KR20120033916A - Encapsulation composition, cured layer and organic light emitting device, liquid crystal display, plasma display display and solar cell - Google Patents
Encapsulation composition, cured layer and organic light emitting device, liquid crystal display, plasma display display and solar cell Download PDFInfo
- Publication number
- KR20120033916A KR20120033916A KR1020100095673A KR20100095673A KR20120033916A KR 20120033916 A KR20120033916 A KR 20120033916A KR 1020100095673 A KR1020100095673 A KR 1020100095673A KR 20100095673 A KR20100095673 A KR 20100095673A KR 20120033916 A KR20120033916 A KR 20120033916A
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- group
- formula
- cured film
- compound represented
- platinum
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- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
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Abstract
Description
본 발명은 봉지재 조성물, 이를 경화하여 얻어지는 경화막 및 이를 포함하는 유기발광소자에 관한 것이다.
The present invention relates to an encapsulant composition, a cured film obtained by curing the same, and an organic light emitting device including the same.
일반적으로 유기발광소자는 외부 광원을 필요로 하지 않고, 스스로 발광하는 발광 소자로, 특히, 높은 발광 효율을 가지며, 휘도 및 시야각이 뛰어나며 응답속도가 빠르다는 장점을 갖지만, 대기 중의 수분이나 산소가 발광소자의 내측으로 유입되어 전극이 산화되거나 소자 자체의 열화가 진행되면서 수명이 단축된다는 단점이 있다. 이에, 수분과 산소에 안정한 발광소자를 제작하기 위한 다양한 연구가 진행되고 있다. In general, the organic light emitting device does not require an external light source and emits light by itself. In particular, the organic light emitting device has a high luminous efficiency, an excellent brightness and viewing angle, and a fast response speed. However, moisture or oxygen in the air emits light. As the electrode flows into the inside of the device and the electrode is oxidized or the device itself deteriorates, the service life is shortened. Accordingly, various researches for producing light emitting devices stable to moisture and oxygen have been conducted.
한편, 유기발광소자는 일정 기간 소자를 구동한 때 발광 휘도, 발광 효율 및 발광 균일성과 같은 발광특성이 초기 단계(stage)의 경우와 비교하여 현저히 열화된다는 문제점이 있다. 이러한 발광 특성의 열화 원인의 예에는, 소자 내로 침투한 산소에 의한 전극의 산화, 구동 중 발열에 의해 야기된 유기 재료의 산화 분해, 및 유기 재료의 변성 등을 들 수 있다. 발광 특성 열화의 원인에는 구조의 기계적 열화가 추가적으로 포함되는데, 예를 들어 구조의 계면의 박리는 산소 및 수분의 영향으로 인해 발생하고 또한 구동 중 열 발생 및 고온 환경이 각 구성요소의 열팽창 계수의 차이로 인한 구조의 계면에서의 응력 발생을 유발하여 계면의 박리로 이어진다.On the other hand, the organic light emitting device has a problem that when the device is driven for a certain period of time, the light emission characteristics such as light emission luminance, light emission efficiency, and light emission uniformity are significantly degraded compared to the case of the initial stage. Examples of the cause of deterioration of the luminescence properties include oxidation of the electrode by oxygen penetrating into the element, oxidative decomposition of the organic material caused by heat generation during driving, and denaturation of the organic material. The deterioration of the luminescence properties further includes mechanical deterioration of the structure, for example, delamination of the interface of the structure occurs due to the influence of oxygen and moisture, and also the difference in the coefficient of thermal expansion of each component due to heat generation and high temperature environment during operation. This causes stress generation at the interface of the structure resulting in delamination of the interface.
이러한 문제점을 방지하기 위하여, 수분 및 산소와의 접촉을 억제하기 위해 유기 EL 소자를 밀봉하는 다양한 기술이 연구되었다. 예를 들어, 기재와 이 기재 상에 형성된 투명 전극, 유기기능층 및 금속 캐소드 전극을 포함하는 유기 발광 소자를 구비하는 화소 영역(picture element area) 상에 흡습제가 내벽에 접착된 밀봉 캡을 놓고, 내부를 질소 기체로 채우고, 접착제를 사용하여 밀봉캡을 기재에 고정시킴으로써 유기 발광 소자에 수분이 도달하는 것을 방지하는 방법이 개시되어 있다.In order to prevent this problem, various techniques for sealing the organic EL element have been studied in order to suppress contact with moisture and oxygen. For example, a sealing cap having an absorbent attached to an inner wall is placed on a picture element area including a substrate and an organic light emitting element including a transparent electrode formed on the substrate, an organic functional layer, and a metal cathode electrode. A method of preventing moisture from reaching the organic light emitting device by filling the interior with nitrogen gas and fixing the sealing cap to the substrate using an adhesive is disclosed.
이 때 흡습제로는 다양한 물질들이 연구되어 왔는데, 산화바륨 (BaO) 또는 산화칼슘(CaO)과 같은 알칼리 토금속 산화물은 실리카 겔 또는 제올라이트와 같은 물리적으로 물을 흡착하는 흡습제와는 달리 화학 반응에 의해 확실히 물분자를 포획할 수 있고 고온에서 물분자를 방출시키지 않기 때문에 널리 연구되어왔다. At this time, various materials have been studied as an absorbent. Alkaline earth metal oxides such as barium oxide (BaO) or calcium oxide (CaO) are reliably chemically reacted, unlike an absorbent that physically adsorbs water such as silica gel or zeolite. It has been widely studied because it can trap water molecules and does not release water molecules at high temperatures.
그러나, 이들 흡습제는 이들이 무기 화합물의 입자이고 소자 내에 접착되기 위해 오목한 기재를 필요로 하고, 따라서 생성된 소자가 두꺼워진다는 단점이 있다. 또한, 알칼리 토금속 산화물은 불투명하므로 기재측으로부터 디스플레이 광을 내보내는 소위 하부 발광형 디스플레이 소자에 적용될 수 있다. 그러나, 알칼리토금속 산화물이 기재의 반대쪽인 밀봉 캡 측으로 디스플레이 광을 방출하는 소위 상부 발광형 디스플레이 소자에 적용되는 경우, 흡습제에 의해 발광이 차단될 수 있으므로 흡습제는 이미지 화소 영역(image picture area)으로 들어가지 않도록 배치되어야만 하고 설치 장소가 제공되어야만 한다. However, these humectants have the disadvantage that they are particles of inorganic compounds and require a concave substrate to adhere in the device, thus resulting in thickening of the resulting device. In addition, since the alkaline earth metal oxide is opaque, it can be applied to a so-called bottom emission type display element that emits display light from the substrate side. However, when the alkaline earth metal oxide is applied to a so-called top emitting display element that emits display light toward the sealing cap side opposite to the substrate, light absorbing may be blocked by the absorbent so that the absorbent enters the image picture area. It must be arranged so that it does not go and an installation site must be provided.
상부 발광형 디스플레이 소자에 흡습제를 적용하기 위해서는, 예를 들어, 투명하고 물 흡수 특성을 갖는 폴리비닐 알코올 및 나일론과 같은 중합체를 물 흡습제로서 적용하는 것을 쉽게 생각할 수 있다. 그러나, 이들 중합체는 물을 물리적으로 흡착하고 상기한 바와 같은 충분한 물 흡수 특성을 갖지 않는다. In order to apply the absorbent to the top emitting display element, it is easy to think of applying, for example, polymers such as polyvinyl alcohol and nylon having transparent and water absorbing properties as the water absorbent. However, these polymers physically adsorb water and do not have sufficient water absorption properties as described above.
