JP4411270B2 - 有機発光ダイオード及びその製造方法 - Google Patents
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- 238000004519 manufacturing process Methods 0.000 title claims description 20
- 238000000034 method Methods 0.000 title description 16
- 239000010410 layer Substances 0.000 claims description 211
- 239000002019 doping agent Substances 0.000 claims description 62
- 239000000463 material Substances 0.000 claims description 40
- 239000012044 organic layer Substances 0.000 claims description 22
- 230000005525 hole transport Effects 0.000 claims description 19
- 239000011368 organic material Substances 0.000 claims description 17
- 150000001454 anthracenes Chemical class 0.000 claims description 8
- 238000002347 injection Methods 0.000 claims description 7
- 239000007924 injection Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 description 14
- 238000010586 diagram Methods 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 9
- 239000000758 substrate Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- -1 polycyclic hydrocarbon compounds Chemical class 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 229910000861 Mg alloy Inorganic materials 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 4
- 239000006163 transport media Substances 0.000 description 4
- 150000001339 alkali metal compounds Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 229910018068 Li 2 O Inorganic materials 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000012864 cross contamination Methods 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
- OBAJPWYDYFEBTF-UHFFFAOYSA-N 2-tert-butyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C3=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C4=CC=C(C=C43)C(C)(C)C)=CC=C21 OBAJPWYDYFEBTF-UHFFFAOYSA-N 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-M 4-phenylphenolate Chemical compound C1=CC([O-])=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-M 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- VVJKKWFAADXIJK-UHFFFAOYSA-N allylamine Natural products NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000004697 chelate complex Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
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Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/30—Doping active layers, e.g. electron 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] 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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/155—Hole transporting layers comprising dopants
-
- 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
-
- 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
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- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Electroluminescent Light Sources (AREA)
Description
陽極22:ITO
HI層:CuPc 10nm以下
HT層23:NPB 約30nm
EM層24:Ir(ppy)3 がドーピングされたCBP 30nm以下
正孔ブロック層:BAlq 10nm以下
ET層25:Alq3 40nm
LiF層26: 約0.5〜1nm
陰極(1)27:マグネシウム/マグネシウム合金層
陰極(2)28:金属酸化物層
陽極32:ITO
HI層33:フッ素化ポリマー(fluorinated polymer)CFX(xは1または2)
HT層34:前出のNPB等の芳香族三級アミン
EM層35:Alq3(C545T)
ET層36:Alq3(C545T)
第一バッファ層37:LiF
第二バッファ層38:CuPc
陰極39:Al:Li(3w%)
基板41
陽極42
HI層43:CuPc 15nm
HT層44:NPB 60nm
ET層45:Alq3 75nm
バッファ層46:LiF 0.5nm(LiFは、MgF2、CaF2、Li2OやMgOで代替可能。)
陰極48:AlとMg/Agが使用可(AgやAuでも代替可能)
b)前記ET層に少なくとも一つのn型ドーパントをドーピングする工程。
c)前記EM層に発光ドーパントをドーピングする工程。
d)前記HT層に少なくとも一つのp型ドーパントをドーピングする工程。
b)前記ET層に少なくとも一つのn型ドーパントをドーピングする工程。
c)前記EM層に発光ドーパントをドーピングする工程。
