KR20210156260A - Organic light emitting device - Google Patents
Organic light emitting device Download PDFInfo
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- KR20210156260A KR20210156260A KR1020210179035A KR20210179035A KR20210156260A KR 20210156260 A KR20210156260 A KR 20210156260A KR 1020210179035 A KR1020210179035 A KR 1020210179035A KR 20210179035 A KR20210179035 A KR 20210179035A KR 20210156260 A KR20210156260 A KR 20210156260A
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- KR
- South Korea
- Prior art keywords
- compound
- group
- red
- light emitting
- comparative example
- Prior art date
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- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000007774 positive electrode material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 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
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 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
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Images
Classifications
-
- H01L51/0072—
-
- H01L51/006—
-
- H01L51/5012—
-
- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
Abstract
Description
본 발명은 구동 전압, 효율 및 수명이 개선된 유기 발광 소자에 관한 것이다. The present invention relates to an organic light emitting device having improved driving voltage, efficiency, and lifetime.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기 에너지를 빛 에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 넓은 시야각, 우수한 콘트라스트, 빠른 응답 시간을 가지며, 휘도, 구동 전압 및 응답 속도 특성이 우수하여 많은 연구가 진행되고 있다. In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.
유기 발광 소자는 일반적으로 양극과 음극 및 상기 양극과 음극 사이에 유기물 층을 포함하는 구조를 가진다. 상기 유기물 층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. An organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode. The organic 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, 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. In the structure of the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up.
상기와 같은 유기 발광 소자에서, 구동 전압, 효율 및 수명이 개선된 유기 발광 소자의 개발이 지속적으로 요구되고 있다.In the organic light emitting device as described above, there is a continuous demand for the development of an organic light emitting device having improved driving voltage, efficiency, and lifespan.
본 발명은 구동 전압, 효율 및 수명이 개선된 유기 발광 소자에 관한 것이다. The present invention relates to an organic light emitting device having improved driving voltage, efficiency, and lifetime.
본 발명은 하기의 유기 발광 소자를 제공한다:The present invention provides the following organic light emitting device:
양극, anode,
음극, cathode,
상기 양극과 음극 사이의 발광층을 포함하고, a light emitting layer between the anode and the cathode;
상기 발광층은 하기 화학식 1로 표시되는 화합물 및 하기 화학식 2로 표시되는 화합물을 포함하는,The light emitting layer comprises a compound represented by the following formula (1) and a compound represented by the following formula (2),
유기 발광 소자:Organic light emitting device:
[화학식 1][Formula 1]
상기 화학식 1에서,In Formula 1,
Ar1은 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴이고,Ar 1 is C 2-60 heteroaryl including at least one selected from the group consisting of substituted or unsubstituted N, O and S,
L은 단일결합; 또는 치환 또는 비치환된 C6-60 아릴렌이고,L is a single bond; Or a substituted or unsubstituted C 6-60 arylene,
R1, R2, R3 및 R4는 각각 독립적으로, 수소; 중수소; 할로겐; 시아노; 니트로; 아미노; 치환 또는 비치환된 C1-60 알킬; 치환 또는 비치환된 C3-60 사이클로알킬; 치환 또는 비치환된 C2-60 알케닐; 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴이고, R1, R2, R3 및 R4 중 인접한 둘은 서로 결합하여 C6-60 방향족 고리, 또는 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로방향족 고리를 형성할 수 있고,R 1 , R 2 , R 3 and R 4 are each independently hydrogen; heavy hydrogen; halogen; cyano; nitro; amino; substituted or unsubstituted C 1-60 alkyl; substituted or unsubstituted C 3-60 cycloalkyl; substituted or unsubstituted C 2-60 alkenyl; substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S, R 1 , R 2 , R 3 and R 4 adjacent two are bonded to each other It may form a C 6-60 aromatic ring, or a C 2-60 heteroaromatic ring comprising any one or more selected from the group consisting of N, O and S,
R5, R6, R7 및 R8은 각각 독립적으로, 수소; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴이다.R 5 , R 6 , R 7 and R 8 are each independently hydrogen; Or substituted or unsubstituted C 2-60 heteroaryl comprising any one or more selected from the group consisting of N, O and S.
[화학식 2][Formula 2]
상기 화학식 2에서,In Formula 2,
Ar2 및 Ar3는 각각 독립적으로, 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴이다.Ar 2 and Ar 3 are each independently, substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl comprising any one or more selected from the group consisting of N, O and S.
상술한 유기 발광 소자는, 구동 전압, 효율 및 수명이 우수하다. The above-described organic light emitting device has excellent driving voltage, efficiency, and lifetime.
도 1은, 기판(1), 양극(2), 발광층(3) 및 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.
도 2는, 기판(1), 양극(2), 정공주입층(5) 정공수송층(6), 발광층(4), 정공저지층(7), 전자 주입 및 수송층(8) 및 음극(5)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.FIG. 1 shows an example of an organic light emitting device including a
2 shows a
이하, 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다.Hereinafter, it will be described in more detail to help the understanding of the present invention.
본 명세서에서, 
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 사이클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환 또는 비치환된 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 비페닐기일 수 있다. 즉, 비페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다.As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amino group; a phosphine oxide group; alkoxy group; aryloxy group; alkyl thiooxy group; arylthioxy group; an alkyl sulfoxy group; arylsulfoxy group; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; heteroarylamine group; arylamine group; an arylphosphine group; Or N, O, and S atom means that it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing one or more, or substituted or unsubstituted, two or more of the above-exemplified substituents are linked. . 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 명세서에서 카보닐기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 40인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the number of carbon atoms in the carbonyl group is not particularly limited, but preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
본 명세서에 있어서, 에스테르기는 에스테르기의 산소가 탄소수 1 내지 25의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 25의 아릴기로 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, in the ester group, oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferably from 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
본 명세서에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. However, the present invention is not limited thereto.
본 명세서에 있어서, 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 6이다. 알킬기의 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 사이클로펜틸메틸, 사이클로헥실메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸펜틸, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이들에 한정되지 않는다.In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 10. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group 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 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 6이다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 알릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나 이들에 한정되지 않는다.In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 10. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
본 명세서에 있어서, 사이클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 사이클로프로필, 사이클로부틸, 사이클로펜틸, 3-메틸사이클로펜틸, 2,3-디메틸사이클로펜틸, 사이클로헥실, 3-메틸사이클로헥실, 4-메틸사이클로헥실, 2,3-디메틸사이클로헥실, 3,4,5-트리메틸사이클로헥실, 4-tert-부틸사이클로헥실, 사이클로헵틸, 사이클로옥틸 등이 있으나, 이에 한정되지 않는다.In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. 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, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. 상기 플루오레닐기가 치환되는 경우, 
본 명세서에 있어서, 헤테로고리기는 이종 원소로 O, N, Si 및 S 중 1개 이상을 포함하는 헤테로고리기로서, 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 헤테로고리기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 헤테로고리기의 탄소수는 6 내지 20이다. 헤테로고리기의 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, 벤조옥사졸기, 벤조이미다졸기, 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 heterocyclic group is a heterocyclic group including at least one of O, N, Si and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but it is preferably from 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 6 to 30 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 6 to 20 carbon atoms. Examples of the heterocyclic 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, benzooxazole group, benzoimidazole 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, 아르알킬기, 아르알케닐기, 알킬아릴기, 아릴아민기 중의 아릴기는 전술한 아릴기의 예시와 같다. 본 명세서에 있어서, 아르알킬기, 알킬아릴기, 알킬아민기 중 알킬기는 전술한 알킬기의 예시와 같다. 본 명세서에 있어서, 헤테로아릴아민 중 헤테로아릴은 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 아르알케닐기 중 알케닐기는 전술한 알케닐기의 예시와 같다. 본 명세서에 있어서, 아릴렌은 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로아릴렌은 2가기인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 탄화수소 고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 아릴기 또는 사이클로알킬기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다.In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group is the same as the examples of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the above-described alkyl group. In the present specification, the description of the heterocyclic group described above for heteroaryl among heteroarylamines may be applied. In the present specification, the alkenyl group among the aralkenyl groups is the same as the above-described examples of the alkenyl group. In the present specification, the description of the above-described aryl group may be applied, except that arylene is a divalent group. In the present specification, the description of the above-described heterocyclic group may be applied, except that heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the above-described aryl group or cycloalkyl group may be applied, except that it is formed by combining two substituents. In the present specification, the heterocyclic group is not a monovalent group, and the description of the above-described heterocyclic group may be applied, except that it is formed by combining two substituents.
