EP0897652A1 - Complexes organometalliques destines a etre utilises dans des dispositifs electroluminescents - Google Patents

Complexes organometalliques destines a etre utilises dans des dispositifs electroluminescents

Info

Publication number
EP0897652A1
EP0897652A1 EP97930874A EP97930874A EP0897652A1 EP 0897652 A1 EP0897652 A1 EP 0897652A1 EP 97930874 A EP97930874 A EP 97930874A EP 97930874 A EP97930874 A EP 97930874A EP 0897652 A1 EP0897652 A1 EP 0897652A1
Authority
EP
European Patent Office
Prior art keywords
organic
layer
transporting layer
electron transporting
compound
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.)
Withdrawn
Application number
EP97930874A
Other languages
German (de)
English (en)
Inventor
Sewhan Son
Kong Keum Kim
Hyo-Seok Kim
Okhee Kim
Seokhee Yoon
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LG Corp
Original Assignee
LG Chemical Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by LG Chemical Co Ltd filed Critical LG Chemical Co Ltd
Publication of EP0897652A1 publication Critical patent/EP0897652A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source

Definitions

  • the present invention relates to an electron injecting material for use in organic electroluminescence devices. More particularly, the present invention relates to an electron injecting material, being capable of driving with a lower drive voltage and having an improved efficiency in power conversion, for use in an organic electroluminescent device.
  • the organic electroluminescent device in accordance with the present invention comprises an anode electrode, a cathode electrode, and an organic film layer formed between the anode and cathode electrodes, wherein the organic film layer is made of a 2-(0-hydroxyphenyl)benzthiazole beryllium complex.
  • EL device organic electroluminescence device
  • the organic dye molecules should have the capability of accepting carriers from the electrodes and the high mobility of the carriers inside the electroluminescent layer.
  • the recombination zone of the carriers should be located away from the electrodes to prevent occurrences of exciton quenching by the metallic electrodes.
  • U.S. Patent No. 4,539,507 granted to Steven A. VanSlyke et al., issued on Sep. 3, 1985 teaches a device having two layers which comprises in the order of anode/hole transporting layer/electron transporting layer/cathode.
  • a triphenylamine-containing compound and an aluminum complex of 8-hydroxyquinoline are used as the hole transporting material and the electron transporting material respectively, wherein the latter also functions as an emitting layer of the device. Facile injection of carriers and high mobility of holes and electrons in the two-layer EL device makes the driving voltage to be lowered.
  • the power conversion efficiency of the organic EL device has improved up to 1.5 lm/W and hundreds of cd/m in brightness thereof has been obtained at a voltage of less than 10 V.
  • U.S. Patent No. 4,539,507 also teaches an organic EL device having an improved durability and a higher efficiency than the two-layer device, being fabricated by interposing a hole injecting layer containing a metal phthalocyanine between an anode and a hole transporting layer. Enhancing the carrier injection is therefore considered one of the important factors for the improvement of EL devices.
  • the adhesive layer is composed of a metal complex of 8-hydroxyquinoline or a derivative thereof which is contaminated by adding a small amount of additional compounds to prevent it from crystallization. Therefore the morphologically stabilized adhesive layer provides the device with a uniform light emission and durability thereof.
  • the energy level of the lowest unoccupied molecular orbital (hereinafter referred to as "LUMO") of the metal complex of 8-hydroxyquinoline is located below that of another emissive molecules which are in contact with the adhesive layer in a device comprising in the order of anode/hole injecting layer/hole transporting layer/emitting layer/adhesive layer/cathode to ensure the facile electron injection from the cathode.
  • LUMO lowest unoccupied molecular orbital
  • the objective of the present invention is to provide an electron injecting material having a low drive voltage and an improved power conversion efficiency for organic electroluminescene (EL) devices.
  • EL organic electroluminescene
  • Ri to Rs represent hydrogen or Ci to C 8 alkyl groups, independently.
