WO2010107244A2 - Composés organiques électroluminescents innovants et dispositif organique électroluminescent les utilisant - Google Patents

Composés organiques électroluminescents innovants et dispositif organique électroluminescent les utilisant Download PDF

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WO2010107244A2
WO2010107244A2 PCT/KR2010/001647 KR2010001647W WO2010107244A2 WO 2010107244 A2 WO2010107244 A2 WO 2010107244A2 KR 2010001647 W KR2010001647 W KR 2010001647W WO 2010107244 A2 WO2010107244 A2 WO 2010107244A2
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organic electroluminescent
compound
alkyl
mmol
mono
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PCT/KR2010/001647
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WO2010107244A3 (fr
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Chi Sik Kim
Young Jun Cho
Hyuck Joo Kwon
Bong Ok Kim
Sung Min Kim
Seung Soo Yoon
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Dow Advanced Display Materials, Ltd.
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Priority to CN2010800224996A priority Critical patent/CN102482571A/zh
Priority to JP2012500717A priority patent/JP2012520872A/ja
Publication of WO2010107244A2 publication Critical patent/WO2010107244A2/fr
Publication of WO2010107244A3 publication Critical patent/WO2010107244A3/fr

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Definitions

  • the present invention relates to novel organic electroluminescent compounds and organic electroluminescent devices comprising the same. Specifically, it relates to novel organic electroluminescent compounds employed as electroluminescent material, and organic electroluminescent devices using them as a host.
  • OLED organic light-emitting diode
  • electroluminescent material The most important factor to determine luminous efficiency of an OLED (organic light-emitting diode) is the type of electroluminescent material. Though fluorescent materials has been widely used as an electroluminescent material up to the present, development of phosphorescent materials is one of the best methods to improve the luminous efficiency theoretically up to four(4) times, in view of electroluminescent mechanism.
  • iridium (III) complexes are widely known as phosphorescent material, including (acac)Ir(btp) 2 , Ir(ppy) 3 and Firpic, as the red, green and blue one, respectively.
  • phosphorescent material including (acac)Ir(btp) 2 , Ir(ppy) 3 and Firpic, as the red, green and blue one, respectively.
  • a lot of phosphorescent materials have been recently investigated in Japan, Europe and America.
  • CBP 4,4'-N,N'-dicarbazole-biphenyl
  • the materials in prior art are advantageous in view of light emitting property, they have low glass transition temperature and very poor thermal stability, so that the materials tend to be changed during the process vapor-deposition in vacuo at high temperature.
  • power efficiency ( ⁇ /voltage) x current efficiency.
  • the power efficiency is inversely proportional to the voltage, and the power efficiency should be higher in order to obtain lower power consumption of an OLED.
  • an OLED employing phosphorescent electroluminescent material shows significantly higher current efficiency (cd/A) than an OLED employing fluorescent EL material.
  • the present inventors endeavored to overcome the problems of conventional techniques, and consequently invented novel electroluminescent compounds to realize organic electroluminescent devices having excellent luminous efficiency and remarkably lengthened device life.
  • the object of the invention is to overcome those problems and to provide organic electroluminescent compounds comprising a backbone to result in better luminous efficiency, improved device life, and appropriate color coordinate, as compared to conventional host materials.
  • Another object of the invention is to provide organic electroluminescent devices having high efficiency and long life, which employ such organic electroluminescent compounds as electroluminescent material.
  • the present invention relates to organic electroluminescent compounds represented by one of Chemical Formulas (1) to (5), and organic electroluminescent devices comprising the same. Since the organic electroluminescent compounds according to the present invention provide better luminous efficiency and excellent life property as compared to conventional host material, OLED's having excellent operation life can be obtained therefrom.
