CN1339057A - 电致发光材料 - Google Patents
电致发光材料 Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 55
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- OSNLTXZLCIEOIQ-UHFFFAOYSA-J 2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate;europium(3+);gadolinium(3+) Chemical class [Eu+3].[Gd+3].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O OSNLTXZLCIEOIQ-UHFFFAOYSA-J 0.000 abstract description 3
- WQOWBGUUAHXBGU-UHFFFAOYSA-J sodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate;gadolinium(3+) Chemical compound [Na+].[Gd+3].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O WQOWBGUUAHXBGU-UHFFFAOYSA-J 0.000 abstract description 2
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- 239000000990 laser dye Substances 0.000 description 2
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- 159000000000 sodium salts Chemical class 0.000 description 2
- ZEJPZHDIJNICFN-UHFFFAOYSA-J sodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate;europium(3+) Chemical compound [Na+].[Eu+3].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O ZEJPZHDIJNICFN-UHFFFAOYSA-J 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- IIKNTDMVXBBEHT-UHFFFAOYSA-B 2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate;gadolinium(3+) Chemical compound [Gd+3].[Gd+3].[Gd+3].[Gd+3].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O.[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O.[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O IIKNTDMVXBBEHT-UHFFFAOYSA-B 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- 101100150353 Arabidopsis thaliana SRS8 gene Proteins 0.000 description 1
- 229910000882 Ca alloy Inorganic materials 0.000 description 1
- 150000000921 Gadolinium Chemical class 0.000 description 1
- 229910000733 Li alloy Inorganic materials 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
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- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
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- 238000001194 electroluminescence spectrum Methods 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
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910001510 metal chloride Inorganic materials 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
- 238000005215 recombination Methods 0.000 description 1
