KR20200054078A - Organic light emitting device - Google Patents
Organic light emitting device Download PDFInfo
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- KR20200054078A KR20200054078A KR1020190138523A KR20190138523A KR20200054078A KR 20200054078 A KR20200054078 A KR 20200054078A KR 1020190138523 A KR1020190138523 A KR 1020190138523A KR 20190138523 A KR20190138523 A KR 20190138523A KR 20200054078 A KR20200054078 A KR 20200054078A
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- KR
- South Korea
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- compound
- light emitting
- emitting device
- organic light
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- 150000001875 compounds Chemical class 0.000 claims abstract description 71
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- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 7
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005332 alkyl sulfoxy group Chemical group 0.000 description 1
- 125000005377 alkyl thioxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 150000003974 aralkylamines Chemical group 0.000 description 1
- 125000005165 aryl thioxy group Chemical group 0.000 description 1
- 125000003609 aryl vinyl group Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
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- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
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- 239000011737 fluorine Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
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- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
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- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 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
- 125000004076 pyridyl group Chemical group 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
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- 238000007650 screen-printing Methods 0.000 description 1
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- 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
- 229910052709 silver Inorganic materials 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
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- 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
- 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
- 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
- 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
- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
- H10K50/165—Electron transporting layers comprising dopants
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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Abstract
Description
본 발명은 유기 발광 소자에 관한 것이다. The present invention relates to an organic light emitting device.
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, the organic light emitting phenomenon refers to a phenomenon that converts 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, and a fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies have been 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. The organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layered structure composed of different materials, for example, may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode, and electrons are injected at the cathode, and an exciton is formed when the injected holes meet the electrons. When it falls to the ground again, 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 the organic light emitting device as described above is continuously required.
본 발명은 유기 발광 소자에 관한 것이다. The present invention relates to an organic light emitting device.
본 발명은 하기의 유기 발광 소자를 제공한다:The present invention provides the following organic light emitting device:
양극; 발광층; 제1 화합물을 포함하는 전자조절층; 제2 화합물을 포함하는 전자수송층; 및 음극을 포함하고, anode; Emitting layer; An electron-regulating layer comprising a first compound; An electron transport layer comprising a second compound; And a cathode,
하기 수학식 1 및 2를 만족하는,Satisfying the
유기 발광 소자:Organic light emitting device:
[수학식 1][Equation 1]
cETLLUMO ≤ 2.8 eVcETL LUMO ≤ 2.8 eV
[수학식 2][Equation 2]
-0.7 eV < (cETLLUMO - ETLLUMO) < 0 eV-0.7 eV <(cETL LUMO -ETL LUMO ) <0 eV
상기 수학식 1 및 2에서, In
cETLLUMO는 상기 제1 화합물의 LUMO이고, cETL LUMO is LUMO of the first compound,
ETLLUMO는 상기 제2 화합물의 LUMO이다.ETL LUMO is the LUMO of the second compound.
상술한 유기 발광 소자는 전자조절층과 전자수송층에 포함되는 화합물을 조절하여, 유기 발광 소자에서 효율의 향상, 낮은 구동 전압 및/또는 수명 특성을 향상시킬 수 있다. The above-described organic light-emitting device may improve the efficiency, low driving voltage, and / or lifespan characteristics in the organic light-emitting device by adjusting the compounds included in the electron control layer and the electron transport layer.
도 1은, 기판(1), 양극(2), 정공수송층(3), 발광층(4), 전자조절층(5), 전자수송층(6), 및 음극(7)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.
도 2는, 본 발명의 실험예에서 HOMO 준위를 측정한 결과를 나타낸 것이다.
도 3 내지 9는, 본 발명의 실험예에서 LUMO 준위를 측정한 결과를 나타낸 것이다.1 is an example of an organic light emitting device comprising a
Figure 2 shows the results of measuring the HOMO level in the experimental example of the present invention.
3 to 9 show the results of measuring the LUMO level in the experimental examples of the present invention.
이하, 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다.Hereinafter, it will be described in more detail in order to help the understanding of the present invention.
본 명세서에서, 
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 사이클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환 또는 비치환된 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 비페닐기일 수 있다. 즉, 비페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다.The term "substituted or unsubstituted" as used herein refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amino group; Phosphine oxide group; Alkoxy groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxyl group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Ar alkenyl group; Alkyl aryl groups; Alkylamine groups; 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 substituents among the exemplified substituents above . For example, "a substituent having two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.
본 명세서에서 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 number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
본 명세서에 있어서, 에스테르기는 에스테르기의 산소가 탄소수 1 내지 25의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 25의 아릴기로 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the oxygen of the ester group may be substituted with a straight chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In this specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
본 명세서에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.
