Title of Invention

"A CARBAZOLE COMPOUND AND ORGANIC LIGHT EMITTING DEVICE USING SAME"

Abstract Disclosed is a compound of Formula 1 and an organic light emitting device using the same.
Full Text Description
CARBAZOLE DERIVATIVE AND ORGANIC LIGHT
EMITTING DEVICE USING SAME
Technical Field
[1] The present invention relates to a novel organic compound and an organic light
emitting device using die same.
Background Art
[3] An organic light emitting device has a structure in which an anode, a cathode, and
an organic material layer including a single molecule or polymers between these
electrodes are layered, and is based on a mechanism in which an electron and a hole
which are injected from the cathode and the anode into the organic material layer form
an exciton, and in which light having certain wavelengths is generated when the
exciton drops to a ground state.
[4] The principle of the organic light emitting device was discovered for the first time
by Pope et al. using a single crystal of anthracene in the year 1965. Subsequently, in
the year 1987, Tang in Kodak Co. suggested an organic light emitting device having a
function-separation type of laminate structure in which an organic material layer is
divided into two layers: a hole transport layer and a light emitting layer. It was
confirmed (hat high emission intensity of 1000 cd/m2 or more was obtained at a low
voltage not more than 10 V in the organic light emitting device (Tang, C. W.;
VanSlyke, S.A. AppL Phys. Lett. 1987,57,913). With this as an impetus, the organic
electroluminescent device has started to be watched with keen interest, and, recently,
many studies are being intensely conducted on an organic electroluminescent device
having a function-separation type of laminate structure.
[5] However, the organic light emitting device is problematic in that a light emitting
lifetime is short, and durability and reliability are low. This is known to result from
physical and chemical transformation, photochemical and electrochemical transformation,
delamination, fusion, crystallization, and thermal decomposition of organic
materials constituting layers of the organic light emitting device, and oxidation of a
cathode.
[6] Accordingly, there is a need to develop an organic material which is capable of
being used in the organic light emitting device and to avoid the above problems.
[7] Meanwhile, an organic material including carbazole, particularly an organic
material having a linear structure which includes two carbazole molecules, has
frequently been used for a long time as a drum photosensitive material for £ duplicator
or as a photoconductive material. Furthermore, a trimer type of triindole compound,
which has a nonlinear structure as shown in the following Formula and includes three
carbazoles, is known.
(Figure Removed)
[11] For example, a compound, in which R is H, CH3, or CH2CH2N(CH2CH2)2O in
the above Formula, was known long ago as a byproduct generated in a biochemistry
field (J Org Chem 1998,63(20), 7002-7008, Tetrahedron 1980,36,1439). Japanese
Patent Laid-Open Publication No. 2004-123619 discloses a compound, in which R in
the above Formula is H as an effective component of a stabilizing agent for organic
materials. Additionally, Japanese Patent Laid-Open Publication No. 2004-055240
discloses a compound having the basic structure of the above Formula as an electrode
active material.
[12] In an organic light emitting device field, many studies have been made into the use
of a compound containing carbazole as a donor compound or a light emitting material
capable of injecting or transporting holes. For example, Japanese Patent Laid-Open
Publication No. 2001-261680 discloses the use of a compound in which R is an alkyl
group having a carbon number of 2 to 24 in the above Formula as a photoconductive
material, a nonlinear optical material, or an electroluminescent (EL) material.
[13] However, in the case of the compound having the nonlinear trimer structure as
described above, only a compound in which an amine group is substituted with
hydrogen or an alkyl group can be generated or synthesized as a byproduct in the biochemistry
field. Even if the compound having the trimer structure can be synthesized,
synthesis thereof is difficult and the yield is very low, thus few studies have been made
with respect to this. For example, when using the method disclosed in Japanese Parent
Laid-Open Publication No. 2001-261680, only an alkyl group can be introduced to R
in the above-mentioned Formula.Disclosure of Invention
Disclosure of Invention
Technical Problem
[ 15] The present inventors have conducted extensive studies into the synthesis of a
novel organic compound, resulting in the finding that the compound is used as a hole injection material, a hole transport material, a light emitting host, or a light emitting dopant in an organic light emitting device, thereby improving light emitting efficiency and stability of the device
[16] Accordingly, an object of the present invention is to provide a novel organic
compound and an organic light emitting device using the same
[17] -
Technical Solution
[18] The present invention provides a compound of the following Formula I :
• [19]
[20] Formula 1
[21] (Formula Removed)
[22]
[23] Wherein, XI to X3 each are a substituted or unsubstituted benzene ring, or a
substituted or unsubstituted 5-membered heterocyclic aromatic group which includes
a ring source selected from the group consisting of a substituted or unsubstituted
benzene ring, O, S, and NR' (R'is selected from the group consisting of hydrogen, a
