KR20200068568A - Novel compound and organic light emitting device comprising the same - Google Patents
Novel compound and organic light emitting device comprising the same Download PDFInfo
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- KR20200068568A KR20200068568A KR1020190139629A KR20190139629A KR20200068568A KR 20200068568 A KR20200068568 A KR 20200068568A KR 1020190139629 A KR1020190139629 A KR 1020190139629A KR 20190139629 A KR20190139629 A KR 20190139629A KR 20200068568 A KR20200068568 A KR 20200068568A
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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
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-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
- 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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- H10K50/00—Organic light-emitting devices
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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Abstract
Description
본 발명은 신규한 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. The present invention relates to a novel compound 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 a 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, 전자저지층, 발광층, 정공저지층, 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. The organic material layer is often composed of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, electrons It may be made of an injection layer or 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 an exciton is formed when the injected holes meet the electrons. When it falls to the ground again, it glows.
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.
본 발명은 신규한 유기발광 재료 및 이를 포함하는 유기 발광 소자에 관한 것이다.The present invention relates to a novel organic light emitting material and an organic light emitting device comprising the same.
본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:The present invention provides a compound represented by Formula 1:
[화학식 1][Formula 1]
상기 화학식 1에서,In Chemical Formula 1,
A는 인접한 두 개의 고리와 융합된 벤젠 고리이고,A is a benzene ring fused with two adjacent rings,
X1 및 X2는 각각 독립적으로, O 또는 S이고,X 1 and X 2 are each independently O or S,
Y1 내지 Y3는 각각 독립적으로, N 또는 CH이고, Y1 내지 Y3 중 적어도 하나는 N이고,Y 1 to Y 3 are each independently N or CH, and at least one of Y 1 to Y 3 is N,
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,Ar 1 and Ar 2 are each independently, substituted or unsubstituted C 6-60 aryl; Or a substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,
R1 내지 R3는 각각 독립적으로, 수소; 중수소; 할로겐; 시아노; 니트로; 아미노; 치환 또는 비치환된 C1-60 알킬; 치환 또는 비치환된 C3-60 사이클로알킬; 치환 또는 비치환된 C2-60 알케닐; 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴이고,R 1 to R 3 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 3-60 cycloalkyl; Substituted or unsubstituted C 2-60 alkenyl; Substituted or unsubstituted C 6-60 aryl; Or a substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,
R4 및 R5는 각각 독립적으로, 수소; 중수소; 할로겐; 시아노; 니트로; 아미노; 치환 또는 비치환된 C1-60 알킬; 치환 또는 비치환된 C3-60 사이클로알킬; 치환 또는 비치환된 C2-60 알케닐; 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴이고,R 4 and R 5 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 3-60 cycloalkyl; Substituted or unsubstituted C 2-60 alkenyl; Substituted or unsubstituted C 6-60 aryl; Or a substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,
a 및 b는 각각 독립적으로, 0 내지 4인 정수이고,a and b are each independently an integer from 0 to 4,
c는 0 내지 2인 정수이고,c is an integer from 0 to 2,
d 및 e는 각각 독립적으로, 0 내지 3인 정수이다.d and e are each independently an integer from 0 to 3.
또한, 본 발명은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는, 유기 발광 소자를 제공한다.In addition, the present invention is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one layer of an organic material provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Chemical Formula 1, and provides an organic light emitting device. .
상술한 화학식 1로 표시되는 화합물은 유기 발광 소자의 유기물 층의 재료로서 사용될 수 있으며, 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는 수명 특성을 향상시킬 수 있다. 특히, 상술한 화학식 1로 표시되는 화합물은 정공주입, 정공수송, 정공주입 및 수송, 전자저지, 발광, 정공저지, 전자수송, 또는 전자주입 재료로 사용될 수 있다The compound represented by Chemical Formula 1 may be used as a material for an organic material layer of an organic light emitting device, and may improve efficiency, low driving voltage, and/or life characteristics in the organic light emitting device. In particular, the compound represented by Formula 1 may be used as a hole injection, hole transport, hole injection and transport, electron blocking, light emission, hole blocking, electron transport, or electron injection material
도 1은 기판(1), 양극(2), 발광층(3), 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.
도 2는 기판 (1), 양극(2), 정공수송층(5), 전자저지층(6), 발광층(3), 정공저지층(7), 전자수송층(8), 전자주입층(9) 및 음극(4)로 이루어진 유기 발광 소자의 예를 도시한 것이다.1 shows an example of an organic light emitting device including a
Figure 2 is a substrate (1), anode (2), hole transport layer (5), electron blocking layer (6), light emitting layer (3), hole blocking layer (7), electron transport layer (8), electron injection layer (9) And an example of an organic light-emitting device comprising the
이하, 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다.Hereinafter, it will be described in more detail in order to help the understanding of the present invention.
본 발명은 상기 화학식 1로 표시되는 화합물을 제공한다. The present invention provides a compound represented by Formula 1 above.
본 명세서에서, 는 다른 치환기에 연결되는 결합을 의미한다. In this specification, Means a linkage to another substituent.
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; Ar 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 this 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-butyl dimethyl 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, 사이클로헥실메틸, 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 a straight chain or a branched chain, 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, styrenyl 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, 등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, the fluorenyl group may be substituted, and two substituents may combine with each other to form a spiro structure. When the fluorenyl group is substituted, It can be back. However, it is not limited thereto.
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, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl 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, 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 of the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the above-described alkyl group. In the present specification, heteroarylamine among heteroarylamines may be applied to the description of the aforementioned heterocyclic group. 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.
상기 화학식 1에서, 벤젠 고리 A의 융합 위치에 따라 상기 화학식 1은 하기 화학식 1-1 내지 화학식 1-6 중 어느 하나로 표시될 수 있다: In
[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
[화학식 1-3][Formula 1-3]
[화학식 1-4][Formula 1-4]
[화학식 1-5][Formula 1-5]
[화학식 1-6][Formula 1-6]
상기 화학식 1-1 내지 화학식 1-6에서,In Formula 1-1 to Formula 1-6,
X1, X2, Y1 내지 Y3, Ar1, Ar2, R1 내지 R5 및 a 내지 e에 대한 설명은 상기 화학식 1에서 정의한 바와 같다.Description of X 1 , X 2 , Y 1 to Y 3 , Ar 1 , Ar 2 , R 1 to R 5 and a to e is as defined in
이때, a는 R1의 개수를 나타낸 것으로서, a가 2 이상일 경우, 2 이상의 R1은 서로 동일하거나 상이할 수 있다. b 내지 e에 대한 설명은 상기 a에 대한 설명 및 상기 화학식 1의 구조를 참조하여 이해될 수 있다.At this time, a represents the number of R 1. When a is 2 or more, two or more R 1 may be the same or different. The description of b to e may be understood by referring to the description of a and the structure of
바람직하게는, Y1 내지 Y3는 모두 N일 수 있다.Preferably, Y 1 to Y 3 may all be N.
바람직하게는, Ar1 및 Ar2는 각각 독립적으로, 치환 또는 비치환된 C6-20 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C6-20 헤테로아릴일 수 있고, Preferably, Ar 1 and Ar 2 are each independently, substituted or unsubstituted C 6-20 aryl; Or C 6-20 heteroaryl containing any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
보다 바람직하게는, Ar1 및 Ar2는 각각 독립적으로, 페닐, 비페닐릴, 터페닐릴, 나프틸, 안트라세닐, 페난트레닐, 트리페닐레닐, 플루오레닐, 디벤조퓨라닐, 디벤조티오페닐, 또는 5 개의 중수소로 치환된 페닐일 수 있다.More preferably, Ar 1 and Ar 2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, fluorenyl, dibenzofuranyl, dibenzo Thiophenyl, or phenyl substituted with 5 deuterium.
바람직하게는, Ar1 및 Ar2 중 적어도 하나는 치환 또는 비치환된 C6-60 아릴일 수 있고, Preferably, at least one of Ar 1 and Ar 2 may be substituted or unsubstituted C 6-60 aryl,
보다 바람직하게는 Ar1 및 Ar2 중 적어도 하나는 치환 또는 비치환된 C6-20 아릴일 수 있고,More preferably, at least one of Ar 1 and Ar 2 may be substituted or unsubstituted C 6-20 aryl,
가장 바람직하게는 Ar1 및 Ar2 중 적어도 하나는 페닐 또는 5 개의 중수소로 치환된 페닐일 수 있다.Most preferably, at least one of Ar 1 and Ar 2 may be phenyl or phenyl substituted with 5 deuteriums.
