WO2007108666A1 - New diamine derivatives, preparation method thereof and organic electronic device using the same - Google Patents

New diamine derivatives, preparation method thereof and organic electronic device using the same Download PDF

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Publication number
WO2007108666A1
WO2007108666A1 PCT/KR2007/001448 KR2007001448W WO2007108666A1 WO 2007108666 A1 WO2007108666 A1 WO 2007108666A1 KR 2007001448 W KR2007001448 W KR 2007001448W WO 2007108666 A1 WO2007108666 A1 WO 2007108666A1
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WIPO (PCT)
Prior art keywords
compound
group
mmol
organic
light emitting
Prior art date
Application number
PCT/KR2007/001448
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French (fr)
Inventor
Hye-Young Jang
Jae-Chol Lee
Jin-Kyoon Park
Kong-Kyeom Kim
Ji-Eun Kim
Tae-Yoon Park
Sung-Kil Hong
Sang-Young Jeon
Dong-Seob Jeong
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Lg Chem, Ltd.
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Publication date
Application filed by Lg Chem, Ltd. filed Critical Lg Chem, Ltd.
Priority to US12/225,483 priority Critical patent/US8173272B2/en
Priority to CN2007800102569A priority patent/CN101405255B/en
Priority to JP2009501361A priority patent/JP5165671B2/en
Priority to EP07715784.0A priority patent/EP1996540B1/en
Publication of WO2007108666A1 publication Critical patent/WO2007108666A1/en

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    • 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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/30—Germanium compounds
    • 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
    • C07C211/44—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 only one six-membered aromatic ring
    • C07C211/49—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 only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
    • C07C211/50—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 only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • 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
    • 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
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/917—Electroluminescent

Definitions

  • the present invention relates to a novel diamine derivative, a
  • the organic electronic device refers to a device which requires
  • the organic electronic device can be largely classified
  • the formed electron and hole are transported to a different electrode, respectively and used as a current source (voltage source),
  • Examples of the organic electronic device include an organic light
  • an organic solar cell an organic photoconductor (OPC)
  • the organic light emitting device will be mainly and
  • the hole injecting or hole transporting material the electron
  • organic light emitting phenomenon refers to organic light emitting phenomenon
  • organic light emitting phenomenon has a structure usually comprising an anode, a cathode and an organic material layer interposed therebetween.
  • the organic material layer may be mostly formed in a multilayer
  • the electron transporting layer the electron injecting layer and the like
  • light emitting device can be classified into a light emitting material
  • a charge transport ing material for example, a hole injecting material
  • emitting material can be classified into a high molecular weight type and a low molecular weight type, according to their molecular weight, and
  • the light emitting material can be any organic light emitting material. Further, the light emitting material can be any organic light emitting material. Further, the light emitting material can be any organic light emitting material. Further, the light emitting material can be any organic light emitting material. Further, the light emitting material can be any organic light emitting material. Further, the light emitting material can be any organic light emitting material. Further, the light emitting material can be any organic light emitting material. Further, the light emitting material can be any organic light emitting mechanism. Further, the light emitting material can be any organic light emitting material.
  • the wavelength of the host is moved according to the wavelength of the
  • a light having a desired wavelength can be obtained according the kind of the dopant .
  • the organic material layer in the device for example, a hole injecting
  • the organic light emitting device has not yet been fully realized.
  • the present inventors found a novel diamine derivative, and further
  • the diamine derivative can be used as a hole injecting, hole
  • the diamine derivative according to the present invention can serve as a
  • a light emitting host or a light emitting dopant, in particular, a blue light
  • the organic electronic device according to the present
  • Fig. 1 illustrates the structure of the organic light emitting
  • the present invention provides a diamine derivative represented by the following formula 1.
  • L is a C6 to C30 aryl group
  • Ai and A2 are the same or different from each other, and are
  • n is an integer from 1 to 5
  • At least one of Xs is selected from -GeRR 1 R", -SiRR 1 R" and deuterium
  • arylthiophene group a C3 to C20 cycloalkyl group, -OR, -SR, -SeR, -TeR,
  • Yi and Y 2 are the same or different from each other, and are each
  • Zi and Z2 are the same or different from each other, and are each
  • C20 arylthiophene group a C3 to C20 cycloalkyl group, -OR, -SR, -SeR, -TeR,
  • R, R' and R" are the same or different from each other, and are each
  • L is preferably selected from, for example, anthracenyl
  • Yi and Y2 are preferably selected from, for example, phenyl , biphenyl , naphthalenyl , tetral inyl , anthracenyl , stilbenyl, phenanthrenyl , pyrenyl ,
  • Zi and Z2 are preferably selected from, for example, hydrogen, a C&
  • R, R' and R" are each preferably, for example, a Ci to C20 alkyl group
  • the present invention provides a method for preparing the diamine derivative represented by the formula 1.
  • the diamine derivative according to the present invention can be any diamine derivative according to the present invention.
  • the arylamine compound preferably contains at least one selected
  • the present invention provides an organic electronic
  • the organic electronic device of the present invention can be any organic electronic device of the present invention.
  • the above-described compounds can serve as a hole injecting, hole
  • the organic light emitting device may have a structure that comprises a first electrode
  • FIG. 1 Fig. 1.
  • the organic light emitting device According to the
  • present invention can be prepared by method using a PVD (physical vapor deposition)
  • the organic light emitting device can be prepared by
  • the organic material layer may be of a multilayer structure
  • organic material layer can be produced to have a fewer number of layers
  • the anode material is preferably a material having a large work
  • metals such as vanadium, chromium, copper, zinc and gold
  • metal oxides such as zinc oxide, indium oxide,
  • ITO indium-tin oxide
  • IZO indium zinc oxide
  • poly(3-methylthiophene) poly[3,4-(ethylene-l,2-dioxy)thiophene]
  • PEDT polypyrrole
  • polyaniline but not limited thereto.
  • the cathode material is preferably a material having a small work
  • cathode material examples include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium,
  • gadolinium aluminum, silver, tin and lead, or an alloy thereof;
  • multilayer structure materials such as LiF/Al and Li(VAl, but not limited
  • the hole injecting material is a material facilitating hole
  • the molecular orbital) level of the hole injecting material is preferably
  • injecting material include organic materials of metal porphyrin,
  • the hole transporting material is preferably a material having high
  • hole mobility which can transfer holes from the anode or the hole
  • the light emitting material are a material capable of emitting
  • Alqs aluminum complex
  • the electron transporting material is suitably a material having
  • the light emitting layer includes
  • the organic light emitting device according to the invention may include
  • the compound according to the invention can function in an organic electronic device including an organic solar cell, an organic
  • a compound C (17 g, 78%) was prepared in the same manner as in Preparation Example 2, except that 5,6,7,8-tetrahydro-l-naphthylamine
  • the temperature of the mixture was slowly raised to 0°C for about 1 hour.
  • the temperature of the mixture was raised to room temperature over 1 hour.
  • a compound 21 (4.18 g, 60%) was prepared in the same manner as in
  • a compound 23 (5.05 g, 64%) was prepared in the same manner as in
  • a compound 27 (3.85 g, 62%) was prepared in the same manner as in
  • a compound 36 (4.12 g, 65%) was prepared in the same manner as in
  • a compound 40 (3.42 g, 65%) was prepared in the same manner as in
  • a compound 45 (3.63 g, 65%) was prepared in the same manner as in
  • a compound 53 (2.0Og, 61%) was prepared in the same manner as in
  • a compound 56 (3.9 g, 65%) was prepared in the same manner as in
  • a compound 64 (4.86 g, 62%) was prepared in the same manner as in
  • a compound 73 (5.37 g, 65%) was prepared in the same manner as in
  • a compound 77 (4.87 g, 65%) was prepared in the same manner as in
  • a compound 81 (4.96 g, 65%) was prepared in the same manner as in
  • a compound 86 (4.46 g, 65%) was prepared in the same manner as in
  • a compound 90 (5.24 g, 65%) was prepared in the same manner as in
  • Example 1 except that the compound 1(3.4 g, 8.5 mmol) synthesized in
  • Example 16 Preparation of compound 94 A compound 94 (4.74 g, 65%) was prepared in the same manner as in
  • Example 1 except that the compound 1(3.4 g, 8.5 mmol) synthesized in
  • a compound 98 (3.02 g, 65%) was prepared in the same manner as in
  • Example 1 except that the compound J (3.55 g, 20.4 mmol) was used instead of the compound J (3.55 g, 20.4 mmol).
  • a compound 103 (2.93 g, 62%) was prepared in the same manner as in
  • Example 1 except that the compound K (3.66 g, 20.4 mmol) was used instead of the compound K (3.66 g, 20.4 mmol).