또한 일본 공개특허 제2001-357973호에는 상부 발광형 구조에서 광투과 특성에 불리하게 영향을 미치지 않도록 배치되는 미립자형 물 흡습제를 사용하는 것이 또한 개시되어 있고, 일본 공개특허 제2002-56970호에는 입자 크기가 유기 발광 소자의 발광 파장보다 작은 물 흡습제가 분산되어 있는 플라스틱 기재를 사용하는 것이 기재되어 있다. 그러나, 무기 입자는 배치하기가 어렵고 1차 입자로서 균일하게 분산되기가 어려우므로, 광 산란으로 인한 투과성의 저하를 피할 수 없다.In addition, Japanese Laid-Open Patent Publication No. 2001-357973 also discloses the use of a particulate water absorbent disposed in such a way that it does not adversely affect the light transmission properties in the top emitting structure, and in Japanese Laid-Open Patent Publication No. 2002-56970 a particle. It is described to use a plastic substrate in which a water absorbent having a size smaller than the emission wavelength of the organic light emitting element is dispersed. However, since inorganic particles are difficult to dispose and difficult to be uniformly dispersed as primary particles, a decrease in the transmittance due to light scattering cannot be avoided.
한편, 톨루엔과 같은 활성용매를 이용하여 제조된 종래 봉지재 조성물에서는 제조과정 중 활성용매가 소량 잔류해도 광학 소자에 다크스팟을 일으켜 광학소자의 발광특성을 저해하는 문제점이 있었다.
On the other hand, in the conventional encapsulant composition prepared using an active solvent such as toluene, even if a small amount of the active solvent remains in the manufacturing process, there is a problem of causing a dark spot on the optical device to inhibit the light emission characteristics of the optical device.
본 발명은 광학 소자에 수분의 유입을 차단하면서, 광을 차단하지 않아 광투과율이 우수하여 양면 발광형 디스플레이 소자에 적용할 수 있는 봉지재 조성물을 제공하고자 한다. The present invention is to provide an encapsulant composition that can be applied to a double-sided light emitting display device with excellent light transmittance by not blocking light while blocking the inflow of moisture to the optical device.
본 발명의 일 구현예에서는 또한 이러한 봉지재 조성물로 제조된 경화층으로, 광학 소자의 열화를 방지하여 장기간 발광 특성을 유지할 수 있도록 하는 경화막을 제공하고자 한다. In one embodiment of the present invention is also to provide a cured film made of such an encapsulant composition, to prevent degradation of the optical element to maintain the light emission characteristics for a long time.
본 발명의 예시적인 일 구현예에서는 또한 이러한 경화막이 형성되어 소자 수명이 향상된 유기발광소자, 액정표시장치, 플라즈마 디스플레이 장치 또는 태양전지를 제공하고자 한다.
In another exemplary embodiment of the present invention, such a cured film is formed to provide an organic light emitting device, a liquid crystal display, a plasma display device, or a solar cell having improved device life.
본 발명의 일 구현예에서는 (A) 다음 화학식 1로 표시되는 실리콘 화합물과 다음 화학식 2로 표시되는 유기 금속 화합물과의 반응생성물; (B) 다음 화학식 3으로 표시되는 실리콘 가교제 화합물; 및 (C) 촉매를 포함하는 봉지재 조성물을 제공한다.In one embodiment of the present invention (A) a reaction product of the silicon compound represented by the following formula (1) and the organometallic compound represented by the following formula (2); (B) the silicone crosslinker compound represented by the following formula (3); And (C) provides an encapsulant composition comprising a catalyst.
화학식 1Formula 1
상기 식에서, R1과 R2는 서로 같거나 다른 것으로, 수산기, 알킬기, 아릴기, 및 시클로알킬기로 이루어진 군에서 선택되는 어느 하나로, 단 적어도 하나는 수산기이며, R은 알킬기, 아릴기, 및 시클로알킬기로 이루어진 군에서 선택되는 어느 하나이고, m은 5 내지 1,000의 정수이고, n은 2 내지 400의 정수이다.
Wherein R 1 and R 2 are the same as or different from each other, and any one selected from the group consisting of a hydroxyl group, an alkyl group, an aryl group, and a cycloalkyl group, wherein at least one is a hydroxyl group, and R is an alkyl group, an aryl group, and a cyclo Any one selected from the group consisting of alkyl groups, m is an integer of 5 to 1,000, n is an integer of 2 to 400.
화학식 2Formula 2
MR'MR '
상기 식에서, M은 Al, Ga, In, La 및 Y 중에서 선택되는 3가 금속이고, R'은 메톡시기, 에톡시기, 부톡시기, 헥실옥시기, 시클로헥실옥시기, 옥틸옥시기, 2-에틸헥실옥시기, 데실옥시기, 라우릴옥시기, 미리스틸옥시기, 세틸옥시기, 이소스테아릴옥시기, 이소보르닐옥시기, 콜레스테록시기, 폴리옥시알킬렌 모노알킬 에스테르기, 폴리옥시알킬렌 모노알킬 에테록시기, 폴리옥시에틸렌 모노라우릴 에스테록시기, 폴리옥시에틸렌 모노메틸 에테록시기, 폴리옥시프로필렌 모노부틸 에테록시기 및 폴리테트라히드로푸란 모노메틸 에테록시기 중 어느 하나이다.Wherein M is a trivalent metal selected from Al, Ga, In, La and Y, and R 'is a methoxy group, ethoxy group, butoxy group, hexyloxy group, cyclohexyloxy group, octyloxy group, 2-ethyl Hexyloxy group, decyloxy group, lauryloxy group, myristyloxy group, cetyloxy group, isostearyloxy group, isobornyloxy group, cholesteroxy group, polyoxyalkylene monoalkyl ester group, polyoxyalkyl It is any one of the len monoalkyl etheroxy group, the polyoxyethylene monolauryl ester group, the polyoxyethylene monomethyl etheroxy group, the polyoxypropylene monobutyl etheroxy group, and the polytetrahydrofuran monomethyl etheroxy group.
화학식 3Formula 3
상기 식에서, R은 알킬기, 아릴기, 및 시클로알킬기로 이루어진 군에서 선택되는 어느 하나이다.Wherein R is any one selected from the group consisting of an alkyl group, an aryl group, and a cycloalkyl group.
화학식 AA
화학식(A)는 화학식1로 표시되는 실리콘 화합물과 화학식 2로 표시되는 유기 금속 화합물과의 반응생성물로서 R1과 R2는 서로 같거나 다른 것으로, 수산기, 알킬기, 아릴기, 및 시클로알킬기로 이루어진 군에서 선택되는 어느 하나로, 단 적어도 하나는 수산기이며, R은 알킬기, 아릴기, 및 시클로알킬기로 이루어진 군에서 선택되는 어느 하나이고, m은 5 내지 1,000의 정수이고, n은 2 내지 400의 정수이다.이때 M 은 상기 식에서, M은 Al, Ga, In, La 및 Y 중에서 선택되는 3가 금속이다.Formula (A) is a reaction product of the silicon compound represented by Formula 1 and the organometallic compound represented by Formula 2, wherein R 1 and R 2 are the same as or different from each other, and include a hydroxyl group, an alkyl group, an aryl group, and a cycloalkyl group. Any one selected from the group, at least one is a hydroxyl group, R is any one selected from the group consisting of an alkyl group, an aryl group, and a cycloalkyl group, m is an integer of 5 to 1,000, n is an integer of 2 to 400 Wherein M is a trivalent metal selected from Al, Ga, In, La and Y.