상기 R3는 벤젠 고리 A의 치환기이다.R 3 is a substituent of benzene ring A.
바람직하게는, R1 내지 R3는 각각 독립적으로, 수소; 중수소; 치환 또는 비치환된 C1-20 알킬; 치환 또는 비치환된 C6-20 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C6-20 헤테로아릴일 수 있고, Preferably, R 1 to R 3 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 1-20 alkyl; Substituted or unsubstituted C 6-20 aryl; Or C 6-20 heteroaryl containing any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
보다 바람직하게는, R1 내지 R3는 각각 독립적으로, 수소, 중수소, 또는 페닐일 수 있다.More preferably, R 1 to R 3 may each independently be hydrogen, deuterium, or phenyl.
바람직하게는, R4 및 R5는 각각 독립적으로, 수소; 치환 또는 비치환된 C1-20 알킬; 치환 또는 비치환된 C6-20 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C6-20 헤테로아릴일 수 있고, Preferably, R 4 and R 5 are each independently hydrogen; Substituted or unsubstituted C 1-20 alkyl; Substituted or unsubstituted C 6-20 aryl; Or C 6-20 heteroaryl containing any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
보다 바람직하게는, R4 및 R5는 각각 독립적으로, 수소 또는 중수소일 수 있다.More preferably, R 4 and R 5 may each independently be hydrogen or deuterium.
상기 화학식 1로 표시되는 화합물의 대표적인 예는 다음과 같다: Representative examples of the compound represented by
. .
상기 화학식 1로 표시되는 화합물은 일례로 하기 반응식 1 및 반응식 2와 같은 제조 방법으로 제조할 수 있으며, 그 외 나머지 화합물도 유사하게 제조할 수 있다.The compound represented by
[반응식 1][Scheme 1]
[반응식 2][Scheme 2]
상기 반응식 1 및 2에서, X1, X2, Y1 내지 Y3, Ar1, Ar2 및 R1 내지 R3는 상기 화학식 1에서 정의한 바와 같으며, Z1 및 Z2는 할로겐이고, 바람직하게는 Z1 및 Z2는 클로로 또는 브로모이다.In
상기 반응식 1은 스즈키 커플링 반응으로서, 팔라듐 촉매와 염기 존재 하에 수행하는 것이 바람직하며, 스즈키 커플링 반응을 위한 반응기는 당업계에 알려진 바에 따라 변경이 가능하다. 또한, 상기 반응식 2는 아민 치환 반응으로서, 팔라듐 촉매와 염기 존재 하에 수행하는 것이 바람직하며, 아민 치환 반응을 위한 반응기는 당업계에 알려진 바에 따라 변경이 가능하다. 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다.
또한, 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다. 일례로, 본 발명은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물 층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는, 유기 발광 소자를 제공한다. In addition, the present invention provides an organic light emitting device comprising the compound represented by the formula (1). In one example, the present invention is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one layer of an organic material provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by
본 발명의 유기 발광 소자의 유기물 층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 발광 소자는 유기물 층으로서 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층을 포함할 수 있다.The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and may include fewer organic layers.
또한, 상기 유기물 층은 발광층, 정공수송층, 정공주입층, 또는 정공수송 및 정공주입을 동시에 하는 층을 포함할 수 있고, 상기 발광층, 정공수송층, 정공주입층, 또는 정공수송 및 정공주입을 동시에 하는 층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.In addition, the organic layer may include a light emitting layer, a hole transport layer, a hole injection layer, or a layer simultaneously performing hole transport and hole injection, and the light emitting layer, hole transport layer, hole injection layer, or hole transport and hole injection at the same time The layer may include a compound represented by
또한, 상기 유기물 층은 발광층을 포함할 수 있고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함한다. 특히, 본 발명에 따른 화합물은 발광층의 호스트로 사용할 수 있다. In addition, the organic material layer may include a light emitting layer, and the light emitting layer includes a compound represented by
또한, 상기 유기물 층은 발광층, 전자수송층, 전자주입층, 또는 전자수송 및 전자주입을 동시에 하는 층을 포함할 수 있고, 상기 발광층, 전자수송층, 전자주입층, 또는 전자수송 및 전자주입을 동시에 하는 층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. In addition, the organic material layer may include a light emitting layer, an electron transport layer, an electron injection layer, or a layer simultaneously performing electron transport and electron injection, and the light emitting layer, electron transport layer, electron injection layer, or electron transport and electron injection may be simultaneously performed. The layer may include a compound represented by
또한, 상기 유기물 층은 발광층, 전자저지층 및 정공저지층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. In addition, the organic material layer includes a light emitting layer, an electron blocking layer and a hole blocking layer, and the light emitting layer may include a compound represented by
또한, 본 발명에 따른 유기 발광 소자는, 기판 상에 양극, 1층 이상의 유기물 층 및 음극이 순차적으로 적층된 구조(normal type)의 유기 발광 소자일 수 있다. 또한, 본 발명에 따른 유기 발광 소자는 기판 상에 음극, 1층 이상의 유기물 층 및 양극이 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다. 예컨대, 본 발명의 일실시예에 따른 유기 발광 소자의 구조는 도 1 및 2에 예시되어 있다.Further, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present invention may be an organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, 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), 발광층(3), 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 발광층에 포함될 수 있다. 1 shows an example of an organic light emitting device including a
도 2는 기판 (1), 양극(2), 정공수송층(5), 전자저지층(6), 발광층(3), 정공저지층(7), 전자수송층(8), 전자주입층(9) 및 음극(4)로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 정공수송층, 전자저지층, 발광층, 정공저지층, 전자수송층 및 전자주입층 중 1층 이상에 포함될 수 있다. 2 is a
본 발명에 따른 유기 발광 소자는, 상기 유기물 층 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. 또한, 상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다. The organic light-emitting device according to the present invention can be made of materials and methods known in the art, except that at least one layer of the organic material layer contains the compound represented by
예컨대, 본 발명에 따른 유기 발광 소자는 기판 상에 제1 전극, 유기물층 및 제2 전극을 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 정공수송층, 전자저지층, 발광층, 정공저지층, 전자수송층 및 전자주입층을 포함하는 유기물 층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시켜 제조할 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수 있다. For example, the organic light emitting device according to the present invention can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a positive electrode is formed by depositing a metal or conductive metal oxide or an alloy 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 transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer is formed thereon, and then a material that can be used as a cathode is deposited thereon. In addition to this method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
또한, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물 층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.In addition, the compound represented by
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.
일례로, 상기 제1 전극은 양극이고, 상기 제2 전극은 음극이거나, 또는 상기 제1 전극은 음극이고, 상기 제2 전극은 양극이다.In one example, the first electrode is an anode, the second electrode is a cathode, or the first electrode is a cathode, and the second electrode is an anode.
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 generated in the light emitting layer. A compound that prevents migration of the excitons to the electron injection layer or the electron injection material and has excellent thin film formation ability is preferred. It is preferred that the high 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 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 anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 정공 수송 물질로 양극이나 정공주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. The hole transport layer is a layer that receives holes from the hole injection layer and transports holes from the hole injection layer to the light emitting layer. It is a material that transports holes from the anode or the hole injection layer as a hole transport material and transfers them to the light emitting layer. This is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.
상기 전자저지층은 음극에서 주입된 전자가 발광층에서 재결합되지 않고 정공수송층으로 넘어가는 것을 방지하기 위해 정공수송층과 발광층의 사이에 두는 층으로는 층으로, 전자억제층으로 불리기도 한다. 전자저지층에는 전자수송층보다 전자 친화력이 작은 물질이 바람직하다.The electron blocking layer is a layer interposed between the hole transport layer and the light emitting layer to prevent electrons injected from the cathode from being recombined in the light emitting layer and passing into the hole transport layer, and is also referred to as an electron suppression layer. The electron blocking layer is preferably a material having a smaller electron affinity than the electron transport layer.