  • X and Y are independently selected from N(Ar 1 ), O and S, wherein Ar 1 may be different from one another, and Ar 1 may be represented as Ar 1 or Ar 2 where there are two or more Ar 1 groups;
  • Z 1 through Z 8 are independently selected from C(Ar 3 ) and N, wherein Ar 3 may be different from one another, and adjacent Ar 3 groups may be linked together to form a ring;
  • Ar 1 and Ar 2 are independently selected from (C1-C60)alkyl, (C3-C60)cycloalkyl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O, S, Si and P, (C7-C60)bicycloalkyl, adamantyl, (C2-C60)alkenyl, (C2-C60)alkynyl, (C6-C60)aryl and (C3-C60)heteroaryl;
  • Ar 3 are independently selected from hydrogen, (C1-C60)alkyl, halogen, cyano, (C3-C60)cycloalkyl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O, S, Si and P, (C7-C60)bicycloalkyl, adamantyl, (C2-C60)alkenyl, (C2-C60)alkynyl, (C6-C60)aryl, (C1-C60)alkoxy, (C6-C60)aryloxy, (C3-C60)heteroaryl, (C6-C60)arylthio, (C1-C60)alkylthio, mono- or di(C1-C30)alkylamino, mono- or di(C6-C30)arylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)
  • alkyl, cycloalkyl, heterocycloalkyl, bicycloalkyl, adamantyl, alkenyl, alkynyl, aryl, alkoxy, aryloxy, heteroaryl, arylthio, alkylthio, alkylamino, arylamino, trialkylsilyl, dialkylarylsilyl, triarylsilyl, arylboranyl or alkylboranyl of Ar 1 through Ar 3 may be further substituted by one or more substituent(s) selected from a group consisting of (C1-C60)alkyl, halogen, cyano, (C3-C60)cycloalkyl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O, S, Si and P, (C7-C60)bicycloalkyl, adamantyl, (C2-C60)alkenyl, (C2-C60)alkyn
  • the substituents, as described here, which comprises "(C1-C60)alkyl” moiety may contain from 1 to 60 carbon atoms, from 1 to 20 carbon atoms, or from 1 to 10 carbon atoms.
  • the substituents comprising "(C6-C60)aryl” moiety may contain from 6 to 60 carbon atoms, from 6 to 20 carbon atoms, or from 6 to 12 carbon atoms.
  • Those comprising "(C3-C60)heteroaryl” moiety may contain from 3 to 60 carbon atoms, from 4 to 20 carbon atoms, or from 4 to 12 carbon atoms.
  • Those comprising "(C3-C60)cycloalkyl” moiety may contain from 3 to 60 carbon atoms, from 3 to 20 carbon atoms, or from 3 to 7 carbon atoms.
  • the substituents comprising "(C2-C60)alkenyl or alkynyl” moiety may contain from 2 to 60 carbon atoms, from 2 to 20 carbon atoms, or from 2 to 10 carbon atoms.
  • alkyl' of the present invention include linear or branched saturated monovalent hydrocarbon radicals or combinations thereof, which are composed only of carbon atoms and hydrogen atoms.
  • 'alkoxy' means -O-alkyl group, in which alkyl is defined as above.
  • aryl represents an organic radical derived from aromatic hydrocarbon by deleting one hydrogen atom therefrom.
  • Aryl groups include monocyclic and fused ring system, each ring of which suitably contains from 4 to 7, preferably from 5 or 6 cyclic atoms. Structures wherein two or more aryl groups are combined through chemical bond(s) are also included. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphtacenyl, fluoranthenyl and the like, but are not restricted thereto.
  • heteroaryl means an aryl group containing from 1 to 4 heteroatom(s) selected from N, O and S for the aromatic cyclic backbone atoms, and carbon atom(s) for remaining aromatic cyclic backbone atoms.
  • the heteroaryl may be a 5- or 6-membered monocyclic heteroaryl or a polycyclic heteroaryl which is fused with one or more benzene ring(s), and may be partially saturated.
  • the structures having one or more heteroaryl groups bonded through chemical bond(s) are also included.
  • the heteroaryl groups may include divalent aryl groups of which the heteroatoms are oxidized or quarternized to form N-oxides, quaternary salts, or the like.
  • monocyclic heteroaryl groups such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl; polycyclic heteroaryl groups such as benzofuryl, benzothienyl, isobenzofuryl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cin
  • organic electroluminescent compounds according to the invention can be exemplified by the compounds represented by one of the following chemical formulas:
  • Ar 1 and Ar 2 are defined as in Chemical Formulas (1) to (5).
