WO2002063698A1 - Protective encapsulation for organic electroluminescent devices - Google Patents
Protective encapsulation for organic electroluminescent devices Download PDFInfo
- Publication number
- WO2002063698A1 WO2002063698A1 PCT/EP2002/001134 EP0201134W WO02063698A1 WO 2002063698 A1 WO2002063698 A1 WO 2002063698A1 EP 0201134 W EP0201134 W EP 0201134W WO 02063698 A1 WO02063698 A1 WO 02063698A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- encapsulant
- layer
- organic
- inner layer
- electroluminescent device
- Prior art date
Links
- 238000005538 encapsulation Methods 0.000 title description 9
- 230000001681 protective effect Effects 0.000 title description 6
- 239000008393 encapsulating agent Substances 0.000 claims abstract description 24
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 5
- CSHWQDPOILHKBI-UHFFFAOYSA-N perylene Chemical class C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims abstract description 3
- 239000000758 substrate Substances 0.000 claims abstract description 3
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- 239000011575 calcium Substances 0.000 claims description 5
- 229920000515 polycarbonate Polymers 0.000 claims description 5
- 239000004417 polycarbonate Substances 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 229920001600 hydrophobic polymer Polymers 0.000 claims description 3
- 229910001617 alkaline earth metal chloride Inorganic materials 0.000 claims description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 2
- -1 alkaline earth metal sulfide Chemical class 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 229910001510 metal chloride Inorganic materials 0.000 claims description 2
- 229910044991 metal oxide Inorganic materials 0.000 claims description 2
- 150000004706 metal oxides Chemical class 0.000 claims description 2
- 229910052976 metal sulfide Inorganic materials 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 40
- 239000011368 organic material Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000002250 absorbent Substances 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 230000002745 absorbent Effects 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 238000001771 vacuum deposition Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 230000008021 deposition Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 230000000254 damaging effect Effects 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000013047 polymeric layer Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 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
- 238000002604 ultrasonography Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
- H10K50/844—Encapsulations
- H10K50/8445—Encapsulations multilayered coatings having a repetitive structure, e.g. having multiple organic-inorganic bilayers
Definitions
- the present invention relates to a protective encapsulation for organic electroluminescent devices.
- LED Light Emitting Diode
- inorganic LEDs have a good performance in terms of emission and duration, they are nonetheless complicated and difficult to fabricate, and accordingly the fabrication of displays based on their use is expensive.
- Organic electroluminescent devices known by the acronym OLED (Organic Light Emitting Diode) are constituted by at least one layer of organic material placed between two electrodes. Generally, these devices are constituted by multiple, different and mutually superimposed organic layers, so as to optimize the electric charge transport and recombination properties with respect to OLEDs constituted by a single layer. In OLEDs, both the organic layers and the electrodes are sensitive to the deterioration produced by the presence of oxygen and humidity. This deterioration causes the appearance of non-emissive regions.
- OLED Organic Light Emitting Diode
- an object of the present invention is to solve the above described problem by means of an encapsulant whose characteristics make it suitable to cover effectively organic electroluminescent devices, i.e.:
- insolubility in common organic solvents such as chlorinated solvents, benzene, toluene, xylene, cyclohexane, acetone, ethanol and methanol;
- an object of the present invention is to provide a structure that is relatively easy to provide in practice, safe in use, effective in operation, and relatively low in cost.
- the present encapsulant for organic electroluminescent devices of the type deposited on a supporting substrate and composed of at least two electrodes between which an electroluminescent substance is arranged characterized in that said encapsulant is formed by at least one first inner layer, which is in direct contact with said electroluminescent device, which is constituted by an organic compound of the type of, or selected from quinacridones, acridones, and derivatives of perilene, said organic component being suitable to isolate said electroluminescent device from said atmospheric deteriorants.
- Figure 1 is a partially sectional perspective view of the encapsulant of the organic electroluminescent device
- Figure 2 is a sectional view of the electroluminescent device and of the encapsulant of Figure 1 taken along a first sectional plane;
- Figure 3 is a sectional view of the electroluminescent device and of the encapsulant of Figure 1, taken along a second sectional plane;
- Figure 4 is the structural formula of the quinacridones used in the present encapsulant
- Figure 5 is the structural formula of the acridones used in replacement of the quinacridones of Figure 4;
- Figures 6 and 7 are the structural formulas of the perilene derivatives used in replacement of the quinacridones of Figure 4. Ways to carrying out the Invention
- the reference numeral 1 generally designates a protective encapsulation for organic electroluminescent devices according to the invention.
- the encapsulant 1 is constituted by an inner layer 2 composed of three superimposed layers 2A, 2B, 2C and of an additional outer layer 3, which seals the electroluminescent device 4.
- the encapsulant 1 covers the electroluminescent device 4, which is in turn constituted by two superimposed layers of active organic material 4A, 4B comprised between a first electrode 5 and a second electrode 6.
- the electrode 5 is composed of a series of bands of conducting material which are mutually parallel and adhere both to the supporting layer 7 and to the layer 4A of active organic material.