본 명세서에 있어서, 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, the boron group is specifically a trimethyl boron group, a triethyl boron group, a t-butyl dimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, but is not limited thereto.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 6이다. 알킬기의 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 사이클로펜틸메틸,사이클로헥틸메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸펜틸, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이들에 한정되지 않는다.In the present specification, the alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group are methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 6이다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 알릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나 이들에 한정되지 않는다.In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples 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, styrenyl group, styrenyl group, and the like, but are not limited thereto.
본 명세서에 있어서, 사이클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 사이클로프로필, 사이클로부틸, 사이클로펜틸, 3-메틸사이클로펜틸, 2,3-디메틸사이클로펜틸, 사이클로헥실, 3-메틸사이클로헥실, 4-메틸사이클로헥실, 2,3-디메틸사이클로헥실, 3,4,5-트리메틸사이클로헥실, 4-tert-부틸사이클로헥실, 사이클로헵틸, 사이클로옥틸 등이 있으나, 이에 한정되지 않는다.In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., as a monocyclic aryl 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, and the like, but is not limited thereto.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. 상기 플루오레닐기가 치환되는 경우, 
본 명세서에 있어서, 헤테로고리기는 이종 원소로 O, N, Si 및 S 중 1개 이상을 포함하는 헤테로고리기로서, 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로고리기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤조옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 페난쓰롤린기(phenanthroline), 이소옥사졸릴기, 티아디아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridil 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, isooxazolyl group, tiadiia A sleepy group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.
본 명세서에 있어서, 아르알킬기, 아르알케닐기, 알킬아릴기, 아릴아민기 중의 아릴기는 전술한 아릴기의 예시와 같다. 본 명세서에 있어서, 아르알킬기, 알킬아릴기, 알킬아민기 중 알킬기는 전술한 알킬기의 예시와 같다. 본 명세서에 있어서, 헤테로아릴아민 중 헤테로아릴은 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 아르알케닐기 중 알케닐기는 전술한 알케닐기의 예시와 같다. 본 명세서에 있어서, 아릴렌은 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로아릴렌은 2가기인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 탄화수소 고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 아릴기 또는 사이클로알킬기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다.In the present specification, an aryl group in an aralkyl group, an alkenyl group, an alkylaryl group, and an arylamine group is the same as the exemplified aryl group described above. In the present specification, the alkyl group among the aralkyl group, alkylaryl group, and alkylamine group is the same as the above-described example of the alkyl group. In the present specification, the description of the heteroaryl group among the heteroarylamines described above may be applied. In the present specification, the alkenyl group in the alkenyl group is the same as the exemplified alkenyl group. In the present specification, the description of the aryl group described above may be applied, except that the arylene is a divalent group. In the present specification, the description of the heterocyclic group described above may be applied, except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aryl group or cycloalkyl group described above may be applied, except that two substituents are formed by bonding. In this specification, the heterocycle is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied, except that two substituents are formed by bonding.
이하 각 구성 별로 본 발명을 상세히 설명한다. Hereinafter, the present invention will be described in detail for each configuration.
양극 및 음극Anode and cathode
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 positive electrode material is preferably a material having a large work function so that hole injection into the organic material layer is smooth. Specific examples of the positive electrode 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); A combination of metal and oxide such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 상기 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다. The cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the 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 is a multilayer structure material such as LiF / Al or LiO 2 / Al, but is not limited thereto.
정공주입층Hole injection layer
본 발명에 따른 유기 발광 소자는 필요에 따라 양극 상에 정공주입층을 포함할 수 있다. The organic light emitting device according to the present invention may include a hole injection layer on the anode, if necessary.
상기 정공주입층은 양극으로부터 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 for injecting holes from the anode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and is produced in the light emitting layer. A compound that prevents migration of the excitons to the electron injection layer or the electron injection material and has excellent thin film formation ability is preferred. It is preferred that the high occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic matter, hexanitrile hexaazatriphenylene-based organic matter, quinacridone-based organic matter, and perylene-based Organic materials, anthraquinones, polyaniline and polythiophene-based conductive polymers, and the like, but are not limited thereto.
정공수송층Hole transport layer
본 발명에 따른 유기 발광 소자는 필요에 따라 정공수송층을 포함할 수 있다. The organic light emitting device according to the present invention may include a hole transport layer, if necessary.
본 발명에서 사용되는 정공수송층은 양극 또는 양극 상에 형성된 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 정공 수송 물질로 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. The hole transport layer used in the present invention is a layer that transports holes from the hole injection layer formed on the anode or the anode to the light emitting layer, and transports holes from the anode or the hole injection layer as a hole transport material to be transferred to the light emitting layer. As a material, a material having high mobility for holes is suitable.