  • a zinc derivative of compound (1), 2-(O-hydroxyphenyl)benzthiazole zinc complex, has been known as a blue light emitting electron transporting material (see European. Pat. Publication No. 0652273 and Japanese Patent Application Laid-Open No. 113576/1996).
  • the present inventors discovered that the compounds represented by the above general formula (1) show excellent electron injection and transport properties which have not been found in the aforementioned patents.
  • FIGS. 1 to 3 are schematic diagrams of organic EL devices where the present invention can be used.
  • FIG. 4 is a graph showing a relationship of light intensity (arbitrary unit) vs. voltage respectively in Example 1, Comparative Example 1.1 and Comparative Example 1.2.
  • FIG. 5 is a graph showing a relationship of light intensity (arbitrary unit) vs. voltage respectively in Example 2 and Comparative Example 2.
  • the use of stable cathode having a low work function is a critical factor to commercialize an efficient EL device. Since the LUMO level of the conventional electron injecting layer (a layer being located in contact with a cathode) does not match with the work function of the cathode material, a significant high energy barrier exists when injecting electrons from the cathode into the organic medium. For example, an energy barrier of about 0.6 eV exists when injecting electrons from a Mg:Ag alloy into 8-hydroxyqunoline aluminum salt (hereinafter referred to as Alq3) which is one of the most widely used electron injecting layers in an EL device.
  • Alq3 8-hydroxyqunoline aluminum salt
  • the present invention is based on a discovery that a complex represented by the above formula (1) can provide an EL device with both a high power efficiency and a low driving- voltage when it is interposed as a thin layer between a cathode electrode and the hole-transporting layer of a conventional EL device.
  • FIGS. 1 to 3 show a respective schematic cross section of internal junction organic EL devices. These devices generally comprise a transparent support layer 1 onto which an anode electrode 2 having a high work function is coated. Specific examples of a conductive material for the anode electrode 2 may include Au, Indium Tin Oxide (ITO), Sn0 2 , conducting polymers and ZnO 2 .
  • ITO Indium Tin Oxide
  • Sn0 2 conducting polymers
  • ZnO 2 ZnO 2
  • a cathode electrode 7 is formed by way of a method of vapor deposition or sputtering of electrically conductive material with a low work function.
  • the cathode electrode 7 may be made of a material selected from the group of aluminum, silver, magnesium, lithium, samarium, indium, tin, lead, yttrium, ruthenium and alloys of these (see U.S. Pat. No. 4,885,211; U.S. Pat. No. 4,539,507; U.S. Pat. No. 5,059,862; U.S. Pat. No. 5,429,844; and U.S. Pat. No. 5,500,568), but not limited thereto.
  • a hole transporting layer 3 is made of a material, which is capable of accepting holes from the anode electrode 2 and transporting them with high mobility, preferably a derivative of aryl amine or a mixture of at least two aryl amines with different molecular structure to suppress possible crystallization and to improve the performance of EL devices. Also the hole transporting layer 3 can be divided into multiple sub-layers each of which is made of different hole transporting material.
  • An electron transporting layer 4 is made of a material, which is capable of accepting electrons from the cathode electrode 7 and transporting them. As shown in FIG. 1, the electron transporting layer 4 is located between the cathode electrode 7 and the hole transporting layer 3.
  • FIGS. 2 and 3 are a respective schematic cross section of organic EL devices having a hole injecting layer 5 sandwiched between an anode electrode 2 and a hole transporting layer 3 to enhance the injection of holes from the anode electrode 2 into the hole transporting layer 3 and to improve the lifetime of the organic EL devices as well.
  • the hole injecting layer 5 is made of a material having ability of forming a stable interface with both the anode electrode 2 and the hole transporting layer 3. Also it is preferable that the hole injecting material has an energy level of the highest occupied molecular orbital (HOMO) in between the work function of the anode and the HOMO level of the hole transporting material (see U.S. Pat. No. 4,539,507 and U.S. Pat. No. 4,769,292).
  • HOMO highest occupied molecular orbital
  • the electron transporting layer 4 is made of a material capable of accepting electrons from the cathode electrode 7, upon application of an appropriate forward bias, and transporting them and is located between the cathode electrode 7 and the hole transporting layer 3.
