KR102312478B1 - Compound and organic light emitting device comprising the same - Google Patents
Compound and organic light emitting device comprising the same Download PDFInfo
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- KR102312478B1 KR102312478B1 KR1020190138839A KR20190138839A KR102312478B1 KR 102312478 B1 KR102312478 B1 KR 102312478B1 KR 1020190138839 A KR1020190138839 A KR 1020190138839A KR 20190138839 A KR20190138839 A KR 20190138839A KR 102312478 B1 KR102312478 B1 KR 102312478B1
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- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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- YJSKZIATOGOJEB-UHFFFAOYSA-N thieno[2,3-b]pyrazine Chemical compound C1=CN=C2SC=CC2=N1 YJSKZIATOGOJEB-UHFFFAOYSA-N 0.000 description 1
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- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
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- 229910052719 titanium Inorganic materials 0.000 description 1
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- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 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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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D497/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D497/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- H01L51/0071—
-
- H01L51/0072—
-
- H01L51/5012—
-
- H01L51/5048—
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
Abstract
본 명세서는 화학식 1의 화합물 및 이를 포함한 유기 발광 소자를 제공한다.The present specification provides a compound of Formula 1 and an organic light emitting device including the same.
Description
본 출원은 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. The present application relates to a compound and an organic light emitting device including the same.
본 출원은 2018년 11월 2일에 한국특허청에 제출된 한국 특허 출원 제10- 2018-0133609호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0133609 filed with the Korean Intellectual Property Office on November 2, 2018, the entire contents of which are incorporated herein by reference.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 통상 제1 전극과 제2 전극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어 질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 제1 전극에서는 정공이, 제2 전극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including a first electrode and a second electrode and an organic material layer therebetween. Here, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, 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 the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the first electrode and electrons are injected into the organic material layer at the second electrode, and excitons are formed when the injected holes and electrons meet. , when this exciton falls back to the ground state, it glows.
상기와 같은 유기 발광 소자를 위한 새로운 재료의 개발이 계속 요구되고 있다.The development of new materials for the organic light emitting device as described above is continuously required.
본 출원은 화합물 및 이를 포함하는 유기 발광 소자를 제공하는 것이다.The present application provides a compound and an organic light emitting device including the same.
본 출원은 하기 화학식 1로 표시되는 화합물을 제공한다.The present application provides a compound represented by the following formula (1).
[화학식 1][Formula 1]
X1은 NR, X2는 직접결합; 또는 X1은 직접결합, X2는 NR이며,X1 is NR, X2 is a direct bond; or X1 is a direct bond, X2 is NR,
A는 벤젠이고,A is benzene,
R은 하기 화학식 2로 표시되고,R is represented by the following formula (2),
[화학식 2][Formula 2]
L은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이며,L is a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar은 하기 구조식 중에서 선택되는 어느 하나이고,Ar is any one selected from the following structural formula,
R'은 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,R' is hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
x는 0 내지 5의 정수이고,x is an integer from 0 to 5,
y는 0 내지 7의 정수이고,y is an integer from 0 to 7,
x 또는 y가 2 이상인 경우, 괄호 내의 치환기는 서로 같거나 상이하며,When x or y is 2 or more, the substituents in parentheses are the same as or different from each other,
a는 1 또는 2이고,a is 1 or 2,
a가 2인 경우에, 괄호 내의 치환기는 서로 같거나 상이하다.When a is 2, the substituents in parentheses are the same as or different from each other.
또한, 본 출원은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하고, 상기 유기물층 중 1 층 이상은 전술한 화합물을 포함하는 것인 유기 발광 소자를 제공한다.In addition, the present application is a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound described above.
본 출원의 일 실시상태에 따른 화합물을 사용하는 유기 발광 소자는 낮은 구동전압, 높은 발광효율 또는 장수명이 가능하다.The organic light emitting device using the compound according to the exemplary embodiment of the present application can have a low driving voltage, high luminous efficiency, or a long lifespan.
도 1은 기판(1), 제1 전극(2), 발광층(3), 제2 전극(4)이 순차적으로 적층된 유기 발광 소자의 예를 도시한 것이다.
도 2는 기판 (1), 제1 전극(2), 정공주입층(5), 정공수송층(6), 발광층(3), 전자수송층(7) 및 제2 전극(4)이 순차적으로 적층된 유기 발광 소자의 예를 도시한 것이다.
도 3은 기판(1), 제1 전극(2), 정공주입층(5), 정공수송층(6), 전자억제층(8), 발광층(3), 정공저지층(9), 전자주입 및 수송층(10) 및 제2 전극(4)이 순차적으로 적층된 유기 발광 소자의 예를 도시한 것이다. 1 illustrates an example of an organic light emitting device in which a
2 shows a
3 is a
이하, 본 명세서에 대하여 더욱 상세하게 설명한다.Hereinafter, the present specification will be described in more detail.
본 명세서는 상기 화학식 1로 표시되는 화합물를 제공한다.The present specification provides a compound represented by Formula 1 above.
본 출원의 일 실시상태에 따르면, 상기 화학식 1로 표시되는 화합물은 상기와 같은 코어 구조를 가짐으로써, 삼중항 에너지를 조절할 수 있는 장점이 있고, 장수명 및 고효율의 특성을 나타낼 수 있다.According to an exemplary embodiment of the present application, the compound represented by Chemical Formula 1 has the above-described core structure, and thus has the advantage of controlling triplet energy, and can exhibit long life and high efficiency characteristics.
본 명세서에서 치환기의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다. Examples of substituents in the present specification are described below, but are not limited thereto.
상기 "치환"이라는 용어는 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미하며, 치환되는 위치는 수소 원자가 치환되는 위치 즉, 치환기가 치환 가능한 위치라면 한정하지 않으며, 2 이상 치환되는 경우, 2 이상의 치환기는 서로 동일하거나 상이할 수 있다.The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, a position where the substituent is substitutable, is not limited, and when two or more are substituted , two or more substituents may be the same as or different from each other.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 비페닐기일 수 있다. 즉, 비페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다. As used herein, the term "substituted or unsubstituted" includes hydrogen; halogen group; nitrile group; nitro group; hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.
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 50인 것이 바람직하다. 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, 시클로펜틸메틸, 시클로헥실메틸, 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 linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. Specific examples include 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-dimethyl heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 구체적으로 시클로프로필, 시클로부틸, 시클로펜틸, 3-메틸시클로펜틸, 2,3-디메틸시클로펜틸, 시클로헥실, 3-메틸시클로헥실, 4-메틸시클로헥실, 2,3-디메틸시클로헥실, 3,4,5-트리메틸시클로헥실, 4-tert-부틸시클로헥실, 시클로헵틸, 시클로옥틸 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 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, etc., but are not limited thereto. does not
본 명세서에 있어서, 상기 알콕시기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 20인 것이 바람직하다. 구체적으로, 메톡시, 에톡시, n-프로폭시, 이소프로폭시, i-프로필옥시, n-부톡시, 이소부톡시, tert-부톡시, sec-부톡시, n-펜틸옥시, 네오펜틸옥시, 이소펜틸옥시, n-헥실옥시, 3,3-디메틸부틸옥시, 2-에틸부틸옥시, n-옥틸옥시, n-노닐옥시, n-데실옥시, 벤질옥시, p-메틸벤질옥시 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. may be, but is not limited thereto.
본 명세서에서 상기 아릴기가 단환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나, 탄소수 6 내지 25인 것이 바람직하다. 구체적으로 단환식 아릴기로는 페닐기, 비페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably 6 to 25 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.
상기 아릴기가 다환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나. 탄소수 10 내지 24인 것이 바람직하다. 구체적으로 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it is C10-C24. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.
본 명세서에 있어서, 상기 플루오레닐기는 치환될 수 있으며, 인접한 치환기들이 서로 결합하여 고리를 형성할 수 있다. In the present specification, the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.
상기 플루오레닐기가 치환되는 경우, 
본 명세서에 있어서, 헤테로아릴기는 탄소가 아닌 원자, 이종원자를 1 이상 포함하는 것으로서, 구체적으로 상기 이종 원자는 O, N, Se 및 S 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 헤테로아릴기의 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로아릴기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 트리아졸기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤즈옥사졸기, 벤즈이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 페난쓰롤린기(phenanthroline), 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 벤조티아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heteroaryl group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se and S, and the like. Although the number of carbon atoms of the heteroaryl group is not particularly limited, it is preferably from 2 to 60 carbon atoms. Examples of the heteroaryl group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, a triazole group, Acridyl 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, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.
본 명세서에 있어서, 아릴렌기는 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다. In the present specification, the description of the above-described aryl group may be applied except that the arylene group is a divalent group.
본 명세서에 있어서, 헤테로아릴렌기는 2가기인 것을 제외하고는 전술한 헤테로아릴기에 관한 설명이 적용될 수 있다.In the present specification, the description of the above-described heteroaryl group may be applied, except that the heteroarylene group is a divalent group.
본 출원의 일 실시상태에 따르면, X1은 NR, X2는 직접결합; 또는 X1은 직접결합, X2는 NR이다. 즉, X1 및 X2가 모두 직접결합이거나, X1 및 X2가 모두 NR은 아니며, X1 및 X2 중 하나는 직접결합, 나머지 하나는 NR이다.According to an exemplary embodiment of the present application, X1 is NR, X2 is a direct bond; or X1 is a direct bond, and X2 is NR. That is, both X1 and X2 are a direct bond, or both X1 and X2 are not NR, and one of X1 and X2 is a direct bond and the other is NR.
본 출원의 일 실시상태에 따르면, 상기 A는 벤젠고리이다.According to an exemplary embodiment of the present application, A is a benzene ring.
본 출원의 일 실시상태에 따르면, 상기 R은 하기 화학식 2로 표시된다.According to an exemplary embodiment of the present application, R is represented by the following formula (2).
[화학식 2][Formula 2]
본 출원의 일 실시상태에 따르면, 상기 L은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이다.According to an exemplary embodiment of the present application, L is a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.
본 출원의 일 실시상태에 따르면, 상기 L은 직접결합; 치환 또는 비치환된 탄소수 6 내지 60의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴렌기이다.According to an exemplary embodiment of the present application, L is a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.
