KR102588656B1 - Organic light emitting device - Google Patents
Organic light emitting device Download PDFInfo
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- KR102588656B1 KR102588656B1 KR1020210038233A KR20210038233A KR102588656B1 KR 102588656 B1 KR102588656 B1 KR 102588656B1 KR 1020210038233 A KR1020210038233 A KR 1020210038233A KR 20210038233 A KR20210038233 A KR 20210038233A KR 102588656 B1 KR102588656 B1 KR 102588656B1
- Authority
- KR
- South Korea
- Prior art keywords
- group
- organic light
- light emitting
- independently
- emitting device
- Prior art date
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- -1 biphenylyl Chemical group 0.000 claims description 70
- 150000001875 compounds Chemical class 0.000 claims description 69
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
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- 125000001424 substituent group Chemical group 0.000 claims description 20
- 230000001629 suppression Effects 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
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- 125000002950 monocyclic group Chemical group 0.000 description 2
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- UHSLDBAUKWAWBG-UHFFFAOYSA-N [4-(3-phenylcarbazol-9-yl)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1N1C2=CC=C(C=3C=CC=CC=3)C=C2C2=CC=CC=C21 UHSLDBAUKWAWBG-UHFFFAOYSA-N 0.000 description 1
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- 150000004056 anthraquinones Chemical class 0.000 description 1
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- 125000004433 nitrogen atom Chemical group 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
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- 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
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
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- 229910000027 potassium carbonate Inorganic materials 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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- 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
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- 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
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- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
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- 239000011780 sodium chloride Substances 0.000 description 1
- SIXNTGDWLSRMIC-UHFFFAOYSA-N sodium;toluene Chemical compound [Na].CC1=CC=CC=C1 SIXNTGDWLSRMIC-UHFFFAOYSA-N 0.000 description 1
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- 125000003003 spiro group Chemical group 0.000 description 1
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- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 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
- 150000003918 triazines Chemical class 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
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- H10K50/15—Hole transporting layers
-
- 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]
- H10K50/18—Carrier blocking layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- 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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- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
본 발명은 구동 전압, 효율 및 수명이 개선된 유기발광 소자를 제공한다.The present invention provides an organic light emitting device with improved driving voltage, efficiency, and lifespan.
Description
본 발명은 구동 전압, 효율 및 수명이 개선된 유기 발광 소자에 관한 것이다. The present invention relates to an organic light emitting device with improved driving voltage, efficiency, and lifespan.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기 에너지를 빛 에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 넓은 시야각, 우수한 콘트라스트, 빠른 응답 시간을 가지며, 휘도, 구동 전압 및 응답 속도 특성이 우수하여 많은 연구가 진행되고 있다. In general, organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light-emitting devices using the organic light-emitting phenomenon have a wide viewing angle, excellent contrast, fast response time, and excellent luminance, driving voltage, and response speed characteristics, so much research is being conducted.
유기 발광 소자는 일반적으로 양극과 음극 및 상기 양극과 음극 사이에 유기물 층을 포함하는 구조를 가진다. 상기 유기물 층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. Organic light emitting devices generally have a structure including an anode, a cathode, and an organic layer between the anode and the cathode. The organic material layer is often composed of a multi-layer structure made of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton is When it falls back to the ground state, it glows.
상기와 같은 유기 발광 소자에서, 구동 전압, 효율 및 수명이 개선된 유기 발광 소자의 개발이 지속적으로 요구되고 있다.In organic light-emitting devices as described above, there is a continuous need for development of organic light-emitting devices with improved driving voltage, efficiency, and lifespan.
본 발명은 구동 전압, 효율 및 수명이 개선된 유기 발광 소자에 관한 것이다. The present invention relates to an organic light emitting device with improved driving voltage, efficiency, and lifespan.
본 발명은 하기의 유기 발광 소자를 제공한다:The present invention provides the following organic light emitting device:
양극, anode,
음극, cathode,
상기 양극과 상기 음극 사이의 발광층, A light emitting layer between the anode and the cathode,
상기 양극과 상기 발광층 사이의 전자억제층, 및an electron-suppressing layer between the anode and the light-emitting layer, and
상기 전자억제층과 상기 양극 사이에 정공수송층을 포함하고,Comprising a hole transport layer between the electron suppression layer and the anode,
상기 정공수송층은 하기 화학식 1로 표시되는 화합물을 포함하고,The hole transport layer includes a compound represented by the following formula (1),
상기 전자억제층은 하기 화학식 2로 표시되는 화합물을 포함하는,The electron suppression layer includes a compound represented by the following formula (2),
유기 발광 소자:Organic light emitting device:
[화학식 1][Formula 1]
상기 화학식 1에서,In Formula 1,
Ar1은 치환 또는 비치환된 C6-60 아릴이고,Ar 1 is substituted or unsubstituted C 6-60 aryl,
Ar2 및 Ar3는 각각 독립적으로, -NRR' 또는 하기 화학식 3으로 표시되는 치환기이고,Ar 2 and Ar 3 are each independently -NRR' or a substituent represented by the following formula (3),
여기서, R 및 R'은 각각 독립적으로, 치환 또는 비치환된 C6-60 아릴이고,Here, R and R' are each independently substituted or unsubstituted C 6-60 aryl,
[화학식 3][Formula 3]
상기 화학식 3에서,In Formula 3 above,
A 및 B는 각각 독립적으로, 치환 또는 비치환된 C6-60 아릴이고,A and B are each independently a substituted or unsubstituted C 6-60 aryl,
점선은 상기 화학식 1의 L2 또는 L3와 결합되고,The dotted line is combined with L 2 or L 3 of Formula 1,
L1 내지 L3는 각각 독립적으로, 단일 결합, 또는 치환 또는 비치환된 C6-60 아릴렌이고,L 1 to L 3 are each independently a single bond or a substituted or unsubstituted C 6-60 arylene,
R1 및 R2는 각각 독립적으로, 수소 또는 중수소이고,R 1 and R 2 are each independently hydrogen or deuterium,
a 및 b는 각각 독립적으로, 0 내지 3의 정수이고,a and b are each independently an integer from 0 to 3,
[화학식 2][Formula 2]
상기 화학식 2에서,In Formula 2,
Ar4 및 Ar5는 각각 독립적으로, 치환 또는 비치환된 C6-60 아릴, 또는 아다만틸이고,Ar 4 and Ar 5 are each independently substituted or unsubstituted C 6-60 aryl, or adamantyl,
L4 및 L5는 각각 독립적으로, 단일 결합, 또는 치환 또는 비치환된 C6-60 아릴렌이고,L 4 and L 5 are each independently a single bond or substituted or unsubstituted C 6-60 arylene,
R3 내지 R6은 각각 독립적으로, 수소, 중수소, 또는 치환 또는 비치환된 C6-60 아릴이거나; 또는 인접하는 치환기와 결합하여 방향족 고리를 형성할 수 있고,R 3 to R 6 are each independently hydrogen, deuterium, or substituted or unsubstituted C 6-60 aryl; Or, it can be combined with an adjacent substituent to form an aromatic ring,
c d, e, 및 f는 각각 독립적으로, 0 내지 4의 정수이고,c d, e, and f are each independently an integer from 0 to 4,
m 및 n은 각각 독립적으로, 0 내지 2의 정수이다.m and n are each independently integers from 0 to 2.
상술한 유기 발광 소자는, 구동 전압, 효율 및 수명이 우수하다. The organic light emitting device described above is excellent in driving voltage, efficiency, and lifespan.
도 1은, 기판(1), 양극(2), 정공수송층(3), 전자억제층(4), 발광층(5), 및 음극(6)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.
