WO2018221985A1 - Novel heterocyclic compound and organic light emitting element using same - Google Patents
Novel heterocyclic compound and organic light emitting element using same Download PDFInfo
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- WO2018221985A1 WO2018221985A1 PCT/KR2018/006240 KR2018006240W WO2018221985A1 WO 2018221985 A1 WO2018221985 A1 WO 2018221985A1 KR 2018006240 W KR2018006240 W KR 2018006240W WO 2018221985 A1 WO2018221985 A1 WO 2018221985A1
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- compound
- light emitting
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- 150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 90
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- 239000011368 organic material Substances 0.000 claims description 31
- 239000000126 substance Substances 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 5
- 229910052805 deuterium Inorganic materials 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
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- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 150000002979 perylenes Chemical class 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000007774 positive electrode material Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 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
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
Abstract
The present invention provides a novel heterocyclic compound and an organic light emitting element using the same.
Description
【발명의 명칭】 [Name of invention]
신규한 헤테로 고리 화합물 및 이를 이용한유기발광 소자 Novel heterocyclic compound and organic light emitting device using the same
【기술분야】 Technical Field
관련출원들과의 상호 인용 Cross Citation with Related Applications
본 출원은 2017년 5월 31일자 한국 특허 출원 게 10-2017-0067648호 및 2018년 5월 30일자 한국 특허 출원 게 10-2018-0062154호에 기초한 우선권의 이익을 주장하며, 해당 한국 특허 출원들의 문헌에 개시된 모든 내용은 본 명세서의 일부로서 포함된다. 본 발명은 신규한 헤테로 고리 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. This application claims the benefit of priority based on Korean Patent Application No. 10-2017-0067648 of May 31, 2017 and Korean Patent Application No. 10-2018-0062154 of May 30, 2018, All content disclosed in the literature is included as part of this specification. The present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same.
【배경기술】 Background Art
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 웅답 속도 특성이 우수하여 많은 연구가 진행되고 있다. 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 액시톤 (exciton)이 형성되며， 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. 상기와 같은 유기 발광 소자에 사용되는 유기물에 대하여 새로운
재료의 개발이 지속적으로 요구되고 있다. In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent in brightness, driving voltage and response speed characteristics, many studies have been conducted. The organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. The organic layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows. New to organic materials used in the organic light emitting device as described above The development of materials continues to be demanded.
【선행기술문헌 1 Prior Art Documents 1
[특허문헌] [Patent Documents]
(특허문헌 0001) 한국특허 공개번호 게 10-2000-0051826호 (Patent Document 0001) Korean Patent Publication No. 10-2000-0051826
【발명의 상세한 설명】 [Detailed Description of the Invention]
【기술적 과제】 [Technical problem]
본 발명은 신규한 헤테로고리 화합물 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. The present invention relates to a novel heterocyclic compound compound and an organic light emitting device comprising the same.
【기술적 해결방법】 Technical Solution
본 발명은 하기 화학식 1로 표시되는 바이나프탈렌 (binaphthalene) 화합물을 제공한다. The present invention provides a binaphthalene compound represented by the following Chemical Formula 1.
[
상기 화학식 1에서, [ In Chemical Formula 1,
1^은 단일결합, 또는 치환또는 비치환된 C 0 아릴이고, 1 ^ is a single bond or a substituted or unsubstituted C 0 aryl,
L2는 단일결합, 치환 또는 비치환된 C6 60 아릴, 또는 치환 또 비치환된 C5-60 헤테로아릴이고, L 2 is a single bond, substituted or unsubstituted C 6 60 aryl, or substituted or unsubstituted C 5-60 heteroaryl,
Ai은 하기 화학식 2, 화학식 3, 화학식 4， 또는 화학식 5로 표시되고, Ai is represented by the following Chemical Formula 2, Chemical Formula 3, Chemical Formula 4, or Chemical Formula 5,
[화학식 2]
상기 화학식 2 내지 5에서, [Formula 2] In Chemical Formulas 2 to 5,
XL5 X2, 및 X3는 각각 독립적으로 N또는 CR4이며, 여기서, N은 적어도 1개 이상이고, X L5 X 2 , and X 3 are each independently N or CR 4 , wherein N is at least one,
¾, 및 X5는 각각 독립적으로 N 또는 CR5이며, 여기서, N은 적어도 1개 이상이고, ¾, and X 5 are each independently N or CR 5 , wherein N is at least one,
Ru R2, 및 R3는 각각 독립적으로 치환 또는 비치환된 d_40 알킬, 치환 또는 비치환된 C 0 아릴, 또는 치환 또는 비치환된 C5 60 헤테로아릴이고, 또는 R, , R2, 및 R3는 각각 독립적으로 상기 알킬, 아릴, 헤테로아릴의 수소가 중수소 또는 CN으로 치환된 것이고, R u R 2 , and R 3 are each independently substituted or unsubstituted d_ 40 alkyl, substituted or unsubstituted C 0 aryl, or substituted or unsubstituted C 5 60 heteroaryl, or R,, R 2 , And R 3 are each independently hydrogen of the alkyl, aryl, heteroaryl substituted with deuterium or CN,
R4, 및 R5는 각각 독립적으로 수소， 중수소， 치환 또는 비치환된 CMO 알킬, 치환 또는 비치환된 C6_60 아릴， 또는 치환 또는 비치환된 C5 헤테로아릴이다.
또한, 본 발명은 제 1 전극; 상기 제 1 전극과 대향하여 구비된 제 2 전극 및 상기 게 1 전극과 상기 제 2 전극 사이에 구비된 1층 이상의 유기물 층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 아상은 상기 화학식 1로 표시되는 화합물을 포함하는， 유기 발광 소자를 제공한다. R 4, and R 5 are each independently hydrogen, deuterium, substituted or unsubstituted CMO alkyl, substituted or unsubstituted C 6 _ 60 aryl, or substituted or unsubstituted C 5 heteroaryl. In addition, the present invention is a first electrode; An organic light emitting device including a second electrode provided to face the first electrode and one or more organic material layers provided between the first electrode and the second electrode, wherein one sub-layer of the organic material layer is represented by Chemical Formula 1. Provided is an organic light emitting device comprising the compound represented.
【발명의 효과】 【Effects of the Invention】
상술한 화학식 1로 표시되는 화합물은 유기 발광 소자의 유기물 층의 재료로서 사용될 수 있으며, 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및 /또는 수명 특성을 향상시킬 수 있다. 특히， 상술한 화학식 1로 표시되는 화합물은 정공주입, 정공수송, 정공주입 및 수송, 발광， 전자수송, 또는 전자주입 재료로 '사용될 수 있다. The compound represented by Chemical Formula 1 may be used as a material of the organic material layer of the organic light emitting diode, and may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode. In particular, it represented by the above formula (I) compounds may 'be used as a hole injection, hole transport, hole injection and transport, emission, electron transportation, or the electron injecting material.