  • a compound 110 (3.046 g, 59%) was prepared in the same manner as
  • a compound 111 (4.04 g, 61%) was prepared in the same manner as in
  • a compound 119 (3.68 g, 62%) was prepared in the same manner as in
  • a compound 120 (3.61 g, 60%) was prepared in the same manner as in
  • a compound 121 (4.43 g, 62%) was prepared in the same manner as in
  • a compound 122 (4.75 g, 60%) was prepared in the same manner as in
  • a compound 123 (3.14 g, 62%) was prepared in the same manner as in
  • a compound 124 (2.63 g, 60%) was prepared in the same manner as in
  • a compound 125 (3.96 g, 63%) was prepared in the same manner as in
  • a compound 126 (4.23 g, 60%) was prepared in the same manner as in
  • a compound 141 (3.94 g, 62%) was prepared in the same manner as in
  • a compound 142 (3.87 g, 60%) was prepared in the same manner as in
  • a compound 143 (4.78 g, 63%) was prepared in the same manner as in
  • a compound 144 (5.00 g, 60%) was prepared in the same manner as in
  • a compound 145 (3.57 g, 63%) was prepared in the same manner as in
  • a compound 146 (3.86 g, 60%) was prepared in the same manner as in
  • Example 1 except that 9,10-dibromoanthracene (2.86 g, 8.5 mmol) was used instead of 1,6-dibromopyrene (3.0 g, 8.5 mmol), and the compound M (5.94
  • a compound 156 (4.39 g, 63%) was prepared in the same manner as in
  • a compound 158 (4.86 g, 63%) was prepared in the same manner as in
  • a compound 161 (3.01 g, 62%) was prepared in the same manner as in Example 1, except that 9,10-dibromocrysene(3.28 g, 8.5 mmol) was used
  • a compound 163 (2.97 g, 60%) was prepared in the same manner as in
  • Example I 1 except that 9,10-dibromocrysene(3.28 g, 8.5 mmol) was used
  • a compound 172 (3.83 g, 63%) was prepared in the same manner as in
  • Example 40 Preparation of compound 173 A compound 173 (4.11 g, 60%) was prepared in the same manner as in
  • a compound 174 (3.82 g, 62%) was prepared in the same manner as in
  • Example 1 except that the compound 1(3.4 g, 8.5 mmol) synthesized in
  • a compound 175 (4.00 g, 60%) was prepared in the same manner as in
  • Example 1 except that the compound 1(3.4 g, 8.5 mmol) synthesized in
  • a compound 176 (4.65 g, 63%) was prepared in the same manner as in
  • Example 1 except that the compound 1(3.4 g, 8.5 mmol) synthesized in
  • a compound 177 (4.89 g, 60%) was prepared in the same manner as in
  • Example 1 except that the compound 1(3.4 g, 8.5 mmol) synthesized in
  • a glass substrate (Corning 7059 glass), on which a thin film of ITO
  • the detergent as used herein was a product
  • ultrasonic waves was repeated twice for 10 minutes by using distilled water .
  • washing with distilled water After the completion of washing with distilled water, washing with
  • ultrasonic waves was carried out by using solvents such as isopropyl
  • NPB hole injecting layer
  • the compound 1 (2 wt%)
  • thermal vacuum deposition to form an electron transporting layer.
  • LiF Lithium fluoride
  • lithium fluoride on the cathode was maintained at 0.3 A/sec and the
  • vacuum upon deposition was maintained at 2 x 10 ⁇ 7 to 5 x 10 ⁇ 8 torr.
  • An organic light emitting device was prepared in the same manner
  • An organic light emitting device was prepared in the same manner
  • An organic light emitting device was prepared in the same manner
  • An organic light emitting device was prepared in the same manner
  • An organic light emitting device was prepared in the same manner

Abstract

The present invention relates to a novel diamine derivative, a method for preparation thereof, and an organic electronic device using the same. The diamine derivative according to the present invention can serve as a hole injecting, hole transporting, electron injecting, electron transporting, or light emitting material in an organic electronic device including an organic light emitting device. Particularly, it can be used as a light emitting material as used alone, and also serve as a light emitting host, or a light emitting dopant, in particular, a blue light emitting dopant. The organic electronic device according to the present invention exhibits excellent characteristics in terms of efficiency, drive voltage, life time, and stability.

Description

[DESCRIPTION]
[Invention Title]
NEW DIAMINE DERIVATIVES, PREPARATION METHOD THEREOF AND ORGANIC
ELECTRONIC DEVICE USING THE SAME
[Technical Field]
The present invention relates to a novel diamine derivative, a
method for preparation thereof, and an organic electronic device using
the same.
This application claims priority benefits from Korean Patent
Application No. 10-2006-0026468, filed on March 23, 2006, the entire
contents of which are fully incorporated herein by reference.
[Background Art]
The organic electronic device refers to a device which requires
charge exchange between an electrode and an organic material using holes
and electrons. The organic electronic device can be largely classified
into two types according to its operation principle as follows. One type
is an electronic device having a configuration in which an exciton is
formed in an organic material layer by photons flown from an external light
source into the device and the exciton is separated into an electron and
a hole, the formed electron and hole are transported to a different electrode, respectively and used as a current source (voltage source),
and the other type is an electronic device having a configuration in which
a hole and/or electron are/is injected into an organic material
semiconductor forming an interface with an electrode by applying a voltage
or current to two or more electrodes to allow the device to operate by
means of the injected electron and hole.
Examples of the organic electronic device include an organic light
emitting device, an organic solar cell, an organic photoconductor (OPC)
drum and an organic transistor, which al 1 require a hole injecting or hole
transporting material, an electron injecting or electron transporting
material, or a light emitting material for driving the device.
Hereinafter, the organic light emitting device will be mainly and
specifically described, but in the above-mentioned organic electronic
devices, the hole injecting or hole transporting material, the electron
injecting or electron transporting material, or the light emitting
material injection functions according to a similar principle.
In general, the term "organic light emitting phenomenon" refers to
a phenomenon in which electric energy is converted to 1 ight energy by means
of an organic material. The organic light emitting device using the
organic light emitting phenomenon has a structure usually comprising an anode, a cathode and an organic material layer interposed therebetween.
Herein, the organic material layer may be mostly formed in a multilayer
structure comprising layers of different materials, for example, the hole
injecting layer, the hole transporting layer, the light emitting layer,
the electron transporting layer, the electron injecting layer and the like,
in order to improve efficiency and stability of the organic light emitting
device. In the organic light emitting device having such a structure,
when a voltage is applied between two electrodes, holes from the anode
and electrons from a cathode are injected into the organic material layer,
the holes and the electrons injected are combined together to form excitons.
Further, when the excitons drop to a ground state, lights are emitted.
Such the organic light emitting device is known to have characteristics
such as self-luminescence, high brightness, high efficiency, low drive
voltage, wide viewing angle, high contrast and high-speed response.
The materials used for the organic material layer of the organic
light emitting device can be classified into a light emitting material
and a charge transport ing material, for example, a hole injecting material ,
a hole transporting material, an electron transporting material and an
electron injecting material, according to their functions. The light
emitting material can be classified into a high molecular weight type and a low molecular weight type, according to their molecular weight, and
divided into a fluorescent material from singlet excited states and a
phosphorescent material from triplet excited states according to their
light emitting mechanism. Further, the light emitting material can be
classified into a blue, green or red light emitting material and a yellow
or orange light emitting material required for giving more natural color,
according to a light emitting color.
On the other hand, an efficiency of a device is lowered owing to
maximum luminescence wavelength moved to a longer wavelength due to the
interaction between the molecules, the deterioration of color purity and
the reduction in light emitting efficiency when only one material is used
for the light emitting material, and therefore a host/dopant system can
be used as the light emitting material for the purpose of enhancing the
color purity and the light emitting efficiency through energy transfer.
It is based on the principle that if a small amount of a dopant having
a smaller energy band gap than a host which forms a light emitting layer,
excitons which are generated in the light emitting layer are transported
to the dopant, thus emitting a light having a high efficiency. Here, since
the wavelength of the host is moved according to the wavelength of the
dopant , a light having a desired wavelength can be obtained according the kind of the dopant .
In order to allow the organic light emitting device to fully exhibit
the above-mentioned excellent characteristics, a material constituting
the organic material layer in the device, for example, a hole injecting
material, a hole transporting material, a light emitting material, an
electron transporting material and an electron injecting material should
be essentially composed of a stable and efficient material . However, the
development of a stable and efficient organic material layer material for
the organic light emitting device has not yet been fully realized.
Accordingly, the development of new materials is continuously desired.
The development of such a material is equally required to the
above-mentioned other organic electronic devices.
[Disclosure]
[Technical Problem]
The present inventors found a novel diamine derivative, and further
found that the diamine derivative can be used as a hole injecting, hole
transporting, electron injecting, electron transporting or light emitting
material, and exhibit effects of increased efficiency, lower operating
voltage, increased life-time, and higher stability of an organic
electronic device when forming an organic material layer of the organic electronic device.
[Technical Solution]
Therefore, it is an object of the present invention to provide a
novel diamine derivative, amethod for preparation thereof, and an organic
electronic device using the same.
[Advantageous Effects]
The diamine derivative according to the present invention can serve
as a hole injecting, hole transporting, electron injecting, electron
transporting, or light emitting material in an organic electronic device
including an organic light emitting device. Particularly, itcanbeused
as a light emitting material as used alone, and also serve as a light
emitting host, or a light emitting dopant, in particular, a blue light
emitting dopant. The organic electronic device according to the present
invention exhibits excellent characteristics in terms of efficiency,
drive voltage, life time, and stability.
[Description of Drawings]
Fig. 1 illustrates the structure of the organic light emitting
device according to one embodiment of the present invention.
[Best Mode]
The present invention provides a diamine derivative represented by the following formula 1.
