KR102592082B1 - Novel compound and organic light emitting device comprising the same - Google Patents
Novel compound and organic light emitting device comprising the same Download PDFInfo
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- KR102592082B1 KR102592082B1 KR1020200003805A KR20200003805A KR102592082B1 KR 102592082 B1 KR102592082 B1 KR 102592082B1 KR 1020200003805 A KR1020200003805 A KR 1020200003805A KR 20200003805 A KR20200003805 A KR 20200003805A KR 102592082 B1 KR102592082 B1 KR 102592082B1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 127
- -1 biphenylyl Chemical group 0.000 claims description 67
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 239000011368 organic material Substances 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000006819 (C2-60) heteroaryl group Chemical group 0.000 claims description 8
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- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 5
- 229910052805 deuterium Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004431 deuterium atom Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
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- 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 14
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- 230000000052 comparative effect Effects 0.000 description 8
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
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- RQYIRZGKJJIGSU-UHFFFAOYSA-N 8-bromo-1-chlorodibenzofuran Chemical compound Clc1cccc2oc3ccc(Br)cc3c12 RQYIRZGKJJIGSU-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
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- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 4
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- 238000006069 Suzuki reaction reaction Methods 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 4
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
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- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
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- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
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- 230000008021 deposition Effects 0.000 description 3
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- OCUXAWVQPORIBP-UHFFFAOYSA-N 2,5-dibromo-1,3-difluorobenzene Chemical compound FC1=CC(Br)=CC(F)=C1Br OCUXAWVQPORIBP-UHFFFAOYSA-N 0.000 description 2
- QCGWGYFVRUSBRM-UHFFFAOYSA-N 2-bromo-7-chlorodibenzofuran Chemical compound BrC1=CC2=C(OC3=C2C=CC(=C3)Cl)C=C1 QCGWGYFVRUSBRM-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- ZPZKLVBUXHZVAC-UHFFFAOYSA-N 3-bromo-7-chlorodibenzofuran Chemical compound BrC=1C=CC2=C(OC3=C2C=CC(=C3)Cl)C=1 ZPZKLVBUXHZVAC-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
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- 239000007983 Tris buffer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
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- 125000004185 ester group Chemical group 0.000 description 2
- 150000002219 fluoranthenes Chemical class 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005241 heteroarylamino group Chemical group 0.000 description 2
- 125000005462 imide group Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
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- 239000000203 mixture Substances 0.000 description 2
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- 238000010992 reflux Methods 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
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- LTBWKAYPXIIVPC-UHFFFAOYSA-N 3-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC(Br)=CC=C3NC2=C1 LTBWKAYPXIIVPC-UHFFFAOYSA-N 0.000 description 1
- AZFABGHLDGJASW-UHFFFAOYSA-N 3-bromodibenzofuran Chemical compound C1=CC=C2C3=CC=C(Br)C=C3OC2=C1 AZFABGHLDGJASW-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
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- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
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- QWTDLAXBXQFSGC-UHFFFAOYSA-N 7-bromo-1-chlorodibenzofuran Chemical compound C1=CC2=C(C3=C(O2)C=C(C=C3)Br)C(=C1)Cl QWTDLAXBXQFSGC-UHFFFAOYSA-N 0.000 description 1
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- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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Abstract
본 발명은 신규한 화합물 및 이를 이용한 유기 발광 소자를 제공한다.The present invention provides a novel compound and an organic light-emitting device using the same.
Description
본 발명은 신규한 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.The present invention relates to novel compounds and organic light-emitting devices containing them.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 넓은 시야각, 우수한 콘트라스트, 빠른 응답 시간을 가지며, 휘도, 구동 전압 및 응답 속도 특성이 우수하여 많은 연구가 진행되고 있다. In general, organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light-emitting devices using the organic light-emitting phenomenon have a wide viewing angle, excellent contrast, fast response time, and excellent luminance, driving voltage, and response speed characteristics, so much research is 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. Organic light emitting devices generally have a structure including an anode, a cathode, and an organic layer between the anode and the cathode. The organic material layer is often composed of a multi-layer structure made of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton is When it falls back to the ground state, it glows.
상기와 같은 유기 발광 소자에 사용되는 유기물에 대하여 새로운 재료의 개발이 지속적으로 요구되고 있다.The development of new materials for organic materials used in organic light-emitting devices as described above is continuously required.
본 발명은 신규한 유기발광 재료 및 이를 포함하는 유기 발광 소자에 관한 것이다.The present invention relates to novel organic light-emitting materials and organic light-emitting devices containing the same.
본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:The present invention provides a compound represented by the following formula (1):
[화학식 1][Formula 1]
상기 화학식 1에서,In Formula 1,
X는 O 또는 S이고,X is O or S,
Z1 내지 Z3는 각각 독립적으로, CH 또는 N이고, 단 Z1 내지 Z3 중 적어도 하나는 N이고,Z 1 to Z 3 are each independently CH or N, provided that at least one of Z 1 to Z 3 is N,
Ar1 및 Ar2는 각각 독립적으로, 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴이고,Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 aryl; or C 2-60 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted N, O and S,
R1 및 R2는 각각 독립적으로, 수소; 중수소; 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴이고,R 1 and R 2 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 6-60 aryl; or C 2-60 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted N, O and S,
a1 및 a2는 각각 독립적으로, 0 내지 3의 정수이고,a1 and a2 are each independently an integer from 0 to 3,
A는 하기 화학식 1A로 표시되고;A is represented by the following formula 1A;
[화학식 1A][Formula 1A]
상기 화학식 1A에서,In Formula 1A,
X1 내지 X10은 각각 독립적으로, CH 또는 N이고,X 1 to X 10 are each independently CH or N,
Y1 및 Y2는 각각 독립적으로, O 또는 S이다.Y 1 and Y 2 are each independently O or S.
또한, 본 발명은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는, 유기 발광 소자를 제공한다.In addition, the present invention includes a first electrode; a second electrode provided opposite to the first electrode; and an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Formula 1. .
상술한 화학식 1로 표시되는 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있으며, 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는 수명 특성을 향상시킬 수 있다. 특히, 상술한 화학식 1로 표시되는 화합물은 정공주입, 정공수송, 정공주입 및 수송, 발광, 전자수송, 또는 전자주입 재료로 사용될 수 있다.The compound represented by the above-described formula 1 can be used as a material for the organic layer of an organic light-emitting device, and can improve efficiency, low driving voltage, and/or lifespan characteristics of the organic light-emitting device. In particular, the compound represented by the above-mentioned formula 1 can be used as a hole injection, hole transport, hole injection and transport, light emitting, electron transport, or electron injection material.
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), 전자저지층(7), 발광층(3), 정공저지층(8), 전자수송층(9), 전자주입층(10) 및 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. Figure 1 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (3), a hole blocking layer (8), and an electron transport layer (9). , shows an example of an organic light-emitting device consisting of an electron injection layer 10 and a cathode 4.
이하, 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다.Hereinafter, the present invention will be described in more detail to aid understanding.
본 발명은 상기 화학식 1로 표시되는 화합물을 제공한다. The present invention provides a compound represented by Formula 1 above.
본 명세서에서, 또는 는 다른 치환기에 연결되는 결합을 의미한다. In this specification, or means a bond connected to another substituent.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 사이클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환 또는 비치환된 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 비페닐기일 수 있다. 즉, 비페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다.As used herein, the term “substituted or unsubstituted” refers to deuterium; halogen group; Nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkylthioxy group; Arylthioxy group; Alkyl sulphoxy group; Aryl sulfoxy 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 substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups containing one or more of N, O and S atoms, or substituted or unsubstituted with two or more of the above-exemplified substituents linked. . For example, “a substituent group in which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it 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 this specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound with the following structure, but is not limited thereto.
본 명세서에 있어서, 에스테르기는 에스테르기의 산소가 탄소수 1 내지 25의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 25의 아릴기로 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the oxygen of the ester group may be substituted with a straight-chain, branched-chain, or ring-chain alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In this specification, the carbon number of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound with 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 trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited to this.
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 trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, and phenyl boron group, but is not limited thereto.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In this specification, examples of halogen groups include fluorine, chlorine, bromine, or iodine.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 6이다. 알킬기의 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 사이클로펜틸메틸, 사이클로헥실메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸펜틸, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이들에 한정되지 않는다.In the present specification, the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. According to another embodiment, the carbon number of the alkyl group is 1 to 6. Specific examples of alkyl groups 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, etc., but is not limited to these.
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 straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another 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, etc., but are not limited to these.
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 one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, Examples include, but are not limited to, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl.