【도면의 간단한 설명】 [Brief Description of Drawings]
도 1은 기판 (1), 양극 (2)， 발광층 (3)， 음극 (4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG.
도 2는 기판 (1)， 양극 (2), 정공주입층 (5)， 정공수송층 (6), 발광층 (7), 전자수송층 (8) 및 음극 (4)로 이루어진 유기 발광 소자의 예를 도시한 것이다. 【발명의 실시를 위한 형태】 FIG. 2 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is. [Form for implementation of invention]
이하, 본 발명의 이해를 돕기 위하여 보다상세히 설명한다. 본 명세서에서, *—— 및 ᅥᅳ는 다른 치환기에 연결되는 결합을 의미한다. 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, 0 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 바이페닐기일 수 있다. 즉, 바이페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다. 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. Hereinafter, the present invention will be described in more detail to aid in understanding the present invention. In the present specification, * —— and 의미 refer to a bond connected to another substituent. As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; An alkyl group; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups including one or more of N, 0 and S atoms, or two or more substituents of the above-described substituents connected or substituted. . For example, "a substituent to which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked. Although carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C40. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
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, 아에 한정되는 것은 아니다. 본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. 상가 플루오레닐기가 치환되는 It is preferably 60, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include naphthyl group, anthracenyl group, phenanthryl group, It may be a pyrenyl group, a perrylenyl group, a chrysenyl group, a fluorenyl group and the like, but is not limited thereto. In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. Substituted fluorenyl groups
[ [
[ [
Ll3 L2, Rl3 R2, 및 R3는 상기 화학식 1에서 정의한 바와 같다ᅳ 바람직하게는, 및 L2는 각각 독립적으로 단일결합, 페닐렌기 (phenylene), 또는 바이페닐렌기 (biphenylene)이다. 바람직하게는 , ,¾, , ¾, 및 X5는 각각 독립적으로 N이다.
바람직하게는, Rb R2, R3, R4, 및 R5는 각각 독립적으로 수소, 페닐기, 또는 피리디닐기이다. 이와 같이 바이나프탈렌기에 결합된 두 개의 작용기가 서로 다른 구조를 가질 경우, 전자수송 능력， 밴드갭, 에너지 준위 및 열적 특성을 보다 용이하게 조절할 수 있다. 또한, 나프탈렌의 치환 위치에 따른 전기적， 열적 특성이 쉽게 예측이 가능하며, 특히 정공 및 전자의 수송 특성을 능동적으로 조절할 수 있다. 더욱이, 이러한 비대칭적인 구조적 특징은 대칭적인 구조와 비교하였을 때 다양한 유도체를 합성 가능함에 따라， 소자의 효율, 수명 특성의 능동적인 개선이 가능하다. 상기 화학식 1로 표시되는 화합물의 대표적인 예는 다음과 같다:
L l3 L 2, R l3 R 2, and R 3 are described as eu Preferably, and L 2 defined in formula (I) is a single bond, phenylene group (phenylene), or by phenylene groups (biphenylene) each independently . Preferably,, ¾, ¾, and X 5 are each independently N. Preferably, R b R 2 , R 3 , R 4, and R 5 are each independently hydrogen, a phenyl group, or a pyridinyl group. As such, when the two functional groups bonded to the binaphthalene group have different structures, the electron transport ability, the band gap, the energy level, and the thermal characteristics may be more easily controlled. In addition, the electrical and thermal properties according to the substitution position of naphthalene can be easily predicted, and in particular, the transport properties of holes and electrons can be actively controlled. In addition, this asymmetric structural feature is capable of synthesizing various derivatives as compared with the symmetrical structure, thereby enabling active improvement of device efficiency and lifetime characteristics. Representative examples of the compound represented by Formula 1 are as follows:
01-i900/8T0ra¾/X3d
01-i900 / 8T0ra¾ / X3d
Ο^Ζ900/8ΐΟΖΗΜ/Χ3<Ι
Ο ^ Ζ900 / 8ΐΟΖΗΜ / Χ3 <Ι
Ο^Ζ900/8ΐΟΖΗΜ/Χ3<Ι
SI Ο ^ Ζ900 / 8ΐΟΖΗΜ / Χ3 <Ι SI
Ο^Ζ900/8ΐΟΖΗΜ/Χ3<Ι
91 Ο ^ Ζ900 / 8ΐΟΖΗΜ / Χ3 <Ι 91
Ο^Ζ900/8ΐΟΖΗΜ/Χ3<Ι
LI Ο ^ Ζ900 / 8ΐΟΖΗΜ / Χ3 <Ι LI
Ο^Ζ900/8ΐΟΖΗΜ/Χ3<Ι
81 Ο ^ Ζ900 / 8ΐΟΖΗΜ / Χ3 <Ι 81
Ο^Ζ900/8ΐΟΖΗΜ/Χ3<Ι
61 Ο ^ Ζ900 / 8ΐΟΖΗΜ / Χ3 <Ι 61
Ο^Ζ900/8ΐΟΖΗΜ/Χ3<Ι
Ο ^ Ζ900 / 8ΐΟΖΗΜ / Χ3 <Ι
-Ζ900/8Ϊ0ΖΗΉ/Χ3<1 S86lii/8T0Z OAV
-Ζ900 / 8Ϊ0ΖΗΉ / Χ3 <1 S86lii / 8T0Z OAV
일 예로， 상기 화학식 1로 표시되는 화합물 중 Ar^l 상기 화학식 2로 표시되고, ：^은 페닐렌이며， L2는 단일결합인 화합물은 하기 반웅식 1과 같은 제조 방법으로 제조할 수 있다ᅳ
[반웅식 1]
For example, Ar ^ l of the compound represented by Chemical Formula 1 is represented by Chemical Formula 2, wherein: ^ is phenylene, and L 2 is a single bond compound may be prepared by the same method as in Scheme 1 below. [Banungsik 1]
상기 화학식 1의 화합물 중 나머지 화합물들 또한 치환기를 달리한 반웅물을 적용하여 상기 반웅식 1과 동일한 또는 유사한 방법으로 제조할 수 있다. 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다. 또한, 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다. 일례로, 본 발명은 제 1 전극; 상기 제 1 전극과 대향하여 구비된 제 2 전극; 및 상기 제 1 전극과 상기 제 2 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. 본 발명의 유기 발광 소자의 유기물 층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대，
본 발명의 유기 발광 소자는 유기물 층으로서 정공주입층, 정공수송층, 발광층， 전자수송층, 전자주입층 둥을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층을 포함할 수 있다. 또한, 상기 유기물 층은 정공주입층, 정공수송층, 또는 정공 주입과 수송을 동시에 하는 층을 포함할 수 있고, 상기 정공주입층, 정공수송충， 또는 정공 주입과 수송을 동시에 하는 층은 상기 화학식 1로 표시되는 화합물을 포함한다. 또한, 상기 유기물 층은 발광층을 포함할 수 있고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함한다. 또한, 상기 유기물 층은 전자수송층， 또는 전자주입층을 포함할 수 있고, 상기 전자수송층， 또는 전자주입층은 상기 화학식 1로 표시되는 화합물을 포함한다. 또한, 상기 전자수송층, 전자주입층， 또는 전자수송 및 전자주입을 동시에 하는 층은 상기 화학식 1로 표시되는 화합물을 포함한다. 또한, 상기 유기물 층은 발광층 및 전자수송층을 포함하고, 상기 전자수송층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 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 있다ᅳ 예컨대, 본 발명의 일실시예에 따른 유기 발광 소자의 구조는 도 1 및 도 2에 예시되어 있다. 도 1은 기판 (1), 양극 (2), 발광층 (3), 음극 (4)으로 이루어진 유기 발광
소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 발광층에 포함될 수 있다. 도 2는 기판 (1), 양극 (2), 정공주입층 (5), 정공수송층 (6), 발광층 (7), 전자수송층 (8) 및 음극 (4)로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 정공주입충, 정공수송층, 발광층 및 전자수송층 중 1층 이상에 포함될 수 있다. 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. 예컨대， 본 발명에 따른 유기 발광 소자는 기판 상에 제 1 전극, 유기물층 및 제 2 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 정공 주입층， 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물 층을 형성한후， 그 위에 음극으로 사용할 수 있는 물질을 증착시켜 제조할 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수 있다. 또한, 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.
