KR20200034519A - Novel copolymer and organic light emitting device comprising the same - Google Patents
Novel copolymer and organic light emitting device comprising the same Download PDFInfo
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- KR20200034519A KR20200034519A KR1020180114407A KR20180114407A KR20200034519A KR 20200034519 A KR20200034519 A KR 20200034519A KR 1020180114407 A KR1020180114407 A KR 1020180114407A KR 20180114407 A KR20180114407 A KR 20180114407A KR 20200034519 A KR20200034519 A KR 20200034519A
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- South Korea
- Prior art keywords
- group
- copolymer
- light emitting
- formula
- organic light
- Prior art date
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- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
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- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
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- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
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- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
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Abstract
Description
본 발명은 신규한 공중합체 및 이를 포함하는 유기 발광 소자에 관한 것이다. The present invention relates to a novel copolymer and an organic light emitting device comprising the same.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 넓은 시야각, 우수한 콘트라스트, 빠른 응답 시간을 가지며, 휘도, 구동 전압 및 응답 속도 특성이 우수하여 많은 연구가 진행되고 있다. In general, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies have been conducted.
유기 발광 소자는 일반적으로 양극과 음극 및 상기 양극과 음극 사이에 유기물 층을 포함하는 구조를 가진다. 상기 유기물 층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. The organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often formed of a multi-layered structure composed of different materials, for example, may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode and electrons are injected at the cathode, and excitons are formed when the injected holes meet the electrons. When it falls to the ground again, it will shine.
상기와 같은 유기 발광 소자에 사용되는 유기물에 대하여 새로운 재료의 개발이 지속적으로 요구되고 있다.The development of new materials for organic materials used in the organic light emitting device as described above is continuously required.
한편, 최근에는 공정 비용 절감을 위하여 기존의 증착 공정 대신 용액 공정, 특히 잉크젯 공정을 이용한 유기 발광 소자가 개발되고 있다. 초창기에는 모든 유기 발광 소자 층을 용액 공정으로 코팅하여 유기 발광 소자를 개발하려 하였으나 현재 기술로는 한계가 있어, 정구조 형태에서 HIL, HTL, EML만을 용액 공정으로 진행하고 추후 공정은 기존의 증착 공정을 활용하는 하이브리드(hybrid) 공정이 연구 중이다. Meanwhile, in order to reduce process costs, an organic light emitting device using a solution process, particularly an inkjet process, has been developed instead of a conventional deposition process. In the early days, all organic light-emitting device layers were coated with a solution process to develop an organic light-emitting device, but there are limitations in the current technology, so only HIL, HTL, and EML are used as a solution process in the form of a regular structure, and the subsequent process is an existing deposition process. A hybrid process that utilizes is being studied.
이에 본 발명에서는 유기 발광 소자에 사용될 수 있으면서 동시에 용액 공정으로 증착이 가능한 신규한 유기 발광 소자의 소재를 제공한다. Accordingly, the present invention provides a material for a novel organic light-emitting device that can be used in an organic light-emitting device and can be deposited by a solution process at the same time.
본 발명은 신규한 공중합체 및 이를 포함하는 유기 발광 소자에 관한 것이다. The present invention relates to a novel copolymer and an organic light emitting device comprising the same.
본 발명은 하기 화학식 1로 표시되는 반복 단위, 및 하기 화학식 2로 표시되는 반복 단위를 포함하는 공중합체를 제공한다:The present invention provides a copolymer comprising a repeating unit represented by Chemical Formula 1 and a repeating unit represented by Chemical Formula 2:
[화학식 1][Formula 1]
상기 화학식 1에서, In Chemical Formula 1,
R1 내지 R3는 각각 독립적으로, 수소, 또는 C1-10 알킬이고,R 1 to R 3 are each independently hydrogen, or C 1-10 alkyl,
L1은 단일 결합; 치환 또는 비치환된 C6-60 아릴렌; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴렌이고, L 1 is a single bond; Substituted or unsubstituted C 6-60 arylene; Or C 2-60 heteroarylene comprising any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
Ar1 및 Ar2는 각각 독립적으로, 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴이고, 단 Ar1 및 Ar2는 서로 상이하고,Ar 1 and Ar 2 are each independently, substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S, provided that Ar 1 and Ar 2 are different from each other,
[화학식 2][Formula 2]
상기 화학식 2에서, In Chemical Formula 2,
R4 내지 R6는 각각 독립적으로, 수소, 또는 C1-10 알킬이고,R 4 to R 6 are each independently hydrogen, or C 1-10 alkyl,
L2은 치환 또는 비치환된 C6-60 아릴렌; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴렌이고, L 2 is substituted or unsubstituted C 6-60 arylene; Or C 2-60 heteroarylene comprising any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
x 및 y는 각각 독립적으로 1 내지 100의 정수이다. x and y are each independently an integer from 1 to 100.
또한, 본 발명은 양극; 상기 양극과 대향하여 구비된 음극; 상기 양극과 상기 음극 사이에 구비된 발광층; 및 상기 양극과 상기 발광층 사이에 구비된 정공수송층을 포함하고, 상기 정공수송층은 상기 공중합체를 포함하는 것인, 유기 발광 소자를 제공한다.In addition, the present invention is an anode; A cathode provided opposite the anode; A light emitting layer provided between the anode and the cathode; And a hole transport layer provided between the anode and the light emitting layer, wherein the hole transport layer includes the copolymer.