substituted or unsubstituted alkyl group, and a substituted or unsubstituted aromatic
group);
t
[24] Rl to R3 each are-a substituted or unsubstituted aromatic group or a substituted
or unsubstituted heteroaromatic group with the proviso that XI to X3 are substituted or unsubstituted benzene rings, and Rl to R3 are selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group, and a substituted or unsubstituted heteroaromatic group wife the proviso that X1 to X3 are substituted or unsubstituted 5-membered heterocyclic aromatic group
[25] Furthermore, the present invention provides an organic light emitting device which
comprises a first electrode, one or more organic material layers, and a second electrode
sequentially layered therein. One or more of the organic material layers include the
compound of Formula 1.
[26]
Brief Description of the Drawings
[27] FIG. 1 illustrates an organic light emitting device useful in the present invention;
[28] FIG. 2 illustrates another organic light emitting device useful in the present
invention;
[29] FIG. 3 illustrates still another organic light emitting device useful in die present
invention; and
[30] FIG. 4 illustrates yet another organic light emitting device useful in the present
invention.
Best Mode for Carrying Out the Invention
[32] Hereinafter, a detailed description will be given of Ihe present invention.
[33] In an organic light emitting device field, it is known that carbazole or its derivatives
can be used as a donor compound or a light emitting material capable of injecting or
transporting holes. For example, the use of carbazole having an arylamine group
introduced thereto as a hole transport material and a light emitting material is known
(US 6,649,722). However, as described in the Background Art, up to now, among
compounds of carbazole and its derivatives, an organic material which is capable of
assuring light emitting efficiency and stability of the organic light emitting device so as
to commercialize (he organic light emitting device has not been developed.
[34] A study has been made into the use of trimer compounds of carbazole or its
derivatives as a donor material or a light emitting material, which is capable of
injecting or transporting holes, of an organic light emitting device. However, since it is
difficult to synthesize the trimer compounds of carbazole or its derivatives, variety of
the type of compounds has not been assured, thus there is a limit to the study of the
usage of the above compounds.
[35] The present inventors have conducted repeated studies into trimer compounds of
carbazole or its derivatives, resulting in the synthesis of a novel compound of the
following Formula 1.
(Figure Removed)
In the above Formula 1, XI to X3 and Rl to R3 are the same as in the abovementioned
definition.
Representative examples of the compound of Formula 1 include a compound of
Formula 2 and a compound of Formula 3.
Formula 2
In the above Formula 2, Rl to R3 are a substituted or unsubstituted aromatic group,
or a substituted or unsubstituted heteroaromatic group, and
R4 to R15 are each selected from the group consisting of hydrogen, a halogen atom,
a nitriie group (CN), a Ditto group (NO2), a formyl group, an acetyl group, a benzoyl
group, an amide group, a styryl group, an acetylene group, a quinoline group, a
quinazoline group, a phenanthroline group, a cuproin group, a substituted or unsubstituted
alkyl group, a substituted or unsubstituted aromatic group, a substituted or
unsubstituted aralkyl group, a substituted or unsubstituted arylamine group, a
substituted or unsubstituted alkylamine group, a substituted or unsubstituted aralkylamine
group, and a substituted or unsubstituted heterocyclic group.
Formula 3
In the above Formula 3:
Rl to R3 each are selected from the group consisting of hydrogen, a substituted or
unsubsiHuted alkyl group, a substituted or unsubstiluted aromatic group, and a
substituted or unsubstituted heteroaromatic group;
R4 to R9 each are selected from the group consisting of hydrogen, a halogen atom,
a nitrite group (CN), a nitro group (NO2), a formyl group, an acetyl group, a benzoyl
group, an amide group, a styryl group, an acetylene group, a quinoline group, a
quinazoline group, a phenanthroline group, a cuproin group, a substituted or unsubstituted
alkyl group, a substituted or unsubstituted aromatic group, a substituted or
unsubstituted aralkyl group, a substituted or unsubstituted arylamine group, a
substituted or unsubstituted alkylamine group, a substituted or unsubstituted aralkylamine
group, and a substituted or unsubstituted heterocyclic group; and
Y is selected from the group consisting of 0, S, and NR' (R' is selected from the
group consisting of hydrogen, a substituted or unsubstituted alkyl group, and a
substituted or unsubstituted aromatic group).
Structural characteristics of compounds of Formulae 2 and 3, and their effects are as
follows.
Hie compound of the above Formula 2 has a trimer structure including three
carbazoles, in which an amine group of carbazole is substituted with an aromatic
group. The compound of the above Formula 3 has a trimer structure including three
carbazole derivatives in which a 5-membered hetero ring such as thiophene is
positioned at the position of one benzene of carbazole.
[60] In the compounds of Formulae 2 and 3, monomers, that is, carbazole or its
derivatives, constituting the trimer do not affect each other in view of chemical
structures. Furthermore, in the above compounds, an increase in a conjugation length
due to trimerization is not so big as in a compound having a linear structure. For the
