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WO2012008275A1 - Procédé de production d'un élément électroluminescent organique - Google Patents

Procédé de production d'un élément électroluminescent organique Download PDF

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Publication number
WO2012008275A1
WO2012008275A1 PCT/JP2011/064373 JP2011064373W WO2012008275A1 WO 2012008275 A1 WO2012008275 A1 WO 2012008275A1 JP 2011064373 W JP2011064373 W JP 2011064373W WO 2012008275 A1 WO2012008275 A1 WO 2012008275A1
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WIPO (PCT)
Prior art keywords
film
layer
organic
electrode
roll
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2011/064373
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English (en)
Japanese (ja)
Inventor
伸明 高橋
洋祐 ▲高▼島
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Konica Minolta Inc
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Konica Minolta Inc
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Application filed by Konica Minolta Inc filed Critical Konica Minolta Inc
Priority to JP2012524508A priority Critical patent/JP5772826B2/ja
Publication of WO2012008275A1 publication Critical patent/WO2012008275A1/fr
Anticipated expiration legal-status Critical
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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
    • H10K71/10—Deposition of organic active material
    • H10K71/16—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering
    • H10K71/164—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering using vacuum deposition

Definitions

  • the present invention relates to a method for producing an organic electroluminescence element, and more particularly, to a method for producing an organic electroluminescence element having improved light emission initial characteristics and element lifetime.
  • organic electroluminescence elements also referred to as organic EL elements
  • a first electrode (anode) made of a transparent conductive film such as ITO (Indium tin oxide) is provided on a transparent base material such as a glass base material, and an organic functional layer including at least a light-emitting layer thereon,
  • a second electrode (cathode) made of aluminum or the like is provided in this order, and the first electrode (anode) and the second electrode (cathode) are connected to an external circuit or the peripheral portion of the organic EL element.
  • a first electrode (anode) side extraction electrode and a second electrode (cathode) side extraction electrode for connection to the internal drive circuit are formed.
  • An organic EL element emits light when a very thin thin film (organic functional layer) of an organic compound including a fluorescent or phosphorescent light emitting layer is sandwiched between a first electrode (anode) and a second electrode (cathode) and a current is passed.
  • organic functional layer organic compound including a fluorescent or phosphorescent light emitting layer
  • an organic compound is usually an insulator
  • current can be injected and driven as an organic EL element by making the organic layer very thin. It can be driven at a low voltage of 10 V or less, and it is possible to obtain high-efficiency light emission.
  • the organic EL element is manufactured using a flexible base material (web) in addition to a single-wafer substrate.
  • a dry process method such as a vacuum film forming method and a wet process method such as a coating method are known.
  • the dry process method has a problem that the composition of the metal oxide thin film formed by sputtering during film formation changes when moisture comes out of the web by vacuum or heating. Therefore, in order to reduce the influence of moisture coming out of the web, in the roll coater type continuous sputtering system, the roll chamber and the film forming chamber are separated by a shielding plate, or preheating (removing moisture) in the roll chamber (web). (See, for example, Patent Document 1). However, since it is necessary to pass the web from the roll chamber to the film forming chamber while making contact with the cooling roll, the roll chamber and the film forming chamber cannot be completely separated. Therefore, the problem that moisture generated in the roll chamber is mixed into the film forming chamber and the composition of the metal oxide thin film formed by sputtering cannot be completely solved.
  • the moisture of the substrate increases the moisture partial pressure of the film forming chamber and affects the composition of the sputtered metal oxide film.
  • a material that can ensure a vacuum of 10 ⁇ 4 Pa or less it is preferable to use a material that can ensure a vacuum of 10 ⁇ 4 Pa or less.
  • a cryopump is preferably provided in order to sufficiently reduce the residual gas in the vacuum device, particularly the amount of moisture, and in that case, the moisture partial pressure in the device can be reduced to about 10 ⁇ 5 Pa or less.
  • a large amount of moisture is brought into the apparatus from a substrate or the like, it not only adsorbs to the interface between the light emitting layer and the electron injection layer, but also adversely affects the deposited film, so that sufficient moisture partial pressure management is essential.
  • the device driving voltage can be lowered, the occurrence / growth of dark spots can be suppressed, and the initial light emission characteristics and device lifetime can be improved.
  • maintaining the environment of the film forming chamber in the vacuum film forming apparatus at low moisture for example, by reducing the water partial pressure to 10 ⁇ 5 Pa or less, is effective in improving the initial light emission characteristics and device life of the organic EL device.
  • Patent Document 2 See, for example, Patent Document 2.
  • the method there is no suggestion of a method other than using a cryopump in order to sufficiently reduce the water content.
  • the moisture partial pressure becomes a specified value when a cryopump is used. The problem is that it takes time.
  • the object of the present invention is performed using a flexible film (long substrate), and in the production of an organic electroluminescence device including a vacuum film formation step, the driving voltage is low and the generation / growth of dark spots is suppressed.
  • Another object of the present invention is to provide a method for producing an organic electroluminescence device having improved initial light emission characteristics and lifetime.
  • At least one of a leader film and a side tape comprising at least a step of sequentially forming a first electrode, an organic functional layer including at least a light emitting layer, and a second electrode on a flexible film (long substrate).
  • the process includes a vacuum film forming process performed using a vacuum film forming apparatus.
  • the flexible film and at least one of a leader film and a side tape are put into the vacuum film forming apparatus.
  • a method for producing an organic electroluminescence element wherein the organic electroluminescence element is dried before the film apparatus is charged, and the vacuum film forming process is performed at a moisture partial pressure of the vacuum film forming apparatus of 5 ⁇ 10 ⁇ 5 Pa or less.