본 출원의 일 실시상태에 따르면, 상기 L은 직접결합; 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴렌기이다.According to an exemplary embodiment of the present application, L is a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or
본 출원의 일 실시상태에 따르면, 상기 L은 직접결합; 치환 또는 비치환된 탄소수 6 내지 15의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 15의 헤테로아릴렌기이다.According to an exemplary embodiment of the present application, L is a direct bond; a substituted or unsubstituted arylene group having 6 to 15 carbon atoms; or a substituted or
본 출원의 일 실시상태에 따르면, 상기 L은 직접결합; 탄수소 6 내지 20의 아릴기로 치환 또는 비치환된 탄수소 6 내지 20의 아릴렌기이다. According to an exemplary embodiment of the present application, L is a direct bond; An arylene group having 6 to 20 carbon atoms is unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms.
본 출원의 일 실시상태에 따르면, 상기 L은 직접결합; 치환 또는 비치환된 페닐렌기; 치환 또는 비치환된 나프틸렌기; 또는 치환 또는 비치환된 바이페닐릴렌기이다.According to an exemplary embodiment of the present application, L is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted naphthylene group; or a substituted or unsubstituted biphenylrylene group.
본 출원의 일 실시상태에 따르면, 상기 L은 직접결합; 아릴기로 치환 또는 비치환된 페닐렌기; 아릴기로 치환 또는 비치환된 나프틸렌기; 또는 아릴기로 치환 또는 비치환된 바이페닐릴렌기이다. According to an exemplary embodiment of the present application, L is a direct bond; a phenylene group unsubstituted or substituted with an aryl group; a naphthylene group unsubstituted or substituted with an aryl group; Or a biphenyl rylene group unsubstituted or substituted with an aryl group.
본 출원의 일 실시상태에 따르면, 상기 L은 직접결합; 페닐기로 치환 또는 비치환된 페닐렌기; 페닐기로 치환 또는 비치환된 나프틸렌기; 또는 페닐기로 치환 또는 비치환된 바이페닐릴렌기이다.According to an exemplary embodiment of the present application, L is a direct bond; a phenylene group unsubstituted or substituted with a phenyl group; a naphthylene group unsubstituted or substituted with a phenyl group; or a biphenylrylene group unsubstituted or substituted with a phenyl group.
본 출원의 일 실시상태에 따르면, 상기 Ar은 하기 구조식 중에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present application, Ar is any one selected from the following structural formula.
본 출원의 일 실시상태에 따르면, 상기 R'은 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.According to an exemplary embodiment of the present application, R' is hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 출원의 일 실시상태에 따르면, 상기 R'은 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 60의 알킬기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기이다.According to an exemplary embodiment of the present application, R' is hydrogen; heavy hydrogen; a substituted or
본 출원의 일 실시상태에 따르면, 상기 R'은 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴기이다.According to an exemplary embodiment of the present application, R' is hydrogen; heavy hydrogen; a substituted or
본 출원의 일 실시상태에 따르면, 상기 R'은 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 15의 알킬기; 치환 또는 비치환된 탄소수 6 내지 15의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 15의 헤테로아릴기이다.According to an exemplary embodiment of the present application, R' is hydrogen; heavy hydrogen; a substituted or
본 출원의 일 실시상태에 따르면, 상기 R'은 수소; 중수소; 치환 또는 비치환된 탄소수 6 내지 15의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 15의 헤테로아릴기이다.According to an exemplary embodiment of the present application, R' is hydrogen; heavy hydrogen; a substituted or
본 출원의 일 실시상태에 따르면, 상기 R'은 수소; 중수소; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 아릴기; 또는 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 헤테로아릴기이다.According to an exemplary embodiment of the present application, R' is hydrogen; heavy hydrogen; an aryl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; or a heteroaryl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group.
본 출원의 일 실시상태에 따르면, 상기 R'은 수소; 중수소; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 아릴기; 또는 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 3환고리의 헤테로아릴기이다.According to an exemplary embodiment of the present application, R' is hydrogen; heavy hydrogen; an aryl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; or a tricyclic heteroaryl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group.
본 출원의 일 실시상태에 따르면, 상기 R'은 수소; 중수소; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 페난쓰렌기; 치환 또는 비치환된 플루오렌기; 치환 또는 비치환된 트리페닐렌기; 치환 또는 비치환된 디벤조퓨란기; 치환 또는 비치환된 디벤조티오펜기; 또는 치환 또는 비치환된 카바졸기이다. According to an exemplary embodiment of the present application, R' is hydrogen; heavy hydrogen; a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted fluorene group; a substituted or unsubstituted triphenylene group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.
본 출원의 일 실시상태에 따르면, 상기 R'의 "치환 또는 비치환된"은 중수소, 알킬기, 및 아릴기로 이루어진 군에서 선택되는 1이상의 치환기로 치환 또는 비치환 되는 것을 의미한다. According to an exemplary embodiment of the present application, "substituted or unsubstituted" of R' means unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, and an aryl group.
본 출원의 일 실시상태에 따르면, 상기 R'의 "치환 또는 비치환된"은 중수소, 메틸기, 및 페닐기로 이루어진 군에서 선택되는 1이상의 치환기로 치환 또는 비치환 되는 것을 의미한다. According to an exemplary embodiment of the present application, "substituted or unsubstituted" of R' means unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a methyl group, and a phenyl group.
본 출원의 일 실시상태에 따르면, 상기 R'은 수소; 중수소; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 페닐기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 나프틸기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 바이페닐기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 터페닐기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 페난쓰렌기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 플루오렌기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 트리페닐렌기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 디벤조퓨란기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 디벤조티오펜기; 또는 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 카바졸기이다. According to an exemplary embodiment of the present application, R' is hydrogen; heavy hydrogen; a phenyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a naphthyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a biphenyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a terphenyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a phenanthrene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a fluorene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a triphenylene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a dibenzofuran group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a dibenzothiophene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; Or a carbazole group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group.
본 출원의 일 실시상태에 따르면, 상기 R'은 수소; 중수소; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 페닐기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 나프틸기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 바이페닐기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 터페닐기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 페난쓰렌기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 플루오렌기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 트리페닐렌기; 디벤조퓨란기; 디벤조티오펜기; 또는 아릴기로 치환 또는 비치환된 카바졸기이다. According to an exemplary embodiment of the present application, R' is hydrogen; heavy hydrogen; a phenyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a naphthyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a biphenyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a terphenyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a phenanthrene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a fluorene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a triphenylene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; dibenzofuran group; dibenzothiophene group; Or a carbazole group unsubstituted or substituted with an aryl group.
본 출원의 일 실시상태에 따르면, 상기 R'은 수소; 중수소; 중수소, 메틸기, 또는 페닐기로 치환 또는 비치환된 페닐기; 중수소, 메틸기, 또는 페닐기로 치환 또는 비치환된 나프틸기; 중수소, 메틸기, 또는 페닐기로 치환 또는 비치환된 바이페닐기; 중수소, 메틸기, 또는 페닐기로 치환 또는 비치환된 터페닐기; 중수소, 메틸기, 또는 페닐기로 치환 또는 비치환된 페난쓰렌기; 중수소, 메틸기, 또는 페닐기로 치환 또는 비치환된 플루오렌기; 중수소, 메틸기, 또는 페닐기로 치환 또는 비치환된 트리페닐렌기; 디벤조퓨란기; 디벤조티오펜기; 또는 페닐기로 치환 또는 비치환된 카바졸기이다. According to an exemplary embodiment of the present application, R' is hydrogen; heavy hydrogen; a phenyl group unsubstituted or substituted with deuterium, a methyl group, or a phenyl group; a naphthyl group unsubstituted or substituted with deuterium, a methyl group, or a phenyl group; a biphenyl group unsubstituted or substituted with deuterium, a methyl group, or a phenyl group; a terphenyl group unsubstituted or substituted with deuterium, a methyl group, or a phenyl group; a phenanthrene group unsubstituted or substituted with deuterium, a methyl group, or a phenyl group; a fluorene group unsubstituted or substituted with deuterium, a methyl group, or a phenyl group; a triphenylene group unsubstituted or substituted with deuterium, a methyl group, or a phenyl group; dibenzofuran group; dibenzothiophene group; Or a carbazole group unsubstituted or substituted with a phenyl group.
본 출원의 일 실시상태에 따르면, 상기 R'은 수소; 중수소; 중수소로 치환 또는 비치환된 페닐기; 중수소, 또는 페닐기로 치환 또는 비치환된 나프틸기; 중수소로 치환 또는 비치환된 바이페닐기; 중수소로 치환 또는 비치환된 터페닐기; 중수소로 치환 또는 비치환된 페난쓰렌기; 메틸기, 또는 페닐기로 치환 또는 비치환된 플루오렌기; 중수소로 치환 또는 비치환된 트리페닐렌기; 디벤조퓨란기; 디벤조티오펜기; 또는 페닐기로 치환 또는 비치환된 카바졸기이다. According to an exemplary embodiment of the present application, R' is hydrogen; heavy hydrogen; a phenyl group unsubstituted or substituted with deuterium; a naphthyl group unsubstituted or substituted with deuterium or a phenyl group; a biphenyl group unsubstituted or substituted with deuterium; a terphenyl group unsubstituted or substituted with deuterium; a phenanthrene group unsubstituted or substituted with deuterium; a fluorene group unsubstituted or substituted with a methyl group or a phenyl group; a triphenylene group unsubstituted or substituted with deuterium; dibenzofuran group; dibenzothiophene group; Or a carbazole group unsubstituted or substituted with a phenyl group.
본 출원의 일 실시상태에 따르면, 상기 x는 0 내지 5의 정수이고, y는 0 내지 7의 정수이고, x 또는 y가 2 이상인 경우, 괄호 내의 치환기는 서로 같거나 상이하다.According to an exemplary embodiment of the present application, x is an integer of 0 to 5, y is an integer of 0 to 7, and when x or y is 2 or more, the substituents in parentheses are the same as or different from each other.
본 출원의 일 실시상태에 따르면, 상기 x 및 y는 1이다.According to an exemplary embodiment of the present application, x and y are 1.