[Formula 1]
Figure imgf000009_0001
wherein
L is a C6 to C30 aryl group,
Ai and A2 are the same or different from each other, and are
Figure imgf000009_0002
wherein n is an integer from 1 to 5, and
at least one of Xs is selected from -GeRR1R", -SiRR1R" and deuterium
(D), and the others are each independently selected from the group of
consisting of hydrogen, CN, NO2, a CQ to C20 arylamine group, a C6 to C20
arylthiophene group, a C3 to C20 cycloalkyl group, -OR, -SR, -SeR, -TeR,
-BRR', -AlRR', -SnRR1R", a C6 to C20 aryl group, a C8 to C20 arylalkenyl
group, and a C4 to C20 alkylene group which formed a fused ring with the
phenyl group or the naphthyl group,
Yi and Y2 are the same or different from each other, and are each
a C6 to C20 arylene group or a divalent C5 to C20 heterocyclic group, Zi and Z2 are the same or different from each other, and are each
hydrogen, halogen, deuterium, CN, NO2, a Ci to C20 alkyl group, a Ci to C20
alkoxy group, a Ce to C20 aryl group, a Ce to C20 arylamine group, a Ce to
C20 arylthiophene group, a C3 to C20 cycloalkyl group, -OR, -SR, -SeR, -TeR,
-BRR' , -AlRR1 , -SiRR1R", -GeRR1R", -SnRR1R", a C6 to C20 aryl group, a C8
to C20 arylalkenyl group, and a C4 to C20 alkylene group which formed a fused
ring with the phenyl group or the naphthyl group, and
R, R' and R" are the same or different from each other, and are each
hydrogen, a Ci to C20 alkyl group, a C3 to C20 cycloalkyl group, a C6 to C20
aryl group, or a C5 to C20 heterocyclic group.
In the formula 1,
L is preferably selected from, for example, anthracenyl,
phenanthrenyl , pyrenyl , perylenyl, crycenyl ,
Figure imgf000010_0001
Yi and Y2 are preferably selected from, for example, phenyl , biphenyl , naphthalenyl , tetral inyl , anthracenyl , stilbenyl, phenanthrenyl , pyrenyl ,
perylenyl, crycenyl and carbazolyl,
Zi and Z2 are preferably selected from, for example, hydrogen, a C&
to C20 aryl group, a Ce to C20 arylamine group, -BRR' , -SiRR1R", -GeRR'R"
and a C4 to C20 alkylene group which formed a fused ring with the phenyl
group or the naphthyl group, and
R, R' and R" are each preferably, for example, a Ci to C20 alkyl group,
or a Ce to C20 aryl group.
Specific examples of the compound of the formula 1 according to the
present invention are shown in the following compounds, but are not limited
thereto.
Figure imgf000012_0001
[Compound 1] [Compound 2] [Compound 3]
Figure imgf000012_0002
[Compound 4] [Compound 5] [Compound 6]
Figure imgf000012_0003
[Compound 7] [Compound 8j [Compound 91
Figure imgf000013_0001
[Compound 10] [Compound 11] [Compound 12]
r
Figure imgf000013_0002
[Compound 13] [Compound 14] [Compound Io]
Figure imgf000013_0003
[Compound 16] [Compound 17] [Compound 18]
[Compound 19] [Compound 20] [Compound 21]
Figure imgf000014_0004
Figure imgf000014_0003
Figure imgf000014_0002
[Compound 22] [Compound 23] [Compound 24]
Figure imgf000014_0005
[Compound 25] [Compound 26] [Compound 27]
Figure imgf000015_0001
[Compound 28] [Compound 291 [Compound 30]
Figure imgf000015_0002
[Compound 31] [Compound 32] [Compound 33]
Figure imgf000015_0003
[Compound 34] [Compound 3δ] [Compound 36]
Figure imgf000016_0001
[Compound 37] [Compound 38] [Compound 39]
Figure imgf000016_0002
[Compound 40] [Compound 41 ] [Compound 42]
Figure imgf000016_0003
[Compound 43] [Compound 44] [Compound 45]
Figure imgf000016_0004
[Compound 46] [Compound 47] [Compound 48]
Figure imgf000017_0001
[Compound 49] [Compound 50] [Compound 51]
Figure imgf000017_0002
[Compound 52] [Compound 53] [Compound 54]
Figure imgf000017_0003
[Compound 55] [Compound 56] [Compound 57.]
Figure imgf000017_0004
[Compound b3] [Compound 59^ [Compound 60]
Figure imgf000018_0001
[Compound 61] [Compound 62] [Compound 63]
Figure imgf000018_0002
[Compound 64] [Compound 65] [Compound 66]
Figure imgf000018_0003
[Compound 67] [Compound 68] [Compound 691
Figure imgf000018_0004
[Compound 70] [Compound 71] [Compound 72]
Figure imgf000019_0001
[Compound 73~ [Compound 74] [Compound 7b] LCompound 7GJ
Figure imgf000019_0002
[Compound 77] [Compound 78] [Compound 79] [Compound 80]
Figure imgf000019_0003
[Compound 81] [Compound 82] [Compound 83]
Figure imgf000020_0001
[Compound 84] [Compound 85] [Compound 86]
Figure imgf000020_0002
[Compound 87] LCompound 88] [Compound 89J
Figure imgf000020_0003
[Compound 90] [Compound 91] [Compound 92]
Figure imgf000020_0004
[Compound 93] [Compound 94] [Compound 95]
Figure imgf000021_0001
[Compound 96] LCompound 97] [Compound 98]
Figure imgf000021_0002
[Compound 99] [Compound 100] [Compound 101] [Compound 102]
Figure imgf000021_0003
[Compound 103] [Compound 104] [Compound 105] [Compound 100]
Figure imgf000021_0004
[Compound 107] [Compound 108] [Compound 1091 [Compound UO]
Figure imgf000022_0001
[Compound 111] [Compound 112] [Compound 113] [Compound 114]
Figure imgf000022_0002
[Compound 115] [Compound 116] [Compound 117]
Figure imgf000022_0003
[Compound 118] [Compound 119] [Compound 120]
Figure imgf000023_0001
[Compound 121 [Compound 122 j [Compound 123]
Figure imgf000023_0002
[Compound 12-1] [Compound 125] [Compound 126] [Compound 127 J
Figure imgf000023_0003
[Compound 123] [Compound 12U] [Compound 130] [Compound 131]
Figure imgf000023_0004
[Compound 132] [Compound 133] [Compound 134] [Compound 135]
Figure imgf000024_0001
[Compound 130] [Compound 137] [Compound 138] [Compound 139]
Figure imgf000024_0003
Figure imgf000024_0002
[Compound 140] [Compound 141. [Compound 142] [Compound 143]
Figure imgf000024_0004
[Compound 144] [Compound 145] [Compound 146] [Compound 147]
Figure imgf000025_0001
LCompound 148] [Compound 149] [Compound 150] [Compound 151]
Figure imgf000025_0002
[Compound 152] [Compound 153] [Compound 154] [Compound 155]
Figure imgf000025_0003
[Compound 156] [Compound 157] [Compound 1.58]
Figure imgf000025_0004
[Compound 159] [Compound 160] [Compound 161]
Figure imgf000025_0005
[Compound 162] [Compound 163] [Compound 164] [Compound 165]
Figure imgf000026_0001
[Compound 166] [Compound 167] [Compound 168] [Compound 169]
Figure imgf000026_0002
[Compound 170] [Compound 171] [Compound 172] [Compound 173]
Figure imgf000026_0003
[Compound 174] [Compound 175] [Compound 176]
Figure imgf000026_0004
[Compound 177] [Compound 173] [Compound 179]
Figure imgf000026_0005
[Compound 180] [Compound 181] [Compound 182]
Figure imgf000027_0001
[Compound 183 [Compound 184] [Compound 185]
Figure imgf000027_0002
[Compound 18G] [Compound 187] [Compound 188] [Compound 189]
Figure imgf000027_0003
[Compound 190] LCompound 191] [Compound 192] [Compound 193]
Figure imgf000027_0004
[Compound 194] [Compound 195] [Compound 19(5] [Compound 197]
Further, the present invention provides a method for preparing the diamine derivative represented by the formula 1.
The diamine derivative according to the present invention can be
prepared by reacting a dibromoaryl compound with an arylamine compound
in the presence of a palladium catalyst.
The arylamine compound preferably contains at least one selected
from a germanium group, a si IyI group, and deuterium.
Further, the present invention provides an organic electronic
device using the compound of the formula 1.
The organic electronic device of the present invention can be
prepared by usual methods and materials for preparing an organic
electronic device, except that the above-described compounds are used to
form at least one organic material layer.
Hereinbelow, the organic light emitting device will be exemplified.
The above-described compounds can serve as a hole injecting, hole
transporting, electron injecting, electron transporting, or light
emitting material, and particularly serve as a light emitting material
as used alone, as well as a light emitting host with an appropriate light
emitting dopant or a light emitting dopant, in particular a blue dopant
with an appropriate light emitting host.
In one embodiment of the present invention, the organic light emitting device may have a structure that comprises a first electrode,
a second electrode and organic material layers interposed therebetween,
and can be prepared by usual methods and materials for preparing an organic
light emitting device, except that the above-described compound according
to the present invention is used to form at least one of the organic
material layers in an organic light emitting device.
The structure of the organic light emitting device according to the
present invention is shown in Fig. 1.