상기 발광 물질로는 정공수송층과 전자수송층으로부터 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 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. 특히, 바람직하게는 상기 화학식 1로 표시되는 화합물을 호스트로 포함할 수 있다.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. In particular, preferably, the compound represented by
바람직하게는, 상기 발광층은 하기 화학식 2로 표시되는 화합물을 추가로 포함할 수 있다:Preferably, the light emitting layer may further include a compound represented by the following Chemical Formula 2:
[화학식 2][Formula 2]
상기 화학식 2에서,In
Ar3 및 Ar4는 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,Ar 3 and Ar 4 are each independently, substituted or unsubstituted C 6-60 aryl; Or a substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,
R6 및 R7은 각각 독립적으로, 수소; 중수소; 할로겐; 시아노; 니트로; 아미노; 치환 또는 비치환된 C1-60 알킬; 치환 또는 비치환된 C3-60 사이클로알킬; 치환 또는 비치환된 C2-60 알케닐; 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴이고,R 6 and R 7 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 3-60 cycloalkyl; Substituted or unsubstituted C 2-60 alkenyl; Substituted or unsubstituted C 6-60 aryl; Or a substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,
p 및 q는 각각 독립적으로, 0 내지 7의 정수이다.p and q are each independently an integer from 0 to 7.
바람직하게는, Ar3 및 Ar4는 각각 독립적으로, 치환 또는 비치환된 C6-20 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C6-20 헤테로아릴일 수 있고, Preferably, Ar 3 and Ar 4 are each independently, substituted or unsubstituted C 6-20 aryl; Or C 6-20 heteroaryl containing any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
보다 바람직하게는, Ar3 및 Ar4는 각각 독립적으로, 페닐, 비페닐릴, 터페닐릴, 나프틸, 디벤조퓨라닐, 디벤조티오페닐, 또는 디메틸플루오레닐일 수 있고,More preferably, Ar 3 and Ar 4 may each independently be phenyl, biphenylyl, terphenylyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or dimethylfluorenyl,
가장 바람직하게는, Ar3 및 Ar4는 각각 독립적으로, 페닐, 비페닐릴, 터페닐릴, 나프틸, 디벤조퓨라닐, 디벤조티오페닐, 또는 9,9-디메틸-9H-플루오레닐일 수 있다.Most preferably, Ar 3 and Ar 4 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or 9,9-dimethyl-9H-fluorenylyl Can be.
바람직하게는, R6 및 R7은 각각 독립적으로, 수소; 치환 또는 비치환된 C1-20 알킬; 치환 또는 비치환된 C6-20 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C6-20 헤테로아릴일 수 있고, Preferably, R 6 and R 7 are each independently hydrogen; Substituted or unsubstituted C 1-20 alkyl; Substituted or unsubstituted C 6-20 aryl; Or C 6-20 heteroaryl containing any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
보다 바람직하게는, R6 및 R7은 각각 수소일 수 있다.More preferably, R 6 and R 7 may each be hydrogen.
p 및 q는 각각 R6 및 R7의 개수를 나타낸 것으로서, p가 2 이상일 경우, 2 이상의 R6는 서로 동일하거나 상이할 수 있고, q가 2 이상일 경우, 2 이상의 R7은 서로 동일하거나 상이할 수 있다.p and q represent the number of R 6 and R 7 , respectively, when p is 2 or more, two or more R 6 may be the same or different from each other, and when q is 2 or more, two or more R 7 are the same or different from each other can do.
상기 화학식 2로 표시되는 화합물의 대표적인 예는 다음과 같다: Representative examples of the compound represented by
. .
상기 화학식 2로 표시되는 화합물은 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층에 동시에 포함될 수 있다.The compound represented by
바람직하게는 상기 화학식 1로 표시되는 화합물과 상기 화학식 2로 표시되는 화합물의 중량비가 1:99 내지 99:1일 수 있고, 보다 바람직하게는 10:90 내지 90:10일 수 있다.Preferably, the weight ratio of the compound represented by
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 pyrene, anthracene, chrysene, periplanene, etc. having an arylamino group, and substituted or unsubstituted as a 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. Further, examples of the metal complex include an iridium complex, a platinum complex, and the like, but are not limited thereto.
상기 정공저지층은 양극에서 주입된 정공이 발광층에서 재결합되지 않고 전자수송층으로 넘어가는 것을 방지하기 위해 전자수송층과 발광층의 사이에 두는 층으로, 정공억제층으로 불리기도 한다. 정공저지층에는 이온화에너지가 큰 물질이 바람직하다.The hole blocking layer is a layer placed between the electron transport layer and the light emitting layer to prevent the holes injected from the anode from being recombined in the light emitting layer and passing into the electron transport layer, and is also referred to as a hole suppressing layer. The hole blocking layer is preferably a material having a large ionization energy.
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. 전자수송층은 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 thereto. 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 conventional materials 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, an excellent electron injection effect for a light emitting layer or a light emitting material, and injects holes 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-naphtolato) 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, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자 외에도 유기 태양 전지 또는 유기 트랜지스터에 포함될 수 있다.In addition, the compound represented by
이하, 본 발명의 이해를 돕기 위하여 바람직한 실시예를 제시한다. 그러나 하기의 실시예는 본 발명을 보다 쉽게 이해하기 위하여 제공되는 것일 뿐, 이에 의해 본 발명의 내용이 한정되는 것은 아니다.Hereinafter, preferred embodiments are provided to help understanding of the present invention. However, the following examples are only provided to more easily understand the present invention, and the contents of the present invention are not limited thereby.
제조예 1: 중간체 A의 합성Preparation Example 1: Synthesis of Intermediate A
(중간체 A-1의 합성)(Synthesis of Intermediate A-1)
3구 플라스크에 2,3-difluoro-1,4-diiodobenzene(30.0 g, 82.0 mmol), (4-chloro-2-methoxyphenyl)boronic acid(36.7 g, 196.8 mmol), 2M Na2CO3 수용액(164 mL, 328.0 mmol), DME(165 mL), 톨루엔(165 mL), Pd(PPh3)4(9.5 g, 8.2 mmol)를 넣고, 아르곤 분위기 하에서 8시간 환류 조건하에서 교반하였다. 반응이 종료되면 상온으로 냉각한 후, 반응액을 분액 깔대기에 옮기고, H2O(300 mL)을 넣고 CH2Cl2로 추출했다. 추출액을 MgSO4로 건조 후, 여과 및 농축한 후, 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 중간체 A-1(21.1 g, 수율 65 %)를 수득하였다.2,3-difluoro-1,4-diiodobenzene (30.0 g, 82.0 mmol), (4-chloro-2-methoxyphenyl)boronic acid (36.7 g, 196.8 mmol), 2M Na 2 CO 3 aqueous solution (164) mL, 328.0 mmol), DME (165 mL), toluene (165 mL), Pd(PPh 3 ) 4 (9.5 g, 8.2 mmol) was added, and the mixture was stirred under reflux conditions for 8 hours under an argon atmosphere. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel, H 2 O (300 mL) was added, and extracted with CH 2 Cl 2 . After the extract was dried over MgSO 4 , filtered and concentrated, the sample was purified by silica gel column chromatography to obtain intermediate A-1 (21.1 g, yield 65%).
MS[M+H]+= 395.MS [M+H] + =395.
(중간체 A-2의 합성)(Synthesis of Intermediate A-2)
2구 플라스크에 중간체 A-1(20.0 g, 50.6 mmol), 1M BBr3 in CH2Cl2 용액(121 mL, 121.4 mmol), CH2Cl2(300 mL)를 넣고, 아르곤 분위기 하에서 0 ℃로 맞추고 8시간 교반했다. 그 후, 상온에서 4시간 더 교반 후, 포화 NaHCO3 수용액으로 중화하였다. 이 반응액을 분액 깔대기에 옮겨 CH2Cl2로 추출하고 추출액을 실리카 겔 컬럼 크로마토그래피로 정제하여, 중간체 A-2(15.8 g, 수율 85 %)를 얻었다. Intermediate A-1 (20.0 g, 50.6 mmol), 1M BBr 3 in CH 2 Cl 2 solution (121 mL, 121.4 mmol), CH 2 Cl 2 (300 mL) was added to a 2-neck flask at 0° C. under an argon atmosphere. Fit and stir for 8 hours. Thereafter, the mixture was further stirred at room temperature for 4 hours, and then neutralized with a saturated NaHCO 3 aqueous solution. The reaction solution was transferred to a separatory funnel, extracted with CH 2 Cl 2 , and the extract was purified by silica gel column chromatography to obtain intermediate A-2 (15.8 g, yield 85%).
MS[M+H]+= 367.MS [M+H] + = 367.