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- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- GXFFSKMBMYHTAE-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate;hydrate Chemical compound O.[Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O GXFFSKMBMYHTAE-UHFFFAOYSA-J 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
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- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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Abstract
一种可形成在紫外光谱区发光的电致发光器件的电致发光材料,包括过渡金属、镧系金属或锕系金属与聚酰胺配体的有机金属配合物,特别是乙二胺四乙酸钆的钠盐,Na[Gd(EDTA)]和乙二胺四乙酸铕钆,Gd[Eu(EDTA)]3。
Description
本发明涉及可在紫外光谱区发光的电致发光材料和由该材料制备的器件。
在电流通过其时能够发光的材料是熟知的，且广泛用于各种显示应用，还提出将有机聚合物用于导致发光器件，但用这些聚合物不能获得纯色，它们制备昂贵且效率相当低。
已经提出的另一种化合物是喹啉酚铝，但这需要使用掺杂剂以得到各种颜色，且效率较低。
在“化学通报”(Chemistry letters)(657-660页，1990)的一篇论文中，Kido等人公开，乙酰丙酮合铽(III)配合物是绿色电致发光的，另外在“应用物理学报”(Applied Physics letters)65(17)(1994年10月24日)的一篇论文中，Kido等人公开，铕(III)三亚苯基二胺配合物是红色电致发光的，但它们在大气条件下不稳定且难以制膜。
这些论文中公开的配合物光致发光效率低，且仅能够产生绿色或红色光，而不能产生其它颜色。
专利申请WO98/58037和WO98/55561公开了在可见光谱区发光的电致发光材料，还公开了包括这些材料的电致发光器件。
由电致发光材料的有机金属配合物发出的光的波长取决于金属或配体。
通常，发出的光的波长越短，获得有效电致发光材料越难，特别是迄今不能生产在紫外光谱区发光的电致发光材料。
可发紫外光的电致发光材料具有一定应用范围，且可在不需要高温或复杂的高能或真空装置下使其成为紫外光源，因此可取代这些紫外光源。
例如，存在一些其中将紫外光用于激发其它材料以使这些其它材料在可见光谱中发荧光的器件和显示器等。
我们现在已发明了可发紫外光的有机金属配合物。
根据本发明，提供一种在紫外光谱区发光的电致发光材料，它包括过渡金属、镧系金属或锕系金属与聚酰胺配体的有机金属配合物。
优选的金属为III价态的钆。
优选的配体为乙二胺四乙酸EDTA、DCTA、DTPA和TTHA。
这些化合物的乙酸形式的结构式在下面给出。
有机金属配合物可通过氯化钆与胺的碱金属盐(如钠盐)反应制备，对于EDTA，反应为：
对于其它聚酰胺，使用相应的碱金属盐。
对于三官能以上的聚酰胺，例如EDTA、DCTA、DTPA、TTHA，这些配合物可为盐，例如碱金属盐形式，并可按这种形式使用。此外，可为过渡金属、镧系金属或锕系金属盐，如Ln*[Ln(EDTA)]3，其中Ln和Ln*为过渡金属、镧系金属或锕系金属，优选为镧系金属如Gd、Sm、Eu、Tb、Dy等。
特别优选的混合配合物为钆配合物，如Gd[Eu(EDTA)]3。
已令人吃惊地发现，有机金属配合物的镧系金属盐显示不同于混合有机金属配合物的不同电致发光光谱。
该混合镧系金属盐可通过镧系金属氯化物与镧系金属聚酰胺配合物反应制备。
可将本发明的材料加入发紫外光的电致发光器件中，因此本发明包括这些电致发光器件。
本发明的紫外光发射器件包括一种透明基材，它是一种用作阳极的导电玻璃或塑料，优选的基材是导电玻璃，如氧化锡铟涂覆的玻璃，但可以使用任何导电的或具有导电层的玻璃。导电聚合物和导电聚合物涂布的玻璃或塑料也可用作基材。可将该电致发光材料从有机溶剂的溶液中通过蒸发沉积到基材上。使用的溶剂取决于材料，例如醇如乙醇、酮如丙酮和乙酰丙酮酸甲酯及氯代烃如二氯甲烷在很多情况下时合适的。
此外，该材料可通过旋涂或通过真空沉积从固态沉积例如通过溅射沉积，或可使用任何其它常规方法。
在一个实施方案中，有一层沉积在透明基材上的空穴输送层，且该电致发光材料就沉积在该空穴输送层上。该空穴输送层可用于输送空穴和阻塞电子，这样可防止电子移动到电极中而没有与空穴复合。因此，载流子的复合主要发生在发射体层。
空穴输送层可用于聚合物电致发光器件中，且可使用任何已知的膜形式的空穴输送材料。
空穴输送层可由芳族胺配合物，如聚(乙烯基咔唑)、N，N’-二苯基-N，N’-二(3-甲基苯基)-1，1’-二苯基-4，4’-二胺(TPD)、聚苯胺等的膜制成。
可非必要地包括染料如发荧光的激光染料、发光激光染料，这样这些材料在紫外光中发荧光以给出特定色谱的发射光。
优选将电致发光材料与聚合物材料如聚烯烃(例如聚乙烯、聚丙烯等)，优选聚苯乙烯混合。活性材料在混合物中的优选量为95至5wt％，更优选25至20wt％。