For example, the organic light emitting device according to the
present invention can be prepared by method using a PVD (physical vapor
deposition) process such as sputtering and e-beam evaporation, said method
comprising:
depositing a metal , a metal oxide having conductivity or an alloy thereof
on a substrate to form an anode; forming an organic material layer
comprising a hole injecting layer, a hole transporting layer, a light
emitting layer, and an electron transporting layer on said anode; and
depositing a material, which can be used as a cathode, thereon.
Alternatively, the organic light emitting device can be prepared by
sequentially depositing a cathode material, an organic material layer,
and an anode material on a substrate. The organic material layer may be of a multilayer structure
containing a hole injecting layer, a hole transporting layer, a light
emitting layer, an electron transporting layer, and the like, but not
limited thereto, and may be of a monolayer structure. Further, the
organic material layer can be produced to have a fewer number of layers,
by using a variety of polymeric materials, by means of a solvent process
rather than a deposit process, such as spin coating, dip coating, doctor
blading, screen printing, ink jet printing, and heat transfer processes.
The anode material is preferably a material having a large work
function to facilitate hole injection usually to an organic material layer.
Specific examples of the anode material which can be used in the present
invention include metals such as vanadium, chromium, copper, zinc and gold,
or an alloy thereof; metal oxides such as zinc oxide, indium oxide,
indium-tin oxide (ITO), and indium zinc oxide (IZO); a combination of a
metal and an oxide such as ZnO^Al and Snθ2:Sb; conductive polymers such
as poly(3-methylthiophene) , poly[3,4-(ethylene-l,2-dioxy)thiophene]
(PEDT), polypyrrole and polyaniline, but not limited thereto.
The cathode material is preferably a material having a small work
function to facilitate electron injection usually to an organic material
layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium,
gadolinium, aluminum, silver, tin and lead, or an alloy thereof;
multilayer structure materials such as LiF/Al and Li(VAl, but not limited
thereto.
The hole injecting material is a material facilitating hole
injection from an anode at low voltage. The HOMO (highest occupied
molecular orbital) level of the hole injecting material is preferably
located between the work function of the anode materials and the HOMO level
of its neighboring organic material layer. Specific examples of the hole
injecting material include organic materials of metal porphyrin,
oligothiophene and arylamine series, organic materials of hexanitrile
hexaazatriphenylene and quinacridone series, organic materials of
perylene series, and conductive polymers of anthraquinone, polyaniline,
and polythiophene series, but are not limited thereto.
The hole transporting material is preferably a material having high
hole mobility, which can transfer holes from the anode or the hole
injecting layer toward the light emitting layer. Specific examples
thereof include organic materials of arylamine series, conductive
polymers and block copolymers having both conjugated portions and
non-conjugated portions, but are not limited thereto. The light emitting material are a material capable of emitting
visible light by accepting and recombining holes from the hole
transporting layer and electrons from the electron transporting layer,
preferably a material having high quantum efficiency for fluorescence and
phosphorescence. Specific examples thereof include 8-hydroxy-quinoline
aluminum complex (Alqs); compounds of carbazole series; dimerized styryl
compounds; BAIq; 10-hydroxybenzoquinoline-metal compounds; compounds of
benzoxazole, benzthiazole and benzimidazole series; polymers of
poly(p-phenylenevinylene) (PPV) series; spiro compounds; and compounds
of polyfluorene and rubrene series, but are not limited thereto.
The electron transporting material is suitably a material having
high electron mobility, which can transfer electrons from the cathode to
the light emitting layer. Specific examples thereof include
8-hydroxyquinoline aluminum complex; complexes including Alq3! organic
radical compounds; and hydroxyflavone-metal complexes, but are not
limited thereto.
The organic light emitting device according to the invention may
be of a front-side, backside or double-side light emission according to
the materials used.
The compound according to the invention can function in an organic electronic device including an organic solar cell, an organic
photoconductor and an organic transistor, according to a principle similar
to that applied to the organic light emitting device.
[Mode for Invention]
Hereinbelow, the preferred Examples of the present invention will
be presented for further understanding the present invention. However,
the following Examples are presented merely for illustrative purpose, and
thus do not limit the scope of the present invention.
The compound of the formula I according to the present invention
can be prepared in multi-step chemical reactions. The preparation of the
compound is described by way of Examples below. As will be clear in
Examples, a certain intermediate compound is first prepared, and then the
intermediate compound is used to prepare the compound of the formula I.
Exemplary intermediate compounds are listed below as Compounds A through
M. In these compounds, "Br" may be substituted with any other reactive
atoms or functional groups.
Figure imgf000034_0001
[Compound A] ICompound Bj [Compound C]
Figure imgf000034_0002
[Compound D] [Compound E] [Compound F]
Figure imgf000034_0003
[Compound G] LCompound HJ [Compound I]
Figure imgf000034_0004
[Compound Jl [Compound KJ [Compound L] [Compound M]
Preparation Example 1: Preparation of compound A
Dibromobenzene (20 g, 84.78 mraol) was dissolved in anhydrous
tetrahydrofuran (THF, 200 mL) at room temperature under nitrogen
atmosphere. The solution was cooled to -78°C . n-butyl 1 ithium (34 mL,
2.5 M pentane solution) was added slowly to the solution at -78°C , and
the temperature of the mixture was slowly raised to 0°C for about 1 hour. To the mixture, trimethylgerumanium bromide (18 ml, 101.74 mmol) was added,
and the temperature of the mixture was raised to room temperature over
1 hour. After confirmation of completion of the reaction, the mixture
was extracted from ethyl acetate, dried over magnesium sulfate, and
distilled off under reduced pressure to obtain a compound A (20 g,
MS (M+) 273
Preparation Example 2: Preparation of compound B
The compoundA (18 g, 65.45 mmol), aniline (6.6 ml , 72 mmol), pd(dba)2
(0.125 g, 0.13 mmol), PCt-Bu)3 (0.04 g, 0.2 mmol) and sodium t-butoxide
(1.80 g, 18.7 mmol) were added to toluene (200 mL) under nitrogen
atmosphere, and the mixture was refluxed for about 3 hours. After
completion of the reaction, the mixture was cooled to room temperature,
and the reaction mixture was added to a mixed solution of THF and H2O. The
organic layer was separated, dried over magnesium sulfate, and then
concentrated. The residue was separated by column chromatography to
obtain a compound B (16 g, 85%). MS [M] = 286
Preparation Example 3: Preparation of compound C
A compound C (17 g, 78%) was prepared in the same manner as in Preparation Example 2, except that 5,6,7,8-tetrahydro-l-naphthylamine
(10.6 g, 72 mmol) was used instead of aniline (6.6 ml, 72 mmol) in
Preparation Example 2. MS [M] = 340
Preparation Example 4: Preparation of compound D
Dibromobenzene (20 g, 84.78 mmol) was dissolved in anhydrous
tetrahydrofuran (THF, 200 mL) at room temperature under nitrogen
atmosphere. The solution was cooled to -78°C . n-butyl lithium (34 mL,
2.5 M pentane solution) was added slowly to the solution at -78°C, and
the temperature of the mixture was slowly raised to 0°C for about 1 hour.
To the mixture, chlorotrimethylsilane (13 ml, 101.74 mmol) was added, and
the temperature of the mixture was raised to room temperature over 1 hour.
After confirmation of completion of the reaction, the mixture was
extracted from ethyl acetate, dried over magnesium sulfate, and distilled
off under reduced pressure to obtain a compound D (18 g, 93%). MS (M+)
= 229
Preparation Example 5: Preparation of compound E
The compound D (15 g, 65.45 mmol), aniline (6.6ml , 72 mmol), pd(dba)2
(0.125 g, 0.13 mmol), PCt-Bu)3 (0.04 g, 0.2 mmol) and sodium t-butoxide (1.80 g, 18.7 mmol) were added to toluene (200 mL) under nitrogen
atmosphere, and the mixture was refluxed for about 3 hours. After
completion of the reaction, the mixture was cooled to room temperature,
and the reaction mixture was added to a mixed solution of THF and H2O. The
organic layer was separated, dried over magnesium sulfate, and then
concentrated. The residue was separated by column chromatography to
obtain a compound E (15 g, 86%). MS [M] = 143
Preparation Example 6: Preparation of compound F
1,6-Dibromopyrene (3 g, 8.5 mmol), 4-chlorophenylboronic acid (2.9
g, 18.7 mmol), and Pd(PPlIs)4 (0.29 g, 0.26 mmol) were added to an aqueous
2 M K2CO3 solution (20 mL) and THF (80 mL) under nitrogen atmosphere. The
mixture was refluxed under stirring for about 12 hours. After completing
the reaction, the mixture was cooled to room temperature. The organic
layer was separated from the reaction mixture, dried over magnesium
sulfate, and distilled under reduced pressure. The residue was purified
by column chromatography to prepare a compound F (2.5 g, 70%). MS [M+H]+
= 422
Preparation Example T- Preparation of compound G 3,9-Dibromoperylene (3.5 g, 8.5mmol), 4-chlorophenylboronic acid
(2.9 g, 18.7 mmol), and Pd(PPh3)4 (0.29 g, 0.26 mmol) were added to an
aqueous 2 MK2CO3 solut ion (20 mL) andTHF (80 mL) under nitrogen atmosphere.