same reason, in the compounds of Fonnulae 2 and 3, optical, spectroscopic, and electrochemical
properties of the monomers are not changed significantly.
[61] Accordingly, the compounds of Formulae 2 and 3 have intrinsic properties of
carbazole and carbazole derivatives in which the 5-membered hetero ring such as
thiophene is positioned at one benzene of carbazole, that is, hole injection or transport
properties and/or light emitting properties in the organic light emitting device. Thus,
the compounds of Formulae 2 and 3 can act as a hole injection material, a hole
transport material, a light emitting host, or a light emitting dopant hi the organic light
emitting device.
'62] Additionally, since molecular weight increases while the intrinsic properties of
carbazole or its derivatives are maintained in the compounds of Formulae 2 and 3, they
are thermally more stable man compounds of the monomers. Therefore, the
compounds of the present invention can increase the life of the organic light emitting
device.
63] Furthermore, as described above, since the compounds of Formulae 2 and 3 have
conjugation lengths that are relatively shorter than those of compounds having linear
structures, an energy band gap is wide, thus they are used as a host material, along with
fluorescent guest materials and particularly phosphorescent guest materials, in the
organic light emitting device.
64] Meanwhile, in the compound of Formula 2, an amine group is substituted with an
aromatic group with respect to the conventional carbazole trimer compound hi which
an amine group is substituted with hydrogen or an alkyl group. In Formula 2, the
aromatic group substituting (he amine group affects a HOMO (highest occupied
molecular orbital) energy level of the compound, unlike hydrogen or the alkyl group.
Accordingly, the HOMO energy level of the compound of Formula 2 as the hole
injection and/or transport material or me light emitting material is optimized depending
on the type of aromatic group substituting the amine group, and preferably, depending
on the number of amine contained in the aromatic group.
65] Based on the above description, the compound of Formula 2 can improve the
stability of holes, hole transport properties and/or light emitting properties of the
organic light emitting device hi comparison with the carbazole trimer compound, in
which the amine group is substituted with hydrogen or the alkyl group as disclosed in
the prior art. Thereby, efficiency of the device is improved. For example, in the
compound of the present invention, an aromatic group having excellent light emitting
efficiency is introduced to the ainine group, thereby a light emitting material having
excellent light emitting properties, for example, a host material or a dopant material, is
prepared.
[66] Even though the compound of Formula 2 has the above-mentioned advantages, it
has not been synthesized in the prior art due to difficulty in synthesis. Thus, there has
been no study of die usage of the above compound. A method of producing die
compound of Formula 2 will be described later.
[67] The above-mentioned basic physical properties of the compound according to the
present invention result from a structure in which carbazole is trimerized like the
compound of Formula 2 and the amine group of carbazole is substituted with the
aromatic group, or a structure in which the carbazole derivatives where the
5-membered hetero ring such as thiophene is positioned at one benzene of carbazole
are trimerized like Formula 3. Since the basic structure of the compound of the present
invention is not changed depending on the substituents of (he compound, (he basic
physical properties of the compound according to the present invention are not
changed depending on the substituents. However, in the compounds of Formulae 2 and
3, the degree of realization of basic physical properties, emission wavelength of light
and/or other incidental properties are changed depending on the types of substituents.
[68] The method of producing the compound according to the present invention is as
follows.
[69] In the prior art, the compounds of Formula 2 and Formula 3 cannot be synthesized
because it is difficult to synthesize trimer compounds of carbazole or its derivatives.
Particularly, the compound of Formula 2, in which the amine group is substituted with
die aromatic group in the carbazole trimer, cannot be produced using die mediod of
producing die conventional carbazole trimer compound, in which the amine group is
substituted with die alkyl group in die carbazole trimer. For example, in die prior art, in
order to produce die compound in which die amine group of die carbazole trimer is
substituted with die alkyl group, a carbazole monomer, in which die amine group is
substituted with die alkyl group, is produced and men trimerized. With die above conventional
procedure, however, it is impossible to produce die compound of Formula 2,
in which die amine group is substituted with die aromatic group.
[70] After die compound of Formula 4 is produced, die compound of Formula 4, a
precursor of die aromatic compound which will substitute die amine group, Na(t-BuO),
a Pd2(dab)3 catalyst, and a 2-(di-t-burylphosphino)diphenyl Ugand are reacted in a
xylene solvent to produce die compound of Formula 2.
(Figure Removed)
[75] The compound of Formula 3 may be produced using a niethod in which a carbazole
derivative monomer where a 5-membered hetero ring such as (hiopheae are positioned
at one benzene of carbazole is trimerized and a substituenl is introduced to an amine