이하, 각 구성 별로 본 발명을 상세히 설명한다. Hereinafter, the present invention will be described in detail for each configuration.
양극 및 음극positive and negative
본 발명에서 사용되는 양극 및 음극은, 유기 발광 소자에서 사용되는 전극을 의미한다. The anode and cathode used in the present invention mean electrodes used in an organic light emitting device.
상기 양극 물질로는 통상 유기물 층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 상기 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. As the anode material, 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 anode material 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); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 상기 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다. The cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multi-layered material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
정공주입층hole injection layer
본 발명에 따른 유기 발광 소자는, 상기 양극과 후술할 정공수송층 사이에 정공주입층을 추가로 포함할 수 있다. The organic light emitting diode according to the present invention may further include a hole injection layer between the anode and a hole transport layer to be described later.
상기 정공 주입 물질로는 전극으로부터 정공을 주입하는 층으로, 정공 주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입효과, 발광층 또는 발광재료에 대하여 우수한 정공 주입 효과를 갖고, 발광층에서 생성된 여기자의 전자주입층 또는 전자주입재료에의 이동을 방지하며, 또한, 박막 형성 능력이 우수한 화합물이 바람직하다. 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물 층의 HOMO 사이인 것이 바람직하다. The hole injection material is a layer for injecting holes from the electrode, and the hole injection material has the ability to transport holes, so it has a hole injection effect at the anode, an excellent hole injection effect on the light emitting layer or the light emitting material, and is generated in the light emitting layer A compound that prevents the excitons from moving to the electron injection layer or the electron injection material and is excellent in the ability to form a thin film is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
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. 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. organic materials, anthraquinone, polyaniline and polythiophene-based conductive polymers, and the like, but are not limited thereto.
정공수송층hole transport layer
본 발명에서 사용되는 정공수송층은 양극 또는 양극 상에 형성된 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 정공 수송 물질로 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. The hole transport layer used in the present invention is a layer that receives holes from the hole injection layer formed on the anode or the anode and transports them to the light emitting layer. As a material with high hole mobility, it is suitable.
정공 수송 물질의 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. Specific examples of the hole transport material 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.
발광층light emitting layer
본 발명에서 사용되는 발광층은, 양극과 음극으로부터 전달받은 정공과 전자를 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 층으로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. The light emitting layer used in the present invention is a layer capable of emitting light in the visible ray region by combining the holes and electrons transferred from the anode and the cathode, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
일반적으로, 발광층은 호스트 재료와 도펀트 재료를 포함하며, 상기 화학식 1 및 상기 화학식 2로 표시되는 화합물을 호스트로 포함할 수 있다.In general, the emission layer includes a host material and a dopant material, and may include the compound represented by
바람직하게는, 상기 화학식 1은 하기 화학식 1-1 내지 화학식 1-3 중 어느 하나로 표시될 수 있다:Preferably,
[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
[화학식 1-3][Formula 1-3]
상기 화학식 1-1 내지 화학식 1-3에서,In Formulas 1-1 to 1-3,
Ar1, L, R5, R6, R7 및 R8에 대한 설명은 상기 화학식 1에서 정의한 바와 같다.Ar 1 , L, R 5 , R 6 , R 7 and R 8 are the same as defined in
바람직하게는, Ar1은 치환 또는 비치환된 2 이상의 N을 포함하는 C2-60 헤테로아릴일 수 있고, 보다 바람직하게는, Ar1은 치환 또는 비치환된 2 이상의 N을 포함하는 C2-20 헤테로아릴일 수 있고, 보다 바람직하게는, Ar1은 치환 또는 비치환된 퀴나졸리닐, 또는 치환 또는 비치환된 퀴녹살리닐일 수 있고, 가장 바람직하게는, Ar1은 하기로 구성되는 군으로부터 선택되는 어느 하나일 수 있다:Preferably, Ar 1 may be substituted or unsubstituted C 2-60 heteroaryl containing 2 or more N, and more preferably, Ar 1 is substituted or unsubstituted C 2 - containing 2 or more Ns. 20 heteroaryl, more preferably, Ar 1 may be substituted or unsubstituted quinazolinyl, or substituted or unsubstituted quinoxalinyl, and most preferably, Ar 1 is selected from the group consisting of It may be any one selected:
바람직하게는, L은 단일결합; 또는 치환 또는 비치환된 C6-20 아릴렌일 수 있고, 보다 바람직하게는, L은 단일결합일 수 있다.Preferably, L is a single bond; Or it may be a substituted or unsubstituted C 6-20 arylene, more preferably, L may be a single bond.
바람직하게는, R1, R2, R3 및 R4 중 인접한 둘은 서로 결합하여 벤젠 고리를 형성할 수 있다.Preferably , adjacent two of R 1 , R 2 , R 3 and R 4 may combine with each other to form a benzene ring.
바람직하게는, R5, R6, R7 및 R8은 각각 독립적으로, 수소; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-20 헤테로아릴일 수 있고, 보다 바람직하게는, R5, R6, R7 및 R8은 각각 독립적으로, 수소 또는 카바졸릴일 수 있고, 상기 카바졸릴은 비치환되거나, 페닐, 비페닐릴, 나프틸, 나프틸 페닐, 및 페닐 나프틸 중 어느 하나로 치환될 수 있고, 가장 바람직하게는, R5, R6, R7 및 R8은 각각 독립적으로, 수소 또는 하기로 구성되는 군으로부터 선택되는 어느 하나일 수 있다:Preferably, R 5 , R 6 , R 7 and R 8 are each independently hydrogen; Or it may be a C 2-20 heteroaryl comprising at least one selected from the group consisting of substituted or unsubstituted N, O and S, and more preferably, R 5 , R 6 , R 7 and R 8 . may be each independently hydrogen or carbazolyl, and the carbazolyl may be unsubstituted or substituted with any one of phenyl, biphenylyl, naphthyl, naphthyl phenyl, and phenyl naphthyl, most preferably , R 5 , R 6 , R 7 and R 8 may each independently be hydrogen or any one selected from the group consisting of:
바람직하게는, R5, R6, R7 및 R8 중 적어도 하나는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-20 헤테로아릴일 수 있고, 보다 바람직하게는, R5, R6, R7 및 R8 중 적어도 하나는 치환 또는 비치환된 카바졸릴일 수 있다.Preferably , at least one of R 5 , R 6 , R 7 and R 8 may be C 2-20 heteroaryl including at least one selected from the group consisting of substituted or unsubstituted N, O and S and, more preferably , at least one of R 5 , R 6 , R 7 and R 8 may be a substituted or unsubstituted carbazolyl.