The mixture was refluxed under stirring for about 12 hours. After
completing the reaction, the mixture was cooled to room temperature. The
organic layer was separated from the reaction mixture, dried over
magnesium sulfate, and distilled under reduced pressure. The residue was
purified by column chromatography to prepare a compound G (3.0 g, 75%).
MS [M+H]+ = 472
Preparation Example 8: Preparation of compound H
9,10-Dibromoanthracene (2.86 g, 8.5 mmol), 4-chlorophenylboronic
acid (2.9 g, 18.7 mmol), and Pd(PPh3)4 (0.29 g, 0.26 mmol) were added to
an aqueous 2 M K2CO3 solution (20 mL) and THF (80 mL) under nitrogen
atmosphere. The mixture was refluxed under stirring for about 12 hours.
After completing the reaction, the mixture was cooled to room temperature.
The organic layer was separated from the reaction mixture, dried over
magnesium sulfate, and distilled under reduced pressure. The residue was
purified by column chromatography to prepare a compound H (3.0 g,
MS [M+H]+ = 398 Preparation Example 9: Preparation of compound I
9,10-Dibromocrysene (3.28 g, 8.5mmol), 4-chlorophenylboronic acid
(2.9 g, 18.7 mmol), and Pd(PPh3)4 (0.29 g, 0.26 mmol) were added to an
aqueous 2MK2CO3 solution (2OmL) andTHF (8OmL) under nitrogen atmosphere.
The mixture was refluxed under stirring for about 12 hours. After
completing the reaction, the mixture was cooled to room temperature. The
organic layer was separated from the reaction mixture, dried over
magnesium sulfate, and distilled under reduced pressure. The residue was
purified by column chromatography to prepare a compound I (2.9 g, 75%).
MS [M+H]+ = 448
Preparation Example IQ: Preparation of compound J
Bromobenzene-dδ (10.6 g, 65.45 mmol), aniline (6.6 ml, 72 mmol),
pd(dba)2 (0.125 g, 0.13 mmol), PCt-Bu)3 (0.04 g, 0.2 mmol) and sodium
t-butoxide (1.80 g, 18.7 mmol ) were added to toluene (80 mL) under nitrogen
atmosphere, and the mixture was refluxed for about 3 hours. After
completion of the reaction, the mixture was cooled to room temperature,
and the reaction mixture was added to a mixed solution of THF and H2O. The
organic layer was separated, dried over magnesium sulfate, and then concentrated. The residue was separated by column chromatography to
obtain a compound J (16 g, 85%). MS [M] = 174
Preparation Example 11: Preparation of compound K
Bromobenzene-dδ (10.6 g, 65.45 mmol), aniline-2,3,4,5,6-D5 (6.6 ml,
72 mmol), pd(dba)2 (0.125 g, 0.13 mmol), PCt-Bu)3 (0.04 g, 0.2 mmol) and
sodium t-butoxide (1.80 g, 18.7 mmol) were added to toluene (80 mL) under
nitrogen atmosphere, and the mixture was refluxed for about 3 hours.
After completion of the reaction, the mixture was cooled to room
temperature, and the reaction mixture was added to a mixed solution of
THFandføO. The organic layer was separated, dried over magnesium sulfate,
and then concentrated. The residue was separated by column
chromatography to obtain a compound K (16 g, 85%). MS [M] = 179
Preparation Example 12: Preparation of compound L
The compound D of Preparation Example 4 (15 g, 65.45 mmol),
aniline-2,3,4,5,6-D5 (6.6 ml, 72 mmol), pd(dba)2 (0.125 g, 0.13 mmol),
PCt-Bu)3 (0.04 g, 0.2 mmol) and sodium t-butoxide (1.80 g, 18.7 mmol) were
added to toluene (80 mL) under nitrogen atmosphere, and the mixture was
refluxed for about 3 hours. After completion of the reaction, the mixture was cooled to room temperature, and the reaction mixture was added to a
mixed solution of THF and H2O. The organic layer was separated, dried over
magnesium sulfate, and then concentrated. The residue was separated by
column chromatography to obtain a compound L (16 g, 85%). MS [M] = 246
Preparation Example 13: Preparation of compound M
The compound A of Preparation Example 1 (18 g, 65.45 mmol),
aniline-2,3,4,5,6-05 (6.6 ml, 72 mmol), pd(dba)2 (0.125 g, 0.13 mmol),
PCt-Bu)3 (0.04 g, 0.2 mmol) and sodium t-butoxide (1.80 g, 18.7 mmol) were
added to toluene (80 mL) under nitrogen atmosphere, and the mixture was
refluxed for about 3 hours. After completion of the reaction, the mixture
was cooled to room temperature, and the reaction mixture was added to a
mixed solution of THF and H2O. The organic layer was separated, dried over
magnesium sulfate, and then concentrated. The residue was separated by
column chromatography to obtain a compound M (16 g, 85%). MS [M] = 291
Example l: Preparation of compound 1
1,6-Dibromopyrene (3.0 g, 8.5 mmol), the compound B (5.83 g, 20.4
mmol), Pd(dba)2 (0.097 g, 0.17 mmol), PCt-Bu)3 (0.05 g, 0.255 mmol) and
sodium t-butoxide (2.45 g, 25.5 mmol) were added to toluene (100 mL) under nitrogen atmosphere, and the mixture was refluxed for about 2 hours.
After completion of the reaction, the mixture was cooled to room
temperature, and the reaction mixture was added to a mixed solution of
THF and H2O. The organic layer was separated, dried over MgSO4, and then
concentrated. The residue was separated by column chromatography to
obtain a compound 1 (4.06 g, 62%). MS [M] = 770
Example 2: Preparation of compound 21
A compound 21 (4.18 g, 60%) was prepared in the same manner as in
Example 1, except that 3,9-dibromoρerylene (3.5 g, 8.5 mmol) was used
instead of 1,6-dibromopyrene (3.0 g, 8.5 mmol) in Example 1. MS [M] =
820
Example 3: Preparation of compound 23
A compound 23 (5.05 g, 64%) was prepared in the same manner as in
Example 1, except that 3,9-dibromoperylene (3.5 g, 8.5 mmol) was used
instead of 1,6-dibromopyrene (3.0 g, 8.5 mmol), and the compound C (6.94
g, 20.4 mmol) was used instead of the compound B (5.83 g, 20.4 mmol) in
Example 1. MS [M] = 928 Example 4: Preparation of compound 27
A compound 27 (3.85 g, 62%) was prepared in the same manner as in
Example 1, except that 3,9-dibromoperylene (3.5 g, 8.5 mmol) was used
instead of 1,6-dibromopyrene (3.0 g, 8.5 mmol), and the compound E (2.92
g, 20.4 mmol) was used instead of the compound B (5.83 g, 20.4 mmol) in
Example 1. MS [M] = 730
Example 5: Preparation of compound 36
A compound 36 (4.12 g, 65%) was prepared in the same manner as in
Example 1, except that 9,10-dibromoanthracene (2.86 g, 8.5 mmol) was used
instead of 1,6-dibromopyrene (3.0 g, 8.5 mmol) in Example 1. MS [M] =
746
Example 6: Preparation of compound 40
A compound 40 (3.42 g, 65%) was prepared in the same manner as in
Example 1, except that 9,10-dibromoanthracene (2.86 g, 8.5 mmol) was used
instead of 1,6-dibromopyrene (3.0 g, 8.5 mmol), and the compound C (6.94
g, 20.4 mmol) was used instead of the compound B (5.83 g, 20.4 mmol) in
Example 1. MS [M] = 620 Example T- Preparation of compound 45
A compound 45 (3.63 g, 65%) was prepared in the same manner as in
Example 1, except that 9,10-dibromoanthracene (2.86 g, 8.5 mmol) was used
instead of 1,6-dibromopyrene (3.0 g, 8.5 mmol), and the compound E (4.55
g, 20.4 mmol) was used instead of the compound B (5.83 g, 20.4 mmol) in
Example 1. MS [M] = 656
Example 8: Preparation of compound 53
A compound 53 (2.0Og, 61%) was prepared in the same manner as in
Example 1, except that 9,10-dibromocrysene (3.28 g, 8.5 mmol) was used
instead of 1,6-dibromopyrene (3.0 g, 8.5 mmol), and the compound C (6.94
g, 20.4 mmol) was used instead of the compound B (5.83 g, 20.4 mmol) in
Example 1. MS [M] = 386
Example 9: Preparation of compound 56
A compound 56 (3.9 g, 65%) was prepared in the same manner as in
Example 1, except that 9,10-dibromocrysene (3.28 g, 8.5 mmol) was used
instead of 1,6-dibromopyrene (3.0 g, 8.5 mmol), and the compound E (2.92
g, 20.4 mmol) was used instead of the compound B (5.83 g, 20.4 mmol) in
Example 1. MS [M] = 706 Example IQ: Preparation of compound 64
A compound 64 (4.86 g, 62%) was prepared in the same manner as in
Example 1, except that the compound F(3.6 g, 8.5 mmol) synthesized in
Preparation Example 6 was used instead of 1,6-dibromopyrene (3.0 g, 8.5
mmol) in Example 1. MS [M] = 922
Example 11: Preparation of compound 73
A compound 73 (5.37 g, 65%) was prepared in the same manner as in
Example 1, except that the compound G(4.0 g, 8.5 mmol) synthesized in
Preparation Example 7 was used instead of 1,6-dibromopyrene (3.0 g, 8.5
mmol) in Example 1. MS [M] = 972
Example 12: Preparation of compound 77