본 출원의 일 실시상태에 따르면, 상기 a는 1 또는 2이고; a가 2인 경우에, 괄호 내의 치환기는 서로 같거나 상이하다.According to an exemplary embodiment of the present application, a is 1 or 2; When a is 2, the substituents in parentheses are the same as or different from each other.
본 출원의 일 실시상태에 따르면, 상기 Ar은 하기 구조식 중에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present application, Ar is any one selected from the following structural formula.
상기 구조식에 있어서, R''은 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,In the above structural formula, R'' is hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
x1는 0 내지 4의 정수이고,x1 is an integer from 0 to 4,
y1는 0 내지 6의 정수이고,y1 is an integer from 0 to 6,
x 또는 y가 2 이상인 경우, 괄호 내의 치환기는 서로 같거나 상이하며,When x or y is 2 or more, the substituents in parentheses are the same as or different from each other,
Ra는 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다. Ra is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 출원의 일 실시상태에 따르면, 상기 R"은 수소 또는 중수소이다. According to an exemplary embodiment of the present application, R" is hydrogen or deuterium.
본 출원의 일 실시상태에 따르면, 상기 Ra는 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 아릴기; 또는 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 헤테로아릴기이다.According to an exemplary embodiment of the present application, Ra is an aryl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; or a heteroaryl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group.
본 출원의 일 실시상태에 따르면, 상기 Ra는 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 아릴기; 또는 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 3환고리의 헤테로아릴기이다.According to an exemplary embodiment of the present application, Ra is an aryl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; or a tricyclic heteroaryl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group.
본 출원의 일 실시상태에 따르면, 상기 Ra는 수소; 중수소; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 페난쓰렌기; 치환 또는 비치환된 플루오렌기; 치환 또는 비치환된 트리페닐렌기; 치환 또는 비치환된 디벤조퓨란기; 치환 또는 비치환된 디벤조티오펜기; 또는 치환 또는 비치환된 카바졸기이다. According to an exemplary embodiment of the present application, Ra is hydrogen; heavy hydrogen; a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted fluorene group; a substituted or unsubstituted triphenylene group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.
본 출원의 일 실시상태에 따르면, 상기 Ra의 "치환 또는 비치환된"은 중수소, 알킬기, 및 아릴기로 이루어진 군에서 선택되는 1이상의 치환기로 치환 또는 비치환 되는 것을 의미한다. According to an exemplary embodiment of the present application, "substituted or unsubstituted" of Ra means unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, and an aryl group.
본 출원의 일 실시상태에 따르면, 상기 Ra의 "치환 또는 비치환된"은 중수소, 메틸기, 및 페닐기로 이루어진 군에서 선택되는 1이상의 치환기로 치환 또는 비치환 되는 것을 의미한다. According to an exemplary embodiment of the present application, "substituted or unsubstituted" of Ra means unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a methyl group, and a phenyl group.
본 출원의 일 실시상태에 따르면, 상기 Ra는 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 페닐기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 나프틸기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 바이페닐기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 터페닐기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 페난쓰렌기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 플루오렌기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 트리페닐렌기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 디벤조퓨란기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 디벤조티오펜기; 또는 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 카바졸기이다. According to an exemplary embodiment of the present application, Ra is a phenyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a naphthyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a biphenyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a terphenyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a phenanthrene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a fluorene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a triphenylene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a dibenzofuran group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a dibenzothiophene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; Or a carbazole group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group.
본 출원의 일 실시상태에 따르면, 상기 Ra는 중수소; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 페닐기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 나프틸기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 바이페닐기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 터페닐기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 페난쓰렌기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 플루오렌기; 중수소, 알킬기, 또는 아릴기로 치환 또는 비치환된 트리페닐렌기; 디벤조퓨란기; 디벤조티오펜기; 또는 아릴기로 치환 또는 비치환된 카바졸기이다. According to an exemplary embodiment of the present application, Ra is deuterium; a phenyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a naphthyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a biphenyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a terphenyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a phenanthrene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a fluorene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a triphenylene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; dibenzofuran group; dibenzothiophene group; Or a carbazole group unsubstituted or substituted with an aryl group.
본 출원의 일 실시상태에 따르면, 상기 Ra는 중수소, 메틸기, 또는 페닐기로 치환 또는 비치환된 페닐기; 중수소, 메틸기, 또는 페닐기로 치환 또는 비치환된 나프틸기; 중수소, 메틸기, 또는 페닐기로 치환 또는 비치환된 바이페닐기; 중수소, 메틸기, 또는 페닐기로 치환 또는 비치환된 터페닐기; 중수소, 메틸기, 또는 페닐기로 치환 또는 비치환된 페난쓰렌기; 중수소, 메틸기, 또는 페닐기로 치환 또는 비치환된 플루오렌기; 중수소, 메틸기, 또는 페닐기로 치환 또는 비치환된 트리페닐렌기; 디벤조퓨란기; 디벤조티오펜기; 또는 페닐기로 치환 또는 비치환된 카바졸기이다. According to an exemplary embodiment of the present application, Ra is a phenyl group unsubstituted or substituted with deuterium, a methyl group, or a phenyl group; a naphthyl group unsubstituted or substituted with deuterium, a methyl group, or a phenyl group; a biphenyl group unsubstituted or substituted with deuterium, a methyl group, or a phenyl group; a terphenyl group unsubstituted or substituted with deuterium, a methyl group, or a phenyl group; a phenanthrene group unsubstituted or substituted with deuterium, a methyl group, or a phenyl group; a fluorene group unsubstituted or substituted with deuterium, a methyl group, or a phenyl group; a triphenylene group unsubstituted or substituted with deuterium, a methyl group, or a phenyl group; dibenzofuran group; dibenzothiophene group; Or a carbazole group unsubstituted or substituted with a phenyl group.
본 출원의 일 실시상태에 따르면, 상기 Ra는 중수소로 치환 또는 비치환된 페닐기; 중수소, 또는 페닐기로 치환 또는 비치환된 나프틸기; 중수소로 치환 또는 비치환된 바이페닐기; 중수소로 치환 또는 비치환된 터페닐기; 중수소로 치환 또는 비치환된 페난쓰렌기; 메틸기, 또는 페닐기로 치환 또는 비치환된 플루오렌기; 중수소로 치환 또는 비치환된 트리페닐렌기; 디벤조퓨란기; 디벤조티오펜기; 또는 페닐기로 치환 또는 비치환된 카바졸기이다.According to an exemplary embodiment of the present application, Ra is a phenyl group unsubstituted or substituted with deuterium; a naphthyl group unsubstituted or substituted with deuterium or a phenyl group; a biphenyl group unsubstituted or substituted with deuterium; a terphenyl group unsubstituted or substituted with deuterium; a phenanthrene group unsubstituted or substituted with deuterium; a fluorene group unsubstituted or substituted with a methyl group or a phenyl group; a triphenylene group unsubstituted or substituted with deuterium; dibenzofuran group; dibenzothiophene group; Or a carbazole group unsubstituted or substituted with a phenyl group.
본 출원의 일 실시상태에 따르면, Ar은 하기 구조식 중에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present application, Ar is any one selected from the following structural formula.
상기 구조식의 Ra은 전술한 바와 같다. Ra of the structural formula is as described above.
본 출원의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 1-1로 표시된다.According to an exemplary embodiment of the present application,
[화학식 1-1][Formula 1-1]
상기 화학식 1-1에 있어서,In Formula 1-1,
R은 상기 정의와 같다.R is as defined above.
본 출원의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 1-2로 표시된다.According to an exemplary embodiment of the present application,
[화학식 1-2][Formula 1-2]
상기 화학식 1-2에 있어서,In Formula 1-2,
R은 상기 정의와 같다.R is as defined above.
또한, 본 명세서의 일 실시상태에 따르면, 상기 화학식 1로 표시되는 화합물은 하기 구조식들 중에서 선택되는 어느 하나이다.In addition, according to an exemplary embodiment of the present specification, the compound represented by
또한, 본 명세서는 상기 전술한 화합물을 포함하는 유기 발광 소자를 제공한다. In addition, the present specification provides an organic light emitting device including the above-described compound.
본 명세서의 일 실시상태에 있어서, 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하고, 상기 유기물층 중 1 층 이상은 상기 화합물을 포함하는 것인 유기 발광 소자를 제공한다. In one embodiment of the present specification, the first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.
본 명세서에서 어떤 부재가 다른 부재 "상에" 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 접해 있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 존재하는 경우도 포함한다.In the present specification, when a member is said to be located “on” another member, this includes not only a case in which a member is in contact with another member but also a case in which another member is present between the two members.
본 명세서에서 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다. In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless otherwise stated.
본 명세서의 유기 발광 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 발광 소자는 유기물층으로서 정공주입층, 정공수송층, 전자억제층, 발광층, 전자수송층, 전자주입층, 전자 주입 및 수송층, 정공저지층 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 specification 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, an electron suppression layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 정공주입층 또는 정공수송층을 포함하고, 상기 정공주입층 또는 정공수송층은 상기 화합물을 포함한다. In an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화합물을 포함한다. In an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound.
본 명세서의 일 실시상태에 있어서, 상기 화합물은 상기 발광층의 호스트로 포함된다. In an exemplary embodiment of the present specification, the compound is included as a host of the light emitting layer.
본 명세서의 일 실시상태에 있어서, 상기 화합물은 상기 발광층의 적색 호스트로 포함된다. In an exemplary embodiment of the present specification, the compound is included as a red host of the light emitting layer.