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 one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as a phenyl group, biphenyl group, or terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. 상기 플루오레닐기가 치환되는 경우, 등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. When the fluorenyl group is substituted, It can be etc. However, it is not limited to this.
본 명세서에 있어서, 헤테로고리기는 이종 원소로 O, N, Si 및 S 중 1개 이상을 포함하는 헤테로고리기로서, 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로고리기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 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 containing one or more of O, N, Si, and S as a heterogeneous element, and the number of carbon atoms 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, triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, Examples include isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, and dibenzofuranyl group, but are not limited to these.
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 this specification, the aryl group among the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above. In this specification, the aralkyl group, alkylaryl group, and alkylamine group are the same as the examples of the alkyl group described above. In the present specification, the description regarding the heterocyclic group described above may be applied to heteroaryl among heteroarylamines. In this specification, the alkenyl group among the aralkenyl groups is the same as the example of the alkenyl group described above. In the present specification, the description of the aryl group described above can be applied, except that arylene is a divalent group. In the present specification, the description of the heterocyclic group described above can be applied, except that heteroarylene is a divalent group. In the present specification, the description of the aryl group or cycloalkyl group described above can be applied, except that the hydrocarbon ring is not monovalent and is formed by combining two substituents. In the present specification, the description of the heterocyclic group described above can be applied, except that the heterocycle is not a monovalent group and is formed by combining two substituents.
바람직하게는, A는 하기로 구성되는 군으로부터 선택되는 어느 하나일 수 있다:Preferably, A may be any one selected from the group consisting of:
상기 군에서,In the above group,
Y1 및 Y2에 대한 설명은 상기 화학식 1에서 정의한 바와 같다.The description of Y 1 and Y 2 is as defined in Formula 1 above.
바람직하게는, X1 및 X2는 서로 동일할 수 있다.Preferably, X 1 and X 2 may be identical to each other.
바람직하게는, X3 및 X10은 서로 동일하고, X4 및 X9은 서로 동일하고, X5 및 X8은 서로 동일하고, X6 및 X7은 서로 동일할 수 있다.Preferably, X 3 and X 10 may be equal to each other, X 4 and X 9 may be equal to each other, X 5 and X 8 may be equal to each other, and X 6 and
가장 바람직하게는, X1 및 X2는 서로 동일하고, X3 및 X10은 서로 동일하고, X4 및 X9은 서로 동일하고, X5 및 X8은 서로 동일하고, X6 및 X7은 서로 동일할 수 있다.Most preferably, X 1 and X 2 are identical to each other, X 3 and X 10 are identical to each other, X 4 and X 9 are identical to each other , may be identical to each other.
바람직하게는, Ar1 및 Ar2는 각각 독립적으로, 치환 또는 비치환된 C6-20 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-20 헤테로아릴일 수 있고,Preferably, Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-20 aryl; Or it may be a C 2-20 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted N, O and S,
보다 바람직하게는, Ar1 및 Ar2는 각각 독립적으로, 페닐, 비페닐릴, 나프틸, 디메틸플루오레닐, 디벤조퓨라닐, 디벤조티오페닐, 또는 5 개의 중수소로 치환된 페닐일 수 있고,More preferably, Ar 1 and Ar 2 may each independently be phenyl, biphenylyl, naphthyl, dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, or phenyl substituted with 5 deuterium atoms. ,
가장 바람직하게는, Ar1 및 Ar2는 각각 독립적으로, 페닐, 비페닐릴, 나프틸, 9,9-디메틸-9H-플루오레닐, 디벤조퓨라닐, 디벤조티오페닐, 또는 5 개의 중수소로 치환된 페닐일 수 있다.Most preferably, Ar 1 and Ar 2 are each independently selected from phenyl, biphenylyl, naphthyl, 9,9-dimethyl-9H-fluorenyl, dibenzofuranyl, dibenzothiophenyl, or 5 deuterium. It may be phenyl substituted.
바람직하게는, Ar1 및 Ar2 중 적어도 하나는 치환 또는 비치환된 C6-20 아릴일 수 있고,Preferably, at least one of Ar 1 and Ar 2 may be substituted or unsubstituted C 6-20 aryl,
보다 바람직하게는, Ar1 및 Ar2 중 적어도 하나는 페닐, 비페닐릴, 또는 5 개의 중수소로 치환된 페닐일 수 있다.More preferably, at least one of Ar 1 and Ar 2 may be phenyl, biphenylyl, or phenyl substituted with 5 deuterium atoms.
바람직하게는, R1 및 R2는 각각 독립적으로, 수소; 중수소; 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,Preferably, R 1 and R 2 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 6-20 aryl; Or it may be a C 2-20 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted N, O and S,
보다 바람직하게는, R1 및 R2는 각각 독립적으로, 수소, 중수소, 또는 페닐일 수 있다.More preferably, R 1 and R 2 may each independently be hydrogen, deuterium, or phenyl.
바람직하게는, a1 및 a2는 각각 독립적으로, 0 또는 1일 수 있다.Preferably, a1 and a2 may each independently be 0 or 1.
상기 화학식 1로 표시되는 화합물의 대표적인 예는 다음과 같다: Representative examples of compounds represented by Formula 1 are as follows:
상기 화학식 1로 표시되는 화합물은, 일례로 하기 반응식 1 또는 반응식2와 같은 제조 방법으로 제조할 수 있으며, 그 외 나머지 화합물도 유사하게 제조할 수 있다.The compound represented by Formula 1 can be prepared, for example, by a manufacturing method such as Scheme 1 or Scheme 2 below, and the remaining compounds can be prepared similarly.
[반응식 1][Scheme 1]
[반응식 2][Scheme 2]
상기 반응식 1 및 2에서, X, Z1 내지 Z3, Ar1, Ar2, R1, R2, a1, a2 및 A는 상기 화학식 1에서 정의한 바와 같으며, Q1 내지 Q6는 각각 독립적으로 할로겐이고, 바람직하게는 Q1 내지 Q6는 각각 독립적으로 클로로 또는 브로모이다. In Schemes 1 and 2 , _ _ is a halogen, and preferably Q 1 to Q 6 are each independently chloro or bromo.
상기 반응식 1 및 2는 스즈키 커플링 반응으로서, 팔라듐 촉매와 염기 존재 하에 수행하는 것이 바람직하며, 스즈키 커플링 반응을 위한 반응기는 당업계에 알려진 바에 따라 변경이 가능하다. 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다.Schemes 1 and 2 are Suzuki coupling reactions, which are preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be changed according to what is known in the art. The manufacturing method may be further detailed in the manufacturing examples described later.
또한, 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다. 일례로, 본 발명은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물 층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는, 유기 발광 소자를 제공한다. Additionally, the present invention provides an organic light-emitting device containing the compound represented by Formula 1 above. In one example, the present invention includes a first electrode; a second electrode provided opposite to the first electrode; and an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Formula 1. do.
본 발명의 유기 발광 소자의 유기물 층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 발광 소자는 유기물 층으로서 정공주입층, 정공수송층, 발광층, 전자차단층, 전자수송층, 전자주입층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기물층을 포함할 수 있다.The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited to this and may include a smaller number of organic material layers.
또한, 상기 유기물 층은 발광층을 포함할 수 있고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 특히, 본 발명에 따른 화합물은 발광층의 호스트로 사용될 수 있다.Additionally, the organic layer may include a light-emitting layer, and the light-emitting layer may include the compound represented by Formula 1. In particular, the compound according to the present invention can be used as a host for a light-emitting layer.
또한, 상기 유기물 층은 정공수송층, 정공주입층, 또는 정공수송 및 정공주입을 동시에 하는 층을 포함할 수 있고, 상기 정공수송층, 정공주입층, 또는 정공수송 및 정공주입을 동시에 하는 층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. In addition, the organic material layer may include a hole transport layer, a hole injection layer, or a layer that simultaneously performs hole transport and hole injection, and the hole transport layer, the hole injection layer, or the layer that performs both hole transport and hole injection has the formula above: It may include a compound represented by 1.
또한, 상기 전자수송층, 전자주입층, 또는 전자수송 및 전자주입을 동시에 하는 층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. Additionally, the electron transport layer, the electron injection layer, or the layer that simultaneously performs electron transport and electron injection may include the compound represented by Formula 1 above.
또한, 상기 유기물 층은 발광층 및 정공수송층을 포함하고, 상기 발광층 또는 정공수송층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. Additionally, the organic layer includes a light-emitting layer and a hole transport layer, and the light-emitting layer or the hole transport layer may include the compound represented by Formula 1.