(중간체 A의 합성)(Synthesis of Intermediate A)
2구 플라스크에 중간체 A-2(15.0 g, 40.9 mmol), K2CO3(12.4 g, 89.9 mmol), NMP(170 mL)를 넣고, 아르곤 분위기에서 150 ℃에서 8시간 교반했다. 반응 종료 후, 상온으로 냉각 후 시료를 분액 깔대기에 옮기고, H2O(100 mL)를 가하여 ethyl aceate로 추출하였다. 추출액을 실리카 겔 컬럼 크로마토그래피로 정제하여, 중간체 A(11.9 g, 수율 89 %)를 수득하였다.Intermediate A-2 (15.0 g, 40.9 mmol), K 2 CO 3 (12.4 g, 89.9 mmol), and NMP (170 mL) were added to a 2-neck flask and stirred at 150° C. for 8 hours in an argon atmosphere. After the reaction was completed, after cooling to room temperature, the sample was transferred to a separatory funnel, and H 2 O (100 mL) was added, followed by extraction with ethyl aceate. The extract was purified by silica gel column chromatography to obtain intermediate A (11.9 g, yield 89%).
MS[M+H]+= 327.MS [M+H] + = 327.
제조예 2: 중간체 B의 합성Preparation Example 2: Synthesis of Intermediate B
(중간체 B-1의 합성)(Synthesis of Intermediate B-1)
3구 플라스크에 2,5-dibromobenzene-1,4-diol(20.0 g, 74.7 mmol), (4-chloro-2-fluorophenyl)boronic acid(39.9 g, 156.8 mmol)을 THF(750 mL)에 녹이고 K2CO3(61.9 g, 447.9 mmol)을 H2O(375 mL)에 녹여 넣는다. 여기에 Pd(PPh3)4(1.7 g, 1.5 mmol)를 넣고, 아르곤 분위기 환류 조건하에서 8시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각한 후, 반응액을 분액 깔대기에 옮기고, CH2Cl2로 추출했다. 추출액을 MgSO4로 건조 후, 여과 및 농축한 후, 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 중간체 B-1(21.1 g, 수율 77 %)을 수득하였다. Dissolve 2,5-dibromobenzene-1,4-diol (20.0 g, 74.7 mmol) and (4-chloro-2-fluorophenyl)boronic acid (39.9 g, 156.8 mmol) in THF (750 mL) in a 3-neck flask and K 2 CO 3 (61.9 g, 447.9 mmol) was dissolved in H 2 O (375 mL). Pd(PPh 3 ) 4 (1.7 g, 1.5 mmol) was added thereto, and the mixture was stirred under an argon atmosphere under reflux for 8 hours. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel and extracted with CH 2 Cl 2 . After the extract was dried over MgSO 4 , filtered and concentrated, the sample was purified by silica gel column chromatography to obtain intermediate B-1 (21.1 g, yield 77%).
MS[M+H]+= 367.MS [M+H] + = 367.
(중간체 B의 합성)(Synthesis of Intermediate B)
2구 플라스크에 중간체 B-1(15.0 g, 40.9 mmol), K2CO3(12.4 g, 89.9 mmol), NMP(170 mL)를 넣고, 아르곤 분위기에서 150 ℃에서 8시간 교반했다. 반응 종료 후, 상온으로 냉각 후 시료를 분액 깔대기에 옮기고, H2O(100 mL)을 가하여 ethyl aceate로 추출하였다. 추출액을 실리카 겔 컬럼 크로마토그래피로 정제하여, 중간체 B(10.8 g, 수율 81 %)를 수득하였다.In a 2-neck flask, intermediate B-1 (15.0 g, 40.9 mmol), K 2 CO 3 (12.4 g, 89.9 mmol), and NMP (170 mL) were added and stirred at 150° C. for 8 hours in an argon atmosphere. After the reaction was completed, after cooling to room temperature, the sample was transferred to a separatory funnel, and H 2 O (100 mL) was added, followed by extraction with ethyl aceate. The extract was purified by silica gel column chromatography to obtain intermediate B (10.8 g, yield 81%).
MS[M+H]+= 327.MS [M+H] + = 327.
제조예 3: 중간체 C의 합성Preparation Example 3: Synthesis of Intermediate C
제조예 1에서, 2,3-difluoro-1,4-diiodobenzene을 1,5-dibromo-2,4-difluorobenzene으로 변경하여 사용한 것을 제외하고는, 화합물 중간체 A의 제조 방법과 동일한 제조 방법으로 중간체 C를 제조하였다. In Preparation Example 1, except that 2,3-difluoro-1,4-diiodobenzene was changed to 1,5-dibromo-2,4-difluorobenzene and used, Intermediate C was prepared in the same manner as in Preparation Method of Compound Intermediate A. Was prepared.
MS[M+H]+= 327.MS [M+H] + = 327.
제조예 4: 중간체 D의 합성Preparation Example 4: Synthesis of Intermediate D
(중간체 D-1의 합성)(Synthesis of Intermediate D-1)
3구 플라스크에 2-hydroxydibenzo[b,d]furan(15.0 g, 81.4 mmol), acetic acid(100 mL)을 넣고 여기에 idodine monochloride(4.5 mL, 89.6 mmol)와 conc.HCl(55 mL), acetic acid 용액(34 mL)을 적가한 후, 상온에서 24시간 교반하였다. 반응이 종료되면 H2O(300 mL)를 넣어주고 생성된 침전물을 여과하여 H2O 로 씻어주었다. 여과된 고체를 MeOH로 재결정하여 중간체 D-1(18.9 g, 수율 75 %)을 수득하였다. 2-Hydroxydibenzo[b,d]furan (15.0 g, 81.4 mmol) and acetic acid (100 mL) were added to the 3-neck flask, and idodine monochloride (4.5 mL, 89.6 mmol) and conc.HCl (55 mL), acetic After adding the acid solution (34 mL) dropwise, the mixture was stirred at room temperature for 24 hours. When the reaction was completed, H 2 O (300 mL) was added, and the resulting precipitate was filtered and washed with H 2 O. The filtered solid was recrystallized from MeOH to obtain intermediate D-1 (18.9 g, yield 75%).
MS[M+H]+= 310.MS [M+H] + =310.
(중간체 D-2의 합성)(Synthesis of Intermediate D-2)
3구 플라스크에 중간체 D-1(18.0 g, 58.0 mmol), (4-chloro-2-fluorophenyl)boronic acid(10.6 g, 61.0 mmol)을 THF(600 mL)에 녹이고 K2CO3(32.1 g, 232.2 mmol)을 H2O(300 mL)에 녹여 넣는다. 여기에 Pd(PPh3)4(0.7 g, 0.6 mmol)를 넣고, 아르곤 분위기 환류 조건하에서 8시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각한 후, 반응액을 분액 깔대기에 옮기고, CH2Cl2로 추출했다. 추출액을 MgSO4로 건조 후, 여과 및 농축한 후, 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 중간체 D-2(14.5 g, 수율 80 %)를 수득하였다. Dissolve intermediate D-1 (18.0 g, 58.0 mmol), (4-chloro-2-fluorophenyl)boronic acid (10.6 g, 61.0 mmol) in THF (600 mL) in a 3-neck flask and K 2 CO 3 (32.1 g, 232.2 mmol) was dissolved in H 2 O (300 mL). Pd(PPh 3 ) 4 (0.7 g, 0.6 mmol) was added thereto, and the mixture was stirred under an argon atmosphere under reflux for 8 hours. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel and extracted with CH 2 Cl 2 . After the extract was dried over MgSO 4 , filtered and concentrated, the sample was purified by silica gel column chromatography to obtain intermediate D-2 (14.5 g, yield 80%).
MS[M+H]+= 313.MS [M+H] + = 313.
(중간체 D의 합성)(Synthesis of Intermediate D)
2구 플라스크에 중간체 D-2(14.0 g, 44.8 mmol), K2CO3(9.3 g, 67.2 mmol), NMP(180 mL)를 넣고, 아르곤 분위기에서 150 ℃에서 8시간 교반했다. 반응 종료 후, 상온으로 냉각 후 시료를 분액 깔대기에 옮기고, H2O(200 mL)를 가하여 ethyl acetate로 추출하였다. 추출액을 실리카 겔 컬럼 크로마토그래피로 정제하여, 중간체 D(10.6 g, 수율 81 %)를 수득하였다. To a 2-neck flask, intermediate D-2 (14.0 g, 44.8 mmol), K 2 CO 3 (9.3 g, 67.2 mmol), and NMP (180 mL) were added and stirred at 150° C. for 8 hours in an argon atmosphere. After the reaction was completed, after cooling to room temperature, the sample was transferred to a separatory funnel, and H 2 O (200 mL) was added, followed by extraction with ethyl acetate. The extract was purified by silica gel column chromatography to obtain intermediate D (10.6 g, yield 81%).