도 2는, 기판(1), 양극(2), 정공주입층(7), 정공수송층(3), 전자억제층(4), 발광층(5), 정공억제층(8), 전자 주입 및 수송층(9), 및 음극(6)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.Figure 1 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a hole transport layer 3, an electron suppressing layer 4, a light emitting layer 5, and a cathode 6.
2 shows a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron blocking layer 4, a light emitting layer 5, a hole blocking layer 8, and an electron injection and transport layer. An example of an organic light-emitting device consisting of (9) and a cathode (6) is shown.
이하, 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다.Hereinafter, the present invention will be described in more detail to aid understanding.
본 명세서에서, 또는 는 다른 치환기에 연결되는 결합을 의미한다. In this specification, or means a bond connected to another substituent.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 사이클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환 또는 비치환된 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 비페닐기일 수 있다. 즉, 비페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다.As used herein, the term “substituted or unsubstituted” refers to deuterium; halogen group; Nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkylthioxy group; Arylthioxy group; Alkyl sulphoxy group; Aryl sulfoxy group; silyl group; boron group; Alkyl group; Cycloalkyl group; alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; heteroarylamine group; Arylamine group; Arylphosphine group; or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups containing one or more of N, O and S atoms, or substituted or unsubstituted with two or more of the above-exemplified substituents linked. . For example, “a substituent group in which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.
본 명세서에서 카보닐기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 40인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In this specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound with the following structure, but is not limited thereto.
본 명세서에 있어서, 에스테르기는 에스테르기의 산소가 탄소수 1 내지 25의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 25의 아릴기로 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the oxygen of the ester group may be substituted with a straight-chain, branched-chain, or ring-chain alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In this specification, the carbon number of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound with the following structure, but is not limited thereto.
본 명세서에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. In the present specification, the silyl group specifically includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited to this.
본 명세서에 있어서, 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, the boron group specifically includes trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, and phenyl boron group, but is not limited thereto.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In this specification, examples of halogen groups include fluorine, chlorine, bromine, or iodine.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 6이다. 알킬기의 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 사이클로펜틸메틸,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, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. According to another embodiment, the carbon number of the alkyl group is 1 to 6. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n. -pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but is not limited to these.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 6이다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 아릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나 이들에 한정되지 않는다.In the present specification, the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, aryl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group, etc., but are not limited to these.
본 명세서에 있어서, 사이클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 사이클로프로필, 사이클로부틸, 사이클로펜틸, 3-메틸사이클로펜틸, 2,3-디메틸사이클로펜틸, 사이클로헥실, 3-메틸사이클로헥실, 4-메틸사이클로헥실, 2,3-디메틸사이클로헥실, 3,4,5-트리메틸사이클로헥실, 4-tert-부틸사이클로헥실, 사이클로헵틸, 사이클로옥틸 등이 있으나, 이에 한정되지 않는다.In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, Examples include, but are not limited to, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 비페닐이기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. 상기 플루오레닐기가 치환되는 경우, 등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. When the fluorenyl group is substituted, It can be etc. However, it is not limited to this.
본 명세서에 있어서, 헤테로고리기는 이종 원소로 O, N, Si 및 S 중 1개 이상을 포함하는 헤테로고리기로서, 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로고리기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 트리아졸기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤조옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 페난쓰롤린기(phenanthroline), 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 벤조티아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si, and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, Examples include isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, and dibenzofuranyl group, but are not limited to these.
본 명세서에 있어서, 아르알킬기, 아르알케닐기, 알킬아릴기, 아릴아민기 중의 아릴기는 전술한 아릴기의 예시와 같다. 본 명세서에 있어서, 아르알킬기, 알킬아릴기, 알킬아민기 중 알킬기는 전술한 알킬기의 예시와 같다. 본 명세서에 있어서, 헤테로아릴아민 중 헤테로아릴은 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 아르알케닐기 중 알케닐기는 전술한 알케닐기의 예시와 같다. 본 명세서에 있어서, 아릴렌은 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로아릴렌은 2가기인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 탄화수소 고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 아릴기 또는 사이클로알킬기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다.In this specification, the aryl group among the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above. In this specification, the aralkyl group, alkylaryl group, and alkylamine group are the same as the examples of the alkyl group described above. In the present specification, the description regarding the heterocyclic group described above may be applied to heteroaryl among heteroarylamines. In this specification, the alkenyl group among the aralkenyl groups is the same as the example of the alkenyl group described above. In the present specification, the description of the aryl group described above can be applied, except that arylene is a divalent group. In the present specification, the description of the heterocyclic group described above can be applied, except that heteroarylene is a divalent group. In the present specification, the description of the aryl group or cycloalkyl group described above can be applied, except that the hydrocarbon ring is not monovalent and is formed by combining two substituents. In the present specification, the description of the heterocyclic group described above can be applied, except that the heterocycle is not a monovalent group and is formed by combining two substituents.
이하, 상기 정의를 기초로, 본 발명의 유기 발광 소자를 설명한다.Hereinafter, based on the above definition, the organic light-emitting device of the present invention will be described.
본 발명의 유기 발광 소자는, 상기 화학식 1로 표시되는 화합물을 정공수송층 물질로 사용하고, 상기 화학식 2로 표시되는 화합물을 전자억제층 물질로 동시에 사용한다.The organic light emitting device of the present invention uses the compound represented by Formula 1 as a hole transport layer material, and the compound represented by Formula 2 is simultaneously used as an electron blocking layer material.
구체적으로, 상기 화학식 1로 표시되는 화합물은, 아릴(Ar1)에 의해 N-치환된 카바졸을 포함하고, 2개의 아릴아민계 치환기가 상기 카바졸의 양쪽 벤젠 고리에 각각 결합된 구조를 가진다. 상기 화학식 1로 표시되는 화합물 내에서, 상기 2개의 아릴아민계 치환기는 대칭을 이룰 수 있다.Specifically, the compound represented by Formula 1 includes carbazole N-substituted by aryl (Ar 1 ), and has a structure in which two arylamine-based substituents are bonded to both benzene rings of the carbazole, respectively. . In the compound represented by Formula 1, the two arylamine-based substituents may be symmetrical.
또한, 상기 화학식 2로 표시되는 화합물은, 비페닐렌 링커를 통해 아릴아민과 카바졸의 N이 결합된 구조를 가진다.In addition, the compound represented by Formula 2 has a structure in which the N of arylamine and carbazole are bonded through a biphenylene linker.
일반적으로 유기 발광 소자의 발광 효율 및 수명 특성은 서로 트레이드-오프(Trade-off) 관계를 갖는 점을 고려할 때, 상기 화학식 1 및 2로 표시되는 화합물 중 하나만을 채용하거나 둘 다 채용하지 않는 유기 발광 소자에 비하여, 본 발명의 유기 발광 소자는, 구동 전압, 발광 효율 및 수명 측면 모두에서 우수한 특성을 나타낼 수 있다.Considering that the luminous efficiency and lifespan characteristics of organic light-emitting devices generally have a trade-off relationship, organic light-emitting devices employing only one of the compounds represented by Formulas 1 and 2 or neither of them are used. Compared to other devices, the organic light-emitting device of the present invention can exhibit excellent characteristics in terms of driving voltage, luminous efficiency, and lifespan.
각 구성 별로 본 발명의 유기 발광 소자를 상세히 설명한다. The organic light emitting device of the present invention will be described in detail for each configuration.
양극 및 음극anode and cathode
본 발명에서 사용되는 양극 및 음극은, 유기 발광 소자에서 사용되는 전극을 의미한다. The anode and cathode used in the present invention refer to electrodes used in organic light-emitting devices.
상기 양극 물질로는 통상 유기물 층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 상기 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SNO2:Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. The anode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SNO 2 :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline are included, but are not limited to these.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 상기 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다. The cathode material is generally preferably a material with a small work function to facilitate electron injection into the organic layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are, but are not limited to, multi-layered materials such as LiF/Al or LiO 2 /Al.