또한, 본 발명에 따른 유기 발광 소자는, 기판 상에 양극, 1층 이상의 유기물 층 및 음극이 순차적으로 적층된 구조(normal type)의 유기 발광 소자일 수 있다. 또한, 본 발명에 따른 유기 발광 소자는 기판 상에 음극, 1층 이상의 유기물 층 및 양극이 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다. 예컨대, 본 발명의 일실시예에 따른 유기 발광 소자의 구조는 도 1 및 도 2에 예시되어 있다.Additionally, the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Additionally, the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting device according to an embodiment of the present invention is illustrated in Figures 1 and 2.
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), 전자저지층(7), 발광층(3), 정공저지층(8), 전자수송층(9), 전자주입층(10) 및 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 발광층에 포함될 수 있다. Figure 1 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. 2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (3), a hole blocking layer (8), and an electron transport layer (9). , shows an example of an organic light-emitting device consisting of an electron injection layer 10 and a cathode 4. In this structure, the compound represented by Formula 1 may be included in the light-emitting layer.
본 발명에 따른 유기 발광 소자는, 상기 유기물 층 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. 또한, 상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다. The organic light emitting device according to the present invention can be manufactured using materials and methods known in the art, except that at least one of the organic layers includes the compound represented by Formula 1 above. Additionally, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
예컨대, 본 발명에 따른 유기 발광 소자는 기판 상에 제1 전극, 유기물층 및 제2 전극을 순차적으로 적층시켜 제조할 수 있다. 이때, 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(physical Vapor Deposition)방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공주입층, 정공수송층, 발광층 및 전자수송층을 포함하는 유기물 층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시켜 제조할 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수 있다. For example, the organic light emitting device according to the present invention can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, an anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation. It can be manufactured by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
또한, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물 층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.In addition, the compound represented by Formula 1 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution application method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.
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 can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited to this.
일례로, 상기 제1 전극은 양극이고, 상기 제2 전극은 음극이거나, 또는 상기 제1 전극은 음극이고, 상기 제2 전극은 양극이다.In one example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.
상기 양극 물질로는 통상 유기물 층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 상기 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. The anode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer. Specific examples of the anode 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 SnO 2 :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline are included, but are not limited to these.
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 generally preferably a material with a small work function to facilitate electron injection into the organic layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are, but are not limited to, multi-layered materials such as LiF/Al or LiO 2 /Al.
상기 정공주입층은 전극으로부터 정공을 주입하는 층으로, 정공 주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입효과, 발광층 또는 발광재료에 대하여 우수한 정공 주입 효과를 갖고, 발광층에서 생성된 여기자의 전자주입층 또는 전자주입재료에의 이동을 방지하며, 또한, 박막 형성 능력이 우수한 화합물이 바람직하다. 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물 층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrin), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone)계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정 되는 것은 아니다. The hole injection layer is a layer that injects holes from an electrode. The hole injection material has the ability to transport holes, has an excellent hole injection effect at the anode, a light-emitting layer or a light-emitting material, and has an excellent hole injection effect on the light-emitting layer or light-emitting material. A compound that prevents movement of excitons to the electron injection layer or electron injection material and has excellent thin film forming ability is preferred. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. These include organic materials, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited to these.
상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 정공 수송 물질로 양극이나 정공주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light-emitting layer. It is a hole transport material that can receive holes from the anode or hole injection layer and transfer them to the light-emitting layer, and is a material with high mobility for holes. This is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these.
상기 전자저지층은 음극에서 주입된 전자가 발광층에서 재결합되지 않고 정공수송층으로 넘어가는 것을 방지하기 위해 정공수송층과 발광층의 사이에 두는 층으로, 전자억제층으로 불리기도 한다. 전자저지층에는 전자수송층보다 전자 친화력이 작은 물질이 바람직하다.The electron blocking layer is a layer placed between the hole transport layer and the light emitting layer to prevent electrons injected from the cathode from being recombined in the light emitting layer and passing to the hole transport layer, and is also called an electron blocking layer. A material with lower electron affinity than the electron transport layer is preferred for the electron blocking layer.
상기 발광 물질로는 정공수송층과 전자수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 구체적인 예로 8-히드록시-퀴놀린 알루미늄 착물(Alq3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다. The light-emitting material is a material that can emit light in the visible range by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV) series polymer; Spiro compounds; Polyfluorene, rubrene, etc., but are not limited to these.
상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되지 않는다. 바람직하게는, 상기 화학식 1로 표시되는 화합물을 호스트 재료로 포함할 수 있다.The light emitting layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic ring-containing compounds. 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, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives. Preferably, the compound represented by Formula 1 may be included as a host material.
한편, 상기 발광층은 하기 화학식 2로 표시되는 화합물을 더 포함할 수 있다:Meanwhile, the light-emitting layer may further include a compound represented by the following formula (2):
[화학식 2][Formula 2]
상기 화학식 2에서,In Formula 2,
Ar3 및 Ar4는 각각 독립적으로, 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴이고,Ar 3 and Ar 4 are each independently substituted or unsubstituted C 6-60 aryl; or C 2-60 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted N, O and S,
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,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 C 2-60 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted N, O and S,
a3 및 a4는 각각 독립적으로, 0 내지 7의 정수이다.a3 and a4 are each independently integers from 0 to 7.
바람직하게는, 상기 화학식 2로 표시되는 화합물은 화학식 1로 표시되는 화합물과 함께 호스트 재료로 포함될 수 있다.Preferably, the compound represented by Formula 2 may be included as a host material together with the compound represented by Formula 1.
바람직하게는, Ar3 및 Ar4는 각각 독립적으로, 치환 또는 비치환된 C6-20 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-20 헤테로아릴일 수 있고,Preferably, Ar 3 and Ar 4 are each independently substituted or unsubstituted C 6-20 aryl; Or it may be a C 2-20 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted N, O and S,
보다 바람직하게는, Ar3 및 Ar4는 각각 독립적으로, 페닐, 비페닐릴, 터페닐릴, 나프틸, 디벤조퓨라닐, 디벤조티오페닐, 또는 디메틸플루오레닐일 수 있다.More preferably, Ar 3 and Ar 4 may each independently be phenyl, biphenylyl, terphenylyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or dimethylfluorenyl.
바람직하게는, R3 및 R4는 각각 독립적으로, 수소; 중수소; 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,Preferably, R 3 and R 4 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 6-20 aryl; Or it may be a C 2-20 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted N, O and S,
보다 바람직하게는, R3 및 R4는 각각 독립적으로, 수소; 중수소; 또는 페닐일 수 있다.More preferably, R 3 and R 4 are each independently hydrogen; heavy hydrogen; Or it may be phenyl.
바람직하게는, a3 및 a4는 각각 독립적으로, 0 또는 1일 수 있다.Preferably, a3 and a4 may each independently be 0 or 1.
상기 화학식 2로 표시되는 화합물의 대표적인 예는 다음과 같다: Representative examples of compounds represented by Formula 2 are as follows:
상기 화학식 2로 표시되는 화합물은 일례로 하기 반응식 3과 같은 제조 방법으로 제조할 수 있으며, 그 외 나머지 화합물도 유사하게 제조할 수 있다.For example, the compound represented by Formula 2 can be prepared by the manufacturing method shown in Scheme 3 below, and the remaining compounds can be prepared similarly.
[반응식 3][Scheme 3]
상기 반응식 3에서, Ar3, Ar4, R3, R4, a3 및 a4는 상기 화학식 2에서 정의한 바와 같으며, Q7 및 Q8은 각각 독립적으로 할로겐이고, 바람직하게는 Q7 및 Q8은 각각 독립적으로 클로로 또는 브로모이다.In Scheme 3, Ar 3 , Ar 4 , R 3 , R 4 , a3 and a4 are as defined in Formula 2, and Q 7 and Q 8 are each independently halogen, preferably Q 7 and Q 8 is each independently chloro or bromo.
상기 반응식 3의 첫 번째 단계는 스즈키 커플링 반응으로서, 팔라듐 촉매와 염기 존재 하에 수행하는 것이 바람직하며, 스즈키 커플링 반응을 위한 반응기는 당업계에 알려진 바에 따라 변경이 가능하다. 또한, 상기 반응식 3의 두 번째 단계는 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.The first step in Scheme 3 is a Suzuki coupling reaction, which is preferably performed in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be changed according to what is known in the art. In addition, the second step of Scheme 3 is an amine substitution reaction, which is preferably performed in the presence of a palladium catalyst and a base, and the reactor for the amine substitution reaction can be changed according to what is known in the art. The manufacturing method may be further detailed in the manufacturing examples described later.
