CN101609871A - Organic electroluminescence device and preparation method thereof - Google Patents
Organic electroluminescence device and preparation method thereof Download PDFInfo
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- CN101609871A CN101609871A CNA2008101151840A CN200810115184A CN101609871A CN 101609871 A CN101609871 A CN 101609871A CN A2008101151840 A CNA2008101151840 A CN A2008101151840A CN 200810115184 A CN200810115184 A CN 200810115184A CN 101609871 A CN101609871 A CN 101609871A
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Abstract
A kind of organic electroluminescence device of the present invention is characterized in that, comprising: a transparent anode; One hole injection layer, this hole injection layer is grown in the middle part on the transparent anode, makes the side of transparent anode form a step; One hole transmission layer, this hole transmission layer is grown on the hole injection layer; One luminescent layer, this luminescent layer is grown on the hole transmission layer; One electron injecting layer, this electron injecting layer is grown on the luminescent layer; One metallic cathode, this metallic cathode is grown on the electron injecting layer.
Description
Technical field
The invention belongs to technical field of semiconductors, be meant a kind of organic electroluminescence device and preparation method thereof especially, be specifically related to a kind of adopt the organic electronic acceptor material to mix organic electroluminescence device that organic hole mobile material film is hole injection structure, can be applied to the emission of visible light and near infrared light.
Background technology
Organic electroluminescence device (OLED) has that the material range of choice is wide, driving voltage is low, solidifies active illuminating entirely, in light weight, operating temperature range is wide and can be produced on the first-class characteristics of soft substrate, can satisfy information age today to the more requirement of high-performance and bigger information capacity of Display Technique, become one of popular topic of present scientific circles and industrial circle.In addition, because high efficiency, the low cost of OLED also are expected its application prospect at lighting field.
Thereby the performance that improves organic electroluminescence device strengthens the competitiveness of organic electroluminescent product in market, is crucial for the development of current organic electroluminescent technology.The performance of organic electroluminescence device for example luminosity, luminous efficiency, starting resistor and device stability etc. and charge carrier injection efficiency and inject balance very big relation arranged.Hole mobile material aromatic polyamine compound commonly used is placed through long-time such as TPD or NPB film, all can observe the phenomenon of crystallization, and this is to cause one of reason that the OLED life-span decays.A kind of solution is to add hole injection layer (HIL) between ITO electrode and hole transmission layer (HTL).Kodak company has used this material of phthalein cyanogen copper CuPc as the hole injection layer material the earliest, and the efficient and the life-span of device all increase significantly, but starting resistor has but increased.The hole-injecting material of having reported mostly is m-MTDATA, metal oxide and noble metal etc., but being to use them is can not satisfy simultaneously to reduce starting resistor, the requirement that improves luminosity and efficient and increase device stability as the shortcoming of hole injection layer.By the doping techniques that distils altogether, hole mobile material is modified, under suitable doping ratio, can not influence under the condition of starting resistor, improve the efficient and the stability of device simultaneously.
Such as, this class hole injection structure m-MTDATA:F4-TCNQ has been applied to the preparation of organic electro-optic device.
Summary of the invention
The objective of the invention is to, a kind of adopt the organic electronic acceptor material to mix organic electroluminescence device that organic hole mobile material film is hole injection structure is provided, can be applicable to organic flat panel display and solid state lighting field.
The invention provides a kind of organic electroluminescence device, it is characterized in that, comprising:
One transparent anode;
One hole injection layer, this hole injection layer is grown in the middle part on the transparent anode, makes the side of transparent anode form a step;
One hole transmission layer, this hole transmission layer is grown on the hole injection layer;
One luminescent layer, this luminescent layer is grown on the hole transmission layer;
One electron injecting layer, this electron injecting layer is grown on the luminescent layer;
One metallic cathode, this metallic cathode is grown on the electron injecting layer.
The material of wherein said hole injection layer is: the film that organic electronic acceptor material doping hole-transporting type material forms.