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. 일례로， 상기 게 1 전극은 양극이고, 상기 제 2 전극은 음극이거나， 또는 상기 게 1 전극은 음극이고, 상기 게 2 전극은 양극이다. 상기 양극 물질로는 통상 유기물 층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 상기 양극 물질의 구체적인 예로는 바나듐, 크름, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물 (ΠΌ), 인듐아연 산화물 (IZO)과 같은 금속 산화물; ΖηΟ:Α1 또는 SN02:Sb와 같은 금속과 산화물의 조합; 폴리 (3-메틸티오펜), 폴리 [3,4- (에틸렌 -1,2-디옥시)티오펜] (PEDOT), 폴리피를 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. 상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 상기 음극 물질의 구체적인 예로는 마그네슘, 칼슴, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄， 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 Li02/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다. 상기 정공주입층은 전극으로부터 정공을 주입하는 층으로, 정공 주입 물질로는 정공을 수송하는 능력을 가겨 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, 핵사니트릴핵사아자트리페닐렌 계열의 유기물, 퀴나크리돈 (quinacridone)계열의 '유기물， 페릴렌 (perylene) 계열의 유기물，
안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정 되는 것은 아니다. 상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 정공 수송 물질로 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물， 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다ᅳ 상기 발광 물질로는 정공수송층과 전자수송층으로부터 정공과 전자를 각각 수송 받아 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. 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. 도편트 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 비차환된다. 구체적으로 스티릴아민, 스티릴디아민, 스티릴트리아민, 스티릴테트라아민 등이 있으나， 이에 한정되지 않는다. 또한， 금속 착체로는 이리듐 착체, 백금 착체 등이 있으나， 이에 한정되지 않는다. 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 A1 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본 -금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이 임의의 원하는 캐소드 물질과 함께" 사용할 수 있다. 특히, 적절한 캐소드 물질의 예는 낮은 일함수를 가지고 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로 세슘, 바륨, 칼슘, 이테르븀 및 사마륨이고, 각 경우 알루미늄 층 또는 실버층이 뒤따른다. 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. 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 )(0-크레졸라토)갈륨, 비스 (2-메틸 -8-퀴놀리나토) (1- 나프를라토)알루미늄, 비스 (2-메틸 -8-퀴놀리나토) (2-나프를라토)갈륨 등이 있으나, 이에 한정되지 않는다. 본 발명에 따른 유기 발광 소자는 사용되는재료에 따라 전면 발광형， 후면 발광형 또는 양면 발광형일 수 있다. 또한， 상기 화학식 1로 표시되는 화합물은 유기 발광 소자 외에도 유기 태양 전지 또는 유기 트랜지스터에 포함될 수 있다. 상기 화학식 1로 표시되는 화합물 및 이를 포함하는 유기 발광 소자의 제조를 이하 실시예에서 구체적으로 설명한다. 그러나 하기 실시예는 본 발명을 예시하기 위한 것이며， 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다. The remaining compounds in the compound of Formula 1 may also be prepared by the same or similar method as that of Banung Formula 1 by applying a counterungmul having different substituents. The manufacturing method may be more specific in the production examples to be described later. The present invention also provides an organic light emitting device including the compound represented by Chemical Formula 1. In one embodiment, the present invention comprises a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1. do. The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. for example, The organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer as an organic layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers. The organic layer may include a hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting holes, and the hole injecting layer, a hole transporter, or a layer for simultaneously injecting and transporting a hole may be represented by Formula 1 above. It includes a compound represented. In addition, the organic layer may include a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1. In addition, the organic layer may include an electron transport layer, or an electron injection layer, the electron transport layer, or the electron injection layer comprises a compound represented by the formula (1). In addition, the electron transport layer, the electron injection layer, or the layer for the electron transport and the electron injection at the same time includes a compound represented by the formula (1). In addition, the organic material layer may include a light emitting layer and an electron transport layer, and the electron transport layer may include a compound represented by Chemical Formula 1. In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. In addition, 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 material layers, and an anode are sequentially stacked on a substrate. The structure of the organic light emitting device according to this is illustrated in FIGS. 1 and 2. 1 shows an organic light emitting device consisting of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 An example of the device is shown. In such a structure, the compound represented by Formula 1 may be included in the light emitting layer. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is. In such a structure, the compound represented by Formula 1 may be included in one or more layers of the hole injection worm, hole transport layer, light emitting layer and electron transport layer. The organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1. In addition, 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. For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. In addition, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer may be formed thereon, and then, a material that may be used as a cathode may be deposited thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. In addition, the compound represented by Formula 1 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode ' material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto. In one example, the first electrode is an anode, the second electrode is a cathode, or the first electrode is a cathode, the second electrode is an anode. As the anode material, a material having a large work function is generally preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material include metals such as vanadium, crumb, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ΠΌ), indium zinc oxide (IZO); A combination of a metal and an oxide such as ΖηΟ: Α1 or SN0 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto. no. It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, kale, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or Li0 2 / Al, and the like, but are not limited thereto. The hole injection layer is a layer for injecting holes from an electrode, and has a capability of transporting holes with a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect with respect to a light emitting layer or a light emitting material, and is produced in the light emitting layer. The compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. Preferably, 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 layer. Specific examples of the hole injecting material is a metal porphyrin (porphyrin), oligothiophene, arylamine series of organic matter, hex nitrile hex-aza triphenyl "organic Len based organic material, quinacridone (quinacridone) series of perylene (perylene) Organic matter Anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto. The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer. The hole transport layer is a material that can transport holes from an anode or a hole injection layer to a light emitting layer. This is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto. The light emitting material includes holes and electrons from the hole transport layer and the electron transport layer. As a material capable of emitting light in the visible light region by transporting and binding each of them, a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (P-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto. The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic containing compound. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and the heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto. Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periplanthene having an arylamino group. The styrylamine compound is a compound in which at least one arylvinyl group is substituted with substituted or unsubstituted arylamine, and a substituent selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group Is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like, but is not limited thereto. In addition, the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like. 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 transporting material is a material that can inject electrons well from the cathode and transfer them to the light emitting layer. Suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transporting layer is a conventional material according to any of the examples of "may be used. In particular, suitable cathode material with the desired cathode material after the aluminum layer or silver layer has a low work function, as used according to the prior art. More specifically, Cesium, barium, calcium, ytterbium and samarium, each followed by an aluminum layer or a silver layer, the electron injection layer being a layer for injecting electrons from the electrode, having the ability to transport electrons, the effect of electron injection from the cathode, A compound having an excellent electron injection effect on the light emitting layer or the light emitting material, preventing migration of excitons generated in the light emitting layer to the hole injection layer, and excellent in thin film formation ability is preferable. Methane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, Midazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like, and derivatives thereof, metal complex compounds and nitrogen-containing five-membered ring derivatives, and the like, but are not limited to these metal complex compounds, such as 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) ( 0 -cresolato) gallium , Bis (2-methyl-8-quinolinato) (1-naphlato) aluminum, bis (2-methyl-8-quinolinato) (2-naphlato) gallium and the like, but are not limited thereto. . The organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type according to the material used. In addition, the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device. The production of the compound represented by Chemical Formula 1 and the organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.