경화막 형성 후의 흡습 특성, 코팅 특성, 경화, 충진 특성 등을 고려할 때, 화학식 1로 표시되는 실리콘 화합물과 화학식 2로 표시되는 유기 금속 화합물과의 반응생성물은 전체 조성물 중 60 내지 95중량%로 포함되는 것이 바람직할 수 있다. Considering the hygroscopic properties, coating properties, curing and filling properties after the formation of the cured film, the reaction product of the silicon compound represented by the formula (1) and the organometallic compound represented by the formula (2) is contained in 60 to 95% by weight of the total composition. It may be desirable.
또한 코팅 및 경화특성을 고려할 때, (B) 화학식 3으로 표시되는 실리콘 가교제 화합물은 전체 조성물 중 4 내지 39.999중량%로 포함되는 것이 바람직할 수 있다. In addition, considering the coating and curing properties, (B) it may be preferable that the silicone crosslinker compound represented by the formula (3) is included in 4 to 39.999% by weight of the total composition.
또한 코팅 및 경화특성을 고려할 때, (C) 촉매는 플라티늄 디비닐 착물(Platinum Divinyl Complex), 디비닐 테트라메틸디실록산 중의 플라티늄 농축물(platinum concentration in divinyl tetramethyldisiloxane), 중성의 플라티늄 농축물(platinum concentration Neutral), 비닐 말단 폴리디메틸실록산 중의 플라티늄 농축물(platinum concentration in vinyl terminated polydimethylsiloxane), 플라티늄 사이클로비닐 착물(Platinum Cyclovinyl Complexes), 사이클릭 비닐메틸실록산 중의 플라티늄 농축물(platinum concentration in cyclic vinylmethylsiloxanes) 및 플라티늄 옥타놀/옥타날 착물(Platinum Octanol / Octanal Complexes) 중에서 선택되는 적어도 1종의 것일 수 있고, 전체 조성물 중 0.001 내지 1중량%로 포함되는 것이 바람직할 수 있다.In addition, considering the coating and curing properties, (C) catalysts include Platinum Divinyl Complex, Platinum Concentration in divinyl tetramethyldisiloxane, and Neutral Platinum Concentration. Neutral, platinum concentration in vinyl terminated polydimethylsiloxane, Platinum Cyclovinyl Complexes, Platinum Concentration in Cyclic Vinylmethylsiloxanes, and Platinum Octa It may be at least one selected from phenol / octanal complexes (Platinum Octanol / Octanal Complexes), it may be preferably included in 0.001 to 1% by weight of the total composition.
본 발명은 비활성 용매를 사용하여 광학 소자의 Damage를 최소화하여 장기간 발광 특성을 유지할 수 있도록 하는 광학 소자의 보호막을 제공하고자 한다.An object of the present invention is to provide a protective film of an optical device that can maintain the light emission characteristics for a long time by minimizing the damage of the optical device using an inert solvent.
화학식 A를 합성시 기존의 톨루엔 등의 용매 대신 비활성 용매를 사용하여 광학 소자의 Damage를 최소화하여 장기간의 발광특성을 낼수 있다. 톨루엔등과 같이의 활성용매들은 합성한 화학식 1에 소량 잔류해도 광학 소자에 다크스팟을 일으킬 수 있는 요소이며 이는 광학소자의 발광특성을 저해한다. 이러한 현상을 방지하기 위해 광학소자에 Damage 없는 비활성 용매를 사용하여야 하며 이러한 비활성 용매로는 포화 탄화수소 화합물, 실리콘오일로서 액체 방향족 석유 탄화수소 수지, 폴리아이소부틸렌, 액체 폴리부텐, 왁스류(액상 파라핀)등을 들 수 있으며 구체예로서 상표명 나프비스(NAPVIS) (비피 케미칼스(BP Chemicals)), 칼솔 5120(CALSOL 5120) (나프텐-기재 오일, 칼루메트 루브리컨트 컴퍼니(Calumet Lubricants Co.)), 카이돌(KAYDOL) (파라핀-기재, 백색 광유, 위트코 컴퍼니(Witco Co.)), 테트락스(TETRAX) (니폰 오일 컴퍼니(Nippon Oil Co.)), 파라폴 1300(PARAPOL1300) (엑손 케미칼 컴퍼니) 및 인도폴 H-300(INDOPOL H-300) (비피오 아모코 컴퍼니(BPO Amoco Co.))로 구매 가능한 것들이 포함되지만, 이로 한정되지 않는다. 다른 구체예에는 다른 폴리아이소부틸렌 단일중합 체, 이데미츠 코산 컴퍼니 리미티드(Idemitsu Kosan Co., Ltd.)로부터 구매가능한 물질과 같은 폴리부틸렌, 니혼 유시 컴퍼니 리미티드(Nihon Yushi Co., Ltd.)로부터 구매가능한 물질과 같은 폴리부텐 및 다른 액체 폴리부텐 중합체가 포함된다. 연화제의 또 다른 구체예에는 상표명 에스코레즈 2520(ESCOREZ 2520) (액체 방향족 석유 탄화수소 수지, 엑손 케미칼 컴퍼니), 리갈레즈 1018(REGALREZ 1018) (액체 수소화 방향족 탄화수소 수지,헤라클레스 인크.), 및 실바탁 5N(SYLVATAC 5N) (개질 로진 에스테르의 액체 수지, 아리조나 케미칼 컴퍼니(Arizona Chemical Co.)),유동파라핀 DN-60LP, DN-100LP, DN-150LP, DN-500LP (동남유화)으로 구매가능한 것들이 포함된다. In synthesizing Formula A, inert solvents can be used instead of conventional toluene solvents to minimize the damage of the optical device, thereby providing long-term emission characteristics. Active solvents such as toluene and the like may cause dark spots in the optical device even though a small amount of the active solvent remains in the synthesized Chemical Formula 1, which inhibits the light emission characteristics of the optical device. In order to prevent this phenomenon, an inert solvent without damage should be used in an optical device. As such an inert solvent, a saturated aromatic hydrocarbon compound, a liquid aromatic petroleum hydrocarbon resin, polyisobutylene, liquid polybutene, wax (liquid paraffin) as silicone oil Specific examples include trade names NAPVIS (BP Chemicals), CALSOL 5120 (naphthene-based oil, Callumet Lubricants Co.). , KAYDOL (paraffin-based, white mineral oil, Whitco Co.), TETRAX (Nippon Oil Co.), parapol 1300 (PARAPOL1300) (Exon Chemical) Company) and INDOPOL H-300 (BPO Amoco Co.), but are not limited to these. Other embodiments include other polyisobutylene homopolymers, polybutylenes such as materials commercially available from Idemitsu Kosan Co., Ltd., and Nihon Yushi Co., Ltd. Polybutene and other liquid polybutene polymers such as commercially available materials are included. Still other embodiments of emollients include the trade names ESCOREZ 2520 (liquid aromatic petroleum hydrocarbon resin, Exxon Chemical Company), Regalez 1018 (Liquid Hydrogenated Aromatic Hydrocarbon Resin, Hercules Inc.), and Silvabat 5N. (SYLVATAC 5N) (liquid resins of modified rosin esters, Arizona Chemical Co.), flowable paraffins DN-60LP, DN-100LP, DN-150LP, DN-500LP (Southeast Oil) .
