WO2009082157A2 - Dérivé d'arylamine et dispositif électroluminescent organique faisant appel à ce dérivé - Google Patents

Dérivé d'arylamine et dispositif électroluminescent organique faisant appel à ce dérivé Download PDF

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Publication number
WO2009082157A2
WO2009082157A2 PCT/KR2008/007608 KR2008007608W WO2009082157A2 WO 2009082157 A2 WO2009082157 A2 WO 2009082157A2 KR 2008007608 W KR2008007608 W KR 2008007608W WO 2009082157 A2 WO2009082157 A2 WO 2009082157A2
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WO
WIPO (PCT)
Prior art keywords
group
biphenyl
naphthyl
amine derivative
aryl amine
Prior art date
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PCT/KR2008/007608
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English (en)
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WO2009082157A3 (fr
Inventor
Jung Sub Lee
Kyoung Soo Kim
Tae Hyung Kim
Ho Cheol Park
Sang-Do Lee
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Doosan Corporation
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Publication of WO2009082157A2 publication Critical patent/WO2009082157A2/fr
Publication of WO2009082157A3 publication Critical patent/WO2009082157A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/58—Naphthylamines; N-substituted derivatives thereof
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • C07C2603/50—Pyrenes; Hydrogenated pyrenes

Definitions

  • the present invention relates to a novel aryl amine derivative and an organic electroluminescent device using the same.
  • organic electroluminescence refers to the phenomenon in which electric energy is converted into light energy by means of an organic substance. That is, if a voltage is applied between an anode and a cathode when an organic layer is disposed between both the electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. Then, the injected holes and electrons are recombined to form excitons, and light is emitted when the excitons drop to the ground state.
  • the organic layer As a way to provide a more efficient organic electroluminescent device (OELD) , research has been actively pursued to form an organic layer in the device in a multilayer structure instead of a monolayer structure.
  • the organic layer In most organic electroluminescent devices in use, which have a structure in which an organic layer and electrodes are deposited, the organic layer generally has a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer
  • an organic layer in an organic electroluminescent device is formed in a multilayer structure in this way is that interfaces between electrodes and an organic material are stabilized, or holes and electrons having a large difference in mobility in an organic material can be effectively transported to a light emitting layer by using suitable hole transport and electron transport materials, and luminous efficiency can be improved by balancing the densities of holes and electrons in the light emitting layer. Accordingly, it can be said that hole injection, hole transport, electron injection, and electron transport layers play important roles in an organic electroluminescent device.
  • Organic electroluminescent devices comprising an organic material have been extensively studied since C. W. Tang et al. of the Eastman Kodak Co. developed an organic electroluminescent device by a vacuum deposition method in 1987.
  • An organic photoconductive material that has been developed as a hole transport material has many advantages, such as low cost, flexible processability, and pollution-free, and various compounds have been proposed as the organic photoconductive material.
  • Examples of such compounds include an oxadiazole derivative, an oxazole derivative, a hydrazone derivative, a triarylpyrazoline derivative, an aryl amine derivative, a stylbene derivatives, etc.
  • the aryl amine derivative such as 4, 4' , 4"-tris [N, N- (1- naphthyDphenylamino] triphenylamine ( 1-TNATA) , 4, 4' , 4"-tris [N, N- (m-tolyl)phenylamino] triphenylamine (MTDATA), 4, 4' -bis [N- (1- naphthyl) -N-phenylamino] biphenyl ( ⁇ -NPD) , or 4, 4' -bis [N- (m- tolyl) -N-phenylamino] biphenyl (TPD), is widely used as a hole transport material or a hole injection material.
  • the conventional hole transport material is disadvantageous in that its stability and durability are insufficient.
  • the film is whitened due to crystallization or agglomeration when left for about two weeks because ⁇ -NPD is originally a crystalline compound.
  • 2,7- bis (dinaphthylamino) -9, 9-dimethylfluorene that is a fluorene derivative having a dimethyl group at 9, 9-position, 2,7-bis(N,N- diphenylamino) -9, 9-diphenylfluorene that is a fluorene derivative having diphenyl group at 9, 9-position, and the like are highly crystalline materials, and thus have the same problem as mentioned above. Consequently, when they are applied to an organic film device, such as an organic electroluminescent device, there is a problem in that short-circuiting and dark-spot formation are highly probable. Therefore, there is a need to develop a hole transport material that is excellent in hole transport capability and film stability, and has high glass transition temperature (T 9 ) .
  • the present invention has been made in view of the above-mentioned problems, and the present invention provides an organic electroluminescent device having improved luminous efficiency, luminance, power efficiency, and thermal stability (i.e. heat resistance) by developing a novel synthesized aryl amine derivative comprising a tetrahydropyrene core and applying the developed aryl amine derivative to the organic electroluminescent device.