발광층luminescent layer
본 발명에서 사용되는 발광층은, 양극과 음극으로부터 전달받은 정공과 전자를 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 층을 의미한다. 일반적으로, 발광층은 호스트 재료와 도펀트 재료를 포함한다. The light-emitting layer used in the present invention refers to a layer that can emit light in the visible light range by combining holes and electrons received from the anode and cathode. Generally, the light emitting layer includes a host material and a dopant material.
상기 호스트 재료는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등을 더 포함할 수 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 한정되는 것은 아니다. The host material may further include a condensed aromatic ring derivative or a heterocyclic ring-containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.
상기 도펀트 재료로는 유기 발광 소자에 사용되는 물질이면 특별히 제한되지 않는다. 일례로, 방향족 아민 유도체, 스트릴아민 화합물, 붕소 착체, 플루오란텐 화합물, 금속 착체 등이 있다. 구체적으로 방향족 아민 유도체로는 치환 또는 비치환된 아릴아미노기를 갖는 축합 방향족환 유도체로서, 아릴아미노기를 갖는 피렌, 안트라센, 크리센, 페리플란텐 등이 있으며, 스티릴아민 화합물로는 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로, 아릴기, 실릴기, 알킬기, 사이클로알킬기 및 아릴아미노기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민, 스티릴디아민, 스티릴트리아민, 스티릴테트라아민 등이 있으나, 이에 한정되지 않는다. 또한, 금속 착체로는 이리듐 착체, 백금 착체 등이 있으나, 이에 한정되지 않는다.The dopant material is not particularly limited as long as it is a material used in organic light-emitting devices. Examples include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, and periplanthene, and styrylamine compounds include substituted or unsubstituted arylamino groups. It is a compound in which at least one arylvinyl group is substituted on the arylamine, and is substituted or unsubstituted with one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group, and arylamino group. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc. are included, but are not limited thereto. Additionally, metal complexes include, but are not limited to, iridium complexes and platinum complexes.
정공수송층hole transport layer
본 발명에 따른 유기 발광 소자는, 상기 전자억제층과 양극 사이에 정공수송층을 포함할 수 있다. The organic light emitting device according to the present invention may include a hole transport layer between the electron suppressing layer and the anode.
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. 본 발명에서는 상기 정공수송층을 구성하는 물질로서 상기 화학식 1로 표시되는 화합물을 사용한다.The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light-emitting layer. It is a hole transport material that can receive holes from the anode or hole injection layer and transfer them to the light-emitting layer, and is a material with high mobility for holes. This is suitable. In the present invention, the compound represented by Formula 1 is used as a material constituting the hole transport layer.
바람직하게는, 상기 화학식 1은 하기 화학식 1-1 또는 1-2로 표시된다:Preferably, Formula 1 is represented by the following Formula 1-1 or 1-2:
[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
상기 화학식 1-1 및 1-2에서, Ar1, L1, L2, L3, R1, R2, R, R', A, B, a 및 b의 각 정의는 전술한 바와 같다.In Formulas 1-1 and 1-2, the definitions of Ar 1 , L 1 , L 2 , L 3 , R 1 , R 2 , R, R', A, B, a and b are as described above.
바람직하게는, Ar1은 페닐, 비페닐릴, 터페닐릴, 나프틸, 페난쓰레닐, 또는 트리페닐레닐이다.Preferably, Ar 1 is phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, or triphenylenyl.
바람직하게는, R 및 R'은 각각 독립적으로, 페닐, 비페닐릴, 나프틸, 또는 페난쓰레닐이다.Preferably, R and R' are each independently phenyl, biphenylyl, naphthyl, or phenanthrenyl.
바람직하게는, A 및 B는 각각 독립적으로, 벤젠 또는 나프탈렌이고; 상기 A 및 B는 각각 독립적으로, 비치환되거나, 또는 하나 이상의 페닐로 치환된다.Preferably, A and B are each independently benzene or naphthalene; A and B are each independently unsubstituted or substituted with one or more phenyl.
바람직하게는, L1은 단일 결합, 페닐렌, 또는 비페닐디일이고; 상기 L1은 비치환되거나, 또는 하나 이상의 페닐로 치환된다.Preferably, L 1 is a single bond, phenylene, or biphenyldiyl; The L 1 is unsubstituted or substituted with one or more phenyl.
바람직하게는, L2 및 L3는 각각 독립적으로, 단일 결합 또는 페닐렌이다.Preferably, L 2 and L 3 are each independently a single bond or phenylene.
바람직하게는, R1 및 R2는 모두 수소이다.Preferably, R 1 and R 2 are both hydrogen.
바람직하게는, a 및 b는 각각 독립적으로, 0 내지 3의 정수이다.Preferably, a and b are each independently an integer from 0 to 3.
상기 화학식 1로 표시되는 화합물의 대표적인 예는 다음과 같다: Representative examples of compounds represented by Formula 1 are as follows:
전자억제층electron suppression layer
본 발명에 따른 유기 발광 소자는, 상기 양극과 발광층 사이에 전자억제층을 포함한다. 바람직하게는, 상기 전자억제층은 상기 발광층의 양극 쪽에 접하여 포함된다. The organic light emitting device according to the present invention includes an electron blocking layer between the anode and the light emitting layer. Preferably, the electron blocking layer is included in contact with the anode side of the light emitting layer.
상기 전자억제층은, 음극에서 주입된 전자가 발광층에서 재결합하지 않고 양극 쪽으로 전달되는 것을 억제하여 유기 발광 소자의 효율을 향상시키는 역할을 한다. 본 발명에서는 상기 전자억제층을 구성하는 물질로서 상기 화학식 2로 표시되는 화합물을 사용한다. The electron suppression layer serves to improve the efficiency of the organic light-emitting device by suppressing electrons injected from the cathode from being transferred to the anode without recombining in the light-emitting layer. In the present invention, the compound represented by Formula 2 is used as a material constituting the electron suppression layer.
바람직하게는, 상기 화학식 2는 하기 화학식 2-1 또는 2-2로 표시된다:Preferably, Formula 2 is represented by the following Formula 2-1 or 2-2:
[화학식 2-1][Formula 2-1]
[화학식 2-2][Formula 2-2]
상기 화학식 2-1 및 2-2에서, Ar4, Ar5, L4, L5, R3, R4, R5, R6, c d, e, f, m 및 n의 정의는 전술한 바와 같다.In Formulas 2-1 and 2-2, Ar 4 , Ar 5 , L 4 , L 5 , R 3 , R 4 , R 5 , R 6 , The definitions of cd, e, f, m, and n are as described above.
바람직하게는, Ar4 및 Ar5는 각각 독립적으로, 페닐, 비페닐릴, 터페닐릴, 나프틸, 페난쓰레닐, 디페닐플루오레닐, 또는 아다만틸이다.Preferably, Ar 4 and Ar 5 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, diphenylfluorenyl, or adamantyl.
바람직하게는, L4 및 L5는 각각 독립적으로, 단일 결합, 페닐렌, 비페닐디일, 또는 나프틸렌이고; 상기 L4 및 L5는 각각 독립적으로, 비치환되거나, 또는 하나 이상의 페닐로 치환된다.Preferably, L 4 and L 5 are each independently a single bond, phenylene, biphenyldiyl, or naphthylene; L 4 and L 5 are each independently unsubstituted or substituted with one or more phenyl.
바람직하게는, R3 및 R4는 각각 독립적으로, 수소 또는 페닐이다.Preferably, R 3 and R 4 are each independently hydrogen or phenyl.