d)前記HT層に少なくとも一つのp型ドーパントをドーピングする工程。
構造模式図を図5に示す。ここに示すOLED100は、有機層120が陽極112と陰極130の間に配置された構成となっている。陽極112は、基板110の上に配置される。有機層120は、HI層122、HT層124、EM層126、ET層128で構成されている。そして有機層120の構成ではHI層122、HT層124、EM層126、ET層128に同じ有機系ホスト材料が用いられている。図6と図7に示すように、HI層122に用いられている有機系ホスト材料にはP型ドーパントがドーピングされ、EM層126に用いられている有機系ホスト材料には発光ドーパントまたは染料がドーピングされ、ET層128に用いられている有機系ホスト材料にはn型ドーパントがドーピングされている。EM層126の中の発光ドーパントには、蛍光ドーパント(励起一重項状態)及びリン光ドーパント(励起三重項状態)を用いることができる。
有機層の構成120内の異なる層に単一の有機系ホスト材料を用いうることを示すために、図14に示す構成で試作を実施した。この有機層は以下の構成となっている。陰極は銀であり、陽極はITOである。全ての層は透明基板の上に形成され、形成された層の合計厚さは約110nmである。なお、各層の形成方法に関しては、既に公知の種々の手法の活用が可能であり、特段の限定を要さないために省略する。
ET層: 厚さ約30nmであり、CsFが20w%ドーピングされている。
EM層: 厚さ約30nmであり、青色染料がドーピングされている。
HT層とHI層の接合層: 厚さ約10nmであり、HI層のドーパントは、F4−TCQN(含有率4w%)である。
本試作品の性能を図15〜図19に示す。
11、31、41、110 基板
12、32、42、112 陽極
13、23、34、44、124 正孔輸送層(HT層)
14、24、35、45、126 発光層(EM層)
126’ 蛍光ドーパントを含んだ発光層(EM層)
126’’ リン光ドーパントを含んだ発光層(EM層)
15 金属をドーピングした有機化合物層
16、39、48、130 陰極
21 プラスチック基板
22 ITO陽極
25、36、128 電子輸送層(ET層)
26 アルカリ金属化合物層
27 マグネシウム/マグネシウム合金層
28 金属酸化物層
33、43、122 正孔注入層(HI層)
37 第一バッファ層
38 第二バッファ層
46 バッファ層
120 有機層の構成
Claims (7)
- 陰極、陽極および前記陰極と前記陽極の間に配置された有機物により構成された層を含み、前記有機物により構成された層は、前記陰極に隣接して配置された電子輸送層、前記陽極に隣接して配置された正孔輸送層および前記電子輸送層と前記正孔輸送層との間に配置された発光層で構成されている有機発光ダイオードであって、
前記電子輸送層が少なくとも一つのn型ドーパントをドーピングされており、
前記正孔輸送層が少なくとも一つのp型ドーパントをドーピングされており、
前記発光層が少なくとも一つの発光ドーパントをドーピングされており、
前記電子輸送層、前記発光層及び前記正孔輸送層が同じ有機系ホスト材料を用いて形成されており、
前記有機系ホスト材料がアントラセン誘導体であることを特徴とする有機発光ダイオード。 - 前記発光層が少なくとも一つの蛍光ドーパントをドーピングされた前記有機系ホスト材料により形成されていることを特徴とする請求項1に記載の有機発光ダイオード。
- 前記発光層が少なくとも一つのリン光ドーパントをドーピングされた前記有機系ホスト材料により形成されていることを特徴とする請求項1に記載の有機発光ダイオード。
- 前記有機層は前記正孔輸送層と前記陽極との間に更に正孔注入層が配置された構成であり、当該正孔注入層が少なくとも一つのp型ドーパントをドーピングされた共通の有機系ホスト材料を用いて形成されていることを特徴とする請求項1〜請求項3のいずれかに記載の有機発光ダイオード。
- 陰極、陽極および前記陰極と前記陽極の間に配置された有機物により構成された層が、前記陰極に隣接して配置された電子輸送層、前記陽極に隣接して配置された正孔輸送層および前記電子輸送層と前記正孔輸送層の間に配置された発光層で構成されたものである有機発光ダイオードの製造方法であって、以下の工程を含むことを特徴とする請求項1〜請求項4のいずれかに係る有機発光ダイオードの製造方法。
a)前記電子輸送層、前記発光層と前記正孔輸送層の形成に用いる同一の有機系ホスト材料であるアントラセン誘導体を準備する工程。
b)前記電子輸送層に少なくとも一つのn型ドーパントをドーピングする工程。
c)前記発光層に発光ドーパントをドーピングする工程。
d)前記正孔輸送層に少なくとも一つのp型ドーパントをドーピングする工程。 - 前記有機系ホスト材料により構成され前記陽極に隣接して配置された正孔注入層を含んでなる前記正孔輸送層における前記正孔注入層に少なくとも一つのp型ドーパントをドーピングする工程を含むことを特徴とする請求項5に記載の有機発光ダイオードの製造方法。
- 前記工程c)における発光ドーパントが蛍光ドーパント又はリン光ドーパントであることを特徴とする請求項5に記載の有機発光ダイオードの製造方法。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/014,508 US7351999B2 (en) | 2004-12-16 | 2004-12-16 | Organic light-emitting device with improved layer structure |
Publications (2)
Publication Number | Publication Date |
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JP2006173619A JP2006173619A (ja) | 2006-06-29 |
JP4411270B2 true JP4411270B2 (ja) | 2010-02-10 |
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JP2005360267A Active JP4411270B2 (ja) | 2004-12-16 | 2005-12-14 | 有機発光ダイオード及びその製造方法 |
Country Status (4)
Country | Link |
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US (2) | US7351999B2 (ja) |
JP (1) | JP4411270B2 (ja) |
CN (2) | CN100573970C (ja) |
TW (1) | TWI268738B (ja) |
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TWI502049B (zh) * | 2006-12-28 | 2015-10-01 | Semiconductor Energy Lab | 有機化合物及合成有機化合物與蒽衍生物之方法 |
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JP2006173619A (ja) | 2006-06-29 |
CN100573970C (zh) | 2009-12-23 |
CN1713788A (zh) | 2005-12-28 |
US7351999B2 (en) | 2008-04-01 |
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US20080057609A1 (en) | 2008-03-06 |
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