group of the carbazole derivative, or a method in which the amine group of the
carbazole derivative monomer is substituted with the substituent and the monomer is
then trimerized.
[76] Examples of the halogen atom of the substituents of Formulae 2 and 3 include
fluorine (F), chlorine (Q), bromine (Br), and iodine (I).
[77] An alkyl group of the substituents of Formulae 2 and 3 preferably has a ca/bon
number of 1 - 20, and is exemplified by a straight chain alkyl group, such as a methyl
group, an ethyl group, a propyl group, or a hexyl group, and a branched chain alkyl
group, such as an isopropyl group or a t-butyl group.
[78] Examples of an aromatic group of the substituents of Formulae 2 and 3 include a
monocyclic aromatic group, such as a phenyl group, a polycyclic aromatic group, such
as naphthyl, anthryl, pyrene, and perylene, and a heterocyclic aromatic group, such as
pyridine.
[79] Examples of an aralkyl group of the substituents of Formulae 2 and 3 include an
alkyl group having a carbon number of 1 - 20 which is substituted with aromatic hydrocarbons,
such as phenyl, biphenyl, naphthyl, terphenyl, anthryl, pyrel, and perylene.
[80] Examples of an arylamine group of die substituents of Formulae 2 and 3 include an
amine group which is substituted with aromatic hydrocarbons, such as phenyl,
biphenyl, naphthyl, terphenyl, anthryl, pyrene, and perylene.
[81] Examples of an alkylamine group of (he substituents of Formulae 2 and 3 include
an amine group which is substituted with aliphatic hydrocarbons having a carbon
number of 1-20.
[82] Examples of an aralkylamine group of the substituents of Formulae 2 and 3 include
an amine group which is substituted with aromatic hydrocarbons, such as phenyl,
biphenyl, naphthyl, lerphenyl, anthryl, pyrene, and perylene, and aliphatic hydrocarbons
having a carbon number of 1 - 20.
[83] Examples of a heterocyclic group of the substituents of Formulae 2 and 3 include a
pyrrolyl group, a thienyl group, an indole group, an oxazol group, an imidazole group,
a thiazd group, a pyridyl group, a pyrirnidine group, a piperazine group, a thiophene
group, a ruran group, and a pyridazinyl group.
[84] Substituted alkyl, aromatic, aralkyl, arylamine, alkylamine, aralkylamine, and heterocyclic
groups of the substituenls of Formulae 2 and 3 may include a halogen atom,
such as fluorine, chlorine, bromine, and iodine, a nitrile group, a nitro group, a formyl
group, an acetyl group, an arylamine group, an alkylamine group, an aralkylamine
group, a benzoyl group, an amide group, a styryl group, an acetylene group, a phenyl
group, a naphthyl group, an anthryl group, a pyrene group, a perylene group, a pyridyl
group, a pyridazyl group, a pyrrolyl group, an imidazolyl group, a quinolyl group, an
enthrone group, an acridone group, and an acridine group.
[85] In an embodiment of the present invention, the compound of Formula 2 may be a
compound in which Rl to R3 each are substituted or unsubstituted aromatic groups;
R6, RIO, and R14 each are selected from the group consisting of a halogen atom, a
uitrile group (CN), a nitro group (NO2), a formyl group, an acetyl group, a benzoyl
group, an amide group, a styryl group, an acetylene group, a quinoline group, a
quinazoline group, a phenanthroline group, a cuproin group, a substituted or unsubstituted
alkyl group, a substituted or unsubstituted aromatic group, a substituted or
unsubstituted aralkyl group, a substituted or unsubstituted arylamine group, a
substituted or unsubstituted alkylamine group, a substituted or unsubstituted aralkylamine
group, and a substituted or unsubstituted heterocyclic group; and R4, R5,
R7, R8, R9, Rl 1, R12, R13, and R15 are hydrogen in Formula 2.
[86] In an embodiment of the present invention, the compound of Formula 3 may be a
compound in which Rl to R3 each are selected from the group consisting of hydrogen,
a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aromatic
group; RS, R7, and R9 each are selected from the group consisting of a halogen atom,
a nitrile group (CN), a nitro group (NO2), a formyl group, an acetyl group, a benzoyl
group, an amide group, a styryl group, an acetylene group, a quinoline group, a
quinazoline group, a phenanthroline group, a cuproin group, a substituted or unsubstituted
alkyl group, a substituted or unsubstituted aromatic group, a substituted or
unsubstituted aralkyl group, a substituted or unsubstituted arylamine group, a
substituted or unsubstituted alkylamine group, a substituted or unsubstituled aralkylamine
group, and a substituted or unsubstituted heterocyclic group; and R4, R6,
and R8 are hydrogen in Formula 3.
[87] Illustrative, but non-limiting examples of the compound of Formula 2 include
Formulae 2-1 to 2-23.
(Figure Removed)
[172] Furthermore, the present invention provides an organic light emitting device whic
comprises a first electrode, one or more organic material layers, and a second electrode
sequentially layered therein. One or more layers of the organic material layers
comprise the compound of the above Formula 1.
[ 173] The organic material layer of the organic light emitting device according to the
present invention may have a single layer structure, or alternatively, a multilayered
structure in which two or more organic material layers are layered. For example, as the
organic material layer, the organic light emitting device of the present invention may
have a hole injection layer, a hole transport layer, a light emitting layer, an electron
transport layer, an electron injection layer, or a buffer layer interposed between (he
anode and the hole injection layer. However, the structure of the organic tight emitting