바람직하게는, R5는 각각 독립적으로, 수소 또는 페닐이거나; 또는 인접하는 치환기와 결합하여 방향족 고리를 형성한다.Preferably, R 5 is each independently hydrogen or phenyl; Or, it combines with an adjacent substituent to form an aromatic ring.
바람직하게는, R6은 각각 독립적으로, 수소 또는 페닐이거나; 또는 인접하는 치환기와 결합하여 방향족 고리를 형성한다.Preferably, R 6 is each independently hydrogen or phenyl; Or, it combines with an adjacent substituent to form an aromatic ring.
바람직하게는, c d, e, 및 f는 각각 독립적으로, 0 내지 4의 정수이다.Preferably, c d, e, and f are each independently integers from 0 to 4.
바람직하게는, m 및 n은 각각 독립적으로, 0 내지 2의 정수이다.Preferably, m and n are each independently integers from 0 to 2.
상기 화학식 2로 표시되는 화합물의 대표적인 예는 다음과 같다: Representative examples of compounds represented by Formula 2 are as follows:
정공주입층Hole injection layer
본 발명에 따른 유기 발광 소자는, 필요에 따라 상기 양극과 정공수송층 사이에 정공주입층을 추가로 포함할 수 있다. The organic light emitting device according to the present invention may further include a hole injection layer between the anode and the hole transport layer, if necessary.
상기 정공주입층은 전극으로부터 정공을 주입하는 층으로, 정공 주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입효과, 발광층 또는 발광재료에 대하여 우수한 정공 주입 효과를 갖고, 발광층에서 생성된 여기자의 전자주입층 또는 전자주입재료에의 이동을 방지하며, 또한, 박막 형성 능력이 우수한 화합물이 바람직하다. 또한, 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물 층의 HOMO 사이인 것이 바람직하다. The hole injection layer is a layer that injects holes from an electrode. The hole injection material has the ability to transport holes, has an excellent hole injection effect at the anode, a light-emitting layer or a light-emitting material, and has an excellent hole injection effect on the light-emitting layer or light-emitting material. A compound that prevents movement of excitons to the electron injection layer or electron injection material and has excellent thin film forming ability is preferred. Additionally, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer.
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 한정되는 것은 아니다. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. organic substances, anthraquinone, polyaniline, and polythiophene series conductive polymers, etc., but are not limited to these.
정공억제층Hole suppression layer
본 발명에 따른 유기 발광 소자는, 필요에 따라 상기 발광층 상에 정공억제층을 추가로 포함할 수 있다. The organic light emitting device according to the present invention may additionally include a hole blocking layer on the light emitting layer, if necessary.
상기 정공억제층은 발광층 상에 형성되어, 바람직하게는 발광층에 접하여 구비되어, 전자이동도를 조절하고 정공의 과다한 이동을 방지하여 정공-전자간 결합 확률을 높여줌으로써 유기 발광 소자의 효율을 개선하는 역할을 하는 층을 의미한다. 상기 정공억제층은 정공억제물질을 포함하고, 이러한 정공억제물질의 예로 트리아진을 포함한 아진류 유도체; 트리아졸 유도체; 옥사디아졸 유도체; 페난트롤린 유도체; 포스핀옥사이드 유도체 등의 전자흡인기가 도입된 화합물을 사용할 수 있으나, 이에 한정되는 것은 아니다.The hole suppression layer is formed on the light-emitting layer, preferably in contact with the light-emitting layer, to improve the efficiency of the organic light-emitting device by controlling electron mobility and preventing excessive movement of holes to increase the probability of hole-electron coupling. It refers to the layer that plays a role. The hole blocking layer includes a hole blocking material, and examples of the hole blocking material include azine derivatives including triazine; triazole derivatives; Oxadiazole derivatives; phenanthroline derivatives; Compounds into which electron-withdrawing groups are introduced, such as phosphine oxide derivatives, may be used, but are not limited thereto.
전자 주입 및 수송층Electron injection and transport layer
본 발명에 따른 유기 발광 소자는, 필요에 따라 상기 전자억제층과 양극 사이에 정공수송층을 추가로 포함할 수 있다.The organic light emitting device according to the present invention may further include a hole transport layer between the electron suppressing layer and the anode, if necessary.
상기 전자 주입 및 수송층은 전극으로부터 전자를 주입하고, 수취된 전자를 발광층까지 수송하는 전자수송층 및 전자주입층의 역할을 동시에 수행하는 층으로, 상기 발광층 또는 상기 정공억제층 상에 형성된다. 이러한 전자 주입 및 수송물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 전자 주입 및 수송물질의 예로는 8-히드록시퀴놀린의 Al 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물; 트리아진 유도체 등이 있으나, 이들에만 한정되는 것은 아니다. 또는 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 플루오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물, 또는 질소 함유 5원환 유도체 등과 함께 사용할 수도 있으나, 이에 한정되는 것은 아니다. The electron injection and transport layer is a layer that simultaneously functions as an electron transport layer and an electron injection layer for injecting electrons from an electrode and transporting the received electrons to the light-emitting layer, and is formed on the light-emitting layer or the hole blocking layer. As such an electron injection and transport material, a material that can easily inject electrons from the cathode and transfer them to the light emitting layer, and a material with high mobility for electrons, is suitable. Specific examples of electron injection and transport materials include Al complex of 8-hydroxyquinoline; Complex containing Alq 3 ; organic radical compounds; hydroxyflavone-metal complex; Triazine derivatives, etc., but are not limited to these. or fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, etc. and their derivatives, metal complex compounds. , or a nitrogen-containing 5-membered ring derivative, etc., but is not limited thereto.
상기 전자 주입 및 수송층은 전자주입층 및 전자수송층과 같은 별개의 층으로도 형성될 수 있다. 이와 같은 경우, 전자 수송층은 상기 발광층 또는 상기 정공억제층 상에 형성되고, 상기 전자 수송층에 포함되는 전자 수송 물질로는 상술한 전자 주입 및 수송 물질이 사용될 수 있다. 또한, 전자 주입층은 상기 전자 수송층 상에 형성되고, 상기 전자 주입층에 포함되는 전자 주입 물질로는 LiF, NaCl, CsF, Li2O, BaO, 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 벤조이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 질소 함유 5원환 유도체 등이 사용될 수 있다.The electron injection and transport layer may also be formed as separate layers such as an electron injection layer and an electron transport layer. In this case, the electron transport layer is formed on the light emitting layer or the hole blocking layer, and the electron injection and transport material described above may be used as the electron transport material included in the electron transport layer. In addition, an electron injection layer is formed on the electron transport layer, and electron injection materials included in the electron injection layer include LiF, NaCl, CsF, Li 2 O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, Thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, benzoimidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and their derivatives, metal complex compounds and nitrogen-containing five-membered ring derivatives can be used. You can.
유기 발광 소자organic light emitting device
본 발명에 따른 유기 발광 소자의 구조를 도 1에 예시하였다. 도 1은, 기판(1), 양극(2), 정공수송층(3), 전자억제층(4), 발광층(5), 및 음극(6)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 또한, 정공주입층(7), 정공억제층(8), 그리고 전자 주입 및 수송층(9)을 추가로 포함하는 경우의 유기 발광 소자의 구조를 도 2에 예시하였다.The structure of an organic light-emitting device according to the present invention is illustrated in Figure 1. Figure 1 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a hole transport layer 3, an electron suppressing layer 4, a light emitting layer 5, and a cathode 6. In addition, the structure of the organic light-emitting device in the case where it additionally includes a hole injection layer (7), a hole blocking layer (8), and an electron injection and transport layer (9) is illustrated in FIG. 2.