본 명세서의 일 실시상태에 있어서, 상기 발광층은 도펀트를 더 포함한다. In one embodiment of the present specification, the light emitting layer further includes a dopant.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1의 화합물을 포함하는 유기물층은 상기 화학식 1의 화합물을 호스트로서 포함하고, 다른 유기화합물, 금속 또는 금속화합물을 도펀트로 포함할 수 있다. In an exemplary embodiment of the present specification, the organic material layer including the compound of
본 명세서의 일 실시상태에 있어서, 상기 화학식 1의 화합물을 포함하는 유기물층은 상기 화학식 1의 화합물을 호스트로서 포함하고, 이리듐계 도펀트를 포함할 수 있다. In the exemplary embodiment of the present specification, the organic material layer including the compound of
본 명세서의 일 실시상태에 있어서, 상기 화학식 1의 화합물을 포함하는 유기물층은 상기 화학식 1의 화합물을 호스트로서 포함하고, 인광 도펀트를 포함할 수 있다. In an exemplary embodiment of the present specification, the organic material layer including the compound of
본 명세서의 일 실시상태에 있어서, 상기 화학식 1의 화합물을 포함하는 유기물층은 상기 화학식 1의 화합물을 호스트로서 포함하고, 적색 또는 녹색 인광 도펀트를 포함할 수 있다. In an exemplary embodiment of the present specification, the organic material layer including the compound of
본 명세서의 일 실시상태에 있어서, 상기 화학식 1의 화합물을 포함하는 유기물층은 상기 화학식 1의 화합물을 호스트로서 포함하고, 이리듐계 인광 도펀트를 포함할 수 있다. In an exemplary embodiment of the present specification, the organic material layer including the compound of
본 명세서의 일 실시상태에 따르면, 상기 발광층은 상기 화합물과 도펀트를 1:99 내지 99:1의 중량비로 포함한다.According to an exemplary embodiment of the present specification, the light emitting layer includes the compound and the dopant in a weight ratio of 1:99 to 99:1.
본 명세서의 일 실시상태에 따르면, 상기 발광층은 상기 화합물과 도펀트를 2:1 내지 99:1의 중량비로 포함한다.According to an exemplary embodiment of the present specification, the light emitting layer includes the compound and the dopant in a weight ratio of 2:1 to 99:1.
본 명세서의 일 실시상태에 있어서, 상기 이리듐계 도펀트는 하기 구조에서 선택될 수 있으나, 이에 한정되지 않는다. In the exemplary embodiment of the present specification, the iridium-based dopant may be selected from the following structures, but is not limited thereto.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 전자수송층 또는 전자주입층을 포함하고, 상기 전자수송층 또는 전자주입층은 상기 화합물을 포함한다. In an exemplary embodiment of the present specification, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 정공주입층, 정공수송층, 또는 전자억제층을 포함할 수 있다. In an exemplary embodiment of the present specification, the organic material layer may include a hole injection layer, a hole transport layer, or an electron suppression layer.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 정공주입층, 정공수송층, 및 전자억제층을 포함할 수 있다. In the exemplary embodiment of the present specification, the organic material layer may include a hole injection layer, a hole transport layer, and an electron suppression layer.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 정공저지층; 또는 전자 주입 및 수송층을 포함할 수 있다. In one embodiment of the present specification, the organic material layer is a hole blocking layer; or an electron injection and transport layer.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 정공저지층; 및 전자 주입 및 수송층을 포함할 수 있다. In one embodiment of the present specification, the organic material layer is a hole blocking layer; and an electron injection and transport layer.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 정공주입층, 정공수송층, 전자수송층, 전자주입층, 전자주입 및 수송층, 전자억제층 및 정공저지층으로 이루어진 군에서 선택되는 1층 또는 2층 이상을 더 포함한다. In one embodiment of the present specification, the organic light emitting device is a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, an electron suppression layer and one layer or two selected from the group consisting of a hole blocking layer It further includes more than a layer.
본 출원의 일 실시상태에 있어서, 상기 유기 발광 소자는 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 발광층; 상기 발광층과 상기 제1 전극 사이, 또는 상기 발광층과 상기 제2 전극 사이에 구비된 2층 이상의 유기물층을 포함하고, 상기 2층 이상의 유기물층 중 적어도 하나는 상기 화합물을 포함한다. 본 출원의 일 실시상태에 있어서, 상기 2층 이상의 유기물층은 전자수송층, 전자주입층, 전자 수송과 전자주입을 동시에 하는 층 및 정공저지층으로 이루어진 군에서 2 이상이 선택될 수 있다.In an exemplary embodiment of the present application, the organic light emitting device includes a first electrode; a second electrode provided to face the first electrode; and a light emitting layer provided between the first electrode and the second electrode. and two or more organic material layers provided between the light emitting layer and the first electrode or between the light emitting layer and the second electrode, and at least one of the two or more organic material layers includes the compound. In an exemplary embodiment of the present application, two or more organic material layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer for simultaneously transporting electrons and electron injection, and a hole blocking layer.
본 출원의 일 실시상태에 있어서, 상기 유기물층은 2층 이상의 전자수송층을 포함하고, 상기 2층 이상의 전자수송층 중 적어도 하나는 상기 화합물을 포함한다. 구체적으로 본 명세서의 일 실시상태에 있어서, 상기 화합물은 상기 2층 이상의 전자수송층 중 1층에 포함될 수도 있으며, 각각의 2층 이상의 전자수송층에 포함될 수 있다. In an exemplary embodiment of the present application, the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound. Specifically, in one embodiment of the present specification, the compound may be included in one of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.
또한, 본 출원의 일 실시상태에 있어서, 상기 화합물이 상기 각각의 2층 이상의 전자수송층에 포함되는 경우, 상기 화합물을 제외한 다른 재료들은 서로 동일하거나 상이할 수 있다.In addition, in the exemplary embodiment of the present application, when the compound is included in each of the two or more electron transport layers, materials other than the compound may be the same or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 상기 화합물을 포함하는 유기물층 이외에 아릴아미노기, 카바졸기 또는 벤조카바졸기를 포함하는 화합물을 포함하는 정공주입층 또는 정공수송층을 더 포함한다. In an exemplary embodiment of the present specification, the organic material layer further includes a hole injection layer or a hole transport layer including a compound including an arylamino group, a carbazole group or a benzocarbazole group in addition to the organic material layer including the compound.
또 하나의 실시상태에 있어서, 유기 발광 소자는 기판 상에 제1 전극, 1층 이상의 유기물층 및 제2 전극이 순차적으로 적층된 구조(normal type)의 유기 발광 소자일 수 있다. In another exemplary embodiment, the organic light emitting device may be a normal type organic light emitting device in which a first electrode, one or more organic material layers, and a second electrode are sequentially stacked on a substrate.
또 하나의 실시상태에 있어서, 유기 발광 소자는 기판 상에 제2 전극, 1층 이상의 유기물층 및 제1 전극이 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다. In another exemplary embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a second electrode, one or more organic material layers, and a first electrode are sequentially stacked on a substrate.
예컨대, 본 명세서의 일 실시상태에 따른 유기 발광 소자의 구조는 도 1 및 2에 예시되어 있다. For example, the structure of the organic light emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 and 2 .
도 1은 기판(1), 제1 전극(2), 발광층(3), 제2 전극(4)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화합물은 상기 발광층(3)에 포함될 수 있다. 1 illustrates a structure of an organic light emitting device in which a
도 2는 기판 (1), 제1 전극(2), 정공주입층(5), 정공수송층(6), 발광층(3), 전자수송층(7) 및 제2 전극(4)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서 상기 화합물은 상기 정공주입층(5), 정공 수송층(6), 발광층(3) 및 전자 수송층(7) 중 1층 이상에 포함될 수 있다. 2 is a substrate (1), a first electrode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (3), an electron transport layer (7) and a second electrode (4) are sequentially stacked The structure of the organic light emitting device is exemplified. In this structure, the compound may be included in one or more of the
도 3은 기판(1), 제1 전극(2), 정공주입층(5), 정공수송층(6), 전자억제층(8), 발광층(3), 정공저지층(9), 전자주입 및 수송층(10) 및 제2 전극(4)이 순차적으로 적층된 유기 발광 소자의 구조사 예시되어 있으며, 상기 화합물은 발광층(3)에 포함될 수 있으나, 이에 한정되지 않는다. 3 is a
이와 같은 구조에 있어서, 상기 화합물은 상기 정공주입층, 정공수송층, 발광층 및 전자수송층 중 1층 이상에 포함될 수 있다. In such a structure, the compound may be included in one or more of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.
본 명세서의 유기 발광 소자는 유기물층 중 1층 이상이 본 명세서의 화합물, 즉 상기 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다.The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present specification, that is, the compound.
상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다. When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
본 명세서의 유기 발광 소자는 유기물층 중 1층 이상이 상기 화합물, 즉 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer includes the compound, that is, the compound represented by
예컨대, 본 명세서의 유기 발광 소자는 기판 상에 제1 전극, 유기물층 및 제2 전극을 순차적으로 적층시킴으로써 제조할 수 있다. 이 때 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 제1 전극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물층을 형성한 후, 그 위에 제2 전극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 제2 전극 물질부터 유기물층, 제1 전극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수 있다. For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or a conductive metal oxide or an alloy thereof is deposited on a substrate to deposit the first electrode After forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, it can be prepared by depositing a material that can be used as a second electrode thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate.
또한, 상기 화학식 1의 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.In addition, the compound of
이와 같은 방법 외에도, 기판 상에 제2 전극 물질로부터 유기물층, 제1 전극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수도 있다 (국제 특허 출원 공개 제 2003/012890호). 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 first electrode material on a substrate from the second electrode material (International Patent Application Laid-Open No. 2003/012890). However, the manufacturing method is not limited thereto.
본 명세서의 일 실시상태에 있어서, 상기 제1 전극은 양극이고, 상기 제2 전극은 음극이다. In the exemplary embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.
또 하나의 실시상태에 있어서, 상기 제1 전극은 음극이고, 상기 제2 전극은 양극이다. In another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.
상기 제1 전극 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 본 발명에서 사용될 수 있는 제1 전극 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. As the material for the first electrode, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer. Specific examples of the first electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO 2 : a combination of a metal such as Sb and an oxide; 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 제2 전극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 제2 전극 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 second electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the second electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
상기 정공 주입 물질로는 전극으로부터 정공을 주입하는 층으로, 정공 주입 물질로는 정공을 수송하는 능력을 가져 제1 전극에서의 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 제1 전극 물질의 일함수와 주변 유기물층의 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 material is a layer for injecting holes from the electrode, and the hole injection material has the ability to transport holes and has an excellent hole injection effect on the first electrode, the light emitting layer or the light emitting material, and the light emitting layer A compound which prevents the movement of excitons generated in the electron injection layer or the electron injection material and 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 first 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 material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers, and the like, but are not limited thereto.
본 출원의 일 실시상태에 있어서, 상기 유기물층은 정공주입층을 포함하고, 상기 정공주입층은 p-도핑된다. In an exemplary embodiment of the present application, the organic material layer includes a hole injection layer, and the hole injection layer is p-doped.