  • the recombination of carriers generally takes place, but not necessarily, in the electron transporting layer 4, and it is preferable to select the electron transporting material among molecules having a high fluorescent quantum efficiency.
  • highly fluorescent materials may be doped into the electron transporting layer 4 with a low concentration.
  • the band gap of the dopant material there are two important requirements such as the band gap of the dopant material and the location of it in the electron transporting layer 4 in the direction of thickness. If the band gap of the dopant material is larger than that of electron transporting material 4, effective energy transfer cannot be obtained. Therefore it is preferable to select a dopant material with a band gap similar to or lower than that of the electron transporting material.
  • Another requirement, i.e., the location of the doped region, should be fulfilled to maximize the power conversion efficiency of organic EL devices. If the LUMO level of the dopant is lower than that of the electron transporting layer 4, the dopant acts as a shallow trap of electrons. Since the shallow trap increases a space charge density, a higher voltage is required to drive the EL devices. Therefore it is preferable to locate the doped region in the direction of thickness where the exiton formation takes place.
  • FIG. 3 schematically illustrates an organic EL device fabricated by interposing a light emitting layer 6 between the electron transporting layer 4 and the hole transporting layer 3 based on an organic EL device as shown in FIG. 2 (see U.S. Pat. No. 4,539,507).
  • this device according to the inventors of above U.S. patent, it is desirable that the thickness of the electron transporting layer 4 is smaller than that of the light emitting layer 6 to minimize the possibility of light emission from the electron transporting layer 4 which has a band gap (energy gap) smaller than that of the light emitting layer 6.
  • the present invention relates to an organic EL device having a low drive voltage and an improved power conversion efficiency. Electron injecting materials of the present invention are represented by the following formula (1):
  • Ri to Rs represent hydrogen or C ⁇ to C 8 alkyl groups, independently.
  • Specific examples of the electron injecting materials of the present invention are represented by the following formula (2) and (3):
  • the energy gap of compound (2) obtained from the wavelength of absorption ends of abso ⁇ tion spectrum ranging from UV light to visible light of a thin film corresponds to 2.82 eV.
  • the emission color is found to be blue (CIE 0.138, 0.149). Therefore the compound (2) is an excellent candidate material for the electron transporting layer 4 and the light emitting layer 6 for emitting blue color.
  • this material expands the possible choice of the dopant material having a band gap energy corresponding to a color range from blue to red compared with that from green to red when Alq3 is used as an electron transporting/host molecule which has a band gap energy corresponding to green color.
  • the compound (2) should meet other requirements such as thermal stability, electrochemical stability, electron accepting ability (low LUMO energy level) and so on. According to a DSC thermogram, compound (2) melts at the onset temperature of 325 °C which is high enough for practical use.
  • TABLE 1 The physical properties described above of the compound (2) are summarized in TABLE 1.
  • the yielded product was further purified by train sublimation.
  • the results of analyzing the product are given as follows: m.p.: 325 °C (onset).
  • compound (2) as an electron injecting material was measured using cyclic voltammeter by comparing its reduction potential with known electron transporting materials.
  • the reference compounds used in this set of experiments is Alq3.
  • organic EL devices were fabricated with and without compound (2) as follows.
  • Commercially available ITO coated glass was subjected to ultrasonic cleaning with methanol, acetone, isopropyl alcohol, acetone and methanol in success for 5 minutes in each solvent, and dried in a vacuum oven for 1 hour at 110 ° C.
  • the cleaned substrate was fixed on a substrate holder in a thermal vacuum deposition chamber.
  • An organic EL device which comprises laminating layers in the order of ITO/TPD/Alq3/compound (2)/Mg:Ag (10:l)/Ag with a film thickness of 60 nm (TPD), 50 nm (Alq3), 20 nm (compound (2)), 100 nm (Mg:Ag) and 150 nm (Ag) respectively (TPD: N, N-diphenyl-N, N-bis(3-methylphenyl)-[l, l-biphenyl]-4, 4-diamine).