도 1은, 기판(1), 양극(2), 전자억제층(3), 발광층(4), 및 음극(5)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 또한, 정공수송층(6) 및 전자수송층(7)을 포함하는 경우의 유기 발광 소자의 구조를 도 2에 예시하였다. Figure 1 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, an electron blocking layer 3, a light emitting layer 4, and a cathode 5. Additionally, the structure of an organic light emitting device including a hole transport layer 6 and an electron transport layer 7 is illustrated in FIG. 2 .
본 발명에 따른 유기 발광 소자는 상술한 구성을 순차적으로 적층시켜 제조할 수 있다. 이때, 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(physical Vapor Deposition)방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 상술한 각 층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시켜 제조할 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 상술한 구성의 역순으로 양극 물질까지 차례로 증착시켜 유기 발광 소자를 만들 수 있다(WO 2003/012890). 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 structures. At this time, an anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation. It can be manufactured by forming each layer described above and then depositing a material that can be used as a cathode on it. In addition to this method, an organic light-emitting device can be made by sequentially depositing a cathode material on a substrate and then an anode material in the reverse order of the above-described configuration (WO 2003/012890). Additionally, the light-emitting layer can be formed by using a solution coating method as well as a vacuum deposition method for the host and dopant. Here, the solution application method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.
한편, 본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.Meanwhile, the organic light emitting device according to the present invention may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.
이하, 본 발명의 이해를 돕기 위하여 바람직한 실시예를 제시한다. 그러나 하기의 실시예는 본 발명을 보다 쉽게 이해하기 위하여 제공되는 것일 뿐, 이에 의해 본 발명의 내용이 한정되는 것은 아니다.Below, preferred embodiments are presented to aid understanding of the present invention. However, the following examples are provided only to make the present invention easier to understand, and the content of the present invention is not limited thereto.
합성예 A-1: 화합물 A-1의 합성Synthesis Example A-1: Synthesis of Compound A-1
합성예 A-2: 화합물 A-2의 합성Synthesis Example A-2: Synthesis of Compound A-2
9-([1,1’-비페닐]-4-일)-3,6-디브로모-9H-카바졸 (20.0 g, 41.91 mmol)과 디페닐아민 (14.19 g, 83.82 mmol)을 이용하여 상기 합성예 A-1과 동일한 방법으로 상기 화합물 A-2 (22.4 g, 79.31 % 수율)를 수득하였다. (MS[M+H]+ = 654)9-([1,1'-biphenyl]-4-yl)-3,6-dibromo- 9H -carbazole (20.0 g, 41.91 mmol) and diphenylamine (14.19 g, 83.82 mmol) Compound A-2 (22.4 g, 79.31% yield) was obtained in the same manner as Synthesis Example A-1. (MS[M+H]+ = 654)
합성예 A-3: 화합물 A-3의 합성Synthesis Example A-3: Synthesis of Compound A-3
3,4-디브로모-9-페닐-9H-카바졸 (20.00 g, 49.86 mmol)과 (4-(디페닐아미노)페닐)보론산 (28.83 g, 99.73 mmol)에 테트라하이드로퓨란(THF) (200 ml)을 가한 후 가열, 교반하였다. 상기 혼합물에 탄산칼륨 (34.46 g, 249.31 mmol) 수용액 (100 ml)을 가한 후 5분 동안 가열, 교반하였다. 상기 혼합물에 테트라하이드로퓨란(THF) (20ml)에 용해시킨 비스(트리-터트-부틸포스핀)팔라듐 (0.25 g, 0.50 mmol)을 천천히 가한 후 1시간 동안 가열 교반하였다. 반응 종결 및 여과 후, 톨루엔과 물로 층분리 하였다. 용매 제거 후 에틸아세테이트로 재결정하여 화합물 A-3 (29.2 g, 80.23 % 수율)을 수득하였다. (MS[M+H]+ = 730)3,4-Dibromo-9-phenyl- 9H -carbazole (20.00 g, 49.86 mmol) and (4-(diphenylamino)phenyl)boronic acid (28.83 g, 99.73 mmol) in tetrahydrofuran (THF). (200 ml) was added and heated and stirred. An aqueous solution (100 ml) of potassium carbonate (34.46 g, 249.31 mmol) was added to the mixture, followed by heating and stirring for 5 minutes. Bis(tri-tert-butylphosphine)palladium (0.25 g, 0.50 mmol) dissolved in tetrahydrofuran (THF) (20 ml) was slowly added to the mixture, followed by heating and stirring for 1 hour. After completion of the reaction and filtration, the layers were separated into toluene and water. After removal of the solvent, recrystallization was performed with ethyl acetate to obtain compound A-3 (29.2 g, 80.23% yield). (MS[M+H]+ = 730)
합성예 A-4: 화합물 A-4의 합성Synthesis Example A-4: Synthesis of Compound A-4
9-([1,1’-비페닐]-4-일)-3,6-디브로모-9H-카바졸 (20.0 g, 41.91 mmol)과 (4-(디페닐아미노)페닐)보론산 (24.24 g, 83.32 mmol)을 이용하여 상기 합성예 A-3과 동일한 방법으로 상기 화합물 A-4 (26.8 g, 79.33 % 수율)를 수득하였다. (MS[M+H]+ = 806)9-([1,1'-biphenyl]-4-yl)-3,6-dibromo- 9H -carbazole (20.0 g, 41.91 mmol) and (4-(diphenylamino)phenyl)boronic acid Compound A-4 (26.8 g, 79.33% yield) was obtained in the same manner as Synthesis Example A-3 using (24.24 g, 83.32 mmol). (MS[M+H]+ = 806)
합성예 A-5: 화합물 A-5의 합성Synthesis Example A-5: Synthesis of Compound A-5
3,6-디브로모-9-(나프탈렌-2-일)-9H-카바졸 (20.0 g, 44.33 mmol)과 (4-(디페닐아미노)페닐)보론산 (25.64 g, 88.66 mmol)을 이용하여 상기 합성예 A-3과 동일한 방법으로 상기 화합물 A-5 (25.6 g, 74.04 % 수율)를 수득하였다. (MS[M+H]+ = 780)3,6-dibromo-9-(naphthalen-2-yl) -9H -carbazole (20.0 g, 44.33 mmol) and (4-(diphenylamino)phenyl)boronic acid (25.64 g, 88.66 mmol) Compound A-5 (25.6 g, 74.04% yield) was obtained in the same manner as Synthesis Example A-3. (MS[M+H]+ = 780)
합성예 A-6: 화합물 A-6의 합성Synthesis Example A-6: Synthesis of Compound A-6
9-([1,1’-비페닐]-3-일)-3,6-디브로모-9H-카바졸 (20.0 g, 41.91 mmol)과 (4-(9H-카바졸-9-일)페닐)보론산 (24.07 g, 83.82 mmol)을 이용하여 상기 합성예 A-3과 동일한 방법으로 상기 화합물 A-6 (24.4 g, 72.59 % 수율)을 수득하였다. (MS[M+H]+ = 802)9-([1,1'-biphenyl]-3-yl)-3,6-dibromo- 9H -carbazole (20.0 g, 41.91 mmol) and (4-( 9H -carbazole-9- Compound A-6 (24.4 g, 72.59% yield) was obtained in the same manner as Synthesis Example A-3 using 1)phenyl)boronic acid (24.07 g, 83.82 mmol). (MS[M+H]+ = 802)