상기 화학식 1로 표시되는 화합물의 대표적인 예는 다음과 같다:Representative examples of the compound represented by
상기 화학식 1로 표시되는 화합물은, 일례로 하기 반응식 1-1과 같은 제조 방법으로 제조할 수 있으며, R5, R6 및 R8이 수소이고, R7이 카바졸인 경우, 일례로 하기 반응식 1-2와 같은 제조 방법으로 제조할 수 있으며, 그 외 나머지 화합물도 유사하게 제조할 수 있다.The compound represented by
[반응식 1-1][Scheme 1-1]
[반응식 1-2][Scheme 1-2]
상기 반응식 1-1 및 1-2에서, Ar1, L 및 R1 내지 R8은 상기 화학식 1에서 정의한 바와 같으며, X1 및 X2는 각각 독립적으로, 할로겐이고, 바람직하게는 X1 및 X2는 각각 독립적으로, 클로로 또는 브로모이다.In Schemes 1-1 and 1-2, Ar 1 , L and R 1 to R 8 are as defined in
상기 반응식 1-1 및 1-2는 아민 치환 반응으로서, 팔라듐 촉매와 염기 존재 하에 수행하는 것이 바람직하며, 아민 치환 반응을 위한 반응기는 당업계에 알려진 바에 따라 변경이 가능하다. 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다.Schemes 1-1 and 1-2 are amine substitution reactions, preferably performed in the presence of a palladium catalyst and a base, and the reactor for the amine substitution reaction can be changed as known in the art. The manufacturing method may be more specific in Preparation Examples to be described later.
바람직하게는, Ar2 및 Ar3는 각각 독립적으로, 치환 또는 비치환된 C6-20 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-20 헤테로아릴일 수 있고, 보다 바람직하게는, Ar2 및 Ar3는 각각 독립적으로, 치환 또는 비치환된 C6-20 아릴일 수 있고, 가장 바람직하게는, Ar2 및 Ar3는 각각 독립적으로, 페닐, 비페닐릴, 터페닐릴, 디메틸 플루오레닐, 나프틸, 나프틸 페닐, 또는 페닐 나프틸일 수 있다.Preferably, Ar 2 and Ar 3 are each independently selected from substituted or unsubstituted C 6-20 aryl; Or it may be a C 2-20 heteroaryl comprising at least one selected from the group consisting of substituted or unsubstituted N, O and S, and more preferably, Ar 2 and Ar 3 are each independently, substituted or unsubstituted C 6-20 aryl, most preferably, Ar 2 and Ar 3 are each independently phenyl, biphenylyl, terphenylyl, dimethyl fluorenyl, naphthyl, naphthyl phenyl; or phenyl naphthyl.
상기 화학식 2로 표시되는 화합물의 대표적인 예는 다음과 같다:Representative examples of the compound represented by
상기 화학식 2로 표시되는 화합물은 일례로 하기 반응식 2와 같은 제조 방법으로 제조할 수 있으며, 그 외 나머지 화합물도 유사하게 제조할 수 있다.The compound represented by
[반응식 2][Scheme 2]
상기 반응식 2에서, Ar2 및 Ar3는 상기 화학식 2에서 정의한 바와 같으며, X3는 할로겐이고, 바람직하게는 X3는 클로로 또는 브로모이다.In
상기 반응식 2는 아민 치환 반응으로서, 팔라듐 촉매와 염기 존재 하에 수행하는 것이 바람직하며, 아민 치환 반응을 위한 반응기는 당업계에 알려진 바에 따라 변경이 가능하다. 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다.
바람직하게는, 상기 발광층에서 상기 화학식 1로 표시되는 화합물 및 상기 화학식 2로 표시되는 화합물의 중량비는 10:90 내지 90:10이고, 보다 바람직하게는 20:80 내지 80:20, 30:70 내지 70:30 또는 40:60 내지 60:40이다. Preferably, the weight ratio of the compound represented by
한편, 상기 발광층은 호스트 외에 도펀트를 추가로 포함할 수 있다. 상기 도펀트 재료로는 유기 발광 소자에 사용되는 물질이면 특별히 제한되지 않는다. 일례로, 방향족 아민 유도체, 스트릴아민 화합물, 붕소 착체, 플루오란텐 화합물, 금속 착체 등이 있다. 구체적으로 방향족 아민 유도체로는 치환 또는 비치환된 아릴아미노기를 갖는 축합 방향족환 유도체로서, 아릴아미노기를 갖는 피렌, 안트라센, 크리센, 페리플란텐 등이 있으며, 스티릴아민 화합물로는 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로, 아릴기, 실릴기, 알킬기, 사이클로알킬기 및 아릴아미노기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민, 스티릴디아민, 스티릴트리아민, 스티릴테트라아민 등이 있으나, 이에 한정되지 않는다. 또한, 금속 착체로는 이리듐 착체, 백금 착체 등이 있으나, 이에 한정되지 않는다.Meanwhile, the light emitting layer may further include a dopant in addition to the host. The dopant material is not particularly limited as long as it is a material used in an organic light emitting device. Examples include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periflanthene, and the like, having an arylamino group. As the styrylamine compound, a substituted or unsubstituted It is a compound in which at least one arylvinyl group is substituted in the arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but is not limited thereto. In addition, examples of the metal complex include, but are not limited to, an iridium complex and a platinum complex.
일례로, 도펀트 재료로 사용될 수 있는 대표적인 화합물은 아래와 같다:As an example, representative compounds that can be used as dopant materials are as follows:
정공저지층hole blocking layer
상기 정공저지층은 양극에서 주입된 정공이 발광층에서 재결합되지 않고 전자수송층으로 넘어가는 것을 방지하기 위해 전자수송층과 발광층의 사이에 두는 층으로, 정공억제층 또는 정공차단층으로 불리기도 한다. 정공저지층에는 이온화에너지가 큰 물질이 바람직하다.The hole blocking layer is a layer placed between the electron transport layer and the light emitting layer to prevent the holes injected from the anode from passing to the electron transport layer without recombination in the light emitting layer, and is also called a hole blocking layer or a hole blocking layer. A material having high ionization energy is preferable for the hole blocking layer.
전자수송층electron transport layer
본 발명에 따른 유기 발광 소자는, 상기 발광층과 음극 사이에 전자수송층을 포함할 수 있다. The organic light emitting device according to the present invention may include an electron transport layer between the light emitting layer and the cathode.
상기 전자수송층은, 음극 또는 음극 상에 형성된 전자주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하고, 또한 발광층에서 정공이 전달되는 것을 억제하는 층으로, 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. The electron transport layer is a layer that receives electrons from the electron injection layer formed on the cathode or the cathode, transports electrons to the light emitting layer, and suppresses the transfer of holes in the light emitting layer. As an electron transport material, electrons are well injected from the cathode As a material that can receive and transfer to the light emitting layer, a material with high electron mobility is suitable. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high electron mobility is suitable.
상기 전자 수송 물질의 구체적인 예로는 8-히드록시퀴놀린의 Al 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이 임의의 원하는 캐소드 물질과 함께 사용할 수 있다. 특히, 적절한 캐소드 물질의 예는 낮은 일함수를 가지고 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로 세슘, 바륨, 칼슘, 이테르븀 및 사마륨이고, 각 경우 알루미늄 층 또는 실버층이 뒤따른다.Specific examples of the electron transport material include an Al complex of 8-hydroxyquinoline; complexes containing Alq 3 ; 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.