본 발명에 따른 공중합체는 유기 발광 소자의 정공수송층의 재료로서 사용될 수 있으며, 또한 용액 공정으로 증착이 가능하며, 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는 수명 특성을 향상시킬 수 있다. The copolymer according to the present invention can be used as a material for the hole transport layer of an organic light emitting device, and can also be deposited by a solution process, and can improve the efficiency, low driving voltage and / or life characteristics in an organic light emitting device. .
도 1은 기판(1), 양극(2), 정공수송층(3), 발광층(4), 음극(5)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.
도 2는 기판 (1), 양극(2), 정공주입층(6), 정공수송층(3), 발광층(4), 전자수송층(7), 전자주입층(8) 및 음극(5)로 이루어진 유기 발광 소자의 예를 도시한 것이다.
도 3은 본 발명의 일실시예에 따른 공중합체의 NMR 데이터를 나타낸 것이다.
도 4는 본 발명의 일실시예에 따른 공중합체의 GPC 데이터를 나타낸 것이다.
도 5는 본 발명의 일실시예에 따른 공중합체의 용매 내성을 나타낸 것이다. 도 5a의 좌측 두 개가 실시예 1의 공중합체의 데이터이고, 우측 두 개가 실시예 2의 공중합체의 데이터이다. 도 5b의 좌측 두 개가 실시예 3의 공중합체의 데이터이고, 우측 두 개가 실시예 4의 공중합체의 데이터이다.FIG. 1 shows an example of an organic light emitting device comprising a
2 is composed of a substrate (1), an anode (2), a hole injection layer (6), a hole transport layer (3), a light emitting layer (4), an electron transport layer (7), an electron injection layer (8) and a cathode (5) An example of an organic light emitting device is shown.
Figure 3 shows the NMR data of the copolymer according to an embodiment of the present invention.
Figure 4 shows the GPC data of the copolymer according to an embodiment of the present invention.
Figure 5 shows the solvent resistance of the copolymer according to an embodiment of the present invention. The left two of FIG. 5A are data of the copolymer of Example 1, and the right two are data of the copolymer of Example 2. The left two of FIG. 5B are data of the copolymer of Example 3, and the right two are data of the copolymer of Example 4.
이하, 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다.Hereinafter, the present invention will be described in more detail to help understanding.
본 명세서에서, 
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 사이클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환 또는 비치환된 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 비페닐기일 수 있다. 즉, 비페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다.The term "substituted or unsubstituted" as used herein refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amino group; Phosphine oxide group; Alkoxy groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxyl group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; An alkenyl group; Alkyl aryl groups; Alkylamine groups; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups containing one or more of N, O and S atoms, or substituted or unsubstituted with two or more substituents among the exemplified substituents above . For example, "a substituent having two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.
본 명세서에서 카보닐기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 40인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
본 명세서에 있어서, 에스테르기는 에스테르기의 산소가 탄소수 1 내지 25의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 25의 아릴기로 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the oxygen of the ester group may be substituted with a straight chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In this specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
본 명세서에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.
본 명세서에 있어서, 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, the boron group is specifically a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, but is not limited thereto.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 6이다. 알킬기의 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 사이클로펜틸메틸,사이클로헥틸메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸펜틸, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이들에 한정되지 않는다.In the present specification, the alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group are methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 6이다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 알릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나 이들에 한정되지 않는다.In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, steelbenyl group, styrenyl group, and the like, but are not limited thereto.
본 명세서에 있어서, 사이클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 사이클로프로필, 사이클로부틸, 사이클로펜틸, 3-메틸사이클로펜틸, 2,3-디메틸사이클로펜틸, 사이클로헥실, 3-메틸사이클로헥실, 4-메틸사이클로헥실, 2,3-디메틸사이클로헥실, 3,4,5-트리메틸사이클로헥실, 4-tert-부틸사이클로헥실, 사이클로헵틸, 사이클로옥틸 등이 있으나, 이에 한정되지 않는다.In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. 상기 플루오레닐기가 치환되는 경우, 
본 명세서에 있어서, 헤테로고리기는 이종 원소로 O, N, Si 및 S 중 1개 이상을 포함하는 헤테로고리기로서, 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로고리기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤조옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 페난쓰롤린기(phenanthroline), 이소옥사졸릴기, 티아디아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si, and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridil group , Pyridazine group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , Carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isooxazolyl group, tiadiia A sleepy group, a phenothiazinyl group and a dibenzofuranyl group, and the like, but are not limited thereto.
본 명세서에 있어서, 아르알킬기, 아르알케닐기, 알킬아릴기, 아릴아민기 중의 아릴기는 전술한 아릴기의 예시와 같다. 본 명세서에 있어서, 아르알킬기, 알킬아릴기, 알킬아민기 중 알킬기는 전술한 알킬기의 예시와 같다. 본 명세서에 있어서, 헤테로아릴아민 중 헤테로아릴은 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 아르알케닐기 중 알케닐기는 전술한 알케닐기의 예시와 같다. 본 명세서에 있어서, 아릴렌은 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로아릴렌은 2가기인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 탄화수소 고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 아릴기 또는 사이클로알킬기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다.In the present specification, an aryl group in an aralkyl group, an alkenyl group, an alkylaryl group, and an arylamine group is the same as the exemplified aryl group described above. In the present specification, the alkyl group among the aralkyl group, alkylaryl group, and alkylamine group is the same as the above-described alkyl group. In the present specification, the description of the heteroaryl group among heteroarylamines may be applied. In the present specification, the alkenyl group in the alkenyl group is the same as the exemplified alkenyl group. In the present specification, the description of the aryl group described above may be applied, except that the arylene is a divalent group. In the present specification, the description of the heterocyclic group described above may be applied, except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aryl group or cycloalkyl group described above may be applied, except that two substituents are formed by bonding. In this specification, the heterocycle is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied, except that two substituents are formed by bonding.