A compound 77 (4.87 g, 65%) was prepared in the same manner as in
Example 1, except that the compound G(4.0 g, 8.5 mmol) synthesized in
Preparation Example 7 was used instead of 1,6-dibromopyrene (3.0 g, 8.5
mmol), and the compound E (2.92 g, 20.4 mmol) was used instead of the
compound B (5.83 g, 20.4 mmol) in Example 1. MS [M] = 882 Example 13: Preparation of compound 81
A compound 81 (4.96 g, 65%) was prepared in the same manner as in
Example 1, except that the compound H(3.4 g, 8.5 mmol) synthesized in
Preparation Example 8 was used instead of 1,6-dibromopyrene (3.0 g, 8.5
mmol) in Example 1. MS [M] = 898
Example 14: Preparation of compound 86
A compound 86 (4.46 g, 65%) was prepared in the same manner as in
Example 1, except that the compound H(3.4 g, 8.5 mmol) synthesized in
Preparation Example 8 was used instead of 1,6-dibromopyrene (3.0 g, 8.5
mmol), and the compound E (2.92 g, 20.4 mmol) was used instead of the
compound B (5.83 g, 20.4 mmol) in Example 1. MS [M] = 808
Example 15: Preparation of compound 90
A compound 90 (5.24 g, 65%) was prepared in the same manner as in
Example 1, except that the compound 1(3.4 g, 8.5 mmol) synthesized in
Preparation Example 9 was used instead of 1,6-dibromopyrene (3.0 g, 8.5
mmol) in Example 1. MS [M] = 948
Example 16: Preparation of compound 94 A compound 94 (4.74 g, 65%) was prepared in the same manner as in
Example 1, except that the compound 1(3.4 g, 8.5 mmol) synthesized in
Preparation Example 9 was used instead of 1,6-dibromopyrene (3.0 g, 8.5
mmol), and the compound E (2.92 g, 20.4 mmol) was used instead of the
compound B (5.83 g, 20.4 mmol) in Example 1. MS [M] = 858
Example 17: Preparation of compound 98
A compound 98 (3.02 g, 65%) was prepared in the same manner as in
Example 1, except that the compound J (3.55 g, 20.4 mmol) was used instead
of the compound B (5.83 g, 20.4 mmol) in Example 1. MS [M] = 546
Example 18: Preparation of compound 103
A compound 103 (2.93 g, 62%) was prepared in the same manner as in
Example 1, except that the compound K (3.66 g, 20.4 mmol) was used instead
of the compound B (5.83 g, 20.4 mmol) in Example 1. MS [M] = 556
Example 19: Preparation of compound 110
A compound 110 (3.046 g, 59%) was prepared in the same manner as
in Example 1, except that the compound L (5.07 g, 20.4 mmol) was used
instead of the compound B (5.83 g, 20.4 mmol) in Example 1. MS [M] = 690 Example 20: Preparation of compound 111
A compound 111 (4.04 g, 61%) was prepared in the same manner as in
Example 1, except that the compound M (5.94 g, 20.4 mmol) was used instead
of the compound B (5.83 g, 20.4 mmol) in Example 1. MS [M] = 780
Example 21: Preparation of compound 119
A compound 119 (3.68 g, 62%) was prepared in the same manner as in
Example 1, except that the compound F(3.6 g, 8.5 mmol) synthesized in
Preparation Example 6 was used instead of 1,6-dibromopyrene (3.0 g, 8.5
mmol), and the compound J (3.55 g, 20.4 mmol) was used instead of the
compound B (5.83 g, 20.4 mmol) in Example 1. MS [M] = 698
Example 22: Preparation of compound 120
A compound 120 (3.61 g, 60%) was prepared in the same manner as in
Example 1, except that the compound F(3.6 g, 8.5 mmol) synthesized in
Preparation Example 6 was used instead of 1,6-dibromopyrene (3.0 g, 8.5
mmol), and the compound K (3.66 g, 20.4 mmol) was used instead of the
compound B (5.83 g, 20.4 mmol) in Example 1. MS [M] = 708 Example 23: Preparation of compound 121
A compound 121 (4.43 g, 62%) was prepared in the same manner as in
Example 1, except that the compound F(3.6 g, 8.5 mmol) synthesized in
Preparation Example 6 was used instead of 1,6-dibromopyrene (3.0 g, 8.5
mmol), and the compound L (5.07 g, 20.4 mmol) was used instead of the
compound B (5.83 g, 20.4 mmol) in Example 1. MS [M] = 842
Example 24: Preparation of compound 122
A compound 122 (4.75 g, 60%) was prepared in the same manner as in
Example 1, except that the compound F(3.6 g, 8.5 mmol) synthesized in
Preparation Example 6 was used instead of 1,6-dibromopyrene (3.0 g, 8.5
mmol), and the compound M (5.94 g, 20.4 mmol) was used instead of the
compound B (5.83 g, 20.4 mmol) in Example 1. MS [M] = 932
Example 25: Preparation of compound 123
A compound 123 (3.14 g, 62%) was prepared in the same manner as in
Example 1, except that 3,9-dibromoperylene (3.5 g, 8.5 mmol) was used
instead of 1,6-dibromopyrene (3.0 g, 8.5 mmol), and the compound J (3.55
g, 20.4 mmol) was used instead of the compound B (5.83 g, 20.4 mmol) in
Example 1. MS [M] = 596 Example 26: Preparation of compound 124
A compound 124 (2.63 g, 60%) was prepared in the same manner as in
Example 1, except that 3,9-dibromoperylene (3.5 g, 8.5 mmol) was used
instead of 1,6-dibromopyrene (3.0 g, 8.5 mmol), and the compound K (3.66
g, 20.4 mmol) was used instead of the compound B (5.83 g, 20.4 mmol) in
Example 1. MS [M] = 606
Example 27: Preparation of compound 125
A compound 125 (3.96 g, 63%) was prepared in the same manner as in
Example 1, except that 3,9-dibromoperylene (3.5 g, 8.5 mmol) was used
instead of 1,6-dibromopyrene (3.0 g, 8.5 mmol), and the compound L (5.07
g, 20.4 mmol) was used instead of the compound B (5.83 g, 20.4 mmol) in
Example 1. MS [M] = 740
Example 28: Preparation of compound 126
A compound 126 (4.23 g, 60%) was prepared in the same manner as in
Example 1, except that 3,9-dibromoperylene (3.5 g, 8.5 mmol) was used
instead of 1,6-dibromopyrene (3.Og, 8.5 mmol), and the compound M (5.94
g, 20.4 mmol) was used instead of the compound B (5.83 g, 20.4 mmol) in Example 1. MS [M] = 830
Example 29: Preparation of compound 141
A compound 141 (3.94 g, 62%) was prepared in the same manner as in
Example 1, except that the compound G(4.0 g, 8.5 mmol) synthesized in
Preparation Example 7 was used instead of 1,6-dibromopyrene (3.0 g, 8.5
mmol), and the compound J (3.55 g, 20.4 mmol) was used instead of the
compound B (5.83 g, 20.4 mmol) in Example 1. MS [M] = 748
Example 30: Preparation of compound 142
A compound 142 (3.87 g, 60%) was prepared in the same manner as in
Example 1, except that the compound G(4.0 g, 8.5 mmol) synthesized in
Preparation Example 7 was used instead of 1,6-dibromopyrene (3.0 g, 8.5
mmol), and the compound K (3.66 g, 20.4 mmol) was used instead of the
compound B (5.83 g, 20.4 mmol) in Example 1. MS [M] = 758
Example 31: Preparation of compound 143
A compound 143 (4.78 g, 63%) was prepared in the same manner as in
Example 1, except that the compound G(4.0 g, 8.5 mmol) synthesized in
Preparation Example 7 was used instead of 1,6-dibromopyrene (3.0 g, 8.5 mmol), and the compound L (5.07 g, 20.4 mmol) was used instead of the
compound B (5.83 g, 20.4 mmol) in Example 1. MS [M] = 892
Example 32: Preparation of compound 144
A compound 144 (5.00 g, 60%) was prepared in the same manner as in
Example 1, except that the compound G(4.0 g, 8.5 mmol) synthesized in
Preparation Example 7 was used instead of 1,6-dibromopyrene (3.Og, 8.5
mmol), and the compound M (5.94 g, 20.4 mmol) was used instead of the
compound B (5.83 g, 20.4 mmol) in Example 1. MS [M] = 982
Example 33: Preparation of compound 145
A compound 145 (3.57 g, 63%) was prepared in the same manner as in
Example 1, except that 9,10-dibromoanthracene (2.86 g, 8.5 mmol) was used
instead of 1,6-dibromopyrene (3.0 g, 8.5 mmol), and the compound L (5.07
g, 20.4 mmol) was used instead of the compound B (5.83 g, 20.4 mmol) in
Example 1. MS [M] = 666
Example 34: Preparation of compound 146
A compound 146 (3.86 g, 60%) was prepared in the same manner as in
Example 1, except that 9,10-dibromoanthracene (2.86 g, 8.5 mmol) was used instead of 1,6-dibromopyrene (3.0 g, 8.5 mmol), and the compound M (5.94
g, 20.4 mmol) was used instead of the compound B (5.83 g, 20.4 mmol) in
Example 1. MS [M] = 756
Example 35: Preparation of compound 156
A compound 156 (4.39 g, 63%) was prepared in the same manner as in
Example 1, except that the compound H(3.4 g, 8.5 mmol) synthesized in
Preparation Example 8 was used instead of 1,6-dibromopyrene (3.0 g, 8.5
mmol), and the compound L (5.07 g, 20.4 mmol) was used instead of the
compound B (5.83 g, 20.4 mmol) in Example 1. MS [M] = 818