  • the driving voltage is low and the generation / growth of dark spots is suppressed.
  • an organic electroluminescence device having improved light emission initial characteristics and lifetime can be produced.
  • the vacuum film forming step can reduce the moisture content of the film to a certain level or less by setting the water partial pressure in the film forming chamber of the vacuum film forming apparatus to a specified value or less. Although it is effective in improving the initial light emission characteristics and the device lifetime, it takes time for the moisture partial pressure to reach the specified value even if a cryopump is used because the amount of moisture brought into the vacuum film forming apparatus is large.
  • the present invention reduces the time for reducing the moisture partial pressure in the film forming chamber to a certain value.
  • the original roll components such as the belt-like flexible support, the leader for passing the original roll, and the side tape for non-contact winding are put into the vacuum film formation process.
  • the above problem was solved by drying it.
  • the water content of a roll-shaped resin film or the like can be measured using a coulometric titration method of Karl Fischer method. Ten samples are taken at random and measured by the coulometric titration method of Karl Fischer method and averaged.
  • the moisture of the film forming material (deposition source) supplied to the film forming chamber of the vacuum film forming apparatus is also dried in advance.
  • the moisture partial pressure in the film forming chamber can be measured by, for example, ULVAC small partial pressure monitor MALIN (model MA-01). Incidentally, contamination such as moisture, nitrogen and oxygen can be seen.
  • the present invention is an organic material comprising at least a step of sequentially forming a first electrode, at least one organic functional layer, and a second electrode on a belt-like flexible support, and a step of forming a sealing layer.
  • the present invention relates to the supply of the original winding constituent material and the vacuum film forming material in the vacuum film forming process included in the method of manufacturing the electroluminescent element.
  • an organic electroluminescence element hereinafter referred to as an organic EL element
  • FIG. 1 is a schematic cross-sectional view showing an example of a layer structure of an organic EL element.
  • FIG. 1A is a schematic cross-sectional view showing a constituent layer of an organic EL element on which a sealing film is formed.
  • FIG. 1B is a schematic cross-sectional view showing a constituent layer of an organic EL element formed by attaching a sealing film via an adhesive.
  • 1a represents an organic EL element.
  • the organic EL element 1a includes a first electrode 102, a hole transport layer 103, a light emitting layer 104, an electron injection layer 105, a second electrode 106, and a sealing layer 107 in this order on a substrate 101.
  • a first electrode 102 a hole transport layer 103
  • a light emitting layer 104 a light emitting layer 104
  • an electron injection layer 105 a second electrode 106
  • a sealing layer 107 in this order on a substrate 101.
  • 1b represents an organic EL element.
  • the organic EL element 1b includes a first electrode 102, a hole transport layer 103, a light emitting layer 104, an electron injection layer 105, a second electrode 106, and an adhesive layer 108 as a sealing layer on a substrate 101. And the sealing film 109 in this order.
  • a hole injection layer (not shown) may be provided between the first electrode 102 and the hole transport layer 103.
  • an electron transport layer (not shown) may be provided between the light emitting layer 104 and the electron injection layer 105.
  • a gas barrier film (not shown) may be provided between the first electrode 102 and the substrate 101.
  • the present invention relates to a manufacturing method of the organic EL element 1a (1b) shown in FIGS. 1A and 1B and organic EL elements produced by these manufacturing methods.
  • the layer structure of the organic EL element shown in this figure is an example, but the following structure can be given as a layer structure of another typical organic EL element.
  • Base material / anode / light emitting layer / electron transport layer / cathode / sealing layer (2) Base material / anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode / sealing layer (3) substrate / anode / hole transport layer (hole injection layer) / light emitting layer / hole blocking layer / electron transport layer / cathode buffer layer (electron injection layer) / cathode / sealing layer (4) substrate / Anode / anode buffer layer (hole injection layer) / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode buffer layer (electron injection layer) / cathode / sealing layer Each layer is described later.
  • FIG. 2 is a schematic diagram showing an example of a process for producing an organic EL element.
  • description of the manufacturing process shown by this figure is an example of an organic EL element.
  • a gas barrier layer, a first electrode, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer It carries out about the case of the organic EL element in which each layer is formed in the order of sticking a 2nd electrode and a sealing film.
  • the first electrode forming step is omitted.
  • the manufacturing process 2a includes a supply unit 3 for supplying the original roll 3a1 of the belt-like flexible support, a hole transport layer forming process 4 for forming the hole transport layer, and a light emitting layer for forming the light emitting layer. It consists of a forming step 5 and an electron transport layer forming step 6 for forming an electron transport layer.
  • the belt-like flexible support on which the electron transport layer has been formed is wound up by the take-up unit 7 and becomes the original roll 7a of the belt-like flexible support.
  • the manufacturing process 2b includes a supply unit 8 for supplying the original roll 7a of the belt-like flexible support, an electron injection layer forming process 9 for forming the electron injection layer, and a second electrode for forming the second electrode.
  • the strip-shaped flexible support on which the second electrode has been formed is wound up by the winding unit 11 and becomes the original winding roll 11 a of the strip-shaped flexible support.
  • it consists of a supply unit 12 for supplying the original roll 11a of the belt-like flexible support, a sealing layer forming step 13 for forming a sealing layer, and a cutting step 14 for cutting into individual elements. Thereafter, individual elements are formed, wiring and electric circuits are mounted, and an organic electroluminescence panel is formed.