본 발명은 상기 화학식 1로 표시되는 반복 단위, 및 상기 화학식 2로 표시되는 반복 단위를 포함하는 공중합체를 제공한다. The present invention provides a copolymer comprising a repeating unit represented by
종래에서 사용되던 용액 증착용 물질은, 용매에 대한 용해도가 있더라도 그 다음 층 증착시 사용되는 용매에 상기 물질이 녹아들어가 층이 섞여 소자 성능을 떨어트리는 문제가 있다. The material for solution deposition, which has been used in the related art, has a problem in that, even if there is a solubility in a solvent, the material is dissolved in a solvent used when depositing the next layer and the layers are mixed to degrade device performance.
그러나 본 발명에 따른 공중합체는, 이하 상세히 설명할 바와 같이 상기 화학식 1로 표시되는 반복 단위에 의한 우수한 정공 전달 특성과 함께, 증착 후 상기 화학식 2로 표시되는 반복 단위를 경화시켜 용매 직교성(solvent orthogonality)을 가져 층간 섞임이 억제되는 특징이 있다. However, the copolymer according to the present invention, as described in detail below, together with excellent hole transport properties by the repeating unit represented by the formula (1), after deposition, curing the repeating unit represented by the formula (2) to solve solvent orthogonality (solvent orthogonality) ), Interlayer mixing is suppressed.
본 명세서에서 '제1 반복 단위'란, 발명에 따른 공중합체에 포함되는 화학식 1로 표시되는 반복 단위로서, 우수한 정공 전달 특성을 가진다. In the present specification, the 'first repeating unit' is a repeating unit represented by
바람직하게는, R1 내지 R3는 각각 독립적으로 수소, 또는 메틸이고, 보다 바람직하게는 모두 수소이다. Preferably, R 1 to R 3 are each independently hydrogen or methyl, and more preferably all are hydrogen.
바람직하게는, L1은 단일 결합, 또는 
바람직하게는, Ar1 및 Ar2는 각각 독립적으로, 페닐, 비페닐릴, 또는 디메틸플루오레닐이다. Preferably, Ar 1 and Ar 2 are each independently phenyl, biphenylyl, or dimethylfluorenyl.
바람직하게는, Ar1은 비페닐릴이고, Ar2는 디메틸플루오레닐이다.Preferably, Ar 1 is biphenylyl and Ar 2 is dimethylfluorenyl.
바람직하게는, 상기 화학식 1은 하기 중 어느 하나로 표시되는 반복 단위이다:Preferably,
한편, 상기 화학식 1로 표시되는 화합물은 하기 화학식 1-1로 표시되는 단량체로부터 유래된다:Meanwhile, the compound represented by
[화학식 1-1][Formula 1-1]
상기 화학식 1-1에서, R1 내지 R3, L1, Ar1 및 Ar2는 상기 화학식 1에서 정의한 바와 같다. In Formula 1-1, R 1 to R 3 , L 1 , Ar 1 and Ar 2 are as defined in
본 명세서에서 '제2 반복단위'란, 발명에 따른 공중합체에 포함되는 화학식 2로 표시되는 반복단위로서, 경화 가능한 반응기를 포함한다. 본 발명에 따른 공중합체를 증착한 후 경화시켜 증착된 공중합체가 용매 내성을 가지게 함으로써, 용액 공정으로 유기 발광 소자에 적용할 수 있다. In the present specification, the 'second repeating unit' is a repeating unit represented by
바람직하게는, R4 내지 R6는 각각 독립적으로 수소, 또는 메틸이고, 보다 바람직하게는 모두 수소이다. Preferably, R 4 to R 6 are each independently hydrogen or methyl, and more preferably all are hydrogen.
바람직하게는, L2은 비페닐디일이고, 보다 바람직하게는 비페닐릴-4,4'-디일이다. Preferably, L 2 is biphenyldiyl, more preferably biphenylyl-4,4'-diyl.
바람직하게는, 상기 화학식 2는 하기로 표시된다.Preferably, the formula (2) is represented below.
한편, 상기 화학식 2로 표시되는 화합물은 하기 화학식 2-1로 표시되는 단량체로부터 유래된다:Meanwhile, the compound represented by
[화학식 2-1][Formula 2-1]
상기 화학식 2-1에서, R4 내지 R6, 및 L2은 상기 화학식 2에서 정의한 바와 같다. In Formula 2-1, R 4 to R 6 , and L 2 are as defined in
(공중합체)(Copolymer)
본 발명에 따른 공중합체는 상술한 화학식 1-1로 표시되는 단량체, 및 화학식 2-1로 표시되는 단량체를 중합하여 제조할 수 있다. 바람직하게는, 본 발명에 따른 공중합체는 상기 반복단위를 포함하는 랜덤 공중합체이다. The copolymer according to the present invention can be prepared by polymerizing the monomer represented by the above-described formula 1-1, and the monomer represented by the formula 2-1. Preferably, the copolymer according to the present invention is a random copolymer comprising the repeating unit.
본 발명에 따른 고분자에서, x 및 y는 상기 공중합체 내 상기 화학식 1의 반복단위, 및 화학식 2의 반복단위의 몰비로서, 상술한 화학식 1-1로 표시되는 단량체, 및 화학식 2-1로 표시되는 단량체의 반응 몰비를 조절하여, 상기 고분자의 몰비를 조절할 수 있다. 바람직하게는, 상기 x:y는 70 내지 90: 1 내지 30이다. In the polymer according to the present invention, x and y are the molar ratios of the repeating unit of
바람직하게는, 상기 공중합체의 중량평균분자량은 5,000 내지 100,000이다. Preferably, the weight average molecular weight of the copolymer is 5,000 to 100,000.