전자주입층electron injection layer
본 발명에 따른 유기 발광 소자는 상기 전자수송층과 음극 사이에 전자주입층을 추가로 포함할 수 있다. 상기 전자주입층은 전극으로부터 전자를 주입하는 층으로, 전자를 수송하는 능력을 갖고, 음극으로부터의 전자 주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공주입층에의 이동을 방지하고, 또한, 박막형성능력이 우수한 화합물이 바람직하다. The organic light emitting diode according to the present invention may further include an electron injection layer between the electron transport layer and the cathode. 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 cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer. A compound which prevents movement to a layer and is excellent in the ability to form a thin film is preferable.
상기 전자주입층으로 사용될 수 있는 물질의 구체적인 예로는, 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 질소 함유 5원환 유도체 등이 있으나, 이에 한정되지 않는다. Specific examples of the material that can be used as the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preole nylidene methane, anthrone and the like, derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
상기 금속 착체 화합물로서는 8-하이드록시퀴놀리나토 리튬, 비스(8-하이드록시퀴놀리나토)아연, 비스(8-하이드록시퀴놀리나토)구리, 비스(8-하이드록시퀴놀리나토)망간, 트리스(8-하이드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-하이드록시퀴놀리나토)알루미늄, 트리스(8-하이드록시퀴놀리나토)갈륨, 비스(10-하이드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-하이드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되지 않는다.Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( 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.
유기 발광 소자organic light emitting device
본 발명에 따른 유기 발광 소자의 구조를 도 1 및 도 2에 예시하였다. 도 1은, 기판(1), 양극(2), 발광층(3) 및 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 도 2는, 기판(1), 양극(2), 정공주입층(5) 정공수송층(6), 발광층(4), 정공저지층(7), 전자 주입 및 수송층(8) 및 음극(5)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.The structure of the organic light emitting device according to the present invention is illustrated in FIGS. 1 and 2 . FIG. 1 shows an example of an organic light emitting device including a
본 발명에 따른 유기 발광 소자는 상술한 구성을 순차적으로 적층시켜 제조할 수 있다. 이때, 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(physical Vapor Deposition)방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 상술한 각 층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시켜 제조할 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수 있다. 또한, 발광층은 호스트 및 도펀트를 진공 증착법 뿐만 아니라 용액 도포법에 의하여 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.The organic light emitting device according to the present invention may be manufactured by sequentially stacking the above-described components. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode And, after forming each of the above-mentioned layers thereon, it can be prepared by depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. In addition, the light emitting layer may be formed by a solution coating method as well as a vacuum deposition method for the host and dopant. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
이와 같은 방법 외에도, 기판 상에 음극 물질로부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 제조할 수 있다(WO 2003/012890). 다만, 제조 방법이 이에 한정되는 것은 아니다. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
한편, 본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.On the other hand, the organic light emitting device according to the present invention may be a top emission type, a back emission type, or a double-sided emission type depending on the material used.
이하, 본 발명의 이해를 돕기 위하여 바람직한 실시예를 제시한다. 그러나 하기의 실시예는 본 발명을 보다 쉽게 이해하기 위하여 제공되는 것일 뿐, 이에 의해 본 발명의 내용이 한정되는 것은 아니다.Hereinafter, preferred examples are presented to help the understanding of the present invention. However, the following examples are only provided for easier understanding of the present invention, and thus the content of the present invention is not limited thereto.
제조예 1: 화합물 1의 제조Preparation Example 1: Preparation of
질소 분위기에서 중간체 1-1(20 g, 83.3 mmol), 중간체 1-2(38.2 g, 83.3 mmol), tripotassium phosphate(35.4 g, 166.6 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.9 g, 1.7 mmol)을 투입했다. 2 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 1(35.3 g, 수율 64 %, MS: [M+H]+= 663)을 얻었다.In a nitrogen atmosphere, Intermediate 1-1 (20 g, 83.3 mmol), Intermediate 1-2 (38.2 g, 83.3 mmol), and tripotassium phosphate (35.4 g, 166.6 mmol) were added to 400 ml of Xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0)(0.9 g, 1.7 mmol) was added. After 2 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reducing the pressure. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 1 (35.3 g, yield 64%, MS: [M+H]+= 663).
제조예 2: 화합물 2의 제조Preparation Example 2: Preparation of
질소 분위기에서 중간체 2-1(20 g, 83.3 mmol), 중간체 2-2(38.2 g, 83.3 mmol), tripotassium phosphate(35.4 g, 166.6 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.9 g, 1.7 mmol)을 투입했다. 2 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 2(37.5 g, 수율 68 %, MS: [M+H]+= 663)을 얻었다.In a nitrogen atmosphere, Intermediate 2-1 (20 g, 83.3 mmol), Intermediate 2-2 (38.2 g, 83.3 mmol), and tripotassium phosphate (35.4 g, 166.6 mmol) were added to 400 ml of Xylene, and stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0)(0.9 g, 1.7 mmol) was added. After 2 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reducing the pressure. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 2 (37.5 g, yield 68%, MS: [M+H]+=663).
제조예 3: 화합물 3의 제조Preparation Example 3: Preparation of
질소 분위기에서 중간체 3-1(20 g, 83.3 mmol), 중간체 3-2(44.5 g, 83.3 mmol), tripotassium phosphate(35.4 g, 166.6 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.9 g, 1.7 mmol)을 투입했다. 3 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 3(33.2 g, 수율 54 %, MS: [M+H]+= 739)을 얻었다.In a nitrogen atmosphere, Intermediate 3-1 (20 g, 83.3 mmol), Intermediate 3-2 (44.5 g, 83.3 mmol), and tripotassium phosphate (35.4 g, 166.6 mmol) were added to 400 ml of Xylene, and stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0)(0.9 g, 1.7 mmol) was added. After 3 hours, the reaction was terminated, and the solvent was removed under reduced pressure after cooling to room temperature. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 3 (33.2 g, yield 54%, MS: [M+H]+= 739).
제조예 4: 화합물 4의 제조Preparation Example 4: Preparation of
질소 분위기에서 중간체 4-1(20 g, 83.3 mmol), 중간체 4-2(44.5 g, 83.3 mmol), tripotassium phosphate(35.4 g, 166.6 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.9 g, 1.7 mmol)을 투입했다. 2 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 4(33.8g, 수율 55 %, MS: [M+H]+= 739)을 얻었다.In a nitrogen atmosphere, Intermediate 4-1 (20 g, 83.3 mmol), Intermediate 4-2 (44.5 g, 83.3 mmol), and tripotassium phosphate (35.4 g, 166.6 mmol) were added to 400 ml of Xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0)(0.9 g, 1.7 mmol) was added. After 2 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reducing the pressure. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 4 (33.8 g, yield 55%, MS: [M+H]+= 739).
제조예 5: 화합물 5의 제조Preparation Example 5: Preparation of
질소 분위기에서 중간체 5-1(20 g, 83.3 mmol), 중간체 5-2(48.7 g, 83.3 mmol), tripotassium phosphate(35.4 g, 166.6 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.9 g, 1.7 mmol)을 투입했다. 2 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 5(33.5 g, 수율 51 %, MS: [M+H]+= 789)을 얻었다.In a nitrogen atmosphere, Intermediate 5-1 (20 g, 83.3 mmol), Intermediate 5-2 (48.7 g, 83.3 mmol), and tripotassium phosphate (35.4 g, 166.6 mmol) were added to 400 ml of Xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0)(0.9 g, 1.7 mmol) was added. After 2 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reducing the pressure. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 5 (33.5 g, yield 51%, MS: [M+H]+=789).