  • Ar 1 to Ar 4 , X 1 , and X 2 are each independently a
  • C 5 -C 30 aromatic ring group that is an aromatic ring group substituted or unsubstituted by at least one kind selected from the group consisting of a Ci-C 30 alkyl group, a C 2 -C 30 alkenyl group , a C 2 -C 30 al kynyl group, a C 5 -C 3O aryl group, a Cs-C 3O heteroaryl group, a Cs-C 30 aryloxy group, a Ci-C 30 alkyloxy group, a C 5 -C 30 arylamino group, a C 5 -C 30 diarylamino group, a C 6 -C 30 arylalkyl group, a C 3 -C 30 cycloalkyl group, a C 3 -C 3 O heterocycloalkyl group, and a halogen atom;
  • R 1 to R 11 are each independently selected from the group consisting of a hydrogen atom, a Ci-C 30 alkyl group, a C 2 -C 30 alkenyl group, a C 2 -C 30 alkynyl group, a C 5 -C 30 aryl group, a C 5 -C 30 heteroaryl group, a C 5 -C 30 aryloxy group, a Ci-C 30 alkyloxy group, a C 5 -C 30 arylamino group, a C 5 -C 30 diarylamino group, a C 6 -C 30 arylal kyl group , a C 3 -C 30 cycloal kyl group , a C 3 -C 30 heterocycloalkyl group, and a halogen atom; and n and m are each independently an integer of 0 to 2 .
  • the Ci-C 30 alkyl group, the C 2 -C 3O alkenyl group, the C 2 -C 3 O alkynyl group, the C 5 -C 30 aryl group, the C 5 -C 30 heteroaryl group, the C 5 -C 30 aryloxy group, the Ci-C 30 alkyloxy group, the C 5 -C 30 arylamino group, the C 5 -C 30 diarylamino group, the C 6 -C 30 arylalkyl group, the C 3 -C 30 cycloalkyl group, and the C 3 -C 30 heterocycloalkyl group in Ar 1 to Ar 4 , X 1 , X 2 , and R 1 to R 11 may be each independently further substituted or unsubstituted by at least one kind of substituent selected from the group consisting of halogen, an amino group, a nitrile group, a nitro group, a Ci-C 40 alkyl group, a C 2 -C 40
  • an organic electroluminescent device comprising (i) an anode; (ii) a cathode; and (iii) one or more organic layers between the anode and the cathode, at least one of the one or more organic layers comprising the above aryl amine derivative represented by Formula 1.
  • the organic layer comprising the above aryl amine derivative represented by Formula 1 comprises a hole transport layer.
  • the aryl amine derivative represented by Formula 1 according to the present invention can ensure the stability of a material by an increased glass transition temperature (T 9 ) .
  • T 9 glass transition temperature
  • the stability, luminous efficiency, luminance, and power efficiency of an organic electroluminescent device can be improved.
  • the aryl amine derivative according to the present invention can significantly contribute to an improvement in the hole transport capability of an organic electroluminescent device, and particularly such an improved hole transport capability is very effective to maximize the performance of a full-color organic EL panel .
  • the aryl amine derivative represented by Formula 1 is a compound comprising a tetrahydropyrene core, amine groups (-NAr 1 Ar 2 and -NAr 3 Ar 4 ) each independently substituted at 2 and 7 positions of the tetrahydropyrene, and aromatic ring groups (X 1 and X 2 ) each independently substituted or unsubstituted between the tetrahydropyrene core and the amine groups (-NAr 1 Ar 2 and -NAr 3 Ar 4 ) .
  • Ar 1 to Ar 4 , X 1 , and X 2 are each independently a
  • C 5 -C 30 aromatic ring group that is preferably, but not limited to, a monovalent or divalent group selected from the group consisting of benzene, biphenyl, terphenyl, naphthalene, anthracene, triphenylamine, phenanthrene, pyrene, fluorene, and xanthene .
  • the aryl amine derivative represented by Formula 1 may be expressed by compounds presented below in Tables 1 to 3. However, the following compounds in Tables 1 to 3 are illustrative merely, and the aryl amine derivative represented by Formula 1 according to the present invention is not limited thereto.
  • HT-155 4, 4-biphenyl 4-biphenyl 3-biphenyl HT-156 4, 4-biphenyl 4-biphenyl HT-157 4, 4-biphenyl 4-biphenyl 2-p-terphenyl HT-158 1, 5-naphthyl 1-naphthyl 1-naphthyl HT-159 1, 5-naphthyl 1-naphthyl 2-naphthyl HT-160 1, 5-naphthyl 1-naphthyl 9-phenanthryl HT-161 1, 5-naphthyl 1-naphthyl 1-pyrenyl HT-162 1, 5-naphthyl 1-naphthyl phenyl HT-163 1, 5-naphthyl 1-naphthyl 2-biphenyl HT-164 1, 5-naphthyl 1-naphthyl 3-
  • S-group that is S-I to S-47
  • S-I to S-47 corresponds to non-limitative examples of amine substituents (-NAr 1 Ar 2 and - NAr 3 Ar 4 ) in Formula 1.
  • -NAr 1 Ar 2 and -NAr 3 Ar 4 may be each independently selected from, but not limited to, the following S- group, that is, S-I to S-47.
  • the organic electroluminescent device comprises (i) an anode, (ii) a cathode, and
  • the aryl amine derivative represented by Formula 1 may be a mixture of at least two kinds of aryl amine derivatives represented by Formula 1.
  • the aryl amine derivative represented by Formula 1 may be included as a hole transport material in the organic electroluminescent device to thereby improve the luminous efficiency, luminance, power efficiency, and thermal stability of the organic electroluminescent device.
  • the organic layer comprising the aryl amine derivative represented by Formula 1 is preferably a hole transport layer.
  • the organic layers other than the organic layer comprising the aryl amine derivative of the present invention may be a hole injection layer, a hole transport layer, a light emitting layer, and/or an electron transport layer.