(코팅 조성물)(Coating composition)
본 발명에 따른 공중합체는 용액 공정으로 유기 발광 소자의 유기물 층, 특히 정공수송층을 형성할 수 있다. 이를 위하여, 본 발명은 상술한 본 발명에 따른 공중합체 및 용매를 포함하는 코팅 조성물을 제공한다. The copolymer according to the present invention may form an organic material layer, particularly a hole transport layer, of an organic light emitting device by a solution process. To this end, the present invention provides a coating composition comprising a copolymer and a solvent according to the present invention described above.
상기 용매는 본 발명에 따른 공중합체를 용해 또는 분산시킬 수 있는 용매이면 특별히 제한되지 않으며, 일례로 클로로포름, 염화메틸렌, 1,2-디클로로에탄, 1,1,2-트리클로로에탄, 클로로벤젠, o-디클로로벤젠 등의 염소계 용매; 테트라하이드로퓨란, 디옥산 등의 에테르계 용매; 톨루엔, 크실렌, 트리메틸벤젠, 메시틸렌 등의 방향족 탄화수소계 용매; 시클로헥산, 메틸시클로헥산, n-펜탄, n-헥산, n-헵탄, n-옥탄, n-노난, n-데칸 등의 지방족 탄화수소계 용매; 아세톤, 메틸에틸케톤, 시클로헥사논 등의 케톤계 용매; 아세트산에틸, 아세트산부틸, 에틸셀로솔브아세테이트 등의 에스테르계 용매; 에틸렌글리콜, 에틸렌글리콜모노부틸에테르, 에틸렌글리콜모노에틸에테르, 에틸렌글리콜모노메틸에테르, 디메톡시에탄, 프로필렌글리콜, 디에톡시메탄, 트리에틸렌글리콜모노에틸에테르, 글리세린, 1,2-헥산디올 등의 다가 알코올 및 그의 유도체; 메탄올, 에탄올, 프로판올, 이소프로판올, 시클로헥산올 등의 알코올계 용매; 디메틸술폭사이드 등의 술폭사이드계 용매; 및 N-메틸-2-피롤리돈, N,N-디메틸포름아미드 등의 아미드계 용매; 부틸벤조에이트, 메틸-2-메톡시벤조에이트 등의 벤조에이트계 용매; 테트랄린; 3-페녹시-톨루엔 등의 용매를 들 수 있다. 또한, 상술한 용매를 1종 단독으로 사용하거나 2종 이상의 용매를 혼합하여 사용할 수 있다. The solvent is not particularly limited as long as it is a solvent capable of dissolving or dispersing the copolymer according to the present invention. For example, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, chlorine-based solvents such as o-dichlorobenzene; Ether-based solvents such as tetrahydrofuran and dioxane; Aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene and mesitylene; Aliphatic hydrocarbon-based solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; Ketone solvents such as acetone, methyl ethyl ketone, and cyclohexanone; Ester solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; Polyvalent values of ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol, etc. Alcohols and derivatives thereof; Alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; Sulfoxide-based solvents such as dimethyl sulfoxide; And amide solvents such as N-methyl-2-pyrrolidone and N, N-dimethylformamide; Benzoate solvents such as butyl benzoate and methyl-2-methoxybenzoate; Tetralin; And solvents such as 3-phenoxy-toluene. Further, the above-described solvent may be used alone or in combination of two or more solvents.
또한, 상기 코팅 조성물의 점도는 1 cP 내지 10 cP가 바람직하며, 상기의 범위에서 코팅이 용이하다. 또한, 상기 코팅 조성물 내 본 발명에 따른 공중합체의 농도는 0.1 wt/v% 내지 20 wt/v%인 것이 바람직하다. In addition, the viscosity of the coating composition is preferably 1 cP to 10 cP, and the coating is easy in the above range. In addition, the concentration of the copolymer according to the present invention in the coating composition is preferably 0.1 wt / v% to 20 wt / v%.
또한, 본 발명은 상술한 코팅 조성물을 사용하여 정공수송층을 형성하는 방법을 제공한다. 구체적으로, 양극 상에, 또는 양극 상에 형성된 정공주입층 상에, 상술한 본 발명에 따른 코팅 조성물을 용액 공정으로 코팅하는 단계; 및 상기 코팅된 코팅 조성물을 열처리하는 단계를 포함한다. In addition, the present invention provides a method for forming a hole transport layer using the above-described coating composition. Specifically, on the positive electrode, or on the hole injection layer formed on the positive electrode, coating the coating composition according to the present invention described above by a solution process; And heat-treating the coated coating composition.
상기 용액 공정은 상술한 본 발명에 따른 코팅 조성물을 사용하는 것으로, 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.The solution process refers to the use of the coating composition according to the present invention described above, which means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
상기 열처리 단계에서 열처리 온도는 150 내지 230℃가 바람직하다. 또한, 상기 열처리 시간은 1분 내지 3시간이고, 보다 바람직하게는 10분 내지 1시간이다. 또한, 상기 열처리는 아르곤, 질소 등의 불활성 기체 분위기에서 수행하는 것이 바람직하다. 또한, 상기 코팅 단계와 상기 열처리 또는 광처리 단계 사이에 용매를 증발시키는 단계를 추가로 포함할 수 있다. In the heat treatment step, the heat treatment temperature is preferably 150 to 230 ° C. In addition, the heat treatment time is 1 minute to 3 hours, more preferably 10 minutes to 1 hour. In addition, the heat treatment is preferably performed in an inert gas atmosphere such as argon and nitrogen. In addition, a step of evaporating the solvent between the coating step and the heat treatment or light treatment step may be further included.