<제조예 1><Manufacture example 1>
MS[M+H]+ = 622 MS [M + H] + = 622
<제조예 2> <Manufacture example 2>
MS[M+H]+ = 738 MS [M + H] + = 738
<제조예 3>
<Manufacture example 3>
질소 분위기에서 500 mL등근 바닥 플라스크에 화합물 A (20.00 g, 27.26 mmol), 화합물 D (9.68 g, 27.26 mmol)을 테트라하이드로퓨란 300 mL에 완전히 녹인 후 2M 탄산칼륨 수용액 (150 mL)을 첨가하고, ' 테트라키스- (트리페닐포스핀)팔라듐 (0.94 g, 0.82 mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온 (23±5 °C)으로 온도를 낮추고 물층을 제거하고, 무수 황산마그네슘으로 건조한 후 감압농축시키고, 에틸아세테이트 180 mL로 재결정하여 화합물 3 (compound 3; 10.9 g, 60%)을 제조하였다. In a 500 mL back-bottom flask in a nitrogen atmosphere, Compound A (20.00 g, 27.26 mmol) and Compound D (9.68 g, 27.26 mmol) were completely dissolved in 300 mL of tetrahydrofuran and 2M aqueous potassium carbonate solution (150 mL) was added thereto. 'tetrakis- insert (triphenylphosphine) palladium (0.94 g, 0.82 mmol) was stirred under heating for 3 hours. The mixture was cooled to room temperature (23 ± 5 ° C.), the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 180 mL of ethyl acetate to obtain compound 3 (compound 3; 10.9 g, 60%).
MS[M+H]+ = 622 MS [M + H] + = 622
<계 예 4> <Example 4>
MS[M+H]+ = 622 MS [M + H] + = 622
<제조예 5> Production Example 5
[F] {E] [compound 5.1 [F] {E] [compound 5 . One
질소 분위기에서 500 mL둥근 바닥 플라스크에 화합물 F (20.00 g, 27.26 mmol), 화합물 E (9.68 g, 27.26 mmol)을 테트라하이드로퓨란 300 mL에 완전히 녹인 후 2M 탄산칼륨 수용액 (150 mL)을 첨가하고， 테트라키스- (트리페닐포스핀)팔라듐 (0.94 g, 0.82 mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온 (23±5 °C)으로 온도를 낮추고 물층을 제거하고, 무수 황산마그네슘으로 건조한 후 감압농축시키고, 에틸아세테이트 180 mL로 재결정하여 화합물 5 (compound 5; 9.8 g, 54%)을 제조하였다. In a 500 mL round-bottom flask in a nitrogen atmosphere, Compound F (20.00 g, 27.26 mmol) and Compound E (9.68 g, 27.26 mmol) were completely dissolved in 300 mL of tetrahydrofuran, followed by 2M aqueous potassium carbonate solution (150 mL). Tetrakis- (triphenylphosphine) palladium (0.94 g, 0.82 mmol) was added thereto, followed by heating and stirring for 3 hours. The mixture was cooled to room temperature (23 ± 5 ° C.), the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 180 mL of ethyl acetate to obtain compound 5 (compound 5; 9.8 g, 54%).
MS[M+H]+ = 622 MS [M + H] + = 622
<제조예 6>
<Manufacture example 6>
질소 분위기에서 500 mL 등근 바닥 훌라스크에 화합물 G (20.00 g, 27.35 mmol), 화합물 E (9.71 g, 27.35 mmol)을 테트라하이드로퓨란 300 mL에 완전히 녹인 후 2M 탄산칼륨 수용액 (150 mL)을 첨가하고, 테트라키스- (트리페닐포스핀)팔라듐 (0.94 g, 0.82 mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온 (23±5 °C)으로 온도를 낮추고 물층을 제거하고, 무수 황산마그네슘으로 건조한 후 감압농축시키고, 에틸아세테이트 180 mL로 재결정하여 화합물 6 (compound 6; 11.5 g, 63%)을 제조하였다. Dissolve Compound G (20.00 g, 27.35 mmol) and Compound E (9.71 g, 27.35 mmol) in 300 mL of tetrahydrofuran in a 500 mL back bottom hulask under nitrogen atmosphere, then add 2M aqueous potassium carbonate solution (150 mL). Tetrakis- (triphenylphosphine) palladium (0.94 g, 0.82 mmol) was added thereto, followed by heating and stirring for 3 hours. The mixture was cooled to room temperature (23 ± 5 ° C.), the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 180 mL of ethyl acetate to prepare compound 6 (compound 6; 11.5 g, 63%).