Example 36: Preparation of compound 158
A compound 158 (4.86 g, 63%) was prepared in the same manner as in
Example 1, except that the compound H(3.4 g, 8.5 mmol) synthesized in
Preparation Example 8 was used instead of 1,6-dibromopyrene (3.0 g, 8.5
mmol), and the compound M (5.94 g, 20.4 mmol) was used instead of the
compound B (5.83 g, 20.4 mmol) in Example 1. MS [M] = 908
Example 37: Preparation of compound 161
A compound 161 (3.01 g, 62%) was prepared in the same manner as in Example 1, except that 9,10-dibromocrysene(3.28 g, 8.5 mmol) was used
instead of 1,6-dibromopyrene (3.0 g, 8.5 mmol), and the compound J (3.55
g, 20.4 mmol) was used instead of the compound B (5.83 g, 20.4 mmol) in
Example 1. MS [M] = 572
Example 38: Preparation of compound 163
A compound 163 (2.97 g, 60%) was prepared in the same manner as in
Example I1 except that 9,10-dibromocrysene(3.28 g, 8.5 mmol) was used
instead of 1,6-dibromopyrene (3.0 g, 8.5 mmol), and the compound K (3.66
g, 20.4 mmol) was used instead of the compound B (5.83 g, 20.4 mmol) in
Example 1. MS [M] = 582
Example 39: Preparation of compound 172
A compound 172 (3.83 g, 63%) was prepared in the same manner as in
Example 1, except that 9,10-dibromocrysene(3.28 g, 8.5 mmol) was used
instead of 1,6-dibromopyrene (3.0 g, 8.5 mmol), and the compound L (5.07
g, 20.4 mmol) was used instead of the compound B (5.83 g, 20.4 mmol) in
Example 1. MS [M] = 716
Example 40: Preparation of compound 173 A compound 173 (4.11 g, 60%) was prepared in the same manner as in
Example 1, except that 9,10-dibromocrysene(3.28 g, 8.5 mmol) was used
instead of 1,6-dibromopyrene (3.0 g, 8.5 mmol), and the compound M (5.94
g, 20.4 mmol) was used instead of the compound B (5.83 g, 20.4 mmol) in
Example 1. MS [M] = 806
Example 41: Preparation of compound 174
A compound 174 (3.82 g, 62%) was prepared in the same manner as in
Example 1, except that the compound 1(3.4 g, 8.5 mmol) synthesized in
Preparation Example 9 was used instead of 1,6-dibromopyrene (3.0 g, 8.5
mmol), and the compound J (3.55 g, 20.4 mmol) was used instead of the
compound B (5.83 g, 20.4 mmol) in Example 1. MS [M] = 724
Example 42: Preparation of compound 175
A compound 175 (4.00 g, 60%) was prepared in the same manner as in
Example 1, except that the compound 1(3.4 g, 8.5 mmol) synthesized in
Preparation Example 9 was used instead of 1,6-dibromopyrene (3.0 g, 8.5
mmol), and the compound K (3.66 g, 20.4 mmol) was used instead of the
compound B (5.83 g, 20.4 mmol) in Example 1. MS [M] = 734 Example 43: Preparation of compound 176
A compound 176 (4.65 g, 63%) was prepared in the same manner as in
Example 1, except that the compound 1(3.4 g, 8.5 mmol) synthesized in
Preparation Example 9 was used instead of 1,6-dibromopyrene (3.Og, 8.5
mmol), and the compound L (5.07 g, 20.4 mmol) was used instead of the
compound B (5.83 g, 20.4 mmol) in Example 1. MS [M] = 868
Example 44: Preparation of compound 177
A compound 177 (4.89 g, 60%) was prepared in the same manner as in
Example 1, except that the compound 1(3.4 g, 8.5 mmol) synthesized in
Preparation Example 9 was used instead of 1,6-dibromopyrene (3.0 g, 8.5
mmol), and the compound M (5.94 g, 20.4 mmol) was used instead of the
compound B (5.83 g, 20.4 mmol) in Example 1. MS [M] = 958
Experimental Example 1:
A glass substrate (Corning 7059 glass), on which a thin film of ITO
(indium tin oxide) was coated to a thickness of 1000 A, was immersed in
distilled water having a detergent dissolved therein to wash the substrate
with ultrasonic waves. The detergent as used herein was a product
commercially available from Fisher Co. and the distilled water was one which had been twice filtered by using a filter commercially available
from Millipore Co. ITO was washed for 30 minutes, and then washing with
ultrasonic waves was repeated twice for 10 minutes by using distilled water .
After the completion of washing with distilled water, washing with
ultrasonic waves was carried out by using solvents such as isopropyl
alcohol , acetone and methanol . The resultant product was dried, and then
transported to a plasma washing machine. The substrate was washed for
5 minutes using an oxygen plasma, and then transported to a vacuum
depositing machine.
On the ITO electrode,
3,6-bis-2-naphthy1pheny1amino-N-[4-(2-naphthy1pheny1 )aminopheny1]carb
azole (800 A), and 4,4'-bis[N-(l-naphthyl)-N-ρhenyl amino]biphenyl
(NPB) (300 A) were sequentially deposited to form a hole injecting layer
and a hole transporting layer, respectively. The compound 1 (2 wt%)
prepared in the Example 1 was deposited thereon with the following compound
N (300 A) to form a light emitting layer, and then 9,10-bis-2-naphthyl-2-
[4-(N-phenylbenzoimidazoyl)phenyl]anthracene (300 A) was coated by
thermal vacuum deposition to form an electron transporting layer.
Lithium fluoride (LiF) and aluminum were sequentially deposited on
the electron transporting layer to thicknesses of 12 A and 2000 A respectively, to form a cathode, thereby obtaining an organic light
emitting device. In the above process, the deposition rate of the organic
material was maintained at 0.4 to 0.7 A/sec and the deposition rate of
lithium fluoride on the cathode was maintained at 0.3 A/sec and the
deposition rate of aluminum was maintained at 2 A/sec. The degree of
vacuum upon deposition was maintained at 2 x 10~7 to 5 x 10~8 torr.
When a forward electric field of 7.8 V was applied to the organic
light emitting device as prepared above, blue light emission of 4.9 cd/A,
which corresponds to x = 0.170, and y = 0.150 based on the 1931 CIE color
coordinate, was observed at a current density of 100 mA/cπf.
Figure imgf000058_0001
[Compound N]
Experimental Example 2'-
An organic light emitting device was prepared in the same manner
as in Experimental Example 1, except that the compound 56 was used instead
of the compound 1 in Experimental Example 1.
When a forward electric field of 7.9 V was applied to the organic light
emitting device as prepared above, blue light emission of 4.7 cd/A, which corresponds to x = 0.170, and y = 0.151 based on the 1931 CIE color
coordinate, was observed at a current density of 100 mA/cnf.
Experimental Example 3:
An organic light emitting device was prepared in the same manner
as in Experimental Example 1, except that the compound 86 was used instead
of the compound 1 in Experimental Example 1.
When a forward electric field of 7.7 V was applied to the organic
light emitting device as prepared above, blue light emission of 4.8 cd/A,
which corresponds to x = 0.171, and y = 0.153 based on the 1931 CIE color
coordinate, was observed at a current density of 100 mA/cπf.
Experimental Example 4:
An organic light emitting device was prepared in the same manner
as in Experimental Example 1, except that the compound 111 was used instead
of the compound 1 in Experimental Example 1.
When a forward electric field of 7.7 V was applied to the organic
light emitting device as prepared above, blue light emission of 4.9 cd/A,
which corresponds to x = 0.171, and y = 0.153 based on the 1931 CIE color
coordinate, was observed at a current density of 100 mA/cm\ Experimental Example 5:
An organic light emitting device was prepared in the same manner
as in Experimental Example 1, except that the compound 156 was used instead
of the compound 1 in Experimental Example 1.
When a forward electric field of 7.8 V was applied to the organic
light emitting device as prepared above, blue light emission of 4.8 cd/A,
which corresponds to x = 0.172, and y = 0.153 based on the 1931 CIE color
coordinate, was observed at a current density of 100 mA/cπf.
Experimental Example 6:
An organic light emitting device was prepared in the same manner
as in Experimental Example 1, except that the compound 173 was used instead
of the compound 1 in Experimental Example 1.
When a forward electric field of 7.9 V was applied to the organic
light emitting device as prepared above, blue light emission of 4.9 cd/A,
which corresponds to x = 0.173, and y = 0.152 based on the 1931 CIE color
coordinate, was observed at a current density of 100 mA/cnf.