도펀트 재료로는 방향족 아민 유도체, 스트릴아민 화합물, 붕소 착체, 플루오란텐 화합물, 금속 착체 등이 있다. 구체적으로 방향족 아민 유도체로는 치환 또는 비치환된 아릴아미노기를 갖는 축합 방향족환 유도체로서, 아릴아미노기를 갖는 피렌, 안트라센, 크리센, 페리플란텐 등이 있으며, 스티릴아민 화합물로는 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로, 아릴기, 실릴기, 알킬기, 사이클로알킬기 및 아릴아미노기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민, 스티릴디아민, 스티릴트리아민, 스티릴테트라아민 등이 있으나, 이에 한정되지 않는다. 또한, 금속 착체로는 이리듐 착체, 백금 착체 등이 있으나, 이에 한정되지 않는다.Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, and periplanthene, and styrylamine compounds include substituted or unsubstituted arylamino groups. It is a compound in which at least one arylvinyl group is substituted on the arylamine, and is substituted or unsubstituted with one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group, and arylamino group. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc. are included, but are not limited thereto. Additionally, metal complexes include, but are not limited to, iridium complexes and platinum complexes.
상기 정공저지층은 양극에서 주입된 정공이 발광층에서 재결합되지 않고 전자수송층으로 넘어가는 것을 방지하기 위해 전자수송층과 발광층의 사이에 두는 층으로, 정공억제층으로 불리기도 한다. 정공저지층에는 이온화에너지가 큰 물질이 바람직하다.The hole blocking layer is a layer placed between the electron transport layer and the light emitting layer to prevent holes injected from the anode from being recombined in the light emitting layer and passing to the electron transport layer, and is also called a hole blocking layer. A material with high ionization energy is preferred for the hole blocking layer.
상기 전자수송층은 전자주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층으로 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 전자수송층은 종래기술에 따라 사용된 바와 같이 임의의 원하는 캐소드 물질과 함께 사용할 수 있다. 특히, 적절한 캐소드 물질의 예는 낮은 일함수를 가지고 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로 세슘, 바륨, 칼슘, 이테르븀 및 사마륨이고, 각 경우 알루미늄 층 또는 실버층이 뒤따른다.The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light-emitting layer. The electron transport material is a material that can easily inject electrons from the cathode and transfer them to the light-emitting layer, and a material with high electron mobility is suitable. do. Specific examples include Al complex of 8-hydroxyquinoline; Complex containing Alq 3 ; organic radical compounds; Hydroxyflavone-metal complexes, etc., but are not limited to these. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials with a low work function followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.
상기 전자주입층은 전극으로부터 전자를 주입하는 층으로, 전자를 수송하는 능력을 갖고, 음극으로부터의 전자 주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공주입층에의 이동을 방지하고, 또한, 박막형성능력이 우수한 화합물이 바람직하다. 구체적으로는 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 질소 함유 5원환 유도체 등이 있으나, 이에 한정되지 않는다. The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an excellent electron injection effect from the cathode, a light-emitting layer or a light-emitting material, and hole injection of excitons generated in the light-emitting layer. A compound that prevents movement to the layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metals. These include, but are not limited to, complex compounds and nitrogen-containing five-membered ring derivatives.
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 compounds 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-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato) aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato) gallium, etc. It is not limited to this.
본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present invention may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.
또한, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자 외에도 유기 태양 전지 또는 유기 트랜지스터에 포함될 수 있다.Additionally, the compound represented by Formula 1 may be included in organic solar cells or organic transistors in addition to organic light-emitting devices.
이하, 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다. 단, 하기의 실시예는 본 발명을 예시하는 것일 뿐, 본 발명의 내용이 하기의 실시예에 의하여 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail to aid understanding. However, the following examples only illustrate the present invention, and the content of the present invention is not limited by the following examples.
[제조예][Manufacturing example]
제조예 A: 중간체 A의 제조Preparation Example A: Preparation of Intermediate A
단계 1) 중간체 A-1의 제조Step 1) Preparation of Intermediate A-1
질소 분위기에서 2,5-dibromo-1,3-difluorobenzene(15.0 g, 55.2 mmol), phenol(11.4 g, 121.4 mmol), potassium carbonate(15.2 g, 110.3 mmol)를 NMP 225 ml에 넣고 교반 및 환류하였다. 9 시간 반응하고 상온으로 식히고 클로로포름과 물을 이용하여 유기층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 중간체 A-1를 18.1 g 제조하였다. (수율 78 %, MS: [M+H]+= 421)In a nitrogen atmosphere, 2,5-dibromo-1,3-difluorobenzene (15.0 g, 55.2 mmol), phenol (11.4 g, 121.4 mmol), and potassium carbonate (15.2 g, 110.3 mmol) were added to 225 ml of NMP, stirred, and refluxed. . After reacting for 9 hours, the reaction mixture was cooled to room temperature, the organic layer was separated using chloroform and water, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.1 g of Intermediate A-1. (Yield 78%, MS: [M+H]+= 421)
단계 2) 중간체 A의 제조Step 2) Preparation of Intermediate A
질소 분위기에서 중간체 A-1(15 g, 35.7 mmol)를 tert-butylbenzene 300 ml에 녹인 후 0 ℃까지 냉각하였다. 여기에 1.7 M의 tert-butyllithium in pentane(31.5 ml, 53.6 mmol)을 투입하고 60 ℃에서 2 시간 교반하였다. 이 후 다시 반응물을 0 ℃까지 냉각하고 boron tribromide(5.2 ml, 53.6 mmol)을 첨가한 후 상온에서 0.5 시간 교반하였다. 다시 반응물을 0 ℃까지 냉각하고 N,N-diisopropylethylamine(9.3 ml, 53.6 mmol)을 투입한 후 60 ℃에서 2 시간 교반하였다. 반응이 종료되면 상온으로 냉각한 후, 클로로포름과 물을 이용하여 유기층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 중간체 A를 6.9 g 제조하였다. (수율 55 %, MS: [M+H]+= 350)Intermediate A-1 (15 g, 35.7 mmol) was dissolved in 300 ml of tert-butylbenzene in a nitrogen atmosphere and then cooled to 0°C. 1.7 M of tert-butyllithium in pentane (31.5 ml, 53.6 mmol) was added thereto and stirred at 60°C for 2 hours. Afterwards, the reaction was cooled to 0°C again, boron tribromide (5.2 ml, 53.6 mmol) was added, and the mixture was stirred at room temperature for 0.5 hours. The reaction was again cooled to 0°C, N,N-diisopropylethylamine (9.3 ml, 53.6 mmol) was added, and the mixture was stirred at 60°C for 2 hours. When the reaction was completed, the reaction was cooled to room temperature, the organic layer was separated using chloroform and water, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 6.9 g of Intermediate A. (Yield 55%, MS: [M+H]+= 350)
제조예 B: 중간체 B의 제조Preparation Example B: Preparation of Intermediate B
제조예 A에서, phenol을 pyridin-4-ol로 변경하여 사용한 것을 제외하고는, 중간체 A의 제조 방법과 동일한 제조 방법으로 중간체 B를 제조하였다. (MS: [M+H]+= 352)In Preparation Example A, Intermediate B was prepared using the same preparation method as that of Intermediate A, except that phenol was changed to pyridin-4-ol. (MS: [M+H] + = 352)
제조예 C: 중간체 C의 제조Preparation Example C: Preparation of Intermediate C
제조예 A에서, 2,5-dibromo-1,3-difluorobenzene을 2,5-dichloro-4,6-difluoropyrimidine으로 변경하여 사용한 것을 제외하고는, 중간체 A의 제조 방법과 동일한 제조 방법으로 중간체 C를 제조하였다. (MS: [M+H]+= 308)In Preparation Example A, Intermediate C was prepared using the same manufacturing method as that of Intermediate A, except that 2,5-dibromo-1,3-difluorobenzene was changed to 2,5-dichloro-4,6-difluoropyrimidine. Manufactured. (MS: [M+H] + = 308)