본 출원의 일 실시상태에 있어서, 상기 유기물층은 정공주입층을 포함하고, 상기 정공주입층은 p-도핑된다. In an exemplary embodiment of the present application, the organic material layer includes a hole injection layer, and the hole injection layer is p-doped.
본 명세서의 일 실시상태에 있어서, 상기 정공주입층은 p-도핑물질을 더 포함한다. In an exemplary embodiment of the present specification, the hole injection layer further includes a p-doping material.
본 명세서에서 상기 p 도핑 물질이란, 호스트 물질을 p 반도체 특성을 갖도록 하는 물질을 의미한다. p 반도체 특성이란 HOMO(highest occupied molecular orbital)에너지 준위로 정공을 주입받거나 수송하는 특성 즉, 정공의 전도도가 큰 물질의 특성을 의미한다.상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 정공 수송 물질로는 제1 전극이나 정공 주입층으로부터 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. In the present specification, the p-doped material refers to a material that allows the host material to have p-semiconductor properties. The p-semiconductor property refers to a property of receiving or transporting holes at the highest occupied molecular orbital (HOMO) energy level, that is, a property of a material with high hole conductivity. The hole transport layer receives holes from the hole injection layer and reaches the light emitting layer. As the hole transport material, a material capable of transporting holes from the first electrode or the hole injection layer to the light emitting layer is suitable for the hole transport material. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.
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 예로는 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. The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
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 화합물, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되지 않는다. The emission layer may include a host material and a dopant material. The host material includes a condensed aromatic ring derivative or a compound containing a hetero ring. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic-containing compounds include compounds, dibenzofuran derivatives, ladder-type furan compounds. , pyrimidine derivatives, and the like, but are not limited thereto.
상기 전자 수송 층은 전자주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층으로 전자 수송 물질로는 제2 전극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al착물; 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 them to the light emitting layer. material is suitable. Specific examples include Al complex of 8-hydroxyquinoline; complexes comprising Alq3; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function and followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by an aluminum layer or a silver layer.
상기 전자주입층은 전극으로부터 전자를 주입하는 층으로, 전자를 수송하는 능력을 갖고, 제2 전극으로부터의 전자주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공 주입층에의 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 함질소 5원환 유도체 등이 있으나, 이에 한정되지 않는다. The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the second electrode, an excellent electron injection effect on the light emitting layer or the light emitting material, and A compound that prevents migration to the hole injection layer and is excellent in the ability to form a thin film is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, 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) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.
상기 정공저지층은 정공의 제2 전극 도달을 저지하는 층으로, 일반적으로 정공주입층과 동일한 조건으로 형성될 수 있다. 구체적으로 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, BCP, 알루미늄 착물 (aluminum complex) 등이 있으나, 이에 한정되지 않는다. The hole blocking layer is a layer that blocks holes from reaching the second electrode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, and the like, but is not limited thereto.
본 명세서에 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 specification may be a top emission type, a back emission type, or a double side emission type depending on the material used.
상기 화학식 1의 화합물의 제조방법 및 이들을 이용한 유기 발광 소자의 제조는 이하의 실시예에서 구체적으로 설명한다. 그러나, 하기 실시예는 본 발명을 예시하기 위한 것이며, 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다.A method for preparing the compound of
본 발명의 화합물은 대표적인 반응으로 Buchwald-Hartwig coupling reaction, Suzuki coupling reaction, Heck coupling reaction 등을 이용하여 제조하였다.The compound of the present invention was prepared using the Buchwald-Hartwig coupling reaction, the Suzuki coupling reaction, and the Heck coupling reaction as representative reactions.
제조예 1.Preparation Example 1.
1-브로모트리페닐렌 100.0g (1.0 eq), (2-니트로페닐)보로닉산 60.04 g (1.1 eq)을 테트라하이드로퓨란(THF) 1000ml 에 녹인 후 물 300ml 에 녹인 K2CO3 90.33 g (2.0 eq)을 같이 넣어 주었다. Pd(t-Bu3P)2 1.59 g (0.005 eq) 을 넣어 주고 환류하여 교반하였다. 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 무수황산마그네슘으로 처리하여 다시 감압하여 용매를 제거하고 이를 컬럼크로마토그래피하여 화합물 A-1 84.42 g, 수율 74 %)를 얻었다. [M+H]+=3501-bromotriphenylene 100.0 g (1.0 eq), (2-nitrophenyl) boronic acid 60.04 g (1.1 eq) was dissolved in 1000 ml of tetrahydrofuran (THF), and then 90.33 g of K 2 CO 3 dissolved in 300 ml of water ( 2.0 eq) was added. 1.59 g (0.005 eq) of Pd( t -Bu 3 P) 2 was added, followed by reflux and stirring. When the reaction was completed, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, treated with anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and column chromatography was performed to obtain Compound A-1 (84.42 g, yield 74%). [M+H] + =350
화학식 A-1 84.42g (1.0 eq) 트리에틸포스파이트 200 mL에 넣고 환류하여 교반하였다. 2시간 후 반응 종결하고 에탄올 2L에 반응물을 부어서 고체를 떨어트렸다. 이 고체를 CHCl3에 완전히 녹인 후 물로 씻어주고 무수황산마그네슘으로 처리하여 용액을 감압 농축하고 컬럼크로마토그래피를 이용하여 정제하였다. 화합물 A 48.31g, 수율 63 %)을 얻었다. [M+H]+=31884.42 g (1.0 eq) of Formula A-1 was added to 200 mL of triethylphosphite, refluxed and stirred. After 2 hours, the reaction was terminated and the solid was dropped by pouring the reactant into 2L of ethanol. The solid was completely dissolved in CHCl 3 , washed with water, treated with anhydrous magnesium sulfate, the solution was concentrated under reduced pressure, and purified using column chromatography. Compound A 48.31 g, yield 63%) was obtained. [M+H] + =318
제조예 2.Preparation Example 2.
2-클로로아닐린 100.0g (1.0 eq), 1-브로모트리페닐렌 240.9 g (1.1 eq)을 톨루엔 1000ml 에 녹인 후 NaOtBu 151.33 g (2.0 eq)을 같이 넣어 주었다. Pd(t-Bu3P)2 4.02 g (0.01 eq) 을 넣어 주고 환류하여 교반하였다. 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 무수황산마그네슘으로 처리하여 다시 감압하여 용매를 제거하고 이를 컬럼크로마토그래피하여 화합물 B-1 205.71 g, 수율 74 %)를 얻었다. [M+H]+=354100.0 g (1.0 eq) of 2-chloroaniline and 240.9 g (1.1 eq) of 1-bromotriphenylene were dissolved in 1000 ml of toluene, followed by 151.33 g (2.0 eq) of NaOtBu. Pd( t -Bu 3 P) 2 4.02 g (0.01 eq) was added, and the mixture was stirred under reflux. When the reaction was completed, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, treated with anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and column chromatography was performed to obtain Compound B-1 (205.71 g, yield 74%). [M+H] + =354
화합물 B-1 205.0 g (1.0 eq) 을 디메틸아세트아미드(DMAc) 1000ml 에 녹인 후 K3PO4 247.33 g (2.0 eq), Pd(t-Bu3P)2 2.97 g (0.01 eq) 을 넣어 주고 환류하여 교반하였다. 반응이 종료되면 식힌 후 물에 부어서 교반 및 고체화 진행 후 여과하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 무수황산마그네슘으로 처리하여 다시 감압하여 용매를 제거하고 이를 컬럼크로마토그래피하여 화합물 B 136.7 g, 수율 74 %)를 얻었다. [M+H]+=318205.0 g (1.0 eq) of Compound B-1 was dissolved in 1000 ml of dimethylacetamide (DMAc), and then 247.33 g (2.0 eq) of K 3 PO 4 and 2.97 g (0.01 eq) of Pd(t- Bu 3 P) 2 were added. The mixture was stirred under reflux. When the reaction was completed, it was cooled, poured into water, stirred and solidified, and then filtered. After that , it was completely dissolved in CHCl 3 , washed with water, treated with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure, and the resultant was subjected to column chromatography to obtain Compound B (136.7 g, yield 74%). [M+H] + =318
<합성예><Synthesis example>
합성예Synthesis example 1 One
화합물 A 10.0 g (1.0 eq), 3-([1,1'-비페닐]-4-일)-2-클로로벤젠 [4,5]티에노[2,3-b]피라진 12.90 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), K3PO4 13.39 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 1 (15.03 g, 수율 73 %)을 얻었다. [M+H]+=654Compound A 10.0 g (1.0 eq), 3-([1,1'-biphenyl]-4-yl)-2-chlorobenzene [4,5] thieno [2,3-b] pyrazine 12.90 g (1.1 eq), Pd(t-Bu 3 P) 2 0.16 g (0.01 eq), K 3 PO 4 13.39 g (2.0 eq) were put in 250 ml of xylene, and the mixture was refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 1 (15.03 g, yield 73%). [M+H] + =654
합성예 2Synthesis Example 2
화합물 A 10.0 g (1.0 eq), 3-클로로-2-(9-페닐-9H-카바졸-2-일)벤조 [4,5]티에노[2,3-b]피라진 15.99 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), K3PO4 13.39 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 2 (16.38 g , 수율 70 %)를 얻었다. [M+H]+=743Compound A 10.0 g (1.0 eq), 3-chloro-2- (9-phenyl-9H-carbazol-2-yl) benzo [4,5] thieno [2,3-b] pyrazine 15.99 g (1.1 eq) ), Pd(t-Bu 3 P) 2 0.16 g (0.01 eq), K 3 PO 4 13.39 g (2.0 eq) were put in 250 ml of xylene, and the mixture was refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 2 (16.38 g , yield 70%). [M+H] + =743