Organic electronic acceptor material in the wherein said hole injection layer is following arbitrary material: ten hexafluoro phthalein cyanogen copper, 3,4,9,10-perylene tetracarboxylic acid dianhydride, N, N '-2-dimethyl-3,4,9,10-perylene tetracarboxylic imidodicarbonic diamide or carbon 60.
Hole-transporting type material in the wherein said hole injection layer is identical with the material of hole transmission layer, be following any material: N, N '-two (1-naphthyl)-N, N '-diphenyl-1,1 '-diphenyl-4,4 '-diamines or N, N '-two (3-aminomethyl phenyl)-N, N '-diphenyl-1,1 '-diphenyl-4,4 '-diamines.
The film that organic electronic acceptor material doping hole-transporting type material in the wherein said hole injection layer forms, the weight ratio of its doping content is 1%～50%.
The film that organic electronic acceptor material doping hole-transporting type material in the wherein said hole injection layer forms, the thickness of film is 5～40 nanometers.
The invention provides a kind of manufacture method of organic electroluminescence device, it is characterized in that, comprise following step:
Step 1: transparent anode is cleaned up through mixed liquor, deionized water, acetone and the ethanol of isopropyl alcohol and concentrated ammonia liquor successively;
Step 2: the transparent anode that cleans up is carried out ozone treatment, put into the vacuum film coating chamber plated film again, obtain material structure;
Step 3: in the metal coating chamber, evaporation metal negative electrode on material structure is finished the making of organic electroluminescence device.
Wherein said plated film is at vacuum film coating chamber evaporation hole injection layer, hole transmission layer, luminescent layer and electron injecting layer successively.
The material of wherein said hole injection layer is: the film that organic electronic acceptor material doping hole-transporting type material forms.
Organic electronic acceptor material in the wherein said hole injection layer is following arbitrary material: ten hexafluoro phthalein cyanogen copper, 3,4,9,10-perylene tetracarboxylic acid dianhydride, N, N '-2-dimethyl-3,4,9,10-perylene tetracarboxylic imidodicarbonic diamide or carbon 60.
Hole-transporting type material in the wherein said hole injection layer is identical with the material of hole transmission layer, be following any material: N, N '-two (1-naphthyl)-N, N '-diphenyl-1,1 '-diphenyl-4,4 '-diamines or N, N '-two (3-aminomethyl phenyl)-N, N '-diphenyl-1,1 '-diphenyl-4,4 '-diamines.
The film that organic electronic acceptor material doping hole-transporting type material in the wherein said hole injection layer forms, the weight ratio of its doping content is 1%～50%.
The film that organic electronic acceptor material doping hole-transporting type material in the wherein said hole injection layer forms, the thickness of film is 5～40 nanometers.
Wherein the manufacture method of the organic electronic acceptor material doping hole-transporting type material in the hole injection layer is that the doping way of two kinds of materials with Subjective and Objective steamed altogether, forms p type structure; The evaporation rate of every kind of material and temperature all are independent control; Minimum evaporation rate is 0.1
/ s.
The gross thickness of wherein said material structure is 140 nanometers, and wherein the gross thickness of hole injection layer and hole transmission layer is 80 nanometers, and the thickness of metallic cathode is greater than 120 nanometers.
Description of drawings
For further specifying concrete technology contents of the present invention below in conjunction with embodiment and accompanying drawing, describe in detail as after, wherein:
Fig. 1 is a kind of adopt the organic electronic acceptor material to mix structural representation that organic hole mobile material film is the organic electroluminescence device of hole injection structure;
Fig. 2 is that the photoelectric properties of five kinds of devices compare;
Wherein:
Device A: indium oxide tin glass (ITO)/N, N '-two (1-naphthyl)-N, N '-diphenyl-1,1 '-diphenyl-4,4 '-diamines (NPB), 80 nanometers/oxine aluminium (Alq
3) 60 nanometers/lithium fluoride (LiF), 1 nanometer/aluminium (Al)
Device B: indium oxide tin glass (ITO)/3,4,9,10-perylene tetracarboxylic acid dianhydride (PTCDA) 10 nanometers/N, N '-two (1-naphthyl)-N, N '-diphenyl-1,1 '-diphenyl-4,4 '-diamines (NPB), 70 nanometers/oxine aluminium (Alq
3) 60 nanometers/lithium fluoride (LiF), 1 nanometer/aluminium (Al)
Device C, D, E: indium oxide tin glass (ITO)/N, N '-two (1-naphthyl)-N, N '-diphenyl-1,1 '-diphenyl-4,4 '-diamines (NPB): x%3,4,9,10-perylene tetracarboxylic acid dianhydride (PTCDA) 10 nanometers/N, N '-two (1-naphthyl)-N, N '-diphenyl-1,1 '-diphenyl-4,4 '-diamines (NPB), 70 nanometers/oxine aluminium (Alq
3) photoelectric properties of 60 nanometers/lithium fluoride (LiF), 1 nanometer/aluminium (Al).x＝10、20、30
Embodiment
See also shown in Figure 1ly, a kind of organic electroluminescence device of the present invention comprises:
One transparent anode 101; In the present invention, transparent anode 101 is generally ITO (tin indium oxide) glass.
