KR102145020B1 - Novel cyclic compound and organic light emitting device comprising the same - Google Patents
Novel cyclic compound and organic light emitting device comprising the same Download PDFInfo
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- KR102145020B1 KR102145020B1 KR1020170137662A KR20170137662A KR102145020B1 KR 102145020 B1 KR102145020 B1 KR 102145020B1 KR 1020170137662 A KR1020170137662 A KR 1020170137662A KR 20170137662 A KR20170137662 A KR 20170137662A KR 102145020 B1 KR102145020 B1 KR 102145020B1
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- 150000001923 cyclic compounds Chemical class 0.000 title abstract description 6
- 239000011368 organic material Substances 0.000 claims abstract description 38
- 150000001875 compounds Chemical class 0.000 claims description 86
- 238000000034 method Methods 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 37
- 239000010410 layer Substances 0.000 description 152
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 42
- 238000002347 injection Methods 0.000 description 37
- 239000007924 injection Substances 0.000 description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- -1 hole transport Substances 0.000 description 35
- 230000032258 transport Effects 0.000 description 32
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 27
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- 230000000052 comparative effect Effects 0.000 description 24
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- 239000012299 nitrogen atmosphere Substances 0.000 description 20
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 19
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- 238000010438 heat treatment Methods 0.000 description 16
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- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 13
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- 230000000903 blocking effect Effects 0.000 description 9
- 238000000151 deposition Methods 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 8
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- 125000000217 alkyl group Chemical group 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 239000010406 cathode material Substances 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
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- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
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- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 4
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- 0 *C1(*)c2ccccc2C2(c(cccc3)c3-c3c2cccc3)C(C=CC=*)=C1C=* Chemical compound *C1(*)c2ccccc2C2(c(cccc3)c3-c3c2cccc3)C(C=CC=*)=C1C=* 0.000 description 3
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 3
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 3
- IZYQYWHHPQRWFX-UHFFFAOYSA-N [3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]boronic acid Chemical compound OB(O)C1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 IZYQYWHHPQRWFX-UHFFFAOYSA-N 0.000 description 3
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- 125000001769 aryl amino group Chemical group 0.000 description 3
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 3
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- 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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Abstract
본 발명은 신규한 고리 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다. 상기 고리 화합물은 유기 전계 발광 소자의 유기물 층의 재료로서 사용될 수 있으며, 유기 전계 발광 소자에서 효율의 향상, 낮은 구동 전압 및/또는 수명 특성을 향상시킬 수 있다.The present invention relates to a novel cyclic compound and an organic electroluminescent device comprising the same. The cyclic compound may be used as a material for an organic material layer of an organic electroluminescent device, and may improve efficiency, low driving voltage, and/or lifetime characteristics in an organic electroluminescent device.
Description
본 발명은 신규한 고리 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel cyclic compound and an organic electroluminescent device comprising the same.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 전계 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 emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. The organic electroluminescent 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 전계 발광 소자는 일반적으로 양극과 음극 및 상기 양극과 음극 사이에 유기물 층을 포함하는 구조를 가진다. 상기 유기물 층은 유기 전계 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 주입층 등으로 이루어질 수 있다. An organic electroluminescent device generally has a structure including an anode and a cathode, and an organic material layer between the anode and the cathode. The organic material layer is often made of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic electroluminescent device, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. .
이러한 유기 전계 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물 층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥 상태로 떨어질 때 빛이 나게 된다.In the structure of such an organic electroluminescent device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when the exciton falls back to the ground state.
상기와 같은 유기 전계 발광 소자에 사용되는 유기물에 대하여 새로운 재료의 개발이 지속적으로 요구되고 있다.Development of new materials for organic materials used in organic electroluminescent devices as described above is continuously required.
본 발명은 유기 전계 발광 화합물로서 신규한 고리 화합물을 제공하기 위한 것이다.The present invention is to provide a novel cyclic compound as an organic electroluminescent compound.
그리고, 본 발명은 상기 고리 화합물을 포함하는 유기 전계 발광 소자를 제공하기 위한 것이다.In addition, the present invention is to provide an organic electroluminescent device comprising the cyclic compound.
본 발명에 따르면, 하기 화학식 1로 표시되는 화합물이 제공된다:According to the present invention, a compound represented by the following
[화학식 1][Formula 1]
상기 화학식 1에서,In Formula 1,
R1은 각각 독립적으로 수소, C1-30의 알킬기 또는 C6-30의 아릴기이고,R 1 is each independently hydrogen, a C 1-30 alkyl group or a C 6-30 aryl group,
L1 은 직접 결합; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, 또는 C6-30의 아릴기로 치환되거나 치환되지 않은 C6-50의 아릴렌기; 또는 N, O 및 S로 이루어진 군으로부터 선택된 어느 하나 이상의 헤테로원자를 포함하고 C6-30의 아릴기로 치환되거나 치환되지 않은 C2-60의 헤테로아릴렌기이고,L 1 is a direct bond; Deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryloxy group, or arylene group that is not substituted with a C 6-30 aryl substituted C 6-50; Or a C 2-60 heteroarylene group that includes any one or more heteroatoms selected from the group consisting of N, O and S and is substituted or unsubstituted with an aryl group of C 6-30 ,
X1, X2 및 X3는 각각 독립적으로 N 또는 C(Ra)로서, 상기 X1, X2 및 X3 중 적어도 하나는 N이고,X 1 , X 2 and X 3 are each independently N or C (R a ), wherein at least one of X 1 , X 2 and X 3 is N,
Ra는 수소 또는 C1-30의 알킬기이고,R a is hydrogen or a C 1-30 alkyl group,
Ar1 및 Ar2는 각각 독립적으로 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, 또는 C6-30의 아릴기로 치환되거나 치환되지 않은 C6-50의 아릴기; 또는 N, O 및 S로 이루어진 군으로부터 선택된 어느 하나 이상의 헤테로원자를 포함하고 C6-30의 아릴기로 치환되거나 치환되지 않은 C2-60의 헤테로아릴기이다.Ar 1 and Ar 2 are each independently deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy A group, a C 6-30 aryloxy group, or a C 6-50 aryl group substituted or unsubstituted with a C 6-30 aryl group; Or a C 2-60 heteroaryl group that includes any one or more heteroatoms selected from the group consisting of N, O and S, and is substituted or unsubstituted with a C 6-30 aryl group.
또한, 본 발명에 따르면, Further, according to the present invention,
제 1 전극, 상기 제 1 전극과 대향하여 구비된 제 2 전극, 및 상기 제 1 전극과 제 2 전극 사이에 구비된 1 층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서;An organic electroluminescent device comprising a first electrode, a second electrode provided opposite to the first electrode, and one or more organic material layers provided between the first electrode and the second electrode;
상기 유기물층 중 적어도 한 층은 상기 화학식 1로 표시되는 화합물을 포함하는, 유기 전계 발광 소자가 제공된다.At least one of the organic material layers is provided with an organic electroluminescent device including the compound represented by Formula 1.
상기 화학식 1로 표시되는 화합물은 유기 전계 발광 소자의 유기물 층의 재료로서 사용될 수 있으며, 유기 전계 발광 소자에서 효율의 향상, 낮은 구동 전압 및/또는 수명 특성을 향상시킬 수 있다. 특히, 상기 화학식 1로 표시되는 화합물은 정공 주입, 정공 수송, 정공 주입 및 수송, 발광, 전자 수송, 또는 전자 주입 재료로 사용될 수 있다.The compound represented by Formula 1 may be used as a material for an organic material layer of an organic electroluminescent device, and may improve efficiency, low driving voltage, and/or lifetime characteristics in an organic electroluminescent device. In particular, the compound represented by Formula 1 may be used as a hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection material.