합성예 3Synthesis Example 3
화합물 A 10.0 g (1.0 eq), 2-(9H-카바졸-9-일)-3-클로로벤조퓨로[2,3-b]피라진 12.80 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), K3PO4 13.39 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 3 (13.12 g, 수율 64 %)를 얻었다. [M+H]+=651Compound A 10.0 g (1.0 eq), 2-(9H-carbazol-9-yl)-3-chlorobenzofuro[2,3-b]pyrazine 12.80 g (1.1 eq), Pd(t-Bu 3 P ) 2 0.16 g (0.01 eq), K 3 PO 4 13.39 g (2.0 eq) were put in 250 ml of xylene, and the mixture was refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 3 (13.12 g, yield 64%). [M+H] + =651
합성예 4Synthesis Example 4
화합물 A 10.0 g (1.0 eq), 3-([1,1'-비페닐]-3-일)-2-클로로-9,9-디메틸-9H-인데노[1,2-b]피라진 13.25 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), K3PO4 13.39 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 4 (12.75 g, 수율 61 %)를 얻었다. [M+H]+=664Compound A 10.0 g (1.0 eq), 3-([1,1'-biphenyl]-3-yl)-2-chloro-9,9-dimethyl-9H-indeno[1,2-b]pyrazine 13.25 g (1.1 eq), Pd(t-Bu 3 P) 2 0.16 g (0.01 eq), K 3 PO 4 13.39 g (2.0 eq) was put in 250ml of xylene, and the mixture was refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 4 (12.75 g, yield 61%). [M+H] + =664
합성예 5Synthesis Example 5
화합물 A 10.0 g (1.0 eq), 2-클로로-9,9-디메틸-3-(9-페닐-9H-카바졸-4-일)-9H-인데노[1,2-b]피라진 16.34 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), K3PO4 13.39 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 5 (14.94 g, 수율 63 %)를 얻었다. [M+H]+=753Compound A 10.0 g (1.0 eq), 2-chloro-9,9-dimethyl-3-(9-phenyl-9H-carbazol-4-yl)-9H-indeno[1,2-b]pyrazine 16.34 g (1.1 eq), Pd(t-Bu 3 P) 2 0.16 g (0.01 eq), K 3 PO 4 13.39 g (2.0 eq) were put in 250 ml of xylene, and the mixture was refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 5 (14.94 g, yield 63%). [M+H] + =753
합성예 6Synthesis Example 6
화합물 A 10.0 g (1.0 eq), 2-클로로-4-(디벤조[b,d]티오펜-1-일)벤조[h]퀴나졸린 13.73 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), K3PO4 13.39 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 6 (13.02 g, 수율 61 %)를 얻었다. [M+H]+=678Compound A 10.0 g (1.0 eq), 2-chloro-4- (dibenzo [b,d] thiophen-1-yl) benzo [h] quinazoline 13.73 g (1.1 eq), Pd (t-Bu 3 P ) 2 0.16 g (0.01 eq), K 3 PO 4 13.39 g (2.0 eq) was put into 250ml of xylene, refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 6 (13.02 g, yield 61%). [M+H] + =678
합성예Synthesis example 7 7
화합물 A 10.0 g (1.0 eq), 3-클로로-1-(페난쓰렌-2-일)벤조[f]퀴나졸린 13.53 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), K3PO4 13.39 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 7 (13.75 g, 수율 65 %)를 얻었다. [M+H]+=672Compound A 10.0 g (1.0 eq), 3-chloro-1-(phenanthren-2-yl)benzo[f]quinazoline 13.53 g (1.1 eq), Pd(t-Bu 3 P) 2 0.16 g (0.01 eq) ), K 3 PO 4 13.39 g (2.0 eq) was put into 250 ml of xylene, and the mixture was refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 7 (13.75 g, yield 65%). [M+H] + =672
합성예 8Synthesis Example 8
화합물 A 10.0 g (1.0 eq), 3-([1,1':3',1''-터페닐]-5'-일)-1-클로로벤조[f]퀴나졸린15.33 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), K3PO4 13.39 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 8 (13.91 g, 수율 61 %)를 얻었다. [M+H]+=724Compound A 10.0 g (1.0 eq), 3-([1,1':3',1''-terphenyl]-5'-yl)-1-chlorobenzo[f]quinazoline 15.33 g (1.1 eq) , Pd(t-Bu 3 P) 2 0.16 g (0.01 eq), K 3 PO 4 13.39 g (2.0 eq) were put in 250 ml of xylene, and the mixture was refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 8 (13.91 g, yield 61%). [M+H] + =724
합성예 9Synthesis Example 9
화합물 A 10.0 g (1.0 eq), 2-클로로-3-(나프탈렌-1-일)벤조[f]퀴녹살린 11.79 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), K3PO4 13.39 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 9 (13.12 g, 수율 67 %)를 얻었다. [M+H]+=622Compound A 10.0 g (1.0 eq), 2-chloro-3- (naphthalen-1-yl) benzo [f] quinoxaline 11.79 g (1.1 eq), Pd (t-Bu 3 P) 2 0.16 g (0.01 eq) , K 3 PO 4 13.39 g (2.0 eq) was put into 250ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 9 (13.12 g, yield 67%). [M+H] + =622
합성예 10Synthesis Example 10
화합물 A 10.0 g (1.0 eq), 2-([1,1':4',1''-터페닐]-4-일)-3-클로로벤조[f]퀴녹살린 15.33 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), K3PO4 13.39 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 10 (14.14 g, 수율 62 %)를 얻었다. [M+H]+=724Compound A 10.0 g (1.0 eq), 2-([1,1':4',1''-terphenyl]-4-yl)-3-chlorobenzo[f]quinoxaline 15.33 g (1.1 eq), Pd(t-Bu 3 P) 2 0.16 g (0.01 eq), K 3 PO 4 13.39 g (2.0 eq) was put into 250ml of xylene, refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 10 (14.14 g, yield 62%). [M+H] + =724
합성예 11Synthesis Example 11
화합물 A 10.0 g (1.0 eq), 2-클로로-3-(4-페닐나프탈렌-1-일)퀴녹산린 12.69 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), K3PO4 13.39 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 11 (13.87 g, 수율 68 %)를 얻었다. [M+H]+=648 Compound A 10.0 g (1.0 eq), 2-chloro-3-(4-phenylnaphthalen-1-yl)quinoxanline 12.69 g (1.1 eq), Pd(t-Bu 3 P) 2 0.16 g (0.01 eq) , K 3 PO 4 13.39 g (2.0 eq) was put into 250ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 11 (13.87 g, yield 68%). [M+H] + =648
합성예 12Synthesis Example 12
화합물 A 10.0 g (1.0 eq), 2-([1,1'-비페닐]-4-일)-3-(3'-브로모-[1,1'-비페닐]-4-일)벤조[4,5]티에노[2,3-b]피라진 19.70 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 12 (18.02 g, 수율 71 %)를 얻었다. [M+H]+=806Compound A 10.0 g (1.0 eq), 2-([1,1'-biphenyl]-4-yl)-3-(3'-bromo-[1,1'-biphenyl]-4-yl) Benzo[4,5]thieno[2,3-b]pyrazine 19.70 g (1.1 eq), Pd(t-Bu 3 P) 2 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq) xylene 250ml It was put into reflux and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 12 (18.02 g, yield 71%). [M+H] + =806
합성예 13Synthesis Example 13
화합물 A 10.0 g (1.0 eq), 2-(2-브로모페닐)-3-(디벤조[b,d]퓨란-1-일)벤조[4,5]티에노[2,3-b]피라진 17.55 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 13 (14.45 g, 수율 67 %)를 얻었다. [M+H]+=744Compound A 10.0 g (1.0 eq), 2-(2-bromophenyl)-3-(dibenzo[b,d]furan-1-yl)benzo[4,5]thieno[2,3-b] Pyrazine 17.55 g (1.1 eq), Pd(t-Bu 3 P) 2 0.16 g (0.01 eq), and NaOtBu 6.06 g (2.0 eq) were added to 250 ml of xylene and stirred under reflux. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 13 (14.45 g, yield 67%). [M+H] + =744
합성예 14Synthesis Example 14
화합물 A 10.0 g (1.0 eq), 3-(5-브로모-[1,1'-비페닐]-2-일)-2-(나프탈렌-1-일)벤조퓨로[2,3-b]피라진 18.24 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 14 (17.81 g, 수율 74 %)를 얻었다. [M+H]+=764Compound A 10.0 g (1.0 eq), 3-(5-bromo-[1,1'-biphenyl]-2-yl)-2-(naphthalen-1-yl)benzofuro[2,3-b ]Pyrazine 18.24 g (1.1 eq), Pd(t-Bu 3 P) 2 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq) were put in 250 ml of xylene, and the mixture was refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 14 (17.81 g, yield 74%). [M+H] + =764
합성예 15Synthesis Example 15
화합물 A 10.0 g (1.0 eq), 4-(4-브로모나프탈렌-1-일)-2-(트리페닐렌-2-일)벤조[h]퀴나졸린 21.16 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 15 (17.90 g, 수율 67 %)를 얻었다. [M+H]+=848Compound A 10.0 g (1.0 eq), 4-(4-bromonaphthalen-1-yl)-2-(triphenylen-2-yl)benzo[h]quinazoline 21.16g (1.1 eq), Pd(t -Bu 3 P) 2 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq) were put in 250 ml of xylene, and the mixture was refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 15 (17.90 g, yield 67%). [M+H] + =848
합성예 16Synthesis Example 16
화합물 A 10.0 g (1.0 eq), 2-(4-브로모나프탈렌-2-일)-4-(디벤조[b,d]티오펜-1-일)벤조[h]퀴나졸린 19.63 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 16 (15.45 g, 수율 61 %)를 얻었다. [M+H]+=804Compound A 10.0 g (1.0 eq), 2-(4-bromonaphthalen-2-yl)-4-(dibenzo[b,d]thiophen-1-yl)benzo[h]quinazoline 19.63g (1.1 eq), Pd(t-Bu 3 P) 2 0.16 g (0.01 eq), and NaOtBu 6.06 g (2.0 eq) were put in 250 ml of xylene, and the mixture was refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 16 (15.45 g, yield 61%). [M+H] + =804
합성예Synthesis example 17 17
화합물 A 10.0 g (1.0 eq), 2-(2-브로모페닐)-3-(4-페닐나프탈렌-1-일)퀴녹살린 16.86 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 17 (13.00 g, 수율 57 %)를 얻었다. [M+H]+=724Compound A 10.0 g (1.0 eq), 2-(2-bromophenyl)-3-(4-phenylnaphthalen-1-yl)quinoxaline 16.86 g (1.1 eq), Pd(t-Bu 3 P) 2 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq) was put in 250ml of xylene and stirred under reflux. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 17 (13.00 g, yield 57%). [M+H] + =724
합성예 18Synthesis Example 18
화합물 B 10.0 g (1.0 eq), 2-클로로-3-(나프탈렌-2-일)벤조퓨로[2,3-b]피라진 11.44 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), K3PO4 13.39 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 18 (11.75 g, 수율 61 %)를 얻었다. [M+H]+=612Compound B 10.0 g (1.0 eq), 2-chloro-3- (naphthalen-2-yl) benzofuro [2,3-b] pyrazine 11.44 g (1.1 eq), Pd (t-Bu 3 P) 2 0.16 g (0.01 eq), K 3 PO 4 13.39 g (2.0 eq) was put into 250 ml of xylene, and the mixture was refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 18 (11.75 g, yield 61%). [M+H] + =612
합성예 19Synthesis Example 19