  • the manufacturing apparatus shown in the figure is configured so that the atmospheric pressure is continuously reduced from the supply unit 3 to the hole transport layer forming step 4, the light emitting layer forming step 5, the electron transport layer forming step 6 and the winding unit 7 in the manufacturing process 2a.
  • the supply unit 8 to the electron injection layer forming step 9, the second electrode forming step 10, and the winding unit 11 are subjected to a vacuum process, and the supply unit in the manufacturing step 2b.
  • 12 shows a case where the sealing layer forming step 13 and the cutting step 14 are performed under an atmospheric pressure inert gas process or a vacuum process.
  • the supply unit 3 includes a feeding unit 301 and a surface treatment unit 302.
  • a strip-shaped flexible support hereinafter referred to as a strip-shaped flexible support A
  • a gas barrier film and an anode layer including a first electrode are already formed in this order is wound around a winding core. Supplied in the taken roll state.
  • 3a1 shows the former roll of the belt-like flexible support A.
  • the surface treatment unit 302 includes a cleaning surface modification processing apparatus and antistatic means, but the antistatic means is omitted here.
  • the cleaning surface modification apparatus performs cleaning modification on the surface of the first electrode (not shown) of the belt-like flexible support sent from the supplying step 3 before the application of the organic functional layer.
  • a low pressure mercury lamp an excimer is used.
  • a low-pressure mercury lamp having a wavelength of 184.2 nm is irradiated at an irradiation intensity of 5 to 20 mW / cm 2 and a distance of 5 to 15 mm.
  • the antistatic means includes a non-contact type static elimination prevention device, a contact type static elimination prevention device, and the like, and is performed using, for example, a non-contact type ionizer, a static elimination roll, or a conductive brush connected to the ground.
  • the non-contact type antistatic device is preferably used on the first electrode surface side of the belt-like flexible support A, and the contact-type antistatic device is preferably used on the back surface side of the belt-like flexible support A.
  • the strip-shaped flexible support A is unwound from the roll and enters the hole transport layer forming step 4.
  • the first wet coating is performed by coating the backup roll 4a and the hole transport layer forming coating liquid on the first electrode of the strip-like flexible support A held by the backup roll 4a.
  • the first drying device 4c for removing the solvent of the hole transport layer formed on the first electrode of the belt-like flexible support A, and the first for heating the hole transport layer from which the solvent has been removed.
  • a heat treatment device 4d for heating the hole transport layer from which the solvent has been removed.
  • an antistatic means may be provided, but it is omitted in the figure.
  • the coating liquid for forming a hole transport layer by the first wet coater 4b is applied on the first electrode except for a part of one end of the already formed first electrode, for example.
  • the first wet coater 4b applies a light emitting layer on the first electrode in accordance with the pattern of the first electrode formed by patterning.
  • a die coating method stripe & intermittent coater
  • an inkjet method etc. It is possible to use various coating apparatuses used for a flexographic printing method, an offset printing method, a gravure printing method, a screen printing method, a spray coating method using a mask, and the like.
  • the first drying device 4c is a drying processing device that removes the solvent by a heated airflow.
  • the height is 100 mm from the ejection port of the slit nozzle type toward the film formation surface, the ejection air velocity is 1 m / s, and the width. Carry out with a hand distribution of 5% and a drying temperature of 100 ° C.
  • the heat treatment device 4d heats the hole transport layer from the back surface side of the belt-like flexible support A by the back surface heat transfer method, for example, a back surface heat transfer type heat treatment device having a plurality of, for example, 200 ° C. heating rollers. After removing the solvent, the substrate is sucked and conveyed by sucking heat rolls with a temperature of 200 ° C. arranged closely, and heat treatment is performed by heating by backside heat transfer. By this heat treatment, smoothness of the film, removal of residual solvent, curing of the coating film, and the like are performed.
  • the back surface heat transfer method for example, a back surface heat transfer type heat treatment device having a plurality of, for example, 200 ° C. heating rollers.
  • the belt-like flexible support A enters the light emitting layer forming step 5 after the hole transport layer forming step 4.
  • a second wet coater 5b for applying a light emitting layer forming coating solution on the hole transporting layer of the belt-like flexible support A having the hole transporting layer held by the backup roll 5a.
  • a second drying device 5c for removing the solvent of the light emitting layer formed on the hole transport layer, and a second heat treatment device 5d for heating the light emitting layer from which the solvent has been removed.
  • the same antistatic means as described above may be used, but is omitted.
  • the second wet coater 5b is preferably of the same type as the first wet coater 4b.
  • the second drying device 5c has the same structure as the first drying device 4c.
  • the second heat treatment apparatus 5d has the same structure as that of the first heat treatment apparatus 4d, and heats the light emitting layer formed on the hole transport layer from the back surface side of the belt-like flexible support by the back surface heat transfer method. It is supposed to be.
  • the belt-like flexible support is in the electron transport layer coating step 6 after the light emitting layer forming step 5.
  • a third wet coater 6b for applying a coating liquid for forming an electron transport layer on the light emitting layer of the belt-like flexible support A held by the backup roll 6a, and on the light emitting layer It has the 3rd drying apparatus 6c which removes the solvent of the formed electron carrying layer, and the 3rd heat processing apparatus 6d which heats the electron carrying layer from which the solvent was removed.
  • the same antistatic means as described above may be used, but is omitted.
  • the hole transport layer forming step 4, the light emitting layer forming step 5, and the electron transport layer forming step 6 shown in this figure show the case where there is one wet coating device, a drying device, and a heat treatment device, respectively. It is possible to increase according to.