도 1은 기판(1), 양극(2), 발광층(3), 및 음극(4)으로 이루어진 유기 전계 발광 소자의 예를 도시한 것이다.
도 2는 기판(1), 양극(2), 정공 주입층(5), 정공 수송층(6), 발광층(7), 전자 수송층(8), 및 음극(4)로 이루어진 유기 전계 발광 소자의 예를 도시한 것이다.1 shows an example of an organic electroluminescent device comprising a
2 is an example of an organic electroluminescent device comprising a
이하, 본 발명의 이해를 돕기 위하여 발명의 구현 예들에 따른 화합물 및 이를 포함하는 유기 전계 발광 소자에 대해 상세히 설명하기로 한다.Hereinafter, a compound according to exemplary embodiments of the present invention and an organic electroluminescent device including the same will be described in detail in order to aid understanding of the present invention.
본 명세서에서 명시적인 언급이 없는 한, 전문용어는 단지 특정 실시예를 언급하기 위한 것이며, 본 발명을 한정하는 것을 의도하지 않는다.Unless expressly stated in the specification, terminology is only intended to refer to specific embodiments and is not intended to limit the invention.
본 명세서에서 사용되는 단수 형태들은 문구들이 이와 명백히 반대의 의미를 나타내지 않는 한 복수 형태들도 포함한다.Singular forms used in this specification also include plural forms unless the phrases clearly indicate the opposite.
본 명세서에서 사용되는 "포함"의 의미는 특정 특성, 영역, 정수, 단계, 동작, 요소 및/또는 성분을 구체화하며, 다른 특정 특성, 영역, 정수, 단계, 동작, 요소, 성분 및/또는 군의 존재나 부가를 제외시키는 것은 아니다.As used herein, the meaning of “comprising” specifies a specific characteristic, region, integer, step, action, element and/or component, and other specific characteristic, region, integer, step, action, element, component and/or group It does not exclude the existence or addition of
본 명세서에서 또는 표시는 해당 그룹이 다른 그룹과 연결되는 부분을 나타낸다.In this specification or The mark indicates the part where the group is connected to other groups.
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.In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Arylsulfoxy group; Silyl group; Boron group; Alkyl group; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or it means substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing one or more of N, O, and S atoms, or substituted or unsubstituted with two or more substituents connected among the aforementioned substituents. . For example, "a substituent to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent to which two phenyl groups are connected.
본 명세서에서, 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 6이다. 알킬기의 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 사이클로펜틸메틸,사이클로헥틸메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸펜틸, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이들에 한정되지 않는다.In the present specification, the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group 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, cycloheptylmethyl, 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 명세서에서, 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. 알케닐기의 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 alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples of the alkenyl group 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, and styrenyl group, but are not limited thereto. .
본 명세서에서, 알키닐기는 탄소수 2 내지 30의 알킨 혹은 그 유도체로부터 수소 1 원자를 제거한 형태의 1가 그룹이다.In the present specification, an alkynyl group is a monovalent group in the form of removing 1 hydrogen atom from an alkyne having 2 to 30 carbon atoms or a derivative thereof.
본 명세서에서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the number of carbon atoms in the aryl group is 6 to 30. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but the monocyclic aryl group 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 명세서에서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. 상기 플루오레닐기가 치환되는 경우, , , , 등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted, , , , Etc. However, it is not limited thereto.
본 명세서에서, 헤테로고리기는 이종 원소로 O, N, Si, 및 S 중 1개 이상을 포함하는 고리기로서, 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로고리기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤조옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 페난쓰롤린기(phenanthroline), 이소옥사졸릴기, 티아디아졸릴기, 페노티아지닐기, 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group is a cyclic group containing at least one of O, N, Si, and S as a heterogeneous element, and the number of carbons is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine 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, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isoxazolyl group, thiiadia There are a zolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.
본 명세서에서, 아릴렌은 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다. 헤테로아릴렌은 2가기인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다.In the present specification, the description of the aryl group described above may be applied except that the arylene is a divalent group. Except that the heteroarylene is a divalent group, the above description of the heterocyclic group may be applied.
한편, 발명의 일 구현 예에 따르면, 하기 화학식 1로 표시되는 화합물이 제공된다.Meanwhile, according to an embodiment of the present invention, a compound represented by the following formula (1) is provided.
[화학식 1][Formula 1]
본 발명자들의 계속적인 연구 결과, 상기 화학식 1로 표시되는 화합물은 10H-spiro[anthracene-9,9'-fluorene] 유도체를 코어로 L1, X1, X2, X3, Ar1, 및 Ar2를 포함한 치환기가 도입된 형태의 화합물로서, 상기 구조적 특징을 가짐에 따라 유기 전계 발광 소자에 적용되어 소자의 효율과 수명 특성의 향상을 가능하게 한다.As a result of continuous research of the present inventors, the compound represented by Formula 1 is a 10H-spiro[anthracene-9,9'-fluorene] derivative as a core L 1 , X 1 , X 2 , X 3 , Ar 1 , and Ar As a compound in which a substituent including 2 is introduced, it is applied to an organic electroluminescent device as it has the above structural characteristics, thereby enabling improvement of the efficiency and lifetime characteristics of the device.
바람직하게는, 상기 화학식 1의 화합물은 결합 위치에 따라 하기 화학식 2-a 내지 2-c 중 어느 하나로 표시되는 화합물일 수 있다:Preferably, the compound of Formula 1 may be a compound represented by any one of the following Formulas 2-a to 2-c depending on the bonding position:
[화학식 2-a][Formula 2-a]
[화학식 2-b][Formula 2-b]
[화학식 2-c][Formula 2-c]
상기 화학식 2-a 내지 2-c에서,In Formulas 2-a to 2-c,
R1, L1, X1, X2, X3, Ar1, 및 Ar2는 각각 상기 화학식 1에서 정의된 바와 같다.R 1 , L 1 , X 1 , X 2 , X 3 , Ar 1 , and Ar 2 are each as defined in
상기 화학식 1에서, R1는 각각 독립적으로 수소, C1-30의 알킬기 또는 C6-30의 아릴기이다. 바람직하게는, R1은 각각 독립적으로 메틸기 또는 페닐기일 수 있다.In
상기 화학식 1에서, L1은 직접 결합; 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, 또는 C6-30의 아릴기로 치환되거나 치환되지 않은 C6-50의 아릴렌기; 또는 N, O 및 S로 이루어진 군으로부터 선택된 어느 하나 이상의 헤테로원자를 포함하고 C6-30의 아릴기로 치환되거나 치환되지 않은 C2-60의 헤테로아릴렌기일 수 있다.In
바람직하게는, L1은 직접 결합 또는 하기로 구성되는 군으로부터 선택된 어느 하나의 그룹일 수 있다:Preferably, L 1 may be a direct bond or any one group selected from the group consisting of:
. .
상기 화학식 1에서, X1, X2 및 X3는 각각 독립적으로 N 또는 C(Ra)로서, 상기 X1, X2 및 X3 중 적어도 하나는 N이다. In
여기서, Ra는 수소 또는 C1-30의 알킬기이고, 바람직하게는 수소이다.Here, R a is hydrogen or a C 1-30 alkyl group, preferably hydrogen.
