer 16 in sections.
- the first sub-pixel 12A and the second sub-pixel 12B respectively have different organic material layers 18 .
- each sub-pixel includes an independent electrode 14 and an organic material layer 18 disposed on the electrode 14 .
- operation 101 of method 100 includes forming a photoresist composition layer 22 on substrate 10 of the device.
- Photoresist composition layer 22 includes a photoresist composition.
- the photoresist composition includes a polymer polymerized by a first monomer and a second monomer, wherein the first monomer is an acrylic monomer containing a polymerizable group and a fluorine-containing group, and the second monomer is The monomer is a monomer containing a polymerizable group and a solubility-changing reactive group, a photobase generator, a thermal acid generator, and a first fluorinated solvent.
- the photoresist composition is as described above and will not be described again here.
- a sacrificial layer 21 is formed on the organic material layer 18 and the first light emitting layer 13A. In some embodiments, sacrificial layer 21 covers over organic material layer 18 . In some embodiments, the photoresist composition layer 22 is formed on the sacrificial layer 21 .
- the sacrificial layer 21 can be disposed between the photoresist composition layer 22 and the substrate 10 .
- the sacrificial layer 21 can be disposed between the photoresist composition layer 22 and the organic material layer 18 .
- the sacrificial layer 21 can be used as a planarization layer to improve the flatness of the photoresist composition layer 22 or an adhesion layer to improve the bonding between the photoresist composition layer 22 and the organic material layer 18 .
- a barrier layer (not shown in the figure) is further included between the sacrificial layer 21 and the photoresist composition layer 22 .
- the etching rate of the barrier layer is different from that of the sacrificial layer 21 and the photoresist composition layer 22 . Therefore, highly selective etching can be performed without damaging the underlying material (sacrificial layer 21).
- operation 102 of method 100 includes exposing photoresist composition layer 22 to patterned radiant energy to form exposed regions 23 and unexposed areas in photoresist composition layer 22 . Exposure area 24. In some embodiments, the photoresist composition layer 22 forms at least one exposed area 23 and at least one unexposed area 24 . In certain embodiments, the substrate 10 with the photoresist composition layer 22 is transferred to a photolithography exposure tool for an exposure process.
- the exposure process is The photoresist composition layer 22 is exposed to radiant energy, such as deep ultraviolet light (DUV for short) or extreme ultraviolet light (EUV for short) through a photomask 25 with a pre-layout pattern, to obtain a plurality of exposure areas 23 and a plurality of The photoresist composition layer 22 in the unexposed area 24 .
- radiant energy may be, for example, but not limited to, a 248 nm beam emitted by a krypton fluoride (KrF) excimer laser, or a 193 nm beam emitted by an argon fluoride (ArF) excimer laser.
- the radiant energy may be, for example, but not limited to, EUV having a wavelength below about 13.5 nm.
- the exposed areas of photoresist composition layer 22 are 23 Alkali is produced.
- the thermal acid generator in photoresist composition layer 22 is unresponsive to radiant energy (light energy).
- operation 103 of method 100 includes baking exposed areas 23 and unexposed areas 24 .
- the substrate 10 having the photoresist composition layer 22 is subjected to a post-exposure bake process.
- the exposed areas 23 and the unexposed areas of the photoresist composition layer 22 are heated by the thermal acid generator in the photoresist composition layer 22. 24 generates acid, and an acid-base neutralization reaction occurs with the alkali generated in the exposed area 23.
- the unexposed area 24 can prevent the photoresist composition layer 22 from being dissolved in the developer under the condition that the thermal acid generator generates acid.
- the temperature of the baked exposed area 23 and the unexposed area 24 is 90°C or less. In some embodiments, the temperature of baking the exposed area 23 and the unexposed area 24 is between 80 and 90°C.
- operation 104 of method 100 includes removing exposed areas 23 of photoresist composition layer 22 to form developed structures 26 .
- the photoresist composition layer 22 is subjected to a development process, for example but not limited to, the photoresist composition layer 22 is immersed in a developer (not shown in the figure) or the developer is coated on the photoresist layer 22 .
- the photoresist composition layer 22 includes a positive photoresist, and the developer dissolves the exposed areas 23 .
- the developer includes at least 50% by volume of a second fluorinated solvent.
- the second fluorinated solvent and the first fluorinated solvent agents are the same or different.
- the developer contains at least 90% by volume of one or more hydrofluoroether solvents.
- the exposed portion of the sacrificial layer 21 from the developing structure 26 is removed, so that a portion of the organic material layer 18 is exposed from the sacrificial layer 21 .
- the sacrificial layer 21 is patterned to form the recess 27.
- the sacrificial layer 21 is patterned to form the recess 27 and further etched horizontally to form an undercut 28, such that More organic material layer 18 is exposed from sacrificial layer 21 .
- the method 100 further includes forming a second light-emitting layer 13B above the photoresist composition layer 22 and on the second sub-pixel 12B through the recess 27 .
- the second luminescent layer 13B may further cover the sidewalls of the recess 27 .