제조예 6: 화합물 6의 제조Preparation Example 6: Preparation of
질소 분위기에서 중간체 6-1(20 g, 43.9 mmol), 중간체 6-2(7.3 g, 43.9 mmol), sodium tert-butoxide(8.4 g, 87.9 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.4 g, 0.9 mmol)을 투입했다. 2 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 6(13.4 g, 수율 52 %, MS: [M+H]+= 587)을 얻었다.In a nitrogen atmosphere, Intermediate 6-1 (20 g, 43.9 mmol), Intermediate 6-2 (7.3 g, 43.9 mmol), and sodium tert-butoxide (8.4 g, 87.9 mmol) were added to 400 ml of Xylene, and stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0)(0.4 g, 0.9 mmol) was added. After 2 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reducing the pressure. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 6 (13.4 g, yield 52%, MS: [M+H]+=587).
제조예 7: 화합물 7의 제조Preparation Example 7: Preparation of
질소 분위기에서 중간체 7-1(20 g, 69 mmol), 중간체 7-2(35 g, 69 mmol), tripotassium phosphate(29.3 g, 137.9 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.7 g, 1.4 mmol)을 투입했다. 2 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 7(35.2 g, 수율 67 %, MS: [M+H]+= 763)을 얻었다.In a nitrogen atmosphere, Intermediate 7-1 (20 g, 69 mmol), Intermediate 7-2 (35 g, 69 mmol), and tripotassium phosphate (29.3 g, 137.9 mmol) were added to 400 ml of Xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0)(0.7 g, 1.4 mmol) was added. After 2 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reducing the pressure. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 7 (35.2 g, yield 67%, MS: [M+H]+=763).
제조예 8: 화합물 8의 제조Preparation 8: Preparation of
질소 분위기에서 중간체 8-1(20 g, 54.6 mmol), 중간체 8-2(29.2 g, 54.6 mmol), tripotassium phosphate(23.2 g, 109.3 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.6 g, 1.1 mmol)을 투입했다. 2 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 8(27.4 g, 수율 58 %, MS: [M+H]+= 865)을 얻었다.In a nitrogen atmosphere, Intermediate 8-1 (20 g, 54.6 mmol), Intermediate 8-2 (29.2 g, 54.6 mmol), and tripotassium phosphate (23.2 g, 109.3 mmol) were added to 400 ml of Xylene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.1 mmol) was added thereto. After 2 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reducing the pressure. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 8 (27.4 g, yield 58%, MS: [M+H]+= 865).
제조예 9: 화합물 9의 제조Preparation Example 9: Preparation of compound 9
질소 분위기에서 중간체 9-1(20 g, 69 mmol), 중간체 9-2(40.3 g, 69 mmol), tripotassium phosphate(29.3 g, 137.9 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.7 g, 1.4 mmol)을 투입했다. 3 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 9(32.9 g, 수율 57 %, MS: [M+H]+= 839)을 얻었다.In a nitrogen atmosphere, Intermediate 9-1 (20 g, 69 mmol), Intermediate 9-2 (40.3 g, 69 mmol), and tripotassium phosphate (29.3 g, 137.9 mmol) were added to 400 ml of Xylene, and stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0)(0.7 g, 1.4 mmol) was added. After 3 hours, the reaction was terminated, and the solvent was removed under reduced pressure after cooling to room temperature. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 9 (32.9 g, yield 57%, MS: [M+H] + = 839).
제조예 10: 화합물 10의 제조Preparation 10: Preparation of compound 10
질소 분위기에서 중간체 10-1(20 g, 39.6 mmol), 중간체 10-2(6.6 g, 39.6 mmol), sodium tert-butoxide(7.6 g, 79.2 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.4 g, 0.8 mmol)을 투입했다. 2 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물10(14.1 g, 수율 56 %, MS: [M+H]+= 637)을 얻었다.In a nitrogen atmosphere, Intermediate 10-1 (20 g, 39.6 mmol), Intermediate 10-2 (6.6 g, 39.6 mmol), and sodium tert-butoxide (7.6 g, 79.2 mmol) were added to 400 ml of Xylene, and stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0)(0.4 g, 0.8 mmol) was added. After 2 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reducing the pressure. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 10 (14.1 g, yield 56 %, MS: [M+H] + = 637).
제조예 11: 화합물 11의 제조Preparation 11: Preparation of compound 11
질소 분위기에서 중간체 11-1(20 g, 54.6 mmol), 중간체 11-2(25 g, 54.6 mmol), tripotassium phosphate(23.2 g, 109.3 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.6 g, 1.1 mmol)을 투입했다. 3 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 11(21.5 g, 수율 50 %, MS: [M+H]+= 789)을 얻었다.In a nitrogen atmosphere, Intermediate 11-1 (20 g, 54.6 mmol), Intermediate 11-2 (25 g, 54.6 mmol), and tripotassium phosphate (23.2 g, 109.3 mmol) were added to 400 ml of Xylene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.1 mmol) was added thereto. After 3 hours, the reaction was terminated, and the solvent was removed under reduced pressure after cooling to room temperature. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 11 (21.5 g, yield 50%, MS: [M+H]+= 789).
제조예 12: 화합물 12의 제조Preparation 12: Preparation of compound 12
질소 분위기에서 중간체 12-1(20 g, 54.6 mmol), 중간체 12-2(27.8 g, 54.6 mmol), tripotassium phosphate(23.2 g, 109.3 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.6 g, 1.1 mmol)을 투입했다. 2 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 12(29.3 g, 수율 64 %, MS: [M+H]+= 839)을 얻었다.In a nitrogen atmosphere, Intermediate 12-1 (20 g, 54.6 mmol), Intermediate 12-2 (27.8 g, 54.6 mmol), and tripotassium phosphate (23.2 g, 109.3 mmol) were added to 400 ml of Xylene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 1.1 mmol) was added thereto. After 2 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reducing the pressure. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 12 (29.3 g, yield 64%, MS: [M+H]+= 839).
제조예 13: 화합물 13의 제조Preparation 13: Preparation of compound 13
질소 분위기에서 중간체 13-1(20 g, 63.3 mmol), 중간체 13-2(33.8 g, 63.3 mmol), tripotassium phosphate(26.9 g, 126.6 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.6 g, 1.3 mmol)을 투입했다. 3 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 13(31.9 g, 수율 62 %, MS: [M+H]+= 815)을 얻었다.In a nitrogen atmosphere, Intermediate 13-1 (20 g, 63.3 mmol), Intermediate 13-2 (33.8 g, 63.3 mmol), and tripotassium phosphate (26.9 g, 126.6 mmol) were added to 400 ml of Xylene, stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0)(0.6 g, 1.3 mmol) was added. After 3 hours, the reaction was terminated, and the solvent was removed under reduced pressure after cooling to room temperature. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 13 (31.9 g, yield 62%, MS: [M+H]+= 815).
제조예 14: 화합물 14의 제조Preparation 14: Preparation of compound 14
질소 분위기에서 중간체 14-1(20 g, 63.3 mmol), 중간체 14-2(33.8 g, 63.3 mmol), tripotassium phosphate(26.9 g, 126.6 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.6 g, 1.3 mmol)을 투입했다. 2 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 14(25.8 g, 수율 50 %, MS: [M+H]+= 815)을 얻었다.In a nitrogen atmosphere, Intermediate 14-1 (20 g, 63.3 mmol), Intermediate 14-2 (33.8 g, 63.3 mmol), and tripotassium phosphate (26.9 g, 126.6 mmol) were added to 400 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0)(0.6 g, 1.3 mmol) was added. After 2 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reducing the pressure. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 14 (25.8 g, yield 50%, MS: [M+H]+= 815).