예를 들어, 상기 화학식 1에서 X1, X2 및 X3를 포함한 그룹은 하기 화학식 3-a 내지 3-f로 표시되는 그룹 중에서 선택되는 어느 하나일 수 있다:For example, the group including X 1 , X 2 and X 3 in
[화학식 3-a][Formula 3-a]
[화학식 3-b][Formula 3-b]
[화학식 3-c][Formula 3-c]
[화학식 3-d][Formula 3-d]
[화학식 3-e][Formula 3-e]
[화학식 3-f][Formula 3-f]
상기 화학식 3-a 내지 3-f에서,In Formulas 3-a to 3-f,
L1, Ar1 및 Ar2는 각각 상기 화학식 1에서 정의된 바와 같다.L 1 , Ar 1 and Ar 2 are as defined in
상기 화학식 1에서, Ar1 및 Ar2는 각각 독립적으로 중수소, 할로겐, 아미노기, 니트릴기, 니트로기, C1-30의 알킬기, C2-30의 알케닐기, C2-30의 알키닐기, C1-30의 알콕시기, C6-30의 아릴옥시기, 또는 C6-30의 아릴기로 치환되거나 치환되지 않은 C6-50의 아릴기; 또는 N, O 및 S로 이루어진 군으로부터 선택된 어느 하나 이상의 헤테로원자를 포함하고 C6-30의 아릴기로 치환되거나 치환되지 않은 C2-60의 헤테로아릴기이다.In
구체적으로, Ar1 및 Ar2는 각각 독립적으로 하기로 구성되는 군으로부터 선택된 어느 하나의 그룹일 수 있다:Specifically, Ar 1 and Ar 2 may each independently be any one group selected from the group consisting of:
바람직하게는, 상기 화학식 1로 표시되는 화합물은 하기로 구성되는 군으로부터 선택된 어느 하나일 수 있다.Preferably, the compound represented by
상기 화학식 1로 표시되는 화합물은 하기 반응식 1을 통해 제조될 수 있다.The compound represented by
[반응식 1][Scheme 1]
상기 반응식 1에서,In
Z1은 할로겐이고,Z 1 is halogen,
L1, X1, X2, X3, Ar1, 및 Ar2 는 각각 상기 화학식 1에서 정의된 바와 같다.L 1 , X 1 , X 2 , X 3 , Ar 1 , and Ar 2 are as defined in
비제한적인 예로, 상기 화학식 1로 표시되는 화합물의 제조 방법에 사용되는 중간체는 다음과 같은 방법으로 제조될 수 있다.As a non-limiting example, the intermediate used in the method for preparing the compound represented by
[반응식 I-A][Scheme I-A]
[반응식 I-B][Scheme I-B]
[반응식 I-C][Reaction Scheme I-C]
[반응식 I-D][Scheme I-D]
[반응식 I-E][Scheme I-E]
[반응식 I-F][Scheme I-F]
[반응식 I-A' 내지 I-F'][Scheme I-A' to I-F']
상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다.The manufacturing method may be more specific in the manufacturing examples to be described later.
한편, 발명의 다른 일 구현 예에 따르면, 상기 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자가 제공된다.Meanwhile, according to another embodiment of the present invention, an organic electroluminescent device including the compound represented by
일례로, 본 발명에 따르면, 제 1 전극, 상기 제 1 전극과 대향하여 구비된 제 2 전극, 및 상기 제 1 전극과 제 2 전극 사이에 구비된 1 층 이상의 유기물층을 포함 하는 유기 전계 발광 소자로서; 상기 유기물층 중 적어도 한 층은 제 1 항의 화학식 1로 표시되는 화합물을 포함하는, 유기 전계 발광 소자가 제공된다.For example, according to the present invention, an organic electroluminescent device comprising a first electrode, a second electrode provided opposite to the first electrode, and one or more organic material layers provided between the first electrode and the second electrode, ; An organic electroluminescent device is provided in which at least one of the organic material layers includes the compound represented by
본 발명의 유기 전계 발광 소자의 유기물 층은 단층 구조로 이루어질 수도 있으며, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. The organic material layer of the organic electroluminescent device of the present invention may have a single-layer structure, or may have a multilayer structure in which two or more organic material layers are stacked.
예컨대, 본 발명의 유기 전계 발광 소자는 유기물 층으로서 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 주입층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 전계 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층을 포함할 수 있다.For example, the organic electroluminescent device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic material layer. However, the structure of the organic electroluminescent device is not limited thereto and may include a smaller number of organic layers.
또한, 상기 유기물 층은 정공 주입층, 정공 수송층, 또는 정공 주입과 수송을 동시에 하는 층을 포함할 수 있고, 상기 정공 주입층, 정공 수송층, 또는 정공 주입과 수송을 동시에 하는 층은 상기 화학식 1로 표시되는 화합물을 포함한다.In addition, the organic material layer may include a hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting holes, and the hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting holes is represented by
또한, 상기 유기물 층은 발광층을 포함할 수 있고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함한다.In addition, the organic material layer may include an emission layer, and the emission layer includes the compound represented by
또한, 상기 유기물 층은 전자 수송층, 또는 전자 주입층을 포함할 수 있고, 상기 전자 수송층 또는 전자 주입층은 상기 화학식 1로 표시되는 화합물을 포함한다.In addition, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound represented by
또한, 상기 전자 수송층, 전자 주입층, 또는 전자수송 및 전자주입을 동시에 하는 층은 상기 화학식 1로 표시되는 화합물을 포함한다.In addition, the electron transport layer, the electron injection layer, or a layer that simultaneously transports electrons and injects electrons includes the compound represented by
또한, 상기 유기물 층은 발광층 및 전자 수송층을 포함하고, 상기 전자 수송층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.In addition, the organic material layer may include an emission layer and an electron transport layer, and the electron transport layer may include a compound represented by
또한, 본 발명에 따른 유기 전계 발광 소자는, 기판 상에 양극, 1층 이상의 유기물 층 및 음극이 순차적으로 적층된 구조(normal type)의 유기 전계 발광 소자일 수 있다.Further, the organic electroluminescent device according to the present invention may be a normal type organic electroluminescent device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
또한, 본 발명에 따른 유기 전계 발광 소자는 기판 상에 음극, 1층 이상의 유기물 층 및 양극이 순차적으로 적층된 역방향 구조(inverted type)의 유기 전계 발광 소자일 수 있다. In addition, the organic electroluminescent device according to the present invention may be an inverted type organic electroluminescent device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
예컨대, 본 발명의 일 실시예에 따른 유기 전계 발광 소자의 구조는 도 1 및 도 2에 예시되어 있다.For example, the structure of an organic electroluminescent device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
도 1은 기판(1), 양극(2), 발광층(3), 음극(4)으로 이루어진 유기 전계 발광 소자의 예를 도시한 것이다. 도 1과 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 발광층에 포함될 수 있다.1 shows an example of an organic electroluminescent device comprising a
도 2는 기판(1), 양극(2), 정공 주입층(5), 정공 수송층(6), 발광층(7), 전자 수송층(8), 및 음극(4)로 이루어진 유기 전계 발광 소자의 예를 도시한 것이다. 도 2와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 정공 주입층, 정공 수송층, 및 전자 수송층 중 1층 이상; 바람직하게는 상기 정공 수송층에 포함될 수 있다.2 is an example of an organic electroluminescent device comprising a
한편, 본 발명에 따른 유기 전계 발광 소자는, 상기 유기물 층 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다.Meanwhile, the organic electroluminescent device according to the present invention may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by
또한, 상기 유기 전계 발광 소자가 복수개의 유기물 층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다.In addition, when the organic electroluminescent device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
예컨대, 본 발명에 따른 유기 전계 발광 소자는 기판 상에 제1 전극, 유기물층 및 제2 전극을 순차적으로 적층시켜 제조할 수 있다.For example, the organic electroluminescent device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
이때, 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(physical Vapor Deposition)방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물 층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시켜 제조할 수 있다.At this time, using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, the anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate. And, 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 cathode thereon.
이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물 층, 양극 물질을 차례로 증착시켜 유기 전계 발광 소자를 만들 수 있다.In addition to this method, an organic electroluminescent device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
또한, 상기 화학식 1로 표시되는 화합물은 유기 전계 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물 층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.In addition, the compound represented by
이와 같은 방법 외에도, 기판 상에 음극 물질로부터 유기물층, 양극 물질을 차례로 증착시켜 유기 전계 발광 소자를 제조할 수 있다(WO 2003/012890).In addition to such a method, an organic electroluminescent 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).