  • a non-limitative example of the organic electroluminescent device according to the present invention may have a structure in which, for example, a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are laminated in sequence, and the hole transport layer of them comprises the aryl amine derivative represented by Formula 1.
  • An electron injection layer may be disposed on the electron transport layer.
  • the organic electroluminescent device according to the present invention may further comprise an insulating layer or adhesive layer that is inserted at the interfaces of the electrodes and the organic layers respectively.
  • the organic layer comprising the aryl amine derivative represented by Formula 1 may be formed by a vacuum deposition method or solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, thermal transfer, and the like.
  • the organic electroluminescent device according to the present invention may be manufactured by forming the organic layers and the electrodes by use of materials and methods well known in the art, except that at least one of the organic layers is formed in such a manner as to comprise the aryl amine derivative of the present invention.
  • a silicon wafer for example, a silicon wafer, a quartz or glass plate, a metal plate, a plastic film or sheet, etc. may be used as a substrate.
  • anode material examples include, but are not limited to, metal, such as vanadium, chrome, copper, zinc, and gold, or alloy thereof; metal oxide, such as zinc oxide, indium oxide, indium tin oxide (ITO) , and indium zinc oxide (IZO) ; ZnO; Al or SnO 2 ; a combination of metal, such as Sb, and oxide; conductive polymer, such as polythiophene, poly (3-methylthiophene) , poly [3, 4- (ethylene-1, 2-dioxy) thiophene] (PEDT), polypyrrole, and polyaniline; and carbon black.
  • metal such as vanadium, chrome, copper, zinc, and gold, or alloy thereof
  • metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO) , and indium zinc oxide (IZO)
  • ZnO zinc oxide
  • Al or SnO 2 a combination of metal, such as Sb, and oxide
  • conductive polymer such as polythiophene, poly
  • Examples of a cathode material include, but are not limited to, metal, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloy thereof; and a material having a multilayer structure, such as LiF/Al or LiO 2 ZAl. Further, there is no particular limitation on the materials of the hole injection, light emitting, electron transport, and electron injection layers, and they may be formed using conventional materials. Reference will now be made in detail to exemplary embodiments of the present invention. However, the following examples are illustrative merely, and the scope of the present invention is not limited thereto.
  • An OELD was manufactured by the following method: A glass substrate, on which an ITO (indium tin oxide) film was coated to a thickness of 1500A, was ultrasonically cleaned with distilled water. On completion of the cleaning with distilled water, the substrate was ultrasonically cleaned with a solvent, such as isopropyl alcohol, acetone, or methanol, was dried, and then was delivered to a plasma cleaner. In the plasma cleaner, the substrate was cleaned using oxygen plasma for 5 minutes, and then was delivered to a vacuum deposition apparatus.
  • a solvent such as isopropyl alcohol, acetone, or methanol
  • DS-205 Doosan, Korea was thermally vacuum-deposited to a thickness of 800A on the so-prepared ITO (anode) to form a hole injection layer, and the aryl amine derivative represented by Formula 1-5 (HT-I) was vacuum-deposited to a thickness of 150A on the hole injection layer to form a hole transport layer.
  • DS-H45 the aryl amine derivative represented by Formula 1-5
  • An OELD was manufactured in the same manner as in Example 1, except that the aryl amine derivative represented by Formula 1-1 (HT-2), obtained in Preparation Example 2, was used as the hole transport material, instead of the aryl amine derivative represented by Formula 1-5 (HT-I) , obtained in Preparation Example 1.
  • HT-2 aryl amine derivative represented by Formula 1-1
  • HT-I aryl amine derivative represented by Formula 1-5
  • An OELD was manufactured in the same manner as in Example 1, except that the aryl amine derivative represented by Formula 1-14 (HT-3) , obtained in Preparation Example 3, was used as the hole transport material, instead of the aryl amine derivative represented by Formula 1-5 (HT-I) , obtained in Preparation Example 1.
  • Example 1 had a luminance of 608cd/m 2 and thus exhibited a luminous efficiency of 6.1cd/A at a current density of lOmA/cm 2 and a voltage of 5.2V
  • Example 2 had a luminance of 618cd/m 2 and thus exhibited a luminous efficiency of 6.5cd/A at a current density of lOmA/cm 2 and a voltage of 5.3V
  • Example 3 had a luminance of 602cd/m 2 and thus exhibited a luminous efficiency of 6.1cd/A at a current density of lOmA/cm 2 and a voltage of 5.5V
  • Example 4 had a luminance of 609cd/m 2 and thus exhibited a luminous efficiency of ⁇ .Ocd/A at a current density of lOmA/cm 2 and a voltage of 5.7V.
  • Comparative Example 1 had a luminance of 560cd/m 2 and thus exhibited a luminous efficiency of
  • the inventive materials have an effect of reducing a driving voltage as compared to existing NPB because material stability ensured by their increased glass transition temperature (T 9 ) contributes to device stability, and additionally can also improve luminous efficiency.