device is not limited to mis, but may comprise a smaller number of organic material
layers.
[174] Illustrative, but non-limiting examples of the structures of the organic light emitting
device according to the present invention are shown in FIGS. 1 to 4.
[175] FIG. 1 illustrates the structure of an organic light enduing device in which an anode
102, a light emitting layer 105, and a cathode 107 are sequentially layered on a
substrate 101. in this structure, the light emitting layer 105 may be formed using the
compound of Formula 1.
[176] FIG. 2 illustrates the structure of an organic light emitting device in which an anode
102, a hole transport and light emitting layer 105, a light emitting and electron
transport layer 106, and a cathode 107 are sequentially layered on a substrate 101. in
this structure, the hole transport and light emitting layer 105 may be formed using the
compound of Formula 1.
[177] FIG. 3 illustrates the structure of an organic light emitting device in which a
substrate 101, an anode 102, a hole injection and transport layer 104, a light emitting
layer 105, an electron transport layer 106, and a cathode 107 are sequentially layered,
in this structure, the hole injection and transport layer 104 and/or the light emitting
layer 105 may be formed using the compound of Formula 1.
[178] FIG. 4 illustrates the structure of an organic light emitting device in which a
substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, a
light emitting layer 105, an electron transport layer 106, and a cathode 107 are sequentially
layered, in this structure, the hole injection layer 103, the hole transport
layer 104, and/or the light emitting layer 105 may be formed using the compound of
Formula 1.
[179] In the organic light emitting device of the present invention, the layer including the
compound of Formula 1 may be formed between the anode and the cathode through a
vacuum deposition method or a solution coating method. Illustrative, but non-limiting
examples of the solution coating method include a spin coating method, a dip coating
method, a doctor blading method, an InkJet printing method, and a heat transcription
method.
[180] The thickness of the organic material layer containing the compound of Formula 1
is 10 |im or less, preferably 0.5 urn or less, and more preferably 0.001 - 0.5 tun.
[181] The layer including the compound of Formula 1 may further comprise other
materials which are capable of conducting injection of holes, transport of (he holes,
light emission, transport of electrons, and injection of the electrons known in the art, if
necessary.
(182] The organic light emitting device of the present invention can be produced using
known materials through a known process, modified only in that one or more layers of
organic material layers include the compound of the present invention, mat is, the
compound of Formula 1.
[183] For example, the organic light emitting device of the present invention may be
produced by sequentially layering a first electrode, an organic material layer, and a
second electrode on a substrate. In connection with this, a physical vapor deposition
(PVD) method, such as a sputtering method or an e-beam evaporation method, may be
used, but the method is not limited to these.
Mode for the Invention
[185] A better understanding of the present invention may be obtained hi light of the
following examples which are set forth to illustrate, but are not to be construed to limit
the present invention.
[ 187] Preparation of a compound of Formula 4
[192] A mixture of oxindole (1.3 g, 10 nunol) and 5 mL of POC13 was reacted at 120 for 15 hours.
[193] After the reaction was completed, excess POC13 was removed by distillation, 10
mL of ice water were added to the remaining product, and sat. Na2CO3 was added
thereto to conduct neutralization. Subsequently, the reactants were filtered, washed
with wafer and ethanol, and vacuum dried. The resulting compound was separated
using column chromatography (ethyl acetate: n-Hexane - 1:4) to produce die pure
compound of Formula 4 (0.65 g, Yield=54 %): MS[M+1]+ 346.
[202] 0.13 g (1.36 mmol) of Na(t-BuO), 331 mg (0.03 mmol) of Pd2(dba)3, and 10 mg
(0.05 mmol) of 2-(di-t-butylphosphino)diphenyl were added to a mixture of 1.2 g (3.4
mmol) of die compound of Fonnula 4 and 2.8 g (1.36 mmol) of iodobenzene in 70 mL
of xylene, and reacted at 120°C for 1 hour. After the reaction was finished, cooling to
room temperature was conducted, and the precipitate was filtered, washed with water
and ethanol, and vacuum dried. The resulting compound was dissolved in 80 mL of a
THF solvent, and treated with acidic white clay to remove inorganic metals, such as
Pd. The filtrate was concentrated and precipitated in ethanol. The precipitate was then
vacuum dried (1.0 g, Yield = 62 %): Mp 35TC (DSC); MSfM+lf 574.
[204] PREPARATION EXAMPLE 2
[206] Preparation of the compound of Fonnula 2-2
[208] Fonnula 2-2
The procedure of preparadon example 1 was repeated to produce the compound of
Formula 2-2 except that 3-iodotoluene was used instead of iodobcnzene.
(1.2 g, Yield = 58 %):Mp J» 380«C, To 149JVC (DSC); MS[M+1]+ 616
PREPARATION EXAMPLE 3
Preparation of the compound of Formula 2-9
Formula 2-9
[220]
[221] The procedureof preparation example 1 was repealed to produce the compound of
Formula 2-9 except that 4-bromobiphenyl was used instead of iodobenzene.
[222] (1.5 g, Yield = 56 %):Mp 314.4°C (DSC); MS[M+1]+ 802
PREPARATION EXAMPLE 4
Preparation of the compound of Formula 2-15
Formula 2-15
[230]
[231] The procedure of preparation example 1 was repeated to produce the compound