본 발명의 다른 일 구현예에서는 또한 이와 같은 봉지재 조성물의 경화막을 제공한다. In another embodiment of the present invention also provides a cured film of such an encapsulant composition.
이와 같은 경화막은 광학소자용 보호막으로 유용하다. Such a cured film is useful as a protective film for optical elements.
본 발명의 예시적인 일 구현예에서는 이와 같은 경화막을 포함하는 유기발광소자를 제공할 수 있다.In an exemplary embodiment of the present invention can provide an organic light emitting device comprising such a cured film.
또한 본 발명의 다른 예시적인 일 구현예에서는 이와 같은 경화막을 봉지 공정 중에 적용하여 얻어지는 액정표시장치를 제공할 수 있다.In another exemplary embodiment of the present invention, a liquid crystal display device obtained by applying such a cured film during an encapsulation process may be provided.
또한 본 발명의 다른 예시적인 일 구현예에서는 이와 같은 경화막을 봉지 공정 중에 적용하여 얻어지는 플라즈마 디스플레이 장치를 제공할 수 있다.In another exemplary embodiment of the present invention, a plasma display device obtained by applying such a cured film during an encapsulation process may be provided.
본 발명의 예시적인 일 구현예에서는 이와 같은 경화막을 포함하는 태양전지를 제공할 수 있다.
In an exemplary embodiment of the present invention can provide a solar cell including such a cured film.
도 1은 본 발명의 일 구현예들에 의한 봉지재 조성물로부터 얻어지는 경화막의 효과를 평가하기 위해 OLED 소자와 합착한 구조의 일예.1 is an example of a structure bonded to the OLED device to evaluate the effect of the cured film obtained from the encapsulant composition according to one embodiment of the present invention.
본 발명의 봉지재 조성물 중 포함되는 (A) 다음 화학식 1로 표시되는 실리콘 화합물과 다음 화학식 2로 표시되는 유기 금속 화합물과의 반응생성물은 실질적으로 경화막 형성시 흡착능을 발현할 수 있으면서 코팅, 경화, 충진특성을 가진 화합물이다. The reaction product of (A) the silicone compound represented by the following formula (1) and the organometallic compound represented by the following formula (2) included in the encapsulant composition of the present invention may be coated and cured while being capable of expressing adsorption capacity upon formation of a cured film. It is a compound with filling properties.
화학식 1Formula 1
상기 식에서, R1과 R2는 서로 같거나 다른 것으로, 수산기, 알킬기, 아릴기, 및 시클로알킬기로 이루어진 군에서 선택되는 어느 하나로, 단 적어도 하나는 수산기이며, R은 알킬기, 아릴기, 및 시클로알킬기로 이루어진 군에서 선택되는 어느 하나이고, m은 5 내지 1,000의 정수이고, n은 2 내지 400의 정수이다.Wherein R 1 and R 2 are the same as or different from each other, and any one selected from the group consisting of a hydroxyl group, an alkyl group, an aryl group, and a cycloalkyl group, wherein at least one is a hydroxyl group, and R is an alkyl group, an aryl group, and a cyclo Any one selected from the group consisting of alkyl groups, m is an integer of 5 to 1,000, n is an integer of 2 to 400.
화학식 2Formula 2
MR'MR '
상기 식에서, M은 Al, Ga, In, La 및 Y 중에서 선택되는 선택되는 3가 금속이고, R'은 메톡시기, 에톡시기, 부톡시기, 헥실옥시기, 시클로헥실옥시기, 옥틸옥시기, 2-에틸헥실옥시기, 데실옥시기, 라우릴옥시기, 미리스틸옥시기, 세틸옥시기, 이소스테아릴옥시기, 이소보르닐옥시기, 콜레스테록시기, 폴리옥시알킬렌 모노알킬 에스테르기, 폴리옥시알킬렌 모노알킬 에테록시기, 폴리옥시에틸렌 모노라우릴 에스테록시기, 폴리옥시에틸렌 모노메틸 에테록시기, 폴리옥시프로필렌 모노부틸 에테록시기 및 폴리테트라히드로푸란 모노메틸 에테록시기 중 어느 하나이다.
Wherein M is a trivalent metal selected from Al, Ga, In, La and Y, and R 'is a methoxy group, ethoxy group, butoxy group, hexyloxy group, cyclohexyloxy group, octyloxy group, 2 -Ethylhexyloxy group, decyloxy group, lauryloxy group, myristyloxy group, cetyloxy group, isostearyloxy group, isobornyloxy group, cholesteroxy group, polyoxyalkylene monoalkyl ester group, poly Oxyalkylene monoalkyl etheroxy group, polyoxyethylene monolauryl esteroxy group, polyoxyethylene monomethyl etheroxy group, polyoxypropylene monobutyl etheroxy group, and polytetrahydrofuran monomethyl etheroxy group.
상기 화학식 1에 있어서, 알킬기의 구체적인 예로는 메틸기, 에틸기, 프로필기, 부틸기, sec-부틸기, tert-부틸기, 펜틸기, 헥실기, 헵틸기, 옥틸기, 노닐기, 데실기, 운데실기, 도데실기, 트리데실기, 테트라데실기, 펜타데실기, 헥사데실기, 헵타데실기, 옥타데실기, 노나데실기, 이코실기, 헨이코실기, 도코실기 등을 들 수 있다. 또한 아릴기의 구체적인 예로는 페닐기, 톨릴기, 4-시아노페닐기, 비페닐기, o, m, p-테르페닐기, 나프틸기, 안트라닐기, 페난트레닐기, 플루오레닐기, 9-페닐안트라닐기, 9,10-디페닐안트라닐기, 피레닐기 등을 들 수 있다.In Formula 1, specific examples of the alkyl group include methyl, ethyl, propyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, and undecylenate. A real group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an ecosyl group, a hencosyl group, a docosyl group, etc. are mentioned. Specific examples of the aryl group include a phenyl group, tolyl group, 4-cyanophenyl group, biphenyl group, o, m, p-terphenyl group, naphthyl group, anthranyl group, phenanthrenyl group, fluorenyl group, 9-phenylanthranyl group, 9,10- diphenyl anthranyl group, a pyrenyl group, etc. are mentioned.
또한 시클로알킬기의 구체적인 예로는 시클로펜틸기, 시클로헥실기, 노르보난기, 아다만탄기, 4-메틸시클로헥실기, 4-시아노시클로헥실기 등을 들 수 있다.Specific examples of the cycloalkyl group include a cyclopentyl group, a cyclohexyl group, a norbornane group, an adamantane group, a 4-methylcyclohexyl group, and a 4-cyanocyclohexyl group.
상기 화학식 2로 표시되는 유기 금속 화합물은 자체적으로 물리적으로 수분을 흡착할 수 있으면서, 한번 흡착하면 흡착 성분이 분리되지 않는, 화학적으로 수분을 흡착하는 건조제 기능을 수행할 수 있다.
The organometallic compound represented by Chemical Formula 2 may perform a function of a desiccant that chemically adsorbs water, while being capable of adsorbing water on its own physically, once adsorbing components are not separated.