MS[M+H]+ = 620 MS [M + H] + = 620
<제조예 7> <Manufacture example 7>
33.11 mmol), 화합물 D (11.75 g, 33.11 mmol)을 테트라하이드로퓨란 300 mL에
완전히 녹인 후 2M 탄산칼륨 수용액 (150 mL)을 첨가하고, 테트라키스- (트리페닐포스핀)팔라듐 (1.14 g, 0.99 mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온 (23±5 °C)으로 온도를 낮추고 물층을 제거하고, 무수 황산마그네슘으로 건조한 후 감압농축시키고, 에틸아세테이트 180 mL로 재결정하여 화합물 7 (compound 7; 10.2 g, 58%)을 제조하였다. 33.11 mmol), Compound D (11.75 g, 33.11 mmol) in 300 mL of tetrahydrofuran After complete dissolution, 2M aqueous potassium carbonate solution (150 mL) was added thereto, and tetrakis- (triphenylphosphine) palladium (1.14 g, 0.99 mmol) was added thereto, followed by heating and stirring for 3 hours. The mixture was cooled to room temperature (23 ± 5 ° C.), the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 180 mL of ethyl acetate to obtain compound 7 (compound 7; 10.2 g, 58%).
MS[M+H]+ = 533 MS [M + H] + = 533
<제조예 8><Manufacture example 8>
[I] [B] [compound 8] 질소 분위기에서 500 mL등근 바닥 플라스크에 화합물 I (20.00 g, 37.52 mmol), 화합물 B (13.32 g, 37.52 mmol)을 테트라하이드로퓨란 300 mL에 완전히 녹인 후 2M 탄산칼륨 수용액 (150 mL)을 첨가하고， 테트라키스- (트리페닐포스핀)팔라듐 (1.30 g, 1.12 mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온 (23±5 °C)으로 온도를 낮추고 물층을 제거하고, 무수 황산마그네슴으로 건조한 후 감압농축시키고, 에틸아세테이트 180 mL로 재결정하여 화합물 8 (compound 8; 10.4 g, 56%)을 제조하였다. [I] [B] [compound 8] After dissolving Compound I (20.00 g, 37.52 mmol) and Compound B (13.32 g, 37.52 mmol) in 300 mL of tetrahydrofuran in a 500 mL back-bottom flask in a nitrogen atmosphere, 2M carbonate Aqueous potassium solution (150 mL) was added, tetrakis- (triphenylphosphine) palladium (1.30 g, 1.12 mmol) was added thereto, and the mixture was heated and stirred for 3 hours. The mixture was cooled to room temperature (23 ± 5 ° C.), the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 180 mL of ethyl acetate to obtain compound 8 (compound 8; 10.4 g, 56%). .
MS[M+H]+ = 482 MS [M + H] + = 482
<제조예 9>
<Manufacture example 9>
[J] [ ] [compound 9】 질소 분위기에서 500 mL등근 바닥 플라스크에 화합물 J (20.00 g, 30.44 mmol), 화합물 K (10.80 g, 30.44 mmol)을 테트라하이드로퓨란 300 mL에 완전히 녹인 후 2M 탄산칼륨 수용액 (150 mL)을 첨가하고, 테트라키스- (트리페닐포스핀)팔라듐 (1.05 g, 0.91 mmol)을 넣은 후 3 시간 동안 가열 교반하였다. 상온 (23±5 °C)으로 온도를 낮추고 물층을 제거하고, 무수 황산마그네슘으로 건조한 후 감압농축시키고, 에틸아세테이트 180 mL로 재결정하여 화합물 9 (compound 9; 11.2 g, 63%)을 제조하였다ᅳ [J] [] [compound 9] Dissolve Compound J (20.00 g, 30.44 mmol) and Compound K (10.80 g, 30.44 mmol) in 3 00 mL of tetrahydrofuran in a 500 mL back-bottom flask in nitrogen atmosphere, and then dissolve 2M carbonate. Aqueous potassium solution (150 mL) was added, tetrakis- (triphenylphosphine) palladium (1.05 g, 0.91 mmol) was added and the mixture was heated and stirred for 3 hours. The mixture was cooled to room temperature (23 ± 5 ° C.), the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 180 mL of ethyl acetate to obtain compound 9 (compound 9; 11.2 g, 63%).
MS[M+H]+ = 586 MS [M + H] + = 586
<제조예 10>Production Example 10
[L] [ ] [compound 10] 질소 분위기에서 500 mL등근 바닥플라스크에 화합물 L (20.00 g, 36.10 mmol), 화합물 M (12.81 g, 36.10 mmol)을 테트라하이드로퓨란 300 mL에 완전히 녹인 후 2M 탄산칼륨 수용액 (150 mL)을 첨가하고, 테트라키스- (트리페닐포스핀)팔라듐 (1.25 g, 1.08 mmol)을 넣은 후 3 시간 동안 가열
교반하였다. 상온 (23±5 °C)으로 온도를 낮추고 물층을 제거하고, 황산마그네슘으로 건조한 후 감압농축시키고, 에틸아세테이트 180 재결정하여 화합물 10 (compound 10; 9.8 g, 56%)을 제조하였다. [L] [] [compound 10] Compound M (20.00 g, 36.10 mmol) and compound M (12.81 g, 36.10 mmol) were completely dissolved in 300 mL of tetrahydrofuran in a 500 mL isometric bottom flask in a nitrogen atmosphere. Aqueous solution (150 mL) was added, tetrakis- (triphenylphosphine) palladium (1.25 g, 1.08 mmol) was added, followed by heating for 3 hours. Stirred. The temperature was lowered to room temperature (23 ± 5 ° C.), the water layer was removed, dried over magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate 180 to obtain compound 10 (compound 10; 9.8 g, 56%).
MS[M+H]+ = 483 MS [M + H] + = 483
<제조예 11>Production Example 11
MS[M+H]+ = 586 MS [M + H] + = 586
<실시예 1-1> <Example 1-1>
ITO(indium tin oxide)가 1,000 A의 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. ΠΌ를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알코올, 아세톤, 메탄올의 용제로 초음파 세척을 하고
건조시킨 후 플라즈마 세정기로 수송시켰다. 또한， 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한후 진공 증착기로 기판을 수송시켰다. 이렇게 준비된 ΠΌ 투명 전극 위에 하기 화합물 [HI-A]를 600 A의 두께로 열 진공증착하여 정공 주입층을 형성하였다. 상기 정공 주입층 위에 하기 화합물 [HAT] (50 A) 및 하기 화합물 [HT-A] (600 A)를 순차적으로 진공증착하여 정공 수송층을 형성하였다. 이어서, 상기 정공 수송층 위에 막 두께 200 A으로 하기 화합물 [BH]와 [BD]를 25:1의 중량비로 진공증착하여 발광층을 형성하였다. 상기 발광층 위에 상기 제조예 1에서 제조한 화합물 1과 하기 화합물 [LiQ](Lithiumquinolate)를 1 :1 중량비로 진공증착하여 350 A의 두께로 전자 주입 및 수송층을 형성하였다. 상기 전자 주입 및 수송층 위에 순차적으로 10 A 두께로 리튬 플루라이드 (LiF)와 1,000 A 두께로 알루미늄을 증착하여 음극을 형성하였다ᅳA glass substrate coated with a thickness of 1,000 A of ITO (indium tin oxide) was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. product was used as a detergent, and distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water. After washing ΠΌ for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic cleaning with a solvent of isopropyl alcohol, acetone, methanol After drying it was transported to a plasma scrubber. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator. The following compound [HI-A] was vacuum-deposited to a thickness of 600 A on the πΌ transparent electrode thus prepared to form a hole injection layer. The following compound [HAT] (50 A) and the following compound [HT-A] (600 A) were sequentially vacuum deposited on the hole injection layer to form a hole transport layer. Subsequently, the following Compounds [BH] and [BD] were vacuum-deposited at a weight ratio of 25: 1 on the hole transport layer to have a film thickness of 200 A to form a light emitting layer. Compound 1 prepared in Preparation Example 1 and the following compound [LiQ] (Lithiumquinolate) were vacuum-deposited at a weight ratio of 1: 1 on the emission layer to form an electron injection and transport layer at a thickness of 350 A. Lithium fluoride (LiF) and aluminum at 1,000 A thickness were sequentially deposited on the electron injection and transport layer to form a cathode.