Formula 2-15 except that N-(4-bromophenyl)-N-naphthyl-l-yl-N-phenylamine was
used instead of iodobenzene.
[232] (1.9 g, YieJd = 45 %):Mp 360.9°C TG 189.7°C (DSC); MS[M+lf 1225
(Figure Removed)
[244] Preparation of the compound of Formula Sa
[245] The same procedure disclosed in Chem. Pharm. Bull. 1993.41. 1293-1296 was
used to prepare the compound of Formula 5a.
[246] MS [M+1H 286.
[248] Preparation of the compound of Formula 5b
[249] The same procedure disclosed in J. Org. Chem. Vol. 69. No. 14.2004 was used to
prepare the compound of Formula Sb.
[250] MS[M+l]+292.
[251]
[252] Preparation of the compound of Formula 3-1
[253] A mixture of compound 5b (2.9 g, 10 mmol) and 5 mL of POC13 was reacted at
100 °C for 10 hours.
[254] After the reaction was completed, excess POC13 was removed by distillation, 10
mL of ice water were added to the remaining product, and saturated Na2CO3 was
added thereto to conduct neutralization. Subsequently, the reactants were filtered,
washed with water and ethanol, and dried under vacuum. The resulting compound was
separated using column chromatography (ethyl acetate: n-Hexane = 1:10) to produce
the pure compound of Formula 3-1 (1.6 g, Yield=60%): MS [M+l]+ 820.
[255]
[256] EXAMPLE 1
[257]
[258] Preparation of an organic light emitting device
[259]
[260] A glass substrate, on which ITO (indium tin oxide) was applied to a thickness of
1500 A to form a thin film, was put in distilled water, in which a detergent was
dissolved, and washed for 30 min using ultrasonic waves. Subsequently, ultrasonic
washing was conducted in distilled water twice for 10 min. A product manufactured by
Fischer Inc. was used as the detergent, and distilled water was produced by filtering
twice using a filter manufactured by Millipore Inc. After the washing using distilled
water was finished, ultrasonic washing was conducted sequentially using isopropyl
alcohol, acetone, and methanol solvents, and drying was then conducted. Next, it was
transported to a plasma washing machine. Subsequently, the substrate was washed
using nitrogen plasma for 5 min, and then transported to a vacuum evaporator.
[261] Hexanitrile hexaazalriphenylene of the following Formula 5 was vacuum deposited
to a thickness of 500 A by heating on a transparent ITO electrode, which was prepared
through the above procedure, so as to form a hole injection layer. The compound of
Formula 2-1, which was a material transporting holes and was produced in preparation
example 1, was vacuum deposited thereonto in a thickness of 400 A, and the
compound (Alq3) of Formula 6 was vacuum deposited thereonto in a thickness of 300
A, to form a light emitting layer. A compound of Formula 7 was vacuum deposited on
the light emitting layer to a thickness of 200 A so as to form an electron transport
layer. Lithium fluoride (LiF) having a thickness of 10 A and aluminum having a
thickness of 2500 A were sequentially deposited to form a cathode.
[262] In the above procedure, the deposition speed of an organic material was maintained
at 1 A/sec, and lithium fluoride and aluminum were deposited at a speed of 0.2 A/sec
and 3 7 A/sec, respectively.
[263] In the resulting organic light emitting device, an intrinsic green spectrum of Alq3
having brightness of 4000 cd/m2 was observed at a forward current density of 100 mAJ
cm2, and corresponded to x of 0.34 and y of 0.56 based on a 1931 Cffi color
coordinate.
(Figure Removed)
EXAMPLE 2
The procedure of example 1 was repeated to produce an organic light emitting
device except that the compound of Fonnula 2-2 was used as a hole transport material
instead of the compound of Fonnula 2-1.
la the resulting organic light emitting device, an intrinsic green spectrum of Alq3
having brightness of 4960 cd/m2 was observed at a forward current density of 100 mA/
cm2, and corresponded to x of 0.33 and y of 0.56 based on a 1931CEE color
coordinate.
[278]
[279] EXAMPLE 3
[280]
c The procedure of example 1 was repeated to produce an organic light emitting
device, except that the compound of Formula 2-9 was used as a hole transport material
instead of the compound of Formula 2-1.
[282] In the resulting organic light emitting device, an intrinsic green spectrum of AJq3
having brightness of 49S9 cd/m2 was observed at a forward current density of 100 mA/
cm2, and corresponded to x of 0.33 and y of 0.56 based on a 1931 CDE color
coordinate.
[283]
[284] COMPARATIVE EXAMPLE 1
[285]
[286] The procedure of example 1 was repeated to produce an organic light emitting
device except that NPB, which was conventionally known as a hole transport material,
was vacuum deposited to a thickness of 400 A on a hole injection layer instead of the
compound of Formula 2-1 to form a hole transport layer.
[287] In the resulting organic light emitting device, an intrinsic green spectrum of Alq3
having brightness of 340 cd/m1 was observed at a forward current density of 100 mA/
cm2, and corresponded to x of 0.32 and y of 0.56 based on a 1931 CDE color
coordinate.
[288]
[289] From the results of the above-mentioned examples and comparative example, it can
be seen that the compounds of the present invention function to transport holes like
NPB, which is a conventional hole transport material, and improve the efficiency of a
device at the same current density in comparison with NPB.
[290]
Industrial Applicability
[291] A compound of the present invention is a novel compound which acts as a hole
injection material, a hole transport material, a light emitting host, or a light emitting
dopant in an organic light emitting device.