  • strip-shaped flexible support 7b in which each layer of the organic functional layer is formed by the winding unit 7 is wound around a winding core with the organic functional layer side outside, and the strip-shaped flexible support (hereinafter, strip-shaped flexible support) is wound.
  • the side tape 7c is wound around at least both ends other than the organic functional layer forming portion of the belt-like flexible support B, and wound in a non-contact manner so as to form a space in the intermediate organic functional layer forming portion. .
  • non-contact winding it is possible to prevent the organic functional layer which is easily damaged by a thin film from being deteriorated in quality due to scratches or adhesion of foreign substances.
  • the roll-shaped side tape 7c is supplied to the winding unit 7, and the roll-shaped flexible support 7a is wound by winding the belt-shaped flexible support 7b and the side tape 7c together.
  • the winding-up part 7 is kept in nitrogen atmosphere whose water content is 100 ppm or less, Preferably it is 50 ppm or less.
  • a step of wiping unnecessary portions of the formed organic functional layer with a solvent or the like that can dissolve each layer may be provided.
  • the wiping step for example, there is a wiping device described in JP-T-2007-515756, etc., and using these, wiping is carried out according to the position of the alignment mark previously formed on the belt-like flexible support. .
  • a continuous wiping method is preferred, and when carrying out wiping in the width direction by stopping conveyance, an accumulator mechanism or the like is provided at the front and back to continuously perform from application to winding of the organic functional layer. desirable.
  • the wound roll 7a of the strip-like flexible support B is stored in a storage box under reduced pressure (10 ⁇ 6 to 10 ⁇ 2 Pa) or inert gas (for example, nitrogen) environment which is a low moisture environment. Also good.
  • the storage period in the storage box is preferably 1 to 200 hours.
  • a temperature may be applied to remove oxygen and trace moisture resulting from element deterioration.
  • an electron injection layer and a second electrode are formed on the strip-shaped flexible support B once wound up by the manufacturing process 2b.
  • Supplied section 8 has a feeding section.
  • the strip-shaped flexible support B on which each organic functional layer is formed is supplied in a roll state wound around a winding core.
  • 7a shows the roll-shaped strip
  • the connecting portion of the supply portion 8, the electron injection layer forming step 9 and the second electrode forming step 10 is separated by the shutter G1, and the supply portion 8 is supplied so that the roll-shaped strip-like flexible support 7a can be supplied. Part 8 is returned to atmospheric pressure.
  • the former roll of the leader film is placed in the belt-like flexible support supplying step 8, the leading end of the leader film is joined to the end of the belt-like flexible substrate B, and the belt-like flexible substrate winding is performed.
  • the both ends of the leader film are cut and left in the process, or the leader film is wound around the end of the belt-like flexible support B of the original winding roll, that is, the winding core side in advance.
  • There is a method of cutting the both ends of the film of the leader after taking it and leaving it in the process.
  • a roll-shaped strip-like flexible support 7a wound together with the side tape 7c is set on the feeding portion of the supply unit 8, and the strip-like flexible support 7b and the side are arranged at the time of unwinding.
  • the tape 7c is separated, the belt-like flexible support 7b is supplied to the electron injection layer forming step 9, and the side tape 7c is wound up.
  • the electron injection layer forming step 9 and the second electrode forming step 10 for forming the second electrode are vacuum process steps.
  • the electron injection layer forming step 9 and the second electrode forming step 10 are performed by vacuum deposition.
  • a sputtering method, a reactive sputtering method, a molecular beam epitaxy method, a cluster ion beam method, an ion plating method, or the like can be used.
  • the belt-like flexible support B is unwound from the roll and enters the electron injection layer forming step 9.
  • the electron injection layer forming step 9 and the second electrode forming step 10 are the same vacuum process step, and two vapor deposition portions are continuously provided. If there is a difference in vapor deposition rate between the two vapor deposition sections, the two vapor deposition sections that become the electron injection layer forming step 9 and the second electrode forming step 10 in the same vacuum chamber through an accumulator mechanism so that it can be adjusted. May be provided.
  • the electron injection layer forming step 9 the vapor deposition material boat of the second electrode formation part (vapor deposition apparatus) is heated to perform mask vapor deposition, and an electron injection layer is formed on the electron transport layer.
  • 9a schematically shows an evaporation source container
  • 9b schematically shows a support holder of the vapor deposition apparatus.
  • the vapor deposition material boat of the second electrode forming portion (vapor deposition apparatus) is heated to perform mask vapor deposition, and the second electrode is formed on the electron injection layer.
  • 10b denotes a support holder
  • 10a denotes an evaporation source container.
  • the belt-like flexible support B on which the electron injection layer is formed in the electron injection layer formation step 9 is configured to be sent to the second electrode formation step 10 via an accumulator mechanism.
  • the strip-shaped flexible support 11b formed up to the second electrode by the winding unit 11 is wound around the winding core with the second electrode side outside, and a roll-shaped flexible support 11a (hereinafter, strip-shaped flexible support) Let flexible support C).
  • the side tape 11c is wound around at least both ends other than the organic functional layer forming portion of the belt-like flexible support C, and wound in a non-contact manner so as to form a space in the intermediate organic functional layer forming portion. .
  • non-contact winding it is possible to prevent the organic functional layer which is easily damaged by a thin film from being deteriorated in quality due to scratches or adhesion of foreign substances.
  • the roll-shaped side tape 11c When using a side tape, the roll-shaped side tape 11c is supplied to the winding part 11, and it forms by winding together the strip
  • the leader film, side tape, and other members used here are preferably dried in advance because the time until the degree of vacuum at which a film can be formed becomes long if a large amount of moisture is brought in, and the amount of water is preferably 300 ppm. Hereinafter, it is more desirably 50 ppm or less.