구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.
발광층Emitting layer
상기 발광층에 포함되는 발광 물질로는 정공수송층과 전자수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. The light-emitting material included in the light-emitting layer is a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
상기 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. The light emitting layer may include a host material and a dopant material. The host material may be a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
도펀트 재료로는 방향족 아민 유도체, 스트릴아민 화합물, 붕소 착체, 플루오란텐 화합물, 금속 착체 등이 있다. 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.Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periplanene, etc. having an arylamino group, and substituted or unsubstituted as a styrylamine compound. A compound in which at least one arylvinyl group is substituted with the arylamine, a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. Further, examples of the metal complex include an iridium complex, a platinum complex, and the like, but are not limited thereto.
전자조절층 및 전자수송층Electronic control layer and electron transport layer
본 발명에 따른 유기 발광 소자는 발광층에 인접한 전자조절층 및 전자조절층에 인접한 전자수송층을 포함한다. 상기 전자조절층은 양극에서 주입된 정공이 발광층에서 재결합되지 않고 전자수송층으로 넘어가는 것을 방지하는 역할을 하며, 상기 전자수송층은 음극 또는 전자주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 역할을 한다. The organic light emitting device according to the present invention includes an electron control layer adjacent to the light emitting layer and an electron transport layer adjacent to the electron control layer. The electron regulating layer serves to prevent holes injected from the anode from being recombined in the light emitting layer and to pass to the electron transport layer, and the electron transport layer serves to receive electrons from the cathode or electron injection layer and transport electrons to the light emitting layer. do.
특히, 본 발명에서는, 전자조절층을 구성하는 물질과 전자수송층을 구성하는 물질이 특정 조건을 만족함으로써, 유기 발광 소자에서 효율의 향상, 낮은 구동 전압 및/또는 수명 특성을 향상시킬 수 있다. Particularly, in the present invention, the material constituting the electron-controlling layer and the material constituting the electron-transporting layer satisfy specific conditions, thereby improving efficiency in the organic light-emitting device, and improving low driving voltage and / or life characteristics.
구체적으로, 상기 제1 화합물을 포함하는 전자조절층과 상기 제2 화합물을 포함하는 전자수송층은 하기 수학식 1 및 2를 만족한다:Specifically, the electron regulating layer comprising the first compound and the electron transporting layer containing the second compound satisfy
[수학식 1][Equation 1]
cETLLUMO ≤ 2.8 eVcETL LUMO ≤ 2.8 eV
[수학식 2][Equation 2]
-0.7 eV < (cETLLUMO - ETLLUMO) < 0 eV-0.7 eV <(cETL LUMO -ETL LUMO ) <0 eV
상기 수학식 1 및 2에서, In
cETLLUMO는 상기 제1 화합물의 LUMO이고, cETL LUMO is LUMO of the first compound,
ETLLUMO는 상기 제2 화합물의 LUMO이다.ETL LUMO is the LUMO of the second compound.
한편, 본 명세서에서, 상기 cETLLUMO 및 ETLLUMO는 각 LUMO의 절대값을 의미한다. Meanwhile, in the present specification, the cETL LUMO and ETL LUMO mean the absolute value of each LUMO.
바람직하게는, 상기 제1 화합물의 LUMO 값이 2.0 eV 이상이다. Preferably, the LUMO value of the first compound is 2.0 eV or more.
상기 수학식 1 및 2에 따라 상기 전자조절층을 구성하는 화합물의 LUMO 값이 적정 범위에 있으면서, 동시에 상기 전자수송층을 구성하는 화합물의 LUMO 값이 수학식 2와 같은 범위에 있음으로 인하여, 전자조절층층과 전자수송층의 LUMO 차이로 전자의 이동을 효과적으로 조절하여 유기 발광 소자의 성능을 향상시킬 수 있다.According to
바람직하게는, 상기 수학식 2의 (cETLLUMO - ETLLUMO) 값이 -0.69 eV 초과, 0.68 eV 초과, 또는 0.67 eV 초과이고, -0.1 eV 미만, -0.2 eV 미만, -0.3 eV 미만, -0.4 eV 미만, 또는 -0.5 eV 미만이다. Preferably, the (cETL LUMO -ETL LUMO ) value of
바람직하게는, 상기 제1 화합물은 하기 화학식 1로 표시되는 화합물이다:Preferably, the first compound is a compound represented by
[화학식 1][Formula 1]
상기 화학식 1에서, In
X1 및 X2는 각각 독립적으로 NR1, O, 또는 S이되, X1 및 X2 중 적어도 하나는 NR1이고, X 1 and X 2 are each independently NR 1 , O, or S, wherein at least one of X 1 and X 2 is NR 1 ,
R1은 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 C1-60 알킬; 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O, 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이고, R 1 is each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S,
R2 및 R3는 각각 독립적으로, 수소; 중수소; 치환 또는 비치환된 C1-60 알킬; 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O, 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이다.R 2 and R 3 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S.