화합물 B 10.0 g (1.0 eq), 3-클로로-2-(디벤조[b,d]퓨란-3-일)-9,9-디메틸-9H-인데노[1,2-b]피라진 13.73 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), K3PO4 13.39 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 19 (12.17 g, 수율 57 %)를 얻었다. [M+H]+=678Compound B 10.0 g (1.0 eq), 3-chloro-2-(dibenzo[b,d]furan-3-yl)-9,9-dimethyl-9H-indeno[1,2-b]pyrazine 13.73 g (1.1 eq), Pd(t-Bu 3 P) 2 0.16 g (0.01 eq), K 3 PO 4 13.39 g (2.0 eq) were put in 250 ml of xylene, and the mixture was refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 19 (12.17 g, yield 57%). [M+H] + =678
합성예Synthesis example 20 20
화합물 B 10.0 g (1.0 eq), 3-클로로-9,9-디메틸-2-페닐-9H-인데노[1,2-b]피라진 10.61 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), K3PO4 13.39 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 20 10.92 g, 수율 59 %)를 얻었다. [M+H]+=588Compound B 10.0 g (1.0 eq), 3-chloro-9,9-dimethyl-2-phenyl-9H-indeno[1,2-b]pyrazine 10.61 g (1.1 eq), Pd(t-Bu 3 P) 2 0.16 g (0.01 eq), K 3 PO 4 13.39 g (2.0 eq) was put in 250 ml of xylene, and the mixture was refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain 10.92 g of Compound 20, yield 59%). [M+H] + =588
합성예 21Synthesis Example 21
화합물 B 10.0 g (1.0 eq), 3-(9H-카바졸-9-일)-1-클로로벤조[f]퀴나졸린 13.14 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), K3PO4 13.39 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 21 (11.24 g, 수율 54 %)를 얻었다. [M+H]+=661Compound B 10.0 g (1.0 eq), 3-(9H-carbazol-9-yl)-1-chlorobenzo[f]quinazoline 13.14 g (1.1 eq), Pd(t-Bu 3 P) 2 0.16 g ( 0.01 eq), K 3 PO 4 13.39 g (2.0 eq) was put in 250 ml of xylene, and the mixture was refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 21 (11.24 g, yield 54%). [M+H] + =661
합성예 22Synthesis Example 22
화합물 B 10.0 g (1.0 eq), 3-클로로-2-(나프탈렌-2-일)벤조[f]퀴녹살린 11.79 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), K3PO4 13.39 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 22 (11.16 g, 수율 57 %)를 얻었다. [M+H]+=622Compound B 10.0 g (1.0 eq), 3-chloro-2- (naphthalen-2-yl) benzo [f] quinoxaline 11.79 g (1.1 eq), Pd (t-Bu 3 P) 2 0.16 g (0.01 eq) , K 3 PO 4 13.39 g (2.0 eq) was put into 250ml of xylene and refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 22 (11.16 g, yield 57%). [M+H] + =622
합성예 23Synthesis Example 23
화합물 B 10.0 g (1.0 eq), 2-클로로-3-(페닐-d5)퀴녹살린 8.50 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), K3PO4 13.39 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 23 (11.11 g, 수율 67 %)를 얻었다. [M+H]+=527Compound B 10.0 g (1.0 eq), 2-chloro-3-(phenyl-d5)quinoxaline 8.50 g (1.1 eq), Pd(t-Bu 3 P) 2 0.16 g (0.01 eq), K 3 PO 4 13.39 g (2.0 eq) was put into 250ml of xylene, refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 23 (11.11 g, yield 67%). [M+H] + =527
합성예 24Synthesis Example 24
화합물 B 10.0 g (1.0 eq), 2-클로로-3-페닐퀴녹살린 8.32 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), K3PO4 13.39 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 24 (11.34 g, 수율 69 %)를 얻었다. [M+H]+=522Compound B 10.0 g (1.0 eq), 2-chloro-3-phenylquinoxaline 8.32 g (1.1 eq), Pd(t-Bu 3 P) 2 0.16 g (0.01 eq), K 3 PO 4 13.39 g (2.0 eq) ) was put into 250ml of xylene, refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 24 (11.34 g, yield 69%). [M+H] + =522
합성예 25Synthesis Example 25
화합물 B 10.0 g (1.0 eq), 2-(4'-브로모-[1,1'-비페닐]-4-일)-3-(4-(나프탈렌-2-일)페닐)퀴녹살린 19.49 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 25 (17.64 g, 수율 70 %)를 얻었다. [M+H]+=800Compound B 10.0 g (1.0 eq), 2-(4'-bromo-[1,1'-biphenyl]-4-yl)-3-(4-(naphthalen-2-yl)phenyl)quinoxaline 19.49 g (1.1 eq), Pd(t-Bu 3 P) 2 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq) were put in 250 ml of xylene, and the mixture was refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 25 (17.64 g, yield 70%). [M+H] + =800
합성예Synthesis example 26 26
화합물 B 10.0 g (1.0 eq), 3-(4-브로모나프탈렌-1-일)-2-(디벤조[b,d]퓨란-3-일)벤조[4,5]티에노[2,3-b]피라진 19.28 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 26 (18.00 g, 수율 72 %)를 얻었다. [M+H]+=794Compound B 10.0 g (1.0 eq), 3-(4-bromonaphthalen-1-yl)-2-(dibenzo[b,d]furan-3-yl)benzo[4,5]thieno[2, 3-b] Pyrazine 19.28 g (1.1 eq), Pd(t-Bu 3 P) 2 0.16 g (0.01 eq), and NaOtBu 6.06 g (2.0 eq) were added to 250 ml of xylene, and the mixture was refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 26 (18.00 g, yield 72%). [M+H] + =794
합성예 27Synthesis Example 27
화합물 B 10.0 g (1.0 eq), 3-(3-브로모페닐)-2-(디벤조[b,d]티오펜-3-일)벤조[4,5]티에노[2,3-b]피라진 18.10 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 27 (16.03 g, 수율 67 %)를 얻었다. [M+H]+=760Compound B 10.0 g (1.0 eq), 3- (3-bromophenyl) -2- (dibenzo [b, d] thiophen-3-yl) benzo [4,5] thieno [2,3-b ]Pyrazine 18.10 g (1.1 eq), Pd(t-Bu 3 P) 2 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq) were put into 250 ml of xylene, and the mixture was refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 27 (16.03 g, yield 67%). [M+H] + =760
합성예Synthesis example 28 28
화합물 B 10.0 g (1.0 eq), 3-(4-브로모나프탈렌-1-일)-2-(페난쓰렌-2-일)벤조퓨로[2,3-b]피라진 19.08 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 28 (15.88 g, 수율 64 %)를 얻었다. [M+H]+=788Compound B 10.0 g (1.0 eq), 3-(4-bromonaphthalen-1-yl)-2-(phenanthren-2-yl)benzofuro[2,3-b]pyrazine 19.08 g (1.1 eq) , Pd(t-Bu 3 P) 2 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq) were put in 250 ml of xylene, and the mixture was refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 28 (15.88 g, yield 64%). [M+H] + =788
합성예 29Synthesis Example 29
화합물 B 10.0 g (1.0 eq), 3-(3-브로모페닐)-2-(트리페닐렌-2-일)벤조퓨로[2,3-b]피라진 19.08 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 29 (17.62 g, 수율 71 %)를 얻었다. [M+H]+=788Compound B 10.0 g (1.0 eq), 3- (3-bromophenyl) -2- (triphenylen-2-yl) benzofuro [2,3-b] pyrazine 19.08 g (1.1 eq), Pd ( t-Bu 3 P) 2 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq) were put in 250 ml of xylene, and the mixture was refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 29 (17.62 g, yield 71%). [M+H] + =788
합성예 30Synthesis Example 30
화합물 B 10.0 g (1.0 eq), 3-([1,1'-비페닐]-4-일)-2-(4-브로모페닐)벤조[4,5]티에노[2,3-b]피라진 17.06 g (1.1 eq), Pd(t-Bu3P)2 0.16 g (0.01 eq), NaOtBu 6.06 g (2.0 eq)를 자일렌 250ml에 넣어서 환류하여 교반하였다. 2 시간 후 반응이 종료되면 감압하여 용매를 제거하였다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거하였다. 다시 환류 상태에서 에틸아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과하였다. 이를 컬럼크로마토그래피하여 화합물 30 (17.01 g, 수율 74 %)를 얻었다. [M+H]+=730Compound B 10.0 g (1.0 eq), 3-([1,1'-biphenyl]-4-yl)-2-(4-bromophenyl)benzo[4,5]thieno[2,3-b ]Pyrazine 17.06 g (1.1 eq), Pd(t-Bu 3 P) 2 0.16 g (0.01 eq), and NaOtBu 6.06 g (2.0 eq) were put into 250 ml of xylene, and the mixture was refluxed and stirred. When the reaction was completed after 2 hours, the solvent was removed under reduced pressure. After that , it was completely dissolved in CHCl 3 , washed with water, and again under reduced pressure to remove about 50% of the solvent. Again, ethyl acetate was added under reflux, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 30 (17.01 g, yield 74%). [M+H] + =730
<실험예><Experimental example>
비교예 1Comparative Example 1
ITO(indium tin oxide)가 1,000Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(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, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다.A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에 정공주입층으로 하기 HI-1 화합물을 1150Å의 두께로 형성하되 하기 A-1 화합물을 1.5% 농도로 p-도핑 하였다. 상기 정공주입층 위에 하기 HT-1 화합물을 진공 증착하여 막 두께 800Å 의 정공수송층을 형성하였다. 이어서, 상기 정공수송층 위에 막 두께 150Å으로 하기 EB-1 화합물을 진공 증착하여 전자억제층을 형성하였다. 이어서, 상기 EB-1 증착막 위에 하기 RH-1 화합물과 하기 Dp-7 화합물을 98:2의 중량비로 진공 증착하여 400Å 두께의 적색 발광층을 형성하였다. 상기 발광층 위에 막 두께 30Å으로 하기 HB-1 화합물을 진공 증착하여 정공저지층을 형성하였다. 이어서, 상기 정공저지층 위에 하기 ET-1 화합물과 하기 LiQ 화합물을 2:1의 중량비로 진공 증착하여 300Å의 두께로 전자 주입 및 수송층을 형성하였다. 상기 전자 주입 및 수송층 위에 순차적으로 12Å 두께로 리튬플로라이드(LiF)와 1,000Å 두께로 알루미늄을 증착하여 음극을 형성하였다. The following HI-1 compound was formed as a hole injection layer on the thus prepared ITO transparent electrode to a thickness of 1150 Å, but the following compound A-1 was p-doped at a concentration of 1.5%. The following HT-1 compound was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 800 Å. Then, the following EB-1 compound was vacuum-deposited to a thickness of 150 Å on the hole transport layer to form an electron blocking layer. Then, the following RH-1 compound and the following Dp-7 compound were vacuum-deposited on the EB-1 deposited film in a weight ratio of 98:2 to form a red light emitting layer having a thickness of 400 Å. A hole blocking layer was formed by vacuum-depositing the following HB-1 compound to a thickness of 30 Å on the light emitting layer. Then, on the hole blocking layer, the following ET-1 compound and the following LiQ compound were vacuum-deposited at a weight ratio of 2:1 to form an electron injection and transport layer to a thickness of 300 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.