MS[M+H]+= 293.MS [M+H] + =293.
제조예 5: 중간체 E의 합성Preparation Example 5: Synthesis of Intermediate E
(중간체 E-1의 합성)(Synthesis of Intermediate E-1)
3구 플라스크에 3-fluorodibenzo[b,d]furan(15.0 g, 80.6 mmol), THF(400 mL)을 넣고, -78 ℃로 냉각했다. n-BuLi(1.6M n-헥세인용액, 55 mL, 88.6 mmol)을 적가하고, -78 ℃에서 20분간 교반했다. 붕산 트라이아이소프로필(45.5 g, 241.7 mmol)을 가하여 -78 ℃에서 1시간 교반 후, 상온에서 4시간 더 교반하였다. 이 후 1N HCl(130 mL)를 가하여 실온에서 1시간 교반 후 반응액을 농축하여, 분액 깔대기에 옮기고, H2O(200 mL)를 가한 후 CH2Cl2로 추출하였다. 추출액을 MgSO4로 건조 후, 여과, 농축한 후, 톨루엔-헥세인을 이용해 재결정을 하여 중간체 E-1(11.1 g, 수율 60 %)을 수득하였다. 3-fluorodibenzo[b,d]furan (15.0 g, 80.6 mmol) and THF (400 mL) were added to a 3-neck flask and cooled to -78 °C. n-BuLi (1.6M n-hexane solution, 55 mL, 88.6 mmol) was added dropwise and stirred at -78°C for 20 minutes. Triisopropyl borate (45.5 g, 241.7 mmol) was added, followed by stirring at -78°C for 1 hour, followed by further stirring at room temperature for 4 hours. Thereafter, 1N HCl (130 mL) was added, stirred at room temperature for 1 hour, and the reaction solution was concentrated, transferred to a separatory funnel, and H 2 O (200 mL) was added, followed by extraction with CH 2 Cl 2 . The extract was dried over MgSO 4 , filtered and concentrated, and then recrystallized using toluene-hexane to obtain intermediate E-1 (11.1 g, yield 60%).
MS[M+H]+= 230.MS [M+H] + =230.
(중간체 E-2의 합성)(Synthesis of Intermediate E-2)
3구 플라스크에 중간체 E-1(10.0 g, 43.5 mmol), 5-chloro-2-iodophenol(11.6 g, 45.7 mmol)을 THF(430 mL)에 녹이고 K2CO3(24.0 g, 173.9 mmol)을 H2O(220 mL)에 녹여 넣는다. 여기에 Pd(PPh3)4(0.5 g, 0.4 mmol)를 넣고, 아르곤 분위기 환류 조건하에서 8시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각한 후, 반응액을 분액 깔대기에 옮기고, CH2Cl2로 추출했다. 추출액을 MgSO4로 건조 후, 여과 및 농축한 후, 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 중간체 E-2(10.5 g, 수율 77 %)를 수득하였다. Dissolve intermediate E-1 (10.0 g, 43.5 mmol) and 5-chloro-2-iodophenol (11.6 g, 45.7 mmol) in THF (430 mL) in a 3-neck flask and dissolve K 2 CO 3 (24.0 g, 173.9 mmol). Dissolve in H 2 O (220 mL). Pd(PPh 3 ) 4 (0.5 g, 0.4 mmol) was added thereto, and the mixture was stirred under an argon atmosphere under reflux for 8 hours. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel and extracted with CH 2 Cl 2 . After the extract was dried over MgSO 4 , filtered and concentrated, the sample was purified by silica gel column chromatography to obtain intermediate E-2 (10.5 g, yield 77%).
MS[M+H]+= 313.MS [M+H] + = 313.
(중간체 E의 합성)(Synthesis of Intermediate E)
2구 플라스크에 화합물 E-2(10.0 g, 32.0 mmol), K2CO3(6.6 g, 48.0 mmol), NMP(130 mL)를 넣고, 아르곤 분위기에서 150 ℃에서 8시간 교반했다. 반응 종료 후, 상온으로 냉각 후 시료를 분액 깔대기에 옮기고, H2O(100 mL)을 가하여 ethyl acetate로 추출하였다. 추출액을 실리카 겔 컬럼 크로마토그래피로 정제하여, 중간체 E(6.2 g, 수율 66 %)를 수득하였다. Compound E-2 (10.0 g, 32.0 mmol), K 2 CO 3 (6.6 g, 48.0 mmol), and NMP (130 mL) were added to a 2-neck flask and stirred at 150° C. for 8 hours in an argon atmosphere. After the reaction was completed, after cooling to room temperature, the sample was transferred to a separatory funnel, and H 2 O (100 mL) was added, followed by extraction with ethyl acetate. The extract was purified by silica gel column chromatography to obtain intermediate E (6.2 g, yield 66%).
MS[M+H]+= 293.MS [M+H] + =293.
제조예 6: 중간체 F의 합성Preparation Example 6: Synthesis of Intermediate F
제조예 5에서, 3-fluorodibenzo[b,d]furan을 3-fluorodibenzo[b,d] thiophene으로 변경하여 사용한 것을 제외하고는, 중간체 E의 제조 방법과 동일한 제조 방법으로 중간체 F를 제조하였다. In Preparation Example 5, Intermediate F was prepared by the same method as in Intermediate E, except that 3-fluorodibenzo[b,d]furan was changed to 3-fluorodibenzo[b,d] thiophene.
MS[M+H]+= 309.MS [M+H] + = 309.
제조예 7: 화합물 1의 합성Preparation Example 7: Synthesis of
(화합물 1-1의 합성)(Synthesis of Compound 1-1)
3구 플라스크에 중간체 A(15.0 g, 45.8 mmol), 중간체 a-1(17.3 g, 48.1 mmol)을 THF(460 mL)에 녹이고 K2CO3(25.3 g, 183.4 mmol)을 H2O(230 mL)에 녹여 넣는다. 여기에 Pd(PPh3)4(0.5 g, 0.5 mmol)를 넣고, 아르곤 분위기 환류 조건하에서 8시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각한 후, 반응액을 분액 깔대기에 옮기고, CH2Cl2로 추출했다. 추출액을 MgSO4로 건조 후, 여과 및 농축한 후, 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 1-1(16.3 g, 수율 68 %)을 수득하였다. Dissolve intermediate A (15.0 g, 45.8 mmol) and intermediate a-1 (17.3 g, 48.1 mmol) in THF (460 mL) in a 3-neck flask and dissolve K 2 CO 3 (25.3 g, 183.4 mmol) in H 2 O (230 mL). Pd(PPh 3 ) 4 (0.5 g, 0.5 mmol) was added thereto, and the mixture was stirred under an argon atmosphere under reflux for 8 hours. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel and extracted with CH 2 Cl 2 . After the extract was dried over MgSO 4 , filtered and concentrated, the sample was purified by silica gel column chromatography to obtain compound 1-1 (16.3 g, yield 68%).
MS[M+H]+= 524.MS [M+H] + = 524.
(화합물 1의 합성)(Synthesis of Compound 1)
3 구 플라스크에 화합물 1-1(15.0 g, 28.6 mmol), 중간체 b-1(5.3 g, 31.5 mmol)을 toluene(285 mL)에 녹이고 sodium tert-butoxide(4.1 g, 42.9 mmol), Bis(tri-tert-butylphosphine)palladium(0)(0.3 g, 0.6 mmol)을 넣은 후, 아르곤 분위기 환류 조건하에서 6시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각한 후, H2O(160 mL)를 넣고 반응액을 분액 깔대기에 옮겨 추출하였다. 추출액을 MgSO4로 건조, 농축하고 시료를 실리카 겔 컬럼 크로마토그래피로 정제한 후, 승화정제를 통해 화합물 1(6.0 g, 수율 32 %)을 수득하였다.Dissolve compound 1-1 (15.0 g, 28.6 mmol), intermediate b-1 (5.3 g, 31.5 mmol) in toluene (285 mL) in a 3-neck flask, sodium tert-butoxide (4.1 g, 42.9 mmol), Bis (tri -tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added, followed by stirring under argon atmosphere reflux for 6 hours. After the reaction was completed, after cooling to room temperature, H 2 O (160 mL) was added and the reaction solution was transferred to a separatory funnel and extracted. The extract was dried, concentrated with MgSO 4 and the sample was purified by silica gel column chromatography to obtain compound 1 (6.0 g, yield 32%) through a sublimation tablet.
