KR20150079001A - anti-yellowing composition of OLED for encapsulants - Google Patents
anti-yellowing composition of OLED for encapsulants Download PDFInfo
- Publication number
- KR20150079001A KR20150079001A KR1020130168932A KR20130168932A KR20150079001A KR 20150079001 A KR20150079001 A KR 20150079001A KR 1020130168932 A KR1020130168932 A KR 1020130168932A KR 20130168932 A KR20130168932 A KR 20130168932A KR 20150079001 A KR20150079001 A KR 20150079001A
- Authority
- KR
- South Korea
- Prior art keywords
- thiol
- group
- epoxy
- triazole
- composition
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 34
- 238000004383 yellowing Methods 0.000 title claims abstract description 11
- 239000008393 encapsulating agent Substances 0.000 title claims description 4
- 239000000945 filler Substances 0.000 claims abstract description 22
- 239000004593 Epoxy Substances 0.000 claims abstract description 19
- 239000000463 material Substances 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 239000003999 initiator Substances 0.000 claims abstract description 5
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 5
- -1 thiol compound Chemical class 0.000 claims description 85
- 229920002050 silicone resin Polymers 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 12
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 claims description 10
- 239000003822 epoxy resin Substances 0.000 claims description 9
- 229920000647 polyepoxide Polymers 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000011521 glass Substances 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
- 229910010272 inorganic material Inorganic materials 0.000 claims description 6
- 238000004394 yellowing prevention Methods 0.000 claims description 6
- 238000011049 filling Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 239000011342 resin composition Substances 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 244000028419 Styrax benzoin Species 0.000 claims description 4
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 4
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 235000019382 gum benzoic Nutrition 0.000 claims description 4
- 150000002484 inorganic compounds Chemical class 0.000 claims description 4
- 239000011256 inorganic filler Substances 0.000 claims description 4
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 4
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 claims description 3
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 claims description 3
- 229960002130 benzoin Drugs 0.000 claims description 3
- 239000000919 ceramic Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 230000001681 protective effect Effects 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- CHTYYFOORKYAAV-UHFFFAOYSA-N 2,3-dimethyl-2-(3-methyl-7-oxabicyclo[4.1.0]heptan-3-yl)-7-oxabicyclo[4.1.0]heptane-3-carboxylic acid Chemical compound C1CC2OC2CC1(C)C1(C)C2OC2CCC1(C)C(O)=O CHTYYFOORKYAAV-UHFFFAOYSA-N 0.000 claims description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 2
- OVUCUBMCRPYGJA-UHFFFAOYSA-N 3,4-dimethyl-2-[(4-methyl-7-oxabicyclo[4.1.0]heptan-3-yl)methyl]-7-oxabicyclo[4.1.0]heptane-3-carboxylic acid Chemical compound CC1CC2OC2CC1CC1C2OC2CC(C)C1(C)C(O)=O OVUCUBMCRPYGJA-UHFFFAOYSA-N 0.000 claims description 2
- BHXPPJKKWUKLDS-UHFFFAOYSA-N 3,5-dimethyl-2-(5-methyl-7-oxabicyclo[4.1.0]heptan-3-yl)-7-oxabicyclo[4.1.0]heptane-3-carboxylic acid Chemical compound C1C2OC2C(C)CC1C1C2OC2C(C)CC1(C)C(O)=O BHXPPJKKWUKLDS-UHFFFAOYSA-N 0.000 claims description 2
- IKYAJDOSWUATPI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propane-1-thiol Chemical compound CO[Si](C)(OC)CCCS IKYAJDOSWUATPI-UHFFFAOYSA-N 0.000 claims description 2
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 claims description 2
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 claims description 2
- UXQFGCIAJSWBTO-UHFFFAOYSA-N 5-methyl-4-[(5-methyl-7-oxabicyclo[4.1.0]heptan-4-yl)methyl]-7-oxabicyclo[4.1.0]heptane-4-carboxylic acid Chemical compound C1CC2OC2C(C)C1(C(O)=O)CC1CCC2OC2C1C UXQFGCIAJSWBTO-UHFFFAOYSA-N 0.000 claims description 2
- WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims description 2
- RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 2
- 235000001258 Cinchona calisaya Nutrition 0.000 claims description 2
- 229910020366 ClO 4 Inorganic materials 0.000 claims description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910018068 Li 2 O Inorganic materials 0.000 claims description 2
- 101100496858 Mus musculus Colec12 gene Proteins 0.000 claims description 2
- 241000080590 Niso Species 0.000 claims description 2
- 150000001266 acyl halides Chemical class 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- DJUWPHRCMMMSCV-UHFFFAOYSA-N bis(7-oxabicyclo[4.1.0]heptan-4-ylmethyl) hexanedioate Chemical compound C1CC2OC2CC1COC(=O)CCCCC(=O)OCC1CC2OC2CC1 DJUWPHRCMMMSCV-UHFFFAOYSA-N 0.000 claims description 2
- LHQZPSHKKVHDTB-UHFFFAOYSA-N bis(7-oxabicyclo[4.1.0]heptan-4-ylmethyl) oxalate Chemical compound C1CC2OC2CC1COC(=O)C(=O)OCC1CC2OC2CC1 LHQZPSHKKVHDTB-UHFFFAOYSA-N 0.000 claims description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 claims description 2
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000007857 hydrazones Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
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- 229910044991 metal oxide Inorganic materials 0.000 claims description 2
- 150000004706 metal oxides Chemical class 0.000 claims description 2
- 150000002828 nitro derivatives Chemical class 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 239000013034 phenoxy resin Substances 0.000 claims description 2
- 229920006287 phenoxy resin Polymers 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 claims description 2
- MNRILEROXIRVNJ-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=NC=N[C]21 MNRILEROXIRVNJ-UHFFFAOYSA-N 0.000 claims description 2
- 229960003087 tioguanine Drugs 0.000 claims description 2
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims 2
- 150000002118 epoxides Chemical class 0.000 claims 2
- LTQBNYCMVZQRSD-UHFFFAOYSA-N (4-ethenylphenyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)C1=CC=C(C=C)C=C1 LTQBNYCMVZQRSD-UHFFFAOYSA-N 0.000 claims 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims 1
- DOYKFSOCSXVQAN-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CCO[Si](C)(OCC)CCCOC(=O)C(C)=C DOYKFSOCSXVQAN-UHFFFAOYSA-N 0.000 claims 1
- XXCIGBFAFCNEOZ-UHFFFAOYSA-N 3-[ethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CCO[SiH](C)CCCOC(=O)C(C)=C XXCIGBFAFCNEOZ-UHFFFAOYSA-N 0.000 claims 1
- KSCAZPYHLGGNPZ-UHFFFAOYSA-N 3-chloropropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCl KSCAZPYHLGGNPZ-UHFFFAOYSA-N 0.000 claims 1
- LVNLBBGBASVLLI-UHFFFAOYSA-N 3-triethoxysilylpropylurea Chemical compound CCO[Si](OCC)(OCC)CCCNC(N)=O LVNLBBGBASVLLI-UHFFFAOYSA-N 0.000 claims 1
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
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- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 claims 1
- 238000005401 electroluminescence Methods 0.000 claims 1
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- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 claims 1
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- WLJVNTCWHIRURA-UHFFFAOYSA-M pimelate(1-) Chemical compound OC(=O)CCCCCC([O-])=O WLJVNTCWHIRURA-UHFFFAOYSA-M 0.000 claims 1
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- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 claims 1
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- 230000000052 comparative effect Effects 0.000 description 10
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- 238000005259 measurement Methods 0.000 description 4
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- C08L83/04—Polysiloxanes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
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Abstract
Description
본 발명은 유기발광 소자 봉지재용 황변방지 조성물에 관한 것으로 화학식 1로 표시되는 실리콘 수지, 에폭시 화합물, 열경화성개시제, 용제, 충진제, 무기물, 티올계화합물 및 실란커플링제를 포함한다. The present invention relates to a composition for preventing yellowing for an encapsulating material for an organic light emitting diode, which comprises a silicone resin, an epoxy compound, a thermosetting initiator, a solvent, a filler, an inorganic compound, a thiol compound and a silane coupling agent.
본 발명의 조성물은 지환족 에폭시수지와 실리콘 수지를 혼합 사용하여 에폭시의 높은 경도를 그대로 유지하면서 경화 후에 높은 투명도를 제공할 수 있다.The composition of the present invention can provide a high transparency after curing while maintaining the high hardness of the epoxy by mixing alicyclic epoxy resin and silicone resin.
OLED (Organic Light Emitting Diodes)는 유기 재료에 전류를 가하여 전기에너지를 빛으로 바꾸어주는 소자로 양극 (anode)과 음극 (cathode) 사이에 기능성 유기물 층이 삽입된 구조로 이루어져 있다. 소자의 전기적인 특성은 LED (Light Emitting Diodes)와 유사하며 양극에서 정공 (hole)이 주입되고 음극에서 전자 (electron)가 주입된 후 각각의 정공과 전자는 서로 상대편 전극을 향해 이동하다가 재결합(recombination)에 의해 에너지가 높은 여기전자 (exciton)를 형성하게 된다. 이때 형성된 여기자가 기저 상태(ground state)로 이동하면서 특정한 파장을 갖는 빛이 발생되도록 하는 디스플레이 기술이다. OLED (Organic Light Emitting Diodes) is a device that converts electric energy into light by applying electric current to organic materials, and has a structure in which a functional organic layer is inserted between an anode and a cathode. The electrical characteristics of the device are similar to those of LED (Light Emitting Diodes). After the hole is injected from the anode and the electron is injected from the cathode, the holes and electrons move toward each other and recombination The excitons having a high energy are formed. In this case, the exciton formed is a display technology for generating light having a specific wavelength while moving to a ground state.