합성예 A-7: 화합물 A-7의 합성Synthesis Example A-7: Synthesis of Compound A-7
3,6-디브로모-9-페닐-9H-카바졸 (20.0 g, 49.86 mmol)과 (4-(3-페닐-9H-카바졸-9-일)페닐)보론산 (36.22 g, 99.73 mmol)을 이용하여 상기 합성예 A-3과 동일한 방법으로 상기 화합물 A-7 (32.7 g, 74.68 % 수율)을 수득하였다. (MS[M+H]+ = 878)3,6-dibromo-9-phenyl- 9H -carbazole (20.0 g, 49.86 mmol) and (4-(3-phenyl-9 H -carbazol-9-yl)phenyl)boronic acid (36.22 g, Compound A-7 (32.7 g, 74.68% yield) was obtained in the same manner as Synthesis Example A-3 using 99.73 mmol). (MS[M+H]+ = 878)
합성예 B-1: 화합물 B-1의 합성Synthesis Example B-1: Synthesis of Compound B-1
9-(4’-클로로-[1,1’-비페닐]-2-일)-9H-카바졸 (20.0 g, 56.52 mmol), 디([1,1’-비페닐]-4-일)아민 (18.53 g, 57.65 mmol) 그리고 소듐 터트-부톡사이드(7.60 g, 79.13 mmol)에 톨루엔(200 ml)을 가한 후, 10분 동안 가열 교반하였다. 상기 혼합물에 톨루엔(20ml)에 용해시킨 비스(트리-터트-부틸포스핀)팔라듐 (0.14 g, 0.28 mmol)을 가한 후 1시간 동안 가열 교반하였다. 반응 종결 및 여과 후, 톨루엔과 물로 층분리 하였다. 용매 제거 후 에틸아세테이트로 재결정하여 상기 화합물 B-1 (28.5 g, 78.94 % 수율)을 수득하였다. (MS[M+H]+ = 639)9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9 H -carbazole (20.0 g, 56.52 mmol), di([1,1'-biphenyl]-4- Toluene (200 ml) was added to 1)amine (18.53 g, 57.65 mmol) and sodium tert-butoxide (7.60 g, 79.13 mmol), and then heated and stirred for 10 minutes. Bis(tri-tert-butylphosphine)palladium (0.14 g, 0.28 mmol) dissolved in toluene (20 ml) was added to the mixture, followed by heating and stirring for 1 hour. After completion of the reaction and filtration, the layers were separated into toluene and water. After removal of the solvent, recrystallization was performed with ethyl acetate to obtain compound B-1 (28.5 g, 78.94% yield). (MS[M+H]+ = 639)
합성예 B-2: 화합물 B-2의 합성Synthesis Example B-2: Synthesis of Compound B-2
9-(4’-클로로-[1,1’-비페닐]-2-일)-9H-카바졸 (20.0 g, 56.52 mmol)과 N-([1,1’-비페닐]-4-일)-[1,1’:4’,1’’-터페닐]-4-아민 (22.92 g, 57.65 mmol)을 이용하여 상기 합성예 B-1과 동일한 방법으로 상기 화합물 B-2 (32.0 g, 79.19 % 수율)를 수득하였다. (MS[M+H]+ = 715)9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9 H -carbazole (20.0 g, 56.52 mmol) and N -([1,1'-biphenyl]-4 Compound B-2 ( 32.0 g, 79.19% yield) was obtained. (MS[M+H]+ = 715)
합성예 B-3: 화합물 B-3의 합성Synthesis Example B-3: Synthesis of Compound B-3
합성예 B-4: 화합물 B-4의 합성Synthesis Example B-4: Synthesis of Compound B-4
9-(4’-클로로-[1,1’-비페닐]-2-일)-9H-카바졸 (20.0 g, 56.52 mmol)과 비스(4-(나프탈렌-1-일)페닐)아민 (24.30 g, 57.65 mmol)을 이용하여 상기 합성예 B-1과 동일한 방법으로 상기 화합물 B-4 (33.0 g, 79.01 % 수율)를 수득하였다. (MS[M+H]+ = 739)9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9 H -carbazole (20.0 g, 56.52 mmol) and bis(4-(naphthalen-1-yl)phenyl)amine Compound B-4 (33.0 g, 79.01% yield) was obtained in the same manner as Synthesis Example B-1 using (24.30 g, 57.65 mmol). (MS[M+H]+ = 739)
합성예 B-5: 화합물 B-5의 합성Synthesis Example B-5: Synthesis of Compound B-5
7-(4’-클로로-[1,1’-비페닐]-2-일)-7H-벤조[c]카바졸 (20.0 g, 49.52 mmol)과 디([1,1’-비페닐]-4-일)아민 (16.23 g, 50.51 mmol)을 이용하여 상기 합성예 B-1과 동일한 방법으로 상기 화합물 B-5 (27.0 g, 79.15 % 수율)를 수득하였다. (MS[M+H]+ = 689)7-(4'-chloro-[1,1'-biphenyl]-2-yl)-7 H -benzo[ c ]carbazole (20.0 g, 49.52 mmol) and di([1,1'-biphenyl ]-4-yl)amine (16.23 g, 50.51 mmol) was used to obtain compound B-5 (27.0 g, 79.15% yield) in the same manner as in Synthesis Example B-1. (MS[M+H]+ = 689)
합성예 B-6: 화합물 B-6의 합성Synthesis Example B-6: Synthesis of Compound B-6
9-(4’-클로로-[1,1’-비페닐]-2-일)-3-페닐-9H-카바졸 (20.0 g, 46.52 mmol)과 N-(4-(나프탈렌-1-일)페닐)-[1,1’-비페닐]-4-아민 (17.63 g, 47.45 mmol)을 이용하여 상기 합성예 B-1과 동일한 방법으로 상기 화합물 B-6 (28.0 g, 78.68 % 수율)을 수득하였다. (MS[M+H]+ = 765)9-(4'-chloro-[1,1'-biphenyl]-2-yl)-3-phenyl-9 H -carbazole (20.0 g, 46.52 mmol) and N -(4-(naphthalene-1- 1) phenyl)-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) was used to produce the compound B-6 (28.0 g, 78.68% yield) in the same manner as in Synthesis Example B-1. ) was obtained. (MS[M+H]+ = 765)
합성예 B-7: 화합물 B-7의 합성Synthesis Example B-7: Synthesis of Compound B-7
9-(4’-클로로-[1,1’-비페닐]-3-일)-9H-카바졸 (20.0 g, 56.52 mmol), 디([1,1’-비페닐]-4-일)아민 (18.53 g, 57.65 mmol) 이용하여 상기 합성예 B-1과 동일한 방법으로 상기 화합물 B-7 (28.2 g, 78.10 % 수율)을 수득하였다. (MS[M+H]+ = 639)9-(4'-chloro-[1,1'-biphenyl]-3-yl)-9 H -carbazole (20.0 g, 56.52 mmol), di([1,1'-biphenyl]-4- Compound B-7 (28.2 g, 78.10% yield) was obtained in the same manner as in Synthesis Example B-1 using 1)amine (18.53 g, 57.65 mmol). (MS[M+H]+ = 639)
합성예 B-8: 화합물 B-8의 합성Synthesis Example B-8: Synthesis of Compound B-8
9-(4’-클로로-[1,1’-비페닐]-3-일)-9H-카바졸 (20.0 g, 56.52 mmol)과 비스(4-(나프탈렌-1-일)페닐)아민 (24.30 g, 57.65 mmol)을 이용하여 상기 합성예 B-1과 동일한 방법으로 상기 화합물 B-8 (30.4 g, 72.79 % 수율)를 수득하였다. (MS[M+H]+ = 739)9-(4'-chloro-[1,1'-biphenyl]-3-yl)-9 H -carbazole (20.0 g, 56.52 mmol) and bis(4-(naphthalen-1-yl)phenyl)amine Compound B-8 (30.4 g, 72.79% yield) was obtained in the same manner as Synthesis Example B-1 using (24.30 g, 57.65 mmol). (MS[M+H]+ = 739)
실시예 1Example 1