- the electrode 6 is instead composed of a series of mutually parallel bands arranged at right angles to the bands of the electrode 5.
- Each band of the electrode 6 is composed of a first layer 6A and of a second layer 6B, which are superimposed and adhere respectively to the layer 4B of the device 4 and to the first layer 2A of the encapsulant 1.
- the layers 2A, 2C of the encapsulant 1 are constituted by organic material, while the layer 2B is made of a mixture of organic material and gas-absorbent material in percentages varying from 0 to 100%, i.e., the absorbent material can be present to the extent of constituting all of said mixture.
- the absorbent material used to capture any molecules of water and oxygen, is composed of metallic calcium.
- the deposition of the layers 2A, 2B, 2C of the encapsulant 1 occurs by vacuum evaporation of the organic material and of the absorbent material.
- the total thickness of the layers that constitute the inner layer 2 of the encapsulant 1 has a minimum limit of effectiveness approximately around 300-500 nm.
- the encapsulant organic material used for the inner layer 2 is constituted by molecules such as quinacridones.
- the outer layer 3 of the encapsulant 1 is constituted by a hydrophobic polymer such as polycarbonate.
- the outer layer 3 is applied to the inner layer 2 by using various methods: spin-coating, spray-coating, lamination, coating by immersion and screen printing.
- EXAMPLE 1 An electroluminescent device 4 was produced in the following manner: a) a glass plate coated with a layer of indium and tin oxide (ITO) with a thickness of approximately 100 nm, with the property of being transparent to light, was used as supporting layer 7. The plate was cleaned chemically by immersing it in solutions of acetone and ethyl alcohol brought to a boil, and was then placed in an ultrasound washing unit for approximately 30 minutes. b) this was followed by the deposition of the two active organic layers 4A and 4B on the electrode 5 of ITO, using an evaporator which operated with a vacuum of 10 "6 mm Hg.
- ITO indium and tin oxide
- a layer 6B of metallic silver with a thickness of 100 nm, acting as protection and electrical contact.
- the electroluminescent device 4 thus fabricated exhibits uniform emission on the entire active surface; non-emissive regions are noted 5 hours after fabrication.
- EXAMPLE 2 An electroluminescent device 4 produced as in Example 1 is then coated, by high-vacuum deposition, by a layer 2A of quinacridone with a thickness of 200 nm.
- the electroluminescent device thus fabricated exhibits at first uniform emission on its entire active surface; 48 hours after fabrication, non-emissive regions are noted.
- An electroluminescent device 4, provided as in Example 1, is then coated by high-vacuum deposition with a layer 2A of quinacridone with a thickness of 600 nm.
- the resulting electroluminescent device at first exhibits uniform emission on its entire active surface; non-emissive regions are noted 30 days after fabrication.
- EXAMPLE 4 An electroluminescent device 4 as in Example 1 is then coated by high- vacuum deposition by a layer 2A of quinacridone with a thickness of 1200 nm.
- the electroluminescent device thus fabricated exhibits at first uniform emission on its entire active surface; non-emissive regions are noted 110 days after fabrication.
- EXAMPLE 5 An OLED device fabricated as in Example 1 is then coated, by high- vacuum deposition, by a layer 2A of quinacridones with a thickness of 1200 nm and by a layer 3 of polycarbonate.
- the electroluminescent device thus fabricated exhibits at first uniform emission on its entire active surface; non-emissive regions are noted 150 days after fabrication.
- EXAMPLE 6 An OLED device fabricated as in Example 1 is then coated, by high- vacuum deposition, with a layer 2A which is constituted by quinacridone with a thickness of approximately 200 nm, with a layer 2B constituted by metallic calcium (absorbent) with a thickness of approximately 1000 nm, with a layer 2C constituted by quinacridone with a thickness of approximately 300 nm, and finally with an outer layer 3 of polycarbonate with a thickness of 1500 nm.
- a layer 2A which is constituted by quinacridone with a thickness of approximately 200 nm
- a layer 2B constituted by metallic calcium (absorbent) with a thickness of approximately 1000 nm
- a layer 2C constituted by quinacridone with a thickness of approximately 300 nm
- an outer layer 3 of polycarbonate with a thickness of 1500 nm.
- the electroluminescent device thus fabricated exhibits at first uniform emission on its entire active surface, and non-emissive regions are still not noted 180 days after fabrication.
- Figure 4 illustrates the structural formula of the quinacridones used.
- the groups Rl, R2, ... , R8 are each independently an atom of hydrogen, a halogen, an alkyl group or an alkoxy group, and R is independently a hydrogen or an alkyl group.
- Figure 5 illustrates the structural formula of the compounds, acridones, used as an alternative to quinacridones, which are preferable.
- the groups Rl, R2, ... , R8 are each independently an atom of hydrogen, a halogen, an alkyl group or an alkoxy group, and R is a hydrogen or an alkyl group.
- Figures 6 and 7 illustrate the structural formulas of the compounds, perilene derivatives, used as an alternative to quinacridones, which are preferable.
- Rl and R2 are independently a hydrogen, an alkyl, a phenyl, a naphthyl, and R3, R4, ... , RIO can be each independently a hydrogen or an alkyl.