OLED를 이용한 디스플레이의 장점은 자체발광, 고속응답, 광시야각, 초박형, 고화질, 내구성, 넓은 온도 범위 등 디스플레이로서 필요한 모든 요소를 갖추고 있어 이상적인 디스플레이로 각광받고 있다. OLED는 구동 방식에 따라 PM(passive matrix) OLED와 AM(active matrix) OLED로 나뉘며, PM의 경우 양극과 음극 사이의 교차점에서 발광이 되도록 설계된 구조로 제작이 용이하고 중소형 제품에 응용/생산이 가능하여 현재 mobile용 제품으로 생산되고 있다. AM의 경우 각각의 화소에 구동을 담당하는 TFT가 붙어 있어 화소를 독립적으로 구동시켜 저소비전력과 우수한 해상도 구현이 용이하나 각 픽셀 당 2~4개 정도의 TFT가 필요하여 공정이 많고 복잡하여 양산적용에 어려움이 있으나 향후 대형화 및 고해상도 디스플레이에 적용하기 위해서는 능동형 유기발광 다이오드(AMOLED)가 가장 적합하다고 할 수 있다. AMOLED는 수동형 유기발광 다이오드(PMOLED)의 양산이후 꾸준히 개발되어 최근 모바일용 양산을 시작으로 디스플레이로서 확고한 자리를 구축하기 위한 시도가 전세계적으로 확산되어지고 있다. The advantage of OLED displays is that they are ideal displays because of their self-emission, high-speed response, wide viewing angle, ultra-thin, high picture quality, durability and wide temperature range. OLED is divided into PM (passive matrix) OLED and AM (active matrix) OLED depending on the driving method. PM is designed to emit light at the intersection between anode and cathode, and can be easily applied to small / medium products. And is currently being produced as a mobile product. In the case of AM, each pixel is equipped with a TFT which is responsible for driving, so it is easy to realize low power consumption and excellent resolution by independently driving pixels, but it requires about 2 to 4 TFTs for each pixel, However, active organic light emitting diode (AMOLED) is most suitable for future large-sized and high-resolution displays. Since the mass production of passive organic light emitting diodes (PMOLED), AMOLED has been developed steadily, and attempts to establish a solid position as a display have been spreading all over the world.
일반적으로 AMOLED의 수명은 TV의 경우 30,000시간 이상, 모니터용에서는 50,000시간 이상을 요구하고 있으나 PDP 나 LCD의 수명에 비교한다면 ?은 것으로 발표되고 있다. 이러한 상대적 약점을 보완하기 위해 OLED 소자를 개발하는 연구진들은 끊임없이 수명 연장에 대한 연구를 진행하고 있다. 제품의 수명에 대한 연구는 발광층 또는 공통층의 재료 개발로 해결을 하려는 시도도 있지만 AMOLED의 광추출 효율 증가 기술과 산소와 수분에 민감한 재료를 보호하기 위한 봉지 기술(encapsulation Technology)은 패널 업체의 성공을 좌우하는 기술로 알려지고 있다. Generally, the lifetime of AMOLED is more than 30,000 hours for TV and more than 50,000 hours for monitor, but it is reported to be compared with the lifetime of PDP or LCD. In order to compensate for this relative weakness, researchers developing OLED devices are constantly working on extending their lifetime. Although studies on the lifetime of the product have attempted to solve the problem by developing materials for the light emitting layer or the common layer, the encapsulation technology for protecting the oxygen and moisture sensitive materials and the light extraction efficiency technology of the AMOLED have been the success Is known as a technology that influences.
OLED를 봉지하는 방식에는 유리/금속 캔을 이용한 봉지 방법, 박막 봉지 방법 그리고 박막과 유리를 동시에 이용하는 hybrid 봉지 방법의 3가지가 있다. 유리/금속 캔을 이용하는 방식은 일정한 형태로 가공된 유리나 금속 캔의 내부에 흡습제를 부착하고 캔과 소자를 광경화성 수지로 고정시키는 것이다. 이러한 방식은 현재 2인치 이하의 PMOLED에 적용되어 양산되고 있다. 금속 캔을 이용한 봉지 방식은 AMOLED에서 요구되는 전면 발광 구조를 사용할 수 없으며 패널의 크기에 비례하여 변형이 심해지고 무게가 급격히 무거워지는 단점이 있다. 유리 캔을 이용한 봉지 방식은 전면 발광 구조에 채택은 가능하나 패널의 크기가 증가함에 따라서 외부충격에 의한 파손 가능성이 매우 높아진다. 또한 기존에 사용하는 흡습제는 불투명하기 때문에 AM OLED에 적용하기 위해서는 이를 대체할 기술이 개발되어야만 한다. 본 발명과 관련되는 종래기술로는 한국특허공개번호 10-2011-0014692(접착성 캡슐화 조성물 및 그로 제조된 전자 소자)는 접착성 캡슐화 조성물은 선택적인 다작용성 (메트)아크릴레이트 단량체 및/또는 선택적인 점착 부여제와 조합하여 하나 이상의 폴리아이소부틸렌 수지를 포함하는 감압 접착제를 포함한다. 한국특허등록번호 10-1030019(봉지재용 투광성 수지 및 이를 포함하는 전자 소자)화학식 1로 표현되는 제1 실리콘 화합물과 화학식 2로 표현되는 화합물을 포함하는 제2 실리콘 화합물을 공중합하여 얻어지는 폴리실록산을 포함하는 봉지재용 투광성 수지 조성물 및 이를 경화하여 얻어진 봉지재를 포함하는 전자 소자를 제공한다. 한국특허록번호 10-0976461(봉지재용 투광성 수지 및 이를 포함하는 전자 소자)은 화학식 1A 내지 화학식 1D로 표현되는 금속 화합물 중 적어도 하나, 그리고 화학식 2로 표현되는 화합물을 포함하는 실리콘 화합물을 공중합하여 얻어지는 폴리메탈로실록산(polymetallosiloxane)을 포함하는 봉지재용 투광성수지 조성물 및 이를 경화하여 얻어진 봉지재를 포함하는 전자 소자를 제공한다. 한국특허등록번호 10-1342034(봉지재, 태양 전지 모듈 및 발광 다이오드)는 일반식 (1) 및／또는 일반식 (2)로 표시되는 구조 단위와, 실라놀기 및／또는 가수 분해성 실릴기를 갖는 폴리실록산 세그먼트(a1)와, 알코올성 수산기를 갖는 비닐계 중합체 세그먼트(a2)가, 일반식 (3)으로 표시되는 결합에의해 결합된 복합 수지(A), 폴리이소시아네이트(B)를 함유하고, 상기 폴리실록산 세그먼트(a1)의 함유율이 경화성 수지 조성물의 전 고형분량에 대하여 10∼50중량％이며, 또한, 폴리이소시아네이트(B)의 함유율이 경화성 수지 조성물의 전 고형분량에 대하여 5∼50중량％인 봉지재와, 상기 봉지재를 사용하는 태양 전지 모듈 및 발광 다이오드를 제공한다. 한국특허등록번호 10-1169031(발광 다이오드 봉지재용 열경화성 실리콘 조성물)(a) 최소 2개 이상의 탄소-탄소 이중결합을 포함하는 유기기를 포함하는 실리콘 수지; (b) 규소원자에결합된 수소를 최소 2개 이상 포함하는 경화제; (c) 부가 반응 촉매; (d) 탄소-탄소 삼중결합을 포함하는 알코올; 및 (e) 에스테르기를 포함하는 유기첨가제를 포함하며, 선팽창계수가 300 ppm/K 이하의 값을 갖는 것을 특징으로 하는 발광 다이오드 봉지재용 열경화성 실리콘 조성물에 관한 것이다. There are three methods of encapsulating OLED: sealing using glass / metal can, thin sealing, and hybrid sealing using thin film and glass simultaneously. In the method using a glass / metal can, a desiccant is attached to the inside of a glass or metal can which is processed into a certain shape, and the can and the element are fixed with a photo-curable resin. This method is currently being applied to PMOLEDs of 2 inches or less. The encapsulation method using a metal can has a disadvantage in that the total light emitting structure required by the AMOLED can not be used and the deformation is increased in proportion to the size of the panel and the weight is drastically increased. The encapsulation method using a glass can can be adopted for the entire light emitting structure, but as the size of the panel increases, the possibility of breakage due to an external impact becomes very high. In addition, since the conventional moisture absorber is opaque, a technology for replacing it with AM OLED must be developed. Korean Patent Laid-Open No. 10-2011-0014692 (an adhesive encapsulating composition and an electronic device made therefrom) discloses that the adhesive encapsulating composition comprises an optional multifunctional (meth) acrylate monomer and / Sensitive adhesive comprising at least one polyisobutylene resin in combination with a tackifier. Korean Patent Registration No. 10-1030019 (Transparent resin for encapsulant and electronic device containing the same) A polysiloxane obtained by copolymerizing a first silicone compound represented by the formula (1) and a second silicone compound containing the compound represented by the formula (2) An electronic device comprising a light-transmitting resin composition for an encapsulating material and an encapsulating material obtained by curing the same. Korean Patent No. 10-0976461 (a translucent resin for an encapsulating material and an electronic device including the same) can be obtained by copolymerizing a silicone compound containing at least one of the metal compounds represented by Chemical Formulas 1A to 1D and a compound represented by Chemical Formula 2 An electronic device comprising a light-transmitting resin composition for encapsulating material comprising polymetallosiloxane and a sealing material obtained by curing the same. Korean Patent Registration No. 10-1342034 (encapsulant, solar cell module, and light emitting diode) has a structure in which a structural unit represented by the general formula (1) and / or the general formula (2) and a polysiloxane having a silanol group and / or a hydrolyzable silyl group (A) and a polyisocyanate (B) in which a segment (a1) and a vinyl-based polymer segment (a2) having an alcoholic hydroxyl group are bonded by a bond represented by the general formula (3), and the polysiloxane segment (B) in an amount of 5 to 50% by weight based on the total solid content of the curable resin composition, and the content of the polyisocyanate (B) in the total solid content of the curable resin composition is 10 to 50% A solar cell module using the sealing material, and a light emitting diode. (A) a silicone resin comprising an organic group containing at least two carbon-carbon double bonds; (b) a curing agent containing at least two hydrogen atoms bonded to silicon atoms; (c) an addition reaction catalyst; (d) an alcohol comprising a carbon-carbon triple bond; And (e) an organic additive including an ester group, and has a linear expansion coefficient of 300 ppm / K or less.
그러나 이 들 종래기술은 본 발명과 기술적구성이 다른 것이다.However, these prior arts have different technical constructions from the present invention.
본 발명이 해결하고자 하는 과제는 유기발광 소자의 수분과 산소의 차단을 높이며, 내구성과 광학적 특성을 높이고 경화 후의 황변을 방지하여 높은 투과율을 가지는 조성 및 제조방법을 제공하는 데 있다. 그러나 Bis-A와 Bis-F 에폭시의 경우, 경화 후 황변이 있어 OLED소자의 전면 광부에 적용하는 에 어려움이 있다. SUMMARY OF THE INVENTION The object of the present invention is to provide a composition and a method of manufacturing the organic light emitting device having high transmittance by increasing the interception of moisture and oxygen in the organic light emitting device, enhancing durability and optical characteristics, and preventing yellowing after curing. However, Bis-A and Bis-F epoxy resins have yellowing after curing, making it difficult to apply them to the frontal part of OLED devices.