(유기 발광 소자)(Organic light emitting element)
또한, 본 발명은 상술한 본 발명에 따른 공중합체를 포함하는 유기 발광 소자를 제공한다. 구체적으로, 본 발명은 양극; 상기 양극과 대향하여 구비된 음극; 상기 양극과 상기 음극 사이에 구비된 발광층; 및 상기 양극과 상기 발광층 사이에 구비된 정공수송층을 포함하고, 상기 정공수송층은 본 발명에 따른 공중합체를 포함하는, 유기 발광 소자를 제공한다. In addition, the present invention provides an organic light emitting device comprising the copolymer according to the present invention described above. Specifically, the present invention is an anode; A cathode provided opposite the anode; A light emitting layer provided between the anode and the cathode; And a hole transport layer provided between the anode and the light emitting layer, wherein the hole transport layer includes the copolymer according to the present invention.
본 발명의 일실시예에 따른 유기 발광 소자의 구조는 도 1 및 2에 예시되어 있다.The structure of the organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
도 1은 기판(1), 양극(2), 정공수송층(3), 발광층(4), 음극(5)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 도 2는 기판 (1), 양극(2), 정공주입층(6), 정공수송층(3), 발광층(4), 전자수송층(7), 전자주입층(8) 및 음극(5)로 이루어진 유기 발광 소자의 예를 도시한 것이다.FIG. 1 shows an example of an organic light emitting device comprising a
본 발명에 따른 유기 발광 소자는, 상기 정공수송층이 본 발명에 따른 공중합체를 포함하고, 상술한 방법과 같이 제조되는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조할 수 있다.The organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that the hole transport layer includes the copolymer according to the present invention and is prepared as described above.
예컨대, 본 발명에 따른 유기 발광 소자는 기판 상에 양극, 유기물층 및 음극을 순차적으로 적층시켜 제조할 수 있다. 이때, 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(physical Vapor Deposition) 방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물 층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시켜 제조할 수 있다. For example, the organic light emitting device according to the present invention may be manufactured by sequentially laminating an anode, an organic material layer, and a cathode on a substrate. At this time, a positive electrode is formed by depositing metal or conductive metal oxides or alloys thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. Then, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed thereon, and a material that can be used as a cathode is deposited thereon.
이와 같은 방법 외에도, 기판 상에 음극 물질로부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 제조할 수 있다(WO 2003/012890). 다만, 제조 방법이 이에 한정되는 것은 아니다. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
상기 양극 물질로는 통상 유기물 층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 상기 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SNO2:Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. The positive electrode material is preferably a material having a large work function so that hole injection into the organic material layer is smooth. Specific examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO: Al or SNO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 상기 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다. The cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There is a multilayer structure material such as LiF / Al or LiO 2 / Al, but is not limited thereto.
상기 정공주입층은 전극으로부터 정공을 주입하는 층으로, 정공 주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입효과, 발광층 또는 발광재료에 대하여 우수한 정공 주입 효과를 갖고, 발광층에서 생성된 여기자의 전자주입층 또는 전자주입재료에의 이동을 방지하며, 또한, 박막 형성 능력이 우수한 화합물이 바람직하다. 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물 층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrin), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone)계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정 되는 것은 아니다. The hole injection layer is a layer for injecting holes from an electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is produced in the light emitting layer. A compound which prevents migration of the excitons to the electron injection layer or the electron injection material, and which has excellent thin film formation ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic matter, hexanitrile hexaazatriphenylene-based organic matter, quinacridone-based organic matter, and perylene-based Organic materials, anthraquinones, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
상기 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 구체적인 예로 8-히드록시-퀴놀린 알루미늄 착물(Alq3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다. As the light-emitting material, a material capable of emitting light in the visible light region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, is preferably a material having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly (p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.
상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되지 않는다. The light emitting layer may include a host material and a dopant material. The host material may be a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
도펀트 재료로는 방향족 아민 유도체, 스트릴아민 화합물, 붕소 착체, 플루오란텐 화합물, 금속 착체 등이 있다. 구체적으로 방향족 아민 유도체로는 치환 또는 비치환된 아릴아미노기를 갖는 축합 방향족환 유도체로서, 아릴아미노기를 갖는 피렌, 안트라센, 크리센, 페리플란텐 등이 있으며, 스티릴아민 화합물로는 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로, 아릴기, 실릴기, 알킬기, 사이클로알킬기 및 아릴아미노기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민, 스티릴디아민, 스티릴트리아민, 스티릴테트라아민 등이 있으나, 이에 한정되지 않는다. 또한, 금속 착체로는 이리듐 착체, 백금 착체 등이 있으나, 이에 한정되지 않는다.Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes arylamino groups such as pyrene, anthracene, chrysene, periplanten, and the substituted or unsubstituted styrylamine compound. A compound in which at least one arylvinyl group is substituted with the arylamine, a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, examples of the metal complex include an iridium complex and a platinum complex, but are not limited thereto.
상기 전자수송층은 전자주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층으로 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이 임의의 원하는 캐소드 물질과 함께 사용할 수 있다. 특히, 적절한 캐소드 물질의 예는 낮은 일함수를 가지고 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로 세슘, 바륨, 칼슘, 이테르븀 및 사마륨이고, 각 경우 알루미늄 층 또는 실버층이 뒤따른다.The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited to these. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are those that have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, each case followed by an aluminum layer or a silver layer.