제조예 15: 화합물 15의 제조Preparation 15: Preparation of compound 15
질소 분위기에서 중간체 15-1(20 g, 37.7 mmol), 중간체 15-2(6.3 g, 37.7 mmol), sodium tert-butoxide(7.2 g, 75.3 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.4 g, 0.8 mmol)을 투입했다. 3 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 15(17 g, 수율 68 %, MS: [M+H]+= 663)을 얻었다.In a nitrogen atmosphere, Intermediate 15-1 (20 g, 37.7 mmol), Intermediate 15-2 (6.3 g, 37.7 mmol), and sodium tert-butoxide (7.2 g, 75.3 mmol) were added to 400 ml of Xylene, and stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0)(0.4 g, 0.8 mmol) was added. After 3 hours, the reaction was terminated, and the solvent was removed under reduced pressure after cooling to room temperature. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 15 (17 g, yield 68%, MS: [M+H]+=663).
제조예 16: 화합물 16의 제조Preparation 16: Preparation of compound 16
질소 분위기에서 중간체 16-1(20 g, 50.8 mmol), 중간체 16-2(16.3 g, 50.8 mmol), sodium tert-butoxide(9.8 g, 101.5 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.5 g, 1 mmol)을 투입했다. 3 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 16(19.3 g, 수율 60 %, MS: [M+H]+= 636)을 얻었다.In a nitrogen atmosphere, Intermediate 16-1 (20 g, 50.8 mmol), Intermediate 16-2 (16.3 g, 50.8 mmol), and sodium tert-butoxide (9.8 g, 101.5 mmol) were added to 400 ml of Xylene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1 mmol) was added. After 3 hours, the reaction was terminated, and the solvent was removed under reduced pressure after cooling to room temperature. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 16 (19.3 g, yield 60%, MS: [M+H]+= 636).
제조예 17: 화합물 17의 제조Preparation 17: Preparation of compound 17
질소 분위기에서 중간체 17-1(20 g, 50.8 mmol), 중간체 17-2(20.2 g, 50.8 mmol), sodium tert-butoxide(9.8 g, 101.5 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.5 g, 1 mmol)을 투입했다. 3 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 17(19.5 g, 수율 54 %, MS: [M+H]+= 712)을 얻었다.In a nitrogen atmosphere, Intermediate 17-1 (20 g, 50.8 mmol), Intermediate 17-2 (20.2 g, 50.8 mmol), and sodium tert-butoxide (9.8 g, 101.5 mmol) were added to 400 ml of Xylene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1 mmol) was added. After 3 hours, the reaction was terminated, and the solvent was removed under reduced pressure after cooling to room temperature. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 17 (19.5 g, yield 54%, MS: [M+H]+=712).
제조예 18: 화합물 18의 제조Preparation 18: Preparation of compound 18
질소 분위기에서 중간체 18-1(20 g, 50.8 mmol), 중간체 18-2(18.3 g, 50.8 mmol), sodium tert-butoxide(9.8 g, 101.5 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.5 g, 1 mmol)을 투입했다. 2 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 18(18.9 g, 수율 55 %, MS: [M+H]+= 676)을 얻었다.In a nitrogen atmosphere, Intermediate 18-1 (20 g, 50.8 mmol), Intermediate 18-2 (18.3 g, 50.8 mmol), and sodium tert-butoxide (9.8 g, 101.5 mmol) were added to 400 ml of Xylene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1 mmol) was added. After 2 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reducing the pressure. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 18 (18.9 g, yield 55%, MS: [M+H]+= 676).
제조예 19: 화합물 19의 제조Preparation 19: Preparation of compound 19
질소 분위기에서 중간체 19-1(20 g, 50.8 mmol), 중간체 19-2(18.3 g, 50.8 mmol), sodium tert-butoxide(9.8 g, 101.5 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.5 g, 1 mmol)을 투입했다. 2 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 19(18.5 g, 수율 54 %, MS: [M+H]+= 676)을 얻었다.In a nitrogen atmosphere, Intermediate 19-1 (20 g, 50.8 mmol), Intermediate 19-2 (18.3 g, 50.8 mmol), and sodium tert-butoxide (9.8 g, 101.5 mmol) were added to 400 ml of Xylene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1 mmol) was added. After 2 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reducing the pressure. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 19 (18.5 g, yield 54%, MS: [M+H]+= 676).
제조예 20: 화합물 20의 제조Preparation 20: Preparation of compound 20
질소 분위기에서 중간체 20-1(20 g, 50.8 mmol), 중간체 20-2(20.4 g, 50.8 mmol), sodium tert-butoxide(9.8 g, 101.5 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.5 g, 1 mmol)을 투입했다. 2 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 20(23.6 g, 수율 65 %, MS: [M+H]+= 716)을 얻었다.In a nitrogen atmosphere, Intermediate 20-1 (20 g, 50.8 mmol), Intermediate 20-2 (20.4 g, 50.8 mmol), and sodium tert-butoxide (9.8 g, 101.5 mmol) were added to 400 ml of Xylene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1 mmol) was added. After 2 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reducing the pressure. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 20 (23.6 g, yield 65%, MS: [M+H]+= 716).
제조예 21: 화합물 21의 제조Preparation 21: Preparation of compound 21
질소 분위기에서 중간체 21-1(20 g, 50.8 mmol), 중간체 21-2(18.8 g, 50.8 mmol), sodium tert-butoxide(9.8 g, 101.5 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.5 g, 1 mmol)을 투입했다. 3 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 21(20.5 g, 수율 59 %, MS: [M+H]+= 686)을 얻었다.In a nitrogen atmosphere, Intermediate 21-1 (20 g, 50.8 mmol), Intermediate 21-2 (18.8 g, 50.8 mmol), and sodium tert-butoxide (9.8 g, 101.5 mmol) were added to 400 ml of Xylene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1 mmol) was added. After 3 hours, the reaction was terminated, and the solvent was removed under reduced pressure after cooling to room temperature. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 21 (20.5 g, yield 59%, MS: [M+H]+= 686).
제조예 22: 화합물 22의 제조Preparation 22: Preparation of compound 22
질소 분위기에서 중간체 22-1(20 g, 50.8 mmol), 중간체 22-2(20.2 g, 50.8 mmol), sodium tert-butoxide(9.8 g, 101.5 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.5 g, 1 mmol)을 투입했다. 2 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 22(22.4 g, 수율 62 %, MS: [M+H]+= 712)을 얻었다.In a nitrogen atmosphere, Intermediate 22-1 (20 g, 50.8 mmol), Intermediate 22-2 (20.2 g, 50.8 mmol), and sodium tert-butoxide (9.8 g, 101.5 mmol) were added to 400 ml of Xylene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1 mmol) was added. After 2 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reducing the pressure. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 22 (22.4 g, yield 62%, MS: [M+H]+=712).
제조예 23: 화합물 23의 제조Preparation 23: Preparation of compound 23
질소 분위기에서 중간체 23-1(20 g, 50.8 mmol), 중간체 23-2(17 g, 50.8 mmol), sodium tert-butoxide(9.8 g, 101.5 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.5 g, 1 mmol)을 투입했다. 2 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 23(16.8 g, 수율 51 %, MS: [M+H]+= 650)을 얻었다.In a nitrogen atmosphere, Intermediate 23-1 (20 g, 50.8 mmol), Intermediate 23-2 (17 g, 50.8 mmol), and sodium tert-butoxide (9.8 g, 101.5 mmol) were added to 400 ml of Xylene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1 mmol) was added. After 2 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reducing the pressure. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 23 (16.8 g, yield 51%, MS: [M+H]+=650).