이에 따라 지환족에폭시수지(Cycloaliphatic Epoxy Resin)와 실리콘수지(resin)를 혼합 사용함으로써, 에폭시의 높은 경도(hardness)를 그대로 유지하면서 경화 후의 높은 투명도를 가질 수 있도록 하는데 있다.Accordingly, by using a mixture of a cycloaliphatic epoxy resin and a silicone resin, it is possible to maintain high hardness of epoxy while maintaining high transparency after curing.
본 발명의 실리콘 수지를 포함하는 유기발광 소자 봉지재용 황변방지 조성물은 지환족 에폭시수지와 실리콘 수지를 혼합 사용함으로써, 에폭시의 높은 경도를 그대로 유지하면서 경화 후에 높은 투명도를 가질 수 있도록 하는데 그 목적이 있다. 상기와 같은 본 발명의 목적을 달성하기 위한 일 구현예는 하기 화학식 1로 표시되는 실리콘 수지 10~30%, 지환족 에폭시 화합물 30~50%, 고분자 에폭시(페녹시) 10~30%, 열경화성개시제 0.5~5%, 무기물0~20%, 티올계화합물 0~20%, 실란커플링제 0.5~5%를 포함할 수 있다. It is an object of the present invention to provide a composition for preventing yellowing of an encapsulating material for an organic light emitting diode comprising a silicone resin, which has high transparency after curing while maintaining high hardness of epoxy by using an alicyclic epoxy resin and a silicone resin . In an embodiment of the present invention, the silicone resin comprises 10 to 30% of a silicone resin represented by the following formula (1), 30 to 50% of an alicyclic epoxy compound, 10 to 30% of a polymer epoxy (phenoxy) 0.5 to 5% of an inorganic compound, 0 to 20% of an inorganic compound, 0 to 20% of a thiol compound, and 0.5 to 5% of a silane coupling agent.
<화학식 1>≪ Formula 1 >
상기 화학식 1에서, R1은 각각 독립적으로 불포화 결합을 1개 이상 가지는 탄소수 2 내지 10의 유기기, 머캅토기이고, R2는 각각 독립적으로 히드록시기, 수소, 불소, 탄소수 1 내지 10의 직쇄 또는 분지쇄 알킬기, 탄소수 3 내지 15의 시클로알킬기, 탄소수 2 내지 10의 아릴기, 에폭시기 또는 페닐렌기이다. Wherein R1 is independently an organic group having 2 to 10 carbon atoms and at least one unsaturated bond and is a mercapto group; R2 is independently selected from the group consisting of a hydroxyl group, hydrogen, fluorine, a linear or branched alkyl group having 1 to 10 carbon atoms , A cycloalkyl group having 3 to 15 carbon atoms, an aryl group having 2 to 10 carbon atoms, an epoxy group or a phenylene group.
본 발명의 바람직한 일 구현예에서, 위 화학식 1에서, R1은 각각 독립적으로 비닐기, 메타크릴기, 메타크릴옥시기, 아세테이트기, 아크릴기 및 아크릴옥시기, 머캅토기로 구성된 군에서 선택되는 것을 특징으로 할 수 있다. In a preferred embodiment of the present invention, R1 in the above formula (1) is independently selected from the group consisting of a vinyl group, a methacrylic group, a methacryloxy group, an acetate group, an acryl group and an acryloxy group, .
경화성 수지로는 방향족 또는 지방족 또는 직쇄형 또는 분지쇄형의 에폭시 수지를 사용할 수 있다.고리지방족 에폭시드에는 3,4-에폭시씨클로헥실메틸-3,4-에폭시씨클로헥산 카르복실레이트 예컨대 3,4-에폭시씨클로헥실메틸-3,4-에폭시씨클로헥산 카르복실레이트; 3,4-에폭시-1-메틸씨클로헥실-메틸-3,4-에폭시-1-메틸씨클로헥산 카르복실레이트; 6-메틸-3,4-에폭시씨클로헥실메틸메틸-6-메틸-3,4-에폭시씨클로헥산 카르복실레이트; 3,4-에폭시-2-메틸씨클로헥실메틸-3,4-에폭시-2-메틸씨클로헥산 카르복실레이트; 3,4-에폭시-3-메틸씨클로헥실-메틸-3,4-에폭시-3-메틸씨클로헥산 카르복실레이트; 3,4-에폭시-5-메틸씨클로헥실-메틸-3,4-에폭시-5-메틸씨클로헥산 카르복실레이트 등이 포함된다.As the curable resin, an aromatic or aliphatic or linear or branched epoxy resin can be used. The cycloaliphatic epoxy includes 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate such as 3,4- Epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate; 3,4-epoxy-1-methylcyclohexyl-methyl-3,4-epoxy-1-methylcyclohexanecarboxylate; 6-methyl-3,4-epoxycyclohexylmethylmethyl-6-methyl-3,4-epoxycyclohexanecarboxylate; 3,4-epoxy-2-methylcyclohexylmethyl-3,4-epoxy-2-methylcyclohexanecarboxylate; 3,4-epoxy-3-methylcyclohexyl-methyl-3,4-epoxy-3-methylcyclohexanecarboxylate; 3,4-epoxy-5-methylcyclohexyl-methyl-3,4-epoxy-5-methylcyclohexanecarboxylate and the like.
에폭시 화합물은 고리지방족 또는 지환족 에폭시드일 수 있다. 고리지방족 에폭시드의 예에는 비스(3,4-에폭시씨클로헥실메틸)옥살레이트, 비스(3,4-에폭시씨클로헥실메틸)아디페이트, 비스(3,4-에폭시-6-메틸씨클로헥실메틸)아디페이트, 비스(3,4-에폭시씨클로헥실메틸)피멜레이트와 같은 디카르복실산의 고리지방족 에스테르의 디에폭시드 비닐씨클로헥센 디에폭시드; 리모넨 디에폭시드; 디씨클로펜타디엔 디에폭시드 등이 포함된다. 바람직하게는 싸이클로아리파틱 에폭시 레진을 사용한다. 지환족 에폭시드로는 다음 종류의 화합물(n은 1~30 정수)일 수 있다.
The epoxy compound may be a cyclic aliphatic or alicyclic epoxide. Examples of cyclic aliphatic epoxides include bis (3,4-epoxycyclohexylmethyl) oxalate, bis (3,4-epoxycyclohexylmethyl) adipate, bis (3,4-epoxy-6-methylcyclohexylmethyl) Adepate, diepoxidized vinylcyclohexene diepoxide of cycloaliphatic esters of dicarboxylic acids such as bis (3,4-epoxycyclohexylmethyl) pimelate; Limonene diepoxide; Dicyclopentadiene diepoxide, and the like. Preferably, cycloaliphatic epoxy resin is used. The alicyclic epoxide may be the following type of compound (n is an integer of 1 to 30).
열경화성개시제로는 아조화합물, 퀴닌, 니트로 화합물, 아실 할라이드, 하이드라존, 메르캅톤 화합물, 피릴륨화합물, 이미다졸, 클로로트라이아진, 벤조인, 벤조인 알킬 에테르, 다이-케톤, 페논 및 유기 과산화물을 들수 있으며, 혼합물의 0.05~10 wt%로 사용된다.Examples of the thermosetting initiator include azo compounds, quinines, nitro compounds, acyl halides, hydrazones, mercapton compounds, pyrylium compounds, imidazoles, chlorotriazines, benzoins, benzoin alkyl ethers, And 0.05 to 10 wt% of the mixture is used.
용제의 종류에는 특별히 한정하지는 않지만, 필름화할 경우에는 쉽게 휘발이 될 수 있도록 끓는점 120℃ 이하의 용매를 사용할 수 있다. 메틸에틸케톤, 아세톤, 톨루엔, 디메틸포름아미드, 메틸셀로솔브, 테트라하이드로 퓨란, N-메틸피롤리돈 등의 일종 또는 이종이상의 혼합을 들수 있으나, 이에 한정하지는 않는다. The kind of the solvent is not particularly limited, but when it is made into a film, a solvent having a boiling point of 120 ° C or less can be used so that it can be easily volatilized. But are not limited to, methyl ethyl ketone, acetone, toluene, dimethylformamide, methyl cellosolve, tetrahydrofuran, N-methylpyrrolidone and the like, or mixtures of two or more thereof.
만약 충진제를 필름화하지 않고, 액상충진액으로 유기발광소자에 코팅하고자 한다면, 비점이 120℃ 이상의 용매와 혼합하여 사용할 수 있으며, 점도는 100~10000cps 사이가 적합하다.If the filler is to be coated on the organic light emitting device without using a film as a film, it may be mixed with a solvent having a boiling point of 120 ° C or higher, and a viscosity of 100 to 10,000 cps is suitable.
충진액의 일정 두께를 유지시켜 주며, 외부의 충격을 줄이고자 무기입자의 필러를 함유하는 것이 특징으로 세라믹 필러, 글라스 필러, 금속산화물 필러등이 포함될 수 있으며, 입자의 모양은 판상, 구형, 바늘 형태 등이 될 수 있다. A glass filler, a metal oxide filler and the like, which is characterized in that it contains a filler of an inorganic particle in order to maintain a certain thickness of the filling liquid and reduce an external impact. The shape of the particle is a plate, And the like.
무기물의 종류에는 실리카, 또는 알루미나 등과 같은 세라믹 필러, P2O5, Li2O, Na2O, BaO, CaO, MgO, LiSO4, CaSO4, MgSO4, CoSO4, Ga2(SO4)3, Ti(SO4)2, NiSO4, CaCl2, MgCl2, SrCl2, YCl3, CuCl2, MgBr2, Mg(ClO4)2등의 일종 또는 이종 이상의 혼합을 들 수 있으나, 이에 제한되는 것은 아니다. The type of inorganic material of ceramic filler such as silica, or alumina, P 2 O 5, Li 2 O, Na 2 O, BaO, CaO, MgO, LiSO 4, CaSO 4, MgSO 4, CoSO 4, Ga 2 (SO 4) 3 , Ti (SO 4 ) 2 , NiSO 4 , CaCl 2 , MgCl 2 , SrCl 2 , YCl 3 , CuCl 2 , MgBr 2 and Mg (ClO 4 ) 2 . It is not.
무기물 충진제의 분산을 위해서 티올계화합물을 넣고 충진제의 표면에 티올계 화합물이 둘러 쌀 수 있도록 교반한다. To disperse the inorganic filler, the thiol compound is added and stirred so that the thiol compound can be surrounded on the surface of the filler.