[HI-A] [HAT] [HT-A] [HI-A] [HAT] [HT-A]
[BH] [BD] [LiQ] 상기의 과정에서 유기물의 증착속도는 0.4 내지 0.9 A/sec를 유지하였고, 음극의 리튬플루오라이드는 0.3 A/sec, 알루미늄은 2 A/sec의 증착 속도를 유지하였으며, 증착시 진공도는 l xl(r7 내지 5xl(r8 torr를 유지하여, 유기
발광 소자를 제작하였다. [BH] [BD] [LiQ] In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 A / sec, the lithium fluoride at the cathode was maintained at 0.3 A / sec, and the aluminum was maintained at 2 A / sec. In the deposition, the degree of vacuum was l xl (r 7 to 5xl (r 8 torr was maintained, and organic A light emitting device was produced.
<실시예 1-2 내지 1-11> <Examples 1-2 to 1-11>
상기 실시예 1-1에서 화합물 1 대신 표 1에 기재된 바와 같이 화합물 2 내지 11 중 한 화합물을 사용하는 것을 제외하고는, 상기 실시예 1-1과 동일한 방법으로 유기 발광 소자를 제조하였다. An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using one compound of Compounds 2 to 11 as described in Table 1 instead of Compound 1 in Example 1-1.
<비교예 1-1 내지 1-3> <Comparative Examples 1-1 to 1-3>
상기 실시예 1-1에서 화합물 1 대신 표 1에 기재된 바와 같이 하기 구조의 화합물 (I), (II), 또는 (III)를 사용하는 것을 제외하고는 실시예 1-1과 동일한 방법으로 유기 발광소자를 제작하였다. Except for using the compound (I), (II), or (III) of the structure shown in Table 1 instead of compound 1 in Example 1-1 in the same manner as in Example 1-1 The device was produced.
<비교예 1-4> <Comparative Example 1-4>
상기 실시예 1-1에서 화합물 1 대신 표 1에 기재된 바와 같이 하기 구조의 화합물 (IV)를 사용하는 것을 제외하고는 실시예 1-1과 동일한 방법으로 유기 발광 소자를 제작하였다. An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using Compound (IV) having the following structure as described in Table 1 instead of Compound 1 in Example 1-1.
(IV)
<실험예 1> (IV) Experimental Example 1
상기 실시예 1-1 내지 1-11， 및 비교예 1-1 내지 1-4에서 제조한 유기 발광 소자에 대하여 10 mA/cm2의 전류 밀도에서 구동 전압과 발광 효율을 측정하였으며， 또 20 mA/cm2의 전류 밀도에서 초기 휘도 대비 90%가 되는 시간 (T90)을 측정하였다. 그 결과를 하기 표 1에 나타내었다. The driving voltage and the luminous efficiency of the organic light emitting diodes manufactured in Examples 1-1 to 1-11 and Comparative Examples 1-1 to 1-4 were measured at a current density of 10 mA / cm 2 , and 20 mA. The time (T 90 ) of 90% of the initial luminance at a current density of / cm 2 was measured. The results are shown in Table 1 below.
【표 1】 Table 1
ITO(indium tin oxide)가 1,000 A의 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 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알코올， 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한후 진공 증착기로 기판을 수송시켰다. 이렇게 준비된 ITO 투명 전극 위에 하기 화합물 [HI-A]를 600 A의 두께로 열 진공증착하여 정공 주입층을 형성하였다. 상기 정공 주입층 위에 하기 화합물 [HAT] (50 A) 및 하기 화합물 [HT-A] (600 A)를 순차적으로 진공증착하여 정공 수송층을 형성하였다. 이어서, 상기 정공 수송층 위에 막 두께 200 A으로 하기 화합물 [BH]와 [BD]를 25:1의 중량비로 진공증착하여 발광층을 형성하였다. 상기 발광층 위에 상기 제조예 1에서 제조한 화합물 1을 진공증착하여 200 A의 두께로 전자조절층을 형성하였다. 상기 전자조절층 위에 하기 화합물 [ET] 및 하기 화합물 [LiQ](Lithiumquinolate)를 1:1 중량비로 진공증착하여 150 A의 두께로 전자 주입 및 수송층을 형성하였다. 상기 전자 주입 및 수송층 위에 순차적으로 10 A 두께로 리튬 플루라이드 (LiF)와 1,000 A 두께로 알루미늄을 증착하여 음극을 형성하였다.
A glass substrate coated with a thickness of 1,000 A of ITO (indium tin oxide) was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. product was used as a detergent, and distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator. The following compound [HI-A] was thermally vacuum deposited to a thickness of 600 A on the prepared ITO transparent electrode to form a hole injection layer. The following compound [HAT] (50 A) and the following compound [HT-A] (600 A) were sequentially vacuum deposited on the hole injection layer to form a hole transport layer. Subsequently, the following Compounds [BH] and [BD] were vacuum-deposited at a weight ratio of 25: 1 on the hole transport layer to have a film thickness of 200 A to form a light emitting layer. Compound 1 prepared in Preparation Example 1 was vacuum-deposited on the emission layer to form an electron control layer with a thickness of 200 A. The following compound [ET] and the following compound [LiQ] (Lithiumquinolate) were vacuum-deposited at a weight ratio of 1: 1 on the electron control layer to form an electron injection and transport layer at a thickness of 150 A. Lithium fluoride (LiF) and aluminum at 1,000 A thickness were sequentially deposited on the electron injection and transport layer to form a cathode.