일례로, 상기 제1 전극은 양극이고, 상기 제2 전극은 음극이거나, 또는 상기 제1 전극은 음극이고, 상기 제2 전극은 양극이다.For example, the first electrode is an anode, the second electrode is a cathode, or the first electrode is a cathode, and the second electrode is an anode.
상기 양극 물질로는 통상 유기물 층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. As the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer.
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.Specific examples of the cathode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SNO2:Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.
상기 음극 물질로는 통상 유기물 층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
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.Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multilayered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
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. The hole injection material is a layer that injects 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 for 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 has excellent thin film formation ability is preferable.
정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물 층의 HOMO 사이인 것이 바람직하다.It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
상기 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, perylene There are a series of organic substances, anthraquinone, and polyaniline and a polythiophene series of conductive polymers, but are not limited thereto.
상기 정공 수송층은 정공 주입층으로부터 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 is a layer that receives holes from the hole injection layer and transports holes to the emission layer.A material capable of transporting holes to the emission layer by receiving holes from the anode or the hole injection layer as a hole transport material, and having high mobility for holes This is suitable.
상기 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.
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. The light-emitting material is a material capable of emitting light in a visible light region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
상기 발광 물질의 구체적인 예로 8-히드록시-퀴놀린 알루미늄 착물(Alq3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다.Specific examples of the light-emitting material 8-hydroxy-quinoline aluminum complex (Alq3); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. The emission layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds.
구체적으로 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되지 않는다.Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
도펀트 재료로는 방향족 아민 유도체, 스트릴아민 화합물, 붕소 착체, 플루오란텐 화합물, 금속 착체 등이 있다.Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
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.Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group, and the styrylamine compound is substituted or unsubstituted As a compound in which at least one arylvinyl group is substituted on the arylamine, one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc., but are not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
상기 전자 수송 물질로는 전자 주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층으로 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. The electron transport material is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer. The electron transport material is a material that can receive electrons from the cathode and transfer them to the emission layer, and has high mobility for electrons. This 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.Specific examples of the electron transport material include 8-hydroxyquinoline Al complex; Complexes including Alq3; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
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 can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium and samarium, and in each case an aluminum layer or a silver layer follows.
상기 전자 주입층은 전극으로부터 전자를 주입하는 층으로, 전자를 수송하는 능력을 갖고, 음극으로부터의 전자 주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공 주입층에의 이동을 방지하고, 또한, 박막 형성 능력이 우수한 화합물이 바람직하다. 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 injects holes of excitons generated in the light emitting layer A compound that prevents migration to a layer and is excellent in thin film formation ability is preferable.
상기 전자 주입층의 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 electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone And derivatives thereof, metal complex compounds, and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
상기 금속 착체 화합물로는 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 lithium 8-hydroxyquinolinato, 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-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. , Is not limited thereto.
본 발명에 따른 유기 전계 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic electroluminescent device according to the present invention may be of a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
또한, 상기 화학식 1로 표시되는 화합물은 유기 전계 발광 소자 외에도 유기 태양 전지 또는 유기 트랜지스터에 적용될 수 있다.In addition, the compound represented by
이하, 발명의 이해를 돕기 위하여 바람직한 실시예들을 제시한다. 그러나 하기의 실시예들은 발명을 예시하기 위한 것일 뿐, 발명을 이들만으로 한정하는 것은 아니다.Hereinafter, preferred embodiments are presented to aid in understanding the invention. However, the following examples are for illustrative purposes only, and the invention is not limited thereto.
제조예Manufacturing example 1 One
질소 분위기에서 500 ml 둥근 바닥 플라스크에 상기 화합물 A (7.46 g, 17.11 mmol), (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (6.95 g, 19.68 mmol)을 테트라하이드로퓨란 240 ml에 완전히 녹인 후 2M 탄산칼륨수용액(120 ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.59 g, 0.51 mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 테트라하이드로퓨란 180 ml로 재결정하여 상기 화합물 1 (8.89 g, 수율 78%)을 얻었다.Compound A (7.46 g, 17.11 mmol), (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (6.95 g,) in a 500 ml round bottom flask in a nitrogen atmosphere 19.68 mmol) was completely dissolved in 240 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (120 ml) was added, tetrakis-(triphenylphosphine) palladium (0.59 g, 0.51 mmol) was added, followed by heating and stirring for 3 hours. I did. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 180 ml of tetrahydrofuran to obtain Compound 1 (8.89 g, yield 78%).
MS[M+H]+ = 666MS[M+H] + = 666
제조예Manufacturing example 2 2
질소 분위기에서 500 ml 둥근 바닥 플라스크에 상기 화합물 A (6.75 g, 15.48 mmol), (3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (6.28 g, 17.80 mmol)을 테트라하이드로퓨란 220 ml에 완전히 녹인 후 2M 탄산칼륨수용액(110 ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.54g, 0.46 mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에틸아세테이트 260 ml로 재결정하여 상기 화합물 2 (7.39 g, 수율 72%)를 얻었다.Compound A (6.75 g, 15.48 mmol), (3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (6.28 g,) in a 500 ml round bottom flask in a nitrogen atmosphere 17.80 mmol) was completely dissolved in 220 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (110 ml) was added, tetrakis-(triphenylphosphine) palladium (0.54g, 0.46 mmol) was added, followed by heating and stirring for 3 hours. I did. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with ethyl acetate 260 ml to obtain the compound 2 (7.39 g, yield 72%).
MS[M+H]+ = 666MS[M+H] + = 666
제조예Manufacturing example 3 3
질소 분위기에서 500 ml 둥근 바닥 플라스크에 상기 화합물 A (7.13 g, 16.35 mmol), (3-(2,6-diphenylpyrimidin-4-yl)phenyl)boronic acid(6.62 g, 18.81 mmol)을 테트라하이드로퓨란 190 ml에 완전히 녹인 후 2M 탄산칼륨수용액(95 ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.57 g, 0.49 mmol)을 넣은 후 4 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에틸아세테이트 240 ml로 재결정하여 상기 화합물 3 (6.38 g, 수율 59%)을 얻었다.Compound A (7.13 g, 16.35 mmol), (3-(2,6-diphenylpyrimidin-4-yl)phenyl)boronic acid (6.62 g, 18.81 mmol) in a 500 ml round bottom flask in a nitrogen atmosphere was added to tetrahydrofuran 190 After completely dissolved in ml, 2M aqueous potassium carbonate solution (95 ml) was added, tetrakis-(triphenylphosphine) palladium (0.57 g, 0.49 mmol) was added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 240 ml of ethyl acetate to obtain the compound 3 (6.38 g, yield 59%).
MS[M+H]+ = 665MS[M+H] + = 665
제조예Manufacturing example 4 4
질소 분위기에서 500 ml 둥근 바닥 플라스크에 상기 화합물 A (5.46 g, 12.52 mmol), (3-(4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (6.38 g, 14.40 mmol)을 테트라하이드로퓨란 180 ml에 완전히 녹인 후 2M 탄산칼륨수용액(90 ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.43 g, 0.38 mmol)을 넣은 후 4 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에틸아세테이트 230 ml로 재결정하여 상기 화합물 4 (6.29 g, 수율 66%)를 얻었다.Compound A (5.46 g, 12.52 mmol), (3-(4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-) in a 500 ml round bottom flask in a nitrogen atmosphere After completely dissolving triazin-2-yl)phenyl)boronic acid (6.38 g, 14.40 mmol) in 180 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (90 ml) was added, and tetrakis-(triphenylphosphine)palladium ( 0.43 g, 0.38 mmol) was added and then heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 230 ml of ethyl acetate to obtain the compound 4 (6.29 g, yield 66%).