- an alkaline metal an alkaline earth metal, an alkaline metal oxide, an alkaline earth metal oxide, an alkaline metal sulfide, an alkaline earth metal sulfide, an alkaline metal chloride, an alkaline earth metal chloride.
- An advantage of the present invention is the use of organic material, optionally mixed with an absorbent, deposited by means of the same deposition methods as the active layers and the electrodes. In this manner, it is possible to provide the first encapsulation process in situ, i.e., in the same place where the device is fabricated, avoiding manipulations and passages that might introduce oxygen, water or other contaminants.
- This encapsulation further protects the active layers, allowing the deposition of a contiguous polymeric layer as an additional protection, also from a mechanical standpoint, of the device. It has thus been shown that the invention achieves the intended aim and objects.
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- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP02719758A EP1364415A1 (en) | 2001-02-07 | 2002-02-04 | Protective encapsulation for organic electroluminescent devices |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ITBO2001A000066 | 2001-02-07 | ||
IT2001BO000066A ITBO20010066A1 (en) | 2001-02-07 | 2001-02-07 | PROTECTIVE ENCAPSULATION FOR ORGANIC ELECTROLUMINESCENT DEVICES |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2002063698A1 true WO2002063698A1 (en) | 2002-08-15 |
Family
ID=11439069
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2002/001134 WO2002063698A1 (en) | 2001-02-07 | 2002-02-04 | Protective encapsulation for organic electroluminescent devices |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP1364415A1 (en) |
IT (1) | ITBO20010066A1 (en) |
WO (1) | WO2002063698A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10339629A1 (en) * | 2003-08-05 | 2005-03-03 | Technische Universität Braunschweig Carolo-Wilhelmina | Process to encapsulate an organic electronic component with a layer of hydrophobic, linear or two-dimensional polycyclic aromatic material |
JP2007501510A (en) * | 2003-08-05 | 2007-01-25 | テヒニシェ・ウニベルジテート・ブラウンシュバイク・カロロ−ビルヘルミナ | Use of a layer composed of a hydrophobic linear or two-dimensional polycyclic aromatic compound as a barrier layer or encapsulation and an electronic component constructed by this type of layer and comprising an organic polymer |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05101886A (en) * | 1991-10-08 | 1993-04-23 | Tdk Corp | Protection of electroluminescent element |
WO1999031741A1 (en) * | 1997-12-15 | 1999-06-24 | International Business Machines Corporation | Compound-metal contacts for organic devices and method for making the same |
US5952778A (en) * | 1997-03-18 | 1999-09-14 | International Business Machines Corporation | Encapsulated organic light emitting device |
-
2001
- 2001-02-07 IT IT2001BO000066A patent/ITBO20010066A1/en unknown
-
2002
- 2002-02-04 EP EP02719758A patent/EP1364415A1/en not_active Withdrawn
- 2002-02-04 WO PCT/EP2002/001134 patent/WO2002063698A1/en not_active Application Discontinuation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05101886A (en) * | 1991-10-08 | 1993-04-23 | Tdk Corp | Protection of electroluminescent element |
US5952778A (en) * | 1997-03-18 | 1999-09-14 | International Business Machines Corporation | Encapsulated organic light emitting device |
WO1999031741A1 (en) * | 1997-12-15 | 1999-06-24 | International Business Machines Corporation | Compound-metal contacts for organic devices and method for making the same |
Non-Patent Citations (2)
Title |
---|
BURROWS P E ET AL: "RELIABILITY AND DEGRADATION OF ORGANIC LIGHT EMITTING DEVICES", APPLIED PHYSICS LETTERS, AMERICAN INSTITUTE OF PHYSICS. NEW YORK, US, vol. 65, no. 23, 5 December 1994 (1994-12-05), pages 2922 - 2924, XP000483815, ISSN: 0003-6951 * |
PATENT ABSTRACTS OF JAPAN vol. 017, no. 450 (E - 1416) 18 August 1993 (1993-08-18) * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10339629A1 (en) * | 2003-08-05 | 2005-03-03 | Technische Universität Braunschweig Carolo-Wilhelmina | Process to encapsulate an organic electronic component with a layer of hydrophobic, linear or two-dimensional polycyclic aromatic material |
DE10339629B4 (en) * | 2003-08-05 | 2005-08-25 | Technische Universität Braunschweig Carolo-Wilhelmina | Process to encapsulate an organic electronic component with a layer of hydrophobic, linear or two-dimensional polycyclic aromatic material |
JP2007501510A (en) * | 2003-08-05 | 2007-01-25 | テヒニシェ・ウニベルジテート・ブラウンシュバイク・カロロ−ビルヘルミナ | Use of a layer composed of a hydrophobic linear or two-dimensional polycyclic aromatic compound as a barrier layer or encapsulation and an electronic component constructed by this type of layer and comprising an organic polymer |
Also Published As
Publication number | Publication date |
---|---|
EP1364415A1 (en) | 2003-11-26 |
ITBO20010066A0 (en) | 2001-02-07 |
ITBO20010066A1 (en) | 2002-08-07 |
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