One hole injection layer 102, this hole injection layer 102 is grown in the middle part on the transparent anode 101, makes the side of transparent anode 101 form a step; The material of wherein said hole injection layer 102 is: the film that organic electronic acceptor material doping hole-transporting type material forms; Organic electronic acceptor material in the wherein said hole injection layer 102 is following arbitrary material: ten hexafluoro phthalein cyanogen copper, 3,4,9,10-perylene tetracarboxylic acid dianhydride, N, N '-2-dimethyl-3,4,9,10-perylene tetracarboxylic imidodicarbonic diamide or carbon 60; Their common ground is the decomposition temperature height, good stability; Good electron acceptor also can be used as the hole cushioning layer material simultaneously separately.Hole-transporting type material in the wherein said hole injection layer 102 is identical with the material of hole transmission layer 103, be following any material: N, N '-two (1-naphthyl)-N, N '-diphenyl-1,1 '-diphenyl-4,4 '-diamines or N, N '-two (3-aminomethyl phenyl)-N, N '-diphenyl-1,1 '-diphenyl-4,4 '-diamines; The film that the organic electronic acceptor material doping hole-transporting type material that wherein said hole injection layer is 102 li forms, the weight ratio of its doping content is 1%～50%; The film that the organic electronic acceptor material doping hole-transporting type material that wherein said hole injection layer is 102 li forms, the thickness of film is 5～40 nanometers.
One hole transmission layer 103, this hole transmission layer 103 is grown on the hole injection layer 102; Hole transmission layer 103 is identical with hole-transporting type material in the hole injection layer 102, is meant that those possess the organic molecule material of higher hole mobility, preferential conduction hole.Be following any material: N, N '-two (1-naphthyl)-N, N '-diphenyl-1,1 '-diphenyl-4,4 '-diamines or N, N '-two (3-aminomethyl phenyl)-N, N '-diphenyl-1,1 '-diphenyl-4,4 '-diamines.
One luminescent layer 104, this luminescent layer 104 is grown on the hole transmission layer 103; Luminescent layer 104 materials should send visible light, can have widely to select, and organic luminous layer can be sent out blue streak (J.Appl.Phys.84,2324 (1998)); (Appl.Phys.Lett.75,1682 (1999)) can glow; Can send out triplet state light (J.Appl.Phys.97,044505 (2005)); Also can be a kind of combination emit white light (Appl.Phys.Lett.86,113507 (2005)); It also can be near-infrared (Appl.Phys.Lett.88,071117 (2006)).
One electron injecting layer 105, this electron injecting layer 105 is grown on the luminescent layer 104; Electron injecting layer 105 materials should have stronger electron transport ability, and lumo energy is relatively near the work content of using cathode material usually.In the present invention, can use the laminated film of metal and organic electronic acceptor material, Mg:CuPc or Mg:PTCDA.
One metallic cathode 106, this metallic cathode 106 is grown on the electron injecting layer 105.In the present invention, metallic cathode 106 can be lithium fluoride/aluminium or magnesium silver alloy.