MS[M+H]+ = 756MS[M+H] + = 756
제조예Manufacturing example 5 5
질소 분위기에서 500 ml 둥근 바닥 플라스크에 상기 화합물 B (5.92 g, 13.58 mmol), (3'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl)boronic acid (6.70 g, 15.61 mmol)을 테트라하이드로퓨란 200 ml에 완전히 녹인 후 2M 탄산칼륨수용액(100 ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.47 g, 0.41 mmol)을 넣은 후 4 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 테트라하이드로퓨란 210 ml로 재결정하여 상기 화합물 5 (5.7 6 g, 수율 57%)를 얻었다.Compound B (5.92 g, 13.58 mmol), (3'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-) in a 500 ml round bottom flask in a nitrogen atmosphere After completely dissolving biphenyl]-3-yl)boronic acid (6.70 g, 15.61 mmol) in 200 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (100 ml) was added, followed by tetrakis-(triphenylphosphine)palladium (0.47). g, 0.41 mmol) was added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 210 ml of tetrahydrofuran to obtain Compound 5 (5.7 6 g, yield 57%).
MS[M+H]+ = 742MS[M+H] + = 742
제조예Manufacturing example 6 6
질소 분위기에서 500 ml 둥근 바닥 플라스크에 상기 화합물 B (5.26 g, 12.06 mmol), (7-(4,6-diphenyl-1,3,5-triazin-2-yl)-9,9-dimethyl-9H-fluoren-2-yl)boronic acid (6.51 g, 13.87 mmol)을 테트라하이드로퓨란 280 ml에 완전히 녹인 후 2M 탄산칼륨수용액(140 ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.42 g, 0.36 mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 테트라하이드로퓨란 250 ml로 재결정하여 상기 화합물 6 (5.18 g, 수율 76%)을 얻었다.Compound B (5.26 g, 12.06 mmol), (7-(4,6-diphenyl-1,3,5-triazin-2-yl)-9,9-dimethyl-9H in a 500 ml round bottom flask in a nitrogen atmosphere. After completely dissolving -fluoren-2-yl)boronic acid (6.51 g, 13.87 mmol) in 280 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (140 ml) was added, and tetrakis-(triphenylphosphine)palladium (0.42 g, 0.36 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 ml of tetrahydrofuran to obtain the compound 6 (5.18 g, yield 76%).
MS[M+H]+ = 782MS[M+H] + = 782
제조예Manufacturing example 7 7
질소 분위기에서 500 ml 둥근 바닥 플라스크에 상기 화합물 B (6.12 g, 14.04mmol), (3-(2,6-diphenylpyrimidin-4-yl)phenyl)boronic acid(5.68g, 16.14mmol)을 테트라하이드로퓨란 210 ml에 완전히 녹인 후 2M 탄산칼륨수용액(105 ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.49 g, 0.42 mmol)을 넣은 후 4 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에틸아세테이트 240 ml로 재결정하여 상기 화합물 7 (6.34 g, 수율 68%)을 얻었다.Compound B (6.12 g, 14.04mmol), (3-(2,6-diphenylpyrimidin-4-yl)phenyl)boronic acid (5.68g, 16.14mmol) was added to tetrahydrofuran 210 in a 500 ml round bottom flask in a nitrogen atmosphere. After completely dissolving in ml, 2M aqueous potassium carbonate solution (105 ml) was added, tetrakis-(triphenylphosphine)palladium (0.49 g, 0.42 mmol) was added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 240 ml of ethyl acetate to give the compound 7 (6.34 g, yield 68%).
MS[M+H]+ = 665MS[M+H] + = 665
제조예Manufacturing example 8 8
질소 분위기에서 500 ml 둥근 바닥 플라스크에 상기 화합물 C (5.55 g, 12.73 mmol), (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (5.17 g, 14.64 mmol)을 테트라하이드로퓨란 200 ml에 완전히 녹인 후 2M 탄산칼륨수용액(100 ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.44 g, 0.38 mmol)을 넣은 후 5 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 테트라하이드로퓨란 190 ml로 재결정하여 화합물 8 (6.62 g, 수율 78%)을 얻었다.Compound C (5.55 g, 12.73 mmol), (4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (5.17 g,) in a 500 ml round bottom flask in a nitrogen atmosphere 14.64 mmol) was completely dissolved in 200 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (100 ml) was added, tetrakis-(triphenylphosphine) palladium (0.44 g, 0.38 mmol) was added, followed by heating and stirring for 5 hours. I did. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 190 ml of tetrahydrofuran to obtain compound 8 (6.62 g, yield 78%).
MS[M+H]+ = 666MS[M+H] + = 666
제조예Manufacturing example 9 9
질소 분위기에서 500 ml 둥근 바닥 플라스크에 상기 화합물 C (4.92 g, 11.28mmol), (3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (4.58g, 12.98mmol)을 테트라하이드로퓨란 160 ml에 완전히 녹인 후 2M 탄산칼륨수용액(80 ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.39 g, 0.34 mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 테트라하이드로퓨란 210 ml로 재결정하여 상기 화합물 9 (5.16 g, 수율 69%)를 얻었다.Compound C (4.92 g, 11.28 mmol), (3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (4.58 g,) in a 500 ml round bottom flask in a nitrogen atmosphere 12.98mmol) was completely dissolved in 160 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (80 ml) was added, tetrakis-(triphenylphosphine) palladium (0.39 g, 0.34 mmol) was added, followed by heating and stirring for 3 hours. I did. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 210 ml of tetrahydrofuran to obtain the compound 9 (5.16 g, yield 69%).
MS[M+H]+ = 666MS[M+H] + = 666
제조예Manufacturing example 10 10
질소 분위기에서 500 ml 둥근 바닥 플라스크에 상기 화합물 A (5.36 g, 12.29 mmol), (3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (6.07 g, 14.14 mmol)을 테트라하이드로퓨란 260 ml에 완전히 녹인 후 2M 탄산칼륨수용액(130 ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.43 g, 0.37 mmol)을 넣은 후 4 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에틸아세테이트 210 ml로 재결정하여 상기 화합물 10 (6.12 g, 수율 67%)을 얻었다.Compound A (5.36 g, 12.29 mmol), (3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (6.07 g,) in a 500 ml round bottom flask in a nitrogen atmosphere 14.14 mmol) was completely dissolved in 260 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (130 ml) was added, tetrakis-(triphenylphosphine) palladium (0.43 g, 0.37 mmol) was added, followed by heating and stirring for 4 hours. I did. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 210 ml of ethyl acetate to obtain the compound 10 (6.12 g, yield 67%).
MS[M+H]+ = 742MS[M+H] + = 742
제조예Manufacturing example 11 11
질소 분위기에서 500 ml 둥근 바닥 플라스크에 상기 화합물 A-1 (13.40 g, 27.69 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.43 g, 24.08 mmol)을 테트라하이드로퓨란 200 ml에 완전히 녹인 후 2M 탄산칼륨수용액(100 ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.83 g, 0.72 mmol)을 넣은 후 4 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 아세트니트릴 290 ml로 재결정하여 상기 화합물 11 (10.67 g, 수율 75%)을 얻었다.Compound A-1 (13.40 g, 27.69 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.43 g, 24.08 mmol) was added to tetrahydrofuran in a 500 ml round bottom flask in a nitrogen atmosphere. After completely dissolving in 200 ml, a 2M aqueous potassium carbonate solution (100 ml) was added, tetrakis-(triphenylphosphine) palladium (0.83 g, 0.72 mmol) was added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 290 ml of acetonitrile to obtain the compound 11 (10.67 g, yield 75%).