상기의 과정에서 유기물의 증착속도는 0.4 내지 으9 A/sec를 유지하였고, 음극의 리튬플루오라이드는 0.3 A/sec, 알루미늄은 2 A/sec의 증착 속도를 유지하였으며， 증착시 진공도는 l xlO-7 내지 5xl(r8 torr를 유지하여, 유기 발광 소자, 제작하였다. In the above process, the deposition rate of the organic material was maintained at 0.4 to 9 A / sec, the lithium fluoride of the cathode was maintained at 0.3 A / sec, and the aluminum was maintained at the deposition rate of 2 A / sec. An organic light emitting device was manufactured by maintaining 7 to 5xl (r 8 torr).
<실시예 2-2 내지 2-10> <Examples 2-2 to 2-10>
상기 실시예 2-1에서 화합물 1 대신 표 2에 기재된 바와 같이 화합물 2 내지 11 중 한 화합물을 사용하는 것을 제외하고는， 상기 실시예 2-1과 동일한 방법으로 유기 발광 소자를 제조하였다. An organic light-emitting device was manufactured in the same manner as in Example 2-1, except for using one compound of Compounds 2 to 11 as described in Table 2 instead of Compound 1 in Example 2-1.
<비교예 2-1 내지 1-3> <Comparative Examples 2-1 to 1-3>
상기 실시예 2-1에서 화합물 1 대신 표 2에 기재된 바와 같이 하기 구조의 화합물 (I), (II), 또는 (III)를 사용하는 것을 제외하고는 실시예 2-1과 동일한 방법으로 유기 발광소자를 제작하였다.
Except for using the compound (I), (II), or (III) of the structure shown in Table 2 instead of compound 1 in Example 2-1 in the same manner as in Example 2-1 The device was produced.
(I) (II) (I) (II)
<비교예 2-4> <Comparative Example 2-4>
상기 실시예 2-1에서 화합물 1 대신 표 2에 기재된 바와 같이 하기 구조의 화합물 (IV)를 사용하는 것을 제외하고는 실시예 2-1과 동일한 방법으로 유기 발광 소자를 제작하였다. An organic light emitting diode was manufactured according to the same method as Example 2-1 except for using the compound (IV) having the following structure as described in Table 2 instead of the compound 1 in Example 2-1.
(IV) (IV)
<실험예 2> Experimental Example 2
상기 실시예 2-1 내지 2-11, 및 비교예 2-1 내지 2-4에서 제조한 유기 발광 소자에 대하여 10 mA/cm2의 전류밀도에서 구동전압과 발광 효율을 측정하였으며, 또 20 mA/cm2의 전류밀도에서 초기 휘도 대비 90%가 되는 시간 (T90)을 측정하였다. 그 결과를 하기 표 2에 나타내었다. For the organic light emitting diodes manufactured in Examples 2-1 to 2-11 and Comparative Examples 2-1 to 2-4, the driving voltage and the luminous efficiency were measured at a current density of 10 mA / cm 2 , and 20 mA. The time (T 90 ) of 90% of the initial luminance at the current density of / cm 2 was measured. The results are shown in Table 2 below.
【표 2】 Table 2
화합물 ᄌ O 효율 색좌표 수명 (h) Compound ᄌ O Efficiency Color coordinate lifetime (h)
(V@10mA/cm2) (cd/A@10mA/cm2) (x,y) T90 at (V @ 10mA / cm 2 ) (cd / A @ 10mA / cm 2 ) (x, y) T90 at
20mA/cm2 실시예 2-1 1 4.11 5.59 (0.142, 0.096) 246 실시예 2-2 2 4.09 5.69 (0.142, 0.096) 237
실시예 2-3 3 4.17 5.57 (0.142, 0.099) 277 실시예 2-4 4 4.21 5.06 (0.142, 0.096) 169 실시예 2-5 5 4.15 5.49 (0.142, 0.098) 248 실시예 2-6 6 4.20 5.46 (0.142, 0.096) 260 실시예 2-7 7 4.36 5.03 (0.142, 0.096) 159 실시예 2-8 8 4.08 5.68 (0.142, 0.096) 225 실시예 2-9 9 4.23 4.96 (0.142, 0.099) 158 실시예 2-10 10 4.18 5.50 (0.141, 0.046) 234 실시예 2-11 11 4.21 5.69 (0.142, 0.096) 240 비교예 2-1 I 4.74 3.77 (0.142, 0.099) 85 비교예 2-2 II 4.52 3.89 (0.151, 0.109) 88 비교예 2-3 III 4.51 3.92 (0.151, 0.109) 84 비교예 2-4 IV 4.81 5.11 (0.151, 0.100) 81 상가 표 2의 결과로부터, 상기 화학식 1로 표시되는 헤테로고리 화합물이 유기 발광 소자의 전자조절층에 사용될 수 있음을 확인할 수 있다. 20 mA / cm 2 Example 2-1 1 4.11 5.59 (0.142, 0.096) 246 Example 2-2 2 4.09 5.69 (0.142, 0.096) 237 Examples 2-3 3 4.17 5.57 (0.142, 0.099) 277 Examples 2-4 4 4.21 5.06 (0.142, 0.096) 169 Examples 2-5 5 4.15 5.49 (0.142, 0.098) 248 Examples 2-6 6 4.20 5.46 (0.142, 0.096) 260 Example 2-7 7 4.36 5.03 (0.142, 0.096) 159 Example 2-8 8 4.08 5.68 (0.142, 0.096) 225 Example 2-9 9 4.23 4.96 (0.142, 0.099) 158 Example 2-10 10 4.18 5.50 (0.141, 0.046) 234 Example 2-11 11 4.21 5.69 (0.142, 0.096) 240 Comparative Example 2-1 I 4.74 3.77 (0.142, 0.099) 85 Comparative Example 2-2 II 4.52 3.89 (0.151 , 0.109) 88 Comparative Example 2-3 III 4.51 3.92 (0.151, 0.109) 84 Comparative Example 2-4 IV 4.81 5.11 (0.151, 0.100) 81 Addition From the results of Table 2, the heterocyclic compound represented by Formula 1 is organic. It can be seen that it can be used for the electron control layer of the light emitting device.