  • the deposition rate was maintained in a range of 1 ⁇ 3 A/sec in a high vacuum of about 10 "6 torr with a substrate temperature set at room temperature.
  • a shadow mask was used for the patterning of the cathode electrode to make 0.15 cm of active device area.
  • the schematic cross section of this organic EL device is analogous to the device described in FIG. 1 except that the former has an additional layer made of compound (2) inbetween the electron transporting layer 4 and the cathode electrode 7.
  • An organic EL device which comprises laminating layers in the order of ITO/TPD/Alq3/Mg:Ag(10:l)/Ag was obtained in the same manner as in EXAMPLE 1 except that the electron injecting material (2) was excluded.
  • the schematic cross section of this organic EL device is described in FIG. 1.
  • the power conversion efficiency of this device was 1.2 lm/W at the brightness of 100 cd/m . 1 mA/cm 2 of current density was injected at 9.1 V. The results are summarized in TABLE 3.
  • An organic EL device which comprises laminating layers in the order of ITO/TPD/Alq3/2-(0-hydroxyphenyl)benzthiazole zinc complex/Mg:Ag(10:l)/Ag was obtained in the same manner as in EXAMPLE 1 except that the electron injecting material (2) was replaced with the zinc complex of material (2) with the same thickness as the compound (1).
  • the schematic cross section of this organic EL device is analogous to a device described in FIG. 1 except that the former has an additional layer made of 2-(O-hydroxyphenyl)benzthiazole zinc complex inbetween the electron transporting layer 4 and the cathode electrode 7.
  • the power conversion efficiency of this device was 1.6 lm/W at the brightness of 100 cd/m 2 . 1 mA/cm 2 of current density was injected at 8.4 V. The results are summarized in TABLE 3.
  • An organic EL device which comprises laminating layers in the order of ITO/TPD/Alq3/compound (2)/Ag was obtained in the same manner as in EXAMPLE 1 with a film thickness of 60 nm (TPD), 20 nm (Alq3), 50 nm (compound (2)), and 200 nm (Ag) respectively.
  • TPD 60 nm
  • Alq3 20 nm
  • compound (2) 50 nm
  • Ag electron injecting/transporting material
  • low work function magnesium silver (Mg:Ag) alloy was replaced with the high work function silver (Ag) electrode.
  • the schematic cross section of this organic EL device is analogous to a device depicted in FIG.
  • An organic EL device which comprises laminating layers in the order of ITO/TPD/Alq3/2-(0-hydroxyphenyl)benzthiazole zinc complex/Ag was obtained in the same manner as in EXAMPLE 1 with a film thickness of 60 nm (TPD), 20 nm (Alq3), 50 nm (2-(0-hydroxyphenyl)benzthiazole zinc complex), and 200 nm (Ag) respectively.
  • TPD 60 nm
  • Alq3 20 nm
  • 200 nm (Ag) respectively.
  • Alq3 was used as light emitting material
  • the 2-(0-hydroxyphenyl)benzthiazole zinc complex as an electron injecting/transporting material.
  • a low work function magnesium silver alloy was replaced with a high work function silver electrode.
  • FIG. 5 which depicts a graph of plotted light intensities (arbitrary unit) at various voltages from devices used for EXAMPLE 2 and Comparative Example 2 clearly illustrates the performance of compound (2) superior to its zinc analogue. At the same voltage, the device in EXAMPLE 2 gives off much higher light intensity compared with that in Comparative Example 2.
  • An organic EL device which comprises laminating layers in the order of ITO/TPD/compound (2): coumarine 540(100:l)/Mg:Ag/Ag was obtained in the same manner as in EXAMPLE 1 with a film thickness of 60 nm (TPD), 50 nm (compound (2): coumarine 540), 100 nm (Mg:Ag) and 150 nm (Ag) respectively.
  • coumarine 540 was used as a dopant molecule and compound (2) as a host molecule with the role of electron injecting and transporting at the same time.
  • the chemical structure of coumarine 540 is illustrated below and the schematic cross section of this organic EL device is illustrated in FIG. 1.
  • An organic EL device which comprises laminating layers in the order of ITO/TPD/Alq3:coumarine 540(100:l)/Mg:Ag/Ag was obtained in the same manner as in EXAMPLE 3 with a film thickness of 60 nm (TPD), 50 nm (compound (2): coumarine 540), 100 nm (Mg:Ag) and 150 nm (Ag) respectively.
  • coumarine 540 was used as a dopant molecule and Alq3 as a host molecule with the role of electron injecting and transporting at the same time.
  • the schematic cross section of this organic EL device is illustrated in FIG. 1. The results are summarized in TABLE 5.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