MS[M+H]+= 655.MS [M+H] + = 655.
제조예 8: 화합물 2의 합성Preparation Example 8: Synthesis of
제조예 7에서, 중간체 a-1을 중간체 a-2로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 2를 제조하였다. In Production Example 7,
MS[M+H]+= 731.MS [M+H] + = 731.
제조예 9: 화합물 3의 합성Preparation Example 9: Synthesis of
제조예 7에서, 중간체 a-1을 중간체 a-3로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 3을 제조하였다. In Preparation Example 7,
MS[M+H]+= 745.MS [M+H] + =745.
제조예 10: 화합물 4의 합성Preparation Example 10 Synthesis of
제조예 7에서, 중간체 A를 중간체 B로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 4를 제조하였다. In Production Example 7,
MS[M+H]+= 655.MS [M+H] + = 655.
제조예 11: 화합물 5의 합성Preparation Example 11: Synthesis of
제조예 7에서, 중간체 A를 중간체 B로, 중간체 a-1을 중간체 a-4로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 5를 제조하였다.In Preparation Example 7,
MS[M+H]+= 731.MS [M+H] + = 731.
제조예 12: 화합물 6의 합성Preparation 12: Synthesis of
제조예 7에서, 화합물 1-1을 화합물 4-1로, 중간체 b-1을 중간체 b-2로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 6을 제조하였다. In Production Example 7,
MS[M+H]+= 731.MS [M+H] + = 731.
제조예 13: 화합물 7의 합성Preparation Example 13 Synthesis of
제조예 7에서, 중간체 A를 중간체 C로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 7을 제조하였다. In Preparation Example 7,
MS[M+H]+= 655.MS [M+H] + = 655.
제조예 14: 화합물 8의 합성Preparation 14: Synthesis of
제조예 7에서, 화합물 1-1을 화합물 7-1로, 중간체 b-1을 중간체 b-3으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 8을 제조하였다. In Production Example 7,
MS[M+H]+= 731.MS [M+H] + = 731.
제조예 15: 화합물 9의 합성Preparation 15: Synthesis of
제조예 7에서, 화합물 1-1을 화합물 7-1로, 중간체 b-1을 중간체 b-4로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 9를 제조하였다. In Production Example 7,
MS[M+H]+= 731.MS [M+H] + = 731.
제조예 16: 화합물 10의 합성Preparation Example 16: Synthesis of Compound 10
(화합물 10-1의 합성)(Synthesis of Compound 10-1)
3구 플라스크에 중간체 D(20.0 g, 68.3 mmol), 중간체 a-1(25.8 g, 71.7 mmol)을 THF(680 mL)에 녹이고 K2CO3(37.8 g, 273.3 mmol)을 H2O(340 mL)에 녹여 넣는다. 여기에 Pd(PPh3)4(0.8 g, 0.7 mmol)를 넣고, 아르곤 분위기 환류 조건하에서 8시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각한 후, 반응액을 분액 깔대기에 옮기고, CH2Cl2로 추출했다. 추출액을 MgSO4로 건조 후, 여과 및 농축한 후, 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 10-1(22.4 g, 수율 67 %)을 수득하였다. Dissolve intermediate D (20.0 g, 68.3 mmol), intermediate a-1 (25.8 g, 71.7 mmol) in THF (680 mL) in a 3-neck flask and dissolve K 2 CO 3 (37.8 g, 273.3 mmol) in H 2 O (340 mL). Pd(PPh 3 ) 4 (0.8 g, 0.7 mmol) was added thereto, and the mixture was stirred under an argon atmosphere under reflux for 8 hours. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel and extracted with CH 2 Cl 2 . After the extract was dried over MgSO 4 , filtered and concentrated, the sample was purified by silica gel column chromatography to obtain compound 10-1 (22.4 g, yield 67%).
MS[M+H]+= 490.MS [M+H] + =490.
(화합물 10-2의 합성)(Synthesis of Compound 10-2)
2구 플라스크에 화합물 10-1(20.0 g, 40.9 mmol), NBS(8.0 g, 44.9 mmol), DMF(410 mL)를 넣고, 아르곤 분위기 하에서 상온에서 8시간 교반하였다. 반응 종료 후, 반응액을 분액 깔대기에 옮기고, H2O(200 mL)를 가하여 ethyl acetate로 추출했다. 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 10-2(19.0 g, 수율 82 %)를 수득하였다. Compound 10-1 (20.0 g, 40.9 mmol), NBS (8.0 g, 44.9 mmol), and DMF (410 mL) were added to a 2-neck flask and stirred at room temperature for 8 hours under an argon atmosphere. After completion of the reaction, the reaction solution was transferred to a separatory funnel, and H 2 O (200 mL) was added, followed by extraction with ethyl acetate. The sample was purified by silica gel column chromatography to obtain compound 10-2 (19.0 g, yield 82%).
MS[M+H]+= 568.MS [M+H] + =568.
(화합물 10의 합성)(Synthesis of Compound 10)
3구 플라스크에 화합물 10-2(18.0 g, 31.7 mmol), 중간체 b-1(5.8 g, 34.8 mmol)을 toluene(320 mL)에 녹이고 sodium tert-butoxide(4.6 g, 47.5 mmol), Bis(tri-tert-butylphosphine)palladium(0)(0.3 g, 0.6 mmol)을 넣은 후, 아르곤 분위기 환류 조건하에서 6시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각한 후, H2O(200 mL)를 넣고 반응액을 분액 깔대기에 옮겨 추출하였다. 추출액을 MgSO4로 건조, 농축하고 시료를 실리카 겔 컬럼 크로마토그래피로 정제한 후, 승화정제를 통해 화합물 10(5.8 g, 수율 28 %)을 수득하였다. Dissolve compound 10-2 (18.0 g, 31.7 mmol), intermediate b-1 (5.8 g, 34.8 mmol) in toluene (320 mL) in a 3-neck flask, sodium tert-butoxide (4.6 g, 47.5 mmol), Bis (tri -tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added, followed by stirring under argon atmosphere reflux for 6 hours. After the reaction was completed, after cooling to room temperature, H 2 O (200 mL) was added and the reaction solution was transferred to a separatory funnel and extracted. The extract was dried, concentrated with MgSO 4 and the sample was purified by silica gel column chromatography to obtain compound 10 (5.8 g, yield 28%) through sublimation purification.
MS[M+H]+= 655.MS [M+H] + = 655.
제조예 17: 화합물 11의 합성Preparation Example 17: Synthesis of Compound 11
제조예 16에서, 중간체 D를 중간체 E로 변경하여 사용한 것을 제외하고는, 화합물 10의 제조 방법과 동일한 제조 방법으로 화합물 11을 제조하였다. In Production Example 16, Compound 11 was prepared by the same method as the method for preparing Compound 10, except that Intermediate D was changed to Intermediate E.
MS[M+H]+= 655.MS [M+H] + = 655.
제조예 18: 화합물 12의 합성Preparation 18: Synthesis of Compound 12
(화합물 12-1의 합성)(Synthesis of Compound 12-1)
3구 플라스크에 중간체 F(15.0 g, 48.6 mmol), 중간체 b-1(8.9 g, 53.4 mmol)을 toluene(480 mL)에 녹이고 sodium tert-butoxide(7.0 g, 72.9 mmol), Bis(tri-tert-butylphosphine)palladium(0)(0.5 g, 1.0 mmol)을 넣은 후, 아르곤 분위기 환류 조건하에서 6시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각한 후, H2O(200 mL)를 넣고 반응액을 분액 깔대기에 옮겨 추출하였다. 추출액을 MgSO4로 건조, 농축하고 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 12-1(16.7g, 수율 78 %)을 수득하였다. Dissolve intermediate F (15.0 g, 48.6 mmol), intermediate b-1 (8.9 g, 53.4 mmol) in toluene (480 mL) in a 3-neck flask, sodium tert-butoxide (7.0 g, 72.9 mmol), Bis (tri-tert) -butylphosphine)palladium(0) (0.5 g, 1.0 mmol) was added, followed by stirring under argon atmosphere reflux for 6 hours. After the reaction was completed, after cooling to room temperature, H 2 O (200 mL) was added and the reaction solution was transferred to a separatory funnel and extracted. The extract was dried over MgSO 4 , concentrated and the sample was purified by silica gel column chromatography to obtain compound 12-1 (16.7 g, yield 78%).