  • organic electroluminescent compounds according to the present invention can be exemplified by the compounds represented by one of the following chemical formulas:
  • Ar 1 and Ar 2 are defined as in Chemical Formulas (1) to (5).
  • organic electroluminescent compounds according to the present invention can be specifically exemplified by the compounds represented by one of the following chemical formulas:
  • Ar 1 is defined as in Chemical Formulas (1) to (5).
  • Ar 1 and Ar 2 independently represent phenyl, 1-naphthyl or 2-naphthyl, or a substituent represented by one of the following chemical formulas, but they are not restricted thereto.
  • the present invention also provides an organic electroluminescent device which is comprised of a first electrode; a second electrode; and at least one organic layer(s) interposed between the first electrode and the second electrode; wherein the organic layer comprises one or more organic electroluminescent compound(s) represented by one of Chemical Formulas (1) to (5).
  • the organic electroluminescent device is characterized in that the organic layer comprises an electroluminescent layer, which comprises one or more compound(s) represented by one of Chemical Formulas (1) to (5) as electroluminescent host, and one or more phosphorescent dopant(s).
  • the dopant is not particularly restricted.
  • the organic electroluminescent device according to the invention may further comprise one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds, as well as one or more organic electroluminescent compound(s) represented by one of Chemical Formulas (1) to (5).
  • the organic layer may further comprise one or more metal(s) selected from a group consisting of organic metals of Group 1, Group 2, 4 th period and 5 th period transition metals, lanthanide metals and d-transition elements, or complex(es) thereof, as well as one or more organic electroluminescent compound(s) represented by one of Chemical Formulas (1) to (5).
  • the organic layer may comprise an electroluminescent layer and a charge generating layer.
  • the organic electroluminescent device may also comprise one or more organic electroluminescent layer(s) emitting blue, green or red light, in addition to the organic electroluminescent compound(s) as described above, to form an organic electroluminescent device emitting white light.
  • organic electroluminescent compounds according to the invention exhibit excellent luminous efficiency and very good life property of material when they are employed as host material of organic electroluminescent material of an OLED, so that OLED's having very good operation life can be manufactured therefrom.
  • Compound (A-6) (7 g, 12.33 mmol) was mixed with triethylphosphite (100 mL), and the same procedure as for synthesis of Compound (A-2) was carried out to give Compound (A-7) (4 g, 7.46 mmol, 58.33%).
  • Organic electroluminescent compounds (TA, TB and TC) were prepared according to the procedures of Preparation Examples (1)-(6).
  • the substituents (Ar 1 , Ar 2 ) of those organic electroluminescent compounds thus prepared, and 1 H NMR and MS/FAB data of the compounds are listed in Tables 1 and 2.
  • OLED devices were manufactured by using the electroluminescent compounds according to the invention.
  • a transparent electrode ITO thin film (15 ⁇ / ⁇ ) prepared from glass for OLED (produced by Samsung-Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use.
  • an ITO substrate was equipped in a substrate folder of a vacuum vapor-deposit device, and 4,4',4''-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA)(of which the chemical structure is shown below) was placed in a cell of the vacuum vapor-deposit device, which was then ventilated up to 10 -6 torr of vacuum in the chamber. Electric current was applied to the cell to evaporate 2-TNATA, thereby providing vapor-deposit of a hole injection layer having 60 nm of thickness on the ITO substrate.
  • 2-TNATA 4,4',4''-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine
  • NPB N,N'-bis( ⁇ -naphthyl)-N,N'-diphenyl-4,4'-diamine
  • a compound according to the present invention which had been purified via vacuum sublimation under 10 -6 torr (for example, Compound TA8-H4-H2), and an electroluminescent dopant (for example, compound (piq) 2 Ir(acac)) to another cell, respectively.