  • the winding portion 11 When the roll-shaped strip-shaped flexible support 11a is wound up, the winding portion 11, the electron injection layer forming step 9 and the second electrode forming step 10 are separated by the shutter G2, and the roll-shaped strip-shaped flexible support 11a is separated.
  • the winding portion 11 is returned to atmospheric pressure so that the support 11a can be taken out.
  • a leader similar to the belt-like flexible support is attached to the end of the belt-like flexible support C, and when the leading end of the leader comes to the roll-like belt-like flexible support 11a, the leader The tip of is cut.
  • a leader is disposed to guide the next strip-shaped flexible support.
  • Supplied part 12 has a feeding part.
  • the belt-like flexible support C formed up to the second electrode is supplied in a roll state wound around the winding core.
  • the belt-like flexible support 11b is unwound from the roll 11a and enters the sealing layer forming step 13.
  • the belt-like flexible support C wound together with the side tape is set in the feeding portion of the supplying step 12, and the belt-like flexible support 11b and the side tape 11c are separated at the time of unwinding. Then, the belt-like flexible support 11b is supplied to the sealing layer forming step 13, and the side tape 11c is wound up.
  • the sealing layer forming step 13 is a sealing film sticking step.
  • the sealing layer is unwound from the roll-like sealing film 13b1 and sealed with a sealing resin (adhesive).
  • the stop film 13b is pressure-bonded to the belt-like flexible support 11b at the sticking portion constituted by the pressure-bonding roll 13b2, and is further cured and sealed by a curing processing portion (not shown in the drawing).
  • the adhesive is applied on the sealing film 13b in this example, but may be applied on the second electrode of the strip-shaped flexible support 11b.
  • a hardening process part consists of a heating part or an ultraviolet irradiation part, for example, and is arrange
  • the organic electroluminescence element produced on the continuous flexible film in the cutting step 14 is cut into a product size.
  • the alignment mark attached to the belt-like flexible support is detected, and the product is punched and cut into a product size according to the position of the alignment mark.
  • the continuous flexible film after the organic EL element is punched is then wound into a roll by a winder.
  • FIG. 1 An example of an element formed by punching and cutting is schematically shown in FIG.
  • (a) is a view of the device when viewed from above
  • (b) is a cross-sectional view taken along line O-O ′
  • (c) is a cross-sectional view taken along line P-P ′.
  • 101 is a base material which is a flexible support
  • 102 is a first electrode
  • 102a is a first electrode extraction electrode
  • 103 to 105 are a hole transport layer, a light emitting layer, an electron transport layer and a hole injection layer
  • 106 represents a second electrode
  • 106a represents a second electrode extraction electrode
  • 108 represents an adhesive layer
  • 109 represents a sealing film.
  • A indicates the width direction of the belt-like flexible support of the fabricated element
  • B indicates the transport direction.
  • An organic electroluminescence panel is formed by mounting an electric circuit on each element cut and punched into a product size.
  • the sealing layer forming step 13 is preferably sealed by an atmospheric pressure process of an inert gas such as a rare gas or nitrogen gas in order to keep harmful components to a minimum.
  • an inert gas such as a rare gas or nitrogen gas
  • the cutting process is not necessarily performed in an inert gas atmosphere, but here, an example is shown in which processing is performed continuously with sealing in an inert gas atmosphere.
  • sealing layer forming step 13 has been described as an inert gas atmospheric pressure process in the above, sealing may be performed in a vacuum process, for example.
  • This flexible film cutting process is preferably performed in an air atmosphere.
  • An organic electroluminescence panel is formed by mounting an electric circuit on each element cut and punched into a product size.
  • a method of forming a sealing layer on the electrode layer instead of sticking the sealing film may be used.
  • a sealing layer forming step for example, a sealing layer forming step such as a silicon oxide layer by a vacuum process such as sputtering, ion plating, or plasma CVD is added.
  • a sealing layer forming step combined with a process pressure replacement step similar to the above is added.
  • organic light emitting materials contained in the light emitting layer include aromatic heterocyclic compounds such as carbazole, carboline, diazacarbazole, triarylamine derivatives, stilbene derivatives, polyarylenes, aromatic condensed polycycles.
  • aromatic heterocyclic compounds such as carbazole, carboline, diazacarbazole, triarylamine derivatives, stilbene derivatives, polyarylenes, aromatic condensed polycycles.
  • a dopant may be contained in the light emitting material.
  • the dopant include known fluorescent dyes such as perylene derivatives and pyrene derivatives, and in the case of phosphorescent light emitting layers, for example, tris (2-phenylpyridine) iridium, bis (2-phenylpyridine) (acetylacetonate).
  • a complex compound such as an orthometalated iridium complex represented by iridium, bis (2,4-difluorophenylpyridine) (picolinato) iridium, and the like is also contained in an amount of about 0.1 to 20% by mass.
  • the phosphorescent light emitting method is relatively less likely to cause light emission unevenness due to unevenness of the layer interface due to coating because it has a light emitting region inside the light emitting layer.
  • the thickness of the light emitting layer ranges from 1 nm to several hundred nm.
  • Examples of materials used in the hole injection / transport layer include phthalocyanine derivatives, heterocyclic azoles, aromatic tertiary amines, polyvinyl carbazole, polyethylene dioxythiophene / polystyrene sulfonic acid (PEDOT: PSS), and the like.