MS[M+H]+ = 590MS[M+H] + = 590
제조예Manufacturing example 12 12
질소 분위기에서 500 ml 둥근 바닥 플라스크에 상기 화합물 A-1 (8.03 g, 16.60 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (4.95 g, 14.43 mmol)을 테트라하이드로퓨란 160 ml에 완전히 녹인 후 2M 탄산칼륨수용액(80 ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.50 g, 0.43 mmol)을 넣은 후 4 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 아세트니트릴 230 ml로 재결정하여 상기 화합물 12 (7.65 g, 수율 80%)를 얻었다.Compound A-1 (8.03 g, 16.60 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3 in a 500 ml round bottom flask in a nitrogen atmosphere ,5-triazine (4.95 g, 14.43 mmol) was completely dissolved in 160 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (80 ml) was added, and tetrakis-(triphenylphosphine) palladium (0.50 g, 0.43 mmol) After putting it, it was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 230 ml of acetonitrile to obtain the compound 12 (7.65 g, yield 80%).
MS[M+H]+ = 590MS[M+H] + = 590
제조예Manufacturing example 13 13
질소 분위기에서 500 ml 둥근 바닥 플라스크에 상기 화합물 A-1 (11.24 g, 23.22 mmol), 4-chloro-2,6-diphenylpyrimidine (5.37 g, 20.19 mmol)을 테트라하이드로퓨란 220 ml에 완전히 녹인 후 2M 탄산칼륨수용액(110 ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.70 g, 0.61 mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 아세트니트릴 220 ml로 재결정하여 상기 화합물 13 (8.52 g, 수율 72%)을 얻었다.Compound A-1 (11.24 g, 23.22 mmol) and 4-chloro-2,6-diphenylpyrimidine (5.37 g, 20.19 mmol) were completely dissolved in 220 ml of tetrahydrofuran in a 500 ml round bottom flask in a nitrogen atmosphere, and then 2M carbonic acid. Potassium aqueous solution (110 ml) was added, tetrakis-(triphenylphosphine) palladium (0.70 g, 0.61 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 220 ml of acetonitrile to obtain the compound 13 (8.52 g, yield 72%).
MS[M+H]+ = 589MS[M+H] + = 589
제조예Manufacturing example 14 14
질소 분위기에서 500 ml 둥근 바닥 플라스크에 상기 화합물 B-1 (7.93 g, 16.38 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine (4.87 g, 14.24 mmol)을 테트라하이드로퓨란 180 ml에 완전히 녹인 후 2M 탄산칼륨수용액(90 ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.49 g, 0.43 mmol)을 넣은 후 2 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에틸아세테이트 260 ml로 재결정하여 상기 화합물 14 (6.28 g, 수율 6%)를 얻었다.Compound B-1 (7.93 g, 16.38 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenylpyrimidine (4.87 g, above) in a 500 ml round bottom flask in a nitrogen atmosphere 14.24 mmol) was completely dissolved in 180 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (90 ml) was added, tetrakis-(triphenylphosphine) palladium (0.49 g, 0.43 mmol) was added, followed by heating and stirring for 2 hours. I did. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with ethyl acetate 260 ml to obtain the compound 14 (6.28 g, yield 6%).
MS[M+H]+ = 665MS[M+H] + = 665
제조예Manufacturing example 15 15
질소 분위기에서 500 ml 둥근 바닥 플라스크에 상기 화합물 B-1 (12.31 g, 25.43 mmol), 2-chloro-4,6-diphenylpyridine (5.86 g, 22.11 mmol)을 테트라하이드로퓨란 240 ml에 완전히 녹인 후 2M 탄산칼륨수용액(120 ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.77 g, 0.66 mmol)을 넣은 후 4 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에탄올 180 ml로 재결정하여 상기 화합물 15 (7.76 g, 수율 60%)를 얻었다.Compound B-1 (12.31 g, 25.43 mmol) and 2-chloro-4,6-diphenylpyridine (5.86 g, 22.11 mmol) were completely dissolved in 240 ml of tetrahydrofuran in a 500 ml round-bottom flask in a nitrogen atmosphere, and then 2M carbonic acid. Potassium aqueous solution (120 ml) was added, tetrakis-(triphenylphosphine) palladium (0.77 g, 0.66 mmol) was added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with ethanol 180 ml to obtain the compound 15 (7.76 g, yield 60%).
MS[M+H]+ = 588MS[M+H] + = 588
제조예Manufacturing example 16 16
질소 분위기에서 500 ml 둥근 바닥 플라스크에 상기 화합물 A-1 (7.20 g, 14.88 mmol), 4'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-carbonitrile (4.76 g, 12.93 mmol)을 테트라하이드로퓨란 140 ml에 완전히 녹인 후 2M 탄산칼륨수용액(70 ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.45 g, 0.39 mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에틸아세테이트 250 ml로 재결정하여 상기 화합물 16 (6.30 g, 수율 70%)을 얻었다.Compound A-1 (7.20 g, 14.88 mmol), 4'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1, above in a 500 ml round bottom flask in a nitrogen atmosphere After completely dissolving 1'-biphenyl]-3-carbonitrile (4.76 g, 12.93 mmol) in 140 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (70 ml) was added, and tetrakis-(triphenylphosphine)palladium (0.45 g, 0.39 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 ml of ethyl acetate to give the compound 16 (6.30 g, yield 70%).
MS[M+H]+ = 691MS[M+H] + = 691
제조예Manufacturing example 17 17
질소 분위기에서 500 ml 둥근 바닥 플라스크에 상기 화합물 C-1 (7.70 g, 15.92 mmol), 2-chloro-4,6-di(naphthalen-1-yl)-1,3,5-triazine (5.08 g, 13.84 mmol)을 테트라하이드로퓨란 220 ml에 완전히 녹인 후 2M 탄산칼륨수용액(110 ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.48 g, 0.42 mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에틸아세테이트 260 ml로 재결정하여 상기 화합물 17 (7.26 g, 수율 76%)을 얻었다.Compound C-1 (7.70 g, 15.92 mmol), 2-chloro-4,6-di(naphthalen-1-yl)-1,3,5-triazine (5.08 g, 13.84 mmol) was completely dissolved in 220 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (110 ml) was added, tetrakis-(triphenylphosphine) palladium (0.48 g, 0.42 mmol) was added, followed by heating and stirring for 3 hours. I did. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with ethyl acetate 260 ml to obtain the compound 17 (7.26 g, yield 76%).
MS[M+H]+ = 690MS[M+H] + = 690
제조예Manufacturing example 18 18
질소 분위기에서 500 ml 둥근 바닥 플라스크에 상기 화합물 B-1 (8.74 g, 18.05 mmol), 2-chloro-4,6-di(naphthalen-2-yl)-1,3,5-triazine (5.76 g, 15.69 mmol)을 테트라하이드로퓨란 260 ml에 완전히 녹인 후 2M 탄산칼륨수용액(130 ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.54 g, 0.47 mmol)을 넣은 후 4 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에틸아세테이트 220 ml로 재결정하여 상기 화합물 18 (6.27 g, 수율 58%)을 얻었다.Compound B-1 (8.74 g, 18.05 mmol), 2-chloro-4,6-di(naphthalen-2-yl)-1,3,5-triazine (5.76 g, above) in a 500 ml round bottom flask in a nitrogen atmosphere 15.69 mmol) was completely dissolved in 260 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (130 ml) was added, tetrakis-(triphenylphosphine) palladium (0.54 g, 0.47 mmol) was added, followed by heating and stirring for 4 hours. I did. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 220 ml of ethyl acetate to obtain the compound 18 (6.27 g, yield 58%).