MS[M+H]+= 440.MS [M+H] + =440.
(화합물 12-2의 합성)(Synthesis of Compound 12-2)
건조된 3구 플라스크에 화합물 12-1(16.0 g, 36.4 mmol)을 질소 분위기 하에서 THF(160 mL)에 녹인 후, -10 ℃에서 교반하면서 1.6M n-butyllithium(24 mL, 38.2 mmol)을 천천히 적가하였다. 적가가 완료되면 동일온도에서 4시간 더 교반한 후, -78 ℃로 온도를 내리고 trimethyl borate(4.9 g, 47.3 mmol)을 천천히 적가한 후, 상온으로 올려서 밤새 교반하였다. 반응이 종료되면 2N HCl 수용액을 적가하여 산성화한 후 30분동안 교반하였다. 반응액을 분액 깔대기에 옮기고 물과 ethyl acetate를 이용해 유기층을 추출하여 감압 농축한 후, 재결정하여 화합물 12-2(10.6 g, 수율 60 %)를 수득하였다 After dissolving compound 12-1 (16.0 g, 36.4 mmol) in THF (160 mL) under a nitrogen atmosphere in a dried 3-neck flask, 1.6M n-butyllithium (24 mL, 38.2 mmol) was slowly added while stirring at -10 °C. Dropwise. When the dropwise addition was completed, the mixture was further stirred at the same temperature for 4 hours, the temperature was lowered to -78°C, trimethyl borate (4.9 g, 47.3 mmol) was slowly added dropwise, and the temperature was raised to room temperature and stirred overnight. After the reaction was completed, 2N HCl aqueous solution was added dropwise and acidified, followed by stirring for 30 minutes. The reaction solution was transferred to a separatory funnel, and the organic layer was extracted with water and ethyl acetate, concentrated under reduced pressure, and recrystallized to obtain compound 12-2 (10.6 g, yield 60%).
MS[M+H]+= 483.MS [M+H] + = 483.
(화합물 12의 합성)(Synthesis of Compound 12)
3구 플라스크에 화합물 12-2(10.0 g, 20.7 mmol), 중간체 a-5(5.8 g, 21.7 mmol)을 THF(200 mL)에 녹이고 K2CO3(11.4 g, 82.8 mmol)을 H2O(100 mL)에 녹여 넣는다. 여기에 Pd(PPh3)4(0.2 g, 0.2 mmol)를 넣고, 아르곤 분위기 환류 조건하에서 8시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각한 후, 반응액을 분액 깔대기에 옮기고, CH2Cl2로 추출했다. 추출액을 MgSO4로 건조 후, 여과 및 농축한 후, 시료를 실리카 겔 컬럼 크로마토그래피로 정제한 후, 승화정제를 통해 화합물 12(4.6 g, 수율 33 %)을 수득하였다. Dissolve compound 12-2 (10.0 g, 20.7 mmol), intermediate a-5 (5.8 g, 21.7 mmol) in THF (200 mL) in a 3-neck flask, and dissolve K 2 CO 3 (11.4 g, 82.8 mmol) in H 2 O (100 mL). Pd(PPh 3 ) 4 (0.2 g, 0.2 mmol) was added thereto, and the mixture was stirred under an argon atmosphere under reflux for 8 hours. After the reaction was completed, after cooling to room temperature, the reaction solution was transferred to a separatory funnel and extracted with CH 2 Cl 2 . After the extract was dried with MgSO 4 , filtered and concentrated, the sample was purified by silica gel column chromatography, and then compound 12 (4.6 g, yield 33%) was obtained through a sublimation tablet.
MS[M+H]+= 671MS[M+H] + = 671
제조예 19: 화합물 13의 합성Preparation 19: Synthesis of Compound 13
제조예 7에서, 중간체 A를 중간체 G로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 13을 제조하였다. In Preparation Example 7, compound 13 was prepared by the same method as the method for preparing
MS[M+H]+= 687.MS [M+H] + =687.
제조예 20: 화합물 14의 합성Preparation 20: Synthesis of Compound 14
제조예 7에서, 중간체 a-1을 중간체 a-6로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 14를 제조하였다. In Production Example 7, compound 14 was prepared by the same method as the method for preparing
MS[M+H]+= 665.MS [M+H] + = 665.
실시예 1Example 1
ITO(Indium Tin Oxide)가 1,400 Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이 때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30 분간 세척한 후 증류수로 2 회 반복하여 초음파 세척을 10 분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5 분간 세정한 후 진공 증착기로 기판을 수송시켰다.ITO (Indium Tin Oxide) was coated with a thin film coated with a thickness of 1,400 Å 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 2 minutes with distilled water twice. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and then transported to a plasma cleaner. In addition, after the substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transferred to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에 하기 화합물 HT-A과 5 중량%의 화합물 PD를 100 Å의 두께로 열 진공 증착하고 이어서 화합물 HT-A만 1150 Å의 두께로 증착하여 정공수송층을 형성하였다. 그 위에 전자저지층으로 하기 화합물 HT-B를 450 Å 두께로 열 진공 증착하였다. 이어서 제1 호스트로 화합물 PGH-1, 제2 호스트로 상기 제조예 7의 화합물 1을 60:40 중량비로 호스트를 구성하고 15 중량%의 화합물 GD를 도펀트로 하여 400 Å의 두께로 진공 증착하였다. 이어서, 정공저지층으로 하기 화합물 ET-A를 50 Å의 두께로 진공 증착하였다. 이어서 전자수송 및 주입층으로 하기 화합물 ET-B와 Liq를 2:1의 비율로 250 Å의 두께로 열 진공 증착하고 이어서 LiF와 마그네슘을 1:1의 비율로 30 Å의 두께로 진공 증착하였다. 상기 전자주입층 위에 마그네슘과 은을 1:4의 비율로 160 Å의 두께로 증착하여 음극을 형성하여, 유기 발광 소자를 제조하였다.The following compound HT-A and 5 wt% of compound PD were thermally vacuum-deposited to a thickness of 100 증착 on the prepared ITO transparent electrode, and then only the compound HT-A was deposited to a thickness of 1150 Å to form a hole transport layer. The compound HT-B below was thermally vacuum-deposited to a thickness of 450 MPa as an electron blocking layer thereon. Subsequently, the compound PGH-1 as the first host and the
실시예 2 내지 실시예 20Examples 2 to 20
호스트 물질을 하기 표 1과 같이 변경하였다는 점을 제외하고는, 상기 실시예 1과 동일한 방법을 이용하여 실시예 2 내지 실시예 20의 유기 발광 소자를 각각 제작하였다. 이때, 호스트로서 2종의 화합물의 혼합물을 사용한 경우, 괄호 안은 호스트 화합물간의 중량비 의미한다.Each of the organic light emitting devices of Examples 2 to 20 was manufactured using the same method as in Example 1, except that the host material was changed as shown in Table 1 below. In this case, when a mixture of two types of compounds is used as the host, the parentheses indicate the weight ratio between the host compounds.
비교예 1 내지 비교예 6Comparative Examples 1 to 6
호스트 물질을 하기 표 1과 같이 변경하였다는 점을 제외하고는, 상기 실시예 1과 동일한 방법을 이용하여 비교예 1 내지 비교예 6의 유기 발광 소자를 각각 제작하였다. 이때, 호스트로서 2종의 화합물의 혼합물을 사용한 경우, 괄호 안은 호스트 화합물간의 중량비 의미한다. 하기 표 1의 화합물 GH-A, GH-B, GH-C 및 GH-D는 아래와 같다.Each of the organic light emitting devices of Comparative Examples 1 to 6 was manufactured using the same method as in Example 1, except that the host material was changed as shown in Table 1 below. In this case, when a mixture of two types of compounds is used as the host, the parentheses indicate the weight ratio between the host compounds. Compounds GH-A, GH-B, GH-C and GH-D of Table 1 below are as follows.