  • the two materials were evaporated at different rates to carry out doping in a concentration from 4 to 10 mol%, thereby vapor-depositing an electroluminescent layer having 30 nm of thickness on the hole transport layer.
  • tris(8-hydroxyquinoline)aluminum (III) (Alq) [of which the structure is shown below] was vapor-deposited as an electron transport layer with a thickness of 20 nm, and lithium quinolate (Liq) was vapor-deposited as an electron injection layer with a thickness of 1 to 2 nm. Thereafter, an Al cathode was vapor-deposited with a thickness of 150 nm by using another vacuum vapor-deposit device to manufacture an OLED.
  • OLED's were manufactured according to the same procedure as for OLED s of Examples 1 to 10, but using compounds according to the present invention (for example: Compound TA4-H4-H4) as host material, and organic iridium complex (Ir(ppy) 3 ) represented by the chemical formula below as electroluminescent dopant.
  • compounds according to the present invention for example: Compound TA4-H4-H4
  • organic iridium complex Ir(ppy) 3
  • OLED's were manufactured according to the same procedure described in Examples 1 and 11, but another cell of the vacuum vapor-deposition device was charged with bis(2-methyl-8-quinolinato)(p-phenylphenolato)aluminum (III) (BAlq), instead of the electroluminescent compound according to the invention, as host material.
  • BAlq bis(2-methyl-8-quinolinato)(p-phenylphenolato)aluminum (III)
  • the organic electroluminescent compounds developed by the present invention exhibited superior properties in terms of device performances as compared to conventional materials.
  • the compounds developed by the present invention showed excellent properties in terms of luminescent properties as compared to the conventional materials.
  • the devices manufactured according to the present invention showed excellent current properties as compared to the device of Comparative Example 1 which was manufactured with conventional material, thereby providing operation voltage lowered by 1 V or more. They also showed higher current efficiency properties of at least 1.4 folds as compared to the device of Comparative Example 1, due to the remarkably improved luminous properties.
  • the device when the compounds developed by the present invention were used as host for green electroluminescence, the device showed, due to their excellent luminous properties, far higher power efficiency of at least 1.6 folds as compared to the device of Comparative Example 2. Excellent luminous properties were confirmed as compared to the conventional materials. Particularly, the device of Example 14 was operated at a lower voltage by 2.7 V as compared to that of Comparative Example 1, and the device of Example 17 showed 5.5 V of operation voltage and 15.9 lm/W of power efficiency at 1000 cd/m 2 .
  • the devices employing the electroluminescent compounds according to the present invention as host material for emitting red or green light exhibited excellent luminous properties, with lowering the operation voltage, so that the device for emitting green light, in particular, induces increase of power efficiency by 5.1 to 7.7 lm/W to result in improvement in power consumption.

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  • Electroluminescent Light Sources (AREA)
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Abstract

La présente invention se rapporte à un composé organique électroluminescent innovant et à un dispositif organique électroluminescent l'utilisant. Quand il est utilisé comme matériau hôte du matériau organique électroluminescent d'un dispositif OLED, le composé organique électroluminescent de la présente invention démontre une efficacité lumineuse élevée et une excellente caractéristique de durée du matériau en comparaison d'un matériau hôte conventionnel. Dans ces conditions, le composé organique électroluminescent de la présente invention peut être utilisé pour fabriquer des OLED dotés d'une excellente durée de service.
PCT/KR2010/001647 2009-03-20 2010-03-17 Composés organiques électroluminescents innovants et dispositif organique électroluminescent les utilisant WO2010107244A2 (fr)

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JP2012500717A JP2012520872A (ja) 2009-03-20 2010-03-17 新規有機電界発光化合物およびこれを使用する有機電界発光素子

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KR20100105099A (ko) 2010-09-29
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