티올계 화합물의 예로는 티오글리콜산, 머캅토벤조산, 티오구아닌, 머캅토에탄올, 프로판티올, 터페닐티올(Terphenylthiol), 프로펜티올(Propenethiol), 티아졸린티올(Thiazolinethiol), 페닐이미다졸티올(Phenylimidazolethiol), 페닐티아졸티올(Phenylthiazolethiol), 아미노티아졸티올(Aminothiadiazolethiol), 브로모벤조아졸티올(Bromobenzoxazolethiol), 브로모피리딘티올(Bromopyridinethiol), 플루오로벤조아졸티올(Fluorobenzoxazolethiol), 메톡시벤조아졸티올(Methoxybenzoxazolethiol), 카르보란티올(Carboranethiol), 멘타-8-티올-3-온(Mentha-8-thiol-3-one), 1-4-(하이드록시벤질)이미다졸-2-티올[1-(4-Hydroxybenzyl)imidazole-2-thiol], 1-메틸-1H-벤즈이미다졸-2-티올(1-Methyl-1H-benzimidazole-2-thiol), 1-페닐-1H-테트라졸-5-티올(1-Phenyl-1H-tetrazole-5-thiol), 1H-1,2,4-트리아졸-3-티올(1H-1,2,4-Triazole-3-thiol), 3-아미노-1,2,4-트리아졸-5-티올(3-Amino-1,2,4-triazole-5-thiol), 4-(트리플루오로메틸)피리미딘-2-티올[4-(Trifluoromethyl)pyrimidine-2-thiol], 4-아미노-5-(4-피리elf)-4H-1,2,4-트리아졸-3-티올[4-Amino-5-(4-pyridyl)-4H-1,2,4-triazole-3-thiol], 4-하이드록시-6-(트리플루오로메틸)피리미딘-2-티올[4-Hydroxy-6-(trifluoromethyl)pyrimidine-2-thiol], 4-메틸-4H-1,2,4-트리아졸-3-티올[4-Methyl-4H-1,2,4-triazole-3-thiol], 5-(3-피리딜)-1,3,4-옥사디아졸-2-티올[5-(3-Pyridyl)-1,3,4-oxadiazole-2-thiol], 5-(4-아미노페닐)-1,3,4-옥사디아졸-2-티올[5-(4-Aminophenyl)-1,3,4-oxadiazole-2-thiol], 5-(4-클로로페닐)1,3,4-옥사디아졸-2-티올[5-(4-Chlorophenyl)-1,3,4-oxadiazole-2-thiol], 5-(4-피리딜)-1,3,4-옥사디아졸-2-티올[5-(4-Pyridyl)-1,3,4-oxadiazole-2-thiol], 5-메틸-1,3,4-티아디아졸-2-티올[5-Methyl-1,3,4-thiadiazole-2-thiol], 5-메틸티오-1,3,4-티아디아졸-2-티올[5-Methylthio-1,3,4-thiadiazole-2-thiol], 5-페닐-1,3,4-옥사디아졸-2-티올[5-Phenyl-1,3,4-oxadiazole-2-thiol], 5-페닐-1H-1,2,4-트리아졸-3-티올[5-Phenyl-1H-1,2,4-triazole-3-thiol], 7-(트리플루오로메틸)퀴놀린-4-티올[7-(Trifluoromethyl)quinoline-4-thiol], 1-[2-(디메틸아미노)에틸]-1H-테트라졸-5-티올(1-[2-(Dimethylamino)ethyl]-1H-tetrazole-5-thiol), 11-(1H-피롤-1-일)운데칸-1-티올[11-(1H-pyrrol-1-yl)undecane-1-thiol], O-(2-카르복시에틸)-O'-(2-머캅토에틸)헵타에틸렌 글리콜[O-(2-Carboxyethyl)-O'-(2-mercaptoethyl)heptaethylene glycol], O-(2-머캅토에틸)-O'-메틸-헥사(에틸렌글리콜)[O-(2-Mercaptoethyl)-O'-methyl-hexa(ethylene glycol)], O-[2-(3-머캅토프로피오닐아미노)에틸]-O'-메틸폴리에틸렌 글리콜[O-[2-(3-Mercaptopropionylamino)ethyl]-O'-methylpolyethylene glycol], 1-나프탈렌티올(1-Naphthalenethiol),11-머캅토-1-운데카놀(11-Mercapto-1-undecanol), 2-티오바르비투르산(2-Thiobarbituric acid), 시스테아민하이트로클로라이드(Cysteamine hydrochloride), 티오콜레스테롤(Thiocholesterol), 1-(11-머캅토운데실)이미다졸[1-(11-Mercaptoundecyl)imidazole], 스피로놀락톤(Spironolactone), 1-에틸테트라졸-5-티올(1-Ethyltetrazole-5-thiol), 1-(3-하이드록시페닐)-1H-테트라졸-5-티올[1-(3-Hydroxyphenyl)-1H-Tetrazole-5-Thiol],1-(2-메톡시페닐)-4-(4-니트로페닐)1-H-이미다졸-2-티올[1-(2-Thoxyphenyl)-4-(4-Nitrophenyl)-1H-Imidazole-2-Thiol], 1-(3-메틸페닐)-4-(4-메틸페닐)-1H-이미다졸-2-티올 하이드로브로마이드[1-(3-Methylphenyl)-4-(4-Methylphenyl)-1H-Imidazole-2-Thiol Hydrobromide], 1-(4-(디플루오로메톡시)벤조일)-1,4,5,6-테트라하이드로사이클로펜타(D)이미다졸-2-티올[1-(4-(Difluomethoxy)Benzoyl)-1,4,5,6-Tetrahydrocyclopenta(D)Imidazole-2-Thiol], 1-(4-아미노페닐)-4-페닐-1H-이미다졸-2-티올[1-(4-Aminophenyl)-4-Phenyl-1H-Imidazole-2-Thiol], 1-(4-아미노페닐)테트라졸-5-티올 하이드로클로라이드[1-(4-Aminophenyl)Tetrazole-5-Thiol Hydrochloride], 1-(4-아미노페닐)테트라졸 -5-티올 하이드로클로라이드[1-(4-Aminophenyl)Tetrazole-5-Thiol Hydrochloride], 1-메틸-1H-이미다졸-2-티올(1-Methyl-1H-Imidazole-2-Thiol), 1-메틸-1H-테트라졸-5-티올(1-Methyl-1H-Tetrazole-5-Thiol), 1-나프탈렌-2-일-1H-테트라졸-5-티올(1-Naphthalen-2-YL-1H-Tetrazole-5-Thiol), 1-페닐-1H-(1,2,4)트리아졸-3-티올91-Phenyl-1H-(1,2,4)Triazole-3-Thiol], 1-(메틸티오)-7H-피롤로(2,3-D)피리미딘-4-티올[2-(Methylthio)-7H-Pyrrolo(2,3-D)Pyrimidine-4-Thiol], 1-아미노-5-(2-클로로-페닐)-피리미딘-4-티올[2-Amino-5-(2-Chloro-Phenyl)-Pyrimidine-4-Thiol], 2-메틸-9H-퓨린-6-티올(2-Methyl-9H-Purine-6-Thiol), 3-O-톨릴-6-톨릴-피라진-2-티올(3-O-Tolyl-6-P-Tolyl-Pyrazine-2-Thiol), 3-페닐-1,2,4-옥사디아졸-5-티올(3-Phenyl-1,2,4-Oxadiazole-5-Thiol), 4,5-비스(4-메톡시페닐)-4H-1,2,4-트리아졸-3-티올(4,5-BIS(4-Methoxyphenyl)-4H-1,2,4-Triazole-3-Thiol), 4,5-디벤질-4H-1,2,4-트리아졸-3-티올(4,5-Dibenzyl-4H-1,2,4-Triazole-3-Thiol), 4,5-디페닐-4H-1,2,4-트리아졸-3-티올(4,5-Diphenyl-4H-1,2,4-Triazole-3-Thiol), 4,6-디메틸-피리미딘-2-티올(4,6-Dimethyl-Pyrimidine-2-Thiol), 4-(2,3-디메틸페닐)-5-메틸-4H-1,2,4-트리아졸-3-티올[4-(2,3-Dimethylphenyl)-5-Methyl-4H-1,2,4-Triazole-3-Thiol], 4-(2,4-디메틸페닐)-5-(4-메톡시페닐)-4H-1,2,4-트리아졸-3-티올[4-(2,4-Dimethylphenyl)-5-(4-Methoxyphenyl)-4H-1,2,4-Triazole-3-Thiol],4-(2,4-디메틸페닐5-페닐-4H-1,2,4-트리아졸-3-티올[4-(2,4-Dimethylphenyl)-5-Phenyl-4H-1,2,4-Triazole-3-Thiol], 4-(4-브로모페닐)-1,3-티아졸-2-티올[4-(4-Bromophenyl)-1,3-Thiol-2-Thiol], 4-(4-브로모페닐)-5-(4-클로로페닐)-4H-1,2,4-트리아졸-3-티올[4-(4-Bromophenyl)-5-(4-Chlorophenyl)-4H-1,2,4-Triazole-3-Thiol], 4-(4-브로모페닐)-5-(4-메톡시페닐)-4H-1,2,4-트리아졸-3-티올[4-(4-Bromophenyl)-5-(4-Methoxyphenyl)-4H-1,2,4-Triazole-3-Thiol], 4-(4-클로로페닐)-1,3-티아졸-2-티올[4-(4-Chlorophenyl)-1,3-Thiazole-2-Thiol], 4-(4-클로로페닐)-5-(4-메톡시페닐)-4H-1,2,4-트리아졸-3-티올[4-(4-Chlorophenyl)-5-(4-Methoxyphenyl)-4H-1,2,4-Triazole-3-Thiol], 4-(4-에톡시페닐)-1,5-디페닐-1H-이미다졸-2-티올 하이드로브로마이드[4-(4-Ethoxyphenyl)-1,5-Diphenyl-1H-Imiadazole-2-Thiol Hydrobromide], 4-(4-메톡시페닐)-1-(4-메톡시페닐)-1H-이미다졸-2-티올 하이드로브로미드4-(4-Methoxyphenyl)-1-(4-Methylphenyl)-1H-Imidazole-2-Thiolhydrobromide],4-(벤질리덴아미노)-5-(2,4-디클로로페닐)-4H-1,2,4-트리아졸-3-티올[4-(Benzylideamino)-5-(2,4-Dichlorophenyl)-4H-1,2,4-Triazole-3-Tiol], 4-(벤질리덴아미노)-5-(2-브로모페닐)-4H-1,2,4-트리아졸-3-티올[4-(Benzylideneamino)-5-(2-Bromophenyl)-4H-1,2,4-Triazole-3-Thiol], 4-(벤질리덴아미노)-5-(2-클로로페닐)-4H-1,2,4-트리아졸-3-티올[4-(Benzylideneamino)-5-(2-Chlorophenyl)-4H-1,2,4-Triazole-3-Thiol], 4-(벤질리덴아미노)-5-(2-플루오로페닐)-4H-1,2,4-트리아졸-3-티올[4-(Benzylideneamino)-5-(2-Fluorophenyl)-4H-1,2,4-Triazole-3-Thiol], 4-(벤질리덴아미노)-5-(2-푸릴)-4H-1,2,4-트리아졸-3-티올[4-(Benzylideneamino)-5-(2-Furyl)-4H-1,2,4-Triazole-3-Thiol], 4-(벤질리덴아미노)-5-(2-메톡시페닐)-4H-1,2,4-트리아졸-3-티올[4-(Triazole-3-Thiol)-5-(2-Methoxyphenyl)-4H-1,2,4-Triazol-3-Thiol], 4-(벤질리덴아미노)-5-(2-메틸페닐)-4H-1,2,4-트리아졸-3-티올[4-(Benzylideneamino)-5-(2-Methylphenyl)-4H-1,2,4-Triazole-3-Thiol], 4-(벤질리덴아미노)-5-(2-피리디닐)-4H-1,2,4-트리아졸-3-티올[4-(Benzylideneamino)-5-(2-Pyridinyl)-4H-1,2,4-Triazole-3-Thiol], 