바람직하게는, R1은 페닐, 비페닐릴, 터페닐릴, 나프틸, 페난쓰레닐, 디벤조퓨라닐, 또는 디벤조티오페닐이다. Preferably, R 1 is phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, dibenzofuranyl, or dibenzothiophenyl.
바람직하게는, R2 및 R3은 수소, 디벤조퓨라닐, 또는 디벤조티오페닐이다. Preferably, R 2 and R 3 are hydrogen, dibenzofuranyl, or dibenzothiophenyl.
바람직하게는, 상기 화학식 1로 표시되는 화합물은 하기로 구성되는 군으로부터 선택되는 어느 하나이다:Preferably, the compound represented by
한편, 상기 화학식 1로 표시되는 화합물은 하기 반응식 1과 같은 방법으로 제조할 수 있다.Meanwhile, the compound represented by
[반응식 1][Scheme 1]
상기 반응식 1에서 X'를 제외한 나머지 정의는 앞서 정의한 바와 같으며, X'는 할로겐이고, 바람직하게는 브로모, 또는 클로로이다. 상기 반응은 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.In
바람직하게는, 상기 제2 화합물은 하기 화학식 2로 표시되는 화합물이다:Preferably, the second compound is a compound represented by
[화학식 2][Formula 2]
상기 화학식 2에서, In
X3는 각각 독립적으로 N, 또는 CH이도, X3 중 2개 이상이 N이고, X 3 are each independently N, or CH, and two or more of X 3 are N,
Ar1 및 Ar2는 각각 독립적으로 치환 또는 비치환된 C6-60 아릴이고,Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 aryl,
n은 1 또는 2이고, n is 1 or 2,
L은 직접 결합; n+1가의 치환 또는 비치환된 C6-60 방향족 고리; 또는 n+1가의 치환 또는 비치환된 O, N, Si 및 S 중 1개 이상을 포함하는 C2-60 헤테로방향족 고리이고, 단 n이 2인 경우 L은 직접 결합이 아니고, L is a direct bond; n + 1 monovalent substituted or unsubstituted C 6-60 aromatic ring; Or a C 2-60 heteroaromatic ring containing one or more of n + 1 monovalent substituted or unsubstituted O, N, Si and S, provided that when n is 2, L is not a direct bond,
Ar3은 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O, 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이다.Ar 3 is substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S.
바람직하게는, Ar1 및 Ar2는 각각 독립적으로, 페닐, 또는 비페닐릴이다. Preferably, Ar 1 and Ar 2 are each independently phenyl or biphenylyl.
바람직하게는, L은 단일 결합; 2가의 벤젠; 3가의 벤젠; 또는 하기로 구성되는 군으로부터 선택되는 어느 하나이다:Preferably, L is a single bond; Divalent benzene; Trivalent benzene; Or any one selected from the group consisting of:
바람직하게는, Ar3는 하기로 구성되는 군으로부터 선택되는 어느 하나이다:Preferably, Ar 3 is any one selected from the group consisting of:
바람직하게는, 상기 화학식 2로 표시되는 화합물은 하기로 구성되는 군으로부터 선택되는 어느 하나이다:Preferably, the compound represented by
한편, 상기 화학식 2로 표시되는 화합물은 하기 반응식 2와 같은 방법으로 제조할 수 있다.Meanwhile, the compound represented by
[반응식 2][Scheme 2]
상기 반응식 2에서 X"를 제외한 나머지 정의는 앞서 정의한 바와 같으며, X"는 할로겐이고, 바람직하게는 브로모, 또는 클로로이다. 상기 반응은 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.In
한편, 상기 전자주입층이 음극과 인접하여 형성되는 경우, 상기 전자주입층은 금속 착체 화합물 또는 유기 화합물을 추가로 포함할 수 있다. 이때, 상기 전자주입층 내에서, 상기 제2 화합물과 상기 금속 착체 화합물 또는 유기 화합물의 중량비는, 1:99 내지 99:1, 10:90 내지 90:10, 20:80 내지 80:20, 30:70 내지 70:30, 또는 40:60 내지 60:40일 수 있다. Meanwhile, when the electron injection layer is formed adjacent to the cathode, the electron injection layer may further include a metal complex compound or an organic compound. At this time, in the electron injection layer, the weight ratio of the second compound and the metal complex compound or organic compound is 1:99 to 99: 1, 10:90 to 90:10, 20:80 to 80:20, 30 : 70 to 70:30, or 40:60 to 60:40.