제조예 24: 화합물 24의 제조Preparation 24: Preparation of compound 24
질소 분위기에서 중간체 24-1(20 g, 50.8 mmol), 중간체 24-2(15 g, 50.8 mmol), sodium tert-butoxide(9.8 g, 101.5 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.5 g, 1 mmol)을 투입했다. 2 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 24(21 g, 수율 68 %, MS: [M+H]+= 610)을 얻었다.In a nitrogen atmosphere, Intermediate 24-1 (20 g, 50.8 mmol), Intermediate 24-2 (15 g, 50.8 mmol), and sodium tert-butoxide (9.8 g, 101.5 mmol) were added to 400 ml of Xylene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1 mmol) was added. After 2 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reducing the pressure. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 24 (21 g, yield 68%, MS: [M+H]+=610).
제조예 25: 화합물 25의 제조Preparation 25: Preparation of compound 25
질소 분위기에서 중간체 25-1(20 g, 50.8 mmol), 중간체 25-2(18.8 g, 50.8 mmol), sodium tert-butoxide(9.8 g, 101.5 mmol)을 Xylene 400 ml에 넣고 교반 및 환류했다. 이 후 bis(tri-tert-butylphosphine)palladium(0)(0.5 g, 1 mmol)을 투입했다. 3 시간 후 반응이 종결 되어서 상온으로 식히고 감압하여 용매를 제거했다. 이 후 화합물을 다시 클로로포름에 완전히 녹이고 물로 2회 세척 후에 유기층을 분리하여 무수황산마그네슘 처리 후 여과하여 여액을 감압 증류했다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제해서 화합물 25(21.6 g, 수율 62 %, MS: [M+H]+= 686)을 얻었다.In a nitrogen atmosphere, Intermediate 25-1 (20 g, 50.8 mmol), Intermediate 25-2 (18.8 g, 50.8 mmol), and sodium tert-butoxide (9.8 g, 101.5 mmol) were added to 400 ml of Xylene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1 mmol) was added. After 3 hours, the reaction was terminated, and the solvent was removed under reduced pressure after cooling to room temperature. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 25 (21.6 g, yield 62%, MS: [M+H]+= 686).
비교예 1Comparative Example 1
ITO(indium tin oxide)가 1000 Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척했다. 이때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용했다. ITO를 30 분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10 분간 진행했다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5 분간 세정한 후 진공 증착기로 기판을 수송시켰다.A glass substrate coated with indium tin oxide (ITO) to a thickness of 1000 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, and after drying, it was 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 화합물 HI-1을 1150 Å의 두께로 형성하되 하기 화합물 A-1을 1.5% 농도로 p-doping 했다. 상기 정공주입층 위에 하기 화합물 HT-1을 진공 증착하여 막 두께 800 Å 의 정공수송층을 형성했다. 이어서, 앞서 제조한 화합물 1과 하기 화합물 Dp-7을 98:2의 중량비로 진공 증착하여 400 Å 두께의 적색 발광층을 형성했다. 상기 발광층 위에 막 두께 30 Å으로 하기 화합물 HB-1을 진공 증착하여 정공저지층을 형성했다. 이어서, 상기 정공저지층 위에 하기 화합물 ET-1과 하기 화합물 LiQ을 2:1의 중량비로 진공 증착하여 300 Å의 두께로 전자 주입 및 수송층을 형성했다. 상기 전자 주입 및 수송층 위에 순차적으로 12 Å 두께로 리튬플로라이드(LiF)와 1000 Å 두께로 알루미늄을 증착하여 음극을 형성했다. The following compound HI-1 was formed to a thickness of 1150 Å as a hole injection layer on the prepared ITO transparent electrode, but the following compound A-1 was p-doped at a concentration of 1.5%. The following compound HT-1 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 800 Å. Then, the
상기의 과정에서 유기물의 증착속도는 0.4~0.7 Å/sec를 유지하였고, 음극의 리튬플로라이드는 0.3 Å/sec, 알루미늄은 2 Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 2ⅹ10-7 ~ 5ⅹ10-6 torr를 유지하여, 유기 발광 소자를 제작했다.In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å/sec, the deposition rate of lithium fluoride of the negative electrode was maintained at 0.3 Å/sec, and the deposition rate of aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was 2×10 -7 ~ 5×10 -6 torr was maintained to manufacture an organic light emitting device.
비교예 2 내지 비교예 25Comparative Examples 2 to 25
비교예 1의 유기 발광 소자에서 화합물 1 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 비교예 1과 동일한 방법으로 유기 발광 소자를 제조했다. 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
비교예 26 내지 비교예 73Comparative Examples 26 to 73
비교예 1의 유기 발광 소자에서 화합물 1 및 화합물 HT-1 대신 하기 표 2에 기재된 화합물을 각각 발광층 및 정공수송층에 사용하는 것을 제외하고는, 상기 비교예 1과 동일한 방법으로 유기 발광 소자를 제조했다. In the organic light emitting device of Comparative Example 1, an organic light emitting device was prepared in the same manner as in Comparative Example 1, except that the compound shown in Table 2 below was used in the light emitting layer and the hole transport layer, respectively, instead of
비교예 74 내지 비교예 105Comparative Examples 74 to 105
비교예 1의 유기 발광 소자에서 화합물 1 대신 표 3에 기재된 제1 호스트와 제2 호스트 화합물을 1:1의 중량비로 발광층에 사용하는 것을 제외하고는, 상기 비교예 1과 동일한 방법으로 유기 발광 소자를 제조했다. 표 3에 기재된 화합물 C-1 내지 C-4는 아래와 같다.In the organic light emitting device of Comparative Example 1, in the organic light emitting device in the same manner as in Comparative Example 1, except that the first host and the second host compound of Table 3 were used in the light emitting layer in a weight ratio of 1:1 instead of
비교예 106 내지 비교예 137Comparative Examples 106 to 137
비교예 1의 유기 발광 소자에서 화합물1 대신 표 4에 기재된 제1 호스트와 제2 호스트 화합물을 1:1의 중량비로 발광층에 사용하는 것을 제외하고는, 상기 비교예 1과 동일한 방법으로 유기 발광 소자를 제조했다. 표 4에 기재된 화합물 C-5 내지 C-12는 아래와 같다.In the organic light emitting device of Comparative Example 1, in the organic light emitting device in the same manner as in Comparative Example 1, except that the first host and the second host compound described in Table 4 were used in the light emitting layer in a weight ratio of 1:1 instead of
실시예 1 내지 실시예 70Examples 1-70
비교예 1의 유기 발광 소자에서 화합물1 대신 표 5에 기재된 제1 호스트와 제2 호스트 화합물을 1:1의 중량비로 발광층에 사용하는 것을 제외하고는, 상기 비교예 1과 동일한 방법으로 유기 발광 소자를 제조했다. In the organic light emitting device of Comparative Example 1, in the organic light emitting device in the same manner as in Comparative Example 1, except that the first host and the second host compound described in Table 5 were used in the light emitting layer in a weight ratio of 1:1 instead of
실험예Experimental example
상기 실시예 및 비교예에서 제조한 유기 발광 소자에 대하여 10 mA/cm2의 전류 밀도를 갖는 전류를 인가하였을 때, 전압, 효율, 수명을 측정(6000 nit 기준)하고 그 결과를 하기 표 1 내지 표 5에 나타내었다. 수명 T95는 휘도가 초기 휘도(6000 nit)에서 95%로 감소되는데 소요되는 시간을 의미한다. When a current having a current density of 10 mA/cm 2 was applied to the organic light-emitting devices prepared in Examples and Comparative Examples, voltage, efficiency, and lifespan were measured (based on 6000 nits), and the results are shown in Tables 1 to Table 5 shows. The lifetime T95 means the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.