4-(벤질리덴아미노)-5-(3,4,5-트리메톡시페닐)-4H-1,2,4-트리아졸-3-티올[4-(Benzylideneamino)-5-(3,4,5-Trimethoxyphenyl)-4H-1,2,4-Triazole-3-Thiol], 4-(벤질리덴아미노)-5-(3-클로로페닐)-4H-1,2,4-트리아졸-3-티올[4-(Benzylideneamino)-5-(3-Chlorophenyl)-4H-1,2,4-Triazole-3-Thiol], 4-(벤질리덴아미노)-5-(3-에톡시페닐)-4H-1,2,4-트리아졸-3-티올[4-(Benzylideneamino)-5-(3-Ethoxyphenyl)-4H-1,2,4-Triazole-3-Thiol], 4-(벤질리덴아미노)-5-(3-이소프로폭시페닐)-4H-1,2,4-트리아졸-3-티올[4-(Benzylideneamino)-5-(3-Isopropoxyphenyl)-4H-1,2,4-Triazole-3-Thiol], 4-(벤질리덴아미노)-5-(3-메톡시페닐)-4H-1,2,4-트리아졸-3-티올[4-(Benzylideneamino)-5-(3-Methoxyphenyl)-4H-1,2,4-Triazole-3-Thiol], 4-(벤질리덴아미노)-5-(3-메틸페닐)-4H-1,2,4-트리아졸-3-티올[4-(Benzylideneamino)-5-(3-Methylphenyl)-4H-1,2,4-Triazole-3-Thiol], 4-(벤질리덴아미노)-5-(3-피리디닐)-4H-1,2,4-트리아졸-3-티올[4-(Benzylideneamino)-5-(3-Pyridyl)-4H-1,2,4-Triazole-3-Thiol],4-(벤질리덴아미노)-5-(4-브로모페닐)-4H-1,2,4-트리아졸-3-티올[4-(Benzylideneamino)-5-(4-Bromophenyl)-4H-1,2,4-Triazole-3-Thiol], 4-(벤질리덴아미노)-5-(4-클로로페닐)-4H-1,2,4-트리아졸-3-티올[4-(Benzylideneamino)-5-(4-Chlorophenyl)-4H-1,2,4-Triazole-3-Thiol],4-(벤질리덴아미노)-5-(4-플루오로페닐)-4H-1,2,4-트리아졸-3-티올[4-Benzylideneamino)-5-(4-Fluorophenyl)-4H-1,2,4-Trizole-3-Thiol], 4-(벤질리덴아미노)-5-(4-메톡시페닐)-4H-1,2,4-트리아졸-3-티올[4-(Benzylideneamino)-5-(4-Methoxyphenyl)-4H-1,2,4-Trizole-3-Thiol],4-(벤질리덴아미노)-5-(4-메틸페닐)-4H-1,2,4-트리아졸-3-티올[4-(Benzylideneamino)-5-(4-Methoxyphenyl)-4H-1,2,4-Triazole-3-Thiol], 4-(벤질리덴아미노)-5-(4-Tert-부틸페닐)-4H-1,2,4-트리아졸-3-티올[4-(Benzylideneamino)-5-(4-Tert-Butylphenyl)-4H-1,2,4-Triazole-3-Thiol],4-(벤질리덴아미노)-5-(페녹시메틸)-4H-1,2,4-트리아졸-3-티올[4-(Benzylideneamino)-5-(Phenoxymethyl)-4H-1,2,4-Triazole-3-Thiol], 4-(벤질리덴아미노)-5-사이클로헥실-4H-1,2,4-트리아졸-3-티올[4-(Benzylideneamino)-5-Cyclohexyl-4H-1,2,4-Triazole-3-Thiol], 4-(벤질리덴아미노)-5-페닐-4H-1,2,4-트리아졸-3-티올[4-(Benzylideneamino)-5-Phenyl-4H-1,2,4-Triazole-3-Thiol], 4-알릴-5-페녹시메틸-4H-(1,2,4)트리아졸-3-티올[4-Allyl-5-Phenoxymethyl-4H-(1,2,4)Triazole-3-Thiol], 4-아미노-4H-1,2,4-트리아졸-3-티올(4-Amino-4H-1,2,4-Triazole-3-Thiol), 4-아미노-5-(2,4-디클로로페닐)-4H-1,2,4-트리아졸-3-티올[4-Amino-5-(2,4-Dichlorophenyl)-4H-1,2,4-Triazole-3-Thiol], 4-아미노-5-(2-브로모페닐)-4H-1,2,4-트리아졸-3-티올[4-AMINO-5-(2-Bromophenyl)-4H-1,2,4-Triazole-3-Thiol], 4-아미노-5-(2-클로로페닐)-피리미딘-2-티올[4-Amino-5-(2-Chloro-Phenyl)-Pyrimidine-2-Thiol], 4-아미노-5-(3,4,5-트리메톡시페닐)-4H-1,2,4-트리아졸-3-티올[4-Amino-5-(3,4,5-Trimethoxyphenyl)-4H-1,2,4-Triazole-3-Thiol], 4-아미노-5-(3-피리디닐)-4H-1,2,4-트리아졸-3-티올[4-Amino-5-(3-Pyridinyl)-4H-1,2,4-Triazole-3-Thiol], 4-아미노-5-(4-아미노페닐)-피리미딘-2-티올[4-Amino-5-(4-Amino-Phenyl)-Pyrimidine-2-Thiol], 4-아미노-5-(페녹시메틸)-4H-1,2,4-트리아졸-3-티올[4-Amino-5-(Phenoxymethyl)-4H-1,2,4-TRIAZOLE-3-THIOL], 4-아미노-5-부틸-4H-1,2,4-트리아졸-3-티올(4-Amino-5-Buthyl-4H-1,2,4-Triazole-3-Thiol), 4-아미노-5-에틸-4H-1,2,4-트리아졸-3-티올[4-Amino-5-Ethyl-4H-1,2,4-Triazole-3-Thiol], 4-아미노-5-메틸-4H-1,2,4-트리아졸-3-티올[4-Amino-5-Methyl-4H-1,2,4-Triazole-3-Thiol], 4-벤질-5-(2,4-디클로로페닐)-4H-1,2,4-트리아졸-3-티올[4-Benzyl-5-(2,4-Dichlorophenyl)-4H-1,2,4-Triazole-3-Thiol], 4-벤질-5-(3,4-디메톡시페닐)-4H-1,2,4-트리아졸-3-티올[4-Benzyl-5-(3,4-Dimethoxyphenyl)-4H-1,2,4-Triazole-3-Thiol], 4-벤질-5-(4-피리디닐)-4H-1,2,4-트리아졸-3-티올[4-Benzyl-5-(4-Pyridinyl)-4H-1,2,4-Triazole-3-Thiol], 4-벤질-5-(4-Tert-부틸페닐)-4H-1,2,4-트리아졸-3-티올[4-Benzyl-5-(4-Tert-Butylphenyl)-4H-1,2,4-Triazole-3-Thiol], 4-사이클로헥실-5-(2,4-디클로로페닐)-4H-1,2,4-트리아졸-3-티올[4-Cyclohexyl-5-(2,4-Dichlorophenyl)-4H-1,2,4-Triazole-3-Thiol], 4-사이클로헥실-5-(2-메톡시페닐)-4H-1,2,4-트리아졸-3-티올[4-Cyclohexyl-5-(2-Methoxyphenyl)-4H-1,2,4-Triazole-3-Thiol],4-사이클로헥실-5-(3,4,5-트리메톡시페닐)-4H-1,2,4-트리아졸-3-티올[4-Cyclohexyl-5-(3,4,5-Trimethoxyphenyl)-4H-1,2,4-Triazole-3-Thiol], 4-사이클로헥실-5-(3,4-디메톡시페닐)-4H-1,2,4-트리아졸-3-티올[4-Cyclohexyl-5-(3,4-Dimethoxyphenyl)-4H-1,2,4-Triazole-3-Thiol], 4-에틸-5-(4-니트로페닐)-4H-1,2,4-트리아졸-3-티올[4-Ethyl-5-(4-Nitrophenyl)-4H-1,2,4-Triazole-3-Thiol], 4-에틸-5-M-톨릴-4H-(1,2,4)트리아졸-3-티올[4-Ethyl-5-M-Tolyl-4H-(1,2,4)Triazole-3-Thiol], 4-에틸-5-페녹시메틸-4H-(1,2,4)트리아졸-3-티올[4-Ethyl-5-Phenoxymethyl-4H-(1,2,4)Triazole-3-Thiol], 4-메틸-6-트리플루오로메틸-피리미딘-2-티올(4-Methyl-6-Trifluoromethyl-Pyrimidine-2-Thiol), 4-O-톨릴-5-P-톨릴-4H-(1,2,4)트리아졸-3-티올[4-O-Tolyl-5-P-Trimethoxyphenyl)-4H-1,2,4-Triazole-3-Thiol], 4-페닐-5-M-톨릴-4H-(1,2,4)트리아졸-3-티올[4-Phenyl-5-M-Tolyl-4H-(1,2,4)Triazole-3-Thiol],5,5'-(에틸렌디티오)비스(1,3,4-티아디아졸-2-티올)[5,5'-(Ethylendituio)Bis(1,3,4-Thiadiazole-2-Thiol)],5,5'-테트라메틸렌비스(4-페닐-4H-1,2,4-트리아졸-3-티올[5,5'-Tetramethylenebis(4-Phenyl-4H-1,2,4-Triazole-3-Thiol), 5,6,7,8-테트라하이드로-퀴나졸린-2-티올(5,6,7,8-Tetrahydro-Quinazoline-2-Thiol),5,6-디하이드로-4H-(1,3)티아진-2-티올[5,6-Dihydro-4H-(1,3)Thiazine-2-Thiol], 5,7-비스(에틸아미노)(1,2,4)트리아졸로(4,3-A)(1,3,5)트리아진-3-티올[5,7-BIS(Ethylamino)(1,2,4)Triazolo(4,3-A)(1,3,5)Triazine-3-Thiol], 5-((1-나프틸메틸)설패닐)-1,3,4-티아디아졸-2-티올[5-((1-Naphthylmethyl)Sulfanyl)-1,3,4-Thiadiazole-2-Thiol], 5-(2,4-디클로로페녹시메틸)-(1,3,4)옥사디아졸-2-티올[5-(2,4-Dichloro-Phenoxymethyl)-(1,3,4)Oxadiazole-2-Thiol], 5-(2,4-디클로로페닐)-4-(4-메틸페닐)-4H-1,2,4-트리아졸-3-티올[5-(2,4-Dichlorophenyl)-4-(4-Methylphenyl)-4H-1,2,4-Triazole-3-Thiol], 5-(2,4-디클로로페닐)-4-에틸-4H-1,2,4-트리아졸-3-티올[5-(2,4-Dichlorophenyl)-4-Ethyl-4H-1,2,4-Triazole-3-Thiol], 5-(2-클로로에틸티오)-1,3,4-티아디아졸-2-티올[5-(2-Chloroethylthio)-1,3,4-Thiadiazole-2-Thiol], 5-(2-푸릴)-4-(4-메톡시페닐)-4H-1,2,4-트리아졸-3-티올[5-(2-Furyl)-4-(4-Methoxyphenyl)-4H-1,2,4-Triazole-3-Thiol], 5-(3-클로로페닐)-4-(4-플루오로페닐)-4H-1,2,4-트리아졸-3-티올[5-(3-Chlorophenyl)-4-(4-Fluorophenyl)-4H-1,2,4-Triazole-3-Thiol], 5-(3-클로롤페닐)-4-이소부틸-4H-1,2,4-트리아졸-3-티올[5-(3-Chlorophenyl)-4-Isobutyl-4H-1,2,4-Triazole-3-Thiol], 5-(3-메틸페닐)-4-(4-메틸페닐)-4H-1,2,4-트리아졸-3-티올[5-(3-Methylphenyl)-4-(4-Methylphenyl)-4H-1,2,4-Triazole-3-Thiol], 5-(4-브로모페닐)-4-(2,4-디메틸페닐)-4H-1,2,4-트리아졸-3-티올[5-(4-Bromophenyl)-4-(2,4-Dimethylphenyl)-4H-1,2,4-Triazole-3-Thiol],5-(4-브로모페닐)-4-(2-메틸페닐)-4H-1,2,4-트리아졸-3-티올[5-(4-Bromophenyl)-4-(2-Methylphenyl)-4H-1,2,4-Triazole-3-Thiol], 