화학식 (A)Formula (A)
화학식(A)는 이와 같은 화학식 2로 표시되는 유기 금속 화합물과 상기 화학식 1로 표시되는 실리콘계 화합물을 반응시키면 모핵이 금속인 폴리디메틸실록산 아크릴레이트(poly dimetyl siloxane acrylate) 또는 실리콘 아크릴레이트 등과 같은 화합물을 얻을 수 있다. R1과 R2는 서로 같거나 다른 것으로, 수산기, 알킬기, 아릴기, 및 시클로알킬기로 이루어진 군에서 선택되는 어느 하나로, 단 적어도 하나는 수산기이며, R은 알킬기, 아릴기, 및 시클로알킬기로 이루어진 군에서 선택되는 어느 하나이고, m은 5 내지 1,000의 정수이고, n은 2 내지 400의 정수이다.이때 M 은 상기 식에서, M은 Al, Ga, In, La 및 Y 중에서 선택되는 3가 금속이다.Formula (A) is a compound such as poly dimetyl siloxane acrylate (silicone acrylate) or silicon acrylate, the mother nucleus is a metal when reacting the organometallic compound represented by the formula (2) and the silicon-based compound represented by the formula (1) You can get it. R 1 and R 2 are the same as or different from each other, and any one selected from the group consisting of a hydroxyl group, an alkyl group, an aryl group, and a cycloalkyl group, wherein at least one is a hydroxyl group, and R is an alkyl group, an aryl group, and a cycloalkyl group M is an integer from 5 to 1,000, n is an integer from 2 to 400, wherein M is a trivalent metal selected from Al, Ga, In, La and Y. .
경화막 형성 후의 흡습 특성, 코팅 특성, 경화, 충진 특성 등을 고려할 때, 화학식1로 표시되는 실리콘 화합물과 화학식 2로 표시되는 유기 금속 화합물과의 반응생성물은 전체 조성물 중 60 내지 95중량%로 포함되는 것이 바람직할 수 있다. In consideration of the hygroscopic properties, coating properties, curing and filling properties after the formation of the cured film, the reaction product of the silicon compound represented by the formula (1) and the organometallic compound represented by the formula (2) is contained in 60 to 95% by weight of the total composition. It may be desirable.
본 발명의 봉지재 조성물은 이와 같은 반응생성물을 포함한다. The encapsulant composition of the present invention includes such a reaction product.
이러한 반응생성물은 경화막 형성시 흡습특성, 코팅 특성, 경화, 충진 특성 등을 발현하는 역할을 하는 것으로, 그 함량은 전체 조성물 중 60 내지 95중량%, 좋기로는 80 내지 95중량%인 것이 코팅 및 경화 측면에서 바람직할 수 있다.
These reaction products are responsible for expressing the hygroscopic properties, coating properties, curing, filling properties, etc. when the cured film is formed, the content is 60 to 95% by weight of the total composition, preferably 80 to 95% by weight of the coating And in terms of curing.
상기 (A) 화합물은 가교제 및 촉매와 함께 조성되어 경화막을 형성할 수 있는데, 이때 실리콘 가교제로는 다음 화학식 3으로 표시되는 것을 포함할 수 있다.The compound (A) may be formed together with a crosslinking agent and a catalyst to form a cured film, wherein the silicon crosslinking agent may include a compound represented by the following Formula 3.
화학식 3Formula 3
상기 식에서, R은 알킬기, 아릴기, 및 시클로알킬기로 이루어진 군에서 선택되는 어느 하나이다.
Wherein R is any one selected from the group consisting of an alkyl group, an aryl group, and a cycloalkyl group.
상기 화학식 3에 있어서의 알킬기의 구체적인 예로는 메틸기, 에틸기, 프로필기, 부틸기, sec-부틸기, tert-부틸기, 펜틸기, 헥실기, 헵틸기, 옥틸기, 노닐기, 데실기, 운데실기, 도데실기, 트리데실기, 테트라데실기, 펜타데실기, 헥사데실기, 헵타데실기, 옥타데실기, 노나데실기, 이코실기, 헨이코실기, 도코실기 등을 들 수 있다. 또한 아릴기의 구체적인 예로는 페닐기, 톨릴기, 4-시아노페닐기, 비페닐기, o, m, p-테르페닐기, 나프틸기, 안트라닐기, 페난트레닐기, 플루오레닐기, 9-페닐안트라닐기, 9,10-디페닐안트라닐기, 피레닐기 등을 들 수 있다.Specific examples of the alkyl group in Formula 3 include methyl, ethyl, propyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, and undecylenate. A real group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an ecosyl group, a hencosyl group, a docosyl group, etc. are mentioned. Specific examples of the aryl group include a phenyl group, tolyl group, 4-cyanophenyl group, biphenyl group, o, m, p-terphenyl group, naphthyl group, anthranyl group, phenanthrenyl group, fluorenyl group, 9-phenylanthranyl group, 9,10- diphenyl anthranyl group, a pyrenyl group, etc. are mentioned.
또한 시클로알킬기의 구체적인 예로는 시클로펜틸기, 시클로헥실기, 노르보난기, 아다만탄기, 4-메틸시클로헥실기, 4-시아노시클로헥실기 등을 들 수 있다.Specific examples of the cycloalkyl group include a cyclopentyl group, a cyclohexyl group, a norbornane group, an adamantane group, a 4-methylcyclohexyl group, and a 4-cyanocyclohexyl group.
이와 같은 실리콘 가교제의 함량은 전체 봉지재 조성물 중 4 내지 39.999중량%인 것이 코팅 및 경화 측면에서 유리할 수 있다. 더욱 좋기로는 4 내지 19.999중량%인 것이다.
The content of such silicone crosslinking agent may be 4 to 39.999% by weight of the total encapsulant composition may be advantageous in terms of coating and curing. More preferably, it is 4 to 19.999 weight%.
한편 일정 온도에서의 가교반응을 촉진하기 위해 촉매를 포함하는데, 촉매의 일예로는 플라티늄 디비닐 착물(Platinum Divinyl Complex), 디비닐 테트라메틸디실록산 중의 플라티늄 농축물(platinum concentration in divinyl tetramethyldisiloxane), 중성의 플라티늄 농축물(platinum concentration Neutral), 비닐 말단 폴리디메틸실록산 중의 플라티늄 농축물(platinum concentration in vinyl terminated polydimethylsiloxane), 플라티늄 사이클로비닐 착물(Platinum Cyclovinyl Complexes), 사이클릭 비닐메틸실록산 중의 플라티늄 농축물(platinum concentration in cyclic vinylmethylsiloxanes), 플라티늄 옥타놀/옥타날 착물(Platinum Octanol / Octanal Complexes) 등을 들 수 있다.On the other hand, a catalyst is included to promote the crosslinking reaction at a constant temperature. Examples of the catalyst include platinum divinyl complex, platinum concentration in divinyl tetramethyldisiloxane, and neutral. Platinum Concentration Neutral, Platinum Concentration in Vinyl Terminated Polydimethylsiloxane, Platinum Cyclovinyl Complexes, Platinum Concentration in Cyclic Vinylmethylsiloxane in cyclic vinylmethylsiloxanes), platinum octanol / octanal complexes, and the like.
이와 같은 촉매의 양은 전체 조성물 중 0.001 내지 1중량%인 것이 바람직하다.
The amount of such catalyst is preferably 0.001 to 1% by weight of the total composition.
이와 같은 봉지재 조성물을 이용하여 경화막을 형성시에 경화온도는 100℃ 이하, 좋기로는 70 내지 90℃일 수 있다. 이와 같이 낮은 온도에서 경화시킬 수 있으며, 별도의 용매를 필요로 하지 않기 때문에 소자 제작시 소자에 데미지를 입히는 것을 방지할 수 있다.When the cured film is formed using such an encapsulant composition, the curing temperature may be 100 ° C. or less, preferably 70 ° C. to 90 ° C. As such, it can be cured at a low temperature, and since it does not require a separate solvent, it is possible to prevent damage to the device during device fabrication.