상기 전자주입층은 전극으로부터 전자를 주입하는 층으로, 전자를 수송하는 능력을 갖고, 음극으로부터의 전자 주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공주입층에의 이동을 방지하고, 또한, 박막형성능력이 우수한 화합물이 바람직하다. 구체적으로는 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 질소 함유 5원환 유도체 등이 있으나, 이에 한정되지 않는다. The electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect on a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
상기 금속 착체 화합물로서는 8-하이드록시퀴놀리나토 리튬, 비스(8-하이드록시퀴놀리나토)아연, 비스(8-하이드록시퀴놀리나토)구리, 비스(8-하이드록시퀴놀리나토)망간, 트리스(8-하이드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-하이드록시퀴놀리나토)알루미늄, 트리스(8-하이드록시퀴놀리나토)갈륨, 비스(10-하이드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-하이드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되지 않는다.Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.
본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present invention may be a front emission type, a back emission type, or a double-sided emission type depending on the material used.
또한, 본 발명에 따른 공중합체는 유기 발광 소자 외에도 유기 태양 전지 또는 유기 트랜지스터에 포함될 수 있다.In addition, the copolymer according to the present invention may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
본 발명에 따른 공중합체 및 이를 포함하는 유기 발광 소자의 제조는 이하 실시예에서 구체적으로 설명한다. 그러나 하기 실시예는 본 발명을 예시하기 위한 것이며, 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다.The production of the copolymer according to the present invention and the organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the invention, and the scope of the invention is not limited by them.
실시예Example 1 One
화합물 1-1(0.5 g, 0.93 mmol), 화합물 1-2(0.2 g, 0.72 mmol), 및 AIBN(5.0 mg, 0.03 mmol)을 schlenk flask에 넣고 THF(1.5 ml)에 녹인 후, freeze-evacuate-thaw를 3번 반복하고 60℃에서 17시간 동안 교반하였다. 반응 종료 후, 용액을 메탄올에 부어 침전을 잡아 공중합체를 수득하였다. 여과하여 얻은 공중합체를 vacuum oven에서 밤새 보관하였다. 이렇게 얻어진 공중합체를 0℃에서 THF(10 ml)에 녹인 후, TBAF(5 ml)을 첨가하고 3시간 동안 교반한 후, 물을 넣어 반응을 종료하고 메탄올에 침전을 잡았다. 흡착 컬럼(Hex:MC=8:2)으로 남아 있는 단량체들을 제거하고 THF를 흘려 얻은 공중합체 용액을 evaporation 후, 메탄올에 침전을 잡고 여과 후, vacuum oven 에서 건조하여 공중합체를 얻었다. 1H NMR 및 GPC 분석을 통하여 공중합체 중합 여부, copolymer의 block 비율, 분자량 및 분자량 분포를 확인하였다. Compound 1-1 (0.5 g, 0.93 mmol), compound 1-2 (0.2 g, 0.72 mmol), and AIBN (5.0 mg, 0.03 mmol) were placed in a schlenk flask, dissolved in THF (1.5 ml), and then freeze-evacuate The -thaw was repeated 3 times and stirred at 60 DEG C for 17 hours. After completion of the reaction, the solution was poured into methanol to precipitate and obtain a copolymer. The copolymer obtained by filtration was stored in a vacuum oven overnight. The copolymer thus obtained was dissolved in THF (10 ml) at 0 ° C., and TBAF (5 ml) was added and stirred for 3 hours, water was added to terminate the reaction, and precipitate was precipitated in methanol. After removing the remaining monomers with an adsorption column (Hex: MC = 8: 2) and flowing THF, the copolymer solution obtained was evaporated, precipitated in methanol, filtered, and dried in a vacuum oven to obtain a copolymer. Through 1H NMR and GPC analysis, the copolymer polymerization, block ratio of the copolymer, molecular weight and molecular weight distribution were confirmed.
실시예Example 2 2
실시예 1과 동일한 방법으로 제조하되, 화합물 1-2를 0.05 g 사용하여, 공중합체를 얻었다. Prepared in the same manner as in Example 1, using a compound 1-2 of 0.05 g, to obtain a copolymer.
실시예Example 3 3
실시예 1과 동일한 방법으로 제조하되, 화합물 1-1 대신 화합물 3-1을 0.5 g 사용하고, 화합물 1-2를 0.05 g 사용하여, 공중합체를 얻었다. Prepared in the same manner as in Example 1, using 0.5 g of compound 3-1 instead of compound 1-1, and 0.05 g of compound 1-2 to obtain a copolymer.
실시예Example 4 4
실시예 3과 동일한 방법으로 제조하되, 화합물 1-2를 0.2 g 사용하여, 공중합체를 얻었다. Prepared in the same manner as in Example 3, 0.2 g of Compound 1-2 was used to obtain a copolymer.
[[ 실험예Experimental example ]]
실험예Experimental example 1 One
앞서 제조한 공중합체의 1H NMR 및 GPC 분석을 통하여 공중합체 중합 여부, copolymer의 block 비율, 분자량 및 분자량 분포를 확인하였다. 구체적으로, 1H NMR은 도 3에 나타내었고, GPC 분석 결과는 도 4에 나타내었다. 또한, ethynyl proton peak의 integration 값을 바탕으로 각 공중합체에서 ethynyl group을 포함하고 있는 block의 wt%를 계산하여 이하 표 1에 나타내었다. Through the 1H NMR and GPC analysis of the previously prepared copolymer, it was confirmed whether the copolymer was polymerized, the block ratio of the copolymer, and the molecular weight and molecular weight distribution. Specifically, 1H NMR is shown in Figure 3, GPC analysis results are shown in Figure 4. In addition, based on the integration value of the ethynyl proton peak, the wt% of the block containing the ethynyl group in each copolymer was calculated and shown in Table 1 below.