5-(4-브로모페닐)-4-(2-메틸페닐)-4H-1,2,4-트리아졸-3-티올[5-(4-Bromophenyl)-4-(2-Methylphenyl-4H-1,2,4-Triazole-3-Thiol], 5-(4-클로로페닐)-(1,3,4)옥사디아졸-2-티올[5-(4-Chlorophenyl)-(1,3,4)Oxadizole-2-Thiol], 5-(4-클로로페닐)-피리미딘-4-티올[5-(4-Chlorophenyl)-Pyrimidine-4-Thiol], 5-(4-클로로페닐)-4-(4-메톡시페닐)-4H-1,2,4-트리아졸-3-티올[5-(4-Chlorophenyl)-4-(4-Methoxaphenyl)-4H-1,2,4-Triazole-3-Thiol], 5-(4-클로로페닐)-4-이소부틸-4H-1,2,4-트리아졸-3-티올[5-(4-Chlorophenyl)-4-Isobutyl-4H-1,2,4-Triazole-3-Thiol], 5-(벤질티오)-1,3,4-티아디아졸-2-티올[5-(Benzylthio)-1,3,4-Thiadiazole-2-Thiol], 5-(부틸티오)-1,3,4-티아디아졸-2-티올[5-(Buthylthio)-1,3,4-Thiadiazole-2-Thiol], 5-(도데실티오)-1,3,4-티아디아졸-2-티올[5-(Dodecylthio)-1,3,4-Thiadiazole-2-Thiol], 5-(에틸티오)-1,3,4-티아디아졸-2-티올[5-(Eethylthio)-1,3,4-Thiadiazole-2-Thiol], 5-(헥실티오)- 1,3,4-티아디아졸-2-티올[5-(Hexylthio)-1,3,4-Thiadiazole-2-Thiol], 5-(페닐티오)-1,3,4-티아디아졸-2-티올[5-(Pentylthio)-1,3,4-Thiadiazole-2-Thiol], 5-아미노-1,3,4-티아디아졸-2-티올[5-Amino-1,3,4-Thiadiazole-2-Thiol], 5-아미노-4-페닐-4H-(1,2,4)트리아졸-3-티올[5-Amino-4-Phenyl-4H-(1,2,4)Triazole-3-Thiol], 5-벤질-4-페닐-4H-(1,2,4)트리아졸-3-티올[5-Benzyl-4-Phenyl-4H-(1,2,4)Triazole-3-Thiol], 등으로 이루어진 군에서 선택된 1종 이상의 것일 수 있다.
Examples of thiol compounds include thioglycolic acid, mercaptobenzoic acid, thioguanine, mercaptoethanol, propanethiol, terphenylthiol, propenethiol, thiazolinethiol, phenylimidazole thiol For example, phenylimidazolethiol, phenylthiazolethiol, aminothiadiazolethiol, bromobenzoxazolethiol, bromopyridinethiol, fluorobenzoxazolethiol, methoxybenzazolyl, Methoxybenzoxazolethiol, Carboranethiol, Mentha-8-thiol-3-one, 1-4- (hydroxybenzyl) imidazole-2-thiol [1 Methyl-1H-benzimidazole-2-thiol, 1-phenyl-1H-tetrazole-2-thiol, 1H-tetrazole-5-thiol, 1H-1,2,4-triazole-3-thiol, 3-amino- 1,2,4-triazole-5-thiol (3-Amino-1,2, 4-triazole-5-thiol, 4- (trifluoromethyl) pyrimidine-2-thiol and 4-amino-5- (4-pyridyl) 3-thiol], 4-hydroxy-6- (tri (4-pyridyl) Pyrimidine-2-thiol], 4-methyl-4H-1,2,4-triazole-3-thiol [4-Methyl- 4H-1,2,4-triazole-3-thiol], 5- (3-pyridyl) -1,3,4-oxadiazole- 4-oxadiazole-2-thiol], 5- (4-aminophenyl) -1,3,4-oxadiazole- thiol], 5- (4-chlorophenyl) 1,3,4-oxadiazole-2-thiol], 5- (4-chlorophenyl) Pyridyl) -1,3,4-oxadiazole-2-thiol], 5-methyl-1,3,4- Thiadiazole-2-thiol], 5-methylthio-1,3,4-thiadiazole-2-thiol [5-Methylthio- 3,4-thiadiazole-2-thiol], 5-phenyl-1,3,4-oxadiazole-2-thiol [ 1,3,4-oxadiazole-2-thiol], 5-phenyl-1H-1,2,4-triazole-3-thiol, , 7- (trifluoromethyl) quinoline-4-thiol, 1- [2- (dimethylamino) ethyl] -1H- [11- (1H-pyrrol-1-yl) undecane-1-yl] ethyl] -1H-tetrazole- -thiol], O- (2-carboxyethyl) -O '- (2-mercaptoethyl) heptaethylene glycol O- (2-mercaptoethyl) heptaethylene glycol] (2-mercaptoethyl) -O'-methyl-hexa (ethylene glycol)], O- [2- (3-mercaptopropionyl) Amino] ethyl] -O'-methylpolyethylene glycol [O- [2- (3-Mercaptopropionylamino) ethyl] -O'-methyl polyethylene glycol, 1-naphthalenethiol, 1-undecanol, 2-thiobarbituric acid, cysteamine hydrochloride, thiobarbituric acid, (1-Ethyltetrazole-5-thiol), thioglycerol, thiocholesterol, 1- (11-mercaptoundecyl) imidazole, spironolactone, -thiol), 1- (3-hydroxyphenyl) -1H-tetrazole-5-thiol, 1- (4-nitrophenyl) -1H-imidazole-2-thiol], 1- (3-methylphenyl) (4-methylphenyl) -1H-imidazole-2-thiol hydrobromide], 1- (3-methylphenyl) Benzoyl) -1,4,5,6-tetrahydrocyclopenta (D) imidazole-2-thiol [1- (4- (Difluoromethoxy) benzoyl) 6-Tetrahydrocyclopenta (D) Imidazole-2-Thiol], 1- (4-aminophenyl) -4-phenyl-1H-imidazole- -2-thiol], 1- (4-aminophenyl) tetrazole-5-thiol hydrochloride [1- (4- Aminophenyl) Tetrazole- 1-methyl-1H-imidazole-2-thiol (1- (4-aminophenyl) Methyl-1H-imidazole-2-thiol), 1-methyl-1H-tetrazole-5-thiol, 1-naphthalen- 1-Naphthalen-2-YL-1H-Tetrazole-5-Thiol), 1-phenyl-1H- (1,2,4) triazole-3-thiol 91- , 4) triazole-3-thiol], 1- (methylthio) -7H-pyrrolo (2,3-D) pyrimidin- Pyrimidine-4-thiol], 1-amino-5- (2-chloro-phenyl) 2-methyl-9H-purine-6-thiol, 3-O-tolyl-6-tolyl-pyrazine- 2-thiol), 3-phenyl-1,2,4-oxadiazole-5-thiol, 4,5-bis (4-methoxyphenyl) -4H-1,2,4-triazole-3-thiol), 4 (4-methoxyphenyl) -4H-1,2,4- , 5-dibenzyl-4H-1,2,4-tri 4,5-Dibenzyl-4H-1,2,4-triazole-3-thiol, 4,5-diphenyl-4H-1,2,4-triazole- 4-triazole-3-thiol), 4,6-dimethyl-pyrimidine-2-thiol, 4- (2-thiophene- , 3-dimethylphenyl) -5-methyl-4H-1,2,4-triazole [4- (2,3-Dimethylphenyl) -5- 3-thiol], 4- (2,4-dimethylphenyl) -5- (4-methoxyphenyl) -4H-1,2,4- triazole- Phenyl-4H-1,2,4-triazol-3-thiol], 4- (2,4- 4-triazole-3-thiol], 4- (4-bromophenyl) -1,3-thiazole- 2- Thiol-2-thiol], 4- (4-bromophenyl) -5- (4-chlorophenyl) -4H-1,2,4-triazole -4-triazole-3-thiol], 4- (4-bromophenyl) -5- (4-chlorophenyl) 4-Bromophenyl) -5- (4-methoxyphenyl) -4H-1,2,4-triazole-3-thiol ], 4- (4-chlorophenyl) -1,3-thi 2-thiol], 4- (4-chlorophenyl) -5- (4-methoxyphenyl) -4H- 4-triazole-3-thiol], 4- (4-methoxyphenyl) -4H-1,2,4- 1,5-diphenyl-1H-imidazole-2-thiol hydrobromide, 4- (4-methoxyphenyl) (4-methoxyphenyl) -1H-imidazole-2-thiolhydrobromide], 4- (4-methoxyphenyl) (Benzylideneamino) -5- (2,4-dichlorophenyl) -4H-1,2,4-triazole [ 1,2,4-Triazole-3-Tiol], 4- (benzylideneamino) -5- (2-bromophenyl) -4H-1,2,4- triazole [4- (2-bromophenyl) -4H-1,2,4-triazole-3-thiol], 4- (benzylideneamino) 3-thiol], 4- (benzylideneamino) -5- (2-chlorophenyl) -4H- 4H-1,2,4-triazole-3-thiol], 4 (4-fluorophenyl) -4H-1,2,4- - (benzylideneamino) -5- (2-furyl) -4H-1,2,4-triazol- 4-triazole-3-thiol], 4- (benzylideneamino) -5- (2-methoxyphenyl) -4H-1,2,4- triazole [ (2-methoxyphenyl) -4H-1,2,4-triazol-3-thiol], 4- (benzylideneamino) -5- 4-triazole-3-thiol], 