Please consult Fig. 1 again, the invention provides a kind of manufacture method of organic electroluminescence device, comprise following step:
Step 1: transparent anode 101 is passed through mixed liquor, deionized water, acetone and the ethanol of isopropyl alcohol and concentrated ammonia liquor successively by ultrasonic cleaning 15-20 minute;
Step 2: the transparent anode 101 that cleans up was carried out ozone treatment 10 minutes in homemade UV ozone machine, put into the vacuum film coating chamber plated film again, obtain material structure;
Step 3: in the metal coating chamber, evaporation metal negative electrode 106 on material structure is finished the making of organic electroluminescence device.
Wherein said plated film is at vacuum film coating chamber evaporation hole injection layer 102 successively, hole transmission layer 103, luminescent layer 104 and electron injecting layer 105.
The material of described hole injection layer 102 is: the film that organic electronic acceptor material doping hole-transporting type material forms; Organic electronic acceptor material in the described hole injection layer 102 is following arbitrary material: ten hexafluoro phthalein cyanogen copper, 3,4,9,10-perylene tetracarboxylic acid dianhydride, N, N '-2-dimethyl-3,4,9,10-perylene tetracarboxylic imidodicarbonic diamide or carbon 60; Hole-transporting type material in the described hole injection layer 102 is identical with the material of hole transmission layer 103, be following any material: N, N '-two (1-naphthyl)-N, N '-diphenyl-1,1 '-diphenyl-4,4 '-diamines or N, N '-two (3-aminomethyl phenyl)-N, N '-diphenyl-1,1 '-diphenyl-4,4 '-diamines; The film that the organic electronic acceptor material doping hole-transporting type material that described hole injection layer is 102 li forms, the weight ratio of its doping content is 1%～50%; The film that the organic electronic acceptor material doping hole-transporting type material that described hole injection layer is 102 li forms, the thickness of film is 5～40 nanometers; The manufacture method of the organic electronic acceptor material doping hole-transporting type material in the hole injection layer 102 is that the doping way of two kinds of materials with Subjective and Objective steamed altogether, forms p type structure; The evaporation rate of every kind of material and temperature all are independent control; Minimum evaporation rate is 0.1
/ s; The gross thickness of described material structure is 140 nanometers, and wherein the gross thickness of hole injection layer 102 and hole transmission layer 103 is 80 nanometers, and the thickness of metallic cathode 106 is greater than 120 nanometers.
Characteristics of the present invention and advantage:
(1) the invention provides a kind of novel organic hole implanted layer structure-organic electronic acceptor material doping hole-transporting type material film, effectively raise device efficiency.Because general hole-transporting type material all is good electron donor material, by the doping of organic electronic acceptor material, produce coupling between them, improved the injection efficiency in hole.
(2) the invention provides a kind of novel organic hole implanted layer structure-organic electronic acceptor material doping hole-transporting type material film, effectively raise device lifetime.There are long-time characteristics of placing crystallization in the organic hole transferring material that adopts in the general organic electroluminescence device, causes decay device lifetime.Adopt the organic electronic acceptor material of high stability to mix, effectively improve the stability of hole injection layer film, thereby effectively improve the stability of device.
(3) luminescent spectrum of device is not subjected to the influence of dopant material and concentration, guarantees colorimetric purity.
(4) the invention provides a kind of novel organic hole implanted layer structure-organic electronic acceptor material doping hole-transporting type material film, realize controlled distillation easily.Because two kinds of materials that use the hole injection structure the inside are organic material, to control the effective doping between them and guarantee that the uniformity ratio of doping is easier to, the condition of realization is fairly simple.