실험예Experimental example 2 2
톨루엔 및 사이클로헥사논을 사용하여, 상기 제조한 공중합체의 용매 내성을 평가하였다. Toluene and cyclohexanone were used to evaluate the solvent resistance of the prepared copolymer.
구체적으로, 상기 제조한 공중합체를 2 wt%로 톨루엔에 녹인 용액을 제조한 후, 이를 스핀코팅으로 quartz 기판에 100nm 두께로 코팅하였다. 그 후 질소 분위기에서 1시간 동안 190 내지 200℃에서 열처리한 후 UV-Vis absorption spectrum을 측정하였다. 이어, 동일한 샘플을 톨루엔 또는 사이클로헥사논에 10분 동안 담궈 두었다가 꺼내어, 용매가 건조된 뒤 다시 UV-Vis absorption spectrum을 측정하였다.Specifically, after preparing the solution in which the prepared copolymer was dissolved in toluene at 2 wt%, it was coated with a thickness of 100 nm on a quartz substrate by spin coating. Thereafter, heat treatment was performed at 190 to 200 ° C. for 1 hour in a nitrogen atmosphere, and then UV-Vis absorption spectrum was measured. Subsequently, the same sample was immersed in toluene or cyclohexanone for 10 minutes, then taken out, and the UV-Vis absorption spectrum was measured again after the solvent was dried.
상기 측정 결과를 도 5에 나타내었다. 도 5에 나타난 바와 같이, 사이클로헥사논에 대해서는 모두 막유지율이 100%로 나타났으며, 톨루엔에 대해서도 높은 막 유지율을 나타내었다. The measurement results are shown in FIG. 5. As shown in FIG. 5, all of the cyclohexanone exhibited a membrane retention ratio of 100%, and also exhibited a high membrane retention ratio for toluene.
실험예Experimental example 3 3
ITO(indium tin oxide)가 1,500Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이 때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀리포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후, 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필, 아세톤의 용제로 초음파 세척을 하고 건조시킨 후, 상기 기판을 5분간 세정한 후 글로브박스로 기판을 수송시켰다.A glass substrate coated with a thin film coated with ITO (indium tin oxide) at a thickness of 1,500 에 was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer Co. was used as a detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl and acetone, followed by drying, and then the substrate was washed for 5 minutes and then transferred to a glove box.
정공주입층의 호스트로 하기 VNBP 화합물, 및 정공주입층의 도펀트로 하기 IB 화합물을 용매(cyclohexanone)에 녹여 코팅 조성물을 준비하였다. 정공주입층의 호스트와 도펀트의 비율은 무게비로 8:2로 혼합하였다. 이렇게 제조된 정공주입층 혼합물을 앞서 준비한 ITO 기판 위에 400Å 두께로 스핀코팅하고, Ar 분위기 하에 230℃ 조건에서 30분 동안 경화시켜 정공주입층을 형성하였다. 이후, 상기 정공주입층 위에 하기 표 1과 같이 앞서 실시예에서 제조한 공중합체를 1.0 wt/v%로 톨루엔에 녹여 스핀코팅하여 200Å의 두께로 성막하고 질소 분위기 하에 200℃로 1시간 동안 가열하여 정공수송층을 형성하였다. 이어서 상기 정공 수송층 위에 하기 HOST 화합물과 DOPANT 화합물을 94:6의 중량비로 포함하는 톨루엔 용액을 200Å으로 스핀코팅하고 질소 분위기 하에서 120℃로 10분간 가열하여 발광층을 형성하였다. 발광층 위에 하기 ETL 화합물을 200Å의 두께로 진공 증착하여 전자 주입 및 수송층을 형성하였다. 상기 전자 주입 및 수송층 위에 순차적으로 10Å의 두께로 LiF와 1000Å의 두께로 알루미늄을 증착하여 캐소드를 형성하였다.A coating composition was prepared by dissolving the following VNBP compound as a host for the hole injection layer and the following IB compound as a dopant for the hole injection layer in a solvent (cyclohexanone). The ratio of the host and the dopant in the hole injection layer was mixed at a weight ratio of 8: 2. The thus prepared hole injection layer mixture was spin coated on a previously prepared ITO substrate to a thickness of 400
상기의 과정에서 유기물의 증착 속도는 0.4 내지 0.7Å/sec 를 유지하였고, 캐소드의 LiF는 0.3Å/sec, 알루미늄은 2Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 2×10-7 내지 5×10-8 torr를 유지하였다. 그 후, 유리에 밀봉 유리와 유리 기판을, 광경화성 에폭시 수지를 이용하여 접합시킴으로써 밀봉을 행하여, 다층 구조의 유기 발광 소자를 제작했다. 이후의 조작은 대기중, 실온(25℃)에서 행했다.In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Pa / sec, the LiF of the cathode was maintained at a deposition rate of 0.3 Pa / sec and aluminum at 2 Pa / sec, and the vacuum degree during deposition was 2 × 10 -7 to 5 × 10 −8 torr was maintained. Thereafter, sealing was performed by bonding the sealing glass and the glass substrate to the glass using a photocurable epoxy resin, thereby producing an organic light emitting device having a multilayer structure. Subsequent operation was performed at room temperature (25 ° C) in the air.