  • Polymer materials such as conductive polymers are also used for the light emitting layer, for example, carbazole-based light emitting materials such as 4,4′-dicarbazolylbiphenyl, 1,3-dicarbazolylbenzene, ) Low molecular light emitting materials represented by pyrene light emitting materials such as azacarbazoles, 1,3,5-tripyrenylbenzene, polymer light emitting materials represented by polyphenylene vinylenes, polyfluorenes, polyvinyl carbazoles, etc. Etc.
  • carbazole-based light emitting materials such as 4,4′-dicarbazolylbiphenyl, 1,3-dicarbazolylbenzene
  • Low molecular light emitting materials represented by pyrene light emitting materials such as azacarbazoles, 1,3,5-tripyrenylbenzene, polymer light emitting materials represented by polyphenylene vinylenes, polyfluorenes, polyvinyl carbazoles, etc.
  • Examples of the electron injection / transport layer material include metal complex compounds such as 8-hydroxyquinolinate lithium and bis (8-hydroxyquinolinate) zinc, and the following nitrogen-containing five-membered ring derivatives. That is, oxazole, thiazole, oxadiazole, thiadiazole or triazole derivatives are preferred.
  • the film thickness of the organic EL element and each organic layer needs to be about 0.05 to 0.3 ⁇ m, preferably about 0.1 to 0.2 ⁇ m.
  • a wet process such as coating and printing is preferable.
  • a wet process such as coating and printing is preferable.
  • die coat method, screen printing method, flexographic printing method, ink jet method, wire bar method, cap coating method, spray coating method, casting method, roll coating method, bar coating method, gravure coating method, etc. can be used. It is. The use of these wet coating machines can be appropriately selected according to the material of the organic compound layer.
  • Each organic material has its own solubility characteristics (solubility parameters, ionization potential, polarity), and there are limitations on the solvents that can be dissolved. In this case, since the solubility is different from each other, the concentration cannot be generally determined.
  • the type of the solvent used in the present invention is suitable for the above conditions depending on the organic EL material to be formed.
  • halogenated hydrocarbon solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, tetrachloroethane, trichloroethane, chlorobenzene, dichlorobenzene, chlorotoluene, dibutyl ether, tetrahydrofuran, Ether solvents such as dioxane and anisole, alcohol solvents such as methanol, ethanol, isopropanol, butanol, cyclohexanol, 2-methoxyethanol, ethylene glycol, glycerin, benzene, toluene, xylene, ethylben Aromatic hydrocarbon solvents such as hexane, paraffin solvents such as hexane, octane, decane, tetralin, ester solvents such as ethyl acetate, butyl a
  • the solvent which can be used is not restricted to these, You may mix and use 2 or more types of these as a solvent.
  • organic EL material preferable examples are different depending on each functional layer material.
  • a good solvent for example, an aromatic solvent, a halogen solvent, an ether solvent, and the like are preferable.
  • the poor solvent include alcohol solvents, ketone solvents, paraffin solvents, and the like. Among them, alcohol solvents and paraffin solvents are used.
  • an organic compound having a reactive group may be used in each functional layer.
  • an organic compound having a reactive group may be used in each functional layer.
  • An organic material having a function having a reactive group in each functional layer may be used.
  • the reactive organic compound coating layer After forming the reactive organic compound coating layer, it can be reacted on the substrate to form a network polymer of organic molecules and be cured.
  • production of a network polymer can suppress element deterioration by Tg (glass transition point) adjustment of a structure layer.
  • the lower layer does not dissolve in the upper layer coating solution. Therefore, the upper layer can be applied by resinating the lower layer and degrading solvent solubility. be able to.
  • the hole transport layer is resinized as an organic layer thus crosslinked, dissolution and penetration of the lower layer can be prevented when the light emitting layer is applied as the upper layer.
  • the reactive group that can be used is not particularly limited, but typically includes a vinyl group, an ethynyl group, an isocyanate group, an epoxy group, and the like.
  • a conductive material used for the anode for injecting holes which is the first electrode, is preferably a material having a work function larger than 4 eV, and is silver, gold, platinum, palladium. And their alloys, metal oxides such as tin oxide, indium oxide and ITO, and organic conductive resins such as polythiophene and polypyrrole are used. It is preferable that it is translucent, and ITO is preferable as a transparent electrode. As a method for forming the ITO transparent electrode, mask vapor deposition or photolithography patterning can be used, but is not limited thereto.
  • the conductive material used as the cathode as the second electrode those having a work function smaller than 4 eV are suitable, such as magnesium and aluminum.
  • Typical examples of the alloy include magnesium / silver and lithium / aluminum.
  • the formation method can be mask vapor deposition, photolithography patterning, plating, printing, or the like, but is not limited thereto.
  • Transparent resin films include polyethylene, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, polypropylene, polystyrene, polymethyl methacrylate, polyvinyl chloride, polyvinyl alcohol, polyvinyl butyral, nylon, polyether ether ketone.
  • gas barrier film in which a gas barrier layer is formed on these supports.
  • gas barrier layer include a thin film having a low moisture permeability made of a material having a low moisture permeability such as silicon oxide, silicon nitride, silicon oxynitride having a thickness of several nanometers to several hundred nanometers.
  • the sealing film used in the present invention is preferably a gas barrier resin film having a low moisture permeability.
  • a transparent film having a thickness of several nm to several hundreds nm is formed on the above-mentioned flexible support such as polyester such as polyethylene terephthalate, polycarbonate, polyethylene, ethylene-vinyl alcohol copolymer, and polypropylene.