Example:
We have prepared a kind of organic electroluminescence device that the present invention relates to, and its device architecture is indium oxide tin glass (ITO)/N, N '-two (1-naphthyl)-N, N '-diphenyl-1,1 '-diphenyl-4,4 '-diamines (NPB): x%3,4,9,10-perylene tetracarboxylic acid dianhydride (PTCDA) 10 nanometers/N, N '-two (1-naphthyl)-N, N '-diphenyl-1,1 '-diphenyl-4,4 '-diamines (NPB), 70 nanometers/oxine aluminium (Alq
3) photoelectric properties (x=10,20 and 30) of 60 nanometers/lithium fluoride (LiF), 1 nanometer/aluminium (Al).With itself and the device A that does not have this hole injection structure: indium oxide tin glass (ITO)/N, N '-two (1-naphthyl)-N, N '-diphenyl-1,1 '-diphenyl-4,4 '-diamines (NPB), 80 nanometers/oxine aluminium (Alq
3) 60 nanometers/lithium fluoride (LiF), 1 nanometer/aluminium (Al) and device B: indium oxide tin glass (ITO)/3,4,9,10-perylene tetracarboxylic acid dianhydride (PTCDA) 10 nanometers/N, N '-two (1-naphthyl)-N, N '-diphenyl-1,1 '-diphenyl-4,4 '-diamines (NPB), 70 nanometers/oxine aluminium (Alq
3) 60 nanometers/lithium fluoride (LiF), 1 nanometer/aluminium (Al) comparison, Fig. 2 has provided the photoelectric properties of device.At 20mA/cm
2Under the current density, using the device starting resistor of the doping type hole injection structure that the present invention relates to is respectively 5.8,5.6, and 5.7V (x=10,20 and 30) is lower than the voltage 6.8V of device B.Simultaneously, at 2000cd/m
2Under the brightness, use the device of the hole injection structure that the present invention relates to, current efficiency reaches 2.0cd/A, is higher than the 1.6cd/A of device A.
In addition, use the device lifetime of the hole injection structure that the present invention relates to longer than the normal component A that does not have this structure.By the optical imagery before and after relatively NPB film and NPB:PTCDA laminated film are annealed, large-area dewetting spot appears in the NPB film after can being clear that 120 degrees centigrade of annealing, and because the stability of PTCDA itself is high, before and after the annealing crystallization can not take place, after making the NPB:PTCDA laminated film through 120 degrees centigrade of annealing, it is more smooth that film surface still keeps, and the large tracts of land crystalline polamer do not occur, and this just helps improving the stability of the device that uses this hole injection structure.
Claims (15)
1, a kind of organic electroluminescence device is characterized in that, comprising:
One transparent anode;
One hole injection layer, this hole injection layer is grown in the middle part on the transparent anode, makes the side of transparent anode form a step;
One hole transmission layer, this hole transmission layer is grown on the hole injection layer;
One luminescent layer, this luminescent layer is grown on the hole transmission layer;
One electron injecting layer, this electron injecting layer is grown on the luminescent layer;
One metallic cathode, this metallic cathode is grown on the electron injecting layer.
2, organic electroluminescence device according to claim 1 is characterized in that, the material of wherein said hole injection layer is: the film that organic electronic acceptor material doping hole-transporting type material forms.
3, organic electroluminescence device according to claim 2, it is characterized in that, organic electronic acceptor material in the wherein said hole injection layer is following arbitrary material: ten hexafluoro phthalein cyanogen copper, 3,4,9,10-perylene tetracarboxylic acid dianhydride, N, N '-2-dimethyl-3,4,9,10-perylene tetracarboxylic imidodicarbonic diamide or carbon 60.
4, organic electroluminescence device according to claim 1, it is characterized in that the hole-transporting type material in the wherein said hole injection layer is identical with the material of hole transmission layer, be following any material: N, N '-two (1-naphthyl)-N, N '-diphenyl-1,1 '-diphenyl-4,4 '-diamines or N, N '-two (3-aminomethyl phenyl)-N, N '-diphenyl-1,1 '-diphenyl-4,4 '-diamines.
5, organic electroluminescence device according to claim 2 is characterized in that, the film that the organic electronic acceptor material doping hole-transporting type material in the wherein said hole injection layer forms, and the weight ratio of its doping content is 1%～50%.
6, according to claim 2 or 3 or 5 described organic electroluminescence devices, it is characterized in that, the film that the organic electronic acceptor material doping hole-transporting type material in the wherein said hole injection layer forms, the thickness of film is 5～40 nanometers.