4- (benzylideneamino) -5- (2-pyridinyl) ) -4H-1,2,4-triazole-3-thiol], 4- (benzylideneamino) -5- (3,4,5-trimethoxyphenyl) -4H-1,2,4-triazole [4- (Benzylideneamino) -5- (3,4,5-trimethoxyphenyl) ) -4H-1,2,4-triazole-3-thiol], 4- (benzylideneamino) -5- (3- chlorophenyl) -4H- - (Benzylideneamino) -5- (3-chlorophenyl) -4H- 1,2,4-triazole-3-thiol], 4- (3-ethoxyphenyl) -4H-1,2,4-triazol-3-yl] 4-triazole-3-thiol], 4- (benzylideneamino) -5- (3-isopropoxyphenyl) -4H-1,2,4- triazole- - (3-Isopropoxyphenyl) -4H-1,2,4-triazole-3-Thiol], 4- (benzylideneamino) -5- (3- methoxyphenyl) -4H- -3-thiol], 4- (benzylideneamino) -5- (3-methoxyphenyl) -4H-1,2,4-triazole- 4H-1,2,4-triazole-3-thiol], 4- (benzylideneamino) -5- 4- (Benzylideneamino) -5- (3-pyridyl) -4H-1,2,4-triazole- 3-thiol], 4- (benzylideneamino) -5- (4-bromophenyl) -4H-1,2,4-triazole [ -4H-1,2,4-triazole-3-thiol], 4- (benzylideneamino) -5- (4- chlorophenyl) -4H- - (Benzylideneamino) -5- (4-chlorophenyl) -4H-1 , 2,4-triazole-3-thiol], 4- (benzylideneamino) -5- (4-fluorophenyl) -4H-1,2,4- triazole- (4-fluorophenyl) -4H-1,2,4-trizole-3-thiol], 4- (benzylideneamino) Benzylideneamino) -5- (4-methoxyphenyl) -4H-1,2,4-trizole-3-thiol], 4- (benzylideneamino) -4H-1,2,4-triazole-3-thiol], 4- (benzylideneamino) -5- (4-tert-butylphenyl) -4H-1,2,4-triazole [4- (Benzylideneamino) -5- , 4-triazole-3-thiol], 4- (benzylideneamino) -5- (phenoxymethyl) -4H-1,2,4- triazole- [4- (Benzylideneamino) -5- 3-thiol], 4- (benzylideneamino) -5-cyclohexyl-4H-1,2,4-triazole [4- (Benzylideneamino -5-Cyclohexyl-4H-1,2,4-triazole-3-thiol], 4- (benzylideneamino) (Benzylideneamino) -5-Phenyl-4H-1,2 4-triazole-3-thiol], 4-allyl-5-phenoxymethyl-4H- (1,2,4) triazole-4-Allyl-5-phenoxymethyl- 4) triazole-3-thiol], 4-amino-4H-1,2,4-triazole-3-thiol, 4- Amino-5- (2,4-dichlorophenyl) -4H-1,2,4-triazole [4-Amino-5- (2,4- Triazole-3-thiol], 4-amino-5- (2-bromophenyl) -4H-1,2,4- triazole-4-AMINO- 1,2,4-triazole-3-thiol], 4-amino-5- (2-chlorophenyl) -pyrimidine- -Thiol], 4-amino-5- (3,4,5-trimethoxyphenyl) -4H-1,2,4-triazole-3-thiol [ (4-amino-5- (3-pyridinyl) -4H-1,2,4-triazole-3-thiol [4-Amino Amino-5- (4-aminophenyl) -pyrimidine-2-thiol [4-Amino-5- (4-Amino-Phenyl) -Pyrimidine-2-Thiol], 4-amino-5- (phenoxymethyl) -4H-1,2,4- triazole- 4-amino-5-buthyl-4H-1,2,4-triazol-3- Amino-5-ethyl-4H-1,2,4-triazole-3-thiol [4-Amino-5- 4-triazole-3-thiol], 4-amino-5-methyl-4H-1,2,4-triazole [ -3-thiol], 4-benzyl-5- (2,4-dichlorophenyl) -4H-1,2,4- 4H-1,2,4-triazole-3-thiol], 4-benzyl-5- (3,4- dimethoxyphenyl) -4H- 3-thiol], 4-benzyl-5- (4-pyridinyl) -4H-1,2,4-triazole-3 4-benzyl-5- (4-pyridinyl) -4H-1,2,4-triazole-3-thiol], 4-benzyl-5- (4-tert- 4-Benzyl-5- (4-tert-butylphenyl) -4H-1,2,4-triazole-3-thiol], 4-cyclohexyl- -Dichlorophenyl) -4H-1,2,4-triazole-3-thiol 4-Cyclohexyl-5- (2,4-dichlorophenyl) -4H- -Cyclohexyl-5- (2-methoxy 4H-1,2,4-triazole-3-thiol], 4-cyclohexyl-5- 4-cyclohexyl-5- (3,4,5-trimethoxyphenyl) -4H-1,2,4-triazole [ 2,4-triazole-3-thiol], 4-cyclohexyl-5- (3,4-dimethoxyphenyl) -4H-1,2,4- triazole- 3-thiol], 4-ethyl-5- (4-nitrophenyl) -4H-1,2,4-triazole-3-thiol [ 4-Ethyl-5- (4-Nitrophenyl) -4H-1,2,4-triazole-3-Thiol] Triazole-3-thiol], 4-ethyl-5-phenoxymethyl-4H- (1,2,4) triazole 3-thiol], 4-methyl-6-trifluoromethyl-pyrimidine-2-thiol (4-Methyl 5-P-tolyl-4H- (1,2,4) triazole-3-thiol [4-O-Tolyl-5-P- 4-phenyl-5-M-tolyl-4H- (1,2,4) triazole-3-thiol [4-Phenyl -5-M-Tolyl-4H- (1,2,4) Triazole-3-Thiol], 5,5 '- (Ethylenedithio) bis (1,3,4-thiadiazole- 5,5'- (Ethylendituio) Bis (1,3,4-Thiadiazole-2-Thiol), 5,5'-tetramethylene bis (4-phenyl- Thiol [5,5'-Tetramethylenebis (4-Phenyl-4H-1,2,4-Triazole-3-Thiol), 5,6,7,8-tetrahydro- quinazoline- 7,8-Tetrahydro-Quinazoline-2-Thiol), 5,6-dihydro-4H- (1,3) thiazine- -Thiol], 5,7-bis (ethylamino) (1,2,4) triazolo (4,3-A) (1,3,5) triazine- Triazine-3-thiol], 5 - ((1-naphthylmethyl) sulfanyl) -1,3,4- Thiadiazole-2-thiol], 5- (2,4-dichlorophenoxymethyl) - (1, 3-dihydro- 4) Oxadiazole-2-thiol [5- (2,4-Dichloro-Phenoxymethyl) - (1,3,4) Oxadiazole- 4-methylphenyl) -4H-1,2,4-triazole [5- (2,4-Dichlorophenyl) -4- e-3-thiol], 5- (2,4-dichlorophenyl) -4-ethyl-4H-1,2,4- triazole [5- -4H-1,2,4-triazole-3-thiol], 5- (2-chloroethylthio) -1,3,4-thiadiazole- 3,4-thiadiazole-2-thiol], 5- (2-furyl) -4- (4-methoxyphenyl) -4H- (4-methoxyphenyl) -4H-1,2,4-triazole-3-thiol], 5- (3- chlorophenyl) -4- 4-triazole-3-thiol], 5- (3-chlorophenyl) - 4-Isobutyl-4H-1,2,4-triazole-3-thiol], 5- ( Methylphenyl) -4H-1,2,4-triazol-3-thiol [5- (3-Methylphenyl) -4- (4-methylphenyl) 4-triazole-3-thiol], 5- (4-bromophenyl) -4- (2,4- (4-bromophenyl) -4- (2-methylphenyl) -4H-1, 2,4-triazole- 2,4-triazole-3-thiol [5- (4- Bromophenyl) -4- (2-methylphenyl) -4H-1,2,4-triazole-3-thiol] 4-Bromophenyl-4H-1,2,4-triazole-3-thiol], 5- (4-chlorophenyl) - , 3,4) oxadiazole-2-thiol, 5- (4-chlorophenyl) -pyrimidine-4-thiol 4- [4-methoxyphenyl] -4H-1,2,4-triazole-3-thiol [5- (4-chlorophenyl) 3-thiol], 5- (4-chlorophenyl) -4-isobutyl-4H-1,2 4-Isobutyl-4H-1,2,4-triazole-3-thiol], 5- (benzylthio) -1,3,4- Thiadiazole-2-thiol], 5- (butylthio) -1,3,4-thiadiazole-2-thiol [5- Thiadiazole-2-thiol], 5- (dodecylthio) -1,3,4-thiadiazole-2-thiol [5- (Dodecylthio) -1,3,4 -Thiadiazole-2-thiol], 5- (ethylthio) -1,3,4-thiadiazole-2-thiol [5- (Eethylthio) -1,3,4- azole-2-thiol], 5- (hexylthio) -1,3,4-thiadiazole-2-thiol, Phenylthio) -1,3,4-thiadiazole-2-thiol], 5-amino-1,3,4-thiadiazole Thiadiazole-2-thiol], 5-amino-4-phenyl-4H- (1,2,4) triazole-3-thiol [5-Amino- Benzyl-4-phenyl-4H- (1,2,4) triazole-3-thiol] Phenyl-4H- (1,2,4) triazole-3-thiol], and the like.