Claims

[CLAIMS]
[Claim 1]
A diamine derivative represented by the following formula 1:
[Formul a 1]
Figure imgf000061_0001
wherein
L is a Ce to C30 aryl group,
A1 and A2 are the same or different from each other, and are
Figure imgf000061_0002
wherein n is an integer from 1 to 5, and
at least one of Xs is selected from the group consisting of -GeRR1R",
-SiRR1R" and deuterium (D) , and the others are each independently selected
from the group consisting of hydrogen, CN, NO2, a Ce to C20 arylamine group,
a Ce to C20 arylthiophene group, a C3 to C20 cycloalkyl group, -OR, -SR,
-SeR, -TeR, -BRR', -AlRR', -SnRR1R", a C6 to C20 aryl group, a C8 to C20
arylalkenyl group, and a C4 to C20 alkylene group which formed a fused ring
with the phenyl group or the naphthyl group, Yi and Y2 are the same or different from each other, and are each
a Cβ to C20 arylene group or a divalent C5 to C20 heterocyclic group,
Zi and Z2 are the same or different from each other, and are each
hydrogen, halogen, deuterium, CN, NO2, a Ci to C20 alkyl group, a Ci to C20
alkoxy group, a Ce to C20 aryl group, a Ce to C20 arylamine group, a Ce to
C20 arylthiophene group, a C3 to C20 cycloalkyl group, -OR, -SR, -SeR, -TeR,
-BRR1 , -AlRR1 , -SiRR1R", -GeRR1R", -SnRR1R", a C6 to C20 aryl group, a C8
to C20 arylalkenyl group, and a C4 to C20 alkylene group which formed a fused
ring with the phenyl group or the naphthyl group, and
R, R1 and R" are the same or different from each other, and are each
hydrogen, a Ci to C20 alkyl group, a C3 to C20 cycloalkyl group, a Ce to C20
aryl group, or a C5 to C20 heterocyclic group.
[Claim 2]
The diamine derivative according to claim 1, wherein L is selected
from the group consisting of anthracenyl , phenanthrenyl , pyrenyl ,
perylenyl, crycenyl ,
Figure imgf000063_0001
[Claim 3]
The diamine derivative according to claim 1, wherein Yi and Y2 are
selected from the group consisting of phenyl, biphenyl , naphthalenyl ,
tetralinyl, anthracenyl , stilbenyl, phenanthrenyl , pyrenyl , perylenyl,
crycenyl and carbazolyl .
[Claim 4]
The diamine derivative according to claim 1, wherein the compound
of the formula 1 is selected from the group consisting of the following
compounds:
Figure imgf000064_0001
[Compound 1. [Compound 2] [Compound 3]
Figure imgf000064_0002
[Compound 4] [Compound 5] [Compound 6]
Figure imgf000064_0003
[Compound 7] [Compound 8] [Compound 9]
Figure imgf000065_0001
[Compound 10] [Compound 11] [Compound 12]
Figure imgf000065_0002
Figure imgf000065_0003
[Compound 13]
Figure imgf000065_0004
[Compound lδ]
Figure imgf000065_0005
[Compound 16] [Compound 17] [Compound 18]
Figure imgf000066_0001
[Compound IU] [Compound 20] [Compound 21]
Figure imgf000066_0002
[Compound 22] [Compound 23] [Compound 24]
Figure imgf000066_0003
[Compound 25j [Compound 26j [Compound 27]
Figure imgf000067_0002
Figure imgf000067_0001
[Compound 28] [Compound 291 [Compound 30]
Figure imgf000067_0003
[Compound 31J [Compound 32' [Compound 33]
Figure imgf000067_0004
[Compound 34] [Compound 35] [Compound 3(5]
Figure imgf000068_0001
[Compound 37] [Compound 38] [Compound 39]
Figure imgf000068_0002
[Compound 40] [Compound 41] [Compound 42]
Figure imgf000068_0003
[Compound 43j [Compound 44, [Compound 45]
Figure imgf000068_0004
[Compound 46] [Compound 47] [Compound 48]
Figure imgf000069_0001
[ Compound 49] [Compound 50] [Compound 51]
Figure imgf000069_0002
[Compound 52] [Compound 53] [Compound ;:>4]
Figure imgf000069_0003
[Compound 55] [Compound 56] [Compound 57]
Figure imgf000069_0004
[Compound 58] [Compound 59] [Compound 60]
Figure imgf000070_0001
[Compound 61] [Compound 62] [Compound 63]
Figure imgf000070_0002
[Compound 64] [Compound 6b. [Compound 66J
Figure imgf000070_0003
[Compound 67. [Compound 68] [Compound 69]
Figure imgf000070_0004
[Compound 70] [Compound 71] [Compound 72]
Figure imgf000071_0001
[Compound 73] [Compound 74] [Compound 75] [Compound 7CJ
Figure imgf000071_0002
[Compound 77] [Compound 78] [Compound 79] [Compound 80]
Figure imgf000071_0003
[Compound 81] [Compound 82] [Compound 83]
Figure imgf000072_0001
[Compound 84] [Compound 85] [Compound 86]
Figure imgf000072_0002
[Compound 87] [Compound 88 [Compound 89]
Figure imgf000072_0003
[Compound 90] [Compound 91] [Compound 92]
Figure imgf000072_0004
[Compound 93" [Compound 94] [Compound 95]
Figure imgf000073_0001
[Compound 96] [Compound 97. [Compound 98]
Figure imgf000073_0002
[Compound 99] [Compound 100] [Compound 101] [Compound 102 ]
Figure imgf000073_0003
[Compound 103] [Compound 104] [Compound 10b] [Compound 106]
Figure imgf000073_0004
[Compound 107] [Compound 108] [Compound 109] [Compound 110]
Figure imgf000074_0001
[Compound 111] [Compound 112] [Compound 113] [Compound 114]
Figure imgf000074_0002
[Compound 115] [Compound 116] [Compound 117]
Figure imgf000074_0003
[Compound 118] [Compound 119] [Compound 120]
Figure imgf000075_0001
LCompound 121] [Compound 122] LCompound 123]
Figure imgf000075_0002
[Compound 124] [Compound 125] [Compound 126] [Compound 127]
Figure imgf000075_0003
[Compound 128] [Compound 129] LCompound 13Oj [Compound 131]
Figure imgf000075_0004
[Compound 132] [Compound 133] [Compound 134] [Compound 135]
Figure imgf000076_0001
[Compound 130] [Compound 137] [Compound 138] [Compound 139]
Figure imgf000076_0002
[Compound 140] [Compound 141]
Figure imgf000076_0003
Figure imgf000076_0004
[Compound 144] [Compound 145] [Compound 146] [Compound 147]
Figure imgf000077_0001
[Compound 148] [Compound 149] [Compound 150] [Compound 151]
Figure imgf000077_0002
[Compound Ib2] [Compound 153] [Compound 154] [Compound 155]
Figure imgf000077_0003
[Compound 156] [Compound 157] [Compound 158]
Figure imgf000077_0004
LCompound 159] [Compound 160] [Compound 161]
Figure imgf000077_0005
[Compound 162] [Compound 163] [Compound 164] [Compound 165]
Figure imgf000078_0001
[Compound 166] [Compound 167] [Compound 168] [Compound 169]
Figure imgf000078_0002
[Compound 170] [Compound 171] [Compound 172] [Compound 173]
Figure imgf000078_0003
[Compound 174] [Compound .175] [Compound 176]
Figure imgf000078_0004
[Compound 177] [Compound 178] [Compound 179]
Figure imgf000078_0005
[Compound 180] [Compound 181] [Compound 182]
Figure imgf000079_0001
[Compound 183 [Compound 184] [Compound 185]
Figure imgf000079_0002
[Compound 186] [Compound 187] [Compound 188] [Compound 189]
Figure imgf000079_0003
[Compound 190] [Compound 191] [Compound 192'; [Compound 193]
Figure imgf000079_0004
[Compound 194] [Compound 195] [Compound 19(5] [Compound 197]
[Claim 5] A method for preparing the diamine derivative of claim 1, comprising
the step of reacting a dibromoaryl compound with an arylamine compound
in the presence of a palladium catalyst.
[Claim 6]
The method for preparing the diamine derivative according to claim
5, wherein the arylamine compound contains at least one selected from the
group consisting of a germanium group, a si IyI group, and deuterium.
[Claim 7]
An organic electronic device comprising a first electrode, a second
electrode, and at least one organic material layer interposed between the
first electrode and the second electrode, wherein at least one layer of
the organic material layers comprises the compound according to any one
of claims 1 to 4.
[Claim 8]
The organic electronic device according to claim 7, wherein the
organic material layer comprises at least one of a hole injecting layer,
a hole transporting layer, and a hole injecting and hole transporting layer,
and one of the layers comprise the compound according to any one of claims
1 to 4.
[Claim 9] The organic electronic device according to claim 7, wherein the
organic material layer comprises a light emitting layer, and the light
emitting layer comprises the compound according to any one of claims 1
to 4.
[Claim 10]
The organic electronic device according to claim 7, wherein the
organic material layer comprises an electron transporting layer, and the
electron transporting layer comprises the compound according to any one
of claims 1 to 4.
[Claim 11]
The organic electronic device according to claim 7, wherein the
organic electronic device is selected from the group consisting of an
organic light emitting device, an organic photovoltaic cell, an organic
photoconductor (OPC) and an organic transistor.
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