- the method of forming the second light-emitting layer 13B can be the same as or different from that of forming the first light-emitting layer 13A, and can be through various deposition processes, such as but not limited to vapor deposition, sputtering, atomic layer deposition (ALD), Thermal evaporation, coating or jetting.
- the second light-emitting layer 13B can be used to display an image of the second color. In some embodiments, the second light-emitting layer 13B can be used to display red color.
- the method 100 further includes removing the photoresist composition layer 22 and the sacrificial layer 21 .
- the photoresist composition layer 22 and the sacrificial layer 21 are removed using a stripping process.
- sacrificial layer 21 is removed using a third fluorinated solvent.
- the third fluorinated solvent is the same as or different from the second fluorinated solvent.
- the third fluorinated solvent includes at least 90% by volume of one or more hydrofluoroether solvents.
- a stripping process is used to remove the photoresist composition layer 22 and the sacrificial layer 21 while simultaneously removing the portion of the second light-emitting layer 13B located above the photoresist composition layer 22 .
- the portion of the second light-emitting layer 13B located on the surface of the photoresist composition layer 22 is washed away together with the photoresist composition layer 22 , and the portion of the second light-emitting layer 13B located in the first concave portion 27 remains.
- a pixel structure in which the first light-emitting layer 13A is located on the first sub-pixel 12A and the second light-emitting layer 13B is located on the second sub-pixel 12B can be formed.
- the sequence of forming multiple light-emitting layers includes forming a first light-emitting layer 13A, then forming a second light-emitting layer 13B, and finally forming a third light-emitting layer (not shown in the figure) that displays a third color. But not limited to the above order.
- the sequence of forming multiple light-emitting layers in this disclosure is designed to form more stable light-emitting layers first, and then form one or more less stable light-emitting layers, but is not limited to the above order. Other suitable sequences for forming the light emitting layer may also be used.
- the word “simultaneously” refers to removing the second light-emitting layer 13B, the photoresist composition layer 22 and the second light-emitting layer 13B above the photoresist composition layer 22 in a single stripping process. part.
- the sacrificial layer 21 and the portion of the second light-emitting layer 13B located above the photoresist composition layer 22 may be removed at different steps in the stripping process, but are not limited thereto.
- the method 100 further includes forming a conductive layer 19 on the substrate 10 of the device.
- the conductive layer 19 is formed on the organic material layer 18, the first luminescent layer 13A and the second luminescent layer 13B.
- conductive layer 19 includes a transparent conductive material or an opaque conductive material.
- conductive layer 19 includes magnesium.
- Conductive layer 19 may include a similar conductive material as electrode 14 .
- conductive layer 19 is designed to serve as the cathode of the device.
- the conductive layer 19 can be connected to a driving circuit in the substrate 10 to receive a driving signal for driving the electroluminescent device.
- the conductive layer 19 is continuously connected to the first sub-pixel 12A and the second sub-pixel 12B, but is not limited thereto.
- the conductive layer 19 can be divided into several sections, wherein each section is vertically aligned with the first light-emitting layer 13A and the second light-emitting layer 13B respectively.
- the second carrier transport layer and the second carrier injection layer can also be configured for each sub-pixel based on the above description, or shared with other sub-pixels, and the implementation shown in the figure It should not be considered as a limitation of the invention.
- the method 100 further includes forming a second carrier transport layer and a second carrier injection layer between the first luminescent layer 13A and the second luminescent layer 13B and the conductive layer 19, or a combination of the foregoing.
- the second carrier injection layer can be used for electron injection or hole injection.
- the second carrier injection layer can be used for electron transport or hole transport.
- the second carrier is an electron
- the first light-emitting layer 13A An electron transport layer (ETL) is formed between the first luminescent layer 13A and the second luminescent layer 13B, and an electron injection layer (EIL) is formed between the ETL and the conductive layer 19.
- ETL electron transport layer
- EIL electron injection layer
- a photoresist composition includes: a polymer polymerized from a first monomer and a second monomer, wherein the first monomer contains polymerizable An acrylic monomer with a group and a fluorine-containing group, the second monomer is a monomer containing a polymerizable group and a reactive group that can change the solubility; a photobase generator; a thermal acid generator; and monofluorinated solvents.
- the polymer is formed by free radical polymerization of the first monomer and the second monomer, the first monomer is a monomer represented by formula (I), and the second monomer is The monomer is the monomer shown in formula (II):
- R 1 represents a hydrogen atom, a cyano group, a methyl group or an ethyl group
- R 2 represents a substituted or unsubstituted alkyl group having at least 5 fluorine atoms
- R 3 represents a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms.
- the alkyl group of R2 is a cyclic or acyclic hydrofluorocarbon or hydrofluoroether having at least as many fluorine atoms as carbon atoms.
- the monomer represented by formula (II) is selected from the group consisting of: formula (II-1), formula (II-2), formula (II-3), formula (II) -4), or formula (II-5)
- the thermal acid generator is selected from the group consisting of p-toluenesulfonic acid, dodecylbenzenesulfonic acid, fluorantibonic acid, triflate groups, and tris( Pentafluorophenyl)borane.