We Claim:
1. A carbazole compound of Formula 1:
(Formula Removed)
wherein,
X1 to X3 each are a substituted or unsubstituted benzene ring, or a substituted or unsubstituted 5-membered heterocyclic aromatic group which includes a ring source selected from the group consisting of a substituted or unsubstituted benzene ring, O, S, and NR' (R1 is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aromatic group);
Rl to R3 each are selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group, and a substituted or unsubstituted heterocyclic aromatic group with a proviso that XI to X3 be a substituted or unsubstituted 5-membered heterocyclic aromatic group.
2. The compound as claimed in claim 1, wherein the compound of Formula 1 is a
compound of Formula 2:
(Formula Removed)
wherein,
R1 to R3 each are a substituted or unsubstituted aromatic group, or a substituted or unsubstituted heteroaromatic group; and
R4 to R15 are each selected from the group consisting of hydrogen, a halogen atom, a nitrile group (CN), a nitro group (N02), a formyl group, an acetyl group, a benzoyl group, an amide group, a styryl group, an acetylene group, a quinoline group, a quinazoline group, a phenanthroline group, a cuproin group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aralkylamine group, and a substituted or unsubstituted heterocyclic group.
3. The compound as claimed in claim 1, wherein the compound of Formula 1 is a compound of Formula 3:
(Formula Removed)
wherein,
Rl to R3 each are selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group, and a substituted or unsubstituted heterocyclic aromatic group;
R4 to R9 each are selected from the group consisting of hydrogen, a halogen atom, a nitrile group (CN), a nitro group (N02), a formyl group, an acetyl group, a benzoyl group, an amide group, a styryl group, an acetylene group, a quinoline group, a quinazoline group, a phenanthroline group, a cuproin group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted alkylamine group,
a substituted or unsubstituted aralkylamine group, and a substituted or unsubstituted heterocyclic group; and
Y is selected from the group consisting of 0, S, and NR' (R' is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted aromatic group).
4. An organic light emitting device, comprising:
a first electrode;
one or more organic material layers including a light emitting layer;
and a second electrode,
wherein said first electrode, the one or more organic material layers, and the second electrode are sequentially layered, and the one or more organic material layers include the use of compound as claimed in any of the preceding claims 1 to 3.
5. The organic light emitting device as claimed in claim 4, wherein the light emitting layer of the organic material layers includes the use of compound as claimed in any of the preceding claims 1 to 3.
6. The organic light emitting device as claimed in claim 4, wherein the organic material layers comprise a hole injection layer, and the hole injection layer includes the use of compound as claimed in any of the preceding claims 1 to 3.
7. The organic light emitting device as claimed in claim 4, wherein the organic material layers comprise a hole transport layer, and the hole transport layer includes the compound according to any one of claims 1 to 3.
8. The organic light emitting device as claimed in claim 4, wherein the organic material layers comprise a layer which both injects and transports holes and which includes the use of compound as claimed in any of the preceding claims 1 to 3.