상기 금속 착체 화합물로, 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.As the metal complex compound, 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-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, etc. , But is not limited to this.
전자주입층Electron injection layer
본 발명에 따른 유기 발광 소자는 필요에 따라 전자주입층을 포함할 수 있다. The organic light emitting device according to the present invention may include an electron injection layer, if necessary.
상기 전자주입층은 음극으로부터 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 cathode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration 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 and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
유기 발광 소자Organic light emitting diode
본 발명에 따른 유기 발광 소자의 구조를 도 1에 예시하였다. 도 1은, 기판(1), 양극(2), 정공수송층(3), 발광층(4), 전자조절층(5), 전자수송층(6), 및 음극(7)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.The structure of the organic light emitting device according to the present invention is illustrated in FIG. 1. 1 is an example of an organic light emitting device comprising a
본 발명에 따른 유기 발광 소자는 상술한 구성을 순차적으로 적층시켜 제조할 수 있다. 이때, 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(physical Vapor Deposition)방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공수송층, 발광층, 전자조절층 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. 또한, 발광층은 호스트 및 도펀트를 진공 증착법 뿐만 아니라 용액 도포법에 의하여 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.The organic light emitting device according to the present invention can be manufactured by sequentially stacking the above-described configuration. At this time, a positive electrode is formed by depositing a metal or conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. Then, an organic material layer including a hole transport layer, a light emitting layer, an electron control layer, and an electron transport layer is formed thereon, and a material that can be used as a cathode is deposited thereon. In addition to this method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate. In addition, the light emitting layer may be formed by a host and a dopant by a vacuum deposition method as well as a solution application method. Here, the solution application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, 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 may be manufactured by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
한편, 본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.On the other hand, the organic light emitting device according to the present invention may be a front emission type, a back emission type or a double-sided emission type depending on the material used.
이하, 발명의 이해를 돕기 위하여 바람직한 실시예들을 제시한다. 그러나 하기의 실시예들은 발명을 예시하기 위한 것일 뿐, 발명을 이들만으로 한정하는 것은 아니다.Hereinafter, preferred embodiments are presented to help understanding of the invention. However, the following examples are only for illustrating the invention, and the invention is not limited thereto.
[제조예 1] [Production Example 1]
제조예 1-1: 화합물 cET-1의 제조Preparation Example 1-1: Preparation of compound cET-1
상기 cET-1-sm1 화합물(10 g, 25.1 mmol)과 상기 cET-1-sm2 화합물(9.3 g, 25.1 mmol)을 THF(100 mL)에 완전히 녹인 후, 탄산 칼륨(10.4 g, 75.3 mmol)을 물(40 mL)에 용해시켜 첨가하였다. 테트라키스(트리페닐포스핀) 팔라듐(0)(0.87 g, 0.753 mmol)을 넣은 후, 8시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 반응을 종결한 후, 탄산 칼륨 용액을 제거하여 흰색 고체를 여과하였다. 여과된 흰색 고체를 THF 및 에틸 아세테이트로 각각 2번씩 세척하여 상기 cET-1 화합물(10.6 g, 수율 75%)을 제조하였다.The cET-1-sm1 compound (10 g, 25.1 mmol) and the cET-1-sm2 compound (9.3 g, 25.1 mmol) were completely dissolved in THF (100 mL), followed by potassium carbonate (10.4 g, 75.3 mmol). It was dissolved in water (40 mL) and added. After adding tetrakis (triphenylphosphine) palladium (0) (0.87 g, 0.753 mmol), the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed to filter the white solid. The filtered white solid was washed twice each with THF and ethyl acetate to prepare the cET-1 compound (10.6 g, yield 75%).
MS: [M+H]+ = 561MS: [M + H] + = 561
제조예 1-2: 화합물 cET-2의 제조Preparation Example 1-2: Preparation of compound cET-2
각 출발 물질을 상기 반응식과 같이 하는 것을 제외하고는, 제조예 1의 제조 방법과 동일한 방법으로 상기 cET-2 화합물을 제조하였다.The cET-2 compound was prepared in the same manner as in Preparation Example 1, except that each starting material was in the same manner as in the above scheme.
MS: [M+H]+ = 502MS: [M + H] + = 502
[제조예 2] [Production Example 2]
제조예 2-1: 화합물 ET-1의 제조Preparation Example 2-1: Preparation of Compound ET-1
각 출발 물질을 상기 반응식과 같이 하는 것을 제외하고는, 제조예 1-1의 제조 방법과 동일한 방법으로 상기 ET-1 화합물을 제조하였다.The ET-1 compound was prepared in the same manner as in Preparation Example 1-1, except that each starting material was as in the above reaction scheme.