본 발명의 봉지재 조성물은 경화막 형성시 자체적으로 접착제로서의 기능을 발휘할 수 있어서, 별도의 점착제를 필요로 하지 않는다. The sealing material composition of this invention can exhibit the function as an adhesive itself at the time of cured film formation, and does not require a separate adhesive.
또한 소자의 전면에 합착할 수 있음에 따라 유기 발광 소자 내에 갭을 두지 않아 외부의 충격이나 4인치 이상의 대면적시 상판 유리가 쳐지는 것을 방지할 수 있다.In addition, since the organic light emitting device can be bonded to the front surface of the device, it is possible to prevent external impact or the top glass from sagging in a large area of 4 inches or more.
또한 무용매 타입으로 소자에 직접 코팅할 수 있어 사용이 용이하고, 무용매 타입이어서 아웃 개싱이 적어 이로 인한 소자에의 피해를 방지할 수 있다.
In addition, the solvent-free type can be directly coated on the device is easy to use, since the solvent-free type is less out-gassing can prevent damage to the device due to this.
본 발명에 따른 봉지재 조성물을 이용하여 유기발광 소자에 봉지재층을 형성한 합착된 유기발광소자의 일예를 도 1을 참조하여 설명하면, 기판(10) 상에는 양극(20), 유기층(30) 및 광투과형 음극(40)이 적층되고, 그 상부로 무기수분배리어층(50)이 형성되어 소자부가 형성된다. 상기 무기수분배리어층(50) 상에 상기 유기층(30)과 음극(40)을 둘러싸는 위치에 본 발명의 봉지재 조성물의 경화막인 봉지재층(60)이 둘러싸며 형성되고 상부에는 밀봉기판(80)이, 주위에는 UV 경화형 seal제(70)가 설치될 수 있다. Referring to FIG. 1, an example of a bonded organic light emitting device in which an encapsulant layer is formed on an organic light emitting device using the encapsulation material composition according to the present invention is described with reference to FIG. 1, on the
유기발광소자에 봉지재층을 형성하기 위해 상술한 봉지재 조성물을 무기수분배리어층(50)에 직접 코팅하거나 밀봉기판(80) 하부에 코팅하여 무기수분배리어층(50)과 합착할 수 있다. In order to form the encapsulant layer on the organic light emitting device, the encapsulant composition may be directly coated on the inorganic
이와 같이 형성되는 경화막은 광학소자용 보호막으로, 이는 흡습율이 높아 발광소자의 수명을 향상시킬 수 있으며, 또한 연성 디스플레이에도 연성을 저해하지 않으므로 무리없이 적용될 수 있다. The cured film formed as described above is a protective film for an optical device, which can improve the lifespan of the light emitting device due to its high moisture absorption rate, and can be applied without any difficulty since it does not inhibit ductility in the flexible display.
이와 같은 경화막은 유기발광소자(OLED) 뿐만 아니라 반도체, 액정표시장치(Liquid Crystal Display : LCD), 플라즈마 디스플레이 장치(Plasma Display panel : PDP) 및 태양전지의 봉지 공정에 적용할 수 있다.
Such a cured film may be applied to an encapsulation process of a semiconductor, a liquid crystal display (LCD), a plasma display panel (PDP), and a solar cell as well as an organic light emitting diode (OLED).
이하, 본 발명을 실시예를 통하여 보다 상세히 설명하나, 본 발명의 범위가 하기 실시예로 한정되는 것은 아니다. Hereinafter, the present invention will be described in more detail with reference to Examples, but the scope of the present invention is not limited to the following Examples.
(제조예 1: 화학식 1 화합물 제조)Preparation Example 1: Preparation of Compound of Formula 1
옥타메틸사이클로테트라실록산(octamethylcyclotetrasiloxane, 삼호 CNE) 148.5g, 테트라메틸테트라비닐사이클로테트라실록산(tetramethyltetravinylcyclotetrasiloxane, 삼호 CNE) 1.5g에 황산 0.7ml를 가하여 90℃에서 2시간 동안 반응시켜 합성한 후, 흡습제를 사용한 수분 제거 및 톨루엔을 사용한 축합반응 생성 수분을 제거하여 중량평균분자량 500인 상기 화학식 1로 표시되는 화합물(화학식 1에 있어서, R1=OH, R2= CH3, R= CH3인 화합물)을 수득하였다.
After 148.5 g of octamethylcyclotetrasiloxane (Samho CNE) and 1.5 g of tetramethyltetravinylcyclotetrasiloxane (Samho CNE), 0.7 ml of sulfuric acid was added and reacted at 90 ° C. for 2 hours, followed by synthesis. Moisture Removal and Condensation Reaction Production Using Toluene Compounds represented by the formula (1) having a weight average molecular weight of 500 by removing water (in Formula 1, R 1 = OH, R 2 = CH 3 , and R = CH 3 ) Obtained.
(제조예 2: 화학식 1 화합물 제조)Preparation Example 2: Preparation of Compound of Formula 1
메타페닐사이클로테트라실록산(SH SF 1421,삼호 CNE) 148.5g, 테트라메틸테트라비닐사이클로테트라실록산(tetramethyltetravinylcyclotetrasiloxane, 삼호 CNE) 1.5g에 황산 0.7ml를 가하여 90℃에서 2시간 동안 반응시켜 합성한 후, 흡습제를 사용한 수분 제거 및 톨루엔을 사용한 축합반응 생성 수분을 제거하여 중량평균분자량 500인 상기 화학식 1로 표시되는 화합물(화학식 1에 있어서, R1=OH, R2= C6H5, R= CH3인 화합물)을 수득하였다.
148.5 g of metaphenylcyclotetrasiloxane (SH SF 1421, Samho CNE) and 1.5 g of tetramethyltetravinylcyclotetrasiloxane (tetramethyltetravinylcyclotetrasiloxane (Samho CNE)) were added 0.7 ml of sulfuric acid and reacted at 90 ° C. for 2 hours, followed by synthesis. Water removal and condensation reaction production using toluene to remove the water represented by the formula (1) having a weight average molecular weight of 500 (In Formula 1, R 1 = OH, R 2 = C 6 H 5 , R = CH 3 Phosphorus compound).
(제조예 3: A-1 화합물 제조)Preparation Example 3: A-1 Compound Preparation
유동 파라핀(DN-100LP, 동남 유화) 300g에 알루미늄 부톡사이드(ALDRICH) 50g, 제조예 1로부터 얻어진 화학식 1 화합물 300g을 혼합하여 800rpm으로 강하게 24시간 동안 교반한 후 증발기(evaporater)를 이용하여 150℃에서 2시간 동안 감압하여, 화학식 1 화합물과 화학식 2로 표시되는 화합물의 반응생성물인 A-1 화합물을 수득하였다.
300 g of liquid paraffin (DN-100LP, Southeast Emulsification) was mixed with 50 g of aluminum butoxide (ALDRICH) and 300 g of the compound of Formula 1 obtained from Preparation Example 1, and stirred vigorously at 800 rpm for 24 hours using 150 ° C. using an evaporator. At 2 hours under reduced pressure, the compound A-1, which is a reaction product of the compound represented by formula 1 and compound 2, was obtained.