상기의 과정에서 유기물의 증착속도는 0.4~0.7Å/sec를 유지하였고, 음극의 리튬플로라이드는 0.3Å/sec, 알루미늄은 2Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 2×10-7 ~ 5×10-6 torr를 유지하여, 유기 발광 소자를 제작하였다In the above process, the deposition rate of organic material was maintained at 0.4~0.7Å/sec, the deposition rate of lithium fluoride of the negative electrode was maintained at 0.3Å/sec, and the deposition rate of aluminum was maintained at 2Å/sec, and the vacuum degree during deposition was 2×10 - By maintaining 7 to 5×10 -6 torr, an organic light emitting device was manufactured
실시예 1 내지 실시예 30Examples 1 to 30
비교예 1의 유기 발광 소자에서 RH-1 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 비교예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. An organic light emitting device was manufactured in the same manner as in Comparative Example 1, except that the compound shown in Table 1 was used instead of RH-1 in the organic light emitting device of Comparative Example 1.
비교예 2 내지 비교예 21Comparative Examples 2 to 21
비교예 1의 유기 발광 소자에서 RH-1 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 비교예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. An organic light emitting device was manufactured in the same manner as in Comparative Example 1, except that the compound shown in Table 1 was used instead of RH-1 in the organic light emitting device of Comparative Example 1.
[비교예 화합물][Comparative Example Compound]
상기 실시예 1 내지 실시예 30, 및 비교예 1 내지 비교예 21 에서 제조한 유기 발광 소자에 전류를 인가하였을 때, 전압, 효율, 수명을 측정하고 그 결과를 하기 표 1에 나타내었다. T95은 휘도가 초기 휘도(10,000 nit)에서 95%로 감소되는데 소요되는 시간을 의미한다. When a current was applied to the organic light emitting diodes prepared in Examples 1 to 30 and Comparative Examples 1 to 21, voltage, efficiency, and lifetime were measured, and the results are shown in Table 1 below. T95 denotes a time required for the luminance to decrease from the initial luminance (10,000 nits) to 95%.
상기 비교예 1의 적색 유기 발광 소자는 종래 널리 사용되고 있는 물질을 사용하였다. 비교예 2 내지 21은 RH-1 대신 C-1 내지 C-20을 사용하여 유기 발광 소자를 제조하였다. 상기 표 1의 결과를 보면 본 발명의 화합물이 적색 발광층의 호스트로 사용 ?을 때 비교예 물질에 비해서 구동전압이 크게는 20% 가까이 낮아졌으며, 효율 측면에서도 20% 이상 상승을 한 것으로 보아 호스트에서 적색 도펀트로의 에너지 전달이 잘 이뤄진다는 것을 알 수 있었다. 또한 높은 효율을 유지하면서도 수명 특성을 1.5배 이상 크게 개선되는 것을 확인하였다.이것은 결국 본원 발명의 화학식 1의 구조를 만족하지 않거나 (비교예 10 내지 15 및 21), 본원 발명의 Ar을 만족하지 않는 화합물 (비교예 2 내지 21) 보다 본 발명의 화합물이 전자와 정공에 대한 안정도가 높으며 OLED Red 소자내에서 전자와 정공 이동의 균형이 잘 맞기 때문이라 판단 할 수 있다. 결론적으로 본 발명의 화합물을 적색 발광층의 호스트로 사용하였을 때 유기 발광 소자의 구동전압, 발광 효율 및 수명 특성을 개선할 수 있다는 것을 확인할 수 있다.For the red organic light emitting diode of Comparative Example 1, a conventionally widely used material was used. In Comparative Examples 2 to 21, organic light emitting devices were manufactured using C-1 to C-20 instead of RH-1. Looking at the results of Table 1, when the compound of the present invention is used as a host for the red light emitting layer, the driving voltage is largely lowered by nearly 20% compared to the comparative example material, and it is seen that the efficiency is also increased by 20% or more. It was found that the energy transfer to the red dopant was well performed. In addition, it was confirmed that the lifespan characteristics were greatly improved by 1.5 times or more while maintaining high efficiency. This eventually does not satisfy the structure of
1: 기판
2: 제1 전극
3: 발광층
4: 제2 전극
5: 정공주입층
6: 정공수송층
7: 전자수송층
8: 전자억제층
9: 정공저지층
10: 전자주입 및 수송층1: substrate
2: first electrode
3: light emitting layer
4: second electrode
5: hole injection layer
6: hole transport layer
7: electron transport layer
8: electron suppression layer
9: hole blocking layer
10: electron injection and transport layer
Claims (9)
[화학식 1]
화학식 1에 있어서,
X1은 NR, X2는 직접결합; 또는 X1은 직접결합, X2는 NR이며,
A는 벤젠이고,
R은 하기 화학식 2로 표시되고,
[화학식 2]
L은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이며,
Ar은 하기 구조식 중에서 선택되는 어느 하나이고,
R''은 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,
x1는 0 내지 4의 정수이고,
y1는 0 내지 6의 정수이고,
x1 또는 y1이 2 이상인 경우, 괄호 내의 치환기는 서로 같거나 상이하며,
Ra는 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.A compound represented by the following formula (1):
[Formula 1]
In Formula 1,
X1 is NR, X2 is a direct bond; or X1 is a direct bond, X2 is NR,
A is benzene,
R is represented by the following formula (2),
[Formula 2]
L is a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar is any one selected from the following structural formula,
R'' is hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
x1 is an integer from 0 to 4,
y1 is an integer from 0 to 6,
When x1 or y1 is 2 or more, the substituents in parentheses are the same as or different from each other,
Ra is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
상기 화학식 1은 하기 화학식 1-1로 표시되는 것인 화합물:
[화학식 1-1]
상기 화학식 1-1에 있어서,
R은 청구항 1에서의 정의와 같다.The method according to claim 1,
The compound of Formula 1 is represented by the following Formula 1-1:
[Formula 1-1]
In Formula 1-1,
R is as defined in claim 1.
상기 화학식 1은 하기 화학식 1-2로 표시되는 것인 화합물:
[화학식 1-2]
상기 화학식 1-2에 있어서,
R은 청구항 1에서의 정의와 같다.The method according to claim 1,
The compound of Formula 1 is represented by the following Formula 1-2:
[Formula 1-2]
In Formula 1-2,
R is as defined in claim 1.
상기 화학식 1로 표시되는 화합물은 하기 화합물 중에서 선택되는 것인 화합물:
The compound represented by Formula 1 is a compound selected from the following compounds:
상기 유기물층 중 1층 이상은 청구항 1 내지 4 중 어느 하나의 항에 따른 화합물을 포함하는 것인 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,
At least one of the organic material layers is an organic light emitting device comprising the compound according to any one of claims 1 to 4.
상기 유기물층은 발광층을 포함하고,
상기 발광층은 상기 화합물을 포함하는 것인 유기 발광 소자.6. The method of claim 5,
The organic material layer includes a light emitting layer,
The light emitting layer is an organic light emitting device comprising the compound.
상기 유기물층은 정공주입층 또는 정공수송층을 포함하고,
상기 정공주입층 또는 정공수송층은 상기 화합물을 포함하는 것인 유기 발광 소자.6. The method of claim 5,
The organic layer includes a hole injection layer or a hole transport layer,
The hole injection layer or the hole transport layer is an organic light emitting device comprising the compound.
상기 유기물층은 전자수송층 또는 전자주입층을 포함하고,
상기 전자수송층 또는 전자주입층은 상기 화합물을 포함하는 것인 유기 발광 소자.6. The method of claim 5,
The organic layer includes an electron transport layer or an electron injection layer,
The electron transport layer or the electron injection layer is an organic light emitting device comprising the compound.
상기 유기 발광 소자는 정공주입층, 정공수송층, 전자수송층, 전자주입층, 전자주입 및 수송층, 전자억제층 및 정공저지층으로 이루어진 군에서 선택되는 1층 또는 2층 이상을 더 포함하는 것인 유기 발광 소자.6. The method of claim 5,
The organic light emitting device further comprises one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, an electron suppression layer and a hole blocking layer. light emitting element.
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