MS: [M+H]+ = 550MS: [M + H] + = 550
제조예 2-2: 화합물 ET-2의 제조Preparation Example 2-2: Preparation of Compound ET-2
각 출발 물질을 상기 반응식과 같이 하는 것을 제외하고는, 제조예 1-1의 제조 방법과 동일한 방법으로 상기 ET-2 화합물을 제조하였다.The ET-2 compound was prepared in the same manner as in Production Example 1-1, except that each starting material was as in the above reaction scheme.
MS: [M+H]+ = 613MS: [M + H] + = 613
제조예 2-3: 화합물 ET-3의 제조Preparation Example 2-3: Preparation of compound ET-3
각 출발 물질을 상기 반응식과 같이 하고, 상기 ET-3-sm2 화합물의 당량을 상기 ET-3-sm1 화합물 대비 2배의 당량을 사용하는 것을 제외하고는, 제조예 1-1의 제조 방법과 동일한 방법으로 상기 화학식 ET-3로 표시되는 화합물을 제조하였다.Each starting material is the same as the reaction scheme, and the same method as in Production Example 1-1, except that the equivalent amount of the ET-3-sm2 compound is twice the equivalent of the ET-3-sm1 compound. By the method, a compound represented by Chemical Formula ET-3 was prepared.
MS: [M+H]+ = 743MS: [M + H] + = 743
제조예 2-4: 화합물 ET-4의 제조Preparation Example 2-4: Preparation of compound ET-4
각 출발 물질을 상기 반응식과 같이 하는 것을 제외하고는, 제조예 1-1의 제조 방법과 동일한 방법으로 상기 ET-4 화합물을 제조하였다.The ET-4 compound was prepared by the same method as the production method of Preparation Example 1-1, except that each starting material was as in the above reaction scheme.
MS: [M+H]+ = 580MS: [M + H] + = 580
[실험예 1][Experimental Example 1]
앞서 제조한 화합물의 HOMO 에너지 및 LUMO 에너지 값을 측정하였다. 비교를 위하여, 하기 ET-A 화합물도 함께 측정하였다. HOMO energy and LUMO energy values of the previously prepared compounds were measured. For comparison, the following ET-A compounds were also measured.
구체적으로, 상기 HOMO 준위는 대기하 광전자 분광 장치(RIKEN KEIKI Co., Ltd. 제조: AC3)를 이용하여 측정하였으며(도 2), 상기 LUMO 준위는 photoluminescence(PL)을 통하여 측정된 파장 값으로 계산하였다. 이에 측정된 결과를 하기 표 1에 나타내었다.Specifically, the HOMO level was measured using an atmospheric photoelectron spectroscopy device (manufactured by RIKEN KEIKI Co., Ltd .: AC3) (FIG. 2), and the LUMO level was calculated as a wavelength value measured through photoluminescence (PL). Did. The measured results are shown in Table 1 below.
실험예 2-1Experimental Example 2-1
ITO (indium tin oxide)가 1000 Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이때, 세제로는 피셔사 (Fischer Co.) 제품을 사용하였으며, 증류수로는 밀리포어사 (Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다. A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1000 에 was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer Co. product was used as the detergent, and distilled water filtered secondarily by a filter of 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, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and transporting to a plasma cleaner. In addition, after the substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transferred to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에 하기 HI-A 화합물을 600 Å의 두께로 열 진공 증착하여 정공주입층을 형성하였다. 상기 정공주입층 상에 하기 HAT 화합물을 50 Å의 두께로, 하기 HT-A 화합물을 60 Å의 두께로 순차적으로 진공 증착하여 정공수송층을 형성하였다. 상기 정공수송층 상에 하기 BH 화합물 및 하기 BD 화합물을 25:1의 중량비로 200 Å의 두께로 진공 증착하여 발광층을 형성하였다. 상기 발광층 상에 앞서 제조한 화합물 cET-1을 50 Å의 두께로 진공 증착하여 전자조절층을 형성하였다. 상기 전자조절층 상에 앞서 제조한 화합물 ET-1과 하기 LiQ 화합물을 1:1의 중량비로 300 Å의 두께로 진공 증착하여 전자수송층을 형성하였다. 상기 전자수송층 상에 리튬 플루오라이드(LiF)를 10 Å의 두께로, 알루미늄을 1000 Å의 두께로 순차적으로 증착하여 음극을 형성하였다. The following HI-A compound was thermally vacuum-deposited to a thickness of 600 위에 on the prepared ITO transparent electrode to form a hole injection layer. On the hole injection layer, the following HAT compound was sequentially vacuum deposited to a thickness of 50, and the following HT-A compound to a thickness of 60 Å to form a hole transport layer. On the hole transport layer, the following BH compound and the following BD compound were vacuum deposited to a thickness of 200 Pa in a weight ratio of 25: 1 to form a light emitting layer. The compound cET-1 prepared above was vacuum-deposited to a thickness of 50 Å on the light emitting layer to form an electronic control layer. The electron transport layer was formed by vacuum-depositing the compound ET-1 prepared above and the following LiQ compound on a thickness of 300 로 in a weight ratio of 1: 1 on the electron control layer. Lithium fluoride (LiF) was sequentially deposited on the electron transport layer to a thickness of 10, and aluminum to a thickness of 1000 순차적 to form a negative electrode.