7, a kind of manufacture method of organic electroluminescence device is characterized in that, comprises following step:
Step 1: transparent anode is cleaned up through mixed liquor, deionized water, acetone and the ethanol of isopropyl alcohol and concentrated ammonia liquor successively;
Step 2: the transparent anode that cleans up is carried out ozone treatment, put into the vacuum film coating chamber plated film again, obtain material structure;
Step 3: in the metal coating chamber, evaporation metal negative electrode on material structure is finished the making of organic electroluminescence device.
8, the manufacture method of organic electroluminescence device according to claim 7 is characterized in that, wherein said plated film is at vacuum film coating chamber evaporation hole injection layer, hole transmission layer, luminescent layer and electron injecting layer successively.
9, the manufacture method of organic electroluminescence device according to claim 7 is characterized in that, the material of wherein said hole injection layer is: the film that organic electronic acceptor material doping hole-transporting type material forms.
10, the manufacture method of organic electroluminescence device according to claim 9, it is characterized in that, organic electronic acceptor material in the wherein said hole injection layer is following arbitrary material: ten hexafluoro phthalein cyanogen copper, 3,4,9,10-perylene tetracarboxylic acid dianhydride, N, N '-2-dimethyl-3,4,9,10-perylene tetracarboxylic imidodicarbonic diamide or carbon 60.
11, the manufacture method of organic electroluminescence device according to claim 7, it is characterized in that the hole-transporting type material in the wherein said hole injection layer is identical with the material of hole transmission layer, be following any material: N, N '-two (1-naphthyl)-N, N '-diphenyl-1,1 '-diphenyl-4,4 '-diamines or N, N '-two (3-aminomethyl phenyl)-N, N '-diphenyl-1,1 '-diphenyl-4,4 '-diamines.
12, the manufacture method of organic electroluminescence device according to claim 8 is characterized in that, the film that the organic electronic acceptor material doping hole-transporting type material in the wherein said hole injection layer forms, and the weight ratio of its doping content is 1%～50%.
13, according to Claim 8 or the manufacture method of 9 or 11 described organic electroluminescence devices, it is characterized in that, the film that the organic electronic acceptor material doping hole-transporting type material in the wherein said hole injection layer forms, the thickness of film is 5～40 nanometers.
14, the manufacture method of organic electroluminescence device according to claim 9, it is characterized in that, wherein the manufacture method of the organic electronic acceptor material doping hole-transporting type material in the hole injection layer is that the doping way of two kinds of materials with Subjective and Objective steamed altogether, forms p type structure; The evaporation rate of every kind of material and temperature all are independent control; Minimum evaporation rate is
15, the manufacture method of organic electroluminescence device according to claim 7, it is characterized in that, the gross thickness of wherein said material structure is 140 nanometers, and wherein the gross thickness of hole injection layer and hole transmission layer is 80 nanometers, and the thickness of metallic cathode is greater than 120 nanometers.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104051632A (en) * | 2013-03-11 | 2014-09-17 | 海洋王照明科技股份有限公司 | Organic light-emitting device and preparation method thereof |
| CN107623088A (en) * | 2012-11-26 | 2018-01-23 | 株式会社半导体能源研究所 | Light-emitting component, light-emitting device, electronic equipment and lighting device |
| CN108666435A (en) * | 2018-07-27 | 2018-10-16 | 京东方科技集团股份有限公司 | The manufacturing method of OLED display panel, display device and display panel |
-
2008
- 2008-06-18 CN CNA2008101151840A patent/CN101609871A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107623088A (en) * | 2012-11-26 | 2018-01-23 | 株式会社半导体能源研究所 | Light-emitting component, light-emitting device, electronic equipment and lighting device |
| US10629823B2 (en) | 2012-11-26 | 2020-04-21 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, light-emitting device, electronic device, and lighting device |
| CN104051632A (en) * | 2013-03-11 | 2014-09-17 | 海洋王照明科技股份有限公司 | Organic light-emitting device and preparation method thereof |
| CN108666435A (en) * | 2018-07-27 | 2018-10-16 | 京东方科技集团股份有限公司 | The manufacturing method of OLED display panel, display device and display panel |
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Open date: 20091223 |