Documents:

2032-delnp-2007-abstract.pdf

2032-delnp-2007-assigment.pdf

2032-DELNP-2007-Claims-(15-03-2007).pdf

2032-DELNP-2007-Claims-(16-05-2011).pdf

2032-DELNP-2007-Claims-(21-02-2012).pdf

2032-delnp-2007-claims.pdf

2032-delnp-2007-Correspondence Others-(03-07-2012).pdf

2032-DELNP-2007-Correspondence Others-(21-02-2012).pdf

2032-DELNP-2007-Correspondence-Others(16-05-2011).pdf

2032-delnp-2007-correspondence-others.pdf

2032-DELNP-2007-Description (Complete)-(15-03-2007).pdf

2032-delnp-2007-description (complete).pdf

2032-delnp-2007-drawings.pdf

2032-DELNP-2007-Form-1-(16-05-2011).pdf

2032-DELNP-2007-Form-1-(21-02-2012).pdf

2032-delnp-2007-form-1.pdf

2032-delnp-2007-form-18.pdf

2032-DELNP-2007-Form-2-(21-02-2012).pdf

2032-delnp-2007-form-2.pdf

2032-delnp-2007-Form-3-(03-07-2012).pdf

2032-DELNP-2007-Form-3-(16-05-2011).pdf

2032-delnp-2007-form-3.pdf

2032-delnp-2007-form-5.pdf

2032-DELNP-2007-GPA-(21-02-2012).pdf

2032-delnp-2007-gpa.pdf

2032-delnp-2007-pct-210.pdf

2032-delnp-2007-pct-301.pdf

2032-delnp-2007-pct-304.pdf

2032-DELNP-2007-petition-137-(16-05-2011).pdf


Patent Number 253223
Indian Patent Application Number 2032/DELNP/2007
PG Journal Number 27/2012
Publication Date 06-Jul-2012
Grant Date 05-Jul-2012
Date of Filing 15-Mar-2007
Name of Patentee LG CHEM. LTD.
Applicant Address 20, YOIDO-DONG, YOUNGDUNGPO-GU, SEOUL, 150-721, REPUBLIC OF KOREA
Inventors:
# Inventor's Name Inventor's Address
1 JUN GI JANG 7-401 LG PARTNER APT., DORYONG-DONG, YUSEONG-GU, DAEJEON METROPOLITAN CITY, 305-340, REPUBLIC OF KOREA
2 KONG KYEOM KIM 107-703 EXPO APT., JEONMIN-DONG, YUSEONG-GU, DAEJEON METROPOLITAN CITY, 305-761, REPUBLIC OF KOREA
PCT International Classification Number C09K 11/06
PCT International Application Number PCT/KR2005/003077
PCT International Filing date 2005-09-15
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 10-2004-0074920 2004-09-20 Republic of Korea