상기의 과정에서 유기물의 증착 속도는 0.4 내지 0.9 Å/sec를 유지하였고, 음극의 리튬 플루오라이드는 0.3 Å/sec, 알루미늄은 2 Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 1×10-7 내지 5×10-5 torr를 유지하여, 유기 발광 소자를 제조하였다.In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 Å / sec, the lithium fluoride of the negative electrode was maintained at a deposition rate of 0.3 Å / sec and aluminum at 2 2 / sec, and the vacuum degree during deposition was 1 × 10. An organic light-emitting device was manufactured by maintaining -7 to 5 x 10 -5 torr.
실시예 2-2 내지 2-8 Examples 2-2 to 2-8
상기 실시예 2-1에서, 화합물 cET-1 및/또는 ET-1 대신 하기 표 2의 화합물을 사용한 것을 제외하고는 실시예 2-1과 동일한 방법으로 유기 발광 소자를 제조하였다.In Example 2-1, an organic light emitting device was manufactured according to the same method as Example 2-1 except for using the compound of Table 2 below instead of the compounds cET-1 and / or ET-1.
비교예 2-1 및 2-12Comparative Examples 2-1 and 2-12
상기 실시예 2-1에서, 화합물 cET-1 및/또는 ET-1 대신 하기 표 2의 화합물을 사용한 것을 제외하고는 실시예 2-1과 동일한 방법으로 유기 발광 소자를 제조하였다. 하기 표 2에서 화합물 ET-A은 하기와 같다. In Example 2-1, an organic light emitting device was manufactured according to the same method as Example 2-1 except for using the compound of Table 2 below instead of the compounds cET-1 and / or ET-1. In Table 2, the compound ET-A is as follows.
상기 실시예 및 비교예에서 제조한 유기 발광 소자에 대하여 10 mA/cm2의 전류 밀도에서 구동 전압과 발광 효율을 측정하였고, 20 mA/cm2의 전류 밀도에서 초기 휘도 대비 90%가 되는 시간(T90)을 측정하였다. 상기 결과를 하기 표 2에 나타내었다.The driving voltage and luminous efficiency were measured at the current density of 10 mA / cm 2 for the organic light-emitting device manufactured in the above Examples and Comparative Examples, and the time to be 90% compared to the initial luminance at the current density of 20 mA / cm 2 ( T90). The results are shown in Table 2 below.
조절층Electronic
Control layer
수송층Electronic
Transport layer
(V)Voltage
(V)
(cd/A)efficiency
(cd / A)
(x, y)Color coordinate
(x, y)
(hr)T90
(hr)
1: 기판
2: 양극
3: 정공수송층
4: 발광층
5: 전자조절층
6: 전자수송층
7: 음극1: substrate 2: anode
3: hole transport layer 4: light emitting layer
5: electron control layer 6: electron transport layer
7: Cathode
Claims (10)
발광층;
제1 화합물을 포함하는 전자조절층;
제2 화합물을 포함하는 전자수송층; 및
음극을 포함하고,
하기 수학식 1 및 2를 만족하는,
유기 발광 소자:
[수학식 1]
cETLLUMO ≤ 2.8 eV
[수학식 2]
-0.7 eV < (cETLLUMO - ETLLUMO) < 0 eV
상기 수학식 1 및 2에서,
cETLLUMO는 상기 제1 화합물의 LUMO이고,
ETLLUMO는 상기 제2 화합물의 LUMO이다.
anode;
Emitting layer;
An electron-regulating layer comprising a first compound;
An electron transport layer comprising a second compound; And
A cathode,
Satisfying the following equations 1 and 2,
Organic light emitting device:
[Equation 1]
cETL LUMO ≤ 2.8 eV
[Equation 2]
-0.7 eV <(cETL LUMO -ETL LUMO ) <0 eV
In Equations 1 and 2,
cETL LUMO is LUMO of the first compound,
ETL LUMO is the LUMO of the second compound.