MS[M+H]+ = 690MS[M+H] + = 690
제조예Manufacturing example 19 19
질소 분위기에서 500 ml 둥근 바닥 플라스크에 상기 화합물 A-1 (8.66 g, 17.90 mmol), 2-chloro-4-(9,9-dimethyl-9H-fluoren-2-yl)-6-phenyl-1,3,5-triazine (5.96 g, 15.56 mmol)을 테트라하이드로퓨란 180 ml에 완전히 녹인 후 2M 탄산칼륨수용액(90 ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.54 g, 0.47 mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에틸아세테이트 260 ml로 재결정하여 상기 화합물 19 (5.29 g, 수율 48%)를 얻었다.Compound A-1 (8.66 g, 17.90 mmol), 2-chloro-4-(9,9-dimethyl-9H-fluoren-2-yl)-6-phenyl-1, in a 500 ml round bottom flask in a
MS[M+H]+ = 706MS[M+H] + = 706
제조예Manufacturing example 20 20
질소 분위기에서 500 ml 둥근 바닥 플라스크에 상기 화합물 A-1 (9.15 g, 18.90 mmol), 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine (6.13 g, 16.43 mmol)을 테트라하이드로퓨란 220 ml에 완전히 녹인 후 2M 탄산칼륨수용액(110 ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.57 g, 0.49 mmol)을 넣은 후 4 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에틸아세테이트 260 ml로 재결정하여 상기 화합물 20 (5.29 g, 수율 48%)을 얻었다.Compound A-1 (9.15 g, 18.90 mmol), 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3, in a 500 ml round bottom flask in a nitrogen atmosphere After completely dissolving 5-triazine (6.13 g, 16.43 mmol) in 220 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (110 ml) was added, and tetrakis-(triphenylphosphine) palladium (0.57 g, 0.49 mmol) was added. After adding, the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with ethyl acetate 260 ml to obtain the compound 20 (5.29 g, yield 48%).
MS[M+H]+ = 696MS[M+H] + = 696
제조예Manufacturing example 21 21
질소 분위기에서 500 ml 둥근 바닥 플라스크에 상기 화합물 C-1 (6.83 g, 14.10 mmol), 2-chloro-4-(phenanthren-9-yl)-6-(triphenylen-2-yl)-1,3,5-triazine (6.34 g, 12.26 mmol)을 테트라하이드로퓨란 240 ml에 완전히 녹인 후 2M 탄산칼륨수용액(120 ml)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.43 g, 0.37 mmol)을 넣은 후 5 시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에틸아세테이트 260 ml로 재결정하여 상기 화합물 21 (7.26 g, 수율 76%)을 얻었다.Compound C-1 (6.83 g, 14.10 mmol), 2-chloro-4-(phenanthren-9-yl)-6-(triphenylen-2-yl)-1,3, in a 500 ml round bottom flask in a nitrogen atmosphere After completely dissolving 5-triazine (6.34 g, 12.26 mmol) in 240 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (120 ml) was added, and tetrakis-(triphenylphosphine) palladium (0.43 g, 0.37 mmol) was added. After adding, the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with ethyl acetate 260 ml to obtain the compound 21 (7.26 g, yield 76%).
MS[M+H]+ = 840MS[M+H] + = 840
비교예Comparative example 1-1 1-1
ITO(indium tin oxide)가 1,000 Å의 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 10 분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다.A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1,000 Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. 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 하기 화학식의 헥사니트릴 헥사아자트리페닐렌 (hexaazatriphenylene; HAT)를 50 Å의 두께로 열 진공 증착하여 정공 주입층을 형성하였다.On the thus prepared ITO transparent electrode, hexaazatriphenylene (HAT) of the following formula was thermally vacuum deposited to a thickness of 50 Å to form a hole injection layer.
상기 정공 주입층 위에 정공을 수송하는 물질인 하기 화합물 HT 1 (4,4'-(9-phenyl-9H-carbazole-3,6-diyl)bis(N,N-diphenylaniline))을 1300 Å의 두께로 진공 증착하여 정공 수송층을 형성하였다.The following compound, HT 1 (4,4'-(9-phenyl-9H-carbazole-3,6-diyl)bis(N,N-diphenylaniline)), which is a material for transporting holes on the hole injection layer, is 1300 Å A hole transport layer was formed by vacuum vapor deposition.
이어서, 상기 정공 수송층 위에 막 두께 150 Å으로 하기 화합물 EB 1을 진공 증착하여 전자 저지층을 형성하였다.Subsequently, the following
이어서, 상기 전자 저지층 위에 막 두께 200 Å으로 하기 화합물 BH와 화합물 BD를 25:1의 중량비로 진공증착하여 발광층을 형성하였다.Subsequently, a light emitting layer was formed by vacuum depositing the following compound BH and compound BD at a weight ratio of 25:1 on the electron blocking layer with a film thickness of 200 Å.
상기 발광층 위에 상기 정공 수송층 위에 막 두께 50 Å으로 하기 화합물 HB 1을 진공 증착하여 정공 저지층을 형성하였다.A hole blocking layer was formed by vacuum-depositing the following
이어서, 상기 정공 저지층 위에 하기 화합물 ET 1과 하기 화합물 LiQ(Lithium Quinolate)를 1:1의 중량비로 진공증착하여 310 Å의 두께로 전자 주입 및 수송층을 형성하였다.Subsequently, the following
상기 전자 주입 및 수송층 위에 순차적으로 12 Å두께로 리튬플로라이드(LiF)와 1,000 Å 두께로 알루미늄을 증착하여 음극을 형성하였다.Lithium fluoride (LiF) with a thickness of 12 Å and aluminum with a thickness of 1,000 Å were sequentially deposited on the electron injection and transport layer to form a negative electrode.
상기의 과정에서 유기물의 증착속도는 0.4 내지 0.7 Å/sec를 유지하였고, 음극의 리튬플로라이드는 0.3 Å/sec, 알루미늄은 2 Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 2X10-7 torr 내지 5X10-6 torr를 유지하여, 유기 발광 소자를 제조하였다.In the above process, the deposition rate of organic materials was maintained at 0.4 to 0.7 Å/sec, lithium fluoride at the cathode was maintained at a deposition rate of 0.3 Å/sec, and for
실시예Example 1-1 내지 1-11 1-1 to 1-11
상기 비교예 1-1에서 화합물 HB 1 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that the compound shown in Table 1 below was used instead of the
비교예Comparative example 1-2 내지 1-4 1-2 to 1-4
상기 비교예 1-1에서 화합물 HB 1 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제조하였다. 하기 표 1에서 화합물 HB 2, HB 3 및 HB 4는 다음과 같다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that the compound shown in Table 1 below was used instead of the
시험예Test example 1 One
상기 실시예 1-1 내지 1-11 및 비교예 1-1 내지 1-4에서 제조한 유기 발광 소자에 전류를 인가하였을 때, 전압, 효율, 색좌표 및 수명을 측정하고 그 결과를 하기 표 1에 나타내었다. T95은 휘도가 초기 휘도(1300 nit)에서 95%로 감소되는데 소요되는 시간을 의미한다.When a current was applied to the organic light emitting devices prepared in Examples 1-1 to 1-11 and Comparative Examples 1-1 to 1-4, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. Indicated. T95 refers to the time it takes for the luminance to decrease from the initial luminance (1300 nit) to 95%.