제조예 1: 화합물 1의 제조Preparation Example 1: Preparation of Compound 1
단계 1) 화합물 1-1의 제조Step 1) Preparation of Compound 1-1
질소 분위기에서 8-bromo-1-chlorodibenzo[b,d]furan(15.0 g, 53.3 mmol)와 bis(pinacolato)diboron(14.9 g, 58.6 mmol)를 1,4-dioxane 300 ml에 환류시키며 교반하였다. 이 후 potassium acetate(7.8 g, 79.9 mmol)를 투입하고 충분히 교반한 후 bis(dibenzylideneacetone)palladium(0)(0.9 g, 1.6 mmol) 및 tricyclohexylphosphine(0.9 g, 3.2 mmol)을 투입하였다. 9 시간 반응하고 상온으로 식히고 클로로포름과 물을 이용하여 유기층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 1-1을 11.0 g 제조하였다. (수율 63 %, MS: [M+H]+= 330)In a nitrogen atmosphere, 8-bromo-1-chlorodibenzo[b,d]furan (15.0 g, 53.3 mmol) and bis(pinacolato)diboron (14.9 g, 58.6 mmol) were refluxed and stirred in 300 ml of 1,4-dioxane. Afterwards, potassium acetate (7.8 g, 79.9 mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium(0) (0.9 g, 1.6 mmol) and tricyclohexylphosphine (0.9 g, 3.2 mmol) were added. After reacting for 9 hours, the reaction mixture was cooled to room temperature, the organic layer was separated using chloroform and water, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.0 g of compound 1-1. (Yield 63%, MS: [M+H]+= 330)
단계 2) 화합물 1-2의 제조Step 2) Preparation of Compound 1-2
질소 분위기에서 화합물 1-1(15.0 g, 45.6 mmol)와 중간체 A(17.5 g, 50.2 mmol)를 THF 300 ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(25.2 g, 182.6 mmol)를 물 76 ml에 녹여 투입하고 충분히 교반한 후 tetrakis(triphenylphosphine)palladium(0)(1.6 g, 1.4 mmol)을 투입하였다. 9 시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 1-2를 14.6 g 제조하였다. (수율 68 %, MS: [M+H]+= 472)In a nitrogen atmosphere, Compound 1-1 (15.0 g, 45.6 mmol) and Intermediate A (17.5 g, 50.2 mmol) were added to 300 ml of THF, stirred, and refluxed. Afterwards, potassium carbonate (25.2 g, 182.6 mmol) was dissolved in 76 ml of water, stirred sufficiently, and then tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.4 mmol) was added. After reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.6 g of compound 1-2. (Yield 68%, MS: [M+H]+= 472)
단계 3) 화합물 1-3의 제조Step 3) Preparation of compounds 1-3
질소 분위기에서 화합물 1-2(15.0 g, 31.9 mmol)와 bis(pinacolato)diboron(8.9 g, 35.1 mmol)를 1,4-dioxane 300 ml에 환류시키며 교반하였다. 이 후 potassium acetate (4.7 g, 47.8 mmol)를 투입하고 충분히 교반한 후 bis(dibenzylideneacetone)palladium(0) (0.5 g, 1 mmol) 및 tricyclohexylphosphine(0.5 g, 1.9 mmol)을 투입하였다. 8 시간 반응하고 상온으로 식히고 클로로포름과 물을 이용하여 유기층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 1-3을 12.2 g 제조하였다. (수율 68 %, MS: [M+H]+= 563)Compound 1-2 (15.0 g, 31.9 mmol) and bis(pinacolato)diboron (8.9 g, 35.1 mmol) were refluxed in 300 ml of 1,4-dioxane and stirred in a nitrogen atmosphere. Afterwards, potassium acetate (4.7 g, 47.8 mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium(0) (0.5 g, 1 mmol) and tricyclohexylphosphine (0.5 g, 1.9 mmol) were added. After reacting for 8 hours, the reaction mixture was cooled to room temperature, the organic layer was separated using chloroform and water, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.2 g of compound 1-3. (Yield 68%, MS: [M+H]+= 563)
단계 4) 화합물 1의 제조Step 4) Preparation of Compound 1
질소 분위기에서 화합물 1-3(15.0 g, 26.7 mmol)과 2-chloro-4,6-diphenyl-1,3,5-triazine(7.9 g, 29.3 mmol)을 THF 300 ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(14.7 g, 106.7 mmol)를 물 44 ml에 녹여 투입하고 충분히 교반한 후 tetrakis(triphenylphosphine)palladium(0)(0.9 g, 0.8 mmol)을 투입하였다. 10 시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제한 후, 승화정제를 통해 화합물 1을 12.1 g 제조하였다. (수율 68 %, MS: [M+H]+= 669)In a nitrogen atmosphere, compound 1-3 (15.0 g, 26.7 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (7.9 g, 29.3 mmol) were added to 300 ml of THF, stirred and refluxed. Afterwards, potassium carbonate (14.7 g, 106.7 mmol) was dissolved in 44 ml of water, stirred sufficiently, and then tetrakis(triphenylphosphine)palladium(0) (0.9 g, 0.8 mmol) was added. After reacting for 10 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, and then 12.1 g of Compound 1 was prepared through sublimation purification. (Yield 68%, MS: [M+H]+= 669)
제조예 2: 화합물 2의 제조Preparation Example 2: Preparation of Compound 2
제조예 1에서, 8-bromo-1-chlorodibenzo[b,d]furan을 3-bromo-7-chlorodibenzo[b,d]furan으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 2를 제조하였다. (MS: [M+H]+= 669)In Preparation Example 1, the same manufacturing method as that of Compound 1, except that 8-bromo-1-chlorodibenzo[b,d]furan was changed to 3-bromo-7-chlorodibenzo[b,d]furan. Compound 2 was prepared as follows. (MS: [M+H] + = 669)
제조예 3: 화합물 3의 제조Preparation Example 3: Preparation of Compound 3
제조예 1에서, 8-bromo-1-chlorodibenzo[b,d]furan을 3-bromo-7-chlorodibenzo[b,d]furan으로, 2-chloro-4,6-diphenyl-1,3,5-triazine을 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 3을 제조하였다. (MS: [M+H]+= 745)In Preparation Example 1, 8-bromo-1-chlorodibenzo[b,d]furan is changed to 3-bromo-7-chlorodibenzo[b,d]furan, 2-chloro-4,6-diphenyl-1,3,5- The same method for preparing compound 1 was used, except that triazine was changed to 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine. Compound 3 was prepared using the preparation method. (MS: [M+H] + = 745)
제조예 4: 화합물 4의 제조Preparation Example 4: Preparation of Compound 4
제조예 1에서, 8-bromo-1-chlorodibenzo[b,d]furan을 2-bromo-7-chlorodibenzo[b,d]furan으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 4를 제조하였다. (MS: [M+H]+= 669)In Preparation Example 1, the same manufacturing method as that of Compound 1, except that 8-bromo-1-chlorodibenzo[b,d]furan was changed to 2-bromo-7-chlorodibenzo[b,d]furan. Compound 4 was prepared as follows. (MS: [M+H] + = 669)
제조예 5: 화합물 5의 제조Preparation Example 5: Preparation of Compound 5
제조예 1에서, 8-bromo-1-chlorodibenzo[b,d]furan을 2-bromo-7-chlorodibenzo[b,d]furan으로, 중간체 A를 중간체 C로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 5를 제조하였다. (MS: [M+H]+= 671)In Preparation Example 1, Compound 1, except that 8-bromo-1-chlorodibenzo[b,d]furan was changed to 2-bromo-7-chlorodibenzo[b,d]furan and Intermediate A was changed to Intermediate C. Compound 5 was prepared using the same manufacturing method as that of . (MS: [M+H] + = 671)
제조예 6: 화합물 6의 제조Preparation Example 6: Preparation of Compound 6
제조예 1에서, 8-bromo-1-chlorodibenzo[b,d]furan을 7-bromo-1-chlorodibenzo[b,d]furan으로, 중간체 A를 중간체 B로, 2-chloro-4,6-diphenyl-1,3,5-triazine을 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 6을 제조하였다. (MS: [M+H]+= 681)In Preparation Example 1, 8-bromo-1-chlorodibenzo[b,d]furan is converted to 7-bromo-1-chlorodibenzo[b,d]furan, intermediate A is converted to intermediate B, and 2-chloro-4,6-diphenyl -1,3,5-triazine was prepared using the same manufacturing method as that of Compound 1, except that 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine was used. Compound 6 was prepared. (MS: [M+H] + = 681)
제조예 7: 화합물 7의 제조Preparation Example 7: Preparation of Compound 7
단계 1) 화합물 7-1의 제조Step 1) Preparation of compound 7-1