기판과의 접착력을 높이고자 실란커플링제를 첨가제로 0.01 wt%~3 wt%를 사용할 수 있다. 실란커플링제의 종류에는 비닐트리메톡시실란, 비닐트리에톡시실란, 2-(3,4-에폭시시클로헥실)에틸트리메톡시실란, 3-글리시독시프로필트리메톡시실란, 3-글리시독시프로필메틸디에톡시실란, 3-글리시독시프로필트리에톡시실란, p-스티릴트리메톡시실란, 3-메타크릴록시프로필메틸디에톡시실란, 3-메타크릴록시프로필트리메톡시실란, 3-메타크릴록시프로필메틸디에톡시실란, 3-메타크릴록시프로필트리에톡시실란, 3-아크릴록시프로필트리메톡시실란, 3-우레이도프로필트리에톡시실란, 3-클로로프로필트리메톡시실란, 3-메르캅토프로필메틸디메톡시실란, 3-메르캅토프로필트리메톡시 실란, 3-이소시아네이트프로필트리에톡시실란 등을 들 수 있다. A silane coupling agent may be used as an additive in an amount of 0.01 wt% to 3 wt% in order to increase the adhesion to the substrate. Examples of the silane coupling agent include vinyltrimethoxysilane, vinyltriethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3- 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, Methacryloxypropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-mercaptopropylmethyldimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-isocyanatepropyltriethoxysilane and the like.
상기의 충진액 도포방법으로는 롤 코트, 스프레이 코트, 그라비어 코트, 콤마 코트 또는 립 코트등과 같은 방법이 있으며, 이에 한정하지는 않는다.Examples of the method of applying the filling liquid include roll coating, spray coating, gravure coating, comma coating and lip coating, but the present invention is not limited thereto.
본 발명의 유기발광 소자 봉지재용 황변방지 조성물은 높은 Hardness를 가질 뿐만 아니라, 경화 후의 높은 투명도를 가지기 때문에 전면발광유기 소자에 적용할 수 있다. 또한 수분 및 산소의 차단을 높여 소자의 수명을 높이며, 액상형태, 필름형태로 제조되어 OLED 패널제조의 공정성이 용이하다.The yellowing prevention composition for an encapsulating material for an organic luminescent element of the present invention not only has high hardness, but also has high transparency after curing, so that it can be applied to a top emission organic EL device. In addition, the lifetime of the device is increased by increasing the interception of moisture and oxygen, and it is manufactured in a liquid form and a film form, so that the manufacturing process of the OLED panel is easy.
도 1은 본 발명의 투과율(%)을 UV / Vis spectrometer를 사용하여 측정한 결과이다.1 shows the results of measurement of the transmittance (%) of the present invention using a UV / Vis spectrometer.
이하에서 실시예 및 비교예를 통하여 본 발명을 보다 구체적으로 설명하나, 다음의 실시예는 본 발명의 이해를 돕기 위하여 예시하는 것일 뿐 본 발명이 이에 의하여 국한되는 것은 아니다.
Hereinafter, the present invention will be described in more detail with reference to examples and comparative examples. However, the following examples are provided to illustrate the present invention, but the present invention is not limited thereto.
<실시예 1-3>≪ Example 1-3 >
1) 충진용액의 제조 1) Preparation of filling solution
티올계 화합물(아라카와 SQ 102-1) 10 wt%를 무기필러(한국 합성 펄 공업 TALC MM) 10 wt%와 먼저 교반기에 넣고 혼합하였다. 실리콘 화합물(화학식 1, 삼호 CNE,SH 504-1) 및 나머지 재료들을 표 1과 같이 Bis A epoxy(국도화학 YH 120) 10~50wt%, Bis F epoxy(국도화학 YH 170) 10∼50wt%, Cycloaliphatic epoxy resin(다이셀 3150CE) 30∼50wt%, 페녹시 수지(미츠비시 케미칼 JER 1256) 10∼30wt%, 경화제 (아데카 CP 66) 0.5∼5wt%, 첨가제 (신에츠 KBM 403)0.5∼5wt%를 교반기에 넣고 혼합한다.
10 wt% of a thiol compound (Arakawa SQ 102-1) was mixed with 10 wt% of an inorganic filler (TALC MM, Korea Synthetic Pearl Industry Co., Ltd.) in a stirrer. 10 to 50 wt% of Bis A epoxy (National Chemical Industries YH 120), 10 to 50 wt% of Bis F epoxy (National Chemical Co. YH 170) as shown in Table 1, , 0.5 to 5 wt% of a curing agent (Adeka CP 66), 0.5 to 5 wt% of an additive (Shin-Etsu KBM 403), 10 to 30 wt% of a phenolic resin (Mitsubishi Chemical JER 1256) Mix in an agitator.
2) 충진필름의 제조 2) Manufacture of filled film
필름의 이형면에 충진용액을 도포하고 (도포의 방법으로는 한정하지 아니한다.) 60~80℃에서 수 분간 건조하여 두께가 20㎛이하의 두께를 가지는 충진필름층을 형성하였다. 충진필름층이 코팅된 이형필름층과 보호필름층을 합착하여 충진필름을 제조하였다.
A filler solution is applied to the release surface of the film (it is not limited to the coating method) and dried at 60 to 80 ° C for several minutes to form a filler film layer having a thickness of 20 μm or less. A release film layer coated with a filler film layer and a protective film layer were adhered to each other to prepare a filled film.
<비교예 1~2>≪ Comparative Examples 1 and 2 &
실시예 1~3과 동일한 방법과 재료를 사용하고 표 1의 배합비의 범위로 사용하여 충진용액을 제조하고 충진층이 코팅된 이형필름층과 보호필름층을 합착하여 충진필름을 제조하였다.
Using the same method and materials as those of Examples 1 to 3, the filler solution was prepared in the range of the compounding ratio shown in Table 1, and a release film layer coated with a filler layer and a protective film layer were laminated to prepare a filler film.
상기 물질의 구체적인 물질 및 사용예는 과제의 해결수단에 열거되어 있다.
Specific materials and examples of use of these materials are listed in the solution of the problem.
<시험예 1-3>; 물성측정 실험≪ Test Example 1-3 > Physical property measurement experiment
1) 경도(hardness) 1) Hardness
본 발명의 조성물을 대상으로 하여 100℃/ 2hrs. 경화 후 연필경도를 측정하였으며 JIS-D5400 규격에 준하는 Test기 및 연필을 사용하여 9.8N의 부하를 가하여 물성을 측정하여 그 결과를 다음의 표 2 나타내었다.
The composition of the present invention was subjected to a heat treatment at 100 DEG C / 2hrs. After curing, the pencil hardness was measured. Using a test machine and a pencil according to JIS-D5400 standard, a load of 9.8 N was applied, and physical properties were measured. The results are shown in Table 2 below.
상기의 결과로부터 본 발명의 조성물은 비교예에 비하여 연필경도가 2H이상 우수한 것으로 나타났다.
From the above results, the composition of the present invention showed a pencil hardness of 2H or more superior to the comparative example.
2) 투과율( transmissivity)2) Transmissivity
본 발명의 조성물을 대상으로 하여 UV / Vis spectrometer를 사용하여 투과율(%)를 측정하여 그 결과를 다음의 도 1에 나타내었다.
The transmittance (%) of the composition of the present invention was measured using a UV / Vis spectrometer and the results are shown in FIG.
3) 황변성(Yellowness Index)3) Yellowness Index
본 발명의 조성물을 대상으로 하여 황변성을 측정하여 표 3에 나타내었다.
The composition of the present invention was subjected to measurement of sulfur denaturation and is shown in Table 3.
상기의 결과로부터 본 발명의 조성물이 비교예 보다도 황변성이 0.23-0.25 정도 우수한 것으로 나타났다.From the above results, it was found that the composition of the present invention was superior to the comparative example by about 0.23-0.25 in the sulfur change.
본 발명의 조성물은 지환족 에폭시수지와 실리콘 수지를 혼합 사용하여 에폭시의 높은 경도를 그대로 유지하면서 경화 후에 높은 투명도를 제공할 수 있으므로 산업상 이용가능성이 있다.
The composition of the present invention can be used industrially because a high transparency can be provided after curing while maintaining the high hardness of epoxy by using alicyclic epoxy resin and silicone resin.
Claims (13)
상기 조성물은 하기 화학식 1로 표시되는 경화용 실리콘 수지, 에폭시 화합물, 열경화성 개시제, 용제, 충진제, 무기물, 티올계 화합물 및 실란커플링제를 포함하는 것을 특징으로 하는 유기발광 소자 봉지재용 황변방지 조성물
<화학식 1>
상기 화학식 1에서, R1은 독립적으로 불포화 결합을 1개 이상 가지는 탄소수 2 내지 10의 비닐기, 메타크릴기, 메타크릴옥시기, 아세테이트기, 아크릴기, 아크릴옥시기 및 머캅토기이고,
R2는 독립적으로 히드록시기, 수소, 불소, 탄소수 1 내지 10의 직쇄 또는 분지쇄 알킬기, 탄소수 3 내지 15의 시클로알킬기, 탄소수 2 내지 10의 아릴기, 에폭시기 및 페닐렌기로 이루어진 군으로부터 선별되며,
Me는 금속이다A yellowing prevention composition for encapsulating an organic light emitting element comprising a curable silicone resin,
Wherein the composition comprises a silicone resin for curing represented by the following formula (1), an epoxy compound, a thermosetting initiator, a solvent, a filler, an inorganic compound, a thiol compound and a silane coupling agent
≪ Formula 1 >
Wherein R1 is independently a vinyl group, a methacryl group, a methacryloxy group, an acetate group, an acrylic group, an acryloxy group and a mercapto group having 2 to 10 carbon atoms and having at least one unsaturated bond,
R2 is independently selected from the group consisting of a hydroxyl group, hydrogen, fluorine, a linear or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 15 carbon atoms, an aryl group having 2 to 10 carbon atoms, an epoxy group,
Me is a metal
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2013
- 2013-12-31 KR KR1020130168932A patent/KR20150079001A/en not_active Application Discontinuation
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