ITO(Indium Tin Oxide)가 1,400Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 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) with a thickness of 1,400 Å was placed in distilled water with a detergent dissolved in it and washed ultrasonically. At this time, a detergent manufactured by Fischer Co. was used, and distilled water filtered secondarily using a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, it was ultrasonic washed with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned for 5 minutes using oxygen plasma and then transported to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에 하기 화학식 HAT로 표시되는 화합물을 100Å의 두께로 열 진공 증착하여 정공주입층을 형성하였다. 그 위에 정공수송층으로 상기 합성예 A-1에서 제조된 화합물 A-1을 1150Å 두께로 진공 증착한 후, 전자억제층으로 상기 합성예 B-1에서 제조된 화합물 B-1을 150Å의 두께로 열 진공 증착하였다. 이어서, 발광층으로 하기 화학식 BH로 표시되는 화합물 및 하기 화학식 BD로 표시되는 화합물을 25:1의 중량비로 200Å의 두께로 진공 증착하였다. 이어서, 정공억제층으로 하기 화학식 HB1으로 표시되는 화합물을 50Å의 두께로 진공 증착하였다. 이어서, 전자수송 및 전자주입을 동시에 하는 층으로 하기 화학식 ET1로 표시되는 화합물과 하기 Liq로 표시되는 화합물을 1:1의 중량비로 310Å의 두께로 열 진공 증착하였다. 상기 전자 수송 및 전자 주입층 위에 순차적으로 12Å의 두께로 리튬플로라이드(LiF)와 1000Å 두께로 알루미늄을 증착하여 음극을 형성하여, 유기 발광 소자를 제조하였다.On the ITO transparent electrode prepared in this way, a hole injection layer was formed by thermally vacuum depositing a compound represented by the following chemical formula HAT to a thickness of 100 Å. On top of this, Compound A-1 prepared in Synthesis Example A-1 was vacuum deposited as a hole transport layer to a thickness of 1150 Å, and then Compound B-1 prepared in Synthesis Example B-1 was heated to a thickness of 150 Å as an electron suppressing layer. Vacuum deposited. Next, a compound represented by the following formula BH and a compound represented by the following formula BD were vacuum deposited as a light emitting layer to a thickness of 200 Å at a weight ratio of 25:1. Next, a compound represented by the following chemical formula HB1 was vacuum deposited to a thickness of 50 Å as a hole blocking layer. Next, as a layer that simultaneously performs electron transport and electron injection, a compound represented by the formula ET1 and a compound represented by Liq below were thermally vacuum deposited at a weight ratio of 1:1 to a thickness of 310 Å. Lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1000 Å were sequentially deposited on the electron transport and electron injection layer to form a cathode, thereby manufacturing an organic light emitting device.
실시예 1 내지 46Examples 1 to 46
하기 표 1에 기재된 바와 같이, 상기 실시예 1에서 전공수송층에는 화합물 A-1 내지 A-7 화합물 중 어느 하나를 사용하고, 전자억제층에는 화합물 B-1 내기 B-8 중 어느 하나를 사용하는 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. As shown in Table 1 below, in Example 1, any one of compounds A-1 to A-7 was used in the electroporation transport layer, and any one of compounds B-1 or B-8 was used in the electron suppression layer. An organic light emitting device was manufactured in the same manner as in Example 1 except that.
비교예 1 내지 8Comparative Examples 1 to 8
하기 표 1에 기재된 바와 같이, 상기 실시예 1에서 전공수송층에는 화합물 A-1, A-4, A-5, HT-1, 또는 HT-2를 사용하고, 전자억제층에는 화합물 EB-1, EB-2, B-1, B-2, 또는 B-5를 사용하는 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. As shown in Table 1 below, in Example 1, compounds A-1, A-4, A-5, HT-1, or HT-2 were used in the electromagnetic transport layer, and compounds EB-1, An organic light emitting device was manufactured in the same manner as Example 1, except for using EB-2, B-1, B-2, or B-5.
실험예Experiment example
실시예 및 비교예에서 제조한 각 유기 발광 소자에 10 mA/cm2의 전류를 인가하였을 때, 전압, 효율, 색좌표 및 수명을 측정하고 그 결과를 하기 표 1에 나타내었다. 한편, T95는 휘도가 초기 휘도(6000 nit)에서 95%로 감소되는 데 소요되는 시간을 의미한다. When a current of 10 mA/cm 2 was applied to each organic light emitting device manufactured in Examples and Comparative Examples, the voltage, efficiency, color coordinate, and lifespan were measured, and the results are shown in Table 1 below. Meanwhile, T95 refers to the time it takes for the luminance to decrease from the initial luminance (6000 nit) to 95%.
(V)Voltage
(V)
(cd/A)efficiency
(cd/A)
(x,y)Color coordinates
(x,y)
(hr)T 95
(hr)
상기 표 1에서, 상기 화학식 A-1로 표시되는 화합물을 정공수송층 물질로 사용함과 동시에 상기 화학식 B-1로 표시되는 화합물을 전자억제층 물질로 사용한 본 발명에 따른 실험예의 유기 발광 소자는 효율 및 수명 특성이 동시에 향상됨이 확인된다. In Table 1, the organic light emitting device of an experimental example according to the present invention using the compound represented by Formula A-1 as a hole transport layer material and the compound represented by Formula B-1 as an electron suppression layer material has efficiency and It is confirmed that the lifespan characteristics are simultaneously improved.
구체적으로, 상기 화학식 A-1로 표시되는 화합물을 정공수송층 물질로 사용함과 동시에 상기 화학식 B-1로 표시되는 화합물을 전자억제층 물질로 사용한 실시예의 유기 발광 소자는, 상기 화학식 A-1 및 B-1로 표시되는 화합물 중 하나를 채용하는 비교예 1 내지 8의 유기 발광 소자에 비하여, 구동 전압, 발광 효율 또는 수명 측면에서 우수한 특성을 나타내었다. Specifically, the organic light-emitting device of the example in which the compound represented by Formula A-1 is used as a hole transport layer material and the compound represented by Formula B-1 is used as an electron blocking layer material is, Compared to the organic light-emitting devices of Comparative Examples 1 to 8 employing one of the compounds represented by -1, it exhibited excellent characteristics in terms of driving voltage, luminous efficiency, and lifespan.
이는 일반적으로 유기 발광 소자의 발광 효율 및 수명 특성은 서로 트레이드-오프(Trade-off) 관계를 갖는 점을 고려할 때, 본 발명의 화합물간의 조합을 채용한 유기 발광 소자가 비교예 소자 대비 현저히 향상된 소자 특성을 나타냄을 알 수 있다.Considering that the luminous efficiency and lifespan characteristics of organic light-emitting devices generally have a trade-off relationship, the organic light-emitting devices employing the combination of compounds of the present invention are significantly improved compared to the comparative devices. It can be seen that it exhibits characteristics.