질소 분위기에서 3-bromodibenzo[b,d]furan(15.0 g, 60.7 mmol)과 bis(pinacolato)diboron(17.0 g, 66.8 mmol)를 1,4-dioxane 300 ml에 환류시키며 교반하였다. 이 후 potassium acetate (8.9 g, 91.1 mmol)를 투입하고 충분히 교반한 후 bis(dibenzylideneacetone)palladium(0) (1.0 g, 1.8 mmol) 및 tricyclohexylphosphine(1.0 g, 3.6 mmol)을 투입하였다. 8 시간 반응하고 상온으로 식히고 클로로포름과 물을 이용하여 유기층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 7-1을 13.9 g 제조하였다. (수율 78 %, MS: [M+H]+= 295)In a nitrogen atmosphere, 3-bromodibenzo[b,d]furan (15.0 g, 60.7 mmol) and bis(pinacolato)diboron (17.0 g, 66.8 mmol) were refluxed and stirred in 300 ml of 1,4-dioxane. Afterwards, potassium acetate (8.9 g, 91.1 mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium(0) (1.0 g, 1.8 mmol) and tricyclohexylphosphine (1.0 g, 3.6 mmol) were added. After reacting for 8 hours, the reaction mixture was cooled to room temperature, the organic layer was separated using chloroform and water, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.9 g of compound 7-1. (Yield 78%, MS: [M+H]+= 295)
단계 2) 화합물 7-2의 제조Step 2) Preparation of compound 7-2
질소 분위기에서 화합물 7-1(15.0 g, 51.0 mmol)와 2-chloro-4,6-diphenyl-1,3,5-triazine(15.0 g, 56.1 mmol)를 THF 300 ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(28.2 g, 204.0 mmol)를 물 120 ml에 녹여 투입하고 충분히 교반한 후 tetrakis(triphenylphosphine)palladium(0)(1.8 g, 1.5 mmol)을 투입하였다. 9 시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 7-2를 7.7 g 제조하였다. (수율 38 %, MS: [M+H]+= 400)In a nitrogen atmosphere, compound 7-1 (15.0 g, 51.0 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (15.0 g, 56.1 mmol) were added to 300 ml of THF, stirred and refluxed. Afterwards, potassium carbonate (28.2 g, 204.0 mmol) was dissolved in 120 ml of water, stirred sufficiently, and then tetrakis(triphenylphosphine)palladium(0) (1.8 g, 1.5 mmol) was added. After reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 7.7 g of compound 7-2. (Yield 38%, MS: [M+H]+= 400)
단계 3) 화합물 7-3의 제조Step 3) Preparation of compound 7-3
플라스크에 화합물 7-2(10.0 g, 25.0 mmol), THF 100 ml를 넣고, -78 ℃로 냉각했다. 1.6M의 n-butyllithium in hexane(16.4 ml, 26.3 mmol)을 적가하고, -78 ℃에서 20 분간 교반했다. 붕산 트라이아이소프로필(2.9 g, 27.5 mmol)을 가하여 -78 ℃에서 1 시간 교반 후, 상온에서 4 시간 더 교반하였다. 이 후 1N HCl을 가하여 실온에서 1 시간 교반후 반응액을 농축하여, 분액 깔대기에 옮기고, H2O 200 ml을 가한 후 CH2Cl2로 추출하였다. 추출액에 무수황산마그네슘을 넣고 건조후, 여과, 농축한 후, 재결정을 하여 화합물 7-3을 6.7 g 제조하였다. (수율 60 %, MS: [M+H]+= 444)Compound 7-2 (10.0 g, 25.0 mmol) and 100 ml of THF were added to the flask, and cooled to -78°C. 1.6M of n-butyllithium in hexane (16.4 ml, 26.3 mmol) was added dropwise, and stirred at -78°C for 20 minutes. Triisopropyl borate (2.9 g, 27.5 mmol) was added and stirred at -78°C for 1 hour, then stirred at room temperature for an additional 4 hours. Afterwards, 1N HCl was added and the reaction solution was concentrated at room temperature after stirring for 1 hour, transferred to a separatory funnel, 200 ml of H 2 O was added, and extracted with CH 2 Cl 2 . Anhydrous magnesium sulfate was added to the extract, dried, filtered, concentrated, and recrystallized to prepare 6.7 g of compound 7-3. (Yield 60%, MS: [M+H] + = 444)
단계 4) 화합물 7의 제조Step 4) Preparation of Compound 7
질소 분위기에서 화합물 7-3(15.0 g, 33.8 mmol)와 중간체 A(13.0 g, 37.2 mmol)를 THF 300 ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(18.7 g, 135.4 mmol)를 물 56 ml에 녹여 투입하고 충분히 교반한 후 tetrakis(triphenylphosphine)palladium(0)(1.2 g, 1.0 mmol)을 투입하였다. 11 시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제한 후, 승화정제를 통해 화합물 7을 7.5 g 제조하였다. (수율 33 %, MS: [M+H]+= 669)In a nitrogen atmosphere, Compound 7-3 (15.0 g, 33.8 mmol) and Intermediate A (13.0 g, 37.2 mmol) were added to 300 ml of THF, stirred, and refluxed. Afterwards, potassium carbonate (18.7 g, 135.4 mmol) was dissolved in 56 ml of water, stirred sufficiently, and then tetrakis(triphenylphosphine)palladium(0) (1.2 g, 1.0 mmol) was added. After reacting for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, and then 7.5 g of Compound 7 was prepared through sublimation purification. (Yield 33%, MS: [M+H]+= 669)
제조예 8: 화합물 8의 제조Preparation Example 8: Preparation of Compound 8
제조예 7에서, 2-chloro-4,6-diphenyl-1,3,5-triazine을 2-chloro-4-(9,9-dimethyl-9H-fluoren-1-yl)-6-phenyl-1,3,5-triazine으로 변경하여 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 제조 방법으로 화합물 8을 제조하였다. (MS: [M+H]+= 785)In Preparation Example 7, 2-chloro-4,6-diphenyl-1,3,5-triazine was reacted with 2-chloro-4-(9,9-dimethyl-9H-fluoren-1-yl)-6-phenyl-1 Compound 8 was prepared using the same manufacturing method as that of Compound 1, except that it was changed to 3,5-triazine. (MS: [M+H] + = 785)
제조예 9: 화합물 9의 제조Preparation Example 9: Preparation of Compound 9
단계 1) 화합물 9-1의 제조Step 1) Preparation of Compound 9-1
질소 분위기에서 dibenzo[b,d]thiophen-4-ylboronic acid(15.0 g, 65.8 mmol)와 2-chloro-4,6-diphenyl-1,3,5-triazine(19.4 g, 72.3 mmol)를 THF 300 ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(36.4 g, 263.1 mmol)를 물 109 ml에 녹여 투입하고 충분히 교반한 후 tetrakis(triphenylphosphine)palladium(0)(2.3 g, 2.0 mmol)을 투입하였다. 12 시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 9-1을 18 g 제조하였다. (수율 66 %, MS: [M+H]+= 417)Dibenzo[b,d]thiophen-4-ylboronic acid (15.0 g, 65.8 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (19.4 g, 72.3 mmol) were mixed with THF 300 in a nitrogen atmosphere. ml, stirred and refluxed. Afterwards, potassium carbonate (36.4 g, 263.1 mmol) was dissolved in 109 ml of water, stirred sufficiently, and then tetrakis(triphenylphosphine)palladium(0) (2.3 g, 2.0 mmol) was added. After reacting for 12 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18 g of compound 9-1. (Yield 66%, MS: [M+H]+= 417)
단계 2) 화합물 9-2의 제조Step 2) Preparation of Compound 9-2
질소 분위기에서 화합물 9-1(20 g, 48.1 mmol), N-bromosuccinimide (9 g, 50.5 mmol)을 dimethylformamide 400 ml에 넣고 상온에서 교반하였다. 5 시간 반응 후, 클로로포름과 물을 이용하여 유기층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 9-2를 19 g 제조하였다. (수율 80 %, MS: [M+H]+= 495)In a nitrogen atmosphere, compound 9-1 (20 g, 48.1 mmol) and N-bromosuccinimide (9 g, 50.5 mmol) were added to 400 ml of dimethylformamide and stirred at room temperature. After reaction for 5 hours, the organic layer was separated using chloroform and water, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 19 g of compound 9-2. (Yield 80%, MS: [M+H]+= 495)
단계 3) 화합물 9-3의 제조Step 3) Preparation of compound 9-3
질소 분위기에서 화합물 9-2(15 g, 30.3 mmol)와 bis(pinacolato)diboron(8.5 g, 33.4 mmol)를 1,4-dioxane 300 ml에 환류시키며 교반하였다. 이 후 potassium acetate (4.5 g, 45.5 mmol)를 투입하고 충분히 교반한 후 bis(dibenzylideneacetone)palladium(0) (0.5 g, 0.9 mmol) 및 tricyclohexylphosphine(0.5 g, 1.8 mmol)을 투입하였다. 8 시간 반응하고 상온으로 식히고 클로로포름과 물을 이용하여 유기층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 9-3을 12.3 g 제조하였다. (수율 75 %, MS: [M+H]+= 542)Compound 9-2 (15 g, 30.3 mmol) and bis(pinacolato)diboron (8.5 g, 33.4 mmol) were refluxed in 300 ml of 1,4-dioxane and stirred in a nitrogen atmosphere. Afterwards, potassium acetate (4.5 g, 45.5 mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium(0) (0.5 g, 0.9 mmol) and tricyclohexylphosphine (0.5 g, 1.8 mmol) were added. After reacting for 8 hours, the reaction mixture was cooled to room temperature, the organic layer was separated using chloroform and water, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.3 g of compound 9-3. (Yield 75%, MS: [M+H]+= 542)