[부호의 설명】 [Explanation of code]
1 : 기판 2: 이:그ᅳ 1: Substrate 2: 2:
3: 발광층 4: ᄋ그 3: light emitting layer 4:
ᄆ — ㅁ —
5: 정공주입층 6: 고 소 ¾■ 5: hole injection layer 6: height ¾
7: 발광층 8: 전자수송층
7: light emitting layer 8: electron transport layer
Claims
【청구항 1】 [Claim 1]
하기 화학식 1로 표시되는 바이나프탈렌 (binaphthalene) 화합물: Binaphthalene compound represented by the following formula (1):
！^은 단일결합, 또는 치환또는 비치환된 C6 60 아릴이고, ！ ^ Is a single bond or a substituted or unsubstituted C 6 60 aryl,
L2는 단일결합, 치환 또는 비치환된 C6_60 아릴, 또는 비치환된 C5 60 헤테로아릴이고, L 2 is a single bond, a substituted or unsubstituted C 6 _ 60 aryl, or an unsubstituted C 5 60 heteroaryl,
Arr& 하기 화학식 2， 화학식 3, 화학식 4, 또는 화학식 5로 표시되고 Arr & is represented by the following formula (2), (3), (4), or (5)
[화학식 2] [Formula 2]
[
[
[화학식 4] [Formula 4]
[화학식 5]
[Formula 5]
상기 화학식 2 내지 5에서, In Chemical Formulas 2 to 5,
Χ,, X2, 및 X3는 각각독립적으로 N또는 CR4이며, 여기서， N은 적어도 1개 이상이고, X, X 2 , and X 3 are each independently N or CR 4, wherein N is at least one,
¾, 및 X5는 각각 독립적으로 N 또는 CR5이며, 여기서， N은 적어도 1개 이상이고, ¾, and X 5 are each independently N or CR 5 , wherein N is at least one,
Ru 2, 및 R3는 각각 독립적으로 치환 또는 비치환된 알킬, 치환 또는 비치환된 C6_60 아릴, 또는 치환 또는 비치환된 C5 60 헤테로아릴이고， 또는Ru 2 , and R 3 are each independently substituted or unsubstituted alkyl, substituted or unsubstituted C 6 _ 60 aryl, or substituted or unsubstituted C 5 60 heteroaryl, or
R1; R2, 및 R3는 각각 독립적으로 상기 알킬, 아릴, 헤테로아릴의 수소가 중수소 또는 CN으로 치환된 것이고, R 1; R 2 , and R 3 are each independently hydrogen of the alkyl, aryl, heteroaryl substituted with deuterium or CN,
R4, 및 R5는 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 CM0 알킬, 치환 또는 비치환된 C6_60 아릴, 또는 치환 또는 비치환된 C5 헤테로아릴이다. R 4, and R 5 are each independently hydrogen, deuterium, substituted or unsubstituted C M0 alkyl, substituted or unsubstituted C 6 _ 60 aryl, or substituted or unsubstituted C 5 heteroaryl.
【청구항 2】 [Claim 2]
거 U항에 있어서， In U,
상기 화학식 1로 표시되는 화합물은 하기 화학식 1-1, 1-2, 1-3， 1-4, 1-5, 1-6, 또는 1-7로 표시되는， Compound represented by Formula 1 is represented by the following formula 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, or 1-7,
화합물: compound:
[화학식 1-1] [Formula 1-1]
, , Ri, R2, 및 ¾는 게 1항에서 정의한 바와 같다. ,, Ri, R 2 , and ¾ are as defined in item 1.
【청구항 3】 [Claim 3]
제 1항에 있어서, The method of claim 1,
L,, 및 Lr 결합, 페닐렌， 또는 바이페닐렌인， L, and Lr bond, phenylene or biphenylene
화합물. compound.
【청구항 4】 [Claim 4]
제 1항에 있어서, The method of claim 1,
Xi, X2, X3, X4, 및 X5는 N인, Xi, X 2 , X 3 , X4, and X 5 are N,
화합물. compound.
【청구항 5】 [Claim 5]
게 1항에 있어서, According to claim 1,
R!,R2,R3, R4, 및 ¾는 수소， 페닐, 또는 피리디닐인, R !, R 2 , R 3 , R 4, and ¾ are hydrogen, phenyl, or pyridinyl,
화합물. compound.
【청구항 6】 [Claim 6]
제 1항에 있어서, The method of claim 1,
상기 화학식 1로 표시되는 화합물은 하기로 구성되는 군으로부터 선택되는 어느 하나인， The compound represented by Formula 1 is any one selected from the group consisting of
화합물:
f compound: f
Ο^Ζ900/8ΐΟΖΗΜ/Χ3<Ι
Ο ^ Ζ900 / 8ΐΟΖΗΜ / Χ3 <Ι
^Ζ900/8Ϊ0ΖΗΜ/Χ3«Ι ^ Ζ900 / 8Ϊ0ΖΗΜ / Χ3 «Ι
S86TZi/8lOZ OAV
OS S86TZi / 8lOZ OAV OS
Ο^Ζ900/8ΐΟΖΗΜ/Χ3<Ι
ig Ο ^ Ζ900 / 8ΐΟΖΗΜ / Χ3 <Ι ig
Ο^Ζ900/8ΐΟΖΗΜ/Χ3<Ι
Ο ^ Ζ900 / 8ΐΟΖΗΜ / Χ3 <Ι
Ο^Ζ900/8ΐΟΖΗΜ/Χ3<Ι
S9 Ο ^ Ζ900 / 8ΐΟΖΗΜ / Χ3 <Ι S9
Ο^Ζ900/8ΐΟΖΗΜ/Χ3<Ι
Ο ^ Ζ900 / 8ΐΟΖΗΜ / Χ3 <Ι
Ο^Ζ900/8ΐΟΖΗΜ/Χ3<Ι
99 Ο ^ Ζ900 / 8ΐΟΖΗΜ / Χ3 <Ι 99
Ο^Ζ900/8ΐΟΖΗΜ/Χ3<Ι
9S Ο ^ Ζ900 / 8ΐΟΖΗΜ / Χ3 <Ι 9S
Ο^Ζ900/8ΐΟΖΗΜ/Χ3<Ι
Ο ^ Ζ900 / 8ΐΟΖΗΜ / Χ3 <Ι
【청구항 7] [Claim 7]
거] 1 전극; 상기 게 1 전극과 대향하여 구비된 제 2 전극; 및 상기 제 1 전극과 상기 제 2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 제 1항 내지 제 6항 중 어느 하나의 항에 따른 화합물을 포함하는 것인, 유기 발광 소자.
1 electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound according to any one of claims 1 to 6. That is, an organic light emitting device.
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| US16/609,199 US11453650B2 (en) | 2017-05-31 | 2018-05-31 | Heterocyclic compound and organic light emitting device comprising the same |
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| KR20120051598A (en) * | 2010-11-12 | 2012-05-22 | 주식회사 엘지화학 | New compounds and organic electronic device using the same |
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| KR20150039486A (en) * | 2013-10-02 | 2015-04-10 | 삼성디스플레이 주식회사 | Compound and organic light emitting device comprising same |
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| KR20120061056A (en) * | 2010-11-04 | 2012-06-12 | 주식회사 엘지화학 | New nitrogen-containing heterocyclic compounds and organic electronic device using the same |
| KR20120051598A (en) * | 2010-11-12 | 2012-05-22 | 주식회사 엘지화학 | New compounds and organic electronic device using the same |
| KR20150025259A (en) * | 2013-08-28 | 2015-03-10 | 삼성디스플레이 주식회사 | Compound and organic light emitting device comprising the same |
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