1: 기판 2: 양극
3: 정공수송층 4: 전자억제층
5: 발광층 6: 음극
7: 정공주입층 8: 정공억제층
9: 전자 주입 및 수송층1: Substrate 2: Anode
3: hole transport layer 4: electron suppression layer
5: emitting layer 6: cathode
7: hole injection layer 8: hole suppression layer
9: Electron injection and transport layer
Claims (16)
음극,
상기 양극과 상기 음극 사이의 발광층,
상기 양극과 상기 발광층 사이의 전자억제층, 및
상기 전자억제층과 상기 양극 사이에 정공수송층을 포함하고,
상기 정공수송층은 하기 화학식 1로 표시되는 화합물을 포함하고,
상기 전자억제층은 하기 화학식 2-2로 표시되는 화합물을 포함하는,
유기 발광 소자:
[화학식 1]
상기 화학식 1에서,
Ar1은 치환 또는 비치환된 C6-60 아릴이고,
Ar2 및 Ar3는 각각 독립적으로, -NRR' 또는 하기 화학식 3으로 표시되는 치환기이고,
여기서, R 및 R'은 각각 독립적으로, 치환 또는 비치환된 C6-60 아릴이고,
[화학식 3]
상기 화학식 3에서,
A 및 B는 각각 독립적으로, 치환 또는 비치환된 C6-60 아릴이고,
점선은 상기 화학식 1의 L2 또는 L3와 결합되고,
L1 내지 L3는 각각 독립적으로, 단일 결합, 또는 치환 또는 비치환된 C6-60 아릴렌이고,
R1 및 R2는 각각 독립적으로, 수소 또는 중수소이고,
a 및 b는 각각 독립적으로, 0 내지 3의 정수이고,
[화학식 2-2]
상기 화학식 2-2에서,
Ar4 및 Ar5는 각각 독립적으로, 치환 또는 비치환된 C6-60 아릴, 또는 아다만틸이고,
L4 및 L5는 각각 독립적으로, 단일 결합, 또는 치환 또는 비치환된 C6-60 아릴렌이고,
R3 내지 R6은 각각 독립적으로, 수소, 중수소, 또는 치환 또는 비치환된 C6-60 아릴이거나; 또는 인접하는 치환기와 결합하여 방향족 고리를 형성할 수 있고,
c d, e, 및 f는 각각 독립적으로, 0 내지 4의 정수이고,
m 및 n은 각각 독립적으로, 0 내지 2의 정수이다.
anode,
cathode,
A light emitting layer between the anode and the cathode,
an electron-suppressing layer between the anode and the light-emitting layer, and
Comprising a hole transport layer between the electron suppression layer and the anode,
The hole transport layer includes a compound represented by the following formula (1),
The electron suppression layer includes a compound represented by the following formula 2-2,
Organic light emitting device:
[Formula 1]
In Formula 1,
Ar 1 is substituted or unsubstituted C 6-60 aryl,
Ar 2 and Ar 3 are each independently -NRR' or a substituent represented by the following formula (3),
Here, R and R' are each independently substituted or unsubstituted C 6-60 aryl,
[Formula 3]
In Formula 3 above,
A and B are each independently a substituted or unsubstituted C 6-60 aryl,
The dotted line is combined with L 2 or L 3 of Formula 1,
L 1 to L 3 are each independently a single bond or a substituted or unsubstituted C 6-60 arylene,
R 1 and R 2 are each independently hydrogen or deuterium,
a and b are each independently an integer from 0 to 3,
[Formula 2-2]
In Formula 2-2,
Ar 4 and Ar 5 are each independently substituted or unsubstituted C 6-60 aryl, or adamantyl,
L 4 and L 5 are each independently a single bond or substituted or unsubstituted C 6-60 arylene,
R 3 to R 6 are each independently hydrogen, deuterium, or substituted or unsubstituted C 6-60 aryl; Or, it can be combined with an adjacent substituent to form an aromatic ring,
cd, e, and f are each independently integers from 0 to 4,
m and n are each independently integers from 0 to 2.
상기 화학식 1은 하기 화학식 1-1 또는 1-2로 표시되는,
유기 발광 소자:
[화학식 1-1]
[화학식 1-2]
상기 화학식 1-1 및 1-2에서, Ar1, L1, L2, L3, R1, R2, R, R', A, B, a 및 b의 각 정의는 제1항과 같다.
According to paragraph 1,
Formula 1 is represented by the following formula 1-1 or 1-2,
Organic light emitting device:
[Formula 1-1]
[Formula 1-2]
In the above formulas 1-1 and 1-2, the definitions of Ar 1 , L 1 , L 2 , L 3 , R 1 , R 2 , R, R', A, B, a and b are the same as in clause 1. .
Ar1은 페닐, 비페닐릴, 터페닐릴, 나프틸, 페난쓰레닐, 또는 트리페닐레닐인,
유기 발광 소자.
According to paragraph 1,
Ar 1 is phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, or triphenylenyl,
Organic light emitting device.
R 및 R'은 각각 독립적으로, 페닐, 비페닐릴, 나프틸, 또는 페난쓰레닐인,
유기 발광 소자.
According to paragraph 1,
R and R' are each independently phenyl, biphenylyl, naphthyl, or phenanthrenyl,
Organic light emitting device.
A 및 B는 각각 독립적으로, 벤젠 또는 나프탈렌이고;
상기 A 및 B는 각각 독립적으로, 비치환되거나, 또는 하나 이상의 페닐로 치환되는,
유기 발광 소자.
According to paragraph 1,
A and B are each independently benzene or naphthalene;
Wherein A and B are each independently unsubstituted or substituted with one or more phenyl,
Organic light emitting device.
L1은 단일 결합, 페닐렌, 또는 비페닐디일이고;
상기 L1은 비치환되거나, 또는 하나 이상의 페닐로 치환되는,
유기 발광 소자.
According to paragraph 1,
L 1 is a single bond, phenylene, or biphenyldiyl;
wherein L 1 is unsubstituted or substituted with one or more phenyl,
Organic light emitting device.
L2 및 L3는 각각 독립적으로, 단일 결합 또는 페닐렌인,
유기 발광 소자.
According to paragraph 1,
L 2 and L 3 are each independently a single bond or phenylene,
Organic light emitting device.
R1 및 R2는 모두 수소인,
유기 발광 소자.
According to paragraph 1,
R 1 and R 2 are both hydrogen,
Organic light emitting device.
상기 화학식 1은 하기 화합물로 구성되는 군으로부터 선택되는 어느 하나인,
유기 발광 소자:
According to paragraph 1,
Formula 1 is any one selected from the group consisting of the following compounds,
Organic light emitting device:
Ar4 및 Ar5는 각각 독립적으로, 페닐, 비페닐릴, 터페닐릴, 나프틸, 페난쓰레닐, 디페닐플루오레닐, 또는 아다만틸인,
유기 발광 소자.
According to paragraph 1,
Ar 4 and Ar 5 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, diphenylfluorenyl, or adamantyl,
Organic light emitting device.
L4 및 L5는 각각 독립적으로, 단일 결합, 페닐렌, 비페닐디일, 또는 나프틸렌이고;
상기 L4 및 L5는 각각 독립적으로, 비치환되거나, 또는 하나 이상의 페닐로 치환되는,
유기 발광 소자.
According to paragraph 1,
L 4 and L 5 are each independently a single bond, phenylene, biphenyldiyl, or naphthylene;
wherein L 4 and L 5 are each independently unsubstituted or substituted with one or more phenyl,
Organic light emitting device.
R3 및 R4는 각각 독립적으로, 수소 또는 페닐인,
유기 발광 소자.
According to paragraph 1,
R 3 and R 4 are each independently hydrogen or phenyl,
Organic light emitting device.
R5는 각각 독립적으로, 수소 또는 페닐이거나; 또는 인접하는 치환기와 결합하여 방향족 고리를 형성하는,
유기 발광 소자.
According to paragraph 1,
R 5 is each independently hydrogen or phenyl; Or combining with an adjacent substituent to form an aromatic ring,
Organic light emitting device.
R6은 각각 독립적으로, 수소 또는 페닐이거나; 또는 인접하는 치환기와 결합하여 방향족 고리를 형성하는,
유기 발광 소자.
According to paragraph 1,
R 6 is each independently hydrogen or phenyl; Or combining with an adjacent substituent to form an aromatic ring,
Organic light emitting device.
상기 화학식 2-2는 하기 화합물로 구성되는 군으로부터 선택되는 어느 하나인,
유기 발광 소자:
.According to paragraph 1,
Formula 2-2 is any one selected from the group consisting of the following compounds,
Organic light emitting device:
.
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