상기 제1 화합물은 하기 화학식 1로 표시되는 화합물인,
유기 발광 소자:
[화학식 1]
상기 화학식 1에서,
X1 및 X2는 각각 독립적으로 NR1, O, 또는 S이되, X1 및 X2 중 적어도 하나는 NR1이고,
R1은 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 C1-60 알킬; 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O, 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이고,
R2 및 R3는 각각 독립적으로, 수소; 중수소; 치환 또는 비치환된 C1-60 알킬; 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O, 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이다.
According to claim 1,
The first compound is a compound represented by the following formula (1),
Organic light emitting device:
[Formula 1]
In Chemical Formula 1,
X 1 and X 2 are each independently NR 1 , O, or S, wherein at least one of X 1 and X 2 is NR 1 ,
R 1 is each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S,
R 2 and R 3 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S.
R1은 페닐, 비페닐릴, 터페닐릴, 나프틸, 페난쓰레닐, 디벤조퓨라닐, 또는 디벤조티오페닐인,
유기 발광 소자.
According to claim 2,
R 1 is phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, dibenzofuranyl, or dibenzothiophenyl,
Organic light emitting device.
상기 화학식 1로 표시되는 화합물은 하기로 구성되는 군으로부터 선택되는 어느 하나인,
유기 발광 소자:
According to claim 2,
The compound represented by Formula 1 is any one selected from the group consisting of,
Organic light emitting device:
상기 제2 화합물은 하기 화학식 2로 표시되는 화합물인,
유기 발광 소자:
[화학식 2]
상기 화학식 2에서,
X3는 각각 독립적으로 N, 또는 CH이도, X3 중 2개 이상이 N이고,
Ar1 및 Ar2는 각각 독립적으로 치환 또는 비치환된 C6-60 아릴이고,
n은 1 또는 2이고,
L은 직접 결합; n+1가의 치환 또는 비치환된 C6-60 방향족 고리; 또는 n+1가의 치환 또는 비치환된 O, N, Si 및 S 중 1개 이상을 포함하는 C2-60 헤테로방향족 고리이고, 단 n이 2인 경우 L은 직접 결합이 아니고,
Ar3은 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O, 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이다.
According to claim 2,
The second compound is a compound represented by the following formula (2),
Organic light emitting device:
[Formula 2]
In Chemical Formula 2,
X 3 are each independently N, or CH, and two or more of X 3 are N,
Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 aryl,
n is 1 or 2,
L is a direct bond; n + 1 monovalent substituted or unsubstituted C 6-60 aromatic ring; Or a C 2-60 heteroaromatic ring containing one or more of n + 1 monovalent substituted or unsubstituted O, N, Si and S, provided that when n is 2, L is not a direct bond,
Ar 3 is substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S.
L은 단일 결합; 2가의 벤젠; 3가의 벤젠; 또는 하기로 구성되는 군으로부터 선택되는 어느 하나인,
유기 발광 소자:
The method of claim 5,
L is a single bond; Divalent benzene; Trivalent benzene; Or any one selected from the group consisting of,
Organic light emitting device:
Ar3는 하기로 구성되는 군으로부터 선택되는 어느 하나인,
유기 발광 소자:
The method of claim 5,
Ar 3 is any one selected from the group consisting of,
Organic light emitting device:
상기 화학식 2로 표시되는 화합물은 하기로 구성되는 군으로부터 선택되는 어느 하나인,
유기 발광 소자:
The method of claim 5,
The compound represented by Formula 2 is any one selected from the group consisting of,
Organic light emitting device:
상기 전자수송층은 금속 착체 화합물 또는 유기 화합물을 추가로 포함하는,
유기 발광 소자.
According to claim 1,
The electron transport layer further comprises a metal complex compound or an organic compound,
Organic light emitting device.
상기 금속 착체 화합물은, 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, 또는 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨인,
유기 발광 소자.The method of claim 9,
The metal complex compound is 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, or bis (2-methyl-8-quinolinato) (2-naphtolato) gallium,
Organic light emitting device.
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2019
- 2019-11-01 CN CN201980051797.9A patent/CN112534595B/en active Active
- 2019-11-01 WO PCT/KR2019/014717 patent/WO2020096286A1/en active Application Filing
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| KR20000051826A (en) | 1999-01-27 | 2000-08-16 | 성재갑 | New organomattalic complex molecule for the fabrication of organic light emitting diodes |
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| Publication number | Publication date |
|---|---|
| CN112534595A (en) | 2021-03-19 |
| CN112534595B (en) | 2024-08-02 |
| WO2020096286A1 (en) | 2020-05-14 |
| KR102238703B1 (en) | 2021-04-09 |
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