(제조예 4: A-2 화합물 제조)Preparation Example 4: A-2 Compound Preparation
유동 파라핀(DN-100LP, 동남 유화) 300g에 알루미늄 부톡사이드(ALDRICH) 50g, 제조예 2로부터 얻어진 화학식 1 화합물 300g을 혼합하여 800rpm으로 강하게 24시간 동안 교반한 후 증발기(evaporater)를 이용하여 150℃에서 2시간 동안 감압하여, 화학식 1 화합물과 화학식 2로 표시되는 화합물의 반응생성물인 A-2 화합물을 수득하였다.
300 g of liquid paraffin (DN-100LP, Southeast Emulsification) was mixed with 50 g of aluminum butoxide (ALDRICH) and 300 g of the compound of Formula 1 obtained from Preparation Example 2, and stirred vigorously at 800 rpm for 24 hours, followed by 150 ° C. using an evaporator. At 2 hours under reduced pressure, to obtain an A-2 compound which is a reaction product of the compound represented by formula (1) and the compound represented by formula (2).
(실시예 1~4)(Examples 1-4)
상기 제조예 3 내지 4로부터 얻어진 각각의 A화합물, 화학식 3으로 표시되는 실리콘 가교제 화합물(삼호 CNE 제품, 상품명 0.50 MMOLE/GM Crosslinker ), 촉매로서 플라티늄 디비닐 착물(0.05% Platinum Complex In Vinyl Polymer 500, cSt제품)을 하기 표 1에 나타낸 배합량으로 배합하여 봉지재용 조성물을 제조하였다. A compound obtained from each of Preparation Examples 3 to 4, a silicone crosslinker compound represented by Formula 3 (Samho CNE, trade name 0.50 MMOLE / GM Crosslinker), a platinum divinyl complex (0.05% Platinum Complex In Vinyl Polymer 500, as a catalyst) cSt product) was blended in the blending amounts shown in Table 1 to prepare a composition for encapsulant.
하기 표 1에 있어서 단위는 중량%이다.In Table 1, the unit is% by weight.
상기 실시예 1 내지 4에 따라 제조된 봉지재용 조성물을 스핀코팅 방법으로 OLED에 소자에 직접 코팅하여 밀봉 기판과 합착 후 90℃에서 30분 동안 가열하여 경화시켜, 두께 20㎛의 봉지재층을 포함하는 유기발광소자를 얻었다. The encapsulant composition prepared according to Examples 1 to 4 was directly coated on the device to the OLED by spin coating, bonded to the encapsulation substrate, and cured by heating at 90 ° C. for 30 minutes to include an encapsulant layer having a thickness of 20 μm. An organic light emitting device was obtained.
도 1을 참조하여 합착된 OLED 구조를 설명하면, 기판(10) 상에는 양극(20), 유기층(30) 및 광투과형 음극(40)이 적층되고, 그 상부에 무기수분베리어층(50)이 형성되어 소자부가 형성된다. 상기 무기수분배리어층(50) 상에 상기 유기층(30)과 음극(40)을 둘러싸도록 봉지재층(60)이 형성되며, 상부에는 밀봉기판(80)이, 봉지재층 주변에는 UV 경화형 실란트(70)가 설치되어 있다.
Referring to the bonded OLED structure with reference to Figure 1, the
<비교예 1>Comparative Example 1
톨루엔 300g에 알루미늄 부톡사이드(ALDRICH) 50g, 제조예 1로부터 얻어진 화학식 1 화합물 300g을 혼합하여 800rpm으로 강하게 24시간 동안 교반한 후 증발기(evaporater)를 이용하여 150℃에서 2시간 동안 감압하여, 반응생성물 수득하였다. 수득된 반응 생성물과 90중량부 실리콘 가교제 화합물 9.9 중량부 촉매 0.1 중량부를 혼합하여 스핀코팅 방법으로 OLED에 소자에 직접 코팅하여 밀봉 기판과 합착 후 90℃에서 30분 동안 가열하여 경화시켜, 두께 20㎛의 봉지재층을 포함하는 유기발광소자를 얻었다.
50 g of aluminum butoxide (ALDRICH) and 300 g of the compound of formula (I) obtained from Preparation Example 1 were mixed with 300 g of toluene, stirred at 800 rpm strongly for 24 hours, and then decompressed for 2 hours at 150 ° C. using an evaporator. Obtained. The obtained reaction product was mixed with 0.1 parts by weight of a 9.9 parts by weight of a 90 parts by weight of a silicone crosslinker compound and directly coated on the device in an OLED by a spin coating method, bonded to a sealing substrate, and then cured by heating at 90 ° C. for 30 minutes. An organic light emitting device comprising an encapsulant layer of was obtained.
상기 실시예 1 내지 4에 따라 제조된 조성물을 유기 기판 상에 코팅한 후 90℃에서 30분간 가열한 후 두께 20㎛인 경화막을 형성하였다. 한편 상기 비교예 1에 따라 제조된 조성물을 유리 기판 상에 코팅한 후 90℃에서 30분간 가열한 후 두께 20㎛인 경화막을 형성하였다. The composition prepared according to Examples 1 to 4 was coated on an organic substrate, and then heated at 90 ° C. for 30 minutes to form a cured film having a thickness of 20 μm. Meanwhile, the composition prepared according to Comparative Example 1 was coated on a glass substrate, and then heated at 90 ° C. for 30 minutes to form a cured film having a thickness of 20 μm.
얻어진 각각의 경화막에 대하여 다음과 같은 방법으로 광투과율을 측정하여 그 결과를 다음 표 2에 나타내었다.
The light transmittance of each obtained cured film was measured by the following method, and the results are shown in Table 2 below.
(1) 광투과율: 얻어진 유리 기판 상의 경화막에 대하여, UV-Visible Spectrophotometer를 이용하여 400nm 내지 800nm까지의 가시광선 영역에서 투과도를 측정하였다.
(1) Light transmittance: About the obtained cured film on the glass substrate, the transmittance | permeability was measured in the visible light region from 400 nm to 800 nm using a UV-Visible Spectrophotometer.
한편 실시예 1 내지 4 및 비교예 1에 따라 제조된 경화막을 포함하는 유기발광소자의 소자 수명을 하기 방법으로 측정하여 그 결과를 표 2에 나타내었다.
On the other hand, the device life of the organic light emitting device including the cured film prepared according to Examples 1 to 4 and Comparative Example 1 was measured by the following method and the results are shown in Table 2.
(2) 소자 수명(2) device life
도 1에 나타낸 구조를 갖도록 합착한 OLED 소자에 대해 초기 발광 세기를 IVL TEST(전류-전압공급기(키슬리 2400, 키슬리), 휘도측정기 (CS-2000, 미놀타), 지그부(영풍 CMC)로 구성)를 이용하여 측정하고, 이를 70℃ RH 80% 항온 항습기에서 보관하면서 시간 경과에 따른 최초 다크 스팟이 생기는 시간을 나타내었다.