- the photobase generator is selected from the group consisting of: formula (III-1), formula (III-2), formula (III-3), formula (III-4), Or formula (III-5):
- a method of patterning a device includes forming a photoresist composition layer on a substrate of a device, the photoresist composition including a first unit A polymer formed by polymerizing a monomer and a second monomer, wherein the first monomer is an acrylic monomer containing a polymerizable group and a fluorine-containing group, and the second monomer is an acrylic monomer containing a polymerizable group.
- a monomer with a solubility-modifying reactive group a photobase generator, a thermal acid generator, and a first fluorinated solvent
- exposing the photoresist composition layer to patterned radiation to The photoresist composition layer forms an exposed area and an unexposed area; the exposed area and the unexposed area are baked; and the exposed area of the photoresist composition layer is removed to form a developed structure.
- the device is an organic light emitting diode device
- the substrate includes one or more layers of organic materials.
- the exposed area is removed by contacting the exposed area with a developer including a second fluorinated solvent.
- the content of the polymer ranges from 1 to 50wt%
- the content of the photobase generator ranges from 0.1 to 20wt%
- the thermal acid generator The content of the agent ranges from 0.1 to 20 wt%
- the content of the fluorinated solvent ranges from 1 to 99 wt%.
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- General Physics & Mathematics (AREA)
- Electroluminescent Light Sources (AREA)
- Materials For Photolithography (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
Abstract
Une composition de résine photosensible, celle-ci comprenant : un polymère qui est formé en polymérisant un premier monomère et un second monomère, le premier monomère étant un monomère acrylique contenant un groupe polymérisable et un groupe d'atomes contenant du fluor, et le second monomère étant un monomère contenant un groupe polymérisable et un groupe réactif capable de modifier la solubilité ; un générateur de photobase ; un générateur d'acide thermique ; et un solvant fluoré. Un procédé permettant de former des motifs sur un dispositif, celui-ci consistant à : former une couche de composition de résine photosensible (22) sur un substrat (10) d'un dispositif, la couche de composition de résine photosensible (22) comprenant une composition de résine photosensible (S101) ; exposer la couche de composition de résine photosensible (22) à un rayonnement à motifs pour former une région exposée (23) et une région non exposée (24) sur la couche de composition de résine photosensible (22) (S102) ; cuire la région exposée (23) et la région non exposée (24) (S103) ; et retirer la région exposée (23) de la couche de composition de résine photosensible (22) pour former une structure développée (26) (S104).
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US202263332241P | 2022-04-18 | 2022-04-18 | |
US63/332,241 | 2022-04-18 | ||
CN202210975763.2A CN116954021A (zh) | 2022-04-18 | 2022-08-15 | 一种光刻胶组成物及使装置图案化的方法 |
CN202210975763.2 | 2022-08-15 |
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Citations (6)
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US20030215735A1 (en) * | 2000-05-05 | 2003-11-20 | Wheland Robert Clayton | Copolymers for photoresists and processes therefor |
US20140356788A1 (en) * | 2013-05-31 | 2014-12-04 | Orthogonal, Inc. | Fluorinated photoresist with integrated sensitizer |
US20150030982A1 (en) * | 2013-07-24 | 2015-01-29 | Orthogonal, Inc. | Fluorinated photopolymer with fluorinated sensitizer |
US20150140289A1 (en) * | 2013-11-19 | 2015-05-21 | Bioflex Devices | Method of patterning a bioresorbable material |
CN107112440A (zh) * | 2014-08-01 | 2017-08-29 | 正交公司 | 装置的光刻图案化 |
JP2021123652A (ja) * | 2020-02-05 | 2021-08-30 | 富士フイルム株式会社 | 樹脂組成物、硬化膜、積層体、硬化膜の製造方法、及び、半導体デバイス |
-
2023
- 2023-04-07 WO PCT/CN2023/086787 patent/WO2023202390A1/fr unknown
- 2023-04-18 TW TW112114410A patent/TW202343140A/zh unknown
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030215735A1 (en) * | 2000-05-05 | 2003-11-20 | Wheland Robert Clayton | Copolymers for photoresists and processes therefor |
US20140356788A1 (en) * | 2013-05-31 | 2014-12-04 | Orthogonal, Inc. | Fluorinated photoresist with integrated sensitizer |
US20150030982A1 (en) * | 2013-07-24 | 2015-01-29 | Orthogonal, Inc. | Fluorinated photopolymer with fluorinated sensitizer |
US20150140289A1 (en) * | 2013-11-19 | 2015-05-21 | Bioflex Devices | Method of patterning a bioresorbable material |
CN107112440A (zh) * | 2014-08-01 | 2017-08-29 | 正交公司 | 装置的光刻图案化 |
JP2021123652A (ja) * | 2020-02-05 | 2021-08-30 | 富士フイルム株式会社 | 樹脂組成物、硬化膜、積層体、硬化膜の製造方法、及び、半導体デバイス |
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