空穴输送材料可非必要地与电致发光材料进行混合，电致发光材料与空穴输送化合物的比率为(5-95％)∶(95-5％)。在本发明的另一实施方案中，在阴极和电致发光材料层之间有一层电子注入材料，该电子注入材料优选为一种金属配合物，如8-喹啉酚的金属盐(如，喹啉酚铝)，它能够在电流通过其时输送电子。另外，该电子注入材料可与电致发光材料混合，然后与其共沉积。
在一个优选结构中，其基材由作为阳极的透明导电材料组成，在该基材上相继沉积有空穴输送层、电致发光材料层和连接到阳极上的电子注入层。该阳极可以是任何功函数低的金属，如铝、钙、锂、银/镁合金等。
可在器件中存在含荧光材料的一层或多层，这样发出的紫外光将使材料发荧光并发出特定色谱的光。
在下面的实施例中描述。
实施例1
乙二胺四乙酸钆的钠盐，Na[Gd(EDTA)]
将氯化钆(10mmol)溶于水(5ml)中。将乙二胺四乙酸，四钠盐水合物(10mmol)溶于水(10ml)中并按部分加入氯化钆溶液中。该溶液变温热，约15分钟后，形成白色沉淀物。将该混合物进一步放置2小时。将沉淀物滤出得到白色固体，将该白色固体用水(2×5ml)洗涤并在空气中干燥，得到乙二胺四乙酸钆的钠盐，Na[Gd(EDTA)]。
实施例2
乙二胺四乙酸铕钆，Gd[Eu(EDTA)]3
将乙二胺四乙酸铕的钠盐，Na[Eu(EDTA)](4.5mmol)溶于甲醇(30ml)中。将氯化钆(1.5mmol)溶于水(5ml)中并按部分加入乙二胺四乙酸铕的钠盐溶液中。立即形成白色沉淀物。将该混合物进一步放置1小时。将沉淀物滤出得到白色固体，将该白色固体用甲醇(2×10ml)洗涤并在空气中干燥，得到乙二胺四乙酸铕钆，Gd[Eu(EDTA)]3。
光致发光用Liconix 4207 NB，He/Cd激光器的324mn线激发。用Liconix 55PM激光器功率仪测量入射到样品上的激光器功率(0.3mWcm-2)。使用Bentham亮度标准(Bentham SRS8，灯电流4000A，由国家物理实验室(英国)校正的)，进行亮度校正。对样品或薄膜进行PL研究。对实施例的配合物进行试验，结果在后面所附的光谱中给出。
当将低电压沿薄膜施加时，由实施例1和2的化合物的薄膜与作为阳极的涂铟的玻璃和铝阴极构成的电致发光器件在紫外光谱中发出光。在与图1和2中所示的相同光谱范围内发光。
Claims (24)
1.一种在紫外光谱区发光的电致发光材料，它包括过渡金属、镧系金属或锕系金属与聚酰胺配体的有机金属配合物。
2.如权利要求1的电致发光材料，其中金属为III价态的钆。
3.如权利要求1或2的电致发光材料，其中配体为乙二胺四乙酸、DCTA、DTPA或TTHA。
4.如权利要求3的电致发光材料，其中配合物为盐形式。
5.如权利要求4的电致发光材料，其中配合物为碱金属盐形式。
6.如权利要求4的电致发光材料，其中盐为过渡金属、镧系金属或锕系金属盐。
7.如权利要求7的电致发光材料，其中盐为Ln*[Ln(EDTA)]3，其中Ln和Ln*选自过渡金属、镧系金属或锕系金属。
8.如权利要求7的电致发光器件，其中Ln和Ln*选自Gd、Sm、Eu、Tb、Dy。
9.如权利要求1、4或5任何一项的电致发光器件，其中金属配合物为Gd[Eu(EDTA)]3。
10.一种电致发光器件，包括一透明基材，在该透明基材上沉积如前述权利要求1-9中任何一项的电致发光材料。
11.如权利要求1至10任何一项的电致发光器件，其中透明基材为起到阳极作用的导电玻璃或塑料材料。
12.如权利要求10至11任何一项的电致发光器件，其中有一层沉积到透明基材上的空穴输送层，且电致发光材料沉积在该空穴输送层上。
13.如权利要求10至12任何一项的电致发光器件，其中将空穴输送材料与电致发光材料进行混合，电致发光材料与空穴输送化合物的比率为5至95％∶95至5％。
14.如权利要求12或13的电致发光器件，其中空穴输送层为芳胺配合物。
15.如权利要求14的电致发光器件，其中空穴输送层为聚(乙烯基咔唑)、N，N’-二苯基-N，N’-二(3-甲基苯基)-1，1’-二苯基-4，4’-二胺(TPD)或聚苯胺。
16.如权利要求11至15的任何一项的电致发光器件，其中存在一与电致发光材料接触的金属阳极。
17.如权利要求10至16的任何一项的电致发光器件，其中在阴极与电致发光材料层之间存在一电子注入材料层。
18.如权利要求10至17的任何一项的电致发光器件，其中将电子注入材料与电致发光材料混合并与其共沉积。
19.如权利要求17或18的电致发光器件，其中电子注入材料为金属配合物或噁二唑或噁二唑衍生物。
20.如权利要求19的电致发光器件，其中电子注入材料为喹啉酚铝或2-(4-联苯基)-5-(4-叔丁基苯基)-1，3，4-噁二唑。
21.如前述权利要求10至20任何一项的电致发光器件，其中阳极为金属。
22.如权利要求21的电致发光器件，其中阳极为铝、镁、锂、钙、或银/镁合金。
23.如前述权利要求10至22任何一项的电致发光器件，其中存在多个电致发光材料层。
24.如前述权利要求10至23任何一项的电致发光器件，其中存在包括染料的一层或多层，所述染料在紫外光中发荧光，如此在色谱中获得发出的光。
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| GB9901971.3 | 1999-02-01 | ||
| GBGB9901971.3A GB9901971D0 (en) | 1999-02-01 | 1999-02-01 | Electroluminescent material |