Matière à injection d'électrons, capable d'excitation à l'aide d'une tension d'excitation plus faible et présentant une meilleure efficacité de conversion de puissance, destinée à être utilisée dans un dispositif électroluminescent organique. Pour répondre aux caractéristiques techniques de la présente invention, ledit dispositif comprend une électrode anode, une électrode cathode et un film organique placé entre les électrodes, ledit film organique étant constitué d'un complexe organométallique de formule (1) dans laquelle R1 à R8 sont indépendamment hydrogène ou des groupes alkyle C1 à C8.
EP97930874A 1997-02-22 1997-07-08 Complexes organometalliques destines a etre utilises dans des dispositifs electroluminescents Withdrawn EP0897652A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
KR19970005406 1997-02-22
KR1997540 1997-02-22
PCT/KR1997/000134 WO1998037736A1 (fr) 1997-02-22 1997-07-08 Complexes organometalliques destines a etre utilises dans des dispositifs electroluminescents

Publications (1)

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EP0897652A1 true EP0897652A1 (fr) 1999-02-24

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EP97930874A Withdrawn EP0897652A1 (fr) 1997-02-22 1997-07-08 Complexes organometalliques destines a etre utilises dans des dispositifs electroluminescents

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EP (1) EP0897652A1 (fr)
JP (1) JP2000515926A (fr)
KR (1) KR100259398B1 (fr)
TW (1) TW373211B (fr)
WO (1) WO1998037736A1 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6558817B1 (en) * 1998-09-09 2003-05-06 Minolta Co., Ltd. Organic electroluminescent element
KR100373203B1 (ko) * 1999-03-31 2003-02-25 주식회사 엘지화학 새로운 큐마린계 착물 및 이를 이용한 유기 발광 소자
AU2003230308A1 (en) 2002-05-07 2003-11-11 Lg Chem, Ltd. New organic compounds for electroluminescence and organic electroluminescent devices using the same
TWI468490B (zh) 2007-07-24 2015-01-11 Gracel Display Inc 新穎紅色電場發光化合物及使用該化合物之有機電場發光裝置
KR100970713B1 (ko) * 2007-12-31 2010-07-16 다우어드밴스드디스플레이머티리얼 유한회사 유기발광화합물을 발광재료로서 채용하고 있는 전기 발광소자
KR101294620B1 (ko) * 2010-06-07 2013-08-07 롬엔드하스전자재료코리아유한회사 유기발광화합물을 발광재료로서 채용하고 있는 전기 발광 소자
JP6115395B2 (ja) * 2013-08-14 2017-04-19 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子用金属錯体、並びに表示装置及び照明装置

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Publication number Priority date Publication date Assignee Title
US5529853A (en) * 1993-03-17 1996-06-25 Sanyo Electric Co., Ltd. Organic electroluminescent element
JPH07133483A (ja) * 1993-11-09 1995-05-23 Shinko Electric Ind Co Ltd Ｅｌ素子用有機発光材料及びｅｌ素子
US5486406A (en) * 1994-11-07 1996-01-23 Motorola Green-emitting organometallic complexes for use in light emitting devices

Non-Patent Citations (1)

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Title
See references of WO9837736A1 *

Also Published As

Publication number Publication date
TW373211B (en) 1999-11-01
WO1998037736A1 (fr) 1998-08-27
JP2000515926A (ja) 2000-11-28
KR19980071472A (ko) 1998-10-26
KR100259398B1 (ko) 2000-06-15

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