Abstract

L'invention concerne un nouveau dérivé d'arylamine et un dispositif électroluminescent organique faisant appel à ce dérivé. Plus particulièrement, le dérivé d'arylamine est un composé comprenant un noyau tétrahydropyrène, des groupes amine (-NAr1Ar2 et -NAr3Ar4) dont chacun est indépendamment substitué en positions 2 et 7 du tétrahydropyrène, et des groupes cycliques aromatiques (X1 et X2) dont chacun est indépendamment substitué ou non substitué entre le noyau tétrahydropyrène et les groupes amine (-NAr1Ar2 et -NAr3Ar4). L'invention concerne également un dispositif électroluminescent organique comprenant (i) une anode, (ii) une cathode et (iii) une ou plusieurs couches organiques entre l'anode et la cathode, l'une au moins de ces couches organiques comprenant le dérivé d'arylamine. De préférence, la couche organique comprenant le dérivé d'arylamine est une couche de transport de trous.
PCT/KR2008/007608 2007-12-24 2008-12-23 Dérivé d'arylamine et dispositif électroluminescent organique faisant appel à ce dérivé WO2009082157A2 (fr)

Applications Claiming Priority (2)

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KR1020070136431A KR100974139B1 (ko) 2007-12-24 2007-12-24 아릴 아민 유도체 및 이를 이용한 유기 전계 발광 소자
KR10-2007-0136431 2007-12-24

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WO2009082157A2 true WO2009082157A2 (fr) 2009-07-02
WO2009082157A3 WO2009082157A3 (fr) 2009-08-13

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0823669B1 (fr) * 1996-08-08 2001-03-14 Canon Kabushiki Kaisha Elément électrophotographique photosensible, cartouche de traitement et appareil électrophotographique le comprenant
US20020137969A1 (en) * 2000-09-05 2002-09-26 Idemitsu Kosan Co., Ltd. Novel arylamine compound and organic electroluminescence device
US20030157364A1 (en) * 1997-05-19 2003-08-21 Akihiro Senoo Organic compound and electroluminescent device using the same

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2408979B (en) 2002-09-10 2006-03-08 Sankio Chemical Co Ltd New process for producing arylamines
KR100525408B1 (ko) 2002-12-24 2005-11-02 엘지전자 주식회사 유기 전계 발광 소자

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0823669B1 (fr) * 1996-08-08 2001-03-14 Canon Kabushiki Kaisha Elément électrophotographique photosensible, cartouche de traitement et appareil électrophotographique le comprenant
US20030157364A1 (en) * 1997-05-19 2003-08-21 Akihiro Senoo Organic compound and electroluminescent device using the same
US20020137969A1 (en) * 2000-09-05 2002-09-26 Idemitsu Kosan Co., Ltd. Novel arylamine compound and organic electroluminescence device

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KR20090068707A (ko) 2009-06-29
WO2009082157A3 (fr) 2009-08-13
KR100974139B1 (ko) 2010-08-04

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