  • polyester such as polyethylene terephthalate, polycarbonate, polyethylene, ethylene-vinyl alcohol copolymer, and polypropylene.
  • examples thereof include a film in which a thin film made of a material having low moisture permeability such as silicon oxide, silicon nitride, and silicon oxynitride is formed, and a film in which an alumina vapor deposition film or the like that is a gas barrier film is formed.
  • a metal vapor-deposited film such as Toppan Printing, a GX film, a silica vapor-deposited film such as Tech Barrier (Mitsubishi Resin), or the above-mentioned film on which a gas barrier layer such as an alumina vapor-deposited film is formed can be used.
  • a UV curable adhesive composition made of an acrylic resin, an epoxy resin, a fluorine resin, or the like can be used.
  • a UV resin XNR5516 manufactured by Nagase Chemtech Co., Ltd. UV curable adhesive (resin) can be used.
  • a heat bonding resin may be used.
  • a polyethylene terephthalate film (PET film) having a width of 700 mm and a thickness of 100 ⁇ m was prepared, and a low-density layer made of silicon oxide having a total film thickness of about 90 nm on the prepared PET film by an atmospheric pressure plasma discharge treatment method.
  • a transparent gas barrier film in which four layers of medium density layer, high density layer, and medium density layer were laminated was prepared.
  • oxygen permeability by a method based on JIS K 7126-1987 it was 1.0 ⁇ 10 ⁇ 3 cm 3 / (m 2 ⁇ 24 hr ⁇ MPa) or less.
  • an original winding was introduced into a roll-to-roll vacuum chamber, and an ITO film was formed to a thickness of 130 nm in an argon atmosphere to form a transparent conductive film.
  • the surface resistivity of the ITO film was 40 ⁇ / ⁇ .
  • a photolithographic resin that is polymerized with ultraviolet light is applied to a rectangular region with a width direction of 670 mm and a longitudinal direction of 720 mm, and after passing through a drying oven at 90 ° C., After aligning the position and exposing the pattern, it was developed, etched, and subjected to alkali treatment while being transported, washed with ion-exchanged water, sprayed with clean air, sufficiently dried, and then wound up.
  • an organic functional layer was applied to a roll-shaped PET film obtained by winding the PET film on which the electrode pattern was produced as follows.
  • a hole transport layer was formed in the hole transport layer forming step 4.
  • Polyethylene dioxythiophene / polystyrene sulfonate (PEDOT / PSS, Baytron P AI4083 manufactured by Bayer) diluted with 65% pure water and 5% methanol for the hole transport layer forming coating solution for forming the hole transport layer Prepared as a coating solution.
  • the surface tension of the coating solution for forming the hole transport layer was 40 mN / m (manufactured by Kyowa Interface Chemical Co., Ltd .: surface tension meter CBVP-A3).
  • the roll-shaped PET film on which the prepared first electrode is formed is subjected to a charge removal treatment, and then the hole transport layer forming coating solution is applied to the PET film at a temperature of 25 ° C. using a die coat type coating machine.
  • the wet coating method was applied so that the thickness after drying was 30 nm.
  • a drying device and a heat treatment device are used.
  • the height from the slit nozzle type discharge port to the film formation surface is 100 mm
  • the discharge air speed is 1 m / s
  • the wide air speed distribution is 5%
  • the temperature is 120 ° C.
  • heat treatment by a back surface heat transfer method was performed at a temperature of 150 ° C. by a heat treatment apparatus to form a hole transport layer.
  • the conveyance speed was 3 m / min.
  • a light emitting layer was formed.
  • a light emitting layer forming coating solution 1% by mass of host dicarbazole derivative (CBP) and 0.05% by mass of dopant iridium complex (Ir (ppy) 3 ) with respect to toluene as solvent What was dissolved was prepared as a coating solution.
  • the surface tension of the coating solution for forming the light emitting layer was 28 mN / m at 25 ° C. (manufactured by Kyowa Interface Chemical Co., Ltd .: using surface tension meter CBVP-A3).
  • the light emitting layer forming coating solution is formed on the PET film at a temperature of 25 ° C., similar to the hole transport layer forming step. It apply
  • a heat treatment of the backside heat transfer method was subsequently performed at a temperature of 150 ° C. by a heat treatment apparatus to form a light emitting layer.
  • a coating solution for forming an electron transport layer 2- (4-biphenylyl) -5- (pt-butylphenyl) -1,3,4-oxadiazole (t-Bu--) with respect to ethyl lactate as a solvent. What dissolved PBD) at 1 mass% was prepared as a coating liquid.
  • the surface tension of the coating solution for forming an electron transport layer was 29 mN / m at 25 ° C. (manufactured by Kyowa Interface Chemical Co., Ltd .: using a surface tension meter CBVP-A3).
  • the electron transport layer forming coating solution is formed on the PET film at a temperature of 25 ° C. in the same die coating method as in the hole transport layer forming step. It applied so that a dry film thickness might be set to 30 nm by the wet application method using the applicator of No.1.
  • drying equipment and heat treatment equipment used for drying and heat treatment of the hole transport layer coating film, and the drying equipment discharges 100mm from the slit nozzle type discharge port to the film formation surface.
  • a back heat transfer type heat treatment was subsequently performed at a temperature of 150 ° C. by a heat treatment apparatus to form an electron transport layer.
  • the unnecessary portion of the formed organic functional layer is wiped off using a wiping apparatus described in, for example, JP-T-2007-515756 using a solvent (for example, acetone) that can dissolve each layer.