실험예Experimental Example
상기 실시예 1 내지 실시예 20 및 비교예 1 내지 비교예 6에서 제작된 유기 발광 소자에 전류를 인가하여, 전압, 효율, 수명(T95)을 측정하고 그 결과를 하기 표 1에 나타내었다. 이때, 전압, 효율은 10 mA/cm2의 전류 밀도를 인가하여 측정되었으며, 수명(T95)은 전류 밀도 20 mA/cm2에서 초기휘도가 95 %로 저하할 때까지의 시간을 의미한다.By applying a current to the organic light-emitting device prepared in Examples 1 to 20 and Comparative Examples 1 to 6, voltage, efficiency, and lifetime (T95) were measured and the results are shown in Table 1 below. At this time, the voltage and efficiency were measured by applying a current density of 10 mA/cm 2 , and the lifespan (T95) means the time from the current density of 20 mA/cm 2 until the initial luminance decreases to 95%.
(중량비)Host material
(Weight ratio)
상기 표 1에서 보는 바와 같이 화학식 1의 화합물을 유기 전계 발광 소자의 호스트로 사용 시 저전압, 고효율, 장수명의 특성을 나타냄을 알 수 있다. 특히, PGH-1과 같은 화학식 2의 화합물과 함께 혼합하여 사용할 경우 그 효과가 더 현저해지며, 다른 구조의 화합물을 화학식 2의 화합물과 혼합하여 사용한 경우보다 더 우수한 효과를 나타낸다.As shown in Table 1, it can be seen that when the compound of
1: 기판
2: 양극
3: 발광층
4: 음극
5: 정공수송층
6: 전자저지층
7: 정공저지층
8: 전자수송층
9: 전자주입층1: substrate 2: anode
3: light emitting layer 4: cathode
5: hole transport layer 6: electron blocking layer
7: hole blocking layer 8: electron transport layer
9: Electronic injection layer
Claims (14)
[화학식 1]
상기 화학식 1에서,
A는 인접한 두 개의 고리와 융합된 벤젠 고리이고,
X1 및 X2는 각각 독립적으로, O 또는 S이고,
Y1 내지 Y3는 각각 독립적으로, N 또는 CH이고, Y1 내지 Y3 중 적어도 하나는 N이고,
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,
R1 내지 R3는 각각 독립적으로, 수소; 중수소; 할로겐; 시아노; 니트로; 아미노; 치환 또는 비치환된 C1-60 알킬; 치환 또는 비치환된 C3-60 사이클로알킬; 치환 또는 비치환된 C2-60 알케닐; 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴이고,
R4 및 R5는 각각 독립적으로, 수소; 중수소; 할로겐; 시아노; 니트로; 아미노; 치환 또는 비치환된 C1-60 알킬; 치환 또는 비치환된 C3-60 사이클로알킬; 치환 또는 비치환된 C2-60 알케닐; 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴이고,
a 및 b는 각각 독립적으로, 0 내지 4인 정수이고,
c는 0 내지 2인 정수이고,
d 및 e는 각각 독립적으로, 0 내지 3인 정수이다.
Compound represented by the formula (1):
[Formula 1]
In Chemical Formula 1,
A is a benzene ring fused with two adjacent rings,
X 1 and X 2 are each independently O or S,
Y 1 to Y 3 are each independently N or CH, and at least one of Y 1 to Y 3 is N,
Ar 1 and Ar 2 are each independently, substituted or unsubstituted C 6-60 aryl; Or a substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,
R 1 to R 3 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 3-60 cycloalkyl; Substituted or unsubstituted C 2-60 alkenyl; Substituted or unsubstituted C 6-60 aryl; Or a substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,
R 4 and R 5 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 3-60 cycloalkyl; Substituted or unsubstituted C 2-60 alkenyl; Substituted or unsubstituted C 6-60 aryl; Or a substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,
a and b are each independently an integer from 0 to 4,
c is an integer from 0 to 2,
d and e are each independently an integer from 0 to 3.
상기 화학식 1은 하기 화학식 1-1 내지 화학식 1-6으로 표시되는,
화합물:
[화학식 1-1]
[화학식 1-2]
[화학식 1-3]
[화학식 1-4]
[화학식 1-5]
[화학식 1-6]
상기 화학식 1-1 내지 화학식 1-6에서,
X1, X2, Y1 내지 Y3, Ar1, Ar2, R1 내지 R5 및 a 내지 e에 대한 설명은 제1항에서 정의한 바와 같다.
According to claim 1,
Formula 1 is represented by the following Formula 1-1 to Formula 1-6,
compound:
[Formula 1-1]
[Formula 1-2]
[Formula 1-3]
[Formula 1-4]
[Formula 1-5]
[Formula 1-6]
In Formula 1-1 to Formula 1-6,
Descriptions of X 1 , X 2 , Y 1 to Y 3 , Ar 1 , Ar 2 , R 1 to R 5 and a to e are as defined in claim 1.
Y1 내지 Y3는 모두 N인,
화합물.
According to claim 1,
Y 1 to Y 3 are all N,
compound.
Ar1 및 Ar2는 각각 독립적으로, 페닐, 비페닐릴, 터페닐릴, 나프틸, 안트라세닐, 페난트레닐, 트리페닐레닐, 플루오레닐, 디벤조퓨라닐, 디벤조티오페닐, 또는 5 개의 중수소로 치환된 페닐인,
화합물.
According to claim 1,
Ar 1 and Ar 2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, or 5 Phenyl substituted with deuterium of dogs,
compound.
Ar1 및 Ar2 중 적어도 하나는 치환 또는 비치환된 C6-60 아릴인,
화합물.
According to claim 1,
At least one of Ar 1 and Ar 2 is substituted or unsubstituted C 6-60 aryl,
compound.
R1 내지 R3는 각각 독립적으로, 수소, 중수소, 또는 페닐인,
화합물.
According to claim 1,
R 1 to R 3 are each independently hydrogen, deuterium, or phenyl,
compound.
R4 및 R5는 각각 독립적으로, 수소 또는 중수소인,
화합물.
According to claim 1,
R 4 and R 5 are each independently hydrogen or deuterium,
compound.
상기 화학식 1로 표시되는 화합물은 하기로 구성되는 군으로부터 선택되는 어느 하나인,
화합물:
.
According to claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of,
compound:
.
유기 발광 소자.
A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound according to any one of claims 1 to 8. doing,
Organic light emitting device.
상기 유기물층은 발광층인,
유기 발광 소자.
The method of claim 9,
The organic layer is a light emitting layer,
Organic light emitting device.
상기 유기물층은 하기 화학식 2로 표시되는 화합물을 추가로 포함하는,
유기 발광 소자:
[화학식 2]
상기 화학식 2에서,
Ar3 및 Ar4는 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,
R6 및 R7은 각각 독립적으로, 수소; 중수소; 할로겐; 시아노; 니트로; 아미노; 치환 또는 비치환된 C1-60 알킬; 치환 또는 비치환된 C3-60 사이클로알킬; 치환 또는 비치환된 C2-60 알케닐; 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴이고,
p 및 q는 각각 독립적으로, 0 내지 7의 정수이다.
The method of claim 9,
The organic layer further comprises a compound represented by the following formula (2),
Organic light emitting device:
[Formula 2]
In Chemical Formula 2,
Ar 3 and Ar 4 are each independently, substituted or unsubstituted C 6-60 aryl; Or a substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,
R 6 and R 7 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 3-60 cycloalkyl; Substituted or unsubstituted C 2-60 alkenyl; Substituted or unsubstituted C 6-60 aryl; Or a substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,
p and q are each independently an integer from 0 to 7.
Ar3 및 Ar4는 각각 독립적으로, 페닐, 비페닐릴, 터페닐릴, 나프틸, 디벤조퓨라닐, 디벤조티오페닐, 또는 디메틸플루오레닐인,
유기 발광 소자.
The method of claim 11,
Ar 3 and Ar 4 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or dimethylfluorenyl,
Organic light emitting device.
R6 및 R7은 각각 수소인,
유기 발광 소자.
The method of claim 11,
R 6 and R 7 are each hydrogen,
Organic light emitting device.
상기 화학식 2로 표시되는 화합물은 하기로 구성되는 군으로부터 선택되는 어느 하나인,
유기 발광 소자:
.The method of claim 11,
The compound represented by Formula 2 is any one selected from the group consisting of,
Organic light emitting device:
.
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