단계 4) 화합물 9의 제조Step 4) Preparation of Compound 9
질소 분위기에서 화합물 9-3(15.0 g, 27.7 mmol)와 중간체 A(10.6 g, 30.5 mmol)를 THF 300 ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(15.3 g, 110.8 mmol)를 물 46 ml에 녹여 투입하고 충분히 교반한 후 tetrakis(triphenylphosphine)palladium(0)(1.0 g, 0.8 mmol)을 투입하였다. 12 시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제한 후, 승화정제를 통해 화합물 9를 7.1 g 제조하였다. (수율 34 %, MS: [M+H]+= 685)In a nitrogen atmosphere, compound 9-3 (15.0 g, 27.7 mmol) and intermediate A (10.6 g, 30.5 mmol) were added to 300 ml of THF, stirred, and refluxed. Afterwards, potassium carbonate (15.3 g, 110.8 mmol) was dissolved in 46 ml of water, stirred sufficiently, and then tetrakis(triphenylphosphine)palladium(0) (1.0 g, 0.8 mmol) was added. After reacting for 12 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, and then 7.1 g of Compound 9 was prepared through sublimation purification. (Yield 34%, MS: [M+H]+= 685)
제조예 10: 화합물 PGH-1의 제조Preparation Example 10: Preparation of compound PGH-1
3 구 플라스크에 3-bromo-9H-carbazole(10.0 g, 40.6 mmol), 중간체 a(19.0 g, 42.7 mmol)를 THF(400 ml)에 녹이고 K2CO3(22.5 g, 162.5 mmol)를 물(200 ml)에 녹여 넣었다. 여기에 tetrakis(triphenylphosphine)palladium(0)(0.5 g, 0.4 mmol)를 넣고, 아르곤 분위기 환류 조건하에서 8 시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각한 후, 반응액을 분액 깔대기에 옮기고, CH2Cl2로 추출했다. 추출액을 MgSO4로 건조 후, 여과 및 농축한 후, 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 중간체 M1을 14.8 g 제조하였다. (수율 75 %, MS: [M+H]+= 484)In a three-necked flask, 3-bromo-9H-carbazole (10.0 g, 40.6 mmol) and intermediate a (19.0 g, 42.7 mmol) were dissolved in THF (400 ml), and K 2 CO 3 (22.5 g, 162.5 mmol) was dissolved in water ( 200 ml) and dissolved in it. Tetrakis(triphenylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added here, and stirred for 8 hours under reflux conditions in an argon atmosphere. When the reaction was completed, the reaction solution was cooled to room temperature, transferred to a separatory funnel, and extracted with CH 2 Cl 2 . The extract was dried over MgSO 4 , filtered and concentrated, and the sample was purified by silica gel column chromatography to prepare 14.8 g of intermediate M1. (Yield 75%, MS: [M+H] + = 484)
3 구 플라스크에 중간체 M1(14.0 g, 28.9 mmol), 중간체 b(7.4 g, 31.8 mmol)를 toluene 280 ml에 녹이고 sodium tert-butoxide(4.2 g, 43.3 mmol), bis(tri-tert-butylphosphine)palladium(0)(0.3 g, 0.6 mmol)을 넣은 후, 아르곤 분위기 환류 조건하에서 6 시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각한 후, 물 200 ml을 넣고 반응액을 분액 깔대기에 옮겨 추출하였다. 추출액을 MgSO4로 건조, 농축하고 시료를 실리카 겔 컬럼 크로마토그래피로 정제한 후, 승화정제를 통해 화합물 PGH-1을 6.4 g 제조하였다. (수율 35 %, MS: [M+H]+= 636)In a three-neck flask, intermediate M1 (14.0 g, 28.9 mmol) and intermediate b (7.4 g, 31.8 mmol) were dissolved in 280 ml of toluene and sodium tert-butoxide (4.2 g, 43.3 mmol) and bis(tri-tert-butylphosphine)palladium were added. (0) (0.3 g, 0.6 mmol) was added and stirred for 6 hours under reflux conditions in an argon atmosphere. When the reaction was completed, it was cooled to room temperature, 200 ml of water was added, and the reaction solution was transferred to a separatory funnel and extracted. The extract was dried and concentrated with MgSO 4 , the sample was purified by silica gel column chromatography, and then 6.4 g of compound PGH-1 was prepared through sublimation purification. (Yield 35%, MS: [M+H] + = 636)
제조예 11: 화합물 PGH-2의 제조Preparation Example 11: Preparation of compound PGH-2
중간체 a 대신 중간체 c를, 중간체 b 대신 중간체 d를 사용한 것을 제외하고는, 제조예 10과 동일한 방법으로 화합물 PGH-2를 제조하였다. (MS: [M+H]+= 574)Compound PGH-2 was prepared in the same manner as Preparation Example 10, except that Intermediate c was used instead of Intermediate a and Intermediate d was used instead of Intermediate b. (MS: [M+H] + = 574)
[실시예][Example]
실시예 1Example 1
ITO(Indium Tin Oxide)가 1400 Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이 때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30 분간 세척한 후 증류수로 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 5 분간 세정한 후 진공 증착기로 기판을 수송시켰다.A glass substrate coated with a thin film of ITO (Indium Tin Oxide) with a thickness of 1400 Å was placed in distilled water with a detergent dissolved in it and washed ultrasonically. At this time, a detergent from Fischer Co. was used, and distilled water filtered secondarily using a filter from Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, it was ultrasonic washed with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned for 5 minutes using oxygen plasma and then transported to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에, 하기 화합물 HT-A와 하기 화합물 PD를 95:5의 중량비로 100 Å의 두께로 열 진공 증착하고, 이어서 하기 화합물 HT-A만 1150 Å의 두께로 증착하여 정공수송층을 형성하였다. 상기 정공수송층 위에, 하기 화합물 HT-B를 450 Å의 두께로 열 진공 증착하여 전자저지층을 형성하였다. 상기 전자저지층 위에, 앞서 제조한 화합물 1과 하기 화합물 GD를 94:6의 중량비로 400 Å의 두께로 진공 증착하여 발광층을 형성하였다. 상기 발광층 위에, 하기 화합물 ET-A를 50 Å의 두께로 진공 증착하여 정공저지층을 형성하였다. 상기 정공저지층 위에, 하기 화합물 ET-B와 하기 화합물 Liq를 2:1의 중량비로 250 Å의 두께로 열 진공 증착하고, 이어서 LiF와 마그네슘을 1:1의 중량비로 30 Å의 두께로 진공 증착하여 전자 수송 및 주입층을 형성하였다. 상기 전자주입층 위에, 마그네슘과 은을 1:4의 중량비로 160 Å의 두께로 증착하여 음극을 형성하여, 유기 발광 소자를 제조하였다.On the ITO transparent electrode prepared in this way, the following compound HT-A and the following compound PD were thermally vacuum deposited at a weight ratio of 95:5 to a thickness of 100 Å, and then only the following compound HT-A was deposited to a thickness of 1150 Å to form a hole transport layer. formed. On the hole transport layer, the following compound HT-B was thermally vacuum deposited to a thickness of 450 Å to form an electron blocking layer. On the electron blocking layer, Compound 1 prepared previously and Compound GD below were vacuum deposited to a thickness of 400 Å at a weight ratio of 94:6 to form an emitting layer. On the light emitting layer, the following compound ET-A was vacuum deposited to a thickness of 50 Å to form a hole blocking layer. On the hole blocking layer, the following compound ET-B and the following compound Liq were thermally vacuum deposited to a thickness of 250 Å at a weight ratio of 2:1, and then LiF and magnesium were vacuum deposited to a thickness of 30 Å at a weight ratio of 1:1. Thus, an electron transport and injection layer was formed. On the electron injection layer, magnesium and silver were deposited at a weight ratio of 1:4 to a thickness of 160 Å to form a cathode, thereby manufacturing an organic light-emitting device.
상기의 과정에서 유기물의 증착속도는 0.4 ~ 0.7 Å/sec를 유지하였고, 음극의 리튬플로라이드는 0.3 Å/sec, 은과 마그네슘은 2 Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 2×10-7 ~ 5×10-6 torr를 유지하여, 유기 발광 소자를 제작하였다.In the above process, the deposition rate of organic matter was maintained at 0.4 ~ 0.7 Å/sec, the deposition rate of lithium fluoride of the cathode was maintained at 0.3 Å/sec, silver and magnesium were maintained at 2 Å/sec, and the vacuum degree during deposition was 2. An organic light emitting device was manufactured by maintaining ×10 -7 to 5 × 10 -6 torr.