  • a solvent for example, acetone
  • the PET film in which each layer of the organic functional layer was patterned in the winding part 7 was wound around a winding core with the electron transport layer side inside, and wound as a roll film.
  • a side tape having a thickness of 500 ⁇ m was wound around both ends of the belt-like flexible support other than the organic functional layer forming portion, and wound in a non-contact manner so as to form a space in the intermediate organic functional layer forming portion.
  • the supply unit 8 joins the roll tip of the PET film formed up to the electron transport layer to the end of the leader arranged in the process, and unwinds the electron injection layer. Then, the second electrode and the like were laminated and wound up as a roll-shaped film once around the winding core with the second electrode side inside. At this time, the original winding of the side tape is supplied to the winding unit 11, and a side tape having a thickness of 500 ⁇ m is wound around both ends of the belt-like flexible support other than the organic functional layer forming unit, and the intermediate organic functional layer forming unit is inserted. It wound up non-contactingly so that a space might be formed.
  • the roll of PET film formed from the supply unit 8 to the electron transport layer was unwound, and the electron injection layer was formed by mask vapor deposition.
  • layer formation was performed by changing the moisture partial pressure in the film forming chamber as shown in Table 1.
  • the moisture partial pressure was measured using a ULVAC small partial pressure monitor MALIN (model MA-01).
  • the moisture partial pressure change in the film formation chamber was changed by drying the PET film, leader, and side tape formed up to the electron transport layer to be input into the film formation chamber in advance before entering the film formation chamber. .
  • lithium fluoride (0.5 nm) is mask-deposited in the electron injection layer forming step 9, and aluminum is further mask-deposited in a second vacuum film forming chamber constituting the second electrode forming step 10 in the subsequent stage.
  • the PET film in which the second electrode was patterned in the winding part 11 was wound around a winding core with the second electrode side facing outside, and was wound up as a roll film.
  • a leader made of a PET film was joined to the end of the PET film, and the leader was placed in the process by cutting the leading end of the leader after winding.
  • a gas barrier layer (90 nm silicon oxide layer) coated with 40 ⁇ m of a sealing resin (adhesive) is formed in the laminating chamber constituting the roll-out of the PET film from the supply unit 12 and the sealing layer forming step.
  • Lamination was performed by thermocompression bonding using a used PET film (PET thickness of 80 microns) under a pressure of 0.1 MPa in a nitrogen stream at atmospheric pressure, followed by main curing.
  • unwinding of the roll of PET film from the supply unit 12 and winding after lamination are linked to this, and the alignment mark attached to the PET is detected by using the punching device 14a in the cutting process. Cut and punched according to the position.
  • the organic EL element schematically shown in FIG. 3 is obtained.
  • FIG. 1 An example of a punched device is shown schematically in FIG.
  • 101 is a substrate made of PET film
  • 102 is a first electrode made of ITO
  • 102a is a first electrode extraction electrode
  • 103 to 105 are a hole transport layer, a light emitting layer, an electron transport layer
  • An organic layer made of a hole injection layer
  • 106 a a take-out electrode for the second electrode
  • 108 an adhesive layer 109 a sealing film (PET film on which a gas barrier layer has been formed) is there.
  • PET film on which a gas barrier layer has been formed is there.
  • the organic EL element sealed on the long PET film was formed by roll-to-roll, and the effectiveness of the present invention was confirmed.
  • an organic EL element is obtained by mounting a power supply circuit.
  • the average value of the light-emitting elements was used as the drive voltage for each element, and the ratio of the element 4 to the drive voltage was determined and evaluated using the following indices. ⁇ or more is preferable, and ⁇ or more is more preferable.
  • A No dark spots are generated.
  • O One or more dark spots and less than five.
  • ⁇ Five or more dark spots and less than ten.
  • X Ten or more dark spots.
  • Example 2 In the manufacturing apparatus 2b used in Example 1, the roll 7a of the strip-shaped flexible support B wound around the supply unit 8 together with the side tape 7c having different moisture content and the side having different moisture content on the winding unit 11 are used.
  • the tape 11c was supplied, the time change until the water partial pressure reached 5 ⁇ 10 ⁇ 5 Pa was measured in the electron injection layer forming step 9 and the second electrode forming step 10, and the results are shown in Table 2.

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  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

<span lang=FR style='font-family:"Courier New"'>La présente invention concerne un procédé de production d'un élément électroluminescent organique qui comprend une étape de formation d'un film sous vide à l'aide d'un film flexible et qui peut améliorer la tension d'attaque, l'apparition de points noirs ou similaires, les propriétés électroluminescentes et la durée de vie de l'élément électroluminescent organique. Plus spécifiquement, l'invention concerne un procédé de production d'un élément électroluminescent organique qui comprend au moins une étape de formation d'une première électrode, d'une couche fonctionnelle organique comprenant une couche électroluminescente et d'une seconde électrode, dans cet ordre, sur un film flexible (matériau de base longitudinal) et qui utilise au moins un film d'amorce ou une bande latérale. Le procédé est caractérisé en ce que l'étape comprend une étape de formation de film sous vide à l'aide d'un appareil de formation de film sous vide, le film flexible étant introduit dans l'appareil de formation de film sous vide et au moins soit le film d'amorce, soit la bande latérale étant séché avant l'introduction dans l'appareil de formation de film sous vide. L'étape de formation du film sous vide est exécutée à une pression partielle d'eau de 5 </span>× 10-5 Pa ou moins.
PCT/JP2011/064373 2010-07-16 2011-06-23 Procédé de production d'un élément électroluminescent organique Ceased WO2012008275A1 (fr)

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