상기 제조한 유기 발광 소자를 10 mA/cm2의 전류 밀도에서 구동 전압, 효율, QE 및 색좌표를 측정하여 하기 표 2에 나타내었다. The manufactured organic light emitting device was measured in the current density of 10 mA / cm 2 , and the driving voltage, efficiency, QE, and color coordinates were measured and shown in Table 2 below.
수송층Hole
Transport layer
(V)Voltage
(V)
(Cd/A)efficiency
(Cd / A)
(%)QE
(%)
1: 기판
2: 양극
3: 정공수송층
4: 발광층
5: 음극
6: 정공주입층
7: 전자수송층
8: 전자주입층1: substrate 2: anode
3: hole transport layer 4: light emitting layer
5: cathode 6: hole injection layer
7: electron transport layer 8: electron injection layer
Claims (9)
[화학식 1]
상기 화학식 1에서,
R1 내지 R3는 각각 독립적으로, 수소, 또는 C1-10 알킬이고,
L1은 단일 결합; 치환 또는 비치환된 C6-60 아릴렌; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴렌이고,
Ar1 및 Ar2는 각각 독립적으로, 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴이고, 단 Ar1 및 Ar2는 서로 상이하고,
[화학식 2]
상기 화학식 2에서,
R4 내지 R6는 각각 독립적으로, 수소, 또는 C1-10 알킬이고,
L2은 치환 또는 비치환된 C6-60 아릴렌; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴렌이고,
x 및 y는 각각 독립적으로 1 내지 100의 정수이다.
A copolymer comprising a repeating unit represented by Formula 1 and a repeating unit represented by Formula 2 below:
[Formula 1]
In Chemical Formula 1,
R 1 to R 3 are each independently hydrogen, or C 1-10 alkyl,
L 1 is a single bond; Substituted or unsubstituted C 6-60 arylene; Or C 2-60 heteroarylene comprising any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
Ar 1 and Ar 2 are each independently, substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S, provided that Ar 1 and Ar 2 are different from each other,
[Formula 2]
In Chemical Formula 2,
R 4 to R 6 are each independently hydrogen, or C 1-10 alkyl,
L 2 is substituted or unsubstituted C 6-60 arylene; Or C 2-60 heteroarylene comprising any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
x and y are each independently an integer from 1 to 100.
L1은 단일 결합, 또는
공중합체.
According to claim 1,
L 1 is a single bond, or
Copolymer.
Ar1 및 Ar2는 각각 독립적으로, 페닐, 비페닐릴, 또는 디메틸플루오레닐인,
공중합체.
According to claim 1,
Ar 1 and Ar 2 are each independently phenyl, biphenylyl, or dimethylfluorenyl,
Copolymer.
Ar1은 비페닐릴이고,
Ar2는 디메틸플루오레닐인,
공중합체.
According to claim 1,
Ar 1 is biphenylyl,
Ar 2 is dimethylfluorenyl,
Copolymer.
상기 화학식 1은 하기 중 어느 하나로 표시되는,
공중합체:
According to claim 1,
Formula 1 is represented by any one of the following,
Copolymer:
L2는 비페닐디일인,
공중합체.
According to claim 1,
L 2 is biphenyldiyl,
Copolymer.
상기 화학식 2는 하기로 표시되는,
공중합체:
According to claim 1,
Formula 2 is represented by the following,
Copolymer:
상기 공중합체 의 중량평균분자량은 5,000 내지 100,000인,
공중합체.
According to claim 1,
The weight average molecular weight of the copolymer is 5,000 to 100,000,
Copolymer.
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|---|---|---|---|---|
| KR20000051826A (en) | 1999-01-27 | 2000-08-16 | 성재갑 | New organomattalic complex molecule for the fabrication of organic light emitting diodes |
| KR20140004422A (en) * | 2012-07-02 | 2014-01-13 | 광주과학기술원 | Hole transport high molecular polymeric compound and polymer light emitting diode using the same |
| KR20150105755A (en) * | 2014-03-10 | 2015-09-18 | 광주과학기술원 | Hole transport high molecular random copolymer and polymer light emitting diode using the Same |
| WO2018005318A1 (en) * | 2016-06-28 | 2018-01-04 | Dow Global Technologies Llc | Quantum dot light emitting devices |
| US20180022865A1 (en) * | 2015-01-13 | 2018-01-25 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Conjugated polymer containing ethynyl crosslinking group, mixture composition, organic electronic device continaing the same and application therof |
| KR20180059379A (en) * | 2016-11-25 | 2018-06-04 | 주식회사 엘지화학 | Organic light emitting device |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20000051826A (en) | 1999-01-27 | 2000-08-16 | 성재갑 | New organomattalic complex molecule for the fabrication of organic light emitting diodes |
| KR20140004422A (en) * | 2012-07-02 | 2014-01-13 | 광주과학기술원 | Hole transport high molecular polymeric compound and polymer light emitting diode using the same |
| KR20150105755A (en) * | 2014-03-10 | 2015-09-18 | 광주과학기술원 | Hole transport high molecular random copolymer and polymer light emitting diode using the Same |
| US20180022865A1 (en) * | 2015-01-13 | 2018-01-25 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Conjugated polymer containing ethynyl crosslinking group, mixture composition, organic electronic device continaing the same and application therof |
| WO2018005318A1 (en) * | 2016-06-28 | 2018-01-04 | Dow Global Technologies Llc | Quantum dot light emitting devices |
| KR20180059379A (en) * | 2016-11-25 | 2018-06-04 | 주식회사 엘지화학 | Organic light emitting device |
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