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| CN1339057A true CN1339057A (zh) | 2002-03-06 |
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| CN1729198B (zh) * | 2002-12-19 | 2010-11-03 | 株式会社半导体能源研究所 | 有机金属配合物及应用上述有机金属配合物的电致发光元件和发光装置 |
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| WO2002075820A1 (en) * | 2001-03-16 | 2002-09-26 | Elam-T Limited | Electroluminescent devices |
| GB0109758D0 (en) * | 2001-04-20 | 2001-06-13 | Elam T Ltd | Mixed metal organic complexes |
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| WO2002090466A1 (en) * | 2001-05-04 | 2002-11-14 | Elam-T Limited | Electroluminescent devices |
| TWI303533B (en) | 2001-06-15 | 2008-11-21 | Oled T Ltd | Electroluminescent devices |
| GB0116644D0 (en) | 2001-07-09 | 2001-08-29 | Elam T Ltd | Electroluminescent materials and devices |
| WO2003014256A1 (en) | 2001-08-04 | 2003-02-20 | Elam-T Limited | Electroluminescent device |
| GB0202997D0 (en) * | 2002-02-08 | 2002-03-27 | Elam T Ltd | Method for forming electroluminescent devices |
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| GB0210203D0 (en) * | 2002-05-03 | 2002-06-12 | Elam T Ltd | Electroluminescent devices |
| AU2003290341A1 (en) * | 2002-12-24 | 2004-07-22 | Elam-T Limited | Electroluminescent materials and devices |
| JP2008509238A (ja) | 2004-08-07 | 2008-03-27 | オーエルイーディー−ティー リミテッド | エレクトロルミネセンス物質およびデバイス |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1729198B (zh) * | 2002-12-19 | 2010-11-03 | 株式会社半导体能源研究所 | 有机金属配合物及应用上述有机金属配合物的电致发光元件和发光装置 |
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| CA2363840A1 (en) | 2000-08-03 |
| WO2000044851A3 (en) | 2000-12-07 |
| ID29780A (id) | 2001-10-11 |
| AU759615B2 (en) | 2003-04-17 |
| DE60014038T2 (de) | 2005-01-20 |
| JP2002535477A (ja) | 2002-10-22 |
| WO2000044851A2 (en) | 2000-08-03 |
| ATE277143T1 (de) | 2004-10-15 |
| MXPA01007733A (es) | 2003-06-24 |
| KR20010101745A (ko) | 2001-11-14 |
| ES2223450T3 (es) | 2005-03-01 |
| EP1155095B1 (en) | 2004-09-22 |
| BR0008761A (pt) | 2001-11-27 |
| AU2304100A (en) | 2000-08-18 |
| TWI257945B (en) | 2006-07-11 |
| PT1155095E (pt) | 2005-01-31 |
| GB9901971D0 (en) | 1999-03-17 |
| EP1155095A2 (en) | 2001-11-21 |
| DE60014038D1 (de) | 2004-10-28 |
| US6717354B1 (en) | 2004-04-06 |
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