실시예 2 내지 실시예 12Examples 2 to 12
화합물 1 대신 하기 표 1에 기재된 화합물을 사용한 것을 제외하고는, 상기 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. 하기 표 1에서 각 화합물의 비율은 중량비를 의미하며, 각 화합물의 중량의 총합은 실시예 1에서 화합물 1의 총량과 같다.An organic light-emitting device was manufactured in the same manner as Example 1, except that the compounds listed in Table 1 below were used instead of Compound 1. In Table 1 below, the ratio of each compound refers to the weight ratio, and the total weight of each compound is the same as the total amount of Compound 1 in Example 1.
비교예 1 내지 비교예 5Comparative Examples 1 to 5
화합물 1 대신 하기 표 1에 기재된 화합물을 사용한 것을 제외하고는, 상기 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. 하기 표 1에서 각 화합물의 비율은 중량비를 의미하며, 각 화합물의 중량의 총합은 실시예 1에서 화합물 1의 총량과 같다. 표 1의 화합물 GH-A, GH-B 및 GH-C는 각각 아래와 같다.An organic light-emitting device was manufactured in the same manner as Example 1, except that the compounds listed in Table 1 below were used instead of Compound 1. In Table 1 below, the ratio of each compound refers to the weight ratio, and the total weight of each compound is the same as the total amount of Compound 1 in Example 1. Compounds GH-A, GH-B and GH-C in Table 1 are respectively as follows.
[실험예][Experimental example]
상기 실시예 1 내지 9 및 비교예 1 내지 3에서 제조한 유기 발광 소자를 110 ℃ 오븐에서 30 분간 보관하여 열처리한 후, 전류를 인가하여 전압, 효율, 수명(T95)을 측정하고 그 결과를 하기 표 1에 나타내었다. 이때, 전압 및 효율은 10 mA/cm2의 전류 밀도를 인가하여 측정하였다. 또한, 하기 표 1의 T95은 전류 밀도 20 mA/cm2에서 초기 휘도가 95 %로 저하할 때까지 측정한 시간을 의미한다.The organic light emitting devices prepared in Examples 1 to 9 and Comparative Examples 1 to 3 were heat treated by storing them in an oven at 110°C for 30 minutes, and then applying current to measure the voltage, efficiency, and lifespan (T95), and the results are presented below. It is shown in Table 1. At this time, voltage and efficiency were measured by applying a current density of 10 mA/cm 2 . Additionally, T95 in Table 1 below refers to the time measured until the initial luminance decreases to 95% at a current density of 20 mA/cm 2 .
(V)Voltage
(V)
(cd/A)efficiency
(cd/A)
(T95, hr)life span
(T95, hr)
표 1의 결과로 미루어볼 때 화학식 1의 화합물을 유기 발광 소자의 호스트로 적용 시 비교예에 적용된 화합물을 유기 발광 소자의 호스트로 사용한 경우와 비교해 보다 저전압, 고효율, 장수명의 특성을 나타냄을 확인할 수 있었다. Judging from the results in Table 1, it can be confirmed that when the compound of Formula 1 is applied as a host for an organic light-emitting device, it exhibits lower voltage, higher efficiency, and longer lifespan characteristics than when the compound applied in the comparative example is used as a host for an organic light-emitting device. there was.
1: 기판 2: 양극
3: 발광층 4: 음극
5: 정공주입층 6: 정공수송층
7: 전자저지층 8: 정공저지층
9: 전자수송층 10: 전자주입층1: Substrate 2: Anode
3: light emitting layer 4: cathode
5: hole injection layer 6: hole transport layer
7: electron blocking layer 8: hole blocking layer
9: electron transport layer 10: electron injection layer
Claims (12)
[화학식 1]
상기 화학식 1에서,
X는 O 또는 S이고,
Z1 내지 Z3는 각각 독립적으로, CH 또는 N이고, 단 Z1 내지 Z3 중 적어도 하나는 N이고,
Ar1 및 Ar2는 각각 독립적으로, 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴이고,
R1 및 R2는 각각 독립적으로, 수소; 중수소; 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴이고,
a1 및 a2는 각각 독립적으로, 0 내지 3의 정수이고,
A는 하기 화학식 1A로 표시되고;
[화학식 1A]
상기 화학식 1A에서,
X1 내지 X10은 각각 독립적으로, CH 또는 N이고,
Y1 및 Y2는 각각 독립적으로, O 또는 S이다.
Compound represented by Formula 1:
[Formula 1]
In Formula 1,
X is O or S,
Z 1 to Z 3 are each independently CH or N, provided that at least one of Z 1 to Z 3 is N,
Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 aryl; or C 2-60 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted N, O and S,
R 1 and R 2 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 6-60 aryl; or C 2-60 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted N, O and S,
a1 and a2 are each independently an integer from 0 to 3,
A is represented by the following formula 1A;
[Formula 1A]
In Formula 1A,
X 1 to X 10 are each independently CH or N,
Y 1 and Y 2 are each independently O or S.
A는 하기로 구성되는 군으로부터 선택되는 어느 하나인,
화합물:
상기 군에서,
Y1 및 Y2에 대한 설명은 제1항에서 정의한 바와 같다.
According to paragraph 1,
A is any one selected from the group consisting of:
compound:
In the above group,
The description of Y 1 and Y 2 is as defined in paragraph 1.
X1 및 X2는 서로 동일하고, X3 및 X10은 서로 동일하고, X4 및 X9은 서로 동일하고, X5 및 X8은 서로 동일하고, X6 및 X7은 서로 동일한,
화합물.
According to paragraph 1,
X 1 and X 2 are the same as each other, X 3 and X 10 are the same as each other , X 4 and X 9 are the same as each other, X 5 and
compound.
Ar1 및 Ar2는 각각 독립적으로, 페닐, 비페닐릴, 나프틸, 디메틸플루오레닐, 디벤조퓨라닐, 다이벤조싸이오페닐, 또는 5 개의 중수소로 치환된 페닐인,
화합물.
According to paragraph 1,
Ar 1 and Ar 2 are each independently phenyl, biphenylyl, naphthyl, dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, or phenyl substituted with 5 deuterium atoms,
compound.
R1 및 R2는 각각 독립적으로, 수소, 중수소, 또는 페닐인,
화합물.
According to paragraph 1,
R 1 and R 2 are each independently hydrogen, deuterium, or phenyl,
compound.
a1 및 a2는 각각 독립적으로, 0 또는 1인,
화합물.
According to paragraph 1,
a1 and a2 are each independently 0 or 1,
compound.
상기 화학식 1로 표시되는 화합물은 하기로 구성되는 군으로부터 선택되는 어느 하나인,
화합물:
According to paragraph 1,
The compound represented by Formula 1 is any one selected from the group consisting of:
compound:
유기 발광 소자.
first electrode; a second electrode provided opposite to the first electrode; And an organic light emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer contains the compound according to any one of claims 1 to 7. doing,
Organic light emitting device.
상기 화합물을 포함하는 유기물층은 발광층인,
유기 발광 소자.
According to clause 8,
The organic material layer containing the compound is a light emitting layer,
Organic light emitting device.
발광층은 하기 화학식 2로 표시되는 화합물을 포함하는,
유기 발광 소자:
[화학식 2]
상기 화학식 2에서,
Ar3 및 Ar4는 각각 독립적으로, 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상을 포함하는 C2-60 헤테로아릴이고,
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,
a3 및 a4는 각각 독립적으로, 0 내지 7의 정수이다.
According to clause 9,
The light-emitting layer contains a compound represented by the following formula (2),
Organic light emitting device:
[Formula 2]
In Formula 2,
Ar 3 and Ar 4 are each independently substituted or unsubstituted C 6-60 aryl; or C 2-60 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted N, O and S,
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 C 2-60 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted N, O and S,
a3 and a4 are each independently integers from 0 to 7.
Ar3 및 Ar4는 각각 독립적으로, 페닐, 비페닐릴, 터페닐릴, 나프틸, 디벤조퓨라닐, 다이벤조싸이오페닐, 또는 디메틸플루오레닐인,
유기 발광 소자.
According to clause 10,
Ar 3 and Ar 4 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or dimethylfluorenyl,
Organic light emitting device.
상기 화학식 2로 표시되는 화합물은 하기로 구성되는 군으로부터 선택되는 어느 하나인,
유기 발광 소자:
The compound represented by Formula 2 is any one selected from the group consisting of:
Organic light emitting device:
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