(정공차단층)compound
(Hole Blocking Layer)
(V@10mA
/cm2)Voltage
(V@10mA
/cm 2 )
(cd/A@10mA
/cm2)efficiency
(cd/A@10mA
/cm 2 )
(x,y)Color coordinates
(x,y)
(hr)T95
(hr)
상기 표 1에서 보는 바와 같이, 본원 발명의 화합물을 정공차단층으로 사용하여 제조된 유기 발광 소자의 경우에 유기 발광 소자의 효율, 구동전압 및/또는 안정성 면에서 우수한 특성을 나타낸다.As shown in Table 1, in the case of an organic light-emitting device manufactured using the compound of the present invention as a hole blocking layer, the organic light-emitting device exhibits excellent characteristics in terms of efficiency, driving voltage and/or stability.
fluorene 계열의 HB 2 내리 HB 4를 정공차단층으로 사용하여 제조된 유기 발광 소자보다 저전압, 고효율 및 장수명의 특성을 보인다.Compared to an organic light-emitting device manufactured using fluorene-based
본 발명의 코어는 Spirobifluorene, 9,10-diphenylfluorene 및 9,10-dimetylfluorene 코어보다 전자의 함량이 상대적으로 높으며 정공차단층으로 사용하였을 때 전압 및 효율에서 강점을 보이는 동시에 수명이 크게 상승하는 결과를 얻었다.The core of the present invention has a relatively higher electron content than the Spirobifluorene, 9,10-diphenylfluorene, and 9,10-dimetylfluorene cores, and when used as a hole blocking layer, it has strengths in voltage and efficiency, and the lifespan is significantly increased. .
상기 표 1의 결과와 같이, 본 발명에 다른 화합물은 정공 차단 능력이 우수하여 유기 발광 소자에 적용 가능함을 확인할 수 있었다.As shown in the results of Table 1, it was confirmed that the other compounds in the present invention have excellent hole blocking ability and thus can be applied to an organic light-emitting device.
실시예Example 2-1 내지 2-21 2-1 to 2-21
상기 비교예 1-1에서 전자수송층의 형성에 화합물 ET 1 대신 하기 표 2에 기재된 화합물을 사용하는 것을 제외하고는, 상기 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that the compound shown in Table 2 below was used instead of the
비교예Comparative example 2-1 내지 2-3 2-1 to 2-3
상기 비교예 1-1에서 전자수송층의 형성에 화합물 ET 1 대신 하기 표 2에 기재된 화합물을 사용하는 것을 제외하고는, 상기 비교예 1-1과 동일한 방법으로 유기 발광 소자를 제조하였다. 하기 표 2에서 화합물 ET 2, ET 3 및 ET 4는 다음과 같다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except that the compound shown in Table 2 below was used instead of the
시험예Test example 2 2
상기 실시예 2-1 내지 2-21 및 비교예 2-1 내지 2-3에서 제조한 유기 발광 소자에 전류를 인가하였을 때, 전압, 효율, 색좌표 및 수명을 측정하고 그 결과를 하기 표 2에 나타내었다. T95은 휘도가 초기 휘도(1300 nit)에서 95%로 감소되는데 소요되는 시간을 의미한다.When current was applied to the organic light emitting devices prepared in Examples 2-1 to 2-21 and Comparative Examples 2-1 to 2-3, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 2 below. Indicated. T95 refers to the time it takes for the luminance to decrease from the initial luminance (1300 nit) to 95%.
(전자수송층)compound
(Electron transport layer)
(V@10mA
/cm2)Voltage
(V@10mA
/cm 2 )
(cd/A@10mA
/cm2)efficiency
(cd/A@10mA
/cm 2 )
(x,y)Color coordinates
(x,y)
(hr)T95
(hr)
상기 표 2에서 보는 바와 같이, 본원 발명의 화합물을 전자수송층으로 사용하여 제조된 유기 발광 소자의 경우에 유기 발광 소자의 효율, 구동전압 및/또는 안정성 면에서 우수한 특성을 나타낸다.As shown in Table 2, in the case of an organic light-emitting device manufactured using the compound of the present invention as an electron transport layer, the organic light-emitting device exhibits excellent characteristics in terms of efficiency, driving voltage, and/or stability.
Spirobifluorene 코어의 비교예 4, 9,10-diphenylfluorene 코어의 비교예 5 및 9,10-dimetylfluorene 코어의 비교예 6의 화합물을 전자수송층으로 사용하여 제조된 유기 발광 소자보다 저전압, 고효율 및 장수명의 특성을 보인다.Compared to the organic light emitting device manufactured by using the compounds of Comparative Example 4 of Spirobifluorene Core, Comparative Example 5 of 9,10-diphenylfluorene Core and Comparative Example 6 of 9,10-dimetylfluorene core as an electron transport layer, characteristics of low voltage, high efficiency, and long life were obtained. see.
본 발명의 코어는 Spirobifluorene, 9,10-diphenylfluorene 및 9,10-dimetylfluorene 코어보다 전자의 함량이 상대적으로 높으며 전자수송층으로 사용하였을 때 수명이 20%~30% 상승하면서 전압 및 효율에서도 강점을 보인다는 결과를 얻었다.The core of the present invention has a relatively higher electron content than the Spirobifluorene, 9,10-diphenylfluorene and 9,10-dimetylfluorene cores, and when used as an electron transport layer, the lifespan is increased by 20% to 30%, showing strengths in voltage and efficiency. I got the result.
이상을 통해 본 발명의 바람직한 실시예에 대하여 설명하였지만, 본 발명은 이에 한정되는 것이 아니고 청구범위와 발명의 상세한 설명의 범위 안에서 여러 가지로 변형하여 실시하는 것이 가능하고 이 또한 발명의 범주에 속한다.Although preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the claims and the detailed description of the invention, and this also belongs to the scope of the invention.
1: 기판
2: 양극
3: 발광층
4: 음극
5: 정공 주입층
6: 정공 수송층
7: 발광층
8: 전자 수송층1: substrate
2: anode
3: light emitting layer
4: cathode
5: hole injection layer
6: hole transport layer
7: light emitting layer
8: electron transport layer
Claims (7)
[화학식 1]
상기 화학식 1에서,
R1은 각각 독립적으로 메틸기 또는 페닐기이고,
L1 은 직접 결합, , , 또는 이고,
X1, X2 및 X3는 각각 독립적으로 N 또는 C(Ra)로서, 상기 X1, X2 및 X3 중 적어도 하나는 N이고,
Ra는 수소이고,
Ar1 및 Ar2는 각각 독립적으로 , , , , , , , , , , , , 또는 이다.
Compound represented by the following formula (1):
[Formula 1]
In Formula 1,
Each R 1 is independently a methyl group or a phenyl group,
L 1 is a direct bond, , , or ego,
X 1 , X 2 and X 3 are each independently N or C (R a ), wherein at least one of X 1 , X 2 and X 3 is N,
R a is hydrogen,
Ar 1 and Ar 2 are each independently , , , , , , , , , , , , or to be.
상기 화학식 1은 하기 화학식 2-a 내지 2-c 중 어느 하나로 표시되는,
화합물:
[화학식 2-a]
[화학식 2-b]
[화학식 2-c]
상기 화학식 2-a 내지 2-c에서,
R1, L1, X1, X2, X3, Ar1, 및 Ar2는 각각 상기 화학식 1에서 정의된 바와 같다.
The method of claim 1,
Formula 1 is represented by any one of the following Formulas 2-a to 2-c,
compound:
[Formula 2-a]
[Formula 2-b]
[Formula 2-c]
In Formulas 2-a to 2-c,
R 1 , L 1 , X 1 , X 2 , X 3 , Ar 1 , and Ar 2 are each as defined in Formula 1 above.
상기 화학식 1로 표시되는 화합물은 하기로 구성되는 군으로부터 선택된 어느 하나인, 화합물.
The method of claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of:
상기 유기물층 중 적어도 한 층은 제 1 항의 화학식 1로 표시되는 화합물을 포함하는 것인, 유기 전계 발광 소자.An organic electroluminescent device comprising a first electrode, a second electrode provided opposite to the first electrode, and one or more organic material layers provided between the first electrode and the second electrode;
At least one layer of the organic material layer comprises a compound represented by Formula 1 of claim 1, wherein the organic electroluminescent device.
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