실시예 1 내지 70 및 비교예 1 내지 137에 의해 제작된 유기 발광 소자에 대하여, 상기 표 1 내지 표 5의 결과를 얻었다. 상기 결과를 보면 발광층에 화학식 1로 표시되는 화합물과 화학식 2로 표시되는 화합물을 코호스트로 사용하여 공증착한 유기 발광 소자의 구동전압, 효율, 수명 측정 결과가 가장 우수했다. 발광층에 화학식 1로 표시되는 화합물과 화학식 2로 표시되는 화합물을 사용한 유기 발광 소자는 화학식 1로 표시되는 화합물 또는 화학식 2로 표시되는 화합물만을 단일 호스트로 포함하는 유기 발광 소자(비교예 1 내지 비교예 25)보다 우수한 결과를 나타냈다. 또한, 본 발명의 일 실시예는 화학식 2로 표시되는 화합물을 정공 수송 영역에 사용한 경우(비교예 26 내지 비교예 73)보다 우수하였으며, 화학식 1로 표시되는 화합물 또는 화학식 2로 표시되는 화합물을 포함하되, 본 발명에 포함되지 않는 화합물 C-1 내지 C-12 중 어느 하나를 코호스트로 포함하는 유기 발광 소자(비교예 74 내지 비교예 137) 보다도 우수한 결과를 나타냈다. For the organic light emitting devices manufactured in Examples 1 to 70 and Comparative Examples 1 to 137, the results in Tables 1 to 5 were obtained. Looking at the above results, the driving voltage, efficiency, and lifespan measurement results of the organic light emitting device co-deposited using the compound represented by
이상의 결과로부터, 화학식 1로 표시되는 화합물 및 화학식 2로 표시되는 화합물을 조합하면 발광층 내에서 정공의 양이 많아지면서 발광층 내에 전자와 정공이 더 안정적인 균형을 유지하여 효율과 수명이 상승함을 유추할 수 있다. 결론적으로 본 발명의 화합물 조합을 발광층의 호스트로 사용하였을 때 유기 발광 소자의 구동전압, 발광 효율 및 수명 특성을 개선할 수 있다. From the above results, it can be inferred that when the compound represented by
1: 기판
2: 양극
3: 발광층
4: 음극
5: 정공주입층
6: 정공수송층
7: 정공저지층
8: 전자 주입 및 수송층1: Substrate 2: Anode
3: light emitting layer 4: cathode
5: hole injection layer 6: hole transport layer
7: hole blocking layer 8: electron injection and transport layer
Claims (11)
음극,
상기 양극과 음극 사이의 발광층을 포함하고,
상기 발광층은 하기 화학식 1-1 또는 화학식 1-2로 표시되는 화합물 및 하기 화학식 2로 표시되는 화합물을 포함하는,
유기 발광 소자:
[화학식 1-1]
[화학식 1-2]
상기 화학식 1-1 또는 화학식 1-2에서,
Ar1은 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴이고,
L은 단일결합; 또는 치환 또는 비치환된 C6-60 아릴렌이고,
R5, R6, R7 및 R8은 각각 독립적으로, 수소; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴이고,
[화학식 2]
상기 화학식 2에서,
Ar2 및 Ar3는 각각 독립적으로, 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴이다.
anode,
cathode,
a light emitting layer between the anode and the cathode;
The light emitting layer comprises a compound represented by the following Chemical Formula 1-1 or 1-2 and a compound represented by the following Chemical Formula 2,
Organic light emitting device:
[Formula 1-1]
[Formula 1-2]
In Formula 1-1 or Formula 1-2,
Ar 1 is C 2-60 heteroaryl including at least one selected from the group consisting of substituted or unsubstituted N, O and S,
L is a single bond; Or a substituted or unsubstituted C 6-60 arylene,
R 5 , R 6 , R 7 and R 8 are each independently hydrogen; Or substituted or unsubstituted C 2-60 heteroaryl comprising any one or more selected from the group consisting of N, O and S,
[Formula 2]
In Formula 2,
Ar 2 and Ar 3 are each independently, substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl comprising any one or more selected from the group consisting of N, O and S.
Ar1은 치환 또는 비치환된 2 이상의 N을 포함하는 C2-60 헤테로아릴인,
유기 발광 소자.
According to claim 1,
Ar 1 is substituted or unsubstituted C 2-60 heteroaryl containing 2 or more N,
organic light emitting device.
Ar1은 치환 또는 비치환된 퀴나졸리닐, 또는 치환 또는 비치환된 퀴녹살리닐인,
유기 발광 소자.
According to claim 1,
Ar 1 is a substituted or unsubstituted quinazolinyl, or a substituted or unsubstituted quinoxalinyl,
organic light emitting device.
Ar1은 하기로 구성되는 군으로부터 선택되는 어느 하나인,
유기 발광 소자:
According to claim 1,
Ar 1 is any one selected from the group consisting of
Organic light emitting device:
L은 단일결합인,
유기 발광 소자.
According to claim 1,
L is a single bond,
organic light emitting device.
R5, R6, R7 및 R8은 각각 독립적으로, 수소 또는 카바졸릴이고,
상기 카바졸릴은 비치환되거나, 페닐, 비페닐릴, 나프틸, 나프틸 페닐 및 페닐 나프틸 중 어느 하나로 치환된,
유기 발광 소자.
According to claim 1,
R 5 , R 6 , R 7 and R 8 are each independently hydrogen or carbazolyl,
The carbazolyl is unsubstituted or substituted with any one of phenyl, biphenylyl, naphthyl, naphthyl phenyl and phenyl naphthyl,
organic light emitting device.
R5, R6, R7 및 R8은 각각 독립적으로, 수소 또는 하기로 구성되는 군으로부터 선택되는 어느 하나인,
유기 발광 소자:
According to claim 1,
R 5 , R 6 , R 7 and R 8 are each independently any one selected from the group consisting of hydrogen or the following,
Organic light emitting device:
R5, R6, R7 및 R8 중 적어도 하나는 치환 또는 비치환된 카바졸릴인,
유기 발광 소자.
According to claim 1,
At least one of R 5 , R 6 , R 7 and R 8 is substituted or unsubstituted carbazolyl;
organic light emitting device.
상기 화학식 1로 표시되는 화합물은 하기로 구성되는 군으로부터 선택되는 어느 하나인,
유기 발광 소자:
According to claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of
Organic light emitting device:
Ar2 및 Ar3는 각각 독립적으로, 페닐, 비페닐릴, 터페닐릴, 디메틸 플루오레닐, 나프틸, 나프틸 페닐, 또는 페닐 나프틸인,
유기 발광 소자.
According to claim 1,
Ar 2 and Ar 3 are each independently phenyl, biphenylyl, terphenylyl, dimethyl fluorenyl, naphthyl, naphthyl phenyl, or phenyl naphthyl;
organic light emitting device.
상기 화학식 2 표시되는 화합물은 하기로 구성되는 군으로부터 선택되는 어느 하나인,
유기 발광 소자:
According to claim 1,
The compound represented by Formula 2 is any one selected from the group consisting of
Organic light emitting device:
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