The initial luminous intensity of the OLED devices bonded to have the structure shown in FIG. 1 is IVL TEST (current-voltage supply (Kisley 2400, Keithley), luminance meter (CS-2000, Minolta), jig part (Youngpoong CMC) Constitution) and stored at 70 °
(hr)Element Life
(hr)
상기 표 2의 결과로부터, 본 발명의 봉지재 조성물의 경화막은 광투과율이 97% 이상으로, 투명성을 확보할 수 있음을 알 수 있다. 이러한 결과로부터 본 발명의 봉지재 조성물의 경화막은 광을 차단하지 않아 광투과율이 우수하여 양면 발광형 디스플레이 소자에 적용할 수 있을 것을 기대할 수 있다. From the result of the said Table 2, it turns out that the cured film of the sealing material composition of this invention can ensure transparency with a light transmittance of 97% or more. From these results, it is expected that the cured film of the encapsulant composition of the present invention does not block light and thus can be applied to a double-sided light emitting display device with excellent light transmittance.
또한 소자의 수명이 기존의 흡습재를 포함하는 경우에 비하여 현저히 향상됨을 알 수 있다. 이로부터 본 발명의 봉지재 조성물의 경화막은 흡습능이 우수하고 봉지재 조성물로부터 얻어짐에 따라 아웃개싱이 없어 광학 소자의 열화를 방지하여 장기간 발광 특성을 유지할 수 있도록 함을 알 수 있다.
In addition, it can be seen that the life of the device is remarkably improved compared to the case of including the existing moisture absorbent material. From this, it can be seen that the cured film of the encapsulant composition of the present invention has excellent hygroscopicity and is obtained from the encapsulant composition so that there is no outgassing so that the deterioration of the optical element can be prevented to maintain the light emission characteristics for a long time.
10 : 기판 20 : 양극
30 : 유기층 40 : 광투과형 음극
50 : 무기수분배리어층 60 : 봉지재층
70 : UV 경화형 실링제 80 : 밀봉기판
10
30: organic layer 40: light transmitting cathode
50: inorganic moisture barrier layer 60: encapsulant layer
70: UV curable sealing agent 80: sealing substrate
Claims (12)
(B) 다음 화학식 3으로 표시되는 실리콘 가교제 화합물; 및
(C) 촉매를 포함하는 봉지재 조성물.
화학식 1
상기 식에서, R1과 R2는 서로 같거나 다른 것으로, 수산기, 알킬기, 아릴기, 및 시클로알킬기로 이루어진 군에서 선택되는 어느 하나로, 단 적어도 하나는 수산기이며, R은 알킬기, 아릴기, 및 시클로알킬기로 이루어진 군에서 선택되는 어느 하나이고, m은 5 내지 1,000의 정수이고, n은 2 내지 400의 정수이다.
화학식 2
MR'
상기 식에서, M은 Al, Ga, In, La 및 Y 중에서 선택되는 3가 금속이고, R'은 메톡시기, 에톡시기, 부톡시기, 헥실옥시기, 시클로헥실옥시기, 옥틸옥시기, 2-에틸헥실옥시기, 데실옥시기, 라우릴옥시기, 미리스틸옥시기, 세틸옥시기, 이소스테아릴옥시기, 이소보르닐옥시기, 콜레스테록시기, 폴리옥시알킬렌 모노알킬 에스테르기, 폴리옥시알킬렌 모노알킬 에테록시기, 폴리옥시에틸렌 모노라우릴 에스테록시기, 폴리옥시에틸렌 모노메틸 에테록시기, 폴리옥시프로필렌 모노부틸 에테록시기 및 폴리테트라히드로푸란 모노메틸 에테록시기 중 어느 하나이다.
화학식 3
상기 식에서, R은 알킬기, 아릴기, 및 시클로알킬기로 이루어진 군에서 선택되는 어느 하나이다.
(A) a reaction product of a silicon compound represented by the following Chemical Formula 1 and an organometallic compound represented by the following Chemical Formula 2;
(B) the silicone crosslinker compound represented by the following formula (3); And
(C) The sealing material composition containing a catalyst.
Formula 1
Wherein R 1 and R 2 are the same as or different from each other, and any one selected from the group consisting of a hydroxyl group, an alkyl group, an aryl group, and a cycloalkyl group, wherein at least one is a hydroxyl group, and R is an alkyl group, an aryl group, and a cyclo Any one selected from the group consisting of alkyl groups, m is an integer of 5 to 1,000, n is an integer of 2 to 400.
(2)
MR '
Wherein M is a trivalent metal selected from Al, Ga, In, La and Y, and R 'is a methoxy group, ethoxy group, butoxy group, hexyloxy group, cyclohexyloxy group, octyloxy group, 2-ethyl Hexyloxy group, decyloxy group, lauryloxy group, myristyloxy group, cetyloxy group, isostearyloxy group, isobornyloxy group, cholesteroxy group, polyoxyalkylene monoalkyl ester group, polyoxyalkyl It is any one of the len monoalkyl etheroxy group, the polyoxyethylene monolauryl ester group, the polyoxyethylene monomethyl etheroxy group, the polyoxypropylene monobutyl etheroxy group, and the polytetrahydrofuran monomethyl etheroxy group.
(3)
Wherein R is any one selected from the group consisting of an alkyl group, an aryl group, and a cycloalkyl group.
The encapsulation composition of claim 1, wherein the reaction product of (A) the silicon compound represented by the formula (1) and the organometallic compound represented by the formula (2) is included in an amount of 60 to 95 wt% in the total composition.
The encapsulant composition of claim 1, wherein the silicone crosslinker compound represented by Formula (B) is included in an amount of 4 to 39.999% by weight in the total composition.
The catalyst of claim 1, wherein the catalyst (C) comprises: Platinum Divinyl Complex, Platinum Concentration in divinyl tetramethyldisiloxane, Neutral Platinum Concentration Neutral, Platinum concentration in vinyl terminated polydimethylsiloxane, Platinum Cyclovinyl Complexes, Platinum concentration in cyclic vinylmethylsiloxanes, Platinum Octanol / Octane Encapsulant composition of at least one selected from blade complexes (Platinum Octanol / Octanal Complexes).
The encapsulant composition according to claim 1 or 4, wherein (C) the catalyst is contained in 0.001 to 1% by weight of the total composition.
The cured film manufactured from the sealing material composition of Claim 1.
The cured film of Claim 6 hardened | cured at the curing temperature of 100 degrees C or less.
The cured film of Claim 6 which is a protective film for optical elements.
An organic light emitting device comprising the cured film of claim 6.
A liquid crystal display device comprising the cured film of claim 6.
A plasma display device comprising the cured film of claim 6.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020100095673A KR20120033916A (en) | 2010-09-30 | 2010-09-30 | Encapsulation composition, cured layer and organic light emitting device, liquid crystal display, plasma display display and solar cell |
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| KR1020100095673A KR20120033916A (en) | 2010-09-30 | 2010-09-30 | Encapsulation composition, cured layer and organic light emitting device, liquid crystal display, plasma display display and solar cell |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140038662A (en) * | 2012-09-21 | 2014-03-31 | 코오롱인더스트리 주식회사 | Absorbent and composition for forming passivation layer of optical element comprising same |
| WO2015046734A1 (en) * | 2013-09-25 | 2015-04-02 | 삼성에스디아이 주식회사 | Composition for composite sheet, composite sheet manufactured using same, and display device comprising same |
-
2010
- 2010-09-30 KR KR1020100095673A patent/KR20120033916A/en not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140038662A (en) * | 2012-09-21 | 2014-03-31 | 코오롱인더스트리 주식회사 | Absorbent and composition for forming passivation layer of optical element comprising same |
| WO2015046734A1 (en) * | 2013-09-25 | 2015-04-02 | 삼성에스디아이 주식회사 | Composition for composite sheet, composite sheet manufactured using same, and display device comprising same |
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